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INSECT

ANTIFEEDANTS

© 2005 by CRC Press LLC


INSECT
ANTIFEEDANTS

Opender Koul
Insect Biopesticide Research Centre
Jalandhar, India

CRC PR E S S
Boca Raton London New York Washington, D.C.

© 2005 by CRC Press LLC


Library of Congress Cataloging-in-Publication Data

Koul, Opender.
Insect antifeedants / by Opender Koul.
p. cm.
Includes bibliographical references (p. ).
ISBN 0-415-33400-4 (alk. paper)
1. Insect antifeedants. 2. Biological insecticides. 3. Insecticidal plants. I. Title

SB931.K786 2004
632'.7--dc22
2004051077

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ACKNOWLEDGMENTS
I thank Prof. Sukh Dev (India), Prof. Murray B. Isman (Canada), Prof. A. J. Mordue Luntz
(UK), Prof. W. Kraus (Germany), Prof. L. M. Schoonhoven (Netherlands), and Dr. Michael
J. Smirle (Canada) for critical reading and valuable suggestions on various chapters in this
book. I also thank my students, particularly Gurmeet Singh for editorial assistance in arrang-
ing references.

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© 2005 by CRC Press LLC
PREFACE
In the recent past, the virtual dependence on neurotoxic chemicals to control pest insects has
provided the impetus for studies into alternative methods of pest control that could avoid the
environmental hazards associated with broad-spectrum insecticides. Overuse of synthetic
insecticides that share a neurotoxic mode of action for pest management in agriculture,
forestry, and managed landscapes has often induced negative impacts on natural enemies,
pollinators, and other non-target organisms and often leads to the development of resistance.
Fortunately new alternatives for pest control can be found within the large group of natural
products or the synthetic derivatives thereof, which have the advantage of providing novel
modes of action, therefore reducing the risk of cross-resistance. Naturally occurring mixtures
of substances provide a multifactorial selective pressure on pests that also slows down the
development of resistance. More important, research in this area has uncovered subtle but
effective mechanisms of pest control, such as the behavior-modifying method of feeding
deterrence.
Therefore, the concept of using insect antifeedants as crop protectants is intuitively
attractive. Most plant defensive chemicals discourage insect herbivory, either by deterring
feeding and oviposition or by impairing larval growth, rather than by killing insects outright.
One application of our understanding of plant defensive chemistry, then, is the identification
of putative deterrent substances that could be isolated in sufficient quantities or synthesized
for use as crop protectants. In fact, an insect antifeedant is a behavior-modifying substance
that deters feeding through a direct action on peripheral sensilla in insects. This definition
excludes chemicals that suppress feeding by acting on the central nervous system (following
ingestion and absorption), or a substance that has sublethal toxicity to the insect. During the
past three decades scores of compounds have been isolated from various natural sources, or
semi-synthetic derivatives have been prepared that have the potential to inhibit feeding of a
variety of insect species. However, all these studies are scattered through the biological and
chemical literature, and it was felt necessary to assemble this data in the form of a compre-
hensive treatise on this expanding area of study and application that would aid investigators
and lead them to more effective and desirable solutions to insect control.
The present volume, therefore, is an attempt to compile all the data as a single text that
deals specifically, as far as possible, with various aspects of insect antifeedants discussed in
seven chapters. Chapter 1 introduces the subject with an emphasis on definitions and the role
of antifeedants as a whole. Food selection among insect herbivores is a highly specialized
phenomenon. While olfactory and physical aspects of plants or their organs can be important
in insect host finding and acceptance, the choice of food is based primarily upon contact
chemoreception of various allelochemicals. In particular, dietary experience has been found
to influence the ability of insects to taste plant chemicals that may serve as signals of suitability
or unsuitability. Certain dietary constituents appear to suppress the development of taste
sensitivity to deterrents in an insect. Avoidance of allelochemicals, when looked at from a
behavioral point of view, is the outcome of interactions with chemoreceptors characterized
by an often-broad sensitivity spectrum of deterrents; therefore, Chapter 2 discusses the
concepts and mechanisms involved in the process.

vii
© 2005 by CRC Press LLC
In relation to the response of insects to these chemicals, the aspect of evaluation is
important and accordingly various bioassay procedures have been developed, which are
discussed in Chapter 3 and are mostly species specific. The overall picture, which emerges
from various evaluations, shows that small structural variations can produce drastic changes
in the activity profile of compounds. A critical examination of functional groups present in
the active molecules provides crucial information about the optimal relative stereochemistry
required to stimulate an antifeedant response in insects. The main aim of Chapter 4 is directed
in this direction and generalizes sufficient structure-activity information within specific skel-
etal systems to allow rational modification of readily available feeding deterrents to be made
into potential insect control agents. Commercialization aspects, practical applications, and
conclusions drawn from various studies are discussed in Chapters 5 and 6. The last chapter
is the monograph section, which presents relevant information on nearly 900 compounds (in
alphabetical order) that is directly accessible. It has been the endeavor to give complete details
on the latest structural information and biological data for those compounds that deter feeding
of insects.
I hope the book will prove useful to all those interested in promoting the cause of new
pest control allelochemicals so that sustainability in agriculture systems and environmental
protection for future generations is achieved.

viii
© 2005 by CRC Press LLC
Dedicated to the memory
of my mother Uma Koul

© 2005 by CRC Press LLC


ABOUT THE AUTHOR
Opender Koul, Fellow of the National Academy of Agricultural Sciences and the Indian
Academy of Entomology, is an insect toxicologist/physiologist/chemical ecologist and cur-
rently the Director of the Insect Biopesticide Research Centre, Jalandhar, India. After obtain-
ing his Ph.D. in 1975 he joined the Regional Research Laboratory (CSIR), Jammu, and then
became Senior Group Leader of Entomology at Malti-Chem Research Centre, Vadodara,
India (1980–1988). He has been a visiting scientist at the University of Kanazawa, Japan
(1985–1986), University of British Columbia, Canada (1988–1992), and Institute of Plant
Protection, Poznan, Poland (2001). His extensive research experience concerns insect–plant
interactions, spanning toxicological, physiological, and agricultural aspects. Honored with
an Indian National Science Academy medal (INSA) and the Kothari Scientific Research
Institute award, he has authored over 140 research papers and articles, and is the author or
editor of the books Insecticides of Natural Origin, Phytochemical Biopesticides, Microbial
Biopesticides, Predators and Parasitoids, Neem: Today and in the New Millennium, Integrated
Pest Management: Potential, Constraints and Challenges, and Transgenic Crop Protection:
Concepts and Strategies. He has also been an informal consultant to BOSTID, NRC of the
United States at ICIPE, Nairobi.

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© 2005 by CRC Press LLC
CONTENTS

1 Introduction........................................................................................................................1
References............................................................................................................................6

2 Concepts and Mechanisms ...............................................................................................9


Chemosensory System.......................................................................................................10
Stereoselective Perception.................................................................................................11
Mechanisms .......................................................................................................................14
GABA Antagonistic Mechanism.......................................................................................15
Biogenic Amine Inhibition Mechanism ............................................................................17
Mechanisms Related to Specific Allelochemicals ............................................................17
References..........................................................................................................................19

3 Bioassays...........................................................................................................................25
Leaf Disk Assay ................................................................................................................26
Artificial Diet Feeding.......................................................................................................29
Styropor Assay ..................................................................................................................31
Glass Fiber Disk Test ........................................................................................................31
Paper Towel Disk Test.......................................................................................................31
Wafer Assay.......................................................................................................................32
Electrophysiological Assay ...............................................................................................33
Other Miscellaneous Methods...........................................................................................34
Simulation Bioassay .....................................................................................................34
Dipteran Assays ............................................................................................................35
WireWorm (Melanotus Communis) Assay...................................................................36
Boll Weevil Assay.........................................................................................................36
Scale Insect Assay ........................................................................................................36
Sawfly Assay.................................................................................................................36
Leaf Beetle Assay .........................................................................................................37
Oral Dosing...................................................................................................................37
Field Trials ....................................................................................................................38
References..........................................................................................................................38

4 Structure-Activity Relationships....................................................................................43
Limonoids ..........................................................................................................................43
Quassinoids........................................................................................................................50
Diterpenes ..........................................................................................................................53
Sesquiterpenes ...................................................................................................................56
Monoterpenes ....................................................................................................................58
Coumarins..........................................................................................................................59

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Isoflavonoids ......................................................................................................................63
Alkaloids............................................................................................................................64
Maytansinoids....................................................................................................................65
Ellagitannins ......................................................................................................................65
Aristolochic Acids .............................................................................................................67
References..........................................................................................................................68

5 Commercialization...........................................................................................................73
References..........................................................................................................................77

6 Practical Applications and Conclusions........................................................................79


Conclusions........................................................................................................................82
References..........................................................................................................................83

7 Bioefficacy Monographs..................................................................................................85

© 2005 by CRC Press LLC


1 INTRODUCTION
Research over the last 35 years has provided substantial evidence that plants and animals
often produce substances that affect the growth, development, behavior, and distribution of
other organisms. Such naturally occurring substances are called “allelochemicals.” The term
“allelochemic” was first proposed by Whitaker and Feeny (1971) and has been defined as a
chemical that is significant to organisms of a species different from its source for reasons
other than food as such (Nordlund, 1981). In fact, the term allelochemical comes from many
terms that have been designated for chemicals that convey information between organisms;
“semiochemicals” is the umbrella term, which comprises both information-conveying chem-
icals and toxins. Dicke and Sabelis (1988) have rightly used the term “information conveying
chemicals,” as they differ from general toxins and nutrients in that the former are not
themselves detrimental or beneficial, but may be through the responses they elicit. Thus using
the term “infochemicals” is based on:

1. Whether the interaction is intra- or interspecific (pheromone versus allelochemical)


2. Which costs and benefits fall to each of the two interacting organisms
3. The identity of the producer and the receiver

Four major categories of allelochemicals have now been recognized: the allomones,
kairomones, synomones, and apneumones. However, Whitman (1988) has added another
category, in which neither interactant benefits, and called them antimones. There is also a
possibility that one chemical that benefits an organism in one interaction may also have side
effects in other interactions (Whitman, 1988). However, all terms are context specific rather
than chemical specific. To be precise, “infochemicals” in the present context is appropriate
and can be characterized as in Figure 1.1.

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2 Opender Koul

INFOCHEMICALS

PHEROMONES ALLELOCHEMICALS

1. (+, −) Pheromone 1. Allomone


Benefit to emitter

2. Kairomone
2. (−, +) Pheromone
Benefit to receiver 3. Synomone

4. Apneumone
3. (+, +) Pheromone
Benefit to both 5. Antimone

FIGURE 1.1 Infochemical terminology.

The objective of this book is to explore the studies of insect antifeedants and accordingly
deal with allelochemicals in general and allomones in particular. “Allomones” have been
defined as substance(s) produced or acquired by an organism that, when it contacts an
individual of another species in the natural context, evokes in the receiver a behavioral or
physiological response that is adaptively favorable to the emitter but not to the receiver
(Nordlund, 1981). As such, allomones are differentiated from pheromones because they
mediate interspecific, rather than intraspecific interactions. Receiving organisms respond to
allomones in a variety of ways. Subtle changes in behavior and physiology of the receiver
can result in host-shifts in phytophages or parasites, or extended developmental times due to
reductions in nutritional value of foodstuffs. At the other end of the spectrum, violent reactions
leading quickly to injury and death are often the result of encounters with highly toxic
defensive allomones. This tremendous diversity, coupled with the intensity of allomone-
mediated interspecific interactions, makes allomonal chemicals potential agents for insect
pest control.
Although allomones mediate a wide variety of complex interactions, allomonal chemicals
fall into one of two basic categories. The first of these includes materials produced by the
organisms and released into the environment, mostly volatile compounds that exert their
influences at some distance from the emitter. For instance, it is well known that green plants
release characteristic volatiles arising from the metabolism of leaf lipids such as linoleic
acids, which by oxidative degradation produce a variety of 6-carbon alcohols and aldehydes.
Such volatiles include a wide variety of short chain alcohol and aldehydes, ketones, esters,
aromatic phenols, mono- and sesquiterpenes, and a host of other secondary metabolites. The
second group of allomones includes compounds produced or acquired for defense, which
remain in the body of the producer. This group includes toxins sequestered by insects for
defense and the vast array of plant allelochemicals or secondary plant compounds. There are
several characteristics required for the evolution of the ability of polyphagous insects (in
category II) to use plant secondary metabolites as defense compounds. The main prerequisites
for the evolution of unpalatability due to such compounds could be the:

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Insect Antifeedants 3

• Feeding on a toxic plant thus having potential defense compounds in the insect’s
diet
• Elimination of detoxification mechanism by inactivating detoxification enzymes
so that defense compounds are not broken down
• Ability of compounds to move through the gut and reach the haemolymph
• Accumulation of defense compounds in the haemolymph against an osmotic gra-
dient and retention of compounds through the stadium (Bowers, 1992)

In other words, the allomones are the phytochemicals produced from secondary metabolic
pathways and are the major mechanisms by which plants are protected from excessive
herbivory. Behavioral mechanisms provide a system of avoidance of non-host chemicals by
which insects select their food, though the molecular basis for action of chemical deterrents
on both gustatory and olfactory sensory systems in insects is only poorly understood. Among
plant anti-herbivore chemistry, a strong link does not exist between feeding deterrence and
internal toxicity in insects, suggesting that behavioral rejection is not an adaptation to ingested
effects but more an outcome of deterrent receptors with wide chemical sensitivity (Mullin et
al., 1991, 1994). Many of these substances are bitter, and acceptance of host plants by
herbivores requires chemoreception of favorable levels of phagostimulants relative to anti-
feedants (Dethier, 1980). This restricts the application of a very liberal definition for an
antifeedant, namely, “any substance that reduces consumption by an insect” to a more precise
definition: “A peripherally mediated behavior-modifying substance (i.e., acting directly on
the chemosensilla in general and deterrent receptors in particular) resulting in feeding deter-
rence” (Isman, 1994). This definition, however, excludes chemicals that suppress feeding by
acting on the central nervous system (following ingestion or absorption), or a substance that
has sublethal toxicity to the insect (Isman, 2002).
Feeding deterrents with a wide diversity of structures are not known to directly interfere
with insect taste cell responses to phagostimulants such as sugars (Lam and Frazier, 1991;
Schoonhoven et al., 1992). Presently the mode of action of feeding modifying chemicals in
insect gustatory systems is largely unknown (Frazier, 1992; Schoonhoven et al., 1992), though
some molecular targets have been identified (Koul, 1997). Taste receptor proteins are only
now beginning to be biochemically purified and cloned. The determination of the molecular
basis for action of feeding deterrents in the insect gustatory system is thus a primary goal
among basic and applied entomologists interested in insect–plant interactions or in the control
of herbivore pests.
According to the theory of biochemical coevolution it should be possible to develop an
evolutionary pattern of antifeedants on the basis of their distribution in different plant families
and their biosynthetic pathways. Accordingly it has been possible to draw an evolutionary
scheme as shown in Figure 1.2 (modified from Harborne, 1988). However, the pattern of
distribution varies among families. One plant family may concentrate on one type of deterrent
molecule, like limonoids in the Rutales (Champagne et al., 1992) and also, within a family,
individual members may have developed further barriers to feeding. For instance, it is clear
that flavonoids in plants can modulate the feeding behavior of insects, though mechanisms
associated with these behavioral responses are not clearly understood (Simmonds, 2001).
Other families may diversify their deterrents; for example, non-protein amino acids
(e.g., L-canavanine), alkaloids, cyanogens, and isoflavones are found in the Fabaceae. Plants
produce all these and many varied compounds in the first instance as protective devices
against insect feeding. Thus a majority of plant families rely on secondary plant metabolites
for protection from phytophagous insects. One might surmise that within such a family the
more advanced members are better protected than others. Berenbaum (1983) has pointed to

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4 Opender Koul

Sesquiterpene Lactones Flavones


Alkaloids

Monoterpene Lactones
HERBACIOUS
Sesquiterpenes Non-protein
Aminoacids
Cardiac Glycosides

Cucurbitacins

Limonoids WOODY

Diterpenes

Saponins Quassinoids

Polyacetylenes Coumarins

ANGIOSPERMS
------------------------------------------------------------------------------------------------------------
---------
Ecdysteroids Tannins Cyanogens

Juvenoids
GYMNOSPERMS
FERNS

FATTY ACID TERPENOID PHENOLICS NITROGEN

BIOSYNTHETIC PATHWAYS

FIGURE 1.2 Possible evolutionary scheme of insect antifeedants in plants (modified from Harborne,
1988).

good evidence in the Apiaceae where plant defense is based on hydroxycoumarins, linear
furanocoumarins, and angular furanocoumarins, which are biosynthetically and toxicologi-
cally related.
It is also evident from various studies that as a result of coevolutionary pressures, plants
have a startling number of plant chemicals including chromenes, polyacetylenes, saponins,
quassinoids, cuccurbitacins, cyclopropanoid acids, phenolics, alkaloids, various types of
terpenes, and their derivatives, and each insect species may process these allomones in a
thoroughly idiosyncratic way, so that the same compound may have very different fates and
consequences in different species of insects (Koul, 1993; Blum et al., 1987). These various
insect–plant interactions are consistent with the idea of reciprocal evolutionary interactions
based on secondary metabolites. This, however, could be related to the evolution of deterrent

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Insect Antifeedants 5

receptors in insects, too. There is a clear indication that no two insect species are equipped
with an identical sensory system. Each species has a unique sensory window, which can
discriminate between host and non-host plants (Schoonhoven, 1982). Even in very closely
related species the chemical senses show striking differences (Drongelen, 1979). It can be
visualized from such information that the contact chemical senses may in evolutionary terms
be easily adapted to changing circumstances, as has been well evidenced in two strains of
Mamestra brassicae in response to sinigrin and naphtyl-β-glucoside (Wieczorek, 1976).
It can also be visualized that insect feeding deterrents may be perceived either by
stimulation of specialized deterrent receptors or by distortion of the normal function of
neurons, which perceive phagostimulating compounds. Some sugars are very important
components of an insect’s sustained feeding; the inhibition of the receptors is an effective
antifeedant action. Some antifeedants influence the feeding activity through a combination
of the two principal modes of action mentioned above.
Initial discoveries of antifeedant chemicals were simply made by chance when organo-
metallic compounds and a few insecticides were found to reduce insect feeding (Ascher and
Rones, 1964; Jermy and Metolcsy, 1967). This clearly emphasizes the point that many
synthetic compounds could be potential antifeedants for insect pests (Koul, 1993), of course
in addition to the allomones or their derivatives from natural sources. As early as 1932 Metzger
and Grant tested about 500 plant extracts against Popillia japonica, though results were not
substantially encouraging. Pradhan et al. (1962) evaluated extracts of the Indian neem tree,
Azadirachta indica, which prevented feeding by the desert locusts, and today nearly 900
compounds have been identified to possess feeding deterrence against insects (see Chapter 7),
though terrestrial plants produce a diverse array of secondary metabolites, likely more than
100,000 unique compounds (Isman, 2002). In addition to various compounds isolated or
synthesized as insect antifeedants, a number of studies demonstrate the antifeedant efficacy
in metabolite mixtures of plant essential oils or total extracts against a variety of insect species.
In recent years studies have revealed the antifeedant potential of plant essential oils against
post-harvest pests, aphids, thrips, lepidopterans, termites, and mite pests (Hori, 1999; Hou-
HouaMin et al., 2002a, 2002b; Koschier et al., 2002; Maistrello et al., 2003). Similarly, during
the past few years ample emphasis has been in demonstrating the antifeedant efficacy in total
plant extracts (Mancebo et al., 2000a, 2000b; Wang et al., 2000; Jannet et al., 2001; Lababidi
and Koudseieh, 2001; Schlyter, 2001; Wheeler and Isman, 2001; Mehta et al., 2002; Jayas-
inghe et al., 2003) as they seem to exhibit the activity as multicomponent systems. However,
it is also well known that antifeedants show interspecific variability (Chapman, 1974;
Schoonhoven and Jermy, 1977; Isman, 1993). Such interspecific differences, as shown for
many insect species, encourage the need to search selectively for specific feeding deterrents.
Van Beek and deGroot (1986) have suggested three considerations for the selection of
plants that are to be evaluated for antifeedant activity:

1. The species can be selected at random.


2. They could be selected on chemotaxonomic bases.
3. The species can be selected on the basis of ethnobotanical or entomological data.

All three methods have been used, and the second method has led to the most frequent
successes. It is, therefore, necessary to focus attention on particular chemical groups occurring
naturally in various sources, or environmentally safe synthetics, and thus obtain a large
number of active antifeedant compounds, which could be successfully introduced in Insect
Pest Management (IPM) programs. However, simultaneous to such developments it is nec-
essary to understand the concepts and mechanisms involved in antifeedant interactions. It is

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6 Opender Koul

also important to point out here that not much success has been achieved so far in establishing
a good commercial antifeedant for crop protection. However, the commercial potential and
the drawbacks will be discussed in Chapter 6.
Recently, it has also been demonstrated that neuropeptide-based pesticides potentially
offer levels of activity, specificity, and environmental compatibility absent in conventional
insecticides. However, neuropeptides are generally poor candidates for insecticides because
they do not easily penetrate the cuticle and degrade rapidly in the environment and insect
gut. Manduca sexta allatostatin (Manse-AS) regulates juvenile hormone biosynthesis in moths
and has myoregulatory action on the gut. Moreover, Manse-AS produces marked reductions
in feeding and growth when injected into larvae of the tomato moth, Lacanobia oleracea.
Snowdrop lectin (GNA) is detectable in the haemolymph of larvae following oral adminis-
tration. To determine whether GNA could transport neuropeptides across the gut, a recom-
binant expression system was used to produce a GNA/Manse-AS fusion protein (FP). Fol-
lowing expression in Escherichia coli, purified FP was incorporated in an artificial diet and
offered to tomato moth larvae. Intact FP appeared in the haemolymph following oral admin-
istration, which resulted in an almost total cessation of feeding and growth by larvae exposed
to the FP diet. These results offer the possibility of developing a whole range of novel, orally
active, target-specific antifeedants based on insect neuropeptides (Edwards et al., 2002).

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Insect Antifeedants 7

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damage caused by the onion thrips, Thrips tabaci. Crop Protection, 21, 419–425.
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(eds.), Synthesis and Chemistry of Agrochemicals II, ACS Symp. Ser. 443, American
Chemical Society, Washington, D.C., pp. 400–412.
Maistrello, L., Henderson, G., and Laine, R.A. (2003) Comparative effects of vetiver oil,
nootkatone, and disodium octaborate tetrahydrate on Coptotremes formosanus and its
symbiotic fauna. Pest Managm. Sci., 59, 58–68.
Mancebo, F., Hilje, L., Mora, G.A., and Salazar, R. (2000a) Antifeedant activity of plant
extracts on Hypsipyla grandella larvae. Rev. Fores. Centroamericana, 31, 11–15.
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Mehta, P.K., Sood, A.K., Parmar, S., and Kashyap, N.P. (2002) Antifeedant activity of some
plants of North-Western Himalayas against cabbage caterpillar, Pieris brassicae (L.).
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from plants immune to attack. Tech. Bull. USDA No. 299, 21 pp.
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2 CONCEPTS AND MECHANISMS
Food selection among insect herbivores is a highly specialized phenomenon. While olfactory
and physical aspects of plants or their organs can be important in insect host finding and
acceptance (Miller and Strickler, 1984), the choice of food is primarily based upon contact
chemoreception of various allelochemicals (Frazier, 1986; Stadler, 1992). In particular, dietary
experience has been found to influence the ability of insects to taste plant chemicals that may
serve as signals of suitability or unsuitability. Certain dietary constituents appear to suppress
the development of taste sensitivity to deterrents in an insect (Renwick, 2001). Avoidance of
allelochemicals, when looked at from a behavioral point of view, is the outcome of interactions
with chemoreceptors characterized by an often-broad sensitivity spectrum of deterrents (Mul-
lin et al., 1994). According to Schoonhoven et al. (1992) there are four basic reasons why
the chemosensory perception of feeding deterrents by phytophagous insects warrants special
attention:

1. Feeding deterrents are apparently more important in host-plant recognition than


phagostimulants.
2. A huge number of feeding deterrents exist with variable molecular structures
adding to their diversity.
3. There are fewer deterrent receptors.
4. Different deterrents may elicit different behavioral reactions, indicating the pres-
ence of a differential sensory coding system.

On the whole the mode of action of feeding modifying chemicals in insect chemoreceptor
systems is largely unknown, and no biochemically purified or cloned taste receptor proteins

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10 Opender Koul

have been identified. However, a number of molecular targets for feeding deterrents have
been identified (Koul, 1997), and there is evidence to show the existence of several sensory
mechanisms involved. Therefore, to understand the concepts and mechanisms of feeding
deterrents in an insect gustatory system, a search for candidate neuroreceptors and various
behavioral end points is required. To achieve this, at first place one must look into the
chemosensory equipment involved in the process.

CHEMOSENSORY SYSTEM
The surface of the insect body is richly supplied with sensilla of various shapes and densities.
The sensillum is the structural unit from which the majority of insect sensory organs are
derived. Ectodermal in origin, a sensillum develops by differentiation from a mother epidermal
cell. It consists of cuticular parts, one or more sense cells, and two or more sheath cells.
The sense cells vary in number from 1 to 40 or more and have large nuclei located below
the epidermis. These bipolar sense cells send their dendrites to the cuticular parts where their
form, ultrastructural features, and methods of attachment are characteristic for cells of dif-
ferent modalities. Their axons extend into the sensory nerve parallel with other sensory axons,
often extending directly to the central nervous system (CNS) before making synaptic con-
nections to second-order neurons. Thus, they are primary sense cells that contain both a
sensory receptor area on their dendrites and an impulse-conducting membrane along their
axons.
Usually sheath cells vary in number and are of three types: the basal, the outer, and the
inner sheath cells. These cells have tight and gap junctions among them and form a sort of
insulating barrier between the extracellular space surrounding the dendrites and the
haemolymph space below the epidermis (Kuppers and Thurm, 1982).
The cuticular projections of insect sensilla are the most visible portions, and their size,
shape, and position have been the basis for classifying them. With various microscopic
examinations and impulse recording techniques, various features of structure and function
have been demonstrated. Insect sensilla on the outside of the body consist of the major types
based on shape of the cuticular part, the presence or absence of pores, and the type of
attachment to the cuticle (Frazier, 1985). They have been classified as:

• Sensillum in a flexible socket with a single sense cell containing a tubular body
• Sensillum without a flexible socket containing a sense cell with lamellated dendrite
• Uniporous sensillum in a flexible socket containing one cell with a tubular body
and one or more cells with dendrites extending to the terminal pore
• Uniporous sensillum without a flexible socket containing two or more cells with
unbranched dendrites
• Multiporous sensillum with a single wall and multiple cells with branched dendrites
• Multiporous sensillum with a double wall and multiple cells with unbranched
dendrites

Out of these six major types the sensilla that possess only a single terminal pore (thick-
walled) are of gustatory nature and are concentrated on the mouth parts, though taste hairs
also occur on tarsae, antennae, and ovipositors. They possess flexible sockets; 2 to 20 sensory
cells, 1 dendrite with tubular unbranched body or inflexible sockets; 2 to 9 sensory cells and
unbranched dendrites. They are usually uniporus. However, uniporous sensilla with inflexible
sockets are fewer in number, but dome-shaped sensilla occur often in the preoral cavity, where
they serve to monitor the food being eaten.

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Insect Antifeedants 11

Lepidopterous larvae have been observed to carry in each maxilla a palpus and a galea,
the latter carrying two sensilla styloconica, non-socketed pegs with an apical papilla. These
taste hairs are innervated by four bipolar neurons, the dendrites of which extend through the
length of the hollow cuticular peg ending just below the pore at the tip (i.e., within a few
milliseconds of diffusion time from the external chemical environment) (Schoonhoven, 1987;
Descoins, 2001). The tip of the maxillary palp is covered with eight sensilla basiconica. The
palp tip sensilla are innervated by 14 to 19 neurons in total (Schoonhoven and Dethier, 1966).
This number, however, varies in different insect species (Devitt and Smith, 1982). As most
of these sensilla are gustatory in nature, they are also involved in food recognition (Descoins,
2001). Palpation of the intact leaf surface, prior to biting activity, is related to contact
chemoreception during which chemicals on the leaf cuticle are perceived (Devitt and Smith,
1985).
An epipharyngeal taste sensillum in Leptinotarsa decemlineata larvae was studied using
electron microscopy, which showed that the sensillum is innervated by five neurons. Elec-
trophysiological experiments showed that one of these cells responds to water, a second to
sucrose, and a third to two feeding deterrents that were also effective in a behavioral test.
The response of the sucrose-sensitive cell was strongly inhibited by one of the two feeding
deterrents and only slightly by the other feeding deterrent. It was concluded that probably
both the response of the deterrent cell and peripheral interactions exerted by feeding deterrents
on the sucrose-sensitive cell determine the potency of feeding deterrents. These results provide
a physiological basis for the hypothesis that the presence or absence of feeding deterrents in
potential food plants is a decisive cue in food plant selection by L. decemlineata larvae
(Messchendorp et al., 1998). However, differential neurosecretory response of this insect
species has also been recorded, for instance, against glycoalkaloids (Hollister et al., 2001).
Thus one can easily surmise that gustatory chemosensilla must be regulating feeding
behavior. It is obvious that many cells furnish information during the feeding sequence. In
grasshoppers, for instance, receptor complement is large in number and low in specificity,
and in caterpillars the number is low and relatively high in specificity (Frazier, 1986). In both
extremes there is, however, redundancy among chemosensory cells, both with respect to
specificity as well as overlap of sensitivity ranges of individual receptor cells (Blom, 1978).
Obviously it is vital to have extensive and dependable information about plant allelochemicals
that reduce or inhibit feeding. This link between single chemosensory cell input and behavioral
output must be known before we are able to correlate the effects of allelochemicals on single
cells in electrophysiological studies with their effects on the feeding behavior of the whole
insect (Frazier, 1986).

STEREOSELECTIVE PERCEPTION
Antifeedant properties of a plant compound may be revealed either by direct observation or
by using electrophysiological methods that need thorough understanding of an insect’s
chemoreceptory system. The latter procedure provides information on sensory mechanisms
underlying the perception of antifeedant chemicals. However, no two insects possess fully
identical chemoreceptory systems, but rather show different responses to various stimuli.
Consequently, plant compounds may evoke different behavioral reactions even in closely
related insect species (Schoonhoven, 1987). According to Schoonhoven (1988) life at a
macroscopic scale usually presents itself in symmetrical forms. At the molecular level,
however, asymmetry prevails. Nature often produces only one type of a stereospecific mol-
ecule and not its stereoisomer(s). Since chemoreception is a process of molecular interactions,
the phenomenon of stereoisomerism may have consequences for the process of stimulus

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12 Opender Koul

recognition. Therefore, the question arises: What is the role of stereospecificity of insect
chemoreceptors vis-a-vis antifeedants?
As mentioned above, the sense of taste in insects is localized in specialized receptors on
the mouthparts, on the preoral cavity, on the tarsi, and on the antennae—often at several of
these sites in the same insect. Extensive studies performed mainly on blowfly (Dethier, 1976)
and lepidoteran larvae (Schoonhoven, 1987) have shown that receptors are usually not highly
specific, and responses could be multineural. A correlation of the electrophysiological
response with behavioral discrimination in caterpillars has provided evidence supporting the
idea that patterns of multireceptor activity constitutes the basic code for recognition and
discrimination.
The sensory code may be altered due to the stimulation of specialized receptors or
modulation of the activity of receptors tuned to other compounds. In lepidopteran larvae
several specialized deterrent receptors have been described that respond to various alkaloids,
phenolic compounds, and glycosides and that inhibit food intake. The deterrent receptors in
different species often overlap in their sensitivity spectra, but show at the same time charac-
teristic interspecific variations (Schoonhoven, 1982).
Feeding deterrents may also change the activity of receptors that signal the presence of
feeding stimulants, for instance when suppressing sugar receptors, and thereby act as strong
antifeedants (Kennedy and Halpern, 1980). Azadirachtin, a terpenoid isolated from the neem
tree, stimulates a deterrent receptor in a number of herbivorous insects (Schoonhoven, 1988),
but appears to suppress sugar and inositol receptors in other species (Schoonhoven, 1988).
On the whole, several specialized deterrent receptors have been described mainly in
lepidopteran larvae. For instance, Bombyx mori possesses a bitter receptor that is located in
one of the two sensilla styloconica on the maxilla and responds to various alkaloids acting
as feeding inhibitors (Ishikawa, 1966) or responds to limonoid inhibitors, in the case of
Helicoverpa armigera and H. assulta (Tang et al., 2000). Pieris brassicae larvae and several
other lepidopteran species have one or more deterrent receptors, which overlap in their
sensitivity spectra (Schoonhoven, 1982; Chapman, 1982). Colorado beetles also have deter-
rent receptors in their tarsal sensilla, responding to various solanaceous plant alkaloids
(Sturckow, 1959). Specific deterrent receptors are also present in the preoral cavity of lepi-
dopteran larvae (Ma, 1972; de Boer et al., 1977). Electrophysiological studies of Blaney
(1980) emphasize the fact that deterrent receptors cannot be of a single and simple category.
Therefore, even today the conclusion of Dethier (1980) that in insects with few receptors,
multiple receptor sensitivity occurs and that “there is no generalized deterrent receptor,” seems
to be highly plausible. As it is clear now that deterrent receptors vary from species to species,
it won’t be an exaggeration to conclude that the contact chemical senses may in evolutionary
terms be easily adapted to changing circumstances (Schoonhoven, 1982).
Receptor sensitivity and specificity, however, is genetically determined, and changes in
them apparently occur by a gradual replacement of certain receptor sites in the dendritic
membrane by other types of sites, which bind different stimulants. For example, Wieczorek
(1976) showed that the deterrent cell in two strains of Mamestra brassicae show quantitative
differences in their response to some chemicals (Table 2.1), which may be explained by a
different ratio between two types of receptor sites present in the receptor membrane. As
shown in Table 2.1, one strain is very sensitive due to the presence of many sinigrin receptor
sites, whereas the other strain is more easily stimulated by naphtyl-β-glucoside (Wieczorek,
1976). This is consistent with the model of Bernays and Chapman (1994), which suggests
that differences in taste sensitivity to deterrent compounds could account for the difference
in host range. It is also possible that diet breadth has a direct link with sensitivity of the
deterrent receptor cells. For instance, genetic differences in the sensitivity of the deterrent

© 2005 by CRC Press LLC


Insect Antifeedants 13

TABLE 2.1 Sensitivity (in impulses/sec.) of a deterrent


receptor to a standard concentration of sinigrin and
1-naph-β-glucoside in two strains of Mamestra brassicae
(calculated from Wieczorek, 1976).
Strain Response
1 16–21
Sinigrin Imp. Freq.
2 21–30

1 38–46
1-naph-β-glucoside Imp. Freq.
2 23–29

receptor cells of Bombyx mori in relation to diet breadth (Asaoka, 1994) imply that the effect
could not be peripheral; however, the same interpretation does not hold true for Heliothis
species and suggests central nervous system mediated differences (Bernays et al., 2000).
Reduced feeding on deterrent diets is, in fact, a consequence either of rejection without any
ingestion or of rejection following some ingestion. Rejection without ingestion indicates that
deterrent compound is detected by chemoreceptors on the mouthparts. Rejection following
some ingestion apparently results from the accumulation of sensory information, since deter-
rent receptors sometimes adapt relatively slowly (Schoonhoven et al., 1998). There could be
post-ingestive feedbacks that allow limited intake (Bernays et al., 2000).
An intriguing question concerns the origin of deterrent receptors. It has been suggested
that herbivorous insects, rather than evolving receptors for some specific deterrents, have
developed from a “common chemical sense,” resulting in a receptor type that is sensitive to
a wide variety of compounds, even including chemicals to which a particular species has
never been exposed before (Dethier, 1980). It may be concluded from state-of-the-art studies
that insect deterrent receptors cannot be considered as a primitive or uniform type of receptor,
but rather as compound receptor types with a high degree of plasticity. According to
Schoonhoven (1982) this plasticity on the one hand insures that the insect may quickly adapt
to changes in its environment, but maintain the capacity to recognize unpalatable plants, and
on the other hand, has led to considerable divergence resulting in no two insects being
identical.
In terms of CNS interpretation of the sensory code, feeding activity obviously requires
motor output from the CNS, whereas the presence of feeding deterrents signaled via
chemosensory input may inhibit feeding motor output, leading to a refusal to eat (Ma, 1972).
Presently it is difficult to study the process as underlying the evaluation of sensory input by
the CNS, and resulting in either continuation or cessation of feeding activity. However, the
sensory inputs can be analyzed and the principles upon which central neural integration is
based can be hypothesized. Some basic considerations put forth are:

• The gustatory sense has a leading role in feeding activity. The epipharyngeal organs
do not add new information to that of the maxillary hairs.
• Sensory input from the maxillae is sent to the suboesophageal ganglion, that from
the epipharyngeal organ to the tritocerebrum.
• The message indicating whether a plant is acceptable or not must be hidden in the
sensory pattern it evokes (Schoonhoven, 1987).

© 2005 by CRC Press LLC


14 Opender Koul

If the CNS is able to read this message, it is in principle also decipherable to us, and
accordingly some messages may permit feeding activity and others may not. Sensory coding
of feeding deterrents is based upon neural activity in one or more neurons. Three basic types
of sensory coding are known (Schoonhoven et al., 1992):

1. Labeled lines: Each neuron conveys a specific message, which can be understood
by the CNS without additional information from other neurons.
2. Across-fiber patterns: The message is contained in a neural activity pattern, trans-
mitted by two or more receptors, possessing different stimulus spectra.
3. Temporal patterns: Stimulus quality affects nerve impulse interval patterns and
adaptation rates, which may contain additional information.

These coding principles could be cited in several cases and often occur in combination
in insects (Dethier and Crnjar, 1982; Schoonhoven and Blom, 1988). A temporary distortion
of such sensory codes can result in the inhibition of feeding. When in Leptinotarsa decem-
lineata the responses were compared between host and non-host potato saps. The response
patterns for the non-host stimuli appeared to be considerably less consistent than the patterns
evoked by the sap from the host plant (Mitchell et al., 1990; Schoonhoven et al., 1992). This
suggests that such variable patterns are interpreted by the CNS as “nonsense,” with the result
that no feeding or only limited feeding occurs, a pattern that has also been observed in various
lepidopteran larvae (Simmonds and Blaney, 1990).
Several chemicals, including some heavy metal ions, may distort the functioning of
chemoreceptors in such a way that, even in the presence of an acceptable plant, the neural
acceptance profile that the CNS requires for initiating feeding behavior is not evoked
(Schoonhoven, 1987; Schoonhoven and Jermy, 1977).

MECHANISMS
Secondary plant substances are in principle noxious because they interfere with the normal
structure and function of insect cells and thus disturb their integrity. Thus insects, like other
animals, have developed various mechanisms to reduce or prevent harmful effects of second-
ary plant substances when contacting them or after ingesting them (Brattsten and Ahmad,
1986). As we have seen, chemoreceptors in insects are primary sense cells and thus true
neurons generally protected from the deleterious effects of secondary plant compounds. This
is supported by the fact that insects have sensory neurons that respond to sugars, amino acids,
or salts and function normally despite the presence of these host-specific noxious compounds,
as was demonstrated in the case of polyhydroxy alkaloids against Spodoptera and Helicoverpa
species (Simmonds et al., 1990).
If some receptor cells have retained their primordial sensitivity to different kinds of
secondary plant compounds, they would be ideally suited to signal the presence of chemicals
to be avoided. Thus, the primitive, unmodified taste cell may be considered as the primordial
deterrent receptor, which still possesses a sensitivity to odd plant substances originally shown
by all primitive neurons. That does not mean that the present-day deterrent receptors are
unchanged and wholly identical to their ancestral neural cell type. The modern deterrent
receptors, while retaining sensitivity to various secondary plant compounds, have developed
a physiological mechanism, which protects them against the harmful effects of their adequate
stimuli. Not only has the basic sensitivity to secondary plant substances been preserved in
these receptors, it also became connected to the action potential generating system, resulting
in a change of impulse frequency upon stimulation (Schoonhoven, 1991). Thus, in contrast

© 2005 by CRC Press LLC


Insect Antifeedants 15

to sugar and salt receptors, deterrent receptors have preserved their general sensitivity, which
has been linked to a neural response mechanism. In fact, all lepidopteran larvae possess a
pair of maxillary palps that “drum” the surface of foods during feeding. These chemosensory
organs contain over 65 percent of a larva's taste receptor cells, but their functional significance
remains largely unknown.
Their role in rejection of plant allelochemicals was examined, using the tobacco horn-
worm, Manduca sexta, as a model insect and an extract from a plant species, Grindelia
glutinosa, as a model stimulus. This system was selected because hornworms reject foods
containing Grindelia extract, and because preliminary studies indicated that their maxillary
palps respond to this extract. It was hypothesized that Grindelia extract elicits rejection
through stimulating (i) olfactory receptor cells, (ii) taste receptor cells, (iii) oral mechanore-
ceptors, and (iv) a post-ingestive response mechanism. The results were consistent only with
hypothesis (ii); larvae approached Grindelia-treated diets without apparent hesitation, but
rejected it within 6 seconds of initiating biting. Grindelia-treated solutions stimulated taste
receptor cells in the maxillary palp, but not the other gustatory chemosensilla, and ablating
the maxillary palps eliminated rejection of Grindelia-treated diets. The results demonstrate
that taste receptor cells in the maxillary palps mediate rejection of Grindelia extract and
provide the first direct evidence for a role of maxillary palps in rejection of plant allelochem-
icals (Glendinning et al., 1998).
The possibility exists that insects use some other codes for taste quality, such as assess-
ment of the temporal sequence of firing, which gives a continuous evaluation of the activity
of individual neurons. It is also likely that simultaneous evaluation of inputs from different
neurons allows contradictory signals, indicating the presence of phagostimulants or antifeed-
ants, and is assessed concurrently (Schoonhoven, 1987).
In addition to these neural mechanisms, it should be mentioned that some other targets
are also vulnerable to antifeedants, like γ-amino butyric acid (GABA) antagonistic mecha-
nisms, biogenic amine inhibition, and so on.

GABA ANTAGONISTIC MECHANISM


GABA and related aminobutyric acids are known to stimulate feeding and evoke taste cell
responses among herbivorous insects of various taxa, like Orthoptera, Homoptera, Coleoptera,
and Lepidoptera (Mullin et al., 1994). However, it has also been established that allelochem-
icals antagonize GABA phagostimulants, like the isoquinoline alkaloid papavarine does in
the Colorado potato beetle, thereby inducing feeding deterrence (Mitchell, 1987). GABA-
gated chloride channels respond to many classes of chemicals in insects (Sattelle, 1990;
Anthony et al., 1993). The antagonism of GABA binding allows increased depolarization
within an excitable cell and functions at both the neuromuscular junction and central synapses
within the nervous system of insects. The present view is that inhibitory GABAA (Cl– con-
ducting) receptors belong to a gene superfamily of ligand-gated ion channels that include
excitatory nicotinic acetylcholine (Na+, K+) and inhibitory glycine (Cl–) receptors (Anthony
et al., 1993). In turn, the α-carboxylated and precursor form of GABA, glutamic acid, gates
a more distantly related family of both excitatory K+/Na+ and inhibitory Cl– channels (Darlison,
1992; Sattelle, 1992). On the whole it has been shown that the GABAA and glycine receptor
complexes must incorporate two or three different four-transmembrane-domain subunits
(Mullin et al., 1994).
Association of GABA/glycine receptors with sensory systems has been demonstrated.
For instance, bicuculline insensitivity at GABAA sites in insects has been found in CNS
interneurons of the cockroach (Walker et al., 1971) and Manduca sexta (Waldrop et al., 1987).

© 2005 by CRC Press LLC


16 Opender Koul

TABLE 2.2 Neuroreceptor antagonists on Western corn rootworm


showing feeding deterrency.
ED50
Chemical nmol/dish Neuroreceptor Type
Strychnine HCl 2.2 Glycine (also GABAA)
β-Hydrastine 4.6 GABAA
Bicuculline 6.3 GABAA
PK 11195 7.1 Periphral benzodiazepine
Gabazine 9.1 GABAA
Bulbocapnine HCl 17.0 Dopaminergic
d-Tubocararine Cl 29.0 GABAA
Cyproheptadine HCl 30.0 5HT2
7-Chlorokynurenic acid 35.0 NMDA glutamergic
Harmine 40.0 GABAA
2-Hydroxysaclofen > 50.0 GABAA
Piperine 110.0 Voltage sensitive Na gate
Azadirachtin 0.1 mM GABAA ?
Parthenolide 1.5 mM GABAA ?
Agrophyllin A 2.15 mM GABAA ?

Source: Mullin et al. (1994).

In M. sexta GABA was found to mediate olfactory behavior via inhibitory interneurons in
the antennal lobe of the deutocerebrum. However, only β-like subunits of GABA receptors
from the CNS of Drosophila spp. (Henderson et al. 1993) and yellow fever mosquito, Aedes
aegypti (Thompson et al., 1993), have been cloned from insect species.
An interesting study of Mullin et al. (1991a, 1991b) shows the association of an anti-
feedant with a GABA/glycine receptor. Epoxy sesquiterpene lactone antifeedants from sun-
flower exhibit picrotoxinin-like GABA-gated chloride channel neurotoxicities in adult West-
ern corn rootworm. In fact, terpenoid epoxides and isoquinoline and related alkaloids, such
as azadirachtin, a strong antifeedant from neem (Koul, 1996), bicuculline, and so on, are
interesting antifeedants of this category (Table 2.2).
Mullin and coworkers (1994) have used three-dimensional structure-function relation-
ships in Diabrotica to demonstrate antifeedant potency of compounds proposed to interact
at a common binding site. Compounds were co-fitted through use of Alchemy III molecular
modeling software (Tripos Associates). Common binding features for high antifeedant activity
among the polycyclic terpenoid epoxides like azadirachtin, agrophylin, picrotoxinin, and
caryophyllene oxide include an epoxide and π bonding sites separated by 0.5 to 0.6 nm, one
or more electronegative oxygen centers, and a trisubstituted oxirane. Polyoxygenation may
maintain sufficient polarity to allow diffusion to and interaction with the taste receptor. The
3D structural similarity between argophyllin (Mullin et al., 1991b) and picrotoxinin and
dieldrin (Matsumura et al., 1987) suggest action through a shared picrotoxinin receptor site.
The above studies also indicate that optimal polarity for molecular interactions at an
exterior chemosensory receptor is different from internal interaction requirements with excit-
able cells, since membrane penetration and transport by binding proteins are not necessary
(Mullin et al., 1994). A hydrophobic nature of compounds makes them non-inhibitory to
feeding, as has been determined by using partition coefficient techniques. Many deterrents
tested against Diabrotica have been shown to cause firing of a single taste neuron, and this
chemosensory response correlates well with their feeding deterrency. In fact, GABA antag-
onism at the taste cell level may after neural processing result in net inhibition or excitation,

© 2005 by CRC Press LLC


Insect Antifeedants 17

respectively, of the dominant adductor, with a converse effect on the adductor. Clearly higher
CNS inputs into mandibular opening and closing are also required. The actual inhibitory and
excitatory inputs at each synaptic level, their means of integration, and the responsible
neurotransmitters, receptors, and ion movements for insect gustation mostly remain to be
clarified (Frazier, 1992).

BIOGENIC AMINE INHIBITION MECHANISM


Biogenic amines are widely distributed within the insect CNS and thought to act as neuro-
hormones, neuromodulators, or neurotransmitters (Evans, 1980). To get information about
the mechanism of insect feeding, the insect response at biogenic amine levels against the
feeding deterrents has been investigated (Ikemoto et al., 1995). For example, chlordimeform
and aristolochic acid are well-known insect antifeedants and have been used as a probe of
antifeedant activity. Five typical biogenic amines (5-hydroxytryptamine, dopamine, epineph-
rine, norepinephrine, and octopamine) using HPLC with an electrochemical detector have
been investigated in the CNS of last instar Spodoptera litura larvae. It has been demonstrated
that chlordimeform causes an increase in N-acetyldopamine levels in cerebral and suboe-
sophageal ganglia and a decrease in 5-hydroxytryptamine (5HT) and n-acetyloctopamine
levels in the cerebral, suboesophageal, and thoracic ganglia. On the other hand, aristolochic
acid I, an antifeedant from Aristolochia species, did not cause any significant change in any
amine levels except for dopamine and 5-hydroxytryptamine in suboesophageal ganglia and
tyranine in thoracic ganglia (Ikemoto et al., 1995). Decrease in 5HT has also been reported
in the cockroach cerebral ganglia (Omar et al., 1982). Inhibitory activity of chlordimeform
against N-acetyltransferase has been shown in several insect species (Wierenga and Holling-
worth, 1990).
Although these studies suggest that some antifeedants have a mechanism of action through
bioamine system in insects, comparing the effect on biogenic amine levels, no similar
alterations have been observed. The relationship between such alterations and the antifeedant
treatment is not clear as yet, but this could be one of the directions to study the mechanism
of antifeedants and to understand the biochemical and physiological meaning of such alter-
ations occurring due to feeding deterrents.

MECHANISMS RELATED TO SPECIFIC


ALLELOCHEMICALS
Chapter 7 illustrates more than 800 compounds that inhibit feeding of a variety of insect
species using various bioefficacy procedures. However, the question remains: How do these
chemicals affect the insect chemosensory cells, though a generalistic concept has been
discussed above, and do they indicate the multiplicity of actions that can reduce feeding?
Substantial data has been obtained in this regard for a diverse group of allelochemicals, the
alkaloids. They inhibit impulse generation in sugar-sensitive cells in lepidopterans (Frazier, 1986;
Simmonds et al., 1990) and competitively block sucrose responses in flesh flies (Morita et al.,
1977). They also reduce the firing of the sugar-sensitive cells. Alkaloids as inhibitors of pyranose
and furanose receptor sites have been established for flies (Wieczorek et al., 1988).
The steroidal glycoalkaloids elicit irregular firing from several cells in the galeal and tarsal
sensilla of adult and the larval α-sensilla of the Colorado potato beetle (Mitchell and Harrison,
1985). On the contrary, deterrent effects of various alkaloids, when tested against black blow
flies, Phormia regina, in order to determine tarsal threshold for mixtures of sucrose and alkaloids,
using kinetic analysis of electrophysiological data, ruled out competitive, no competitive, and

© 2005 by CRC Press LLC


18 Opender Koul

un-competitive inhibition at receptor sites. Even no correlation of thresholds with available


data on lipid solubility or octanol/water partition coefficients was observed. This suggests
that there is no uniform limiting mechanism for this multiform array of compounds (Dethier
and Bowdan, 1989).
Terpenes of various classes also inhibit insect feeding. Azadirachtin, one of the most
potent deterrents known, has been shown to induce the firing of one cell in the labial palps
and one in the A3 sensillum of the clypeo-labrum of Schistocerca gregaria (Haskell and
Schoonhoven, 1969). It also induces the firing of cells in the medial sensilla styloconica of
Pieris brassicae and Lymantria dispar larvae (Schoonhoven and Jermy, 1977; Schoonhoven,
1982). Azadirachtin effects in other caterpillar species are characterized by the firing of large
spikes in the lateral and medial sensilla styloconica. This cell appears to fire independently
of the sugar-sensitive cell (Simmonds and Blaney, 1984). This confirms a general observation
that the effects of azadirachtin (and many other compounds as well) are different in different
species; that is, affecting more than one chemosensory cell type in more than one way. Luo
et al. (1995) describe a significant correlation between behavior and response of the medial
deterrent cell for three triterpenoids, azadirachtin, salannin, and toosendanin. They showed
a relationship between sensory input and feeding inhibition, supporting the hypothesis that
the response of the medial deterrent cell directly causes inhibition of feeding in Pieris
brassicae (Messchendorp et al., 1996).
However, interference with the lateral glucosinolate- and sugar-sensitive receptor cells
measured for toosendanin (Schoonhoven and Luo, 1994) did not contribute to a closer
relationship between sensory response and inhibition of feeding on cabbage leaf disks in
P. brassicae, mentioned above. Toosendanin has been shown to modulate the sensory code
underlying feeding behavior via several different peripheral sensory mechanisms; that is,
stimulation of the deterrent receptor cell located in the medial maxillary sensillum styloconi-
cum and inhibition of responses of both the sugar and glycosinolate receptor cells
(Schoonhoven and Luo, 1994).
Other limonoids have also been shown to deter feeding in a variety of insect species
(Champagne et al., 1992), but there is no electrophysiological data available to compare the
effects on taste receptor cells. This information gap is mainly due to the fact that limonoids
are insoluble in water, and this makes it difficult to apply the tip recording technique in an
electrophysiological bioassay of limonoids. Some workers have solved the problem by using
mixtures of 50% tetrahydrofuran and 50% aqueous sodium chloride as a solvent system
(Waladde et al., 1989). In these studies the compounds, like deoxylimonin, obacunone, and
pedonin, were used to investigate responses of Eldana saccharina maxillary styloconic
sensilla and exhibited an inhibition of the sugar receptor cells.
The sesquiterpene warburganal produces irregular firing of more than one cell and then
blocks the responsiveness of the sucrose- and inositol-sensitive styloconic cell of Spodoptera
exempta (Ma, 1977). It was suggested that in this case the deterrent acts via interaction with
protein sulfhydral groups located at the receptor membrane. Some studies also suggest that
warburganal reversibly blocks chemoreceptors, but the observation that feeding behavior of
larvae of Spodoptera eridania, Schistocerca gregaria, and Manduca sexta is little affected
may indicate that sensory input to the brain in these species does not inhibit food intake
(Schoonhoven and Yan, 1989). It is well evident that such dialdehydic sesquiterpenoids
(including polygodial, muzigadiol, etc.) affect not only the phagostimulant receptors, but also
the deterrent cells located in the medial hair of insects (Schoonhoven and Yan, 1989). This
suggests a mechanism of interference common to all taste receptors. Therefore, it remains
unexplained why different receptors show different degrees of inhibition and different recov-
ery periods. However, what is certain is that these sesquiterpenoids induce antifeedant effects

© 2005 by CRC Press LLC


Insect Antifeedants 19

in various insect species by (i) stimulation of a deterrent receptor and (ii) decreased sensitivity
of most or all other receptors.
Clerodin, an antifeedant diterpene, induces greater feeding deterrency when applied to
the maxillary palps as compared to the sensilla styloconica (Antonious et al., 1984), which
is in contrast to what has been observed in formamidine compounds (discussed above).
Ginkgolides from Ginkgo biloba, when tested electrophysiologically for neural responses
in the maxillary taste sensilla, show a strong stimulation of the deterrent receptors of two
types in Pieris brassicae and P. rapae. However, in P. brassicae the medial sensillum is more
strongly stimulated than the lateral sensillum, whereas in P. rapae the reverse is true (Yan et
al., 1990). This illustrates the marked difference between the chemoreceptory systems of the
two species.
Drimanes with a lactone group on the B-ring appear to be the most potent antifeedants
at 5 mM level (Messchendorp et al., 1996). The positive correlation between feeding inhibition
and response of the deterrent cell suggests that these compounds exert a direct inhibitory
effect on the feeding centers in the CNS. At the same time few compounds, though highly
deterrent, do not evoke strong responses from the deterrent cells. This suggests that other
mechanisms, either sensory or post-ingestive, are also involved in feeding inhibition. One of
the drimanes tested in the above studies depressed the neurons sensitive to feeding stimulants.
Whether or not this interference contributes to feeding inhibition remains to be elucidated.
What could be concluded from this study is that highly effective drimane antifeedants can
be selected electrophysiologically on the basis of response intensity of the medial deterrent
cells, but further details of the mechanisms underlying feeding inhibition await to be revealed.
There is also the evidence that mechanisms for antifeedants may vary within a species.
In another study, for instance, 11 analogous synthetic drimane antifeedant compounds were
evaluated for their feeding-inhibiting effects on larvae of the large white butterfly Pieris
brassicae in no-choice tests on the host plant Brassica oleracea. The results show that the
five analogous antifeedants differentially influence feeding behavior and locomotion activity.
Some are most likely sensory-mediated antifeedants. Habituation to these compounds occurs
soon after the onset of the tests (i.e., within 0.5 to 1.5 h). Others, like confertifolin, probably
are not direct sensory-mediated antifeedants and rather induce post-ingestive anorexia. In
conclusion, the behavioral observations performed in this research indicate that analogous
drimanes inhibit feeding by P. brassicae larvae through multiple mechanisms of action
(Messchendorp et al., 2000).
The antifeedant activity of chalcones, flavones, and flavanones is due to the predominant
stimulation of the deterrent neurons in the medial sensillum stylonicum, and more than one
receptor may be involved (Simmonds et al., 1990). These studies suggest that there are at least
two different receptor types involved, each having a different structure-function type of response.
From the preceding discussion it is clear that the molecular structure of compounds vis-
a-vis the neural responses associated with feeding deterrence mechanisms should throw some
light on various molecular parameters such as chirality, functional groups, molecular size,
and lipophilicity of the compounds. However, it appears difficult, if not impossible, to
ascertain any common molecular conformation to all active molecules and their induction of
a specific type of neural/receptor response towards a specific deterrent.

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Wierenga, J.M. and Hollingworth, R.M. (1990) Octopamine uptake and metabolism in the
insect nervous system. J. Neurochem., 54, 479–489.
Yan Fu-shun, Evans, K.A., Stevens, L.H., van Beek, T.A., and Schoonhoven, L.M. (1990)
Deterrents extracted from the leaves of Ginkgo biloba: effects on feeding and contact
chemoreceptors. Entomol. Exp. Appl., 54, 57–64.

© 2005 by CRC Press LLC


3 BIOASSAYS
Bioassays against insects have been used for decades as a means of elucidating the activity
of many chemical components. The major goals achieved by employing bioassay techniques
are to determine the roles of naturally occurring chemicals, identify the mechanism of
resistance in crop plants, and to find various insect control agents. As the aim of this book
is to understand chemicals that inhibit feeding, the emphasis will be on antifeedant alle-
lochemical bioassays. However, before going into the details of various types of bioassays
for feeding-deterrent activity, it is imperative to know about certain fundamental requirements
for such evaluations. The basic design to study deterrents is to present to an insect a substrate
with the candidate chemical and to measure the response of the insect. Therefore, substrate
choice and presentation are important factors for a successful bioassay. Both natural and
artificial substrates are used, depending upon the goal of the experiment. On one hand one
may emphasize that artificial substrates offer uniformity, but at the same time studies have
shown that thresholds for the same deterrent may vary as much as 1000 times between natural
and artificial substrates (Schoonhoven, 1982), perhaps due to differences in porosity or uptake
rates by the insect. For sucking insects, the principal artificial substrate used has been a
chemically defined liquid presented between natural or artificial membranes (Mittler and
Dadd, 1962).
However, whatever the substrate may be, it is important that no textural differences should
occur between the control and test substrates. Color differences may also influence insects
tested (Meisner and Ascher, 1973). Care is needed to ensure the least hindrance with the
insect’s chemoreceptor’s encounter, which should be in the usual way (i.e., for edge feeders
substrates are placed above the floor level). Natural substrates could be whole plant, leaves,
leaf disks (more frequently used), or specialized substrates like twigs, blocks of wood, board,
and paper towel disks. Artificial substrates usually include agar-based artificial diets, simple

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26 Opender Koul

liquid-based artificial diets, styropors (which are good model substrates for many insects using
lamellae), or disks of foamed polystyrene, styrofoam, or polyurethane, and glass fiber disks.
After the choice of the substrate, an important step is the chemical application. For
antifeedant testing, concentrations need to be selected to achieve the goal of finding the
effective concentrations for crop protection. Higgins and Pedigo (1979a) used a foliar phy-
totoxicity threshold base as the presence of leaf necrosis to determine maximum acceptable
concentration. One could use the sensitivity of the insect chemosensilla as a criterion for
concentration, but it is difficult as very little is known about these sensitivities.
The role of solvents is another important factor. Ascher et al. (1981) found that grades
of a common solvent, methanol, could differ in their effects. My studies with antifeedant
evaluations have revealed that alcohols interfere with the texture of natural substrates (par-
ticularly leaf materials), and therefore should be avoided. The best way is to depend on water-
based emulsified solutions, which hold a small quantity of the solvent. Therefore, natural
control substrates with and without solvent should be tested to verify that there is no alteration
in palatability due to solvents. In electrophysiological studies appropriate electrolyte use is
essential.
The next important factors for evaluation are the conditions of the test. Jermy et al. (1968)
used a sytem of evaluation where tests were terminated when 50% of either substrate in a
choice trial was consumed, so the insects did not lose discrimination due to hunger. This
system is adopted even today in many studies. There is also evidence that previous experiences
affect insect diet choice by induction, habituation, food aversion learning, and associative
learning. Therefore, such problems need to be avoided and apparently could be achieved by
using insects only once in a test and for a short duration. Pilot observations are necessary to
establish time of maximum feeding, which varies among various insect species. Temperature,
humidity, light levels, and population of test insects are other parameters that need to be
determined from field observations for better results in the antifeedant assay. In fact, per-
forming short- and long-term tests provides the most information, as data on changes in
behavior through lengthy exposure to a chemical may be useful (Lewis and Bernays, 1985).
The above-mentioned step is then followed by measurements and observations. These
parameters will depend upon the feeding behavior of the insect; that is, methodologies will
depend upon whether the bioassay is conducted against a chewing insect, a sucking insect,
and so on. Depending on the different modes of feeding in insects, various types of bioassay
procedures have been developed in laboratories to evaluate insect antifeedants. I have cate-
gorized these bioassays as shown in Figure 3.1. However, some specific assays used against
specific insect species are also described.

LEAF DISK ASSAY


Leaf disks are commonly used in insect bioassays of preference or consumption with chewing
insects. This assay can be conducted in two basic ways: i) choice assay and ii) no-choice
assay. Insects can choose either control or treated disks (choice) or insects may be exposed
to the test substance only (no-choice). The no-choice situation often is more representative
of our agricultural system, especially for monophagous species, but at the same time it is
very sensitive.
The general procedure adopted in this test is that measured leaf disks are punched out
from substrates and treated either on one side or both sides with a known quantity of test
material in a carrier solvent. It is preferable to use emulsified solutions in water in order to
avoid interference with leaf disk texture due to solvents (Koul et al., 1990). A method has
been described by which leaf surfaces can be covered with a uniform amount of a test chemical

© 2005 by CRC Press LLC


Insect Antifeedants 27

LEAF DISC TEST


LOCUSTS, GRASSHOPPERS
MOSTLY LEPIDOPTERANS

ARTIFICIAL
DIET TEST ARGENTINE STEM WEEVIL
GREEN BUGS,
LEPIDOPTERANS
PAPER TOWEL
DISC TEST TERMITES

WHEAT WAFER
ASSAY STORED GRAIN PESTS

STYROPOR
ASSAY LEPIDOPTERANS
SUCKING INSECTS
ANTIFEEDANT
BIOASSAYS

GLASS FIBER
DISC ASSAY LEPIDOPTERANS, LOCUSTS
ACRIDIDS

PIPET
ASSAY
DIPTERANS

SIMULATION
ASSAY MANY PHYTOPHAGOUS
INSECTS

IMPREGNATION BEAN BEETLES, SCALE


ASSAY INSECTS, WHITE FLIES,
CITRUS MITES,
WIREWORMS,
ELECTRO - LEPIDOPTERANS
PHYSIOLOGICAL
ASSAY LEPIDOPTERANS
LEAFHOPPERS
COCKROACHES

FIGURE 3.1 Bioassay methods.

for bioassay with leaf-feeding insects. Chemicals are dissolved in gelatin solutions, which
can be sprayed evenly and which will adhere well to many leaf surfaces. However, calibrations
of rates of application are required (Wolfson and Murdock, 1987).
After application, the leaf disks are dried at room temperature and then fed to candidate
insects. Usually the arenas used are petri dishes of variable sizes (9-cm-diameter size is most
common for lepidopteran larvae) in which one treated and one control disk is placed (choice),
or both the leaf disks are treated (no-choice). In certain experiments five to ten treated and

© 2005 by CRC Press LLC


28 Opender Koul

untreated leaf disks are used and placed alternately in the petri dishes in a choice situation.
The number of larvae introduced into each arena is variable depending upon the size and
stadium of the larvae used. There is also considerable variation in the duration of experiments
(see Chapter 7), both long term and short term. The consumption in each experiment is
measured using various digitizing leaf area meters.
In certain studies the choice tests have been referred to as dual choice tests. In these
experiments individual larvae are confined for a short term (5 to 6 hours) in a petri dish
containing two leaf disks. The treatment disks are painted with an aliquot of test solution
and the control disks with solvent solution only. The bioassay is conducted for very short
duration or until 50% of either disk is consumed. The amount eaten is then assessed and
calculated. In certain cases even more than two leaf disks have been used. For instance, while
testing drimane-type antifeedants in dual-choice tests against Pieris brassicae, six cabbage
leaf disks (3.8 cm2 area) placed in a circle were assayed in a glass petri dish. The upper
surface of alternate disks was painted with 10 µl drimane or control solution, after which
they were left to dry for 30 minutes. After 3 hours of ad libitum feeding, the remaining disk
areas were measured with a leaf area meter (Messchendorp et al., 1996).
However, some findings have implications to the design of disk bioassays. Clearly, the
ratio of cut edge to overall leaf disk surface area is an important variable that should be taken
into account (Jones and Coleman, 1988). The decision to choose one disk size over another
has often been a matter of convenience for the experimenter. Thus, it has been suggested that
selection of the appropriate disk size will depend upon several variables (Jones and Coleman,
1988):

• Whether the insect feeds in the center or edges of the leaves


• The size of the insect, particularly the ratio of insect size to disk size
• The type of bioassay being carried out

For example, if a leaf disk from the host plant of a center-feeding insect were painted
with a deterrent chemical, one would predict the deterrent effects would be greater in a large
disk assay than in a small disk assay. This is because the cut edge would contribute coun-
teracting host-plant attractant or stimulant signals to a greater extent on small disks.
In order to measure and calculate the effective concentrations of insect antifeedants, there
is no standard size terminology. In certain cases the consumed area of treated leaf disks is
expressed as a percentage of the consumed area of control leaf disks. In others, antifeedance
has been calculated on the basis of feeding ratios (i.e., test consumption/control consumption
followed by grading) (Zalkow et al., 1979). This ratio has also been calculated as:
Feeding control = 100 { 1 – % feeding/% feeding by stock} and graded as +++ (90–100%);
++ (60–90%); + (30–60%) protection, and – (0–30%) showing no protection (Lidert et al.,
1985).
In many cases an antifeedant is considered to be effective when feeding inhibition of
80–100% is achieved (Bernays and Chapman, 1978). EC90 and EC95 values have also been
calculated. On the whole some generalized formulas have been devised to calculate feeding
deterrence quantitatively:

• D = (1 – T/C) × 100, where T and C are percent weights of treated and control leaf
disks (dry weight basis) and D is the percent deterrence (Hosozawa et al., 1974).
• Protection (%) = (% PTS – % PIC)/100 – % PIC, where PTS is protection in
treated samples and PIC is protection in control samples (Singh and Pant, 1980).

© 2005 by CRC Press LLC


Insect Antifeedants 29

• Feeding inhibition (%) = % CTD × 100/% CTD + % CUD; where CTD is


consumption of treated disks and CUD is consumption of untreated disks (Reed
and Jacobson, 1983).
• Feeding deterrence (%) = (C – T)/(C + T) × 100, where C and T are the consumption
of control and treated disks, respectively (Koul et al., 1990). This formula is
preferred for the measurement of deterrence.

Recently, leaf disk choice bioassay has been very successfully used to study aphids
(Lowery and Isman, 1993; Koul et al., 1997). In this procedure two leaf disks with the test
material and two disks with carrier alone are allowed to dry and then arranged alternately in
small petri dishes (9 × 50 mm) with their edges barely touching. Deterrence of the test
material is determined by the proportion of aphids on the treated disks relative to the total
number of aphids on treated and untreated disks in each dish.
An improved antifeedant bioassay has been devised that allows an accurate measurement
of consumed disk surfaces, using a video camera interfaced with a computer. The scanned
image of the leaf disk is stored and the eaten areas are measured with the help of video-
image analysis software. This method allows for precise quantification of insect antifeedant
activity tested on leaf material (Escoubas et al., 1993). The process of storing the image
involves selection of the interesting area in the scanning window via cut-and-paste functions.
By this method, the image can be edited, enhanced, and used in later measurements.

ARTIFICIAL DIET FEEDING


Artificial diet tests are also commonly used against many lepidopterans, green bugs, and
weevils. A general procedure for this evaluation is to incorporate the test material into artificial
diets, feed to test insects, and calculate mean percent feeding depression. However, artificial
diets usually have one of two problems: they are suboptimal or they can be superoptimal
(Wolfson, 1988). Compared with the most susceptible host plants, artificial diets often foster
more rapid growth (Reese and Field, 1986) and thus can make insects less susceptible to the
allelochemicals being tested. According to Berenbaum (1986), tests of chemicals in artificial
diets could be compromised by eliminating naturally occurring synergistic interactions
between nutrients and allelochemicals.
However, there are some specific examples where artificial diets have been successfully
used for evaluation. For instance, artificial diet plugs of known weight were placed in an
arena (35 × 10 mm petri dishes) along with two sixth instar larvae of spruce budworm,
Choristoneura fumiferana. Both choice and no-choice situations were established. Larvae
were allowed to feed for 48 hours, at which time remaining portions of diet plugs were
weighed. Results were expressed as weight of plugs consumed/insect/48h. Each group was
replicated three times for a total of 24 insects/treatment (Alford and Bentley, 1986). Mean
percent feeding depression was calculated as = [ 1 – treatment consumption/control con-
sumption × 100 ].
In the case of the boll weevil, bioassay chambers were constructed by pouring a layer
(5 mm thick) of beeswax paraffin (2:1 by weight) into the bottom of a petri dish (1.5 × 10
cm). Three to six media wells were cut into the cooling paraffin with a No. 9 cork borer (13
mm diameter), 2 cm from the center of the dish and equidistant apart. The wells were filled
with cooling 2.5% nonnutrient agar solution plus 3.0% pharmamedia or freeze-dried cotton
square powder. A lens paper disk cut with a No. 10 cork borer (15 mm diameter) was placed
on top of the solidified medium surface. Water (20 µl) was applied to the paper to provide

© 2005 by CRC Press LLC


30 Opender Koul

moisture for the insects and to hold the papers to the medium surface. Chemicals were
randomly applied to the lens papers as 20 µl aliquots in methanol and allowed to dry for 30
minutes. 10 male or female boll weevils were released into each assay chamber and the tops
were applied to prevent escape. The scores for the number of punctures after 3 to 6 hours
were noted using a dissecting microscope, and deterrence effects were calculated (Bird and
Hedin, 1986).
For Eurema hecabe mandarina (yellow butterfly), larvae pre-starved for 4 hours were
placed on each of the following diets:

1. The basal diet (1% agar only).


2. The control diet prepared by incorporating dried leaf powder of Lespedeza cuneata
(0.39 g) in 1.4 ml of 1% agar.
3. The test diets prepared by incorporating plant powders or fractions or compounds
into dried leaf powder as in (2) in 1 ml of 1% agar at a total weight of 1.28 g.

The number of frass pellets deposited during the test period (20 h) was then counted.
The feeding inhibition activity was calculated on the basis of feeding ratio:

Mean frass count/test diet – Mean frass count for the basal diet
Feeding ratio =
Mean frass count for the control diet – Mean fraass count for the basal diet

When the ratio was < 50% it was considered to be a positive inhibition. When the response
was between 0 and 20% the test material was a very strong inhibitor (Numata et al., 1984).
Agar-based diets have also been used for Argentine stem weevils, Listronotus bonariensis
(Rowan and Gaynor, 1986). After cooling, these diets were cut into 35 to 40 disks with a
cork borer (1 cm × 3 mm thick) in a choice bioassay. For treatment experiments, cellulose
powder was mixed with the candidate chemical at 2 g of extract/4 g of cellulose powder. The
suspensions were made, evaporated to dryness, and agar disks were made.
There are artificial diets developed for evaluating antifeedant chemicals against aphids.
A generalized pattern has been adopted for Schizaphis graminum. In this procedure small
(35 ml) polystyrene catsup cups are used as test chambers. For each test 50 to 75 aphids of
all ages are transferred from the colony by brushing them carefully off the plant with a hair
paint brush. The polystyrene test chambers consist of tight-fitting plastic snap-on caps, which
possess circular holes (1.5 cm) punched with a cork borer for the placement of the diet
container. The container is usually made from a soft polyethylene vial cap, which fits snuggly
into the hole prepared with the cork borer in the lid. A thin sheet of parafilm is stretched
across the vial cap to create a sealed diet chamber. Diet containing the test material is added
by injection with a syringe through the topside of each polyethylene cap. The diet-filled
containers are placed by a snug fit into the hole bored in the lid of the test chamber with the
parafilm membrane facing the interior of the test chamber towards the aphids.
The tests are maintained for 24 hours at 24˚C. After 24 hours the number of aphids
feeding and the number wandering are counted and compared with appropriate controls. One
week later an identical set of experiments is run and all the replicates are averaged (Dreyer
et al., 1981). In certain cases in synthetic diet feeding, each substance is tested at a series of
concentrations so that a dose-dependent curve could be constructed. From this curve a
concentration could be obtained at which half of the aphids (ED50 values) would not feed
(Rose et al., 1981). Calculations can also be based on the difference in weight of the larvae
in each group of treatments, multiplied by 100 and divided by the average weight of larvae
in the control group to obtain a larval weight index (Warthen et al., 1982).

© 2005 by CRC Press LLC


Insect Antifeedants 31

STYROPOR ASSAY
This method is usually used for lepidopterans and sucking types of insects (Koul, 1993).
Thin 0.6 mm lamellae (6 × 4 cm) of styropor (foamed polystyrene) of density 0.016 (P16)
are dipped into solutions of the test compounds of different concentrations containing 5%
sucrose. The lamellae are left to dry for 24 hours and then weighed individually. They are
then offered singly in large 15-cm-diameter petri dishes to one early sixth instar larvae (e.g.,
Spodoptera littoralis of 170 to 190 mg body weight), together with water absorbed in cotton
wads. The number of replicates varies from five to ten for each level of treatment. The weight
of styropor after consumption and the weight of fecal pellets voided are recorded for each
larva after 48 hours and used as criteria for antifeedant activity (Ascher and Meisner, 1973).

GLASS FIBER DISK TEST


This type of antifeedant bioassay, though used for lepidopteran larvae, has also been useful
to evaluate compounds against locusts and other acridids. In this method the test compounds
are added to glass fiber disks (Whatman GF/A), a pair of which are presented dry to each
individual insect. The disk size varies from 2.1 to 4.25 cm, which are usually dried in a cool
air stream. The loading of the disks varies from 100 to 400 µl of test material.
Locusts are confined individually in clear plastic boxes (27 × 15 × 10 cm), each screened
from its neighbor so that insects in adjacent boxes do not disturb each other. Disks are
presented in pairs to facilitate feeding for 24 hours until 30 to 50% of the control disk has
been consumed; the amount of disk eaten is measured by an area meter.
Lepidopteran larvae are confined in petri dishes (9 cm diameter) with a pair of disks for
up to 8 hours so that never more than 50% of any disk is eaten. After removal of the larvae
disks are redried and the amount eaten is determined by weight (Blaney et al., 1984).
For acridids, glass fiber disks of 4.5 cm diameter have been used by adding known
quantities of sucrose solutions to give either 5% or 12% dry weight of sucrose. After drying,
disks are treated with a known amount of compound in solution. Approximately 0.4 ml
solution saturates this size of disk and gives an average concentration of 0.02 to 2.0% on a
dry weight basis. After evaporation of solvent the disks are checked by weight and then fed
to insects. All choice tests are carried with well-fed insects approximately halfway through
the final larval instar. Experiments are run for 3 hours and usually as 10 to 15 replicates.
After the test each remaining disk is measured with an area meter or in certain cases weighed
and the amount of each disk eaten/insect is calculated (Bernays and DeLuca, 1981).

PAPER TOWEL DISK TEST


Commonly used for termites, this method has been very well described by Scheffrahn and
Rust (1983). The natural paper towels, cut into 9.6-cm-diameter disks (72 cm2 area and 360 mg
average weight) are individually placed in glass petri dishes. Predetermined amounts of wood
extract or pure compounds that would yield calculated specific mass per unit area of paper
(mg/cm2) are weighed in glass shell vials (e.g., 36 mg of a compound applied to a disk
provided a deposit of 0.5 mg/cm2). The test compound dissolved in 2 ml of an appropriate
solvent is poured from the vial evenly onto the disk resting inside a petri dish cover. The
cover is then placed on a warm hot plate to evaporate the solvent. Trial tests using an ether-
soluble dye can be used for practice to get uniform deposits. Each treated disk is cut into
four smaller disks (3.9 cm diameter) and held overnight at room temperature before testing.
For deterrency bioassays 0.5 mg/cm2 application is presented for 3 days. A choice test
is conducted in which four disks are constructed from two half disks; one is treated with test

© 2005 by CRC Press LLC


32 Opender Koul

material and the other half a solvent blank to demonstrate feeding preference. The half disks
are joined with a thin strip of cellophane tape on the surface not exposed to termites.
Evaluation of weight loss of the disks due to feeding is averaged for each treatment and a
comparison of their means determined statistically (Scheffrahn and Rust, 1983). There are
many statistical procedures valid to use in antifeedant assays to establish the significance of
the data obtained.
In some cases feeding bioassays are based on a comparison of feeding on 1.2-cm-round
paper penicillin assay disks. Penicillin disks are prepared by placing them on a clean enam-
elated tray, and then treated with 50 µl of test material in 95% ethanol (controls with carrier
alone). Disks are allowed to dry and placed in 35 × 1.0 mm plastic petri dishes (1/dish). Each
disk then receives 50 µl of 0.03M L-proline and 0.3M sucrose solutions. For example, sixth
instars of spruce budworm (24- to 48-h-old) have been used in this type of bioassay and
placed in petri dishes with test or control disks (three replicates or more). At 48 h after
initiation of the test, the larvae were removed and frass pellets counted. The yellowish brown
frass pellets derived from the artificial food in this insect species were easily differentiated
from the white pellets derived from the paper disks. Frass pellets from artificial food were
not included in counts (Bentley et al., 1984). The percentage of deterrence was calculated as:

No. of pellets of frass from disks in teest


1– × 100
No. of pellets of frass from disks in coontrol

WAFER ASSAY
Wafer assays have been successfully used in assessing antifeedants against stored product
insects (Nawrot et al., 1982; Harmatha and Nawrot, 1984). In this method wheat wafer disks
(1 cm diameter) are immersed in test solution (in ethanol). After ethanol evaporation, stored
grain insects (e.g., Tribolium, Trogoderma, Sitophilus, etc.) are provided with either two wafer
disks immersed in ethanol (CC) or two disks saturated with test solution (TT), or they have
a choice between ethanol or test material treated disks (CT). On the basis of amount of food
consumed (on a weight difference basis) in the experiments where the insects have a possi-
bility of choice, a relative index of deterrence is calculated (Paruch et al., 2000). The weight
of food supersaturated with test material and consumed by the control group is used for the
calculation of the absolute index. A compound for which both indices reach the value of 100
and the sum = 200 is called an ideal deterrent. The classification of indices is as follows:

Below 0 = Attractant
0 – 50 = Poor deterrent
51 – 100 = Medium deterrent
101 – 150 = Good deterrent
151 – 200 = Very good deterrent

The coefficients are calculated as:

Absolute coefficient of deterrency = [ (CC – TT)/(CC + TT) × 100 ] {A}


Relative coefficient of deterrency = [ (C – T)/(C + T) × 100 ] {R}
Total coefficient of deterrency = ∑ {A} + {R}

A very specific wafer assay to evaluate feeding deterrents against plant weevils has been
documented (Thomas and Bradley, 1975). In this assay compounds have been used on pith

© 2005 by CRC Press LLC


Insect Antifeedants 33

wafers of American elder, Sambucus camadensis L., in petri dishes; 2-mm-thick wafers were
initially treated with some feeding stimulant, which would produce uniform feeding. The
feeding deterrents were then added and the amount of feeding on the wafers treated with
deterrent was compared with the feeding on control wafers (i.e., those treated with stimulants
only). Wafers first treated with sucrose solution (15% dry weight) were dried for 1 hour at
65˚C. An ethanol extract of mature Loblolly pine phloem (20 mg/ml) was made and 0.1 ml
pipetted evenly over the surface of each wafer and dried again at 65˚C for 1 hour. This was
followed by the application of the feeding deterrent in appropriate solvent at the rate of
0.1 ml/wafer. The wafers were then dried to a constant weight for 1 hour at 70˚C under a
vacuum. The wafers were then weighed to the nearest 0.1 mg and placed in petri dishes
having a 1-cm-thick layer of moistened plaster of paris in the bottom. After feeding for
7 hours by the weevils, the wafers were removed, dried to constant weight for 1 hour at 70˚C
under vacuum, and reweighed. The mean weight losses resulting from feeding were ranked
by analysis of variance as the parameter of antifeedance.

ELECTROPHYSIOLOGICAL ASSAY
Electrophysiological assays are modern techniques to evaluate the physiological deterrency
of chemicals. The generalized approach is that two microelectrodes are inserted into the
maxillary palp and the sensilla. The electrophysiological responses are then recorded with
an oscilloscope as impulses/sec. by contacting the tips of sensilla with filter paper impregnated
with the test material. The maximum number of impulses that can be evoked under treatment
and control conditions are recorded. The functions of all the receptors, though not clear, it
is now known that some respond to feeding deterrents (Ma, 1977; Nakanishi and Kubo,
1977), and is discussed separately in Chapter 2.
For instance, a procedure adopted for Spodoptera litura larvae was that larvae were fixed
ventral side upwards on a piece of plastic foam plate with three loops of steel around the
neck, thorax, and the posterior abdomen segments. Recording was accomplished by means
of stainless steel electrodes (5 µm diameter). The electrode was inserted into the proximal
part of the hypopharynx by means of micromanipulator. This method permitted simultaneous
recording of muscle potential and nerve impulses. Impulses were conducted proximally
towards the CNS and also distally towards the hypopharynx tip. The effectiveness was based
on the number of impulses. The test compounds were applied topically to various mouthparts
and antennae by means of a fine glass capillary adapted to a microsyringe attached to a
manual applicator. The recording was done on an oscilloscope to which a recording camera
was attached (Antonious et al., 1984).
Some specific techniques in electrophysiological evaluation have been used that could
be generalized if tested against a variety of insect species. In the case of Ostrinia furnacalis,
an attempt has been made to study the gustatory chemoreceptor in larval taste systems for
bioassay-guided fractionation of antifeedants. This tip recording technique (Shang et al.,
1993) has been used to detect the antifeedant activity by placing electrodes in contact with
the tip of medial or lateral sensilla styloconica of the isolated maxillae. The nerve action
potential yielding high frequencies of spikes are recorded and relative effects calculated.
Jones (1979) established an automatic feeding detector (AFD) for use in evaluating insect
angles to form a flat plate. This plate fits through a 1.4-cm-diameter hole drilled in the center
of a small petri dish base. The dish is maintained on two small pneumatic pistons (disposable
2 ml syringes)—one fixed and the other free—that permit the dish height and the alignment
of the trembler to be adjusted. A lid covers the petri dish base with a gauze guard (the guard
prevents the larva from moving over the disk). At an approximate central position on the
trembler is located a needle fixed to the central brass rod of a clamped linear differential

© 2005 by CRC Press LLC


34 Opender Koul

transductor. The transductor output is connected to a chart recorder and a light source positioned
over the petri dish. The whole apparatus is mounted on a leveled, vibration-free bench.
Movement of the trembler results in a deflection on the chart recorder. This deflection is
calibrated by adding known weights to the end plate and by moving the end plate a vertical
distance. Changes in weight are measurable at an accuracy of ±10 mg from 20 to 500 mg
and ±30 mg from 500 to 1000 mg. Vertical distance is measurable at an accuracy of ±0.2
mm over the range of 0.2 to 3.6 mm.
A pre-weighed leaf disk is fixed to the end plate using a small amount of inert silicon
grease, and the recorder offset adjusted to center the pen at mid-scale. A single insect larva
is introduced into the petri dish and behavioral observations made over a 30- to 40-minute
period. A number of such trials are carried out to establish a correlation between traces and
feeding behavior. The behavior of larvae on disks treated with deterrent chemicals results in
characteristic traces, which differ from those obtained with natural host-plant controls. Quan-
titative measurements of consumption, duration of feeding, number of test bites, and number
of rejections of the disk are then made and compared. This detector system is cheap to
construct, is robust in operation, and gives rapid analyses. This method can be used with any
insect capable of causing a deflection of greater than 0.2 mm.
Another interesting device has been used to study aphids. Synthetic diets treated with
chemicals (like DIMBOA) are prepared just prior to the recording assay. The diet is injected
into plastic vial caps (300 µl) over which is stretched a parafilm membrane. A platinum wire,
inserted through the plastic cap into the diet, serves as the voltage input electrode. A gold
wire fixed to the dorsum of the test aphid with silver conductive paint serves as a lead to the
input of the amplifier. The analysis is based on the duration of I-waves (ingestion), S-waves
(salivation), and non-probing over 2 h assay period (Argandona et al., 1983).
A similar useful electronically recorded feeding behavior for rice hoppers, Nephotettix
virescens, is known to evaluate the efficacy of allelochemicals (Saxena and Khan, 1985). In
this experimental bioassay a 5 cm fine (18 µm) gold wire is attached by a small quantity of
silver paint to the dorsum of an 8- to 10-h-old female reared on a virus-free 45-d-old TN1-
rice plant. Before attaching the wire, insects are anesthetized with carbon dioxide gas. The
insects are starved but water satiated for 2 hours and then placed on an intact leaf blade of
a treated or control plant. The gold wire is connected directly to the negative input terminal
of a transistorized automatic null balancing DC chart recorder having 250 nm recording width
and input resistance of 1MΩ. The voltage source consists of two 1.5v DC batteries connected
in series. The positive battery terminal is connected with plant roots through moistened filter
paper and an aluminium foil. The negative battery terminal is connected directly to the positive
input terminal of the chart recorder. The recorder pen is adjusted to the chart baseline and
insect feeding is monitored for 180 minutes. A chart speed of 1.5 cm/min at 500 mV amplifier
power is adequate for distinguishing various waveforms and associated voltage reversals.
Each treatment including the control is replicated ten times. The evaluation is based on the
reduction in phloem feeding compared with controls. Phloem feeding shows erratic response
in treated plants, evidenced by repeated voltage reversals in associated waveforms, which
indicates the antifeedant behavior (Saxena and Khan, 1985).

OTHER MISCELLANEOUS METHODS


Simulation bioassay
Higgins and Pedigo (1979b) developed a simulation bioassay procedure to demonstrate
feeding deterrence in phytophagous insects. This method involved rearing of two cohorts of
green clover worm larvae, Plathypene scabra (F), under optimal conditions, but separated in

© 2005 by CRC Press LLC


Insect Antifeedants 35

time of oviposition by 3 days. Thereafter the mean development of the cohort to be used in
the chemically defined treatments remained 3 days ahead of the average age and development
of the physically stressed individuals.
Trifoliates of the primary host, soybean (Glycine max), always were available in amounts
exceeding requirements during the pre-experimental rearing period. Twenty-four hours before
experimental initiation, larvae were removed from the growth chamber and allowed to accli-
matize to room temperature. Upon reaching fourth stage plus 1 day, larvae in the chemically
treated cohort were individually presented premeasured leaves selectively dip treated with
solutions of guazitine triacetate and allowed to feed for 48 hours in 0.55 liter paper cartons.
No significant larval weight differences existed at this stage (test initiation).
Every 48 hours until pupation or death, leaves were replaced with equivalent treated
trifoliates. Damaged leaves were removed and remeasured to determine the mean of 48 h
consumption (An) under chemical stress. This cycle was then replaced until pupation or
population extinction through toxicity or starvation.
Upon reaching 4th stage +1 larvae of the second cohort (physically stressed) were
presented untreated leaf material (Bn) equal in area to the mean daily consumption ±SE of
the equivalently aged larvae feeding on chemically treated leaves. Preliminary trials revealed
that split offerings of the food into 24 h treatments (Bn and Bn') would more closely model
the stress imposed by the antifeedant.
Area Bn' = An – (actual mean of Bn), ±1SE of An/2 (maximum of 1 cm2). In this way
equal amounts of food were available for consumption by each cohort. This delayed cycle
of leaf exchange was continued until pupation or population death or until forced absolute
starvation was caused by the lack of feeding by the chemically treated cohort.
Larvae of the physical cohort were individually placed in 9.53 × 6.99 × 2.24 cm ventilated,
clear plastic snap-lid boxes. To obtain the proper untreated area, leaves were measured and
then remeasured after the tip of the terminal leaflet was turned under to simulate feeding
loss. The area to be presented to the physical cohort (the area turned under) was found by
subtraction. The area turned under was then adjusted, by allowing the leaf to refold until it
was within the acceptable bounds set by the average daily consumption of the corresponding
chemically treated cohort. The leaflet was then slightly creased and the cage was snapped
shut on the fold line (turned under area inside larval cage). As area determination continued,
an effort was made to maintain equal numbers of larvae above and below the true desired
mean. Thus, mean areas presented to the physical cohort were equivalent ±1SE to that
consumed by individuals of the chemical cohort. Two trials exhibited feeding restriction of
40 to 75% depending upon the level of treatment (Higgins and Pedigo, 1979b).

Dipteran Assays
In a test against Phormia regina, an adjustable pipette rack was fashioned from wood to hold
pipettes and vials (each vial containing one fly). Disposable pipettes of 100 µl capacity in
10 µl graduation were used in combination with 25 ml vials fitted with plastic caps. A central
hole for entry of the pipette tip and several smaller ventilation holes were drilled in each vial
cap. Male and female flies were used, raised on beef liver and maintained on skim milk
powder and sugar.
Test compounds were mixed with 0.5 molar stock solution (control) of sucrose at a
concentration of 0.01 M and stored at 4˚C in darkness for the duration of each trial (6 days).
To ensure that the fly could easily ingest the test solution, the pipette racks were adjusted to
an angle that allowed the solution to be readily absorbed on Whatman No. 1 filter paper.
Newly emerged adults (1, 3, and 5 days old) were anesthetized with carbon dioxide gas
prior to transfer to the vials in which they were given one day to acclimate and starve. Eleven

© 2005 by CRC Press LLC


36 Opender Koul

of the twelve pipettes on each rack were connected to vials containing flies and the 12th
served as an evaporation control. Three of the four racks held pipettes with alkaloid diets
and the fourth held the 0.5 M solution of sucrose control. Readings were taken 6 hours and
24 hours after the beginning of the trial to determine the volume consumed to the nearest
microliter (Blades and Mitchell, 1986).

WireWorm (Melanotus communis) Assay


For wireworms both choice and no-choice designs have been adopted (Villani and Gould,
1985). In the choice design two experiments were performed. Plexiglas containers of 2.5 cm3
(Experiment 1) and 30 × 15 × 4 cm (Experiment 2) were filled with moist soil. A treated
potato section (Experiment 1) or treated corn seed (Exp eriment 2) was placed 2.5 cm below
the surface at one end of each container and a control for each at the opposite end. A single
corn wireworm was buried head downwards in the center of the container; 25 containers were
used in Experiment 1 and 50 containers in Experiment 2. The containers were placed in the
dark, and after 36 hours (Experiment 1) and 8 days (Experiment 2) baits were checked for
feeding damage. A potato section or corn seed and sprout, which showed any indication of
having been fed upon, was considered damaged.
The no-choice test design was as above with the exception that only one bait, either
treated or untreated (control), was placed in each Plexiglas container.

Boll Weevil Assay


A 1% solution of test fraction or compound was used, and an unpunctured debracted bud
from a greenhouse-grown cotton plant was dipped momentarily in the solution. Ten 1- or
2-day-old adult boll weevils unfed from time of emergence or starved for 24 hours were
placed in a petri dish with one treated and one untreated bud (dipped in solvent alone) and
held for 4 hours. Five control and five test dishes were prepared for each test. The number
of feeding punctures per bud was counted under a dissecting microscope (Bird et al., 1987).

Scale Insect Assay


Test for red scale, Aonidiella aurantii, and yellow scale, A. citrina, have been conducted by
spraying (with an atomizer) half of a green lemon fruit with a dilution of 0.01 to 1.0% as an
aqueous emulsion and covering the other half with parafilm to protect it. The crawlers were
allowed to migrate from heavily infested lemons onto the treated lemons. The insects were
counted after 5 and 25 days post-treatment. A similar test has been conducted for citrus red
mite, Panonychus citri (Jacobson et al., 1978).

Sawfly Assay
A standard bioassay for sawflies used a 7- to 10-cm twig of 1-year-old jack pine foliage.
Foliage was stripped from the twig until ten pairs of needles remained at each end. Twigs
were rinsed in distilled water and allowed to dry. Needles at one end of each twig were
covered with the resin acid/methanol solution by pipetting a few drops at the base of the
needle and allowing it to flow to the tip. Needles on the other end were treated with solvent
only. A similar twig received the solvent at one end and nothing at the other, to serve as an
additional control. The treated needles were allowed to dry at room temperature for a
minimum of 30 minutes. The treated twig was suspended horizontally on an insect pin that
passed through the center of the twig; the pin was then inserted through 6.2 cm2 moss-green

© 2005 by CRC Press LLC


Insect Antifeedants 37

paper and into a No. 11.5 rubber stopper. Five 4th or 5th instar sawflies, Neodiprion dubiosus,
N. lecontei, and N. rugifrons, were placed on the needles at each end of the twig. Replicates
were placed in an environmental chamber at 20˚C under continuous light. A test concentration
was recognized as biologically active in inhibiting larval feeding if > 70% of the total number
of larvae settled on the end treated with solvent only after 4 hours (Schuh and Benjamin,
1984).

Leaf Beetle Assay


Matsuda and Senbo (1986) described a method to test feeding deterrents against leaf beetles
of various families. The bioassay procedure was based on a comparison of nibbling by adult
beetles on 2 × 2 cm filter papers. The assay chamber was composed of a plastic petri dish
of 9 cm diameter and 1.5 cm in depth. Three 7-cm-diameter filter papers were immersed in
2 ml of water and were placed on the bottom of the petri dish, and a doughnut-like plastic
disk (3 cm ID and 7 cm OD) was put on the papers. Four pieces of filter paper per dish were
equidistantly placed on the doughnut-like disk. Filter papers were treated with 0.075 ml of
test chemical in methanol; control papers were treated with carrier alone. Papers were allowed
to dry for several minutes, then placed in a petri dish, four to a dish. Twenty adult beetles
starved for 24 hours were released into a petri dish with test or control material. All assays
were completed in darkness at 24 to 25˚C. Five replicates of test and controls were run for
each compound tested. Twenty-four hours after release of the beetles, the feeding response
was judged from the differences between test and control pieces and expressed as (- - -) =
no nibbling, (- -) = less nibbling than controls, (±) = same nibbling as in controls, and (+) =
more nibbling than controls. A negative score was considered to indicate feeding deterrence.

Oral Dosing
In this procedure a preliminary assessment is made for potential feeding deterrent compounds.
In fact, several earlier studies have shown that deterrent chemicals could be consumed after
elimination of chemoreceptors. Recently cannulas have been used to place test compounds
into the gut lumen via the oesophagous in order to avoid behavior rejection in some grass-
hoppers (Cottee et al., 1988). Sutherland et al. (1981) have also used cannulas for oral dosing
of scarabid grubs. This technique, however, has problems particularly in handling, which
induces deleterious and damaging effects to the foregut during ingestion. Another problem
is that doses are necessarily sporadic and do not mimic normal intake patterns.
Semi-microgelatin capsules have been successfully used with grasshoppers (Cottee et al.,
1988), which conceals the taste completely and there is rapid release in the gut. However,
this technique is not feasible for smaller insects and is time consuming.
Another technique of oral dosing for feeding deterrents was recently demonstrated for
various insect species (Usher et al., 1989). In this method deterrent solutions are enclosed
inside lipid vesicles and suspended in non-deterrent solutions that can be offered to the insects
to drink. Liposomes containing an aqueous solution can be formed in a number of ways,
such as reverse phase evaporation, where reverse micelles are formed of phosphatidylcholine
around the aqueous phase in an excess of diethyl ether. The ether is evaporated, causing the
lipid to form bilayer vesicles, or liposomes, which are sized to approximately 1 µm in diameter
by passage through a polycarbonate filter. The liposomes can be separated from any remaining
deterrent in the surrounding medium by passage through a gel filtration column. The lipo-
somes are collected in the void volume of the eluting solvent, while deterrent molecules not
inside liposomes are retained in the column.

© 2005 by CRC Press LLC


38 Opender Koul

In the assay each insect is weighed immediately before and after a drinking bout and the
volume drunk determined by the weight change. Amounts drunk by control and treatment
groups of insects are compared. Thus this technique is a very useful approach to dose insects
with compounds that normally deter feeding.
Some other processes on similar lines use microspheres, microcoating, and molecular
encapsulation (Usher et al., 1989; Clancy et al., 1992).

Field Trials
Not many studies are available where feeding deterrents have been used in large-scale field
trials. The vast majority of feeding bioassays with plant-derived chemicals have been per-
formed under laboratory (or in some cases greenhouse) conditions, although field tests of
metal-containing fungicides as antifeedants have been done (Jermy and Matolcsy, 1967;
Ascher, 1979). Though field tests have confirmed laboratory results for some naturally
occurring chemicals (All and Benjamin, 1976; Metcalf et al., 1980), laboratory results cannot
necessarily be extrapolated to field conditions due to:

• Alteration of the chemicals in the field by environmental factors


• Habituation of insects
• Use of artificial substrates in the laboratory experiments
• Insect movement away from treated plants
• Composition of the plant community (Lewis and van Emden, 1986)

In fact there is no specific procedural design devised for field evaluation of antifeedants. The
procedures are similar to those used for conventional chemical pesticides and have been followed
for various field trials in a similar fashion. Among the antifeedant plant chemicals, the most
extensive field trials have been carried out with neem products, mostly due to broad international
cooperation (Schmutterer and Ascher, 1987). Ladd et al. (1978) carried out the earliest neem
seed extract evaluation in the field against Japanese beetles, Popillia japonica, using plots
consisting of four to five plants. Similarly, field trials with Colorado potato beetles, European
corn borer, diamond back moth, and various aphids have been conducted to show reasonable
control by foliar application of neem extracts and azadirachtin (Isman et al., 1991; Lowery et
al., 1993). The proceedings of the World Neem Conference held in Bangalore, India, in 1993
(Singh et al., 1996) reports 24 papers on successful field application of various neem-based
formulations. These results show the effect of these formulations on a variety of insects like
grasshoppers, rice pests, bean flies, various Helicoverpa species, cotton pests, pod borers, maize
pests, fruit flies, mango hoppers, and others. Such studies definitely demonstrate the potential of
antifeedants on a large scale. However, there is a need to evaluate other identified antifeedant
compounds in the field to determine the practical application potential of such compounds.

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Usher, B.F., Bernays, E.A., Barbehenn, R.V., and Wrubel, R.P. (1989) Oral dosing of insects
with feeding deterrent compounds. Entomol. Exp. Appl., 52, 119–133.
Villani, M.G. and Gould, F. (1985) Screening of crude plant extracts as feeding deterrents
of the corn wire worm, Melanotus communis. Entomol. Exp. Appl., 37, 69–75.
Warthen, J.D. Jr., Redfern, R.E., Uebel, E.C., and Mills, G.D. Jr. (1982) Antifeedant screening
of 39 local plants with fall armyworm larvae. J. Environ. Sci. Health, 17A, 885–895.
Wolfson, J.L. (1988) Bioassay techniques: An ecological perspective. J. Chem. Ecol., 14,
1951–1963.
Wolfson, J.L. and Murdock, L.L. (1987) Method for applying chemicals to leaf surfaces for
bioassay with herbivorous insects. J. Econ. Entomol., 80, 1334–1336.
Zalkow, L.H., Gordon, M.M., and Lanir, N. (1979) Antifeedants from rayless goldenrod and
oil of pennyroyal: Toxic effects for the fall armyworm. J. Econ. Entomol., 72, 812–815.

© 2005 by CRC Press LLC


4 STRUCTURE-ACTIVITY RELATIONSHIPS
Biologically active compounds are found among all major classes of secondary plant sub-
stances and especially among the higher oxidized metabolites. The diversity of structures is
usually large, and many of the biological effects are interpreted in terms of plant defense
against predation and pathogenecity. Insect antifeedants are one of such biologically active
substances that induce the cessation of feeding either temporarily or permanently. Various
aspects of behavioral physiology in response to such chemicals have been described in the
previous chapter, but quantitative structural-activity relationships have posed several problems.
The overall picture that emerges from various evaluations shows that small structural
variations can produce drastic changes in the activity profile of compounds. A critical exam-
ination of functional groups present in the active molecules provides crucial information
about the optimal relative stereochemistry required to stimulate an antifeedant response in
insects, but an analysis based on functionality and skeletal types appears to be difficult to produce
any generalization, albeit one can certainly discuss activity variations within a skeletal type.
The main aim of this chapter is directed in this direction and generalizes sufficient
structure-activity information within specific skeletal systems to allow rational modification
of readily available feeding deterrents to be made into potential insect control agents. Accord-
ingly some specific class of compounds will be discussed in terms of structural-activity
relationships to bring forth some generalizations.

LIMONOIDS
This group of compounds, today, are considered to be most potential antifeedant allelochem-
icals that could be introduced in an Insect Pest Management (IPM) system. A specific example
like azadirachtin (1), a tetranortriterpenoid from the Indian neem tree Azadirachta indica, is

© 2005 by CRC Press LLC


44 Opender Koul

known for its potent antifeedant characteristics (Koul, 1992). It is widely reported that
azadirachtin affects the feeding behavior of many insect species (Koul, 1996), and a variation
in the structure influences the activity of this compound (Blaney et al., 1990; Rembold, 1989;
Ley et al., 1993). For instance, hydrogenation of the dihydrofuran ring as in dihydroaza-
dirachtin (4) does not affect the activity of the molecule, and esters on the A ring do not
affect the activity of the compound (Yamasaki and Klocke, 1987), although they could be
important in transporting the compounds to the receptor sites. The difference in the level of
antifeedance, for instance, among compounds 1 to 7 evaluated against four noctuid larvae
(Blaney et al., 1990), has been attributed to the ability of the respective esters at C-1 or C-3
to transport the molecule to the target site.

COOCH3 COOCH3

R1O R4 OH R4
O R1O O OH
11 11
O 22
O
1 1 23

3 O 3 O
O O
OR3 OR3
R2O R 2O
H3COOC O H3COOC O
O O

(1) R1 = , R2 = Ac, R3 = H, R4 = OH (4) R1 = , R2 = Ac, R3 = H, R4 = OH


O

(2) R1 = H, R2 = , R 3 = R4 = H (5) R1 = 2 methylbutenate, R2 = Ac, R3 = H, R4 = OH

(6) R1 = pyruvate, R2 = Ac, R3 = H, R4 = OH


(3) R1 = R2 = R3 = R4 = H
(7) R1 = R3 = H, R2 = Ac, R4 = OH

However, change in C-1 or C-3 ester in combination with a structural variation at C-11
resulted in decrease of feeding deterrent activity, especially in H. armigera. This suggests
that the type of ester present at C-11 is important. These results also show that hydrogenation
of C-22,23 double bond in azadirachtin does not significantly influence antifeedant activity,
thus confirming the observations of Yamasaki and Klocke (1987). Hein et al. (1999) also
report the hydroxy group at C-11 in azadirachtin A is important for high mortality rates, and
a single bond between C-22 and C-23 increases the degree of efficiency. An exchange of the
large ester group ligands at C-1 and C-3 with hydroxy groups in combination with a single
bond between C-22 and C-23 and a hydroxy group at C-11 leads to high feeding activity and
a degree of efficiency of about 100 percent. Ley and his co-workers have synthesized a large
number of compounds to establish structure-activity relationships. Ley et al. (1993) report
screening of 31 compounds related to azadirachtin against Spodoptera littoralis and point to
the importance of hydroxyfuranacetal moeity in the high level of potency of this compound.
Stereochemistry at C-7 is crucial, and the bridging oxygen substituent at C-6 may play some
role. The precise spatial and electrostatic requirements of all the various oxygen substituents,
according to Ley, need more detailed studies. These studies also reveal reduction in activity
by increasing bulk at C-23. However, similar things do not hold true for other evaluated
species like S. frugiperda or H. armigera. In fact the bulky isopropoxy substitute results in
a compound with very potent antifeedant activity against S. frugiperda (Blaney et al., 1990)
and less bulky ethoxy substitution quite active against H. armigera.

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Insect Antifeedants 45

φ8
O OCH3
O
C
φ2
φ7
OH
O O OH
φ1 11 φ11 φ12
D O 13
E 20
1 14
F G
8
A B φ9
O
O φ3 3 7 O
φ4 4
OH
CH3C O C φ10

CH3O C φ5 O
φ6
O

FIGURE 4.1 Azadirachtin key structural features. The designation of torsional angles and notation of
the different rings are shown.

These studies, therefore, imply that large numbers of functional groups present in aza-
dirachtin and the sensitivity of azadirachtin in different bioassays exhibit variable results.
Therefore, the question still remains that specificity of structural features responsible for such
an activity remains unpredicted. A recent theoretical study on the conformations of azadirach-
tin has provided some cruical information by critically examining the functional groups
present in this compound and its methyl ether derivatives, which provide the data about the
optimal relative conformations required to stimulate antifeedant response (Baldoni et al.,
1996). In this study, uniform scanning using molecular mechanics calculations were carried
out, and accordingly the conformations arising from the combinations of torsional analysis
φ – φ (Figure 4.1) were considered (Dewar et al., 1985).
In order to obtain a structure-activity relationship, the results obtained for azadirachtin
were compared with those for its 7-methyl ether derivatives (Figure 4.2). In case of aza-
dirachtin the substituents at C-1, C-3, C-4, and C-11 showed a moderate but significant
conformational flexibility; in contrast, the tricyclic dihydrofuran ring showed a restricted
rotation about the single bond with a highly preferred conformation at φ 9 ≈ 70°. Similar
conformations were obtained for methyl ether derivatives. However, different results were
obtained for the energy profiles, which reflected the influence of the dihydrofuran ring
orientation. After comparing various results it was obvious that OH groups at C-11 and C-20
could collectively play a significant role in conferring the appropriate structural conformation
and thus significant decrease in activity. Similarly the monomethyl substituent on C-7, C-11,
or C-20 may not be critical to confer the structural conformation leading to biological activity
for these compounds. In contrast, the presence of two methyl groups at C-11 and C-20
respectively or trimethylation introduces important changes in the conformational behavior
of these compounds, which may be responsible for the lack of the activity (Baldoni et al.,
1996).
Similar studies with 3-tigloyl azadirachtol and other derivatives of azadirachtin have
established that lack of antifeedant activity of 7-keto derivative and other inactive compounds
can be explained on the basis of their different conformational behavior (Baldoni et al., 1997).
For instance, on the three 2D conformational energy maps a total of 18 conformations were
selected on energetic grounds for 3-tigloyl azadirachtol from molecular mechanism calcula-
tions. These data together with other experimental findings on the antifeedant activity of
closely related compounds suggest that specific ester groups are not required at positions C-1
and C-3 in the azadirachtin nucleus in order to maintain a high level of activity. However,
the presence of certain ester groups (e.g., tigloyl) at these positions may provide a favorable
hydrophilic/lipophilic balance, necessary for optimum transport across various membranes

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46 Opender Koul

O COOCH3 O COOCH3
OH OH OCH3 OH
O O O O
11 11
O 13 O 13
1 14 20 1 14 20
8 8
3 O 3 O
7 O 7 O
4 4
CH3COO OCH3 H CH3COO OCH3 H

H3COOC O H3COOC O

AZADIRACHTIN-7-METHYLETHER AZADIRACHTIN-7,11-DIMETHYLETHER

O COOCH3 O COOCH3
OH
OCH3 OH OCH3
O O O O
11 11
O 13 O 13
1 14 20 14 20
1
8 8
3 O 3 O
7 O 7 O
4 4
CH3COO OH H OCH3 H
CH3COO

H3COOC O H3COOC O

AZADIRACHTIN-11-METHYLETHER AZADIRACHTIN-7,20-METHYLETHER

O COOCH3 O COOCH3
OH OCH3 OCH3 OCH3
O O O O
11 11
O 13 O 13
14 20 1 14 20
1
7 7
3 O 3 O
8 O 8 O
4 4
OH H CH3COO OH H
CH3COO

H3COOC O H3COOC O

AZADIRACHTIN-20-METHYLETHER AZADIRACHTIN-11,20-METHYLETHER

FIGURE 4.2 7-methylether derivatives of azadirachtin

and physiological partitions, as these molecules make their way to their target sites or
receptors — an observation made by earlier workers as well. It is essential, therefore, to point
out here that the highest level of biological activity was obtained when C-1 and C-3 positions
were occupied by only OH functional groups (Hansen et al., 1994).
Another interesting example of a limonoid from neem showing potential antifeedant
activity is salannin (Yamasaki and Klocke, 1989; Koul et al. 1996). Fourteen derivatives of
salannin (8) when bioassayed against Colorado potato beetle, Leptinotarsa decemlineata,
larvae have revealed four target points which after modification change the activity pattern
of salannin. These targets are (i) hydrogenation of the furan ring, (ii) replacement of the
acetoxy group, (iii) modification of the tigloyl group, and (iv) saponification of the methyl
ester. The hydrogenation of the furan ring to the tetrahydrofuran ring increases the antifeedant
activity. The replacement of the acetoxy group at position 3 by a methoxy group increases

© 2005 by CRC Press LLC


Insect Antifeedants 47

the activity, and a similar increase occurs when the acetoxy group at position 3 is replaced
by hydrogen. The modification of a tigloyl function, such as hydrogenation, increases the
activity at least twofold. On the contrary, deesterfication of the tigloyl or the α-methyl
butyrene groups result in a reduction of activity. Saponification of the methyl ester at C-11
increases the activity, for instance, salannic acid (9) is at least eightfold more active than
1,3-diol derivative (10).

O
O OH

O O O
O OH
O

3 3
O O
CH3COO HO

O O

(8) (9)

O
O
O

OH O
O
O O

3 O
O
O 7
HO
OH
O

(10) (11)

However, other derivatives in which the methyl ester is chemically modified need to be
prepared in order to ascertain the activity of the carbomethoxyl group (Yamasaki and Klocke,
1989).
Another group that has shown potential as antifeedant limonoids is that of citrus
limonoids. It appears that furan and epoxide groups have to play a major role in the activity
of these compounds. A possible role of C-7 is implied by the modest activity of the 7-hydrox-
ylated de-epoxy system (Bentley et al., 1988). For instance, highly reduced activity of
deoxyepilimonol (11) against epilimonol (12) and Limonin (13) demonstrate the above
conclusion. In certain cases the cyclohexenone A ring and the α-hydroxy enone group in the
B ring appear to be important for antifeedant activity. Also, the absence of 14-15 epoxide
may not drastically reduce antifeedant activity (Govindachari et al., 1995). Recently,
23 semisynthetic derivatives of citrus limonoids, with a focus on the changes in C-7 carbonyl
and the furan ring, have been evaluated against Spodoptera frugiperda larvae. In particular,
reduction at C-7 afforded the related alcohols, and from these their acetates, oximes, and
methoximes were prepared. Hydrogenation of the furan ring was also performed on limonin
and obacunone to establish the significance of the furan ring in the antifeedant activity against
insects (Ruberto et al., 2002).

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48 Opender Koul

O O

O O

O O O
O
A C D
14 14
15 15
O O
O O O A' B O
7 7

OH O

(12) (13)

If we look at the overall system of limonoid compounds there are several impediments
to developing a quantitative understanding of structure-activity relationships. Different inves-
tigators seldom utilize the same bioassay species, interspecific differences in the response of
the test insect can easily mask any meaningful observations, and differences in larval stadium
make comparisons invalid (Champagne et al., 1992). Although some specific examples from
neem and citrus have been discussed above and despite the difficulties inherent in comparing
data from such diverse array of studies, some qualitative trends could be generalized. Aside
from the C-seco limonoids mentioned above, the most active compounds appear to be intact
apo-euphol limonoids (14) with a 14,15-epoxide and either a 19/28 lactol bridge or a cyclo-
hexenone (3-oxo-1-ene) A ring. Absence of the 14,15-epoxide results in reduced activity as
with azadiradione (15) in comparison to cedrelone (16) or anthothecol (17).

OH
O
O

OH

HO O OAc

(14) (15)

O
O

O
(16) RH
14 15

(17) ROH O
O
O

O O O OAc

OH
(18)

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Insect Antifeedants 49

Oxidation to a D-seco limonoid (18) appears to correlate with reduced activity. For
example, azadirone (19) is almost inactive as a feeding deterrent, but the 16-keto intermediate
azadiradione (20) is quite active. Further oxidation to 14-epoxy-azadiradione (21) results in
considerable loss of activity, which is scarcely improved by formation of the lactone-D ring
in gedunin (18).

O O

16 O

O OAc O OAc

(19) (20)

O
O

AcO
O

O
O
O O
O
O
O
O OAc

(21) (22)

OAc O
O
O
OH

O O
O
O O AcO OH
O
O AcO
H

(23) (24)

The A,D-secolimonoids like liminin (13), nomilin (22), and obacunone (23) are usually
less active than D-seco and many apo-euphol compounds. Model compounds based on the
C and D rings, the associated furan ring are slightly more active than limonin, suggesting
that this region of the molecule is most critical for bioactivity (Bently et al., 1990). However,
few A, B, or B-seco limonoids seem to be less active than above A,D-seco limonoids, but it

© 2005 by CRC Press LLC


50 Opender Koul

is difficult to ascertain functional comparisons due to substantial variability in bioassay


procedures. At this point of time it is not possible to draw any specific conclusions due to
the paucity of structure-activity data based on monophyletic biosynthetic pathways of
limonoids and the process of ring modification represented by the O and S values, which are
likely independent of each other. However, there is some relationship in structure activity to
some cytotoxicity studies against mammals. Pettit et al. (1983) bioassayed 38 limonoids from
Meliaceae and Rutaceae for inhibition of a murine P-388 lymphocytic leukemia cell line.
The most active compounds were 14,15-epoxy D ring and a 19-28 lactol bridge compounds
like sendanin (24). Compounds with the epoxide and a 3-oxo-1-ene A ring (anthothecol)
were somewhat less active and the reduction of the olefin eliminated the activity.
In a very recent study, structure-related insect antifeedant relationship of 56 limonoids
of both natural ones from various plants and modified forms belonging to the order Rutales
was attempted, considering substitution patterns, oxidation states, and hydrophobicity, as well
as distant geometry derived through conformational analysis on molecular modeling. It was
demonstrated that orientation of the furan and hydroxylation at specific carbon sites influence
the antifeedant activity against Spodoptera litura (Suresh et al., 2002). These studies suggest
that molecular modeling could be a significant helping tool for designing of compounds. For
instance, relaxed bond distance between oxygen atom at C-3 and C-20 of the azadirachtin
molecule was found comparable to that of 20-β-hydroxyecdysone, which has a significance
in binding to ecdysone receptors; therefore, such a change of the distance between the active
sites could have an impact on antifeedant activity as well. These studies also suggest that the
most active limonoid could be either an intact apoeuphol compound or a C-seco compound
with a hydroxylated furan (an –OH that may overlap with a C-20 –OH in azadirachtins) and
a dihydroxy A-ring.

QUASSINOIDS
Quassinoids, which are, like limonoids, degraded triterpenes, exhibit some structural rela-
tionship vis-a-vis the antifeedant activity. Discovery of bruceantin (25), a quassinoid from
Brucea antidysenterica, as a potent antineoplastic compound has generated tremendous
interest in quassinoid type of natural and synthetic biologically active compounds (Lidert et
al., 1987). Apart from anticancer, antiviral, antiamoebic, antimalarial, and anti-inflamatory
properties of such compounds, quassinoids possess anti-insect properties as well, particularly
the feeding deterrent effects (Leskinen et al., 1984). The structure activity correlation pattern

OH

HO COOCH3
O

O OCO

HO O O

(25)

for the feeding inhibition, as demonstrated against tobacco budworm, Heliothis virescens,
can be summarized as follows:

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Insect Antifeedants 51

• The A-ring enerone function is essential for activity. Reduction of the electrophilic
capacity of this michael acceptor results in lowering of activity. Thus the A-ring
diosphenols are on the whole less active, as can be seen in compounds 26 versus
27 (Lidert et al., 1987). However, higher electrophilicity of diosphenol achieved
by placement of the electron withdrawing trifluoromethyl sulfonyl substituent onto
the 3-hydroxy group (28) did not result in increased activity.

OH OH

HO COOCH3 HO COOCH3
HO
O O

O O O OCO

HO O O O

(26) (27)

OH

HO COOCH3
O
O OCO

SO2F3CO O O

(28)

• The C-ring oxomethylene bridge is very important (compound 29 is of poor


activity). C-8 and C-13 linkages seem to be somewhat more advantageous than
C-8 to C-11 (compound 30 versus 31 and 32).
• Ester side chains have in many cases great influence on activity (compound 33
more active than 34). On the whole hydrophilic side-chains seem to be deterimental
(35 versus 36) while hydrophobic, unsaturated side chains improve activity (37, 38).

OH

HO
HO

C
O

O O

(29)

Compounds lacking side chains altogether can be fairly active (30). Their pattern of
structure-activity relationships is similar to the ones reported by other workers, too (Klocke
et al., 1985; Odjo et al., 1981).

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52 Opender Koul

OH OH

HO HO
HO HO
O O

O OH O OH

OH
O O O O

(30) (31)

OH

HO
HO
O

O OCO

O O

(32)

OH OH

HO OAc HO OAc
O O
O OCO O OAc

HO O O HO O O

(33) (34)

OH OH

HO OAc HO OAc
O O OH

O OCO O OCO

HO O O HO O O

(35) (36)

OH OH

HO OAc HO OAc
HO HO
O O
O OCO O OCO

O O O O

(37) (38)

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Insect Antifeedants 53

DITERPENES
Various diterpene acids and clerodane types of diterpenes have been identified from various
plant sources and shown to deter feeding in various insect species (Hosozawa et al., 1974;
Rose et al., 1981; Miyase et al., 1981; Koul, 1982; Wagner et al., 1983; Schuh and Benjamin,
1984; Belles et al., 1985; Enriz et al., 1994; Giordano et al., 2000). In fact, clerodanes occur
in different isomeric forms, and the general problem of a structure-activity relationship exists
here too, due to variability in bioassay evaluations. Nevertheless, it is possible to draw some
conclusions. For instance taking clerodin (39) as the parent compound, changes in different
carbons vis-a-vis the activity can be discussed. There are few derivatives that bear a substituent
at C-1 as in ajugareptansin (40) and ajugareptansone A (41), but these are weak antifeedants.
According to Belles et al. (1985) this may be accounted for by a Skew boat confirmation of
the A ring, caused by sterical hinderence between substituents at C-1 and C-9. In clerodendrin
A (42) aceylation at C-2 position results in a complete loss of activity; however, in Ivaine I
(43), aceylation has no effect on the activity.
O

O
O O 15
14
16

O O O
COO

1 1 9 O
2 10 8
3 5 7
4 6 CO
HO
O
O O OAc
OAc OAc AcO
AcO AcO

(39) (40) (41)

O O

O O

HO HO
2 2

COO COO
OAc
O O
OAc OAc
AcO AcO

(42) (43)

In any case, stereochemistry at C-2 is important, which is evident from higher activity
in 14,15-dihydroajugapitin (44) than Ivaine IV (45). The substitution or stereochemistry at
C-3 does not seem to affect the activity in any case. The epoxy ring also does not appear to

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54 Opender Koul

hinder the activity due to the similarity in activity among ajugarin II and III (46, 47) and
tafricanins (48, 49). On the other hand, stereochemistry at C-4 seems to play an important
role in the activity of these compounds. Several decalins with an epoxide of the opposite
stereochemistry are less active (Ley et al., 1982; Geuskens et al., 1983) than otherwise
identical decalins of the normal stereochemistry.

O
O O

O O

HO HO
2 2

COO COO

O O O
OAc OAc OH
AcO AcO AcO

(44) (45) (46)

O (48) R1 = O, R2 = H, R3 = Cl, R4+R5 = O

(49) R1 = O, R2 = R4 = H, R3 = Cl, R5 = OAc

R1
HO R2O R5
R4
OAc R3 AcO
HO AcO

(47)

According to vanBeek and deGroot (1986), an important feature of the clerodane diter-
penes might well be the α-CH2OAc side chain at C-5. All derivatives, including those with
an intact epoxy group, lacking the acetyl substitution at C-19, are only very weakly active
or inactive, like ajugarin V and clerodendrin A tetraol (50, 51). A loss of acetyl group at C-
6 does not affect the activity, as ajugarin I (52) and ajugarin II (46) do not differ in their
antifeedant action. The necessity of some oxygen-containing substituent at C-9 is immediately
obvious from the low level of activity of several synthesized decalins relative to clerodin and
other natural clerodanes. Many different furofuran side chains in the ajugarin series and a
furan side chain in the tefricanins all give rise to deterrent activity. Geuskens et al. (1983)
suggest that activity of clerodanes is neither located in the side chain nor the decalin moiety
alone but rather two groups appear to exert a synergistic effect on each other with regard to
antifeedant activity.

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Insect Antifeedants 55

O O O

O O

HO

HO

O O O
OAc OH OAc
HO HO AcO

(50) (51) (52)

Considering the feeding deterrent activity exhibited towards Tenebrio molitor of several
diterpenes with clerodane skeleton using electronic and conformational behaviors (Enriz et
al., 1994), they seem to mediate at least through two binding sites. The presence of an α,β-
unsaturated system, or one spiroepoxide substituent at C-4 in the clerodane structure, together
with the β-furyl moiety at C-9 is important to evoke antifeedant activity. In addition the free
rotation of the β-furyl group could play a significant role in the biological activity. These
results will be apparently helpful in the structural identification and understanding of the
minimal structural requirements for these molecules and can provide a guide in the design
of compounds with antifeedant activity (Enriz et al., 1994).
Enriz and his co-workers (2000) have further emphasized that steroelectronic factors are
more important than the hydrophobic aspects. A conformational study indicates that the
optimum interatomic distance between furan ring in the side chain and a spiro-epoxide range
between 9.5 and 10.5 Å. They also found similar steroelectronic response among withanolides
and azadirachtin, which for the first time gives an indication of a relative chemical mechanism
for these compounds (Enriz et al., 2000). Certain structural transformations in this respect
by synthesizing such derivatives have proved the importance of furan moiety and cleavage
of the oxirane ring, which causes almost total disappearance of activity (Gallardo et al., 1996).
To be precise the presence of β-axial spiro epoxy at C-4 together with β-ethylfuran ring, an
ethyl butenolide or a hexahydrofurofuran substituent at C-9 is necessary to elicit the anti-
feedant activity of neoclerodanes against insects (Camps and Coll, 1993; Rodriguez et al.,
1993; Malakov et al., 1994; Urones et al., 1995).
Recently a new class of insect antifeedants, the ryanodine diterpenes (53), have been
isolated from Persea indica (a Lauraceae plant). The structure-activity relationship of these
compounds show that C-14 and C-1 substituents play an important role. Aceylation of these
centers results in loss of activity, whereas pyrrolecarboxylate at C-14 (54) confers high
OH

1
HO OH
14
O
R= C
RO
N
OH
HO O

(53) (54)

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56 Opender Koul

potency (Gonzalez-Coloma et al., 1996). The comparisons of the mammalian toxicity and
insect feeding deterrency of these compounds suggest a mechanism of action of these diter-
penes in insects different from the Ca2+ release channel (Gonzalez-Coloma et al., 1996).

SESQUITERPENES
Caryophyllene oxide, spathalenol, guaianol, helenalin, eupatoriopicrin, bakkenolide A, bis-
abolangelone, and various sesquiterpene lactones are active antifeedants against a variety of
insect species (see Chapter 7). In fact antifeedant activity of a number of sesquiterpene
lactones has been comprehensively reviewed (Picman, 1986), but as usual due to efficacy
variabilities it has been difficult to generalize structural features responsible for this activity.
Two conclusions that could be emphasized here are the importance of α-methylene group
evidenced by diethylamine and methanol adducts of eupatolide being more deterrent than
eupatolide (55). Michael type addition with the α-methylene on γ-lactone as well as with
α,β-unsaturated ketone or with other exomethylenes could explain the activity of sesquiter-
pene lactones, which do not contain the α-methylene-γ-lactone moeity and, therefore, are
worth consideration.
Similarly antifeedant activity of 53 sesquiterpenes of Lactarius origin is known against
stored grain pests (Daniewski et al., 1995). The sesquiterpenes with lactarane (56) and
marasmane (57) skeletons are much more active than those with an isolactarane skeleton
(58). The activity of furans is generally higher than their lactonic counterparts. The activity
of furans depends upon the presence of hydroxyl groups in their molecules. The greater the
number of OH groups the lower the activity. However, no simple correlation is possible
between the antifeedant activity of lactones and the number of –OH groups in their molecules.
A change in the position of a carbonyl group from C-5 to C-13 in the lactone ring does not
improve the activity. Alteration in the natural characteristic configuration at C-8 causes a
decrease in antifeeedant activity in both lactones and furans of lactarane skeleton (Daniewski
et al., 1995).

R1
OH O

CH2 O
O

O
CH2R4
R3 R1
O R2 R2

(55) (56) (57)

O OH OH
OH

O OHC O

R HOH2C OH

(58) (59) (60)

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Insect Antifeedants 57

CHO
CHO CHO OH
OH CHO
CHO CHO

CH2

(61) (62) (63)

It could be further demonstrated that a mixture of hemiacetal and γ-hydroxyaldehyde


form of isolactarane sesquiterpenes (59) are very active compounds compared with those that
exist only in hemiacetal form (60) (Daniewski et al., 1997).
Sesquiterpene drimane antifeedants like warburganal (61), polygodial (62), and muziga-
dial (63) are also known active compounds (Lam and Frazier, 1987) with a reactive enedial
functionality that interacts with a chemoreceptor site via pyrrole formation. A series of natural
drimanes and related synthetic compounds, when tested against aphids, show least activity
due to polygodial or those compounds that do not possess the trans-decalin ring of the natural
drimane aldehydes. Despite the high activity of (-) warburganal, of the other 9 α-hydroxy
compounds only compound (64), the 9 α-hydroxy analogue of cinnamolide (65), is active.
In fact, these compounds, which have been reported to be active against several species of
Spodoptera and Heliothis (Blaney et al., 1987), are inactive against aphids.
O 9
8 CHO

OH
O
O CHO

(64) (65) (66)

At the molecular level most active dialdehydes have a double bond in common between
C-7 and C-8 and an 11-12 β dialdehyde (Gols et al., 1996). The importance of such a
configuration is supported by the lack of activity of compound (66) and (±) isotadeonal (67).
The deterrence of lactones is higher when the lactone group is present at the C-8/C-9 position.
Forty-one sesquiterpenes with a dihydro-β-agarofuran skeleton (68) and 14 related syn-
thetic compounds have been evaluated against Spodoptera littoralis larvae (Gonzalez et al.,
1997). These studies show activity in 38 compounds, the most active being those with isoalatol
(69) and 4 β-hydroxyalatol (70) skeletons. Comparing the activities of the compounds with
the same skeleton, the activity seems to increase with the number of acetate esters and decrease
with the number of benzoate esters. In general products with aromatic esters at C-1 and C-9,
whatever the stereochemistry, are moderately active. The introduction of ester groups at C-2
does not seem to change the activity of the compounds.

CHO 9
1
11 8
(69) 4β - OH, 9α - OBz, 1α,6β,15 - OAc, 8α -
12 2 10 OCH3
8 CHO A B
3 5 7
4 6
C
7 O 12 4β - OH, 9α - OBz, 2α,6β,8α,15 − OAc, 1α −
(70) OAng
11
14
13

(67) (68)

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58 Opender Koul

Silphenene sesquiterpenes are established chrysomelid antifeedants and have been eval-
uated against S. littoralis, L. decemlineata, Myzus persicae, Rhopalosiphum padi, Metopol-
ophium dirhodum, Diuraphis noxia, and Sitobion avenae (Gonzalez-Coloma et al., 2002).
Small structural changes (see Chapter 7) resulted in drastic differences in antifeedant activity,
suggesting a high molecular selectivity for silphinene derivatives on chemoreceptors. The
changes from angelate to acetate or tiglate or isobutyrate as C-5 substitution induces a great
impact on the antifeedant potency. Esterification at C-5 with different substituents has strong
effect on the activity (e.g., 5α-acetoxysilfinen-3-one; see Chapter 7) (Reina et al., 2002).
Significant to moderate increase depending on the type of C-5 substituent (258-fold for ang.,
187-fold for tig., 4-fold for isobut., and 3-fold for Ac) has been demonstrated (Reina et al.,
2002). Importance of C-11 acetate has also been demonstrated and apparently the tricyclic
silphinene sesquiterpenes are good antifeedant candidates for future study.

MONOTERPENES
Many monoterpenes have been evaluated against insects to show feeding deterrence against
them (Koul, 1982). However, capillin (71), capillarin (72), methyl eugenol (73), and ar-
curcumene (74) isolated from Artemisia capillaris have a promise as antifeedant compounds
against cabbage butterfly larvae, Pieris rapae crucivora. The relative strong antifeedant
activity of capillin and capillarin suggest that C=O carbonyl group instead of CH2 methylene
group, a C ≡ C in a side chain, and a lactone ring are some of the many factors that contribute
to the biological activity (Yano, 1987). Various derivatives of these base compounds like
methyl eugenol reveal that the 3,4-dimethyl group and 1-substituent of 3,4-dimethoxy-1-
substituted benzenes (75) contribute to the antifeedant activity (Yano and Kamimura, 1993).
Similarly capillin structure has an aromatic carbonyl group and two C ≡ C bonds. In order
to demonstrate the importance of these two functions for the candidate activity, various
derivatives evaluated against P. rapae crucivora reveal that arylmethyl ketone with a CH3
group (76), instead of an H atom combined with C = O group of aromatic aldehyde, is more
active than that of aromatic aldehyde (Yano and Tanaka, 1995). Also a relationship between
antifeedant activity using phenyl alkynes suggests that C ≡ C triple bond in the side chain is
associated with antifeedant activity. It has also been observed that terminal groups (R) of
side chain of C6H5-C≡C-R influences activity considerably, and the intensity of activity of
various compounds shows a reasonable trend (77). This suggests that charge separation of
C ≡ C triple bond by electron donative effect of alkyl group combination with C ≡ C bond
may be correlated with an increase in antifeedant activity, and that a carbon chain enlargement
of the alkyl group results in a decrease of antifeedant activity, probably because of the
stereochemical hindrance (Yano, 1986).

OCH3

OCH3

O CH2

(71) (72) (73)

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Insect Antifeedants 59

OCH3

OCH3

C=O R = CH3

R R

(74) (75) (76)

> >
>

>

(77)

It has also been established that the 3,4-dimethoxy group and the 1-substituent of
3,4-dimethoxy-1-substituted benzenes related to methyl eugenol contribute to the activity. As
for aromatic carbonyl compounds related to capillin, arylmethylketones [Ar – C(CH3)=O]
became more active than aromatic aldehydes [Ar–C(H)=O], when an H atom of aldehyde
group of aromatic aldehydes was replaced with a CH3 group (Yano, 1998).

COUMARINS
Inhibitory activity of feeding by coumarins isolated from Atlanta recemosa and other related
species against Spodoptera litura larvae have made it possible to draw some structural patterns
for the said activity in this class of allelochemicals. Xanthotoxin (78) is known from decades
to induce inhibitory effects in insects and accordingly has been shown to deter feeding as
well (and so has its derivatives). Amongst these, xanthotoxol ethyl ether (79) has shown the
highest feeding inhibition. Demethylated products like xanthotoxol (80) and its acetate (81)
totally lack activity. Methyl and ethyl ethers of rutaretin (82), which are 2-(α-hydroxyiso-
propyl) dihydrofurano analogues of xanthotoxin are also inactive. Similarly 2-isopropylex-
anthotoxin (83) and its ethyl analogues (84) are also inactive (Luthria et al., 1989).

OCH3 OC2H5 OH

O O O O O O O O O

(78) (79) (80)

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60 Opender Koul

OAc OH OR
R = CH3
O O O O O O
or

R = C2H5

(81) (82)

OCH3 OC2H5

ipr O O O ipr O O O O O O

(83) (84) (85)

OCH3

O O O
OCH3

O O O O
O O

OCH3

(86) (87) (88)

OCH3

O O O R1

RO O
O O O

OCH3 R2

(89) (90) (91)

Psoralen (85), which has a linearly fused furan ring like xanthotoxin but lacks a methoxyl
group, is moderately active. However, its isomer angelicin (86), with an angularly fused furan
ring, shows several-fold reduction in activity. Isopimpinellin (87), which has an additional
methoxyl group at C-4, is sixfold more active than the former compounds. An interesting
observation is the least activity in luvangetin (88), racemosin (89) and xanthyletin (90), which
are corresponding pyrano-analogues of xanthotoxin, isopimpinellin, and psoralen respec-
tively. Substituted coumarins like umbelliferones (91) without furano and pyrano moieties
are also inactive (Luthria et al., 1989). The conclusions that can be drawn from the compar-
isons are:

• A linearly fused furan ring along with alkoxy groups at positions 4 and 9 play an
important role in determining antifeedant activity.
• A substituent in the furan ring causes a loss of antifeedant activity.

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Insect Antifeedants 61

A series of 3-acyl-4-hydroxy coumarins structurally related to dicoumarol are also known


to induce feeding inhibition in insects (Dreyer et al., 1987). It has been suggested that increase
in 3-acyl group size in such compounds decreases the activity. These compounds are known
antibacterial agents against gram positive bacteria but inactive against gram negative bacteria
(Toda et al., 1958).
Similar studies on furochromones have revealed some distinctive features responsible for
antifeedant activity against insects (Luthria et al., 1993). The assumptions made on the basis of
activity suggest that substitution at C-2 lowers the actviity (92 versus 93). Saturation of the
2,3-double bond as in 2,3-dihydronomellin (94) also diminishes the activity compared to that
of khellin (95). Absence of cleavage of the furan ring results in drastic reduction in activity,
which is evident from the reduced activity in chromones (96) and chromonones (97). Changes
at the substituents at the pyrone ring (C-7 position) reduces activity. Thus compounds 98 and
99, which contain a CH2OH group at C-7 and are analogues of 92 and 95, are significantly
active. The furanoflavones (100), the aryl analogues of 95, also do not show any significant
antifeedant activity.

O O Ac O O
2

>

CH2 CH3O O

(92) (93)

OCH3 OCH3

O O O O
2

3
<

OCH3 OCH3 O

(94) (95)

R4
R3 R2
O R O

R2
R1

R1 O R O

(96) (97)

Similarly, benzofurans (101) obtained by the cleavage of the γ-pyrone rings of 95 and
92 do not deter feeding of the larvae, and saturation of the the 6,7 double bond of the pyrones
causes reduction in activity (102). Thus an intact pyrone ring seems to be essential with
methyl substitution at C-7 for inducing a potential feeding deterrence.

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62 Opender Koul

OCH3

O O CH2OH O O CH2OH

OCH3 O OCH3 O

(98) (99)

OCH3
OCH3

O O
R1

R2

OCH3 O

(100)

R1 OCH3 OCH3

OH 1 O O
O O O
2 7
3 6
R2 4 5

OCH3 OCH3 O OH O

(101) (102) (103)

OCH3
OH
O 9 O
O O O O

O O
OH O OH O

(104) (105) (106)

Another interesting aspect of the structure-activity relationship of these compounds is


the alkoxy groups on the aromatic ring. Complete or partial dealkylation of compounds 95
and 92, as in compounds 103, 104, and 105, causes total loss of activity. On the other hand
synthetic ethyl ether derivative (106) shows increased activity compared to the natural product
(Luthria et al., 1993). A number of naturally occurring benzofurans that differ in their
substitution pattern and oxidation state have been investigated for their ability to inhibit the
feeding of third-instar larvae of common cutworm, Spodoptera litura, in a leaf disk bioassay.
The introduction of methoxy and acetyl groups increased antifeedant activity. Insect anti-
feedant activity also increased with decreasing lipophilicity of the test compounds (Morimoto
et al., 1999).

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Insect Antifeedants 63

Overall analysis of the activity suggests that among furanochromones the presence of an
unsaturated furan ring and an alkoxy substitution at positions C-4 or C-9 are essential for
antifeedant activity. Also both heterocyclic (furan and pyran) rings are essential. Cleavage or
saturation of either of the heterocyclic rings as well as replacement of C-7 methyl diminishes
the activity.

ISOFLAVONOIDS
A comprehensive study against Costelytra zealandica using various naturally occurring isofla-
vonoids of different substitution patterns and oxidation states reveals that these compounds
are significantly active in the range of 0.2 to 1.0 µg/g level (Russel et al., 1978; Lane et al.,
1985). Out of 36 isoflavonoids including optical isomers, 18 are active antifeedants. Phaseolin
(107) (and related compounds with a cyclic isoprenoid unit fused to ring B) and rotenone
(108) are particularly active with a significant effect on feeding. The deterrent activity is not
restricted to a particular isoflavonoid class. While all the pterocarpins (like 107) show feeding
deterrence, none of the coumestans (109) are active. Similarly isoflavans, isoflavones, and
isoflavonones belong to both active as well as inactive categories (Lane et al., 1985).

HO 7 O
2 O O
A C O
6 3 6' A C D
1' 2'
5 4 5' 1'
D B 3'
O 4' B
2' 6' 4'
3' O O
5' OCH3
α
β OCH3
(108)

(107) (108)

HO O
R O O

R1

O RO O
OH

R = OH, R1 = H or R = H, R1 = OH R = H or R = CH3

(109) (110)

Two structural features that are characteristic of most of the highly active isoflavonoid
feeding deterrents are:

• The presence of 2′-oxy function.


• The occurrence of a 2,2-dimethyl-1, H-pyran (cyclic isoprenoid group) fused to
ring B (107, 110).

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64 Opender Koul

There is a difficulty of comparing inactive compounds with those of the marginal activity.
However, the balance of evidence supports the view that the difference in activity between
2′-deoxy compounds and their 2′-oxy counterparts is real. Several inactive or marginally
active compounds do contain 2-oxy function (109, 111, 112), and the contrast between the
inactivity of the coumestans (109) and the active pterocarpins (107) suggests that 2′-oxygen-
ation is a feature of all the active feeding deterrents of this class, but its occurrence does not
correlate with activity.

HO O

HO O OH O
HO OH

H3CO OCH3

(111) (112)

Recent studies with flavonoids against termites have revealed some basic requirements
in a structure-activity relationship. It was found that compounds containing two hydroxyl
groups at C-5 and C-7 in A-rings showed high antifeedant activity. Furthermore, the presence
of a carbonyl group at C-4 in the pyran rings of the compounds was necessary for the
occurrence of high activity. 3-Hydroxyflavones and 3-hydroxyflavanones with 3',4'-dihydrox-
ylated B-rings exhibited higher activity than those with 4'-hydroxylated B-rings (Ohmura et
al., 2000).

ALKALOIDS
Various alkaloids have been evaluated in insect herbivore relationships (Levinson, 1976) and
possess considerable toxicity and phagodeterrency effects against variety of organisms (Levin,
1976). Insect larval feeding deterrence due to pyrrolizidine alkaloids, lupine alkaloids, and
solanum alkaloids (Chapter 7) is well known (Bentley et al., 1984a, 1984b, 1984c). However,
from the structure-activity relationship point of view there is a wide variation in feeding
response to alkaloids in different species of insects. Even in the studies against the same
species, like spruce budworm (a species with a rather narrow range of coniferous host plants
that do not contain glycoalkaloids; therefore, a fortuitous choice of a test insect), it is still
difficult to generalize any functionalities responsible for activity in these compounds. What
has been postulated is that at least with alkaloids, the evolution of host–herbivore interactions
may be a function of the class of alkaloids present or of nonchemical selective factors (Bentley,
1984c). However, in case of lycorine alkaloids, increase in nucleophilicity attributes to
increased activity (Evidente et al., 1986) and an undissociated phenolic group leads to a
marked decrease in activity. The insect antifeedant activity of the Delphinium diterpene

© 2005 by CRC Press LLC


Insect Antifeedants 65

alkaloids, 15-acetylcardiopentamine and cardiopentamine, are known to inhibit feeding of


Spodoptera littoralis and Leptinotarsa decemlineata (Gonzalez-Coloma et al., 1998). Struc-
ture-activity studies point to C-13 and C-15 hydroxy substituents as essential features of the
active molecules against S. littoralis, but C-13 hydroxy or C-15 acetate as responsible for
feeding inhibition in L. decemlineata. This again implies that species-specific structural
functionalities in a molecule determine their antifeedant activity.

MAYTANSINOIDS
Powell et al. (1981, 1982) isolated a series of biologically active maytansinoids from ethanolic
extract of Trewia nudiflora L. (Euphorbiaceae), of which trewiasine (113) is the most abun-
dant. These compounds are unique in that they contain a 15-methoxyl group, thus far found
only in maytansinoids from Trewia. Moreover, some of these also contain two fused macro-
cyclic rings, as in treflorine (114).

O H

O
HO C C N CH
O
N CH
O
O Cl CH2 O
Cl O O

H3CO O
H3CO O N
N 1 3 5
18 2 4 6
17 7
O
16 8 O

15 13 11 9
10 N O
14 12 N O H3CO
H3CO
OH
OH
OCH3
OCH3

(113) (114)

In addition to the 19-membered ring characteristic structure, a 12-membered ring joining


C-3 and the amide nitrogen at C-18 have been identified (Madrigal, 1985). These compounds
inhibit feeding in the corn borer, Ostrinia nubilalis. The correlation among structures suggest
that unique maytansinoid ring system, the hydroxyl at C-3 esterified with an amino acid, is
essential for activity. A methoxyl group at C-15 seems to make little difference. However,
more comprehensive study of such compounds is required to bring forth genuine conclusions.

ELLAGITANNINS
Feeding-deterrent activity of ellagic acid (115), ellagitannin (116), gallic acid (117), geraniin
(118), and several gallic acid derivatives towards various aphid species have revealed some
structural basis for the activity (Jones and Klocke, 1987). Ellagitannins are characterized by
the tanning property of forming hydrogen bonds between the phenolic hydroxyls of the tannin
and the free amino and amide groups of proteins (McManus et al., 1983). This property has
been hypothesized to be responsible for feeding deterrence in insects (Swain, 1979; Rhoades
and Cates, 1976).

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66 Opender Koul

OH

HO O O HO O
COOH

O O OH HO OH HO OH

OH OH OH

(115) (116) (117)

HO OH HO OH

HO OH
O O
HO
O
O
O O

HO
O O
O O
OH
O

OH
HO
O
HO O
OH
OH

(118)

Ellagic acid, formed by oxidative coupling of two molecules of gallic acid, is tenfold
more active as a feeding deterrent against Schizophis graminum than the gallic acid itself.
A free ortho-hydroxyl group in gallic acid is important for deterrent activity, but esterfi-
cation of its carboxyl group with alkyl chains of increasing length results in increased activity.
Thus there is considerable increase in activity from methyl gallate (119) and n-propyl gallate
(120) to n-octyl gallate (121) and n-decyl gallate (122); the latter is as active as ellagic acid
(Jones and Klocke, 1987).

COOCH3 COOCH2CH2CH3 CH3(CH2)9OOC


COO(CH2)7CH3

HO OH HO OH HO OH HO OH

OH OH OH OH

(119) (120) (121) (122)

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Insect Antifeedants 67

ARISTOLOCHIC ACIDS
The antifeedant activity of the metabolites of Aristolochia albida root extracts against S. litura
larvae (Lajide et al., 1993a) is due to aristolochic acids (123). While 6-hydroxy aristolochic
acid (128) is moderately active, aristolic acid (124), aristolactam (125), and aristolone (126)
are inactive up to 0.1% treatment level. The synthetic analogues like methyl aristolochiate
(127) and methyl-6-hydroxy aristolochiate (127) are lower in activity than parent compounds.
Decarboxylation of parent acid also results in decreased activity. On comparing aristolochic
acids, phenanthrene and 1,3-benzodioxole derivatives (Lajide et al., 1993b), aristolochic acids
(123, 124) are most potent. Of the phenanthrene analogues, only phenanthridine (129) has a
significant activity against S. litura larvae.

2
3 1 COOH COOH
O O O
NH
10 NO2
O 4 O O

9
5

6 8
OCH3 OCH3 OCH3
7

(123) (124) (125)

O COOCH3
O COOH
NO2
O
NO2
O O

R OCH3
R = H or R = OH HO OCH3

(126) (127) (128)

These observations reveal that the location of a –COOH group in close proximity to an
–NO2 group is essential for activity, and the modification of the –COOH group results in
reduced activity. In the series of aristolochic acid derivatives it is suggestive that more oxidized
or unsaturated structures are efficient antifeedants. Such oxidized or unsaturated compounds
like p-benzoquinones against p-hydroquinones (Chapter 7) are also known potential antifeed-
ants (Norris, 1986).
However, on analyzing the structures for specific structural features no single factor
emerges predominantly among the compounds tested for antifeedant activity against S. litura
larvae. Antifeedant activity seems to be strongly reduced upon modification of natural aris-
tolochic acid structure, in particular the carboxylic acid group. The compounds that possess
the ability to form reactive quinone intermediates such as (130, 131), as well as phenanthrene,
are quite toxic, suggesting different mechanism of action and different molecular targets
(Lajide et al., 1993b).

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68 Opender Koul

NO2
N O

O H

O NO2

(129) (130) (131)

The above discussion, therefore, clearly implies that there seems to be an inherent
difficulty with respect to drawing meaningful generalized quantitative structural-activity
relationship profile vis-à-vis the antifeedant activity. The basic explanation for this in part
could be attributed to interspecific differences among bioassay organisms, i.e., use of insect
growth stages, diversity of bioassays, and variations in the modes of application. Despite all
these impediments, the above discussion has brought to the fore some specific relationships
in basic skeletons that suggest that changes in substitution patterns, oxidation state, hydro-
phobicity, molecular connectivity, electrostatic potential, conformation, and distance geom-
etry play a significant role in influencing the antifeedant activity of the compounds.

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© 2005 by CRC Press LLC


5 COMMERCIALIZATION
The present state-of-the-art situation of insect antifeedants, from a commercial point of view,
indicates that such chemicals have not really made headway on a large scale because of the
lack of technology to produce them in sufficient quantity and the time-consuming and labor-
intensive procedures to prepare them. Therefore, in spite of the wide recognition that many
allelochemicals possess potential insect control properties, only a handful are in use in some
parts of the world. At best, botanical insecticides constitute 1% of the world insecticide
market, but annual sales growth in the range of 10 to 15% is entirely possible. The impact,
however, in the range of 25% market share within 5 years, has been envisaged in the home-
and-garden sector (Isman, 1997).
Among more than 800 insect antifeedant compounds known today (Chapter 7) only the
compounds from neem, Azadirachta indica, have shown commercial potential; quite a few
products are in the market that have met regulatory requirements and received firm or
provisional registrations. The overall picture makes one surmise that commercial neem
products have gained greater significance in the Indian subcontinent, where there are com-
mercially marketed products for virtually all types of usage. Many products occupy a large
share of the market, e.g., neem-based soap, toothpaste, pesticides, and fertilizers (Koul, 1996).
In all other countries, commercial neem products count for only a modest share of the market.
Throughout the world, in those countries where neem trees are grown, the prices for dried
seeds are between U.S. $0.10 and $2.00 per kg. To effectively control most pests, one hectare
of crops must be treated once with between 20 and 60 g of the main active ingredient,
azadirachtin. Thus, given the fact that there are approximately 2 g of azadirachtin per kg of
seeds on an average, somewhere between 10 and 30 kg of neem seeds are needed in all. This
means that the seed costs alone for the single treatment of one hectare of crops are between
U.S. $1.00 and U.S. $60.00, although in most countries they are somewhere in the narrower
range between U.S. $5.00 and U.S. $20.00 (Status Report on Global Neem Usage, 2000).

© 2005 by CRC Press LLC


74 Opender Koul

COMMERCIAL NEEM INSECTICIDE PRODUCTS


BY COUNTRIES or REGIONS, IN % OF THE
RESPONSES FROM THE GIVEN REGIONS
Asia 71%
Africa 38%
Caribbean/Latin America 50%
Industrialized Countries 100%

An additional factor when calculating the cost of manufacturing formulated, neem-based


pesticides are the costs of extraction, which means that production of this kind is most
probably only profitable in those countries with low seed prices. However, these costs decrease
in relation to the quality of pesticides produced. For instance, according to the estimates of
Neem Foundation (2003), environmental service rendered by neem tree at $10 per month,
would yield a value of U.S. $24,000 to $36,000 in its 200- to 300-year lifetime. Further, the
alternative uses in organic agriculture (like fertilizer) and medicinal products give commer-
cialized neem huge economic potential. However, it is to be seen how exclusive rights to
produce and export botanical biopesticides are going to be handled globally; this has tremen-
dous legal implications. So it is to be seen what happens in 2005 when the real effects of
TRIPS (Trade Related Intellectual Property Rights) will be felt. When assessing the economic
efficiency of neem, it is important not to forget that other secondary products can be obtained
from the tree, which not only constitute additional biological activity potential but also their
own marketing right. Present status of commercial neem-based pesticides on the market and
their respective registration status is given in Table 5.1.
However, apart from neem products, there are few actual demonstrations of antifeedant
efficacy in the field. Application of polygodial or methyl salicylate at the IARC-Rothamsted
showed that aphid populations are reduced with concomitant increases in yields of winter
wheat, in one case comparable to that achieved with the pyrethroid insecticide cypermethrin
(Pickett et al., 1997). Similarly, toosendanin, an antifeedant limonoid from the bark of the
trees Melia toosendan and M. azedarach (Meliaceae), has been subjected to considerable
research as a botanical pesticide (Chiu, 1989, Zhang et al., 1992, Chen et al., 1995, Koul et
al., 2002). Vertebrate selectivity of this compound is very favorable (LD50 mice = 10 g/kg)
(Isman, 1994). Production of a botanical insecticide based on toosendanin, using a refined
bark extract containing approximately 3% toosendanin (racemic mixture) as the active ingre-
dient, has recently begun in P.R. China (Zhang et al., 1992). This could become a potential
commercial product worldwide, as formulations based on the technical concentrate are under
evaluation in Canada to assess its potential against pests of agriculture and forestry in North
America. Triphenyltin acetate, used as a fungicide, algicide, and molluscicide, had shown
potential for use as a crop protectant against lepidopteran pests through antifeedant action,
but this pesticide has fallen from favor owing to environmental concerns (Perry et al., 1998).
At this stage it is imperative to know that, in spite of the wide recognition that many
plants possess antifeedant compounds, only neem allelochemicals have made some impact.
The reason is that neem allelochemicals apparently have admirably met most of the criteria
for useful pest control agent as compared to other isolated compounds from various plants.
Still, the commercialization of neem products for use in North America and Europe has taken
many years, incurring the cost in millions of U.S. dollars. Obviously, in addition to being an
efficacious and safe product, there are apparently other considerations required to be satisfied
in order to compete with conventional pesticides. In fact, the commercialization of new
feeding deterrents is hindered by three basic factors:

© 2005 by CRC Press LLC


Insect Antifeedants 75

• Limitations in natural resources


• Quality control and standardization
• Regulatory constraints

From a commercial point of view it is very essential to have an abundance of starting


material, which can meet market demand on a consistent basis. The main aim is to obtain
sufficient biomass for extraction or subsequent isolation of pure active ingredients. Therefore,
it is very essential to get such material through cultivation or plantation of such trees, as has
been established in the case of neem in Australia, Brazil, Kenya, Philippines, and so on. It
is very useful to have a source of biomass in a convenient fashion such as seeds, because it
is easy to collect and process them. This has been achieved in the case of neem (Koul, 1996),
citrus fruit seeds (Klocke and Kubo, 1982), and Annona seeds (McLaughlin et al., 1997).
Tissue culture technique is a useful procedure for obtaining bioactive products on a large
scale. There are a number of plants that have been subjected to this technique for obtaining
bioactive materials (Koul, 1996; Koul and Wahab, 2004) but only the substantial success in
terms of feeding deterrents is azadirachtin, where cell suspension cultures have produced
azadirachtin in good yields (Holowach et al., 1994).
The second important hindrance is that of standardization and quality control. Standard-
ization of active ingredients in natural products has several constraints, particularly:

• Ecotypical differences for the same species that influence active ingredients
• Activity due to complex mixtures
• Synergistic action of co-occurring toxins within a natural mixture

These factors affect the standardization of a material considerably and are well evidenced
in many compounds like pyrethrins, rotenones, isoflavonoids, azadirachtins, and toosendanins
(Isman, 1997). However, complex mixtures could be advantageous, too, from pest resistance
and behavioral desensitization points of view. Regulatory requirements for active ingredient
specifications are a must, but very difficult to achieve in case of mixtures. That is why in
neem-based formulations, quantification of azadirachtin A and azadirachtin B is a minimum
requirement under regulatory measures, although other active ingredients such as salannin
and others (Koul, 1992) are also the components of such formulations.
Regulatory requirements are essential for the commercialization of a product and thus
applicable to feeding deterrents as well. Neem-based products have been successful to some
extent in obtaining registration for a number of formulations in various parts of the world
(Table 5.1). However, the registration of a new feeding deterrent is a tough task because most
of the regulatory parameters are based specifically around synthetic chemicals. Some orga-
nizations ask for toxicological data for every characterized active component, which will cost
millions of dollars. However, some solace comes from the actions taken in Canada by the
Pest Management Regulatory Agency, which approved an experimental use permit allowing
the aerial application of neem to control forest-defoliating sawflies based on HPLC analysis
of the neem concentrate (in which the major ten limonoids, accounting for 90% of the
UV-visible material, were identified and quantified) (Isman, 1997). In North America, this
“reduced risk” pesticide category identified through product identicality has been emphasized
every time it is manufactured.
Because the large multinationals have no serious interest in the development of non-
persistent nature-based biological pesticides (like feeding deterrents), commercialization of
such products is mainly taken by small manufacturers. In fact in India to achieve this goal,
provisional registrations have been given to manufacturers, and the products are being sold

© 2005 by CRC Press LLC


76 Opender Koul

TABLE 5.1 Commercial Neem-Based Pesticides in Various Countries


Country Number of products Status

Australia 2 About to be registered


Austria 3 Registration for eco-cropping
Benin 1 Unclear
Brazil Unclear Imported from Germany
Canada 1 Temporary registration for forest pests
China 1 Provisional registration
Colombia 3 Unclear
Costa Rica 2 Registered
Cuba 3 Registered
Denmark 2 Under registration
Dominican Republic 3 Registered
Dutch Antilles 2 Registered
Ecuador 4 Unclear, imported from U.S.
Egypt 5 Registered, imported from Germany and Sweden
Fiji 1 Registered
Germany 5 Registered and offered as raw material
Ghana 3 Provisional registration, imported from India, U.S.
India ~100 Limited number of products registered
Indonesia 1 Registration pending
Israel 3 Registered and imported from U.S.
Italy 2 Registered products from India and Germany
Kenya 8 Variable registration status, imported from India and U.S.
Mauritius 1 Registered and imported from India
Myanmar 3 Registered
Nepal 1 Registered and imported from India
Nicaragua 4 Registered
Niger 2 About to be registered
Pakistan 2 Unclear
Saudi Arabia 4 Registered, imported from U.S.
Senegal 2 Provisional registration
Spain 2 Registered formulated products
Sri Lanka 2 Registered products from India, local unclear
Sweden 2 Registered
Switzerland 3 Registered for fruit crops, offered as raw material
Thailand 3 Registered
Togo 2 Registration not required
Uganda 2 Registered, imported from Kenya
U.S. 5 Registered
Venezuela 3 Unclear, imported from U.S.

Modified from Status Report on Global Neem Usage (2000), GTZ, Germany.

in the market. However, it becomes imperative for producers to fulfill the requirements within
the stipulated time frame, as provided by the regulatory authorities. I believe that Western
countries should adopt this policy, if biological pesticides are to make any impact in the near
future in the conventional insecticide market. Neem has already provided a modern paradigm
for the development of biopesticides, and others have to follow the direction.
Another operational problem specific to antifeedants is the potential for insects to rapidly
desensitize (habituate) to a feeding deterrent. Several investigations have demonstrated that
individual (naïve) insects initially deterred by an antifeedant become increasingly tolerant

© 2005 by CRC Press LLC


Insect Antifeedants 77

upon repeated exposures or through continuous exposure. Under no-choice conditions, feed-
ing by tobacco cutworm larvae on cabbage disks treated with azadirachtin was initially
deterred by 90%, but with continuous exposure, the response had waned by more than one
half within 5 hours (Bomford and Isman, 1996). With another insect antifeedant, toosendanin
from Melia toosendan (Chiu and Zhang, 1987) and Melia azedarach (Koul et al., 2002),
feeding deterrence was completely abolished at 4.5 hours (Isman, 2002). This implies that a
crop treated with an antifeedant might only enjoy protection from a pest for a few hours
before the insect becomes habituated and can then feed with impunity. This also shows that
caterpillars can become habituated to a variety of plant secondary metabolites, and impor-
tantly, they can become cross-habituated (Isman, 2002). However, use of mixtures could help
in mitigating the habituation process in insects, by presenting mixtures of antifeedants. Recent
studies have shown that mixtures of compounds play a significant role in the activity within
a plant system (Koul et al., 2003). It is also well documented that Spodoptera litura larvae
could habituate to pure azadirachtin, but less so to a neem extract containing the same absolute
amount of azadirachtin (Bomford and Isman, 1996).
In conclusion, given the aforementioned limitations to the use of insect antifeedants
(differences in response between pest species, potential desensitization of pests, and rapid
environmental degradation), it is most unlikely that an antifeedant will emerge with sufficient
field efficacy to act as a standalone crop protectant. According to Isman (2002), assuming
that there are insect antifeedants (i) with minimal bioactivity in mammals and other non-
target organisms, and (ii) are available on a commercial scale, there are likely specific
crop–pest combinations where an antifeedant can play a significant role as part of an integrated
pest management system. Whether the market(s) for such a specific protectant can justify the
costs of development remains to be seen. Ongoing research into insect sensory systems,
neuropharmacology, and organic chemistry may ultimately mitigate the limitations to anti-
feedants observed at present and lead to a suite of new crop protectants based on deterrence
of insect feeding and oviposition.

REFERENCES
Bomford, M.K. and Isman, M.B. (1996) Desensitization of fifth instar Spodoptera litura to
azadirachtin and neem. Entomol. Exp. Appl., 81, 301–313.
Chen, W., Isman, M.B., and Chiu, S.-F. (1995) Antifeedant and growth inhibitory effects of
the limonoid toosendanin and Melia toosendan extracts on the variegated cutworm,
Peridroma saucia (Lep., Noctuidae). J. Appl. Ent., 119, 367–370.
Chiu, S.-F. (1989) Recent advances in research on botanical insecticides in China. In J.T.
Arnason, B.J.R. Philogene, and P. Morand (eds.), Insecticides of Plant Origin, ACS
Symp. Ser. 387, Am. Chem. Soc., Washington, D.C., pp. 69–77.
Chiu, S.-F. and Zhang, X. (1987) A critical review of toosendanin, a novel insecticide isolated
from Melia toosendan Sieb. et Zucc. (Meliaceae). J. South China Agric. Univ., 8,
57–67.
Holowach, K., Lorraine, P., Birman, I., and Patterson, D.R. (1994) A method for producing
azadirachtin. Eur. Patent EP 605139, 21 pp.
Isman, M.B. (1994) Botanical insecticides. Pestic. Outlook, 5, 26–31.
Isman, M.B. (1997) Neem and other botanical insecticides: Barriers for commercialization.
Phytoparasitica, 25, 339–344.
Isman, M.B. (2002) Insect antifeedants. Pestic. Outlook, 13, 152–157.
Klocke, J.A. and Kubo, I. (1982) Citrus limonoid by-products as insect control agents.
Entomol. Exp. Appl., 32, 299–301.

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78 Opender Koul

Koul, O. (1992) Neem allelochemical and insect control. In S.J.H. Rizvi and V. Rizvi (eds.),
Allelopathy: Basic and Applied Aspects, Chapman & Hall, London, pp. 389–413.
Koul, O. (1996) Natural product leads as anti-insect compounds: Prospects for biotechnology.
In T.N. Ananthakrishnan (ed.), Biotechnological Perspectives in Chemical Ecology of
Insects, Oxford & IBH Publishing Co. Pvt. Ltd., New Delhi, pp. 15–27.
Koul, O. and Wahab, S. (2004) Neem: Today and in the New Millennium, Kluwer Academic
Publishers, The Netherlands.
Koul, O., Multani, J.S., Singh, G., and Wahab, S. (2002) Bioefficacy of toosendanin from
Melia dubia (syn. M. azedarach) against gram pod-borer, Helicoverpa armigera
(Hubner). Curr. Sci., 83, 1387–1391.
Koul, O., Multani, J.S., Singh G., Daniewski, W.M., and Berlozecki, S. (2003) 6β-Hydrox-
ygedunin from Azadirachta indica, its potentiation effects with some non-azadirachtin
limonoids in neem against lepidopteran larvae. J. Agric. Food Chem., 51, 2937–2942.
McLaughlin, J.L., Zeng, L., Oberlies, N.H., Alfonso, D., Jhonson, H.A., and Cummings, B.A.
(1997) Annonaceous acetogenins as new pesticides: recent progress. In P.A. Hedin,
R.M. Hollingworth, E.P. Masler, J. Miyamoto, and D.G. Thompson (eds.), Phytochem-
icals for Pest Control, ACS Symp. Ser. 658, Am. Chem. Soc., Washington, D.C., pp.
117–133.
Neem Foundation (2003) www.neemfoundation.org.
Perry, A.S., Yamamoto, I., Ishaaya, I., and Perry, R.Y. (1998) Insecticides in Agriculture and
Environment. Springer Verlag, Berlin.
Pickett, J.A., Wadhams, L.J., and Woodcock, C.M. (1997) Developing sustainable pest control
from chemical ecology. Agric. Ecosyst. Environ., 64, 149–156.
Status report on global neem usage (2000) Deutsche Gesellschaft fur Technische Zusamme-
narbeit (GTZ), Eschborn, Germany.
Zhang, X., Wang, X.-L., and Chiu, S.-F. (1992) Studies on the bioactivities and applications
of Chinese botanical insecticide: toosendanin. XIX Intl. Congr. Entomol., Beijing,
abstracts, p. 570.

© 2005 by CRC Press LLC


6 PRACTICAL APPLICATIONS
AND CONCLUSIONS
The use of antifeedants in pest-management programs has enormous intuitive appeal. They
satisfy the need to protect specific crops while avoiding damage to non-target organisms, so
that potential value is very great. In fact, insect damage to plants results from feeding or from
transmission of pathogens during feeding; therefore, the chemicals that reduce pest injury by
rendering plants unattractive or unpalatable can be considered as potential substitutes for
conventional insecticides. Programs have been launched in several countries for developing
feeding deterrents known to occur naturally in plants (Saxena, 1987); killing and destruction
of pests is not always necessary if using antifeedants can incapacitate them.
According to Jermy (1983), research on the practical use of antifeedants of plant origin
should consider:

• The wide capability of the chemosensory mechanism governing feeding behavior


in polyphagous insects
• The complexity of the inhibitory biochemical profile of plants deterring a given
insect species
• The difference of these profiles in relation to different insect species
• The variation in feeding behavior of different populations of the same insect species
• The changes of plant constituents in time and space (polychemism)
• The problem of formulation of antifeedants for plant protection purposes

The question, therefore, is, What have we achieved in terms of research in this relatively
new and promising field? When we look at the role of antifeedants in pest management

© 2005 by CRC Press LLC


80 Opender Koul

strategies, the answer is quite deplorable that only a few allelochemicals have been subjected
to large-scale field experimentation to prove the practicability of such approaches. However,
the outcome of many studies is that there is increasing interest in the use of insect antifeedants
against agricultural pests, but their effects are often short lived, either because the compounds
themselves are non-persistent or because, after a period of starvation, insects habituate to
such materials. This aspect has been very well demonstrated in neem and azadirachtin studies.
For instance, in a very recent study the deterrence of azadirachtin, in its pure form and as a
constituent of neem seed extract, to fifth instar Spodoptera litura larvae has been measured.
The effects of hunger and habituation on desensitization have been demonstrated. After
repeated exposure, larvae become desensitized to pure azadirachtin in both choice and no-
choice tests. Hunger was responsible for approximately one third of the desensitization
response (Bomford and Isman, 1996).
This means that new strategies have to be devised that allow for possible changes in
insect behavior. The future for the use of antifeedants in crop protection lies in their integration
into pest management programs, in combination with other agents of control.
In a study the insect growth regulator teflubenzuron, which acts by the oral route and is
relatively inactive as an antifeedant against mustard beetles or diamond back moth larvae,
has been used in a similar program. Two methods of combining the use of teflubenzuron
with insect antifeedant have been studied (Griffiths et al., 1991). The strategy of applying
the antifeedant and growth inhibitor together relies on stopping the overshoot in feeding that
occurs when the insects are poisoned by teflubenzuron. The insect needs to eat < 1% of the
leaf disk to acquire a toxic dose but, in the absence of an antifeedant, it eats > 40% even at
the highest doses, during the lag phase that occurs between treatment and effect. In laboratory
conditions, the combination of antifeedant with teflubenzuron decreased feeding damage by
Plutella xylostella and Phaedon cochlearae without diminishing the toxic effect (Griffiths et
al., 1991).
In the alternative strategy teflubenzuron and antifeedant were applied separately. Treat-
ment of the growing tips of mustard plants with antifeedant forced insects down the plant to
the lower leaves, where they were killed by diflubenzuron. Manipulation of insect populations
in this way now forms part of various insect control studies, such as the stimulo-deterrent
diversionary cropping strategy (Miller and Cowles, 1990) and the push pull strategies
described by Pyke et al. (1987).
In terms of toxicological aspects the most important aspect of practical application is
mammalian toxicity. It is theoretically possible to find antifeedants lacking any harmful effects
to humans, such as Margosan-O (Larson, 1987), mint compounds, and quinine (Jermy, 1990).
Unfortunately, for the known plant antifeedants, reports regarding mammalian toxicity are
mostly lacking (see Chapter 7). This may be due to the belief that secondary plant compounds
are of natural origin and highly degradable, and therefore pose lesser environmental hazards
than synthetic chemicals. Of course, this does not eliminate the safety procedures required
for new product development.
Persistence is another prerequisite for practical application. The persistence of metal-
organic antifeedants such as copper and tin fungicides is well known but persistence is largely
unknown for plant allelochemicals. Again detailed studies are known for neem products.
Stokes and Redfern (1982) have shown azadirachtin losing its antifeedant activity by more
than 50% in 7 days when exposed to sunlight. Ermel et al. (1987) showed that azadirachtin
was degraded to 50% in 12 days in greenhouse. Saxena (1987) lost the activity of neem oil
in 4 days in rice plants. Half-life of azadirachtin sprayed on conifer and deciduous foliage
was only 20 hours (Isman, 1997); however, exposure of neem insecticides on glass plate to

© 2005 by CRC Press LLC


Insect Antifeedants 81

light at one-quarter of intensity of sunlight (at the latitude of southern Canada) resulted in a
half-life for azadirachtin of 5 days (Sunderam and Curry, 1996). The half-life of azadirachtin
in normal soil at 25°C is 20 days, but is 31.5 days in autoclaved soil, indicating that organisms
are involved in its degradation (Stark and Walter, 1995). The persistence of antifeedants,
however, is affected by behavioral desensitization (Bomford and Isman, 1996); a generalized
model for quantifying the behavioral desensitization using lepidopteran larvae has been
developed (Raffa and Frazier, 1988). Along with the persistence, of course, it is important
that antifeedants do not have phytotoxic effects on the plants to be protected. Few secondary
compounds have been studied for their phytotoxicity, which indicates little or no phytotoxicity
(Schoonhoven, 1982), but it may be expected that several feeding deterrents will be toxic
because of their known allelopathic function.
Systemic action of antifeedants is another useful aspect of their practical application. On
one hand it will exert uniform distribution within the plant, and on the other it will counter-
balance the phagostimulatory effects of plant surface chemicals (Chapman and Bernays,
1989). The systemic action of neem extracts is well documented (Gill and Lewis, 1971; Abdul
Kareem et al., 1989; Osman and Port, 1990; Koul and Shankar, 1995). Thus gradual release
of neem compounds from neem seed powder incorporated in the soil and their gradual
translocation by plant gives neem a considerable persistence as a control agent.
Similarly extracts of Amora ruhituka and A. squamosa (Islam, 1987) have also been
shown to have systemic action. Coumarin is transported in grass leaves and thus unpalatable
to Chorthippus parallelus, and sinigrin is absorbed from water solution and transported to
stems and leaves of various plant species. However, if a promising antifeedant is to be
established for insect control, further investigations into systemic studies are unavoidable.
Antifeedant study is also dependent on monocomponent systems, testing single com-
pounds, which could sometimes be totally artificial. In fact, additive effects of antifeedant
compounds have been demonstrated against Locusta migratoria (Adams and Bernays, 1978).
In several cases, a plant containing a combination of antifeedants acts in unison to protect
itself from insect attack. Therefore, a mixture of compounds is likely to be more effective as
an antifeedant and accordingly quite useful in response to great interspecific variations among
insects. De facto, neem preparations have clearly shown this (Koul et al., 2003a, 2003b), and
Jermy (1990) rightfully suggested that comparative trials with simple antifeedant compounds
and with their combinations, especially under field conditions, are indispensable.
Lack of resistance is also very useful for practical application of antifeedants, as it is
unlikely that oligophagous insects could develop general resistance to such deterrents, because
this would result in rapid change of their host-plant range, which is determined mainly by
the occurrence of such chemicals in the non-host plants. Different molecular structures of
possible antifeedant compounds could be another advantage. However, permanent application
of a feeding deterrent may result in the development of resistance. This has been indicated
in the studies of selection of resistance to azadirachtin in the green peach aphid, Myzus
persicae (Feng and Isman, 1995). When two lines of this aphid were treated repeatedly with
pure azadirachtin, after 40 generations the AZA-selected line developed ninefold resistance
to AZA compared to a non-selected control line. Interestingly this type of resistance did not
develop in extract-treated (with same amount of AZA) insects. These results suggest that a
blend of active constituents might diffuse the selection process, mitigating the development
of resistance compared to that expected with a single active ingredient. This also supports
the earlier-mentioned contention that combination mixtures of antifeedants could be more
effective than individual compounds.

© 2005 by CRC Press LLC


82 Opender Koul

CONCLUSIONS
Most of the research to date on the antifeedant compounds has been motivated by the desire
to find useful compounds for specific agricultural applications. As a result bioassay designs
and choice bioassays have varied considerably. Many of the various types of structures of
antifeedants appear to be highly oxidized, with a variety of functional groups present in the
molecules. From the high level of activity of more than 800 antifeedant compounds, only
azadirachtin or neem preparations have made a real impact. Accordingly limited progress has
been made in this field, particularly from a commercial point of view.
Several aspects deserve more attention in order to implement use of antifeedants in
integrated pest management programs.

• Bioassays used should have close conformity with the field conditions.
• Extensive structure-bioactivity relationships combined with behavioral and elec-
trophysiological studies are required.
• Systemic action of antifeedants should be stressed, which could be highly useful
in pest control.
• Formulation aspects should be used strictly in laboratory conditions, so that there
is less variation from lab to field.
• Modes of action and influence on insect behavior and ecological systems should
be monitored closely.
• Phytochemistry studies should be continued and new or known antifeedants should
be isolated and identified with the right bioassay and phytotoxicity evaluation. In
fact, a combination of co-occurring molecules should be given priority for better
results.
• An alternative approach could be the introduction of antifeedant in the plant itself,
either by breeding experiments or by genetic manipulation. However, one has to
keep fingers crossed because such approaches could prop up new problems of
toxicity and resistance.
• Use of antifeedants with a synergist deserves attention.

On the whole, for a characteristic and ideal antifeedant for insect control, van Beck and
de Groot (1986) proposed a list of conditions that seem to be very appropriate for obtaining
a suitable insect feeding deterrent:

• They should be non-toxic to the ecosystem.


• They should not be phytotoxic.
• They should be as far as possible a generalistic antifeedant.
• They should be preferably also toxic against the same insect.
• They should be active at a very low concentration.
• They should be persistent when applied to crops.
• They should yield no toxic or bad-tasting metabolites.
• They should have systemic action.
• They should be easily applied.
• They should be low cost and supplied without disruptions.
• They should be compatible with other forms of pest management.
• They should not lead to habituation or resistance easily.
• They should be stable during storage, but biodegradable to some extent in field.

© 2005 by CRC Press LLC


Insect Antifeedants 83

REFERENCES
Abdul Kareem, A., Saxena, R.C., Boncodin, M.E.M., Krishnasamy, V., and Seshu, D.V. (1989)
Neem and seed treatment for rice before sowing. Effect on two homopteran insects
and seedling vigour. J. Econ. Entomol., 82, 1219–1223.
Adams, C.A. and Bernays, E.A. (1978) The effect of combination of deterrents on the feeding
behaviour of Locusta migratoria. Entomol. Exp. Appl., 23, 107–109.
Bomford, M.K. and Isman, M.B. (1996) Desensitization of fifth instar Spodoptera litura to
azadirachtin and neem. Entomol. Exp. Appl. 81, 307–313.
Chapman, R.F. and Bernays, E.A. (1989) Insect behaviour at the leaf surface and learning
as aspects of host plant relation. Experientia, 45, 215–222.
Ermel, K., Pahlich, E., and Schmutterer, H. (1987) Azadirachtin content of neem kernels
from different geographical locations and its dependence on temperature, relative
humidity and light. In H. Schmutterer and K.R.S. Ascher (eds.), Natural Pesticides
from Neem Tree and Other Tropical Plants, GTZ, Eschborn, pp. 171–184.
Feng, R. and Isman, M.B. (1995) Selection for resistance to azadirachtin in the green peach
aphid, Myzus persicae. Experientia, 51, 831–833.
Gill, J.S. and Lewis, C.T. (1971) Systemic action of an insect feeding deterrent. Nature
London, 232, 402–403.
Griffiths, D.C., Maniar, S.P., Merritt, L.A., Mudd, A., Pickett, J.A., Pye, B.J., Smart, L.E.,
and Wadhams, L.J. (1991) Laboratory evaluation of pest management strategies com-
bining antifeedants with insect growth regulator insecticides. Crop Protection, 10,
145–151.
Islam, B.N. (1987) Use of some extracts from Meliaceae and Annonaceae for control of rice
hispa, Dicladispa armigera and pulse beetle, Callosobruchus chinensis. In H. Schu-
mutterer and K.R.S. Ascher (eds.), Natural Pesticides from Neem Tree and Other
Tropical Plants, GTZ, Eschborn, pp. 217–242.
Isman, M.B. (1997) Neem insecticides. Pesticide Outlook, 8, 32–38.
Jermy, T. (1983) Multiplicity of insect antifeedants in plants. In D.L. Whitehead and W.S.
Bowers (eds.), Natural Products for Innovative Pest Management, Pergamon Press,
New York, pp. 223–236.
Jermy, T. (1990) Prospects of antifeedant approach to pest control: A critical review. J. Chem.
Ecol., 16, 3151–3161.
Koul, O. and Shankar, J.S. (1995) Systemic uptake of azadirachtin into Ricinus communis:
Effect on larvae of Spodoptera litura. Ind. J. Expt. Biol., 33, 865–867.
Koul, O., Multani, J.S., Singh G., Daniewski, W.M., and Berlozecki, S. (2003) 6β-Hydrox-
ygedunin from Azadirachta indica, its potentiation effects with some non-azadirachtin
limonoids in neem against lepidopteran larvae. J. Agric. Food Chem., 51, 2937–2942.
Koul, O., Multani, J.S., Goomber S., Daniewski, W.M., and Berlozecki, S. (2004) Activity
of some non-azadirachtin limonoids from Azadirachta indica against lepidopteran
larvae. Aust. J. Entomol. 43, 189–195.
Larson, R.O. (1987) Development of Margosan-O, a pesticide from neem seed. In H. Schmut-
terer and K.R.S. Ascher (eds.), Natural Pesticides from Neem Tree and Other Tropical
Plants, GTZ, Eschborn, pp. 243–250.
Miller, J.R. and Cowles, R.S. (1990) Stimulo-deterrent diversionary cropping: a concept and
its possible application to onion maggot control. J. Chem. Ecol., 16, 3197–3212.
Osman, M.Z. and Port, G.R. (1990) Systemic action of neem seed substances against Pieris
brassicae. Entomol. Exp. Appl., 54, 297–300.

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84 Opender Koul

Pyke, B., Rice, M., Sabine, B., and Zalucki, M.S. (1987) The push-pull strategy: behavioural
control of Heliothis. Aust. Cotton Grower, 7–9.
Raffa, K.F. and Frazier, J.L. (1988) A generalised model for quantifying behavioural de-
sensitization to antifeedants. Entomol. Exp. Appl., 46, 93–100.
Saxena, R.C. (1987) Antifeedants in tropical pest management. Insect Sci. Applic., 8, 731–736.
Schoonhoven, L.M. (1982) Biological aspects of antifeedants. Entomol. Exp. Appl., 31, 57–69.
Stark, J.D. and Walter, J.F. (1995) Persistence of azadirachtin A & B in soil: effect of
temperature and microbial activity. J. Environ. Sci. Health, 30B, 685–698.
Stokes, J.B. and Redfern, R.E. (1982) Effect of sunlight on azadirachtin: Antifeeding potency.
J. Environ. Sci. Health, 17A, 57–65.
Sundaram, K.M.S. and Curry, J. (1996) Effect of some UV light absorbers on the photosen-
sitization of azadirachtin, a neem-based biopesticide. Chemosphere, 32, 649–659.
Van Beek, T.A. and de Groot, A.C. (1986) Terpenoid antifeedants I. An overview of terpenoid
antifeedants of natural origin. Recueil des Trav. Chimiq. des Pays-Bas, 105, 513–527.

© 2005 by CRC Press LLC


7 BIOEFFICACY MONOGRAPHS
A resurgent interest in plant-derived chemicals to control pest insects stems from the need
of pesticide products with less environmental hazards and health impacts than the toxic
synthetic chemicals. Although many natural products show lower mammalian toxicity than
organochlorine, carbamate, or other synthetic insecticides, they do not get free license for
use just because they are natural products. When searching for new insect control agents,
one has to be cautious about the risk that target insect species may become resistant to them
and non-target invertebrates and natural enemies are not harmed. Accordingly, compounds
that modify the behavior of target species and have a primarily nontoxic mode of action may
in the long term provide the most dependable and environmentally safe method of chemical
control. Insect antifeedants are one of the major categories of such compounds and have been
extensively studied during the past decade or two as a method of insect pest management.
As various aspects of antifeedant chemicals have been discussed in preceding chapters,
it is essential to know such compounds from their chemical and bioefficacy point of view.
Since fewer than 1% of all secondary plant substances, estimated to number 400,000 or more
plus many other synthetic analogues, have been tested, and then on a limited number of insect
species only, several effective compounds may remain to be discovered. Various compounds
evaluated specifically as antifeedants are, therefore, presented in the form of monographs to
get firsthand information about any antifeedant evaluated so far. Though it would have been
more appropriate to list the compounds on the basis of their chemical structures like acyclic,
alicyclic (all isoprenoids: mono-, sesqui-, di-, and triterpenoids), aromatic, heterocyclic,
specific alkaloids, and so on, I have deliberately placed them in alphabetical order. The reason
for this is to have an easy access to each and every compound so that a nonchemist and
general reader could approach the details of efficacy and other aspects with ease. It has been
the endeavor to find as much about each compound and also to relate the bioefficacy data on

© 2005 by CRC Press LLC


86 Opender Koul

a single scale, and accordingly the feeding inhibition concentration to deter 50% of the
population has been calculated in all those cases where it was possible to do so from the data
presented in respective publications.
However, success has been little in the sense that due to the tremendous variations in
evaluations of results it was difficult to correlate the efficacy of compounds even within a
group. This probably has been due to the great differences between species in their sensitivity
to a given antifeedant compound. Researchers, when testing candidate compounds, employ
only a few or even only one species for evaluation, so effective feeding deterrents to a
particular insect will easily escape attention. For example, with a well-known antifeedant,
azadirachtin, tested against seven orthopterans, the inter-specific differences span six orders
of magnitude. However, the effort in the present compilation has been to put whole data on
antifeedant compounds at one place in a comprehensive volume, which should give strong
impetus for continual exploration of such compounds for future research, and make the
practical use of insect antifeedants a reality.
Here are some abbreviations used in the data sheets:

B.p. = Boiling point


EC50 = Effective concentration to deter 50% of the population
ED50 = Effective dose to deter 50% of the population
FI50 = Effective feeding inhibition index level to deter 50% of the population
FR50 = Feeding ratio when 50% of control leaf disk area is consumed
i.p. = Intraperitonial
ivn. = Intravenous
LD50 = Lethal dose to kill 50% of the population
M.p. = Melting point
PC50 = Concentration to achieve 50% protection
PC95 = Concentration to achieve 95% protection
s.c. = Subcutaneous
[α]D = Optical rotation

© 2005 by CRC Press LLC


Insect Antifeedants 87

ABIETIC ACID C20H30O2


(7,13-Abietadien-18-oic acid) (302.46)
M.p. : 172–174°

[α]D24 : −106° (EtoH)

H COOH

(1, 2) (1)

SOURCE: Pinus lambertiana Dougl., sugar pine (Pinnaceae) (2)


Commercial sample also tested (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Incisitermes minor (Hagan) Paper towel 0.05 mg/cm2 Feeding deterrence = 1. Treatment to
(Western drywood termite) disk test 27% nymphs of 10–13 mg
body weight for 6
days.

0.25 mg/cm2 Feeding deterrence = Treatment to nymphs


55% of 10–13 mg body
weight for 7 days.
(2)
2. Neodiprion dubiosus Schedl. Pine needle 5.0 mg/ml Feeding deterrence = 2. Treatment to 4th
(Brownhead jack pine sawfly) application 70% and 5th instar larvae
for 4 h.
(3)
3. N. rugifrons Middleton Pine needle 7.8 mg/ml Feeding deterrence = 3. Treatment to 4th
(Redhead jack pine sawfly) application 70% and 5th instar larvae
for 4 h.
(3)
4. N. lecontei (Fitch) Pine needle 12.5 mg/ml Feeding deterrence = 4. Treatment to 4th
(Redhead pine sawfly) application 70% and 5th instar larvae
for 4 h.
(3)

LD50 (rats): 180 mg/kg (ivn.) (4)

(1) Burgstahler, A.W. and Worden, L.R. (1961) J. Am. Chem. Soc., 83, 2587.
(2) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Soc., 9, 39.
(3) Schuh, B.A. and Benjamin, D.M. (1984) J. Econ. Entomol., 77, 802.
(4) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8tth edition, Van Nostrand Reinhold.

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88 Opender Koul

ABSINTHIN C30H40O6
(496.64)
M.p. : 182–183° (dec.)
OH

H [α]20
D : +180° (CHCl3)

H H
OH

H H O
H
H
O

O
(1, 2, 4) (1, 2, 3)

SOURCE: Artemisia absinthium L., wormwood (Asteraceae) (1, 3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera littoralis (Boisd) Leaf disk 0.125% Feeding inhibition = Treatment to 10- to
(Egyptian cotton leafworm) test 100% 13-d-old larvae.
There was absolute
deterrence in
feeding.
(4)
0.063% Feeding inhibition =
95%

(1) Novotny, L., Herout, V., and Sorm, F. (1960) Collect. Czech. Chem. Commun., 25, 1492.
(2) Beauhaire, J., Fourrey, J.L., Vuilhorgne, M., and Lallemand, J.Y. (1980) Tetrahedron Lett., 21, 3191.
(3) Beauhaire, J., Fourrey, J.L., Vuilhorgne, M., and Lallemand, J.Y. (1981) Tetrahedron Lett., 22, 2269.
(4) Wada, K. and Munakata, K. (1971) Agric. Biol. Chem., 35, 115.

© 2005 by CRC Press LLC


Insect Antifeedants 89

ABYSSININ C27H30O8
(482.53)
M.p. : 278°
O

O
H
CHO

OCH3
H

O
OCOCH3
(1) (1)

SOURCE: Bersama abyssinica Fressen., African medicinal plant (Melianthaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Helicoverpa zea (Boddie) Leaf disk 5 µg/cm2 Feeding inhibition = Treatment to larvae.
(Cotton bollworm) choice test 95% The treatment
concentration =
PC95, i.e., 95%
protection of foliage
was achieved.
(1)

(1) Kubo, I. and Matsumoto, T. (1984) Tetrahedron Lett., 25, 4601.

© 2005 by CRC Press LLC


90 Opender Koul

2-ACETONAPHTHONE C12H10O
(170.21)
M.p. : 56°

B.p. : 171–173°/17 mm

(1, 2) (1)

SOURCE: Commercial sample (2)


(Occurs in many essential oils)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Pieris rapae crucivora Boisd. Leaf disk 5 × 10–7 Feeding inhibition = Treatment to 5th
(Cabbage butterfly) dual-choice mol/cm2 99.2% instar larvae pre-
test starved for 3 h.
The treatment given
for 2 h.
(2)

LD50 (mice): 599 mg/kg (oral) (3)

(1) Immediata, T. and Day, A.R. (1940) J. Org. Chem., 5, 512.


(2) Yano, K. and Tanaka, N. (1995) Biosci. Biotech. Biochem., 59, 1130.
(3) Opdyke, D.L.J. (1975) Food Cosmet. Toxicol., 13, 867.

© 2005 by CRC Press LLC


Insect Antifeedants 91

2α-ACETOXY-1α-ACETOXYMETHYL-5,5- C18H28O5
DIMETHYL-1α,6β-10 O, α-BICYCLO DECANE (324.42)
-10-SPIRO-2′-OXIRAN M.p. : 105.5–106°

O
OCOCH3
OCOCH3

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Locusta migratoria L. Glass fiber 100 ppm Feeding inhibition = Treatment to last-
(Migratory locust) disk test 70% stage nymphs.
(1)

(1) Ley, S.V., Neuhaus, D., Simpkins, N.S., and Whittle, A.J. (1982) J. Chem. Soc. Perkin I, 2157.

© 2005 by CRC Press LLC


92 Opender Koul

2β-ACETOXY-1α-ACETOXYMETHYL-5,5- C18H28O5
DIMETHYL-1α,6α-10 O,α-BICYCLO DECANE (324.42)
-10-SPIRO-2′-OXIRAN M.p. : 64°

O
OCOCH3

OCOCH3

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Locusta migratoria L. Glass fiber 1000 ppm Feeding inhibition = Treatment to last-
(Migratory locust) disk test 72% stage nymphs.
This isomer,
however, inhibited
72% feeding at a
high concentration of
1000 ppm.
(1)

(1) Jackson, W.P. and Ley, S.V. (1981) J. Chem. Soc. Perkin I, 1516.

© 2005 by CRC Press LLC


Insect Antifeedants 93

19-ACETOXY-18 CHLORO-4α-HYDROXY-6- C22H31O6Cl


OXONEOCLEROD-13-EN-15,16 OLIDE (426.94)
M.p. : 154–156°
O
[α]D22 : –41.7° (CHCl3)
O

HO
O
Cl OAc
(1) (1)

SOURCE: Semisynthetic, prepared from ajugarin II (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera exigua (Hubner) Leaf disk test 1000 ppm Feeding inhibition = Treatment to newly
(Beet armyworm) emerged 5th instar
No-choice 29.9% larvae pre-starved for
Choice 91.7% 6 h until 50% of the
control disks were
consumed in choice
situation and 75% in
no-choice assay.
Assayed against
Leptinotarsa
decemlineata as well
but found inactive
against this species.
(1)

(1) Caballero, C., Castanera, P., Ortego, F., Fontana, G., Pierro, P., Savona, G., and Rodriguez, B. (2001)
Phytochemistry, 58, 249.

© 2005 by CRC Press LLC


94 Opender Koul

19-ACETOXY-4,6-DIOXO-18-NOR- C21H28O6
NEOCLEROD-13-EN-15,16 OLIDE (376.45)
M.p. : 176–177°
O

O [α]22
D : +8.2° (CHCl3)

O O
OAc (1) (1)

SOURCE: Semisynthetic, prepared from ajugarin II (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera exigua (Hubner) Leaf disk test 1000 ppm Feeding inhibition = Treatment to newly
(Beet armyworm) emerged 5th instar
No-choice 9.9% larvae pre-starved for
Choice 72.9% 6 h until 50% of the
control disks were
consumed in choice
situation and 75% in
no-choice assay.
Assayed against
Leptinotarsa
decemlineata as well
but found inactive
against this species.
(1)

(1) Caballero, C., Castanera, P., Ortego, F., Fontana, G., Pierro, P., Savona, G., and Rodriguez, B. (2001)
Phytochemistry, 58, 249.

© 2005 by CRC Press LLC


Insect Antifeedants 95

11β-ACETOXY-5α-ISOBUTYRYLOXYSILPHINEN-3-ONE C21H30O5
(362.21)
Oil

Only spectral data given


OAc

O C
O

(1) (1)

SOURCE: Senecio palmensis Chr.Sm., groundsel (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera littoralis (Boisd.) Choice leaf ~100 Feeding deterrence = 1. Treatment to L6


(Egyptian cotton leaf worm) disk feeding nmol/cm2 50.0% larvae for 24 h.
assay Concentration = EC50

2. Leptinotarsa decemlineata Choice leaf 0.08 Feeding deterrence = 2. Treatment to


(Say) disk feeding nmol/cm2 50.0% adults for 24 h.
(Colorado potato beetle) assay Concentration = EC50

3. Diuraphis noxia (Mordvilko) Choice 8.0 Feeding deterrence = 3. Treatment to


(Solanum aphid) feeding assay nmol/cm2 50.0% adults for 24 h.
Concentration = EC50

4. Myzus persicae (Sulzer) Choice 29.3 Feeding deterrence = 4. Treatment to


(Green peach aphid) feeding assay nmol/cm2 50.0% adults for 24 h.
Concentration = EC50
(1)

(1) Gonzalez-Coloma, A., Valencia, F., Martin, N., Hoffmann, J.J., Hutter, L., Marco, J.A., and Reina, M. (2002)
J. Chem. Ecol., 28, 117.

© 2005 by CRC Press LLC


96 Opender Koul

11β-ACETOXY-5α-TIGLOYLOXYSILPHINEN-3-ONE C22H30O5
(374.21)
Oil
OAc
Only spectral data given

O O

(1) (1)

SOURCE: Senecio palmensis Chr.Sm., groundsel (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera littoralis (Boisd.) Choice leaf >200 Feeding deterrence = 1. Treatment to L6


(Egyptian cotton leaf worm) disk feeding nmol/cm2 50.0% larvae for 24 h.
assay Concentration = EC50

2. Leptinotarsa decemlineata Choice leaf 0.17 Feeding deterrence = 2. Treatment to


(Say) disk feeding nmol/cm2 50.0% adults for 24 h.
(Colorado potato beetle) assay Concentration = EC50

3. Diuraphis noxia (Mordvilko) Choice >120 Feeding deterrence = 3. Treatment to


(Solanum aphid) feeding nmol/cm2 50.0% adults for 24 h.
assay Concentration = EC50
(1)

(1) Gonzalez-Coloma, A., Valencia, F., Martin, N., Hoffmann, J.J., Hutter, L., Marco, J.A., and Reina, M. (2002)
J. Chem. Ecol., 28, 117.

© 2005 by CRC Press LLC


Insect Antifeedants 97

11β-HYDROXY-5α-ANGELOYLOXYSILPHINEN-3-ONE C20H28O4
(332.44)
Oil

Only spectral data given


OH

O OAng

(1) (1)

SOURCE: Senecio palmensis Chr.Sm., groundsel (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera littoralis (Boisd.) Choice leaf >150 Feeding deterrence = 1. Treatment to L6


(Egyptian cotton leaf worm) disk feeding nmol/cm2 50.0% larvae for 24 h.
assay Concentration = EC50

2. Leptinotarsa decemlineata Choice leaf 21.6 Feeding deterrence = 2. Treatment to


(Say) disk feeding nmol/cm2 50.0% adults for 24 h.
(Colorado potato beetle) assay Concentration = EC50

3. Diuraphis noxia (Mordvilko) Choice 38.8 Feeding deterrence = 3. Treatment to


(Solanum aphid) feeding nmol/cm2 50.0% adults for 24 h.
assay Concentration = EC50
(1)

(1) Gonzalez-Coloma, A., Valencia, F., Martin, N., Hoffmann, J.J., Hutter, L., Marco, J.A., and Reina, M. (2002)
J. Chem. Ecol., 28, 117.

© 2005 by CRC Press LLC


98 Opender Koul

11β-ACETOXY-5α (ANGELOYLOXY) C22H30O5


SILPHINEN-3-ONE (374.48)
Oil

[α]D : –69° (CHCl3)


OAc

O OAng

(1, 3) (1, 3)

SOURCE: Senecio palmensis Chr.Sm., groundsel (Asteraceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Leptinotarsa decemlineata Leaf disk 1.69 µg/cm2 Feeding inhibition = Treatment to newly
(Say) choice 50% emerged 4th instar
(Colorado potato beetle) assay larvae for ≤ 6 h.

14.43 µg/cm2 Feeding inhibition = Treatment to newly


50% emerged 4th instar
larvae for 24 h.

Concentration = FI50
values.
(2)

(1) Gonzalez-Coloma, A., Reina, M., Cabrera, R., Castanera, P., and Gutierrez, C. (1995) J. Chem. Ecol., 21, 1255.
(2) Gonzalez-Coloma, A., Gutierrez, C., Cabrera, R., and Reina, M. (1997) J. Agric. Food Chem., 45, 946.
(3) Jakupovic, J. and Abraham, W.R. (1985) Phytochemistry, 24, 3048.

© 2005 by CRC Press LLC


Insect Antifeedants 99

12-α-ACETOXYFRAXINELLONE C16H18O5
(290.32)
M.p. : 102–104°C

O
O

structure under review


(1) (1)

SOURCE: Melia azedarach L., darekh (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera littoralis (Boisd.) Leaf disk 10 µg/cm2 Feeding inhibition = Treatment to 3rd
(Egyptian cotton leaf worm) choice test 100% instar larvae.
(1)

(1) Nakatani, M., Huang, R.C., Okamura, H., Iwagawa, T., and Tadera, K. (1998) Phytochemistry, 49, 1773.

© 2005 by CRC Press LLC


100 Opender Koul

12β-ACETOXYHARRISONIN C29H34O12
(574.58)
M.p. : 253–254°
O

OAc

O
O
O
HO OH
O
O
O

(1, 2) (1)

SOURCE: Harrisonia abyssinica Oliv., East African medicinal plant (Simaroubaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera eridania Leaf disk 500 ppm Feeding inhibition = 1. Treatment to 3rd
(Cramer) choice 100% instar larvae. Only
(Southern armyworm) assay one of the few
antifeedants active
against this
voracious herbivore.
(2)

2. Eldana saccharina Walker Leaf disk 100 µg/disk Feeding inhibition = 2. Treatment to 12-h
(sugar cane borer) choice 54 ± 8% pre-starved late 5th
assay instar larvae.
(3)

3. Maruca testulalis (Geyer) Leaf disk 100 µg/disk Feeding deterrence = 3. Treatment to 12-h
(bean pod borer) choice test 84 ± 10% pre-starved late 5th
instar larvae.
10 µg/disk Feeding deterrence = (3)
46 ± 15%

(1) Liu, H., Kubo, I., and Nakanishi, K. (1982) Heterocycles, 17, 67.
(2) Rajab, M.S., Rugutt, J.K., Fronczek, F.R., and Fischer, N.H. (1997) J. Nat. Prod., 60, 822.
(3) Hassanali, A., Bentley, M.D., Sitayo, E.N.O., Njoroge, P.E.W., and Yatagai, M. (1986) Insect Sci. Applic., 7,
495.

© 2005 by CRC Press LLC


Insect Antifeedants 101

7β-ACETOXY (–)-KAUR-16-EN-19-OIC ACID C22H32O4


(360.49)
Only spectral data given

H
OAc
COOH

(1) (1)

SOURCE: Xylopia aethiopica A. Rich., African pepper (Anonaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Reticulitermes speratus Kolbe Paper disk 2500 ppm Feeding inhibition Treatment to 2nd
(Subterranean termite) choice index = 0 instar workers where
bioassay feeding was
1000 ppm Feeding inhibition continued for 14
index = 5.4 days.
Antifeedant index
value below 20 was
considered highly
deterrent in this
evaluation.
(1)

(1) Lajide, L., Escoubas, P., and Mizutani, J. (1995) Phytochemistry, 40, 1105.

© 2005 by CRC Press LLC


102 Opender Koul

15β-ACETOXY (–)-KAUR-16-EN-19-OIC ACID C22H32O4


(360.49)
Only spectral data given

OAc

COOH

(1) (1)

SOURCE: Xylopia aethiopica A. Rich., African pepper (Anonaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Reticulitermes speratus Kolbe Paper disk 2500 ppm Feeding inhibition Treatment to 2nd
(Subterranean termite) choice index = 32.9 instar workers where
bioassay feeding was
continued for 14
days.
Antifeedant index
value below 20 was
considered highly
deterrent in this
evaluation.
(1)

(1) Lajide, L., Escoubas, P., and Mizutani, J. (1995) Phytochemistry, 40, 1105.

© 2005 by CRC Press LLC


Insect Antifeedants 103

5α-ACETOXYSILPHINEN-3-ONE C17H24O3
(276.37)
Oil

[α]D : –3° (CH2Cl2)

O OAc

(1) (1)

SOURCE: Senecio palmensis Chr.Sm., groundsel (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera littoralis (Boisd.) Choice >200 Feeding deterrence = 1. Treatment to 6th


(Eygyptian cotton leaf worm) feeding assay nmol/cm2 50.0% instar larvae.

2. Leptinotarsa decemlineata Choice 2.81 Feeding deterrence = 2. Treatment to


(Say) feeding assay nmol/cm2 50.0% adults.
(Colorado potato beetle)

3. Myzus persicae (Sulzer) Choice >500 Feeding deterrence = 3. Treatment to


(Green peach aphid) feeding assay nmol/cm2 50.0% apterous adult
aphids.

4. Rhopalosiphum padi (L.) Choice >200 Feeding deterrence = 4. Treatment to


(Cereal aphid) feeding assay nmol/cm2 50.0% apterous adult
aphids.

5. Sitobion avenae (Fab.) Choice >200 Feeding deterrence = 5. Treatment to


(Grass aphid) feeding assay nmol/cm2 50.0% apterous adult
aphids.

6. Diuraphis noxia (Mordvilko) Choice 57.4 Feeding deterrence = 6. Treatment to


(Wheat aphid) feeding assay nmol/cm2 50.0% apterous adult
aphids.
Concentrations =
EC50 values.
(1)

(1) Reina, M., Nold, M., Santana, O., Orihuela, J.C., and Gonzalez-Coloma, A. (2002) J. Nat. Prod., 65, 448.

© 2005 by CRC Press LLC


104 Opender Koul

21-ACETOXYTOONACILID C33H40O12
(628.67) [α]20
D : +47.5° (CHCl3)
O

O
OAc

AcO OAc

O
CH2
O

COOCH3
(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Epilachna varivestis Muls. Leaf 0.05% Feeding inhibition = Treatment to adult


(Mexican bean beetle) disk test 100% beetles, absolute
feeding deterrence
achieved within 24 h.
(1)

(1) Kraus, W. and Grimminger, W. (1980) Nour. J. de Chimie, 4, 651.

© 2005 by CRC Press LLC


Insect Antifeedants 105

6-ACETOXYTOONACILIN C33H40O11
(612.67)
M.p. : 215°

O [α]D20 : +42.5° (CHCl3)


OAc

AcO

O
H2C
O OAc

COOCH3

(1) (1)

SOURCE: Toona ciliata M.J. Roem, red cedar (Meliaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Epilachna varivestis Muls. Leaf 0.2% Feeding inhibition = Treatment to adult


(Mexican bean beetle) disk test 100% beetles, absolute
feeding deterrence
achieved within 24 h.
(2)

(1) Kraus, W., Grimminger, W., and Sawitzki, G. (1978) Angew. Chemie., 17, 452.
(2) Kraus, W. and Grimminger, W. (1980) Nour. J. de Chimie, 4, 651.

© 2005 by CRC Press LLC


106 Opender Koul

1β-ACETOXY-2β,8β,9α-TRIBENZOYLOXY-4α, C38H40O11
6α-DIHYDROXY-β-DIHYDROAGAROFURAN (672.73)
M.p. : 245–246°

OAc OBz

BzO OBz

O
HO
OH

(1) (1)

SOURCE: Celastrus rosthornianus Loes., bitter tree (Celastraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Pieris rapae (L.) Macerated 500 ppm Feeding inhibition = Treatment to larvae
(Imported cabbage worm) leaf 49.0% pre-starved for 3 h.
feeding (1)

(1) Tu, Y.Q. (1991) J. Chem. Soc. Perkin Trans. I, 425.

© 2005 by CRC Press LLC


Insect Antifeedants 107

12-O-ACETYLAZEDARACHIN–A C35H46O12
(658.74)
[α]22
D : +7.5° (MeOH)
O

OAc

O
HO

O O

AcO
OH

OCO

(1, 2) (1)

SOURCE: Melia azedarach L., chinaberry (Meliaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera eridania Leaf disk 400 ppm Feeding inhibition 1. Treatment to 3rd
(Cramer) choice assay or instar larvae for 6 to
(Southern armyworm) 8 µg/cm2 24 h, during which
period 50% of one of
the disks was
consumed.
(2)

2. Spodoptera exigua (Hubner) Leaf disk 400 ppm Feeding inhibition 2. Treatment to 3rd
(Beet armyworm) choice assay or instar larvae for 6 to
8 µg/cm2 24 h, during which
period 50% of one of
the disks was
consumed.
Concentration =
minimum level
required for
inhibition.
(2)

(1) Huang, R.C., Okamura, H., Iwagawa, T., and Nakatani, M. (1994) Bull. Chem. Soc. Jap., 67, 2468.
(2) Nakatani, M., Huang, R.C., Okamura, H., Iwagawa, T., Tadera, K., and Naoki, H. (1995) Tetrahedron, 51,
11731.

© 2005 by CRC Press LLC


108 Opender Koul

12-O-ACETYLAZEDARACHIN–B C34H44O12
(644.71)
D : −55° (MeOH)
[α]22
O

OAc

O
HO

O O

AcO
OH

OCO

(1, 2) (1)

SOURCE: Melia azedarach L., chinaberry (Meliaceae)


M. Toosendan Sieb. et Zucc., Chinese melia (Meliaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera eridania Leaf disk 400 ppm Feeding inhibition 1. Treatment to 3rd
(Cramer) choice assay or instar larvae for 6 to
(Southern armyworm) 8 µg/cm2 24 h, during which
period 50% of one of
the disks was
consumed.
(2)

2. Spodoptera exigua (Hubner) Leaf disk 400 ppm Feeding inhibition 2. Treatment to 3rd
(Beet armyworm) choice assay or instar larvae for 6 to
8 µg/cm2 24 h, during which
period 50% of one of
the disks was
consumed.
Concentration =
minimum level
required for
inhibition.
(2)

(1) Zhou, J., Okamura, H., Iwagawa, T., and Nakatani, M. (1996) Phytochemistry, 41, 117.
(2) Nakatani, M., Huang, R.C., Okamura, H., Iwagawa, T., Tadera, K., and Naoki, H. (1995) Tetrahedron, 51,
11731.

© 2005 by CRC Press LLC


Insect Antifeedants 109

1-O-ACETYL-3-DEACETYL-1- C28H36O8
DETIGLOYLSALANNIN (500.56)
Only spectral data given

AcO COOCH3

O
HO
H
O

(1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera littoralis (Boisd.) Glass fiber 1.0 ppm Feeding inhibition = Treatment to starved
(Egyptian cotton leafworm) disk choice 44.0% final stadium larvae
assay (24 to 36 h old).
Bioassay terminated
2. Spodoptera frugiperda Glass fiber 1.0 ppm Feeding inhibition = after the larvae had
(J.E. Smith) disk choice 31.0% eaten approximately
(Fall armyworm) assay 50% of one of the
disks in each case.

3. Heliothis virescens (Fab.) Glass fiber 1.0 ppm Feeding inhibition = EC50 approximately
(Tobacco budworm) disk choice 11.0% 1.5 ppm to 2.0 ppm
test in this bioassay.
(1)
4. Helicoverpa armigera Glass fiber 1.0 ppm Feeding inhibition =
(Hubner) disk choice 21.0%
(Gram pod borer) test

(1) Blaney, W.M., Simmonds, M.S.J., Ley, S.V., Anderson, J.C., and Toogood, P.L. (1990) Entomol. Exp. Appl.,
55, 149.

© 2005 by CRC Press LLC


110 Opender Koul

1-O-ACETYL-1-DETIGLOYLSALANNIN C31H40O9
(556.65)
Only spectral data given

COOCH3
AcO

AcO O
H
O

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Leptinotarsa decemlineata Leaf disk >400 µg/cm2 Feeding inhibition = Treatment to newly
(Say) choice 50% emerged 3rd instar
(Colorado potato beetle) assay larvae.
Leaf disks examined
every 2 h until 95%
of control disks were
eaten.
Concentration used
here is protection.
Concentration = PC50
value.
(1)

(1) Yamasaki, R.B. and Klocke, J.A. (1989) J. Agric. Food Chem., 37, 1118.

© 2005 by CRC Press LLC


Insect Antifeedants 111

2-ACETYL-14,15-DIHYDRO AJUGAPTIN C31H46O11


(594.70)
Only spectral data given
H

O
H

O
H H

CH3COO H

COO
O
OCOCH3
OCOCH3

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera littoralis (Boisd.) Leaf disk 1.0 µg/cm2 Feeding ratio = Treatment to newly
(Egyptian cotton leaf worm) choice assay 0.06 ± 0.02 ecdysed 5th instar
larvae.
(i.e., FR50 value: the FR50 = < 0.5
ratio when 50% of Considered as
control disk area has excellent antifeedant
been consumed) activity.
(1)

(1) Belles, X., Camps, F., Coll, J., and Piulachs, M.D. (1985) J. Chem. Ecol., 11, 1439.

© 2005 by CRC Press LLC


112 Opender Koul

ACETYLISOMONTANOLIDE C24H32O8
(448.51)
M.p. : 134°

OOCCH3 D : −78.2° (CHCl3)


[α]20

OOC

OOCCH3

(1, 2) (1)

SOURCE: Laserpitium siler L., mountain lasser wort (Apiaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius L. Wafer disk 1.0% Feeding deterrence 1. Treatment given to


(Grain weevil) test coefficient = adults.
103 (adults)

2. Tribolium confusum Jacq. Wafer disk 1.0% Feeding deterrence 2. Treatment given to
Duv. test coefficient = both adults and
(Confused flour beetle) 106 (adults) larvae.
85 (larvae)

3. Trogoderma granarium Wafer disk 1.0% Feeding deterrence 3. Treatment given to


Everts test coefficient = adults.
(Khapra beetle) 43 (larvae)
Neutral value = 0
Absolute feeding
deterrence value =
200.
(2)

(1) Holub, M., Motl, O., Samek, Z., and Herout, V. (1972) Collect. Czech. Chem. Commun., 37, 1186.
(2) Belles, X., Camps, F., Coll, J., and Piulachs, M.D. (1985) J. Chem. Ecol., 11, 1439.

© 2005 by CRC Press LLC


Insect Antifeedants 113

2-ACETYLIVAIN-1 C31H46O11
(580.67)
[α]20
D : +15.9° (CHCl3)
H

O
H

O
H H

CH3COO H

COO
O
OCOCH3
OCOCH3

(1, 2) (1)

SOURCE: Ajuga pseudoiva (L.) Schreber., African ajuga (Labiatae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera littoralis (Boisd.) Leaf disk 1.0 µg/cm2 Feeding ratio = Treatment to newly
(Egyptian cotton leaf worm) choice assay 0.12 ± 0.04 ecdysed 5th instar
larvae.
(i.e., FR50 value: the FR50 = < 0.5
ratio when 50% of Considered as
control disk area has excellent antifeedant
been consumed) activity.

0.1 µg/cm2 Feeding ratio =


0.51 ± 0.05 (2)

(1) Camps, F., Coll, J., and Dargallo, O. (1984) Phytochemistry, 23, 387.
(2) Belles, X., Camps, F., Coll, J., and Piulachs, M.D. (1985) J. Chem. Ecol., 11, 1439.

© 2005 by CRC Press LLC


114 Opender Koul

6-ACETYLNIMBANDIOL C28H34O8
(498.57)
M.p. : 178°

[α]D20 : +245° (CHCl3)


OCH3 O

O
O

HO
OAc

(1) (1)

SOURCE: Azadirachta indica A. Juss., neem (Meliaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Epilachna varivestis Muls. Bean leaf 0.011% Feeding inhibition = Treatment to 4th
(Mexican bean beetle) choice assay 50% instar larvae for 24 h.
Concentration = EC50
value.
(2)

(1) Kraus, W. and Cramer, R. (1981) Chem. Ber., 114, 2375.


(2) Schwinger, M., Ehhammer, B., and Kraus, W. (1984) In H. Schmutterer and K.R.S. Ascher (eds.), Proc. 2nd
Int. Neem Conf., Rauischholzhausen, GTZ, Eschborn, Germany, pp. 181–198.

© 2005 by CRC Press LLC


Insect Antifeedants 115

3-O-ACETYLOHCHINOLAL C36H46O11
(654.75)
Amorphous powder

O O [α]D : +62°(CH3OH)
COOCH3
O

O
AcO

CHO
OAc

(1) (1)

SOURCE: Melia toosendan Sieb. et Zucc., Chinese melia (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera eridania(Cramer) Leaf disk 1000 ppm Feeding deterrence = Treatment given to
(Southern armyworm) choice test (20 µg/ml) 50% 3rd instar larvae for 6
to 24 h, during which
period 50% of one of
the disks was
consumed.
(1)

(1) Zhou, J., Minami, Y., Yagi, F., Tadera, K., and Nakatani, M.(1997) Phytochemistry, 46, 911.

© 2005 by CRC Press LLC


116 Opender Koul

19-ACETYLTEUPOLIN–IV C24H28O9
(460.48)
M.p. : 230–234°
O
[α]24
D : +132.3° (pyridine)

OAc
O
O
OAc

(1, 2) (1, 2)

SOURCE: Teucrium polium pilosum, (L.) Decne., golden germander (Labiatae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

No specific insect species Leaf disk Feeding deterrent Reported as insect


mentioned choice test feeding deterrent but
no specific
quantitative data
have been recorded.
(1)

(1) De la Torre, M.C., Piozzi, F., Rizk, A.-F., Rodriguez, B., and Savona, G. (1986) Phytochemistry, 25, 2239.
(2) Hundal, G. and Martinez-Ripoll, M. (1996) Acta Cryst., 52C, 3157.

© 2005 by CRC Press LLC


Insect Antifeedants 117

7-ACETYLTRICHILIN–A C37H48O14
(716.78)
Only spectral data given
O

OH

O
HO

AcO

O O

AcO
OAc

OCO

(1, 2) (1)

SOURCE: Trichilia roka (Forsk.) Chiov., East African trichilia (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera eridania Leaf disk 500 ppm Feeding deterrent for Treatment given to
(Cramer) choice test all the three species. larvae for 6–24 h.
(Southern armyworm)
No quantitative data
2. Epilachna varivestis Muls. Leaf disk 500 ppm recorded for any of
(Mexican bean beetle) choice test the species for this
compound.
3. Spodoptera littoralis (Boisd.) Leaf disk 500 ppm (1)
(Egyptian cotton leafworm) choice test

(1) Nakatani, M., Iwashita, T., Naoki, H., and Hase, T. (1985) Phytochemistry, 24, 195.
(2) Nakanishi, K., Cooper, R., and Nakatani, M. (1981) Proc. Inst. Org. Phys. Chem. Wroclaw, 7, 1091.

© 2005 by CRC Press LLC


118 Opender Koul

12-O-ACETYLTRICHILIN–B C37H48O14
(716.78)
D : −2.5° (MeOH)
[α]22
O

OAc

O
HO

AcO

O O

AcO
OH

OCO

(1, 2) (1)

SOURCE: Melia azedarach L., chinaberry (Meliaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera eridania Leaf disk 400 ppm Feeding inhibition 1. Treatment to 3rd
(Cramer) choice assay or instar larvae for 6 to
(Southern armyworm) 8 µg/cm2 24 h, during which
period 50% of one of
the disks was
consumed.
(2)

2. Spodoptera exigua (Hubner) Leaf disk 400 ppm Feeding inhibition 2. Treatment to 3rd
(Beet armyworm) choice assay or instar larvae for 6 to
8 µg/cm2 24 h, during which
period 50% of one of
the disks was
consumed.
Concentration =
minimum level
required for
inhibition.
(2)

(1) Nakatani, M., Huang, R.C., Okamura, H., Naoki, H., and Iwagawa, T. (1994) Phytochemistry, 36, 39.
(2) Nakatani, M., Huang, R.C., Okamura, H., Iwagawa, T., Tadera, K., and Naoki, H. (1995) Tetrahedron, 51,
11731.

© 2005 by CRC Press LLC


Insect Antifeedants 119

ACETYLVISMINONE–B C23H24O6
(396.44)
M.p. : 115–120° (dec.)

O OH O

OCH3
AcO

(1, 2) (1, 2)

SOURCE: Synthetic (1)


Visma japuransis (Hypericaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Locusta migratoria L. Glass fiber 10–3 M Feeding inhibition = Treatment to last


(migratory locust) disk test 100% stage nymphs.
(1)

(1) Simmonds, M.S.J., Blaney, W.M., DelleMonache, F., Mac-Quhae, M.M., and Bettolo, G.B.M. (1985) J. Chem.
Ecol., 11, 1593.
(2) Pinheiro, R.M., Quhae, M.M., Bettolo, G.B.M., and Monache, F.D. (1984) Phytochemistry 23, 1737.

© 2005 by CRC Press LLC


120 Opender Koul

ACROPTILLIN C19H23O7Cl
(398.84)
M.p. : 197–199°

CH2 [α]D : +100° (MeOH)

Cl
HO OOC
OH
O
CH2
O

(1, 2, 3) (1, 2, 3)

SOURCE: Centaurea bella Trautv., tumbleweed (Cynaraceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius L. Wafer disk 10.0 mg/cm3 Feeding deterrence 1. Treatment given to
(Grain weevil) test coefficient = adults.
57 (adults)

2. Tribolium confusum Jacq. Wafer disk 10.0 mg/cm3 Feeding deterrence 2. Treatment given to
Duv. test coefficient = both adults and
(Confused flour beetle) 88.7 (adults) larvae.
47.5 (larvae)

3. Trogoderma granarium Wafer disk 10.0 mg/cm3 Feeding deterrence 3. Treatment given to
Everts test coefficient = adults.
(Khapra beetle) 47.4 (larvae)
Neutral value = 0
Absolute feeding
deterrence value =
200.
(2)

(1) Evstratova, R.I., Sheichenko, V.I., and Rybalko, K.S. (1973) Khim. Prir. Soedin., 9, 161.
(2) Nawrot, J., Bloszyk, E., Girabarczyk, H., Dorzdz, B., Daniewski, W.M., and Holub, M. (1983) Prace. Nauk.
Inst. Ochr. Roslin., 25, 91.
(3) Stevens, K.L. (1982) Phytochemistry, 21, 1093.

© 2005 by CRC Press LLC


Insect Antifeedants 121

AFLAVAZOLE C28H35O2N
(417.59)
M.p. : 156–160° (dec.)

OH [α]D : +2.8° (CH3OH)

OH

N
H

(1) (1)

SOURCE: Aspergillus flavus Link, common mould (Fungi) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Carpophilus hemipterus (L.) Artificial diet 100 ppm Feeding deterrence = Treatment given to
(Dried fruit beetle) test Threshold level adults.

200–600 Feeding deterrence = Variation obtained in


ppm 100% achieving absolute
feeding deterrence in
different
experiments.
(1)

(1) TePaske, M.R., Gloer, J.B., Wicklow, D.T., and Dowd, P.F. (1990) J. Org. Chem., 55, 5299.

© 2005 by CRC Press LLC


122 Opender Koul

AGERATRIOL C15H24O3
(252.35)
M.p. : 195°

[α]20
D : +30.5° (CH3OH)

OH OH
CH2

OH
CH2 CH2

(1, 2) (1)

SOURCE: Achillea ageratum L., yarrow (Asteraceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius L. Wafer disk 10.0 mg/cm3 Feeding deterrence 1. Treatment given to
(Grain weevil) test coefficient = adults.
55.8 (adults) (2)

2. Tribolium confusum Jacq. Wafer disk 10.0 mg/cm3 Feeding deterrence 2. Treatment given to
Duv. test coefficient = both adults and
(Confused flour beetle) 64.6 (adults) larvae.
52.7 (larvae) (2)

3. Trogoderma granarium Wafer disk 10.0 mg/cm3 Feeding deterrence 3. Treatment given to
Everts test coefficient = adults.
(Khapra beetle) 97.2 (adults)
Neutral value = 0
Absolute feeding
deterrence value =
200.
(2)

(1) Garanti, L., Marchesini, A., Pagnoni, U.M., and Trave, R. (1972) Tetrahedron Lett., 13, 1397.
(2) Nawrot, J., Bloszyk, E., Girabarczyk, H., Dorzdz, B., Daniewski, W.M., and Holub, M. (1983) Prace. Nauk.
Inst. Ochr. Roslin., 25, 91.

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Insect Antifeedants 123

AGINOSIDE C50H82O24
(1067.18)
M.p. : 272–276° (dec.)

O
[α]D29 : –66.7° (CHCl3)

HO

xyl gul gul O

OH

(1, 3) (3)

SOURCE: Allium porrum (L.) Regel., elephant garlic (Amaryllidaceae) (1)


A. giganteum L.

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Peridroma saucia Hubner Leaf disk 2.85 µg/cm2 Feeding deterrence = Treatment to 5th
(Variegated cutworm) choice test 67.3% instar larvae for 5 h.
(2)
11.4 µg/cm2 Feeding deterrence =
84.7% EC50 calculated =
2.27 µg/cm2
28.5 µg/cm2 Feeding deterrence =
95.5%

57.0 µg/cm2 Feeding deterrence =


100%

(1) Harmatha, J., Mauchamp, B., Arnault, C., and Slama, K. (1987) Biochem. Syst. Ecol., 15, 113.
(2) Nawrot, J., Koul, O., Isman, M.B., and Harmatha, J. (1991) J. Appl. Ent., 112, 194.
(3) (1994) Dictionary of Natural Products, Chapman & Hall, London.

© 2005 by CRC Press LLC


124 Opender Koul

AILANTHINONE C25H34O9
(478.54)
M.p. : 227–230°

[α]27
D : +90° (CHCl3)
OH

HO
HO
O
O OCO

O O

(1, 2) (1)

SOURCE: Pierreodendron kerstingii (Simaroubaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Heliothis virescens Fab. Leaf disk 19.8 µg/cm2 Feeding deterrence = Treatment to 3rd
(Tobacco budworm) choice test 60–90% after 2 days instar larvae.
(2)
Feeding deterrence =
30–60% after 6 days

(1) Kupchan, S.M. and Lacadie, J.A. (1975) J. Org. Chem., 40, 654.
(2) Lidert, Z., Wiing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y., Kiyokawa, H., and Lee, K.
(1987) J. Nat. Prod., 50, 442.

© 2005 by CRC Press LLC


Insect Antifeedants 125

AJUGAREPTANSIN C29H44O10
(552.66)
Amorphous
H

O [α]D20 : –28° (CCl4)


H

O
COO H
H
H
H

HO
O
OCOCH3
OCOCH3

(1, 2) (1)

SOURCE: Ajuga reptans L., Catlins giant (Labiatae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera littoralis (Boisd.) Leaf disk 10.0 µg/cm2 Feeding ratio = Treatment to newly
(Egyptian cotton leaf worm) choice test 0.20 ± 0.07 ecdysed 5th instar
larvae.
(i.e., FR50 value: the FR50 = < 0.5
ratio when 50% of considered as
control disk area is excellent feeding
consumed) deterrent.
(2)

(1) Camps, F., Coll, J., Cortel, A., and Messeguer, A. (1979) Tetrahedron Lett., 20, 1709.
(2) Belles, X., Camps, F., Coll, J., and Piulachs, M.D. (1985) J. Chem. Ecol., 11, 1439.

© 2005 by CRC Press LLC


126 Opender Koul

AJUGAREPTANSONE–A C29H40O10
(548.63)
M.p. : 177–180°
O

O [α]D : –6° (CHCl3)

COO
O
OCOCH3
OCOCH3
(1, 2) (1)

SOURCE: Ajuga reptans L., Catlins giant (Labiatae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera littoralis (Boisd.) Leaf disk 25.0 µg/cm2 Feeding ratio = Treatment to newly
(Egyptian cotton leaf worm) choice test 0.74 ± 0.12 ecdysed 5th instar
larvae.
(i.e., FR50 value: the FR50 = < 0.5
ratio when 50% of considered as
control disk area is excellent feeding
consumed) deterrent. Thus this
compound has
moderate activity.
(2)

(1) Camps, F., Coll, J., and Cortel, A. (1981) Chem. Lett., 1093.
(2) Belles, X., Camps, F., Coll, J., and Piulachs, M.D. (1985) J. Chem. Ecol., 11, 1439.

© 2005 by CRC Press LLC


Insect Antifeedants 127

AJUGAPITIN C29H42O10
(Clerodendrin D) (550.65)
M.p. : 196–198°
O
H [α]D20 : –70.3° (CHCl3)

O
H

H H
H

HO

COO
O
OCOCH3
OCOCH3

(1, 2) (1)

SOURCE: Ajuga chamaepitys (L.) Schreb., ground pine (Labiatae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera littoralis (Boisd.) Leaf disk 1.0 µg/cm2 Feeding ratio = Treatment to newly
(Egyptian cotton leaf worm) choice test 0.04 ± 0.0 ecdysed 5th instar
larvae.
(i.e., FR50 value: the FR50 = < 0.5
ratio when 50% of considered as
control disk area is excellent feeding
consumed) deterrent. Thus this
compound has
0.1 µg/cm2 FR50 = 0.24 ± 0.06 moderate activity.
(2)

0.01 µg/cm2 FR50 = 0.41 ± 0.10

(1) Hernandez, A., Pascual, C., Sanz, J., and Rodriguez, B. (1982) Phytochemistry, 21, 2909.
(2) Belles, X., Camps, F., Coll, J., and Piulachs, M.D. (1985) J. Chem. Ecol., 11, 1439.

© 2005 by CRC Press LLC


128 Opender Koul

AJUGARIN–I C24H34O7
(434.53)
M.p. : 155–157°
O

H
O

OAc
CH2OAc

(1) (1,2)

SOURCE: Ajuga remota Benth., African ajuga (Labiatae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera exempta (Walker) Leaf disk 100 ppm Minimum level of 1. Treatment to
(African armyworm) choice test treatment to exhibit larvae at random.
antifeedant activity. (1)

2. Spodoptera littoralis (Boisd.) Leaf disk 300 ppm Minimum level of 2. Treatment to
(Egyptian cotton leaf worm) choice test treatment to exhibit larvae at random.
antifeedant activity. (1)

Glass fiber 100 ppm Feeding deterrence = Treatment to final


disk choice 43% stadium larvae for
test 12 h.
(2)

3. Schistocerca gregaria Forsk. Leaf disk 60 µg/l Minimum level of 3. Treatment to 3- to


(Desert locust) choice test treatment to exhibit 5-day-old well-fed
antifeedant activity. 5th instar larvae.
(3)

4. Spodoptera exigua (Hubner) Leaf disk Feeding deterrence = 4. Treatment to 4th


(Beet armyworm) No-choice test 1000 ppm 70.04% instar larvae pre-
Choice test 1000 ppm 67.9% starved for 6 h.
(4)

(1) Kubo, I., Lee, Y., Balogh-Nair, V., Nakanishi, K., and Chapya, A. (1976) J. Chem. Soc. Chem Commun., 949.
(2) Cole, M.D., Anderson, J.C., Blaney, W.M., Fellows, L.E., Ley, S.V., Sheppard, R.N., and Simmonds, M.S.J.
(1990) Phytochemistry, 29, 1793.
(3) Kubo, I. and Nakanishi, K. (1979) Adv. Pestic. Sci., 2, 284.
(4) Caballero, C., Castanera, P., Ortego, F., Fontana, G., Pierro, P., Savona, G., and Rodriguez, B. (2001)
Phytochemistry, 58, 249.

© 2005 by CRC Press LLC


Insect Antifeedants 129

AJUGARIN–II C22H36O6
(396.52)
M.p. : 188–189°

O [α]D24 : +14.6° (CDCl3)

H
O

O
OH

CH2OAc

(1) (1,2)

SOURCE: Ajuga remota Benth., African ajuga (Labiatae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera exempta (Walker) Leaf disk 100 ppm Minimum level of 1. Treatment to
(African armyworm) choice test treatment to exhibit larvae at random.
antifeedant activity. (1)

2. Spodoptera littoralis (Boisd.) Leaf disk 300 ppm Minimum level of 2. Treatment to
(Egyptian cotton leaf worm) choice test treatment to exhibit larvae at random.
antifeedant activity. (1)

(1) Kubo, I., Lee, Y., Balogh-Nair, V., Nakanishi, K., and Chapya, A. (1976) J. Chem. Soc. Chem. Commun., 949.
(2) (1994) Dictionary of Natural Products, Chapman & Hall, London.

© 2005 by CRC Press LLC


130 Opender Koul

AJUGARIN–III C24H36O8
(452.54)
M.p. : 243–245°
O

H O

HO
HOH2C OAc
CH2OAc
(1) (1)

SOURCE: Ajuga remota Benth., African ajuga (Labiatae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera exempta (Walker) Leaf disk 100 ppm Minimum level of Treatment to larvae
(African armyworm) choice test treatment to exhibit at random.
antifeedant activity. (2)

(1) Kubo, I., Lee, Y., Balogh-Nair, V., Nakanishi, K., and Chapya, A. (1976) J. Chem. Soc. Chem. Commun., 949.
(2) Kubo, I. and Nakanishi, K. (1979) Adv. Pestic. Sci., 2, 284.

© 2005 by CRC Press LLC


Insect Antifeedants 131

ALANTOLACTONE C15H20O2
(232.32)
M.p. : 78.5–80.0°

B.p. : 275°

[α]D : +175° (CHCl3)


O
O

CH2

(1, 2) (1, 2)

SOURCE: Inula helenium L., eleocampane (Asteraceae) (1, 3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius L. Wafer disk 10.0 mg/cm3 Feeding deterrence 1. Treatment given to
(Grain weevil) test coefficient = adults.
119 (adults) (3)

2. Tribolium confusum Jacq. Wafer disk 10.0 mg/cm3 Feeding deterrence 2. Treatment given to
Duv. test coefficient = both adults and
(Confused flour beetle) 197 (adults) larvae.
177 (larvae) (3)

3. Trogoderma granarium Wafer disk 10.0 mg/cm3 Feeding deterrence 3. Treatment given to
Everts test coefficient = adults.
(Khapra beetle) 148 (adults)
Neutral value = 0
Absolute feeding
deterrence value =
200.
(3)

(1) Asselineau, C. and Borg, S. (1958) Comp. Rend., 246, 1874.


(2) Marshall, J.A. and Cohen, N. (1964) J. Org. Chem., 29, 3727.
(3) Streibl, M., Nawrot, J., and Herout, V. (1983) Biochem. Syst. Ecol., 11, 381.

© 2005 by CRC Press LLC


132 Opender Koul

ALATOLIDE C19H26O6
(350.41)
M.p. : 59–61°

[α]D25 : +64.4° (CHCl3)

CH2OH
OCO

CH2

O
CH2OH
O

(1, 2) (1, 2)

SOURCE: Jurinea alata Cass., jurinea weed (Asteraceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius L. Wafer disk 8.0 mg/cm3 Feeding deterrence 1. Treatment given to
(Grain weevil) test coefficient = adults.
51–100 (adults) (2)

2. Tribolium confusum Jacq. Wafer disk 8.0 mg/cm3 Feeding deterrence 2. Treatment given to
Duv. test coefficient = both adults and
(Confused flour beetle) 51–100 (adults) larvae.
101–150 (larvae) (2)

3. Trogoderma granarium Wafer disk 8.0 mg/cm3 Feeding deterrence 3. Treatment given to
Everts test coefficient = larvae.
(Khapra beetle) 151–200 (adults)
Neutral value = 0
Absolute feeding
deterrence value =
200.
(2)

(1) Drozdz, B., Samek, Z., Holub, M., and Herout, V. (1973) Collect. Czech. Chem. Commun., 38, 727.
(2) Nawrot, J., Bloszyk, K.E., Grabarczyk, H., and Drozdz, B. (1982) Prace. Nauk. Inst. Ochr. Roslin, 24, 27.

© 2005 by CRC Press LLC


Insect Antifeedants 133

ALBIZZINE C4H9O3N3
(147.14)
M.p. : 218–220° (dec.)

[α]25
D : –66.2° (H2O)

COOH

H 2N C H

CH2NHCONH2

(1, 2) (1, 2)

SOURCE: Acacia sp. (Fabaceae) (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Locusta migratoria Glass fiber 1.0% Feeding inhibition = Treatment to male 5th
migratoriodes (R & F) disk test of disk 91–100% instar nymphs.
(Migratory locust) weight (3)

(1) Gmelin, R., Strauss, G., and Hasenmaier, G. (1958) Z. Naturforsch., 13B, 252.
(2) Kjaer, A., Larsen, P.O., and Gmelin, R. (1959) Experientia, 15, 253.
(3) Evans, C.S. and Bell, E.A. (1979) Phytochemistry, 18, 1807.

© 2005 by CRC Press LLC


134 Opender Koul

ALLIARINOSIDE C10H15O6N
(245.22)
Colorless gum

Only spectral data given


OH

O
HO O
HO
OH
H CN

(1) (1)

SOURCE: Alliaria petiolata Cavara and Grande, garlic mustard (Cruciferae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Pieris napi oleracea L. Leaf disk 0.1 g leaf Feeding inhibition Treatment to neonate
(Green-veined white butterfly) choice test equivalent/ observed. No larvae for 18 h.
20 µl/1.5 quantitative data (1)
cm disk given.

(1) Haribal, M., Yang, Z., Attygalle, A.B., Renwick, A.J.A., and Meinwald, J. (2001) J. Nat. Prod., 64, 440.

© 2005 by CRC Press LLC


Insect Antifeedants 135

2-AMINO-3-OXALYL AMINO C5H8O5N2


PROPANOIC ACID (176.13)
M.p. : 206° (dec.)

[α]D27 : –36.9° (HCl)

COOH

H C NH2

CH2NHCOCOOH

(1, 2) (1)

SOURCE: Acacia sp. (Fabaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Anacridium melanorhodon Glass fiber 0.5% of Feeding inhibition = 1. Treatment at


arabafrum (Dirsh.) disk test disk weight 61–90% random to 3rd to 6th
(Tree locust) instar nymphs.
1.0% of Feeding inhibition = (2)
disk weight 91–100%

2. Locusta migratoria Glass fiber 1.0% of Feeding inhibition = 2. Treatment to male


migratoriodes disk test disk weight 30–60% 5th instar nymphs.
(R and F) (2)
(Migratory locust) 10.0% of Feeding inhibition =
disk 91–100%
weight

(1) (1994) Dictionary of Natural Products, Chapman & Hall, London.


(2) Evans, C.S. and Bell, E.A. (1979) Phytochemistry, 18, 1807.

© 2005 by CRC Press LLC


136 Opender Koul

AMYGDALIN C20H27O11N
(457.43)
M.p. : 220° (anhydr.)

[α]20
D : –42° (H2O)
CH2OH CN

O O
OH O C H
O
OH
OH

OH OH
OH

(1) (1)

SOURCE: Sorghum bicolor (L.) Moench., grain sorghum (Poaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Schizaphis graminum (Rondani) Synthetic 0.5% Feeding inhibition = Treatment to 50–75


(Wheat aphid) diet feeding 50% aphids of all ages for
24 h.

Concentration = EC50
value.
(2)

LD50 (rats): 522 mg/kg (oral) (3)

(1) Haworth, W.N. and Wylam, B. (1923) J. Chem Soc., 3120.


(2) Dreyer, D.L., Reese, J.C., and Jones, K.C. (1981) J. Chem. Ecol., 7, 273.
(3) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC


Insect Antifeedants 137

ANDROGRAPHOLIDE C20H30O5
(350.45)
M.p. : 230–231°
O
[α]26
D : –126° (AcOH)

HO O

CH2

HO

CH2OH

(1) (2)

SOURCE: Andrographis paniculata (Burm. f.) Wall. ex. Nees, king of bitters (Acanthaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Plutella xylostella (L.) Leaf disk 2.5 µg/2 cm Feeding inhibition = 1. Treatment to 4th
(Diamondback moth) no-choice diameter 50% stadium larvae for 24
test leaf disk h. Insects pre-starved
for 3 h.

Concentration
corresponds to FI50
value calculated
from Reference 1.
(1)

2. Nephotettix cincticeps (Uhler) Artificial 1.0 ppm Feeding inhibition = 2. Treatment to


(Green rice leafhopper) diet feeding 83.4% hoppers for 24 h.
(3)

(1) Hermawan, W., Nakajima, S., Tsukuda, R., Fujisaki, K., and Nakasuji, F. (1997) Appl. Entomol. Zool., 32, 551.
(2) (1982) Dictionary of Organic Compounds, Vol. 1, Chapman & Hall, New York, p. 351.
(3) Widiasta, I.N., Hermawan, W., Oya, S., Nakajima, S., and Nakasuji, F. (1997) Appl. Entomol. Zool., 32, 561.

© 2005 by CRC Press LLC


138 Opender Koul

ANGELICIN C11H6O3
(186.17)
M.p. : 138–139.5°

O O O

(1, 2, 3) (1, 2)

SOURCE: Angelica archangelica L., garden angelica (Apiaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura Fab. Leaf disk no- 1000 ppm Feeding ratio = 4% Treatment to 3rd
(Tobacco armyworm) choice test instar larvae. Activity
ratio between 0 and
20% considered high
active value.
(3)

Artificial diet 616 ppm Feeding inhibition = Treatment to 4th


feeding 50% instar larvae pre-
starved for 4 h.
Treatment given for
48 h.
Concentration = FI50
value.
(4)

LD50 (rats): 322 mg/kg (oral) (5)

(1) Spath, E. and Pailer, M. (1934) Ber., 67, 1212; (1935) Ber., 68, 943.
(2) Spath, E. and Pesta, O. (1934) Ber., 67, 853.
(3) Yajima, T. and Munakata, K. (1979) Agric. Biol. Chem., 43, 1701.
(4) Luthria, D.L., Ramakrishnan, V., Verma, G.S., Prabhu, B.R., and Banerji, A. (1989) J. Agric. Food Chem.,
37, 1435.
(5) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC


Insect Antifeedants 139

8α-ANGELOYLOXYCOSTUNOLIDE C20H26O4
(330.42)
Only spectral data given

O
CH2
O

(1) (1)

SOURCE: Tanacetum argenteum (Lam.) Willd., tansy (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera littoralis (Boisd.) Artificial diet 0.5 µmol/g Feeding inhibition = Treatment to neonate
(Egyptian cotton leaf worm) feeding 37.5% larvae.

1.0 µmol/g Feeding inhibition = EC50 = 0.63 µmol/g


54.9%
(1)
2.5 µmol/g Feeding inhibition =
97.69%

(1) Goren, N., Tahtasakal, E., Pezzuto, J.M., Cordell, G.A., Schwarz, B., and Proksch, P. (1994) Phytochemistry,
36, 389.

© 2005 by CRC Press LLC


140 Opender Koul

5α-ANGELOYLOXYSILPHINEN-3-ONE C20H28O3
(316.42)
Oil

[α]D : –59.2° (CHCl3)

O O

(1) (1)

SOURCE: Senecio palmensis Chr.Sm., groundsel (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera littoralis (Boisd.) Choice >200 Feeding deterrence = 1. Treatment to 6th


(Eygyptian cotton leaf worm) feeding nmol/cm2 50.0% instar larvae.
assay

2. Leptinotarsa decemlineata Choice >150 Feeding deterrence = 2. Treatment to


(Say) feeding nmol/cm2 50.0% adults.
(Colorado potato beetle) assay

3. Myzus persicae (Sulzer) Choice >200 Feeding deterrence = 3. Treatment to


(Green peach aphid) feeding nmol/cm2 50.0% apterous adult
assay aphids.

4. Rhopalosiphum padi (L.) Choice ~190 Feeding deterrence = 4. Treatment to


(Cereal aphid) feeding nmol/cm2 50.0% apterous adult
assay aphids.

5. Sitobion avenae (Fab.) Choice 31.6 Feeding deterrence = 5. Treatment to


(Grass aphid) feeding nmol/cm2 50.0% apterous adult
assay aphids.

6. Diuraphis noxia (Mordvilko) Choice >150 Feeding deterrence = 6. Treatment to


(Wheat aphid) feeding nmol/cm2 50.0% apterous adult
assay aphids.
Concentrations =
EC50 values.
(1)

(1) Reina, M., Nold, M., Santana, O., Orihuela, J.C., and Gonzalez-Coloma, A. (2002) J. Nat. Prod., 65, 448.

© 2005 by CRC Press LLC


Insect Antifeedants 141

ANGULATUEOID–G C33H36O9
(552.62)
Only spectral data given

O
OH
O
H
O OH

O
OAc

(1) (1)

SOURCE: Celastrus angulatus Maxim., bittersweet tree (Celastraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Plutella xylostella (L.) Leaf disk no- 100 ppm Feeding inhibition = 1. Treatment to
(Diamondback moth) choice test 87.7% larvae.

2. Aulacophora femoralis Leaf disk no- 100 ppm Feeding inhibition = 2. Treatment to
(Motsch.) choice test 73.2% beetles.
(Leaf beetle) (1)

(1) Dagang, Wu, Jikai, L., and Chunquan, C. (1992) Phytochemistry, 31, 4219.

© 2005 by CRC Press LLC


142 Opender Koul

ANGUSTONE–A C25H26O6
(422.48)
M.p. : 159–160°

HO O

OH O
HO OH

(1, 2) (1)

SOURCE: Lupinus angustifolius L., European blue lupine (Fabaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Costelytra zealandica Synthetic 200 µg/ml Feeding inhibition = 1. Treatment to 24-h


(White) diet disk 69% starved 3rd instar
(Scarab beetle) feeding larvae for 24 h.
Percentage feeding
inhibition calculated
from Reference 2.
(2)

2. Heteronychus arator Fab. Synthetic 200 µg/ml Feeding inhibition = 2. Treatment to 24-h
(Pasture scarab beetle) diet disk 43.0% starved 3rd instar
feeding larvae for 24 h. Data
calculated from
Reference 3.
(3)

(1) Lane, G.A. and Newman, R.H. (1987) Phytochemistry, 26, 295.
(2) Lane, G.A., Biggs, D.R., Russel, G.B., Sutherland, O.R.W., Williams, E.M., Maindonald, J.H., and Donnell,
D.J. (1985) J. Chem. Ecol., 11, 1713.
(3) Lane, G.A., Sutherland, O.R.W., and Skipp, R.A. (1987) J. Chem. Ecol., 13, 771.

© 2005 by CRC Press LLC


Insect Antifeedants 143

ANGUSTONE–B C25H24O6
(420.46)
M.p. : 160–161°

HO O

OH O
HO O

(1, 2) (1)

SOURCE: Lupinus angustifolius L., European blue lupine (Fabaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Costelytra zealandica (White) Synthetic 20 µg/ml Feeding inhibition = Treatment to 24-h


(Scarab beetle) diet disk 49.0% starved 3rd instar
feeding larvae for 24 h.
100 µg/ml Feeding inhibition = Percentage feeding
64.0% inhibition calculated
from Reference 2.
(2)

(1) Lane, G.A. and Newman, R.H. (1987) Phytochemistry, 26, 295.
(2) Lane, G.A., Sutherland, O.R.W., and Skipp, R.A. (1987) J. Chem. Ecol., 13, 771.

© 2005 by CRC Press LLC


144 Opender Koul

ANGUSTONE–C C25H24O6
(420.46)
M.p. : 170–180°

O O

OH O
HO OH

(1, 2) (1)

SOURCE: Lupinus angustifolius L., European blue lupine (Fabaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Costelytra zealandica (White) Synthetic 20 µg/ml Feeding inhibition = Treatment to 24-h


(Scarab beetle) diet disk 44.0% starved 3rd instar
feeding larvae for 24 h.
Percentage feeding
inhibition calculated
from Reference 2.
(2)

(1) Lane, G.A. and Newman, R.H. (1987) Phytochemistry, 26, 295.
(2) Lane, G.A., Sutherland, O.R.W., and Skipp, R.A. (1987) J. Chem. Ecol., 13, 771.

© 2005 by CRC Press LLC


Insect Antifeedants 145

ANTHOTHECOL C28H32O7
(480.56)
M.p. : 225°

[α]20
D : –63° (CHCl3)
O

AcO

O O

OH

(1, 2) (1, 2)

SOURCE: Khaya anthotheca (Welw.) CDC, khaya wood (Meliaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Ostrinia nubilalis Hubner Leaf disk test 50 µg/g Feeding inhibition = Treatment to neonate
(European corn borer) 80.0% larvae for 48 h.

500 µg/g Feeding inhibition = Data calculated from


91.0% Reference 3.
(3)

(1) Kubo, I. and Klocke, J.A. (1981) Colloques Inst. Nat. Recherches Agric., 7, 117.
(2) (1982) Dictionary of Organic Compounds, Vol. 1, Chapman & Hall, New York, p. 381.
(3) Arnason, J.T., Philogene, B.J.R., Donskov, N., and Kubo, I. (1987) Entomol. Exp. Appl., 43, 221.

© 2005 by CRC Press LLC


146 Opender Koul

ANTHRANILIC ACID C7H7O2N


(137.14)
M.p. : 144–148°

COOH

NH2

(1) (1)

SOURCE: Alchornea triplinervia (Spreng.) Muell. Arg., tapia (Euphorbiaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Anthonomus grandis Bohem. Synthetic 10 mg/4 cm2 Feeding ratio = 12 Treatment to freshly
(Boll weevil) diet feeding emerged boll
weevils.

20 mg/4 cm2 Feeding ratio = 11 Feeding ratio based


on treated/control
values. Total feeding
30 mg/4 cm2 Feeding ratio = 6 inhibition value = 0
and >100 value
denotes attraction.
(1)

LD50 (mice): 1400 mg/kg (oral) (2)

(1) Miles, D.H., Hankinson, B.L., and Randle, S.A. (1985) Proc. ACS Symp. Ser., 276, 469.
(2) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC


Insect Antifeedants 147

ANTHRAQUINONE-2-ALDEHYDE C15H8O3
(236.21)
M.p. : 188–191°

CHO

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk 0.75 µmol/cm2 Feeding deterrence = Treatment to 3rd
(Tobacco armyworm) assay 50% instar larvae for 6 h.
choice
test Concentration =
ED50 value.
(1)

(1) Morimoto, M., Tanimoto, K., Sakatani, A., and Komai, K. (2002) Phytochemistry, 60, 163.

© 2005 by CRC Press LLC


148 Opender Koul

APHANASTATIN C35H46O13
(Trichilin E) (674.74)
O M.p. : 269–271°
20
OH [α]D : –38.9° (Py/CH3OH)

O
AcO

HO

O O

AcO
OH

OCO

(1, 2) (1)

SOURCE: Melia azedarach L., chinaberry (Meliaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera eridania Leaf disk 200 ppm Feeding inhibition = 1. Treatment to 3rd
(Cramer) choice test Threshold level instar larvae for 6–24
(Southern armyworm) h, during which
period 50% of one of
the disks was
consumed.

2. Spodoptera exigua (Hubner) Leaf disk 200 ppm Feeding inhibition =


(Beet armyworm) choice test Threshold level
(2)

(1) Polonsky, J., Varon, Z., Arnoux, B., Pascard, C., Pettit, G.R., Schmidt, J.H., and Lang, L.M. (1978) J. Am.
Chem. Soc., 100, 2575.
(2) Nakatani, M., Huang, R.C., Okamura, H., Iwagawa, T., Tadera, K., and Naoki, H. (1995) Tetrahedron, 51,
11731.

© 2005 by CRC Press LLC


Insect Antifeedants 149

ARCHANGELOLIDE C29H40O10
(548.63)
M.p. : 109–112°

[α]D : –120.2° (MeOH)


OAc
CO.O

OOC

O
OAc

(1, 2) (3)

SOURCE: Laserpitium archangelica Wulf., laserwort (Apiaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius L. Wafer disk 1.0% Feeding deterrence 1. Treatment given to


(Grain weevil) test coefficient = adults.
44 (adults) (2)

2. Tribolium confusum Jacq. Wafer disk 1.0 % Feeding deterrence 2. Treatment given to
Duv. test coefficient = both adults and
(Confused flour beetle) 49 (adults) larvae.
80 (larvae) (2)

3. Trogoderma granarium Wafer disk 1.0% Feeding deterrence 3. Treatment given to


Everts test coefficient = larvae.
(Khapra beetle) 52 (larvae)
Neutral value = 0
Absolute feeding
deterrence value =
200.
(2)

(1) Holub, M. and Samek, Z. (1973) Collect. Czech. Chem. Commun., 38, 731.
(2) Nawrot, J., Smitalova, Z., and Holub, M. (1983) Biochem. Syst. Ecol., 11, 243.
(3) Holub, M., Budesinsky, M., Smitalova, Z., and Saman, D. (1984) Tetrahedron Lett., 25, 3755.

© 2005 by CRC Press LLC


150 Opender Koul

ARCTOLIDE C17H20O6
(320.34)
M.p. : 144–145°

[α]D : +64.1° (MeOH)


H O

AcO O

OH O
CH2
CH2

(1, 2) (1, 2)

SOURCE: Arctotis grandis Thumb., African daisy (Asteraceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius L. Wafer disk 10 mg/cm3 Feeding deterrence 1. Treatment given to


(grain weevil) test coefficient = adults.
95.1 (adults) (2)

2. Tribolium confusum Jacq. Wafer disk 10 mg/cm3 Feeding deterrence 2. Treatment given to
Duv. test coefficient = both adults and
(Confused flour beetle) 145.1 (adults) larvae.
154.4 (larvae) (2)

3. Trogoderma granarium Wafer disk 10 mg/cm3 Feeding deterrence 3. Treatment given to


Everts test coefficient = larvae.
(Khapra beetle) 170.8 (larvae)
Neutral value = 0
Absolute feeding
deterrence value =
200.
(2)

(1) Samek, Z., Holub, M., Grabarczyk, H., and Drozdz, B., (1977) Collect. Czech. Chem. Commun., 42, 2217.
(2) Nawrot, J., Bloszyk, E., Grabarczyk, H., Drozdz, B., Daniewski, W.M., and Holub, M. (1983) Prace. Nauk.
Inst. Ochr. Roslin, 25, 91.

© 2005 by CRC Press LLC


Insect Antifeedants 151

ARECOLINE C8H13O2N
(155.19)
B.p. : 209°

n20
D : 1.4302

COO

(1, 2, 3) (1, 2)

SOURCE: Commercial sample (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Phormia regina Meigen Sucrose 10 mM Feeding inhibition = Treatment to 2-, 4-,


(Blow fly) solution 51% (after 6 h) and 6-day-old adults,
feeding pre-starved for 24 h.
Feeding inhibition = (3)
63% (after 24 h)

LD50 (mice): 100 mg/kg (s.c.) (4)

(1) Johns, E. (1891) Arch. Pharm., 229, 673.


(2) Chemnitius, F. (1928) J. Prakt. Chem., 117, 147.
(3) Blades, D. and Mitchell, B.K. (1986) Entomol. Exp. Appl., 41, 299.
(4) Burrows, R.B. (1973) Progr. Drug Res., 17, 108.

© 2005 by CRC Press LLC


152 Opender Koul

ARGOPHYLLIN–A C20H28O7
(380.44)
M. p.: 190–192°

O [α]D22 : –157° (CHCl3)

O
O
OH

HO CH2
O

(1, 2) (1, 2, 3)

SOURCE: Helianthus annuus L., sunflower (Asteraceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Diabrotica virgifera virgifera Leaf disk 40 µg/1.5 cm2 Feeding inhibition = Treatment to adults.
LeConte test 77% approximately Data based on
(Western corn rootworm) in 24 h. consumption of 32%
after 5 h and 23%
Calculated from after 24 h in
Reference 2. comparison to
controls.
(2)

(1) Melek, F.R., Gage, D.A., Gershenzon, J., and Mabry, T.J. (1985) Phytochemistry, 24, 1537.
(2) Mullin, C.A., Alfatafta, A.A., Harman, J.L., Everett, S.L., and Serino, A.A. (1991) J. Agric. Food Chem., 39,
2293.
(3) Watanabe, K., Ohno, N., Yoshioka, H., Gershenzon, J., and Mabry, T.J. (1982) Phytochemistry 21, 709

© 2005 by CRC Press LLC


Insect Antifeedants 153

ARISTOLOCHIC ACID C17H11O7N


(341.28)
M.p. : 281–286° (dec.)

COOH
O

NO2
O

OCH3

(1) (1)

SOURCE: Aristolochia albida Duch., Nigerian climber (Aristolochiaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera litura Fab. Leaf disk 500 ppm Feeding inhibition 1. Treatment to
(Tobacco armyworm) choice index = 0 4-day-old larvae for
bioassay 1 day.
100 ppm Feeding inhibition Antifeedant index
index = 3.73 value below 20
considered highly
50 ppm Feeding inhibition deterrent.
index = 19.96 (1)

LD50 (rats): 184 mg/kg (oral) (2)

(1) Lajide, L., Escoubas, P., and Mizutani, J. (1993) J. Agric. Food Chem., 41, 669.
(2) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC


154 Opender Koul

ARTECANIN C15H18O5
(Chrysartemin B) (278.30)
M.p. : 244–245°

OH [α]23
D : +26.6° (C2H5OH)
O

O
H CH2
O

(1, 2) (1, 2)

SOURCE: Chrysanthemum macrophyllum W & K, chrysanthemum (Asteraceae) (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius L. Wafer disk 8.0 mg/cm3 Feeding deterrence 1. Treatment given to
(Grain weevil) test coefficient = adults.
51–100 (adults) (3)

2. Tribolium confusum Jacq. Wafer disk 8.0 mg/cm3 Feeding deterrence 2. Treatment given to
Duv. test coefficient = both adults and
(Confused flour beetle) 101–150 (adults) larvae.
101–150 (larvae) (3)

3. Trogoderma granarium Wafer disk 8.0 mg/cm3 Feeding deterrence 3. Treatment given to
Everts test coefficient = larvae.
(Khapra beetle) 101–150 (larvae)
Neutral value = 0
Absolute feeding
deterrence value =
200.
(3)

(1) Lee, K.H., Simpson, R.F., and Geissman, T.A. (1969) Phytochemistry, 8, 1515.
(2) Bhadane, N.R. and Shafizadeh, F. (1975) Phytochemistry, 14, 2651.
(3) Nawrot, J., Bloszyk, E., Grabarczyk, H., and Dorzdz, B. (1982) Prace. Nauk. Inst. Ochr. Roslin, 24, 27.

© 2005 by CRC Press LLC


Insect Antifeedants 155

ARTEMISININ C15H22O5
(282.34)
M. p.: 156–157°

[α]17
D : 66.3° (neat)

O
H
O
O
O
H
O

(1, 2) (1)

SOURCE: Artemisia annua L., annual wormwood (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Diabrotica virgifera virgifera Leaf disk 40 µg/1.5 cm2 Feeding inhibition = Treatment to adults.
LeConte test 59% approximately Data based on
(Western corn rootworm) in 24 h. consumption of 32%
after 5 h and 41%
Calculated from after 24 h in
Reference 2. comparison to
controls.
(2)

80 µg/1.5 cm2 Feeding inhibition = Treatment to adults.


60% approximately Data based on
in 24 h. consumption of 20%
after 5 h and 40%
Calculated from after 24 h in
Reference 2. comparison to
controls.
(2)

LD50 (mice): 5105 mg/kg (oral) (3)

(1) (1994) Dictionary of Natural Products, Chapman & Hall, London.


(2) Mullin, C.A., Mason, C.H., Chou, J., and Linderman, J.R. (1992) In C.A. Mullin and J.G. Scott (eds.),
Molecular Mechanisms of Insecticide Resistance: Diversity Among Insects, ACS Symp. Ser. 505, Washington,
D.C., pp. 288–308.
(3) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC


156 Opender Koul

ASIATIC ACID C30H48O5


(488.71)
M.p. : 300–305°

COOH
HO

HO
HO

(1, 2) (2)

SOURCE: Shorea robusta Gaertn. f., sal (Dipterocarpaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Oxya fuscovittata (Marsh.) Whole leaf 0.5% Feeding inhibition = Treatment to


(Rice grasshopper) application 100% overnight-starved 6th
from Coix (1 ml/g) instar nymphs for
lachryma of leaf 24 h.
leaves (3)

(1) Purushothman, K.K., Saraswathy, A., and Sasikala, E. (1988) Indian Drugs, 26, 146.
(2) (1994) Dictionary of Natural Products, Chapman & Hall, London.
(3) Sanjayan, K.P. and Dhang, P.P. (1993) J. Appl. Ent., 115, 506.

© 2005 by CRC Press LLC


Insect Antifeedants 157

ASIMICIN C37H66O7
(Annonastatin) (622.92)
M.p. : 70–72°
OH
O
[α]D : +21.8° (MeOH)

O
O
OH

OH
(1, 2) (1, 2, 3)

SOURCE: Rollinia sylvatica (A. St.-Hill) Mart., araticum (Annonaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Acalymma vittatum (Fab.) Whole leaf 0.5 ppm Feeding inhibition = Treatment to beetles.
(Striped cucumber beetle) application 100% (2)

(1) Cortes, D. et al. (1991) Tetrahedron Lett. 32, 6133.


(2) Mikolajczak, K.L., McLaughlin, J.L., and Rupprecht, J.K. (1986) U.S. Patent Appl. 860351, 28 pp.
(3) Rupprecht, J.K., Chang, C.J., Cassady, J.M., and McLaughlin, J.L. (1986) Heterocycles, 24, 1197.

© 2005 by CRC Press LLC


158 Opender Koul

ATALANTIN C27H32O9
(500.54)
M.p. : 184–185°
O
[α]D22 : +84.4° (CHCl3)
O
OCH3

O
O O

OH

(1, 2) (1, 2, 3)

SOURCE: Severinia buxifolia (Poir.) Tenore., Chinese box orange (Rutaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Plutella xylostella (L.) Leaf disk 0.0625% Feeding inhibition = Treatment to 3rd
(Diamondback moth) choice test 50% instar larvae.

Concentration = EC50
value.
(1)

(1) Wu, T.S., Leu, Y.L., Chan, Y.Y., Wu, P.L., Kuoh, C.S., Wu, S.J., and Wang, Y. (1997) Phytochemistry, 45, 1393.
(2) Basu, D. and Basu, S.C. (1972) J. Org. Chem., 37, 3035.
(3) Dreyer, D.L., Bennett, R.D., and Basa, S.C. (1976) Tetrahedron, 32, 2367.

© 2005 by CRC Press LLC


Insect Antifeedants 159

ATROPINE C17H23O3N
(289.38)
M.p. : 114–116°
N

CH2OH

OOCCH

(1, 2, 3) (1, 2)

SOURCE: Commercial sample (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Phormia regina Meigen Sucrose 10 mM Feeding inhibition = Treatment to 2-, 4-,


(Blow fly) solution 86.0% after 6 h and and 6-day-old adults
feeding 83.0% after 24 h. pre-starved for 24 h.
(3)

LD50 (rats): 750 mg/kg (oral) (4)

(1) Chemnitius, F. (1927) J. Prakt. Chem., 116, 276.


(2) Schwenker, G., Premtzell, W., Gassuer, U., and Gerber, R. (1966), Ber. 99, 2407.
(3) Blades, D. and Mitchell, B.K. (1986) Entomol. Exp. Appl., 41, 299.
(4) Cahen, R.L. and Tvede, K.M. (1952) J. Pharmacol. Exp. Ther., 105, 166.

© 2005 by CRC Press LLC


160 Opender Koul

AZADIRACHTIN–A C35H44O16
(720.72)
M.p. : 155–158°
(165°)
[α]20
D : –65.4° (CHCl3)
O COOCH3
OH OH
O O

O
O

AcO OH
H
H3COOC O

(1, 2) (1, 2)

SOURCE: Azadirachta indica A. Juss., neem (Meliaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera littoralis (Boisd.) Glass fiber 1.0 ppm Feeding deterrence = 1. Treatment to 24- to
(Egyptian cotton leaf worm) disk choice 99.0%, calculated 36-h-old pre-starved
test from Reference 3 final stadium larvae.
Bioassay terminated
No-choice 1.0 ppm Feeding deterrence = after the larvae had
test 90.0%, calculated eaten approximately
from Reference 3 50% of one of the
disks.
(3)
Artificial diet 10.0 ppm Feeding deterrence = Treatment given to
feeding 100.0% larvae.
(4)

Foiliage 0.06 ppm Feeding deterrence = Treatment for larvae.


spray 50.0% (5)

Foiliage 600 ppm Feeding deterrence = Treatment for larvae.


spray 100.0% (6)

(1) Kraus, W., Bokel, M., Klenk, A., and Pohnl, H.D. (1985) Tetrahedron Lett., 26, 6435.
(2) Kraus, W., Bokel, M., Bruhn, A., Cramer, R., Klaiber, I., Klenk, A., Nagl., G., Pohnl., H., Sadlo, H., and
Vogler, B. (1987) Tetrahedron, 43, 2817.
(3) Blaney, W.M., Simmonds, M.S.J., Ley, S.V., Anderson, J.C., and Toogood, P.L. (1990) Entomol. Exp. Appl.,
55, 149.
(4) Meisner, J., Ascher, K.R.S., Aly, R., and Warthen, J.D. Jr. (1981) Phytoparasitica, 9, 27.
(5) Plieger, D. and Muckenstrum, B. (1987) Tetrahedron Lett., 28, 1519.

© 2005 by CRC Press LLC


Insect Antifeedants 161

AZADIRACHTIN–A (Cont.)

SOURCE:

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

2. Spodoptera frugiperda Glass fiber 1.0 ppm Feeding deterrence = 2. Treatment to 24- to
(J.E. Smith) disk choice- 90.0%, calculated 36-h-old pre-starved
(Fall armyworm) test. from Reference 3 final stadium larvae.
Bioassay terminated
No-choice 1.0 ppm Feeding deterrence = after the larvae had
test 84.3%, calculated eaten approximately
from Reference 3 50% of one of the
disks.
(3)

Leaf disk test 50.0 ppm Feeding deterrence = Treatment to larvae.


43.0% (7)

3. Heliothis virescens (Fab.) Glass fiber 1.0 ppm Feeding deterrence = 3. Treatment to 24- to
(Tobacco budworm) disk choice- 77.0%, calculated 36-h-old pre-starved
test. from Reference 3 final stadium larvae.

(6) Klocke, J.A. and Barnby, M.A. (1989) In C.H. Chou and G.R. Walls (eds.) Phytochemical Ecology: Alle-
lochemicals, Mycotoxins and Insect Pheromones and Allomones, Inst. of Botany, Academia Sinica Monograph
Series No. 9, Taipei, Taiwan.
(7) Raffa, K.F. (1987) J. Econ. Entomol., 80, 384.

© 2005 by CRC Press LLC


162 Opender Koul

AZADIRACHTIN–A (Cont.)

SOURCE:

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

No-choice 1.0 ppm Feeding deterrence = Bioassay terminated


test 88.9%, calculated after the larvae had
from Reference 3 eaten approximately
50% of one of the
disks.
(3)

Artificial diet 0.07 ppm Feeding deterrence = Concentration = EC50


feeding 50.0%. value.
(8)

4. Helicoverpa armigera Glass fiber 1.0 ppm Feeding deterrence = 4.Treatment to 24- to
(Hubner) disk choice 85.0%, calculated 36-h-old pre-starved
(Gram pod borer) test. from Reference 3 final stadium larvae.
(3)

(8) Yamasaki, R.B. and Klocke, J.A. (1987) J. Agric. Food Chem., 35, 467.

© 2005 by CRC Press LLC


Insect Antifeedants 163

AZADIRACHTIN–A (Cont.)

SOURCE:

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

5. Spodoptera litura Fab. Leaf disk 0.015 µg/cm2 Feeding deterrence = 5. Treatment to 5th
(Tobacco armyworm) choice test 50.0% instar larvae for 6 h.
Concentration = EC50
value.
(9)

50 ppm Feeding deterrence = Treatment to freshly


37.0% moulted 4th instar
larvae for 24 h.
(10)

6. Peridroma plorans Artificial 0.4 ppm Feeding deterrence = 6. Treatment to


(Cutworm) diet 50.0% larvae.
feeding Concentration = EC50
value.
(11)

(9) Koul, O., Shankar, J.S., and Kapil, R.S. (1996) Entomol. Exp. Appl., 79, 43.
(10) Ramachandran, R., Mukherjee, S.N., and Sharma, R.N. (1989) Entomol. Exp. Appl., 51, 29.
(11) Champagne, D.E., Isman, M.B., and Towers, G.H.N. (1989) ACS Symp. Ser. 387, Am. Chem. Soc.,
Washington, D.C., pp. 95–109.

© 2005 by CRC Press LLC


164 Opender Koul

AZADIRACHTIN–A (Cont.)

SOURCE:

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

7. Peridroma saucia (Hubner) Leaf disk 2.4 ppm Feeding deterrence = 7. Treatment to 4th
(Variegated cutworm) choice test 50.0% instar larvae for 6 h.
Concentration = EC50
value.
(12)

8. Earias insulana Boisd. Artificial diet 50.0 ppm Feeding deterrence = 8. Treatment to
(Spotted bollworm) feeding 100.0% larvae.
(13)

9. Ostrinia nubilalis (Hubner) Leaf disk test 24.0 ppm Feeding deterrence = 9. Treatment to 3rd
(European corn borer) 50.0%. Data instar larvae up to
calculated on the 72 h.
basis of protection Concentration = PC50
concentration (PC). and PC95 value.
790 ppm Feeding inhibition = (14)
95%

(12) Isman, M.B., Koul, O., Luczynski, A., and Kaminski, J. (1990) J. Agric. Food Chem., 38, 1406.
(13) Schwinger, M., Ehhammer, B., and Kraus, W. (1984) Proc. 2nd Int. Neem Conf., GTZ, Eschborn, Germany,
pp. 181–198.
(14) Arnason, J.T., Philogene, B.J.R., Donskov., N., Hudon, M., McDougall, C., Fortier, G., Morand, P., Gardner,
D., Lambert, J., Morris, C., and Nozzolillo, C. (1985) Entomol. Exp. Appl., 38, 29.

© 2005 by CRC Press LLC


Insect Antifeedants 165

AZADIRACHTIN–A (Cont.)

SOURCE:

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

10. Pieris brassicae L. Systemic 30.0 ppm Feeding deterrence = 10. Treatment to first
(Large white butterfly) 56.0% instar for 72 h.
(15)

11. Achaea janata (L.) Leaf disk test 1.0 ppm Feeding deterrence = 11. Treatment to
(Castor semilooper) 54.0% freshly molted 4th
instar larvae for 24 h.
10.0 ppm Feeding deterrence = (10)
74.0%

12. Epilachna varivestis Muls. Bean half 0.0014% Feeding deterrence = 12. Treatment to 4th
(Mexican bean beetle) leaf test 50.0% instar larvae for up to
24 h.
Concentration = EC50
value.
(13)

(15) Arpaia, S. and Van Loon, J.J.A. (1993) Entomol. Exp. Appl., 66, 39.

© 2005 by CRC Press LLC


166 Opender Koul

AZADIRACHTIN–A (Cont.)

SOURCE:

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

13. Diabrotica undecimpunctata Spray 100 ppm Feeding deterrence = 13. Treatment to
howardi Barber 98.0%. beetles.
(Spotted cucumber beetle) (16)

14. Acalymma vittatum (Fab.) Spray 100 ppm Feeding deterrence = 14. Treatment to
(Striped cucumber beetle) 98.0%. beetles.
(16)

15. Leptinotarsa decemlineata Spray 600 ppm No feeding 15. Treatment to


(Say) deterrence beetles.
(Colorado potato beetle) (16)

(16) Reed, D.K., Warthen, J.D. Jr., Uebel, E.C., and Reed, G.L. (1982) J. Econ. Entomol., 75, 1109.

© 2005 by CRC Press LLC


Insect Antifeedants 167

AZADIRACHTIN–A (Cont.)

SOURCE:

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

16. Myzus persicae (Sulzer) Artificial diet 100 ppm Feeding deterrence = 16. Treatment to
(Green peach aphid) feeding 80.0% adults.
(17)

17. Chaetosiphon fragaefolii Systemic 300 ppm Feeding deterrence = Treatment to adults.
(Cockerell) 30.0% (18)
(Strawberry aphid)

18. Rhopalosiphum padi (L.) Leaf disk 119.5 ppm Feeding deterrence = 17. Treatment to
(Bird cherry aphid) choice test 50.0% adult aphids.
Concentration = EC50
value.
(19)

Leaf disk 250 ppm Feeding deterrence = 18. Treatment to


choice test 50.0% adult aphids and data
assessed after 25 m
Systemic 500 ppm Feeding deterrence = of probing.
18.0% (20)

(17) Nisbet, A.J., Woodford, J.A.T., and Strang, R.H.C. (1992) In S.B.J. Menken, J.H. Viser, and P. Harrewiju
(eds.), Proc. 8th Int. Symp. Insect-Plant Relationships, Kluwer Acad. Publishers, Dordrecht, The Netherlands,
pp. 424.
(18) Nisbet, A.J., Woodford, J.A.T., Strang, R.H.C., and Conolly, J.D. (1993) Entomol. Exp. Appl., 68, 87.
(19) Lowery, D.T. and Isman, M.B. (1993) J. Chem. Ecol., 19, 1761.
(20) West, A.J. and Mordue (Luntz), A.J. (1992) Entomol. Exp. Appl., 62, 75.

© 2005 by CRC Press LLC


168 Opender Koul

AZADIRACHTIN–A (Cont.)

SOURCE:

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

19. Brevicoryne brassicae (L.) Leaf disk 10.7 ppm Feeding deterrence = 19. Treatment to 2nd
(Cabbage aphid) choice test 50.0% instar aphids.
Concentration = EC50
value.
(21)

20. Rhodnius prolixus L. Blood meal 25.0 ppm Feeding deterrence = 20. Treatment to 4th
(Assassin bug) feeding 50.0% instar larvae.
Concentration = EC50
value.
(22)
21. Schistocerca gregaria Filter paper 0.008 ppm Feeding deterrence = 21. Treatment to
(Forska.) disk test 50.0% various nymphal
(Desert locust) 0.005 ppm Feeding deterrence = stages by various
95.0% workers. Range of
0.01 ppm Feeding deterrence = potential activity
100.0% between 0.01 and
0.05 ppm.
(23–26)
Spray 1.0 ppm Feeding deterrence = Foliage spray.
50.0% (27)

(21) Koul, O., Shankar, J.S., and Mehta, N. (1997) Ind. J. Expt. Biol., 35, 994.
(22) Garcia, E.S. and Rembols, H. (1984) J. Insect Physiol., 30, 939.
(23) Haskel, P.T. and Mordue (Luntz), A.J. (1969) Entomol. Exp. Appl., 12, 591.
(24) Morgan, E.D. (1981) Proc. Ist Int. Neem Conf., GTZ, Eschborn, Germany, pp. 43–52.
(25) Butterworth, J.H. and Morgan, E.D. (1968) J. Chem. Soc. Chem. Commun., 23.
(26) Butterworth, J. H. and Morgan, E.D. (1971) J. Insect Physiol., 17, 969.
(27) Nasiruddin, M. and Mordue (Luntz), A.J. (1994) Entomol. Exp. Appl., 70, 247.

© 2005 by CRC Press LLC


Insect Antifeedants 169

AZADIRACHTIN–A (Cont.)

SOURCE:

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

22. Locusta migratoria (L.) Fiber glass 100 ppm Feeding deterrence = 22. Treatment to
(Migratory locust) disk test 50.0% nymphs
Concentration = EC50
value.
(28)

Filter paper 100 ppm Feeding deterrence = Treatment to larvae.


disk test 50.0% Concentration = EC50
value.
(29)

23. Melanoplus sanguinipes Artificial diet 1000 ppm No feeding 23. Treatment to
(Fab.) feeding deterrence various nymphal
(Migratory grasshopper) stages.
(30)
EC50 considered to
be >1000 ppm.
(31)

24. Eyprepocnemis plorans Topical 0.01 ppm Feeding inhibition 24. Treatment to
(Charpentier) treatment to = 54% nymphs.
(Grasshopper) leaves/disks 0.1 ppm = 85% (32)

(28) Cottee, P.K., Bernays, E.A., and Mordue (Luntz), A.J. (1988) Entomol. Exp. Appl., 46, 241.
(29) Pradhan, S., Jotwani, M.G., and Rai, B.K. (1962) Indian Farming, 12, 7.
(30) Mulkern, G.B. and Mongolkiti, S. (1975) Acrida, 4, 95.
(31) Mordue (Luntz), A.J. and Blackwell, A. (1993) J. Insect Physiol., 39, 903.
(32) Ascher, K.R.S., Streloke, M., Schmidt, G.H., and Warthen, J.D. Jr. (1989) Phytoparasitica, 17, 167.

© 2005 by CRC Press LLC


170 Opender Koul

AZADIRACHTIN–A (Cont.)

SOURCE:

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

25. Phyllotreta striolata (Fab.) Cotyledon 0.1% Feeding deterrence = 25. Treatment to
(Flea beetle) painting 54.0%. adult beetles for 24 h.
(33)

26. Coptotermes formosanus Filter 100 ppm Feeding deterrence = 26. Treatment to
Shiraki paper disk 50.0% in terms of workers for 10 days.
(Formosan subterranean test paper mass loss. Data calculated from
termite) Reference 34.
(34)

27. Reticulitermes speratus Paper disk 2157 ppm Feeding deterrence = 27. Treatment to 3rd
Kolbe no-choice 50.0% instar larvae based on
(Subterranean termite) test 65,293 ppm Feeding deterrence = size over 25 days.
95.0% Concentrations =
EC50 and EC95
respectively.
(35)

(33) Meisner, J. and Mitchell, B.K. (1982) Z. Pflanzenkrank. Pflanzen., 89, 463.
(34) Grace, J.K. and Yates, J.R. (1992) Trop. Pest. Manag., 38, 176.
(35) Serit, M., Ishida, M., Hagiwara, N., Kim, M., Yamamoto, T., and Takahashi, S. (1992) J. Chem. Ecol., 18, 593.

© 2005 by CRC Press LLC


Insect Antifeedants 171

AZADIRACHTIN–A (Cont.)

SOURCE:

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

28. Pericallia ricini (Fab.) Leaf disk 1 µg/cm2 Feeding deterrence = 28. Treatment to 3rd
(Tiger moth) dual-choice 79.2% instar larvae for 24 h.
test 10 µg/cm2 Feeding deterrence = (36)
87.5%

29. Oxya fuscovittata Leaf disk 1 µg/cm2 Feeding deterrence = 29. Treatment to 3rd
(Grasshopper) dual-choice 74.2% instar larvae for 24 h.
test 10 µg/cm2 Feeding deterrence = (36)
87.2%

LD50 (rats): >5000 mg/kg (oral) (37)

(36) Govindachari, T.R., Narasimhan, N.S., Suresh, G., Partho, P.D., and Gopalakrishnan, G. (1996) J. Chem
Ecol., 18, 593.
(37) Koul, O. (2003) In M.M. Srivastava and S. Srivastava (eds.), Recent Trends in Chemistry, Discovery
Publishing House, New Delhi, pp. 248–265.

© 2005 by CRC Press LLC


172 Opender Koul

AZADIRACHTIN–B C33H42O14
(662.68)
M.p. : 204–206°

COOCH3
H OH
HO O
11
O
1

3 O
O O
OH
O
H
H3COOC O

(1) (1)

SOURCE: Azadirachta indica A. Juss. neem (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera litura Fab. Leaf disk 50 ppm Feeding deterrence = 1. Treatment to 3rd
(Tobacco armyworm) choice test 81.9% instar freshly
10 ppm Feeding deterrence = moulted larvae for 24
78.4% h.
5 ppm Feeding deterrence = EC50 = 0.85 ppm
77.0% calculated from
1 ppm Feeding deterrence = Reference 2.
54.5% (2)

2. Rhodnius prolixus L. Blood meal 26.0 µg/ml Feeding deterrence = 2. Treatment to 4th
(Assassin bug) feeding 50.0% instar nymphs.
Concentration = EC50
value.
(3)

(1) Rembold, H., Forster, H., and Sonnenbichler, J. (1987) Z. Naturforsch., 42C, 4.
(2) Govindachari, T.R., Suresh, G., and Ganeshwar Prasad, K. (1994) Pestic. Res. J., 6, 20.
(3) Garcia, E.S., Azambuja, P., Forster, H., and Rembold, H. (1984) Z. Naturforsch., 39C, 1155.

© 2005 by CRC Press LLC


Insect Antifeedants 173

AZADIRACHTIN–D C34H44O14
(676.71)
Only spectral data given

O COOCH3 M.p. : 170–176°


OH OH
O O [α]D27 : –1.27° (CHCl3)
O
(for 11 epimer)

O
O
OH
AcO
H
O

(1) (1,3)

SOURCE: Azadirachta indica A. Juss. neem (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura Fab. Leaf disk 50 ppm Feeding deterrence = Treatment to 3rd
(Tobacco armyworm) choice test 81.9% instar freshly
10 ppm Feeding deterrence = moulted larvae for
78.4% 24 h.
5 ppm Feeding deterrence = EC50 = 1.3 ppm
77.0% calculated from
1 ppm Feeding deterrence = Reference 2.
54.5% (2)

No-choice 50 ppm Feeding deterrence = Treatment to 3rd


test 36.5% instar freshly
10 ppm Feeding deterrence = moulted larvae for
33.0% 24 h.
5 ppm Feeding deterrence = EC50 = 65.0 ppm
16.8% calculated from
1 ppm Feeding deterrence = Reference 2.
16.8% (2)

(1) Rembold, H. (1990) ACS Symp. Ser. 387, Am. Chem. Soc., Washington, D.C., pp. 150–163.
(2) Govindachari, T.R., Suresh, G., and Ganeshwar Prasad (1994) Pestic. Res. J., 6, 20.
(3) Ramji, N., Venkatakrishnan, K., and Madyastha, K.M. (1998) Phytochemistry, 49, 265.

© 2005 by CRC Press LLC


174 Opender Koul

AZADIRACHTIN–H C33H42O14
(662.68)
M.p. : 258–261°

[α]D25 : –33.3° (CHCl3)


O H
OH OH
O O

O
O

AcO OH
H
H3COOC O

(1) (1)

SOURCE: Azadirachta indica A. Juss. neem (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura Fab. Leaf disk 50 ppm Feeding deterrence = Treatment to 3rd
(Tobacco armyworm) choice test 53.7% instar freshly
10 ppm Feeding deterrence = moulted larvae for
50.4% 24 h.
5 ppm Feeding deterrence = EC50 could not be
56.8% calculated from the
1 ppm Feeding deterrence = recorded data.
64.6% (2)

No-choice 50 ppm Feeding deterrence = Treatment to 3rd


test 30.2% instar freshly
10 ppm Feeding deterrence = moulted larvae for
24.1% 24 h.
1 ppm Feeding deterrence = EC50 = 70.0 ppm
18.8% calculated from
Reference 2.
(2)

(1) Govindachari, T.R., Sandhya, G., and Ganesh Raj, S.P. (1992) J. Nat. Prod., 55, 596.
(2) Govindachari, T.R., Suresh, G., and Ganeshwar Prasad (1994) Pestic. Res. J., 6, 20.

© 2005 by CRC Press LLC


Insect Antifeedants 175

AZADIRACHTIN–I C32H42O12
(618.68)
M.p. : 198–200°

O H [α] 25
D : –21.8° (CHCl3)

OH OH
O O

O
O
OH
AcO
H
O

(1) (1)

SOURCE: Azadirachta indica A. Juss. neem (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura Fab. Leaf disk 10 ppm Feeding deterrence = Treatment to 3rd
(Tobacco armyworm) choice test 55.3% instar freshly
1 ppm Feeding deterrence = moulted larvae for
37.2% 24 h.
EC50 could not be
calculated from the
No-choice 50 ppm Feeding deterrence = recorded data.
test 9.2% (2)
5 ppm Feeding deterrence =
8.1%

(1) Govindachari, T.R., Sandhya, G., and Ganesh Raj, S.P. (1992) J. Nat. Prod., 55, 596.
(2) Govindachari, T.R., Suresh, G., and Ganeshwar Prasad (1994) Pestic. Res. J., 6, 20.

© 2005 by CRC Press LLC


176 Opender Koul

AZADIRACHTOL C28H37O13
(3-Detigloylazadirachtin B) (581.56)
Only spectral data given

COOCH3
H OH
HO O

O
O
HO OH

H3COOC O

(1, 2) (3)

SOURCE: Azadirachta indica A. Juss., neem (Meliaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera littoralis (Boisd.) Glass fiber 1 ppm Feeding deterrence = Treatment to 24- to
(Egyptian cotton leaf worm) disk choice 86.0% 36-h-old pre-starved
test final stadium larvae.
Bioassay terminated
after the larvae had
Glass fiber 1 ppm Feeding deterrence = eaten approximately
disk no- 38.3% 50% of one of the
choice test disks.
(1)

Deterrence
calculated from
Reference 1 for no-
choice assay, which
was run for 8 to 9 h.

(1) Siddiqui, S., Siddiqui, B.S., Faizi, S., and Mahmood, T. (1988) J. Nat. Prod., 51, 30.
(2) Blaney, W.M., Simmonds, M.S.J., Ley S.V., Anderson, J.C., and Toogood, P.L. (1990) Entomol. Exp. Appl.,
55, 149.
(3) Ley, S.V., Denholm, A.A., and Wood, A. (1993) Nat. Prod. Rep., 10, 109.

© 2005 by CRC Press LLC


Insect Antifeedants 177

AZADIRADIONE C28H34O5
(450.57)
M.p. : 168°

[α]20
D : +35.5° (CHCl3)
O

O OAc

(1) (1)

SOURCE: Azadirachta indica A. Juss. neem (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera litura (Fab.) Leaf disk 1 µg/cm2 Feeding deterrence = 1. Treatment to 3rd
(Tobacco armyworm) dual-choice 57.5% instar freshly
test 5 µg/cm2 Feeding deterrence = moulted larvae for
61.0% 24 h.
10 µg/cm2 Feeding deterrence = (2)
74.1%
20 µg/cm2 Feeding deterrence = EC50 = 0.43 µg/cm2
77.0% calculated from
Reference 2.

2. Epilachna varivestis Muls. Bean leaf 0.033% Feeding inhibition = 2. Treatment to 4th
(Mexican bean beetle) choice assay 50% stadium larvae up to
24 h.
Concentration = EC50
value.
(3)

(1) Lavie, D., Levy, E.C., and Jain, M.K. (1971) Tetrahedron, 27, 3927.
(2) Govindachari, T.R., Narasimhan, N.S., Suresh, G., Partho, P.D., Gopalakrishnan, G., and Krishna Kumari,
G.N. (1995) J. Chem. Ecol., 21, 1586.
(3) Schwinger, M., Ehhammer, B., and Kraus, W. (1984) In H. Schmutterer and K.R.S. Ascher (eds.), Proc. 2nd
Int. Neem Conf., Rauischholzhausen, GTZ, Eschborn, Germany, pp. 181–198.

© 2005 by CRC Press LLC


178 Opender Koul

AZADIRONE C28H36O4
(436.59)
Amorphous

[α]D : +26° (CHCl3)


O

O OAc

(1) (1)

SOURCE: Azadirachta indica A. Juss. neem (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Epilachna varivestis Muls. Bean leaf 0.66% Feeding deterrence = Treatment to 4th
(Mexican bean beetle) choice assay 50% stadium larvae up to
24 h.
Concentration = EC50
value.
(2)

(1) Lavie, D., Levy, E.C., and Jain, M.K. (1971) Tetrahedron, 27, 3927.
(2) Schwinger, M., Ehhammer, B., and Kraus, W. (1984) In H. Schmutterer and K.R.S. Ascher (eds.), Proc. 2nd
Int. Neem Conf., Rauischholzhausen, GTZ, Eschborn, Germany, pp. 181–198.

© 2005 by CRC Press LLC


Insect Antifeedants 179

AZEDARACHIN–A C33H44O11
(616.70)
Amorphous powder
O
[α]22
D : –10° (CH3OH)
OH

O
HO

O O

AcO
OH

OCO

(1) (1)

SOURCE: Melia azedarach L., chinaberry (Meliaceae)


M. toosendan Sieb. et Zucc., Chinese melia (Meliaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera eridania Leaf disk 200 ppm Threshold level for Treatment to 3rd
(Cramer) choice test or feeding deterrence instar larvae for
(Southern armyworm) 4 µg/cm2 6–24 h, during which
period 50% of one of
2. Spodoptera exigua (Hubner) Leaf disk 200 ppm Threshold level for the disks was
(Beet armyworm) choice test or feeding deterrence consumed.
4 µg/cm2 (1, 2)

(1) Zhou, J., Okamura, H., Iwagawa, T., and Nakatani, M. (1996) Phytochemistry, 41, 117.
(2) Nakatani, M., Huang, R.C., Okamura, H., Iwagawa, T., Tadera, K., and Naoki, H. (1995) Tetrahedron, 51,
11731.

© 2005 by CRC Press LLC


180 Opender Koul

AZEDARACHIN–B C32H42O11
(602.68)
Amorphous powder
O
[α]D : –22° (CH3OH)
OH

O
HO

O O

AcO OH

OCO
(1) (1)

SOURCE: Melia toosendan Sieb. et Zucc., Chinese melia (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera littoralis (Boisd.) Leaf disk 200 ppm Threshold level for Treatment to 3rd
(Egyptian cotton leaf worm) choice test or feeding deterrence instar larvae for
4 µg/cm2 6–24 h, during which
period 50% of one of
the disks was
consumed.
(1)

(1) Zhou, J., Minami, Y., Yagi, F., Tadera, K., and Nakatani, M. (1997) Heterocycles, 45, 1718.

© 2005 by CRC Press LLC


Insect Antifeedants 181

AZEDARACHIN–C C32H42O10
(586.68)
O Only spectral data given

O
HO

O O

AcO OH

OCO

(1) (1)

SOURCE: Melia azedarach L., chinaberry (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera eridania Leaf disk 400 ppm Threshold level for Treatment to 3rd
(Cramer) choice test or feeding deterrence instar larvae for
(Southern armyworm) 8 µg/cm2 6–24 h, during which
period 50% of one of
2. Spodoptera exigua (Hubner) Leaf disk 400 ppm Threshold level for the disks was
(Beet armyworm) choice test or feeding deterrence consumed.
8 µg/cm2 (1)

(1) Nakatani, M., Huang, R.C., Okamura, H., Iwagawa, T., Tadera, K., and Naoki, H. (1995) Tetrahedron, 51,
11731.

© 2005 by CRC Press LLC


182 Opender Koul

AZEDARACHOL C25H40O5
(420.59)
M.p. : 231–232°

CH2 [α]24
D : +20° (CHCl3)

H
O
H OH
HO

H
HO
H

(1) (1)

SOURCE: Melia azedarach L. var. japonica Makino, Japanese melia (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Agrotis segetum Denis and Leaf disk 500 ppm Feeding inhibition = Treatment to larvae.
Schiff. choice test 100% (1)
(Turnip cutworm)

(1) Nakatani, M., Takao, H., Miura, I., and Hase, T. (1985) Phytochemistry, 24, 1945.

© 2005 by CRC Press LLC


Insect Antifeedants 183

AZEDARALIDE C15H16O4
(260.11)
Yellowish powder

O [α]D25 : +165° (CH3OH)

CH2OH

(1) (1)

SOURCE: Melia azedarach L., darekh (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera littoralis (Boisd.) Leaf disk 10 µg/cm2 Feeding inhibition = Treatment to 3rd
(Egyptian cotton leaf worm) choice test 100% instar larvae.
(1)

(1) Nakatani, M., Huang, R.C., Okamura, H., Iwagawa, T., and Tadera, K. (1998) Phytochemistry, 49, 1773.

© 2005 by CRC Press LLC


184 Opender Koul

BAKKENOLIDE–A C15H22O2
(234.34)
M.p. : 80.5–80.6°

[α]D22 : +17° (CH3OH)


O

H
CH2

(1, 2) (1, 2)

SOURCE: Homogyne alpina (L.) Cass., alpine colts foot (Asteraceae) (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius L. Wafer disk 10 mg/ml Feeding deterrence 1. Treatment to


(Grain weevil) test coefficient = 140 adults.
(3)

2. Tribolium confusum Duv. Wafer disk 10 mg/ml Feeding deterrence 2. Treatment to


(Confused flour beetle) test coefficient
= 197 Adults
= 141 Larvae
(3)

3. Trogoderma granarium Wafer disk 10 mg/ml Feeding deterrence 3. Treatment to


Everts test coefficient = 187 larvae.
(Khapra beetle) (3)
Data based on a 0 to
200 greater
deterrence scale.

4. Peridroma saucia (Hubner) Leaf disk 28.5 µg/cm2 Feeding inhibition = 4. Treatment to 5th
(Variegated cutworm) choice test 38.3% instar larvae for 5 h.
57.0 µg/cm2 Feeding inhibition = (4)
74.3%

(1) Naya, K., Takagi, I., Hayashi, M., Nakamura, S., Kobayashi, M., Katsumura, S., Harmatha, J., and Samek,
Z. (1968) Chem. Ind., 318.
(2) Synackova, M., Novotny, L., Herout, V., and Sorm, F. (1976) Collect. Czech. Chem. Commun., 41, 2047.
(3) Harmatha, J. and Nawrot, J. (1984) Biochem. Syst. Ecol., 12, 95.
(4) Nawrot, J., Koul, O., Isman, M.B., and Harmatha, J. (1991) J. Appl. Ent., 112, 194.

© 2005 by CRC Press LLC


Insect Antifeedants 185

BENZALDEHYDE C7H6O
(106.12)
M.p. : –26°

B.p. : 179°

CHO n20
D : 1.5456

(1) (1)

SOURCE: Sorghum bicolor (L.) Moench., grain sorghum (Poaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Schizaphis graminum (Rondani) Synthetic 0.4% Feeding deterrence = Treatment to 50–75


(Wheat aphid) diet feeding 50% aphids at random for
24 h.

Concentration = EC50
value.
(2)

LD50 (rats): 1300 mg/kg (oral) (3)

(1) Vogel, A.I. (1959) Practical Organic Chemistry, Longmans, London, p. 693.
(2) Dreyer, D.L., Reese, J.C., and Jones, K..C. (1981) J. Chem. Ecol., 7, 273.
(3) Jenner, P.M., Hagan, E.C., Taylor, J.M., Cook, E.L., and Fitzhugh, O.G. (1964) Food Cosmetics Toxicol., 2, 327.

© 2005 by CRC Press LLC


186 Opender Koul

p-BENZOQUINONE C6H4O2
(108.10)
M.p. : 115.7° (117°)

d20
4 : 1.32

(1, 2) (1)

SOURCE: Commercial sample (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Pieris brassicae (L.) Leaf disk no- 9.3 × 10–2 Feeding deterrence Treatment to 2nd day
(Large white butterfly) choice test M ratio = 32 5th instar un-starved
larvae. Ratio of less
than 20 considered as
effective feeding
deterrence.
(2)

LD50 (rats): 130 mg/kg (oral) (3)

(1) Underwood, H.W. Jr., and Walsh, W.L. (1936) Org. Synth., 16, 73.
(2) Jones, C.G. and Firn, R.D. (1979) Biochem. Syst. Ecol., 7, 187.
(3) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8tth edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC


Insect Antifeedants 187

15-O-BENZOYL BRUCEINE–D C27H30O10


(514.53)
M.p. : 290–298°

[α]22
D : +24.05° (Pyridine)
OH

HO
O

O OCO

H OH
O O

(1, 2) (1)

SOURCE: Soulamea amara Lam., bouati (Simaroubaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Heliothis virescens (Fab.) Leaf disk 12.0 µg/cm2 Feeding deterrence = Treatment to 3rd
(Tobacco budworm) choice test 90–100% after 2 instar larvae.
days; 60–90% after 6
days

3.0 µg/cm2 Feeding deterrence =


60–90% after 2 days;
30–60% after 6 days (2)

(1) Lee, K.H., Imakura, Y., Sumida, Y., Wu, R.-Y., Hall, I.H., and Huang, H.-C. (1979) J. Org. Chem. 44, 2180.
(2) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y.M., Kiyokawa, H., and Lee, K.H.
(1987) J. Nat. Prod., 50, 442.

© 2005 by CRC Press LLC


188 Opender Koul

BENZOYLOXY TETRA-ACETOXY-4- C30H38O12


HYDROXY-DIHYDRO-β-AGAROFURAN (590.62)
M.p. : 75–76°

[α]25
D : –21.7° (CHCl3)
CH2OAc
AcO OBz

OAc

O
HO OAc

(1) (1)

SOURCE: Maytenus canariensis (Loes) Kunk et Sund. (Celastraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera littoralis (Boisd.) Leaf disk 10 µg/cm2 Feeding deterrence = Treatment to larvae.
(Egyptian cotton leaf worm) choice test Threshold level (1)

(1) Gonzalez, A.G., Jimenez, I.A., Ravelo, A.G., Sazatornil, J.G., and Bazzocchi, I.L. (1993) Tetrahedron, 49, 697.

© 2005 by CRC Press LLC


Insect Antifeedants 189

BENZOYLOXY TRIACETOXY-1,4- C28H36O11


DIHYDROXY DIHYDRO-β-AGAROFURAN (548.59)
Oil

[α]25
D : +25° (CHCl3)

CH2OAc
HO OBz

OAc

O
HO OAc

(1) (1)

SOURCE: Maytenus canariensis (Loes) Kunk. & Sund., peralillo (Celastraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera littoralis (Boisd.) Leaf disk 10 µg/cm2 Feeding deterrence = Treatment to larvae.
(Egyptian cotton leaf worm) choice test Threshold level (1)

(1) Gonzalez, A.G., Jimenez, I.A., Ravelo, A.G., Sazatornil, J.G., and Bazzocchi, I.L. (1993) Tetrahedron, 49, 697.

© 2005 by CRC Press LLC


190 Opender Koul

BENZOYLOXY TRIACETOXY-4,8- C28H36O11


DIHYDROXY DIHYDRO-β-AGAROFURAN (548.59)
Oil

[α]25
D : –23.3° (CHCl3)

CH2OAc
AcO OBz

OH

O
HO OAc

(1) (1)

SOURCE: Maytenus canariensis (Loes) Kunk. & Sund., peralillo (Celastraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera littoralis (Boisd.) Leaf disk 10 µg/cm2 Feeding deterrence = Treatment to larvae.
(Egyptian cotton leaf worm) choice test Threshold level (1)

(1) Gonzalez, A.G., Jimenez, I.A., Ravelo, A.G., Sazatornil, J.G., and Bazzocchi, I.L. (1993) Tetrahedron, 49, 697.

© 2005 by CRC Press LLC


Insect Antifeedants 191

BENZYL ALCOHOL C7H8O


(108.13)
M.p. : –15.19°

B.p. : 204.7°/760 mm

CH2OH n20
D : 1.045

d15
15 : 1.05

(1) (1)

SOURCE: Sorghum bicolor (L.) Moench., grain sorghum (Poaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Schizaphis graminum (Rondani) Synthetic 0.08% Feeding deterrence = Treatment to 50–75


(Wheat aphid) diet feeding 50% aphids at random for
24 h.

Concentration = EC50
value.
(2)

LD50 (rats): 3.1 g/kg (oral) (3)

(1) Vogel, A.I. (1959) Practical Organic Chemistry, Longmans, London, p. 711.
(2) Dreyer, D.L., Reese, J.C., and Jones, K.C. (1981) J. Chem. Ecol., 7, 273.
(3) Smyth, H.F. Jr., Carpenter, C.P., and Carol, S.W. (1951) Arch. Ind. Hyg. Occup. Med., 4, 119.

© 2005 by CRC Press LLC


192 Opender Koul

BERBERINE C20H18O4N
(336.37)
No data given

O
O

+
N
CH 3O

OCH3

(1, 2) (2)

SOURCE: Coptis japonica Makino, evergreen rosette (Ranunculaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Hyphantria cunea (Drury) Leaf disk 500 ppm Feeding deterrence = 1. Treatment to 4th
(Fall webworm) assay 75.4% instar larvae pre-
starved for 9 h.
Treatment duration =
24 h.
(2)

2. Agelastica coerulea Baly. Leaf disk 125 ppm Feeding deterrence = 2. Treatment to
(Leaf beetle) assay 57.5% adults pre-starved for
9 h.
250 ppm 91.1% Treatment duration =
24 h.
500 ppm 97.2% (2)

Compound tested as
berberine chloride

LD50 (mice): 329 mg/kg (oral) (3)

(1) (1994) Dictionary of Natural Products, Chapman & Hall, London.


(2) Park, I., Lee, H., Lee, S., Park, J., and Ahn, Y. (2000) J. Econ. Entomol., 93, 331.
(3) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold

© 2005 by CRC Press LLC


Insect Antifeedants 193

BERGAPTEN C12H8O4
(216.19)
M.p. : 188–189°

O O O

OCH3

(1, 2) (2)

SOURCE: Boeninghausenia albiflora (Hook.) Reichb. ex Meissn., flea plant (Rutaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera litura (Fab.) Leaf disk 500 ppm Feeding deterrence = Treatment to 3rd
(Tobacco armyworm) choice test 100% in 2 h instar larvae. The
activity retarded after
6 h, thus compound
was termed as
relative antifeedant.
(2)

2. Peridroma saucia (Hubner) Leaf disk 57.0 µg/cm2 Feeding deterrence = 2. Treatment to 5th
(Variegated cutworm) choice test 5.5% instar larvae for 5 h.
(3)

LD50 (mice): 8100 mg/kg (oral) (4)

(1) Thoms, H. and Baetcke, E. (1912) Chem. Ber., 45, 3705.


(2) Hosozawa, S., Kato, N., Munakata, K., and Chen, Y. (1974) Agric. Biol. Chem., 38, 1045.
(3) Nawrot, J., Koul, O., Isman, M.B., and Harmatha, J. (1991) J. Appl. Ent., 112, 194.
(4) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand, Reinhold.

© 2005 by CRC Press LLC


194 Opender Koul

(+) BICUCULLINE C20H17O6N


(367.36)
M.p. : 215°

[α]D : +130° (CHCl3)


O

N
O
H H

O
O
O

(1) (1)

SOURCE: Dicentra cucullaria L., squirrel corn (Fumariaceae) (1,2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Diabrotica virgifera virgifera Leaf 4.71 µg/1.5 cm2 Feeding deterrence = Treatment to adults
LeConte disk disk 50% of resistant insects.
(Western corn rootworm) choice
test
2.47 µg/1.5 cm2 Feeding deterrence = Treatment to adults
disk 50% of susceptible
insects.

Concentrations =
EC50 values.
(2)

(1) (1982) Dictionary of Organic Compounds, Vol. 1, Chapman & Hall, New York, p. 640.
(2) Mullin, C.A., Mason, C.H., Chou, J. and Linderman, J.R. (1992) In C.A. Mullin and J.G. Scott (eds.),
Molecular Mechanism of Insecticide Resistance: Diversity Among Insects, ACS Symp. Ser. 505, Washington,
D.C., pp. 288–308.

© 2005 by CRC Press LLC


Insect Antifeedants 195

(–) BICUCULLINE C20H17O6N


(367.36)
M.p. : 193–195°

[α]33
D : –128° (CHCl3)
O

+
N
O
H H -
Cl
O

O
O O

(1) (1)

SOURCE: Fumaria parviflora, F. vaillantii, fumitory, and Corydalis swertzovii (Fumariaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Diabrotica virgifera virgifera Leaf disk 69.0 nmol/ Feeding deterrence = Treatment to adults
LeConte choice test 1.5 cm2 50% after 24 h. of cyclodiene-
(Western corn rootworm) disk resistant insects.
(2)

Feeding deterrence = Data calculated from


40% after 48 h. Reference 2.

( – assayed as MeCl)

(1) (1994) Dictionary of Natural Products, Chapman & Hall, London.


(2) Mullin, C.A., Mason, C.H., Chou, J., and Linderman, J.R. (1992) In C.A. Mullin and J.G. Scott (eds.)
Molecular Mechanism of Insecticide Resistance: Diversity Among Insects, ACS Symp. Ser. 505, Washington,
D.C., pp. 288–308.

© 2005 by CRC Press LLC


196 Opender Koul

BILOBALIDE C15H18O8
(326.30)
M.p. : >300°

[α]20
D : –66.6° (Acetone)
O O
O O
OH
O
OH
O

(1, 2) (1)

SOURCE: Ginkgo biloba L., gingko tree (Ginkgoaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Pieris rapae crucivora Boisd. Leaf disk 500 µg/disk Feeding deterrence = Treatment to 3rd
(Japanese cabbage butterfly) no-choice 90% instar larvae.
test (2)

(1) Nakanishi, K., Habaguchi, K., Nakadaira, Y., Woods, M.C., Maruyama, M., Major, R.T., Alauddin, M., Patel,
A.R., Weinges, K., and Bahr, W. (1971) J. Am. Chem. Soc., 93, 3544.
(2) Matsumoto, T. and Sei, T. (1987) Agric. Biol. Chem., 51, 249.

© 2005 by CRC Press LLC


Insect Antifeedants 197

BIOCHANIN C22H22O10
(446.41)
M.p. : 220°

[α]30
D : –35.3° (HCONMe2)
CH2OH
O
O
O
OH

HO H
O
OCH3
OH

(1, 2) (1)

SOURCE: Commercial sample (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Costelytra zealandica Synthetic 200 µg/ml Feeding deterrence = 1. Treatment to 3rd


(White) diet feeding 23% instar larvae after
(Scarab beetle) 24-h starvation.
(2)

2. Heteronychus arator (Fab.) Synthetic 200 µg/ml Feeding deterrence = 2. Treatment to 3rd
(Black beetle) diet feeding 51% instar larvae after
24-h starvation.
(2)

Data calculated from


Reference 2.

(1) Wong, E., Mortimer, P.I., and Geissman, T.A. (1965) Phytochemistry, 4, 89.
(2) Sutherland, O.R.W., Russel, G.B., Biggs, D.R., and Lane, G.A. (1980) Biochem. Syst. Ecol., 8, 73.

© 2005 by CRC Press LLC


198 Opender Koul

(6S)-2,10-BISABOLADIEN-1-ONE C15H24O
(220.18)
Oil

[α]D : –34° (EtOH)


O
H

(1) (1)

SOURCE: Senecio palmensis Chr.Sm., groundsel (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera littoralis (Boisd.) Choice >200 nmol/cm2 Feeding deterrence = 1. Treatment to 6th
(Eygyptian cotton leaf worm) feeding 50.0% instar larvae.
assay

2. Leptinotarsa decemlineata Choice 66.5 nmol/cm2 Feeding deterrence = 2. Treatment to


(Say) feeding 50.0% adults.
(Colorado potato beetle) assay

3. Myzus persicae (Sulzer) Choice 92.2 nmol/cm2 Feeding deterrence = 3. Treatment to


(Green peach aphid) feeding 50.0% apterous adult
assay aphids.

4. Rhopalosiphum padi (L.) Choice 110.0 nmol/cm2 Feeding deterrence = 4. Treatment to


(Cereal aphid) feeding 50.0% apterous adult
assay aphids.

5. Sitobion avenae (Fab.) Choice 84.4 nmol/cm2 Feeding deterrence = 5. Treatment to


(Grass aphid) feeding 50.0% apterous adult
assay aphids.

6. Diuraphis noxia (Mordvilko) Choice 14.9 nmol/cm2 Feeding deterrence = 6. Treatment to


(Wheat aphid) feeding 50.0% apterous adult
assay aphids.
Concentrations =
EC50 values
(1)

(1) Reina, M., Nold, M., Santana, O., Orihuela, J.C., and Gonzalez-Coloma, A. (2002) J. Nat. Prod., 65, 448.

© 2005 by CRC Press LLC


Insect Antifeedants 199

BISABOLANGELONE C15H20O3
(248.32)
M.p. : 148–149°

[α]D20 : +198° (EtOH)


O
OH H

O
H

(1, 2) (1)

SOURCE: Angelica silvestris L., angelica (Apiaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius L. Wafer disk 10 mg/ml Feeding deterrence 1. Treatment to


(Grain weevil) test coefficient = 139 adults.
(2)
2. Tribolium confusum Duv. Wafer disk 10 mg/ml Feeding deterrence 2. Treatment to
(Confused flour beetle) test coefficient
= 195 Adults.
= 200 Larvae.
(2)
3. Trogoderma granarium Wafer disk 10 mg/ml Feeding deterrence 3. Treatment to
Everts test coefficient = 200 larvae. (2)
(Khapra beetle) Data based on a 0 to
200 greater
deterrence scale
4. Peridroma saucia (Hubner) Leaf disk 14.25 µg/cm2 Feeding inhibition = 4. Treatment to 5th
(Variegated cutworm) choice test 55.0% instar larvae for 5 h.
28.5 µg/cm2 Feeding inhibition = (3)
78.8%

5. Pieris brassicae (L.) Leaf disk 5.0 µg/cm2 Feeding inhibition = Treatment to 3rd
(Large white butterfly dual 100.0% instar larvae for 24 h.
choice test (4)

(1) Novotny, L., Samek, Z., and Sorm, F. (1966) Tetrahedron Lett., 7, 3541.
(2) Nawrot, J., Harmatha, J., and Novotny, L. (1984) Biochem. Syst. Ecol., 12, 99.
(3) Nawrot, J., Koul, O., Isman, M.B., and Harmatha, J. (1991) J. Appl. Ent., 112, 194.
(4) Benz, C., Abivardi, C., and Muckensturm, B. (1989) Entomol. Exp. Appl., 53, 257.

© 2005 by CRC Press LLC


200 Opender Koul

N, 3-BIS (4-CHLOROPHENYL)-4,5- C16H11ON3Cl2


DIHYDRO-1H-PYRAZOLE-1 CARBOXAMIDE (332.17)
Only spectral data given

N
NCONH Cl
Cl

(1, 2) (1)

SOURCE: Synthetic (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Ceramica picta (Harris) Leaf dip test 500 ppm Feeding deterrence = 1. Treatment at
(Zebra caterpillar) 91.8% (small) random to small-,
91.2% (medium) medium-, and large-
85.4% (large) sized larvae.
(2)
250 ppm Feeding deterrence =
78.9% (small) Data calculated from
74.5% (medium) Reference 2.
48.7% (large)

125 ppm Feeding deterrence =


14.8% (small)
25.2% (medium)
28.0% (large)

(1) Mulder, R., Wellinga, K., and van Daalen, J.J. (1975) Naturwissenschaften, 62, 531.
(2) Tamaki, G. (1976) J. Econ. Entomol., 63, 644.

© 2005 by CRC Press LLC


Insect Antifeedants 201

BORNEOL C10H18O
(154.25)
M.p. : 208–209°

B.p. : 212°

[α]D20 : –37.74° (EtOH)

HO

(1, 2) (2)

SOURCE: Commercial sample (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Hylobius pales (Herbst.) Twig dip 10.0% Feeding inhibition = Treatment to 22–65
(Pales weevil) treatment 68.0% mg body weight
choice assay weevils for 24 h.
(1)

Data calculated from


Reference 1.

LD50 (rats): 5800 mg/kg (oral) (3)

(1) Salom, S.M., Carlson, J.A., Aug, B.N., Grosman, D.M., and Day, E.R. (1994) J. Entomol. Sci., 29, 407.
(2) (1994) Dictionary of Natural Products, Chapman & Hall, London.
(3) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC


202 Opender Koul

BORNYL ACETATE C12H20O2


(196.28)
M.p. : 27°

B.p. : 103°/14 mm

[α]D : –42.0°, –44.45°

AcO

(1, 2) (1, 2)

SOURCE: Artemisia capillaris Thumb., wormwood (Asteraceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Pieris rapae crucivora Boisd. Leaf disk 10−1 mol/l Feeding inhibition = 1. Treatment to 5th
(Cabbage butterfly) choice assay 100% instar larvae for 2 h.
(2)

2. Hylobius pales (Herbst.) Twig dip 10.0% Feeding inhibition = 2. Treatment to


(Pales weevil) treatment 50% weevils of 22–65 mg
choice assay body weight for 24 h.
(3)

Data calculated from


Reference 3.

(1) Dev, S. and Koul, O. (1997) Insecticides of Natural Origin, Harwood Academic Publishers, Amsterdam, p. 58.
(2) Yano, K. (1987) J. Agric. Food Chem., 35, 889.
(3) Salom, S.M., Carlson, J.A., Aug, B.N., Grosman, D.M., and Day, E.R. (1994) J. Entomol. Sci., 29, 407.

© 2005 by CRC Press LLC


Insect Antifeedants 203

2-BROMODECANOIC ACID C10H19O2Br


(251.16)
M.p. : 40°

Br

COOH

(1, 2) (1)

SOURCE: Synthetic (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Incisitermes minor (Hagen) Paper towel 0.05 mg/cm2 Feeding inhibition = Treatment to larvae
(Western drywood termite) disk assay 52.7% after 6 days of of 10–13 mg body
treatment exposure. weight
(2)

Data calculated from


Reference 2.

(1) Bagard, A. (1907) Bull. Soc. Chim., 1, 310 and 348.


(2) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39.

© 2005 by CRC Press LLC


204 Opender Koul

22-α-BROMO-22,23-DIHYDRO-23- C37H47O17Br
α,β-ETHOXYAZADIRACHTIN (843.63)
No data given

O COOCH3
OH Br
O O OH

O
OC2H5

O
O
OH
AcO
H
H3COOC O

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera littoralis (Boisd.) Glass fiber 1.0 ppm Feeding inhibition = Treatment to starved
(Egyptian cotton leaf worm) disk choice 38.7% 24- to 36-h-old final
assay stadium larvae.
Bioassay terminated
2. Spodoptera frugiperda Glass fiber 1.0 ppm Feeding inhibition = after 1 h of feeding.
(J.E. Smith) disk choice 20.5% (1)
(Fall armyworm) assay
Data calculated from
Reference 1.

(1) Blaney, W.M., Simmonds, M.S.J., Ley, S.V., Anderson, J.C., and Toogood, P.L. (1990) Entomol. Exp. Appl.,
55, 149.

© 2005 by CRC Press LLC


Insect Antifeedants 205

22-α-BROMO-22,23-DIHYDRO-23- C38H49O17Br
α,β-ISOPROPOXYZADIRACHTIN (857.66)
No data given

O COOCH3
OH Br
O O OH

O
OPr

O
O
OH
AcO
H
H3COOC O

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera littoralis (Boisd.) Glass fiber 1.0 ppm Feeding inhibition = Treatment to starved
(Egyptian cotton leaf worm) disk no- 64.7% 24- to 36-h-old final
choice assay stadium larvae.
Bioassay terminated
2. Spodoptera frugiperda Glass fiber 1.0 ppm Feeding inhibition = after 8–9 h of
(J.E. Smith) disk no- 69.0% feeding.
(Fall armyworm) choice assay (1)

Data calculated from


Reference 1.

Approximate EC50 =
0.82 ppm

(1) Blaney, W.M., Simmonds, M.S.J., Ley, S.V., Anderson, J.C., and Toogood, P.L. (1990) Entomol. Exp. Appl.,
55, 149.

© 2005 by CRC Press LLC


206 Opender Koul

22-α-BROMO-22,23-DIHYDRO-23- C36H45O17Br
β-METHOXYZADIRACHTIN (829.60)
No data given

O COOCH3
OH Br
O O OH

O
OCH3

O
O
OH
AcO
H
H3COOC O

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera littoralis (Boisd.) Glass fiber 1.0 ppm Feeding inhibition = Treatment to starved
(Egyptian cotton leaf worm) disk choice 50.0% 24- to 36-h-old final
assay stadium larvae.
Bioassay terminated
Glass fiber 1.0 ppm Feeding inhibition = after the larvae had
disk no- 69.7% eaten approximately
choice assay 50% of one of the
disks.
(1)

Data calculated from


Reference 1 for no-
choice assay, which
was run for 8 to 9 h.

(1) Blaney, W.M., Simmonds, M.S.J., Ley, S.V., Anderson, J.C., and Toogood, P.L. (1990) Entomol. Exp. Appl.,
55, 149.

© 2005 by CRC Press LLC


Insect Antifeedants 207

2-BROMOEICOSANOIC ACID C20H39O2Br


(391.44) No physical data given

HOOC

Br

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Incisitermes minor (Hagen) Paper towel 0.05 mg/cm2 Feeding inhibition = Treatment to larvae
(Western drywood termite) disk assay 55.0% after 6 days of of 10–13 mg body
treatment exposure. weight.
(1)

Data calculated from


Reference 1.

(1) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39.

© 2005 by CRC Press LLC


208 Opender Koul

α-BROMOERGOCRYPTINE C32H40O5N5Br
(654.60)
OH M.p. : 215–218° (dec.)
O
N [α]20
D : –195° (CH2Cl2)

N N
O O
O

HN
Br (1, 2) (1)

SOURCE: Commercial sample (2)


It has been obtained from Lolium perenne L., rye grass (Graminaceae), infected with fungus Neotyphodium lolii.

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Heteronychus arator (Fab.) Artificial diet 5.0 µg/g Feeding inhibition = Treatment to adults
(Black beetle) feeding. 25.0% for 96 h.
Choice test (2)
Data calculated from
Reference 2.
20.0 µg/g Feeding inhibition =
70.4%

LD50 (rats): 72 mg/kg (ivn.) (3)

(1) (1994) Dictionary of Natural Products, Chapman & Hall, London.


(2) Ball, O.J.-P., Miles, C.O., and Prestidge, R.A. (1997) J. Econ. Entomol., 90, 1382.
(3) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC


Insect Antifeedants 209

2-BROMOOCTADECANOIC ACID C18H35O2Br


(363.38)
M.p. : 60°

COOH

Br

(1, 2) (1)

SOURCE: Synthetic (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Incisitermes minor (Hagen) Paper towel 0.05 mg/cm2 Feeding inhibition = Treatment to larvae
(Western drywood termite) disk assay 53.5% after 6 days of of 10–13 mg body
treatment exposure. weight.
(2)

0.25 mg/cm2 Feeding inhibition = Data calculated from


85.4% after 6 days of Reference 2.
treatment exposure.

(1) Radcliffe, L.G. and Gibson, W. (1923) J. Soc. Dyers Colourists, 39, 4.
(2) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39.

© 2005 by CRC Press LLC


210 Opender Koul

BRUCEANOL–A C28H30O11
(542.54)
M.p. : 174–177°

[α]D25 : +60° (EtOH)


OH

HO COOCH3
HO
O

O OCO

H
O O

(1, 2) (1)

SOURCE: Brucea antidysenterica Mill, brucea (Xanthoxylaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Heliothis virescens (Fab.) Leaf disk 6.0 µg/cm2 Feeding inhibition = Treatment to 3rd
(Tobacco budworm) assay 60–90% after 6 days instar larvae.
of treatment.

3.0 µg/cm2 Feeding inhibition =


60–90% after 2 days
of treatment, which
declines to 30–60%
after 6 days of
treatment. (2)

(1) Polonsky, J., Baskevitch Varon, Z., and Sevenet, T. (1975) Experientia, 31, 1113.
(2) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y.M., Kiyokawa, H., and Lee, K.H.
(1987) J. Nat. Prod., 50, 442.

© 2005 by CRC Press LLC


Insect Antifeedants 211

BRUCEANOL–B C27H36O11
(536.58)
Amorphous solid

M.p. : 170–172°
OH
[α]25
D : +32° (MeOH)
HO COOCH3
HO
O

O OCO

H
O O

(1, 2) (1)

SOURCE: Brucea antidysenterica Mill, brucea (Xanthoxylaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Heliothis virescens (Fab.) Leaf disk 12.0 µg/cm2 Feeding inhibition = Treatment to 3rd
(Tobacco budworm) assay 60–90% after 2 days instar larvae.
of treatment and goes
down to 30–60%
after 6 days.

6.0 µg/cm2 Feeding inhibition =


60–90% after 2 days
of treatment, which
declines to 0–30%
after 6 days of
treatment. (2)

(1) Okano, M., Fukamiya, N., Aratani, T., Juichi, M., and Lee, K.-H. (1985) J. Nat. Prod., 48, 972.
(2) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y.M., Kiyokawa, H., and Lee, K.H.
(1987) J. Nat. Prod., 50, 442.

© 2005 by CRC Press LLC


212 Opender Koul

BRUCEANTIN C28H36O11
(548.58)
OH M.p. : 225–226°

HO COOCH3 [α]25
D : –27.7° (Pyridine)

O OCO

HO O O
H
(1, 2) (1)

SOURCE: Brucea antidysenterica Mill., brucea (Xanthoxylaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Heliothis virescens (Fab.) Leaf disk 12.0 µg/cm2 Feeding inhibition = 1. Treatment to 3rd
(Tobacco budworm) assay 90–100% after 2 instar larvae.
days of treatment and
goes down to
60–90% after 6 days.

3.0 µg/cm2 Feeding inhibition =


90–100% after 2
days of treatment,
which declines to (2)
30–60% after 6 days
of treatment.

2. Epilachna varivestis Muls. Whole leaf 500 ppm Feeding inhibition = 2. Treatment to 4th
(Mexican bean beetle) application 90% instar larvae starved
for 2 h. Treatment
250 ppm Feeding inhibition = duration = 24 h.
72.2% Data calculated from
Reference 3.
(3)

3. Spodoptera eridania Whole leaf 500 ppm Feeding inhibition = Treatment to freshly
(Cramer) application 29.0% molted 5th instar
(Southern armyworm) larvae for 24 h.
Data calculated from
Reference 3.
(3)

LD50 (mice): 7 mg/kg (oral) (4)

(1) Kupchan, S.M., Britton, R.W., Lacadie, J.A., Ziegler, M.F., and Sigel, C.W. (1975) J. Org. Chem., 40, 648.
(2) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y.M., Kiyokawa, H., and Lee, K.H.
(1987) J. Nat. Prod., 50, 442.
(3) Leskinen, V., Polonsky, J., and Bhatnagar, S. (1984) J. Chem. Ecol., 10, 1497.
(4) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC


Insect Antifeedants 213

BRUCEINE–A C26H34O11
(522.55)
M.p. : 267–270°

[α]D25 : –86.3° (Pyridine)


OH

HO COOCH3
O

O OCO

H
HO O O
H

(1, 2) (1)

SOURCE: Brucea amarissima (Lour.) Merril., common brucea (Xanthoxylaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Heliothis virescens (Fab.) Leaf disk 12.0 µg/cm2 Feeding inhibition = 1. Treatment to 3rd
(Tobacco budworm) assay 60–90% after 6 days instar larvae.
of treatment.

6.0 µg/cm2 Feeding inhibition =


60–90% after 2 days
of treatment, which
declines to 30–60%
after 6 days of
treatment. (2)

2. Epilachna varivestis Muls. Whole leaf 500 ppm Feeding inhibition = 2. Treatment to 4th
(Mexican bean beetle) application 64.2% instar larvae starved
for 2 h. Treatment
duration = 24 h.
Data calculated from
Reference 3. (3)

3. Spodoptera eridania Whole leaf 500 ppm Feeding inhibition = 3. Treatment to


(Cramer) application 55.8% freshly moulted 5th
(Southern armyworm) instar larvae for 24 h.
Data calculated from
Reference 3. (3)

(1) Polonsky, J., Baskevitch, Z., Gaudemer, A., and Das, B.C. (1967) Experientia, 23, 424.
(2) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y.M., Kiyokawa, H., and Lee, K.H.
(1987) J. Nat. Prod., 50, 442.
(3) Leskinen, V., Polonsky, J., and Bhatnagar, S. (1984) J. Chem. Ecol., 10, 1497.

© 2005 by CRC Press LLC


214 Opender Koul

BRUCEINE–B C23H28O11
(480.47)
M.p. : 264–268°

[α]D : –76° (Pyridine)


OH

HO COOCH3
O

O OCOCH3

H
HO O O
H

(1, 2) (1)

SOURCE: Brucea amarissima (Lour.) Merril., common brucea (Xanthoxylaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Heliothis virescens (Fab.) Leaf disk 19.8 µg/cm2 Feeding inhibition = 1. Treatment to 3rd
(Tobacco budworm) assay 60–90% after 6 days instar larvae.
of treatment. (2)

12.0 µg/cm2 Feeding inhibition =


60–90% after 2 days
of treatment, which
declines to 30–60%
after 6 days of
treatment.

2. Epilachna varivestis Muls. Whole leaf 500 ppm Feeding inhibition = 2. Treatment to 4th
(Mexican bean beetle) application 75.0% instar larvae starved
for 2 h. Treatment
duration = 24 h.
Data calculated from
Reference 3.
(3)

(1) Dev, S. and Koul, O. (1997) Insecticides of Natural Origin, Harwood Academic Publishers, Amsterdam, p. 131.
(2) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y.M., Kiyokawa, H., and Lee, K.H.
(1987) J. Nat. Prod., 50, 442.
(3) Leskinen, V., Polonsky, J., and Bhatnagar, S. (1984) J. Chem. Ecol., 10, 1497.

© 2005 by CRC Press LLC


Insect Antifeedants 215

BRUCEINE–C C28H36O12
(564.58)
M.p. : 175–180°

OH [α]D : –34.2° (Pyridine)

HO COOCH3
OH
O

O OCO

HO O O
H

(1, 2) (1)

SOURCE: Brucea amarissima (Lour.) Merril., common brucea (Xanthoxylaceae)(1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Heliothis virescens Leaf disk 19.8 µg/cm2 Feeding inhibition = 1. Treatment to 3rd
(Fab.) assay 90–100% after 2 days and instar larvae.
(Tobacco budworm) 60–90% after 6 days of (2)
treatment.

12.0 µg/cm2 Feeding inhibition =


60–90% after 2 days of
treatment, which declines
to 30–60% after 6 days of
treatment.

6.0 µg/cm2 Feeding inhibition =


60–90% after 2 days of
treatment, which declines
to 0–30% after 6 days of
treatment.

2. Epilachna varivestis Whole leaf 500 ppm Feeding inhibition = 2. Treatment to 4th
Muls. application 66.3% instar larvae starved
(Mexican bean beetle) for 2 h. Treatment
duration = 24 h.
Data calculated from
Reference 3.
(3)

(1) Polonsky, J., Baskevitch, Z., Gaudemer, A., and Das, B.C. (1967) Experientia, 23, 424.
(2) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y.M., Kiyokawa, H., and Lee,
K.H. (1987) J. Nat. Prod., 50, 442.
(3) Leskinen, V., Polonsky, J., and Bhatnagar, S. (1984) J. Chem. Ecol., 10, 1497.

© 2005 by CRC Press LLC


216 Opender Koul

BRUCEINE–D C20H26O9
(410.42)
M.p. : 285–290°

[α]D : –21° (Pyridine)


OH

HO
HO
O

O OH

H OH

O O
H

(1, 2) (1)

SOURCE: Brucea amarissima (Lour.) Merril., common brucea (Xanthoxylaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Heliothis virescens (Fab.) Leaf disk 6.0 µg/cm2 Feeding inhibition = Treatment to 3rd
(Tobacco budworm) assay 90–100% after 2 instar larvae.
days and 60–90%
after 6 days of
treatment.

3.0 µg/cm2 Feeding inhibition =


60–90% after 2 days
of treatment which (2)
declines to 30–60%
after 6 days of
treatment.

(1) Polonsky, J., Baskevitch, Z., Das, B.C., and Muller, J. (1968) Compt. Rend., 267, 1346.
(2) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y.M., Kiyokawa, H., and Lee, K.H.
(1987) J. Nat. Prod., 50, 442.

© 2005 by CRC Press LLC


Insect Antifeedants 217

BUCHANINOSIDE C32H42O11
(602.68)
M.p. : 259°
O
[α]D : –44.6° (CHCl3)
O

H3CO
OH OAc
O

O
OH
O O

(1) (1)

SOURCE: Elaeodendron buchananii, African tropical tree (Celastraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera exempta (Walker) Leaf disk 100.0 µg/µl Feeding inhibition = Treatment to 6th
(Nutgrass armyworm) choice 70.0% instar larvae pre-
assay starved for 2 h.
Treatment duration =
2 h.
(1)

(1) Tsujino, Y., Ogoche, J.I.J., Tazaki, H., Fujimori, T., and Mori, K. (1995) Phytochemistry, 40, 753.

© 2005 by CRC Press LLC


218 Opender Koul

BUDDLEIN–A C20H22O7
(374.39)
M.p. : 106–108°

[α]D25 : –82.3° (CH3OH)


O

O
O
O
CH2
HO
O

(1, 2) (1)

SOURCE: Viguiera buddleiaeformis, viguiera (Asteraceae) (1,2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk 70.0 µg/ Feeding inhibition = Treatment to 5th
(Tobacco armyworm) no-choice 1.5 cm2 60.2% instar larvae pre-
assay starved for 3 h.
Treatment duration =
30 min.
(1)

(1) Passreiter, C.M. and Isman, M.B. (1997) Biochem Syst. Ecol., 25, 371.
(2) De Vivar, A.R., Guerrero, C., Diaz, E., Bratoeff, E.A., and Jimenez, L. (1976) Phytochemistry, 15, 525.

© 2005 by CRC Press LLC


Insect Antifeedants 219

BUSSEIN C43H54O18
(858.92)
O M.p. : 300–304° (dec.)

OAc [α]20
D : –57° (CHCl3)

AcO
O
O
O
H3COOC O
O
OH
OAc

OH
OCO

(1) (1)

SOURCE: Entandrophragma bussei Sprague, mahogany (Fabaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Peridroma saucia (Hubner) Artificial diet 0.5 µM/g Feeding inhibition = Treatment to neonate
(Variegated cutworm) feeding Weak larvae for 24 h. 34%
of the larvae were
seen on treated diets
against 100% of
controls in a choice
situation.
(2)

2. Ostrinia nubilalis (Hubner) Leaf disk no- 50 µg/g Feeding inhibition = 2. Treatment to
(European corn borer) choice assay 45.0% neonate larvae for
500 µg/g Feeding inhibition = 48 h.
74.0% (3)

Data calculated from


Reference 3.

(1) (1982) Dictionary of Organic Compounds, Vol. 1, Chapman & Hall, New York, p. 900.
(2) Champagne, D.E., Isman, M.B., and Towers, G.H.N. (1989) In J.T. Arnason, B.J.R. Philogene, and P. Morand
(eds.), Insecticides of Plant Origin, ACS Symp. Ser. 387, Am. Chem. Soc., Washington, D.C., pp. 95–109.
(3) Arnason, J.T., Philogene, B.J.R., Donskov., N., and Kubo, I. (1987) Entomol. Exp. Appl., 43, 221.

© 2005 by CRC Press LLC


220 Opender Koul

3β-n BUTYRYLOXY-1-OXOMELIAC- C31H40O8


8 (14)-ENATE (540.65)
M.p. : 65–68°
O
[α]20
D : –135° (CHCl3)

H3COOC O O

OCO

(1) (1)

SOURCE: Khaya ivorensis Chev., African mahogany (Meliaceae) (1,2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Agrotis segetum (L.) Artificial diet 100 ppm Feeding inhibition = Treatment to larvae
(Turnip cutworm) feeding 36.0% for 5 days.
(1)

(1) Vanucci, C., Lange, C., Lhommet, G., Dupont, B., Davoust, D., Vauchot, B., Clement, J.L., and Brunck, F.
(1992) Phytochemistry, 31, 3003.

© 2005 by CRC Press LLC


Insect Antifeedants 221

CAFFEIC ACID C9H8O4


(180.16)
M.p. : 200°

COOH

CH CH

OH

OH

(1, 2) (1)

SOURCE: Pteridium aquilinum (L.) Kuhn, bracken fern (Pteridophyte) (2, 3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Pieris brassicae (L.) Leaf disk 5.6 × 10–2 M Feeding ratio = 2.87 1. Treatment to 2nd
(Large white butterfly) no-choice day 5th instar
test unstarved larvae.
Ratio <20 considered
as effective
deterrence
(2)

2. Locusta migratoria (L.) Glass fiber 0.5% dry Significant deterrent 2. Treatment to
(Migratory locust) disk choice weight effect 3-day-old 5th instar
test nymphs for 3 to 4 h.
(4)

(1) Pacsu, E. and Stieber, C. (1929) Ber., 62, 2974.


(2) Jones, C.G. and Firn, R.D. (1979) Biochem. Syst. Ecol., 7, 187.
(3) Bohm, B.A. and Tryon, R.M. (1967) Can. J. Bot., 45, 585.
(4) Bernays, E.A. (1990) Entomol. Exp. Appl., 54, 53.

© 2005 by CRC Press LLC


222 Opender Koul

CAFFEINE C8H10O2N4
(194.19)
M.p. : 235° (anhyd.)
178° (subl.)

O [α]15
D : +2°

N
N

N
O N

(1, 2) (1)

SOURCE: Commercial sample (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Phormia regina (Meigen) Sucrose 10.0 mM Feeding inhibition = Treatment to 2-, 4-,
(Blow fly) solution 40.0% after 6 h and 6-day-old adults,
feeding 46.0% after 24 h pre-starved for 24 h.
(2)

LD50 (rats): 127 mg/kg (oral) (3)

(1) Biltz, H. and Beck, A. (1928) J. Prakt. Chem., 118, 198.


(2) Blades, D. and Mitchell, B.K. (1986) Entomol. Exp. Appl., 41, 299.
(3) Palm, P.E., Arnold, E.P., Rachwell, P.C., Leyczek, J.C., Teague, K.W., and Kensler, C.J. (1978) Toxicol. Appl.
Pharmacol., 44, 1.

© 2005 by CRC Press LLC


Insect Antifeedants 223

CAMELLIDIN–II C53H84O24
(1105.23)
M.p. : 211–212°

[α]D25 : –6° (MeOH)


HO

OH HO COOH H
HO

O O
O
O
HO OH O
OH O
O
O
O
HO
HO

HO HO HO OH

(1, 2) (1)

SOURCE: Camellia japonica L., common camellia (Theaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Eurema hecabe mandarina Artificial diet 0.25% Feeding ratio = Treatment to 5th
Del’Orza feeding 46.8% instar larvae.
(Yellow butterfly) Deterrence observed
to be of mild nature
only.
(1)

(1) Itokawa, H., Nakajima, H., Ikuta, A., and Iitaka, Y. (1981) Phytochemistry, 20, 2539.
(2) Numata, A., Kitajima, A., Katsuno, T., Yamamoto, K., Nagahama, N., Takahashi, C., Fujiki, R., and Nabae,
M. (1987) Chem. Pharm. Bull., 35, 3948.

© 2005 by CRC Press LLC


224 Opender Koul

CANIN C15H18O5
(278.30)
M.p. : 245–246°

OH (M.p. : 250° for Crystals


O from Me2CO)

[α]23
D : –30.5° (EtOH)

H CH2
O

(1, 2) (1,2)

SOURCE: Chrysanthemum macrophyllum W&K, chrysanthemum (Asteraceae) (3)

ACTIVITY PROFILE

Test Insect Test Conc. / Efficacy Remarks


Method Dose

1. Sitophilus granarius L. Wafer disk 8 mg/cm3 Feeding deterrence 1. Treatment given to


(Grain weevil) test coefficient = adults.
51–100

2. Tribolium confusum Jacq. Wafer disk 8 mg/cm3 Feeding deterrence 2. Treatment given to
Duv. test coefficient = both adults and
(Confused flour beetle) 101–150 larvae.

3. Trogoderma granarium Wafer disk 8 mg/cm3 Feeding deterrence 3. Treatment given to


Everts test coefficient = larvae.
(Khapra beetle) 101–150
Neutral value = 0
Absolute feeding
deterrence value =
200
(3)

(1) Lee, K.H., Simpson, R.F., and Geissman, T.A. (1969) Phytochemistry, 8, 1515.
(2) Bhadane, N.R., and Shafizadeh, F. (1975) Phytochemistry, 14, 2651.
(3) Nawrot, J., Bloszyk, E., Grabarczyk, H., and Dorzdz, B. (1982) Prace. Nauk. Inst. Ochr. Roslin., 24, 27.

© 2005 by CRC Press LLC


Insect Antifeedants 225

(−) – CANNABISIN–B C34H32O8N2


(596.64)
Amorphous powder
OH
O
[α]D : –38° (MeOH)
HO H
N

N
HO H

O
OH

OH

OH
(1) (1)

SOURCE: Xylopia aethiopica A. Rich., African pepper (Anonaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Reticulitermes speratus Kolbe. Paper disk 5000 ppm Antifeedant index Treatment to 3rd
(Subterranean termite) choice test value = 7.10 instar workers.
Feeding duration =
14 days.
Antifeedant index
value below 20.0 for
a compound
considered as highly
deterrent
(1)

(1) Lajide, L., Escoubas, P., and Mizutani, J. (1995) Phytochemistry, 40, 1105.

© 2005 by CRC Press LLC


226 Opender Koul

(–) – CANNABISIN–D C36H36O8N2


(624.69)
M.p. : 164–166°
OH (165–168°)
O

CH3O H
N

N
HO H

O
OH

OCH3

OH
(1, 2) (1, 2)

SOURCE: Xylopia aethiopica A. Rich., African pepper (Anonaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Reticulitermes speratus Kolbe Paper disk 5000 ppm Antifeedant index Treatment to 3rd
(Subterranean termite) choice test value = 12.93 instar workers.
Feeding duration =
14 days.
Antifeedant index
value below 20.0 for
a compound
considered as highly
deterrent
(1)

(1) Lajide, L., Escoubas, P., and Mizutani, J. (1995) Phytochemistry, 40, 1105.
(2) Sakakibara, I., Ikeya, Y., Hayashi, K., and Mitsuhashi, H. (1992) Phytochemistry, 31, 3219.

© 2005 by CRC Press LLC


Insect Antifeedants 227

CAPILLARIN C13H10O2
(198.22)
M.p. : 124°

(1, 2, 3) (1, 2)

SOURCE: Artemisia capillaris Thumb., wormwood (Asteraceae) (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Pieris rapae crucivora Boisd. Leaf disk test 10–1 mol/l Feeding inhibition = Treatment to 5th
(Cabbage butterfly) 97.0% instar larvae for 2 h.
(3)

(1) Harada, R., Noguchi, S., and Sugiyama, N. (1960) Nippon Kagaku Zasshi, 81, 654.
(2) Bohlmann, F. and Kleine, K.–M. (1962) Chem. Ber., 95, 39.
(3) Yano, K. (1987) J. Agric. Food Chem., 35, 889.

© 2005 by CRC Press LLC


228 Opender Koul

CAPILLENE C12H10
(154.21)
Oil

d20
0 : 0.977

(1, 2) (1)

SOURCE: Artemisia capillaris Thumb., wormwood (Asteraceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Pieris rapae crucivora Boisd. Leaf disk 0.3 mg/2 cm Feeding inhibition = Treatment to 5th
(Cabbage butterfly) test diameter 100.0% instar larvae for 2 h.
disk. However,
consumption in
controls was also
50% of the amount
provided
(2)

(1) Harada, R. (1957) J. Chem. Soc. Jap., 78, 415.


(2) Yano, K. (1983) J. Agric. Food Chem., 31, 667.

© 2005 by CRC Press LLC


Insect Antifeedants 229

CAPILLIN C12H8O
(168.19)
M.p. : 79.5–80.5°

(1) (1)

SOURCE: Artemisia capillaris Thumb., wormwood (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Pieris rapae crucivora Boisd. Leaf disk test 10–1 mol/l Feeding inhibition = Treatment to 5th
(Cabbage butterfly) 100.0% instar larvae for 2 h.
(1)

(1) Yano, K. (1987) J. Agric. Food Chem., 35, 889.

© 2005 by CRC Press LLC


230 Opender Koul

(+) CARVONE C10H14O


(150.21)
B.p. : 230°

[α]20
D : +62.3° (H2O)

n20
D : 1.4995
O
d20
4 : 0.9608

CH2

(1, 2) (2)

SOURCE: Commercial sample (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Hylobius pales (Herbst.) Twig dip 10.0% Feeding inhibition = 1. Treatment to


(Pales weevil) treatment 69.0% 22–65 mg weevil
choice assay body weight for 24 h.
Data calculated from
Reference 1.
(1)

2. Locusta migratoria (L.) Wafer disk 0.1% dry Feeding inhibition = 2. Treatment to 5th
(Migratory locust) test weight 50.0% instar 3- to 6-day-old
basis nymphs

(3)

LD50 (rats): 1640 mg/kg (oral) (4)

(1) Salom, S.M., Carlson, J.A., Ang, B.N., Grosman, D.M., and Day, E.R. (1994) J. Entomol. Sci., 29, 407.
(2) Dev, S. and Koul, O. (1997) Insecticides of Natural Origin, Harwood Academic Publishers, Amsterdam, p. 55.
(3) Bernays, E.A. and Chapman, R.F. (1977) Ecol. Entomol., 2, 1.
(4) Jenner, P.M., Hagan, E.C., Taylor, J.M., Cook, E.L., and Fetzhugh, O.G. (1964) Food Cosmetics Toxicol., 2,
327.

© 2005 by CRC Press LLC


Insect Antifeedants 231

(–) CARVONE C10H14O


(150.21)
B.p. : 230°

[α]20
D : +69.1° (H2O)

O n18
D : 1.4999

CH2

(1, 2) (1, 2)

SOURCE: Commercial sample (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Hylobius pales (Herbst.) Twig dip 10.0% Feeding inhibition = 1. Treatment to


(Pales weevil) treatment 65.5% 22–65 mg weevil
choice assay body weight for 24 h.
Data calculated from
Reference 4.
(4)

2. Spodoptera littoralis (Boisd.) Artificial diet 1.0% Only 26.4% of 2. Treatment to


(Egyptian cotton leaf worm) feeding normal pupae 10–20 mg body
developed against weight larvae.
74.4 in controls due
to phagodeterrence (3)

0.5% Only 33.7% of


normal pupae
developed against
74.4 in controls due
to phagodeterrence

(1) Doeuvre, J. (1934) Bull. Soc. Chim., 1, 198.


(2) Naves, Y.R. and Bachmann, P. (1946) Helv. Chim. Acta, 29, 61.
(3) Meisner, J., Fleischer, A., and Eizick, C. (1982) J. Econ. Entomol., 75, 462.
(4) Salom, S.M., Carlson, J.A., Ang, B.N., Grosman, D.M., and Day, E.R. (1994) J. Entomol. Sci., 29, 407.

© 2005 by CRC Press LLC


232 Opender Koul

β-CARYOPHYLLENE C15H24
(204.36)
B.p. : 129–130°/14 mm

H2C
[α]15
D : –5.2° (benzene)

(1, 2) (1)

SOURCE: Artemisia capillaris Thumb., wormwood (Asteraceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Pieris rapae crucivora Boisd. Leaf disk test 10–1 mol/l Feeding inhibition = 1. Treatment to 5th
(Cabbage butterfly) 73.0% instar larvae for 2 h.
(2)

2. Locusta migratoria (L.) Wafer disk 0.01% dry Feeding inhibition = 2. Treatment to 5th
(Migratory locust) test weight 50.0% instar 3- to 6-day-old
basis nymphs.
(3)

(1) Aebi, A., Barton, D.H.R., and Lindsay, A.S. (1953) J. Chem. Soc., 3124.
(2) Yano, K. (1987) J. Agric. Food Chem., 35, 889.
(3) Bernays, E.A. and Chapman, R.F. (1977) Ecol. Entomol., 2, 1.

© 2005 by CRC Press LLC


Insect Antifeedants 233

6,7-EPOXY-3(15)-CARYOPHYLLENE C15H24O
(220.34)
Oil

[α]D : –40° (CHCl3)

H
H
O

CH2

(1) (1)

SOURCE: Senecio palmensis Chr.Sm., groundsel (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera littoralis (Boisd.) Choice 159.1 nmol/cm2 Feeding deterrence = 1. Treatment to 6th
(Eygyptian cotton leaf worm) feeding 50.0% instar larvae.
assay

2. Leptinotarsa decemlineata Choice >200 nmol/cm2 Feeding deterrence = 2. Treatment to


(Say) feeding 50.0% adults.
(Colorado potato beetle) assay

3. Myzus persicae (Sulzer) Choice >500 nmol/cm2 Feeding deterrence = 3. Treatment to


(Green peach aphid) feeding 50.0% apterous adult
assay aphids.

4. Rhopalosiphum padi (L.) Choice 43.3 nmol/cm2 Feeding deterrence = 4. Treatment to


(Cereal aphid) feeding 50.0% apterous adult
assay aphids.

5. Sitobion avenae (Fab.) Choice >200 nmol/cm2 Feeding deterrence = 5. Treatment to


(Grass aphid) feeding 50.0% apterous adult
assay aphids.

6. Diuraphis noxia (Mordvilko) Choice 38.4 nmol/cm2 Feeding deterrence = 6. Treatment to


(Wheat aphid) feeding 50.0% apterous adult
assay aphids.
Concentrations =
EC50 values
(1)

(1) Reina, M., Nold, M., Santana, O., Orihuela, J.C., and Gonzalez-Coloma, A. (2002) J. Nat. Prod., 65, 448.

© 2005 by CRC Press LLC


234 Opender Koul

CARYOPTIN C26H36O9
(492.56)
M.p. : 176–177°
O
[α]D : –91° (CHCl3)
H H

AcO

H
O CH2
OAc

OAc
(1, 2) (1, 2)

SOURCE: Caryopteris divaricata Maxim., snow fairy (Verbenaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk test 200 ppm Feeding inhibition = Treatment to 3rd
(Tobacco armyworm) 100% instar larvae.
Feeding duration =
2 h.
Larvae eventually
starved to death.
Thus compound
termed as absolute
antifeedant.
(2)

(1) Hosozawa, S., Kato, N., and Munakata, K. (1973) Phytochemistry, 12, 1833.
(2) Hosozawa, S., Kato, N., Munakata, K., and Chen, Y. (1974) Agric. Biol. Chem., 38, 1045.

© 2005 by CRC Press LLC


Insect Antifeedants 235

CARYOPTIN HEMIACETAL C26H38O10


OH
(510.58)
M.p. : 188–189°

H H

AcO

H
O CH2
OAc

OAc (1, 2) (1, 2)

SOURCE: Caryopteris divaricata Maxim., snow fairy (Verbenaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk test 200 ppm Feeding inhibition = Treatment to 3rd
(Tobacco armyworm) 100% instar larvae.
Feeding duration =
2 h.
Larvae eventually
starved to death.
Thus compound
termed as absolute
antifeedant.
(2)

(1) Hosozawa, S., Kato, N., and Munakata, K. (1973) Phytochemistry, 12, 1833.
(2) Hosozawa, S., Kato, N., Munakata, K., and Chen, Y. (1974) Agric. Biol. Chem., 38, 1045.

© 2005 by CRC Press LLC


236 Opender Koul

CARYOPTINOL C24H34O8
(450.53)
M.p. : 219–220°

O [α]D : –83° (CHCl3)

H H

HO
O CH2
OAc

OAc (1) (1)

SOURCE: Caryopteris divaricata Maxim., snow fairy (Verbenaceae) (1,2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk test 200 ppm Feeding inhibition = Treatment to 3rd
(Tobacco armyworm) 100% instar larvae.
Feeding duration =
2 h.
Larvae eventually
starved to death.
Thus compound
termed as absolute
antifeedant.
(2)

(1) Hosozawa, S., Kato, N., and Munakata, K. (1973) Phytochemistry, 12, 1833.
(2) Hosozawa, S., Kato, N., Munakata, K., and Chen, Y. (1974) Agric. Biol. Chem., 38, 1045.

© 2005 by CRC Press LLC


Insect Antifeedants 237

CASTANOSPERMINE C8H15O4N
(189.21)
M.p. : 212–215° (dec.)

[α]25
D : +79.7° (H2O)

OH
H OH
HO

N
HO

(1, 2) (1)

SOURCE: Castanospermum australe A. Cunn. and Fraser, black bean (Fabaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Acyrthosiphon pisum (Harris) Artificial diet 0.00002 ± Feeding inhibition = Treatment to aphids
(Pea aphid) feeding 0.00001% 50.0% at random.
Concentration = EC50
value
(2)

(1) Hohenschutz, L.D., Bell, E.A., Jewess, P.J., Leworthy, D.P., Pryce, R.J., Arnold, E., and Clardy, J. (1981)
Phytochemistry, 20, 811.
(2) Dreyer, D.L., Jones, K.C., and Molyneux, R.J. (1985) J. Chem. Ecol., 11, 1045.

© 2005 by CRC Press LLC


238 Opender Koul

CATALPOSIDE C22H26O12
(482.44)
OCO OH M.p. : 215–216°
H

[α]29
D : –167° (MeOH)

O
O
H
HOH2C
O
CH2OH

O
OH

HO H

OH (1) (2)

SOURCE: Catalpa speciosa (Warder) Barney, catalpa (Bignoniaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Lymantria dispar (L.) Artificial diet 1.7 mg/ml Feeding inhibition = Treatment to larvae.
(Gypsy moth) feeding 19.0% (2)

(1) Bobbit, J.M., Schmid, H., and Africa, T.B. (1961) J. Org. Chem., 26, 3090.
(2) El-Naggar, S.F. and Doskotch, R.W. (1980) J. Nat. Prod., 43, 524.

© 2005 by CRC Press LLC


Insect Antifeedants 239

CEDRELONE C26H30O5
O
(422.52)
M.p. : 209–214°

[α]30
D : –65° (CHCl3)

O O

OH (1, 2) (1, 2)

SOURCE: Cedrela toona Roxb., cedro toona (Meliaceae)


Cedrela odorata L., Spanish cedar (Meliaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera litura (Fab.) Leaf disk 0.1% Feeding inhibition = 1. Treatment to


(Tobacco armyworm) choice test 100.0% larvae in the weight
range of 100–130 mg
0.05% Feeding inhibition = for 24 h.
50.0% Data calculated from
Reference 3.
(3)
Leaf disk 5.0 µg/cm2 Feeding inhibition = Treatment to 3rd
dual-choice 50.5% instar larvae for 24 h.
test (4)
50.0 µg/cm2 Feeding inhibition =
75.8%

2. Peridroma saucia (Hubner) Leaf disk 28.6 µg/cm2 Feeding inhibition = 2. Treatment to 5th
(Variegated cutworm) choice test 51.7% instar larvae for 6 h.
(5)
3. Mamestra configurata Walker Leaf disk 28.6 µg/cm2 Feeding inhibition = 3. Treatment to 5th
(Bertha armyworm) choice test 75.9% instar larvae for 6 h.
(5)
4. Ostrinia nubilalis (Hubner) Leaf disk 50 µg/g Feeding inhibition = 4. Treatment to
(European corn borer) no-choice 55.0% neonate larvae for
assay 48 h.
(6)
Data calculated from
Reference 6.

(1) Gopinath, K.W., Govindachari, T.R., Parthasarthy, P.C., Viswanathan, N., Arigoni, D., and Wildmann, W.C.
(1961) Proc. Chem. Soc. (London), 446.
(2) Chaterjee, A., Cjhakraborthy, T., and Chandrasekharan, S. (1971) Phytochemistry, 10, 2533.
(3) Koul, O. (1983) J. Appl. Entomol., 95, 166.
(4) Govindachari, T.R., Narasimhan, N.S., Suresh, G., Partho, P.D., Gopalakrishnan, G., and Krishnakumari, G.N.
(1995) J. Chem Ecol., 21, 1586.
(5) Koul, O. and Isman, M.B. (1992) Entomol. Exp. Appl., 64, 281.
(6) Arnason, J.T., Philogene, B.J.R., Donskov, N., and Kubo, I. (1987) Entomol. Exp. Appl., 43, 221.

© 2005 by CRC Press LLC


240 Opender Koul

CEDRELONE ACETATE C28H32O6


(464.56)
M.p. : 156–159°

[α]D : –56° (CHCl3)


O

O O

OAc

(1, 2) (1)

SOURCE: Synthetic (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk 1 µg/cm2 Feeding inhibition = Treatment to 3rd
(Tobacco armyworm) dual-choice 45.0% instar larvae for 24 h.
test FI50 = 8.2 µg/cm2
5 µg/cm2 Feeding inhibition =
45.2% Data calculated from
Reference 2.
10 µg/cm2 Feeding inhibition = (2)
57.0%

50 µg/cm2 Feeding inhibition =


61.5%

(1) Hodges, R., McGeachin, S.G., and Raphel, R.A. (1963) J. Chem. Soc., 2515.
(2) Govindachari, T.R., Narasimhan, N.S., Suresh, G., Partho, P.D., Gopalakrishnan, G., and Krishnakumari, G.N.
(1995) J. Chem Ecol., 21, 1586.

© 2005 by CRC Press LLC


Insect Antifeedants 241

CEDRELONE EPOXIDE C26H30O6


(438.52)
M.p. : 222–228°

[α]D : –10.6° (CHCl3)


O

O O

OH

(1, 2) (1)

SOURCE: Synthetic (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk 1 µg/cm2 Feeding inhibition = Treatment to 3rd
(Tobacco armyworm) dual-choice 56.5% instar larvae for 24 h.
test FI50 = 0.85 µg/cm2
5 µg/cm2 Feeding inhibition =
59.2% Data calculated from
Reference 2.
10 µg/cm2 Feeding inhibition = (2)
58.5%

50 µg/cm2 Feeding inhibition =


64.5%

(1) Hodges, R., McGeachin, S.G., and Raphel, R.A. (1963) J. Chem. Soc., 2515.
(2) Govindachari, T.R., Narasimhan, N.S., Suresh, G., Partho, P.D., Gopalakrishnan, G., and Krishnakumari, G.N.
(1995) J. Chem Ecol., 21, 1586.

© 2005 by CRC Press LLC


242 Opender Koul

CEDRELONE EPOXIDE ACETATE C28H32O7


(480.56)
M.p. : 214–217°

[α]D : –26° (CHCl3)


O

O O

OAc

(1, 2) (1)

SOURCE: Synthetic (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk 1 µg/cm2 Feeding inhibition = Treatment to 3rd
(Tobacco armyworm) dual-choice 46.8% instar larvae for 24 h.
test FI50 = 4.5 µg/cm2
5 µg/cm2 Feeding inhibition =
52.4% Data calculated from
Reference 2.
10 µg/cm2 Feeding inhibition = (2)
59.2%

50 µg/cm2 Feeding inhibition =


59.1%

(1) Hodges, R., McGeachin, S.G., and Raphel, R.A. (1963) J. Chem. Soc., 2515.
(2) Govindachari, T.R., Narasimhan, N.S., Suresh, G., Partho, P.D., Gopalakrishnan, G., and Krishnakumari, G.N.
(1995) J. Chem Ecol., 21, 1586.

© 2005 by CRC Press LLC


Insect Antifeedants 243

CEDRELONE EPOXIDE-METHYLETHER C27H32O6


(452.55)
Only spectral data given

O O

OCH3

(1, 2) (2)

SOURCE: Synthetic (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk 1 µg/cm2 Feeding inhibition = Treatment to 3rd
(Tobacco armyworm) dual-choice 46.0% instar larvae for 24 h.
test FI50 = 4.8 µg/cm2
5 µg/cm2 Feeding inhibition =
51.6% Data calculated from
Reference 2.
10 µg/cm2 Feeding inhibition = (2)
52.4%

50 µg/cm2 Feeding inhibition =


63.0%

(1) Hodges, R., McGeachin, S.G., and Raphel, R.A. (1963) J. Chem. Soc., 2515.
(2) Govindachari, T.R., Narasimhan, N.S., Suresh, G., Partho, P.D., Gopalakrishnan, G., and Krishnakumari, G.N.
(1995) J. Chem Ecol., 21, 1586.

© 2005 by CRC Press LLC


244 Opender Koul

CEDRELONE METHYLETHER C27H32O5


(436.55)
M.p. : 207–210°

[α]D : –13.4° (CHCl3)


O

O O

OCH3

(1, 2) (1)

SOURCE: Synthetic (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk 1 µg/cm2 Feeding inhibition = Treatment to 3rd
(Tobacco armyworm) dual-choice 44.0% instar larvae for 24 h.
test FI50 = 9.5 µg/cm2
5 µg/cm2 Feeding inhibition =
50.5% Data calculated from
Reference 2.
10 µg/cm2 Feeding inhibition = (2)
48.5%

50 µg/cm2 Feeding inhibition =


57.2%

(1) Hodges, R., McGeachin, S.G., and Raphel, R.A. (1963) J. Chem. Soc., 2515.
(2) Govindachari, T.R., Narasimhan, N.S., Suresh, G., Partho, P.D., Gopalakrishnan, G., and Krishnakumari, G.N.
(1995) J. Chem Ecol., 21, 1586.

© 2005 by CRC Press LLC


Insect Antifeedants 245

CELANGULIN C32H40O14
(648.66)
Amorphous powder

OAc

OAc O
O
CH2
AcO OAc

HO O
OAc (1) (1)

SOURCE: Celastrus angulatus Maxim., bittersweet tree (Celastraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera frugiperda Artificial diet 5 ppm Feeding inhibition = Treatment to 1st


(J.E. Smith) test 39.0% instar larvae.
(Fall armyworm) Calculations made
10 ppm Feeding inhibition = on the basis of
63.0% reduction in weight
due to starvation.
(1)

(1) Wakabayashi, N., Wu, W.J., Waters, R.M., Redfern, R.E., Mills, G.D. Jr., DeMilo, A.B., Lusby, W.R., and
Andrzejewski, D. (1988) J. Nat. Prod., 51, 537–542.

© 2005 by CRC Press LLC


246 Opender Koul

α-CHACONINE C45H73O14N
(solanidine) (852.07)
M.p. : 243°

[α]D : –85° (Pyridine)

2.Rham - glu - O

(1, 2) (1)

SOURCE: Solanum sp. (Solanaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Choristoneura fumiferana Paper 10–3 M Feeding inhibition = 1. Treatment to 6th


(Clemens) penicillin 77.0% instar larvae.
(Spruce budworm) disk assay (2)
10–4 M Feeding inhibition =
41.0%

2. Leptinotarsa decemlineata Sensillum 0.6% wet Feeding inhibition = 2. Treatment to adult


(Say) response weight 50.0% beetles.
(Colorado potato beetle) recording
Concentration = FI50
value.
(3)

LD50 (rats): 84 mg/kg (ipr.) (4)

(1) (1994) Dictionary of Natural Products, Chapman & Hall, London.


(2) Bentley, M.D., Leonard, D.E., and Bushway, R.J. (1984) Ann. Entomol. Soc. Am., 77, 401.
(3) Mitchell, B.K. and Harrison, G.D. (1985) J. Chem. Ecol., 11, 73.
(4) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC


Insect Antifeedants 247

CHALCONE C17H16O5
2′,4′-DIHYDROXY-4,6′-DIMETHOXY (300.29)
M.p. : 194–195°

OH

H3CO OCH3

OH O

(1) (1)

SOURCE: Gnaphalium affine D. Don, cudweed (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera litura (Fab.) Leaf disk 2.1 × 10–5 Feeding inhibition = 1. Treatment to 3rd
(Tobacco armyworm) choice test mol/cm2 50% instar larvae in the
dark for 2 to 5 h.
Concentration = FI50
value
(1)

(1) Morimoto, M., Kumeda, S., and Komai, K. (2000) J. Agric. Food Chem., 48, 1888.

© 2005 by CRC Press LLC


248 Opender Koul

CHALCONE C18H18O5
2′-HYDROXY-4,4′,6′-TRIMETHOXY (314.32)
M.p. : 113°

OCH3

H3CO OCH3

OH O

(1) (1)

SOURCE: Gnaphalium affine D. Don, cudweed (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera litura (Fab.) Leaf disk 9.0 × 10–6 Feeding inhibition = 1. Treatment to 3rd
(Tobacco armyworm) choice test mol/cm2 50% instar larvae in the
dark for 2 to 5 h.
Concentration = FI50
value
(1)

(1) Morimoto, M., Kumeda, S., and Komai, K. (2000) J. Agric. Food Chem., 48, 1888.

© 2005 by CRC Press LLC


Insect Antifeedants 249

CHALCONE C19H20O5
4,2′,4′,6′-TETRAMETHOXY (328.35)
M.p. : 119–121°

OCH3

H3CO OCH3

OCH3 O

(1) (1)

SOURCE: Gnaphalium affine D. Don, cudweed (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera litura (Fab.) Leaf disk 5.2 × 10–7 Feeding inhibition = 1. Treatment to 3rd
(Tobacco armyworm) choice test mol/cm2 50% instar larvae in the
dark for 2 to 5 h.
Concentration = FI50
value
(1)

(1) Morimoto, M., Kumeda, S., and Komai, K. (2000) J. Agric. Food Chem., 48, 1888.

© 2005 by CRC Press LLC


250 Opender Koul

CHALCONE C16H14O5
4,4′,6′-TRIHYDROXY-2′-METHOXY (286.27)
M.p. : 248°

OH

HO OCH3

OH O

(1) (1)

SOURCE: Gnaphalium affine D. Don, cudweed (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera litura (Fab.) Leaf disk 3.8 × 10–7 Feeding inhibition = 1. Treatment to 3rd
(Tobacco armyworm) choice test mol/cm2 50% instar larvae in the
dark for 2 to 5 h.
Concentration = FI50
value
(1)

(1) Morimoto, M., Kumeda, S., and Komai, K. (2000) J. Agric. Food Chem., 48, 1888.

© 2005 by CRC Press LLC


Insect Antifeedants 251

CHAMAEDROXIDE C20H22O7
(374.39)
M.p. : 255–257°
O
[α]20
D : +37.1° (Pyridine)

HO O

O
O
O

(1, 2) (1)

SOURCE: Teucrium chaemaedrys L., wall germander (Labiatae) (1,2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera littoralis (Boisd.) Glass fiber 100 ppm Feeding inhibition = 1. Treatment to final
(Egyptian cotton leaf worm) disk choice 31.8% stadium larvae pre-
test starved for 4 h.
10 ppm Feeding inhibition = Treatment was never
25.6% longer than 18 h so
that not more than
50% of any disk was
consumed.
(2)

2. Leptinotarsa decemlineata Glass fiber 100 ppm Feeding inhibition = 2. Treatment to final
(Say) disk choice 18.9% stadium larvae pre-
(Colorado potato beetle) test starved for 4 h.
10 ppm Feeding inhibition = Treatment was never
16.7% longer than 18 h so
that not more than
50% of any disk was
consumed.
(2)

(1) Eguren, L., Perales, A., Fayos, J., Rodriguez, B., Savona, G., and Piozzi, F. (1982) J. Org. Chem., 47, 4157.
(2) Simmonds, M.S.J., Blaney, W.M., Ley, S.V., Savona, G., Bruno, M., and Rodriguez, B. (1989) Phytochemistry,
28, 1069.

© 2005 by CRC Press LLC


252 Opender Koul

CHAPARRIN C20H28O7
(380.44)
M.p. : 306–308°

[α]26
D : 45.2° (pyridine)
OH

HO
HO
O

HO H

O O
H

(1, 2, 3) (1, 2, 4)

SOURCE: Castela nicholsoni Hook, cockspur (Simaroubeaceae) (2, 3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Heliothis virescens (Fab.) Leaf disk 19.8 µg/cm2 Feeding inhibition = Treatment to 3rd
(Tobacco budworm) choice test 30–60% after 2 days. instar larvae.
(3)

(1) Geissman, T.A. and Chandorkar, K.R. (1961) J. Org. Chem., 26, 1217.
(2) Geissman, T.A. and Ellestad, G.A. (1962) Tetrahedron Lett., 3, 1083.
(3) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y., Kiyokawa, H., and Lee, K. (1987)
J. Nat. Prod., 50, 442.
(4) Davidson, T.A., Hollands, T.R., Mayo, P.D., and Nisbet, M. (1965) Can. J. Chem., 43, 2996.

© 2005 by CRC Press LLC


Insect Antifeedants 253

CHAPARRINONE C20H26O7
(378.42)
M.p. : 238–242°

[α]D : –47° (pyridine)


OH

HO
HO
O
H
O

O O

(1, 2, 3) (1, 2, 4)

SOURCE: Simaba multiflora A. Juss., cajurana (Simaroubaceae) (2, 3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Heliothis virescens (Fab.) Leaf disk 15.0 µg/cm2 Feeding inhibition = 1. Treatment to 3rd
(Tobacco budworm) choice test 95% instar larvae.
Concentration =
PC95.
(3)

2. Spodoptera frugiperda Leaf disk 6.0 µg/cm2 Feeding inhibition = 2. Treatment to 3rd
(J.E. Smith) choice test 95% instar larvae.
(Fall armyworm) Concentration =
PC95.
(3)

3. Epilachna varivestis Muls. Whole leaf 200 ppm Feeding inhibition = 3. Treatment to 4th
(Mexican bean beetle) application 82.4% instar larvae pre-
starved for 2 h.
100 ppm Feeding inhibition = Treatment duration =
78.0% 24 h. Data calculated
from Reference 4.
(4)

(1) Polonsky, J. and Bourguignon-Zylber, N. (1965) Bull. Soc. Chim. Fr., 2793.
(2) Arisawa, M., Kinghorn, A.D., Cordell, G.A., and Farnsworth, N.R. (1983) J. Nat. Prod., 46, 218.
(3) Clocke, J.A., Arisawa, M., Handa, S.S., Kinghorn, A.D., Cordell, G.A., and Farnsworth, N.R. (1985) Expe-
rientia, 41, 7.
(4) Leskinen, V., Polonsky, J., and Bhatnagar, S. (1984) J. Chem. Ecol., 10, 1497.

© 2005 by CRC Press LLC


254 Opender Koul

CHELIDONIC ACID C7H4O6


(184.10)
M.p. : 262° (dec.)

HOOC O COOH

(1) (1)

SOURCE: Sorghum bicolor (L.) Moench., grain sorghum (Poaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Schizaphis graminum (Rondani) Artificial diet 0.15% Feeding inhibition = Treatment to 50 to 75


(Wheat aphid) feeding 50.0% aphids at random in
each treatment.
Concentration = EC50.
(2)

(1) Bough, W.A. and Gander, J.E. (1972) Phytochemistry, 11, 209.
(2) Dreyer, D.L., Reese, J.C., and Jones, K.C. (1981) J. Chem. Ecol., 7, 273.

© 2005 by CRC Press LLC


Insect Antifeedants 255

CHICORIC ACID C22H18O12


(474.37)
M.p. : 206°
OH
[α]D : +383.5° (MeOH)
COOH
OH

H C OOC

COO C H

COOH
HO

OH
(1, 2) (1)

SOURCE: Cichorium intybus L., chicory (Asteraceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Schistocerca gregaria (Forsk.) Glass fiber 1.06% dry Feeding inhibition = Treatment to 2- to 3-
(Desert locust) disk test weight 92.6% day-old adults of
either sex (1:1).
0.83% dry Feeding inhibition =
weight 72.3% Data calculated from
Reference 2.
0.48% dry Feeding inhibition = (2)
weight 56.6%

(1) Scarpati, M.L. and Oriente, G. (1958) Tetrahedron, 4, 43.


(2) Rees, S.B. and Harborne, J.B. (1985) Phytochemistry, 24, 2225.

© 2005 by CRC Press LLC


256 Opender Koul

CHLORDIMEFORM C10H13N2Cl
(196.67)
M.p. : 35°

B.p : 156–157°/0.4 mm

n25
D : 1.5885

Cl N = CHN

(1, 2) (1, 2)

SOURCE: Commercial sample (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk 200 ppm Feeding inhibition = Treatment to 5th
(Tobacco armyworm) choice test 50.0% instar larvae without
subjecting to pre-
starvation.
Concentration = EC50
value.
4493.12 ppm Feeding inhibition = Concentration =
95.0% EC95 value.
(2)

956.0 ppm Feeding inhibition = Treatment to 5th


50.0% instar larvae pre-
starved for 24 h.
Concentration = EC50
value.
(2)

LD50 (rats): 238 mg/kg (i.p.) (3)

(1) Schering, A.G. (1964), Ger. Pat. 1172081.


(2) Antonious, A.G. and Saito, T. (1981) Appl. Ent. Zool., 16, 328.
(3) Robinson, C.P. and Smith, P.W. (1977) J. Toxicol. Environ. Health, 3, 565.

© 2005 by CRC Press LLC


Insect Antifeedants 257

15-O-CHLOROBENZOYL BRUCEOLIDE C28H30O11Cl


(577.99)
Only spectral data given

OH
Cl
HO COOCH3
O

O OCO

A
H
HO O O
H

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Heliothis virescens (Fab.) Leaf disk 12.0 µg/cm2 Feeding inhibition = Treatment to 3rd
(Tobacco budworm) choice test 60–90% after 2 days instar larvae.
and 0–30% after 6 (1)
days

6.0 µg/cm2 Feeding inhibition = Treatment to 3rd


30–60% after 2 days instar larvae.
and 0–30% after 6 (1)
days

(1) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y., Kiyokawa, H., and Lee, K.H.
(1987) J. Nat. Prod., 50, 442.

© 2005 by CRC Press LLC


258 Opender Koul

15-m-CHLOROBENZOYL BRUCEOLIDE C28H30O11Cl


(577.99)
Only spectral data given

OH

HO COOCH3
O
O OCO

A
H
HO O Cl
O
H

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Heliothis virescens (Fab.) Leaf disk 12.0 µg/cm2 Feeding inhibition = Treatment to 3rd
(Tobacco budworm) choice test 60–90% after 2 days instar larvae.
and 0–30% after 6 (1)
days

6.0 µg/cm2 Feeding inhibition = Treatment to 3rd


30–60% after 2 days instar larvae.
and 0–30% after 6 (1)
days

(1) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y., Kiyokawa, H., and Lee, K.H.
(1987) J. Nat. Prod., 50, 442.

© 2005 by CRC Press LLC


Insect Antifeedants 259

CHLOROGENIC ACID C16H18O9


(354.31)
M.p. : 208°
OH

[α]26
D : –35.2° (H2O)
OH

OOCCH = CH

COOH

OH OH

OH

(1, 2) (1, 2)

SOURCE: Many dicotyledenous plants (1, 2, 3)


Pteridium aquilinum L. Kuhn., bracken fern (Pteridophyte) (4)
Salix integra, willow (Salicaceae) (5)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Schizaphis graminum Artificial 0.2% Feeding inhibition = 1. Treatment to


(Rondani) diet feeding 50.0% 50–75 aphids at
(Wheat aphid) random for 24 h.

2. Myzus persicae (Sulzer) Artificial 0.35% Feeding inhibition = 2. Treatment to


(Green peach aphid) diet feeding 50.0% 50–75 aphids at
random for 8 h.
Concentrations =
EC50 values.
(3)

3. Pieris brassicae (L.) Leaf disk 1.4 × 10–2 M Feeding ratio = 2.51 3. Treatment to 2nd
(Large white butterfly) no-choice day 5th instar
test unstarved larvae.
Ratio of < 20 is
effective deterrence.
(4)

4. Lochmaea capreae cribrata Filter paper 0.1 M Feeding inhibition = 4. Treatment to adult
Solsky. disk test 100% beetles starved for
(Leaf beetle) 24 h. No nibbling of
0.01 M Considerably less test material
feeding than observed at 0.1 M.
controls. (5)

5. Plagiodera versicolora Filter paper 0.1 M As much feeding as 5. Treatment to adult


distincta Baly. disk test in controls beetles starved for
(Salicaceae leaf beetle) 24 h.
(5)

© 2005 by CRC Press LLC


260 Opender Koul

6. Altica oleraceae (L.) Filter paper 0.01 M Feeding inhibition = 6. Treatment to adult
(Alder leaf beetles) disk test 100% beetles starved for
24 h.
(5)

7. Galelucella vittaticollis Baly. Filter paper 0.01 M Considerably less 7. Treatment to adult
(Strawberry leaf beetle) disk test feeding than controls beetles starved for
24 h.
(5)

(1) Fischer, H.O.L. and Danyschat, G. (1932) Ber. Dtsch. Chem. Ges., 65, 1037.
(2) Barnes, H.M., Feldman, J.R., and White, W.V. (1950) J. Am. Chem. Soc., 72, 4178.
(3) Dreyer, D.L. and Jones, K.C. (1981) Phytochemistry, 20, 2489.
(4) Jones, C.G. and Firn, R.D. (1979) Biochem. Syst. Ecol., 7, 187.
(5) Matsuda, K. and Senbo, S. (1986) Appl. Ent. Zool., 21, 411.

© 2005 by CRC Press LLC


Insect Antifeedants 261

12α-CHLOROMETHYL ROTENONE C23H23O6Cl


(442.89)
No physical data gven
OCH3

CH3O
O
CH2Cl

O
O O

CH2

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius L. Wafer disk 10 mg/ml Feeding deterrence Treatment given to


(Grain weevil) test coefficient = 81.1 adults.
(1)

2. Tribolium confusum Jacq. Wafer disk 10 mg/ml Feeding deterrence Treatment given to
Duv. test coefficient = both adults and
(Confused flour beetle) Larvae = 132.4 larvae.
Adults = 138.4 (1)

3. Trogoderma granarium Wafer disk 10 mg/ml Feeding deterrence Treatment given to


Everts test coefficient = 192.7 larvae.
(Khapra beetle)
Neutral value = 0
Absolute feeding
deterrence value =
200
(1)

(1) Nawrot, J., Harmatha, J., Kostova, I., and Ognyanov, I. (1982) Biochem. Syst. Ecol., 17, 55.

© 2005 by CRC Press LLC


262 Opender Koul

8′-CHLOROROTENONE C22H20O6Cl
(427.86)
No physical data given
OCH3

CH3O
O

O
O O

C CH2Cl

H
CH2

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius L. Wafer disk 10 mg/ml Feeding deterrence Treatment given to


(Grain weevil) test coefficient = 142.1 adults.
(1)

2. Tribolium confusum Jacq. Wafer disk 10 mg/ml Feeding deterrence Treatment given to
Duv. test coefficient = both adults and
(Confused flour beetle) Larvae = 116.8 larvae.
Adults = 133.8 (1)

3. Trogoderma granarium Wafer disk 10 mg/ml Feeding deterrence Treatment given to


Everts test coefficient = 115.9 larvae.
(Khapra beetle)
Neutral value = 0
Absolute feeding
deterrence value =
200
(1)

(1) Nawrot, J., Harmatha, J., Kostova, I., and Ognyanov, I. (1982) Biochem. Syst. Ecol., 17, 55-57.

© 2005 by CRC Press LLC


Insect Antifeedants 263

CICHORIIN C15H16O9
(340.28)
M.p. : 213–215°

[α]18
D : –105° (dioxane)
HO

O
HO O O O

OH OH HO

(1, 2, 3) (1, 2)

SOURCE: Cichorium intybus L., chicory (Asteraceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Schistocerca gregaria (Forsk.) Glass fiber 0.168% dry Feeding inhibition = Treatment to 2- to 3-
(Desert locust) disk test weight 96.3% day-old adults of
either sex (1:1).

0.084% dry Feeding inhibition = Data calculated from


weight 66.9% Reference 3.
(3)
0.011% dry Feeding inhibition =
weight 66.1%

0.001% dry Feeding inhibition =


weight 51.1%

(1) Merz, K. (1932) Arch. Pharm., 270, 476.


(2) Head, F. and Robertson, A. (1939) J. Chem. Soc., 1266.
(3) Rees, S.B. and Harborne, J.B. (1985) Phytochemistry, 24, 2225.

© 2005 by CRC Press LLC


264 Opender Koul

CINNAMALDEHYDE C9H8O
(132.15)
B.p. : 210°/250 mm

d20
4 : 1.0497
CHO
n20
D : 1.61949

(1, 2, 3) (1, 2)

SOURCE: Commercial sample (3)


Alchornea triplinervia (Spreng.) Muell. Arg., larenjeira (Euphorbiaceae) (4)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Pieris brassicae (L.) Leaf disk 7.6 × 10–2 M Feeding ratio = 1. Treatment to 2nd
(Large white butterfly) no-choice 21.9, considered as day 5th instar
test strong antifeedant unstarved larvae.
effect. (3)

2. Anthonomus grandis Bohem. Artificial 10 mg/4 cm2 Feeding ratio = 2. Treatment to


(Boll weevil) diet 4.0% freshly emerged boll
feeding weevils. Percent
20 mg/4 cm2 Feeding ratio = feeding ratio (T/C)
4.0% value of 0 represents
total feeding
30 mg/4 cm2 Feeding ratio = deterrence and >100
0.0% as attraction.
(4)

LD50 (rats): 2220 mg/kg (oral) (5)

(1) Bert, L. and Anneguin, R. (1931) Compt. Rend., 192, 1315.


(2) Dev, S. and Koul, O. (1997) Insecticides of Natural Origin, Harwood Academic Publishers, Amsterdam, p. 138.
(3) Jones, C.G. and Firn, R.D. (1979) Biochem. Syst. Ecol., 7, 187.
(4) Miles, D.H., Hankinson, B.L., and Randle, S.A. (1985) Proc. ACS Symp. Ser., 276, 469.
(5) Jenner, P.M., Hagan, E.C., Jean, M.T., Cook, E.L., and Fitzhugh, O.G. (1964) Food Cosmet. Toxicol., 2, 327.

© 2005 by CRC Press LLC


Insect Antifeedants 265

CINNAMAMIDE C9H9ON
(147.18)
M.p. : 147°

H2N

(1, 2) (1)

SOURCE: Commercial sample (2)


Cornopteris decurrentialata, fern (Pteridophte) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Pieris brassicae (L.) Leaf disk 6.8 × 10–2 M Feeding ratio = Treatment to 2nd day
(Large white butterfly) no-choice 2.42, considered as 5th instar unstarved
test effective antifeedant. larvae.
(2)

(1) (1994) Dictionary of Natural Products, Chapman & Hall, London.


(2) Jones, C.G. and Firn, R.D. (1979) Biochem. Syst. Ecol., 7, 187.

© 2005 by CRC Press LLC


266 Opender Koul

Trans-CINNAMIC ACID C9H8O2


(148.16)
M.p. : 133°

B.p. : 300°
COOH

(1, 2) (1)

SOURCE: Synthetic (2)


Commercial sample (3)
Alchornea triplinervia (Spreng.) Muell. Arg., larenjeira (Euphorbiaceae) (4)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Incisitermes minor (Hagen) Paper towel 0.05 mg/cm2 Feeding inhibition = 1. Treatment to
(Western drywood termite) disk test 23.5% immature termites
for 6 days.
(2)

2. Pieris brassicae (L.) Leaf disk 6.8 × 10–2 M Feeding ratio = 2. Treatment to 2nd
(Large white butterfly) no-choice 3.11, considered as day 5th instar
test effective antifeedant. unstarved larvae.
(3)

3. Anthonomus grandis Bohem. Artificial 30 mg/4 cm2 Feeding ratio = 3. Treatment to


(Boll weevil) diet feeding 25.0% freshly emerged boll
weevils. Percent
feeding ratio (T/C)
value of 0 represents
total feeding
deterrence and >100
as attraction.
(4)

LD50 (rats): 2500 mg/kg (oral) (5)

(1) Camte, P., Zwingelstein, G., Ville, A., and Mentzer, C. (1957) Compt. Rend., 245, 1144.
(2) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39.
(3) Jones, C.G. and Firn, R.D. (1979) Biochem. Syst. Ecol., 7, 187.
(4) Miles, D.H., Hankinson, B.L., and Randle, S.A. (1985) Proc. ACS Symp. Ser., 276, 469.
(5) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC


Insect Antifeedants 267

CINNAMONITRILE C9H7N
(129.16)
M.p. : 20–21°

B.p. : 134°/12 mm
N

(1, 2) (1)

SOURCE: Commercial sample (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Pieris brassicae (L.) Leaf disk 7.8 × 10–2 M Feeding ratio = Treatment to 2nd day
(Large white butterfly) no-choice 19.5, considered as 5th instar unstarved
test strong antifeedant. larvae.
(2)

(1) (1994) Dictionary of Natural Products, Chapman & Hall, London.


(2) Jones, C.G. and Firn, R.D. (1979) Biochem. Syst. Ecol., 7, 187.

© 2005 by CRC Press LLC


268 Opender Koul

5-CINNAMOYL-9-ACETYL-TAXICIN I C31H38O8
(538.64)
M.p. : 163–165°
OH
OAc [α]25
D : +186° (CHCl3)

OH
OH O
CH2

(1, 2) (1)

SOURCE: Taxus baccata Nutt., yew tree (Taxaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius L. Wafer disk 10 mg/ml Feeding deterrence 1. Treatment given to


(Grain weevil) test coefficient = 115.5 adults.

2. Tribolium confusum Duv. Wafer disk 10 mg/ml Feeding deterrence 2. Treatment given to
(Confused flour beetle) test coefficient both adults and
Adults = 103.4 larvae.
Larvae = 129.0

3. Trogoderma granarium Wafer disk 10 mg/ml Feeding deterrence 3. Treatment given to


Everts test coefficient = 79.0 larvae.
(Khapra beetle)
Neutral value = 0
Absolute feeding
deterrence value =
200
(2)

(1) Appendino, G., Gariboldi, P., Pisetta, A., Bombardelli, E., and Gabetta, B. (1992) Phytochemistry, 31, 4253.
(2) Daniewski, W.M., Gumulka, M., Anczewski, W., Masnyk, M., Bloszyk, E., and Gupta, K.K. (1998) Phy-
tochemistry, 49, 1279.

© 2005 by CRC Press LLC


Insect Antifeedants 269

6-CINNAMOYL-5-HYDROXY-2, C20H17O3
2-DIMETHYLCHROMAN (305.39)
No physical data given

O OH

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera exempta (Walker) Glass fiber 100 ppm Feeding inhibition = 1. Treatment to 24- to
(Nutgrass armyworm) disk dual 52.0% 36-h-old final
choice test stadium larvae for 5
10 ppm Feeding inhibition = h. Larvae pre-starved
41.0% for 4 h.
(1)
2. Spodoptera littoralis (Boisd.) Glass fiber 100 ppm Feeding inhibition = 1. Treatment to 24- to
(Egyptian cotton leaf worm) disk dual 68.0% 36-h-old final
choice test stadium larvae for 5
10 ppm Feeding inhibition = h. Larvae pre-starved
32.0% for 4 h.
(1)

(1) Simmonds, M.S.J., Blaney, W.M., Monache, F.D., and Bettolo, G.B.M. (1990) J. Chem. Ecol., 16, 365.

© 2005 by CRC Press LLC


270 Opender Koul

13-Trans-CINNAMOYL OXYLUPANINE C24H30O3N2


(394.51)
M.p. : 166°

[α]20
D : +42° (neat)

H
O
N

N O
H

(1, 2) (1)

SOURCE: Synthetic (2)


Also isolated from Lupinus angustifolius L., European blue lupine and L. polyphyllus Lindl.,
lupine (Fabaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Choristoneura fumiferana Paper 1.3 × 103 M Feeding inhibition = 1. Treatment to 6th


(Clemens) penicillin 95.0% instar larvae.
(Spruce budworm) disk assay (2)
0.1 × 103 M Feeding inhibition =
54.0%

0.01 × 103 M Feeding inhibition =


2.0%

(1) (1994) Dictionary of Natural Products, Chapman & Hall, London.


(2) Bentley, M.D., Leonard, D.E., Reynolds, E.K., Leach, S., Beck, A.B., and Murakoshi, I. (1984) Ann. Entomol.
Soc. Am., 77, 398.

© 2005 by CRC Press LLC


Insect Antifeedants 271

CINNAMYL ALCOHOL C9H10O


(134.17)
M.p. : 33°

B.p. : 72.6°/1 mm

OH n20 : 1.58190
D

(1, 2) (1)

SOURCE: Commercial sample (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Pieris brassicae (L.) Leaf disk 7.5 × 10–2 M Feeding ratio = Treatment to 2nd day
(Large white butterfly) no-choice 4.76 5th instar unstarved
test larvae.
Ratio <20 considered
as effective
antifeedant.
(2)

LD50 (rats): 2000 mg/kg (oral) (3)

(1) Meerwein, H. and Schmidt, R. (1925), Ann., 444, 221.


(2) Jones, C.G. and Firn, R.D. (1979) Biochem. Syst. Ecol., 7, 187.
(3) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC


272 Opender Koul

CINNZEYLANINE C22H34O8
(426.50)
M.p. : 265–267°

[α]27
D : +45° (CH3OH)

α- OAc
OH

HO HO
O

OH
HO

(1, 2) (2)

SOURCE: Persea indica Spreng., Indian bay (Lauraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk 1000 ppm Feeding inhibition Treatment to 3rd
(Tobacco armyworm) choice assay index = 23.41 instar larvae for 1
day. Feeding
inhibition index
value of < 23 highly
deterrent.
(1)

(1) Gonzalez-Coloma, A., Terrero, D., Parales, A., Escoubas, P., and Fraga, B.M. (1996) J. Agric. Food Chem.,
44, 296.
(2) Dev, S. and Koul, O. (1997) Insecticides of Natural Origin, Harwood Academic Publishers, Amsterdam, p. 97.

© 2005 by CRC Press LLC


Insect Antifeedants 273

CINNZEYLANOL C20H32O7
(384.46)
M.p. : 125–127°

[α]15
D : +18° (CH3OH)

α - OH
OH

HO HO
O

OH
HO

(1, 2) (2)

SOURCE: Persea indica Spreng, Indian bay (Lauraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk 1000 ppm Feeding inhibition Treatment to 3rd
(Tobacco armyworm) choice assay index = 7.28 instar larvae for one
day. Feeding
inhibition index
value of < 23 highly
deterrent.
(1)

LD50 (mice): 11.98 mg/kg (i.p.) (1)

(1) Gonzalez-Coloma, A., Terrero, D., Parales, A., Escoubas, P., and Fraga, B.M. (1996) J. Agric. Food Chem.,
44, 296.
(2) Dev, S. and Koul, O. (1997) Insecticides of Natural Origin, Harwood Academic Publishers, Amsterdam, p. 96.

© 2005 by CRC Press LLC


274 Opender Koul

EPI – CINNZEYLANOL C20H32O7


(384.47)
Only spectral data given

β - OH
OH

HO HO
O

OH
HO

(1) (1)

SOURCE: Persea indica Spreng., Indian bay (Lauraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk 1000 ppm Feeding inhibition Treatment to 3rd
(Tobacco armyworm) choice assay index = 6.6 instar larvae for 1
day. Feeding
inhibition index
value of < 23 highly
deterrent.
(1)

(1) Gonzalez-Coloma, A., Terrero, D., Parales, A., Escoubas, P., and Fraga, B.M. (1996) J. Agric. Food Chem.,
44, 296.

© 2005 by CRC Press LLC


Insect Antifeedants 275

CINNZEYLANONE C20H30O7
(382.45)
Only spectral data given

O
OH

HO HO
O

OH
HO

(1) (1)

SOURCE: Persea indica Spreng., Indian bay (Lauraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk 1000 ppm Feeding inhibition Treatment to 3rd
(Tobacco armyworm) choice assay index = 9.41 instar larvae for 1
day. Feeding
inhibition index
value of < 23
considered highly
deterrent.
(1)

LD50 (mice): >25 mg/kg (i.p.) (1)

(1) Gonzalez-Coloma, A., Terrero, D., Parales, A., Escoubas, P., and Fraga, B.M. (1996) J. Agric. Food Chem.,
44, 296.

© 2005 by CRC Press LLC


276 Opender Koul

CITROLIN C26H28O6
(436.50)
M.p. : 305°
O

O O O

(1, 2) (1)

SOURCE: Synthetic (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Eldana saccharina Walker Leaf disk 100 µg/disk Feeding inhibition = 1. Treatment to 12-h
(Sugar cane borer) choice 55 ± 21% pre-starved late 5th
assay instar larvae.
10 µg/disk 48 ± 10% (2)

2. Maruca testulalis (Geyer) Leaf disk 100 µg/disk Feeding inhibition = 2. Treatment to late
(Bean pod borer) choice 66 ± 5% 5th instar larvae.
assay (2)

(1) Dreyer, D.L. (1965) Tetrahedron, 21, 75.


(2) Hassanali, A., Bentley, M.D., Sitayo, E.N.O., Njoroge, P.E.W., and Yatagai, M. (1986) Insect Sci. Applic., 7,
495.

© 2005 by CRC Press LLC


Insect Antifeedants 277

d-CITRONELLIC ACID C10H18O2


(170.25)
M.p. : 257°

[α]D : +21° (acetone)


: +10.3° (CHCl3)

COOH

(1, 2) (1)

SOURCE: Synthetic (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Incistermes minor Hagen Paper towel 0.05 mg/cm2 Feeding inhibition = Treatment to
(Western drywood termite) disk test 11.4% immature termites
for 6 days.

Data calculated from


Reference 2.
(2)

LD50 (rats): 2610 mg/kg (oral) (3)

(1) (1994) Dictionary of Natural Products, Chapman & Hall, London.


(2) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39.
(3) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC


278 Opender Koul

(–) CLAUSSEQUINONE C16H14O5


(286.28)
M.p. : 189–194° (dec.)
(197–205°)

HO O

O OCH3

(1, 2) (1)

SOURCE: Cyclolobium clausseni Benth. (Fabaceae) (1)


C. vecchii A. Samp.

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Costelytra zealandica (White) Artificial diet 6.5 µg/g Feeding inhibition = Treatment to 24-h
(Scarab beetle) feeding 50.0% starved 3rd instar
larvae.

Concentration = EC50
value.
(2)

(1) Gottlieb, O.R., deOliveira, A.B., Goncalves, T.M.M., deOliveira, G.G., and Pereira, S.A. (1975) Phytochem-
istry, 14, 2495.
(2) Lane, G.A., Biggs, D.R., Russel, G.B., Sutherland, O.R.W., Williams, E.M., Maindonald, J.H., and Donnell,
D.J. (1985) J. Chem. Ecol., 11, 1713.

© 2005 by CRC Press LLC


Insect Antifeedants 279

CLERODENDRIN–A C31H42O12
(606.66)
M.p. : 164–165°

O [α]D : +7.4° (CHCl3)

HO

CCOO

O CH2
OAc
OAc
OAc (1) (1)

SOURCE: Clerodendron tricotomum Thunb., Japanese kusagi (Verbenaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera litura (Fab.) Leaf disk 300 ppm Feeding inhibition = 1. Treatment to 3rd
(Tobacco armyworm) choice test 100% instar larvae.
(2)

2. Ostrinia nubilalis (Hubner) Leaf disk 5000 ppm Feeding inhibition = 2. Treatment to
(European corn borer) choice test 100% larvae at random.
(2)

3. Euproctis subflava (Bremer) Leaf disk 1000 ppm Feeding inhibition = 3. Treatment to
(Oriental tusk moth) choice test 100% larvae at random.
(2)

(1) Kato, N., Shibayama, M., and Munakata, K. (1973) J. Chem. Soc. Perkin I, 712.
(2) Kato, N., Takahashi, M., Shibayama, M., and Munakata, K. (1972) Agric. Biol. Chem., 36, 2579.

© 2005 by CRC Press LLC


280 Opender Koul

CLERODENDRIN–B C31H44O12
(608.68)
M.p. : 207–209°
O (228–230°)

[α]22
D : –66° (CHCl3)

HO

CCOO

O CH2
OAc
OAc
OAc
(1, 2) (2)

SOURCE: Clerodendron tricotomum Thunb., Japanese kusagi (Verbenaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera litura (Fab.) Leaf disk 200 ppm Feeding inhibition = 1. Treatment to 3rd
(Tobacco armyworm) choice test 100% instar larvae.
(1)

2. Ostrinia nubilalis (Hubner) Leaf disk 5000 ppm Feeding inhibition = 2. Treatment to
(European corn borer) choice test 100% larvae at random.
(1)

3. Euproctis subflava (Bremer) Leaf disk 1000 ppm Feeding inhibition = 3. Treatment to
(Oriental tusk moth) choice test 100% larvae at random.
(1)

(1) Kato, N., Takahashi, M., Shibayama, M., and Munakata, K. (1972) Agric. Biol. Chem., 36, 2579.
(2) Rao, L.J.M., Pereira, J., and Gurudutt, K.N. (1993) Phytochemistry, 34, 572.

© 2005 by CRC Press LLC


Insect Antifeedants 281

CLERODIN C24H34O7
(434.53)
M.p. : 161–162°
O (164–165°)

[α]30
D : –37.6° (EtOH)

O CH2
OAc

OAc (1)
(1, 4)

SOURCE: Clerodendron infortunatum Gaertn., Indian bhat tree (Verbenaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera litura (Fab.) Leaf dip 80 ppm Feeding inhibition = 1. Treatment to 3rd or
(Tobacco armyworm) 100% 4th instar larvae.
(2)
This activity was
observed at 50 ppm
within 2 h in later
studies.
(3)

2. Spodoptera littoralis (Boisd.) Glass fiber 100 ppm Feeding inhibition = 2. Treatment to final
(Egyptian cotton leaf worm) disk choice 74.0% stadium larvae pre-
test 50 ppm Feeding inhibition = starved for 4 h.
59.0% Treatment duration =
25 ppm Feeding inhibition = 12 h.
24.0% (4)

FI50 = 46.4 ppm


calculated from
Reference 4.

(1) Barton, D.H.R., Cheung, H.T., Cross, A.D., Jackman, L.M., and Martin-Smith, M. (1961) J. Chem. Soc., 5061.
(2) Kato, N., Takahashi, M., Shibayama, M., and Munakata, K. (1972) Agric. Biol. Chem., 36, 2579.
(3) Hosozawa, S., Kato, N., Munakata, K., and Chen, Y. (1974) Agric. Biol. Chem., 38, 1045.
(4) Cole, M.D., Anderson, J.C., Blaney, W.M., Fellows, L.E., Ley, S.V., Sheppard, R.N., and Simmonds, M.S.J.
(1990) Phytochemistry, 29, 1793.

© 2005 by CRC Press LLC


282 Opender Koul

CLERODIN HEMIACETAL C24H36O8


OH
(452.54)
M.p. : 179–181°

H H

O
H

O CH2
OAc

OAc (1, 2) (1)

SOURCE: Caryopteris divaricata Maxim., snow fairy (Verbenaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk test 50 ppm Feeding inhibition = Treatment to 3rd
(Tobacco armyworm) 100% instar larvae for 2 h.

This activity has


been termed as
absolute antifeedant
effect.
(2)

(1) Hosozawa, S., Kato, N., and Munakata, K. (1974) Agric. Biol. Chem., 38, 823.
(2) Hosozawa, S., Kato, N., Munakata, K., and Chen, Y. (1974) Agric. Biol. Chem., 38, 1045.

© 2005 by CRC Press LLC


Insect Antifeedants 283

CNICIN C20H26O7
(378.42)
M.p. : 143°

OH [α]20
D : +158° (EtOH)

OH
OCO

CH2
CH2

O
CH2OH
O

(1, 2) (1, 2)

SOURCE: Centaurea diffusa Lam., thistle (Cynaraceae) (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius L. Wafer disk 8 mg/cm3 Feeding deterrence Treatment given to


(Grain weevil) test coefficient = adults.
101–150 (3)

2. Tribolium confusum Duv. Wafer disk 8 mg/cm3 Feeding deterrence Treatment given to
(Confused flour beetle) test coefficient = both adults and
Larvae = 51–100 larvae.
Adults = 151–200 (3)

3. Trogoderma granarium Wafer disk 8 mg/cm3 Feeding deterrence Treatment given to


Everts test coefficient = larvae.
(Khapra beetle) 101–150
Neutral value = 0
Absolute feeding
deterrence value =
200
(3)

(1) Suchy, M., Benesova, V., Herout, V., and Sorm, F. (1960) Chem. Ber., 93, 2449.
(2) Suchy, M., Samek, Z., Herout, V., and Sorm, F. (1965) Collect. Chech. Chem. Commun., 30, 3473.
(3) Nawrot, J., Bloszyk, E., Grabarczyk, H., and Drozdz, B. (1982) Prace. Nauk. Inst. Ochr. Roslin., 24, 27.

© 2005 by CRC Press LLC


284 Opender Koul

CORONOPILIN C15H20O4
(264.32)
M.p. : 177–178°

[α]21
D : –30.2° (EtOH)
OH

O O CH2

(1, 2) (1)

SOURCE: Iva xanthifolia Nutt., iva (Asteraceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius L. Wafer disk 8 mg/cm3 Feeding deterrence Treatment given to


(Grain weevil) test coefficient = adults.
101–150 (3)

2. Tribolium confusum Duv. Wafer disk 8 mg/cm3 Feeding deterrence Treatment given to
(Confused flour beetle) test coefficient = both adults and
Larvae = 51–100 larvae.
Adults = 51–100 (3)

3. Trogoderma granarium Wafer disk 8 mg/cm3 Feeding deterrence Treatment given to


Everts test coefficient = larvae.
(Khapra beetle) 151–200
Neutral value = 0
Absolute feeding
deterrence value =
200
(3)

(1) Herz, W. and Hogenauer, G. (1961) J. Org. Chem., 26, 5011.


(2) Nawrot, J., Bloszyk, E., Grabarczyk, H., and Drozdz, B. (1982) Prace. Nauk. Inst. Ochr. Roslin., 24, 27.

© 2005 by CRC Press LLC


Insect Antifeedants 285

o-COUMARIC ACID C9H8O3


(164.16)
M.p. : 207–208° (dec.)

COOH

OH

(1, 2) (1)

SOURCE: Pteridium aquilinum (L.) Kuhn, bracken fern (Pteridophyte) (2,3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Pieris brassicae (L.) Leaf disk 6.1 × 10–2 M Feeding ratio = 1.82 Treatment to 2nd day
(Large white butterfly) no-choice 5th instar unstarved
test larvae.
Ratio considered as
average deterrence.
(2)

LD50 (mice): 180 mg/kg (ivn) (4)

(1) Tiemann, F. (1877) Ber., 10, 284.


(2) Jones, C.G. and Firn, R.D. (1979) Biochem. Syst. Ecol., 7, 187.
(3) Glass, A.D.M. and Bohm, B.A. (1969) Phytochemistry, 8, 371.
(4) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC


286 Opender Koul

p-COUMARIC ACID C9H8O3


(164.16)
M.p. : 210–213°

COOH

OH

(1, 2) (1, 3)

SOURCE: Pteridium aquilinum (L.) Kuhn, bracken fern (Pteridophyte) (2, 3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Pieris brassicae (L.) Leaf disk 6.1 × 10–2 M Feeding ratio = 4.54 Treatment to 2nd day
(Large white butterfly) no-choice 5th instar unstarved
test larvae.
Ratio considered as
effective deterrence.
(2)

LD50 (mice): 657 mg/kg (ipr.) (4)

(1) Ogawa, S. (1927) Bull. Chem. Soc. Jap., 2, 25.


(2) Jones, C.G. and Firn, R.D. (1979) Biochem. Syst. Ecol., 7, 187.
(3) Glass, A.D.M. and Bohm, B.A. (1969) Phytochemistry, 8, 371.
(4) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC


Insect Antifeedants 287

COUMESTROL C15H8O5
(268.22)
M.p. : 385°

OH

HO O

(1) (1)

SOURCE: Commercial sample (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Costelytra zealandica Artificial diet 200 µg/ml Feeding inhibition = 1. Treatment to 3rd
(White) feeding 17.0% instar larvae after
(Scarab beetle) 24-h starvation.
(2)
Data calculated from
Reference 2.

2. Heteronychus arator (Fab.) Artificial diet 200 µg/ml Feeding inhibition = 2. Treatment to 3rd
(Black beetle) feeding 44.0% instar larvae after
24-h starvation.
(2)
Data calculated from
Reference 2.

(1) Bikoff, E.M., Lyman, R.L, Livingston, A.L., and Booth, A.N. (1958) J. Am. Chem Soc., 80, 3969.
(2) Sutherland, O.R.W., Russel, G.B., Biggs, D.R., and Lane, G.A. (1980) Biochem. Syst. Ecol., 8, 73.

© 2005 by CRC Press LLC


288 Opender Koul

CRISPATINE C16H23O5N
(309.36)
M.p. : 137–138°

H
[α]20
D : +40.7° (EtOH)

H O
C C
C C

O C OH O
H
O CH2

(1, 2) (1)

SOURCE: Crotalaria crispata F. Muell et Benth., crotalaria (Fabaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Choristoneura fumiferana Paper 1.6 × 103 M Feeding inhibition = Treatment to 6th


(Clemens) penicillin 65.0% instar larvae.
(Spruce budworm) disk test (2)

(1) Culvenor, C.C.J. and Smith, C.W. (1963) Aust. J. Chem., 16, 239.
(2) Bentley, M.D., Leonard, D.E., Stoddard, W.F., and Zalkow, L.H. (1984) Ann. Entomol. Soc. Am., 77, 393.

© 2005 by CRC Press LLC


Insect Antifeedants 289

CUCURBITACIN–B O C32H46O8
OH (558. 71)
M.p. : 180–182°

OAc [α]25
D : +87.5° (EtOH)
O

OH
HO

O
(1, 2) (1, 2)

SOURCE: Citrullus colocynthis L., cucurbit (Cucurbitaceae) (1)


And many other cucurbit plants. (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Popillia japonica Newman Leaf disk 25 µg/cm Feeding inhibition = 1. Treatments to


(Japanese beetle) dual diameter 57.0% adults until 25–50%
choice test disks were eaten.
(1)
2. Cerotoma trifurcata (Foster) Leaf disk 50 µg/cm Feeding inhibition = 2. Treatments to
(Bean leaf beetle) dual diameter 64.9% adults until 25–50%
choice test disks were eaten.
(1)
3. Leptinotarsa decemlineata Leaf disk 50 µg/cm Feeding inhibition = 3. Treatments to 4th
(Say) dual diameter 90.2% instar larvae until
(Colorado potato beetle) choice test 25–50% disks were
eaten.
(1)
4. Tenebrio molitor L. Oat meal 50 µg/37 mg Feeding inhibition = 4. Treatments to 5th
(Yellow mealworm) flake assay flakes 91.4% instar larvae until
25–50% food was
eaten.
(1)
5. Nauphoeta cinerea (Oliver) Flake 50 µg/37 mg Feeding inhibition = 5. Treatments to
(Cinereous cockroach) treatment flakes 91.4% adults until 25–50%
assay disks were eaten.
(1)
6. Diabrotica virgifera virgifera Disk 10.7 nmol/30 Feeding inhibition = 6. Treatment to
LeConte choice test mm2 38.9% bilaterally ablated
(Western corn rootworm) beetles for 24 h.
EC50 = 0.1 µM.
(4)
Data calculated from
Reference 4.

(1) Tallamy, D.W., Stull, J., Ehresman, P., Gorski, P.M., and Mason, C.E. (1997) Environ. Entomol., 26, 678.
(2) (1982) Dictionary of Organic Compounds, Vol. 2, Chapman & Hall, New York, p. 1315.
(3) Lavie, D. and Glotter, E. (1977) Forts. Chem. Organ. Naturstoffe., 29, 306.
(4) Chyb, S., Eichenseer, H., Hollister, B., Mullin, C.A., and Frazier, J.L. (1995) J. Chem. Ecol., 21 313.

© 2005 by CRC Press LLC


290 Opender Koul

CUCURBITACIN–E C32H44O8
(556. 69)
M.p. : 234°

O [α]20
D : –64.3° (CHCl3)
OH

OAc
O

OH
HO

(1, 2) (1, 2)

SOURCE: Commercial sample (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Hylobius pales (Herbst.) Twig dip 300 ppm Feeding inhibition = Treatments to 22–65
(Pales weevil) choice assay 63.7% mg body weight
weevils for 24 h.
(1)
Data calculated from
Reference 1.

(1) Salom, S.M., Carlson, J.A., Ang, B.N., Grosman, D.M., and Day, E.R. (1994) J. Entomol. Sci., 29, 407.
(2) (1982) Dictionary of Organic Compounds, Vol. 2, Chapman & Hall, New York, p. 1316.

© 2005 by CRC Press LLC


Insect Antifeedants 291

ar – CURCUMENE C15H22
(202.34)
B.p. : 137°/17 mm

[α]D : –34.3°

n20
D : 1.4989

(1)
(1, 2)
SOURCE: Artemisia capillaris Thumb., wormwood (Asteraceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Pieris rapae crucivora Boisd. Leaf disk test 10-1 mol./L Feeding inhibition = Treatment to 5th
(Cabbage butterfly) 85.0% instar larvae for 2 h.
(2)

(1) Carter, F.D., Copp, F.C., Sanjiva Rao, B., Simmonsen, J.L., and Subramanian, K.S. (1939) J. Chem. Soc., 1504.
(2) Yano, K. (1987) J. Agric. Food Chem., 35, 889.

© 2005 by CRC Press LLC


292 Opender Koul

CYCLOEPIATALANTIN C26H28O8
(468.50)
M.p. : 310° (dec.)
O

O O
O

O
O

(1, 2) (1)

SOURCE: Severinia buxifolia (Poir.) Tenore., Chinese box orange (Rutaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Plutella xylostella (L.) Leaf disk 0.25% Feeding inhibition = Treatment to 3rd
(Diamondback moth) choice test 50.0% instar larvae.

Concentration = EC50
value.
(2)

(1) Dreyer, D.L., Bennett, R.D., and Basu, S.C. (1976) Tetrahedron, 32, 2376.
(2) Wu, T.S., Leu, Y.L., Chan, Y.Y., Wu, P.L., Kuoh, C.S., Wu, S.J., and Wang, Yu (1997) Phytochemistry, 45, 1393.

© 2005 by CRC Press LLC


Insect Antifeedants 293

CYPERAQUINONE C14H10O4
(242.23)
M.p. : 182–183°

O O

(1) (1)

SOURCE: Cyperus nipponicus, C. distans L., sedge (Cyperaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk 1.7 × 10–7 Feeding inhibition = Treatment to 3rd
(Tobacco armyworm) assay mol/cm2 50.0% instar larvae up to
5 h.

Concentration = EC50
value.
(1)

(1) Morimoto, M., Fujii, Y., and Komai, K. (1999) Phytochemistry, 51, 605.

© 2005 by CRC Press LLC


294 Opender Koul

CYTISINE C11H14ON2
(sophorine/ulexine) (190. 24)
M.p. : 155°

B.p. : 218°/2 mm

[α]17
D : –119° (H2O)
NH

(1, 2) (1,3)

SOURCE: Commercial sample (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Acyrthosiphon pisum (Harris) Artificial diet 0.00016 ± Feeding inhibition = Treatment to aphids
(Pea aphid) feeding 0.00004% 50.0% at random.

Concentration = EC50
value.
(2)

LD50 (mice): 101 mg/kg (oral) (4)

(1) Govindachari, T.R., Rajadurai, S., Subramanian, M., and Thyagarajan, B.S. (1957) J. Chem. Soc., 3839.
(2) Dreyer, D.L., Jones, K.C., and Molyneux, R.J. (1985) J. Chem. Ecol., 11, 1045.
(3) Murakoshi, I., Fukuchi, K., Haginiwa, J., Ohmiya. S., and Otomasu, H. (1977) Phytochemistry, 16, 1460.
(4) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC


Insect Antifeedants 295

DANIELLIC ACID C20H28O3


(316.44)
M.p. : 129–130.5°

[α]D : –58° (MeOH)

H2C

O OH

(1, 2, 3) (1, 3)

SOURCE: Daniellia oliveri (Rolle) Hutch. and Dalz., copaiba balsam (Fabaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Schizaphis graminum (Rondani) Artificial diet 0.01% Feeding inhibition = Treatment to aphids
(Wheat aphid) feeding 50.0% at random.
Concentration = EC50
value.
(2)

(1) Haeuser, J., and Lombard, R. (1961) Tetrahedron, 12, 205.


(2) Rose, A.F., Jones, K.C., Haddon, W.F., and Dreyer, D.L. (1981) Phytochemistry, 20, 2249.
(3) Mills, J.S. (1973) Phytochemistry, 12, 2479.

© 2005 by CRC Press LLC


296 Opender Koul

DATURALACTONE C28H38O7
(486.60)
M.p. : 264–267°
O

H
OH
O

O
OH
(1,2) (1)

SOURCE: Datura qyercifolia H.B.K., datura


Nicandra physaloides (L.) Gaertn., apple-of-Peru (Solanaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera littoralis (Boisd.) Styropor test 100 ppm Feeding inhibition = Treatment to early 5th
(Egyptian cotton leaf worm) 6.0% instar larvae.
Treatment given in
combination with
anicandrin. Data
calculated from
Reference 2.
(2)

2. Epilachna varivestis Muls. Bean leaf 100 ppm 0.5 mg body weight 2. Treatment to 4th
(Mexican bean beetle) assay against 8.9 mg in instar larvae for 48 h.
controls. (2)
10 ppm 2.8 mg body weight
against 9.8 mg in
controls.

3. Tribolium castaneum Yeast diet 100 ppm 0.8 mg body weight 3. Treatment to 0 to
(Herbst.) feeding against 2.1 mg in 3-h-old larvae for 14
(Red flour beetle) controls. days.
(2)

(1) Kalla, A.K., Raina, M.L., Dhar, K.L., Qurishi, M.A., and Snatzke, G. (1979) Phytochemistry, 18, 637.
(2) Ascher, K.R.S., Eliyahu, M., Glotter, E., Goldman, A., Kirson, I., Abraham, A., Jacobson, M., and Schmutterer,
H. (1987) Phytoparasitica, 15, 15.

© 2005 by CRC Press LLC


Insect Antifeedants 297

3-DEACETOXY-2′,3′,20,21,22,23- C32H48O7
HEXAHYDROSALANNIN (544.73)
Only spectral data given

COOCH3 O
COO

O
H
H
O

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Leptinotarsa decemlineata Leaf disk 10 µg/cm2 Feeding inhibition = Treatment to freshly


(Say) choice test 95.0% molted 3rd instar
(Colorado potato beetle) larvae.
Disks examined
every 2 h until 95%
of control disks were
eaten.
Concentration = PC95
(1)

(1) Yamasaki, R.B. and Klocke, J.A. (1989) J. Agric. Food Chem., 37, 1118.

© 2005 by CRC Press LLC


298 Opender Koul

10-DEACETYL BACCATIN III C29H36O10


(544.60)
Only spectral data given
OH

O
OH
HO

OH
O
OAc
O

(1, 2, 3) (1, 2)

SOURCE: Taxus baccata Nutt., yew tree (Taxaceae) (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius L. Wafer disk 10 mg/ml Feeding deterrence 1. Treatment given to


(Grain weevil) test coefficient = 185.0 adults.

2. Tribolium confusum Duv. Wafer disk 10 mg/ml Feeding deterrence 2. Treatment given to
(Confused flour beetle) test coefficient both adults and
Adults = 180.2 larvae.
Larvae = 149.4

3. Trogoderma granarium Wafer disk 10 mg/ml Feeding deterrence 3. Treatment given to


Everts test coefficient = 115.5 larvae.
(Khapra beetle)
Neutral value = 0
Absolute feeding
deterrence value =
200.
(3)

(1) Miller, R.W., Powell, R.G., and Smith, C.R. (1981) J. Org. Chem., 46, 1469.
(2) Gabetta, B., De Bellis, P., Pace, R., Appendino, G., Barboni, L., Torregiani, E., Gariboldi, P., and Viterbo, D.
(1995) J. Nat. Prod., 58, 1508.
(3) Daniewski, W.M., Gumulka, M., Anczewski, W., Masnyk, M., Bloszyk, E., and Gupta, K.K. (1998) Phy-
tochemistry, 49, 1279.

© 2005 by CRC Press LLC


Insect Antifeedants 299

6-DEACETYLNIMBIN C28H34O8
(498.57)
M.p. : 208°

COOCH3 O
O

H3COOC OH

(1) (1)

SOURCE: Azadirachta indica A. Juss., neem (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera litura (Fab.) Leaf disk 1 µg/cm2 Feeding inhibition = 1. Treatment to 3rd
(Tobacco armyworm) dual-choice 64.6% instar larvae for 24 h.
test 10 µg/cm2 Feeding inhibition = (2)
66.9%

2. Pericallia ricini (Fab.) Leaf disk 1 µg/cm2 Feeding inhibition = 2. Treatment to 3rd
(Tiger moth) dual-choice 64.5% instar larvae for 24 h.
test 10 µg/cm2 Feeding inhibition = (2)
70.2%

3. Oxya fuscovittata (Marsh.) Leaf disk 1 µg/cm2 Feeding inhibition = 3. Treatment to 3rd
(Grasshopper) dual-choice 67.6% instar larvae for 24 h.
test 10 µg/cm2 Feeding inhibition = (2)
79.6%

(1) Narayanan, C.R. and Iyer, K.N. (1967) Ind. J. Chem., 5, 460.
(2) Govindachari, T.R., Narasimhan, N.S., Suresh, G., Partho, P.D., and Gopalakrishnan, G. (1996) J. Chem.
Ecol., 22, 1453.

© 2005 by CRC Press LLC


300 Opender Koul

6-DEACETYLNIMBINENE C26H32O6
(440.54)
M.p. : 141°

OCH3 [α]D20 : +132° (CHCl3)

O
O O

OH

(1, 2) (1)

SOURCE: Azadirachta indica A. Juss., neem (Meliaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Epilachna varivestis Muls. Bean leaf 0.082% Feeding inhibition = Treatment to 4th
(Mexican bean beetle) choice test 50.0% instar larvae for 24 h.
Concentration = EC50
(2)

(1) Kraus, W. and Cramer, R. (1981) Chem. Ber., 114, 2375.


(2) Schwinger, M., Ehhammer, B., and Kraus, W. (1984) In H. Schmutterer and K.R.S. Ascher (eds.), Proc. 2nd
Int. Neem Conf., Rauischholzhausen, Eschborn, Germany, pp. 181–198.

© 2005 by CRC Press LLC


Insect Antifeedants 301

3-DEACETYLSALANNIN C32H42O8
(554.68)
M.p. : 214–215°

O [α]D20 : +134° (CHCl3)

COOCH3 O
O

HO O

H
O

(1, 2) (1, 2)

SOURCE: Azadirachta indica A. Juss., neem (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Epilachna varivestis Muls. Bean leaf 0.0027% Feeding inhibition = Treatment to 4th
(Mexican bean beetle) choice test 50.0% instar larvae for 24 h.
Concentration = EC50
(2)

0.05% Feeding inhibition = At this level of


100% treatment absolute
antifeedance
maintained until 16 h
post-treatment.
Data calculated from
Reference 3.
(3)

(1) Yamasaki, R.B. and Klocke, J.A. (1989) J. Agric. Food Chem., 37, 1118.
(2) Kraus, W. and Cramer, R. (1981) Liebigs Ann. Chem., 2381.
(3) Schwinger, M., Ehhammer, B., and Kraus, W. (1984) In H. Schmutterer and K.R.S. Ascher (eds.), Proc. 2nd
Int. Neem Conf., Rauischholzhausen, Eschborn, Germany, pp. 181–198.

© 2005 by CRC Press LLC


302 Opender Koul

DEACETYL SERGEOLIDE C23H26O10


(462.45)
M.p. : 295–300° (dec.)

[α]D24 : –145° (pyridine)


OH

HO COOCH3
O
OH
O

O H
O O
H

(1, 2) (1, 3)

SOURCE: Picrolemma pseudocoffea Ducke. (Simaroubaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Heliothis virescens (Fab.) Leaf disk 12.0 µg/cm2 Feeding inhibition = Treatment to 3rd
(Tobacco budworm) choice test 60–90% after 6 days instar larvae.
of treatment.

3.0 µg/cm2 Feeding inhibition =


60–90% after 2 days
of treatment and
0–30% after 6 days
of treatment. (2)

(1) Polonsky, J., Bhatnagar, S., and Moretti, C. (1984) J. Nat. Prod., 47, 994.
(2) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y.M., Kiyokawa, H., and Lee, K.H.
(1987) J. Nat. Prod., 50, 442.
(3) Moretti, C., Polonsky, J., Vuilhorgne, M., and Prange, T. (1982) Tetrahedron Lett., 23, 647.

© 2005 by CRC Press LLC


Insect Antifeedants 303

DEACETYL VISMINONE–A C21H24O5


(356.42)
M.p. : 161–164°

O OH OH

OCH3
OH

(1, 2) (1)

SOURCE: Psorospermum febrifugum Spach., Christmas berry (Clusiaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Locusta migratoria (L.) Glass fiber 10–3 M Feeding inhibition = Treatment to last
(Migratory locust) disk test 69.22% instar larvae.
(2)

(1) Botta, B., Monache, F.D., Monache, G.D., Bettolo, G.B.M., and Ogukawa, J.V. (1983) Phytochemistry, 22, 539.
(2) Simmonds, M.S.J., Blaney, W.M., Delle Monache, F., Mac-Quhae, M.M., and Bettolo, G.B.M. (1985) J.
Chem. Ecol., 11, 1593.

© 2005 by CRC Press LLC


304 Opender Koul

DEACYLADENOSTYLONE C15H22O3
(250.34)
M.p. : 177–178°

[α]D24 : 108.8° (CHCl3)


OH

(1, 2) (1)

SOURCE: Adenostyles alliariae (Gouan) Kern., grauer alpino (Asteraceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius L. Wafer disk 10 mg/ml Feeding deterrence 1. Treatment given to


(Grain weevil) test coefficient = 45 adults.

2. Tribolium confusum Duv. Wafer disk 10 mg/ml Feeding deterrence 2. Treatment given to
(Confused flour beetle) test coefficient both adults and
Adults = 112 larvae.
Larvae = 103

3. Trogoderma granarium Wafer disk 10 mg/ml Feeding deterrence 3. Treatment given to


Everts test coefficient = 37 larvae.
(Khapra beetle)
Neutral value = 0
Absolute feeding
deterrence value =
200.
(2)

(1) Harmatha, J., Samek, Z., Novotny, L., Herout, V., and Sorm, F. (1969) Collect. Czech. Chem. Commun., 34,
1739.
(2) Nawrot, J., Harmatha, J., and Novotny, L. (1984) Biochem. Syst. Ecol., 12, 99.

© 2005 by CRC Press LLC


Insect Antifeedants 305

DEAMINOACYLTAXINE–A C24H34O8
(450.53)
M.p. : 204–206°

[α]D25 : –116.9° (CHCl3)


OH O OH

AcO
OH

OAc

(1, 2) (1)

SOURCE: Taxus baccata Nutt., yew tree (Taxaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius L. Wafer disk 10 mg/ml Feeding deterrence 1. Treatment given to


(Grain weevil) test coefficient = 110.3 adults.

2. Tribolium confusum Duv. Wafer disk 10 mg/ml Feeding deterrence 2. Treatment given to
(Confused flour beetle) test coefficient both adults and
Adults = 112.3 larvae.
Larvae = 129.1

3. Trogoderma granarium Wafer disk 10 mg/ml Feeding deterrence 3. Treatment given to


Everts test coefficient = 73.6 larvae.
(Khapra beetle)
Neutral value = 0
Absolute feeding
deterrence value =
200.
(2)

(1) Appendino, G., Cravotto, G., Enriu, R., Jakupovic, J., Gariboldi, P., Bombardelli, E., and Gabetta, B. (1994)
Phytochemistry, 36, 407.
(2) Daniewski, W.M., Gumulka, M., Anczewski, W., Masnyk, M., Bloszyk, E., and Gupta, K.K. (1998) Phy-
tochemistry, 49, 1279.

© 2005 by CRC Press LLC


306 Opender Koul

DECANOIC ACID C10H20O2


(Capric acid) (172.26)
M.p. : 31.5°

B.p. : 268–270°

n40
D : 1.42855

COOH

(1, 2) (1, 2)

SOURCE: Synthetic (3)


Hibiscus syriacus L., rose-of-sharon (Malvaceae) (4)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Incisitermes minor (Hagen) Paper towel 0.05 mg/cm2 Feeding deterrence = 1. Treatment to
(Western drywood termite) disk test 11.7% immature termites.
Duration of
treatment = 6 days.
(3)

2. Anthonomus grandis Bohem. Plate 100 µg per Feeding of 64% of 2. Treatment given to
(Boll weevil) bioassay feeding site controls after 2 h and adult weevils.
63% after 6 h in (4)
males, and 69% and
64%, respectively, in
females.

LD50 (mice): 129 ± 5.4 mg/kg (i.v.) (5)

(1) Kao, C.H. and Ma, S.-Y. (1931) J. Chem. Soc., 2046.
(2) Sisido, K., Kazama, Y., Kodama, H., and Nozaki, H. (1959) J. Am. Chem. Soc., 81, 5817.
(3) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39.
(4) Bird, T.G., Hedin, P.A., and Burks, M.L. (1987) J. Chem. Ecol., 13, 1087.
(5) Oro, L. and Wretlind, A. (1961) Acta Pharmacol. Toxicol., 18, 141.

© 2005 by CRC Press LLC


Insect Antifeedants 307

n-DECYL GALLATE C17H26O5


(310.39)
No data given

COO

HO OH

HO

(1) (1)

SOURCE: Commercial sample (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Schizaphis graminum Artificial diet 16 ppm Feeding deterrence = 1. Treatment to


(Rondani) feeding 50.0% aphids at random
(Wheat aphid) Concentration = EC50
(1)

2. Acyrthosiphon pisum (Harris) Artificial diet 40.7 ppm Feeding deterrence = 2. Treatment to
(Pea aphid) feeding 50.0% aphids at random.
Concentration = EC50
(1)

3. Myzus persicae (Sulzer) Artificial diet 484 ppm Feeding deterrence = 3. Treatment to
(Green peach aphid) feeding 50.0% aphids at random.
Concentration = EC50
(1)

(1) Jones, K.C. and Klocke, J.A. (1987) Entomol. Exp. Appl., 44, 229.

© 2005 by CRC Press LLC


308 Opender Koul

DEHYDROABIETIC ACID C20H28O2


(300.44)
M.p. : 172–173°

[α]D20 : +62° (EtOH)

COOH

(1) (1)

SOURCE: Pinus banksiana Lamb., jack pine (Pinaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Neodiprion dubiosus Schedl. Pine needles 1 mg/ml Feeding deterrence = 1. Treatment to 3rd or
(Brownhead jack pine saw and twig 57.0% 4th instar larvae for
fly) application 13.5 mg/ml Feeding deterrence = 4 h.
>70.0% (2, 3)

2. Neodiprion lecontei (Fitch) Pine needles 10.6 mg/ml Feeding deterrence = 2. Treatment to 3rd or
(Redhead pine saw fly) and twig >70.0% 4th instar larvae for
application 4 h.
(3)

3. Neodiprion rugifrons Pine needles 6.7 mg/ml Feeding deterrence = 3. Treatment to 3rd or
Middleton and twig >70.0% 4th instar larvae for
(Redhead jack pine saw fly) application 4 h.
(3)

Spray 3 mg/ml Feeding deterrence = Treatment to 3rd


24.6% instar larvae. Sprays
made on both larvae
and the host
branches.
(4)

(1) Stork, G. and Schulenberg, J.W. (1962) J. Am. Chem. Soc., 84, 284.
(2) Schuh, B.A. and Benjamin, D.M. (1984) J. Chem. Ecol., 10, 1071.
(3) Schuh, B.A. and Benjamin, D.M. (1984), J. Econ. Entomol., 77, 802.
(4) Ikeda, T., Matsumura, F., and Benjamin, D.M. (1977) J. Chem. Ecol., 3, 677.

© 2005 by CRC Press LLC


Insect Antifeedants 309

14,15-DEHYDROAJUGAREPTANSIN C29H42O10
(550.65)
Only spectral data given
O
O H H

O
O

HO
O CH2
OAc

OAc
(1) (1)

SOURCE: Ajuga reptans L., catlins giant (Labiatae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera littoralis (Boisd.) Glass-fiber 25 ppm Feeding deterrence = Treatment to 6th


(Egyptian cotton leaf worm) disk test 60.0% stadium larvae pre-
starved for 4 h.
100 ppm Feeding deterrence = Treatment removed
92.0% either after 50% of
disk was consumed
or after 14 h.
(1)

(1) Bremner, P.D., Simmonds, M.S.J., Blaney, W.M., and Veitch, N.C. (1998) Phytochemistry, 47, 1227.

© 2005 by CRC Press LLC


310 Opender Koul

DEMETHYLGROSSAMIDE C35H34O8N2
OH (610.66)
Amorphous powder
OH

NH

O HN
O

OH
O

OH
OCH3
(1) (1)

SOURCE: Xylopia aethiopica A. Rich., African pepper (Anonaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Reticulitermes speratus Kolbe Paper disk 500 ppm Feeding inhibition Treatment to 3rd
(Subterranean termite) choice test index = 29.49 instar workers.
Feeding duration =
14 days.
Antifeedant index
value below 20
considered as highly
effective deterrent
value.
(1)

(1) Lajide, L., Escoubas, P., and Mizutani, J. (1995) Phytochemistry, 40, 1105.

© 2005 by CRC Press LLC


Insect Antifeedants 311

DEMETHYLHOMOLYCORINE C17H19O4N
(301.34)
M.p. : 213–214°
(138–140°;
270–272°)

N [α]D : +96.4° (CHCl3)

H
CH3O

O
HO

(1, 2) (1)

SOURCE: Lycoris radiata Herb., red spider lily (Amaryllidaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Eurema hecabe mandarina Artificial diet 0.4% Feeding ratio = 20.9% Treatment to 5th
DelOrza feeding instar larvae after 4 h
(Yellow butterfly) 0.2% Feeding ratio = 20.0% of pre-starvation.
Feeding ratio up to
0.1% Feeding ratio = 19.1% 20% considered as
strong feeding
0.05% Feeding ratio = 22.8% deterrence.
(2)

(1) Uyeo, S. (1960) c.f. Wildman, The Alkaloids, Ed. Manske, 3, 333.
(2) Numata, A., Takemura, T., Ohbayashi, H., Katsuuno, T., Yamamoto, K., Sato, K., and Kobayashi, S. (1983)
Chem. Pharm. Bull., 31, 2146.

© 2005 by CRC Press LLC


312 Opender Koul

DEMISSINE C50H83O20N
(1018.20)
M.p. : 305–308° (Uncor.)

[α]D10 : –20° (Pyridine)

Xyl - Gal - 2Glu - O


H

(1) (1)

SOURCE: Solanum demissum Lindl., solanum (Solanaceae) (1)


Commercial sample (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Leptinotarsa decemlineata Sensillum 0.4% wet Feeding inhibition = Treatment to adult


(Say) response weight 50.0% beetles.
(Colorado potato beetle) recording
Concentration = EC50
(2)

(1) Kuhn, R. and Low, I. (1947) Chem. Ber., 80, 406.


(2) Mitchel, B.K. and Harrison, G.D. (1985) J. Chem. Ecol., 11, 73.

© 2005 by CRC Press LLC


Insect Antifeedants 313

DENATONIUM BENZOATE C21H29N2O⊕


(325.48)
M.p. : 166–170°

+
NHCOCH2N CH2

(1, 2) (2)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Myzus persicae (Sulzer) Leaf disk no- 250 ppm Feeding inhibition = Treatment to 2-day-
(Green peach aphid) choice test 66.0% old larvae for 48 h.
Data calculated from
Reference 1.
(1)

(1) Perera, M.T.M.D.R., Armstrong, G., and Naylor, R.E.L. (1995) Trop. Agric. Res., 7, 39.
(2) (1982) Dictionary of Organic Compounds, Vol. 2, Chapman & Hall, New York, p. 1482.

© 2005 by CRC Press LLC


314 Opender Koul

14-DEOXYANDROGRAPHOLIDE C20H30O4
(334.46)
M.p. : 175°

O [α]D : –30.7° (MeOH)

CH2

HO

CH2OH

(1, 2) (2)

SOURCE: Andrographis paniculata (Burm. f.) Wall. ex. Nees, king of bitters (Acanthaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Plutella xylostella (L.) Leaf disk no- 100 µg/leaf Feeding inhibition = Treatment to 4th
(Diamondback moth) choice test disk of 50.0% stadium larvae for
2 cm 24 h. Insects were
diameter pre-starved for 3 h.
Concentration = EC50
value calculated
from Reference 1.
(1)

(1) Hermawan, W., Nakajima, S., Ritsuko, T., Fujisaki, K., and Nakasuji, F. (1997) Appl. Entomol. Zool., 32, 551.
(2) Balmain, A. and Connolly, J.D. (1973) J. Chem. Soc. Perkin Trans I, 1247.

© 2005 by CRC Press LLC


Insect Antifeedants 315

DEOXYEPILIMONOL C26H32O7
(456.51)
M.p. : 300–305°

[α]D : +61° (Acetone)


O
O

O O

O
O

OH

(1, 2) (1)

SOURCE: Synthetic (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Leptinotarsa decemlineata Leaf disk 100 µg/cm2 Feeding inhibition = Treatment to 4th
(Say) test 75.1% instar larvae for 6 to
(Colorado potato beetle) 8 h.
(2)
31.7 µg/cm2 Feeding inhibition =
36.9% Approximate FI50 =
49.8 µg/cm 2.
Calculated from
10 µg/cm2 Feeding inhibition = Reference 2.
1.4%

(1) Barton. D.H.R., Pradhan, S.K., Sternhell, S., and Templeton, J.F. (1961) J. Chem Soc., 255.
(2) Bentley, M.D., Rajab, M.S., Alford, A.R., Mendel, M.J., and Hassanali, A. (1988) Entomol. Exp. Appl., 49, 189.

© 2005 by CRC Press LLC


316 Opender Koul

8-DEOXYLACTUCIN C15H16O4
(260.29)
M.p. : 143–148°

H
H
CH2
CH2OH O

(1,2) (2)

SOURCE: Cichorium intybus L., chicory (Asteraceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Schistocerca gregaria (Forsk.) Glass fiber 0.49% dry Consumption of Treatment to 2- to


(Desert locust) disk test weight treated food = 19.4% 3-day-old adults of
either sex (1:1)
(2)
0.36% dry Consumption of
weight treated food = 14.1% It was not possible to
calculate EC50 from
this data.
0.24% dry Consumption of
weight treated food = 24.5%

0.22% dry Consumption of


weight treated food = 53.7%

(1) Pyrek, J.S. (1977) Roczniki Chemii., 51, 2165.


(2) Rees, S.B., and Harborne, J.B. (1985) Phytochemistry, 24, 2225.

© 2005 by CRC Press LLC


Insect Antifeedants 317

DEOXYLIMONIN C26H30O7
(454.52)
M.p. : 331–336°

O [α]D : –39° (CHCl3)

O O

O
O

(1,2) (1)

SOURCE: Synthetic (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Eldana saccharina Walker Leaf disk 100 µg/disk Feeding inhibition = 1. Treatment to 12-h
(Sugar cane borer) test 83 ± 9% starved late 5th instar
larvae.
10 µg/disk Feeding inhibition = (2)
81 ± 10%

1 µg/disk Feeding inhibition =


66 ± 11%

2. Maruca testulalis (Geyer) Leaf disk 100 µg/disk Feeding inhibition = 2. Treatment to late
(Bean pod borer) test 46 ± 14% 5th instar larve pre-
starved for 12 h.
10 µg/disk Feeding inhibition = (2)
56 ± 14%

(1) Barton, D.H.R., Pradhan, S.K., Sternhell, S., and Templeton, J.F. (1961) J. Chem. Soc., 255.
(2) Hassanali, A., Bentley, M.D., Sitayo, E.N.O., Njoroge, P.E.W., and Yatagai, M. (1986) Insect. Sci. Applic., 7,
495.

© 2005 by CRC Press LLC


318 Opender Koul

DEOXYLIMONOL C26H33O7
(457.22)
M.p. : 250–252°

O
O

O
O

O
O

OH

(1,2) (1)

SOURCE: Synthetic (2)


Also isolated from Citrus paradisi Macfad., grapefruit (Rutaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Leptinotarsa decemlineata Leaf disk 100 µg/cm2 Feeding inhibition = 1. Treatment to 4th
(Say) test 71.0% instar larvae for
(Colorado potato beetle) 6–8 h.
(2)
31.7 µg/cm2 Feeding inhibition =
30.4%

(1) Bennett, R.D., and Hasegawa, S. (1982) Phytochemistry, 21, 2349.


(2) Bentley, M.D., Rajab, M.S., Alford, A.R., Mendel, M.J., and Hassanali, A. (1988) Entomol. Exp. Appl., 49, 189.

© 2005 by CRC Press LLC


Insect Antifeedants 319

DEOXYVASICINE C11H12N2
(172.23)
M.p. : 99–100°

(1) (1)

SOURCE: Adhatoda vasica L., vasaka (Acanthaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Aulacophora foveicollis Leaf spray 0.05% Feeding inhibition = 1. Treatment to


(Lucas) test 67.8% adults for 24 h.
(Red leaf beetle)
0.1% Feeding inhibition = Data calculated from
30.4% Reference 1.
(1)

2. Epilachna vijintioctopunctata Leaf spray 0.05% Feeding inhibition = 2. Treatment to


(Fab.) test 57.1% adults for 24 h.
(Brinjal beetle)
0.1% Feeding inhibition = Data calculated from
60.2% Reference 1.
(1)

(1) Saxena, B.P., Tikku, K., Atal, C.K., and Koul, O. (1986) Insect Sci. Applic., 7, 489.

© 2005 by CRC Press LLC


320 Opender Koul

DERRICIN C21H22O3
(322.40)
Physical data not given

O OH

(1,2) (1)

SOURCE: Lonchocarpus neuroscapha Bentt., coroa piaca (Fabaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera exempta (Walker) Glass fiber 100 ppm Feeding inhibition = 1. Treatment to 24- to
(Nutgrass armyworm) disk dual- 72.0% 36-h-old final
choice test stadium larvae for
10 ppm Feeding inhibition = 5 h. Larvae pre-
54.0% starved for 4 h.
(2)

2. Spodoptera littoralis (Boisd.) Glass fiber 100 ppm Feeding inhibition = 2. Treatment to 24- to
(Egyptian cotton leaf worm) disk dual- 75.0% 36-h-old final
choice test stadium larvae for
10 ppm Feeding inhibition = 5 h. Larvae pre-
56.0% starved for 4 h.
(2)

(1) Rao, J.M., Subrahmanyam, K., and Rao, K.V.J. (1976) Ind. J. Chem., 14B, 339.
(2) Simmonds, M.S.J., Blaney, W.M., Monache, F.D., and Bettolo, G.B.M. (1990) J. Chem. Ecol., 16, 365.

© 2005 by CRC Press LLC


Insect Antifeedants 321

DESACETYLOARCTOLIDE C15H17O5
(277.34)
Only spectral data given

H O

HO O

O
OH
CH2
CH2

(1, 2) (1)

SOURCE: Arctotis grandis Thunb., African daisy (Asteraceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius L. Wafer disk 10 mg/cm3 Feeding deterrence 1. Treatment given to


(Grain weevil) test coefficient = 98.7 adults.

2. Tribolium confusum Duv. Wafer disk 10 mg/cm3 Feeding deterrence 2. Treatment given to
(Confused flour beetle) test coefficient both adults and
Adults = 194.9 larvae.
Larvae = 114.3

3. Trogoderma granarium Wafer disk 10 mg/cm3 Feeding deterrence 3. Treatment given to


Everts test coefficient = 164.5 larvae.
(Khapra beetle)
Neutral value = 0
Absolute feeding
deterrence value =
200.
(2)

(1) Samek, Z., Holub, M., Grabarczyk, H., and Drozdz, B. (1977) Collect. Czech. Chem. Commun., 42, 2217.
(2) Nawrot, J., Bloszyk, E., Grabarczyk, H., Drozdz, B., Daniewski, W.M., and Holub, M. (1983) Prace. Nauk.
Inst. Ochr. Roslin, 25, 91.

© 2005 by CRC Press LLC


322 Opender Koul

4-DESOXY-8-EPI-IVANGUSTIN C15H20O2
(232.32)
[α]D24 : +35.2°

O
O

CH2

(1, 2) (1)

SOURCE: Eupatorium quadrangularae L., joe-pye-weed (Asteraceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Atta cephalotes (L.) Rye flake 0.6 mg/ml Feeding inhibition = Treatment to adult
(Leaf cutter ant) forced or 29.2% workers.
choice test 12 µg/flake (2)

(1) Bohlmann, F., Mahanta, P.K., Jakupovic, J., Rastogi, R.C., and Natu, A.A. (1978) Phytochemistry, 17, 1165.
(2) Hubert, T.D., Okunade, A.L., and Weimer, D.F. (1987) Phytochemistry, 26, 1751.

© 2005 by CRC Press LLC


Insect Antifeedants 323

1-DETIGLOYL-3-DEACETYLSALANNIN C27H36O7
(472.58)
Only spectral data given

COOCH3

OH O

O
HO
H
O

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Leptinotarsa decemlineata Leaf disk 25 µg/cm2 Feeding inhibition = Treatment to freshly


(Say) choice test 50.0% moulted 3rd instar
(Colorado potato beetle) larvae.
Disks examined
>400 µg/cm2 Feeding inhibition = every 2 h until 95%
95.0% of control disks were
eaten.
Concentrations =
PC50 and PC95 values,
respectively.
(1)

(1) Yamasaki, R.B. and Klocke, J.A. (1989) J. Agric. Food Chem., 37, 1118.

© 2005 by CRC Press LLC


324 Opender Koul

1-DETIGLOYL-3-DEACETYL-20,21,22, C27H40O7
23-TETRAHYDROSALANNIN (476.61)
Only spectral data given

COOCH3

OH O

O
HO
H
O

(1,2) (1)

SOURCE: Synthetic (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Leptinotarsa decemlineata Leaf disk 50 µg/cm2 Feeding inhibition = Treatment to freshly


(Say) choice test 95.0% molted 3rd instar
(Colorado potato beetle) larvae.
Disks examined
every 2 h until 95%
of control disks were
eaten.
Concentration = PC95
value.
(1)

(1) Yamasaki, R.B. and Klocke, J.A. (1989) J. Agric. Food Chem., 37, 1118.

© 2005 by CRC Press LLC


Insect Antifeedants 325

1-DETIGLOYL-22,23-DIHYDROAZADIRACHTIN C30H41O15
(641.61)
No physical data given

COOCH3
OH OH
HO O

O
O
OH
AcO
H
H3COOC O

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera littoralis (Boisd.) Glass fiber 1.0 ppm Feeding inhibition = Treatment to starved
(Egyptian cotton leafworm) disk choice 75.0% final stadium larvae
test (24 to 36 h old).
Bioassays terminated
2. Spodoptera frugiperda Glass fiber 1.0 ppm Feeding inhibition = after the larvae had
(J.E. Smith) disk choice 56.0% eaten approximately
(Fall armyworm) test 50% of one of the
disks.
3. Heliothis virescens (Fab.) Glass fiber 1.0 ppm Feeding inhibition = (1)
(Tobacco budworm) disk choice 58.0%
test

4. Helicoverpa armigera Glass fiber 1.0 ppm Feeding inhibition =


(Hubner) disk choice 40.0%
(Gram pod borer) test

(1) Blaney, W.M., Simmonds, M.S.J., Ley, S.V., Anderson, J.C., and Toogood, P.L. (1990) Entomol. Exp. App.,
55, 149.

© 2005 by CRC Press LLC


326 Opender Koul

1-DETIGLOYL-3-O-METHYL-3- C28H38O7
DEACETYLSALANNIN (486.61)
Only spectral data given

COOCH3

OH O

O
CH3O
H
O

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Leptinotarsa decemlineata Leaf disk 400 µg/cm2 Feeding inhibition = Treatment to freshly
(Say) choice test 50.0% moulted 3rd instar
(Colorado potato beetle) larvae.
Disks examined
every 2 h until 95%
of control disks were
eaten.
Concentration = PC50
value.
(1)

(1) Yamasaki, R.B. and Klocke, J.A. (1989) J. Agric. Food Chem., 37, 1118.

© 2005 by CRC Press LLC


Insect Antifeedants 327

1-DETIGLOYL-3-O-METHYL-3- C28H42O7
DEACETYL-20,21,22,23- (490.64)
TETRAHYDROSALANNIN Only spectral data given

COOCH3

OH O

O
CH3O
H
O

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Leptinotarsa decemlineata Leaf disk 50 µg/cm2 Feeding inhibition = Treatment to freshly


(Say) choice test 95.0% moulted 3rd instar
(Colorado potato beetle) larvae.
Disks examined
every 2 h until 95%
of control disks were
eaten.
Concentration = PC95
value.
(1)

(1) Yamasaki, R.B. and Klocke, J.A. (1989) J. Agric. Food Chem., 37, 1118.

© 2005 by CRC Press LLC


328 Opender Koul

DHURRIN C14H17O7N
(311.28)
M.p. : 165°

[α]D20 : –62.7° (Alcohol)


H
CH2OH

O C OH
O
OH

CN
OH H

OH

(1) (1)

SOURCE: Sorghum bicolor (L.) Moench., grain sorghum (Poaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Schizaphis graminum (Rondani) Artificial diet 0.16% Feeding inhibition = Treatment to 50–75
(Wheat aphid) feeding 50.0% aphids at random.

Concentration = EC50
value.
(2)

(1) Towers, G.H.N., McInnes, A.G., and Neish, A.C. (1964) Tetrahedron, 20, 71.
(2) Dreyer, D.L., Reese, J.C., and Jones, K.C. (1981) J. Chem. Ecol., 7, 273.

© 2005 by CRC Press LLC


Insect Antifeedants 329

DIACETOXY DIBENZOYLOXY-1,4-DI C33H38O11


HYDROXY-DIHYDRO-β-AGAROFURAN (610.66)
Oil

[α]D25 : –39.7° (CHCl3)


AcO

OH OBz

OBz

O
HO OAc

(1) (1)

SOURCE: Maytenus canariensis (Loes) Kunk. & Sund., peralillo (Celastraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera littoralis (Boisd.) Leaf disk 10 µg/cm2 Feeding deterrent Treatment to larvae.
(Egyptian cotton leaf worm) choice test No quantitative
percentage inhibition
given.
(1)

(1) Gonzalez, A.G., Jimenez, I.A., Ravelo, A.G., Sazatornil, J.G., and Bazzochi, I.L. (1993) Tetrahedron, 49, 697.

© 2005 by CRC Press LLC


330 Opender Koul

6α-12-DIACETOXY-2β,9α-DI (β-FURAN C33H39O14


CARBONYLOXY)-4α-HYDROXY-1β-2- (659.66)
METHYLBUTANOYLOXY-β-DIHYDRO Amorphous powder
AGAROFURAN
[α]D14 : 70.8° (CHCl3)

O
AcO
COO OCO

OOC O

O
OAc OH

(1) (1)

SOURCE: Euonymus bungeanus Max., winter berry (Celastraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Pieris rapae (L.) Leaf feeding 200 ppm Feeding inhibition = Treatment to larvae
(Imported cabbage worm) 67.0% for 48 h

500 ppm Feeding inhibition = Treatment to larvae


33.0% pre-starved for 3 h.
(1)

(1) Tu, Y.Q., Wu, D.G., Zhou, J., Chen, Y.Z., and Pan, X.F. (1990) J. Nat. Prod., 53, 603.

© 2005 by CRC Press LLC


Insect Antifeedants 331

6α-12-DIACETOXY-1β,9α-DI (β-FURAN C34H42O14


CARBONYLOXY)-4α-HYDROXY-2β-2- (674.70)
METHYLBUTANOYLOXY-β-DIHYDRO M.p. : 145–146°
AGAROFURAN
[α]D14 : 43.07° (CHCl3)

O O
AcO
COO OOC

OCO

O
OAc OH

(1) (1)

SOURCE: Euonymus bungeanus Max., winter berry (Celastraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Pieris rapae (L.) Leaf feeding 200 ppm Feeding inhibition = Treatment to larvae
(Imported cabbage worm) 31.0% for 48 h

500 ppm Feeding inhibition = Treatment to larvae


28.0% pre-starved for 3 h.
(1)

(1) Tu, Y.Q., Wu, D.G., Zhou, J., Chen, Y.Z., and Pan, X.F. (1990) J. Nat. Prod., 53, 603.

© 2005 by CRC Press LLC


332 Opender Koul

6α-12-DIACETOXY-1β,2β,9α-TRI C34H42O14
(β-FURANCARBONYLOXY)-4α- (684.65)
HYDROXY-β-DIHYDROAGAROFURAN Amorphous powder

[α]D14 : 83.94° (CHCl3)

O
O
AcO
COO OOC
O

OOC

O
OAc OH

(1) (1)

SOURCE: Euonymus bungeanus Max., winter berry (Celastraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Pieris rapae (L.) Leaf feeding 200 ppm Feeding inhibition = Treatment to larvae
(Imported cabbage worm) 42.0% for 48 h

500 ppm Feeding inhibition = Treatment to larvae


22.0% pre-starved for 3 h.
(1)

(1) Tu, Y.Q., Wu, D.G., Zhou, J., Chen, Y.Z., and Pan, X.F. (1990) J. Nat. Prod., 53, 603.

© 2005 by CRC Press LLC


Insect Antifeedants 333

DIACETOXY TRIBENZOYLOXY-4- C40H42O12


HYDROXY-DIHYDRO-β-AGAROFURAN (714.76)
M.p. : 174–175°

[α]D25 : +52.7° (CHCl3)


OAc

BzO OBz

OBz

O
HO OAc

(1) (1)

SOURCE: Maytenus canariensis (Loes) Kunk. & Sund., peralillo (Celastraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera littoralis (Boisd.) Leaf disk 10 µg/cm2 Feeding deterrent Treatment to larvae.
(Egyptian cotton leaf worm) choice test No quantitative
percent inhibition
given.
(1)

(1) Gonzalez, A.G., Jimenez, I.A., Ravelo, A.G., Sazatornil, J.G., and Bazzochi, I.L. (1993) Tetrahedron, 49, 697.

© 2005 by CRC Press LLC


334 Opender Koul

2α,7β-DIACETOXY-15-ISOPIMARENE C24H38O6
3β,8β-DIOL (422.56)
M.p. : 174–176°

OH
AcO CH2

HO OAc

(1) (1)

SOURCE: Satureja gilliesii (Grah.) Briq., savory (Labiatae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera littoralis (Boisd.) Leaf disk 10 µg/cm2 Feeding inhibition Treatment to 3rd
(Egyptian cotton leaf worm) choice test ratio = 0.27 ± 0.09 instar larvae.

Concentration = EC50
value.
(1)

(1) Labbe, C., Castillo, M., Fainia, F., Coll, J., and Connolly, J.D. (1994) Phytochemistry, 36, 735.

© 2005 by CRC Press LLC


Insect Antifeedants 335

6,19 – DIACETYLTEUMASSILIN C24H34O7


(434.53)
M.p. : 155–156°

[α]D20 : –19.3° (CHCl3)


O

OH

O
OAc
OAc

(1, 2) (1)

SOURCE: Teucrium massiliense L., purple germander (Labiatae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera littoralis (Boisd.) Glass fiber 100 ppm Feeding deterrence = 1. Treatment to final
(Egyptian cotton leaf worm) disk choice 32.2% stadium larvae
test starved for 4 h.
Treatment was never
10 ppm Feeding deterrence = longer than 18 h so
21.7% that at no stage more
than 50% of any disk
was consumed.
(2)

2. Helicoverpa armigera Glass fiber 100 ppm Feeding deterrence = 2. Treatment to final
(Hubner) disk choice 63.2% stadium larvae as
(Gram pod borer) test above.
10 ppm Feeding deterrence = (2)
16.9%

(1) Savona, G., Bruno, M., Piozzi, F., Servettaz, O., and Rodriguez, B. (1984) Phytochemistry, 23, 849.
(2) Simmonds, M.S.J., Blaney, W.M., Ley, S.V., Savona, G., Bruno, M., and Rodriguez, B. (1989) Phytochemistry,
28, 1069.

© 2005 by CRC Press LLC


336 Opender Koul

1,12-DI-O-ACETYLTRICHILIN–B C39H50O15
(758.88)
[α]D22 : +0.8° (MeOH)

OAc O

O
OAc

AcO

O O

AcO OH

OCO

(1, 2) (1)

SOURCE: Melia azedarach L., chinaberry (Meliaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera eridania Leaf disk 400 ppm Feeding deterrent 1. Treatment to 3rd
(Cramer) choice test instar larvae for 6 to
(Southern armyworm) 24 h, during which
period 50% of one of
the disks was
consumed.
(2)

2. Spodoptera exigua (Hubner) Leaf disk 400 ppm Feeding deterrent 2. Treatment to 3rd
(Beet armyworm) choice test instar larvae for 6 to
24 h, during which
period 50% of one of
the disks was
consumed.
(2)

Concentration =
Threshold level for
deterrence

(1) Nakatani, M., Huang, R.C., Okamura, H., Naoki, H., and Iwagawa, T. (1994) Phytochemistry, 36, 39.
(1) Nakatani, M., Huang, R.C., Okamura, H., Iwagawa, T., Tadera, K., and Naoki, H. (1995) Tetrahedron, 51,
11731.

© 2005 by CRC Press LLC


Insect Antifeedants 337

DIACETYLVILASININE C30H40O7
(512.64)
M.p. : 157–158°

AcO

AcO OH

(1) (1)

SOURCE: Azadirachta indica A. Juss., neem (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Epilachna varivestis Muls. Bean leaf test 13 ppm Feeding deterrence = Treatment to 4th
(Mexican bean beetle) 50% instar larvae.
(2)

(1) Kraus, W. and Cramer, R. (1981) Liebigs Ann. Chem., 2381.


(2) Kraus, W. (2002) In H. Schmutterer (ed.), The Neem Tree, 2nd edition, The Neem Foundation, Mumbai, India,
pp. 39–111.

© 2005 by CRC Press LLC


338 Opender Koul

β-γ-DIAMINOBUTYRIC ACID C4H10O2N2


(118.14)
M.p. : 222–223° (HCl)

[α]D : +7.9° (H2O)

CH2COOH

H2N C H

CH2NH2

(1, 2) (1, 2)

SOURCE: Lathyrus latifolius L., everlasting pea (Fabaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera littoralis (Boisd.) Glass fiber 0.25% Feeding inhibition = Final stadium larvae
(Egyptian cotton leaf worm) disk test 26.0% treatment pre-starved
for 4 h.
Treatment given until
50% of the disk was
0.5% Feeding inhibition = eaten or 18 h,
61.0% whichever was
achieved first. At
lower concentrations
this compound was
phagostimulant.
(2)

(1) (1994) Dictionary of Natural Products, Chapman & Hall, London.


(2) Bell, E.A., Perera, K.P.W.C., Nunn, P.B., Simmonds, M.S.J., and Blaney, W.M. (1996) Phytochemistry, 43,
1003.

© 2005 by CRC Press LLC


Insect Antifeedants 339

DIAMINOGUANIDINE HYDRAZONE C21H20O3N6F8


(556.42) No physical
data given

H H

NH

=
HCF2F2O CH = N.N.(CH3)2N.CO.CNHN = CH OF2CF2CH

(1, 2) (1, 2)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera eridania (Cramer) Leaf disk test 8.6 ppm Feeding inhibition = Treatment to larvae.
(Southern armyworm) 50.0%
Concentration = EC50
value.
(1)

(1) Addor, R.W., Wright, D.P. Jr., Siddens, J.K., and Hand, J.J. (1986) U.S. patent 4575560, 12 pp.

© 2005 by CRC Press LLC


340 Opender Koul

2,3-DIAMINOPROPANOIC ACID C3H8O2N2


(104.11)
M.p. : 97°
(begins to melt at this
temperature)

COOH

H C NH2

CH2NH2

(1) (1)

SOURCE: Acacia spp. (Fabaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Anacridium melanorhodon Glass fiber 0.5% of Feeding inhibition = 1. Treatment to 3rd to


arabafrum (Dirsh.) disk test disk weight 30.0–60.0% 6th instar larvae at
(Tree locust) random.

5.0% of Feeding inhibition =


disk weight 91.0–100.0%
(2)

2. Locusta migratoria Glass fiber 1.0% of Feeding inhibition = 2. Treatment to male


migratorioides (R & F) disk test disk weight 61.0–90.0% 5th instar larvae.
(Migratory locust) (2)

(1) (1983) Merck Index, p. 431.


(2) Evans, C.S. and Bell, E.A. (1971) Phytochemistry, 18, 1807.

© 2005 by CRC Press LLC


Insect Antifeedants 341

14-15-DIHYDROAJUGAPITIN C29H44O10
(552.66)
M.p. : 212–214°
O
H
[α]D20 : –40° (CHCl3)
O
H H

H
HO

COO
O
CH2
OCOCH3

OCOCH3

(1, 2) (1)

SOURCE: Ajuga pseudoiva (L.) Schreber, African ajuga (Labiatae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera littoralis (Boisd.) Leaf disk 1 µg/cm2 Feeding ratio = Treatment to newly
(Egyptian cotton leaf worm) choice test 0.11 ± 0.04 ecdysed 5th instar
(ratio calculated larvae.
when 50% of control Ratio of < 0.5
disk area was considered as
consumed) excellent feeding
inhibition value.
0.1 µg/cm2 Feeding ratio = (2)
0.22 ± 0.08

0.01 µg/cm2 Feeding ratio =


0.32 ± 0.10

0.001 µg/cm2 Feeding ratio =


0.46 ± 0.20

(1) Camps, F., Coll, J., and Dargallo, O. (1984) Phytochemistry, 23, 387.
(2) Belles, X., Camps, F., Coll, J., and Piulachs, M.D. (1985) J. Chem. Ecol., 11, 1439.

© 2005 by CRC Press LLC


342 Opender Koul

22,23-DIHYDROAZADIRACHTIN C35H46O16
(722.74)
Only spectral data given

O COOCH3
OH
O O OH

O
O

AcO OH
H
H3COOC O

(1, 2) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera littoralis Glass fiber disk 1 ppm Feeding inhibition = Treatment to 24- to
(Boisd.) choice test 100%. 36-h-old starved final
(Egyptian cotton leaf stadium larvae.
worm) Glass fiber disk 1 ppm Feeding inhibition = Bioassay terminated
no-choice test 77.8%. after the larvae had
consumed about 50%
2. Spodoptera frugiperda Glass fiber disk 1 ppm Feeding inhibition = of one of the disks.
(J.E. Smith) choice test 100%. (2)
(Fall armyworm)
Glass fiber disk 1 ppm Feeding inhibition = Deterrence
no-choice test 87.3%. calculated from
Reference 2 for no-
3. Heliothis virescens (Fab.) Glass fiber disk 1 ppm Feeding inhibition = choice assay run for
(Tobacco budworm) choice test 87.3%. 8 to 9 h.

Glass fiber disk 1 ppm Feeding inhibition =


no-choice test 67.0%.

4. Helicoverpa armigera Glass fiber disk 1 ppm Feeding inhibition =


(Hubner) choice test 74.0%.
(Gram pod borer)

(1) Bilton, J.N., Broughton, H.B., Jones, P.S., Ley, S.V., Lidert, Z., Morgan, E.D., Rzepa, H.S., Sheppard, R.N.,
Slawin, A.M.Z., and Williams, D.J., Tetrahedron, 43, 2805.
(2) Blaney, W.M., Simmonds, M.S.J., Ley, S.V., Anderson, J.C., and Toogood, P.L. (1990) Entomol. Exp. Appl.,
55, 149.

© 2005 by CRC Press LLC


Insect Antifeedants 343

[11 RS]-22,23-DIHYDROAZADIRACHTININ C35H46O16


(722.74)
Only spectral data given

O COOCH3

O O OH H
OH
O O
H

O
AcO OH
H
H3COOC O

(1, 2) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera littoralis (Boisd.) Glass fiber 1 ppm Feeding inhibition = Treatment to 24- to
(Egyptian cotton leaf worm) disk choice 96.0%. 36-h-old starved final
test stadium larvae.
Bioassay terminated
2. Spodoptera frugiperda Glass fiber 1 ppm Feeding inhibition = after the larvae had
(J.E. Smith) disk choice 45.0%. consumed about 50%
(Fall armyworm) test of one of the disks.
(2)

3. Heliothis virescens (Fab.) Glass fiber 1 ppm Feeding inhibition =


(Tobacco budworm) disk choice 21.0%.
test

4. Helicoverpa armigera Glass fiber 1 ppm Feeding inhibition =


(Hubner) disk choice 11.0%.
(Gram pod borer) test

(1) Bilton, J.N., Broughton, H.B., Jones, P.S., Ley, S.V., Lidert, Z., Morgan, E.D., Rzepa, H.S., Sheppard, R.N.,
Slawin, A.M.Z., and Williams, D.J., Tetrahedron, 43, 2805.
(2) Blaney, W.M., Simmonds, M.S.J., Ley, S.V., Anderson, J.C., and Toogood, P.L. (1990) Entomol. Exp. Appl.,
55, 149.

© 2005 by CRC Press LLC


344 Opender Koul

22,23-DIHYDROAZADIRACHTOL C28H37O14
(597.59)
Only spectral data given

COOCH3
OH
HO O OH

O
O
OH
HO
H
H3COOC O

(1) (2)

SOURCE: Synthetic (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera littoralis (Boisd.) Glass fiber 1 ppm Feeding inhibition = Treatment to 24- to
(Egyptian cotton leaf worm) disk choice 63.0% 36-h-old starved final
test stadium larvae.
Bioassay terminated
Glass fiber 1 ppm Feeding inhibition = after the larvae had
disk no- 47.4% consumed about 50%
choice test of one of the disks.
(1)
2. Spodoptera frugiperda Glass fiber 1 ppm Feeding inhibition = Approximate EC50
(J.E. Smith) disk choice 60.0% calculated = < 1.0
(Fall armyworm) test ppm.
Deterrence
Glass fiber 1 ppm Feeding inhibition = calculated from
disk no- 51.3% Reference 1 for no-
choice test choice assay run for
8 to 9 h.

(1) Blaney, W.M., Simmonds, M.S.J., Ley, S.V., Anderson, J.C., and Toogood, P.L. (1990) Entomol. Exp. Appl.,
55, 149.
(2) Ley, S.V. (1990) In E. Frehse (ed.), Pesticide Chemistry, VCH, New York, p. 97.

© 2005 by CRC Press LLC


Insect Antifeedants 345

DIHYDROCARYOPTIN C27H38O9
CH2 (506.59)
M.p. : 198.5–199.5°

O [α]D : –63° (CHCl3)

H H

O
H

AcO

H
O CH2
OAc

OAc (1) (1)

SOURCE: Caryopteris divaricata Maxim., snow fairy (Verbenaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera litura (Fab.) Leaf disk 80 ppm Feeding inhibition = Treatment to 3rd
(Tobacco armyworm) choice test 100% within 2 h instar larvae. The
larvae eventually
starve to death. The
compound termed as
absolute antifeedant.
(2)

(1) Hosozawa, S., Kato, N., and Munakata, K. (1973) Phytochemistry, 12, 1833.
(2) Hosozawa, S., Kato, N., Munakata, K., and Chen, Y. (1974) Agric. Biol. Chem., 38, 1045.

© 2005 by CRC Press LLC


346 Opender Koul

DIHYDROCARYOPTINOL C25H36O8
CH2
(464.55)
M.p. : 204–205°

O [α]D : –73° (CHCl3)

H H

O
H

HO
O CH2
OAc

OAc (1) (1)

SOURCE: Caryopteris divaricata Maxim., snow fairy (Verbenaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera litura (Fab.) Leaf disk 100 ppm Feeding inhibition = Treatment to 3rd
(Tobacco armyworm) choice test 100% within 2 h instar larvae. The
larvae eventually
starve to death. The
compound termed as
absolute antifeedant.
(2)

(1) Hosozawa, S., Kato, N., and Munakata, K. (1974) Phytochemistry, 13, 1019.
(2) Hosozawa, S., Kato, N., Munakata, K., and Chen, Y. (1974) Agric. Biol. Chem., 38, 1045.

© 2005 by CRC Press LLC


Insect Antifeedants 347

DIHYDROCLERODIN–I C24H36O7
(436.54)
M.p. : 169–170°

O [α]D24 : –10.9° (CHCl3)

H H

O
H

O CH2
OAc

OAc (1, 2) (1, 2)

SOURCE: Caryopteris divaricata Maxim., snow fairy (Verbenaceae) (1, 2, 3)


Ajuga parviflora Benth, ajuga (Labiatae)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera litura (Fab.) Leaf disk 50 ppm Feeding inhibition = Treatment to 3rd
(Tobacco armyworm) choice test 100% within 2 h instar larvae. The
larvae eventually
starve to death. The
compound termed as
absolute antifeedant.
(3)

(1) Hosozawa, S., Kato, N., and Munakata, K. (1974) Agric. Biol. Chem., 38, 823.
(2) Beauchamp, P.S., Bottini, A.T., Caselles, M.C., Dev, V., Hope, H., Larter, M., Lee, G., Mathela, C.S., Melkani,
A.B., Miller, P.D., Miyatake, M., Pant, A.K., Raffel, R.J., Sharma, V.K. and Wyatt, D. (1996) Phytochemistry,
43, 827.
(3) Hosozawa, S., Kato, N., Munakata, K., and Chen, Y. (1974) Agric. Biol. Chem., 38, 1045.

© 2005 by CRC Press LLC


348 Opender Koul

DIHYDROCEDRELONE C26H32O5
(424.54)
M.p. : 216°

[α]D30 : –55.5° (CHCl3)


O

O O

OH

(1, 2) (1)

SOURCE: Synthetic (1)


Also isolated from Cedrela toona Roxb., cedro toona (Cedrelaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk 1 µg/cm2 Feeding inhibition = Treatment to 3rd
(Tobacco armyworm) dual-choice 49.5% instar larvae for 24 h.
test (2)

5 µg/cm2 Feeding inhibition = Approximate EC50 =


57.1% 1.2 µg/cm2

Calculated from
10 µg/cm2 Feeding inhibition = Reference 2.
70.5%

50 µg/cm2 Feeding inhibition =


67.7%

(1) Hodges, R., McGeachin, S.G., and Raphel, R.A. (1963) J. Chem. Soc., 2515.
(2) Govindachari, T.R., Narasimhan, N.S., Suresh, G., Partho, P.D., Gopalakrishnan, G., and Krishna Kumari,
G.N. (1995) J. Chem. Ecol., 21, 1586.

© 2005 by CRC Press LLC


Insect Antifeedants 349

DIHYDROCEDRELONE METHYL ETHER C27H34O5


(438.57)
Only spectral data given

O O

OCH3

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk 1 µg/cm2 Feeding inhibition = Treatment to 3rd
(Tobacco armyworm) dual-choice 43.5% instar larvae for 24 h.
test (2)

5 µg/cm2 Feeding inhibition = Approximate EC50 =


44.5% 8.8 µg/cm2

Calculated from
10 µg/cm2 Feeding inhibition = Reference 2.
56.5%

50 µg/cm2 Feeding inhibition =


64.2%

(1) Hodges, R., McGeachin, S.G., and Raphel, R.A. (1963) J. Chem. Soc., 2515.
(2) Govindachari, T.R., Narasimhan, N.S., Suresh, G., Partho, P.D., Gopalakrishnan, G., and Krishna Kumari,
G.N. (1995) J. Chem. Ecol., 21, 1586.

© 2005 by CRC Press LLC


350 Opender Koul

DIHYDROERGOCRYSTINE C35H41O5N5
(611.74)
Only spectral data given
OH

O O
N
NH
N
O O

NH

(1) (1)

SOURCE: Commercial sample (2)


Basically obtained from Lolium perenne L., ryegrass (Graminaceae) infected with fungus
Neotyphodium lolii

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Heteronychus arator (Fab.) Artificial diet 5 µg/g Feeding inhibition = Treatment to adults
(Black beetle) choice test 45.5% for 96 h.
(2)

10 µg/g Feeding inhibition =


54.8% Data calculated from
Reference 2.

(1) Coppi, G. (1992) Ayzneim-Forsch, 42, 1381, 1391.


(2) Ball, O.J.-P., Miles, C.O., and Prestidge, R.A. (1997) J. Econ. Entomol., 90, 1382.

© 2005 by CRC Press LLC


Insect Antifeedants 351

DIHYDROERGOTAMINE C33H37O5N5
(583.69)
M.p. : 239°
OH
[α]D20 : –64° (pyridine)
O O
N
N
H N
O O

NH
(1, 2) (1)

SOURCE: Commercial sample (2)


Basically obtained from Lolium perenne L., ryegrass (Graminaceae) infected with fungus
Neotyphodium lolii

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Heteronychus arator (Fab.) Artificial diet 5 µg/g Feeding inhibition = Treatment to adults
(Black beetle) choice test 60.0% for 96 h.
(2)

20 µg/g Feeding inhibition =


60.0% Data calculated from
Reference 2.

(1) (1994) Dictionary of Natural Products, Chapman & Hall, London.


(2) Ball, O.J.-P., Miles, C.O., and Prestidge, R.A. (1997) J. Econ. Entomol., 90, 1382.

© 2005 by CRC Press LLC


352 Opender Koul

22,23-DIHYDRO-23-α,β-ETHOXY C37H50O17
AZADIRACHTIN (766.79)
Only spectral data given

O COOCH3
OH
O O OH

O
OC2H5

O
O

AcO OH
H
H3COOC O

(1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera littoralis (Boisd.) Glass fiber 1 ppm Feeding inhibition = Treatment to 24- to
(Egyptian cotton leaf worm) disk choice 66.0% 36-h-old starved final
test stadium larvae.
Bioassay terminated
2. Spodoptera frugiperda Glass fiber 1 ppm Feeding inhibition = after the larvae had
(J.E. Smith) disk choice 62.0% consumed about 50%
(Fall armyworm) test of one of the disks.
(1)

3. Heliothis virescens (Fab.) Glass fiber 1 ppm Feeding inhibition = EC50 = < 1.0 ppm
(Tobacco budworm) disk choice 64.0%
test

4. Helicoverpa armigera Glass fiber 1 ppm Feeding inhibition =


(Hubner) disk choice 54.0%
(Gram pod borer) test

(1) Blaney, W.M., Simmonds, M.S.J., Ley, S.V., Anderson, J.C., and Toogood, P.L. (1990) Entomol. Exp. Appl.,
55, 149.

© 2005 by CRC Press LLC


Insect Antifeedants 353

DIHYDROISOLONCHOCARPIN C20H20O3
(308.36)
No physical data given

O O

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera exempta (Walker) Glass fiber 100 ppm Feeding inhibition = 1. Treatment to 24- to
(Nutgrass armyworm) disk dual- 75.0%. 36-h-old starved final
choice test stadium larvae for
10 ppm Feeding inhibition = 5 h. Larvae pre-
42.0%. starved for 4 h.
(2)

2. Spodoptera littoralis (Boisd.) Glass fiber 100 ppm Feeding inhibition = 2. Treatment to 24- to
(Egyptian cotton leaf worm) disk dual- 23.0%. 36-h-old starved final
choice test stadium larvae for
10 ppm Feeding inhibition = 5 h. Larvae pre-
33.0%. starved for 4 h.
(2)

(1) Simmonds, M.S.J., Blaney, W.M., Monache, F.D., and Bettolo, G.B.M. (1990) J. Chem. Ecol., 16, 365.

© 2005 by CRC Press LLC


354 Opender Koul

DIHYDROISOPIMPINELLIN C13H12O5
(248.23)
M.p. : 162–163°

OCH3

O O O

OCH3

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk 100 ppm Feeding ratio = Treatment to 3rd
(Tobacco armyworm) test 8.0% instar larvae.
Ratio between 0 and
10 ppm Feeding ratio = 20% considered as
15.0% strong inhibitory
effect.
5 ppm Feeding ratio = (1)
67.0%

(1) Yajima, T. and Munakata, K. (1979) Agric. Biol. Chem., 43, 1701.

© 2005 by CRC Press LLC


Insect Antifeedants 355

22,23-DIHYDRO-23-α,β-ISOPROPOXY C38H52O17
AZADIRACHTIN (780.44)
Only spectral data given

O COOCH3
OH
O O OH

O
OPr

O
O

AcO OH
H
H3COOC O

(1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera frugiperda Glass fiber 1 ppm Feeding inhibition = Treatment to 24- to


(J.E. Smith) disk choice 94.0% 36-h-old starved final
(Fall armyworm) test stadium larvae.
Bioassay terminated
Glass fiber 1 ppm Feeding inhibition = after the larvae had
disk no- 96.7% consumed about 50%
choice test of one of the disks.
(1)

Deterrence
calculated from
Reference 1 for no-
choice assay run for
8 to 9 h.

(1) Blaney, W.M., Simmonds, M.S.J., Ley, S.V., Anderson, J.C., and Toogood, P.L. (1990) Entomol. Exp. Appl.,
55, 149.

© 2005 by CRC Press LLC


356 Opender Koul

14,15-DIHYDROJODRELLIN–T C29H40O10
(548.63)
[α]D20 : –24.4° (CHCl3)
OAc

OAc
O
O

O
O

O
O
(1) (1)

SOURCE: Scutellaria galericulata L., blue skullcap (Labiatae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera littoralis (Boisd.) Glass fiber 100 ppm Feeding inhibition = Treatment to final
(Egyptian cotton leaf worm) disk choice 63.0% stadium larvae pre-
test starved for 4 h.
50 ppm Feeding inhibition = Treatment until
59.0% either 50% of disk
had been consumed
25 ppm Feeding inhibition = or for 12 h.
44.0% (1)

(1) Cole, M.D., Anderson, J.C., Blaney, W.M., Fellows, L.E., Ley, S.V., Sheppard, R.N., and Simmonds, M.S.J.
(1990) Phytochemistry, 29, 1793.

© 2005 by CRC Press LLC


Insect Antifeedants 357

DIHYDROKOKUSAGINE C13H11O4N
(245.23)
M.p. : 165–166°

OCH3

O N
O
O

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera litura (Fab.) Leaf disk 300 ppm Feeding inhibition = 1. Treatment to 3rd
(Tobacco armyworm) test 78.0% instar larvae.
(1)

2. Periplaneta americana (L.) Sugar pellet 0.1 mg/ Feeding inhibition = 2. Treatment to
(American cockroach) test 1.5 g pellet 100.0% adults.
(1)

3. Stylopyga rhombifolia Sugar pellet 0.1 mg/ Feeding inhibition = 3. Treatment to


(Cockroach) test 1.5 g pellet 85.0% adults.
(1)

4. Blatella germanica (L.) Sugar pellet 0.1 mg/ Feeding inhibition = 4. Treatment to
(German cockroach) test 1.5 g pellet 51.0% adults.
(1)

(1) Yajima, T. and Munakata, K. (1979) Agric. Biol. Chem., 43, 1701.

© 2005 by CRC Press LLC


358 Opender Koul

22,23-DIHYDRO-23-β-METHOXY C36H48O17
AZADIRACHTIN (vepaol) (752.76)
[α]D31 : –23° (CHCl3)

O COOCH3
OH
O O OH

O
OCH3

O
O

AcO OH
H
H3COOC O

(1) (2)

SOURCE: Synthetic (1)


Azadirachta indica A. Juss., neem (Meliaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera littoralis (Boisd.) Glass fiber 1 ppm Feeding inhibition = Treatment to 24- to
(Egyptian cotton leaf worm) disk choice 81.0% 36-h-old starved final
test stadium larvae.
Bioassay terminated
No-choice 1 ppm Feeding inhibition = after the larvae had
67.0% consumed about 50%
of one of the disks.

2. Spodoptera frugiperda Glass fiber 1 ppm Feeding inhibition = Approx. EC50 = < 1.0
(J.E. Smith) disk choice 70.0% ppm.
(Fall armyworm) test
No-choice 1 ppm Feeding inhibition = Deterrence
43.9% calculated from
Reference 1 for no-
3. Heliothis virescens (Fab.) Glass fiber 1 ppm Feeding inhibition = choice assay run for
(Tobacco budworm) disk choice 64.0% 8 to 9 h.
test (1)

(1) Blaney, W.M., Simmonds, M.S.J., Ley, S.V., Anderson, J.C., and Toogood, P.L. (1990) Entomol. Exp. Appl.,
55, 149.
(2) Sankaram, A.V.B., Murthy, M.M., Bhaskaraiah, K., Subramanyam, M., Sultana, N., Sharma, H.C., Leuschner,
K., Ramaprasad, G., Sitaramaiah, S., Rukmini, C., and Rao, P.U. (1987) In H.Schmutterer and K.R.S. Ascher
(eds.), Natural Pesticides from Neem and Other Tropical Plants, 3rd Int. Neem Conf., Nairobi, pp. 127–148.

© 2005 by CRC Press LLC


Insect Antifeedants 359

[11 RS]-22,23-DIHYDRO-23-α,β- C36H48O17


METHOXYAZADIRACHTININ (752.76)
Only spectral data given

O COOCH3

O O OH H
OH
O O
OCH3

O
AcO OH
H
H3COOC O

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera littoralis (Boisd.) Glass fiber 1 ppm Feeding inhibition = Treatment to 24- to
(Egyptian cotton leaf worm) disk choice 41.7% 36-h-old starved final
test stadium larvae.
No-choice 1 ppm Feeding inhibition = Observations
75.0% recorded after 1 h.
(1)
2. Heliothis virescens (Fab.) Glass fiber 1 ppm Feeding inhibition =
(Tobacco budworm) disk choice 38.5% Deterrence
test calculated from
No-choice 1 ppm Feeding inhibition = Reference 1 for no-
61.9% choice assay run for
8 to 9 h.
3. Spodoptera frugiperda Glass fiber 1 ppm Feeding inhibition =
(J.E. Smith) disk choice 61.6%
(Fall armyworm) test

(1) Blaney, W.M., Simmonds, M.S.J., Ley, S.V., Anderson, J.C., and Toogood, P.L. (1990) Entomol. Exp. Appl.,
55, 149.

© 2005 by CRC Press LLC


360 Opender Koul

[11 RS]-22,23-DIHYDRO-23-α,β- C41H50O16S


PHENYLTHIOAZADIRACHTININ (830.85)
No physical data given

O COOCH3

O O OH H
OH
O O
SPh

O
AcO OH
H
H3COOC O

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera littoralis (Boisd.) Glass fiber 1 ppm Feeding inhibition = Treatment to 24- to
(Egyptian cotton leaf worm) disk choice 37.0% 36-h-old starved final
test stadium larvae.
Bioassay terminated
2. Spodoptera frugiperda Glass fiber 1 ppm Feeding inhibition = after the larvae had
(J.E. Smith) disk choice 32.0% consumed about 50%
(Fall armyworm) test of one of the disks.
(1)

3. Heliothis virescens (Fab.) Glass fiber 1 ppm Feeding inhibition =


(Tobacco budworm) disk choice 32.0% Approximate EC50
test calculated = 2.0 ppm
except in case of H.
4. Helicoverpa armigera Glass fiber 1 ppm Feeding inhibition = armigera.
(Hubner) disk choice 6.0%
(Gram pod borer) test

(1) Blaney, W.M., Simmonds, M.S.J., Ley, S.V., Anderson, J.C., and Toogood, P.L. (1990) Entomol. Exp. Appl.,
55, 149.

© 2005 by CRC Press LLC


Insect Antifeedants 361

2′,3′-DIHYDROSALANNIN C34H46O9
(598.73)
Only spectral data given

O
O

O O
O

O
AcO
H
O

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Leptinotarsa decemlineata Leaf disk 200 µg/cm2 Feeding inhibition = Treatment to freshly
(Say) choice test 95.0% molted 3rd instar
(Colorado potato beetle) larvae.
Disks examined
every 2 h until 95%
of control disks were
eaten.
Concentration = PC95
value.
(1)

(1) Yamasaki, R.B. and Klocke, J.A. (1989) J. Agric. Food Chem., 37, 1118.

© 2005 by CRC Press LLC


362 Opender Koul

2,3-DIHYDRO WITHAFERIN–A C28H40O6


(472.62)
M.p. : 225–227°
(229–230°)

H OH
[α]D : +8° (CHCl3)

O O

O H

O
OH
(1,2) (1, 3)

SOURCE: Synthetic
Also isolated from Withania sominifera (L.) Dunal., common withania (Solanaceae) (2, 3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera littoralis (Boisd.) Styropor 1000 ppm Feeding inhibition = Treatment to early 5th
(Egyptian cotton leaf worm)) method 5.8% instar larvae for 48 h.
(2)

100 ppm Feeding inhibition = Data calculated from


11.0% Reference 2.

50 ppm Feeding inhibition =


9.5%

(1) Yarden, A. and Lavie, D. (1962) J. Chem. Soc., 2925.


(2) Ascher, K.R.S., Eliyahu, M., Glotter, E., Goldman, A., Kirson, I., Abraham, A., Jacobson, M., and Schmutterer,
H. (1987) Phytoparasitica, 15, 15.
(3) Lavie, D., Glotter, E., and Shuo, Y. (1965) J. Org. Chem., 30, 1774.

© 2005 by CRC Press LLC


Insect Antifeedants 363

2,3-DIHYDRO WITHANOLIDE–E C28H40O7


(488.62)
M.p. : 264–265°
(273–275°)

[α]D : –42°
OH

O O

O OH

OH

(1, 2) (1)

SOURCE: Synthetic (1, 2)


Also isolated from Physalis peruviana L., Peruvian groundcherry (Solanaceae)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera littoralis (Boisd.) Styropor 100 ppm Feeding inhibition = 1. Treatment to early
(Egyptian cotton leaf worm) method 95.7% 5th instar larvae for
48 h.
Data calculated from
Reference 2.
(2)

2. Epilachna varivestis Mulsant Bean leaf test 1000 ppm Feeding inhibition 2. Treatment to 4th
(Mexican bean beetle) determined by loss in instar larvae for 48 h.
weight to 1.5 mg
against 11.7 mg gain
in controls
250 ppm Feeding inhibition Loss in weight due to
determined by loss in starvation.
weight to 1.3 mg (2)
against 12 mg in
controls
3. Tribolium castaneum Yeast diet 500 ppm Feeding inhibition = 3. Treatment to 0 to
(Herbst.) feeding 44.0% 3-h-old larvae.
(Red flour beetle) (2)

(1) Glotter, E., Abraham, A., Gunzberg, G., and Kirson, I. (1977) J. Chem. Soc. Perkin Trans I, 341.
(2) Ascher, K.R.S., Eliyahu, M., Glotter, E., Goldman, A., Kirson, I., Abraham, A., Jacobson, M., Schmutterer,
H. (1987) Phytoparasitica, 15, 15.

© 2005 by CRC Press LLC


364 Opender Koul

DIHYDROXANTHOTOXIN C12H10O4
(218.21)
M.p. : 159–160°

O O O

OCH3

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera litura (Fab.) Leaf disk 500 ppm Feeding ratio = Treatment to 3rd
(Tobacco armyworm) choice test 18% instar larvae for
90 m.
Ratio = 0–20%
300 ppm Feeding ratio = strong feeding
38% inhibition.
(1)

100 ppm Feeding ratio =


62%

(1) Yajima, T. and Munakata, K. (1979) Agric. Biol. Chem., 43, 1701.

© 2005 by CRC Press LLC


Insect Antifeedants 365

2′,4′-DIHYDROOXYCHALCONE C15H12O3
(240.26)
M.p. : 149–150°
(142–143°)

HO OH

(1, 2) (1)

SOURCE: Synthetic (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera littoralis (Boisd.) Glass fiber 500 ppm Feeding inhibition = 1. Treatment to 24- to
(Egyptian cotton leaf worm) disk dual- 59.0% 36-h-old starved final
choice test stadium larvae for
100 ppm Feeding inhibition = 5 h. Larvae pre-
22.0% starved for 4 h.
(2)

(1) Adityachaudhury, N., Kirtaniya, C.L., and Mukherjee, B. (1971) Tetrahedron, 27, 2111.
(2) Simmonds, M.S.J., Blaney, W.M., Monache, F.D., and Bettolo, G.B.M. (1990) J. Chem. Ecol., 16, 365.

© 2005 by CRC Press LLC


366 Opender Koul

2,7-DIHYDROXY-3 (3′-METHOXY-4′-HYDROXY)- C17H14O7


5-METHOXYISOFLAVONE (330.29)
M.p. : 232°

OH

HO O

O O

OH
(1, 2) (1, 2)

SOURCE: Wedelia biflora (L.) DC., sami scandent shrub (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Anthonomous grandis Bohem. Paper disk 2.0% Feeding inhibition = Treatment to


(Boll weevil) test 71.0% weevils. Data
calculated on the
basis of punctures of
test paper per
number of punctures
of control paper.
(1)

(1) Miles, D.H., Chittawong, V., Hedin, P.A., and Kokpol, U. (1993) Phytochemistry, 32, 1427.
(2) Mabry, T.J., Markham, K.R., and Thomas, M.B. (1970) The Systemic Identification of Flavonoids, Academic,
New York.

© 2005 by CRC Press LLC


Insect Antifeedants 367

2,5-DIHYDROXYMETHYL-3,4- C6H13O4N
DIHYDROXY PYRROLIDINE (163.17)
[α]D20 : + 56.4° (H2O)
(DMDP)

HO OH

HOH2C N CH2OH
H

(1, 2) (1)

SOURCE: Derris elliptica Benth., derris plant (Fabaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Locusta migratoria (L.) Glass fiber 10–2 M Feeding inhibition = 1. Treatment to early
(Migratory locust) disk test 80.0 ± 13.34% with 5th instar larvae.
sucrose and 90.0 ± (2)
10.01% with
fructose.

2. Schistocerca gregaria Glass fiber 10–2 M Feeding inhibition = 2. Treatment to 5th


(Forsk.) disk test 100% with sucrose instar larvae.
(Desert locust) (2)

3. Spodoptera littoralis (Boisd.) Glass fiber 4 × 10–2 M Feeding inhibition = 3. Treatment to last
(Egyptian cotton leaf worm) disk test 61.4 ± 16.41% with instar larvae.
sucrose (2)

4. Spodoptera exempta (Walker) Glass fiber 4 × 10–2 M Feeding inhibition = 4. Treatment to last
(Nutgrass armyworm) disk test 93.3 ± 5.99% with instar larvae.
sucrose (2)

(1) Welter, A., Jadot, J., Dardenne, G., Marlier, M., and Casimir, J. (1976) Phytochemistry, 15, 747.
(1) Blaney, W.M., Simmonds, M.S.J., Evans, S.V., and Fellows, L.E. (1984) Entomol. Exp. Appl., 36, 209.

© 2005 by CRC Press LLC


368 Opender Koul

E-3- (3,4-DIHYDROXYPHENYL)-N-2- C17H17O4N


[4-HYDROXYPHENYLETHYL]-2- (299.33)
Only spectral data given
PROPENAMIDE

OH
O

HO
N
H

HO

(1, 2) (1)

SOURCE: Xylopia aethiopica A. Rich., African pepper (Anonaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Reticulitermes speratus Kolbe Paper disk 7500 ppm Feeding inhibition Treatment to 3rd
(Subterranean termite) choice index value = 14.6 instar workers.
bioassay
Feeding duration =
14 days.

Antifeedant index
value below 20.0 is
highly deterrent
value.
(2)

(1) Sakakibara, I., Katsuhara, I., Ikeya, Y., Hayashi, K., and Mitsuhashi, H. (1981) Phytochemistry, 20, 3013.
(2) Lajide, L., Escoubas, P., and Mizutani, J. (1995) Phytochemistry, 40, 1105.

© 2005 by CRC Press LLC


Insect Antifeedants 369

11β,5α-DIHYDROXY SILPHINEN-3-ONE C15H22O3


(250.34)
Only spectral data given

OH

O OH

(1, 2) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Leptinotarsa decemlineata Leaf disk 22.6 µg/cm2 Feeding inhibition = Treatments to newly
(Say) choice 50.0% emerged 4th instar
(Colorado potato beetle) bioassay larvae for ≤ 6 h.

Leaf disk 11.32 µg/cm2 Feeding inhibition = Treatments to newly


no-choice 50.0% emerged 4th instar
bioassay larvae for 24 h.

Concentration = FI50
value.
(1)

(1) Gonzalez-Coloma, A., Gutierrez, C., Cabrera, R., and Reina, M. (1997) J. Agric. Food Chem., 45, 946.
(2) Gonzalez-Coloma, A., Reina, M., Cabrera, R., Castanera, P., and Gutierrez, C. (1995) J. Chem. Ecol., 21, 1255.

© 2005 by CRC Press LLC


370 Opender Koul

DIMBOA C9H9O5N
(211.17)
M.p. : 156–157° (dec.)

H3CO O OH

N O

OH

(1, 2) (1)

SOURCE: Zea mays L., maize (Graminae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Schizaphis graminum (Rondani) Artificial diet 4 nM Feeding inhibition = Treatment to aphids


(Green bug) feeding 83.7.0% at random.

6 nM Feeding inhibition = Absolute antifeedant


100.0% effect achieved
within 20 h.
(2)

(1) Wahlroos, O. and Virtanen, A.I. (1959) Acta Chem. Scand., 13, 1906.
(2) Argandona, V.H., Corcuera, L.J., Niemeyer, H.M., and Campbell, B.C. (1983) Entomol. Exp. Appl., 34, 134.

© 2005 by CRC Press LLC


Insect Antifeedants 371

DIMBOA-GLUCOSYL C15H19O10N
(373.31)
M.p. : 262–263° (dec.)

OH

HO OH

OH
H3CO O O
O

N O

OH

(1, 2, 3) (1, 3)

SOURCE: Zea mays L., maize (Graminae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Schizaphis graminum (Rondani) Artificial diet 4 nM Feeding inhibition = Treatment to aphids


(Wheat aphid) feeding 71.4% at random.

6 nM Feeding inhibition = Absolute antifeedant


100.0% effect achieved
within 20 h.
(2)

(1) Wahlroos, O. and Virtanen, A.I. (1959) Acta Chem. Scand., 13, 1906.
(2) Argandona, V.H., Corcuera, L.J., Niemeyer, H.M., and Campbell, B.C. (1983) Entomol. Exp. Appl., 34, 134.
(3) Hofman, J., Hofmanova, O., and Hanus, V. (1969) Tetrahedron Lett., 5001.

© 2005 by CRC Press LLC


372 Opender Koul

3,4-DIMETHOXYBENZALDEHYDE C9H10O3
(166.18)
M.p. : 44°
(58°)

B.p. : 172–175°/18 mm
OCH3

OCH3

CHO

(1, 2) (1, 2)

SOURCE: Artemisia capillaris Thumb., wormwood (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Pieris rapae crucivora Boisd. Leaf disk 10–1 mol/l Feeding inhibition = Treatment to 5th
(Cabbage butterfly) dual-choice 72.8% instar larvae pre-
test or starved for 3 h.
Treatment duration =
5 × 10–7 2 h.
mol/cm2 (1)

LD50 (rats): 2000 mg/kg (oral) (3)

(1) Yano, K. and Kamimura, H. (1993) Biosci. Biotech. Biochem., 57, 129.
(2) (1994) Dictionary of Natural Products, Chapman & Hall, London.
(3) Opdyke, D.L.J. (1975) Food Cosmet. Toxicol., 13, 923.

© 2005 by CRC Press LLC


Insect Antifeedants 373

3,4-DIMETHOXYBENZAL ALCOHOL C9H12O3


(168.19)
Viscous oil

B.p. : 172°/12 mm

OCH3 d17
17 : 1.179

OCH3

CH2OH

(1, 2) (1, 2)

SOURCE: Artemisia capillaris Thumb., wormwood (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Pieris rapae crucivora Boisd. Leaf disk 10–1 mol/l Feeding inhibition = Treatment to 5th
(Cabbage butterfly) dual-choice 61.7% instar larvae pre-
test or starved for 3 h.
Treatment duration =
5 × 10–7 2 h.
mol/cm2 (1)

(1) Yano, K. and Kamimura, H. (1993) Biosci. Biotech. Biochem., 57, 129.
(2) (1994) Dictionary of Natural Products, Chapman & Hall, London.

© 2005 by CRC Press LLC


374 Opender Koul

3,4-DIMETHOXYETHYLBENZENE C11H14O2
(187.22)
Only spectral data given

OCH3

OCH3

CH2

(1, 2) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Pieris rapae crucivora Boisd. Leaf disk 10–1 mol/l Feeding inhibition = Treatment to 5th
(Cabbage butterfly) dual-choice 77.3% instar larvae pre-
test or starved for 3 h.
Treatment duration =
5 × 10–7 2 h.
mol/cm2 (1)

(1) Yano, K. and Kamimura, H. (1993) Biosci. Biotech. Biochem., 57, 129.

© 2005 by CRC Press LLC


Insect Antifeedants 375

3,5-DIMETHOXYPHENOL C8H10O3
(154.16)
M.p. : 44.5°
(36–38°)

B.p. : 199°/36 mm
OH

H3CO OCH3

(1) (1, 2)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Acalymma vittatum (Fab.) Leaf disk 0.1% Feeding inhibition = Treatment to adult
(Striped cucumber beetle) choice test 100% up to 3 h beetles.
(1)

0.5% Feeding inhibition =


100% up to 22 h

(1) Reed, D.K. and Jacobson, M. (1983) Experientia, 39, 378.


(2) (1994) Dictionary of Natural Products, Chapman & Hall, London.

© 2005 by CRC Press LLC


376 Opender Koul

2,6-DIMETHOXYPHENOL C8H10O3
(154.16)
M.p. : 55–56°

B.p. : 262–267°

OH

H3CO OCH3

(1, 2) (1 ,2)

SOURCE: Synthetic
Also found naturally in the essential oil of Artemisia herba-alba var. densiflora Boisd. (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Acalymma vittatum (Fab.) Leaf disk 0.1% Feeding inhibition = Treatment to adult
(Striped cucumber beetle) choice test 100% up to 6 h beetles.
(1)

0.5% Feeding inhibition =


100% up to 22 h

(1) Reed, D.K. and Jacobson, M. (1983) Experientia, 39, 378.


(2) (1994) Dictionary of Natural Products, Chapman & Hall, London.

© 2005 by CRC Press LLC


Insect Antifeedants 377

3,4-DIMETHOXYPHENOL C8H10O3
(154.16)
M.p. : 79–82°

B.p. : 140–142°/0.1 mm

OH n25
D : 1.5331

OCH3

OCH3

(1) (1, 2)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Acalymma vittatum (Fab.) Leaf disk 0.5% Feeding inhibition = Treatment to adult
(Striped cucumber beetle) choice test 100% up to 24 h beetles.
(1)

(1) Reed, D.K. and Jacobson, M. (1983) Experientia, 39, 378.


(2) (1994) Dictionary of Natural Products, Chapman & Hall, London.

© 2005 by CRC Press LLC


378 Opender Koul

2,3-DIMETHOXYPHENOL C8H10O3
(154.16)
Oil

B.p. : 124–125°/17 mm

OH

OCH3

OCH3

(1, 2) (1, 2)

SOURCE: Synthetic (1)


Also isolated from trunkwood of Machaerium kuhlmannii Benth., jacranda (Fabaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Acalymma vittatum (Fab.) Leaf disk 0.1% Feeding inhibition = Treatment to adult
(Striped cucumber beetle) choice test 100% up to 3 h beetles.
(1)

0.5% Feeding inhibition =


100% up to 22 h

(1) Reed, D.K. and Jacobson, M. (1983) Experientia, 39, 378.


(2) (1994) Dictionary of Natural Products, Chapman & Hall, London.

© 2005 by CRC Press LLC


Insect Antifeedants 379

2,6-DIMETHOXY-4- (2-PROPENYL) PHENOL C11H14O3


(194.23)
Oil

OH B.p. : 166–168°/10 mm
(123–125°/2 mm)
H3CO OCH3

CH2

(1) (2)

SOURCE: Synthetic (1)


Also isolated from oil of Sassafras albidum (Nutt.) Nees, laurus sassafras roots (Lauraceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Acalymma vittatum (Fab.) Leaf disk 0.1% Feeding inhibition = Treatment to adult
(Striped cucumber beetle) choice test 100% up to 6 h beetles.
(1)

0.5% Feeding inhibition =


100% up to 6 h

(1) Reed, D.K. and Jacobson, M. (1983) Experientia, 39, 378.


(2) (1994) Dictionary of Natural Products, Chapman & Hall, London.

© 2005 by CRC Press LLC


380 Opender Koul

3,4-DIMETHOXYPROPYLBENZENE C11H16O2
(180.25)
Only spectral data given

OCH3

OCH3

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Pieris rapae crucivora Boisd. Leaf disk 10–1 mol/l Feeding inhibition = Treatment to 5th
(Cabbage butterfly) dual-choice 100% instar larvae pre-
test starved for 3 h.
Treatment duration =
2 h.
10–2 mol/l Feeding inhibition = (1)
35.3%

(1) Yano, K. and Kamimura, H. (1993) Biosci. Biotech. Biochem., 57, 129.

© 2005 by CRC Press LLC


Insect Antifeedants 381

4,6-DIMETHYL-3,7-p-ACETOXYPHENYL C30H22O8
-2,8-DIOXO-2H,8H-BENZODIPYRAN (510.47)
M.p. : 270°

O O O O

CH3OCO OCOCH3

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk no- Not Feeding inhibition = Treatment to 4th
(Tobacco armyworm) choice test recorded 83.01% instar larvae pre-
starved for 6 h.
(1)

(1) Ashok, D. and Sarma, P.N. (1987) Curr. Sci., 56, 234.

© 2005 by CRC Press LLC


382 Opender Koul

4,6-DIMETHYL-3,7-p-BROMOPHENYL C26H18O4Br2
-2,8-DIOXO-2H,8H-BENZODIPYRAN (554.23)
M.p. : 291°

O O O O

Br Br

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk no- Not Feeding inhibition = Treatment to 4th
(Tobacco armyworm) choice test recorded 98.57% instar larvae pre-
starved for 6 h.
(1)

(1) Ashok, D. and Sarma, P.N. (1987) Curr. Sci., 56, 234.

© 2005 by CRC Press LLC


Insect Antifeedants 383

4,6-DIMETHYL-3,7-p-CHLOROPHENYL C26H18O4Cl2
-2,8-DIOXO-2H,8H-BENZODIPYRAN (565.33)
M.p. : 285°

O O O O

R R

R = p-Cl or o-Cl

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk no- Not Feeding inhibition = Treatment to 4th
(Tobacco armyworm) choice test recorded 97.46% for instar larvae pre-
p-compound and starved for 6 h.
73.96% for (1)
o-compound

(1) Ashok, D. and Sarma, P.N. (1987) Curr. Sci., 56, 234.

© 2005 by CRC Press LLC


384 Opender Koul

1,3,O,O-DIMETHYL-1-DETIGLOYL- C29H40O7
3-DEACETYLSALANNIN (500.63)
Only spectral data given

OCH3 O
O

O
CH3O
H
O

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Leptinotarsa decemlineata Leaf disk 50 µg/cm2 Feeding inhibition = Treatment to freshly


(Say) choice test 95.0% molted 3rd instar
(Colorado potato beetle) larvae.
Disks examined
every 2 h until 95%
of control disks were
eaten.
Concentration = PC95
value.
(1)

(1) Yamasaki, R.B. and Klocke, J.A. (1989) J. Agric. Food Chem., 37, 1118.

© 2005 by CRC Press LLC


Insect Antifeedants 385

1,3,O,O-DIMETHYL-1-DETIGLOYL- C29H44O7
3-DEACETYL-20,21,22,23- (504.66)
Only spectral data given
TETRAHYDROSALANNIN

OCH3 O
O

O
CH3O
H
O

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Leptinotarsa decemlineata Leaf disk 100 µg/cm2 Feeding inhibition = Treatment to freshly
(Say) choice test 95.0% molted 3rd instar
(Colorado potato beetle) larvae.
Disks examined
every 2 h until 95%
of control disks were
eaten.
Concentration = PC95
value.
(1)

(1) Yamasaki, R.B. and Klocke, J.A. (1989) J. Agric. Food Chem., 37, 1118.

© 2005 by CRC Press LLC


386 Opender Koul

4,6-DIMETHYL-3,7-p-HYDROXYPHENYL C26H18O6
-2,8-DIOXO-2H,8H-BENZODIPYRAN (426.42)
M.p. : 310°

O O O O

HO OH

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk no- Not Feeding inhibition = Treatment to 4th
(Tobacco armyworm) choice test recorded 97.36% instar larvae pre-
starved for 6 h.
(1)

(1) Ashok, D. and Sarma, P.N. (1987) Curr. Sci., 56, 234.

© 2005 by CRC Press LLC


Insect Antifeedants 387

4,6-DIMETHYL-3,7-DIPHENYL-2,8- C26H18O4
DIOXO-2H,8H-BENZODIPYRAN (394.43)
M.p. : 278°

O O O O

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk no- Not Feeding inhibition = Treatment to 4th
(Tobacco armyworm) choice test recorded 61.75% instar larvae pre-
starved for 6 h.
(1)

(1) Ashok, D. and Sarma, P.N. (1987) Curr. Sci., 56, 234.

© 2005 by CRC Press LLC


388 Opender Koul

4,6-DIMETHYL-3,7-p-METHOXYDIPHENYL C28H22O6
-2,8-DIOXO-2H,8H-BENZODIPYRAN (454.48)
M.p. : 264°

O O O O

R R

R = p-OCH3 or o-OCH3

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk no- Not Feeding inhibition = Treatment to 4th
(Tobacco armyworm) choice test recorded 89.84% for instar larvae pre-
p-compound and starved for 6 h.
83.49% for (1)
o-compound

(1) Ashok, D. and Sarma, P.N. (1987) Curr. Sci., 56, 234.

© 2005 by CRC Press LLC


Insect Antifeedants 389

3,3′-DI-o-METHYLQUERCETIN C17H14O5
(298.28)
M.p. : 256°

OH O

OH

HO O

(1, 2) (1, 2)

SOURCE: Wedelia biflora (L.) DC., sami scandent shrub (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Anthonomus grandis Bohem. Paper disk 3.5% Feeding inhibition = Treatment to


(Boll weevil) choice test 50.0% weevils.
Data based on
punctures of
compound
impregnated
paper/number of
punctures of control
disks.
(1)

(1) Miles, D.H., Chittawong, V., Hedin, P.A., and Kokpol, V. (1993) Phytochemistry, 32, 1427.
(2) Yang, C.H., Braymer, H.D., Murphy, E.L., Chorney, W., Scully, N., and Wender, S.H. (1960) J. Org. Chem.,
25, 2063.

© 2005 by CRC Press LLC


390 Opender Koul

4,6-DIMETHYL-3,7-p-NITROPHENYL C26H18O8N2
-2,8-DIOXO-2H,8H-BENZODIPYRAN (486.44)
M.p. : >320°

O O O O

NO2 O2N

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk no- Not Feeding inhibition = Treatment to 4th
(Tobacco armyworm) choice test recorded 76.98% instar larvae pre-
starved for 6 h.
(1)

(1) Ashok, D. and Sarma, P.N. (1987) Curr. Sci., 56, 234.

© 2005 by CRC Press LLC


Insect Antifeedants 391

DIONCOPHYLLINE–A C24H27O3N
(377.48)
M.p. : 215°

[α]D20 : –14° (CHCl3)

NH

OH
H3CO

H3CO

(1, 2) (1, 2)

SOURCE: Triphyophyllum peltatum (Hutch et Dalz.) Airy Shaw and Dioncophyllum thollonii Baill.
(Dioncophyllaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera littoralis (Fab.) Artificial diet 0.4 mg/g Feeding inhibition = Treatment to larvae
(Egyptian cotton leaf worm) test 59% approximately of 75 to 85 mg body
weight for 3 days.
Data calculated from
Reference 2.
(2)

(1) Bringmann, G., Rubenacker, M., Jansen, J.R., Schetuzow, D., and Ake Assi, L. (1990) Tetrahedron Lett., 31,
639.
(2) Bringmann, G., Gramatzki, S., Grimm, C., and Proksch, P. (1992) Phytochemistry 31, 3821.

© 2005 by CRC Press LLC


392 Opender Koul

1,5-DIPHENYL-1-PENTANONE C17H18O
(238.31)
Only spectral data given

(1) (1)

SOURCE: Stellera chamaejasme L., Chinese Lang du (Thymelaeaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Aphis gossypii Glov. Coated leaf 2000 Feeding inhibition = Treatment to


(Cotton aphid) assay mg/litre 95.8% apterous adult aphids
up to 12 h.
1000 Feeding inhibition = (1)
mg/litre 86.0%

2. Schizaphis graminum Coated leaf 2000 Feeding inhibition = Treatment to


(Rondani) assay mg/litre 92.7% apterous adult aphids
(Wheat aphid) up to 12 h.
1000 Feeding inhibition = (1)
mg/litre 89.9%

(1) Ping, G, Taiping, H., Rong, G., Qui, C., and Shigui, L. (2001) Pest. Manag. Sci., 57, 307.

© 2005 by CRC Press LLC


Insect Antifeedants 393

1,5-DIPHENYL-2-PENTEN-1-ONE C17H16O
(236.31)
Only spectral data given

(1) (1)

SOURCE: Stellera chamaejasme L., Chinese Lang du (Thymelaeaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Aphis gossypii Glov. Coated leaf 2000 Feeding inhibition = Treatment to


(Cotton aphid) assay mg/litre 100.0% apterous adult aphids
up to 12 h.
1000 Feeding inhibition = (1)
mg/litre 92.4%

2. Schizaphis graminum (Rond.) Coated leaf 2000 Feeding inhibition = Treatment to


(Wheat aphid) assay mg/litre 100.0% apterous adult aphids
up to 12 h.
1000 Feeding inhibition = (1)
mg/litre 95.2%

(1) Ping, G, Taiping, H., Rong, G., Qui, C., and Shigui, L. (2001) Pest. Manag. Sci., 57, 307.

© 2005 by CRC Press LLC


394 Opender Koul

DIPLOPHYLLOLIDE–A C15H20O2
(232.32)
M.p. : 60–62°

[α]D27 : +18.6° (neat)

O
O

CH2

(1) (1, 2)

SOURCE: Eupatorium quadrangularae L., joe-pye-weed (Asteraceae); Diplophyllum albicans (L.) Dum.,
Liverwort (Bryophyta) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Atta cephalotes (L.) Rye flake 0.3 mg/ml Feeding inhibition = Treatment to adult
(Leaf cutter ant) forced or 69.7% workers.
choice test 6 µg/flake (1)
Data calculated from
Reference 1.

(1) Hubert, T.D., Okunade, A.L., and Weimer, D.F. (1987) Phytochemistry, 26, 1751.
(1) Benesova, V., Samek, Z., and Vasickova, S. (1975) Collect. Czech. Chem. Commun., 40, 1966.

© 2005 by CRC Press LLC


Insect Antifeedants 395

DITHYREANITRILE C13H14ON2S2
(278.40)
M.p. : 135°

S S

CN

(1) (1)

SOURCE: Dithyrea wislizenii Engelm., desert lily (Cruciferae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera frugiperda Leaf disk 1.0% Feeding ratio = 0.11 Treatment to larvae
(J.E. Smith) choice test starved overnight for
(Fall armyworm) 3 h.
Ratio below 0.2
considered as highly
deterrent.
(1)

2. Ostrinia nubilalis (Hubner) Leaf disk Feeding deterrent 2. Treatment to


(European corn borer) choice test larvae. No
quantitative data
recorded.
(1)

(1) Powell, R.G., Mikolajczak, K.L., Zilkowski, B.W., Lu, H.S.M., Mantus, E.K., and Clardy, J. (1991) Experi-
entia, 47, 304.

© 2005 by CRC Press LLC


396 Opender Koul

DJENKOLIC ACID C7H14O4N2S2


(254.33)
M.p. : 300–350° (dec.)

[α]D25 : –44.5° (HCl)

COOH COOH

H2N C H H2N C H

CH2 S CH2 S CH2

(1, 2) (1, 2)

SOURCE: Acacia sp. (Fabaceae) (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Locusta migratoria Glass fiber 1.0% of Feeding inhibition = Treatment to male 5th
migratoriodes disk test disk weight 61–90% instar nymphs.
(R & F) (3)
(Migratory locust)

(1) Van Veen, A.G. and Hijman, A.J. (1935) Rec. Trav. Chim., 54, 493.
(2) Armstrong, M.D. and du Vigneaud, V. (1947) J. Biol. Chem., 168, 373.
(3) Evans, C.S. and Bell, E.A. (1979) Phytochemistry, 18, 1807.

© 2005 by CRC Press LLC


Insect Antifeedants 397

DYMALOL C31H54O5
(506.76)
M.p. : 182–184°

H [α]D : +35° (CHCl3)

O
OH

H3COOC

OH

(1) (1)

SOURCE: Dysoxylum malabaricum Bedd. and ex CDC, white cedar (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk 1 µg/cm2 Feeding inhibition = Treatment to 3rd
(Tobacco armyworm) dual-choice 55.6% instar larvae for 24 h.
test (2)
5 µg/cm2 Feeding inhibition =
59.5% EC50 = 0.85 µg/cm2
Calculated from
10 µg/cm2 Feeding inhibition = Reference 2.
72.5%

50 µg/cm2 Feeding inhibition =


75.1%.

(1) Govindachari, T.R., Suresh, G., and Krishna Kumari, G.N. (1994) Phytochemistry, 37, 1127.
(2) Govindachari, T.R., Narasimhan, N.S., Suresh, G., Partho, P.D., Gopalakrishnan, G., and Krishna Kumari,
G.N. (1995) J. Chem. Ecol., 21, 1586.

© 2005 by CRC Press LLC


398 Opender Koul

EICOSANOIC ACID C20H40O2


(Arachidic acid) (312.54)
M.p. : 77°

B.p. : 203–205°/1 mm

HOOC

(1, 2, 3) (1, 2)

SOURCE: Synthetic (3)


Hibiscus syriacus L., rose-of-sharon (Malvaceae) (4)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Incisitermes minor (Hagen) Paper towel 0.05 mg/cm2 Feeding inhibition = 1. Treatment to 10 to
(Western drywood termite) disk test 40.0% 13 mg body weight
larvae for 6 days.
(3)

2. Anthonomus grandis Bohem. Plate 100 µg/ Feeding = 80% of 2. Treatment to adult
(Boll weevil) bioassay feeding site controls after 3 h and weevils.
87% after 6 h in (4)
males and 80% of
controls after 6 h in
females.

(1) Adams, N.K. and Dyer, J.W.W. (1925) J. Chem. Soc., 72.
(2) Bleyburg, W. and Ulrich, H. (1931) Ber., 64, 2512.
(3) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39.
(4) Bird, T.G., Hedin, P.A., and Burks, M.L. (1987) J. Chem. Ecol., 13, 1087.

© 2005 by CRC Press LLC


Insect Antifeedants 399

13-EICOSENOIC ACID C20H38O2


(310.52)
Only spectral data given

HOOC

(1, 2) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Incisitermes minor (Hagen) Paper towel 0.05 mg/cm2 Feeding inhibition = Treatment to 10 to
(Western drywood termite) disk test 26.5% 13 mg body weight
larvae for 6 days.
(2)

Data calculated from


Reference 2.

(1) Richter, I., Mukherjee, K. D., and Weber, N. (1978) Z. Naturforsch., 33C, 629.
(2) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39.

© 2005 by CRC Press LLC


400 Opender Koul

α-ELEOSTEARIC ACID C18H30O2


(278.44)
M.p. : 49–49.2°

HOOC

(1) (1)

SOURCE: Aleurites fordii Hemsl., tung tree (Euphorbiaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Anthonomus grandis grandis Cotton bud 1.0% Feeding inhibition = Treatment to 1- or 2-


Bohem. dip method 82.1% day-old boll weevils
(Boll weevil) for 4 h.

Data based on
punctures made on
buds in both treated
and control
situations.
(1)
Data calculated from
Reference 1.

(1) Jacobson, M., Crystal, M.M., and Warthen, J.D. Jr. (1981) J. Agric. Food Chem., 29, 591.

© 2005 by CRC Press LLC


Insect Antifeedants 401

ELLAGIC ACID C14H6O8


(302.19)
M.p. : >360°

OH O

HO OH

O OH

(1, 2) (1, 2)

SOURCE: Geranium viscosissium Fisch and Meyer, sticky geranium (Geraniaceae) (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Schizaphis graminum Artificial diet 15 ppm Feeding inhibition = 1. Treatment to


(Rondani) feeding 50.0% aphids at random.
(Wheat aphid)
(3)

2. Myzus persicae (Sulzer) Artificial diet 1500 ppm Not active up to this 2. Treatment to
(Green peach aphid) feeding level of treatment aphids at random.
(3)

(1) Perkin, A.G. and Nierenstein, M. (1905) J. Chem. Soc., 1415.


(2) Nierenstein, M. (1931) Helv. Chim. Acta, 14, 912.
(3) Jones, K.C. and Klocke, J.A. (1987) Entomol. Exp. Appl., 44, 229.

© 2005 by CRC Press LLC


402 Opender Koul

EMBELIN C17H26O4
(294.39)
Orange crystals

M.p. : 142–143°
145–146°
O

OH

HO

(1, 2) (2)

SOURCE: Rapanea melanphloes (L.) Mez., East African ethano-plant (Myrsinaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Schistocerca gregaria (Forsk.) Filter paper 100 µg/ml Feeding inhibition = Treatment to mid 5th
(Desert locust) no-choice 88.4% instar females pre-
assay starved for 24 h.

Treatment duration =
24 h.
(1)

(1) Midiwo, J.O., Mwangi, R.W., and Ghebremeskel, Y. (1995) Insect Sci. Applic., 16, 163.
(2) Dev, S. and Koul, O. (1997) Insecticides of Natural Origin, Harwood Academic Publishers, Amsterdam, p. 157.

© 2005 by CRC Press LLC


Insect Antifeedants 403

ENCECALIN C14H16O3
(232.27)
B.p. : 135–137°/0.11 mm

H3CO O

(1, 2) (1)

SOURCE: Encelia farinosa Gray, brittle bush (Asteraceae) (1)


Also in many other species of the desert sunflowers of genus Encelia, Ageratina, etc.

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Epilachana varivestis Muls. Leaf disk test 0.05 µmol/ Feeding inhibition = Treatment to 1- to
(Mexican bean beetle) leaf disk 50.0% 4-day-old insects for
20 to 24 h.

Concentration = FI50
value
(2)

(1) Sukh, Dev and Koul, O. (1997) Insecticides of Natural Origin, Harwood Academic Publishers, Amsterdam,
p. 193.
(2) Srivastava, R.P. and Proksch, P. (1990) Naturwissenschaften, 77, 438.

© 2005 by CRC Press LLC


404 Opender Koul

ENCELIN C15H16O3
(244.29)
M.p. : 195–196°

[α]26
D : –16.5° (CHCl3)

O
O

CH2 CH2

(1, 2) (1)

SOURCE: Encelia asperifolia (S.F. Blake) Clark and Kyhos, brittle bush (Asteraceae) (2)
Encelia actoni Elmer., acton encelia (Asteraceae)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera littoralis (Boisd) Artificial diet 1.0 µmol/g Feeding inhibition = Treatment to 2nd
(Egyptian cotton leaf worm) feeding significant instar larvae for
3 days.

No quantitative data
recorded.
(2)

(1) Geissman, T.A. and Mukherjee, R. (1968) J. Org. Chem., 33, 656.
(2) Srivastava, R.P., Proksch, P., and Wray, V. (1990) Phytochemistry, 29, 3445.

© 2005 by CRC Press LLC


Insect Antifeedants 405

ENHYDRIN C23H28O10
(464.47)
M.p. : 185–186°

O [α]D : –56.6° (CHCl3)


H3COOC

OOC
OAc

CH2
O
O

(1, 2) (1)

SOURCE: Polymnia uvedali L., bear’s foot (Asteraceae) (2)


Enhydra fluctuans Lour., weed (Asteraceae) (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera frugiperda Cellulose 1.0% Mean feeding Treatment to 4th


(J.E. Smith) millipore inhibition rating = instar larvae.
(Fall armyworm) filter disk test 7.1 mg Average deterrence
rating based on
(control-treated) disk
consumption.
(2)

(1) Kartha, G., Go, K.T., and Joshi, B.S. (1972) J. Chem Soc. Chem. Commun., 1327.
(2) Smith, C.M., Kester, K.M., and Fischer, N.H. (1983) Biol. Syst. Ecol., 11, 377.
(3) Joshi, B.S. (1976) J. Sci. Indus. Res., 35, 239.

© 2005 by CRC Press LLC


406 Opender Koul

ENTANDROPHRAGMIN C43H56O17
(844.91)
M.p. : 256°
O
[α]20 : –4°

COO
O
O O
O
O
OH
H3COOC
OCO

OH
OCO O

(1, 2) (1)

SOURCE: Entandrophragma spp. (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Ostrinia nubilalis (Hubner) Leaf disk test 50 µg/g Feeding inhibition = Treatment to neonate
(European corn borer) 73.0% larvae for 48 h.
(2)
500 µg/g Feeding inhibition =
75.0%

(1) Halsall, T.G., Wragg, K., Connolly, J.D., McLellan, M.A., Bredell, L.D., and Taylor, D.A.H. (1977) J. Chem.
Res. Synop., 154.
(2) Arnason, J.T., Philogene, B.J.R., Donskov., N., and Kubo, I. (1987) Entomol. Exp. Appl., 43, 221.

© 2005 by CRC Press LLC


Insect Antifeedants 407

ENT-3,13E-CLERODIEN-15-OIC ACID C20H32O2


(304.47)
Only spectral data given

COOH

(1) (1)

SOURCE: Detarium microcarpum Guill. & Perr., African atokolo (Caesalpiniaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Reticulitermes speratus Kolbe Paper disk 1.0% Feeding inhibition Treatment to 3rd
(Subterranean termite) choice or index value = < 5.0 instar workers.
bioassay 80 µg/cm2 Feeding duration =
14 days.
Antifeedant index
below 20 highly
active.
(2)

(1) Lajide, L., Escoubas, P., and Mizutani, J. (1995) Phytochemistry, 40, 1101.
(2) Lajide, L., Escoubas, P., and Mizutani, J. (1995) Phytochemistry, 40, 1105.

© 2005 by CRC Press LLC


408 Opender Koul

ENT-4 (18),13E-CLERODIEN-15-OIC ACID C20H32O2


(304.47)
Oil

[α]D : +10° (CHCl3)

COOH

CH2

(1) (1)

SOURCE: Detarium microcarpum Guill. & Perr., African atokolo (Caesalpiniaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Reticulitermes speratus Kolbe Paper disk 1.0% Feeding inhibition Treatment to 3rd
(Subterranean termite) choice or index value = < 5.0 instar workers.
bioassay 80 µg/cm2 Feeding duration =
14 days.
Antifeedant index
below 20 highly
effective.
(1)

(1) Lajide, L., Escoubas, P., and Mizutani, J. (1995) Phytochemistry, 40, 1101.

© 2005 by CRC Press LLC


Insect Antifeedants 409

ENTILIN–D C29H38O9
(530.61)
M.p. : 107–110°
(177–178°)
O
[α]20
D : –38.6° (CHCl3)

OAc
O
O
HO
O

OH

(1, 2) (1)

SOURCE: Entandrophragma utile (Dawe et Sprague) Sprague, utile (Meliaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius (L.) Wafer disk 10 mg/ml Feeding deterrence 1. Treatment given to
(Grain weevil) test coefficient = 78.6 adults.

2. Tribolium confusum Duv. Wafer disk 10 mg/ml Feeding deterrence 2. Treatment given to
(Confused flour beetle) test coefficient both adults and
Adults = 188.1 larvae.
Larvae = 180.0

3. Trogoderma granarium Wafer disk 10 mg/ml Feeding deterrence 3. Treatment given to


Everts test coefficient = 157.3 larvae.
(Khapra beetle)
Neutral value = 0
Absolute feeding
deterrence value =
200
(2)

(1) Daniewski, W.M., Ancezewski, W., Gumulka, M., Danikiewicz, W., Jacobson, U., and Norin, T. (1995)
Phytochemistry, 40, 903.
(2) Daniewski, W.M., Gumulka, M., Ancezewski, W., Truszewska, D., Bloszyk, E., and Drozdz, B. (1996) Polish
J. Chem., 70, 1265.

© 2005 by CRC Press LLC


410 Opender Koul

ENT-KAURADIENOIC ACID C20H28O2


(300.44)
M.p. : 171–172°

CH2

COOH

(1) (1)

SOURCE: Wedelia biflora (L.) DC., sami scandent shrub (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Anthonomus grandis grandis Agar plug 5.0 mg/plug Feeding inhibition = Treatment to newly
Bohem. bioassay 83.4% emerged boll weevils
(Boll weevil) in the dark at 80°F
for 4 h.

Plug size for


experiments
In dark = 1.3 cm
In light = 3.6 cm
(1)

(1) Miles, D.H., Chittawong, V., Payne, A.M., Hedin, P.A., and Kokpol, U. (1990) J. Agric. Food Chem., 38, 1591.

© 2005 by CRC Press LLC


Insect Antifeedants 411

3-EPICARYOPTIN C26H36O9
(492.56)
M.p. : 171–172°
O
[α]D : –70° (CHCl3)
H H

AcO
O CH2
OAc

OAc
(1) (1)

SOURCE: Clerodendron calamitosum L., clerodendron (Verbenaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk 200 ppm Feeding inhibition = Treatment to 3rd
(Tobacco armyworm) choice 100% within 2 h instar larvae.
bioassay Compound
considered to be
absolute antifeedant.
(2)

(1) Hosozawa, S., Kato, N., and Munakata, K. (1974) Phytochemistry, 13, 308.
(2) Hosozawa, S., Kato, N., Munakata, K., and Chen, Y. (1974) Agric. Biol. Chem., 38, 1045.

© 2005 by CRC Press LLC


412 Opender Koul

3-EPIDIHYDROCARYOPTIN C27H38O9
(506.59)

CH2
M.p. : 161–162°

O [α]D : –42° (CHCl3)

H H

AcO
O CH2
OAc

OAc (1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk 100 ppm Feeding inhibition = Treatment to 3rd
(Tobacco armyworm) choice 100% within 2 h instar larvae. Larvae
bioassay die within 24 h.
Compound
considered to be
absolute antifeedant.
(2)

(1) Hosozawa, S., Kato, N., and Munakata, K. (1974) Phytochemistry, 13, 308.
(2) Hosozawa, S., Kato, N., Munakata, K., and Chen, Y. (1974) Agric. Biol. Chem., 38, 1045.

© 2005 by CRC Press LLC


Insect Antifeedants 413

(+) EPIEUDESMIN C22H26O6


(386.44)
M.p. : 131–132°

[α]25
D : 130° (CHCl3)

O
O
O

O
O

(1) (1)

SOURCE: Parabenzoin praecox Nakai, Japanese parabenzoin (Lauraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk test 1.0% Feeding inhibition = Treatment to 3rd
(Tobacco armyworm) 90–100% instar larvae for 2 h.
(1)
0.05% Feeding inhibition =
90–100%

0.01% Feeding inhibition =


50–70%

(1) Matsui, K., Wada, K., and Munakata, K. (1976) Agric. Biol. Chem., 40, 1045.

© 2005 by CRC Press LLC


414 Opender Koul

EPILIMONOL C26H32O8
(472.51)
M.p. : 262–266°

[α]D : +9° (Acetone)


O
O

O O

O
O O

OH

(1, 2) (1)

SOURCE: Synthetic (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Leptinotarsa decemlineata Leaf disk 100 µg/cm2 Feeding inhibition = 1. Treatment to 4th
(Say) bioassay 98.5% instar larvae for
(Colorado potato beetle) 6–8 h.
31.7 µg/cm2 Feeding inhibition = (2)
84.9%
FI50 = 8.84 µg/cm2
10.0 µg/cm2 Feeding inhibition = Calculated from
53.9% Reference 2.

3.17 µg/cm2 Feeding inhibition =


19.3%

2. Spodoptera frugiperda Glass-fiber 100 ppm Feeding inhibition = 2. Treament to 24- to


(J.E. Smith) disk test 56.0% 36-h-old last stadium
(Fall armyworm) larvae for 8 h. The
larvae were pre-
starved for 2 h.

(3)

(1) Barton, D.H.R., Pradhan, S.K., Sternhell, S., and Templeton, J.F. (1961) J. Chem. Soc., 255.
(2) Bentley, M.D., Rajab, M.S., Alford, A.R., Mendel, M.J., and Hassanali, A. (1988) Entomol. Exp. Appl., 49, 189.
(3) Ruberto, G., Renda, A., Tringali, C., Napoli, E.M., and Simmonds, M.S.J. (2002) J. Agric. Food Chem., 50,
6766.

© 2005 by CRC Press LLC


Insect Antifeedants 415

EPILIMONOL ACETATE C28H34O9


(514.54)
M.p. : 298–301°

O
O

O O

O
O O

OAc

(1, 2) (1)

SOURCE: Synthetic (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Leptinotarsa decemlineata Leaf disk 100 µg/cm2 Feeding inhibition = Treatment to 4th
(Say) bioassay 97.5% instar larvae for
(Colorado potato beetle) 6–8 h.
31.7 µg/cm2 Feeding inhibition = (2)
86.1%
FI50 = 10.49 µg/cm2
10.0 µg/cm2 Feeding inhibition = Calculated from
53.8% Reference 2.

3.17 µg/cm2 Feeding inhibition =


9.5%

(1) Barton, D.H.R., Pradhan, S.K., Sternhell, S., and Templeton, J.F. (1961) J. Chem. Soc., 255.
(2) Bentley, M.D., Rajab, M.S., Alford, A.R., Mendel, M.J., and Hassanali, A. (1988) Entomol. Exp. Appl., 49, 189.

© 2005 by CRC Press LLC


416 Opender Koul

12-EPI-TEUCVIN C19H20O5
(328.36)
M.p. : 197–199°
O
[α]D : +222.6° (CHCl3)

O
O
(1, 2) (1)

SOURCE: Teucrium flavum glaucum L., geber germander (Labiatae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera littoralis (Boisd.) Glass fiber 100 ppm Feeding inhibition = Treatment to final
(Egyptian cotton leaf worm) disk choice 49.9% stadium larvae
bioassay 10 ppm Feeding inhibition = starved for 4 h.
45.4% Treatment duration =
maximum of 18 h so
2. Helicoverpa armigera Glass fiber 100 ppm Feeding inhibition = that never more than
(Hubner) disk choice 29.6% 50% of any disk was
(Gram pod borer) bioassay 10 ppm Feeding inhibition = consumed.
29.2% (2)

(1) Fayos, J., Fernandez-Gadea, F., Pascual, C., Perales, A., Piozzi, F., Rico, M., Rodriguez, B., and Savona, G.
(1984) J. Org. Chem., 49, 1789.
(2) Simmonds, M.S.J., Blaney, W.M., Ley, S.V., Savona, G., Bruno, M., and Rodriguez, B. (1989) Phytochemistry,
28, 1069.

© 2005 by CRC Press LLC


Insect Antifeedants 417

14-EPOXYAZADIRADIONE C28H34O6
(466.57)
M.p. : 202–204°

[α]D : +45° (CHCl3)


O

O OAc

(1, 2, 3) (1)

SOURCE: Azadirachta indica A. Juss., neem (Meliaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Epilachna varivestis Muls. Bean leaf 0.14% Feeding inhibition = Treatment to 4th
(Mexican bean beetle) choice 50.0% stadium larvae for up
bioassay to 24 h.
Concentration = EC50
value.
(2)

2. Spodoptera litura (Fab.) Leaf disk 1 µg/cm2 Feeding inhibition = 2. Treatment to 3rd
(Tobacco armyworm) dual choice 51.5% instar larvae for 24 h.
bioassay 5 µg/cm2 Feeding inhibition = (3)
61.4%
10 µg/cm2 Feeding inhibition = FI50 = 0.66 µg/cm2
64.8% Calculated from
50 µg/cm2 Feeding inhibition = Reference 3.
73.0%

(1) Lavie, D., Levy, E.C., and Jain, M.K. (1971) Tetrahedron, 27, 3927.
(2) Schwinger, M., Ehhammer, B., and Kraus, W. (1984) In H. Schmutterer and K.R.S. Ascher (eds.), Proc. 2nd
Int. Neem Conf., Rauischholzhausen, GTZ, Eschborn, Germany, pp. 181–189.
(3) Govindachari, T.R., Narasimhan, N.S., Suresh, G., Partho, P.D., Gopalakrishnan, G., and Krishna Kumari,
G.N. (1995) J. Chem. Ecol., 21, 1586.

© 2005 by CRC Press LLC


418 Opender Koul

19β,28-EPOXY-2 (β-D-GLUCO-PYRANO C36H57O8


SYLOXY)-18-α-OLEAN-1-EN-3-ONE (617.84)
M.p. : 157–158°

GluO

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Heliothis zea (Boddie.) Leaf disk 3.17 µg/cm2 Feeding inhibition = Treatment to 4th
(Corn earworm) choice 40.0% stadium larvae for up
bioassay to 19–22 h.
(1)

10 µg/cm2 Feeding inhibition = FI50 = 3.48 µg/cm2


83.0% Calculated from
Reference 1.

100 µg/cm2 Feeding inhibition =


92.0%

(1) Lugemwa, F.N., Huang, F., Bentley, M.D., Mendel, M.J., and Alford, A.R. (1990) J. Agric. Food Chem., 38,
493.

© 2005 by CRC Press LLC


Insect Antifeedants 419

5β,6β-EPOXY-1β,14α,17β,20-TETRA C28H40O7
HYDROXY WITH-24-ENOLIDE (488.61)
No physical data given

OH

O O
OH
OH

OH

O
(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera littoralis (Boisd.) Styropor Feeding inhibition = 1. Treatment to


(Egyptian cotton leaf worm) test larvae of 170–190
0.1% 98.5% mg body weight.
(1)
0.01% 91.0%
FI50 = 0.0019%
0.005% 86.3% Data calculated from
Reference 1.
0.0025% 54.6%

0.0001% 40.7%

2. Epilachna varivestis Muls. Leaf 0.1% Weight gain = − 1.22 mg 2. Treatment to 4th
(Mexican bean beetle) residue test versus control = 12.1 mg instar larvae for 48 h.
0.05% Weight gain = − 1.76 mg Data based on
versus control = 11.5 mg growth rate.
(2)

(1) Ascher, K.R.S., Nemny, N.E., Eliyahu, M., Kirson, I., Abraham, A., and Glotter, E. (1980) Experientia, 36, 998.
(2) Ascher, K.R.S., Schmutterer, H., Glotter, E., and Kirson, I. (1981) Phytoparasitica, 9, 197.

© 2005 by CRC Press LLC


420 Opender Koul

α-ERGOCRYPTINE C32H41O5N5
(575.71)
M.p. : 211–212° (dec.)

OH [α]20
D : –198° (CHCl3)
O
O
N

N N
O O

N
(1, 2) (1)

SOURCE: Commercial sample (2)


Also obtained from Lolium perenne L. (rye grass) infected with fungus Neotyphodium Lolii.

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Heteronychus arator (Fab.) Artificial diet 5 µg/g Feeding inhibition = Treatment to adult
(Black beetle) choice test 47.1% beetles for 96 h.
(2)

10 µg/g Feeding inhibition = Data calculated from


60.0% Reference 2.

LD50 (rats): 0.95 mg/kg (ivn.) (3)

(1) Schlientz, W., Brunner, R., Ruegger, A., Berde, B., Stuermer, E., and Hofmann, A. (1968) Pharm. Acta Helv.,
43, 497.
(2) Ball, O.J.-P., Miles, C.O., and Prestidge, R.A. (1997) J. Econ. Entomol., 90, 1382.
(3) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC


Insect Antifeedants 421

ERGONOVINE C19H23O2N3
(325.41)
M.p. : 162–163° (dec.)
(212°, dec.,
HO dimorph.)
O

NH

(1, 2) (1)

SOURCE: Commercial sample (2)


Also obtained from Lolium perenne L. (rye grass) infected with fungus Neotyphodium Lolii.

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Heteronychus arator (Fab.) Artificial diet 10 µg/g Feeding inhibition = Treatment to adult
(Black beetle) choice test 40.0% beetles for 96 h.
(2)

Data calculated from


Reference 2.

LD50 (mice): 144 mg/kg (ivn.) (3)

(1) Jacobs, W.A. and Craig, L.C. (1935) Science, 82,16.


(2) Ball, O.J.-P., Miles, C.O., and Prestidge, R.A. (1997) J. Econ. Entomol., 90, 1382.
(3) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC


422 Opender Koul

α-ERGOSINE C30H37O5N5
(547.65)
M.p. : 228° (dec.)
OH
[α]20
D : –161° (CHCl3)
O
O
N

N N
O O

(1, 2,3) (1, 2)

SOURCE: Commercial sample (3)


Also obtained from Lolium perenne L. (rye grass) infected with fungus Neotyphodium Lolii.

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Heteronychus arator (Fab.) Artificial diet 5 µg/g Feeding inhibition = Treatment to adult
(black beetle) choice test 69.2% beetles for 96 h.
(3)
10 µg/g Feeding inhibition =
75.8% Data calculated from
Reference 3.
20 µg/g Feeding inhibition =
81.3%

(1) Smith, S. and Timmis, G.M. (1937) J. Chem. Soc., 396.


(2) Stauffacher, D., Tscherter, H., and Hofmann, A. (1965) Helv. Chim. Acta, 48, 1379.
(3) Ball, O.J.-P., Miles, C.O., and Prestidge, R.A. (1997) J. Econ. Entomol., 90, 1382.

© 2005 by CRC Press LLC


Insect Antifeedants 423

ERGOTAMINE C33H35O5N5
(581.67)
M.p. : 213–214° (dec.)
OH
[α]20
D : –160° (CHCl3)
O
O N

N N
O O

(1, 2) (1)

SOURCE: Commercial sample (2)


Also obtained from Lolium perenne L. (rye grass) infected with fungus Neotyphodium Lolii.

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Heteronychus arator (Fab.) Artificial diet 5 µg/g Feeding inhibition = Treatment to adult
(Black beetle) choice test 53.8% beetles for 96 h.
(2)
10 µg/g Feeding inhibition =
60.0% Data calculated from
Reference 2.
20 µg/g Feeding inhibition =
85.7%

(1) Stoll, A., Hofmann, A., and Petrzilka, Th. (1951) Helv. Chim. Acta, 34, 1544.
(2) Ball, O.J.-P., Miles, C.O., and Prestidge, R.A. (1997) J. Econ. Entomol., 90, 1382.

© 2005 by CRC Press LLC


424 Opender Koul

ERGOVALINE C29H35O5N5
(533.63)
M.p. : 207–208° (dec.)
OH
[α]20
D : –172° (CHCl3)
O
O
N

N N
O O

(1, 2) (1)

SOURCE: Commercial sample (2)


Also obtained from Lolium perenne L. (rye grass) infected with fungus Neotyphodium Lolii.

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Heteronychus arator (Fab.) Artificial diet 5 µg/g Feeding inhibition = Treatment to adult
(Black beetle) choice test 42.9% beetles for 96 h.
(2)
10 µg/g Feeding inhibition =
73.9% Data calculated from
Reference 2.

(1) Brunner, R., Stuetz, P.L., Tscherter, H., and Stadler, P.A. (1979) Can. J. Chem., 57, 1638.
(2) Ball, O.J.-P., Miles, C.O., and Prestidge, R.A. (1997) J. Econ. Entomol., 90, 1382.

© 2005 by CRC Press LLC


Insect Antifeedants 425

ERIOCEPHALIN C24H30O9
(462.50)
M.p. : 197–200°
O
[α]20
D : +76.1° (CHCl3)

OAc

OH
O
O
OAc

(1, 2) (1)

SOURCE: Teucrium eriocephalum, germander (Labiatae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera littoralis (Boisd.) Glass fiber 100 ppm Feeding inhibition = 1, 2. Treatment to
(Egyptian cotton leaf worm) disk choice 48.9% final stadium larvae
bioassay 10 ppm Feeding inhibition = starved for 4 h.
40.9% Treatment duration =
2. Helicoverpa armigera Glass fiber 100 ppm Feeding inhibition = maximum of 18 h so
(Hubner) disk choice 23.9% that never more than
(Gram pod borer) bioassay 10 ppm Feeding inhibition = 50% of any disk was
24.0% consumed.
(2)

3. Leptinotarsa decemlineata Leaf disk 1000 ppm Feeding inhibition = 3. Treatment to 4th
(Say) choice test 23.8% instar larvae for 4 h
(Colorado potato beetle) in no-choice assay
Leaf disk no- 1000 ppm Feeding inhibition = and for up to 24 h or
choice test 60.1% until 50% of disks
were consumed in
choice situation.
(3)

(1) Piozzi, F. (1981) Heterocycles, 15, 1489.


(2) Simmonds, M.S.J., Blaney, W.M., Ley, S.V., Savona, G., Bruno, M., and Rodriguez, B. (1989) Phytochemistry,
28, 1069.
(3) Ortego, F., Rodriguez, B., and Castanera, P. (1995) J. Chem. Ecol., 21, 1375.

© 2005 by CRC Press LLC


426 Opender Koul

ERIODICTYOL C15H12O6
(288.25)
M.p. : 257° (dec.)
OH OH

HO O

OH O

(1, 2) (1)

SOURCE: Eriodictyon californicum (Hook and Arn.) Torr., bear’s weed (Hydrophyllaceae) (1)
Semisynthetic as well (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Schizaphis graminum Artificial diet 0.02% Feeding inhibition = 1. Treatment to 50 to


(Rondani) feeding 50.0% 75 aphids at random.
(Wheat aphid) (2)

2. Myzus persicae (Sulzer) Artificial diet 0.02% Feeding inhibition = 2. Treatment to 50 to


(Green peach aphid) feeding 50.0% 75 aphids at random.
(2)

(1) Geissman, T.A. (1940) J. Am. Chem. Soc., 62, 3258.


(2) Dreyer, D.L. and Jones, K.C. (1981) Phytochemistry, 20, 2489.

© 2005 by CRC Press LLC


Insect Antifeedants 427

ERIVANIN C15H22O4
(266.34)
M.p. : 203–205°

[α]20
D : +112° (EtOH)
OH

HO

CH2
O

(1) (1)

SOURCE: Chrysanthemum balsamita L., costmary (Asteraceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius (L.) Wafer disk 10 mg/cm3 Feeding deterrence Treatment given to
(Grain weevil) test coefficient = 98.2 adults.

2. Tribolium confusum Duv. Wafer disk 10 mg/cm3 Feeding deterrence Treatment given to
(Confused flour beetle) test coefficient = both adults and
132.1 (adults) larvae.
81.0 (larvae)

3. Trogoderma granarium Wafer disk 10 mg/cm3 Feeding deterrence Treatment given to


Everts test coefficient = 79.8 larvae.
(Khapra beetle)
Neutral value = 0
Absolute feeding
deterrence value =
200
(2)

(1) Evstratova, R.I., Sheichenko, V.I., Bankovskii, A.I., and Rybalko, K.S. (1969) Khim. Prir. Soedin., 5, 239.
(2) Nawrot, J., Bloszyk, E., Grabarczyk, H., Dorzdz, B., Daniewski, W.M., and Holub, M. (1983) Prace. Nauk.
Inst. Ochr. Roslin., 25, 91.

© 2005 by CRC Press LLC


428 Opender Koul

ERMANIN C17H14O6
(314.29)
M.p. : 235°

OH O

OCH3

HO O

OCH3

(1, 2) (1, 2)

SOURCE: Passiflora foetida L., passionflower weed (Passifloraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Dione juno (Stoll) Plant lobule 40 ppm Feeding deterrence = Treatment to 3rd
(Silverspot butterfly) choice test Significant instar larvae pre-
starved for 12 h.
(1)

No quantitative data
recorded.

(1) Echeverri, F., Cardona, G., Torres, F., Pelaez, C., Quinones, W., and Renteria, E. (1991) Phytochemistry, 30,
153.
(2) Wollenweber, E. and Mann, K. (1984) Z. Naturforsch., 39, 303.

© 2005 by CRC Press LLC


Insect Antifeedants 429

ERYTHRO-9,10-DIHYDROXY-1- C20H40O4
OCTADECANOL ACETATE (344.54)
M.p. : 54°

AcO

OH

OH

(1) (1)

SOURCE: Aleurites fordii Hensl., tung tree (Euphorbiaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Anthonomus grandis grandis Cotton bud 1.0% Feeding deterrence = Treatment to 1- or 2-


Bohem dip test 66.7% day-old boll weevils
(Boll weevil) for 4 h.
Data based on
punctures observed
in test material
versus controls.
(1)

(1) Jacobson, M., Crystal, M.M., and Warthen, J.D. Jr. (1981) J. Agric. Food Chem., 29, 591.

© 2005 by CRC Press LLC


430 Opender Koul

15-ETHOXY-14-HYDRO AJUGAPTIN C31H48O11


OC2H5
(596.71)
[α]20
D : –3.53° (CHCl3)

H H

O
H
H
HO

COO
O CH2
OAc

OAc (1) (1)

SOURCE: Ajuga chamaepitys (L.) Schreb., ground pine (Labiatae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera littoralis (Boisd.) Leaf disk 10 µg/cm2 Feeding ratio = Treatment to newly
(Egyptian cotton leaf worm) choice test 0.11 ± 0.03 ecdysed 5th instar
larvae.
1 µg/cm2 Feeding ratio = Data based on the
0.39 ± 0.07 ratio when 50% of
control disk area was
consumed and
represents FR50
value.
FR50 value < 0.5 is
excellent antifeedant
activity.
(2)

(1) Camps, F., Coll, J., and Dargallo, O. (1984) Phytochemistry, 23, 2577.
(2) Belles, X., Camps, F., Coll, J., and Piulachs, M.D. (1985) J. Chem. Ecol., 11, 1439.

© 2005 by CRC Press LLC


Insect Antifeedants 431

24-ETHYLCOPROSTANONE C29H50O
(414.72)
M.p. : 113–114°

(1) (1)

SOURCE: Wedelia biflora (L.) DC., sami scandent shrub (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Anthonomus grandis grandis Agar plug 2.0 Feeding inhibition = Treatment to newly
Bohem. bioassay mg/plug 90.0% emerged boll weevils
(Boll weevil) in the dark at 80°F
for 4 h.

Plug size for


experiments
In dark = 1.3 cm
In light = 3.6 cm
(1)

(1) Miles, D.H., Chittawong, V., Payne, A.M., Hedin, P.A., and Kokpol, U. (1990) J. Agric. Food Chem., 38, 1591.

© 2005 by CRC Press LLC


432 Opender Koul

EUDESMENE C15H20O2
(232.32)
Oily solid

CH2

HO O

(1) (1)

SOURCE: Helianthus annuus L., sunflower (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Diabrotica virgifera virgifera Leaf disk 4.0 µg/1.5 cm2 Feeding inhibition = Treatment to adults.
LeConte bioassay 47% reduction in (1)
(Western corn rootworm) consumption after 5
h and 25% reduction
in consumption after
24 h.

(1) Alfatafta, A.A. and Mullin, C.A. (1992) Phytochemistry, 31, 4109.

© 2005 by CRC Press LLC


Insect Antifeedants 433

(+) EUDESMIN C22H26O6


(386.44)
M.p. : 107–108°
H3CO

[α]20
D : + 60.5° (Me2CO)

O
H3CO

H H

OCH3

OCH3

(1) (2)

SOURCE: Parabenzoin praecox Nakai, Japanese parabenzoin (Lauraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk 1.0% Feeding inhibition = Treatment to 3rd
(Tobacco armyworm) choice test 90–100% instar larvae.
(1)
0.5% Feeding inhibition =
70–90%

0.1% No activity

(1) Matsui, K., Wada, K., and Munakata, K. (1976) Agric. Biol. Chem., 40, 1045.
(2) (1982) Dictionary of Organic Compounds, Vol. 3, Chapman & Hall, New York, p. 2581.

© 2005 by CRC Press LLC


434 Opender Koul

EUGENOL C10H12O2
(164.20)
M.p. : –9°

CH2 B.p. : 254°

n19
D : 1.5439

d25
4 : 1.0620

CH3O

OH

(1, 2) (1)

SOURCE: Commercial sample (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Pieris brassicae (L.) Leaf disk 6.6 × 10–2 M Feeding ratio = 9.95 Treatment to 2nd day
(Large white butterfly) no-choice 5th instar unstarved
test Considered as strong larvae. Ratio based
deterrence on control/treated
insects
(2)

LD50 (rats): 2680 mg/kg (oral) (3)

(1) Dev, S. and Koul, O. (1997) Insecticides of Natural Origin, Harwood Academic Publishers, Amsterdam, p. 152.
(2) Jones, C.G. and Firn, R.D. (1979) Biochem. Syst. Ecol., 7, 187.
(3) Hagan, E.C., Jenner, P.M., Jones, W.I., Fitzhugh, O.G., Long, E.L., Brouwer, J.G., and Webb, W.K. (1965)
Toxicol. Appl. Pharmacol., 7, 18.

© 2005 by CRC Press LLC


Insect Antifeedants 435

EUPATOLIDE C15H20O3
(248.32)
M.p. : 185–188°

[α]22
D : +20° (Acetone)

OH

CH2

O
O

(1) (2)

SOURCE: Synthetic (1, 3)


(also isolated from Eupatorium formosanum Hayata, bugleweed, E. cannabinum L.,
common water hemp; Asteraceae)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius (L.) Wafer disk 10 mg/ml Feeding deterrence Treatment given to
(Grain weevil) test coefficient = 54 adults.

2. Tribolium confusum Duv. Wafer disk 10 mg/ml Feeding deterrence Treatment given to
(Confused flour beetle) test coefficient = both adults and
97.0 (adults) larvae.
36.0 (larvae)

3. Trogoderma granarium Wafer disk 10 mg/ml Feeding deterrence Treatment given to


Everts test coefficient = 98.0 larvae.
(Khapra beetle)
Neutral value = 0
Absolute feeding
deterrence value =
200
(3)

(1) Harmatha, J., and Samek, Z. (1982) Collect. Czech. Chem. Commun., 47, 2779.
(2) Sukh, Dev and Koul, O. (1997) Insecticides of Natural Origin, Harwood Academic Publishers, Amsterdam,
p. 84.
(3) Harmatha, J. and Nawrot, J. (1984) Biochem. Syst. Ecol., 12, 95.

© 2005 by CRC Press LLC


436 Opender Koul

METHOXY EUPATOLIDE C16H23O3


(263.36)
No physical data given

OH

OCH3

(1) (2)

SOURCE: Synthetic (1, 3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius (L.) Wafer disk 10 mg/ml Feeding deterrence Treatment given to
(Grain weevil) test coefficient = 109 adults.

2. Tribolium confusum Duv. Wafer disk 10 mg/ml Feeding deterrence Treatment given to
(Confused flour beetle) test coefficient = both adults and
124.0 (adults) larvae.
89.0 (larvae)

3. Trogoderma granarium Wafer disk 10 mg/ml Feeding deterrence Treatment given to


Everts test coefficient = 69.0 larvae.
(Khapra beetle)
Neutral value = 0
Absolute feeding
deterrence value =
200
(3)

(1) Harmatha, J. and Samek, Z. (1982) Collect. Czech. Chem. Commun., 47, 2779.
(2) Harmatha, J. and Nawrot, J. (1984) Biochem. Syst. Ecol., 12, 95.

© 2005 by CRC Press LLC


Insect Antifeedants 437

DIETHYL NITRO EUPATOLIDE C20H30O2N


(316.47)
Only spectral data given

OH

(1, 2) (1, 2)

SOURCE: Synthetic (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius (L.) Wafer disk 10 mg/ml Feeding deterrence Treatment given to
(Grain weevil) test coefficient = 68 adults.

2. Tribolium confusum Duv. Wafer disk 10 mg/ml Feeding deterrence Treatment given to
(Confused flour beetle) test coefficient = both adults and
119.0 (adults) larvae.
109.0 (larvae)

3. Trogoderma granarium Wafer disk 10 mg/ml Feeding deterrence Treatment given to


Everts test coefficient = 156.0 larvae.
(Khapra beetle)
Neutral value = 0
Absolute feeding
deterrence value =
200
(2)

(1) Harmatha, J. and Samek, Z. (1982) Collect. Czech. Chem. Commun., 47, 2779.
(2) Harmatha, J. and Nawrot, J. (1984) Biochem. Syst. Ecol., 12, 95.

© 2005 by CRC Press LLC


438 Opender Koul

EUPATORIOPICRIN C20H26O7
(378.42)
M.p. : 157–161°

[α]20
D : +95° (CHCl3)
O

O
CH2
HO OH

O
OH

(1, 2) (1, 2)

SOURCE: Eupatorium cannabinum L., common water hemp (Asteraceae) (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius (L.) Wafer disk 8 mg/cm3 Feeding deterrence Treatment given to
(Grain weevil) test coefficient = adults.
101–150

2. Tribolium confusum Duv. Wafer disk 8 mg/cm3 Feeding deterrence Treatment given to
(Confused flour beetle) test coefficient = both adults and
151–200 (adults) larvae.
101–150 (larvae)

3. Trogoderma granarium Wafer disk 8 mg/cm3 Feeding deterrence Treatment given to


Everts test coefficient = larvae.
(Khapra beetle) 151–200
Neutral value = 0
Absolute feeding
deterrence value =
200
(3)

(1) Dolejs, L. and Herout, V. (1962) Collect. Czech. Chem. Commun., 27, 2654.
(2) Kupchan, S.M., Kelsey, J.E., and Sim, G.A. (1967) Tetrahedron Lett., 2863.
(3) Nawrot, J., Bloszyk, E., Grabarczyk, H., and Drozdz, B. (1982) Prace. Nauk. Inst. Ochr. Roslin, 24, 27.

© 2005 by CRC Press LLC


Insect Antifeedants 439

EVOXINE C18H21O6N
(347.37)
M.p. : 151–152°

OCH3 [α]22
D : +14.6° (EtOH)

O N O

HO OCH3

OH

(1) (1)

SOURCE: Oryxa japonica Thumb., Japanese kokusagi (Rutaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk 500 ppm Feeding inhibition = Treatment to 3rd
(Tobacco armyworm) choice test 50.0% instar larvae.
(1)

(1) Yajima, T., Kato, N., and Munakata, K. (1977) Agric. Biol. Chem., 41, 1263.

© 2005 by CRC Press LLC


440 Opender Koul

FENTIN ACETATE C20H18O2Sn


(409.04)
M.p. : 121-122°

CH3OCO.Sn

(1, 2) (1)

SOURCE: Commercial formulation (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Musca domestica vicina L. Artificial diet 33 ppm Due to starvation 1. Treatment to


(Housefly) feeding only 15 pupae were larvae at random in
formed against 438 breeding media.
in controls. (2)

2. Spodoptera littoralis (Boisd.) Leaf disk 0.058% Feeding inhibition = 2. Treatment to


(Egyptian cotton leaf worm) choice test 95.0% 170–190 mg body
weight larvae.
(3)

3. Gnorimoschema operculella Leaf dip test .05% Feeding inhibition = 3. Treatment to 2nd
(Zell.) 38.5% instar larvae. Data
(Potato tuber moth) calculated from
Reference 3.
(3)

4. Scolytus mediterraneus Twig dip test 0.2% AI Twig penetration = 4. Treatment to 0 to


Eggers 9% 1-day-old females.
(Bark beetle) (4)
0.1% AI Twig penetration =
26%

0.01% AI Twig penetration =


68%

5. Boarmia selenaria Leaf dip test 0.1 g/l AI Only 7.9 pupae 5. Treatment to
(Denis & Schiff.) formed due to larvae at random.
(Giant looper) starvation (5)

© 2005 by CRC Press LLC


Insect Antifeedants 441

6. Spodoptera litura (Fab.) Leaf dip test 0.058% Feeding inhibition = 6. Treatment to 4th
(Tobacco armyworm) 95.0% instar larvae. Data
calculated on the
basis of leaf
protection.
(6)

7. Chilo agamemnon Blesz. Leaf disk test 0.05% Feeding inhibition = 7. Treatment to
(Striped maize borer) 74.7% larvae for 72 h.
(7)

Data calculated from


Reference 7.

LD50 (rats): 140–298 mg/kg (oral) (8)

(1) Ingham, R.K., Rosenberg, S.D., and Gilman, H. (1960) Chem. Rev., 60, 459.
(2) Ascher, K.R.S. and Moscowitz, J. (1968) Int. Pest Contr., 10, 10.
(3) Ascher, K.R.S., Avdat, N., and Kamhi, J. (1970) Int. Pest Contr., 12, 11.
(4) Ascher, K.R.S., Gurevitz, E., Renneh, S., and Nemny, N.E. (1975) Z. Pflkrankh. PflSchutz., 82, 378.
(5) Ascher, K.R.S., Nemny, N.E., Wysoki, M., and Gur-Telzak, L. (1978) Pestic. Sci., 9, 566.
(6) Ascher, K.R.S. and Nissim, S. (1965) Int. Pest Contr., 7, 21.
(7) Meisner, J. and Ascher, K.R.S. (1965) Z. Pflkrankh. PflPath. Pflschutz., 72, 458.
(8) Farms Chem. Handbook (1982) Meister Publishing Co., C300.

© 2005 by CRC Press LLC


442 Opender Koul

FENTIN CHLORIDE C18H15SnCl


(385.50)
M.p. : 105.5–107°

B.p. : 249°/13.5 mm

Cl Sn

(1, 2) (1)

SOURCE: Commercial formulation (2, 3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Boarmia selenaria Leaf dip test 0.1 g /l No larva reached to 1. Treatment to


(Denis & Schiff.) pupal stage due to larvae at random
(Giant looper) starvation (2)

2. Tribolium confusum Duv. Wheat flour 25 µmol/kg Larval weight was 2. Treatment to 0- to
(Confused flour beetle) mixture only 24% of controls 3–h-old larvae.
feeding due to antifeedant (3)
efect.

50 µmol/kg < 5% weight than


controls

LD50 (mice): 8 mg/kg (oral) (4)

(1) Ingram, R.K., Rosenberg, S.D., and Gilman, H. (1960) Chem. Rev., 60, 459.
(2) Ascher, K.R.S., Nemny, N.E., Wysoki, M., and Gur-Telzak, L. (1978) Pestic. Sci., 9, 566.
(3) Ishaaya, I., Ascher, K.R.S., and Yablonski, S. (1982) Phytoparasitica, 10, 205.
(4) Farms Chem. Handbook (1982) Meister Publishing Co., C288.

© 2005 by CRC Press LLC


Insect Antifeedants 443

FENTIN HYDROXIDE C18H16Osn


(367.04)
M.p. : 119–120°

HO Sn

(1, 2) (1)

SOURCE: Commercial formulation (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Musca domestica vicina L. Artificial 33 ppm Due to starvation only 1. Treatment to


(Housefly) diet 48.5 pupae were formed larvae at random in
feeding against 183.2 in controls. breeding media.
(2)

2. Spodoptera littoralis (Boisd.) Leaf disk 0.065% Feeding inhibition = 2. Treatment to 170-
(Egyptian cotton leaf worm) choice test 95.0% 190 mg body weight
larvae.
(3)

3. Gnorimoschema operculella Leaf dip 0.05% Feeding inhibition = 3. Treatment to 2nd


(Zell.) test 38.5% instar larvae. Data
(Potato tuber moth) calculated from
Reference 3.
(3)

4. Scolytus mediterraneus Twig dip 0.2% AI Twig penetration = 8% 4. Treatment to 0- to


Eggers test 1-day-old females.
(Bark beetle) 0.2% AI Twig penetration = 17% (4)

0.02% AI Twig penetration = 44%

5. Boarmia selenaria Leaf dip 0.1 g/l AI No pupae formed due to 5. Treatment to
(Denis & Schiff.) test starvation larvae at random.
(Giant looper) (5)

6. Spodoptera litura Fab. Leaf dip 0.065% Feeding inhibition = 6. Treatment to 4th
(Tobacco armyworm) test 95.0% instar larvae. Data
calculated on the
basis of leaf
protection.
(6)

© 2005 by CRC Press LLC


444 Opender Koul

7. Chilo agamemnon Blesz. Leaf disk 0.05% Feeding inhibition = 7. Treatment to


(Striped maize borer) test 76.7% larvae for 72 h.
(7)

Data calculated from


Reference 7

8. Leptinotarsa decemlineata Leaf disk 0.02% Feeding inhibition = 8. Treatment to F1


(Say) test 89.9% generation adults.
(Colorado potato beetle) (8)

LD50 (rats): 40–298 mg/kg (oral) (9)

(1) Ingham, R.K., Rosenberg, S.D., and Gilman, H. (1960) Chem. Rev., 60, 459.
(2) Ascher, K.R.S. and Moscowitz, J. (1968) Int. Pest Contr., 10, 10.
(3) Ascher, K.R.S., Avdat, N., and Kamhi, J. (1970) Int. Pest Contr., 12, 11.
(4) Ascher, K.R.S., Gurevitz, E., Renneh, S., and Nemny, N.E. (1975) Z. Pflkrankh. PflSchutz., 82, 378.
(5) Ascher, K.R.S., Nemny, N.E., Wysoki, M., and Gur-Telzak, L. (1978) Pestic. Sci., 9, 566.
(6) Ascher, K.R.S. and Nissim, S. (1965) Int. Pest Contr., 7, 21.
(7) Meisner, J. and Ascher, K.R.S. (1965) Z. Pflkrankh. PflPath. Pflschutz., 72, 458.
(8) Hare, J.D., Logan, P.A., and Wright, R.J. (1983) Environ. Entomol., 12, 1470.
(9) Farms Chem. Handbook (1982) Meister Publishing Co., C300.

© 2005 by CRC Press LLC


Insect Antifeedants 445

FERRUGININ–A C30H36O4
(460.61)
M.p. : 168–170°

OH OH O

OH

(1, 2) (1)

SOURCE: Vismia baccifera (L.) Tr. and Planch. var. ferruginea, achiote tigre (Clusiaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera exempta (Walker) Glass fiber 10–3 M Feeding inhibition = 1. Treatment to last
(Nut grass armyworm) disk test 54.29% instar larvae.
(2)

2. Heliothis virescens (Fab.) Glass fiber 10–3 M Feeding inhibition = 2. Treatment to last
(Tobacco bud worm) disk test 72.47% instar larvae.
(2)

(1) Delle Monache, F., Mac-Quhae, M.M., Ferrari, F., and Bettolo, G.B.M. (1985) Tetrahedron, 35, 2143.
(2) Simmonds, M.S.J., Blaney, W.M., Delle Monache, F., Mac-Quhae, M.M., and Bettolo, G.B.M. (1985) J.
Chem. Ecol., 11, 1593.

© 2005 by CRC Press LLC


446 Opender Koul

FERRUGININ–B C30H36O4
(460.61)

M.p. : 110–114°

OH OH O

OH

(1, 2) (1)

SOURCE: Vismia baccifera (L.) Tr. and Planch. var. ferruginea, achiote tigre (Clusiaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Heliothis virescens (Fab.) Glass fiber 10–3 M Feeding inhibition = 1. Treatment to last
(Tobacco bud worm) disk test 57.76% instar larvae.
(2)

2. Locusta migratoria (L.) Glass fiber 10–3 M Feeding inhibition = 2. Treatment to last
(Migratory locust) disk test 65.5% instar larvae.
(2)

(1) Delle Monache, F., Mac-Quhae, M.M., Ferrari, F., and Bettolo, G.B.M. (1985) Tetrahedron, 35, 2143.
(2) Simmonds, M.S.J., Blaney, W.M., Delle Monache, F., Mac-Quhae, M.M., and Bettolo, G.B.M. (1985) J.
Chem. Ecol., 11, 1593.

© 2005 by CRC Press LLC


Insect Antifeedants 447

FLAVONE C20H20O8
5-HYDROXY-3,6,7,8,4′-PENTAMETHOXY (388.35)
M.p. : 122–123°

OCH3
OCH3

H3CO O

H3CO OCH3

OH O

(1) (1)

SOURCE: Gnaphalium affine D. Don, cud weed (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera litura (Fab.) Leaf disk 1.1 × 10–7 Feeding inhibition = 1. Treatment to 3rd
(Tobacco armyworm) choice test mol/cm2 50% instar larvae in the
dark for 2 to 5 h.
Concentration = EC50
value
(1)

(1) Morimoto, M., Kumeda, S., and Komai, K. (2000) J. Agric. Food Chem., 48, 1888.

© 2005 by CRC Press LLC


448 Opender Koul

FLAVONE C19H18O7
5-HYDROXY-3,6,7,8-TETRAMETHOXY (358.33)
M.p. : 98–100°

OCH3

H3CO O

H3CO OCH3

OH O

(1) (1)

SOURCE: Gnaphalium affine D. Don, cud weed (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera litura (Fab.) Leaf disk 2.0 × 10–8 Feeding inhibition = 1. Treatment to 3rd
(Tobacco armyworm) choice test mol/cm2 50% instar larvae in the
dark for 2 to 5 h.
Concentration = EC50
value
(1)

(1) Morimoto, M., Kumeda, S., and Komai, K. (2000) J. Agric. Food Chem., 48, 1888.

© 2005 by CRC Press LLC


Insect Antifeedants 449

FLAVONE C17H14O6
5,6-DIHYDROXY-3,7 DIMETHOXY (314.28)
M.p. : 178°

H3CO O

HO OCH3

OH O

(1) (1)

SOURCE: Gnaphalium affine D. Don, cud weed (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera litura (Fab.) Leaf disk 2.5 × 10–8 Feeding inhibition = 1. Treatment to 3rd
(Tobacco armyworm) choice test mol/cm2 50% instar larvae in the
dark for 2 to 5 h.
Concentration = EC50
value
(1)

(1) Morimoto, M., Kumeda, S., and Komai, K. (2000) J. Agric. Food Chem., 48, 1888.

© 2005 by CRC Press LLC


450 Opender Koul

FORMONONETIN C16H12O4
(268.26)
M.p. : 265–266°
(257–258°)

HO O

O
OCH3

(1) (1)

SOURCE: Trifolium pratense L., red clover (Fabaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Costelytra zealandica Artificial diet 200 µg/ml Feeding inhibition = 1. Treatment to 3rd
(White) feeding 17.0% instar larvae after
(Scarab beetle) 24-h pre-starvation.
(2)

2. Heteronychus arator (Fab.) Artificial diet 200 µg/ml Feeding inhibition = 2. Treatment to 3rd
(Black beetle) feeding 15.0% instar larvae after
24-h pre-starvation.
(2)

(1) Bradbury, R.B. and White, D.E. (1951) J. Chem. Soc., 3447.
(2) Sutherland, O.R.W., Russel, G.B., Biggs, D.R., and Lane, G.A. (1980) Biochem. Syst. Ecol., 8, 73.

© 2005 by CRC Press LLC


Insect Antifeedants 451

8′-FORMYLOXYROTENONE C25H22O8
(450.42)
No physical data given
OCH3

H3CO
O

O
O O

CCH2OC OH

H
CH2

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius (L.) Wafer disk 10 mg/ml Feeding deterrence Treatment given to
(Grain weevil) test coefficient = 142.5 adults.

2. Tribolium confusum Duv. Wafer disk 10 mg/ml Feeding deterrence Treatment given to
(Confused flour beetle) test coefficient = both adults and
140.6 (adults) larvae.
122.1 (larvae)

3. Trogoderma granarium Wafer disk 10 mg/ml Feeding deterrence Treatment given to


Everts test Coefficient = 152.3 larvae.
(Khapra beetle)
Neutral value = 0
Absolute feeding
deterrence value =
200
(1)

(1) Nawrot, J., Harmatha, J., Kostova, I., and Ognyanov, I. (1989) Biochem. Syst. Ecol., 17, 55.

© 2005 by CRC Press LLC


452 Opender Koul

3′-FORMYL-2′,4′,6′-TRIHYDROXY- C17H16O5
5′-METHYLDIHYDROCHALCONE (300.31)
M.p. : 157–158°

[α]25
D : 0° (CHCl3)

CHO

HO
OH

OH O

(1) (1)

SOURCE: Psidium acutangulum DC, para guava (Myrtaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Heliothis virescens (Fab.) Leaf disk 24.8 µg/cm2 Feeding inhibition = Treatment to larvae
(Tobacco bud worm) choice test 90.0% for 2 days.

Feeding inhibition = Treatment to larvae


60.0-90.0% for 4 days
(1)

(1) Miles, D.H., Medeiros, J.M.R.D., Chittawong, V., Swithenbank, C., Lidert, Z., Weeks, J.A., Atwood, J.L. and
Hedin, P.A. (1990) J. Nat. Prod., 53, 1548.

© 2005 by CRC Press LLC


Insect Antifeedants 453

FRAXINELLONE C14H16O3
(232.28)
M.p. : 116°C

[α]22
D : –44° (EtOH)
O

(1, 2) (1)

SOURCE: Melia azedarach L., darekh (Meliaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera littoralis (Boisd.) Leaf disk 10 µg/cm2 Feeding inhibition = Treatment to 3rd
(Egyptian cotton leaf worm) choice test 100% instar larvae.
(2)

(1) Dreyer, D.L. (1983) Chemistry and Chemical Taxonomy of the Rutales, in P.G. Waterman and M.F. Grundon
(eds.), Academic Press, London, p. 215.
(2) Nakatani, M., Huang, R.C., Okamura, H., Iwagawa, T., and Tadera, K. (1998) Phytochemistry, 49, 1773.

© 2005 by CRC Press LLC


454 Opender Koul

FRIEDELIN C30H50O
(426.73)
M.p. : 267–269°
(263–263.5°)

[α]14
D : –27.8° (CHCl3)

(1) (1)

SOURCE: Acokanthera spectabilis Hook, Bushman’s poison (Apocynaceae) (2)


Virola calophylla (Spruce) Warb., virola (Myristicaceae) (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera littoralis (Boisd.) Leaf disk 0.1% Feeding inhibition = 1. Treatment to


(Egyptian cotton leaf worm) choice test 50% larvae.

2. Anthonomus grandis grandis Agar plug 50 µg/mm2 Feeding inhibition = 2. Treatment to


Bohem. bioassay 22.4% newly emerged boll
(Cotton boll weevil) weevils for 4 h in
dark.
(3)

(1) Brownlie, G., Spring, F.S., Stevenson, R., and Strachan, W.S. (1956) J. Chem. Soc., 2419.
(2) Abbassy, M.A., Elshazli, A., and Elgayar, F. (1977) Z. Angew. Entomol., 83, 317.
(3) Miles, D.H., Ly, A.M., Randle, S.E., Hedin, P.A., and Burks, M.L. (1987) J. Agric. Food Chem., 35, 794.

© 2005 by CRC Press LLC


Insect Antifeedants 455

1α-(3′-FURYL)-4β-4aβ-EPOXY-5β,8aα- C15H18O4
DIMETHYL-3-OXOOCTAHYDRO-1H-2- (262.31)
M.p. : 141–143°
BENZOPYRAN

O
O

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Leptinotarsa decemlineata Leaf disk 100 µg/cm2 Feeding inhibition = Treatment to 4th
(Say) bioassay 100% instar larvae for
(Colorado potato beetle) 6–8 h.

31.7 µg/cm2 Feeding inhibition = FI50 = 6.5 µg/cm2 or


82.9% 0.025 µ mol/cm2
(1)

10.0 µg/cm2 Feeding inhibition =


71.0%

3.17 µg/cm2 Feeding inhibition =


30.0%

(1) Bentley, M.D., Rajab, M.S., Mendel, M.J., and Alford, A.R. (1990) J. Agric. Food Chem., 38, 1400.

© 2005 by CRC Press LLC


456 Opender Koul

1β-(3′-FURYL)-4α-4aα-EPOXY-5β,8aα- C15H18O4
DIMETHYL-3-OXOOCTAHYDRO-1H-2- (262.31)
M.p. : 114–115°
BENZOPYRAN

O
O

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Leptinotarsa decemlineata Leaf disk 100 µg/cm2 Feeding inhibition = Treatment to 4th
(Say) bioassay 88.8% instar larvae for
(Colorado potato beetle) 6–8 h.

31.7 µg/cm2 Feeding inhibition = FI50 = 7.0 µg/cm2 or


84.7% 0.027 µ mol/cm2
(1)

10.0 µg/cm2 Feeding inhibition =


83.3%

3.17 µg/cm2 Feeding inhibition =


9.8%

(1) Bentley, M.D., Rajab, M.S., Mendel, M.J., and Alford, A.R. (1990) J. Agric. Food Chem., 38, 1400.

© 2005 by CRC Press LLC


Insect Antifeedants 457

GALACTOPYRANOSYL SAPONIN-3 C53H85O22


(1073.56)
[α]22
D : +0.7° (MeOH)

OH O
OH
HO COOH OH
O OH
O O
HO O O
HO OH
HO HO
O O
HO

OH

(1) (1)

SOURCE: Barringtonia asiatica Kurz, fish killer tree (Lecythidacaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Epilachna spp. Whole 1000 µg/ml Feeding deterrence = Treatment to 3rd


(Bean beetles) leaf 100% and 4th stage
assay larvae pre-
500 µg/ml Feeding deterrence = starved for 2 h.
54.54% Treatment
duration = 24h.
100 µg/ml Feeding deterrence = (1)
0.00%

(1) Herlt, A.J., Mander, L.N., Pongoh, E., Rumampuk, R.J., and Tarigan, P. (2002) J. Nat. Prod., 65, 115.

© 2005 by CRC Press LLC


458 Opender Koul

GALACTOPYRANOSYL SAPONIN-4 C53H83O22


(1071.54)
[α]22
D : +4.6° (MeOH)

OH O
OH
HO COOH OH
O OH
O O
HO O O
HO OH
HO HO
O O
HO

OH

(1) (1)

SOURCE: Barringtonia asiatica Kurz, fish killer tree (Lecythidacaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Epilachna spp. Whole leaf 1000 µg/ml Feeding deterrence = Treatment to 3rd and
(Bean beetles) assay 100% 4th stage larvae pre-
starved for 2 h.
500 µg/ml Feeding deterrence = Treatment duration =
63.35% 24h.
(1)
100 µg/ml Feeding deterrence =
39.09%

50 µg/ml Feeding deterrence =


10.00%

(1) Herlt, A.J., Mander, L.N., Pongoh, E., Rumampuk, R.J., and Tarigan, P. (2002) J. Nat. Prod., 65, 115.

© 2005 by CRC Press LLC


Insect Antifeedants 459

GALANTHAMINE CARBONATE C17H21O3N.½H2CO3


(320.39)
M.p. : 218–222°

[α]24
D : –98.8° (MeOH)
H
H3CO O

OH

+ 2-
N CO3

(1) (1)

SOURCE: Lycoris radiata Herb., red spider lily (Amaryllidaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Eurema hecabe mandarina Artificial diet 0.4% Feeding ratio = Treatment to 5th
delOrza feeding 21.9% instar larvae after 4 h
(Yellow butterfly) (medium feeding of pre-starvation.
inhibition) (1)

0.1% Feeding ratio =


41.4%
(slight feeding
inhibition)

0.05% Feeding ratio =


91.6%
(inactive)

(1) Numata, A., Takemura, T., Ohabayashi, H., Katsuno, T., Yamamoto, K., Sato, K., and Kobayashi, S. (1983)
Chem. Pharm. Bull., 31, 2146.

© 2005 by CRC Press LLC


460 Opender Koul

GALLIC ACID C7H6O5


(170.12)
M.p. : 253° (dec.)
(235–240°)

HO O

HO OH

OH

(1) (1)

SOURCE: Commercial sample (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Schizaphis graminum (Rondani) Artificial diet 146 ppm Feeding inhibition = Treatment to aphids
(Wheat aphid) feeding 50.0% at random.

Concentration = EC50
value.
(2)

LD (rats): 4 g/kg (s.c.), 5 g/kg (oral) (3)

(1) Cochrane, V.W. (1948) Econ. Bot., 2, 145.


(2) Jones, K.C. and Klocke, J.A. (1987) Entomol. Exp. Appl., 44, 229.
(3) (1983) Merck Index, p. 621.

© 2005 by CRC Press LLC


Insect Antifeedants 461

GEDUNIN C28H34O7
(482.57)
M.p. : 157°
(218°)
O
[α]20
D : –44° (CHCl3)

O
O

O OAc

(1, 2) (2,3)

SOURCE: Azadirachta indica A. Juss., neem (Meliaceae) (1, 3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Epilachna varivestis Muls. Bean leaf 0.1% Feeding inhibition = 1. Treatment to 4th
(Mexican bean beetle) choice assay 50.0% instar larvae for 24 h.

Concentration = EC50
value.
(3)

2. Ostrinia nubilalis (Hubner) Leaf disk no- 500 µg/g Feeding inhibition = 2. Treatment to
(European corn borer) choice assay 100.0% neonate larvae for
48 h.
(4)

Data calculated from


Reference 4.

(1) Lavie, D., Levy, E.C., and Jain, M.K. (1971) Tetrahedron, 27, 3927.
(2) Housley, J.R., King, F.E., King, T.J., and Taylor, P.R. (1962) J. Chem. Soc., 5095.
(3) Schwinger, M., Ehhammer, B., and Kraus, W. (1984) In H. Schmutterer and K.R.S. Ascher (eds.), Proc. 2nd
Int. Neem Conf., Rauischholzhausen, GTZ, Eschborn, Germany, pp. 181–198.
(4) Arnason, J.T., Philogene, B.J.R., Donskov, N., and Kubo, I. (1987) Entomol. Exp. Appl., 43, 221.

© 2005 by CRC Press LLC


462 Opender Koul

GENISTEIN 7-RUTINOSIDE C27H30O14


(spherobioside) (578.52)
M.p. : 203–204°

[α]20
D : –73.3° (Pyridine)

HO
O
OH
O
O
HO
O

OH HO O

OH OH OH

(1) (1)

SOURCE: Commercial sample (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Heteronychus arator (Fab.) Artificial diet 200 µg/ml Feeding inhibition = 1. Treatment to 3rd
(Black beetle) feeding 31.6% instar larvae after
24 h of pre-
starvation.
Data calculated from
Reference 2.
(2)

2. Costelytra zealandica Artificial diet 200 µg/ml Feeding inhibition = 2. Treatment to 3rd
(White) feeding 9.3% instar larvae after
(Scarab beetle) 24 h of pre-
starvation.
Data calculated from
Reference 2.
(2)

(1) Rosler, H., Mabry, T.J., and Kogan, J. (1965) Chem. Ber., 98, 2193.
(2) Sutherland, O.R.W., Russel, G.B., Biggs, D.R., and Lane, G.A. (1980) Biochem. Syst. Ecol., 8, 73.

© 2005 by CRC Press LLC


Insect Antifeedants 463

GENTISIC ACID C7H6O4


(154.12)
M.p. : 204.5–205°
(199–200°)

COOH

OH

HO

(1) (1, 2)

SOURCE: Alchornea triplinervia (Spreng.) Muell. Arg., tapia (Euphorbiaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Anthonomus grandis Bohem. Artificial 5 mg/4 cm2 Feeding ratio based Treatment to freshly
(Boll weevil) diet feeding on T/C = 65.0% emerged boll
weevils.
10 mg/4 cm2 Feeding ratio based Treated/Control = 0
on T/C = 8.0% represents absolute
antifeedant effect
12 mg/4 cm2 Feeding ratio based and >100 is
on T/C = 14.0% attractant.
(1)

LD50 (rats): 800 mg/kg (oral) (3)

(1) Miles, D.H., Hankinson, B.L., and Randle, S.A. (1985) Proc. ACS Symp. Ser. 276, 469.
(2) (1994) Dictionary of Natural Products, Chapman & Hall, London.
(3) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC


464 Opender Koul

GERANIIN C41H28O27
HO OH HO OH
(952.65)
M.p. : 360°
HO OH
O [α]15
D : –141° (MeOH)
O
O
HO O
O O

O O
HO O O

OH O

OH
HO

HO O O
OH
OH (1, 2) (1, 2)

SOURCE: Geranium viscosissimum Fisch and Meyer var. viscossissimum, sticky geranium
(Geraniaceae) (2, 3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Schizaphis graminum Artificial diet 179 ppm Feeding inhibition = 1. Treatment to


(Rondani) feeding 50.0% aphids at random.
(Wheat aphid)
Concentration = EC50
value
(3)

2. Myzus persicae (Sulzer) Artificial diet 338 ppm Feeding inhibition = 2. Treatment to
(Green peach aphid) feeding 50.0% aphids at random.

Concentration = EC50
value
(3)

(1) Okuda, T., Yoshida, T., and Nayeshiro, H. (1976) Tetrahedron Lett., 3721.
(2) Yoshida, T., Seno, K., Takama, Y., and Okuda, T. (1982) Phytochemistry, 21, 1180.
(3) Jones, K.C. and Klocke, J.A. (1987) Entomol. Exp. Appl., 44, 229.

© 2005 by CRC Press LLC


Insect Antifeedants 465

GINKGOLIDE–A C20H24O9
(408.40)
M.p. : 280° (dec.)

O [α]D : –39° (Dioxane)


O

O O
OH

OH
O

H
O O H

(1, 2) (1)

SOURCE: Ginkgo biloba L., ginkgo tree (Ginkgoaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Pieris rapae crucivora Boisd. Leaf disk 500 µg/disk Feeding inhibition = Treatment to 3rd
(Cabbage butterfly) test 98.0% instar larvae.
(2)
50 µg/disk Feeding inhibition =
57.0%

(1) Maruyama, M., Terahara, A., Itagaki, Y., and Nakanishi, K. (1967) Tetrahedron Lett., 299.
(2) Matsumoto, T. and Sei, T. (1987) Agric. Biol. Chem., 51, 249.

© 2005 by CRC Press LLC


466 Opender Koul

GINKGOLIDE–B C20H24O10
(424.40)
M.p. : >280° (dec.)

[α]D : –63° (Dioxane)


O
O

O O
OH

OH
O

OH
O H
O

(1, 2) (1)

SOURCE: Ginkgo biloba L., ginkgo tree (Ginkgoaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Pieris rapae crucivora Boisd. Leaf disk 500 µg/disk Feeding inhibition = Treatment to 3rd
(Cabbage butterfly) test 81.0% instar larvae.
(2)

(1) Maruyama, M., Terahara, A., Itagaki, Y., and Nakanishi, K. (1967) Tetrahedron Lett., 299.
(2) Matsumoto, T. and Sei, T. (1987) Agric. Biol. Chem., 51, 249.

© 2005 by CRC Press LLC


Insect Antifeedants 467

GLAUCARUBINE C25H36O10
(496.55)
M.p. : 250–255° (dec.)

[α]25
D : +45° (Pyridine)
OH
+69° (MeOH)
HO
HO
O
HO OCO

OH
O O
H

(1, 2) (2,3)

SOURCE: Simarouba glauca DC, bitter wood (Simaroubaceae) (2, 3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Heliothis virescens (Fab.) Leaf disk 19.8 µg/disk Feeding inhibition = Treatment to 3rd
(Tobacco budworm) test 30–60% after 2 days instar larvae for 24 h.
(4)

(1) Polonsky, J. and Gaudemer, A. (1961) Bull. Soc. Chim., 1432.


(2) Bourguigon, N. and Polonsky, J. (1964) Bull. Soc. Chim. Biol., 47, 1145.
(3) Kartha, G. and Haas, D.J. (1964) J. Am. Chem. Soc., 86, 3630.
(4) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y., Kiyokawa, H., and Lee, K.H.
(1987) J. Nat. Prod., 50, 442.

© 2005 by CRC Press LLC


468 Opender Koul

GLAUCARUBINONE C25H34O10
(494.54)
M.p. : 225–228°
(228–230°)

OH [α]D : +50° (MeOH)

HO
HO
O

O OCO

OH

O O
H

(1, 2) (1)

SOURCE: Simarouba glauca DC, bitter wood (Simaroubaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Heliothis virescens (Fab.) Leaf disk 19.8 µg/disk Feeding inhibition = 1. Treatment to 3rd
(Tobacco budworm) test 60–90% after 2 days instar larvae.
and 30–60% after 6 (2)
days.

2. Epilachna varivestis Muls. Whole leaf 250 ppm Feeding inhibition = 2. Treatment to 4th
(Mexican bean beetle) application 83.5% after 24 h. instar larvae pre-
starved for 2 h.
Data calculated from
Reference 3.
(3)

3. Spodoptera eridania Whole leaf 500 ppm Feeding inhibition = 3. Treatment to


(Cramer) application 50.0% after 24 h. freshly molted 5th
(Southern armyworm) instar larvae pre-
starved for 2 h.
(3)

(1) Bourguigon, N. and Polonsky, J. (1964) Bull. Soc. Chim. Biol., 47, 1145.
(2) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y., Kiyokawa, H., and Lee, K. (1987)
J. Nat. Prod., 50, 442.
(3) Leskinen, V., Polonsky, J., and Bhatnagar, S. (1984) J. Chem. Ecol., 10, 1497.

© 2005 by CRC Press LLC


Insect Antifeedants 469

GLAUCARUBOL C20H28O8
(396.44)
M.p. : 290–292° (dec.)

[α]25
D : +38° (Pyridine)
OH

HO
HO
O
HO OH

O O
H

(1, 2, 3) (1, 2)

SOURCE: Simarouba glauca DC, bitter wood (Simaroubaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Heliothis virescens (Fab.) Leaf disk 19.8 µg/disk Feeding inhibition = Treatment to 3rd
(Tobacco budworm) test 30–60% after 2 days instar larvae for 24 h.
(3)

(1) Polonsky, J. and Gaudemer, A. (1961) Bull. Soc. Chim., 1432.


(2) Stocklin, W. and Geissman, T.A. (1970) Phytochemistry, 9, 1887.
(3) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y., Kiyokawa, H., and Lee, K.H.
(1987) J. Nat. Prod., 50, 442.

© 2005 by CRC Press LLC


470 Opender Koul

GLAUCARUBOLONE C20H26O8
(394.42)
M.p. : 255–258°

[α]D : +34° (Pyridine)


OH

HO
HO
O

O OH

O O

(1, 2) (1)

SOURCE: Hannoa klaineana Pierre et Engler, African guassia (Simaroubaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Heliothis virescens (Fab.) Leaf disk 19.8 µg/disk Feeding inhibition = 1. Treatment to 3rd
(Tobacco budworm) test 60–90% after 2 days instar larvae.
and 30–60% after 6 (2)
days

2. Epilachna varivestis Muls. Whole leaf 500 ppm Feeding inhibition = 2. Treatment to 4th
(Mexican bean beetle) application 77.8% after 24 h instar larvae pre-
starved for 2 h.
Data calculated from
Reference 3.
(3)

3. Spodoptera eridania Whole leaf 500 ppm Feeding inhibition = 3. Treatment to


(Cramer) application 36.0% after 24 h freshly molted 5th
(Southern armyworm) instar larvae pre-
starved for 2 h.
(3)

(1) Gaudemer, A. and Polonsky, J. (1965) Phytochemistry, 4, 149.


(2) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y, Kiyokawa, H., and Lee, K.H.
(1987) J. Nat. Prod., 50, 442.
(3) Leskinen, V., Polonsky, J., and Bhatnagar, S. (1984) J. Chem. Ecol., 10, 1497.

© 2005 by CRC Press LLC


Insect Antifeedants 471

GLAUCOLIDE–A C23H28O10
(464.47)
M.p. : 153–154°

OAc [α]25
CH2 D : –29° (CHCl3)
O

O
H O

O
O

OAc
O

(1, 2) (1)

SOURCE: Vernonia glauca (L.) Willd., vernonia weed (Asteraceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera frugiperda Cellulose 1.0% Feeding inhibition Treatment to 4th


(J.E. Smith) millipore rating = 15.6 mg in stadium larvae.
(Fall armyworm) filter disk test 48 h Average deterrence
rating based on
control-treated disk
consumption.
(2)

(1) Padolina, W.G., Yoshioka, H., Nakatani, N., Mabry, T.J., Monti, S.A., Davis, R.E., Cox, P.J., Sim, G.A.,
Watson, W.H., and Wu, I.B. (1974) Tetrahedron, 30, 1161.
(2) Smith, C.M., Kester, K.M., and Fischer, N.H. (1983) Biol. Syst. Ecol., 11, 377.

© 2005 by CRC Press LLC


472 Opender Koul

GLUCOPYRANOSYL C26H36O13
GLAUCARUBOLONE (556.56)
M.p. : 252–254°

[α]22
D : –25.7° (Pyridine)
OH OH
OH
HO OH
HO
O O CH2OH

O O

O O
H

(1, 2) (1)

SOURCE: Simarouba glauca DC, bitter wood (Simaroubaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Heliothis virescens (Fab.) Leaf disk 19.8 µg/disk Feeding inhibition = Treatment to 3rd
(Tobacco budworm) test 60–90% after 2 days instar larvae.
and 0–30% after (2)
6 days

12.0 µg/disk Feeding inhibition =


30–60% after 2 days
and 0–30% after
6 days

(1) Bhatnagar, S., Polonsky, J., Prange, T., and Pascard, C. (1984) Tetrahedron Lett., 25, 299.
(2) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y., Kiyokawa, H., and Lee, K.H.
(1987) J. Nat. Prod., 50, 442.

© 2005 by CRC Press LLC


Insect Antifeedants 473

GLYCEOLLIN C20H18O5
(338.36)
Only spectral data given

OH

O
H

OH

O O

(1, 2) (1)

SOURCE: Glycine max (L.) Merrill., soybean (Fabaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Epilachna varivestis Mulsant Leaf surface 6.1 µg/mg Feeding inhibition = Treatment to 12-h
(Mexican bean beetle) application leaf dry 50.0% starved adults until
weight half of the leaf
material was
2. Diabrotica undecimpunctata Leaf surface 3.5 µg/mg Feeding inhibition = consumed (6–8 h).
howardi Barber application leaf dry 50.0% Concentration = FI50
(Southern corn rootworm) weight

3. Cerotoma trifurcata (Forster) Leaf surface Highest Feeding inhibition = It was not possible to
(Bean leaf beetle) application conc. < 50.0% at the calculate EC50
highest because 50%
concentration used deterrence was not
achieved at the
highest treatment
level used.
(2)

(1) Burden, R.S. and Bailey, J.A. (1975) Phytochemistry, 14, 1389.
(2) Fischer, D.C., Kogan, M., and Paxton, J. (1990) Environ. Entomol., 19, 1278.

© 2005 by CRC Press LLC


474 Opender Koul

GOSSYPOL C30H30O8
(518.56)
M.p. : 181–183°

D : +445 ± 10° (CHCl3)


[α]19

CHO OH OH CHO

HO OH

HO OH

(1) (1)

SOURCE: Gossypium hirsutum L., cotton (Malvaceae) (2)


Also synthetic from gossypol accetate

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera littoralis (Boisd.) Styropor 1.0% Feeding inhibition = Treatment to larvae


(Egyptian cotton leaf worm) method 73.6% at random.

0.5% Feeding inhibition = Treatment duration =


61.5% 48 h.
(2)
0.25% Feeding inhibition =
34.0% FI50 = 0.42%
calculated from
0.1% Feeding inhibition = Reference 2.
6.2%

LD50 (rats): 2.57 g/kg (oral) (3)

(1) King, T.J. and deSilva, L.B. (1968) Tetrahedron Lett., 261.
(2) Meisner, J., Ascher, K.R.S., and Zur, M. (1977) J. Econ. Entomol., 70, 149.
(3) El-Nockrashy, A.S., Lyman, C.M., and Dollahite, J.W. (1963) J. Am. Oil Chem. Soc., 40, 14.

© 2005 by CRC Press LLC


Insect Antifeedants 475

GRADOLIDE C25H34O7
(446.54)
M.p. : 154°

OH [α]20
D : –50.9°

OOC

OOC
O

(1, 2) (1)

SOURCE: Laserpitium siler L., mountain lasser wort (Umbelliferae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius (L.) Wafer disk 1.0% Feeding deterrence 1. Treatment given to
(Grain weevil) test coefficient = 84 adults.

2. Tribolium confusum Duv. Wafer disk 1.0% Feeding deterrence 2. Treatment given to
(Confused flour beetle) test coefficient both adults and
Adults = 146 larvae.
Larvae = 140

3. Trogoderma granarium Wafer disk 1.0% Feeding deterrence 3. Treatment given to


Everts test coefficient = 94 larvae.
(Khapra beetle)
Neutral value = 0
Absolute feeding
deterrence value =
200
(2)

(1) Holub, M., Motl, O., and Samek, Z. (1978) Collect. Czech. Chem. Commun., 43, 2471.
(2) Nawrot, J., Smitalova, Z., and Holub, M. (1983) Biochem. Syst. Ecol., 11, 243.

© 2005 by CRC Press LLC


476 Opender Koul

GRAMINE C11H14N2
(174.24)
M.p. : 138–139°
(131–132°)

N
H

(1, 2) (1)

SOURCE: Commercial material (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Rhopalosiphum maidis Artificial diet 4 mM Feeding deterrence = 1. Treatment to


(Fitch) feeding 35.9% aphids at random for
(Corn leaf aphid) 5 h.
6 mM Feeding deterrence = (2)
62.6%

2. Schizaphis graminum Artificial diet 4 mM Feeding deterrence = 2. Treatment to


(Rondani) feeding 63.9% aphids at random for
(Wheat aphid) 5 h.
6 mM Feeding deterrence = (2)
66.7%

LD50 (mice): 122 mg/kg (ipr.) (3)

(1) Pachter, I.J., Zacharias, D.E., and Ribeiro, O. (1959) J. Org. Chem., 24, 1285.
(2) Corcuera, L.J. (1984) Phytochemistry, 23, 539.
(3) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC


Insect Antifeedants 477

GRISEOFULVIN C17H17O6Cl
(352.77)
M.p. : 225–226°

[α]17
D : +370° (CHCl3)

OCH3 O OCH3

H3CO O

Cl

(1, 2) (1)

SOURCE: Metabolite of Penicillium griseofulvum Dirck. (filamentous fungi) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Peridroma saucia (Hubner) Leaf disk 28.5 µg/cm2 Feeding inhibition = Treatment to 5th
(Variegated cutworm) choice test 14.3% instar larvae for 5 h.
(2)
57.0 µg/cm2 Feeding inhibition =
72.8%

LD50 (rats): 1200 mg/kg (scu) (3)

(1) Grove, J.F., MacMillan, J., Mulholland, T.P.C., and Zealley, J. (1952) J. Chem. Soc., 3949, 3967.
(2) Nawrot, J., Koul, O., Isman, M.B., and Harmatha, J. (1991) J. Appl. Ent., 112, 194.
(3) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC


478 Opender Koul

(±)- GROSSAMIDE OH C36H36O8N2


OH (624.69)
M.p. : 174–175°
(133–135°)

NH
O HN
O

OCH3 OH

OCH3
(1, 2) (1, 2)

SOURCE: Xylopia aethiopica A. Rich., African pepper (Anonaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Reticulitermes speratus Kolbe Paper disk 5000 ppm Feeding inhibition Treatment to 3rd
(Subterranean termite) choice test index = 1.91 instar workers.

Feeding duration =
14 days.

Antifeedant index
value below 20 is
highly deterrent
effect.
(1)

(1) Lajide, L., Escoubas, P., and Mizutani, J. (1995) Phytochemistry, 40, 1105.
(2) Sakakibara, I., Katsuhara, T., Ikeya, Y., Hayashi, K., and Mitsuhashi, H. (1991) Phytochemistry, 30, 3013.

© 2005 by CRC Press LLC


Insect Antifeedants 479

GROSSHEIMIN C15H18O4
(262.31)
M.p. : 205°

CH2 [α]20
D : +137.7° (MeOH)

O OH

CH2
O

(1, 2) (1, 2)

SOURCE: Grosshimia macrocephala Muss. (Push) D. Sosnet Takcht. (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius (L.) Wafer disk 8 mg/cm3 Feeding deterrence 1. Treatment given to
(Grain weevil) test coefficient = 51–100 adults.

2. Tribolium confusum Duv. Wafer disk 8 mg/cm3 Feeding deterrence 2. Treatment given to
(Confused flour beetle) test coefficient both adults and
Adults = 51–100 larvae.
Larvae = 51–100

3. Trogoderma granarium Wafer disk 8 mg/cm3 Feeding deterrence 3. Treatment given to


Everts test coefficient = larvae.
(Khapra beetle) 101–150
Neutral value = 0
Absolute feeding
deterrence value =
200
(3)

(1) Mukhametzhanov, M.N., Sheichenko, V.I., Rybalko, K.S., and Boryaev, K.I. (1969) Khim. Prir. Soedin., 5, 184.
(2) Samek, Z., Holub, M., Vokac, K., Drozdz, B., Jommi, G., Gariboldi, P., and Corbella, A. (1972) Collect.
Czech. Chem. Commun., 37, 2611.
(3) Nawrot, J., Bloszyk, E., Grabarczyk, H., and Drozdz, B. (1982) Prace Nauk. Inst. Ochr. Roslin, 24, 27.

© 2005 by CRC Press LLC


480 Opender Koul

GRAYANOTOXIN–I C22H36O7
(412.51)
M.p. : 260–272°

[α]D : –8.8° (EtOH)


OH
H
OAc

HO

OH
OH
OH

(1, 2) (1, 2)

SOURCE: Rhododendron molle (B.) G. Don, yellow azalea (Ericaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Leptinotarsa decemlineata Leaf 12.5 µg/50 mm2 Feeding inhibition = 1. Treatment to 4th
(Say) disk 95.0% instar larvae until
(Colorado potato beetle) choice 95% of control disk
test was consumed.
(1)

2. Spodoptera frugiperda Leaf 12.0 µg/50 mm2 Feeding inhibition = 2. Treatment to 3rd
(J.E. Smith) disk 95.0% instar larvae until
(Fall armyworm) choice 95% of control disk
test was consumed.
(1)

(1) Klocke, J.A., Hu, M., Chiu, S., and Kubo, I. (1991) Phytochemistry, 30, 1797.
(2) Sukh, Dev and Koul, O. (1997) Insecticides of Natural Origin, Harwood Academic Publishers, Amsterdam,
p. 94.

© 2005 by CRC Press LLC


Insect Antifeedants 481

GRAYANOTOXIN–III C20H34O6
(370.48)
M.p. : 218°

[α]15
D : –12°

OH
H
OH

HO

OH
OH
OH

(1, 2) (1, 2)

SOURCE: Rhododendron molle (B.) G. Don, yellow azalea (Ericaceae) (2)


Also isolated from several species of Ericaceae family.

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Leptinotarsa decemlineata Leaf disk 12.5 µg/50 mm2 Feeding inhibition = 1. Treatment to 4th
(Say) choice test 95.0% instar larvae until
(Colorado potato beetle) 95% of control disk
was consumed.
(2)

2. Spodoptera frugiperda Leaf disk 12.0 µg/50 mm2 Feeding inhibition = 2. Treatment to 3rd
(J.E. Smith) choice test 95.0% instar larvae until
(Fall armyworm) 95% of control disk
was consumed.
(2)

(1) Hikino, H., Ogura, M., Ohta, T., and Takemoto, T. (1970) Chem. Pharm. Bull., 18, 1071; 2357.
(2) Klocke, J.A., Hu, M., Chiu, S., and Kubo, I. (1991) Phytochemistry, 30, 1797.

© 2005 by CRC Press LLC


482 Opender Koul

HALOSTACHINE C9H13ON
(151.21)
M.p. : 43–45°

H [α]D : –47°
N

H C OH

(1) (1)

SOURCE: Halostachys caspica Meyer ex Schrenk., salt wort (Chenopodiaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Locusta migratoria (L.) Wafer test 0.025% Feeding inhibition = Treatment at random.
(Migratory locust) 98.0% (2)

Leaf test 0.025% Feeding inhibition =


48.0%

(1) (1994) Dictionary of Natural Products, Chapman & Hall, London.


(2) Bernays, E.A. and Chapman, R.F. (1977) Ecol. Ent., 2, 1–18.

© 2005 by CRC Press LLC


Insect Antifeedants 483

HARRISONIN C27H32O10
(516.54)
M.p. : 155–156°
O (164.5–165°)

O
O
H3COOC HO OH

O
O

(1, 4) (1,3)

SOURCE: Harrisonia abyssinica Oliv., East African medicinal plant (Simaroubaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera exempta (Walker) Leaf disk 20 ppm Feeding inhibition = 1. Treatment to


(Nutgrass armyworm) choice test 100% larvae at random.
(2)

100 µg/disk Feeding inhibition = Treatment to early to


32.0 ± 17.0% mid 6th instar larvae.
(3)

2. Eldana saccharina Walker Leaf disk 100 µg/disk Feeding inhibition = 2. Treatment to 12–h
(Sugar cane borer) test 74.0 ± 13.0% pre-starved late 5th
instar larvae.
1 µg/disk Feeding inhibition =
74.0 ± 16.0% (3)

3. Maruca testulalis (Geyer) Leaf disk 100 µg/disk Feeding inhibition = 3. Treatment to late
(Bean pod borer) test 81.0 ± 14.0% 5th instar larvae.
(3)
1 µg/disk Feeding inhibition =
39.0 ± 8.0%

(1) Kubo, I., Tanis, S.P., Lee, Y., Miura, I., Nakanishi, K., and Chapya, A. (1976) Heterocycles, 5, 485.
(2) Kubo, I. and Nakanishi, K. (1978) Adv. Pestic. Chem., 2, 284.
(3) Hassanali, A., Bentley, M.D., Sitayo, E.N.O., Njoroge, P.E.W., and Yatagai, M. (1986) Insect Sci. Applic., 7,
495.
(4) Rajab, M.S., Rugutt, J.K., Fronczek, F.R., and Fischer, N.H. (1997) J. Nat. Prod., 60, 822.

© 2005 by CRC Press LLC


484 Opender Koul

HARUNGANIN C30H36O4
(460.61)
M.p. : 190°

OH OH O

OH

(1, 2) (1)

SOURCE: Harungana madagascariensis Lam. ex Poir., harungana (Clusiaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera exempta (Walker) Glass fiber 10–3 M Feeding inhibition = 1. Treatment to last
(Nutgrass armyworm) disk test 71.18% instar larvae.
(2)

2. Spodoptera littoralis (Boisd.) Glass fiber 10–3 M Feeding inhibition = 2. Treatment to last
(Egyptian cotton leaf worm) disk test 48.27% instar larvae.
(2)

3. Heliothis virescens (Fab.) Glass fiber 10–3 M Feeding inhibition = 3. Treatment to last
(Tobacco bud worm) disk test 60.96% instar larvae.
(2)

4. Locusta migratoria (L.) Glass fiber 10–3 M Feeding inhibition = 4. Treatment to last
(Migratory locust) disk test 42.33% instar larvae.
(2)

(1) Ritchie, E. and Taylor, W.C. (1964) Tetrahedron Lett., 1431.


(2) Simmonds, M.S.J., Blaney, W.M., Delle Monache, F., Mac-Quhae, M.M., and Bettolo, G.B.M. (1985) J.
Chem. Ecol., 11, 1593.

© 2005 by CRC Press LLC


Insect Antifeedants 485

HAUTRIWAIC ACID C20H28O4


(332.44)
M.p. : 183–184°

[α]D : –105°

COOH
OH

(1, 2) (1)

SOURCE: Dodonaea viscosa Jacq., hopseed bush, D. attenuata (Sapindaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera frugiperda Leaf disk 2 ppm Feeding inhibition = Treatment to 3rd


(J.E. Smith) no-choice 25.0% instar larvae pre-
(Fall armyworm) test starved for 4 h.
50 ppm Feeding inhibition = Treatment duration =
50.0% 24 h.
(2)
100 ppm Feeding inhibition =
100.0% Data calculated from
Reference 2.

(1) Bohlmann, F. (1972) Chem Ber., 105, 2123.


(2) Taboada, J., Guerrero, C., Camino, L.M., and Aldama, L.L. (1996) Rev. Latinoamer. Quim., 24, 33.

© 2005 by CRC Press LLC


486 Opender Koul

HELENALIN C15H18O4
(262.30)
M.p. : 225–228°

[α]25
D : –102.8° (CHCl3)

O
O
OH
CH2

(1, 2) (1, 2)

SOURCE: Helenium aromaticum (Hook) Bailey, aromatic weed (Asteraceae) (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius (L.) Wafer disk 8 mg/cm3 Feeding deterrence 1. Treatment given to
(Grain weevil) test coefficient = adults.
151–200

2. Tribolium confusum Duv. Wafer disk 8 mg/cm3 Feeding deterrence 2. Treatment given to
(Confused flour beetle) test coefficient both adults and
Adults = 151–200 larvae.
Larvae = 101–150

3. Trogoderma granarium Wafer disk 8 mg/cm3 Feeding deterrence 3. Treatment given to


Everts test coefficient = larvae.
(Khapra beetle) 151–200
Neutral value = 0
Absolute feeding
deterrence value =
200
(3)

LD50 (rats): 125 mg/kg (oral) (4)

(1) Adams, R. and Herz, W. (1949) J. Am. Chem. Soc., 71, 2546.
(2) Lee, K.H., Anuforo, D.C., Huang, E.-S., and Piantadosi, C. (1972) J. Pharm. Sci., 61, 626.
(3) Nawrot, J., Bloszyk, E., Grabarczyk, H., and Drozdz, B. (1982) Prace Nauk. Inst. Ochr. Roslin, 24, 27.
(4) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC


Insect Antifeedants 487

HELIOTRINE C16H27O5N
(313.39)
M.p. : 128°
(125–126°)

H [α]20
D : +63.8° (CHCl3)
H3CO C
C CH(CH3)2
C O
OH
H O
HO
CH2

(1, 2, 3) (1, 2)

SOURCE: Heliotropium arbainense Fres., heliotrope (Boraginaceae) (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Choristoneura fumiferana Paper 1.6 × 103 M Feeding inhibition = Treatment to 6th


(Clemens) penicillin 35.0% instar larvae.
(Spruce bud worm) disk assay (3)

LD50 (rats): 300 mg/kg (i.p.) (4)

(1) Menshikov, G. (1932) Ber., 65, 974.


(2) Menshikov, G. (1935) Ber., 68, 974.
(3) Bentley, M.D., Leonard, D.E., Stoddard, W.F., and Zalkow, L.H. (1984) An. Entomol. Soc. Am., 77, 393.
(4) Cordell, G.A. (1981) Introduction to Alkaloids, John Wiley & Sons, New York, p. 134.

© 2005 by CRC Press LLC


488 Opender Koul

15 – HEPTYLCHAPARRINONE C27H40O7
(476.61)
Only spectral data given

OH

HO
HO
O

O O
H

(1, 2) (1, 2)

SOURCE: Synthetic (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Heliothis virescens (Fab.) Leaf disk 19.8 µg/cm2 Feeding inhibition = Treatment to 3rd
(Tobacco budworm) test 90–100% after 2 instar larvae for 24 h.
days (2)
and 60–90% after 6
days of treatment.

6.0 µg/cm2 Feeding inhibition =


60–90% after 6 days
of treatment.

3.0 µg/cm2 Feeding inhibition =


30–60% after 2 days
and 0–30% after 6
days of treatment.

(1) Caruso, A.J., Polonsky, J., and Rodriguez, B.S. (1982) Tetrahedron Lett., 23, 2567.
(2) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y., Kiyokawa, H., and Lee, K. (1987)
J. Nat. Prod., 50, 442.

© 2005 by CRC Press LLC


Insect Antifeedants 489

9 – HEXADECENOIC ACID C16H30O2


(254.41)
M.p. : 32–33° (dec.)

B.p. : 180–183°/1 mm

COOH

(1, 2, 3) (1, 2)

SOURCE: Synthetic (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Incisitermes minor (Hagan) Paper towel 0.25 mg/cm2 Feeding inhibition = Treatment to larvae
(Western drywood termite) disk test 22.7% of 10–13 mg body
weight up to 7 days.

0.05 mg/cm2 Feeding inhibition = Treatment to larvae


9.7% of 10–13 mg body
weight up to 6 days.
(3)

Data calculated from


Reference 3.

(1) Armstrong, E.F. and Hilditch, T.P. (1925) J. Soc. Chem Ind., 44, 182T.
(2) Hilditch, T.P. and Vidyarthi, N.L. (1927) J. Soc. Chem Ind., 46, 172T.
(3) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39.

© 2005 by CRC Press LLC


490 Opender Koul

2′,3′,20,21,22,23 – HEXAHYDROSALANNIN C34H50O9


(602.76)
Only spectral data given

COO O
O

O
AcO
H
O

(1) (1, 2)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Leptinotarsa decemlineata Leaf disk 25 µg/cm2 Feeding inhibition = Treatment to freshly


(Say) choice test 95.0% molted 3rd instar
(Colorado potato beetle) larvae.
Leaf disks examined
10 µg/cm2 Feeding inhibition = every 2 h until 95%
50.0% of control disks were
consumed.

Concentrations
denote the protection
levels = PC95 and
PC50, respectively.
(1)

(1) Yamasaki, R.B. and Klocke, J.A. (1989) J. Agric. Food Chem., 37, 1118.

© 2005 by CRC Press LLC


Insect Antifeedants 491

HEXAMETHYLDITIN C6H18Sn2
(327.59)
B.p. : 182°/760 mm

M.p. : 62–63°/12 mm

Sn Sn

(1) (1, 2)

SOURCE: Commercial formulation (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera littoralis (Boisd.) Leaf dip test 0.1% Feeding inhibition = 1. Treatment to 2-
(Egyptian cotton leaf worm) 64.0% cm-long larvae. Field
deposit residue
0.2% Feeding inhibition = leaves were used in
58.0% each treatment.
(1)

2. Scolytus mediterraneus Twig dipping 0.2% No twig penetration 2. Treatment to 0 to


Eggers method 1-day-old females.
(Fruit bark beetle) 0.02% 5% twig penetration (2)

0.002% 48% twig


penetration

LD50 (rats): 10–25 mg/kg (oral) (1)

(1) Ascher, K.R.S. and Moscowitz, J. (1969) Int. Pest Contr., 11, 17.
(2) Ascher, K.R.S., Gurevitz, E., Renneh, S., and Nemny, N.E. (1975) Z. Pflkrankh. Pflschutz., 82, 378.

© 2005 by CRC Press LLC


492 Opender Koul

HILDECARPIN C17H14O7
(330.29)
[α]D : –244° (MeOH)

HO O

OH
O
H3CO
H
O
O

(1) (1)

SOURCE: Tephrosia hildebrandtii Vatke, tephrosia (Fabaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera exempta (Walker) Leaf disk 5000 ppm Inactive up to this 1. Treatment to
(Nutgrass armyworm) choice test level of treatment in larvae at random.
this insect species. (1)

2. Maruca testulalis (Geyer) Leaf disk 100 µg/disk Feeding inhibition = Treatment to 5th
(Bean pod borer) test 85.8% instar larvae.
(1)
10 µg/disk Feeding inhibition =
51.9%

(1) Lwande, W., Hassanali, A., Njoroge, P.W., Bentley, M.D., Monache, F.D., and Jondiko, J.I. (1985) Insect Sci.
Applic., 6, 537.

© 2005 by CRC Press LLC


Insect Antifeedants 493

HIPPEASTRINE C17H17O7N
(315.32)
M.p. : 214–215°

[α]22
D : +160° (CHCl3)

H
O
OH

O
O

(1, 2) (1, 2)

SOURCE: Lycoris radiata Herb., red spider lily (Amaryllidaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Eurema hecabe mandarina Artificial diet 0.3% Medium feeding Treatment to 5th
delOrza feeding inhibition, feeding instar larvae after
(Yellow butterfly) ratio = 27.4% pre-starvation for
4 h.
0.2% Medium feeding (3)
inhibition, feeding
ratio = 23.7%

0.1% Not active at this


level, feeding ratio =
55.3%

(1) Boit, H.G. (1956) Chem Ber., 89, 1129, 2093, 2462.
(2) Kitagawa, T., Uyeo, S., and Yokoyama, N. (1959) J. Chem Soc., 3741.
(3) Numata, A., Takemura, T., Ohbayashi, H., Katsuno, T., Yamamoto, K., Sato, K., and Kobayashi, S. (1983)
Chem. Pharm. Bull., 31, 2146.

© 2005 by CRC Press LLC


494 Opender Koul

HIRSUTOLIDE C19H24O9
(396.39)
Oil

[α]24
D : +36.3° (CHCl3)

O H2C O
HO O

OH
OAc OAc

(1, 2) (1)

SOURCE: Venidium hirsutum Harv., hairy blueberry (Asteraceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius (L.) Wafer disk 8 mg/cm3 Feeding deterrence 1. Treatment given to
(Grain weevil) test coefficient = 51–100 adults.

2. Tribolium confusum Duv. Wafer disk 8 mg/cm3 Feeding deterrence 2. Treatment given to
(Confused flour beetle) test coefficient both adults and
Adults = 101–150 larvae.
Larvae = 151–200

3. Trogoderma granarium Wafer disk 8 mg/cm3 Feeding deterrence 3. Treatment given to


Everts test coefficient = larvae.
(Khapra beetle) 101–150
Neutral value = 0
Absolute feeding
deterrence value =
200
(2)

(1) Grabarczyk, H. (1975) Pol. J. Pharmacol. Pharm., 27, 107.


(2) Nawrot, J., Bloszyk, E., Grabarczyk, H., and Drozdz, B. (1982) Prace Nauk. Inst. Ochr. Roslin, 24, 27.

© 2005 by CRC Press LLC


Insect Antifeedants 495

HISPIDULIN C16H12O6
(300.27)
M.p. : 304–305°
(291–292°)

HO O
OH

H3CO

OH O

(1, 2, 3) (1, 2)

SOURCE: Tithonia diversifolia (Hemsl.) Gray, Mexican sunflower (Asteraceae) (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Philosamia ricini Hutt. Leaf disk test 1.0% Feeding deterrence = Treatment to 0 to
(Eri-silkworm) 96.3% 12–h-old 4th instar
larvae.
0.5% Feeding deterrence = (3)
84.0%

0.25% Feeding deterrence = FI50 = 0.063%


62.7% Calculated from
Reference 3.
0.05% Feeding deterrence =
49.6%

0.02% Feeding deterrence =


32.2%

(1) Herz, W. and Sumi, Y. (1964) J. Org. Chem., 29, 3438.


(2) Herz, W. and Sumi, Y. (1966) Tetrahedron, 22, 1907.
(3) Dutta, P., Bhattacharyya, P.R., Rabha, L.C., Bordoloi, D.N., Barua, N.C., Chowdhury, P.K., Sharma, R.P., and
Barua, J.N. (1986) Phytoparasitica, 14, 77.

© 2005 by CRC Press LLC


496 Opender Koul

HOMOARGININE C7H16O2N4
(188.23)
M.p. : 207–209°

[α]22
D : +13° (HCl)

COOH

H 2N C H
NH

(CH2)4NHC
NH2

(1, 2) (1, 2)

SOURCE: Acacia spp. (Fabaceae) (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Anacridium melanorhodon Glass 1% of disk wt. Feeding deterrence = 1. Treatment to 3rd to


arabafrum (Dirsh.) fiber disk 30–60% 6th instar larvae at
(Tree locust) test random.
2% of disk wt. Feeding deterrence = (3)
91–100%

2. Locusta migratoria Glass 0.1% of Feeding deterrence = 2. Treatment to male


migratoriodes (R & F) fiber disk disk wt. 30–60% 5th instar nymphs.
(Migratory locust) test (3)
0.25% of Feeding deterrence =
disk wt. 61–90%

0.5% of Feeding deterrence =


disk wt. 91–100%

(1) Steib, H. (1926) Z. Physiol. Chem., 155, 292.


(2) Greenstein, J.P. (1937) J. Org. Chem., 2, 480.
(3) Evans, C.S. and Bell, E.A. (1979) Phytochemistry, 18, 1807.

© 2005 by CRC Press LLC


Insect Antifeedants 497

HOMOERIODICTYOL C16H14O6
(302.28)
M.p. : 224°

[α]20
D : –28.2° (EtOH))
OCH3

OH

HO O

OH O

(1, 2) (1, 2)

SOURCE: Eriodictyon californicum (Hook and Arn) Torr., (Hydrophylaceae) (1, 3)


Semisynthetic preparation as well.

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Schizaphis graminum Artificial diet 0.04% Feeding deterrence = 1. Treatment to


(Rondani) feeding 50.0% 50–75 aphids at
(Green bug) random up to 24 h.
(3)

2. Myzus persicae (Sulzer) Artificial diet 0.07% Feeding deterrence = 2. Treatment to


(Green peach aphid) feeding 50.0% 50–75 aphids at
random up to 8 h.

Concentrations =
EC50 values.
(3)

(1) Geissman, T.A. (1940) J. Am. Chem. Soc., 62, 3258.


(2) Shinoda, J. and Sato, S. (1929) J. Pharm. Soc, Jap., 49, 64.
(3) Dreyer, D.L. and Jones, K.C. (1981) Phytochemistry, 20, 2489.

© 2005 by CRC Press LLC


498 Opender Koul

HOMOGYNOLIDE–A C20H28O4
(332.44)
M.p. : 62–65°

H2C O

O
O

(1) (1, 2)

SOURCE: Homogyne alpina (L.) Cass., alpine coltsfoot (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius (L.) Wafer disk 10 mg/ml Feeding deterrence 1. Treatment given to
(Grain weevil) test coefficient = 150 adults.

2. Tribolium confusum Duv. Wafer disk 10 mg/ml Feeding deterrence 2. Treatment given to
(Confused flour beetle) test coefficient both adults and
Adults = 110 larvae.
Larvae = 136

3. Trogoderma granarium Wafer disk 10 mg/ml Feeding deterrence 3. Treatment given to


Everts test coefficient = 160 larvae.
(Khapra beetle)
Neutral value = 0
Absolute feeding
deterrence value =
200
(2)

(1) Harmatha, J., Samek, Z., Synackova, M., Novotny, L., Herout, V., and Sorm, F. (1976) Coll. Czech. Chem.
Commun., 41, 2047.
(2) Nawrot, J., Harmatha, J., and Bloszyk, E. (1986) In E. Donahaye and S. Navarro (eds.), Proc. 4th Int. Work
Conf. Stored Product Protection, Tel Aviv, Israel, pp. 591–597.

© 2005 by CRC Press LLC


Insect Antifeedants 499

HOMOGYNOLIDE–B C20H28O4
(332.44)
Oil
H2C O

(1) (1, 2)

SOURCE: Homogyne alpina (L.) Cass., alpine coltsfoot (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius (L.) Wafer disk 10 mg/ml Feeding deterrence 1. Treatment given to
(Grain weevil) test coefficient = 140 adults.

2. Tribolium confusum Duv. Wafer disk 10 mg/ml Feeding deterrence 2. Treatment given to
(Confused flour beetle) test coefficient both adults and
Adults = 165 larvae.
Larvae = 135

3. Trogoderma granarium Wafer disk 10 mg/ml Feeding deterrence 3. Treatment given to


Everts test coefficient = 170 larvae.
(Khapra beetle)
Neutral value = 0
Absolute feeding
deterrence value =
200
(2)

(1) Harmatha, J., Samek, Z., Synackova, M., Novotny, L., Herout, V., and Sorm, F. (1976) Coll. Czech. Chem.
Commun., 41, 2047.
(2) Nawrot, J., Harmatha, J., and Bloszyk, E. (1986) In E. Donahaye and S. Navarro (eds.), Proc. 4th Int. Work
Conf. Stored Product Protection, Tel Aviv, Israel, pp. 591–597.

© 2005 by CRC Press LLC


500 Opender Koul

HORDENINE-SULPHATE [C10H15ON] 2 H2SO4


(330.47)
M.p. : 209–211°
(205° anhydrous)

H2SO4.2 H2O

2
OH

(1) (1)

SOURCE: Synthetic sample (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Nilaparvata lugens (Stal.) Sucrose 1000 ppm 87% Feeding inhibition 1. Treatment to adult
(Brown planthopper) solution 100 ppm 73% Feeding inhibition females.
feeding 10 ppm 51% Feeding inhibition (1)

2. Sogatella furcifera (Horvath) Sucrose 1000 ppm 86% Feeding inhibition 2. Treatment to adult
(Planthopper) solution 100 ppm 59% Feeding inhibition females.
feeding 10 ppm 52% Feeding inhibition (1)

3. Laodelphax striatella Sucrose 1000 ppm 93% Feeding inhibition 3. Treatment to adult
(Fallen) solution 100 ppm 89% Feeding inhibition females.
(Planthopper) feeding 10 ppm 57% Feeding inhibition (1)

4. Nephotettix cincticeps (Uhler) Sucrose 1000 ppm 83% Feeding inhibition 4. Treatment to adult
(Fruit leafhopper) solution 100 ppm 69% Feeding inhibition females.
feeding 10 ppm 39% Feeding inhibition (1)

(1) Kurata, S. and Sogawa, K. (1976) Appl. Ent. Zool., 11, 89.

© 2005 by CRC Press LLC


Insect Antifeedants 501

6,7-EPOXY-2,9-HUMULADIENE C15H24O
(220.18)
Oil

B.p. : 105–106°/1.5 mm

O [α]30
D : –31.2° (CHCl3)

(1) (1,2)

SOURCE: Senecio palmensis Chr.Sm., groundsel (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera littoralis (Boisd.) Choice >200 nmol/cm2 Feeding deterrence = 1. Treatment to 6th
(Eygyptian cotton leaf worm) feeding 50.0% instar larvae.
assay

2. Leptinotarsa decemlineata Choice 28.7 nmol/cm2 Feeding deterrence = 2. Treatment to


(Say) feeding 50.0% adults.
(Colorado potato beetle) assay

3. Myzus persicae (Sulzer) Choice >200 nmol/cm2 Feeding deterrence = 3. Treatment to


(Green peach aphid) feeding 50.0% apterous adult
assay aphids.

4. Rhopalosiphum padi (L.) Choice >200 nmol/cm2 Feeding deterrence = 4. Treatment to


(Cereal aphid) feeding 50.0% apterous adult
assay aphids.

5. Sitobion avenae (Fab.) Choice >200 nmol/cm2 Feeding deterrence = 5. Treatment to


(Grass aphid) feeding 50.0% apterous adult
assay aphids.

6. Diuraphis noxia (Mordvilko) Choice >180 nmol/cm2 Feeding deterrence = 6. Treatment to


(Wheat aphid) feeding 50.0% apterous adult
assay aphids.
Concentrations =
EC50 values
(1)

(1) Reina, M., Nold, M., Santana, O., Orihuela, J.C., and Gonzalez-Coloma, A. (2002) J. Nat. Prod., 65, 448.
(2) (2000) Dictionary of Natural Products, Chapman & Hall, London.

© 2005 by CRC Press LLC


502 Opender Koul

HYDRASTINE C21H21O6N
(383.40)
M.p. : 162–163.5°

[α]D : –141° (CHCl3)


O

N
O
H H

CH3O

O
OCH3

(1, 2) (1)

SOURCE: Hydrastis canadensis L., goldenseal (Papaveraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Diabrotica virgifera virgifera Leaf disk test 69.0 nmol/ Feeding inhibition = Treatment to adults
LeConte 1.5 cm2 100% after 24 h of cyclodiene-
(Western corn rootworm) disk resistant insects.
Feeding inhibition = (2)
92.5% after 48 h
Data calculated from
Reference 2.

(1) Ohta, M., Tani, H., and Morozumi, S. (1963) Tetrahedron Lett., 859.
(2) Mullin, C.A., Mason, C.H., Chou, J., and Linderman, J.R. (1992) In C.A. Mullin and J.G. Scott (eds.),
Molecular Mechanism of Insecticide Resistance: Diversity Among Insects, ACS Symp. Ser. 505, Washington,
D.C., pp. 288–308.

© 2005 by CRC Press LLC


Insect Antifeedants 503

14-HYDROAJUGAPITIN-2,15-DIONE C29H40O11
(564.63)
O [α]20
D : +1.41° (CHCl3)

O
H

O
H

C2H5CH CH3 COO


O
CH2
OCOCH3

OCOCH3
(1, 2) (1)

SOURCE: Synthetic (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera littoralis (Boisd.) Leaf disk 10 µg/cm2 Feeding ratio = Treatment to newly
(Egyptian cotton leaf worm) choice test 0.48 ± 0.07 ecdysed 5th instar
larvae. Data based on
the ratio when 50%
of control disk was
consumed.
Feeding ratio < 0.5 is
excellent antifeedant
activity.
(2)

(1) Camps, F., Coll, J., and Dargallo, O. (1984) Phytochemistry, 23, 2577.
(2) Belles, X., Camps, F., Coll, J., and Piulachs, M.D. (1985) J. Chem. Ecol., 11, 1439.

© 2005 by CRC Press LLC


504 Opender Koul

14-HYDRO-15-HYDROXYAJUGAPITIN C29H44O11
(568.66)
OH Oil

O [α]20
D : +1.41° (CHCl3)
H

O
H H

HO

C2H5CHCH3COO
O
CH2
OCOCH3

OCOCH3
(1, 2) (1)

SOURCE: Ajuga chamaepitys (L.) Schreb., ground pine (Labiatae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera littoralis (Boisd.) Leaf disk 1 µg/cm2 Feeding ratio = Treatment to newly
(Egyptian cotton leaf worm) choice test 0.30 ± 0.09 ecdysed 5th instar
larvae. Data based on
0.1 µg/cm2 Feeding ratio = the ratio when 50%
0.37 ± 0.08 of control disk was
consumed.
Feeding ratio < 0.5 is
excellent antifeedant
activity.
(2)

(1) Camps, F., Coll, J., and Dargallo, O. (1984) Phytochemistry, 23, 2577.
(2) Belles, X., Camps, F., Coll, J., and Piulachs, M.D. (1985) J. Chem. Ecol., 11, 1439.

© 2005 by CRC Press LLC


Insect Antifeedants 505

6-HYDROXYARISTOLOCHIC ACID C17H11O8N


(357.28)
M.p. : 269–271°

COOH
O

NO2
O

HO OCH3

(1) (1)

SOURCE: Aristolochia albida Duch., Nigerian climber (Aristolochiaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura Fab. Leaf disk 1000 ppm Antifeedant index Treatment to 4-day-
(Tobacco armyworm) choice test value = 0 old larvae for
24 hours.
500 ppm Antifeedant index Antifeedant index
value = 21.4 value below 20
highly deterrent.
(1)

(1) Lajide, L., Escoubas, P., and Mizutani, J. (1993) J. Agric. Food Chem., 41, 669.

© 2005 by CRC Press LLC


506 Opender Koul

11-β-HYDROXY-5α-(ANGELOYLOXY) C20H24O4
SILPHINEN-3-ONE (328.39)
Only spectral data given

OH

O O

(1, 2) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Leptinotarsa decemlineata Leaf disk 14.56 µg/cm2 Feeding inhibition = Treatments to newly
(Say) choice test 50.0% emerged 4th instar
(Colorado potato beetle) larvae for ≤ 6 h.

Leaf disk 15.04 µg/cm2 Feeding inhibition = Treatments to newly


no-choice 50.0% emerged 4th instar
test larvae for 24 h.

Concentration = FI50
value.
(1)

(1) Gonzalez-Coloma, A., Gutierrez, C., Cabrera, R., and Reina, M. (1997) J. Agric. Food Chem., 45, 946.
(1) Jakupovic, J., Abraham, W.R., and Bohlmann, F. (1985) Phytochemistry, 24, 3048.

© 2005 by CRC Press LLC


Insect Antifeedants 507

p-HYDROXYBENZALDEHYDE C7H6O2
(122.12)
M.p. : 115–116°

CHO

HO

(1) (1)

SOURCE: Sorghum bicolor (L.) Moench., grain sorghum (Poaceae) (2, 4)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Schizaphis graminum Artificial diet 0.13% Feeding inhibition = 1. Treatment to


(Rondani) feeding 50.0% 50–75 aphids at
(Green bug) random per test for
24 h.
(2)

2. Myzus persicae (Sulzer) Artificial diet 0.1% Feeding inhibition = 2. Treatment to


(Green peach aphid) feeding 50.0% 50–75 aphids at
random per test for
8 h.
(3)

3. Locusta migratoria (L.) Leaf disk 0.25% Feeding inhibition = 3. Treatment to 3rd
(Migratory locust) choice test 70.0% instar larvae.
(4)
1.0% Feeding inhibition =
95.0%

(1) (1994) Dictionary of Natural Products, Chapman & Hall, London.


(2) Dreyer, D.L., Reese, J.C., and Jones, K.C. (1981) J. Chem. Ecol., 7, 273.
(3) Dreyer, D.L. and Jones, K.C. (1981) Phytochemistry, 20, 2489.
(4) Woodhead, S., Galeffi, C., and Bettolo, G.B.M. (1982) Phytochemistry, 21, 455.

© 2005 by CRC Press LLC


508 Opender Koul

4-HYDROXY-3-ARYLCOUMARYL C15H8O5
QUINONE (268.22)
No physical data given

O O

OH
O

(1) (1)

SOURCE: Synthetic sample (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Costelytra zealandica (White) Artificial diet 200 µg/g Feeding inhibition = Treatment to 24-h
(Scarab beetle) feeding 35.1% pre-starved 3rd instar
larvae.
(1)

Data calculated from


Reference 1.

(1) Lane, G.A., Biggs, D.R., Russel, G.B., Sutherland, O.R.W., Williams, E.M., Maindonald, J.H., and Donnell,
D.J. (1985) J. Chem. Ecol., 11, 1713.

© 2005 by CRC Press LLC


Insect Antifeedants 509

p-HYDROXYBENZOIC ACID C7H6O3


(138.12)
M.p. : 213–214°

COOH

OH

(1) (1)

SOURCE: Sorghum bicolor (L.) Moench., grain sorghum (Poaceae) (2, 4)


Pteridium aquilinum L. Kuhn, bracken fern (Pteridophyta)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Schizaphis graminum Artificial 0.36% Feeding inhibition = 1. Treatment to


(Rondani) diet feeding 50.0% 50–75 aphids at
(Green bug) random per test for
24 h.
(2)

2. Myzus persicae (Sulzer) Artificial 0.2% Feeding inhibition = 2. Treatment to


(Green peach aphid) diet feeding 50.0% 50–75 aphids at
random per test for
8 h.
(3)

3. Pieris brassicae (L.) Leaf disk 7.2 × 10–2 M Feeding inhibition 3. Treatment to
(Large white butterfly) no-choice index = 1.0 2-day-old 5th instar
test Feeding ratio = 2.87 larvae.
(4)

(1) (1994) Dictionary of Natural Products, Chapman & Hall, London.


(2) Dreyer, D.L., Reese, J.C., and Jones, K.C. (1981) J. Chem. Ecol., 7, 273.
(3) Dreyer, D.L. and Jones, K.C. (1981) Phytochemistry, 20, 2489.
(4) Jones, C.G. and Firn, R.D. (1979) Biochem. Syst. Ecol., 7, 187.

© 2005 by CRC Press LLC


510 Opender Koul

6β-HYDROXYEREMOPHILENOLIDE C15H22O3
(250.34)
M.p. : 208°

[α]D : +205.8° (CHCl3)


H

OH

(1, 2) (1)

SOURCE: Petasites albus (L.) J. Gaertn., butterbur (Asteraceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius (L.) Wafer disk 10 mg/ml Feeding deterrence 1. Treatment given to
(Grain weevil) test coefficient = − 3 adults.

2. Tribolium confusum Duv. Wafer disk 10 mg/ml Feeding deterrence 2. Treatment given to
(Confused flour beetle) test coefficient = both adults and
Adults = 84 larvae.
Larvae = 82

3. Trogoderma granarium Wafer disk 10 mg/ml Feeding deterrence = 3. Treatment given to


Everts test coefficient = 59 larvae.
(Khapra beetle)
Neutral value = 0
Absolute feeding
deterrence value =
200
(2)

(1) Novotny, L., Herout, V., and Sorm, F. (1964) Collect. Czech. Chem. Commun., 29, 2187.
(2) Harmatha, J. and Nawrot, J. (1984) Biochem. Syst. Ecol., 12, 95.

© 2005 by CRC Press LLC


Insect Antifeedants 511

γ-HYDROXYFERRUGININ–A C30H36O5
(476.61)
Only spectral data given

OH O
OH

OH

OH
(1, 2) (1)

SOURCE: Synthetic (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera exempta (Walker) Glass fiber 10–3 M Feeding inhibition = 1. Treatment to last
(Nut grass armyworm) disk test 56.36% instar larvae.
(2)

2. Heliothis virescens (Fab.) Glass fiber 10–3 M Feeding inhibition = 2. Treatment to last
(Tobacco bud worm) disk test 47.97% instar larvae.
(2)

3. Helicoverpa armigera Glass fiber 10–3 M Feeding inhibition = 3. Treatment to last


(Hubner) disk test 38.69% instar larvae.
(Gram pod borer) (2)

4. Locusta migratoria (L.) Glass fiber 10–3 M Feeding inhibition = 4. Treatment to last
(Migratory locust) disk test 56.42% instar larvae.
(2)

(1) Delle Monache, F., Torres, F., Bettolo, G.B.M., and Alves De Lima, R. (1980) Lloydia, 43, 487.
(2) Simmonds, M.S.J., Blaney, W.M., Delle Monache, F., Mac-Quhae, M.M., and Bettolo, G.B.M. (1985) J.
Chem. Ecol., 11, 1593.

© 2005 by CRC Press LLC


512 Opender Koul

γ-γ-HYDROXYFERRUGININ–A C30H36O6
(492.61)
No physical data given

OH OH O

OH

OH

OH
(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera exempta (Walker) Glass fiber 10–3 M Feeding inhibition = 1. Treatment to last
(Nut grass armyworm) disk test 62.64% instar larvae.
(1)

(1) Simmonds, M.S.J., Blaney, W.M., Delle Monache, F., Mac-Quhae, M.M., and Bettolo, G.B.M. (1985) J.
Chem. Ecol., 11, 1593.

© 2005 by CRC Press LLC


Insect Antifeedants 513

7-HYDROXYFLAVONONE C15H10O3
(238.24)
M.p. : 244°
(240°)

HO O

(1, 2) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera exempta (Walker) Glass fiber 100 ppm Feeding inhibition = 1. Treatment to 24- to
(Nut grass armyworm) disk dual 73.0% 36-h-old final
choice test stadium larvae for
10 ppm Feeding inhibition = 5 h. Larvae were pre-
59.0% starved for 4 h.
(2)

2. Spodoptera littoralis (Boisd.) Glass fiber 100 ppm Feeding inhibition = 2. Treatment to 24- to
(Egyptian cotton leaf worm) disk dual 17.0% 36-h-old final
choice test stadium larvae for
5 h. Larvae were pre-
starved for 4 h.
(2)

(1) Looker, J.H., and Hanneman, W.W. (1962) J. Org. Chem., 27, 381.
(2) Simmonds, M.S.J., Blaney, W.M., Delle Monache, F., and Bettolo, G.B.M. (1990) J. Chem. Ecol., 16, 365.

© 2005 by CRC Press LLC


514 Opender Koul

2′-HYDROXYFORMONONETIN C16H12O5
(284.27)
M.p. : 215–217°
(220–222°)

HO O

O
HO OCH3

(1) (1)

SOURCE: Synthetic sample (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Costelytra zealandica (White) Artificial diet 14 µg/g Feeding inhibition = Treatment to 24-h
(Scarab beetle) feeding 50.0% pre-starved 3rd instar
larvae.
(1)

Data calculated from


Reference 1.

(1) Lane, G.A., Biggs, D.R., Russel, G.B., Sutherland, O.R.W., Williams, E.M., Maindonald, J.H., and Donnell,
D.J. (1985) J. Chem. Ecol., 11, 1713.

© 2005 by CRC Press LLC


Insect Antifeedants 515

2′-HYDROXYGENISTEIN C15H10O6
(286.24)
M.p. : 270–273°

HO O

OH O
HO OH

(1, 2) (1)

SOURCE: Lupinus angustifolius L., European blue lupine (Fabaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Costelytra zealandica (White) Artificial diet 20 µg/g Feeding inhibition = Treatment to 24-h
(Scarab beetle) feeding 50.0% pre-starved 3rd instar
larvae.
(2)

(1) Lane, G.A., Sutherland, O.R.W., and Skipp, R.A. (1987) J. Cherm. Ecol., 13, 771.
(2) Lane, G.A., Biggs, D.R., Russel, G.B., Sutherland, O.R.W., Williams, E.M., Maindonald, J.H., and Donnell,
D.J. (1985) J. Chem. Ecol., 11, 1713.

© 2005 by CRC Press LLC


516 Opender Koul

3-HYDROXYGRANDIOLIDE C15H22O4
(266.34)
M.p. : 65°

CH2 [α]24
D : –25° (CHCl3)
H OH

HO

H
O

(1, 2) (1)

SOURCE: Arctotis grandis Thunb., African daisy (Asteraceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius (L.) Wafer disk 10 mg/cm3 Feeding deterrence 1. Treatment given to
(Grain weevil) test coefficient = 40.9 adults.

2. Tribolium confusum Duv. Wafer disk 10 mg/cm3 Feeding deterrence 2. Treatment given to
(Confused flour beetle) test coefficient both adults and
Adults = 89.5 larvae.
Larvae = 89.6

3. Trogoderma granarium Wafer disk 10 mg/cm3 Feeding deterrence 3. Treatment given to


Everts test coefficient = − 37.7 larvae.
(Khapra beetle)
Neutral value = 0
Absolute feeding
deterrence value =
200
(2)

(1) Holub, M., Samek, Z., Le, V.N.P., Grabarczyk, H., and Drozdz, B. (1979) Conf. on Isoprenoids, Torun., p. 66.
(2) Nawrot, J., Bloszyk, E., Grabarczyk, H., Drozdz, B., Daniewski, W.M., and Holub, M. (1983) Prace. Nauk.
Inst. Ochr. Roslin, 25, 91.

© 2005 by CRC Press LLC


Insect Antifeedants 517

5-HYDROXY-2-HEXEN-4-OLIDE C6H8O3
(128.13)
Colourless oil
Distilled at
90–100°/0.05 mm

H
H

O
O
OH

(1, 2) (1)

SOURCE: Osmunda japonica (L.) Thunb., flowering fern (Osmundaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Eurema hecabe mandarina Artificial diet 0.78% Medium feeding Treatment to 5th
delOrza feeding inhibition, feeding instar larvae after
(Yellow butterfly) ratio = 38.0% pre-starvation for
4 h.
(2)

(1) Hollenbeak, K.H. and Kuehne, M.E. (1974) Tetrahedron, 30, 2307.
(2) Numata, A., Hokimoto, K., Takemura, T., and Fukui, S. (1983) Appl. Ent. Zool., 18, 129.

© 2005 by CRC Press LLC


518 Opender Koul

5-HYDROXY-1-(4-HYDROXY-3-METHOXY PHENYL) C17H26O4


DECAN-3-ONE (294.39)
Oil

[α]D : +26.5° (CHCl3)

O OH

H3CO

HO

(1, 2) (1, 2, 3)

SOURCE: Aframomum melegueta (Roscoe) K. Schum. Cameroon cardamom (Zingiberaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Reticulitermes speratus Kolbe Paper disk 5000 ppm Antifeedant index Treatment to 3rd
(Subterranean termite) choice assay value = 8.2 instar workers.
Feeding duration =
2500 ppm Antifeedant index 14 days.
value = 3.0 Antifeedant index
value below 20 =
1000 ppm Antifeedant index highly deterrent.
value = 19.6 (2)

(1) Kikuzaki, H., Tsai, S., and Nakatani, N. (1992) Phytochemistry, 31, 1783.
(2) Escoubas, P., Lajide, L., and Mizutani, J. (1995) Phytochemistry, 40, 1097.
(3) Connell, D.W. and Sutherland, M.D. (1969) Aust. J. Chem., 22, 1033.

© 2005 by CRC Press LLC


Insect Antifeedants 519

2α-HYDROXYISOCOSTIC ACID C15H22O3


(250.34)
M.p. : 153–156°

[α]20
D : +48.4° (CHCl3)

HO

CH2

H
COOH

(1) (1)

SOURCE: Dittrichia viscosa (L.) Grenter., inula (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius (L.) Wafer disk 10 mg/cm3 Feeding deterrence 1. Treatment given to
(Grain weevil) test coefficient = 151.1 adults.

2. Tribolium confusum Duv. Wafer disk 10 mg/cm3 Feeding deterrence 2. Treatment given to
(Confused flour beetle) test coefficient both adults and
Adults = 138.2 larvae.
Larvae = 143.9

3. Trogoderma granarium Wafer disk 10 mg/cm3 Feeding deterrence 3. Treatment given to


Everts test coefficient = 69.5 larvae.
(Khapra beetle)
Neutral value = 0
Absolute feeding
deterrence value =
200
(1)

(1) Daniewski, W.M., Kroszczynski, W., Bloszyk, E., Drozdz, B., Nawrot, J., Rychlewska, U., Budesinsky, M.,
and Holub, M. (1986) Collect. Czech. Chem. Commun., 51, 1710.

© 2005 by CRC Press LLC


520 Opender Koul

5-HYDROXYISODERRICIN C21H22O4
(7-methyl-grabanin) (338.40)
No physical data given

H3CO O

OH O

(1) (1)

SOURCE: Tephrosia villosa Pers., tephrosia (Fabaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera exempta (Walker) Glass fiber 100 ppm Feeding inhibition = 1. Treatment to 24- to
(Nut grass armyworm) disk dual- 71.0% 36-h-old final
choice test stadium larvae for
10 ppm Feeding inhibition = 5 h. Larvae were pre-
42.0% starved for 4 h.
(1)

2. Spodoptera littoralis (Boisd.) Glass fiber 100 ppm Feeding inhibition = 2. Treatment to 24- to
(Egyptian cotton leaf worm) disk dual- 53.0% 36-h-old final
choice test stadium larvae for
5 h. Larvae were pre-
starved for 4 h.
(1)

(1) Simmonds, M.S.J., Blaney, W.M., Delle Monache, F., and Bettolo, G.B.M. (1990) J. Chem. Ecol., 16, 365.

© 2005 by CRC Press LLC


Insect Antifeedants 521

3-HYDROXY-4-METHOXY C10H10O4
CINNAMIC ACID (194.19)
M.p. : 233–234°
(228°)

COOH

OH

OCH3

(1, 2) (1, 3)

SOURCE: Commercial sample (2)


Also isolated from Cimicifuga racemosa (L.) Nutt., black bugbane (Ranunculaceae) and Catalpa
ovata Don., catalpa (Bignoneaceae)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Pieris brassicae (L.) Leaf disk 5.2 × 10–2 M Feeding inhibition Treatment to 2-day-
(Large white butterfly) no-choice index = 1.0 old 5th instar larvae.
test Feeding ratio = 2.82 (2)

Ratio < 20 highly


deterrent

(1) Robinson, R. and Sugasawa, S. (1931) J. Chem. Soc., 3169.


(2) Jones, C.G. and Firn, R.D. (1979) Biochem. Syst. Ecol., 7, 187.
(3) Blasé, F.R. and Banerjee, K. (1995) Synth. Commun., 25, 3187.

© 2005 by CRC Press LLC


522 Opender Koul

1- (4-HYDROXY-3-METHOXYPHENYL) C17H26O3
DECAN-3-ONE (278.39)
M.p. : 27–29°
(31–32°)

H3CO

HO

(1, 2) (1, 2)

SOURCE: Aframomum melegueta (Roscoe) K. Schum., Cameroon cardamom (Zingiberaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Reticulitermes speratus Kolbe Paper disk 7500 ppm Antifeedant index Treatment to 3rd
(subterranean termite) choice assay value = 10.2 instar workers.
Feeding duration =
5000 ppm Antifeedant index 14 days.
value = 22.8 Antifeedant index
value below 20
1000 ppm Antifeedant index considered as highly
value = 17.6 deterrent.
(2)

(1) Tackie, A.N., Dwuma-Dadu, D., Ayim, J.S.K., Dabra, T., Knapp, J.E., Slatken, D.J., and Schiff, P.L. (1975)
Phytochemistry, 14, 853.
(2) Escoubas, P., Lajide, L., and Mizutani, J. (1995) Phytochemistry, 40, 1097.

© 2005 by CRC Press LLC


Insect Antifeedants 523

4′-HYDROXY-7-METHOXYFLAVAN C16H16O3
(256.30)
M.p. : 148.5–149.5°

[α]21
D : –15.6° (EtOH)
H

OH
H

H3CO O

(1, 2) (1)

SOURCE: Lycoris radiata Herb., red spider lily (Amaryllidaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Eurema hecabe mandarina Artificial diet 0.8% Medium feeding Treatment to 5th
delOrza feeding inhibition, feeding instar larvae after
(Yellow butterfly) ratio = 20.8% pre-starvation for
4 h.

0.4% Slight feeding 0.2% treatment level


inhibition, feeding has been
ratio = 27.5% exceptionally active
level.
0.2% Strong feeding (2)
inhibition, feeding
ratio = 19.1%

0.05% Not active at this


level, feeding ratio =
66.5%

(1) Cooke, R.G. and Down, J.G. (1971) Aust. J. Chem., 24, 1257.
(2) Numata, A., Takemura, T., Ohbayashi, H., Katsuno, T., Yamamoto, K., Sato, K., and Kobayashi, S. (1983)
Chem. Pharm. Bull., 31, 2146.

© 2005 by CRC Press LLC


524 Opender Koul

(–)-3′-HYDROXY-4′-METHOXY-7- C17H18O4
HYDROXY-8-METHYLFLAVAN (286.33)
[α]20
D : –31° (CHCl3)

OH

OCH3

HO O

(1) (1)

SOURCE: Lycoris radiata Herb., red spider lily (Amaryllidaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Eurema hecabe mandarina Artificial diet 0.8% Strong feeding Treatment to 5th
delOrza feeding inhibition, feeding instar larvae after
(Yellow butterfly) ratio = 7.2% pre-starvation for
4 h.
0.2% Strong feeding (1)
inhibition, feeding
ratio = 11.6%

0.05% Slight feeding


inhibition, feeding
ratio = 35.8%

(1) Numata, A., Takemura, T., Ohbayashi, H., Katsuno, T., Yamamoto, K., Sato, K., and Kobayashi, S. (1983)
Chem. Pharm. Bull., 31, 2146.

© 2005 by CRC Press LLC


Insect Antifeedants 525

2-HYDROXY-4-METHOXY BENZALDEHYDE C8H8O3


(152.15)
B.p. : 75–78°/0.4 mm

n 25
D : 1.5727
CHO

OH

OCH3

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Acalymma vittatum (Fab.) Leaf disk test 0.1% Feeding inhibition = Treatment to adult
(Striped cucumber beetle) 100% up to 6 h. beetles.
(1)
0.5% Feeding inhibition =
100% up to 22 h.

(1) Reed, D.K. and Jacobson, M. (1983) Experientia, 39, 378.

© 2005 by CRC Press LLC


526 Opender Koul

2-HYDROXY-3-METHOXY BENZALDEHYDE C8H8O3


(152.15)
B.p. : 80–85°/0.5 mm

n25
D : 1.5730

CHO

OH

OCH3

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Acalymma vittatum (Fab.) Leaf disk test 0.5% Feeding inhibition = Treatment to adult
(Striped cucumber beetle) 100% up to 22 h. beetles.
(1)

(1) Reed, D.K. and Jacobson, M. (1983) Experientia, 39, 378.

© 2005 by CRC Press LLC


Insect Antifeedants 527

1- (4-HYDROXY-3-METHOXYPHENYL) C17H24O3
DEC-5-EN-3-ONE (276.38)
Oil

H3CO

HO

(1, 2) (1, 2)

SOURCE: Aframomum melegueta (Roscoe) K. Schum. (Cameroon Cardamom Zingiberaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Reticulitermes speratus Kolbe Paper disk 7500 ppm Antifeedant index Treatment to 3rd
(Subterranean termite) choice assay value = 17.5 instar workers.
Feeding duration =
5000 ppm Antifeedant index 14 days.
value = 15.2 Antifeedant index
value below 20
highly deterrent.
(2)

(1) Tackie, A.N., Dwuma-Dadu, D., Ayim, J.S.K., Dabra, T., Knapp, J.E., Slatken, D.J., and Schiff, P.L. (1975)
Phytochemistry, 14, 853.
(2) Escoubas, P., Lajide, L., and Mizutani, J. (1995) Phytochemistry, 40, 1097.

© 2005 by CRC Press LLC


528 Opender Koul

E-3-(4-HYDROXY-3-METHOXYPHENYL) –N-2- C18H19O4N


[4-HYDROXYPHENYLETHYL]-2-PROPENAMIDE (313.35)
Only spectral data given

OH
O

H3CO
N
H

HO

(1, 2) (1, 2)

SOURCE: Xylopia aethiopica A. Rich., African pepper (Anonaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Reticulitermes speratus Kolbe Paper disk 7500 ppm Antifeedant index Treatment to 3rd
(Subterranean termite) choice assay value = 8.5 instar workers.
Feeding duration =
5000 ppm Antifeedant index 14 days.
value = 24.8 Antifeedant index
value below 20
highly deterrent.
(2)

(1) Yoshihara, T., Takamatsu, S., and Sakamura, S. (1978) Agric. Biol. Chem., 42, 623.
(2) Lajide, L., Escoubas, P., and Mizutani, J. (1995) Phytochemistry, 40, 1105.

© 2005 by CRC Press LLC


Insect Antifeedants 529

6α-HYDROXYGRINDELIC ACID C20H32O4


(336.47)
M.p. : 106–108°

[α]D : +19.3° (CHCl3)

COOH
O

OH (α)

(1) (1)

SOURCE: Grindelia humilis Hook and Arn, hairy gumweed (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Schizaphis graminum (Rondani) Artificial diet 0.02% Feeding inhibition = Treatment to 50–75
(Wheat aphid) feeding 50.0% aphids at random per
test for 24 h.
(1)

(1) Rose, A.F., Jones, K.C., Haddon, W.F., and Dreyer, D.L. (1981) Phytochemistry, 20, 2249.

© 2005 by CRC Press LLC


530 Opender Koul

6β-HYDROXYGRINDELIC ACID C20H32O4


(336.47)
M.p. : 147–150°

[α]D : –151.5° (CHCl3)

COOH
O

OH (β)

(1) (1)

SOURCE: Grindelia humilis Hook and Arn, hairy gumweed (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Schizaphis graminum (Rondani) Artificial diet 0.02% Feeding inhibition = Treatment to 50–75
(Wheat aphid) feeding 50.0% aphids at random per
test for 24 h.
(1)

(1) Rose, A.F., Jones, K.C., Haddon, W.F., and Dreyer, D.L. (1981) Phytochemistry, 20, 2249.

© 2005 by CRC Press LLC


Insect Antifeedants 531

18-HYDROXYGRINDELIC ACID C20H32O4


(336.47)
Oil

[α]D : –82.6° (CHCl3)

COOH
O

OH

(1) (1, 2)

SOURCE: Chrysothamnus nauseosus (Pall.) Britt., rubber rabbitbush (Asteraceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Schizaphis graminum (Rondani) Artificial diet 0.002% Feeding inhibition = Treatment to 50–75
(Wheat aphid) feeding 50.0% aphids at random per
test for 24 h.
(1, 2)

(1) Rose, A.F. (1980) Phytochemistry, 19, 2689.


(2) Rose, A.F., Jones, K.C., Haddon, W.F., and Dreyer, D.L. (1981) Phytochemistry, 20, 2249.

© 2005 by CRC Press LLC


532 Opender Koul

6-HYDROXYPICRASIN–B C21H28O7
(392.45)
M.p. : 285–290°

OCH3 [α]D : –48.2° (CHCl3)

O
O

HO O

H
O
H
OH

(1, 2) (1)

SOURCE: Soulamea pancheri Brongn. & Griseb. (Simaroubaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Heliothis virescens (Fab.) Leaf disk 19.8 µg/cm2 Feeding inhibition = 1. Treatment to 3rd
(Tobacco budworm) test 30–60% after 2 days instar larvae.
and 0–30% after (2)
6 days

(1) Viala, B. and Polonsky, J. (1970) Compt. Rend., 271C, 410.


(2) Lidert, Z., Wing, K., Polonsky, J., Imakuram, Y., Okano, M., Tani, S., Lin, Y., Kiyokawa, H., and Lee, K.H.
(1987) J. Nat. Prod., 50, 442.

© 2005 by CRC Press LLC


Insect Antifeedants 533

6-HYDROXYSANDORICIN C31H40O12
(604.65)
M.p. : 250–255° (dec.)

O O
O

O O

O
O

CH2 OH
O
OH
COOCH3

(1) (1)

SOURCE: Sandoricum koetjape (Burm. F.) Merr., Santol (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera frugiperda Artificial diet 25 ppm Feeding inhibition = Treatment to newly


(J.E. Smith) two-choice 64.0% hatched larvae for
(Fall armyworm) assay 16–20 h.
(1)

2. Ostrinia nubilalis (Hubner) Artificial diet 200 ppm Feeding inhibition = Data calculated from
(European corn borer) two-choice 70.0% Reference 1.
assay

(1) Powell, R.G., Mikolajczak, K.L., Zilkowski, B.W., Mantus, E.K., Cherry, D., and Clardy, J. (1991) J. Nat.
Prod., 54, 241.

© 2005 by CRC Press LLC


534 Opender Koul

2-HYDROXYSENEGANOLIDE C27H35O9
(503.54)
Amorphous powder
O
[α]D : +61° (MeOH)

O O
O

O
O
HO H

OH
O
(1) (1)

SOURCE: Khaya senegalensis (Desv.) A. Juss., dry-zone mahogany (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera littoralis Boisd. Leaf disk 200 ppm Feeding inhibition = Treatment to 3rd
(Egyptian cotton leaf worm) choice test (4 µg/cm2) 50% instar larvae until the
larvae had eaten
approximately 50%
of one of the disks.
(1)

(1) Nakatani, M., Abdelgaleil, S.A.M., Kurawaki, J., Okamura, H., Iwagawa, T., and Doe, M. (2001) J. Nat.
Prod., 64, 1261.

© 2005 by CRC Press LLC


Insect Antifeedants 535

21- (R,S)-HYDROXYTOONACILID C31H38O11


(586.63)
M.p. : 188–189°
O
[α]20
D : +37° (CHCl3)
O
AcO

OH
AcO

O
H
CH2
O

COOCH3
(1) (1)

SOURCE: Toona ciliata M.J. Roem var. australis, red cedar (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Epilachna varivestis Muls. Leaf disk test 25–50 ppm Feeding inhibition = Treatment to adult
(Mexican bean beetle) 100%. beetles. Absolute
antifeedant effect at
this level of
treatment within
24 h.
(1)

(1) Kraus, W. and Grimminger, W. (1980) Nouv. J. de Chimie., 4, 651.

© 2005 by CRC Press LLC


536 Opender Koul

23- (R,S)-HYDROXYTOONACILID C31H38O11


(586.63)
M.p. : 163–164°
OH
[α]20
D : +66.7° (CHCl3)
O
AcO
O
AcO

O
H
CH2
O

COOCH3
(1) (1)

SOURCE: Toona ciliata M.J. Roem var. australis, red cedar (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Epilachna varivestis Muls. Leaf disk test 0.2% Feeding inhibition = Treatment to adult
(Mexican bean beetle) 100%. beetles. Absolute
antifeedant effect at
this level of
treatment within
24 h.
(1)

(1) Kraus, W. and Grimminger, W. (1980) Nouv. J. de Chimie., 4, 651.

© 2005 by CRC Press LLC


Insect Antifeedants 537

4β-HYDROXYWITHANOLIDE–E C28H38O8
(502.60)
M.p. : 205–214°
(197–198°)

OH [α]22
D : +107° (dioxane)

O O
OH

OH

O
OH
(1, 2) (1, 2)

SOURCE: Physalis peruviana L., Peruvian ground cherry (Solanaceae) (2, 3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera littoralis (Boisd.) Styropor test 0.1% Feeding inhibition = 1. Treatment to


(Egyptian cotton leaf worm) 98.3% larvae of 170 to 190
mg body weight.
0.01% Feeding inhibition = (3)
72.6% Data calculated from
Reference 3.
0.005% Feeding inhibition =
44.9%

2. Epilachna varivestis Muls. Leaf residue 0.1% Negative weight gain 2. Treatment to 4th
(Mexican bean beetle) test of 3.23 against instar larvae for 48 h.
+12.24 in controls Weight loss
0.05% Negative weight gain considered as a result
of 3.5 against +11.59 of antifeedant effect.
in controls (4)

3. Helicoverpa zea (Boddie) Leaf disk test 250 ppm Feeding inhibition = 3. Treatment to
(Corn earworm) 50.0% larvae.
Concentration is FI50
value.
(5)

(1) Kirson, I., Abraham, A., Sethi, P.D., Subramanian, S.S., and Glotter, E. (1976) Phytochemistry, 15, 340.
(2) Sakurai, K., Ishii, H., Kobayashi, S., and Twao, T. (1976) Chem. Pharm. Bull., 24, 1403.
(3) Ascher, K.R.S., Nemney, N.E., Eliyahu, M., Kirson. I., Abraham, A., and Glotter, E. (1980) Experientia, 36,
998.
(4) Ascher, K.R.S., Schmutterer, H., Glotter, E., and Kirson. I. (1981) Phytoparasitica, 9, 197.
(5) Baumann, T.W. and Meier, C.M. (1993) Phytochemistry, 33, 317.

© 2005 by CRC Press LLC


538 Opender Koul

HYRCANOSIDE O C34H48O14
(680.74)
M.p. : 200–210°
O (177–179°)

[α]20
D : +7.4° (MeOH)

CHO

OH
O

O
HO
OH
O
HO O OH

OH OH
(1, 2) (1)

SOURCE: Coronilla varia L., crownvetch (Fabaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Peridroma saucia (Hubner) Leaf disk 14.25 µg/cm2 Feeding inhibition = 1. Treatment to 5th
(Variegated cutworm) choice test 41.5% instar larvae for 5 h.
(2)
28.5 µg/cm2 Feeding inhibition =
60.5%

57.0 µg/cm2 Feeding inhibition =


87.8%

(1) Hembree, J.A., Chang, C.J., McLaughlin, J.L., Peck, G., and Cassady, J.M. (1979) J. Nat. Prod., 42, 293.
(2) Nawrot, J., Koul, O., Isman, M.B., and Harmatha, J. (1991) J. Appl. Ent., 112, 194.

© 2005 by CRC Press LLC


Insect Antifeedants 539

IMPERATORIN C16H14O4
(270.28)
M.p. : 102°

O O O

(1, 2) (1)

SOURCE: Clausena anisata (Willd.) Hook F. Ex Benth., samanobere (Rutaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera exempta (Walker) Leaf disk test 100 ppm Feeding inhibition Treatment to larvae
(Nutgrass armyworm) observed. pre-starved for 2 h.
No quantitative data
500 ppm Feeding inhibition recorded.
observed. (2)

LD50 (mice): 330 mg/kg (ipr.) (3)

(1) Govindachari, T.R., Pai, B.R., Subramaniam, P.S., and Muthukumaraswamy, N. (1968) Tetrahedron, 24, 753.
(2) Gebreyesus, T. and Chapya, A. (1983) In T.R. Odhiambo (ed.), Natural Products for Innovative Pest Man-
agement, Current Themes in Tropical Science, Pergamon Press, Oxford, 237–241.
(3) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC


540 Opender Koul

2-IODOOCTADECANOIC ACID C18H35O2I


(410.38)
M.p. : 66°

COOH

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Incisitermes minor (Hagen) Paper towel 0.05 mg/cm2 Feeding inhibition = Treatment to larvae
(Western drywood termite) disk test 76.3% of 10 to 13 mg body
weight for 6 days.
(2)

Data calculated from


Reference 2.

(1) Frewing, J.J. (1944) Proc. Roy. Soc., A182, 270.


(2) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39.

© 2005 by CRC Press LLC


Insect Antifeedants 541

IPOLAMIIDE C17H26O11
(406.39)
M.p. : 144–145°

[α]13
D : –136° (dioxane)

COOCH3
OH

H
O

OH H
O-β-Glc

(1, 3) (1, 2)

SOURCE: Stachytarpheta mutabilis Vahl., velvet berry (Verbenaceae) (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera littoralis (Boisd.) Leaf disk test 0.1% Feeding inhibition = 1.Treatment to larvae
(Egyptian cotton leaf worm) 100% on dry weight basis.
(3)

2. Locusta migratoria (L.) Leaf disk test 2.0% Feeding inhibition = 2. Treatment to
(Migratory locust) 100% insects
0.2% Feeding inhibition = approximately
97.0% halfway through final
0.02% Feeding inhibition = larval stadium.
29.0% (3)

3. Schistocerca gregaria Leaf disk test 2.0% Feeding inhibition = 4. Treatment to


(Forsk.) 100% insects
(Desert locust) 0.2% Feeding inhibition = approximately
43.0% halfway through final
0.02% Not active larval stadium.
(3)

(1) Scarpati, M.L. (1969) Gazz. Chim. Ital., 99, 1150.


(2) Tantisewie, B. and Sticher, O. (1975) Phytochemistry, 14, 1462.
(3) Bernays, E. and DeLuca, C. (1981) Experientia, 37, 1289.

© 2005 by CRC Press LLC


542 Opender Koul

ISOALANTOLACTONE C15H20O2
(232.32)
M.p. : 115°
(109–110°)

[α]D : +172° (CHCl3)

O
O

H
CH2
CH2

(1, 2) (1, 2)

SOURCE: Inula helenium L., eleocampane (Asteraceae) (1, 3)


Eupatorium quadrangularae L., joe-pye-weed (Asteraceae) (4)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius (L.) Wafer disk 10 mg/ml Feeding deterrence 1. Treatment given to
(Grain weevil) test coefficient = 108 adults.

2. Tribolium confusum Duv. Wafer disk 10 mg/ml Feeding deterrence 2. Treatment given to
(Confused flour beetle) test coefficient both adults and
Adults = 200 larvae.
Larvae = 175

3. Trogoderma granarium Wafer disk 10 mg/ml Feeding deterrence 3. Treatment given to


Everts test coefficient = 107 larvae.
(Khapra beetle) Neutral value = 0
Absolute feeding
deterrence value =
200
(3)

4. Atta cephalotes (L.) Rye flake 0.2 mg or Feeding inhibition = 4. Treatment given to
(Leaf cutter ant) forced 4 µg/flake 36.4% adult workers. Data
choice test. calculated from
Reference 4.
(4)

(1) Asselineau, C. and Borg, S. (1958) Compt. Rend., 246, 1874.


(2) Marshall, J.A. and Cohen, N. (1964) J. Org. Chem., 29, 3727.
(3) Streibl, M., Nawrot, J., and Herout, V. (1983) Biochem. Syst. Ecol., 11, 381.
(4) Hubert, T.D., Okunade, A.L., and Wiemer, D.F. (1987) Phytochemistry, 26, 1751.

© 2005 by CRC Press LLC


Insect Antifeedants 543

Ent-ISOALANTOLACTONE C15H20O2
(232.32)
M.p. : 112–115°

H
CH2 CH2

(1, 2) (1)

SOURCE: Locopholea heterophylla, liverwort (Pteridophyta) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius (L.) Wafer disk 10 mg/ml Feeding deterrence 1. Treatment given to
(Grain weevil) test coefficient = 117 adults.

2. Tribolium confusum Duv. Wafer disk 10 mg/ml Feeding deterrence 2. Treatment given to
(Confused flour beetle) test coefficient both adults and
Adults = 139 larvae.
Larvae = 170

3. Trogoderma granarium Wafer disk 10 mg/ml Feeding deterrence 3. Treatment given to


Everts test coefficient = 127 larvae.
(Khapra beetle)
Neutral value = 0
Absolute feeding
deterrence value =
200
(3)

(1) Konecny, K., Ubik, K., Vasickova, S., Streibl, M., and Herout, V. (1982) Collect. Czech. Chem. Commun.,
47, 3164.
(2) Streibl, M., Nawrot, J., and Herout, V. (1983) Biochem. Syst. Ecol., 11, 381

© 2005 by CRC Press LLC


544 Opender Koul

ISOASARONE C12H16O3
(208.26)
M.p. : 23.0–23.5°
(25°)
OCH3
B.p. : 145–147°/2 mm
H3CO

OCH3

CH2

(1, 2) (1, 2)

SOURCE: Piper futokadzura Sieb. et Zucc., Japanese piper (Piperaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk test 1% Feeding deterrence = Treatment to 3rd
(Tobacco armyworm) 90–100% instar larvae.
(1)
0.5% Feeding deterrence =
90–100%

0.1% No activity

(1) Matsui, K., Wada, K., and Munakata, K. (1976) Agric. Biol. Chem., 40, 1045.
(2) de O. Santos, B.V., da Cunha, E.V.L., de O. Chaves, M.C., and Gray, A.I. (1998) Phytochemistry, 49, 1381

© 2005 by CRC Press LLC


Insect Antifeedants 545

ISOBERGAPTEN C12H8O4
(216.19)
M.p. : 222°
(217–219°)

OCH3

O O O

(1, 2, 3) (1, 2)

SOURCE: Pimpinella saxifraga L., pimpinella (Apiaceae) (1, 3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk test 100 ppm Feeding ratio = 7.0% Treatment to 3rd
(Tobacco armyworm) instar larvae. Feeding
10 ppm Feeding ratio = 3.0% ratio from 0 to 20%
considered to be
5 ppm Feeding ratio = 4.0% highly deterrent.
(3)

(1) Wessely, F. and Nadler, E. (1932) Montash, 60, 142.


(2) Spath, E. and Simon, A.F.J. (1936) Montash, 67, 349.
(3) Yajima, T. and Munakata, K. (1979) Agric. Biol. Chem., 43, 1701.

© 2005 by CRC Press LLC


546 Opender Koul

ISOBOLDINE C19H21O4N
(327.38)
M.p. : 127°
H3CO
[α]31
D : +60° (CHCl3)

N
HO

H3CO

OH

(1) (1)

SOURCE: Cocculus trilobus DC., Japanese mu fang (Menispermaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Trimeresia miranda Butler Leaf disk test 200 ppm Threshold level of 1. Treatment to
(Cutworm) feeding deterrence larvae at random.
Feeding = 0–20% of
controls.
(1)

2. Spodoptera litura (Fab.) Leaf disk test 200 ppm 0–20% consumption 2. Treatment to 3rd
(Tobacco armyworm) of controls instar larvae.
(1)
100 ppm 20–50%
consumption of
controls

(1) Wada, K. and Munakata, K. (1968) J. Agric. Food Chem., 16, 471.

© 2005 by CRC Press LLC


Insect Antifeedants 547

ISOBRUCEIN–A C26H34O11
(522.55)
M.p. : 200–202°

[α]D : +43° (CHCl3)


OH

HO COOCH3
OH
O
H
O OCO

O O
H H

(1, 2, 3) (1, 2)

SOURCE: Soulamea soulameoides (Gray) Nooteboom (Simaroubaceae) (2, 3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Heliothis virescens (Fab.) Leaf disk test 15 µg/cm2 Feeding inhibition = 1. Treatment to 3rd
(Cotton budworm) 95.0% instar larvae.
Concentration = PC95
(3)

2. Spodoptera frugiperda Leaf disk test 8 µg/cm2 Feeding inhibition = 2. Treatment to 3rd
(J.E. Smith) 95.0% instar larvae.
(Fall armyworm) Concentration = PC95
(3)

3. Epilachna varivestis Muls. Whole leaf 200 ppm Feeding inhibition = 3. Treatment to 4th
(Mexican bean beetle) application 87.1% instar larvae for 24 h.
Larvae pre-starved
for 2 h. Data
calculated from
Reference 4.
(4)

(1) Polonsky, J., Baskevitch-Varon, Z., and Sevenet, T. (1975) Experientia, 31, 1113.
(2) Handa, S.S., Kinghorn, A.D., Cordell, G.A., and Farnsworth, N.R. (1983) J. Nat. Prod., 46, 359.
(3) Klocke, J.A., Arisawa, M., Handa, S.S., Kinghorn, A.D., Cordell, G.A., and Farnsworth, N.R. (1985) Expe-
rientia, 41, 7.
(4) Leskinen, V., Polonsky, J., and Bhatnagar, S. (1984) J. Chem. Ecol., 10, 1497.

© 2005 by CRC Press LLC


548 Opender Koul

ISOBRUCEIN–B C23H28O11
(480.47)
M.p. : 255–258°

[α]22
D : +17° (MeOH)
OH

HO COOCH3
OH
O
H
O OCOCH3

O O
H H

(1, 2) (1)

SOURCE: Picrolemma pseudocoffea Ducke. (Simaroubaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Heliothis virescens (Fab.) Leaf disk 19.8 µg/cm2 Feeding inhibition = 1. Treatment to 3rd
(Cotton budworm) test 60–90% after 6 days instar larvae.
of treatment. (2)

3 µg/cm2 Feeding inhibition =


to 12 µg/cm2 60–90% after 2 days
and 0–30% after 6
days of treatment.

(1) Moretti, C., Polonsky, J., Vuilhorgne, M., and Prange, T. (1982) Tetrahedron Lett., 23, 647.
(2) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y.M., Kiyokawa, H., and Lee, K.H.
(1987) J. Nat. Prod., 50, 442.

© 2005 by CRC Press LLC


Insect Antifeedants 549

3β-ISOBUTYRYLOXY-1-1-OXOMELIAC-8 C31H40O8
O
(30)-ENATE (540.65)
M.p. : 211–213°

O
H3COOC

O O

O (1) (1)

SOURCE: Carapa procera DC, crabwood (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera frugiperda Leaf disk 0.1% Feeding ratio = 0.03 Treatment to 7- to


(J.E. Smith) choice test 9-day-old larvae pre-
(Fall armyworm) Value of 0.25 or less starved for 24 h.
considered to be Treatment duration =
strongly deterrent. 3 h.
(1)

(1) Mikolajczak, K.L., Weisleder, D., Parkanyi, L., and Clardy, J. (1988) J. Nat. Prod., 51, 606.

© 2005 by CRC Press LLC


550 Opender Koul

ISOCEDRELONIC ACID C26H32O6


(440.51)
M.p. : 295–300° (dec.)
O
[α]D : –50°
(CHCl3-EtOH, 1:1)

OH

O
COOH
OH

(1) (1)

SOURCE: Synthetic (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk 1 µg/cm2 Feeding inhibition = Treatment to 3rd
(Tobacco armyworm) dual choice 42.6% instar larvae
test for 24 h.
5 µg/cm2 Feeding inhibition = (2)
46.5%

10 µg/cm2 Feeding inhibition = EC50 = 5.8 µg/cm2


59.8%

50 µg/cm2 Feeding inhibition = Data calculated from


66.4% Reference 2.

(1) Hodges, R., McGeachin, S.G., and Raphel, R.A. (1963) J. Chem. Soc., 2515.
(2) Govindachari, T.R., Narasimhan, N.S., Suresh, G., Partho, P.D., Gopalakrishnan, G., and Krishna Kumatri,
G.N. (1995) J. Chem. Ecol., 21, 1585.

© 2005 by CRC Press LLC


Insect Antifeedants 551

(±) ISODRIMENIN C15H22O2


(234.34)
M.p. : 131–132°

[α]D : +87° (CHCl3)


O
O

(1, 2) (2)

SOURCE: Synthetic (1)


Also occurs in the bark of Drimys winteri Forst., megellanic bay tree (Magnoliaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Leptinotarsa decemlineata Leaf disk 5 mM Feeding inhibition = 1. Treatment to


(Say) dual choice 87.0% larvae of 90 to 120
(Colorado potato beetle) test mg body weight for a
period of 3 h.
(1)

2. Pieris brassicae (L.) Leaf disk 5 mM Feeding inhibition = 2. Treatment to 5th


(Large white butterfly) dual choice 88.0% stadium larvae of 24-
test to 72-h age for a
period of 3 h.
(3)

(1) Gols, G.J.Z., van Loon, J.J.A., and Messchendorp, L. (1996) Entomol. Exp. Appl., 79, 69.
(2) Appel, H.H., Connolly, J.D., Overton, K.H., and Bond, R.P.M. (1960) J. Chem. Soc., 4685.
(3) Messchendorp, L., van Loon, J.J.A., and Gols, G.J.Z. (1996) Entomol. Exp. Appl., 79, 195.

© 2005 by CRC Press LLC


552 Opender Koul

ISOERIOCEPHALIN C24H30O9
(462.50)
M.p. : 232–234°
O
[α]20
D : –33.1° (CHCl3)

O
OAc

O
O
OH
AcO

(1, 2) (1)

SOURCE: Teucrium lanigerum L., forest germander (Labiatae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera littoralis (Boisd.) Glass fiber 100 ppm Feeding inhibition = Treatment to final
(Egyptian cotton leaf worm) disk choice 38.9% stadium larvae pre-
test starved for 4 h.
10 ppm Feeding inhibition = Treatment was never
33.1% longer than 18 h so
that never more than
2. Helicoverpa armigera Glass fiber 100 ppm Feeding inhibition = 50% of any disk was
(Hubner) disk choice 24.8% consumed.
(Gram pod borer) test (2)
10 ppm Feeding inhibition =
20.9%

(1) Fernandez-Gadea, F., Rodriguez, B., Savona, G., and Piozzi, F. (1984) Phytochemistry, 23, 1113.
(2) Simmonds, M.S.J., Blaney, W.M., Ley, S.V., Savona, G., Bruno, M., and Rodriguez, B. (1989) Phytochemistry,
28, 1069.

© 2005 by CRC Press LLC


Insect Antifeedants 553

ISOFRUTICOLONE C22H30O6
(390.48)
Oil

[α]D : –87.8° (CHCl3)


O

AcO OH

(1, 2) (2)

SOURCE: Teucrium fruticans L., bush germander (Labiatae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera littoralis (Boisd.) Glass fiber 100 ppm Feeding inhibition = Treatment to final
(Egyptian cotton leaf worm) disk choice 53.0% stadium larvae pre-
test starved for 4 h.
Treatment was never
longer than 18 h so
that never more than
50% of any disk was
consumed.
(2)

(1) Bruno, M., Ciriminna, R., Piozzi, F., Rosselli, S., and Simmonds, M.S.J. (1999) Phytochemistry, 52, 1055.
(2) Savona, G., Passannanti, S., Paternostro, M.P., Piozzi, F., Hanson, J.R., Hitchcock, P.P., and Siverns, M. (1978)
J. Chem. Soc. Perkin Trans I, 356.

© 2005 by CRC Press LLC


554 Opender Koul

ISOLACTARORUFIN C15H22O4
(266.34)
M.p. : 191°

[α]20
D : +8.4° (CHCl3)

OH O

OH

(1, 2) (1)

SOURCE: Lactarius rufus (Scop.) Fr., fungus (Fungi) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius (L.) Wafer disk 10 mg/cm3 Feeding deterrence 1. Treatment given to
(Grain weevil) test coefficient = 90.3 adults.

2. Tribolium confusum Duv. Wafer disk 10 mg/cm3 Feeding deterrence 2. Treatment given to
(Confused flour beetle) test coefficient both adults and
Adults = 56.8 larvae.
Larvae = 7.7
(inactive)

3. Trogoderma granarium Wafer disk 10 mg/cm3 Feeding deterrence 3. Treatment given to


Everts test coefficient = 8.7 larvae.
(Khapra beetle) (inactive)
Neutral value = 0
Absolute feeding
deterrence value =
200
(2)

(1) Daniewski, W.M., Kocor, M., and Thoren, S. (1976) Heterocycles, 77.
(2) Nawrot, J., Bloszyk, E., Grabarczyk, H., Drozdz, B., Daniewski, W.M., and Holub, M. (1983) Prace. Nauk.
Inst. Ochr. Roslin, 25, 91.

© 2005 by CRC Press LLC


Insect Antifeedants 555

ISOLONCHOCARPIN C20H18O3
(306.36)
M.p. : 115°

[α]24
D : –125° (CHCl3)

O O

(1, 2) (1)

SOURCE: Lonchocarpus eriocaulinalis M. Mich. (Fabaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera exempta (Walker) Glass fiber 100 ppm Feeding inhibition = 1. Treatment to 24- to
(Nut grass armyworm) disk dual- 74.0% 36-h-old final
choice test stadium larvae for
10 ppm Feeding inhibition = 5 h. Larvae were pre-
59.0% starved for 4 h.
(2)

2. Spodoptera littoralis (Boisd.) Glass fiber 100 ppm Feeding inhibition = 2. Treatment to 24- to
(Egyptian cotton leaf worm) disk dual- 88.0% 36-h-old final
choice test stadium larvae for
10 ppm Feeding inhibition = 5 h. Larvae were pre-
87.0% starved for 4 h.
(2)

(1) Delle Monache, F., Cuca Suarez, L.E., and Bettolo, G.B.M. (1978) Phytochemistry, 17, 1812.
(2) Simmonds, M.S.J., Blaney, W.M., Delle Monache, F., and Bettolo, G.B.M. (1990) J. Chem. Ecol., 16, 365.

© 2005 by CRC Press LLC


556 Opender Koul

ISOMONTANOLIDE C22H30O7
(406.47)
M.p. : 174–176°

OH
[α]20
D : –25.2° (CHCl3)

OOC

OAc

(1, 2) (1)

SOURCE: Laserpitium siler L., mountain lasser wort (Apiaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius (L.) Wafer disk 1% Feeding deterrence 1. Treatment given to


(Grain weevil) test coefficient = 77 adults.

2. Tribolium confusum Duv. Wafer disk 1% Feeding deterrence 2. Treatment given to


(Confused flour beetle) test coefficient both adults and
Adults = 171 larvae.
Larvae = 73

3. Trogoderma granarium Wafer disk 1% Feeding deterrence 3. Treatment given to


Everts test coefficient = 71 larvae.
(Khapra beetle)
Neutral value = 0
Absolute feeding
deterrence value =
200
(3)

(1) Holub, M., Motl, O., Samek, Z., and Herout, V. (1972) Collect. Czech. Chem. Commun., 37, 1186.
(2) Nawrot, J., Smitalova, Z., and Holub, M. (1983) Biochem. Syst. Ecol., 11, 243.

© 2005 by CRC Press LLC


Insect Antifeedants 557

ISOPETASIN C20H28O3
(316.44)
M.p. : 99–100°
(82–84°)

[α]20
D : +31° (CHCl3)

O
O

(1, 2) (1)

SOURCE: Petasites kablikianus Tausch ex Bercht. (Asteraceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius (L.) Wafer disk 10 mg/ml Feeding deterrence 1. Treatment given to
(Grain weevil) test coefficient = 29 adults.

2. Tribolium confusum Duv. Wafer disk 10 mg/ml Feeding deterrence 2. Treatment given to
(Confused flour beetle) test coefficient both adults and
Adults = 60 larvae.
Larvae = 99

3. Trogoderma granarium Wafer disk 10 mg/ml Feeding deterrence 3. Treatment given to


Everts test coefficient = 56 larvae.
(Khapra beetle)
Neutral value = 0
Absolute feeding
deterrence value =
200
(3)

(1) Novotny, L., Kotva, K., Toman, J., and Herout, V. (1972) Phytochemistry, 11, 2795.
(2) Nawrot, J., Harmatha, J., and Novotny, L. (1984) Biochem. Syst. Ecol., 12, 99.

© 2005 by CRC Press LLC


558 Opender Koul

ISOPIMARIC ACID C20H30O2


(302.46)
M.p. : 162–164°

[α]24
D : 0° (neat)

CH2

COOH

(1, 2) (1)

SOURCE: Commercial sample (2)


Occurs in Pinus spp.

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Neodiprion dubiosus Schedl. Pine needle 7 mg/ml Feeding inhibition = Treatments to 4th or
(Brownhead jack pine sawfly) and twig 70.0% 5th instar larvae for
application 4 h.
(2)
2. Neodiprion rugifrons Pine needle 5.3 mg/ml Feeding inhibition =
Middleton and twig 70.0%
(Redhead jack pine sawfly) application

3. Neodiprion lecontei (Fitch) Pine needle 10.7 mg/ml Feeding inhibition =


(Redhead pine sawfly) and twig 70.0%
application

(1) Bohlmann, F. and Le Van, N. (1976) Chem. Ber., 109, 1446.


(2) Schuh, B.A. and Benjamin, D.M. (1984) J. Econ. Entomol., 77, 802.

© 2005 by CRC Press LLC


Insect Antifeedants 559

ISOPIMPINELLIN C13H10O5
(246.22)
M.p. : 147–148°
(151°)

OCH3

O O O

OCH3

(1, 2) (1)

SOURCE: Oryxa japonica Thunb., Japanese kokusagi (Rutaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera litura (Fab.) Leaf disk test 5 ppm Feeding inhibition = 1. Treatment to 3rd
(Tobacco armyworm) 50.0% instar larvae.
(1)

100 ppm Feeding inhibition = Treatment to 3rd


100.0% instar larvae for 90
min.
(2)

Artificial diet 5 ppm Feeding inhibition = Treatment to 4th


assay 50.0% instar larvae pre-
starved for 48 h.
(3)

2. Periplaneta americana (L.) Sugar pellet 0.1 mg/ Feeding inhibition = 2. Treatment to adult
(American cockroach) method 1.5 g pellet 57.0% cockroaches.
(2)

3. Blatella germanica (L.) Sugar pellet 0.1 mg/ Feeding inhibition = 3. Treatment to adult
(German cockroach) method 1.5 g pellet 31.0% cockroaches.
(2)

(1) Yajima, T., Kato, N., and Munakata, K. (1977) Agric. Biol. Chem., 41, 1263.
(2) Yajima, T. and Munakata, K. (1979) Agric. Biol. Chem., 43, 1701.
(3) Luthria, D.L., Ramakrishnan, V., Verma, G.S., Prabhu, B.R., and Banerji, A. (1989) J. Agric. Food Chem.,
37, 1435.

© 2005 by CRC Press LLC


560 Opender Koul

ISOPONGAFLAVONE C21H18O4
(334.37)
M.p. : 215–216°

O O

OCH3 O

(1, 2) (1)

SOURCE: Tephrosia elata Deflers, African tephrosia (Fabaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Maruca testulalis (Geyer) Leaf disk test 100 µg Feeding inhibition = 1. Treatment to late
(Bean pod borer) 86.0% 5th instar larvae for
10 µg Feeding inhibition = 6 h.
per 1.8 cm 77.0% (2)
diameter

2. Eldana saccharina Walker Leaf disk test 100 µg Feeding inhibition = 2. Treatment to 5th
(Sugar cane borer) 74.0% instar larvae pre-
10 µg Feeding inhibition = starved for 12 h.
per 1.8 cm 54.0% Feeding duration =
diameter 24 h in the dark.
(2)

3. Spodoptera exempta (Walker) Leaf disk test 100 µg Feeding inhibition = 3. Treatment to mid
(Nutgrass armyworm) 23.0% 6th instar larvae for
2 h. Larvae were pre-
10 µg No inhibition starved for 2 h.
per 1.8 cm (2)
diameter

(1) Chibber, S.S. and Dutt, S.K. (1981) Phytochemistry, 20, 1460.
(2) Bentley, M.D., Hassanali, A., Lwandi, W., Njoroge, P.E.W., Sitayo, E.N.O., and Yatagai, M. (1987) Insect
Sci. Applic., 8, 85.

© 2005 by CRC Press LLC


Insect Antifeedants 561

ISOPROTOSTEMONINE C23H31O6N
(417.50)
M.p. : 165–167°

[α]D : –23.6° (EtOH)

O
O N O
O

OCH3

(1) (1)

SOURCE: Stemona japonica Miq., Japanese stemona (Stemonaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Glass fiber 200 ppm Feeding inhibition = Treatment to last
(Tobacco armyworm) disk test 33.0% instar larvae.
(1)

(1) Ye, Y., Qin, G., and Xu, R. (1994) Phytochemistry, 37, 1205.

© 2005 by CRC Press LLC


562 Opender Koul

ISOSILEROLIDE C22H30O6
(390.48)
M.p. : 141–143°

[α]20
D : –138.9° (CHCl3)
OCOCH3

OCO
O

(1, 2) (1)

SOURCE: Laserpitium siler L., mountain lasser wort (Apiaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius (L.) Wafer disk 1% Feeding deterrence 1. Treatment given to


(Grain weevil) test coefficient = 52 adults.

2. Tribolium confusum Duv. Wafer disk 1% Feeding deterrence 2. Treatment given to


(Confused flour beetle) test coefficient both adults and
Adults = 136 larvae.
Larvae = 20

3. Trogoderma granarium Wafer disk 1% Feeding deterrence 3. Treatment given to


Everts test coefficient = 81 larvae.
(Khapra beetle)
Neutral value = 0
Absolute feeding
deterrence value =
200
(3)

(1) Holub, M., Budesinsky, M., Smitalova, Z., Saman, D., and Rychlewska, U. (1982) Tetrahedron Lett., 4853.
(2) Nawrot, J., Smitalova, Z., and Holub, M. (1983) Biochem. Syst. Ecol., 11, 243.

© 2005 by CRC Press LLC


Insect Antifeedants 563

ISOTADEONAL C15H22O2
(234.34)
Oil

B.p. : 145–153°/1 mm

CHO [α]D : –237.4° (EtOH)

CHO

(1) (2)

SOURCE: Synthetic (1)


Also isolated from Polygonum hydropiper L., water pepper (Polygonaceae)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Leptinotarsa decemlineata Leaf disk 5 mM Feeding inhibition = 1. Treatment to


(Say) dual-choice 51.0% larvae of 90 to 120
(Colorado potato beetle) test mg body weight for a
period of 3 h.
(1)

2. Pieris brassicae (L.) Leaf disk 5 mM Feeding inhibition = 2. Treatment to 5th


(Large white butterfly) dual-choice 45.0% stadium larvae of 24-
test to 72-h-age for a
period of 3 h.
(3)

(1) Gols, G.J.Z., van Loon, J.J.A., and Messchendorp, L. (1996) Entomol. Exp. Appl., 79, 69.
(2) Ohsuka, A. and Matsukawa, A. (1979) Chem. Lett., 63.
(3) Messchendorp, L., van Loon, J.J.A., and Gols, G.J.Z. (1996) Entomol. Exp. Appl., 79, 195.

© 2005 by CRC Press LLC


564 Opender Koul

ISOTENULIN C17H22O5
(306.36)
M.p. : 160–161°

[α]D : +6° (EtOH)

O
O
OAc

(1, 2) (1)

SOURCE: Helenium tenuifolium Nutt., H. arizonicum, H. bigelovii, aster weeds (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Ostrinia nubilalis (Hubner) Leaf disk 3 µmol/g Feeding inhibition = Treatment to larvae
(European corn borer) choice test 65.5% at random.
(2)

(1) Herz, W., de Vivar, A.R., Romo, J., and Viswanathan, N. (1963) Tetrahedron, 19, 1359.
(2) Arnason, J.T., Isman, M.B., Philogene, B.J.R., and Waddel, T.G. (1987) J. Nat. Prod., 50, 690.

© 2005 by CRC Press LLC


Insect Antifeedants 565

ISOTENULIN METHYL IMINE C18H25O4N


(319.40)
No physical data given

O
N
OAc

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Ostrinia nubilalis (Hubner) Leaf disk 3 µmol/g Feeding inhibition = Treatment to larvae
(European corn borer) choice test 67.2% at random.
(1)

(1) Arnason, J.T., Isman, M.B., Philogene, B.J.R., and Waddel, T.G. (1987) J. Nat. Prod., 50, 690.

© 2005 by CRC Press LLC


566 Opender Koul

ISOTENULIN OXIDE C17H24O6


(324.48)
No physical data given

H
H

H O

O
O
OAc

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Ostrinia nubilalis (Hubner) Leaf disk 3 µmol/g Feeding inhibition = Treatment to larvae
(European corn borer) choice test 65.4% at random.
(1)

(1) Arnason, J.T., Isman, M.B., Philogene, B.J.R., and Waddel, T.G. (1987) J. Nat. Prod., 50, 690.

© 2005 by CRC Press LLC


Insect Antifeedants 567

3-ISOTHUJONE C10H16O
(152.24)
B.p. : 85.7–86.2°/17 mm

[α]15
D : +72.5° (neat)

(1, 2) (1, 2)

SOURCE: Thuja plicata Donn. ex Don., Western red cedar (Cupressaceae) (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Pissodes strobi (Peck) Agar disk 75 µg/disk Feeding inhibition = Treatment to adult
(White pine weevil) test 23.7% weevils for 24 h.
(3)

LD50 (mice): 442.2 mg/kg (s.c.) (4)

(1) Eastman, R.H. and Winn, A.V. (1960) J. Am. Chem. Soc., 82, 5908.
(2) Hach, V., Raimondo, R.F., Cartlidge, D.M., and McDonald, E.C. (1970) Tetrahedron Lett., 3175.
(3) Alfaro, R.I., Pierce, H.D., Borden, J.H., and Oehlschlager, A.C. (1981) J. Chem. Ecol., 7, 39.
(4) Rice, K.C. and Wilson, R.S. (1976) J. Med. Chem., 19, 1054.

© 2005 by CRC Press LLC


568 Opender Koul

ISOVELLEROL C15H22O2
(234.35)
Only spectral data given

OHC

HOH2C

(1, 2) (2)

SOURCE: Synthetic (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius (L.) Wafer disk 10 mg/ml Feeding deterrence 1. Treatment given to
(Grain weevil) test coefficient = 176 adults.

2. Tribolium confusum Duv. Wafer disk 10 mg/ml Feeding deterrence 2. Treatment given to
(Confused flour beetle) test coefficient both adults and
Adults = 162 larvae.
Larvae = 161.9

3. Trogoderma granarium Wafer disk 10 mg/ml Feeding deterrence 3. Treatment given to


Everts test coefficient = 200 larvae.
(Khapra beetle)
Neutral value = 0
Absolute feeding
deterrence value =
200
(2)

(1) Sterner, O., Bergman, R., Kihlberg, J., and Wickberg, B. (1985) J. Nat. Prod., 48, 279.
(2) Daniewski, W.M., Gumulka, M., Bloszyk, E., Jacobsson, U., and Norin, T. (1997) Polish J. Chem., 71, 1254.

© 2005 by CRC Press LLC


Insect Antifeedants 569

ISOVITEXIN 6″-O-β-D-GLUCOPYRANOSIDE C27H30O15


HO (594.53)
M.p. : 214–216°

O OH
OH

OH

O
OH
OH

OH
O

HO OH

OH (1) (1)

SOURCE: Alliaria petiolata (M. Bieb.) Cavara and Grande, garlic mustard (Cruciferae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Pieris napi oleracea (L.) Leaf disk Fraction Feeding deterrence 1. Treatment given to
(Cabbage butterfly) choice test containing index = 48.4% for a 4th instar larvae.
compound fraction containing (1)
used. the compound. No
data given for the
pure compound.

(1) Haribal, M. and Renwick, J.A.A. (1998) Phytochemistry, 47, 1237.

© 2005 by CRC Press LLC


570 Opender Koul

IVAIN–1 C28H42O10
(538.63)
Amorphous
H
O [α]D : –8° (CHCl3)
H

O
H H

HO H
H

COO
O
CH2
OCOCH3

OCOCH3
(1, 2) (1)

SOURCE: Ajuga iva Schreber., bugle ivette (Labiatae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera littoralis (Boisd.) Leaf disk 1 µg/cm2 Feeding ratio = Treatment to newly
(Egyptian cotton leaf worm) choice test 0.25 ± 0.07 ecdysed 5th instar
larvae. Feeding ratio
of less than 0.5
considered as
excellent antifeedant
effect.
(2)

(1) Camps, F., Coll, J., and Cortel, A. (1982) Chem. Lett., 1053.
(2) Belles, X., Camps, F., Coll, J., and Piulachs, M.D. (1985) J. Chem. Ecol., 11, 1439.

© 2005 by CRC Press LLC


Insect Antifeedants 571

IVAIN–2 C28H42O9
(522.63)
M.p. : 158–161°
H
O [α]D : –26.8° (CHCl3)
H

O
H H
H
H
H

COO
O
CH2
OCOCH3

OCOCH3
(1, 2) (1)

SOURCE: Ajuga iva Schreber., bugle ivette (Labiatae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera littoralis (Boisd.) Leaf disk 1 µg/cm2 Feeding ratio = Treatment to newly
(Egyptian cotton leaf worm) choice test 0.14 ± 0.02 ecdysed 5th instar
larvae. Feeding ratio
0.1 µg/cm2 Feeding ratio = of less than 0.5
0.25 ± 0.09 considered as
excellent antifeedant
0.01 µg/cm2 Feeding ratio = effect.
0.67 ± 0.10 (2)

(1) Camps, F., Coll, J., and Cortel, A. (1982) Chem. Lett., 1053.
(2) Belles, X., Camps, F., Coll, J., and Piulachs, M.D. (1985) J. Chem. Ecol., 11, 1439.

© 2005 by CRC Press LLC


572 Opender Koul

IVAIN–3 C30H46O11
(582.69)
Amorphous
OC2H5
O [α]D : +31.7° (CHCl3)
H

O
H H
H
H
HO

COO
O
CH2
OCOCH3

OCOCH3
(1, 2) (1)

SOURCE: Ajuga iva Schreber., bugle ivette (Labiatae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera littoralis (Boisd.) Leaf disk 1 µg/cm2 Feeding ratio = Treatment to newly
(Egyptian cotton leaf worm) choice test 0.37 ± 0.10 ecdysed 5th instar
larvae. Feeding ratio
of less than 0.5
considered as
excellent antifeedant
effect.
(2)

(1) Camps, F., Coll, J., and Cortel, A. (1982) Chem. Lett., 1053.
(2) Belles, X., Camps, F., Coll, J., and Piulachs, M.D. (1985) J. Chem. Ecol., 11, 1439.

© 2005 by CRC Press LLC


Insect Antifeedants 573

IVAIN–4 C29H44O10
(552.66)
Amorphous
H
O [α]D : +4.1° (CHCl3)
H

O
H H
H
H
HO

COO
O
CH2
OCOCH3

OCOCH3
(1, 2) (1)

SOURCE: Ajuga iva Schreber., bugle ivette (Labiatae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera littoralis (Boisd.) Leaf disk 1 µg/cm2 Feeding ratio = Treatment to newly
(Egyptian cotton leaf worm) choice test 0.12 ± 0.04 ecdysed 5th instar
larvae. Feeding ratio
of less than 0.5
considered as
excellent antifeedant
effect.
(2)

(1) Camps, F., Coll, J., and Cortel, A. (1982) Chem. Lett., 1053.
(2) Belles, X., Camps, F., Coll, J., and Piulachs, M.D. (1985) J. Chem. Ecol., 11, 1439.

© 2005 by CRC Press LLC


574 Opender Koul

JAPONINE C18H17O3N
(295.34)
M.p. : 143°
(145–146°)

H3CO OCH3

(1) (1, 2)

SOURCE: Oryxa japonica Thunb., Japanese kokusagi (Rutaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk 300 ppm Feeding inhibition = Treatment to 3rd
(Tobacco armyworm) choice test 50.0% instar larvae.
(1)

(1) Yajima, T., Kato, N. and Munakata, K. (1977) Agric. Biol. Chem., 41, 1263.
(2) Ha-Huy-Ke and Luckner, M. (1970) Phytochemistry, 9, 2199.

© 2005 by CRC Press LLC


Insect Antifeedants 575

JODRELLIN–A C24H32O8
(448.51)
Oil
OAc

OAc

O
O

O
(1, 2)
(1)

SOURCE: Scutellaria woronowii Juz., skullcap (Labiatae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera littoralis (Boisd.) Glass fiber 50 ppm Feeding inhibition = Treatment to final
(Egyptian cotton leaf worm) disk choice 100% stadium larvae pre-
test starved for 4 h.
25 ppm Feeding inhibition = Treatment duration
53.0% until 50% of either
disk was consumed
or for 12 h.
(2)

(1) Anderson, J.C., Blaney, W.M., Cole, M.D., Fellows, L.L., Ley, S.V., Sheppard, R.N., and Simmonds, M.S.J.
(1989) Tetrahedron Lett., 30, 4737.
(2) Cole, M.D., Anderson, J.C., Blaney, W.M., Fellows, L.E., Ley, S.V., Sheppard, R.N., and Simmonds, M.S.J.
(1990) Phytochemistry, 29, 1793.

© 2005 by CRC Press LLC


576 Opender Koul

JODRELLIN–B C26H36O8
(476.57)
Oil

[α]20
D : –11.4° (CHCl3)
O
OAc O

O
(1, 2) (1)

SOURCE: Scutellaria woronowii Juz., skullcap (Labiatae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera littoralis (Boisd.) Glass fiber 50 ppm Feeding inhibition = Treatment to final
(Egyptian cotton leaf worm) disk choice 100% stadium larvae pre-
test starved for 4 h.
25 ppm Feeding inhibition = Treatment duration
83.0% until 50% of either
disk was consumed
or for 12 h.
(2)

(1) Anderson, J.C., Blaney, W.M., Cole, M.D., Fellows, L.L., Ley, S.V., Sheppard, R.N., and Simmonds, M.S.J.
(1989) Tetrahedron Lett., 30, 4737.
(2) Cole, M.D., Anderson, J.C., Blaney, W.M., Fellows, L.E., Ley, S.V., Sheppard, R.N., and Simmonds, M.S.J.
(1990) Phytochemistry, 29, 1793.

© 2005 by CRC Press LLC


Insect Antifeedants 577

JUGLONE C10H6O3
(174.16)
M.p. : 155°

OH O

(1, 2) (1)

SOURCE: Commercial sample (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Peridroma saucia (Hubner) Leaf disk 14.25 µg/cm2 Feeding inhibition = Treatment to 5th
(Variegated cutworm) choice test 74.5% instar larvae for 5 h.
(2)
57.0 µg/cm2 Feeding inhibition =
78.2%

LD50 (mice): 2.5 mg/kg (oral) (3)

(1) (1994) Dictionary of Natural Products, Chapman & Hall, London.


(2) Nawrot, J., Koul, O., Isman, M.B., and Harmatha, J. (1991) J. Appl. Ent., 112, 194.
(3) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC


578 Opender Koul

KAEMPFEROL-3-O-β-GLUCOPYRANOSIDE C21H20O11
(448.38)
M.p. : 243–245°

[α]D : –103°
OH
(pyridine:MeOH:H2O)
HO O
(1 : 1 : 1)

HO
OH

O
O
OH
OH O
CH2OH

(1, 2) (1)

SOURCE: Detarium microcarpum Guill. & Perr., African atokolo (Caesalpiniaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Reticulitermes speratus Kolbe Paper disk 80 µg/cm2 Feeding inhibition Treatment to 3rd
(Subterranean termite) choice test index = 5.0 instar workers.
Feeding duration =
14 days.
Antifeedant index
below 20 considered
as highly deterrent.
(2)

(1) Hasan, C.M., Healey, T.M., and Waterman, P.G. (1982) Phytochemistry, 21, 1365.
(2) Lajide, L., Escoubas, P., and Mizutani, J. (1995) Phytochemistry, 40, 1101.

© 2005 by CRC Press LLC


Insect Antifeedants 579

KALMANOL C20H34O6
(370.48)
M.p. : 255–256°
(258–261°)

H [α]25
D : +31° (MeOH)
HO
H

H
HO
OH

OH OH
OH

(1, 2) (1, 2)

SOURCE: Rhododendron molle (B.) G. Don., yellow azalea (Ericaceae) (1)


Kalmia angustifoila L., sheep laurel (Ericaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Leptinotarsa decemlineata Leaf disk 15.0 µg/ Feeding inhibition = 1. Treatment to 4th
(Say) choice test 50 mm2 95.0% instar larvae until
(Colorado potato beetle) 95% of control disk
was consumed.
(1)

2. Spodoptera frugiperda Leaf disk 12.5 µg/ Feeding inhibition = 2. Treatment to 3rd
(J.E. Smith) choice test 50 mm2 95.0% instar larvae until
(Fall armyworm) 95% of control disk
was consumed.
(1)

(1) Klocke, J.A., Hu, M., Chiu, S., and Kubo, I. (1991) Phytochemistry, 30, 1797.
(2) Burke, J.W., Doskotch, R.W., Zhou, C., and Clardy, J. (1989) J. Am. Chem. Soc., 111, 5831.

© 2005 by CRC Press LLC


580 Opender Koul

(–)- KAURAN-16α-OL C20H34O


(290.49)
M.p. : 210–211°

OH

(1, 2) (1)

SOURCE: Xylopia aethiopica A. Rich., African pepper (Anonaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Reticulitermes speratus Kolbe Paper disk 5000 ppm Feeding inhibition Treatment to 3rd
(Subterranean termite) choice test index = 0.0 instar workers.
Feeding duration =
2500 ppm Feeding inhibition 14 days.
index = 14.4 Antifeedant index
below 20 considered
as highly deterrent.
(2)

(1) Bohlmann, F. and le Van, N. (1977) Phytochemistry, 16, 487.


(2) Lajide, L., Escoubas, P., and Mizutani, J. (1995) Phytochemistry, 40, 1105.

© 2005 by CRC Press LLC


Insect Antifeedants 581

(–)-KAURAN-16α-19-DIOL C20H34O2
(306.49)
M.p. : 200–201°

[α]22
D : –40.5° (EtOH)

OH

CH2OH

(1, 2) (1)

SOURCE: Xylopia aethiopica A. Rich., African pepper (Anonaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Reticulitermes speratus Kolbe Paper disk 5000 ppm Feeding inhibition Treatment to 3rd
(Subterranean termite) choice test index = 18.0 instar workers.
Feeding duration =
14 days.
Antifeedant index
below 20 considered
as highly deterrent.
(2)

(1) Henrick, C.A. and Jefferies, P.R. (1964) Aust. J. Chem., 17, 915.
(2) Lajide, L., Escoubas, P., and Mizutani, J. (1995) Phytochemistry, 40, 1105.

© 2005 by CRC Press LLC


582 Opender Koul

KAUR-16-EN-19-OIC ACID C20H30O2


(302.46)
M.p. : 179–181°

[α]D : –110° (CHCl3)

CH2

COOH

(1, 2) (1)

SOURCE: Xylopia aethiopica A. Rich., African pepper (Anonaceae) (2)


Lasianthaea sp. (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Reticulitermes speratus Kolbe Paper disk 2500 ppm Feeding inhibition Treatment to 3rd
(Subterranean termite) choice test index = 7.78 instar workers.
Feeding duration =
1000 ppm Feeding inhibition 14 days.
index = 5.4 Antifeedant index
below 20 considered
as highly deterrent.
(2)

(1) Wiemer, D.F. (1985) Rev. Latinoamer. Quim., 16, 98.


(2) Lajide, L., Escoubas, P., and Mizutani, J. (1995) Phytochemistry, 40, 1105.

© 2005 by CRC Press LLC


Insect Antifeedants 583

KERLINIC ACID C20H28O4


(332.44)
M.p. : 183–185°

[α]22
D : –236.8° (CHCl3)

OH
HOOC

(1, 2) (1)

SOURCE: Salvia keerlii Benth., sage plant (Labiatae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera frugiperda Leaf disk no- 2 ppm Feeding inhibition = Treatment to 3rd
(J.E. Smith) choice test 75.0% instar larvae pre-
(Fall armyworm) starved for 4 h.
50 ppm Feeding inhibition = Treatment duration =
75.0% 24 h.
(2)
100 ppm Feeding inhibition =
100% Data calculated from
Reference 2.

(1) Lidia Rodriguez-Ilahn, L. (1987) Can. J. Chem., 65, 2687.


(2) Taboada, J., Guerrero, C., Camino, L.M., and Aldama, L. L. (1996) Rev. Latinoamer. Quim., 24, 33.

© 2005 by CRC Press LLC


584 Opender Koul

13-KETO-8 (14)-PODOCARPEN-18-OIC ACID C17H24O3


(276.38)
Only spectral data given

COOH

(1) (2)

SOURCE: Pinus banksiana Lamb., jack pine (Pinaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Neodiprion rugifrons Spray 10 mg/ml Feeding inhibition = 1. Treatment to 3rd


Middleton 100% instar larvae. Sprays
(Pine sawfly) applied on both
1 mg/ml Feeding inhibition = larvae as well as host
100% branches.
(1)

2. Neodiprion swainei Spray 5 mg/ml Feeding inhibition = 2. Treatment to 3rd


Middleton 85.8% instar larvae. Sprays
(Pine sawfly) applied on both
1 mg/ml Feeding inhibition = larvae as well as host
75.0% branches.
(1)

(1) Ikeda, T., Matsumura, F., and Benjamin, D.M. (1977) J. Chem. Ecol., 3, 677.
(2) Cheung, H.T.A., Miyase, T., Lenguyeu, M.P., and Small, M.A. (1993) Tetrahedron, 49, 7903

© 2005 by CRC Press LLC


Insect Antifeedants 585

KHAYANOLIDE-A (1-O-ACETYL) C29H35O11


(559.22)
Amorphous powder
O
[α]D : +59° (MeOH)

O
CH3OOC H

HO OAc O
O

O
OH
(1) (1)

SOURCE: Khaya senegalensis (Desv.) A. Juss., dry-zone mahogany (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera littoralis (Boisd.) Leaf disk 100 ppm Feeding inhibition = Treatment to 3rd
(Egyptian cotton leaf worm) choice test (2 µg/cm2) 50% instar larvae until the
larvae had eaten
approximately 50%
of one of the disks.
(1)

(1) Nakatani, M., Abdelgaleil, S.A.M., Kurawaki, J., Okamura, H., Iwagawa, T., and Doe, M. (2001) J. Nat.
Prod., 64, 1261.

© 2005 by CRC Press LLC


586 Opender Koul

KHAYANOLIDE–E C29H35O11
(559.22)
Amorphous powder
O

[α]D : +21° (MeOH)

O
CH3OOC H OH

HO OAc O

O
(1) (1)

SOURCE: Khaya senegalensis (Desv.) A. Juss., dry-zone mahogany (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera littoralis (Boisd.) Leaf disk 100 ppm Feeding inhibition = Treatment to 3rd
(Egyptian cotton leaf worm) choice test (2 µg/cm2) 50% instar larvae until the
larvae had eaten
approximately 50%
of one of the disks.
(1)

(1) Nakatani, M., Abdelgaleil, S.A.M., Kassem, S.M.I., Takezaki, K., Okamura, H., Iwagawa, T., and Doe, M.
(2002) J. Nat. Prod., 65, 1219.

© 2005 by CRC Press LLC


Insect Antifeedants 587

KHAYANONE C27H35O9
(503.23)
M.p. : 170–171°C
O
[α]D : +2.6° (MeOH)

O
CH3OOC H OH

HO O O
H

(1) (1)

SOURCE: Khaya senegalensis (Desv.) A. Juss., dry-zone mahogany (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera littoralis (Boisd.) Leaf disk 300 ppm Feeding inhibition = Treatment to 3rd
(Egyptian cotton leaf worm) choice test (6 µg/cm2) 50% instar larvae until the
larvae had eaten
approximately 50%
of one of the disks.
(1)

(1) Nakatani, M., Abdelgaleil, S.A.M., Kurawaki, J., Okamura, H., Iwagawa, T., and Doe, M. (2001) J. Nat.
Prod., 64, 1261.

© 2005 by CRC Press LLC


588 Opender Koul

KHELLIN C14H12O5 M.p. : 150.3°


(260.24) 154–155° (dimorph.)

B.p. : 180–200°/0.05 mm
OCH3 O

O O

OCH3

(1, 2) (1)

SOURCE: Ammi visnaga (L.) Lamark., visnaga (Apiaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera litura (Fab.) Leaf disk 1000 ppm Feeding inhibition 1. Treatment to 3rd
(Tobacco armyworm) choice test ratio = 20% instar larvae.
Inhibition ratio of
less than 20% is
highly deterrent
value.
(2)

Artificial diet 107.9 ppm Feeding inhibition = Treatment to 4th


feeding 50.0% instar larvae pre-
starved for 4 h.
Treatment duration =
48 h.
Concentration = FI50
(3)

2. Blatella germanica (L.) Sugar pellet 0.1 mg/ Feeding inhibition = 2. Treatment to
(German cockroach) method 1.5 g pellet 87.0% adults.
(2)

3. Periplaneta americana (L.) Sugar pellet 0.1 mg/ Feeding inhibition = 3. Treatment to
(American cockroach) method 1.5 g pellet 33.0% adults.
(2)

4. Stylopyga rhambifolia Sugar pellet 0.1 mg/ Feeding inhibition = 4. Treatment to


(Cockroach) method 1.5 g pellet 34.0% adults.
(2)

LD50 (rats): 69 mg/kg (oral) (4)

(1) Spath, E. and Gruber, W. (1938) Ber., 71, 106.


(2) Yajima, T. and Munakata, K. (1979) Agric. Biol. Chem., 43, 1701.
(3) Luthria, D.L., Ramakrishnan, V., and Banerji, A. (1993) J. Nat. Prod., 56, 671.
(4) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC


Insect Antifeedants 589

KHELLINOL DIETHYL ETHER C16H16O5


(288.22)
Only spectral data given

OC2H5

O O

OC2H5 O

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Artificial diet 28.1 ppm Feeding inhibition = Treatment to 4th
(Tobacco armyworm) assay 50.0% instar larvae pre-
starved for 4 h.
Treatment duration =
48 h.
Concentration = FI50
(1)

(1) Luthria, D.L., Ramakrishnan, V., and Banerji, A. (1993) J. Nat. Prod., 56, 671.

© 2005 by CRC Press LLC


590 Opender Koul

KHELLINOL ETHYL ETHER C15H14O5


(274.21)
Only spectral data given

OCH3

O O

OC2H5 O

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Artificial diet 49.8 ppm Feeding inhibition = Treatment to 4th
(Tobacco armyworm) assay 50.0% instar larvae pre-
starved for 4 h.
Treatment duration =
48 h.
Concentration = FI50
(1)

(1) Luthria, D.L., Ramakrishnan, V., and Banerji, A. (1993) J. Nat. Prod., 56, 671.

© 2005 by CRC Press LLC


Insect Antifeedants 591

KIEVITONE C20H20O6
(356.37)
Only spectral data given

HO O

OH O
HO OH

(1, 2) (1)

SOURCE: Phaseolus vulgaris L., french bean (Fabaceae) (2)


(virus infected)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Costelytra zealandica (White) Artificial diet 120 µg/g Feeding inhibition = Treatment to 24 h
(Scarab beetle) assay 50.0% pre-starved 3 rd
instar larvae.
Concentration = FI50
(2)

(1) Burden, R.S., Bailey, J.A., and Dawson, G.W. (1972) Tetrahedron Lett., 4175.
(2) Lane, G.A., Biggs, D.R., Russel, G.B., Sutherland, O.R.W., Williams, E.M., Maindonald, J.H., and Donnell,
D.J. (1985) J. Chem. Ecol., 11, 1713.

© 2005 by CRC Press LLC


592 Opender Koul

KLAINEANONE C20H28O6
(364.44)
M.p. : 253–258°

[α]22
D : –52° (Pyridine)
OH

HO
HO

H
O O
H

(1, 2) (1)

SOURCE: Hannoa klaineana Pierre et Engler., African quassia (Simaroubaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Heliothis virescens (Fab.) Leaf disk test 12 µg/cm2 Feeding inhibition = Treatment to 3rd
(Tobacco budworm) 60–90% after 2 days instar larvae.
and 0–30% after 6 (2)
days of treatment.

6 µg/cm2 Feeding inhibition =


60–90% after 2 days
and 0–30% after 6
days of treatment.

(1) Polonsky, J. and Zylber, N.B. (1965) Bull. Soc. Chim. Fr., 2793.
(2) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y.M., Kiyokawa, H., and Lee, K.H.
(1987) J. Nat. Prod., 50, 442.

© 2005 by CRC Press LLC


Insect Antifeedants 593

KOKUSAGINE C13H9O4N
(243.22)
M.p. : 202–203°

OCH3

O N O

(1) (1)

SOURCE: Oryxa japonica Thunb., Japanese kokusagi (Rutaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera litura (Fab.) Leaf disk 100 ppm Feeding inhibition = 1. Treatment to 3rd
(Tobacco armyworm) choice test 50.0% instar larvae.
(1)

2. Blatella germanica (L.) Sugar pellet 0.1 mg/ Feeding inhibition = 2. Treatment to
(German cockroach) method 1.5 g pellet 91.0% adults.
(2)

3. Periplaneta americana (L.) Sugar pellet 0.1 mg/ Feeding inhibition = 3. Treatment to
(American cockroach) method 1.5 g pellet 70.0% adults.
(2)

4. Stylopyga rhambifolia Sugar pellet 0.1 mg/ Feeding inhibition = 4. Treatment to


(Cockroach) method 1.5 g pellet 91.0% adults.
(2)

(1) Yajima, T., Kato, N., and Munakata, K. (1977) Agric. Biol. Chem., 41, 1263.
(2) Yajima, T. and Munakata, K. (1979) Agric. Biol. Chem., 43, 1701.

© 2005 by CRC Press LLC


594 Opender Koul

KOLAVENOL C20H34O
(290.49)
Oil

[α]D : –45.7° (CHCl3)

OH

(1) (1)

SOURCE: Melampodium divericatum Rolfe. (Asteraceae) (1)


Also occurs in Hardwickia pinnata Roxb., anjan (Fabaceae); Solidago elongata, goldenrod
(Asteraceae)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Atta cephalotes (L.) Rye flake 4 µg/flake Feeding inhibition = Treatment to adult
(Leaf cutter ant) forced 32% workers. Data
choice test calculated from
Reference 2.
(2)

(1) Hubert, T.D. and Wiemer, D.F. (1985) Phytochemistry, 24, 1197.
(2) Wiemer, D.F. (1985) Rev. Latinoamer. Quim., 16, 98.

© 2005 by CRC Press LLC


Insect Antifeedants 595

LACTARORUFIN–A C15H22O4
(266.34)
M.p. : 156–158°

[α]20
D : +7° (CHCl3)

O
HO OH

(1, 2, 3) (1, 2)

SOURCE: Lactarius rufus (Scop.) Fr., fungus (Fungi) (4)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius (L.) Wafer disk 10 mg/cm3 Feeding deterrence 1. Treatment given to
(Grain weevil) test coefficient = 88.6 adults.

2. Tribolium confusum Duv. Wafer disk 10 mg/cm3 Feeding deterrence 2. Treatment given to
(Confused flour beetle) test coefficient both adults and
Adults = 163.8 larvae.
Larvae = 144.9

3. Trogoderma granarium Wafer disk 10 mg/cm3 Feeding deterrence 3. Treatment given to


Everts test coefficient = 153.6 larvae.
(Khapra beetle)
Neutral value = 0
Absolute feeding
deterrence value =
200
(4)

(1) Daniewski, W.M. and Kocor, M. (1970) Bull. Acad. Pol. Sci. Ser. Sci. Chim., 18, 585.
(2) Daniewski, W.M. and Kocor, M. (1971) Bull. Acad. Pol. Sci. Ser. Sci. Chim., 19, 553.
(3) Baranowska, E. and Daniewski, W.M. (1972) Bull. Acad. Pol. Sci. Ser. Sci. Chim., 20, 313.
(4) Nawrot, J., Bloszyk, E., Grabarczyk, H., Drozdz, B., Daniewski, W.M., and Holub, M. (1983) Prace. Nauk.
Inst. Ochr. Roslin, 25, 91.

© 2005 by CRC Press LLC


596 Opender Koul

LACTARORUFIN–B C15H22O5
(282.34)
M.p. : 213°

[α]20
D : +24° (CHCl3)

HOH2C
O
HO OH

(1, 2) (1, 2)

SOURCE: Lactarius rufus (Scop.) Fr., fungus (Fungi) (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius (L.) Wafer disk 10 mg/cm3 Feeding deterrence 1. Treatment given to
(Grain weevil) test coefficient = 37.2 adults.

2. Tribolium confusum Duv. Wafer disk 10 mg/cm3 Feeding deterrence 2. Treatment given to
(Confused flour beetle) test coefficient both adults and
Adults = 133.3 larvae.
Larvae = 67.9

3. Trogoderma granarium Wafer disk 10 mg/cm3 Feeding deterrence 3. Treatment given to


Everts test coefficient = 92.6 larvae.
(Khapra beetle)
Neutral value = 0
Absolute feeding
deterrence value =
200
(4)

(1) Daniewski, W.M. and Kocor, M. (1970) Bull. Acad. Pol. Sci. Ser. Sci. Chim., 18, 585.
(2) Daniewski, W.M., Kocor, M., and Krol, J. (1976) Rocz. Chem. Ann. Soc. Chem. Pol., 50, 2095.
(3) Nawrot, J., Bloszyk, E., Grabarczyk, H., Drozdz, B., Daniewski, W.M., and Holub, M. (1983) Prace. Nauk.
Inst. Ochr. Roslin, 25, 91.

© 2005 by CRC Press LLC


Insect Antifeedants 597

LACTUPICRIN C23H22O7
(410.42)
M.p. : 132–178°

O [α]D : +73° (pyridine)

OOC

OH
CH2
CH2OH O

(1, 2) (1)

SOURCE: Cichorium intybus L., chicory (Asteraceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Schistocerca gregaria (Forsk.) Glass fiber 1.0% Feeding deterrence = Treatment given to 2-
(Desert locust) disk test 89.0% to 3-day-old adults of
either sex (1:1).
0.68% Feeding deterrence = (2)
83.5%

0.21% Feeding deterrence =


77.5%

0.11% Feeding deterrence =


54.5%
(on dry
weight
basis)

(1) Pyrek, J.S. (1977) Roczniki Chemii., 51, 2165.


(2) Rees, S.B. and Harborne, J.B. (1985) Phytochemistry, 24, 2225.

© 2005 by CRC Press LLC


598 Opender Koul

LAMBERTIANIC ACID C20H28O3


(316.44)
M.p. : 126.5–127.5°

[α]22
D : +55° (EtOH)

CH2

COOH

(1, 2) (1)

SOURCE: Osmunda asiatica (Fern.) Fraser-Jenkins, fern (Osmundaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Schizaphis graminum (Rondani) Artificial diet 0.006% Feeding deterrence = Treatment given to
(Wheat aphid) feeding 50.0% aphids at random.
(2)

(1) Dauben, W.G. and German, V.F. (1969) Tetrahedron, 22, 679.
(2) Rose, A.F., Jones, K.C., Haddon, W.F., and Dreyer, D.L. (1981) Phytochemistry, 20, 2249.

© 2005 by CRC Press LLC


Insect Antifeedants 599

LASEROLIDE C22H30O6
(390.48)
M.p. : 140–141°

[α]20
D : –234°

OAc
O

O
O

(1, 2) (1)

SOURCE: Laser trilobum (L.) Borkh., gladich (Apiaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius (L.) Wafer disk 1% Feeding deterrence 1. Treatment given to


(Grain weevil) test coefficient = 76 adults.

2. Tribolium confusum Duv. Wafer disk 1% Feeding deterrence 2. Treatment given to


(Confused flour beetle) test coefficient both adults and
Adults = 117 larvae.
Larvae = 71

3. Trogoderma granarium Wafer disk 1% Feeding deterrence 3. Treatment given to


Everts test coefficient = 66 larvae.
(Khapra beetle)
Neutral value = 0
Absolute feeding
deterrence value =
200
(3)

(1) Holub, M., Samek, Z., Popa, D.P., Herout, V., and Sorm, F. (1970) Collect. Czech. Chem. Commun., 35, 284.
(2) Nawrot, J., Smitalova, Z., and Holub, M. (1983) Biochem. Syst. Ecol., 11, 243.

© 2005 by CRC Press LLC


600 Opender Koul

LASIDIOL ANGELATE C20H32O3


(320.47)
Oil

OH

(1) (1)

SOURCE: Lasianthaea fruticosa (L.) Becker (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Atta cephalotes (L.) Feeding deterrence Repels leaf cutter


(Leaf cutter ants) ants apparently due
to antifeedant effect.

No quantitative data
given.
(1)

(1) Wiemer, D.F. and Ales, D.C. (1981) J. Org. Chem., 46, 5449.

© 2005 by CRC Press LLC


Insect Antifeedants 601

LASIOCARPINE C21H33O7N
(411.49)
M.p. : 95°
(95.5–97°)

[α]20
D : –4° (EtOH)
C OH
H
CH3 HO C
OCH3
C C C O

O C H O

O CH2

(1, 2) (1)

SOURCE: Heliotropium arbainense Fres., heliotrop (Boraginaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Choristoneura fumiferana Paper 1.2 × 103 M Feeding deterrence = Treatment to 6th


(Clemens) penicillin 88.0% instar larvae.
(Spruce budworm) disk assay (2)

LD50 (rats): 72 mg/kg (i.p.) (3)

(1) Menshikov, G. (1932) Ber., 65, 974.


(2) Bentley, M.D., Leonard, D.E., Stoddard, W.F., and Zalkow, L.H. (1984) An. Entomol. Soc. Am., 77, 393.
(3) Cordell, G.A. (1981) Introduction to Alkaloids, John Wiley & Sons, New York, p. 134.

© 2005 by CRC Press LLC


602 Opender Koul

LAURIC ACID C12H24O2


(dodecanoic acid) (200.32)
M.p. : 44°

B.p. : 225°/100 mm

nD82 : 1.4183

COOH

(1, 2) (1)

SOURCE: Synthetic (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Incisitermes minor (Hagen) Paper towel 0.25 mg/cm2 Feeding deterrence = Treatment to larvae
(Western drywood termite) disk assay 49.4% of 10–13 mg body
weight for 1 week.
0.05 mg/cm2 Feeding deterrence = (2)
16.0%

LD50 (mice): 131.0 + 5.7 mg/kg (i.v.) (3)

(1) Dale, A.P. and Meara, M.L. (1955) J. Sci. Food Agric., 6, 162.
(2) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39.
(3) Oro, L. and Wretlind, A. (1961) Acta Pharmacol. Toxicol., 18, 141.

© 2005 by CRC Press LLC


Insect Antifeedants 603

LEDOL C15H26O
(222.37)
M.p. : 105°

B.p. : 282–283°

[α]D : +8° (EtOH)

OH

(1, 2) (1, 2)

SOURCE: Entandrophragma cylindricum (Sprague) Sprague., penkua (Meliaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius (L.) Wafer disk 10 mg/ml Feeding deterrence 1. Treatment given to
(Grain weevil) test coefficient = 125.2 adults.

2. Tribolium confusum Duv. Wafer disk 10 mg/ml Feeding deterrence 2. Treatment given to
(Confused flour beetle) test coefficient both adults and
Adults = 159.3 larvae.
Larvae = 104.6

3. Trogoderma granarium Wafer disk 10 mg/ml Feeding deterrence 3. Treatment given to


Everts test Coefficient = 178.3 larvae.
(Khapra beetle)
Neutral value = 0
Absolute feeding
deterrence value =
200
(2)

(1) El-Seedi, H., Ghia, F., and Torssell, K.B.G. (1994) Phytochemistry, 35, 1495.
(2) Daniewski, W.M., Gumulka, M., Ancezewski, W., Truszewska, D., Bloszyk, E., and Drozdz, B. (1996) Polish
J. Chem., 70, 1265.

© 2005 by CRC Press LLC


604 Opender Koul

LEPTINE–III
Not well characterized

Unknown structure
Sugar residual not identified

SOURCE: Commercial material (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Leptinotarsa decemlineata Sensillum 0.02% Feeding deterrence = Treatment to adult


(Say) response wet weight 50.0% beetles.
(Colorado potato beetle) recording (1)

(1) Mitchel, B.K. and Harrison, G.D. (1985) J. Chem. Ecol., 11, 73.

© 2005 by CRC Press LLC


Insect Antifeedants 605

LEVOPIMARIC ACID C20H30O2


(302.46)
M.p. : 150–152°

[α]24
D : –276° (EtOH)

COOH

(1, 2) (1, 2)

SOURCE: Pinus banksiana Lamb., jack pine (Pinaceae) (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Neodiprion dubiosus Schedl. Pine needle 0.5 mg/ml Feeding inhibition = 1. Treatment to 3rd or
(Brownhead jack pine sawfly) and twig 1.0 mg/ml 71.0% 4th instar larvae for
application Feeding inhibition = 4 h.
83.0% (3)

2. Neodiprion rugifrons Pine needle 0.5 mg/ml Feeding inhibition = 2. Treatment to 3rd or
Middleton and twig 45.0% 4th instar larvae for
(Redhead jack pine sawfly) application 1.0 mg/ml Feeding inhibition = 4 h.
67.0% (3)

3. Neodiprion lecontei (Fitch) Pine needle 11.3 mg/ml Feeding inhibition = 3. Treatment to 3rd or
(Redhead pine sawfly) and twig 70.0% 4th instar larvae for
application 4 h.
(4)

4. Schizaphis graminum Artificial diet 0.03% Feeding inhibition = 4. Treatment to


(Rondani) feeding 50.0% aphids at random.
(Wheat aphid) (5)

(1) Harris, G.C. and Sanderson, T.F. (1948) J. Am. Chem. Soc., 70, 334.
(2) Schuller, W.H. and Lawrence, R.V. (1961) J. Am. Chem. Soc., 83, 2563.
(3) Schuh, B.A. and Benjamin, D.M. (1984) J. Chem. Ecol., 10, 1071.
(4) Schuh, B.A. and Benjamin, D.M. (1984) J. Econ. Entomol., 77, 802.
(5) Rose, A.F., Jones, K.C., Haddon, W.F., and Dreyer, D.L. (1981) Phytochemistry, 20, 2249.

© 2005 by CRC Press LLC


606 Opender Koul

LICOISOFLAVONE–A C20H18O6
(354.36)
M.p. : 111–114°

HO O

OH O
HO OH

(1, 2) (1, 2)

SOURCE: Lupinus angustifolius L., European blue lupine (Fabaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Costelytra zealandica Artificial diet 200 µg/ml Feeding inhibition = 1. Treatment to 24-h
(White) feeding 31.0% starved 3rd instar
(Scarab beetle) larvae for 24 h.
(3)

2. Heteronychus arator (Fab.) Artificial diet 200 µg/ml Feeding inhibition = 2. Treatment to 24-h
(Pasture scarab beetle) feeding 33.0% starved 3rd instar
larvae for 24 h.
(2)

(1) Kinoshita, T., Saitoh, T., and Shibata, S. (1978) Chem. Pharm. Bull., 26, 141.
(2) Lane, G.A., Sutherland, O.R.W., and Skip, R.A. (1987) J. Chem. Ecol., 13, 771.
(3) Lane, G.A., Biggs, D.R., Russel, G.B., Sutherland, O.R.W., Williams, E.M., Maindonald, J.H., and Donnel,
D.J. (1985) J. Chem. Ecol., 11, 1713.

© 2005 by CRC Press LLC


Insect Antifeedants 607

LICOISOFLAVONE–B C20H16O6
(352.34)
M.p. : 185–186°

HO O
OH

OH O
O

(1, 3) (1, 3)

SOURCE: Lupinus angustifolius L., European blue lupine (Fabaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Costelytra zealandica Artificial diet 1.2 µg/g Feeding inhibition = 1. Treatment to 24-h
(White) feeding 50.0% starved 3rd instar
(Scarab beetle) larvae for 24 h.
(3)

2. Heteronychus arator (Fab.) Artificial diet 200 µg/ml Feeding inhibition = 2. Treatment to 24-h
(Pasture scarab beetle) feeding 50.0% starved 3rd instar
larvae for 24 h.
(2)

(1) Ingham, J.L., Tahara, S., and Harborne, J.B. (1983) Z. Naturforsch, 38C, 194.
(2) Lane, G.A., Sutherland, O.R.W., and Skip, R.A. (1987) J. Chem. Ecol., 13, 771.
(3) Lane, G.A., Biggs, D.R., Russel, G.B., Sutherland, O.R.W., Williams, E.M., Maindonald, J.H., and Donnel,
D.J. (1985) J. Chem. Ecol., 11, 1713.

© 2005 by CRC Press LLC


608 Opender Koul

LIMONILIC ACID C26H30O9


(486.52)
M.p. : 290–292°

O [α]D : +104° (acetone)

O
OH
O

O O
O O

(1, 2) (1)

SOURCE: Synthetic (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Leptinotarsa decemlineata Leaf disk 100 µg/cm2 Feeding deterrence = Treatment to 4th
(Say) test 77.3% instar larvae for
(Colorado potato beetle) 6–8 h.
31.7 µg/cm2 Feeding deterrence = (2)
73.3%
FI50 = 18.28 µg/cm2
10.0 µg/cm2 Feeding deterrence = Calculated from
44.9% Reference 2.

3.17 µg/cm2 Feeding deterrence =


4.7%

(1) Barton, D.H.R., Pradhan, S.K., Sternhell, S., and Templeton, J.F. (1961) J. Chem. Soc., 255.
(2) Bentley, M.D., Rajab, M.S., Alford, A.R., Mendel, M.J., and Hassanali, A. (1988) Entomol. Exp. Appl., 49, 189.

© 2005 by CRC Press LLC


Insect Antifeedants 609

LIMONIN C26H30O8
(470.52)
M.p. : 298°
O
[α]D : –125° (Acetone)
O

O O

O
O O

O
(1, 2) (1)

SOURCE: Many citrus species (2)


Citrus paradis Macfad., grape fruit (Rutaceae) (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Eldana saccharina Walker Leaf disk 100 µg/disk Feeding deterrence = 1. Treatment to 12-h
(Sugarcane borer) test 61.0 ± 10% pre-starved late 5th
instar larvae.
10 µg/disk Feeding deterrence = (2)
42.0 ± 14%

2. Maruca testulalis (Geyer) Leaf disk 100 µg/disk Feeding deterrence = 2. Treatment to 12-h
(Bean pod borer) test 75.0 ± 9% pre-starved late 5th
instar larvae.
10 µg/disk Feeding deterrence = (2)
58.0 ± 21%

3. Spodoptera litura (Fab.) Leaf disk 0.5% Feeding inhibition 3. Treatment to 3rd
(Tobacco armyworm) spray test ratio = + 4 and 4th instar larvae.
(3)
EC50 = 0.78 µg/cm2
calculated from
Reference 4.
(4)

4. Leptinotarsa decemlineata Leaf disk 100 µg/cm2 Feeding deterrence = 4. Treatment to 4th
(Say) test 67.4% instar larvae.
(Colorado potato beetle) (5)
31.7 µg/cm2 Feeding deterrence =
64.4%

5. Reticulitermes speratus Kolbe Paper disk 47,791 ppm Feeding deterrence = 5. Treatment to 3rd
(Subterranean termite) no-choice 50.0% instar larvae based on
test size.
Treatment duration =
25 days.
Concentration =
EC50value.
(6)

© 2005 by CRC Press LLC


610 Opender Koul

6. Spodoptera frugiperda Leaf disk 6.12 µg/disk Feeding inhibition = 6. Treatment to


(J.E. Smith) test 95.0% larvae.
(Fall armyworm) (7)
Glass fiber 100 ppm Feeding inhibition = Treatment to 24-to
disk test 87.0% 36-h-old final
stadium larvae pre-
starved for 2 h for
8 h.
(9)

7. Heliothis zea (Boddie) Leaf disk 60.8 µg/disk Feeding inhibition = 7. Treatment to
(Corn earworm) test 95.0% larvae.
(7)

8. Hylobius pales (Herbst.) Twig dip 10% Feeding inhibition = 8. Treatment to


(Pales weevil) treatment, 59.2% 22–65 mg body
choice test weight weevils for
24 h.
(8)

Data calculated from


Reference 8.

(1) Melera, A., Schaffner, K., Arigoni, D., and Jeger, O. (1957) Helv. Chim. Acta, 40, 1420.
(2) Hassanali, A., Bentley, M.D., Sitayo, E.N.O., Njoroge, P.E.W., and Yatagai, M. (1986) Insect Sci. Applic., 7,
495.
(3) Koul, O. (1983) Z. Angew, Entomol., 95, 166.
(4) Govindachari, T.R., Narasimhan, N.S., Suresg, G., Partho, P.D., Gopalakrishnan, G., and Krishna Kumari,
G.N. (1995) J. Chem. Ecol., 21, 1585.
(5) Alford, A.R., Cullen, J.A., Storch, R.H., and Bentley, M.D. (1987) J. Econ. Entomol., 80, 575.
(6) Serit, M., Ishida, M., Hagiwara, N., Kim, M., Yamamoto, T., and Takahashi, S. (1992) J. Chem Ecol., 18, 593.
(7) Kubo, I. and Klocke, J.A. (1981) Colloques Inst. Nat. Recherches Agric., 7, 117.
(8) Salom, S.M., Carlson, J.A., Ang, B.N., Grosman, D.M., and Day, E.R. (1994) J. Entomol. Sci., 29, 407.
(9) Ruberto, G., Renda, A., Tringali, C., Napoli, E.M., and Simmonds, M.S.J. (2002) J. Agric. Food Chem., 50,
6766.

© 2005 by CRC Press LLC


Insect Antifeedants 611

LIMONIN DIOSPHENOL C26H28O9


(Evodol) (484.50)
M.p. : 273–278°
O (280–285°)

O [α]24
D : –193° (Acetone)

O O

O
O O

OH

(1, 2) (1)

SOURCE: Evodia glauca Miq., Summer fir (Rutaceae) (2)


Synthetic (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera litura (Fab.) Leaf disk 1000 ppm Feeding deterrence = 1. Treatment to
(Tobacco armyworm) test 100% larvae at random.
(2)

2. Leptinotarsa decemlineata Leaf disk 100 µg/cm2 Feeding deterrence = 2. Treatment to 4th
(Say) test 93.8% instar larvae for 6 to
(Colorado potato beetle) 8 h.
31.7 µg/cm2 Feeding deterrence = (3)
81.4%
FI50 = 11.7 µg/cm2
10.0 µg/cm2 Feeding deterrence = Calculated from
56.6% Reference 3.

3.17 µg/cm2 Feeding deterrence =


6.2%

(1) Dreyer, D.L. (1967) J. Org. Chem., 32, 3442.


(2) Nakatani, M., Takao, H., Iwashita, T., Naoki, H., and Hase, T. (1987) Bull. Chem. Soc. Jpn., 60, 2503.
(3) Bentley, M.D., Rajab, M.S., Alford, A.R., Mendel, M.J., and Hassanali, A. (1988) Entomol. Exp. Appl., 49, 189.

© 2005 by CRC Press LLC


612 Opender Koul

LIMONIN-7-METHOXIME C27H33O8N
(499.56)
Amorphous solid
O
[α]25
D : –134.65° (CHCl3)
O

O O

O
O O

OCH3

(1) (1)

SOURCE: Synthetic (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera frugiperda Glass-fiber 100 ppm Feeding deterrence = Treatment for 8 h to


(J. E. Smith) disk test 76.0% 24- to 36-h-old final
(Fall armyworm) stadium larvae pre-
starved for 2 h.
(1)

(1) Ruberto, G., Renda, A., Tringali, C., Napoli, E.M., and Simmonds, M.S.J. (2002) J. Agric. Food Chem., 50,
6766.

© 2005 by CRC Press LLC


Insect Antifeedants 613

LIMONIN-7-OXIME C26H31O8N
(485.53)
Amorphous solid
O
[α]25
D : –159.46° (CHCl3)
O

O O

O
O O

OH

(1) (1)

SOURCE: Synthetic (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera frugiperda Glass-fiber 100 ppm Feeding deterrence = Treatment for 8 h to


(J. E. Smith) disk test 68.0% 24- to 36-h-old final
(Fall armyworm) stadium larvae pre-
starved for 2 h.
(1)

(1) Ruberto, G., Renda, A., Tringali, C., Napoli, E.M., and Simmonds, M.S.J. (2002) J. Agric. Food Chem., 50,
6766.

© 2005 by CRC Press LLC


614 Opender Koul

LIMONOL C26H32O8
(472.53)
[α]25
D : –57.28° (CHCl3)

O O

O
O O

OH

(1, 2) (1)

SOURCE: Synthetic (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera frugiperda Glass-fiber 100 ppm Feeding deterrence = 1. Treatment for 8 h


(J. E. Smith) disk test 68.0% to 24- to 36-h-old
(Fall armyworm) final stadium larvae
pre-starved for 2 h.
(1)

2. Leptinotarsa decemlineata Leaf disk 100 µg/cm2 Feeding deterrence = 2. Treatment to 4th
(Say) test 78.7% instar larvae for 6 to
(Colorado potato beetle) 8 h.
31.7 µg/cm2 Feeding deterrence = (2)
48.4%
FI50 = 24.28 µg/cm2
10.0 µg/cm2 Feeding deterrence = Calculated from
39.4% Reference 2.

3.17 µg/cm2 Feeding deterrence =


11.9%

(1) Ruberto, G., Renda, A., Tringali, C., Napoli, E.M., and Simmonds, M.S.J. (2002) J. Agric. Food Chem., 50,
6766.
(2) Bentley, M.D., Rajab, M.S., Alford, A.R., Mendel, M.J., and Hassanali, A. (1988) Entomol. Exp. Appl., 49, 189.

© 2005 by CRC Press LLC


Insect Antifeedants 615

LINIFOLIN–A C17H20O5
(304.34)
M.p. : 195–198°

[α]26
D : +33° (CHCl3)

O
O
OAc
CH2

(1, 2) (1)

SOURCE: Helenium aromaticum (Hook) Bailey, aromatic aster weed (Asteraceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius (L.) Wafer disk 8 mg/cm3 Feeding deterrence 1. Treatment given to
(Grain weevil) test coefficient = adults.
101–150

2. Tribolium confusum Duv. Wafer disk 8 mg/cm3 Feeding deterrence 2. Treatment given to
(Confused flour beetle) test coefficient both adults and
Adults = 101–150 larvae.
Larvae = 51–100

3. Trogoderma granarium Wafer disk 8 mg/cm3 Feeding deterrence 3. Treatment given to


Everts test coefficient = larvae.
(Khapra beetle) 151–200
Neutral value = 0
Absolute feeding
deterrence value =
200
(2)

(1) Herz, W. (1962) J. Org. Chem., 27, 4043.


(2) Nawrot, J., Bloszyk, E., Grabarczyk, H., and Drozdz, B. (1982) Prace.Nauk. Inst. Ochr. Roslin, 24, 27.

© 2005 by CRC Press LLC


616 Opender Koul

LINOLEIC ACID C18H32O2


(280.45)
B.p. : 230°/16 mm

n20
D : 1.4699

COOH

(1, 2) (1)

SOURCE: Pinus lambertiana Dougl., sugar pine (Pinaceae) (2)


Hibiscus syriacus L., rose-of-sharon (Malvaceae) (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Incisitermes minor (Hagen) Paper towel 0.25 mg/cm2 Feeding deterrence = 1. Treatment to
(Western drywood termite) disk assay 43.4% larvae of 10–13 mg
body weight for one
0.05 mg/cm2 Feeding deterrence = week.
12.4% (2)
Data calculated from
Reference 2.

2. Anthonomus grandis Bohem. Plate 100 µg/ Feeding 25% of 2. Treatment to adult
(Boll weevil) bioassay feeding site controls after 3 h and weevils.
35% after 6 h in (3)
males and 21% and
34% in females,
respectively.

(1) Swern, D. and Parker, W.E. (1953) J. Am. Oil Chem. Soc., 30, 5.
(2) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39.
(3) Bird, T.G., Hedin, P.A., and Burks, M.L. (1987) J. Chem. Ecol.., 13, 1087.

© 2005 by CRC Press LLC


Insect Antifeedants 617

LINOLENIC ACID C18H30O2


(278.44)
M.p. : –11.3°

B.p. : 230–232°/1 mm
COOH

(1, 2) (1)

SOURCE: Pinus lambertiana Dougl., sugar pine (Pinaceae) (2)


Hibiscus syriacus L., rose-of-sharon (Malvaceae) (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Incisitermes minor (Hagen) Paper towel 0.25 mg/cm2 Feeding deterrence = 1. Treatment to
(Western drywood termite) disk assay 45.1% larvae of 10–13 mg
body weight for one
0.05 mg/cm2 Feeding deterrence = week.
22.0% (2)
Data calculated from
Reference 2.

2. Anthonomus grandis Bohem. Plate 100 µg/ Feeding 33% of 2. Treatment to adult
(Boll weevil) bioassay feeding site controls after 2 h and weevils.
34% after 6 h in (3)
males and 23% and
21% in females,
respectively.

(1) Swern, D. and Parker, W.E. (1953) J. Am. Oil Chem. Soc., 30, 5.
(2) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39.
(3) Bird, T.G., Hedin, P.A., and Burks, M.L. (1987) J. Chem. Ecol.., 13, 1087.

© 2005 by CRC Press LLC


618 Opender Koul

LOBATIN–A C22H30O8
(422.47)
M.p. : 154–155°

[α]20
D : –304° (CHCl3)

O O
O
O

OH
O
CH
O

(1, 2) (2)

SOURCE: Neurolaena lobata (L.) R. Br., golden rod (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk no- 70 µg/1.5 cm2 Feeding deterrence = Treatment to 5th
(Tobacco armyworm) choice test 52.2% instar larvae pre-
starved for 3 h.
Treatment duration =
30 min.
(1)

(1) Passreiter, C.M. and Isman, M.B. (1997) Biochem. Syst. Ecol., 25, 371.
(2) Passreiter, C.M., Wendisch, D., and Gondol, D. (1995) Phytochemistry, 39, 133.

© 2005 by CRC Press LLC


Insect Antifeedants 619

LOBATIN–B C20H24O7
(376.40)
Oil

[α]20
D : –11.5° (CHCl3)
O OH

O
O
O
CH2

(1, 2) (3)

SOURCE: Neurolaena lobata (L.) R. Br., golden rod (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk no- 70 µg/1.5 cm2 Feeding deterrence = Treatment to 5th
(Tobacco armyworm) choice test 41.3% instar larvae pre-
starved for 3 h.
Treatment duration =
30 min.
(1)

(1) Passreiter, C.M. and Isman, M.B. (1997) Biochem. Syst. Ecol., 25, 371.
(2) Passreiter, C.M., Wendisch, D., and Gondol, D. (1995) Phytochemistry, 39, 133.
(3) Borges-del-Castillo, J., Manresa-Ferrero, T., Rodriguez-Luis, F., Vazquez-Bueno, P., Gupta, M.P., and Joseph-
Nathan, P. (1987) J. Nat. Prod., 45, 762.

© 2005 by CRC Press LLC


620 Opender Koul

LONCHOCARPIN C20H18O3
(306.36)
M.p. : 108°

O OH

(1, 2) (1)

SOURCE: Lonchocarpus neuroscapha Benth., Coroa piaca (Fabaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera exempta (Walker) Glass fiber 100 ppm Feeding deterrence = 1. Treatment to 24- to
(Nutgrass armyworm) disk dual- 55.0% 36-h-old final
choice test stadium larvae for
10 ppm Feeding deterrence = 5 h. Larvae pre-
39.0% starved for 4 h.
(2)

2. Spodoptera littoralis (Boisd.) Glass fiber 100 ppm Feeding deterrence = 2. Treatment to 24- to
(Egyptian cotton leaf worm) disk dual- 43.0% 36-h-old final
choice test stadium larvae for
5 h. Larvae pre-
starved for 4 h.
(2)

(1) Monache, F.D., Suarez, L.E.C., and Bettolo, G.B.M. (1978) Phytochemistry, 17, 1812.
(2) Simmonds, M.S.J., Blaney, W.M., Monache, F.D., and Bettolo, G.B.M. (1990) J. Chem. Ecol., 16, 365.

© 2005 by CRC Press LLC


Insect Antifeedants 621

LUPANINE C15H24ON2
(248.37)
M.p. : 40°

B.p. : 185–186°/0.8 mm

H
[α]D : +61.4° (Me2CO)
N

N
H

(1, 2) (1)

SOURCE: Lupinus polyphyllus Lindl., lupine (Fabaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Choristoneura fumiferana Paper 2 × 103 M Feeding deterrence = Treatment to 6th


(Clemens) penicillin 25.0% instar larvae.
(Spruce budworm) disk assay (2)

LD50 (rats): 1440 mg/kg (oral) (3)

(1) Clemo, G.R., Raper, R., and Seaton, J.C. (1956) J. Chem. Soc., 3390.
(2) Bentley, M.D., Leonard, D.E., Reynolds, E.K., Leach, S., Beck, A.B., and Murakoshi, I. (1984) Ann. Entomol.
Soc. Am., 77, 398.
(3) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC


622 Opender Koul

LUPININE C10H19ON
(169.27)
M.p. : 68.5–69°

B.p. : 255–257°/ mm

CH2OH [α]17
D : –20.35° (EtOH)
H

(1, 2, 3) (1, 2)

SOURCE: Commercial sample (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Acyrthosiphon pisum (Harris) Artificial diet 0.00082 ± Feeding deterrence = Treatment to aphids
(Pea aphid) feeding 0.0003% 50.0% at random.
Concentration = EC50
(3)

LD50 (mice): 15 mg/kg (ivn.) (4)

(1) Karrer, P. (1928) Helv. Chim. Acta, 11, 1062.


(2) Gouch, J.F. (1934) J. Am. Chem. Soc., 56, 2434.
(3) Dreyer, D.L., Jones, K.C., and Molyneux, R.J. (1985) J. Chem. Ecol., 11, 1045.
(4) (1994) Dictionary of Natural Products, Chapman & Hall, London.

© 2005 by CRC Press LLC


Insect Antifeedants 623

LUTEOLIN C15H10O6
(286.24)
M.p. : 328–330° (dec.)

OH

OH

HO O

OH O

(1) (1)

SOURCE: Semisynthetic (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Schizaphis graminum (Rondani) Artificial diet 0.03% Feeding deterrence = Treatment to 50–75
(Wheat aphid) feeding 50.0% aphids at random for
24 h.
Concentration = EC50
(2)

LD50 (mice): 180 mg/kg (ipr.) (3)

(1) C.f. Merck Index (1983).


(2) Dreyer, D.L. and Jones, K.C. (1981) Phytochemistry, 20, 2489.
(3) Elangovan, V. (1994) Cancer Lett., 87, 107.

© 2005 by CRC Press LLC


624 Opender Koul

LUTEONE C20H18O6
(354.34)
M.p. : 222–223° (dec.)
(225–227°)

HO O

OH O
HO OH

(1) (1)

SOURCE: Lupinus angustifolius L., European blue lupine (Fabaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Costelytra zealandica Artificial diet 2 µg/ml Feeding deterrence = 1. Treatment to 24-h


(White) feeding 45.6% pre-starved 3rd instar
(Scarab beetle) larvae.
100 µg/ml Feeding deterrence = Treatment duration =
92.3% 24 h.
(1)

2. Heteronychus arator (Fab.) Artificial diet 100 µg/ml Feeding deterrence = 2. Treatment to 24–h
(Pasture scarab beetle) feeding 23.9% pre-starved 3rd instar
larvae.
Treatment duration =
24 h.
(1)

(1) Lane, G.A., Sutherland, O.R.W., and Skipp, R.A. (1987) J. Chem. Ecol., 13, 771.

© 2005 by CRC Press LLC


Insect Antifeedants 625

LUVANGETIN C15H14O4
(258.27)
M.p. : 108–109°

OCH3

O O O

(1, 2) (1, 3)

SOURCE: Atalantia racemosa Wight, and Arn., wild lime (Rutaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Artificial diet 220 ppm Feeding deterrence = Treatment to 4th
(Tobacco armyworm) assay 50.0% instar larvae pre-
starved for 4 h.
Treatment duration =
48 h.
Concentration = EC50
(2)

(1) Murray, R.D.H. (1978) Prog. Chem. Org. Nat. Prod., 35, 199.
(2) Luthria, D.L., Ramakrishnan, V., Verma, G.S., Prabhu, B.R., and Banerji, A. (1989) J. Agric. Food Chem.,
37, 1435.
(3) Bose, P.K. (1944) J. Ind. Chem. Soc., 21, 181.

© 2005 by CRC Press LLC


626 Opender Koul

LYCORAMINE CARBONATE C17H23O3N.½H2CO.2H2O


(356.42)
M.p. : 130–135°
(amorphous)

H
H3CO O

OH

+
N 1/2 CO32-

(1) (1)

SOURCE: Lycoris radiata Herb., red spider lily (Amaryllidaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Eurema hecabe mandarina Artificial diet 0.8% Feeding ratio = Treatment to 5th
DelOrza feeding 40.5% instar larvae after 4 h
(Yellow butterfly) (average feeding of pre-starvation.
inhibition) (1)

0.6% Feeding ratio =


62.8%
(no inhibition)

(1) Numata, A., Takemura, T., Ohabayashi, H., Katsuno, T., Yamamoto, K., Sato, K., and Kobayashi, S. (1983)
Chem. Pharm. Bull., 31, 2146.

© 2005 by CRC Press LLC


Insect Antifeedants 627

LYCORICIDINE C14H13O6N
(291.26)
M.p. : 214.5–215.5° (dec.)

OH [α]20
D : +180° (pyridine)

OH

O
OH

NH
O

(1, 2) (1)

SOURCE: Lycoris radiata Herb., red spider lily (Amaryllidaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Eurema hecabe mandarina Artificial diet 0.25% Feeding ratio = Treatment to 5th
DelOrza feeding 21.9% instar larvae after 4 h
(Yellow butterfly) (slight feeding of pre-starvation.
inhibition) (2)

0.1% Feeding ratio =


46.0%
(medium feeding
inhibition)

0.025% Feeding ratio =


44.2%
(medium feeding
inhibition)

(1) Okamoto, T., Torii, Y., and Isogai, Y. (1968) Chem. Pharm. Bull., 16, 1860.
(2) Numata, A., Takemura, T., Ohabayashi, H., Katsuno, T., Yamamoto, K., Sato, K., and Kobayashi, S. (1983)
Chem. Pharm. Bull., 31, 2146.

© 2005 by CRC Press LLC


628 Opender Koul

LYCORICIDINOL C14H13O7N
(narciclasine) (307.26)
M.p. : 232–234°
(216° dec.)
OH
[α]D : +145° (EtOH)
OH

O
OH

NH
O

OH O

(1, 2) (1)

SOURCE: Lycoris radiata Herb., red spider lily (Amaryllidaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Eurema hecabe mandarina Artificial diet 0.25% Feeding ratio = Treatment to 5th
DelOrza feeding 13.0% instar larvae after 4 h
(Yellow butterfly) (strong feeding of pre-starvation.
inhibition) (1)

0.1% Feeding ratio =


15.3%
(strong feeding
inhibition)

0.025% Feeding ratio =


29.3%
(slight feeding
inhibition)

LD50 (mice): 5 mg/kg (s.c.) (3)

(1) Okamoto, T., Torii, Y., and Isogai, Y. (1968) Chem. Pharm. Bull., 16, 1860.
(2) Numata, A., Takemura, T., Ohabayashi, H., Katsuno, T., Yamamoto, K., Sato, K., and Kobayashi, S. (1983)
Chem. Pharm. Bull., 31, 2146.
(3) Piozzi, F. and Marino, M.L. (1969) Phytochemistry, 8, 1745.

© 2005 by CRC Press LLC


Insect Antifeedants 629

LYCORINE C16H17O4N
(287.32)
M.p. : 275–280° (dec.)
(262–264°)

[α]16
D : –129° (EtOH)
OH

HO

H
O
H
N
O

(1, 2) (1, 2)

SOURCE: Hymenocallis littoralis Salisb., lily (Amaryllidaceae) (3)


Lycoris radiata Herb., red spider lily (Amaryllidaceae) (4)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Eurema hecabe mandarina Artificial diet 0.4% Feeding ratio = 1. Treatment to 5th
DelOrza feeding 34.0% instar larvae after 4 h
(Yellow butterfly) (slight feeding of pre-starvation.
inhibition) (4)

0.25% Feeding ratio =


22.8%
(medium feeding
inhibition)

2. Schistocerca gregaria Leaf disk test 0.05% Feeding ratio = 2. Treatment to


(Forsk.) 53.5% sexually immature
(Desert locust) (no inhibition) adults for 24 h.
(3)
0.1% Feeding inhibition =
100%

0.05% Feeding inhibition =


100%

0.025% Feeding inhibition =


90.5%

(1) Takagi, S., Taylor, W.I., Uyeo, S., and Hajima, H. (1955) J. Chem Soc., 4003.
(2) Wildman, W.C. and Kaufman, C.J. (1954) J. Am. Chem. Soc., 76, 5815.
(3) Singh, R.P. and Pant, N.C. (1980) Experientia, 36, 552.
(4) Numata, A., Takemura, T., Ohabayashi, H., Katsuno, T., Yamamoto, K., Sato, K., and Kobayashi, S. (1983)
Chem. Pharm. Bull., 31, 2146.

© 2005 by CRC Press LLC


630 Opender Koul

MAACKIAIN C16H12O5
(284.27)
M.p. : 199–200°
(179–181°)

[α]22
D : –260° (Me2CO)
HO O

H
O
H
O
O

(1, 2) (1, 2, 3)

SOURCE: Sophora japonica L., Japanese sophora (Fabaceae) (1)


Sophora microphylla Ait., sophora (Fabaceae) (2, 4)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Costelytra zealandica Artificial diet 200 µg/ml Feeding inhibition = 1. Treatment to 24-h
(White) feeding 100% starved 3rd instar
(Scarab beetle) larvae for 24 h.
100 µg/ml Feeding inhibition = (4)
100%

2. Heteronychus arator (Fab.) Artificial diet 200 µg/ml Feeding inhibition = 2. Treatment to 24-h
(Pasture scarab beetle) feeding 52.7% starved 3rd instar
larvae for 24 h.
(4)

Data calculated from


Reference 3.

(1) Ollis, W.D. (1966) Experientia, 22, 777.


(2) Briggs, L.H., Cambie, R.C., and Montgomery, R.K. (1975) NZ. J. Sci., 18, 555.
(3) Shibata, S. and Yoshihiro, N. (1963) Chem. Pharm. Bull., 11, 167.
(4) Sutherland, O.R.W., Russel, G.B., Biggs, D.R., and Lane, G.A. (1980) Biochem. Syst. Ecol., 8, 73.

© 2005 by CRC Press LLC


Insect Antifeedants 631

MALTOL C6H6O3
(126.11)
M.p. : 160–162°

OH

(1) (1)

SOURCE: Trifolium repens L., grassland huia (Fabaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Heteronychus arator (Fab.) Artificial diet 200 µg/ml Feeding inhibition = 1. Treatment to 24-h
(Pasture scarab beetle) feeding 25.0% starved 3rd instar
larvae for 24 h.
100 µg/ml Feeding inhibition = (1)
31.6%
Data calculated from
Reference 1.
However, the data
does not have
consistency in
different sets of
experiments.

LD50 (rats): 2330 mg/kg (oral) (2)

(1) Russel, G.B., Sutherland, O.R.W., Christmas, P.E., and Wright, H. (1982) NZ. J. Zool., 9, 145.
(2) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC


632 Opender Koul

MARGARIC ACID C17H34O2


(270.46)
M.p. : 61°

n60
D : 1.4342

COOH

(1, 2) (1)

SOURCE: Pinus lambertiana Dougl., sugar pine (Pinaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Incisitermes minor (Hagen) Paper 0.25 mg/cm2 Feeding deterrence = Treatment to larvae
(Western drywood termite) towel disk 90.7% of 10–13 mg body
assay weight for 1 week.
(2)

Data calculated from


Reference 2.

LD50 (mice): 36.0 ± 0.3 mg/kg (i.v.) (3)

(1) Bhattacharyya, S.C., Chakravarty, K.K., and Kumar, V. (1959) Chem & Indus., 1352.
(2) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39.
(3) Oro, L. and Wretlind, A. (1961) Acta Pharmacol. Toxicol., 18, 141.

© 2005 by CRC Press LLC


Insect Antifeedants 633

MARRUBIN C20H28O4
(332.44)
M.p. : 160°

[α]D : +33.3° (CHCl3)

OH O

O
O

(1, 2, 3) (1, 2)

SOURCE: Marrubium vulgare L., horehound (Labiatae) (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera frugiperda Leaf disk no- 100 ppm Feeding inhibition = Treatment to 4-h
(J.E. Smith) choice test 50.0% starved 3rd instar
(Fall armyworm) larvae for 24 h.
(3)

(1) Fulke, J.W.B., Hederson, M.S., and McCrindle, R. (1968) J. Chem. Soc., 807.
(2) Stephens, L.J. and Wheeler, D.M.S. (1970) Tetrahedron, 26, 1561.
(3) Taboada, J., Camino, M., Gil, N.M., Campos, E., and Guerrero, C. (1994) Rev. Latinoamer. Quim., 23, 120.

© 2005 by CRC Press LLC


634 Opender Koul

MEDICARPIN C16H14O4
(270.28)
M.p. : 127.5–128.5°

HO O

O
OCH3

(1) (1)

SOURCE: Trifolium repens L., grassland huia (Fabaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Heteronychus arator (Fab.) Artificial diet 200 µg/g Feeding inhibition = 1. Treatment to 24-h
(Pasture scarab beetle) feeding 33.0% starved 3rd instar
larvae for 24 h.
100 µg/g Feeding inhibition = (1)
25.8%

2. Costelytra zealandica Artificial diet 200 µg/g Feeding inhibition = 2. Treatment to 3rd
(White) feeding 62.6% instar larvae.
(Scarab beetle) (2)
100 µg/g Feeding inhibition =
39.9% Data calculated from
References 1 and 2.

(1) Russel, G.B., Sutherland, O.R.W., Christmas, P.E., and Wright, H. (1982) NZ. J. Zool., 9, 145.
(2) Sutherland, O.R.W., Russel, G.B., Biggs, D.R., and Lane, G.A. (1980) Biochem Syst. Ecol., 8, 73.

© 2005 by CRC Press LLC


Insect Antifeedants 635

MELAMPODININ–A C25H30O12
(522.50)
M.p. : 208–210°

O OH
COOCH3

O C C C H
OAc
O AcO

CH2
O

(1, 2) (1)

SOURCE: Melampodium americanum L., American blackfoot daisy (Asteraceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera frugiperda Cellulose 1% Feeding inhibition Treatment to 4th


(J.E. Smith) millipore rate = 18.5 mg in instar larvae.
(Fall armyworm) filter disk test 48 h. Average deterrence
rating based on
control-treated disk
consumption.
(2)

(1) Fischer, N.H., Wiley, R.A., Perry, D.L., and Haegele, K.D. (1976) J. Org. Chem., 41, 3956.
(2) Smith, C.M., Kester, K.M., and Fischer, N.H. (1983) Biochem. Syst. Ecol., 11, 377.

© 2005 by CRC Press LLC


636 Opender Koul

MELIACARPININ–A C39H46O14
(738.78)
Data not verified yet

COOCH3

O O OCH3
OH

O
O
AcO OH

(1, 2) (1)

SOURCE: Melia azedarach L., chinaberry (Meliaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera eridania Leaf disk 50 ppm Feeding inhibition = 1. Treatment to 3rd


(Cramer) choice test Threshold level instar larvae for 6 to
(Southern armyworm) 24 h, during which
period 50% of one of
the disks was
consumed.
2. Spodoptera exigua (Hubner) Leaf disk 50 ppm Feeding inhibition = (2)
(Beet armyworm) choice test Threshold level

(1) Nakatani. M., Arikawa, S., Okamura, H., and Iwagawa, T. (1994) Heterocycles, 38, 327.
(2) Nakatani. M., Huang, R.C., Okamura, H., Iwagawa, T., Tadera, K., and Naoki, H. (1995) Tetrahedron, 51,
11731.

© 2005 by CRC Press LLC


Insect Antifeedants 637

MELIACARPININ–B C33H44O12
(632.70)
Amorphous powder

[α]22
D : –6.7° (MeOH)
COOCH3

O OCH3
OH

O O

O
O
O OH

(1) (1)

SOURCE: Melia azedarach L., chinaberry (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera eridania Leaf disk 50 ppm Feeding inhibition = Treatment to 3rd


(Cramer) choice test Threshold level instar larvae for 6 to
(Southern armyworm) 24 h, during which
period 50% of one of
the disks was
consumed.
2. Spodoptera exigua (Hubner) Leaf disk 50 ppm Feeding inhibition = (1)
(Beet armyworm) choice test Threshold level

(1) Nakatani. M., Huang, R.C., Okamura, H., Iwagawa, T., Tadera, K., and Naoki, H. (1995) Tetrahedron, 51,
11731.

© 2005 by CRC Press LLC


638 Opender Koul

MELIACARPININ–C C35H46O14
(690.74)
M.p. : 149–151°
or
Amorphous powder
COOCH3

O OCH3 [α]22
D : +9.1° (MeOH)
H3COOC
OH

O O

O
O
O OH

(1) (1)

SOURCE: Melia azedarach L., chinaberry (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera eridania Leaf disk 50 ppm Feeding inhibition = Treatment to 3rd


(Cramer) choice test Threshold level instar larvae for 6 to
(Southern armyworm) 24 h, during which
period 50% of one of
the disks was
consumed.
2. Spodoptera exigua (Hubner) Leaf disk 50 ppm Feeding inhibition = (1)
(Beet armyworm) choice test Threshold level

(1) Nakatani. M., Huang, R.C., Okamura, H., Iwagawa, T., Tadera, K., and Naoki, H. (1995) Tetrahedron, 51,
11731.

© 2005 by CRC Press LLC


Insect Antifeedants 639

MELIACARPININ–D C35H46O14
(690.74)
M.p. : 165–167°

O [α]22
D : –8.3° (MeOH)

COOCH3

O OCH3
O
OH

O
O
AcO OH

(1) (1)

SOURCE: Melia azedarach L., chinaberry (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera eridania Leaf disk 50 ppm Feeding inhibition = 1. Treatment to 3rd


(Cramer) choice test Threshold level instar larvae for 6 to
(Southern armyworm) 24 h, during which
period 50% of one of
the disks was
consumed.
2. Spodoptera exigua (Hubner) Leaf disk 50 ppm Feeding inhibition = (1)
(Beet armyworm) choice test Threshold level

(1) Nakatani. M., Huang, R.C., Okamura, H., Iwagawa, T., Tadera, K., and Naoki, H. (1995) Tetrahedron, 51,
11731.

© 2005 by CRC Press LLC


640 Opender Koul

MELIACARPININ–E C33H44O13
(648.70)
[α]20
D : –10° (MeOH)

COOCH3

O OCH3
HO
OH

O O

O
O
O OH

(1) (1)

SOURCE: Melia azedarach L., chinaberry (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera eridania (Cramer) Leaf disk 1 µg/cm2 Feeding inhibition = 1. Treatment to 3rd
(Southern armyworm) choice test Threshold level instar larvae for 6 to
24 h, during which
period 50% of one of
the disks was
consumed.
(1)

(1) Huang, R.C., Tadera, K., Yagi, F., Minami, Y., Okamura, H., Iwagawa, T., and Nakatani. M. (1996) Phy-
tochemistry, 43, 581.

© 2005 by CRC Press LLC


Insect Antifeedants 641

MELIANONE C30H46O4
(470.69)
M.p. : 232–233°
O

O
[α]D : –62° (CHCl3)
HO

(1, 2) (1, 2)

SOURCE: Azadirachta indica A. Juss., neem (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Epilachna varivestis Muls. Bean leaf 0.05% Feeding inhibition = Treatment to 4th
(Mexican bean beetle) choice test Threshold level stadium larvae. No
quantitative data
recorded.
(1)

(1) Kraus, W. and Grimminger, W. (1980) Nouv. J. Chim., 4, 651.


(2) Lavie, D., Jain, M.K., and Kirson, I. (1967) J. Chem. Soc. (C), 1347.

© 2005 by CRC Press LLC


642 Opender Koul

MELIANOTRIOL C30H50O5
(490.72)
M.p. : 76–178°

[α]D : –23° (CHCl3)


OH
OH
O

OH

HO

(1) (1)

SOURCE: Melia azedarach L., chinaberry (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera eridania (Cramer) Filter paper 8 γ /cm2 Feeding inhibition = Treatment to 5th mid-
(Southern armyworm) test 100% stadium larvae.
(1)

(1) Lavie, D., Jain, M.K., and Shpan-Gabrielith, S.R. (1967) Chem. Commun., 910.

© 2005 by CRC Press LLC


Insect Antifeedants 643

MELICOPICINE C18H19O5N
(329.35)
M.p. : 133–134°

OCH3 O

H3CO

H3CO N

OCH3

(1, 2) (1)

SOURCE: Teclea trichocarpa Engl., African evergreen teclea (Meliaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera exempta (Walker) Leaf disk 1000 ppm Feeding inhibition = 1. Treatment to 3rd
(Nutgrass armyworm) choice test 100% instar larvae for 2 h.
(2)

(1) Price, J.R. (1949) Aust. J. Sci. Res., A2, 249.


(2) Lwande, W., Gebreyesus, T., Chapya, A., MacFoy, C., Hassanali, A., and Okech, M. (1983) Insect Sci. Applic.,
4, 393.

© 2005 by CRC Press LLC


644 Opender Koul

MELIATOXIN–A2 C34H44O12
(644.71)
M.p. : 155–160° (dec.)
O
[α]22
D : –72.5° (MeOH)

O
OH

AcO

O O

AcO OH
COO

(1, 2) (2)

SOURCE: Melia azedarach L. var. australasia, chinaberry (Meliaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera litura (Fab.) Leaf disk 360 ppm Feeding inhibition = 1. Treatment to
(Tobacco armyworm) choice test 50.0% larvae of 9 to 11 mg
body weight.
Concentration = EC50
(3)

2. Spodoptera eridania Leaf disk 400 ppm Threshold deterrence 2, 3. Treatment to 3rd
(Cramer) choice test level instar larvae for 6 to
(Southern armyworm) 24 h, during which
period 50% of one of
the disks was
consumed.
3. Spodoptera exigua (Hubner) Leaf disk 400 ppm Threshold deterrence (4)
(Beet armyworm) choice test level

(1) Oelrichs, P.B., Hill, M.W., Vallely, P.J., MacLeod, J.K., and Molinski, T.F. (1983) Phytochemistry, 22, 531.
(2) Nakatani, M., Huang, R.C., Okamura, H., Naoki, H., and Iwagawa, T. (1994) Phytochemistry, 36, 39.
(3) MacLeod, J.K., Moeller, P.D.R., Molinski, T.F., and Koul, O. (1990) J. Chem. Ecol., 16, 2511.
(4) Nakatani, M., Huang, R.C., Okamura, H., Iwagawa, T., Tadera, K., and Naoki, H. (1995) Tetrahedron, 51,
11731.

© 2005 by CRC Press LLC


Insect Antifeedants 645

MELIATOXIN–B1 C35H46O12
(658.74)
M.p. : 140–150° (dec.)
O

AcO

O
O
AcO OH
COO

(1, 2) (1, 2)

SOURCE: Melia azedarach L. var. australasia, chinaberry (Meliaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk 450 ppm Feeding inhibition = Treatment to larvae
(Tobacco armyworm) choice test 50.0% of 9 to 11 mg body
weight.
Concentration = EC50
(2)

(1) Oelrichs, P.B., Hill, M.W., Vallely, P.J., MacLeod, J.K., and Molinski, T.F. (1983) Phytochemistry, 22, 531.
(2) MacLeod, J.K., Moeller, P.D.R., Molinski, T.F., and Koul, O. (1990) J. Chem. Ecol., 16, 2511.

© 2005 by CRC Press LLC


646 Opender Koul

o-METHOXYACETOPHENONE C9H10O2
(150.18)
Oil

B.p. : 125–126°/12 mm

OCH3

(1, 2) (2)

SOURCE: Commercial sample (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Pieris rapae crucivora (Boisd.) Leaf disk 5 × 10–7 Feeding inhibition = Treatment to 5th
(Cabbage butterfly) dual-choice mol/cm2 49.3% instar larvae pre-
test starved for 3 h.
Treatment duration =
2 h.
(1)

(1) Yano, K. and Tanaka, N. (1995) Biosci. Biotech. Biochem., 59, 1130.
(2) Laird, R.M. and Parker, R.E. (1961) J. Am. Chem. Soc., 83, 4277.

© 2005 by CRC Press LLC


Insect Antifeedants 647

m-METHOXYACETOPHENONE C9H10O2
(150.18)
Oil

B.p. : 131°/18 mm

OCH3

(1, 2) (1, 2)

SOURCE: Commercial sample (1, 2)


Also found in many plant spp.

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Pieris rapae crucivora (Boisd.) Leaf disk 5 × 10–7 Feeding inhibition = Treatment to 5th
(Cabbage butterfly) dual-choice mol/cm2 96.8% instar larvae pre-
test starved for 3 h.
Treatment duration =
2 h.
(1)

(1) Yano, K. and Tanaka, N. (1995) Biosci. Biotech. Biochem., 59, 1130.
(2) (1994) Dictionary of Natural Products, Chapman & Hall, London.

© 2005 by CRC Press LLC


648 Opender Koul

p-METHOXYACETOPHENONE C9H10O2
(150.18)
M.p. : 37.5–38.5°

B.p. : 138–139°/15 mm
OCH3

(1) (1)

SOURCE: Commercial sample (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Pieris rapae crucivora Boisd. Leaf disk 5 × 10–7 Feeding inhibition = Treatment to 5th
(Cabbage butterfly) dual-choice mol/cm2 78.1% instar larvae pre-
test starved for 3 h.
Treatment duration =
2 h.
(1)

(1) Yano, K. and Tanaka, N. (1995) Biosci. Biotech. Biochem., 59, 1130.

© 2005 by CRC Press LLC


Insect Antifeedants 649

5-METHOXY-N,N-DIMETHYL TRYPTAMINE C13H18ON2


(Bufotenine) (218.30)
M.p. : 67.5–68.5°

B.p. : 208–210°/4 mm

H3CO

N
N
H

(1, 2) (1)

SOURCE: Commercial sample (1, 2)


Occurs in Phalaris tuberosa (Graminae) and Leguminosae plants.

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Rhopalosiphum maidis Artificial 4 mM Feeding inhibition = 1. Treatment to


(Fitch) diet feeding 25.2% aphids at random for
(Corn leaf aphid) 5 h.
(2)

2. Anthonomus grandis Bohem. Agar plug 5.0 µg/mm2 Feeding inhibition = 2. Treatment to
(Boll weevil) bioassay 3.5% newly emerged boll
weevils for 4 h in
dark.
(3)

LD50 (mice): 115 mg/kg (ipr.) (4)

(1) Pachter, I.J., Zacharias, D.E., and Ribeiro, O. (1959) J. Org. Chem., 24, 1283.
(2) Corcuera, L.J. (1984) Phytochemistry, 23, 539.
(3) Miles, D.H., Ly, A.M., Randle, S.A., Hedin, P.A., and Burks, M.L. (1987) J. Agric. Food Chem., 35, 794.
(4) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC


650 Opender Koul

5-METHOXYISOLONCHOCARPIN C21H20O4
(336.39)
Configuration not
determined

O O

OCH3 O

(1)

SOURCE: Tephrosia vogelii Hook F., vogel tephrosia (Fabaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera exempta (Walker) Glass fiber 100 ppm Feeding inhibition = 1. Treatment to 24- to
(Nutgrass armyworm) disk dual- 80.0% 36-h-old final
choice test stadium larvae for
10 ppm Feeding inhibition = 5 hours. Larvae pre-
35.0% starved for 4 h.
(1)

2. Spodoptera littoralis (Boisd.) Glass fiber 100 ppm Feeding inhibition = 2. Treatment to 24- to
(Egyptian cotton leaf worm) disk dual- 64.0% 36-h-old final
choice test stadium larvae for
10 ppm Feeding inhibition = 5 h. Larvae pre-
59.0% starved for 4 h.
(1)

(1) Simmonds, M.S.J., Blaney, W.M., Monache, F.D., and Bettolo, G.B.M. (1990) J. Chem. Ecol., 16, 365.

© 2005 by CRC Press LLC


Insect Antifeedants 651

7-O-METHYL-8-(3-METHYLBUTADIENYL) C22H23O3
-FLAVANONE (335.40)
No physical data given
CH2

H3CO O

(1) (1)

SOURCE: Tephrosia purpurea (L.) Pers., wild indigo (Fabaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera exempta (Walker) Glass fiber 100 ppm Feeding inhibition = 1. Treatment to 24- to
(Nutgrass armyworm) disk dual- 69.0% 36-h-old final
choice test stadium larvae for
10 ppm Feeding inhibition = 5 h. Larvae pre-
42.0% starved for 4 h.
(1)

2. Spodoptera littoralis (Boisd.) Glass fiber 100 ppm Feeding inhibition = 2. Treatment to 24- to
(Egyptian cotton leaf worm) disk dual- 43.0% 36-h-old final
choice test stadium larvae for
10 ppm Feeding inhibition = 5 h. Larvae pre-
85.0% starved for 4 h.
(1)

(1) Simmonds, M.S.J., Blaney, W.M., Monache, F.D., and Bettolo, G.B.M. (1990) J. Chem. Ecol., 16, 365.

© 2005 by CRC Press LLC


652 Opender Koul

(+) 2-METHOXYPHASEOLLINISOFLAVAN C21H22O4


(338.40)
M.p. : 135–136°

[α]24
D : +19.5° (EtOH)
HO O

H3CO O

(1) (1)

SOURCE: Phaseolus vulgaris L., french bean (Fabaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Costelytra zealandica Artificial diet 10 µg/ml Feeding inhibition = 1. Treatment to 24-h


(White) feeding 100% starved 3rd instar
(Scarab beetle) larvae for 24 h.
1 µg/ml Feeding inhibition = (2)
42.9%
Data calculated from
Reference 2.

(1) Van Etten, H.D. (1973) Phytochemistry, 12, 1791.


(2) Sutherland, O.R.W., Russel, G.B., Biggs, D.R., and Lane, G.A. (1980) Biochem. Syst. Ecol., 8, 73.

© 2005 by CRC Press LLC


Insect Antifeedants 653

2-METHOXYPHENOL C7H8O2
(124.14)
M.p. : 32° (prisms)

B.p. : 105–110°/0.3 mm

OH
n25
D : 1.5256

OCH3

(1, 2) (1, 2)

SOURCE: Found in many essential oils and resins (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Acalymma vittatum (Fab.) Leaf disk 0.1% Feeding deterrence = Treatment to adult
(Striped cucumber beetle) assay 100% up to 6 h. beetles.
Reduction in (1)
deterrence by 11% in
22 h. Data calculated from
Reference 1.
0.5% Feeding deterrence =
100% up to 22 h.

LD50 (rats): 725 mg/kg (oral) (3)

(1) Reed, D.K. and Jacobson, M. (1983) Experientia, 39, 378.


(2) Karrer, W. (1958) Konstitution und Vorkommen der Organischen Pflanzenstoffe, Vol. 1, Birkhauser Verlag,
Basel, p. 72.
(3) Opdyke, D.L.J. (1982) Food Cosmet. Toxicol., 20, 697

© 2005 by CRC Press LLC


654 Opender Koul

3-METHOXYPHENOL C7H8O2
(124.14)
B.p. : 110–115°/0.3 mm

n25
D : 1.5276

OH

OCH3

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Acalymma vittatum (Fab.) Leaf disk 0.5% Feeding deterrence = Treatment to adult
(Striped cucumber beetle) assay 100% up to 22 h. beetles.
(1)

(1) Reed, D.K. and Jacobson, M. (1983) Experientia, 39, 378.

© 2005 by CRC Press LLC


Insect Antifeedants 655

4-METHOXYPHENOL C7H8O2
(124.14)
M.p. : 53°

B.p. : 100–103°/0.5 mm

OH n25
D : 1.5228

OCH3

(1) (1, 2)

SOURCE: Synthetic
Also from the leaves of Pirola secunda L., serrated wintergreen (Pyrolaceae) (1,3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Acalymma vittatum (Fab.) Leaf disk 0.5% Feeding deterrence = Treatment to adult
(Striped cucumber beetle) assay 100% up to 22 h. beetles.
(1)

LD50 (rats): 1600 mg/kg (oral) (4)

(1) Reed, D.K. and Jacobson. M. (1983) Experientia, 39, 378.


(2) Penner, G.H. and Wasylishen, R.E. (1989) Can. J. Chem., 67, 525.
(3) Karrer, W. (1958) Konstitution und Vorkommen der Organischen Pflanzenstoffe, Vol. 1, Birkhauser Verlag,
Basel, p. 88.
(4) (1993) Patty’s Ind. Hyg. Toxicol., 4th edition, Vol. 2, Wiley, New York.

© 2005 by CRC Press LLC


656 Opender Koul

5-METHOXYTRYPTAMINE C11H14ON2
(190.24)
M.p. : 121–122°

H3CO

NH2
N
H

(1, 2) (1)

SOURCE: Commercial sample (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Rhopalosiphum maidis (Fitch) Artificial diet 4 mM Feeding inhibition = Treatment to aphids


(Corn leaf aphid) feeding 26.1% at random for 5 h.
(2)

Data calculated from


Reference 2.

LD50 (mice): 176 mg/kg (ipr.) (3)

(1) Suniewski, J. and Misztal, S. (1960) Bull. Acad. Polon. Sci. Ser. Sci. Biol., 8, 479. (cf. CA 55, 15458).
(2) Corcuera, L.J. (1984) Phytochemistry, 23, 539.
(3) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC


Insect Antifeedants 657

METHYL ABIETATE C21H32O2


(316.48)
B.p. : 360–365°

n20
D : 1.530

No structure given

(1, 2) (1)

SOURCE: Commercial mixture of coniferous resin acids and methyl esters (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Incisitermes minor (Hagen) Paper towel 0.05 mg/cm2 Feeding deterrence = Treatment to
(Western drywood termite) disk assay 31.8% after 6 days immature termites of
10–13 mg body
weight.
(2)

(1) (1983), Merck Index, p. 863.


(2) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39.

© 2005 by CRC Press LLC


658 Opender Koul

METHYL 2(Z)-10-ACETOXY-8,9- C13H12O5


EPOXYDECEN-4,6-DIYNOATE (248.23)
Oil

H3COOC OAc

(1) (1)

SOURCE: Chrysothamnus nauseosus (pall.) Britt., rubber rabbit bush (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Leptinotarsa decemlineata Leaf disk < 35 µg/cm2 Feeding deterrence = Treatment to 3rd
(Say) assay threshold level instar larvae.
(Colorado potato beetle) (1)

(1) Rose, A.F., Butt, B.A., and Jermy, T. (1980) Phytochemistry, 19, 563.

© 2005 by CRC Press LLC


Insect Antifeedants 659

METHYL Z,Z-10-ACETOXY C13H12O4


MATRICARIATE (232.23)
Oil

H3COOC OAc

(1) (1)

SOURCE: Chrysothamnus nauseosus (pall.) Britt., rubber rabbit bush (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Leptinotarsa decemlineata Leaf disk 35–70 µg/cm2 Feeding deterrence = Treatment to 3rd
(Say) assay threshold level instar larvae.
(Colorado potato beetle) (1)

(1) Rose, A.F., Butt, B.A., and Jermy, T. (1980) Phytochemistry, 19, 563.

© 2005 by CRC Press LLC


660 Opender Koul

METHYL ARISTOLOCHIATE C18H13O7N


(355.31)
M.p. : 285–286°

COOCH3
O

NO2
O

OCH3

(1) (2)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk 1000 ppm Feeding deterrence Treatment to 4-day-
(Tobacco armyworm) choice assay index = 30.86 old larvae for 1 day.
Antifeedant index
value shows
moderate activity.
The value below 20
is highly deterrent
index.
(1)

(1) Lajide, L., Escoubas, P., and Mizutani, J. (1993a) J. Agric. Food Chem., 41, 2426.
(2) Lajide, L., Escoubas, P., and Mizutani, J. (1993b) J. Agric. Food Chem., 41, 669.

© 2005 by CRC Press LLC


Insect Antifeedants 661

3β-p-METHYLCINNAMATOXYLUP-20-EN- C42H60O4
28-OIC ACID (628.89)
M.p. : 225°
CH2

COOH

COO

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk 100 µg/2 cm Feeding deterrence = Treatment to freshly
(Tobacco armyworm) choice diameter 74.0% molted 4th instar
assay disk larvae for 48 h.
(1)
50 µg/2 cm Feeding deterrence =
diameter 46.0%
disk

25 µg/2 cm Feeding deterrence =


diameter 33.0%
disk

(1) Jagadeesh, S.G., Krupadanam, G.L.D., and Srimannarayana, G. (1998) J. Agric. Food. Chem., 46, 2797.

© 2005 by CRC Press LLC


662 Opender Koul

3-O-METHYL-3-DEACETYLSALANNIN C33H44O8
(568.71)
Only spectral data given

O
O

O O
O

O
H3CO
H
O

(1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Leptinotarsa decemlineata Leaf disk 100 µg/cm2 Feeding deterrence = Treatment to newly
(Say) choice test 95.0% molted 3rd instar
(Colorado potato beetle) larvae.
Disks examined
every 2 h until 95%
of control disks were
consumed.
Concentration = PC95
value.
(1)

(1) Yamasaki, R.B. and Klocke, J.A. (1989) J. Agric. Food Chem., 37, 1118.

© 2005 by CRC Press LLC


Insect Antifeedants 663

3-O-METHYL-3-DEACETYL-2′,3′, C33H50O8
20,21,22,23-HEXAHYDROSALANNIN (574.75)
Only spectral data given

COO O
O

O
H3CO
H
O

(1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Leptinotarsa decemlineata Leaf disk 10 µg/cm2 Feeding deterrence = Treatment to newly


(Say) choice test 95.0% molted 3rd instar
(Colorado potato beetle) larvae.
2 µg/cm2 Feeding deterrence = Disks examined
50.0% every 2 h until 95%
of control disks were
consumed.
Concentrations =
PC95 and PC50 values.
(1)

(1) Yamasaki, R.B. and Klocke, J.A. (1989) J. Agric. Food Chem., 37, 1118.

© 2005 by CRC Press LLC


664 Opender Koul

METHYL α-ELEOSTEARATE C19H32O2


(292.46)
B.p. : 210°/12 mm

n25
D : 1.5000

COOCH3

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Anthonomus grandis grandis Cotton bud 1.0% Feeding deterrence = Treatment to 1- or 2-


Bohem. dip method 73.9% day-old boll weevils
(Boll weevil) for 4 h.
Data based on the
number of bud
punctures in treated
and control
experiments.
(1)

Data calculated from


Reference 1.

(1) Jacobson, M., Crystal, M.M., and Warthen, J.D. Jr. (1981) J. Agric. Food Chem., 29, 591.

© 2005 by CRC Press LLC


Insect Antifeedants 665

METHYL 6,11β-DIHYDROXY-12α-(2-METHYL C31H37O10


PROPANOYLOXY)-3,7-DIOXO-14β,15β-EPOXY- (569.24)
Only spectral data given
1,5-MELIACADIEN-29-OATE
O

O
O

HO

O O
H3COOC
OH
(1) (1)

SOURCE: Trichilia pallida Sw., Kew trichila (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera littoralis (Boisd.) Glass fiber 100 ppm Feeding deterrence = Treatment to final
(Egyptian cotton leaf worm) disk test 46% stadium larvae,
36–48 h into the
2. Spodoptera exigua (Hubner) Glass fiber 100 ppm Feeding deterrence = stadium pre-starved
(Beet armyworm) disk test 40% for 2–3 h.

3. Heliothis virescens (Fab.) Glass fiber 100 ppm Feeding deterrence = Treatment duration =
(Tobacco budworm) disk test 49% 18 h.
(1)
4. Helicoverpa armigera Glass fiber 100 ppm Feeding deterrence =
(Hubner) disk test 42%
(Gram pod borer)

(1) Simmonds, M.S.J., Stevenson, P.C., Porter, E.A., and Veitch, N.C. (2001) J. Nat. Prod., 64, 1117.

© 2005 by CRC Press LLC


666 Opender Koul

3,4-METHYLENEDIOXY BENZYL ALCOHOL C8H8O3


(152.15)
B.p. : 131–135°/0.4 mm

n25
D : 1.5287

CH2OH

O
O

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Acalymma vittatum (Fab.) Leaf disk 0.1% Feeding deterrence = Treatment to adult
(Striped cucumber beetle) assay 100% up to 6 h. beetles.
(1)
0.5% Feeding deterrence =
100% up to 22 h.

(1) Reed, D.K. and Jacobson, M. (1983) Experientia, 39, 378.

© 2005 by CRC Press LLC


Insect Antifeedants 667

3,4-METHYLENEDIOXY PHENOL C7H6O3


(138.12)
B.p. : 120–125°/0.3 mm

nD25 : 1.5368

OH

O
O

(1) (1)

SOURCE: Synthetic (1)


Also occurs naturally in sesame oil (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Acalymma vittatum (Fab.) Leaf disk 0.1% Feeding deterrence = Treatment to adult
(Striped cucumber beetle) assay 100% up to 6 h. beetles.
(1)
0.5% Feeding deterrence =
100% up to 22 h.

(1) Reed, D.K. and Jacobson, M. (1983) Experientia, 39, 378.


(2) Beroza, M. (1954) J. Am. Oil Chem. Soc., 31, 302.

© 2005 by CRC Press LLC


668 Opender Koul

N-METHYL-TRANS-4-HYDROXY-L-PROLINE C6H11O3N
(145.16)
M.p. : 237–241° (dec.)

[α]D : –74° (MeOH)


: –86.6° (H2O)

H H
N
OH H

H COOH
H H

(1) (1)

SOURCE: Copaifera spp., copaiba (Fabaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera littoralis (Boisd.) Leaf disk 100 ppm Feeding inhibition Treatment to larvae
(Egyptian cotton leaf worm) choice test index = 11.2 ± 8.24 at random.
Antifeedant effect
1000 ppm Feeding inhibition significant at 1000
index = 26.7 ± 11.41 ppm level.
(1)

(1) Figliuolo, R., Naylor, S., Wang, T., and Langenheim, J.H. (1987) Phytochemistry, 26, 3255.

© 2005 by CRC Press LLC


Insect Antifeedants 669

E-3- (3,4-METHYLENEDIOXYPHENYL)-N- C28H45O3N


2-[OCTADECYL]-2-PROPENAMIDE (443.67)
M.p. : 100–101°

(CH2)15.CH3
O
N
H

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Reticulitermes speratus (Kolbe) Paper disk 5000 ppm Feeding deterrence Treatment to 3rd
(Subterranean termite) choice assay index = 10.9 instar workers.
Feeding duration =
14 days.
The value below 20
is highly deterrent
effect.
(1)

(1) Lajide, L., Escoubas, P., and Mizutani, J. (1995) Phytochemistry, 40, 1105.

© 2005 by CRC Press LLC


670 Opender Koul

1,5-BIS-(3,4-METHYLENEDIOXYPHENYL) C19H14O5
PENT-1,4-DIEN-3-ONE (322.32)
M.p. : 198–200°

O O

O O

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Reticulitermes speratus (Kolbe) Paper disk 10,000 ppm Feeding deterrence Treatment to 3rd
(Subterranean termite) choice index = 18.0 instar workers.
assay Feeding duration =
14 days.
The value below 20
is highly deterrent
effect.
(1)

(1) Lajide, L., Escoubas, P., and Mizutani, J. (1995) Phytochemistry, 40, 1097.

© 2005 by CRC Press LLC


Insect Antifeedants 671

E-3- (3,4-METHYLENEDIOXYPHENYL)-N- C18H17O4N


2-[4-HYDROXYPHENYLETHYL]- (311.34)
M.p. : 168–170°
2-PROPENAMIDE

OH
O

O
N
H

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Reticulitermes speratus (Kolbe) Paper disk 5000 ppm Feeding deterrence Treatment to 3rd
(Subterranean termite) choice assay index = 25.9 instar workers.
Feeding duration =
14 days.
The value below 20
is highly deterrent
effect.
(1)

(1) Lajide, L., Escoubas, P., and Mizutani, J. (1995) Phytochemistry, 40, 1105.

© 2005 by CRC Press LLC


672 Opender Koul

METHYL ESTER OF VACHANIC ACID C16H26O3


(266.38)
M.p. : 55–56°

[α]20
D : –36.9° (CHCl3)

CH2

H
HO COOCH3

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius (L.) Wafer disk 10 mg/cm3 Feeding deterrence 1. Treatment given to
(Grain weevil) test coefficient = 158.5 adults.

2. Tribolium confusum (Duv.) Wafer disk 10 mg/cm3 Feeding deterrence 2. Treatment given to
(Confused flour beetle) test coefficient both adults and
Adults = 137.7 larvae.
Larvae = 162.2

3. Trogoderma granarium Wafer disk 10 mg/cm3 Feeding deterrence 3. Treatment given to


(Everts) test coefficient = 61.5 larvae.
(Khapra beetle)
Neutral value = 0
Absolute feeding
deterrence value =
200.
(1)

(1) Daniewski, W.M., Kroszczynski, W., Bloszyk, E., Drozdz, B., Grabarczyk, H., Nawrot, J., Rychlewska, U.,
Budesinsky, M., and Holub, M. (1986) Collect. Czech. Chem. Commun., 51, 1710.

© 2005 by CRC Press LLC


Insect Antifeedants 673

METHYL EUGENOL C11H14O2


(178.23)
B.p. : 128–129°/11 mm
(125–127°/12 mm)
OCH3
nD20 : 1.532
OCH3

CH2

(1, 2) (1)

SOURCE: Artemisia capillaris Thumb., wormwood (Asteraceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Pieris rapae crucivora (Boisd.) Leaf disk 10–1 mol/l Feeding inhibition = Treatment to 5th
(Cabbage butterfly) dual-choice 100% instar larvae pre-
test starved for 3 h.
10–2 mol/l Feeding inhibition = Treatment duration =
80.0% 2 h.
(2, 3)

LD50 (rats): 1179 mg/kg (oral) (4)

(1) Nagasawa, M. (1961) J. Pharm. Soc. Jap., 81, 129.


(2) Yano, K. (1987) J. Agric. Food Chem., 35, 889.
(3) Yano, K. and Kamimura, H. (1993) Biosci. Biotech. Biochem., 57, 129.
(4) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC


674 Opender Koul

METHYL GALLATE C8H8O5


(184.15)
M.p. : 157°

COOCH3

HO OH

OH

(1, 2) (1)

SOURCE: Commercial sample (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Schizaphis graminum Artificial diet 103 ppm Feeding inhibition = Treatment to aphids
(Rondani) feeding 50% at random.
(Wheat aphid)

2. Acyrthosiphon pisum (Harris) Artificial diet 218 ppm Feeding inhibition = Concentration = EC50
(Pea aphid) feeding 50.0% values.
(2)
3. Myzus persicae (Sulzer) Artificial diet 303 ppm Feeding inhibition =
(Green peach aphid) feeding 50.0%

LD50 (mice): 1700 mg/kg (oral) (3)

(1) Lajis, N.H. and Khan, M.N. (1994) Ind. J. Chem., 33B, 609.
(2) Jones, K.C. and Klocke, J.A. (1987) Entomol. Exp. Appl., 44, 229.
(3) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC


Insect Antifeedants 675

14 – METHYL HEXADECANOIC ACID C17H34O2


(270.45)
M.p. : 39–40°

[α]29
D : +5.2° (Me2CO)

(CH2)12COOH

H3C C H

CH2.CH3

(1, 2) (1)

SOURCE: Pinus lambertiana Dougl., sugar pine (Pinaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Incisitermes minor (Hagen) Paper towel 0.25 mg/cm2 Feeding deterrence = Treatment to
(Western drywood termite) disk assay 34.7% after 7 days immature termites of
10–13 mg body
0.05 mg/cm2 Feeding deterrence = weight.
16.4% after 6 days (2)

Data calculated from


Reference 2.

(1) Nunn, J.R. (1951) J. Chem. Soc., 1740.


(2) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39.

© 2005 by CRC Press LLC


676 Opender Koul

METHYL-p-HYDROXY BENZOATE C8H8O3


(152.15)
M.p. : 131°
(127–129°)

B.p. : 270–280° (dec.)


COOCH3

OH

(1, 2) (1)

SOURCE: Commercial sample (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Pieris brassicae (L.) Leaf disk 6.6 × 10–2 M Feeding inhibition Treatment to 2nd day
(Large white butterfly) no- choice ratio = 14.21 5th instar un-starved
test larvae. Ratio less
than 20 highly
deterrent.
(2)

(1) (1994) Dictionary of Natural Products, Chapman & Hall, London.


(2) Jones, C.G. and Firn, R.D. (1979) Biochem. Syst. Ecol., 7, 187.

© 2005 by CRC Press LLC


Insect Antifeedants 677

METHYL 2(Z)-10-HYDROXY-8,9- C11H10O4


EPOXYDECEN-4,6-DIYNOATE (206.20)
M.p. : 53–54°
(Uncorrected)

H3COOC OH

(1) (1)

SOURCE: Chrysothamnus nauseosus (pall.) Britt., rubber rabbit bush (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Leptinotarsa decemlineata Leaf disk < 35 µg/cm2 Feeding deterrence = Treatment to 3rd
(Say) assay threshold level. instar larvae.
(Colorado potato beetle) (1)

(1) Rose, A.F., Butt, B.A., and Jermy, T. (1980) Phytochemistry, 19, 563.

© 2005 by CRC Press LLC


678 Opender Koul

METHYL 2(Z), 8(Z)-10-HYDROXY C11H10O3


MATRICARITE (190.20)
M.p. : 38.5–40.5°
(Uncorrected)

CH2OH
H3COOC

(1) (1)

SOURCE: Chrysothamnus nauseosus (pall.) Britt., rubber rabbit bush (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Leptinotarsa decemlineata Leaf disk < 35 µg/cm2 Feeding deterrence = Treatment to 3rd
(Say) assay threshold level. instar larvae.
(Colorado potato beetle) (1)

(1) Rose, A.F., Butt, B.A., and Jermy, T. (1980) Phytochemistry, 19, 563.

© 2005 by CRC Press LLC


Insect Antifeedants 679

METHYLISOCEDRELONATE C26H30O6
(458.52)
Only spectral data given

O
COOCH3
HO
(1) (1, 2)

SOURCE: Synthetic (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk 1 µg/cm2 Feeding inhibition = Treatment to 3rd
(Tobacco armyworm) dual-choice 42.5% instar larvae for 24 h.
test (2)
5 µg/cm2 Feeding inhibition =
52.5%

10 µg/cm2 Feeding inhibition = EC50 = 2.97 µg/cm2


58.5%
Data calculated from
50 µg/cm2 Feeding inhibition = Reference 2.
74.1%

(1) Hodges, R., McGeachin, S.G., and Raphel, R.A. (1963) J. Chem. Soc., 2515.
(2) Govindachari, T.R., Narasimhan, N.S., Suresh, G., Partho, P.D., Gopalakrishnan, G., and Krishna Kumatri,
G.N. (1995) J. Chem. Ecol., 21, 1585.

© 2005 by CRC Press LLC


680 Opender Koul

16-METHYLKAUR-15-EN-19-OIC ACID C20H30O2


(302.46)
M.p. : 171–172°

COOH

(1) (1)

SOURCE: Wedelia biflora (L.) DC., sami scandent shrub (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Anthonomus grandis (Bohem.) Agar plug 13.0 mg/plug Feeding inhibition = Treatment to newly
(Cotton boll weevil) bioassay 100% emerged boll weevils
in the dark at 80°F
for 4 h.
Plug size:
diameter = 1.3 cm
length = 3.6 cm.
(1)

(1) Miles, D.H., Chittawong, V., Payne, A.M., Hedin, P.A., and Kokpol, U.. (1990) J. Agric. Food Chem., 38, 1591.

© 2005 by CRC Press LLC


Insect Antifeedants 681

O-METHYL LYCORENINE C19H25O4N


(331.41)
M.p. : 121–125°

[α]24
D : + 198° (MeOH)

H
H3CO

O
H3CO

H OCH3

(1) (1)

SOURCE: Lycoris radiata Herb., red spider lily (Amaryllidaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Eurema hecabe mandarina Artificial diet 0.8% Feeding ratio = Treatment to 5th
DelOrza feeding 32.4% instar larvae after 4 h
(Yellow butterfly) (moderate feeding of pre-starvation.
inhibition) (1)

(1) Numata, A., Takemura, T., Ohabayashi, H., Katsuno, T., Yamamoto, K., Sato, K., and Kobayashi, S. (1983)
Chem. Pharm. Bull., 31, 2146.

© 2005 by CRC Press LLC


682 Opender Koul

2-METHYL-6-METHOXY-1,2,3,4- C13H16ON2
TETRAHYDRO-β-CARBOLINE (216.28)
M.p. : 207–208°

H3CO

N
N
H

(1) (1)

SOURCE: Virola calophylla (Spruce) Warb., Peruvian virola (Myristicaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Anthonomus grandis (Bohem.) Agar plug 3.0 µg/mm2 Feeding inhibition = Treatment to newly
(Cotton boll weevil) bioassay 49.0% emerged boll weevils
for 4 h in dark.
(1)

(1) Miles, D.H., Ly, A.M., Randle, S.A., Hedin, P.A., and Burks, M.L. (1987) J. Agric. Food Chem., 35, 794.

© 2005 by CRC Press LLC


Insect Antifeedants 683

3-O-METHYLNIVEUSIN–A C21H28O8
(408.45)
Only spectral data given

O
OH

H3CO O
CH2

OH
O

(1) (1)

SOURCE: Helianthus annuus L., sunflower (Asteraceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Diabrotica virgifera virgifera Leaf 40.0 µg/1.5 cm2 Feeding inhibition = Treatment to adults.
(LeConte) disk test about 40.0% in 5 h (2)
(Western corn rootworm) and 25.0% in 24 h

80.0 µg/1.5 cm2 Feeding inhibition =


about 57.0% in 5 h
and 70.0% in 24 h

(1) Alfatafta, A.A. and Mullin, C.A. (1992) Phytochemistry, 31, 4109.
(2) Mullin, C.A., Alfatafta, A.A., Harman, J.L., Everett, S.L., and Serino, A.A. (1991) J. Agric. Food Chem., 39,
2293.

© 2005 by CRC Press LLC


684 Opender Koul

METHYL OCTADECANOATE C19H38O2


(298.51)

M.p. : 39.1°

B.p. : 21.5°/15 mm
H3CO O

(1, 2) (1)

SOURCE: Synthetic (2)


Also occurs in many plant spp.

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Incisitermes minor (Hagen) Paper towel 0.05 mg/cm2 Feeding deterrence = Treatment to
(Western drywood termite) disk assay 8.0% after 6 days immature termites of
10–13 mg body
weight.
(2)

Data calculated from


Reference 2.

(1) (1994) Dictionary of Natural Products, Chapman & Hall, London.


(2) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39.

© 2005 by CRC Press LLC


Insect Antifeedants 685

2 – METHYLOCTADECANOIC ACID C19H38O2


(298.51)
M.p. : 55°

B.p. : 200°/2mm

COOH

H C CH3

CH2 (CH2)14CH3

(1, 2) (1)

SOURCE: Synthetic (2)


Also occurs in the uropygial gland of the night heron

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Incisitermes minor (Hagen) Paper towel 0.05 mg/cm2 Feeding deterrence = Treatment to
(Western drywood termite) disk assay 22.8% after 6 days immature termites of
10–13 mg body
weight.
(2)

Data calculated from


Reference 2.

(1) Morgan, G.T. and Holmes, E. (1927) J. Soc. Chem. Ind., 46, 152T.
(2) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39.

© 2005 by CRC Press LLC


686 Opender Koul

3 – METHYLOCTADECANOIC ACID C19H38O2


(298.51)
M.p. : 44°

[α]20
D : +4.84°

COOH

H3C (CH2)14H2C C H

CH3

(1, 2) (1)

SOURCE: Synthetic (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Incisitermes minor (Hagen) Paper towel 0.05 mg/cm2 Feeding deterrence = Treatment to
(Western drywood termite) disk assay 12.9% after 6 days immature termites of
10–13 mg body
weight.
(2)

Data calculated from


Reference 2.

(1) Stallberg-Stenhagen, S. (1949) Arkiv. Kemi., 1, 187.


(2) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39.

© 2005 by CRC Press LLC


Insect Antifeedants 687

7-O-METHYLPHASEOLLIN C21H20O4
(336.39)
M.p. : 120–122°

H3CO O

H
O
O

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Costelytra zealandica (White) Artificial diet 0.35 µg/g Feeding deterrence = Treatment to 24-h
(Scarab beetle) feeding 50.0% starved 3rd instar
larvae.
Concentration = FI50
value.
(1)

(1) Lane, G.A., Biggs, D.R., Russel, G.B., Sutherland, O.R.W., Williams, E.M., Maindonald, J.H., and Donnell,
D.J. (1985) J. Chem. Ecol., 11, 1731.

© 2005 by CRC Press LLC


688 Opender Koul

(+)-2′-O-METHYLPHASEOLLIN ISOFLAVAN C21H22O4


(338.40)
[α]20
D : + 19.5° (EtOH)

HO O

H3CO O

(1) (2)

SOURCE: Synthetic (1)


(Also from Phaseolus vulgaris L., kidney bean (Fabaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Costelytra zealandica (White) Artificial diet 0.21 µg/g Feeding deterrence = Treatment to 24-h
(Scarab beetle) feeding 50.0% starved 3rd instar
larvae.
Concentration = FI50
value.
(1)

(1) Lane, G.A., Biggs, D.R., Russel, G.B., Sutherland, O.R.W., Williams, E.M., Maindonald, J.H., and Donnell,
D.J. (1985) J. Chem. Ecol., 11, 1731.
(2) V. Etten, H.D. (1973) Phytochemistry, 12, 1791.

© 2005 by CRC Press LLC


Insect Antifeedants 689

7-O-METHYL-8-PRENYLFLAVANONE C22H24O3
(336.41)
No physical data given

H3CO O

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera exempta (Walker) Glass fiber 100 ppm Feeding inhibition = 1. Treatment to 24- to
(Nutgrass armyworm) disk dual- 65.0% 36-h-old final
choice test stadium larvae for
10 ppm Feeding inhibition = 5 h. Larvae pre-
29.0% starved for 4 h.
(2)

2. Spodoptera littoralis (Boisd.) Glass fiber 100 ppm Feeding inhibition = 2. Treatment to 24- to
(Egyptian cotton leaf worm) disk dual- 73.0% 36-h-old final
choice test stadium larvae for
5 h. Larvae pre-
starved for 4 h.
(2)

(1) Simmonds, M.S.J., Blaney, W.M., Monache, F.D., and Bettolo, G.B.M. (1990) J. Chem. Ecol., 16, 365.

© 2005 by CRC Press LLC


690 Opender Koul

METHYLSAINFURAN C17H16O5
(300.31)
M.p. : 147–148°

H3CO OCH3

OH

O
OCH3

(1) (1)

SOURCE: Onobrychis viciifolia Scop., mainfoin (Fabaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Costelytra zealandica (White) Artificial diet 2 µg/g Feeding deterrence Treatment to 24-h
(Scarab beetle) feeding reported statistically starved 3rd instar
significant. larvae.
No quantitative data (1)
given.

(1) Russel, G.B., Shaw, G.J., Christmas, P.E., Yates, M.B., and Sutherland, O.R.W. (1984) Phytochemistry, 23,
1417.

© 2005 by CRC Press LLC


Insect Antifeedants 691

Nω-METHYLTRYPTAMINE C11H14O2
(174.25)
M.p. : 90°
(87–88°)

N NH
H

(1, 2, 3) (1, 2)

SOURCE: Commercial material (3)


Occurs in Myristicaceae and Rutaceae plants

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Rhopalosiphum maidis (Fitch) Artificial diet 4 mM Feeding deterrence = Treatment to aphids


(Corn leaf aphid) feeding 24.3% at random.
Treatment duration =
5 h.
(3)

Data calculated from


Reference 3.

(1) Yurashevskii, N.K. and Stepanov, S.I. (1939) J. Gen. Chem. USSR, 9, 2203.
(2) Yurashevskii, N.K. (1940) J. Gen. Chem. USSR, 10, 1781.
(3) Corcuera, L.J. (1984) Phytochemistry, 23, 539.

© 2005 by CRC Press LLC


692 Opender Koul

MONOCROTALINE C16H23O6N
(325.36)
M.p. : 202–203°
(197–198°)
OH
[α]26
D : –54.7° (CHCl3)

HC C C

COO HO CH2OCO

(1, 2) (1, 2)

SOURCE: Crotalaria spectabilis Roth, showy crotalaria (Fabaceae) (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Acyrthosiphon pisum (Harris) Artificial 0.05 ± 0.03% Feeding inhibition = Treatment to aphids
(Pea aphid) diet 50.0% at random.
feeding Concentration = EC50
value.
(3)

LD50 (rats): 66 mg/kg (oral) (4)

(1) Adams, R. and Rogers, E.F. (1939) J. Am. Chem. Soc., 61, 2815.
(2) Adams, R. and Rogers, E.F. (1950) J. Am. Chem. Soc., 72, 158.
(3) Dreyer, D.L., Jones, K.C., and Molyneux, R.J. (1985) J. Chem. Ecol., 11, 1045.
(4) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC


Insect Antifeedants 693

MONOMETHOXYCHALCONE C21H20O4
(4-Methoxylonchocarpin) (336.39)
M.p. : 130°
(109°)

O
OCH3

OH O

(1) (1)

SOURCE: Millettia pachycarpa Benth., rosewood (Fabaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Philosamia ricini (Hutt.) Leaf disk test 1.0% Feeding inhibition = Treatment to larvae.
(Eri-silkworm) 90.0% (2)

(1) Singhal, A.K., Barua, N.C., Sharma, R.P., and Baruah, J.N. (1983) Phytochemistry, 22, 1005.
(2) Barua, N.C., Barua, P., Goswami, A., Sharma, R.P., and Baruah, J.N. (1983) Chem. & Indus., 23, 900.

© 2005 by CRC Press LLC


694 Opender Koul

MORIN C15H10O7
(302.24)
M.p. : 303–304°
(285–290°,
anhydrous, dec.)
HO OH

HO O

OH

OH O

(1, 2) (1)

SOURCE: Chlophora tinctoria (L.) Candich. Ex Benth. and Hook f., fustic mulberry (Moraceae)
and many other plants (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Schizaphis graminum Artificial diet 0.04% Feeding inhibition = 1. Treatment to


(Rondani) feeding 50.0% 50–75 aphids at
(Wheat aphid) random.

Treatment duration =
24 h.
(2)

2. Myzus persicae (Sulzer) Artificial diet 0.04% Feeding inhibition = 1. Treatment to


(Green peach aphid) feeding 50.0% 50–75 aphids at
random.

Treatment duration =
8 h.
(2)

LD50 (mice): 555 mg/kg (ipr.) (3)

(1) Dave, K.G., Telang, S.A., and Venkataraman, K. (1962) Tetrahedron Lett., 9.
(2) Dreyer, D.L. and Jones, K.C. (1981) Phytochemistry, 20, 2489.
(3) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC


Insect Antifeedants 695

MUTANGIN C35H40O11
(636.69)
M.p. : 234°

OAc O
O O
Ac O

O
OAc

(1) (1)

SOURCE: Elaeodendron buchananii Loes., eukanda poisonous plant of E. Africa (Celastraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Chilo partellus (Swinhoe) Leaf disk 100 µg/1.8-cm Feeding inhibition = Treatment to 3rd
(Spotted stem borer) test diameter disk 64.9% instar larvae pre-
starved for 24 h in
50 µg/1.8-cm Feeding inhibition = dark.
diameter disk 54.8% Treatment duration =
24 h.
25 µg/1.8-cm Feeding inhibition = (1)
diameter disk 9.2%
Approx. EC50 = 61.0
µg/disk.

Calculated from
Reference 1.

(1) Tsanuo, M.K., Hassanali, A., Jondiko, I.J.O., and Torto, B. (1993) Phytochemistry, 34, 665.

© 2005 by CRC Press LLC


696 Opender Koul

MUZIGADIAL C15H20O3
(canellal) (248.32)
M.p. : 127–128°

[α]25
D : –193° (CHCl3)

CHO
OH
CHO

H
CH2

(1, 2) (1, 2)

SOURCE: Warburgia ugandensis Sprague, African muziga (Canellaceae) (1,3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera exempta (Walker) Leaf disk 0.1 ppm Feeding inhibition = 1. Treatment to
(African armyworm) choice test 100% larvae. Treatment
duration = 1 h.
(3)

2. Leptinotarsa decemlineata Leaf disk 5 mM Feeding inhibition = 2. Treatment to


(Say) dual-choice 82.0% larvae of 90–120 mg
(Colorado potato beetle) test body weight.
Treatment duration =
3 h.
(4)

(1) Kubo, I., Miura, I., Pettei, M.J., Lee, Y., Pilkiewicz, F., and Nakanishi, K. (1977) Tetrahedron Lett., 4553.
(2) El-Feraly, F.S., McPhail, A.T., Andrew, T., and Onan, K.D. (1978) Chem. Commun., 75.
(3) Nakanishi, K. and Kubo, I. (1977) Israel J. Chem., 16, 28.
(4) Gols, G.J.Z., van Loon, J.J.A.., and Messchendorp, L. (1996) Entomol. Exp. Appl., 79, 69.

© 2005 by CRC Press LLC


Insect Antifeedants 697

MYRCENE C10H16
(136.24)
Oil

B.p. : 51–51.5°/8.5 mm

(1, 2) (2)

SOURCE: Commercial sample (1)


(Found in many essential oils)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Hylobius pales (Herbst.) Twig dip 10% Feeding deterrence = Treatment to 22 to 65


(Pales weevil) treatment 40.3% mg body weight
choice assay weevils for 24 h.
(1)
Data calculated from
Reference 1.

LD50 (rats): >5000 mg/kg (oral) (3)

(1) Salom, S.M., Carlson, J.A., Ang, B.N., Grosman, D.M., and Day, E.R. (1994) J. Entomol. Sci., 29, 407.
(2) Wrolstad, R.E. and Jennings, W.G. (1964) J. Agric. Food Chem., 12, 507.
(3) Opdyke, D.L.J. (1976) Food Cosmet. Toxicol., 14, 615.

© 2005 by CRC Press LLC


698 Opender Koul

MYRICITRIN C21H20O12
(464.38)
M.p. : 194–197°
OH

OH

HO O
OH
OH

O
OH

OH O
O
OH

(1) (1)

SOURCE: A naturally occurring compound and semisynthetic substance as well (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Schizaphis graminum (Rondani) Artificial diet 0.07% Feeding inhibition = Treatment to 50–75
(Wheat aphid) feeding 50.0% aphids at random.

Treatment duration =
24 h.
(2)

(1) Hattori, S. and Hayashi, K. (1931) Acta Phytochim., 5, 213.


(2) Dreyer, D.L. and Jones, K.C. (1981) Phytochemistry, 20, 2489.

© 2005 by CRC Press LLC


Insect Antifeedants 699

MYRICOSIDE C34H44O19
(756.71)
M.p. : 165–167°
O
OH

HO
O OH
O O
O
HO HO H OH
HO O H
H
O
OH
O
H
HO
H

HO OH

(1) (1)

SOURCE: Clerodendron infortunatum Gaertn., clerodendron (Verbenaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera exempta (Walker) Leaf disk 10 ppm Feeding inhibition = 1. Treatment to


(Nutgrass armyworm) assay 100% larvae at random.

Activity comparable
to ajugarins.
(1)

(1) Cooper, R., Solomon, P.H., Kubo, I., Nakanishi, K., Shoolery, J.N., and Occolowitz, J.L. (1980) J. Am. Chem.
Soc., 102, 7953.

© 2005 by CRC Press LLC


700 Opender Koul

MYRISTIC ACID C14H28O2


(228.37)
M.p. : 54°

B.p. : 250.5°/100 mm

n70
D : 1.4273

COOH

(1, 2) (1, 2)

SOURCE: Pinus lambertiana Dougl., sugar pine (Pinaceae) (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Incisitermes minor (Hagen) Paper towel 0.05 mg/cm2 Feeding deterrence = Treatment to
(Western drywood termite) disk assay 10.5% after 6 days immature termites of
10–13 mg body
0.25 mg/cm2 Feeding deterrence = weight.
59.8% after 7 days (3)

Data calculated from


Reference 3.

LD50 (mice): 43.0 ± 2.6 mg/kg (i.v.) (4)

(1) Merck Index (1983).


(2) Bailey, A.V. and Pittman, R.A. (1971) J. Am. Oil Chem. Soc., 48, 775.
(3) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39.
(4) Oro, L. and Wretlind, A. (1961) Acta Pharmacol. Toxicol., 18, 141.

© 2005 by CRC Press LLC


Insect Antifeedants 701

MYRSINAQUINONE C34H50O7
(570.38)
No physical data given

H O

HO O (CH2)10

HO O OH

(CH2)10 O

(1) (1)

SOURCE: Rapanea melanphloes (L.) Mez., East African medicinal plant (Myrsinaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Schistocerca gregaria (Forsk.) Filter paper 100 µg/ml Feeding inhibition = Treatment to mid 5th
(Desert locust) no-choice 44.5% instar females pre-
assay starved for 24 h.
Treatment duration =
24 h.
(1)

(1) Midiwo, J.O., Mwangi, R.W., and Ghebremeskel, Y. (1995) Insect Sci. Applic., 16, 163.

© 2005 by CRC Press LLC


702 Opender Koul

MYRSINONE C17H26O4
(294.39)
M.p. : 120–122°

HO

HO (CH2)10

(1, 2) (1, 2)

SOURCE: Rapanea melanphloes (L.) Mez., East African medicinal plant (Myrsinaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Schistocerca gregaria (Forsk.) Filter paper 100 µg/ml Feeding inhibition = Treatment to mid 5th
(Desert locust) no-choice 90.2% instar females pre-
assay starved for 24 h.
Treatment duration =
24 h.
(2)

(1) Midiwo, J.O., Ghebremeskel. Y., Arot, L.M., Koyama, K., and Natori, S. (1992) Bull. Chem. Soc. Ethiop., 6, 15
(2) Midiwo, J.O., Mwangi, R.W., and Ghebremeskel, Y. (1995) Insect Sci. Applic., 16, 163.

© 2005 by CRC Press LLC


Insect Antifeedants 703

NAGILACTONE–C C19H22O7
(362.37)
M.p. : 290° (dec.)

O [α]D : +111° (neat)

O
O

HO OH
H
O
O

(1, 2) (1)

SOURCE: Podocarpus nagi Zoll. et Moritizi., pine (Podocarpaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Heliothis virescens (Fab.) Artificial diet 230 ppm Feeding deterrence = Treatment to 5th
(Tobacco budworm) feeding 67.0% instar larvae for
4 days.
(2)
Injection 25 µg/larva Feeding deterrence =
34.0%

(1) Dev, S., and Koul, O. (1997) Insecticides of Natural Origin, Harwood Academic Publishers, Amsterdam, p.
112.
(2) Zhang, M., Ying, B., and Kubo, I. (1992) J. Nat. Prod., 55, 1057.

© 2005 by CRC Press LLC


704 Opender Koul

NAGILACTONE–D C18H20O6
(332.35)
M.p. : 265–266° (dec.)

[α]D : +90° (neat)


O

O
O

HO
H
O
O

(1, 2) (1)

SOURCE: Podocarpus nagi Zoll. et Moritizi., pine (Podocarpaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Heliothis virescens (Fab.) Artificial diet 60 ppm Feeding deterrence = Treatment to 5th
(Tobacco budworm) feeding 70.0% instar larvae for
4 days.
(2)
Injection 25 µg/larva Feeding deterrence =
36.0%

(1) Dev, S. and Koul, O. (1997) Insecticides of Natural Origin, Harwood Academic Publishers, Amsterdam, p. 108.
(2) Zhang, M., Ying, B., and Kubo, I. (1992) J. Nat. Prod., 55, 1057.

© 2005 by CRC Press LLC


Insect Antifeedants 705

1 – NAPHTHALDEHYDE C11H8O
(156.16)
No physical data given

CHO

(1, 2) (1)

SOURCE: Commercial sample (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Pieris rapae crucivoraI (Boisd.) Leaf disk 5 × 10–7 Feeding deterrence = Treatment to 5th
(Cabbage butterfly) dual-choice mol/cm2 76.7% instar larvae pre-
test starved for 3 h.
Treatment duration =
2 h.
(1)

(1) Yano, K. and Tanaka, N. (1995) Biosci. Biotech. Biochem., 59, 1130.

© 2005 by CRC Press LLC


706 Opender Koul

2 – NAPHTHALDEHYDE C11H8O
(156.16)
No physical data given

CHO

(1) (1)

SOURCE: Commercial sample (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Pieris rapae crucivora (Boisd.) Leaf disk 5 × 10–7 Feeding deterrence = Treatment to 5th
(Cabbage butterfly) dual-choice mol/cm2 83.3% instar larvae pre-
test starved for 3 h.
Treatment duration =
2 h.
(1)

(1) Yano, K. and Tanaka, N. (1995) Biosci. Biotech. Biochem., 59, 1130.

© 2005 by CRC Press LLC


Insect Antifeedants 707

NARINGENIN C15H12O5
(272.26)
M.p. : 251°
(227–228°)

OH [α]27
D : –22.5° (MeOH)

HO O

OH O

(1, 2) (1, 2)

SOURCE: Semisynthetic (1,3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Schizaphis graminum Artificial diet 0.15% Feeding inhibition = 1. Treatment to


(Rondani) feeding 50.0% 50–75 aphids at
(Wheat aphid) random.

Treatment duration =
24 h.
(3)

2. Myzus persicae (Sulzer) Artificial diet 0.25% Feeding inhibition = 2. Treatment to


(Green peach aphid) feeding 50.0% 50–75 aphids at
random.

Treatment duration =
8 h.
(3)

(1) Gell, R.J., Pinhey, J.T., and Ritchie, E. (1958) Aust. J. Chem., 11, 372.
(2) Gaffield, W. and Waiss, A.C. Jr. (1968) Chem. Commun., 29.
(3) Dreyer, D.L. and Jones, K.C. (1981) Phytochemistry, 20, 2489.

© 2005 by CRC Press LLC


708 Opender Koul

NEOABIETIC ACID C20H30O2


(302.46)
M.p. : 173–173.5°
(167–169°)

[α]25
D : +161.6° (EtOH)

COOH

(1, 3, 4) (1, 2)

SOURCE: Pinus banksiana Dougl., jack pine (Pinnaceae) (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Neodiprion dubiosus (Schedl.) Pine needle 1.0 mg/ml Feeding inhibition = 1. Treatment to 3rd or
(Brownhead jack pine sawfly) and twig 67.0% 4th instar larvae for
application 4 h.
(3)

2. N. rugifrons (Middleton) Pine needle 1.0 mg/ml Feeding inhibition = 2. Treatment to 3rd or
(Redhead jack pine sawfly) and twig 83.0% 4th instar larvae for
application 4 h.
(3)

3. N. lecontei (Fitch) Pine needle 18.0 mg/ml Feeding inhibition = 3. Treatment to 3rd or
(Redhead pine sawfly) and twig 70.0% 4th instar larvae for
application 4 h.
(4)

(1) Harris, G.C. and Sanderson, T.F. (1948) J. Am. Chem. Soc., 70, 334, 339.
(2) Schuller, W.H. and Ray, V.L. (1961) J. Am. Chem. Soc., 83, 2563.
(3) Schuh, B.A. and Benjamin, D.M. (1984) J. Chem. Ecol., 10, 1071.
(4) Schuh, B.A. and Benjamin, D.M. (1984) J. Econ. Entomol., 77, 802.

© 2005 by CRC Press LLC


Insect Antifeedants 709

NEOADENOSTYLONE C20H24O4
(328.41)
M.p. : 104–109°

[α]24
D : –86° (CHCl3)

O O

(1, 2) (1)

SOURCE: Adenostyles alliariae (Conan) Kern., grauer alpino (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius (L.) Wafer disk 10 mg/ml Feeding deterrence 1. Treatment given to
(Grain weevil) test coefficient = 80.0 adults.

2. Tribolium confusum (Duv.) Wafer disk 10 mg/ml Feeding deterrence 2. Treatment given to
(Confused flour beetle) test coefficient both adults and
Adults = 110.0 larvae.
Larvae = 94.0

3. Trogoderma granarium Wafer disk 10 mg/ml Feeding deterrence 3. Treatment given to


(Everts) test coefficient = 151.0 larvae.
(Khapra beetle)
Neutral value = 0
Absolute feeding
deterrence value =
200
(1)

(1) Harmatha, J., Samek, Z., Novotny, L., Herout, V., and Sorm, F. (1969) Collect. Czech. Chem. Commun., 34,
1739, 2793.
(2) Nawrot, J., Harmatha, J., and Novotny, L. (1984) Biochem. Syst. Ecol., 12, 99.

© 2005 by CRC Press LLC


710 Opender Koul

NEOHESPERIDIN DHC C28H36O15


(612.58)
M.p. : 156–158°

OH
CH2OH

O
HO
O COCH2CH2 OCH3
HO
O
OH OH

HO
OH
OH

(1–4) (1, 2)

SOURCE: Naturally occurring in grapefruit as well as a semisynthetic compound (2, 3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Schizaphis graminum Artificial diet 0.2% Feeding inhibition = 1. Treatment to


(Rondani) feeding 50.0% 50–75 aphids at
(Wheat aphid) random.

Treatment duration =
24 h.
(4)

2. Myzus persicae (Sulzer) Artificial diet 0.2% Feeding inhibition = 2. Treatment to


(Green peach aphid) feeding 50.0% 50–75 aphids at
random.

Treatment duration =
8 h.
(4)

(1) Pratter, P.J. (1981) Perfum. Flavor., 5, 12.


(2) Horowitz, R.M. and Gentili, B. (1969) J. Agric. Food Chem., 17, 696.
(3) Dubios, G.E., Crosby, G.A., Stephenson, R.A., and Wingard, R.E. Jr. (1977) J. Agric. Food Chem., 25, 763.
(4) Dreyer, D.L. and Jones, K.C. (1981) Phytochemistry, 20, 2489.

© 2005 by CRC Press LLC


Insect Antifeedants 711

NERIIFOLIN C30H46O8
(534.69)
M.p. : 214–218°
(218–225°)
O
O [α]D : –49° (MeOH)

OCH3 OH
HO

O
OH

(1, 2) (1, 2)

SOURCE: Thevetia thevetioides (HBK) K.Schum., Mexican yellow oleander (Apocynaceae) (2, 3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Acalymma vittatum (Fab.) Leaf disk test 0.1% Feeding deterrence = 1. Treatment to
(Striped cucumber beetle) 100% for 3 days female beetles only.
(3)

2. Popillia japonica (Newman) Leaflet 0.5% Feeding deterrence 2. Treatment to adult


(Japanese beetle) treatment assessed on the basis beetles.
of 1 to 10% tissue (3)
loss due to feeding
against 50 to 70% in
controls.

LD50 (cat): 0.2 mg/kg (ivn.) (4)

(1) Cruz, A., Garcia, I., Iriarte, J., Muchowski, J.M., and Regla, I. (1977) J. Org. Chem., 42, 3580.
(2) McLaughlin, J.L., Freedman, B., Powell, R.G., and Smith, C.R. Jr. (1980) J. Econ. Entomol., 73, 398.
(3) Reed, D.K., Freedman, B., and Ladd, T.L. Jr. (1982) J. Econ. Entomol., 75, 1093.
(4) Voigtlaender, H.W. (1969) Arch. Pharm., 302, 538.

© 2005 by CRC Press LLC


712 Opender Koul

NEUROLENIN–A C20H28O6
(364.44)
M.p. : 127–128°

[α]25
D : –257.7° (CHCl3)

O
O
OH

O
CH2
O

(1, 2) (1, 2, 3)

SOURCE: Neurolaena lobata (L.) R.Br., golden rod (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk no- 70 µg/1.5 cm2 Feeding deterrence = Treatment to 5th
(Tobacco armyworm) choice test 42.0% instar larvae pre-
starved for 3 h.
Treatment duration =
30 min only.
(1)

(1) Passreiter, C.M. and Isman, M.B. (1997) Biochem. Syst. Ecol., 25, 371.
(2) Passreiter, C.M., Wendisch, D., and Gondol, D. (1995) Phytochemistry, 39, 133.
(3) Manchand, P.S. and Blount, J.F. (1978) J. Org. Chem., 43, 4352.

© 2005 by CRC Press LLC


Insect Antifeedants 713

NEUROLENIN–B C22H30O8
(422.47)
M.p. : 165–166°

O [α]25
D : –350° (CHCl3)

O O
O

OH

O
CH2
O

(1, 2) (1, 2, 3)

SOURCE: Neurolaena lobata (L.) R.Br., golden rod (Asteraceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk 70 µg/1.5 cm2 Feeding deterrence = Treatment to 5th
(Tobacco armyworm) no-choice test 52.0% instar larvae pre-
starved for 3 h.
Treatment duration =
30 min only.
(2)

(1) Manchand, P.S. and Blount, J.F. (1978) J. Org. Chem., 43, 4352.
(2) Passreiter, C.M. and Isman, M.B. (1997) Biochem. Syst. Ecol., 25, 371.
(3) Passreiter, C.M., Wendisch, D., and Gondol, D. (1995) Phytochemistry, 39, 133.

© 2005 by CRC Press LLC


714 Opender Koul

NICALBIN–A C28H40O7
(488.62)
M.p. : 241–243°
O
[α]D : +37° (CHCl3)

OH
O
H
O
OH

OH O

(1, 2) (1)

SOURCE: Nicandra physaloides (L.) Gaertn. Var. albiflora, apple-of-Peru (Solanaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Epilachna varivestis (Muls.) Leaf residue 0.1% Feeding deterrence = Treatment to 4th
(Mexican bean beetle) test 100% instar larvae for 48 h.
Data based on weight
0.05% Feeding deterrence = loss due to
100% antifeedant effect.
(2)
0.025% Feeding deterrence =
100% Data calculated from
Reference 2.
0.01% Feeding deterrence =
100%

(1) Kirson, I., Gottlieb, H.E., Greenberg, M., and Glotter, E. (1980) J. Chem. Res. (S), 69.
(2) Ascher, K.R.S., Schmutterer, H., Glotter, E., and Kirson, I. (1981) Phytoparasitica, 9, 197.

© 2005 by CRC Press LLC


Insect Antifeedants 715

NICALBIN–B C28H38O6
(470.61)
M.p. : 275–276°
O
[α]D : +24.2° (CHCl3)

O O
H
O

OH O

(1, 2) (1)

SOURCE: Nicandra physaloides (L.) Gaertn. Var. albiflora, apple-of-Peru (Solanaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Epilachna varivestis Muls. Leaf residue 0.1% Feeding deterrence = Treatment to 4th
(Mexican bean beetle) test 100% instar larvae for 48 h.
Data based on weight
0.05% Feeding deterrence = loss due to
100% antifeedant effect.
(2)
0.025% Feeding deterrence =
80% Data calculated from
Reference 2.

(1) Kirson, I., Gottlieb, H.E., Greenberg, M., and Glotter, E. (1980) J. Chem. Res. (S), 69.
(2) Ascher, K.R.S., Schmutterer, H., Glotter, E., and Kirson, I. (1981) Phytoparasitica, 9, 197.

© 2005 by CRC Press LLC


716 Opender Koul

NICANDRENONE–1 C28H34O6
(466.57)
M.p. : 117°

O
O
H
O

OH
O
OH

(1, 2) (1)

SOURCE: Physalis peruviana L., Peruvian groundcherry (Solanaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Epilachna varivestis Muls. Leaf residue 0.1% Feeding deterrence = 1. Treatment to 4th
(Mexican bean beetle) test 100% instar larvae for 48 h.
Data based on weight
0.05% Feeding deterrence = loss due to
100% antifeedant effect.
(2)

Data calculated from


Reference 2.

2. Spodoptera littoralis (Boisd.) Styropor test 0.1% Feeding deterrence = 2.Treatment to larvae
(Egyptian cotton leaf worm) 44.3% of 170–190 mg body
weight.
0.01% Feeding deterrence = (3)
16.3%
Data calculated from
Reference 3.

(1) Begley, M.J., Crombie, L., Ham, P.J., and Whiting, D.A. (1972) Chem. Commun., 1250.
(2) Ascher, K.R.S., Schmutterer, H., Glotter, E., and Kirson, I. (1981) Phytoparasitica, 9, 197.
(3) Ascher, K.R.S., Nemny, N.E., Eliyahu, M., Kirson, I., Abraham, A., and Glotter, E. (1980) Experientia, 36, 998.

© 2005 by CRC Press LLC


Insect Antifeedants 717

NIMBANDIOL C26H32O7
(456.53)
M.p. : 121°

OCH3 [α]20
D : +187.9° (CHCl3)

O O
O

HO OH

(1, 2) (1, 2)

SOURCE: Azadirachta indica A. Juss., neem (Meliaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Epilachna varivestis Muls. Bean leaf 0.01% Feeding deterrence = Treatment to 4th
(Mexican bean beetle) choice assay 50.0% instar larvae for 24 h.
Concentration = EC50
value.
(2)

(1) Kraus, W. and Cramer, R. (1981) Chem. Ber., 114, 2375.


(2) Schwinger, M., Ehhammer, B., and Kraus, W. (1984) In H. Schmutterer and K.R.S. Ascher (eds.), Proc. 2nd
Int. Neem Conf., Rauischholzhausen, GTZ, Eschborn, Germany, pp. 181–198.

© 2005 by CRC Press LLC


718 Opender Koul

NIMBIN C30H36O9
(540.61)
M.p. : 205°

OCH3 [α]D : +170° (CHCl3)

O O
O

H3COOC OAc

(1, 2) (1, 2)

SOURCE: Azadirachta indica A. Juss., neem (Meliaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera litura (Fab.) Leaf disk 1 µg/cm2 Feeding deterrence = Treatment to 3rd
(Tobacco armyworm) dual-choice 62.9% instar larvae for 24 h.
test (3)
10 µg/cm2 Feeding deterrence =
65.8%

2. Pericallia ricini (Fab.) Leaf disk 1 µg/cm2 Feeding deterrence =


(Tiger moth) dual-choice 67.5%
test
10 µg/cm2 Feeding deterrence =
69.8%

3. Oxya fuscovittata (Marsh.) Leaf disk 1 µg/cm2 Feeding deterrence =


(Grasshopper) dual-choice 73.8%
test
10 µg/cm2 Feeding deterrence =
81.8%

(1) Harris, M., Henderson, R., McCrindle, R., Overton, K.H., and Turner, D.W. (1968) Tetrahedron, 24, 1517.
(2) Narayanan, C.R., Pachapurkar, R.V., Pradhan, S.K., Shah, V.R., and Narasimhan, N.S. (1964) Ind. J. Chem.,
2, 108.
(3) Govindachari, T.R., Narasimhan, N.S., Suresh, G., Partho, P.D., and Gopalakrishnan, G. (1996) J. Chem.
Ecol., 22, 1453.

© 2005 by CRC Press LLC


Insect Antifeedants 719

NIMBINENE C28H34O7
(482.57)
M.p. : 134°

OCH3 [α]20
D : +168° (CHCl3)

O O
O

OAc

(1, 2) (1, 2)

SOURCE: Azadirachta indica A. Juss., neem (Meliaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Epilachna varivestis (Mulsant) Bean leaf 0.018% Feeding deterrence = Treatment to 4th
(Mexican bean beetle) choice assay 50.0% instar larvae for 24 h.
Concentration = EC50
value.
(2)

(1) Kraus, W. and Cramer, R. (1981) Chem. Ber., 114, 2375.


(2) Schwinger, M., Ehhammer, B., and Kraus, W. (1984) In H. Schmutterer and K.R.S. Ascher (eds.), Proc. 2nd
Int. Neem Conf., Rauischholzhausen, GTZ, Eschborn, Germany, pp. 181–198.

© 2005 by CRC Press LLC


720 Opender Koul

NIMBOLIDIN–C C37H50O12
(686.80)
Amorphous powder

[α]23
D : +14° (MeOH)
OAc
AcO H3COOC

AcO OCO

(1) (1)

SOURCE: Melia toosendan Sieb. and Zucc., Chinese melia (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera eridania (Boisd.) Leaf disk 10 µg/cm2 Feeding deterrence = Treatment to 3rd
(Southern armyworm) choice test Threshold level instar larvae and
visually compared
for the treated and
untreated leaves
consumed by the
larvae.
(1)

(1) Nakatani, M., Zhou, J., Nakayama, N., Okamura, H., and Iwagawa, T. (1996) Phytochemistry, 41, 739.

© 2005 by CRC Press LLC


Insect Antifeedants 721

NIMBOLIDIN–D C41H54O12
(738.87)
Amorphous powder

[α]23
D : –55° (MeOH)
H3COOC OAc
Tig O

AcO O Tig

(1) (1)

SOURCE: Melia toosendan Sieb. & Zucc., Chinese melia (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera eridania (Boisd.) Leaf disk 10 µg/cm2 Feeding deterrence = Treatment to 3rd
(Southern armyworm) choice test Threshold level instar larvae and
visually compared
for the treated and
untreated leaves
consumed by the
larvae.
(1)

(1) Nakatani, M., Zhou, J., Nakayama, N., Okamura, H., and Iwagawa, T. (1996) Phytochemistry, 41, 739.

© 2005 by CRC Press LLC


722 Opender Koul

NIMBOLIDIN–E C40H54O12
(726.86)
Amorphous powder

[α]22
D : +4° (MeOH)
H3COOC OAc
Tig O

AcO OCO

(1) (1)

SOURCE: Melia toosendan Sieb. and Zucc., Chinese melia (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera eridania (Boisd.) Leaf disk 10 µg/cm2 Feeding deterrence = Treatment to 3rd
(Southern armyworm) choice test Threshold level instar larvae and
visually compared
for the treated and
untreated leaves
consumed by the
larvae.
(1)

(1) Nakatani, M., Zhou, J., Nakayama, N., Okamura, H., and Iwagawa, T. (1996) Phytochemistry, 41, 739.

© 2005 by CRC Press LLC


Insect Antifeedants 723

NIMBOLIDIN–F C41H56O12
(740.89)
Amorphous powder

[α]D : +4° (MeOH)

H3COOC OAc
OCO

AcO O Tig

(1) (1)

SOURCE: Melia toosendan Sieb. and Zucc., Chinese melia (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera eridania (Boisd.) Leaf disk 10 µg/cm2 Feeding deterrence = Treatment to 3rd
(Southern armyworm) choice test (500 ppm) 50.0% instar larvae for 6 to
24 h, during which
period 50% of one of
the disks was
consumed.
(1)

(1) Zhou, J., Minami, Y., Yagi, F., Tadera, K., and Nakatani, M. (1997) Phytochemistry, 46, 911.

© 2005 by CRC Press LLC


724 Opender Koul

NIMBOLININ–B C35H46O10
(626.74)
Amorphous powder

OH [α]20
D : –55.5° (CHCl3)

O
OAc

AcO OOC

(1, 2) (1)

SOURCE: Melia azedarach L., Chinaberry (Meliaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera eridania (Boisd.) Leaf disk 1000 ppm Feeding deterrence = 1. Treatment to 3rd
(Southern armyworm) choice test Threshold level instar larvae for 6 to
24 h, during which
period 50% of one of
the disks was
consumed.
(2)

2. Spodoptera exigua (Hubner) Leaf disk 1000 ppm Feeding deterrence = 2. Treatment to 3rd
(Beet armyworm) choice test Threshold level instar larvae for 6 to
24 h, during which
period 50% of one of
the disks was
consumed.
(2)

(1) Kraus, W. and Bokel, M. (1981) Chem. Ber., 114, 267.


(2) Nakatani, M., Huang, R.C., Okamura, H., Iwagawa, T., Tadera, K., and Naoki, H. (1995) Tetrahedron, 51,
11731.

© 2005 by CRC Press LLC


Insect Antifeedants 725

NOMILIN C28H34O9
(514.57)
Only spectral data given
O

OAc
O

O
O O

O O

(1, 2) (1)

SOURCE: Citrus natsudaidai Hayati, Japanese citrus (Rutaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Helicoverpa zea (Boddie) Leaf disk 6.6 µg/disk Feeding deterrence = 1. Treatment to 3rd
(Corn earworm) choice test 95.0% instar larvae for 48 h.
(3)

2. Spodoptera frugiperda Leaf disk 0.66 µg/disk Feeding deterrence = 2. Treatment to 3rd
(J.E. Smith) choice test 95.0% instar larvae for 48 h.
(Fall armyworm) (3)

3. Ostrinia nubilalis (Hubner) Leaf disk Feeding deterrence = 3. Treatment to


(European corn borer) choice test 50 µg/g 71.0% neonate larvae for
48 h.
500 µg/g 87.0% (4)

4. Reticulitermes speratus Paper disk 1387 ppm 50.0% 4. Treatment to 3rd


(Kolbe) no-choice instar larvae for 25
(Subterranean termite) test 4475 ppm 95.0% days.
(5)

(1) Kubo, I. and Klocke, J.A. (1981) Colloques Inst. Nat. Recherches Agric., 7, 117.
(2) Altieri, M.A., Lippmann, M., Schmidt, L.L., and Kubo, I. (1984) Protection Ecol., 6, 91.
(3) Klocke, J.A. and Kubo, I. (1982) Entomol. Exp. Appl., 32, 299.
(4) Arnason, J.T., Philogene, B.J.R., Donskov, N., and Kubo, I. (1987) Entomol. Exp. Appl., 43, 221.
(5) Serit, M., Ishida, M., Hagiwara, N., Kim, M., Yamamoto, T., and Takahashi, S. (1992) J. Chem. Ecol., 18, 593.

© 2005 by CRC Press LLC


726 Opender Koul

NONADECANOIC ACID C19H38O2


(298.51)
M.p. : 68.7°

B.p. : 297–298°/100 mm
HOOC

(1, 2) (1)

SOURCE: Synthetic (2)


(Found in many pine spp.)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Incisitermes minor (Hagen) Paper towel 0.25 mg/cm2 Feeding deterrence = Treatment to 10 to
(Western drywood termite) disk test 79.0% after 7 days 13 mg body weight
larvae.
(2)

0.05 mg/cm2 Feeding deterrence = Data calculated from


39.4% after 6 days Reference 2.

(1) (1994) Dictionary of Natural Products, Chapman & Hall, London.


(2) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39.

© 2005 by CRC Press LLC


Insect Antifeedants 727

NOOTKATONE C15H22O
(218.34)
M.p. : 36–37°

[α]D : + 195.5° (CHCl3)

CH2

(1, 2) (2)

SOURCE: Chamaecyparis nootkatensis (D. Don.) Spach., yellow cedar (Cupressaceae) (1, 2)
Also from grapefruit oil and juice

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Coptotermes formosanus Tunneling 10 g/liter Feeding deterrence = Treatment to workers


(Shiraki) assay choice 100.0% over a period of one
(Formosan subterranean test year to investigate
termite) the longevity of the
effect. Effects were
similar to starvation
effects.
(1)

(1) Maistrello, L., Handerson, G., and Laine, R.A. (2003) Pest Manag. Sci, 59, 58.
(2) MacLeod, W.D. (1965) Tetrahedron Lett., 4779.

© 2005 by CRC Press LLC


728 Opender Koul

NORDAMNACANTHAL C15H8O5
(268.23)
M.p. : 220°

O OH

CHO

OH

(1, 2) (2)

SOURCE: Galium aparine L., bedstraw (Rubiaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk 0.12 µmol/cm2 Feeding deterrence = Treatment to 3rd
(Tobacco armyworm) assay 50.0% instar larvae for 6 h.
choice test
Concentration = EC50
value.
(1)

(1) Morimoto, M., Tanimoto, K., Sakatani, A., and Komai, K. (2002) Phytochemistry, 60, 163.
(2) Zhou, Z., Jiang, S.-H., Zhu, D.-Y., Lin, L.-Z., and Cordell, A.G. (1994) Phytochemistry, 36, 765,

© 2005 by CRC Press LLC


Insect Antifeedants 729

OBACUNONE C26H30O7
(454.52)
M.p. : 229–230°
O (209–211°)

[α]D : –50° (CHCl3)

O
O O

O O

(1, 2) (1, 2)

SOURCE: Harrisonia abyssinica Oliv., East African shrub (Simaroubaceae) (2)


Citrus natsudaidai Hayata, Japanese citrus (Rutaceae) (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera exempta (Walker) Leaf disk 100 µg/disk Feeding deterrence = 1. Treatment to early
(Nutgrass armyworm) test 49.0 ± 13% or mid 6th instar
larvae.
(2)
2. Eldana saccharina (Walker) Leaf disk Feeding deterrence = 2. Treatment to 12–h
(Sugar cane borer) test 100 µg/disk 94.0 ± 4% pre-starved late 5th
1 µg/disk 79.0 ± 9% instar larvae.
(2)
3. Maruca testulalis (Geyer) Leaf disk Feeding deterrence = 3. Treatment to late
(Bean pod borer) test 100 µg/disk 82.0 ± 9% 5th instar larvae.
10 µg/disk 76.0 ± 12% (2)
1 µg/disk 61.0 ± 9%

4. Reticulitermes speratus Paper disk Feeding deterrence = 4. Treatment to 3rd


(Kolbe) no-choice 571 ppm 50.0% instar larvae based on
(Subterranean termite) test 1133 ppm 95.0% size over 25 days.
Concentrations =
EC50 and EC95
respectively.
(3)
5. Helicoverpa zea (Boddie) Leaf disk 6.5 µg/cm2 Feeding deterrence = 5. Treatment to 3rd
(Corn earworm) choice test 95.0% instar larvae for 48 h.
(4)
6. Spodoptera frugiperda Leaf disk 0.6 µg/cm2 Feeding deterrence = 6. Treatment to 3rd
(J.E. Smith) choice test 95.0% instar larvae for 48 h.
(Fall armyworm) (4)

(1) Kubota, T., Matsuura, T., Tokoroyama, T., Kamikawa, T., and Matsumoto, T. (1961) Tetrahedron Lett., 325.
(2) Hassanali, A., Bentley, M.D., Sitayo, E.N.O., Njoroge, P.E.W., and Yatagai, M. (1986) Insect Sci. Applic., 7, 495.
(3) Serit, M., Ishida, M., Hagiwara, N., Kim, M., Yamamoto, T., and Takahashi, S. (1992) J. Chem. Ecol., 18, 593.
(4) Klocke, J.A. and Kubo, I. (1982) Entomol. Exp. Appl., 32, 299.

© 2005 by CRC Press LLC


730 Opender Koul

OCOTILLONE C30H51O3
(459.74)
[α]D : + 50° (dioxane)
H

OH
O

(1, 2) (1, 2)

SOURCE: Dysoxylum malabaricum Bedd. and ex CDC, white cidar (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk 1 µg/cm2 Feeding deterrence = Treatment to 3rd
(Tobacco armyworm) dual-choice 55.5% instar larvae for 24 h.
test (2)
5 µg/cm2 Feeding deterrence =
56.8% EC50 = 0.82 µg/cm2

10 µg/cm2 Feeding deterrence = Calculated from


69.2% Reference 2.

50 µg/cm2 Feeding deterrence =


72.5%

(1) Govindachari, T.R., Suresh, G., and Krishna Kumari, G.N. (1994) Phytochemistry, 37, 1127.
(2) Govindachari, T.R., Narasimhan, N.S., Suresh, G., Partho, P.D., Gopalakrishnan, G., and Krishna Kumari,
G.N. (1995) J. Chem. Ecol., 21, 1586.

© 2005 by CRC Press LLC


Insect Antifeedants 731

1 – OCTADECENE C18H36
(252.49)
M.p. : 17.5°

B.p. : 144–146°/3 mm

n20
D : 1.4448

(1, 2) (1)

SOURCE: Synthetic (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Incisitermes minor (Hagen) Paper towel 0.05 mg/cm2 Feeding deterrence = Treatment to 10- to
(Western drywood termite) disk test 7.2% after 6 days. 13-mg body weight
larvae.
(2)

Data calculated from


Reference 2.

(1) Niemann, C. and Wagner, C.D. (1942) J. Org. Chem., 7, 227.


(2) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39.

© 2005 by CRC Press LLC


732 Opender Koul

11 – OCTADECENOIC ACID C18H34O2


(282.47)
M.p. : 10.5–12°
(14.5–15.5°)

COOH

(1, 2) (1)

SOURCE: Synthetic (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Incisitermes minor (Hagen) Paper towel 0.05 mg/cm2 Feeding deterrence = Treatment to 10- to
(Western drywood termite) disk test 11.8% after 6 days. 13-mg body weight
larvae.
(2)

Data calculated from


Reference 2.

(1) Ahmad, K., Bumpus, F.M., and Strong, F.M. (1948) J. Am. Chem. Soc., 70, 3391.
(2) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39.

© 2005 by CRC Press LLC


Insect Antifeedants 733

OCTANOIC ACID C8H16O2


(144.21)
M.p. : 16°

B.p. : 124°/10 mm

COOH

(1, 2) (1)

SOURCE: Synthetic (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Incisitermes minor (Hagen) Paper towel 0.05 mg/cm2 Feeding deterrence = Treatment to 10- to
(Western drywood termite) disk test 12.7% after 6 days. 13-mg body weight
larvae.
(2)

Data calculated from


Reference 2.

LD50 (rats): 10,000 mg/kg (oral) (3)

(1) Langenbeck, W. and Richter, M. (1956) Chem. Ber., 89, 202.


(2) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39.
(3) Opdyke, D.L.J. (1981) Food Cosmet. Toxicol., 19, 237.

© 2005 by CRC Press LLC


734 Opender Koul

n – OCTYL GALLATE C15H22O5


(282.34)
M.p. : 94–95°

COO

HO OH

OH

(1, 2) (1)

SOURCE: Commercial sample (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Schizaphis graminum Artificial diet 57 ppm Feeding inhibition = 1. Treatment to


(Rondani) feeding 50.0% 50–75 aphids at
(Wheat aphid) random.
Treatment duration =
24 h.
(2)

2. Myzus persicae (Sulzer) Artificial diet 56 ppm Feeding inhibition = 2. Treatment to


(Green peach aphid) feeding 50.0% 50–75 aphids at
random.
Treatment duration =
8 h.
(2)

3. Acyrthosiphon pisum (Harris) Artificial diet 182 ppm Feeding inhibition = 3. Treatment to
(Pea aphid) feeding 50.0% aphids at random.
(2)

(1) Van Der Kerk, G.J.M., Verbeek, J.H., and Cleton, J.C.F. (1951) Rec. Trav. Chim., 70, 277.
(2) Jones, K.C. and Klocke, J.A. (1987) Entomol. Exp. Appl., 44, 229.

© 2005 by CRC Press LLC


Insect Antifeedants 735

OHCHINOLIDE–C C37H48O10
(652.78)
Amorphous powder

[α]D : –23° (MeOH)


O

O
OAc

OCO O Tig

(1) (1)

SOURCE: Melia toosendan Sieb. and Zucc., Chinese melia (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera eridania (Boisd.) Leaf disk 20 µg/cm2 Feeding deterrence = Treatment to 3rd
(Southern armyworm) choice test or 50.0% instar larvae for 6 to
1000 ppm 24 h, during which
period 50% of one of
the disks was
consumed.
(1)

(1) Zhou, J., Minami, Y., Yagi, F., Tadera, K., and Nakatani, M. (1997) Phytochemistry, 46, 911.

© 2005 by CRC Press LLC


736 Opender Koul

OLEIC ACID C18H34O2


(262.47)
Oil

B.p. : 286°/100 mm
COOH
n18
D : 1.463

(1, 2) (1)

SOURCE: Pinus lambertiana Dougl., sugar pine (Pinaceae) (2)


Hibiscus syriacus L., rose-of-sharon (Malvaceae) (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Incisitermes minor (Hagen) Paper towel 0.25 mg/cm2 Feeding deterrence = 1. Treatment to
(Western drywood termite) disk assay 8.2% after 7 days. immature termites of
10–13 mg body
weight.
(2)

Data calculated from


Reference 2.

2. Anthonomus grandis (Bohem.) Plate 100 µg/ Feeding 36% of 2. Treatment to adult
(Boll weevil) bioassay feeding site controls after 3 h and weevils.
32% after 6 h in (3)
males. Females
could feed only 17
and 20% of controls,
respectively

LD50 (mice): 230.0 ± 18.0 mg/kg (i.v.) (4)

(1) Robinson, G.M. and Robinson, R. (1925) J. Chem Soc., 175.


(2) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39.
(3) Bird, T.G., Hedin, P.A., and Burks, M.L. (1987) J. Chem. Ecol., 13, 1087.
(4) Oro, L. and Wretlind, A. (1961) Acta Pharmacol. Toxicol., 18, 141.

© 2005 by CRC Press LLC


Insect Antifeedants 737

ONOPORDOPICRIN C19H24O6
(348.40)
M.p. : 55–56°

[α]20
D : +166.8° (MeOH)
CH2

OCOC.CH2OH

CH2

O
CH2OH
O

(1, 2) (1)

SOURCE: Onopordon acantium L. (Asteraceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius (L.) Wafer disk 8 mg/cm3 Feeding deterrence 1. Treatment given to
(Grain weevil) test coefficient = adults.
101–150

2. Tribolium confusum (Duv.) Wafer disk 8 mg/cm3 Feeding deterrence 2. Treatment given to
(Confused flour beetle) test coefficient: both adults and
Adults = 51–100 larvae.
Larvae = 51–100

3. Trogoderma granarium Wafer disk 8 mg/cm3 Feeding deterrence 3. Treatment given to


(Everts) test coefficient = larvae.
(Khapra beetle) 151–200
Neutral value = 0
Absolute feeding
deterrence value =
200
(1)

(1) Drozdz, B., Grabarczyk, H., Samek, Z., Holub, M., Herout, V., and Sorm, F. (1968) Coll. Czech. Chem.
Commun., 33, 1730; (1972) 37, 1546.
(2) Nawrot, J., Bloszyk, E., Grabarczyk, H., and Drozdz, B. (1982) Prace. Nauk. Inst. Ochr. Roslin, 24, 27.

© 2005 by CRC Press LLC


738 Opender Koul

OSMUNDALACTONE C6H8O3
(128.13)
M.p. : 82–82.5°

[α]22
D : –70.6° (H2O)

HO

H
O O

(1, 2) (1)

SOURCE: Osmunda japonica Thunb., flowering fern (Osmundaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Eurema hecabe mandarina Artificial diet 0.39% Feeding ratio = Treatment to 5th
(DelOrza) feeding 13.0% instar larvae after 4 h
(Yellow butterfly) (strong feeding of pre-starvation.
inhibition) (2)

(1) Hollenbeak, K.H. and Kuehne, M.E. (1974) Tetrahedron, 30, 2307.
(2) Numata, A., Hokimoto, K., Takemura, T., and Fukui, S. (1983) Appl. Ent. Zool., 18, 129.

© 2005 by CRC Press LLC


Insect Antifeedants 739

O-OXALYLHOMOSERINE C6H9O6N
(191.14)
Only spectral data given

O O NH2

HO O O
HO

(1, 2) (1)

SOURCE: Lathyrus latifolius L., everlasting pea (Fabaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera littoralis (Boisd.) Glass fiber 0.125% Feeding deterrence = Final stadium larvae
(Egyptian cotton leaf worm) disk test 53.0% treatment pre-starved
for 4 h.
0.25% Feeding deterrence = Treatment given until
58.0% 50% of the disk was
consumed or 18 h,
whichever came first.
(2)

(1) Murooka, Y. and Harada, T. (1967) Agric. Biol. Chem., 31, 1035.
(2) Bell, E.A., Perera, K.P.W.C., Nunn, P.B., Simmonds, M.S.J., and Blaney, W.M. (1996) Phytochemistry, 43,
1003.

© 2005 by CRC Press LLC


740 Opender Koul

2-OXO-3,13E-CLERODIEN-15-OIC ACID C20H32O3


(320.47)
Oil

COOH

(1, 2) (1, 2)

SOURCE: Detarium microcarpum Guill. & Perr., African atokolo (Caesalpiniaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Reticulitermes speratus Kolbe. Paper disk 80 µg/cm2 Feeding deterrence Treatment to 3rd
(Subterranean termite) choice index = 5 instar workers.
bioassay Feeding duration =
14 days.
Antifeedant index
below 20 highly
deterrent.
(1)

(1) Lajide, L., Escoubas, P., and Mizutani, J. (1995) Phytochemistry, 40, 1101.
(2) Aquino, R., Ciavatla, M.L., DeTomassi, N., and Gacs-Baitz, E. (1992) Phytochemistry, 31, 1823.

© 2005 by CRC Press LLC


Insect Antifeedants 741

18-OXO-3,13E-CLERODIEN-15-OIC ACID C20H30O3


(318.46)
Oil

[α]D : + 7° (CHCl3)

COOH

CHO

(1) (1)

SOURCE: Detarium microcarpum Guill. & Perr., African atokolo (Caesalpiniaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Reticulitermes speratus Kolbe. Paper disk 80 µg/cm2 Feeding deterrence Treatment to 3rd
(Subterranean termite) choice index = 5 instar workers.
bioassay Feeding duration =
14 days.
Antifeedant index
below 20 highly
deterrent.
(1)

(1) Lajide, L., Escoubas, P., and Mizutani, J. (1995) Phytochemistry, 40, 1101.

© 2005 by CRC Press LLC


742 Opender Koul

3-OXOGRANDOLIDE C15H20O4
(264.32)
M.p. : 143–144°

CH2 [α]24
D : +50° (CHCl3)
H OH

H
O

(1, 2) (1)

SOURCE: Arctotis grandis Thunb., African daisy (Asteraceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius (L.) Wafer disk 10 mg/cm3 Feeding deterrence 1. Treatment given to
(Grain weevil) test coefficient = 67.3 adults.

2. Tribolium confusum (Duv.) Wafer disk 10 mg/cm3 Feeding deterrence 2. Treatment given to
(Confused flour beetle) test coefficient both adults and
Adults = 102.7 larvae.
Larvae = 99

3. Trogoderma granarium Wafer disk 10 mg/cm3 Feeding deterrence 3. Treatment given to


(Everts) test coefficient = 88.4 larvae.
(Khapra beetle)
Neutral value = 0
Absolute feeding
deterrence value =
200
(1)

(1) Holub, M., Samek, Z., Le, V.N.P., Grabarczyk, H., and Drozdz, B. (1979) Conf. on Isoprenoids, Torun., p. 66.
(2) Nawrot, J., Bloszyk, E., Grabarczyk, H., Drozdz, B., Daniewski, W.M., and Holub, M. (1983) Prace. Nauk.
Inst. Ochr. Roslin, 25, 91.

© 2005 by CRC Press LLC


Insect Antifeedants 743

5-OXO-1-(4-HYDROXY-3-METHOXY C17H24O4
PHENYL)-DECAN-3-ONE (292.38)
Only spectral data given

O O

H3CO

HO

(1, 2) (1, 2)

SOURCE: Aframomum melegueta (Roscoe) K. Schum., Cameroon cardamom (Zingiberaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Reticulitermes speratus Kolbe. Paper disk 7500 ppm Feeding deterrence Treatment to 3rd
(Subterranean termite) choice index = 8.4 instar workers.
bioassay Feeding duration =
14 days.
1000 ppm Feeding deterrence Antifeedant index
index = 27.3 below 20 highly
deterrent.
(2)

(1) Endo, K., Kanno, E., and Oshima, Y. (1990) Phytochemistry, 29, 797.
(2) Escoubas, P., Lajide, L., and Mizutani, J. (1995) Phytochemistry, 40, 1097.

© 2005 by CRC Press LLC


744 Opender Koul

15-OXO-(−)-KAUR-16-EN-19-OIC ACID C20H28O3


(316.44)

M.p. : 211–213°

[α]20
D : –169° (MeOH)

CH2

COOH

(1, 2) (1, 2)

SOURCE: Xylopia aethiopica A. Rich., African pepper (Anonaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Reticulitermes speratus (Kolbe.) Paper disk 5000 ppm Feeding deterrence Treatment to 3rd
(Subterranean termite) choice index = 0 instar workers.
bioassay Feeding duration =
14 days.
2500 ppm Feeding deterrence Antifeedant index
index = 14.1 below 20 highly
deterrent.
(2)

(1) Murakami, T. (1981) Chem. Pharm. Bull., 29, 657.


(2) Lajide, L., Escoubas, P., and Mizutani, J. (1995) Phytochemistry, 40, 1105.

© 2005 by CRC Press LLC


Insect Antifeedants 745

PALMITIC ACID C16H32O2


(256.43)
M.p. : 62.5°
(63–64°)

B.p. : 268.5°/100 mm
COOH

(1, 3) (1, 2)

SOURCE: Pinus lambertiana Dougl., sugar pine (Pinaceae) (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Incisitermes minor (Hagen) Paper towel 0.25 mg/cm2 Feeding inhibition = Treatment to larvae
(Western drywood termite) disk test 81.9% of 10 to 13 mg body
weight.
Treatment duration =
7 days.

0.05 mg/cm2 Feeding inhibition = Treatment to larvae


33.2% of 10 to 13 mg body
weight.
Treatment duration =
6 days.
(3)

Data calculated from


Reference 3.

LD50 (mouse): 57 mg/kg (ivn.) (4)

(1) Bhattacharyya, S.C., Chakravarty, K.K., and Kumar, V. (1959) Chem & Indus., 1352.
(2) Kincl, F.A., Romo, J., Rosemkranz, G., and Sondheimer, F. (1956) J. Chem. Soc., 4163.
(3) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39.
(4) Oro, L. and Wretlind, A. (1961) Acta Pharmacol. Toxicol., 18, 141.

© 2005 by CRC Press LLC


746 Opender Koul

PALUSTRIC ACID C20H30O2


(302.46)
M.p. : 162–167°

[α]D : +71.6° (EtOH)

COOH

(1, 2, 3) (1, 2)

SOURCE: Pinus banksiana Lamb., jack pine (Pinaceae) (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Neodiprion dubiosus Schedl. Needles and 1.0 mg/ml Feeding inhibition = 1. Treatment to 3rd or
(Brownhead jack pine sawfly) twig 78.0% 4th instar.
application Treatment duration =
4 h.
(3)

2. N. rugifrons Midd. Needles and 1.0 mg/ml Feeding inhibition = 2. Treatment to 3rd or
(Redhead jackpine sawfly) twig 99.0% 4th instar.
application Treatment duration =
4 h.
(3)

3. N. lecontei (Fitch) Needles and 10.3 mg/ml Feeding inhibition = 3. Treatment to 3rd or
(Redhead pine sawfly) twig >70.0 % 4th instar larvae.
application Treatment duration =
4 h.
(4)

(1) Loeblich, V.M., Baldwin, D.E., and Lawrence, R.V. (1955) J. Am. Chem. Soc., 77, 2823.
(2) Schuller, W.H., Moore, R.N., and Lawrence, R.V. (1960) J. Am. Chem. Soc., 82, 1734.
(3) Schuh, B.A. and Benjamin, D.M. (1984) J. Chem. Ecol., 10, 1071.
(4) Schuh, B.A. and Benjamin, D.M. (1984) J. Econ. Entomol., 77, 802.

© 2005 by CRC Press LLC


Insect Antifeedants 747

PAPAVERINE C20H21O4N
(339.39)
M.p. : 146.5–147.5°

OCH3

OCH3

H3CO
N

H3CO

(1, 2) (1)

SOURCE: Commercial sample (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Phormia regina (Meigen) Sucrose 10 mM Feeding inhibition = Treatment to 2-, 4-,


(Blow fly) solution 75.0% and 6-day-old adults,
feeding pre-starved for 24 h.
Feeding inhibition = Treatment duration =
81.0% 6 and 24 h,
respectively.
(2)

LD50 (rats): 750 mg/kg (oral) (3)

(1) Guthrie, D.A., Frank, A.W., and Purves, C.B. (1955) Can. J. Chem., 33, 729.
(2) Blades, D. and Mitchell, B.K. (1986) Entomol. Exp. Appl., 41, 299.
(3) Merck Index (1983), p. 6881.

© 2005 by CRC Press LLC


748 Opender Koul

PARTHENIN C15H18O4
(262.31)
M.p. : 163–166°

[α]25
D : +7.02° (CHCl3)

HO

O CH2
O

(1) (1)

SOURCE: Parthenium heterophorus L., carrot grass (Asteraceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Dysdercus koenigii (Fab.) Oral sucrose 0.01% Feeding inhibition = 1. Treatment to


(Red cotton bug) solution 100% adults.
feeding Treatment duration =
24 h.
(2)

2. Callosobruchus chinensis (L.) Oral sucrose 0.01% Feeding inhibition = 2. Treatment to


(Pulse beetle) solution 25.7% adults. Antifeedance
feeding calculated from
0.03% Feeding inhibition = Reference 2.
76.1% (2)

0.04% Feeding inhibition =


69.9 %

LD50 (rats): 42 mg/kg (ipr) (3)

(1) Herz, W., Watanabe, H., Miyazaki, M., and Kishida, Y. (1962) J. Am. Chem. Soc., 84, 2601.
(2) Sharma, R.N. and Joshi, V.N. (1977) Biovigyanum, 3, 225.
(3) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC


Insect Antifeedants 749

PARTHENOLIDE C15H20O3
(248.32)
M.p. : 116.5–117°

[α]20
D : –81.4° (CHCl3)

CH2

O
O
O

(1, 2) (1)

SOURCE: Chrysanthemum parthenium Bernh., fever few (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius (L.) Wafer disk 10 mg/ml Feeding deterrence 1. Treatment given to
(Grain weevil) test coefficient = 148 adults.

2. Tribolium confusum (Duv.) Wafer disk 10 mg/ml Feeding deterrence 2. Treatment given to
(Confused flour beetle) test coefficient: both adults and
Adults = 165.0 larvae.
Larvae = 150.0

3. Trogoderma granarium Wafer disk 10 mg/ml Feeding deterrence 3. Treatment given to


(Everts) test coefficient = 148.0 larvae.
(Khapra beetle)
Neutral value = 0
Absolute feeding
deterrence value =
200
(2)

4. Spodoptera litura (Fab.) Leaf disk 70 µg/1.5 cm2 Feeding deterrence = 4. Treatment to 5th
(Tobacco armyworm) no-choice 77.7% instar pre-starved for
assay 3 h. Treatment
duration = 30 min
(3)

(1) Hendriks, H., Anderson-Wildeboer, Y., Engels, G., Bos, R., and Woerdenberg, H.J. (1997) Planta Medica,
63, 356.
(2) Nawrot, J., Harmatha, J., and Bloszyk, E. (1986) In E. Donahaye and S. Navarro (eds.), Proc. 4th Int. Work.
Conf. Stored Product Protection, Tel Aviv, Israel, pp. 591–597.
(3) Passreiter, C.M. and Isman, M.B. (1997) Biochem. Syst. Ecol., 25, 371.

© 2005 by CRC Press LLC


750 Opender Koul

PEDONIN C27H32O9
(500.54)
M.p. : 259–261°

OH O

COOCH3

O O

(1) (1)

SOURCE: Harrisonia abyssinica Oliv., African harrisonia shrub (Simaroubaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Eldana saccharina (Walker) Potent antifeedant No quantitative data


(Sugar cane borer) activity recorded has been reported.
against these two
species.
2. Maruca testulalis (Geyer) Compound found to
(Bean pod borer) be inactive against
the armyworm,
Spodoptera exempta
(Walker).
(1)

(1) Hassanali, A., Bentley, M.D., Salwin, A.M.Z., Williams, D.J., Shephard, R.N., and Chapya, A.W. (1987)
Phytochemistry, 26, 573.

© 2005 by CRC Press LLC


Insect Antifeedants 751

PEDUNCULAGIN HO OH C34H24O22
(784.55)
O Amorphous sandy soil
H OH
OH [α]25
D : +106° (MeOH)
O OH
O
O
OH

H O H
O
O OH
O O
OH

OH
HO OH
OH
OH (1, 3) (1, 2)

SOURCE: Casuarina stricta Aiton., drooping she-oak (Casuarinaceae); Stachyurus praecox


Sieb. & Zucc., spiketail (Stachyuraceae), and many other species (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Schizaphis graminum Artificial diet 182 ppm Feeding inhibition = 1. Treatment to


(Rondani) feeding 50% aphids at random.
(Wheat aphid)
Concentration = EC50
(3)

2. Myzus persicae (Sulzer) Artificial diet 261 ppm Feeding inhibition = 2. Treatment to
(Green peach aphid) feeding 50% aphids at random.

Concentration = EC50
(3)

(1) Schmidt, O.T., Wuertele, L., and Harreus, A. (1965) Ann. Chem., 690, 150
(2) Ishimatsu, M., Tanaka, T., Nonaka, G., and Nishioka, I. (1989) Phytochemistry, 28, 3179.
(3) Jones, K.C. and Klocke, J.A. (1987) Entomol. Exp. Appl., 44, 229.

© 2005 by CRC Press LLC


752 Opender Koul

PEPEROMIN–A C22H22O8
(414.41)
M.p. : 145–146°
O O
[α]27
D : +20.6° (CHCl3)
O

H3CO
H

H3CO O
O

(1, 2) (1, 2, 3)

SOURCE: Peperomia dindigulensis Miq., Indian endemic pepper (Piperaceae) (2)


P. japonica, Japanese pepper (Piperaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera litura (Fab.) Leaf disk 47.15 µg/cm2 Feeding inhibition 1. Treatment to
(Tobacco armyworm) test index = 50.0% larvae.
Concentration = FI50
value.

2. Rhaphidopalpa foveicollis Leaf disk 36.20 µg/cm2 Feeding inhibition 2. Treatment to


(Lucas) test index = 50.0% larvae.
(Red leaf beetle) Concentration = FI50
value.

3. Atractomorpha crenulata Leaf disk 42.17 µg/cm2 Feeding inhibition 3. Treatment to


(Fab.) test index = 50.0% larvae.
(Tobacco grasshopper) Concentration = FI50
value.
(2)

(1) Chen, C., Jan, F., Chen, M., and Lee, T. (1989) Heterocycles, 29, 411.
(2) Govindachari, T.R., Krishna Kumari, G.N., and Partho, P.D. (1998) Phytochemistry, 49, 2129.
(3) Delle Monache, F. and Compagnone, R.S. (1996) Phytochemistry, 43, 1097.

© 2005 by CRC Press LLC


Insect Antifeedants 753

PEPEROMIN–B C23H26O8
(430.45)
M.p. : 143–145°
H3CO O
[α]27
D : +28.9° (CHCl3)
H3CO

H3CO
H

H3CO O
O

(1, 2) (1, 2, 3)

SOURCE: Peperomia dindigulensis Miq., Indian endemic pepper (Piperaceae) (2)


P. japonica, Japanese pepper (Piperaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera litura (Fab.) Leaf disk 54.67 µg/cm2 Feeding inhibition 1. Treatment to
(Tobacco armyworm) test index = 50.0% larvae.
Concentration = FI50
value.

2. Rhaphidopalpa foveicollis Leaf disk 37.70 µg/cm2 Feeding inhibition 2. Treatment to


(Lucas) test index = 50.0% larvae.
(Red leaf beetle) Concentration = FI50
value.

3. Atractomorpha crenulata Leaf disk 35.00 µg/cm2 Feeding inhibition 3. Treatment to


(Fab.) test index = 50.0% larvae.
(Tobacco grasshopper) Concentration = FI50
value.
(2)

(1) Chen, C., Jan, F., Chen, M., and Lee, T. (1989) Heterocycles, 29, 411.
(2) Govindachari, T.R., Krishna Kumari, G.N., and Partho, P.D. (1998) Phytochemistry, 49, 2129.
(3) Delle Monache, F. and Compagnone, R.S. (1996) Phytochemistry, 43, 1097.

© 2005 by CRC Press LLC


754 Opender Koul

PEPEROMIN–E C22H20O8
(412.12)
M.p. : 140°
O O
[α]D : +2.7° (CHCl3)
O H 2C

H3CO
H

H3CO O
O

(1) (1)

SOURCE: Peperomia dindigulensis Miq., Indian endemic pepper (Piperaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera litura (Fab.) Leaf disk 33.01 µg/cm2 Feeding inhibition 1. Treatment to
(Tobacco armyworm) test index = 50.0% larvae.
Concentration = FI50
value.

2. Rhaphidopalpa foveicollis Leaf disk 25.90 µg/cm2 Feeding inhibition 2. Treatment to


(Lucas) test index = 50.0% larvae.
(Red leaf beetle) Concentration = FI50
value.

3. Atractomorpha crenulata Leaf disk 24.90 µg/cm2 Feeding inhibition 3. Treatment to


(Fab.) test index = 50.0% larvae.
(Tobacco grasshopper) Concentration = FI50
value.
(1)

(1) Govindachari, T.R., Krishna Kumari, G.N., and Partho, P.D. (1998) Phytochemistry, 49, 2129.

© 2005 by CRC Press LLC


Insect Antifeedants 755

PERAMINE C12H17ON5
(247.30)
M.p. : 242–243°
(HBr)

O
N

N
NH

N NH2
H

(1, 2) (3)

SOURCE: Lolium perenne L., ryegrass infected by an endophytic fungus


Acremonium loliae Latch. (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Listronotus bonariensis Artificial diet 1.3 ppm Threshold feeding Treatment to adults.
(Kuschel) feeding inhibition level (2)
(Argentine stem weevil)

(1) Rowan, D.D., Hunt, M.B., and Gaynor, D.L. (1986) J. Chem. Soc. Chem. Commun., 935.
(2) Rowan, D.D. and Gaynor, D.L. (1986) J. Chem. Ecol., 12, 647.
(3) Rowan, D.D. and Tapper, B.A. (1989) J. Nat. Prod., 52, 193.

© 2005 by CRC Press LLC


756 Opender Koul

(–) PERGULARININE C23H25O4N


(tylophorinine) (379.46)
M.p. : 233–235° (dec.)
(248–249°)
H3CO
HO
H [α]25
D : –16° (CHCl3)

H3CO

OCH3

(1) (1)

SOURCE: Tylophora asthmatica Wight and Arn., tylophora (Asclepiadaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Artificial diet 12.0 ppm Feeding inhibition = Treatment to larvae
(Tobacco armyworm) feeding 50.0% of 60- to 70-mg body
weight pre-starved
for 4 h.
(2)

(1) Mulchandani, N.B. and Venkatachalam, S.R. (1976) Phytochemistry, 15, 1561.
(2) Verma, G.S., Ramakrishna, V., Mulchandani, N.B., and Chadha, M.S. (1986) Entomol. Exp. Appl., 40, 99.

© 2005 by CRC Press LLC


Insect Antifeedants 757

PERLOLINE C20H17O3N2
(333.37)
Only spectral data given
NH

OCH3

OCH3

(1) (1)

SOURCE: Lolium perenne L., perennial rye grass (Gramineae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Locusta migratoria (L.) Wafer test 0.25% Feeding inhibition = Treatment at random.
(Migratory locust) 76.0% (2)

Leaf test 0.25% Feeding inhibition =


25.0%

(1) Jeffreys, J.A.D. (1964) J. Chem. Soc., 4504.


(2) Bernays, E.A. and Chapman, R.F. (1977) Ecol. Entomol., 2, 1.

© 2005 by CRC Press LLC


758 Opender Koul

PETASITOLIDE–B C20H28O4
(332.44)
M.p. : 146°

[α]20
D : +31.8° (CHCl3)

H
O O

(1, 2) (1)

SOURCE: Petasites hybridus (L.) Gaertn., butter dock (Asteraceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius (L.) Wafer disk 10 mg/ml Feeding deterrence 1. Treatment given to
(Grain weevil) test coefficient = 128 adults.

2. Tribolium confusum (Duv.) Wafer disk 10 mg/ml Feeding deterrence 2. Treatment given to
(Confused flour beetle) test coefficient: both adults and
Adults = 98.0 larvae.
Larvae = 85.0

3. Trogoderma granarium Wafer disk 10 mg/ml Feeding deterrence 3. Treatment given to


(Everts) test coefficient = 106.0 larvae.
(Khapra beetle)
Neutral value = 0
Absolute feeding
deterrence value =
200
(2)

(1) Novotny, L., Herout, V., and Sorm, F. (1961) Tetrahedron Lett., 697.
(2) Nawrot, J., Harmatha, J., and Novotny, L. (1984) Biochem. Syst. Ecol., 12, 99.

© 2005 by CRC Press LLC


Insect Antifeedants 759

PEUCEDANIN C15H14O4
(258.27)
M.p. : 109°

H3CO

O O O

(1, 2, 3) (1, 2)

SOURCE: Peucedanum officinale L., brim stone-wort (Apiaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk test 1000 ppm Feeding ratio = 12% Treatment to 3rd
(Tobacco armyworm) instar larvae. Ratio of
0–20% strong
inhibitory activity.
(3)

(1) Spath, E. and Klajer, K. (1933) Ber, 66, 749.


(2) Spath, E., Klajer, K., and Schlosser, C. (1931) Ber., 64, 2203.
(3) Yajima, T. and Munakata, K. (1979) Agric. Biol. Chem., 43, 1701.

© 2005 by CRC Press LLC


760 Opender Koul

(–) PHASEOLIN C20H18O4


(322.36)
M.p. : 177–178°

[α]D : –145° (EtOH)


HO O

O
O

(1) (1, 2)

SOURCE: Phaseolus vulgaris L., kidney bean (Fabaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Costelytra zealandica Synthetic 1 µg/ml Feeding deterrence = 1. Treatment to 3rd


(White) diet feeding to 100% instar larvae after
(Scarab beetle) 100 µg/ml 24-h pre-starvation.
(2)

0.03 µg/g Feeding deterrence = Treatment to 24-h


50.0% pre-starved 3rd instar
larvae.
(3)

2. Heteronychus arator (Fab.) Synthetic 200 µg/ml Feeding deterrence = 2. Treatment to 3rd
(Black beetle) diet feeding 100% instar larvae after
24-h pre-starvation.
100 µg/ml Feeding deterrence =
36.1% Data calculated from
Reference 2.
10 µg/ml Feeding deterrence = (2)
33.3%

(1) Perrin, D.R. (1964) Tetrahedron Lett., 29.


(2) Sutherland, O.R.W., Russel, G.B., Biggs, D.R., and Lane, G.A. (1980) Biochem. Syst. Ecol., 8, 73.
(3) Lane, G.A., Biggs, D.R., Russel, G.B., Sutherland, O.R.W., Williams, E.M., Maindonald, J.H., and Donnell,
D.J. (1985) J. Chem. Ecol., 11, 1713.

© 2005 by CRC Press LLC


Insect Antifeedants 761

(–) PHASEOLLIDIN C20H20O4


(324.38)
M.p. : 67–69°

HO O [α]D : –150 to –250°

O
OH

(1, 2) (1)

SOURCE: Phaseolus vulgaris L., kidney bean (Fabaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Costelytra zealandica (White) Synthetic 1.6 µg/g Feeding deterrence = Treatment to 3rd
(Scarab beetle) diet feeding 50.0% instar larvae after
24-h pre-starvation.

Concentration = EC50
value.
(2)

(1) Perrin, D.R., Whittle, C.P., and Batterham, T.J. (1972) Tetrahedron Lett., 1673.
(2) Lane, G.A., Biggs, D.R., Russel, G.B., Sutherland, O.R.W., Williams, E.M., Maindonald, J.H., and Donnell,
D.J. (1985) J. Chem. Ecol., 11, 1713.

© 2005 by CRC Press LLC


762 Opender Koul

(–) PHASEOLLINISOFLAVAN C20H20O4


(324.38)
[α]D : –9° (MeOH)

HO O

HO O

(1, 2) (1)

SOURCE: Phaseolus vulgaris L., kidney bean (Fabaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Costelytra zealandica (White) Synthetic 10.0 µg/g Feeding deterrence = Treatment to 3rd
(Scarab beetle) diet feeding 100.0% instar larvae after
24-h pre-starvation.
1.0 µg/g Feeding deterrence = Data calculated from
100.0% Reference 2.
(2)

0.02 µg/g Feeding deterrence = Treatment to 3rd


50.0% instar larvae after
24-h pre-starvation.

Concentration = EC50
value.
(3)

(1) Burden, R.S., Bailey, J.A., and Dawson, G.W. (1972) Tetrahedron Lett., 4175.
(2) Sutherland, O.R.W., Russel, G.B., Biggs, D.R., and Lane, G.A. (1980) Biochem. Syst. Ecol., 8, 73.
(3) Lane, G.A., Biggs, D.R., Russel, G.B., Sutherland, O.R.W., Williams, E.M., Maindonald, J.H., and Donnell,
D.J. (1985) J. Chem. Ecol., 11, 1713.

© 2005 by CRC Press LLC


Insect Antifeedants 763

PHELLOPTERIN C17H16O5
(300.31)
M.p. : 102°

OCH3

O O O

(1, 2) (1)

SOURCE: Angelica silvestris L., angelica (Apiaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Peridroma saucia (Hubner) Leaf disk 14.25 µg/cm2 Feeding deterrence = Treatment to 5th
(Variegated cutworm) choice test 45.4% instar larvae for 5 h.
(2)
28.5 µg/cm2 Feeding deterrence =
58.7% FI50 = 18.2 µg/cm2
Calculated from
57.0 µg/cm2 Feeding deterrence = Reference 2.
87.5%

(1) Chaterjee, A., Bose, P.K., and Saha, S.K. (1962) Arch. Pharm., 295, 248.
(2) Nawrot, J., Koul, O., Isman, M.B., and Harmatha, J. (1991) J. Appl. Ent., 112, 194.

© 2005 by CRC Press LLC


764 Opender Koul

PHENANTHRIDINE C13H10N
(180.22)
No physical data given

(1) (1)

SOURCE: Commercial sample (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk 1000 ppm Feeding deterrence Treatment to 4-d-old
(Tobacco armyworm) choice test index = 12.01 larvae for 1 day.

Antifeedant index
value below
20 highly deterrent.
(1)

(1) Lajide, L., Escoubas, P., and Mizutani, J. (1993) J. Agric. Food Chem., 41, 2426.

© 2005 by CRC Press LLC


Insect Antifeedants 765

PHENETHYLAMINE HYDROCHLORIDE C8H11NHCl


(121.18)

M.p. : 159–160°

NH2 - HCl

(1) (1)

SOURCE: Commercial sample (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Nilaparvata lugens (Stal.) Sucrose Treatment to adult


(Brown planthopper) solution Feeding deterrence = females.
sucking 1000 ppm 90.0% FI50 = 54.31 ppm
method 500 ppm 75.0%
50 ppm 51.0%

2. Sogatella furcifera (Horvath) 1000 ppm 94.0% FI50 = 38.72 ppm


(Planthopper) 100 ppm 71.0%
10 ppm 55.0%

3. Laodelphax striatella (Fallen) 1000 ppm 76.0% FI50 = 151.24 ppm


(Planthopper) 100 ppm 53.0%
10 ppm 41.0%

4. Nephotettix cincticeps (Uhler) 1000 ppm 97.0% FI50 = 71.32 ppm


(Fruit leaf hopper) 100 ppm 77.0%
10 ppm 47.0%

Calculated from
Reference 1.
(1)

(1) Kurata, S. and Sogawa, K. (1976) Appl. Ent. Zool., 11, 89.

© 2005 by CRC Press LLC


766 Opender Koul

PHENOL C6H6O
(94.11)
B.p. : 68–71°/0.5 mm

n25
D : 1.5210

OH

(1) (1, 2)

SOURCE: Naturally occurring in number of essential oils and resins (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Acalymma vittatum (Fab.) Leaf disk test 0.5% Feeding inhibition = Treatment to adult
(Striped cucumber beetle) 100% beetles and inhibition
achieved in 3 h.
(1)

(1) Reed, D.K. and Jacobson, M. (1983) Experientia, 39, 378.


(2) Karrer, W. (1958) Konstitution und Vorkommen der Organischen Pflanzenstoffe, Vol. 1, Berkhauser Verlag,
Basel, p. 72.

© 2005 by CRC Press LLC


Insect Antifeedants 767

1-PHENYL-4-(2-O-ALKYL-BENZOYL) C20H18O4N2
PYRAZOLE–A (350.37)
M.p. : 105°

COOC2H5
O

N N

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk 1000 ppm Feeding deterrence = Treatment to larvae.
(Tobacco armyworm) choice test 100% after 8 h (1)

Feeding deterrence =
75.0% after 24 h

(1) Reddy, G.J., Sbitha, G., and Rao, A.V.S. (1984) Ind. J. Chem., 23B, 99.

© 2005 by CRC Press LLC


768 Opender Koul

1-PHENYL-4-(2-O-ALKYL-BENZOYL) C21H20O4N2
PYRAZOLE–B (364.40)
M.p. : 118°

COOC2H5
O

N N

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk 1000 ppm Feeding deterrence = Treatment to larvae.
(Tobacco armyworm) choice test 100% after 24 h
Very active
compound.
(1)

(1) Reddy, G.J., Sbitha, G., and Rao, A.V.S. (1984) Ind. J. Chem., 23B, 99.

© 2005 by CRC Press LLC


Insect Antifeedants 769

1-PHENYL-4-(2-O-ALKYL-BENZOYL) C20H17O4N2Cl
PYRAZOLE–C (384.82)
M.p. : 120°

COOC2H5
O
Cl

N N

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk 1000 ppm Feeding deterrence = Treatment to larvae.
(Tobacco armyworm) choice test 100% after 24 h
Very active
compound.
(1)

(1) Reddy, G.J., Sbitha, G., and Rao, A.V.S. (1984) Ind. J. Chem., 23B, 99.

© 2005 by CRC Press LLC


770 Opender Koul

1-PHENYL-4-(2-O-ALKYL-BENZOYL) C20H17O4N2Br
PYRAZOLE–D (384.82)
M.p. : 111°

COOC2H5
O
Br

N N

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk 1000 ppm Feeding deterrence = Treatment to larvae.
(Tobacco armyworm) choice test 100% after 4 h but
followed by Activity poor.
considerable (1)
reduction in activity

(1) Reddy, G.J., Sbitha, G., and Rao, A.V.S. (1984) Ind. J. Chem., 23B, 99.

© 2005 by CRC Press LLC


Insect Antifeedants 771

1-PHENYL-4-(2-O-ALKYL-BENZOYL) C22H22O4N2
PYRAZOLE–E (378.43)
M.p. : 114°

COOC2H5
O

N N

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk 1000 ppm Feeding deterrence = Treatment to larvae.
(Tobacco armyworm) choice test 100% up to 8 h and
subsequently Moderate activity.
reduced to 75.0% by (1)
24 h

(1) Reddy, G.J., Sbitha, G., and Rao, A.V.S. (1984) Ind. J. Chem., 23B, 99.

© 2005 by CRC Press LLC


772 Opender Koul

1-PHENYL-1-BUTYNE C10H10
(130.19)
B.p. : 201–203°

n18
D : 1.537

(1, 2, 3) (1, 2)

SOURCE: Commercial sample (purified) (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Pieris rapae crucivora (Boisd.) Leaf disk test 10–1 mol/l Feeding inhibition = Treatment to 5th
(Cabbage butterfly) 83.0% instar larvae for 24 h.
(3)

(1) Truchet, R. (1931) Ann. Chim., 16, 397.


(2) Bergmann, E. and Bondi, A. (1933) Ber., 66, 286.
(3) Yano, K. (1986) Insect Biochem., 16, 717.

© 2005 by CRC Press LLC


Insect Antifeedants 773

1-PHENYL-1-ETHYNE C8H6
(102.14)
Only spectral data given

CH

(1)

SOURCE: Commercial sample (purified) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Pieris rapae crucivora (Boisd.) Leaf disk test 10–1 mol/l Feeding inhibition = Treatment to 5th
(Cabbage butterfly) 64.0% after 2 h instar larvae.
(1)

(1) Yano, K. (1986) Insect Biochem., 16, 717.

© 2005 by CRC Press LLC


774 Opender Koul

1-PHENYL-1-HEXYNE C12H14
(158.24)
Only spectral data given

(1)

SOURCE: Commercial sample (purified) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Pieris rapae crucivora (Boisd.) Leaf disk test 10–1 mol/l Feeding inhibition = Treatment to 5th
(Cabbage butterfly) 51.0% after 2 h instar larvae.
(1)

(1) Yano, K. (1986) Insect Biochem., 16, 717.

© 2005 by CRC Press LLC


Insect Antifeedants 775

1-PHENYL-2,4-PENTADIYNE C11H8
(140.18)
B.p. : 45–50°/.001 mm

(1, 2) (1)

SOURCE: Artemisia capillaris Thumb., wormwood (Asteraceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Pieris rapae crucivora (Boisd.) Leaf disk test 0.3 mg per Feeding inhibition = Treatment to 5th
(Cabbage butterfly) 2 cm 100% after 24-h instar larvae.
diameter exposure (2)
disk

(1) Bohlman, F. and Kleine, K.-M. (1962) Chem. Ber., 95, 39.
(2) Yano, K. (1983) J. Agric. Food Chem., 31, 667.

© 2005 by CRC Press LLC


776 Opender Koul

1-PHENYL-1-PENTYNE C11H12
(144.22)
Only spectral data given

(1) (1)

SOURCE: Commercial sample (purified) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Pieris rapae crucivora (Boisd.) Leaf disk test 10–1 mol/l Feeding inhibition = Treatment to 5th
(Cabbage butterfly) 80.0% after 2 h instar larvae.
(1)

(1) Yano, K. (1986) Insect Biochem., 16, 717.

© 2005 by CRC Press LLC


Insect Antifeedants 777

PHENYL PROPANOID OCH3 C23H30O7


(418.49)
OH M.p. : 65.5–66.5°

H3CO

OCH3 O

H3CO OCH3

CH2
(1) (1)

SOURCE: Myristica fragrans Houtt., nutmeg (Myristicaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Bombyx mori (L.) Artificial diet 50.0 ppm Feeding inhibition = Treatment to 4th
(Silkworm) feeding 100% resulting in instar larvae.
inhibition of growth (2)

(1) Isogai, A., Murakoshi, S., Suzuki, A., and Tamura, S. (1973) Agric. Biol. Chem., 37, 889.

© 2005 by CRC Press LLC


778 Opender Koul

1-PHENYL-1-PROPYNE C9H8
(116.16)
B.p. : 182–183°

n18
D : 1.561

(1, 2, 3) (1, 2)

SOURCE: Commercial sample (purified) (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Pieris rapae crucivora (Boisd.) Leaf disk test 10–1 mol/l Feeding inhibition = Treatment to 5th
(Cabbage butterfly) 96.0% after 2 h instar larvae.
(3)

(1) Wohl, A. and Jaschinowski, K. (1921) Ber., 54, 476.


(2) Truchet, R. (1931) Ann. Chim., 16, 309.
(3) Yano, K. (1986) Insect Biochem., 16, 717.

© 2005 by CRC Press LLC


Insect Antifeedants 779

3-(1-PHENYL-1H-PYRAZOL-4YL) C18H12O3N2
BENZOFURAN-2-CARBOXYLIC ACID–A (304.31)
M.p. : 236°

O COOH

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk 1000 ppm Feeding deterrence = Treatment to larvae.
(Tobacco armyworm) choice test 100% up to 8 h and
subsequently Moderate activity.
reduced to 75.0% by (1)
24 h

(1) Reddy, G.J., Sbitha, G., and Rao, A.V.S. (1984) Ind. J. Chem., 23B, 99.

© 2005 by CRC Press LLC


780 Opender Koul

3-(1-PHENYL-1H-PYRAZOL-4YL) C19H14O3N2
BENZOFURAN-2-CARBOXYLIC ACID–B (318.33)
M.p. : 210°

O COOH

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk 1000 ppm Feeding deterrence = Treatment to larvae.
(Tobacco armyworm) choice test 100% up to 24 h
High activity.
(1)

(1) Reddy, G.J., Sbitha, G., and Rao, A.V.S. (1984) Ind. J. Chem., 23B, 99.

© 2005 by CRC Press LLC


Insect Antifeedants 781

3-(1-PHENYL-1H-PYRAZOL-4YL) C18H11O3N2Cl
BENZOFURAN-2-CARBOXYLIC ACID–C (338.75)
M.p. : 215°

O COOH

Cl
N

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk 1000 ppm Feeding deterrence = Treatment to larvae.
(Tobacco armyworm) choice test 100% up to 24 h
High activity.
(1)

(1) Reddy, G.J., Sbitha, G., and Rao, A.V.S. (1984) Ind. J. Chem., 23B, 99.

© 2005 by CRC Press LLC


782 Opender Koul

3-(1-PHENYL-1H-PYRAZOL-4YL) C18H11O3N2Br
BENZOFURAN-2-CARBOXYLIC ACID–D (383.20)
M.p. : 223°

O COOH

Br
N

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk 1000 ppm Feeding deterrence = Treatment to larvae.
(Tobacco armyworm) choice test 100% up to 8 h and
subsequently Moderate activity.
reduced to 75.0% by (1)
24 h

(1) Reddy, G.J., Sbitha, G., and Rao, A.V.S. (1984) Ind. J. Chem., 23B, 99.

© 2005 by CRC Press LLC


Insect Antifeedants 783

3-(1-PHENYL-1H-PYRAZOL-4YL) C20H16O3N2
BENZOFURAN-2-CARBOXYLIC ACID–E (332.36)
M.p. : 213°

O COOH

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk 1000 ppm Feeding deterrence = Treatment to larvae.
(Tobacco armyworm) choice test 100% up to 8 h and
subsequently Moderate activity.
reduced to 75.0% by (1)
24 h

(1) Reddy, G.J., Sbitha, G., and Rao, A.V.S. (1984) Ind. J. Chem., 23B, 99.

© 2005 by CRC Press LLC


784 Opender Koul

PHLORETIN C15H14O5
(274.27)
M.p. : 262° (dec.)

OH

HO OH

OH O

(1) (1)

SOURCE: Naturally occurring flavonoid in grasses and apple trees (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Schizaphis graminum Artificial diet 0.04% Feeding inhibition = 1. Treatment to


(Rondani) feeding 50% 50–75 aphids at
(Wheat aphid) random for 24 h.

Concentration = EC50
(2)

2. Myzus persicae (Sulzer) Artificial diet 0.14% Feeding inhibition = 2. Treatment to


(Green peach aphid) feeding 50% 50–75 aphids at
random for 8 h.

Concentration = EC50
(2)

(1) Seshadri, T.R. (1951) Ann. Rev. Biochem., 20, 495.


(2) Dreyer, D.L. and Jones, K.C. (1981) Phytochemistry, 20, 2489.

© 2005 by CRC Press LLC


Insect Antifeedants 785

PHLORETIN 4′-O-β-D-GLUCOPYRANOSIDE C21H24O10


(436.41)
CH2OH M.p. : 128–130°
O
O O [α]25
D : –65° (EtOH)
HO H

HO OH O
H
H

OH

OH (1) (1)

SOURCE: Malus pumila var. dulcissima Mill., apple (Rosaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Schizaphis graminum (Rondani) Artificial diet 200 ppm Feeding inhibition = Treatment to 50–75
(Wheat aphid) feeding 50% aphids at random for
24 h.

Concentration = EC50
(1)

(1) Kubo, I. and Matsumoto, A. (1985) Chem. Pharm. Bull., 33, 3817.

© 2005 by CRC Press LLC


786 Opender Koul

PHLORIZIN C21H24O10
(436.41)
M.p. : 110°
OH
[α]25
D : –52° (EtOH)

HO OH

HO OH
O

O OH

OH

(1, 2) (1)

SOURCE: Naturally occurring flavonoid in grasses and apple trees (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Schizaphis graminum Artificial diet 0.02% Feeding inhibition = 1. Treatment to


(Rondani) feeding 50% 50–75 aphids at
(Wheat aphid) random for 24 h.

Concentration = EC50
(2)

2. Myzus persicae (Sulzer) Artificial diet 0.14% Feeding inhibition = 2. Treatment to


(Green peach aphid) feeding 50% 50–75 aphids at
random for 8 h.

Concentration = EC50
(2)

(1) Williams, A.H. (1961) J. Chem. Soc., 4133.


(2) Dreyer, D.L. and Jones, K.C. (1981) Phytochemistry, 20, 2489.

© 2005 by CRC Press LLC


Insect Antifeedants 787

PHTHALIC ACID C8H6O4


(166.13)
M.p. : 212–213°
(210° dec.)

COOH

COOH

(1, 2) (1)

SOURCE: Synthetic (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Incisitermes minor (Hagen) Paper towel 0.05 mg/cm2 Feeding inhibition = Treatment to larvae
(Western drywood termite) disk test 11.4% of 10 to 13 mg body
weight.
Treatment duration =
6 days.
(2)

Data calculated from


Reference 2.

LD50 (rats): 7.9 g/kg (oral) (3)

(1) Cross, B.E., Galt, R.H.B., Hanson, J.R., Curtis, P.J., Grove, J.F., and Morrison, A. (1963) J. Chem. Soc., 2937.
(2) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39.
(3) Shaffer, C.B., Carpenter, C.P., and Smyth, H.F. Jr. (1945) J. Ind. Hyg. Toxicol., 27, 130.

© 2005 by CRC Press LLC


788 Opender Koul

PHYTOL C20H40O
(296.54)
B.p. : 150–151°/0.06 mm

n25
D : 1.4637

[α]18
D : +0.2°
H H

OH

(1, 2, 3) (1, 2)

SOURCE: Callicarpa japonica Thunb., beauty berry (Verbenaceae) (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab,) Leaf disk test 5000 ppm Feeding inhibition = Treatment to 3rd
(Tobacco armyworm)) 100% within 2 h instar larvae. Activity
retards after 6 h.
Therefore,
compound is termed
as relative
antifeedant.
(3)

LD50 (rats): >5000 mg/kg (oral) (4)

(1) Fujisawa, T., Sato, T., Kawara, T., and Ohashi, K. (1981) Tetrahedron Lett., 22, 4823.
(2) von Bader, F . (1951) Helv. Chim. Acta, 34, 1632.
(3) Hosozawa, S., Kato, N., Munakata, K., and Chen, Y. (1974) Agric. Biol. Chem., 38, 1045.
(4) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC


Insect Antifeedants 789

PICRASIN–B C21H28O6
(376.45)
M.p. : 255–257°

[α]D : +16.4° (CHCl3)


OCH3

O
O

HO

H
O O
H
H

(1, 2) (1, 2)

SOURCE: Picrasma quassioides Benn., Indian quassia (Simaroubaceae)


Also found in Soulamea pancheri Brongn. & Griseb. (Simaroubaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Heliothis virescens (Fab.) Leaf disk 19.8 µg/cm2 Feeding inhibition = 1. Treatment to 3rd
(Tobacco budworm) test 30–60% after 2 days instar larvae.
and 0–30% after 6 (3)
days

2. Epilachna varivestis Mulsant Whole leaf 500 ppm Feeding inhibition = 2. Treatment to 4th
(Mexican bean beetle) application 85.9% instar larvae for 24 h.
Larvae pre-starved
for 2 h.
Data calculated from
Reference 4.

3. Spodoptera eridania Whole leaf 500 ppm Feeding inhibition = 3. Treatment to 5th
(Cramer) application 25.0% instar larvae as
(Southern armyworm) above.
(4)

(1) Hiniko, H., Ohta, T., and Takemoto, T. (1970) Chem. Pharm. Bull., 18, 219.
(2) Viala, B. and Polonsky, J. (1970) Compt. Rend., 271C, 410.
(3) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y., Kiyokawa, H., and Lee, K.H.
(1987) J. Nat. Prod., 50, 442.
(4) Leskinen, V., Polonsky, J., and Bhatnagar, S. (1984) J. Chem. Ecol., 10, 1497.

© 2005 by CRC Press LLC


790 Opender Koul

PICROTOXININ C15H16O6
(292.29)
M.p. : 209.5°

[α]D : –5.85° (CHCl3)


O O

O
O
O OH

(1, 2) (1)

SOURCE: Anamirta cocculus (L.) Wight and Arn., fishberry (Menispermaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Diabrotica virgifera virgifera Leaf disk 115 µg/1.5 cm2 Feeding inhibition = 1. Treatment to
(LeConte) test 50.0% adults of resistant
(Western corn rootworm) insects.

51.9 µg/1.5 cm2 Feeding inhibition = Treatment to adults


50.0% of susceptible
insects.

Concentration = EC50
value.
(2)

2. Spodoptera litura (Fab.) Leaf disk 70.0 µg/1.5 cm2 Feeding inhibition = 2. Treatment to 5th
(Tobacco armyworm) no-choice 43.3% instar larvae pre-
assay starved for 3 h.
Treatment duration =
30 min.
(3)

(1) Conroy, H. (1957) J. Am. Chem. Soc., 79, 5550.


(2) Mullin, C.A., Mason, C.H., Chou, J., and Linderman, J.R. (1992) In C.A. Mullin and Scott, J.G. (eds.),
Molecular Mechanisms of Insecticide Resistance: Diversity Among Insects, ACS Symp. Ser. 505, Washington,
D.C., pp. 288–308.
(3) Passreiter, C.M. and Isman, M.B. (1997) Biochem. Syst. Ecol., 25, 371.

© 2005 by CRC Press LLC


Insect Antifeedants 791

PIMPINELLIN C13H10O5
(246.22)
M.p. : 119°

OCH3

H3CO

O O O

(1, 2, 3) (1, 2)

SOURCE: Pimpinella saxifraga L., pimpinella (Apiaceae) (1, 3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk test 1000 ppm Feeding ratio = 2.0% Treatment to 3rd
(Tobacco armyworm) instar larvae. Ratio
level between 0–20%
100 ppm Feeding ratio = 1.0% considered to be
highly active.
(3)

(1) Heut, J. (1898) Arch. Pharm., 236, 162.


(2) Wessely, F. and Kallab, F. (1908) Montash, 59, 161.
(3) Yajima, T. and Munakata, K. (1979) Agric. Biol. Chem., 43, 1701.

© 2005 by CRC Press LLC


792 Opender Koul

PINGUISONE C15H20O2
(232.32)
M.p. : 63–63.5°

[α]25
D : +64.3° (Benzene)

(1, 2) (1)

SOURCE: Aneura pinguis L., liverwort (Metzgeriales) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera littoralis (Boisd.) Leaf disk test 0.5% Feeding inhibition = Treatment to 10- to
(Egyptian cotton leaf worm) 100% 13-day-old larvae.
(2)
0.25% Feeding inhibition =
100%

0.125% Feeding inhibition =


93.0%

(1) Benesova, V., Samek, Z., Herout, V., and Sorm, F. (1969) Collect. Czech. Chem. Commun., 34, 582.
(2) Wada, K. and Munakata, K. (1971) Agric. Biol. Chem., 35, 115.

© 2005 by CRC Press LLC


Insect Antifeedants 793

PIPECOLIC ACID C6H11O2N


(129.16)
M.p. : 270°

[α]25
D : +24.5°

H
N COOH

(1, 2) (1, 2)

SOURCE: Acacia spp. (Fabaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Anacridium melanorhodon Glass fiber 1.0% of Feeding inhibition = 1. Treatment to


arabafrum (Dirsh) disk test disk weight 30–60% nymphs at random.
(Tree locust) (2)
5.0% of Feeding inhibition =
disk weight 90–100%

2. Locusta migratoria Glass fiber 0.5% of Feeding inhibition = 2. Treatment to male


migratoriodes (R and F) disk test disk weight 30–60% 5th instar nymphs.
(Migratory locust) (2)

(1) Stevens, C.M. and Ellman, P.B. (1950) J. Biol. Chem., 182, 75.
(2) Evans, C.S. and Bell, E.A. (1979) Phytochemistry, 18, 1807.

© 2005 by CRC Press LLC


794 Opender Koul

PIPERENONE C22H28O6
(388.46)
M.p. : 86–88°
H3CO
[α]20
D : –129° (MeOH)

H3CO O
OCH3

H3CO

(1) (1)

SOURCE: Piper futokadzura Sieb. et Zucc., Japanese piper (Piperaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk test 0.05% Feeding inhibition = Treatment to 3rd
(Tobacco armyworm) 90–100% instar larvae.
(1)
0.01% Feeding inhibition =
90–100%

0.005% Feeding inhibition =


90–100%

0.001% No activity

(1) Matsui, K., Wada, K., and Munakata, K. (1976) Agric. Biol. Chem., 40, 1045.

© 2005 by CRC Press LLC


Insect Antifeedants 795

(+) PISATIN C17H14O6


(314.29)
M.p. : 188–190°

H3CO O

OH
O

O
O

(1, 2) (1)

SOURCE: Pisum sativum L., green pea (Fabaceae) (2, 3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Costelytra zealandica Artificial 200.0 µg/ml Feeding inhibition = 1. Treatment to 3rd


(White) diet feeding 100% instar larvae after
(Scarab beetle) 24-h pre-starvation.
100.0 µg/ml Feeding inhibition =
100% Negative feeding
response observed.
(3)

2. Heteronychus arator (Fab.) Artificial 200.0 µg/ml Feeding inhibition = 2. Treatment to 3rd
(Black beetle) diet feeding 4.0% instar larvae after
24-h pre-starvation.
(3)

(1) Bevan, C.W.L., Birch, A.J., Moore, B., and Mukerjee, S.K. (1964) J. Chem. Soc., 5991.
(2) Keen, N.T. (1975) Phytopathology, 65, 91.
(3) Sutherland, O.R.W., Russel, G.B., Biggs, D.R., and Lane, G.A. (1980) Biochem. Syst. Ecol., 8, 73.

© 2005 by CRC Press LLC


796 Opender Koul

PISCIDINOL–C C32H46O8
(558.71)
M.p. : 215°
OH

O O

AcO
HO

O OH

(1, 2, 3) (1, 2)

SOURCE: Walsura piscida Roxb., walasura (Meliaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk 1.0 µg/cm2 Feeding inhibition = Treatment to 3rd
(Tobacco armyworm) dual-choice 47.5% instar larvae for 24 h.
test
5.0 µg/cm2 Feeding inhibition = EC50 = 1.84 µg/cm2
51.5%
Data calculated from
10.0 µg/cm2 Feeding inhibition = Reference 3.
61.6% (3)

50.0 µg/cm2 Feeding inhibition =


62.4%

(1) Purushothaman, K.K., Duraiswamy, K., Connolly, J.D., and Rycroft, D.S. (1985) Phytochemistry, 28, 2349.
(2) Govindachari, T.R., Krishna Kumari, G.N., and Suresh, G. (1995) Phytochemistry, 39, 167.
(3) Govindachari, T.R., Narasimhan, N.S., Suresh, G., Partho, P.D., Gopalakrishnan, G., and Krishna Kumari,
G.N. (1995) J. Chem. Ecol., 21, 1586.

© 2005 by CRC Press LLC


Insect Antifeedants 797

PLAGIOCHILINE–A C19H26O6
(350.41)
Oil

[α]D : +32.3° (CHCl3)

AcO O
H

H H
AcO

(1, 2) (1, 2)

SOURCE: Plagiochila yokogurensis Inoue, liverwort (Fungi) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera exempta (Walker) Leaf disk 1–10 ng/cm2 Feeding inhibition = Treatment to larvae
(Nutgrass armyworm) test 100% for 2 h.
(1)

(1) Asakawa, Y., Toyota, M., Takemoto, T., Kubo, I., and Nakanishi, K. (1980) Phytochemistry, 19, 2147.
(2) Matsuo, A., Atsumi, K., and Nakayama, M. (1981) J. Chem. Soc. Perkin I, 2816.

© 2005 by CRC Press LLC


798 Opender Koul

PLICTRAN C18H34OSn
(385.16)
M.p. : 195–198°

HO Sn

(1, 2) (1)

SOURCE: Commercial material (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera littoralis (Boisd.) Leaf dip test 0.05% Feeding inhibition = 1. Treatment to
(Egyptian cotton leaf worm) 95.0% larvae weighing
170–190 mg.
(2)

2. Scolytus mediterraneus Twig dip test 0.05–0.2% Feeding inhibition = 2. Treatment to 0- to


Eggers 28–75% 1-day-old females.
(Fruit bark beetle) Observation based
on twig penetration.
(3)
0.05%
3. Gnorimoschema operculella Leaf dip test Feeding inhibition = 3. Treatment to 2nd
(Zell.) 67.4% instar larvae. Data
(Potato tuber moth) based on larval
mining calculated
from Reference 4.
(4)

LD50 (rats): 540 mg/kg (oral) (5)

(1) The Agrochemicals Handbook (1986), Roy. Soc. Chem.


(2) Ascher, K.R.S., Avdat, N., and Kamhi, J. (1970) Int. Pest Contr., 12, 11.
(3) Ascher, K.R.S., Gurevitz, E., Renneh, S., and Nemny, N.E. (1975) Z. Pflkrankh. Pflschutz., 82, 378.
(4) Ascher, K.R.S. and Meisner, J. (1969) Z. Pflkrankh. Pflpath. Pflschutz., 76, 564.
(5) Farms Chem. Handbook (1982) Meister Publishing Co., C232.

© 2005 by CRC Press LLC


Insect Antifeedants 799

PODOPHYLLOTOXIN C22H22O8
(414.41)
M.p. : 183.3–184.0°
OH
[α]20
D : –132.7° (CHCl3)

O
O
O

H3CO OCH3

OCH3

(1, 2) (1)

SOURCE: Podophyllum peltatum L., may apple, mandrake (Berberidaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Peridroma saucia (Hubner) Leaf disk 5.7 µg/cm2 Feeding inhibition = Treatment to 5th
(Variegated cutworm) test 51.7% instar larvae for 5 h.
(2)
11.4 µg/cm2 Feeding inhibition =
75.5%

28.5 µg/cm2 Feeding inhibition =


81.8%

LD50 (mouse): 100 mg/kg (oral) (3)

(1) Dev, S. and Koul, O. (1997) Insecticides of Natural Origin, Harwood Academic Publishers, Amsterdam, p. 184.
(2) Nawrot, J., Koul, O., Isman, M.B., and Harmatha, J. (1991) J. Appl. Ent., 112, 194.
(3) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC


800 Opender Koul

POLHOVOLIDE C23H32O8
(436.50)
M.p. : 98–99°

[α]20
D : –83.5° (CHCl3)
OAc

OAc
O
O

(1, 2) (1)

SOURCE: Laserpitium siler L., mountain lasser-wort (Apiaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius (L.) Wafer disk 1.0% Feeding deterrence 1. Treatment given to
(Grain weevil) test coefficient = 121 adults.

2. Tribolium confusum Duv. Wafer disk 1.0% Feeding deterrence 2. Treatment given to
(Confused flour beetle) test coefficient: both adults and
Adults = 132 larvae.
Larvae = 137

3. Trogoderma granarium Wafer disk 1.0% Feeding deterrence 3. Treatment given to


Everts test coefficient = 54.0 larvae.
(Khapra beetle) Neutral value = 0
Absolute feeding
deterrence value =
200
(2)

(1) Holub, M., Motl, O., and Samek, Z. (1978) Collect. Czech. Chem. Commun., 43, 2471.
(2) Nawrot, J., Smitalova, Z., and Holub, M. (1983) Biochem. Syst. Ecol., 11, 243.

© 2005 by CRC Press LLC


Insect Antifeedants 801

POLYGODIAL C15H22O2
(234.34)
M.p. : 57°
(50°)

B.p. : 138–140°/0.8 mm
CHO
[α]24
D : –131° (EtOH)
CHO

(1, 2) (1, 2)

SOURCE: Warburgia stuhlmanni L., warburgia (Canellaceae)


Polygonum hydropiper L., marsh pepper (Polygonaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera exempta (Walker) Leaf disk >0.1 ppm Considered weaker 1. Treatment to
(Nutgrass armyworm) choice test antifeedant than larvae. Exact
warburganal quantitative data not
recorded.
(2)

2. Leptinotarsa decemlineata Leaf disk 5 mM Feeding inhibition = 2. Treatment to


(Say) dual-choice 92.0% larvae of 90–120 mg
(Colorado potato beetle) assay body weight for a
period of 3 h.
(3)

(1) Barnes, C.S. and Loder, J.W. (1962) Aust. J. Chem., 15, 322.
(2) Nakanishi, K. and Kubo, I. (1977) Israel J. Chem., 16, 28.
(3) Gols, G.J.Z., van Loon, J.J.A., and Messchendorp, L. (1996) Entomol. Exp. Appl., 79, 69.

© 2005 by CRC Press LLC


802 Opender Koul

7-O-PRENYL FLAVONONE C21H20O3


(320.37)
No physical data given

O
O

(1) (1)

SOURCE: Lonchocarpus neuroscapha Bentt., coroa piaca (Fabaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera exempta (Walker) Glass fiber 100 ppm Feeding inhibition = 1. Treatment to 24- to
(Nutgrass armyworm) disk dual- 74.0% 36-h-old final
choice test stadium larvae for
10 ppm Feeding inhibition = 5 h. Larvae pre-
36.0% starved for 4 h.
(1)

2. Spodoptera littoralis (Boisd.) Glass fiber 500 ppm Feeding inhibition = 2. Treatment to 24- to
(Egyptian cotton leaf worm) disk dual- 29.0% 36-h-old final
choice test stadium larvae for
5 h. Larvae pre-
starved for 4 h.
(1)

(1) Simmonds, M.S.J., Blaney, W.M., Monache, F.D., and Bettolo, G.B.M. (1990) J. Chem. Ecol., 16, 365.

© 2005 by CRC Press LLC


Insect Antifeedants 803

8 – PRENYL FLAVANONE C21H22O8


(322.39)
No physical data given

HO O

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera exempta (Walker) Glass fiber 100 ppm Feeding inhibition = 1. Treatment to 24- to
(Nutgrass armyworm) disk dual- 79.0% 36-h-old final
choice test stadium larvae for
10 ppm Feeding inhibition = 5 h. Larvae pre-
34.0% starved for 4 h.
(1)

2. Spodoptera littoralis (Boisd.) Glass fiber 500 ppm Feeding inhibition = 2. Treatment to 24- to
(Egyptian cotton leaf worm) disk dual- 41.0% 36-h-old final
choice test stadium larvae for
5 h. Larvae pre-
starved for 4 h.
(1)

(1) Simmonds, M.S.J., Blaney, W.M., Monache, F.D., and Bettolo, G.B.M. (1990) J. Chem. Ecol., 16, 365.

© 2005 by CRC Press LLC


804 Opender Koul

PRIEURIANIN C38H50O16
(762.80)
OH M.p. : 214–218°

O [α]D20 : +13.3° (CHCl3)


O

COOH
AcO

O
OH
O
O CH2

COOCH3
CH2OAc
(1, 2) (2, 3)

SOURCE: Nymania capensis (Thunb.) Lindb., Chinese lantern (Meliaceae) (1, 2)


Entandrophragma candolei Harms, candollei (Meliaceae) (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Epilachna varivestis Muls. Leaf disk 19.8 µg/cm2 Feeding inhibition = 1. Treatment to 3rd
(Mexican bean beetle) choice test 60.0% instar larvae for
2 days.
6.0 µg/cm2 Feeding inhibition =
30.0%

2. Spodoptera eridania Leaf disk 19.8 µg/cm2 Feeding inhibition = 2. Treatment to 3rd
(Cramer) choice test 30.0% instar larvae for
(Southern armyworm) 2 days.

3. Heliothis virescens (Fab.) Leaf disk 19.8 µg/cm2 Feeding inhibition = 3. Treatment to 3rd
(Tobacco budworm) choice test 60.0% instar larvae for
2 days.
6.0 µg/cm2 Feeding inhibition = (1)
30.0%

4. Sitophilus granarius (L.) Wafer disk 10 mg/ml Feeding deterrence 4. Treatment given to
(Grain weevil) test coefficient = 175.8 adults.

5. Tribolium confusum Duv. Wafer disk 10 mg/ml Feeding deterrence 5. Treatment given to
(Confused flour beetle) test coefficient: both adults and
Adults = 100 larvae.
Larvae = 139.1

6. Trogoderma granarium Diet choice 10 mg/ml Feeding deterrence 6. Treatment given to


Everts assay coefficient = 166.7 larvae.
(Khapra beetle) Neutral value = 0
Absolute feeding
deterrence value =
200
(3)

© 2005 by CRC Press LLC


Insect Antifeedants 805

7. Helicoverpa armigera Wafer disk 91.4 ppm Feeding deterrence = 7. Treatment to 3rd
(Hubner) test 50% instar larvae, pre-
(Gram pod borer) starved for 4 h.
(4)

(1) Lidert, Z., Taylor, D.A., and Thirugnanam, M. (1985) J. Nat. Prod., 48, 843.
(2) Gullo, V.P., Miura, L., Nakanishi, K., Cameron, A.F., Connoly, J.D., Harding, A.E., McCrindle, R., and Taylor,
D.A.H. (1975), J. Chem. Soc. Chem. Commun., 345.
(3) Daniewski, W.M., Gumulka, M., Ancezewski, W., Truszewska, D., Bloszyk, E., and Drozdz, B. (1996) Polish
J. Chem., 70, 1265.
(4) Koul, O., Daniewski, W.M., Multani, J.S., Gumulka, M., and Singh, G. (2003) J. Agric. Food Chem., 51, 7271.

© 2005 by CRC Press LLC


806 Opender Koul

PRIEURIANIN ACETATE C40H52O17


OAc (804.84)
M.p. : 183°

O [α]D25 : 56.4° (pyridine)


O

COOH
AcO

O
OH
O
O CH2

COOCH3
CH2OAc
(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Epilachna varivestis Mulsant Leaf disk 6.0 µg/cm2 Feeding inhibition = 1. Treatment to 3rd
(Mexican bean beetle) choice test 90.0% instar larvae for
2 days.
1.5 µg/cm2 Feeding inhibition =
30.0%

2. Spodoptera eridania Leaf disk 19.8 µg/cm2 Feeding inhibition = 2. Treatment to 3rd
(Cramer) choice test 90.0% instar larvae for
(Southern armyworm) 2 days.
6.0 µg/cm2 Feeding inhibition =
60.0%

3. Heliothis virescens (Fab.) Leaf disk 19.8 µg/cm2 Feeding inhibition = 3. Treatment to 3rd
(Tobacco budworm) choice test 60.0% instar larvae for
2 days.
6.0 µg/cm2 Feeding inhibition = (1)
60.0%

4. Sitophilus granarius (L.) Wafer disk 10 mg/ml Feeding deterrence 4. Treatment given to
(Grain weevil) test coefficient = 164.5 adults.

5. Tribolium confusum Duv. Wafer disk 10 mg/ml Feeding deterrence 5. Treatment given to
(Confused flour beetle) test coefficient. both adults and
Adults = 168.4 larvae.
Larvae = 140.8

© 2005 by CRC Press LLC


Insect Antifeedants 807

6. Trogoderma granarium Wafer disk 10 mg/ml Feeding deterrence 6. Treatment given to


Everts test coefficient = 167.8 larvae.
(Khapra beetle) Neutral value = 0
Absolute feeding
deterrence value =
200
(2)

7. Helicoverpa armigera Diet 82.7 ppm Feeding deterrence = 7. Treatment to 3rd


(Hubner) choice 50% instar larvae, pre-
(Gram pod borer) assay starved for 2 h.
(3)

(1) Lidert, Z., Taylor, D.A., and Thirugnanam, M. (1985) J. Nat. Prod., 48, 843.
(2) Daniewski, W.M., Gumulka, M., Ancezewski, W., Truszewska, D., Bloszyk, E., and Drozdz, B. (1996) Polish
J. Chem., 70, 1265.
(3) Koul, O., Daniewski, W.M., Multani, J.S., Gumulka, M., and Singh, G. (2003) J. Agric. Food Chem., 51, 7271.

© 2005 by CRC Press LLC


808 Opender Koul

epoxy-PRIEURIANIN C38H50O15
(746.80)
OH [α]D : +24.5° (CHCl3)

COOH
AcO
O

O CH2

COOCH3
CH2OAc
(1, 2) (1)

SOURCE: Entandrophragma candolei Harms, candolei (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius (L.) Wafer disk 10 mg/ml Feeding deterrence 1. Treatment given to
(Grain weevil) test coefficient = 196.5 adults.

2. Tribolium confusum Duv. Wafer disk 10 mg/ml Feeding deterrence 2. Treatment given to
(Confused flour beetle) test coefficient: both adults and
Adults = 196.5 larvae.
Larvae = 141.8

3. Trogoderma granarium Wafer disk 10 mg/ml Feeding deterrence 3. Treatment given to


Everts test coefficient = 67.7 larvae.
(Khapra beetle) Neutral value = 0
Absolute feeding
deterrence value =
200
(1)

4. Helicoverpa armigera Diet choice 62.0 ppm Feeding deterrence = 4. Treatment to 3rd
(Hubner) assay 50% instar larvae, pre-
(Gram pod borer) starved for 4 h.
(3)

(1) Lukacova, V., Polonsky, J., Moretti, C., Pettit, G.R., and Schmidt, J.M. (1982) J. Nat. Prod., 45, 288.
(2) Daniewski, W.M., Gumulka, M., Ancezewski, W., Truszewska, D., Bloszyk, E., and Drozdz, B. (1996) Polish
J. Chem., 70, 1265.
(3) Koul, O., Daniewski, W.M., Multani, J.S., Gumulka, M., and Singh, G. (2003) J. Agric. Food Chem., 51, 7271.

© 2005 by CRC Press LLC


Insect Antifeedants 809

epoxy-PRIEURIANIN ACETATE C40H52O16


(788.84)
OAc Only spectral data given

COOH
AcO
O

O CH2

COOCH3
CH2OAc
(1, 2) (2)

SOURCE: Synthetic (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius (L.) Wafer disk 10 mg/ml Feeding deterrence 1. Treatment given to
(Grain weevil) test coefficient = 187.0 adults.

2. Tribolium confusum Duv. Wafer disk 10 mg/ml Feeding deterrence 2. Treatment given to
(Confused flour beetle) test coefficient: both adults and
Adults = 167.6 larvae.
Larvae = 163.4

3. Trogoderma granarium Wafer disk 10 mg/ml Feeding deterrence 3. Treatment given to


Everts test coefficient = 200 larvae.
(Khapra beetle) Neutral value = 0
Absolute feeding
deterrence value =
200
(1)

4. Helicoverpa armigera Diet choice 48.3 ppm Feeding deterrence = 4. Treatment to 3rd
(Hubner) assay 50% instar larvae, pre-
(Gram pod borer) starved for 4 h.
(2)

(1) Daniewski, W.M., Gumulka, M., Ancezewski, W., Truszewska, D., Bloszyk, E., and Drozdz, B. (1996) Polish
J. Chem., 70, 1265.
(2) Koul, O., Daniewski, W.M., Multani, J.S., Gumulka, M., and Singh, G. (2003) J. Agric. Food Chem., 51, 7271.

© 2005 by CRC Press LLC


810 Opender Koul

PRONAMIDE C12H11ONCl2
(256.13)
M.p. : 155–157°

Cl CONHC C CH

Cl

(1) (1)

SOURCE: Commercial sample (a herbicide) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera littoralis (Boisd.) Leaf dip test 0.3% a.i. Weight gain of 70.9 Treatment to larvae
(Egyptian cotton leaf worm) from WP mg against 211.5 mg of 90–100 mg body
50% in controls weight.
Antifeedant effect
0.2% a.i. Weight gain of 87.5 based on weight gain
from WP mg against 211.5 mg after 48 h.
50% in controls (2)

0.1% a.i. Weight gain of 116.5


from WP mg against 211.5 mg
50% in controls

(1) Swithenbank, C., McNulty, P.J., and Viste, K.L. (1971) J. Agric. Food Chem., 19, 417.
(2) Meisner, J., Lifshitz, N., and Ascher, K.R.S. (1987) J. Econ. Entomol., 80, 724.

© 2005 by CRC Press LLC


Insect Antifeedants 811

n-PROPYL GALLATE C10H12O5


(212.20)
M.p. : 150°

COO

OH
HO

OH

(1) (1)

SOURCE: Commercial sample (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Schizaphis graminum Artificial diet 96 ppm Feeding inhibition = 1. Treatment to


(Rondani) feeding 50.0% aphids at random.
(Wheat aphid)
Concentration = EC50
value.

2. Acyrthosiphon pisum (Harris) Artificial diet 304 ppm Feeding inhibition = 2. Treatment to
(Pea aphid) feeding 50.0% aphids at random.

Concentration = EC50
value.

3. Myzus persicae (Sulzer) Artificial diet 198 ppm Feeding inhibition = 3. Treatment to
(Green peach aphid) feeding 50.0% aphids at random.

Concentration = EC50
value.
(2)

LD50 (rats): 3.8 g/kg (oral) (3)

(1) Jasim, F. (1970) Talanta, 17, 103.


(2) Jones, K.C. and Klocke, J.A. (1987) Entomol. Exp. Appl., 44, 229.
(3) Clayton, G.D. and Clayton, F.E. (1981) Patty’s Industrial Hygiene and Toxicology, 2A, 2326.

© 2005 by CRC Press LLC


812 Opender Koul

PROTOCATECHUIC ACID C 7 H 6O 4
(154.12)
M.p. : ~200° (dec.)
(195–196°, anhyd.)

COOH

OH

OH

(1, 2) (1, 3)

SOURCE: Pteridium aquilinum L. Kuhn, bracken fern (Pteridophyta) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Pieris brassicae (L.) Leaf disk 6.5 × 10–2 M Feeding ratio = 2.87 Treatment to 2nd day
(Large white butterfly) no-choice 5th instar larvae.
test Feeding ratio < 20
strong antifeedant
effect.
(2)

(1) Horhammer, L. and Scherm, A. (1955) Arch. Pharm., 288, 441.


(2) Jones, C.G. and Firn, R.D. (1979) Biochem. Syst. Ecol., 7, 187.
(3) (1994) Dictionary of Natural Products, Chapman & Hall, London.

© 2005 by CRC Press LLC


Insect Antifeedants 813

PSORALEN C11H6O3
(186.17)
M.p. : 171°
(161–162°, 165°)

O O O

(1, 2) (1, 2)

SOURCE: Commercial sample used for evaluation. (2)


However, compound occurs in Psoralea spp. and some plants of family Fabaceae.

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Artificial diet 170 ppm Feeding inhibition = Treatment to 4th
(Tobacco armyworm) test 50.0% instar larvae, pre-
starved for 4 h.

Treatment duration =
48 h.

Concentration = EC50
value.
(2)

(1) Murray, R.D.H. (1982) The Natural Coumarins, John Wiley, New York.
(2) Luthria, D.L., Ramakrishnan, V., Verma, G.S., Prabhu, B.R., and Banerji, A. (1989) J. Agric. Food Chem.,
37, 1435.

© 2005 by CRC Press LLC


814 Opender Koul

PTEROSIN–F C14H17OCl
(236.74)
M.p. : 66–67°

[α]D : –9.2° (benzene)

Cl

(1, 2) (1, 2)

SOURCE: Pteridium aquilinum L. Kuhn, bracken fern (Pteridophyta) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Pieris brassicae (L.) Leaf disk no- 100 mg/kg Feeding ratio = 4.0 1. Treatment to 2nd
(Large white butterfly) choice test fresh disk day 5th instar
weight unstarved larvae.
(3)

2. Chilo partellus (Swinhoe) Leaf disk no- 100 mg/kg Feeding ratio = 5.0 2. Treatment to 2nd
(Maize borer) choice test fresh disk day 5th instar
weight unstarved larvae.
(3)
Feeding ratio
< 20 very strong
antifeedant effect.

(1) Yoshihira, K., Fukuoka, M., Kuroyanagi, M., and Natori, S. (1971) Chem. Pharm. Bull., 19, 1491.
(2) Yoshihira, K., Fukuoka, M., Kuroyanagi, M., and Natori, S. (1972) Chem. Pharm. Bull., 20, 426.
(3) Jones, C.G. and Firn, R.D. (1979) Biochem. Syst. Ecol., 7, 95.

© 2005 by CRC Press LLC


Insect Antifeedants 815

PUNGENIN C14H18O8
(314.29)
M.p. : 198–199°
(190–191)
O
[α]D22 : –96.8° (H2O)

CH2OH

O
O
HO
OH
HO OH

(1, 2) (1)

SOURCE: Picea pungens Engelm., Colorado spruce


P. glauca (Moench) Voss, white spruce (Pinaceae)
Synthetic (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Choristoneura fumiferana Paper disk 5.0% Modest antifeedant Treatment to 6th


(Clem.) test effect instar larvae.
(Spruce budworm)
No quantitative data
recorded.
(2)

(1) Neish, A.C. (1957) Can. J. Biochem., 35, 161.


(2) Strunz, G.M., Ciguere, P., and Thomas, A.W. (1986) J. Chem. Ecol., 12, 251.

© 2005 by CRC Press LLC


816 Opender Koul

PYROGALLOL C6H6O3
(126.11)
M.p. : 133–134°

B.p. : 171.5°/12 mm

OH
HO

OH

(1) (1)

SOURCE: Commercial sample (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Schizaphis graminum Artificial diet 144 ppm Feeding inhibition = 1. Treatment to


(Rondani) feeding 50.0% aphids at random.
(Wheat aphid) Concentration = EC50
value.

2. Acyrthosiphon pisum (Harris) Artificial diet 455 ppm Feeding inhibition = 2. Treatment to
(Pea aphid) feeding 50.0% aphids at random.
Concentration = EC50
value.

3. Myzus persicae (Sulzer) Artificial diet 276 ppm Feeding inhibition = 3. Treatment to
(Green peach aphid) feeding 50.0% aphids at random.
Concentration = EC50
value.
(2)

LD50 (rats): 789 mg/kg (oral) (3)

(1) Rindrknecht, H. and Niemann, C. (1948) J. Am. Chem. Soc., 70, 2605.
(2) Jones, K.C. and Klocke, J.A. (1987) Entomol Exp. Appl., 44, 229.
(3) Lewis, R.J. and Tatken, R.L. (1980) RTECS, 2, 539.

© 2005 by CRC Press LLC


Insect Antifeedants 817

1-O-PYRUVYL-22,23-DIHYDROAZADIRACHTININ
No physical data given

COOCH3
OH OH
pyruvate - O O

O
O
OH
AcO
H
H3COOC O

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera littoralis (Boisd.) Glass fiber 1 ppm Feeding inhibition = Treatment to 24- to
(Egyptian cotton leaf worm) disk choice 55.0% 36-h-old starved final
test stadium larvae.
Bioassay terminated
2. Spodoptera frugiperda Glass fiber 1 ppm Feeding inhibition = after the larvae had
(J.E. Smith) disk choice 52.0% consumed about 50%
(Fall armyworm) test of one of the disks.
(1)
3. Heliothis virescens (Fab.) Glass fiber 1 ppm Feeding inhibition =
(Tobacco budworm) disk choice 63.0%
test

4. Helicoverpa armigera Glass fiber 1 ppm Feeding inhibition =


(Hubner) disk choice 44.0%
(Gram pod borer) Test

(1) Blaney, W.M., Simmonds, M.S.J., Ley, S.V., Anderson, J.C., and Toogood, P.L. (1990) Entomol. Exp. Appl.,
55, 149.

© 2005 by CRC Press LLC


818 Opender Koul

QUADRANGOLIDE C15H20O3
(248.32)
M.p. : 118–120°

[α]D22 : +227° (neat)

O
O

CH2
O

(1) (1)

SOURCE: Eupatorium quadrangularae L., joe-pye-weed (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test insect Efficacy Remarks
Method Dose

Atta cephalotes (L.) Rye flake 6 mg/ml or Feeding inhibition = Treatment to adult
(Leaf cutter ant) forced- 120 µg/flake 94.1% workers.
choice
feeding Data calculated from
Reference 1.
(1)

(1) Hubert, T.D., Okunade, A.L., and Wiemer, D.F. (1987) Phytochemistry, 26, 1751.

© 2005 by CRC Press LLC


Insect Antifeedants 819

QUASSIN C22H28O6
(388.46)
M.p. : 221–222°

[α]D20 : +34.5° (CHCl3)


OCH3

O
O

H3CO

H
O O

(1, 2) (1)

SOURCE: Quassia amara L., Surinam quassia (Simaroubiceae) (1,2)

ACTIVITY PROFILE

Test Conc. /
Test insect Efficacy Remarks
Method Dose

1. Heliothis virescens (Fab.) Leaf disk 19.8 µg/cm2 Feeding inhibition = 1. Treatment to 3rd
(Tobacco budworm) test 30–60% instar larvae for
2 days.
(2)

2. Epilachna varivestis Muls. Whole leaf 250 ppm Feeding deterrence = 2. Treatment to 4th
(Mexican bean beetle) application 90.0% instar larvae for 24 h.
Larvae pre-starved
100 ppm Feeding deterrence = for 2 h.
92.0%
Data calculated from
50 ppm Feeding deterrence = Reference 3.
87.8% (3)

(1) Valenta, Z., Papadopoulos, S., and Podesva, C. (1961) Tetrahedron, 15, 100.
(2) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y., Kiyokawa, H., and Lee, K.H.
(1987) J. Nat. Prod., 50, 442.

© 2005 by CRC Press LLC


820 Opender Koul

QUERCETIN C15H10O7
(302.23)
M.p. : 314° (dec.)
(anhydrous)
OH

OH

HO O

OH

OH O

(1) (1)

SOURCE: Rhodendron cinnabaricum Hook, rhododendron (Ericaceae) and many other plant species (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test insect Efficacy Remarks
Method Dose

1. Schizaphis graminum Artificial diet 0.08% Feeding inhibition = 1. Treatment to


(Rondani) feeding 50.0% 50–75 aphids at
(Wheat aphid) random for 24 h.

Concentration = EC50
value.
(2)

2. Myzus persicae (Sulzer) Artificial diet 0.03% Feeding deterrence = 2. Treatment to


(Green peach aphid) feeding 50.0% 50–75 aphids at
random for 8 h.

Concentration = EC50
value.
(2)

LD50 (mice): 180 mg/kg (oral) (3)

(1) Rangaswami, S., Sambamurthy, K., and Mallayya Sastry, K. (1962) Proc. Ind. Acad. Sci., 56A, 239.
(2) Dreyer, D.L. and Jones, K.C. (1981) Phytochemistry, 20, 2489.
(3) Sullivan, M., Folks, R.H. Jr., and Hilgartner, M. (1951) Proc. Soc. Exp. Biol. Med., 77, 269.

© 2005 by CRC Press LLC


Insect Antifeedants 821

QUERCITRIN C21H20O11
(448.38)
M.p. : 182–185°
OH (250–252°)
(anhydrous)
OH
[α]15
D : –158° (MeOH)

HO O

O OH
O
OH O

HO OH (1) (1, 2)

SOURCE: Semisynthetic and many plant species (3)

ACTIVITY PROFILE

Test Conc. /
Test insect Efficacy Remarks
Method Dose

1. Schizaphis graminum Artificial diet 0.06% Feeding inhibition = 1. Treatment to


(Rondani) feeding 50.0% 50–75 aphids at
(Wheat aphid) random for 24 h.

Concentration = EC50
value.
(3)

2. Myzus persicae (Sulzer) Artificial diet 0.06% Feeding deterrence = 2. Treatment to


(Green peach aphid) feeding 50.0% 50–75 aphids at
random for 8 h.

Concentration = EC50
value.
(3)

(1) Zemplen, G., Csuros, Z., Gerecs, A., and Aczel, S. (1928) Ber., 61, 2486.
(2) Horhammer, L., Wagner, H., Arndt, H., Dirschrel, R., and Farkas, L. (1968) Chem. Ber., 101, 450.
(3) Dreyer, D.L. and Jones, K.C. (1981) Phytochemistry, 20, 2489.

© 2005 by CRC Press LLC


822 Opender Koul

QUININE C20H24O2N2
(324.42)
M.p. : 177° (anhydrous)

[α]15
D : –159° (EtOH)

CH2

HO
N
H
H3CO

(1, 2) (1)

SOURCE: Commercial sample (1)

ACTIVITY PROFILE

Test Conc. /
Test insect Efficacy Remarks
Method Dose

Phormia regina (Meigen) Sucrose 10 mM Feeding inhibition = Treatment to 2-, 4-,


(Blowfly) solution 93.0% and 6-day-old adults,
feeding pre-starved for 24 h.

Treatment duration =
6–24 h.
(2)

LD50 (mice): 115 mg/kg (ipr.) (3)

(1) Merck Index (1983) p. 7963.


(2) Blades, D. and Mitchell, B.K. (1986) Entomol. Exp. Appl., 41, 299.
(3) Hahn, F.E. (1979) Antibiotics, 5, 353.

© 2005 by CRC Press LLC


Insect Antifeedants 823

RACEMOSIN C16H16O5
(288.30)
M.p. : 126–127°

OCH3

O O O

OCH3

(1, 2) (1)

SOURCE: Atalantia racemosa Wight and Arn., wild lime (Rutaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Artificial diet 778 ppm Feeding inhibition = Treatment to 4th
(Tobacco armyworm) feeding 50.0% instar larvae, pre-
starved for 4 h.

Treatment duration =
48 h.

Concentration = EC50
value.
(2)

(1) Joshi, B.S., Gawad, D.H., and Ravindranath, K.R. (1978) Proc. Ind. Acad. Sci., 87A, 173–179.
(2) Luthria, D.L., Ramakrishnan, V., Verma, G.S., Prabhu, B.R., and Banerji, A. (1989) J. Agric. Food Chem.,
37, 1435.

© 2005 by CRC Press LLC


824 Opender Koul

REMIROL C14H16O4
(248.28)
M.p. : 76–77°

[α]D25 : +66.5°

O OH

O CH 2
CH3O

(1) (1)

SOURCE: Cyperus nipponicus, C. distans L., sedge (Cyperaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk 1.3 × 10–7 Feeding inhibition = Treatment to 3rd
(Tobacco armyworm) assay mol/cm2 50.0% instar larvae up to
5 h.

Concentration = EC50
value.
(1)

(1) Morimoto, M., Fujii, Y., and Komai, K. (1999) Phytochemistry, 51, 605.

© 2005 by CRC Press LLC


Insect Antifeedants 825

RHODOJAPONIN–III C20H32O6
(368.46)
M.p. : 274° (dec.)
285–287°

OH
H
O OH

OH

OH
OH

(1, 2) (1, 2)

SOURCE: Rhododendron molle (B.) G.Don, yellow azalea (Ericaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test insect Efficacy Remarks
Method Dose

1. Leptinitarsa decemlineata Leaf disk 2.8 µg/50 Feeding inhibition = 1. Treatment to 4th
(Say) choice test mm2 95.0% instar larvae until
(Colorado potato beetle) 95% of control disk
was eaten.

Leaf disk no- 1.1 µg/50 Feeding inhibition = Concentration = PC95


choice test mm2 95.0% value.
(1)

2. Spodoptera frugiperda Leaf disk 6.4 µg/50 Feeding inhibition = 2. Treatment to 3rd
(J.E. Smith) choice test mm2 95.0% instar larvae until
(Fall armyworm) 95% of control disk
was eaten.

Leaf disk no- 1.6 µg/50 Feeding inhibition = Concentration = PC95


choice test mm2 95.0% value.
(1)

(1) Klocke, J.A., Hu, M., Chiu, S., and Kubo, I. (1991) Phytochemistry, 30, 1797.
(2) Dev, S. and Koul, O. (1997) Insecticides of Natural Origin, Harwood Academic Publishers, Amsterdam, p. 95.

© 2005 by CRC Press LLC


826 Opender Koul

RIDDELLINE C18H23O6N
(349.38)
M.p. : 197–198°

[α]25
D : –109.5° (CHCl3)
CH2 OH
H

C C H2C C C CH2OH

COO CH2OCO

(1, 2) (1)

SOURCE: Senecio riddellii L., groundsel (Asteraceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test insect Efficacy Remarks
Method Dose

Acyrthosiphon pisum (Harris) Artificial 0.03 ± 0.006% Feeding inhibition = Treatment to aphids
(Pea aphid) diet 50.0% at random.
feeding
Concentration = EC50
value.
(2)

LD50 (mice): 105 mg/kg (ivn.) (3)

(1) Adams, R., Hanlin, K.E. Jr., Jelinck, C.F., and Phillips, R.F. (1942) J. Am. Chem. Soc., 64, 2760.
(2) Dreyer, D.L., Jones, K.C., and Molyneux, R.J. (1985) J. Chem. Ecol., 11, 1045.
(3) Mattocks, A.R. (1986) Chemistry and Toxicology of Pyrrolizidine Alkaloids, Academic Press, New York.

© 2005 by CRC Press LLC


Insect Antifeedants 827

ROHITIUKA–7 C35H44O13
OH (672.72)
M.p. : 239–242°
O
[α]D : –32°
O

COOH

O OH
OAc
O CH2

O
O (1, 2) (1, 2)

SOURCE: Aphanamixis polystacha Wall & Parker, tiktara (Meliaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test insect Efficacy Remarks
Method Dose

1. Heliothis virescens (Fab.) Leaf disk 19.8 µg/cm2 Feeding deterrence = 1. Treatment to 3rd
(Tobacco budworm) choice test 60–90% instar larvae for
2 days.
(1)

2. Epilachna varivestis Muls. Leaf disk 19.8 µg/cm2 Feeding inhibition = 2. Treatment to 3rd
(Mexican bean beetle) choice test No activity instar larvae for
6 days.
(1)

(1) Lidert, Z., Taylor, D.A., and Thirugnanam, M. (1985) J. Nat. Prod., 48, 843.
(2) Brown, D.A. and Taylor, D.A.H. (1978) Phytochemistry, 17, 1955.

© 2005 by CRC Press LLC


828 Opender Koul

ROTENONE C23H22O6
(394.42)
M.p. : 162.5–164°
H
[α]25
D : –225° (benzene)

H2C
H
O O O

H
O
OCH3

OCH3

(1, 2) (1)

SOURCE: Isolated from various species of Derris and Lonchocarpus (Fabaceae) (1)
Commercial sample (2)

ACTIVITY PROFILE

Test Conc. /
Test insect Efficacy Remarks
Method Dose

1. Costelytra zealandica Artificial 0.06 µg/g Feeding inhibition = 1. Treatment to 24-h


(White) diet 50.0% starved 3rd instar
(Scarab beetle) feeding larvae.

Concentration = EC50
value.
(2)

2. Sitophilus granarius (L.) Wafer disk 10 mg/ml Feeding deterrence 2. Treatment to


(Grain weevil) assay coefficient = 200 adults. Data on
0–200 greater
deterrence scale.
(3)

3. Trogoderma granarium Wafer disk 10 mg/ml Feeding deterrence 3. Treatment to


Everts assay coefficient = 200 adults. Data on
(Khapra beetle) 0–200 greater
deterrence scale.
(3)

4. Tribolium confusum Duv. Wafer disk 10 mg/ml Feeding deterrence 4. Treatment to


(Confused flour beetle) assay coefficient = 200 adults and larvae.
Data on 0–200
greater deterrence
scale.
(3)

5. Spodoptera exempta (Walker) Leaf disk 10 µg/2 cm Feeding deterrence = 5. Treatment to mid-
(Nutgrass armyworm) choice test diameter disk 82.0% 6th instar larvae for
2 h. Larvae pre-
10 µg/2 cm Feeding deterrence = starved for 2 h.
diameter disk 52.0% (5)

© 2005 by CRC Press LLC


Insect Antifeedants 829

6. Eldana saccharina Walker Leaf disk 100 µg/1.8 Feeding deterrence = 6. Treatment to 5th
(Sugar cane borer) choice test cm disk 89.0% instar larvae, pre-
starved for 12 h and
10 µg/1.8 cm Feeding deterrence = allowed to feed for
disk 92.0% 24 h in dark.
(5)
1 µg/1.8 cm Feeding deterrence =
disk 81.0%

7. Maruca testulalis (Geyer) Leaf disk 100 µg/1.8 Feeding deterrence = 7. Treatment to late
(Bean pod borer) choice test cm disk 97.0% 5th instar larvae for
6 h.
10 µg/1.8 cm Feeding deterrence = (4)
disk 86.0%

1 µg/1.8 cm Feeding deterrence =


disk 45.0%

LD50 (mice): 2.8 mg/kg (i.p.) (5)

(1) Dev, S. and Koul, O. (1997) Insecticides of Natural Origin, Harwood Academic Publishers, Amsterdam, p. 207.
(2) Lane, G.A., Biggs, D.R., Russel, G.B., Sutherland, O.R.W., Williams, E.M., Maindonald, J.H., and Donnell,
D.J. (1985) J. Chem. Ecol., 11, 1713.
(3) Nawrot, J., Harmatha, J., Kostova, I., and Ognyanov, I. (1989) Biochem. Syst. Ecol., 17, 55.
(4) Bentley, M.D., Hassanali, A., Lwandi, W., Nijoroge, P.E.W., Sitayo, E.N.O., and Yatagai, M. (1987) Insect
Sci. Applic., 8, 85.
(5) Fukami, J., Yamamoto, I., and Casida, J.E. (1967) Science, 155, 713.

© 2005 by CRC Press LLC


830 Opender Koul

RUTAEVIN C26H30O9
(486.52)
M.p. : 300°
O
[α]26
D : –130° (Me2CO)
O

O O

O
O O

OH

(1, 2) (1)

SOURCE: Evodia rutaecarpa Hook f. et Thoms., Chinese Wu-Chu-Yu (Rutaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test insect Efficacy Remarks
Method Dose

Helicoverpa zea (Boddie) Leaf disk 125 µg/disk Feeding deterrence = Treatment to larvae.
(Corn earworm) choice test 95% (2)

(1) Dreyer, D.L., Bennett, R.D., and Basa, S.C. (1976) Tetrahedron, 32, 2367.
(2) Kubo, I. and Klocke, J.A. (1981) Colloques Inst. Nat. Recherches Agric., 7, 117.

© 2005 by CRC Press LLC


Insect Antifeedants 831

RUTIN C27H30O16
(610.52)
M.p. : 214–215° (dec.)
(anhydrous)
OH
[α]23
D : +13.82° (EtOH)
OH

HO O

O rutinose

OH O

(1) (1)

SOURCE: Found in many plants; also semisynthetic (2)

ACTIVITY PROFILE

Test Conc. /
Test insect Efficacy Remarks
Method Dose

Schizaphis graminum (Rondani) Artificial diet 0.02% Feeding inhibition = Treatment to 50–75
(Wheat aphid) feeding 50.0% aphids at random for
24 h.

Concentration = EC50
value.
(2)

LD50 (mice): 950 mg/kg (i.v.) (3)

(1) Merck Index (1983).


(2) Dreyer, D.L. and Jones, K.C. (1981) Phytochemistry, 20, 2489.
(3) Harrison, G. (1950) J. Am. Pharm. Assoc., 39, 557.

© 2005 by CRC Press LLC


832 Opender Koul

RYANODINE C25H35O9N
(493.55)
M.p. : 219–220°

OH [α]D : +26° (MeOH)


OH

HO OH
O O
O
OH
HO

NH

(1, 2) (1, 2)

SOURCE: Ryania speciosa Vahl, ryania (Flacourtiaceae) (1)


Persea indica Spreng., canary wood (Lauraceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk 1000 ppm Feeding inhibition = Treatment to 3rd
(Tobacco armyworm) choice test 100% instar larvae for 1
day. Data based on
antifeedant index =
0. Index less than 23
considered highly
deterrent.
(2)

LD50 (rats): 750 mg/kg (oral); (mice): 0.1 mg/kg (i.p.) (3)

(1) Dev, S. and Koul, O. (1997) Insecticides of Natural Origin, Harwood Academic Publishers, Amsterdam, p. 98.
(2) Gonzalex-Coloma, A., Terrero, D., Perales, A., Escoubas, P., and Fraga, B.M. (1996) J. Agric. Food Chem.,
44, 296.
(3) Crosby, D.G. (1971) In M. Jacobson and D.G. Crosby (eds.), Naturally Occurring Insecticides, Marcel Dekker,
New York, pp. 177–139.

© 2005 by CRC Press LLC


Insect Antifeedants 833

RYANODOL C20H32O8
(400.47)
M.p. : 345–347°

OH
OH

HO OH
O
HO
OH
HO

(1) (1)

SOURCE: Persea indica spreng., canary wood (Lauraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk 1000 ppm Feeding inhibition = Treatment to 3rd
(Tobacco armyworm) choice test Approx. 100% instar larvae for 1
day. Data based on
antifeedant index =
0.51. Index less than
23 considered highly
deterrent.
(1)

LD50 (mice): 17.92 mg/kg (i.p.) (1)

(1) Gonzalex-Coloma, A., Terrero, D., Perales, A., Escoubas, P., and Fraga, B.M. (1996) J. Agric. Food Chem.,
44, 296.

© 2005 by CRC Press LLC


834 Opender Koul

SAINFURAN C16H14O5
(286.28)
M.p. : 150–152°

H3CO OH

OH

O
OCH3

(1) (1)

SOURCE: Onobrychis viciifolia Scop., sainfoin (Fabaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Costelytra zealandica (White) Artificial diet 2 µg/g Feeding of insect Treatment to 3rd
(Scarab beetle) feeding larvae significantly instar larvae.
reduced (P < 0.05) (1)
within 24 h of
assessment.

(1) Russel, G.B., Shaw, G.J., Christmas, P.E., Yates, M.B., and Sutherland, O.R.W. (1984) Phytochemistry, 23,
1417.

© 2005 by CRC Press LLC


Insect Antifeedants 835

SALANNIC ACID C26H34O7


(458.55)
M.p. : 228–230°

COOH
OH O

O
HO
H
O

(1) (1)

SOURCE: Synthetic (1)


Occurs in Melia dubia Cav., M. volkensii Guerke, Azadirachta indica A. Juss. (Meliaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Leptinotarsa decemlineata Leaf disk 50 µg/cm2 Feeding inhibition = Treatment to newly


(Say) choice test 95.0%. moulted 3rd instar
(Colorado potato beetle) larvae.
Disks examined
every 2 h until >95%
of control disks were
eaten.
(1)

(1) Yamasaki, R.B. and Klocke, J.A. (1989) J. Agric. Food Chem., 37, 1118.
(2) Handerson, R., McCrindle, R., Melera, A., and Overton, K.H. (1968) Tetrahedron, 24, 1525.

© 2005 by CRC Press LLC


836 Opender Koul

SALANNIN C34H44O9
(596.72)
M.p. : 167–170°

O [α]D : +167° (CHCl3)


O

O O
O

O
AcO
H
O

(1) (2)

SOURCE: Azadirachta indica A. Juss., neem (Meliaceae)


Melia azedarach L., china berry; M. dubia Cav., and M. volkensii Guerke (Meliaceae) (1–5)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Leptinotarsa decemlineata Leaf disk >400 µg/disk Feeding inhibition = 1. Treatment to


(Say) choice test 95.0% newly moulted 3rd
(Colorado potato beetle) instar larvae.

150 µg/disk Feeding inhibition = Disks examined


50.0% every 2 h until > 95%
of control disks were
eaten.

Concentrations
denote protection
levels.
(1)

2. Spodoptera littoralis (Boisd.) Styropor 0.1% 62.6% protection 2. Treatment to


(Egyptian cotton leaf worm) lemellar against controls larvae of 100–120
test mg body weight for
0.01% 48.4% protection 48 h.
against controls
Data calculated from
Reference 6.
(6)

3. Earias insulana (Boisd.) Styropor 0.1% 78.6% protection 3. Treatment to


(Spotted bollworm) lemellar against controls larvae of 20 mg body
test weight for 48 h.
0.01% 57.1% protection
against controls Data calculated from
Reference 6.
(6)

© 2005 by CRC Press LLC


Insect Antifeedants 837

4. Epilachna varivestis Bean half 0.0082% Feeding inhibition = 4. Treatment to 4th


(Mulsant) leaf assay 50.0% instar larvae for 12 h.
(Mexican bean beetle)
Concentration = EC50
value.
(7)

5. Diabrotica undecimpunctata Leaf disk 0.1% Feeding deterrence = 5. Treatment to adult


howardi Barber choice test 79.0% beetles for 24 h.
(Spotted cucumber beetle) 0.5% Feeding deterrence = Data calculated from
76.0% Reference 8.
1.0% Feeding deterrence = (8)
90.0%

6. Acalymma vittatum (Fab.) Leaf disk 0.1% Feeding deterrence = 6. Treatment to adult
(Striped cucumber beetle) choice test 86.0% beetles for 24 h.
0.5% Feeding deterrence =
98.0% Data calculated from
1.0% Feeding deterrence = Reference 8.
100% (8)

7. Musca domestica L. Solution 0.1% Feeding deterrence = 7. Treatment to


(Housefly) feeding 100% adults.
(9)

8. Spodoptera litura (Fab.) Leaf disk 1 µg/cm2 Feeding deterrence = 8. Treatment to 3rd
(Tobacco armyworm) dual- 63.5% instar larvae for 24 h.
choice test 10 µg/cm2 Feeding deterrence = (10)
69.8%

9. Pericallia ricini (Fab.) Leaf disk 1 µg/cm2 Feeding deterrence = 9. Treatment to 3rd
(Tiger moth) dual- 70.7% instar larvae for 24 h.
choice test 10 µg/cm2 Feeding deterrence = (10)
77.5%

10. Oxya fuscovittata (Marsh.) Leaf disk 1 µg/cm2 Feeding deterrence = 10. Treatment to 3rd
(Grasshopper) dual- 71.2% instar larvae for 24 h.
choice test 10 µg/cm2 Feeding deterrence = (10)
84.6%

(1) Yamasaki, R.B. and Klocke, J.A. (1989) J. Agric. Food Chem., 37, 1118.
(2) Henderson, R., McCrindle, R., Melera, A., and Overton, K.H. (1968) Tetrahedron, 24, 1525.
(3) Srivastava, S.D. (1986) J. Nat. Prod., 49, 56.
(4) Srivastava, S.D. and Srivastava, S.K. (1996) Fitoterapia, LXVII, 113.
(5) Rajab, M.S., Bentley, M.D., Alford, A.R., and Mendel, M.J. (1988) J. Nat. Prod., 51, 168.
(6) Meisner, J., Ascher, K.R.S., Aly, R., and Warthen, J.D. Jr. (1981) Phytoparasitica, 9, 27.
(7) Schwinger, M., Ehhammer, B., and Kraus, W. (1983) In H. Schmutterer and K.R.S. Ascher (eds.), Proc. 2nd
Int. Neem Conf., GTZ, Eschborn, Germany, pp. 181–198.
(8) Reed, D.K., Jacobson, M., Warthen, J.D. Jr., Uebel, E.C., Tromley, N.J., Jurd, L., and Freedman, B. (1981)
USDA, ESA Tech. Bull. 1641, 1–13.
(9) Warthen, J.D. Jr., Uebel, E.C., Dutky, S.R., Lusby, W.R., and Finigold, H. (1978) USDA, SEA, ARS
Northeastern Series 2, 1–11.
(10) Govindachari, T., Narasimhan, N.S., Suresh, G., Partho, P.D., and Gopalakrishnan, G. (1996) J. Chem. Ecol.,
22, 1453.

© 2005 by CRC Press LLC


838 Opender Koul

SALANNOL C32H44O8
(556.70)
M.p. : 208°

O [α]20
D : +108.7° (CHCl3)
O

O O
O

O
HO
H
O

(1, 2) (1, 2)

SOURCE: Azadirachta indica A. Juss., neem (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Epilachna varivestis Muls. Leaf disk 0.05% Activity comparable Treatment to 4th
(Mexican bean beetle) choice test to azadirachtin stadium larvae for up
to 24 h.

No quantitative data
reported.
(1)

10 ppm Feeding inhibition = Concentration = EC50


50% value.
(3)

(1) Kraus, W., Baumann, S., Bokel, M., Keller, U., Klenk, A., Klingele, M., Pohnl, H., and Schwinger, M. (1987)
In H. Schmutterer and K.R.S. Ascher (eds.), Proc. 3rd Int. Neem Conf., Nairobi, Kenya, GTZ, Eschborn,
Germany, pp. 111–125.
(2) Kraus, W. and Cramer, R. (1981) Liebigs Ann. Chem., 2381.
(3) Kraus, W., Bokel, M., Schwinger, M., Vogler, B., Soellner, R., Wendisch, D., Steffens, R., and Wachendorff,
U. (1993) In T. van Beek and H. Breteler (eds.), Phytochemistry and Agriculture, Oxford University Press,
pp. 18–39.

© 2005 by CRC Press LLC


Insect Antifeedants 839

SALANNOL ACETATE C34H46O9


(598.73)
Gummy material

[α]D : +118° (CHCl3)


O
O

O O
O

O
AcO
H
O

(1, 2) (1, 2)

SOURCE: Azadirachta indica A. Juss., neem (Meliaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Epilachna varivestis Muls. Leaf disk 0.00085% Feeding inhibition = 1. Treatment to 4th
(Mexican bean beetle) choice test 50.0% stadium larvae for up
to 24 h.

Data calculated from


Reference 2.

EC50 = 9 ppm
(2)

2. Popillia japonica Newman Leaf disk 260 ppm Feeding inhibition = 2. Treatment to
(Japanese beetle) choice test 50.0% larvae.

Concentration = EC50
value.
(3)

(1) Rajatkar, S.R., Bhat, V.S., Kulkarni, M.M., Joshi, V.S., and Nagasampagi, B.A. (1989) Phytochemistry, 28, 203.
(2) Champagne, D.E., Koul, O., Isman, M.B., Scudder, G.G.E., and Towers, G.H.N. (1992) Phytochemistry, 31,
377.
(3) Kraus, W. (2002) In H. Schmutterer (ed.), The Neem Tree, 2nd edition, Neem Foundation, Mumbai, India,
pp. 39–111.

© 2005 by CRC Press LLC


840 Opender Koul

SALANNOLACTAM–I C34H45O9N
(611.73)
M.p. : 213°

O [α]20
D : 121.8° (CH2Cl2)
O

O NH
O

H
O

O
AcO
H
O

(1) (1)

SOURCE: Azadirachta indica A. Juss., neem (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Epilachna varivestis Muls. Leaf disk 0.01% Activity better than Treatment to 4th
(Mexican bean beetle) choice test salannins stadium larvae for up
to 24 h.

Activity refers to No quantitative data


about 95% inhibition reported.
(2)

(1) Kraus, W., Klenk, A., Bokel, M., and Vogler, B. (1987) Liebigs Ann. Chem., 337.
(2) Kraus, W., Baumann, S., Bokel, M., Keller, U., Klenk, A., Klingele, M., Pohnl, H., and Schwinger, M. (1987)
In H. Schmutterer and K.R.S. Ascher (eds.), Proc. 3rd Int. Neem Conf., Nairobi, Kenya, GTZ, Eschborn,
Germany, pp. 111–125.

© 2005 by CRC Press LLC


Insect Antifeedants 841

SALANNOLACTAM–II C34H45O9N
(611.73)
[α]20
D : 126.3° (CH2Cl2)

O
O
O

O NH
O

O
AcO
H
O

(1) (1)

SOURCE: Azadirachta indica A. Juss., neem (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Epilachna varivestis Muls. Leaf disk 0.01% Activity better than Treatment to 4th
(Mexican bean beetle) choice test salannins. stadium larvae for up
to 24 h.

Activity refers to No quantitative data


about 95% inhibition reported.
(2)

(1) Kraus, W., Klenk, A., Bokel, M., and Vogler, B. (1987) Liebigs Ann. Chem., 337.
(2) Kraus, W., Baumann, S., Bokel, M., Keller, U., Klenk, A., Klingele, M., Pohnl, H., and Schwinger, M. (1987)
In H. Schmutterer and K.R.S. Ascher (eds.), Proc. 3rd Int. Neem Conf., Nairobi, Kenya, GTZ, Eschborn,
Germany, pp. 111–125.

© 2005 by CRC Press LLC


842 Opender Koul

SALONITENOLIDE C15H20O4
(264.32)
M.p. : 136°

[α]20
D : 199.4° (MeOH)

OH

CH2

O
CH2OH
O

(1, 2) (1, 2)

SOURCE: Centaurea salonitana Vis., tumbleweed (Asteraceae) (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius (L.) Wafer disk 8 mg/cm3 Feeding deterrence 1. Treatment given to
(Grain weevil) test coefficient = 51–100 adults.

2. Tribolium confusum Duv. Wafer disk 8 mg/cm3 Feeding deterrence 2. Treatment given to
(Confused flour beetle) test coefficient: both adults and
Adults = 51–100 larvae.
Larvae = 51–100

3. Trogoderma granarium Wafer disk 8 mg/cm3 Feeding deterrence 3. Treatment given to


Everts test coefficient = larvae.
(Khapra beetle) 101–150
Neutral value = 0
Absolute feeding
deterrence value =
200
(3)

(1) Suchy, M., Samek, Z., Herout, V., and Sorm, F. (1967) Collect. Czeck. Chem. Commun., 32, 2016.
(2) Yoshioka, H., Renold, W., and Mabry, T.J. (1970) Chem. Commun., 148.
(3) Nawrot, J., Bloszyk, E., Grabarczyk, H., and Drozdz, B. (1982) Prace. Nauk. Inst., Ochr. Roslin, 24, 27.

© 2005 by CRC Press LLC


Insect Antifeedants 843

SAMADERINE–B C19H22O7
(362.38)
M.p. : 235–240°

[α]D : +67.5° (pyridine)


O

HO
HO
O O

O
H

(1, 2) (1)

SOURCE: Samadera indica Gaertn., niepa bark tree (Simaroubaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Heliothis virescens (Fab.) Leaf disk 19.8 µg/cm2 Feeding deterrence = Treatment to 3rd
(Tobacco budworm) choice test 60–90% after 2 days instar larvae.
and 30–60% after 6 (2)
days of treatment

12.0 µg/cm2 Feeding deterrence =


60–90% after 2 days
and 0–30% after 6
days of treatment

(1) Zylber, J. and Polonsky, J. (1964) Bull. Soc. Chim. Fr., 2016.
(2) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y.M., Kiyokawa, H., and Lee, K.H.
(1987) J. Nat. Prod., 50, 442.

© 2005 by CRC Press LLC


844 Opender Koul

SANDARACOPIMARIC ACID C20H30O2


(302.46)
M.p. : 171–173°
(softens at 163°)

[α]D : –20° (CHCl3)

CH2

COOH

(1, 2) (1)

SOURCE: Cryptomeria japonica D. Don., Japanese cedar (Taxodiaceae), also isolated from Pinus,
Juniperus, Cupressus, and Calltris spp. (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Schizaphis graminum (Rondani) Artificial diet 0.1% Feeding deterrence = Treatment to aphids
(Wheat aphid) feeding 50.0% at random.
(2)

(1) Bohlmann, F. and le Van, N. (1976) Chem. Ber., 109, 1446.


(2) Rose, A.F., Jones, K.C., Halden, W.F., and Dreyer, D.L. (1981) Phytochemistry, 20, 2249.

© 2005 by CRC Press LLC


Insect Antifeedants 845

SANDORICIN C31H40O11
(588.65)
M.p. : 215–217°
O

O O

O
O

O
O

CH2 OH
O

COOCH3

(1) (1)

SOURCE: Sandoricum koetjape (Burm. F.) Merr., santol (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera frugiperda Artificial diet 25 ppm Feeding deterrence = 1. Treatment to


(J.E. Smith) dual-choice 57.0% newly hatched larvae
(Fall armyworm) assay for 16–20 h.

2. Ostrinia nubilalis (Hubner) Artificial diet 200 ppm Feeding deterrence = 2. Treatment to
(European corn borer) dual-choice 66.0% newly hatched larvae
assay for 16–20 h.

Data calculated from


Reference 1.
(1)

(1) Powell, R.G., Mikolajczak, K.L., Zilkowski, B.W., Mantus, E.K., Cherry, D., and Clardy, J. (1991) J. Nat.
Prod., 54, 241.

© 2005 by CRC Press LLC


846 Opender Koul

SANTONIN C15H18O3
(246.31)
M.p. : 174–176°

[α]18
D : –173° (EtOH)

O
O

(1, 2) (1)

SOURCE: Product of British drug houses (2)


Helianthus annuus L., sunflower (Asteraceae) (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius (L.) Wafer 8 mg/cm3 Feeding deterrence 1. Treatment given to


(Grain weevil) disk test coefficient = 51–100 adults.

2. Tribolium confusum Duv. Wafer 8 mg/cm3 Feeding deterrence 2. Treatment given to


(Confused flour beetle) disk test coefficient: both adults and
Adults = 51–100 larvae.
Larvae = 51–100

3. Trogoderma granarium Wafer 8 mg/cm3 Feeding deterrence 3. Treatment given to


Everts disk test coefficient = larvae.
(Khapra beetle) 101–150 Neutral value = 0
Absolute feeding
deterrence value =
200
(2)

4. Diabrotica virgifera virgifera Leaf disk 40 µg/1.5 cm2 Feeding deterrence = 4. Treatment to
LeConte choice 79.0% adults for 5 h.
(Western corn rootworm) test (3)

LD50 (mice): 900 mg/kg (oral) (4)

(1) Clemo, G.R. and Haworth, R.D. (1930) J. Chem. Soc., 2579.
(2) Nawrot, J., Bloszyk, E., Grabarczyk, H., and Drozdz, B. (1982) Prace. Nauk. Inst., Ochr. Roslin, 24, 27.
(3) Mullin, C.A., Mason, C.H., Chou, J., and Linderman, J.R. (1992) In C.A. Mullin and J.G. Scott (eds.),
Molecular Mechanism of Insecticidal Resistance: Diversity Among Insects, ACS Symp. Ser. 505, Washington,
D.C., pp. 288–308.
(4) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC


Insect Antifeedants 847

8-β-SARRACINOYLOXYCUMAMBRANOLIDE C20H26O6
(362.42)
M.p. : 129–130°

OH
OH

O
CH2
O

(1, 2) (1)

SOURCE: Helianthus maximillani Schrader, perennial sunflower (Asteraceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera eridania Leaf coating 1.0% Feeding deterrence = 1. Treatment to


(Cramer) 44.0% starved 5th instar
(Southern armyworm) larvae.

Data calculated from


Reference 2.
(2)

2. Melanoplus sanguinipes Filter disk 0.25% per 0.30 ± 0.46 cm2 of 2. Treatment to
(Fab.) test dry weight control disk eaten in starved grasshoppers
(Migratory grasshopper) of disk excess of test disk for 48 h.
(2)
2.5% per 1.19 ± 0.99 cm2 of
dry weight control disk eaten in
of disk excess of test disk

(1) Gershenzon, J. and Mabry, T.J. (1984) Phytochemistry, 23, 1959.


(2) Gershenzon, J., Rossiter, M., Mabry, T.J., Rogers, C.E., Blust, M.H., and Hopkins, T.L. (1985) ACS Symp.
Ser. 276, 433.

© 2005 by CRC Press LLC


848 Opender Koul

SCABEQUINONE C15H16O4
(260.29)
M.p. : 108–110°

O O

(1) (1)

SOURCE: Cyperus nipponicus, C. distans L., sedge (Cyperaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insectt Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk 2.6 × 10–9 Feeding inhibition = Treatment to 3rd
(Tobacco armyworm) assay mol/cm2 50.0% instar larvae up to
5 h.

Concentration = EC50
value.
(1)

(1) Morimoto, M., Fujii, Y., and Komai, K. (1999) Phytochemistry, 51, 605.

© 2005 by CRC Press LLC


Insect Antifeedants 849

SCHKUHRIN–I C22H28O8
(420.46)
M.p. : 59–61°

[α]D : –121° (CHCl3)


O

O
O

CH2
OH

(1) (1, 2)

SOURCE: Schkuhria pinnata (Lam.) O. Kuntze canchalagua (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insectt Efficacy Remarks
Method Dose

1. Spodoptera exempta (Walker) Leaf disk Absolute feeding Treatment given to


(Nutgrass armyworm) test deterrence larvae.

2. Epilachna varivestis Muls. Leaf disk Absolute feeding No quantitative data


(Mexican bean beetle) test deterrence recorded.
(1)

(1) Pettei, M.J., Miura, I., Kubo, I., and Nakanishi, K. (1978) Heterocycles, 11, 471.
(2) Dictionary of Natural Products (1994) Chapman & Hall, London.

© 2005 by CRC Press LLC


850 Opender Koul

SCHKUHRIN–II C25H34O9
(478.54)
M.p. : 65–66°

OC H

AcO
CH2OH
O CH2OH
CH2

(1) (1)

SOURCE: Schkuhria pinnata (Lam.) O. Kuntze, canchalagua (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera exempta (Walker) Leaf disk Absolute feeding Treatment given to


(Nutgrass armyworm) test deterrence larvae.

2. Epilachna varivestis Muls. Leaf disk Absolute feeding No quantitative data


(Mexican bean beetle) test deterrence recorded.
(1)

(1) Pettei, M.J., Miura, I., Kubo, I., and Nakanishi, K. (1978) Heterocycles, 11, 471.

© 2005 by CRC Press LLC


Insect Antifeedants 851

SCHKUHRIOLIDE C15H18O4
(262.31)
M.p. : 155–157°

[α]20
D : + 84.6° (MeOH)
O
O
OH
OC H

O
CH2OH
O CH2OH
H
CH2

(1, 2)
(1)

SOURCE: Schkuhria schkuhrioides (Link et Otto) Thell., mountain weed (Asteraceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insectt Efficacy Remarks
Method Dose

1. Sitophilus granarius (L.) Wafer disk 10 mg/cm3 Feeding deterrence 1. Treatment given to
(Grain weevil) test coefficient = 99.5 adults.

2. Tribolium confusum Duv. Wafer disk 10 mg/cm3 Feeding deterrence 2. Treatment given to
(Confused flour beetle) test coefficient: both adults and
Adults = 88.6 larvae.
Larvae = 98.0

3. Trogoderma granarium Wafer disk 10 mg/cm3 Feeding deterrence 3. Treatment given to


Everts test coefficient = 98.9 larvae.
(Khapra beetle)
Neutral value = 0
Absolute feeding
deterrence value =
200
(3)

(1) Samek, Z., Holub, M., Bloszyk, E., and Drozdz, B. (1979) Z. Chem., 19, 449.
(2) Nawrot, J., Bloszyk, E., Grabarczyk, H., Drozdz, B., Daniewski, W.M., and Holub, M. (1983) Prace. Nauk.
Inst., Ochr. Roslin, 25, 91

© 2005 by CRC Press LLC


852 Opender Koul

SCUTALBIN–C C22H32O8
(424.49)
M.p. : 133–138°
OH
[α]20
D : –6.8° (MeOH)
O

O
OAc
OH (1, 2) (2)

SOURCE: Scutellaria rubicunda Hornem subsp. Linneana Carnel, skullcap (Labiatae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera littoralis (Boisd.) Glass fiber 100 ppm Feeding inhibition = Treatment to starved
(Egyptian cotton leaf worm) disk choice 32.0% final stadium larvae
test (24–36 h old).
Bioassays terminated
2. Spodoptera frugiperda Glass fiber 100 ppm Feeding inhibition = after the larvae had
(J.E. Smith) disk choice 32.0% eaten approximately
(Fall armyworm) test 50% of one of the
disks.
3. Mamestra brassicae (L.) Glass fiber 100 ppm Feeding inhibition = (1)
(Cabbage moth) disk choice 41.0%
test

4. Helicoverpa armigera Glass fiber 100 ppm Feeding inhibition =


(Hubner) disk choice 14.0%
(Gram pod borer) test

5. Pieris brassicae (L.) Glass fiber 100 ppm Feeding inhibition =


(Large white butterfly) disk choice 12.0%
test

(1) Bruno, M., Vassallo, N., and Simmonds, M.S.J. (1999) Phytochemistry, 50, 973.
(2) Bruno, M., Piozzi, F., Rodriguez, B., de la Torre, M.C., Vassallo, N., and Servettaz, O. (1996) Phytochemistry,
42, 1059.

© 2005 by CRC Press LLC


Insect Antifeedants 853

SCUTALPIN–C C27H38O9
(506.59)
M.p. : 156–158°

[α]20
D : +5° (CHCl3)

O
HO

O O

O O
O
OH
O

(1) (1)

SOURCE: Scutellaria alpina javalambrensis Pau. alpine skullcap (Labiatae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera littoralis (Boisd.) Glass fiber 100 ppm Feeding inhibition = Treatment to 24- to
(Egyptian cotton leaf worm) disk choice 96.8% 36-h-old final
test stadium larvae until
50% of the disks
were eaten. Larvae
pre-starved for 4 h.
(2)

(1) De la Torre, M.C., Rodriguez, B., Bruno, M., Malakov, P.Y., Papanov, G.Y., Piozzi, F., and Savona, G. (1993)
Phytochemistry, 34, 1589.
(2) Munoz, D.M., de la Torre, M.C., Rodriguez, B., Simmonds, M.S.J., and Blaney, W.M. (1997) Phytochemistry,
44, 593.

© 2005 by CRC Press LLC


854 Opender Koul

SCUTECYPROL–B C27H38O9
OH (506.59)
Only spectral data given

O
OAc
OCO
(1) (1)

SOURCE: Scutellaria rubicunda Hornem subsp. Linneana Carnel., skullcap (Labiatae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera littoralis (Boisd.) Glass fiber 100 ppm Feeding inhibition = Treatment to starved
(Egyptian cotton leaf worm) disk choice 100.0% final stadium larvae
test (24–36 h old).
Bioassays terminated
2. Spodoptera frugiperda Glass fiber 100 ppm Feeding inhibition = after the larvae had
(J.E. Smith) disk choice 85.0% eaten approximately
(Fall armyworm) test 50% of one of the
disks.
3. Mamestra brassicae (L.) Glass fiber 100 ppm Feeding inhibition = (1)
(Cabbage moth) disk choice 86.0%
test

4. Helicoverpa armigera Glass fiber 100 ppm Feeding inhibition =


(Hubner) disk choice 65.0%
(Gram pod borer) test

5. Pieris brassicae (L.) Glass fiber 100 ppm Feeding inhibition =


(Large white butterfly) disk choice 75.0%
test

(1) Bruno, M., Vassallo, N., and Simmonds, M.S.J. (1999) Phytochemistry, 50, 973.

© 2005 by CRC Press LLC


Insect Antifeedants 855

SCUTEGALIN–A C32H44O10
(588.69)
M.p. : 105–110°

[α]23
D : +17° (CHCl3)

O O

O
O O

O O

O
O
O
(1)
(1)

SOURCE: Scutellaria galericulata L., blue skullcap (Labiatae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera littoralis (Boisd.) Glass fiber 100 ppm Feeding inhibition = Treatment to 24- to
(Egyptian cotton leaf worm) disk choice 41% 36-h-old final
test stadium larvae until
50% of the disk was
eaten. Larvae pre-
starved for 4 h.
(1)

(1) Rodriguez, B., de la Torre, M.C., Rodriguez, M., Bruno, M., Piozzi, F., Savona, G., Simmonds, M.S.J., Blaney,
W.M., and Perales, A. (1993) Phytochemistry, 33, 309.

© 2005 by CRC Press LLC


856 Opender Koul

SENECIOIC ACID C5H8O2


(100.12)
M.p. : 70°

B.p. : 199°

COOH

(1) (1)

SOURCE: Alchornea triplinervia (Spreng.) Muell. Arg., tapia (Asteraceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Anthonomus grandis Bohem. Artificial 10 mg/4 cm2 Feeding deterrence = Treatment given to
(Boll weevil) diet 15% freshly emerged boll
feeding weevils. Ratio value
15 mg/4 cm2 Feeding deterrence = of 0 represents
17% absolute antifeedant
effect and >100 =
40 mg/4 cm2 Feeding deterrence = attraction.
2% (2)

LD50 (rats): 3560 mg/kg (oral) (3)

(1) Dictionary of Organic Compounds (1994) Chapman & Hall, London.


(2) Miles, D.H., Hankinson, B.L., and Randle, S.A. (1985) Proc. ACS Symp. Ser., 276, 469.
(3) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC


Insect Antifeedants 857

SENECIONINE C18H25O5N
(335.40)
M.p. : 232–233°

[α]D : –54.6° (CHCl3)


H

C
C H2C C
C C O
H
OH
O C O
H
O CH2

(1, 2) (1, 2)

SOURCE: Senecio anonymous, groundsel (Asteraceae) (3)


Senecio triangularis, groundsel (Asteraceae) (4)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Choristoneura fumiferana Paper 1.6 × 103 M Feeding deterrence = 1. Treatment to 6th


(Clemens) penicillin 36.0% instar larvae.
(Spruce budworm) disk assay (3)

2. Acyrthosiphon pisum (Harris) Artificial 0.17 ± 0.05% Feeding deterrence = 2. Treatment to


(Pea aphid) diet 50.0% aphids at random.
feeding (4)

LD50 (rats): 85.0 mg/kg (ipr.) (5)

(1) Manske, R.H.F. (1931) Can. J. Res., 5, 651.


(2) Manske, R.H.F. (1939) Can. J. Res., 17B, 1.
(3) Bentley, M.D., Leonard, D.E., Stoddard, W.F., and Zalkow, L.H. (1984) An. Entomol. Soc. Am., 77, 393.
(4) Dreyer, D.L., Jones, K.C., and Molyneux, R.J. (1985) J. Chem. Ecol., 11, 1045.
(5) Cordell, G.A. (1981) Introduction to Alkaloids, John Wiley & Sons, New York, p. 134.

© 2005 by CRC Press LLC


858 Opender Koul

6α-SENECIOYLOXY CHAPARRINONE C25H32O9


(structure under review) (476.52)
M.p. : 255–257°

OH [α]25
D : +213° (pyridine)

HO
HO
O

O O
H H
OOC

(1, 2)
(1)

SOURCE: Simaba multiflora A. Juss., cajurana (Simaroubaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Heliothis virescens (Fab.) Leaf disk 15 µg/cm2 Feeding deterrence = 1. Treatment to 3rd
(Tobacco budworm) choice test 95.0% instar larvae.

Concentration = 95%
protection
concentration.
(2)

2. Spodoptera frugiperda Leaf disk 8 µg/cm2 Feeding deterrence = 2. Treatment to 3rd


(J. E. Smith) choice test 95.0% instar larvae.
(Fall armyworm)
Concentration = 95%
protection
concentration.
(2)

(1) Arisawa, M., Kinghorn, A.D., Cordell, G.A., and Farnsworth, N.R. (1983) J. Nat. Prod., 46, 218.
(2) Klocke, J.A., Arisawa, M., Handa, S.S., Kinghorn, A.D., Cordell, G.A., and Farnsworth, N.R. (1985) Expe-
rientia, 41, 7.

© 2005 by CRC Press LLC


Insect Antifeedants 859

SENECIPHYLLINE C18H23O5N
(333.38)
M.p. : 217–218° (dec.)

OH [α]17
D : –139° (CHCl3)

CH2 O
O O H

(1, 2) (1)

SOURCE: Senecio douglasii var. longilobus, groundsel (Asteraceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Acyrthosiphon pisum (Harris) Artificial 0.04 ± 0.006% Feeding deterrence = Treatment to aphids
(Pea aphid) diet 50.0% at random.
feeding
Concentration = EC50
value.
(2)

LD50 (rats): 77.0 mg/kg (ipr.) (3)

(1) Bradbury, R.B. and Culvenor, C.C.J. (1954) Aust. J. Chem., 7, 378.
(2) Dreyer, D.L., Jones, K.C., and Molyneux, R.J. (1985) J. Chem. Ecol., 11, 1045.
(3) Mattocks, A.R. (1986) Chemistry and Toxicology of Pyrrolizidine Alkaloids, Academic Press, New York.

© 2005 by CRC Press LLC


860 Opender Koul

SENKIRKINE C19H27O6N
(365.43)
M.p. : 196.5–197.5°
H
[α]25
D : –16° (MeOH)
C
H2C C
C
C C O
H
OH
O C O
O
O CH2

(1, 2) (1)

SOURCE: Tussilago farfara L., colts foot (Asteraceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Choristoneura fumiferana Paper 0.2 × 103 M Feeding deterrence = Treatment to 6th


(Clemens) penicillin 44.0% instar larvae.
(Spruce budworm) disk assay (2)

1.0 × 103 M Feeding deterrence = FI50 = 0.31 × 103 M


68.0%
Calculated from
5.0 × 103 M Feeding deterrence = Reference 2.
89.0%

LD50 (rats): 220 mg/kg (ipr.) (3)

(1) Briggs, L.H., Cambie, R.C., Candy, B.J., Donovan, G.M., Russel, R.H., and Sedye, R.N. (1965) J. Chem.
Soc., 2492.
(2) Bentley, M.D., Leonard, D.E., Stoddard, W.F., and Zalkow, L.H. (1984) An. Entomol. Soc. Am., 77, 393.
(3) Mattocks, A.R. (1986) Chemistry and Toxicology of Pyrrolizidine Alkaloids, Academic Press, New York.

© 2005 by CRC Press LLC


Insect Antifeedants 861

SERGEOLIDE C25H28O11
(504.49)
M.p. : 202–206°

[α]22
D : –103.3° (MeOH)
OH

HO COOCH3
O
OCOCH3
O
O
H
O O
H

(1, 2) (1)

SOURCE: Picrolemma pseudocoffea Ducke (Simaroubaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Heliothis virescens (Fab.) Leaf disk 12.0 µg/cm2 Feeding deterrence = Treatment to 3rd
(Tobacco budworm) choice test 90–100% after 6 instar larvae.
days of treatment (2)

6.0 µg/cm2 Feeding deterrence =


90–100% after
2 days and 60–90%
after 6 days of
treatment

3.0 µg/cm2 Feeding deterrence =


90–100% after
2 days and 30–60%
after 6 days of
treatment

(1) Moretti, C., Polonsky, J., Vuilhorgne, M., and Prange, T. (1982) Tetrahedron Lett., 23, 647.
(2) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y.M., Kiyokawa, H., and Lee, K.H.
(1987) J. Nat. Prod., 50, 442.

© 2005 by CRC Press LLC


862 Opender Koul

SEVERINOLIDE C31H38O11
(586.63)
M.p. : 219–221°
O
[α]D : +53.08° (CHCl3)
O
OCH3

O
O O

OAc

OAc

(1) (1)

SOURCE: Severinia buxifolia (Poir.) Tenore., Chinese box orange (Rutaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Plutella xylostella (L.) Leaf disk 0.0625% Feeding deterrence = Treatment to 3rd
(Diamondback moth) choice test 50.0% instar larvae.

Concentration = EC50
value.
(1)

(1) Wu, T.S., Leu, Y.L., Chan, Y.Y., Wu, P.L., Kuoh, C.S., Wu, S.J., and Wang, Y. (1997) Phytochemistry, 45, 1393.

© 2005 by CRC Press LLC


Insect Antifeedants 863

SHIROMODIOL DIACETATE C19H30O5


(338.44)
M.p. : 109–112°

[α]25
D : –61.9° (CHCl3)

OCOCH3

O
OCOCH3

(1, 2) (2)

SOURCE: Parabenzoin trilobum Nakai, Japanese shiromoji (Lauraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera littoralis (Boisd.) Leaf disk 0.5% Feeding deterrence = 1. Treatment to 3rd
(Egyptian cotton leaf worm) choice test 94.0% instar larvae.

0.25% Feeding deterrence = Data calculated from


86.0% Reference 1.
(1)

2. Trimeresia miranda Butler Leaf disk 0.25% Feeding deterrence = 2. Treatment to 3rd
(Borneo moth) choice test 100% instar larvae.

0.03% Feeding deterrence = Data calculated from


70.0% Reference 1.
(1)

(1) Wada, K., Matsui, K., Enomoto, Y., Ogiso, O., and Munakata, K. (1970) Agric. Biol. Chem., 34, 941.
(2) Wada, K., Enomoto, Y., and Munakata, K. (1970) Agric. Biol. Chem., 34, 946.

© 2005 by CRC Press LLC


864 Opender Koul

SHIROMODIOL MONOACETATE C17H28O4


(296.41)
M.p. : 78–80°

[α]25
D : –44.8° (CHCl3)

OCOCH3

O
OH

(1, 2) (2)

SOURCE: Parabenzoin trilobum Nakai, Japanese shiromoji (Lauraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera littoralis (Boisd.) Leaf disk 0.5% Feeding deterrence = 1. Treatment to 3rd
(Egyptian cotton leaf worm) choice test 100% instar larvae.

0.25% Feeding deterrence = Data calculated from


70.0% Reference 1.
(1)

2. Trimeresia miranda Butler Leaf disk 0.25% Feeding deterrence = 2. Treatment to 3rd
(Borneo moth) choice test Approx. 70.0% instar larvae.

Data calculated from


Reference 1.
(1)

(1) Wada, K., Matsui, K., Enomoto, Y., Ogiso, O., and Munakata, K. (1970) Agric. Biol. Chem., 34, 941.
(2) Wada, K., Enomoto, Y., and Munakata, K. (1970) Agric. Biol. Chem., 34, 946.

© 2005 by CRC Press LLC


Insect Antifeedants 865

SHIROMOOL C15H26O2
(238.37)
M.p. : 72–73°

[α]25
D : +85.5° (CHCl3)

O
OH

(1, 2) (2)

SOURCE: Parabenzoin trilobum Nakai, Japanese shiromoji (Lauraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera littoralis (Boisd.) Leaf disk 0.5% Feeding deterrence = Treatment to 3rd
(Egyptian cotton leaf worm) choice test 97.0% instar larvae.

0.25% Feeding deterrence = Data calculated from


44.0% Reference 1.
(1)

(1) Wada, K., Matsui, K., Enomoto, Y., Ogiso, O., and Munakata, K. (1970) Agric. Biol. Chem., 34, 941.
(2) Wada, K., Enomoto, Y., and Munakata, K. (1970) Agric. Biol. Chem., 34, 946.

© 2005 by CRC Press LLC


866 Opender Koul

SHOREIC ACID C30H50O4


(474.72)
H M.p. : 92–94°
OH
[α]D : +40° (Me ester)

HOOC

H2C

(1, 2) (1, 3)

SOURCE: Dysoxylum malabaricum Bedd. and ex C.DC. white cidar (Meliaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk 1.0 µg/cm2 Feeding deterrence = Treatment to 3rd
(Tobacco armyworm) dual- 51.8% instar larvae for 24 h.
choice test
5.0 µg/cm2 Feeding deterrence = EC50 = 0.76 µg/cm2
55.8%
Data calculated from
10.0 µg/cm2 Feeding deterrence = Reference 2.
74.6% (2)

50.0 µg/cm2 Feeding deterrence =


75.5%

(1) Govindachari, T.R., Suresh, G., and Krishna Kumari, G.N. (1994) Phytochemistry, 37, 1127.
(2) Govindachari, T.R., Narasimhan, N.S., Suresh, G., Partho, P.D., Gopalakrishnan, G., and Krishna Kumari,
G.N. (1995) J. Chem. Ecol., 21, 1586.
(3) Lantz, J.-P. (1968) Bull. Soc. Chim. Fr., 2131

© 2005 by CRC Press LLC


Insect Antifeedants 867

SIDEROXOL C20H32O3
(320.47)
M.p. : 245–246°

OH

OH

(1, 2) (1, 2)

SOURCE: Sideritis akmanii L., iron-wort, also from S. niveotomentosa, S. rubiflora (Labiatae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera littoralis (Boisd.) Glass fiber 100 ppm Feeding deterrence = Treatment to final
(Tobacco armyworm) disk test 50% instar larvae.
(2)
2. Spodoptera frugiperda Glass fiber 100 ppm Feeding deterrence =
(J.E. Smith) disk test 50%
(Fall armyworm)

(1) Piozzi, F., Venturella, P., Bellino, A.C., and Mendelli, R. (1968) Ric. Sci., 38, 462.
(2) Bondi, M.L., Bruno, M., Piozzi, F., Husnu, K., Baser, C., and Simmonds, M.S.J. (2000) Biochem. Syst. Ecol.,
28, 299.

© 2005 by CRC Press LLC


868 Opender Koul

SILPHINEN-3,5-DIONE C15H20O2
(232.15)
Oil

Only spectral data given

O O

(1) (1)

SOURCE: Senecio palmensis Chr.Sm., groundsel (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera littoralis (Boisd.) Choice >100 nmol/cm2 Feeding deterrence = 1. Treatment to 6th
(Egyptian cotton leaf worm) feeding 50.0% instar larvae.
assay

2. Leptinotarsa decemlineata Choice 4.82 nmol/cm2 Feeding deterrence = 2. Treatment to


(Say) feeding 50.0% adults.
(Colorado potato beetle) assay

3. Myzus persicae (Sulzer) Choice >200 nmol/cm2 Feeding deterrence = 3. Treatment to


(Green peach aphid) feeding 50.0% apterous adult
assay aphids.

4. Rhopalosiphum padi (L.) Choice >150 nmol/cm2 Feeding deterrence = 4. Treatment to


(Cereal aphid) feeding 50.0% apterous adult
assay aphids.

5. Sitobion avenae (Fab.) Choice >200 nmol/cm2 Feeding deterrence = 5. Treatment to


(Grass aphid) feeding 50.0% apterous adult
assay aphids.

6. Diuraphis noxia (Mordvilko) Choice 25.6 nmol/cm2 Feeding deterrence = 6. Treatment to


(Wheat aphid) feeding 50.0% apterous adult
assay aphids.

Concentrations =
EC50 value.
(1)

(1) Reina, M., Nold, M., Santana, O., Orihuela, J.C., and Gonzalez-Coloma, A. (2002) J. Nat. Prod., 65, 448.

© 2005 by CRC Press LLC


Insect Antifeedants 869

SILPHINEN-3,5,11-TRIONE C15H18O3
(246.13)
Oil

O O

(1) (1)

SOURCE: Semisynthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera littoralis Boisd. Choice 42.4 nmol/cm2 Feeding deterrence = 1. Treatment to 6th
(Egyptian cotton leaf worm) leaf disk 50.0% instar larvae for 24 h.
feeding
assay Concentration = EC50
value.

2. Leptinotarsa decemlineata Choice >100 nmol/cm2 Feeding deterrence = 2. Treatment to


(Say) leaf disk 50.0% adults for 24 h.
(Colorado potato beetle) feeding
assay Concentration = EC50
value.

3. Diuraphis noxia (Mordvilko) Choice >200 nmol/cm2 Feeding deterrence = 3. Treatment to


(Wheat aphid) feeding 50.0% adults for 24 h.
assay
Feeding deterrence = Concentration = EC50
75.5% value.
(1)

(1) Gonzalez-Coloma, A., Valencia, F., Martin, N., Hoffmann, J.J., Hutter, L., Marco, J.A., and Reina, M. (2002)
J. Chem. Ecol., 28, 117.

© 2005 by CRC Press LLC


870 Opender Koul

SILYBIN C25H22O10
(482.44)
M.p. : 167°

[α]20
D : +11° (Me2CO)
OH
O

OH OH

O
HO O OCH3

O CH2OH

(1, 2) (1, 2)

SOURCE: Silybum marrianum (L.) Gaertn., blessed thistle (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Peridroma saucia (Hubner) Leaf disk 28.5 µg/cm2 Feeding deterrence = Treatment to 5th
(Variegated cutworm) choice test 29.3% instar larvae for 5 h.
(2)
57.0 µg/cm2 Feeding deterrence =
58.9%

(1) Pelter, A. and Haensel, R. (1975) Chem. Ber., 108, 790.


(2) Nawrot, J., Koul, O., Isman, M.B., and Harmatha, J. (1991) J. Appl. Ent., 112, 194.

© 2005 by CRC Press LLC


Insect Antifeedants 871

SIMALIKALACTONE–A C22H32O6
(392.49)
M.p. : 278.5°

[α]D : +17° (EtOH)


OCH3

HO
O

H3CO

H
O O

(1, 2) (1, 2)

SOURCE: Picrasma ailanthoides Planchon., quassia (Simaroubaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Heliothis virescens Fab. Leaf disk 19.8 µg/cm2 Feeding deterrence = Treatment to 3rd
(Tobacco budworm) choice test 60–90% after 2 days instar larvae.
and 30–60% after 6 (3)
days of treatment

12.0 µg/cm2 Feeding deterrence =


60–90% after 2 days
and 0–30% after 6
days of treatment

3.0 µg/cm2 Feeding deterrence =


60–90% after 2 days
and 0–30% after 6
days of treatment

(1) Murae, T., Tsuyuki, T., Ikeda, T., Nishihama, T., Masuda, S., and Takahashi, T. (1971) Tetrahedron, 27, 1545.
(2) Tresca, J.-P., Alais, L., and Polonsky, J. (1971) Compt. Rend., 273C, 601.
(3) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y.M., Kiyokawa, H., and Lee, K.H.
(1987) J. Nat. Prod., 50, 442.

© 2005 by CRC Press LLC


872 Opender Koul

SIMALIKALACTONE–D C25H34O9
(478.54)
M.p. : 228–230°

[α]D : +53°
OH

HO
HO
O
O OCO

H
O O

(1, 2) (1)

SOURCE: Quassia africana Baillon, African otapaa (Simaroubaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Epilachna varivestis Muls. Whole leaf 200 ppm Feeding deterrence = 1. Treatment to 4th
(Mexican bean beetle) application 85.5% instar larvae for 24 h.
Larvae pre-starved
for 2 h.

Data calculated from


Reference 2.
(2)

2. Spodoptera eridania Whole leaf 200 ppm Feeding deterrence = 2. Treatment to 5th
(Cramer) application 89.2% instar larvae for 24 h.
(Southern armyworm) Larvae pre-starved
for 2 h.

Data calculated from


Reference 2.
(2)

(1) Tresca, J.-P., Alais, L., and Polonsky, J. (1971) Compt. Rend., 273C, 601.
(2) Leskinen, V., Polonsky, J., and Bhatnagar, S. (1984) J. Chem. Ecol., 10, 1497.

© 2005 by CRC Press LLC


Insect Antifeedants 873

SIMAROLIDE C27H36O9
(504.58)
M.p. : 264–270°

[α]D : +73.6° (CHCl3)


O

H3CCOO
O
O
HO

H O
O O

(1, 2) (1, 2)

SOURCE: Simarouba amara Aubl., bitter damson (Simaroubaceae) (1,3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Heliothis virescens (Fab.) Leaf disk 19.8 µg/cm2 Feeding deterrence = 1. Treatment to 3rd
(Tobacco budworm) choice test 30–60% after 2 days instar larvae.
and 0–30% after 6 (3)
days of treatment

2. Epilachna varivestis Muls. Whole leaf 500 ppm Feeding deterrence = 2. Treatment to 4th
(Mexican bean beetle) application 83.3% instar larvae for 24 h.
Larvae pre-starved
for 2 h.

Data calculated from


Reference 4.
(4)

(1) Polonsky, J. (1959) Bull. Soc. Chim. Fr., 1546.


(2) Polonsky, J. (1964) Proc. Chem. Soc., 292.
(3) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y.M., Kiyokawa, H., and Lee, K.H.
(1987) J. Nat. Prod., 50, 442.
(4) Leskinen, V., Polonsky, J., and Bhatnagar, S. (1984) J. Chem. Ecol., 10, 1497.

© 2005 by CRC Press LLC


874 Opender Koul

SINAPIC ACID C11H12O5


(224.21)
M.p. : 192°

COOH

H3CO OCH3

OH

(1, 2, 3) (1, 2)

SOURCE: Commercial sample (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Pieris brassicae (L.) Leaf disk 4.4 × 10–2 M Feeding deterrence Treatment to 2nd day
(Large white butterfly) no-choice test ratio = 2.36 5th instar unstarved
larvae.

Ratio between 0 and


20 effective
deterrence.
(3)

(1) Spath, E. (1920) Monatsh. Chem., 41, 271.


(2) Bate-Smith, E.C. (1956) Sci. Proc. R. Dublin Soc., 27, 165.
(3) Jones, C.G. and Firn, R.D. (1979) Biochem. Syst. Ecol., 7, 187.

© 2005 by CRC Press LLC


Insect Antifeedants 875

SINIGRIN C10H17O9NS2
(359.38)
No physical data given
O O
M.p. : 125–127°
S (for potassium salt)
OH
O
N

HO
O
OH
HO

OH (1, 2) (1, 2)

SOURCE: Commercial sample (3)


Present in many crucifers (major glucosinolate in Brassica oleracea L., Brassicaceae)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Locusta migratoria (L.) Wafer disk 0.05% dry Feeding deterrence = Treatment to 3-day-
(Migratory locust) choice test weight 50% old 5th instar nymphs
for 3–4 h.
(3)

(1) Benn, M.H. and Ettlinger, M.G. (1965) Chem. Commun., 445.
(2) Matsuo, M. (1968) Tetrahedron Lett., 4101.
(3) Bernays, E.A. and Chapman, R.F. (1977) Ecol. Entomol., 2, 1.

© 2005 by CRC Press LLC


876 Opender Koul

SOLANIDINE C27H43ON
(397.65)
M.p. : 218–219°

[α]21
D : –29° (CHCl3)

HO

(1, 2) (1)

SOURCE: Synthetic (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Choristoneura fumiferana Paper 10–3 M Feeding deterrence = Treatment to 6th


(Clemens) penicillin 94.0% instar larvae.
(Spruce budworm) disk assay (2)

10–4 M Feeding deterrence =


74.0%

(1) Reichstein, T. and Reich, H. (1946) Ann. Rev. Biochem., 15, 155.
(2) Bentley, M.D., Leonard, D.E., and Bushway, R.J. (1984) Ann. Entomol. Soc. Am., 77, 401.

© 2005 by CRC Press LLC


Insect Antifeedants 877

α-SOLANINE C45H73O15N
(868.07)
M.p. : 285° (dec.)

[α]20
D : –60° (pyridine)

Rham-glu-gal-O

(1, 2) (1)

SOURCE: Solanum species (Solanaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Choristoneura fumiferana Paper 10–3 M Feeding deterrence = 1. Treatment to 6th


(Clemens) penicillin 59.0% instar larvae.
(Spruce budworm) disk assay (2)

2. Leptinotarsa decemlineata Sensillum 0.4% wet Feeding deterrence = 2. Treatment to adult


(Say) response weight 50.0% beetles.
(Colorado potato beetle) recording
Concentration = EC50
value.
(3)

LD50 (mice): 42 mg/kg (i.p.) (3)

(1) Kuhn, R. and Low, I. (1954) Angew. Chem., 66, 639.


(2) Bentley, M.D., Leonard, D.E., and Bushway, R.J. (1984) Ann. Entomol. Soc. Am., 77, 401.
(3) Mitchell, B.K. and Harrison, G.D. (1985) J. Chem. Ecol., 11, 73.

© 2005 by CRC Press LLC


878 Opender Koul

SOULAMEANONE C20H28O8
(396.44)
M.p. : 263–265°

[α]22
D : +101°
OH (MeOH/CHCl3, 2:1)

HO
HO
OH
O OH

O O

(1, 2) (1)

SOURCE: Soulamea muelleri Brongn. & Gris (Simaroubaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Epilachna varivestis Muls. Whole leaf 500 ppm Feeding deterrence = 1. Treatment to 4th
(Mexican bean beetle) application 10.0% instar larvae for 24 h.
Larvae pre-starved
for 2 h.

Data calculated from


Reference 2.
(2)

2. Spodoptera eridania Whole leaf 500 ppm Feeding deterrence = 2. Treatment to 5th
(Cramer) application 50.0% in one case instar larvae for 24 h.
(Southern armyworm) only Larvae pre-starved
for 2 h.

Data calculated from


Reference 2.
(2)

(1) Polensky. J., Tri, M.V., Varon, Z., Prange, T., Pascard, C., Sevenet, T., and Pusset, J. (1980) Tetrahedron, 36,
2983.
(2) Leskinen, V., Polonsky, J., and Bhatnagar, S. (1984) J. Chem. Ecol., 10, 1497.

© 2005 by CRC Press LLC


Insect Antifeedants 879

SOULAMEOLIDE C25H32O8
(460.52)
M.p. : 261–263°

CH2OH [α]22
D : –72.6° (MeOH)

HO O
HO O

O H

H
O O
H

(1, 2) (1)

SOURCE: Soulamea tomentosa Brongn. & Gris (Simaroubaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Heliothis virescens (Fab.) Leaf disk 19.8 µg/cm2 Feeding deterrence = Treatment to 3rd
(Tobacco budworm) choice test 30–60% after 2 days instar larvae.
and 0–30% after 6 (2)
days of treatment

(1) Polonsky, J., Tri, M.V., Prange, T., and Pascard, C. (1979) J. Chem. Soc. Chem. Commun., 641.
(2) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y.M., Kiyokawa, H., and Lee, K.H.
(1987) J. Nat. Prod., 50, 442.

© 2005 by CRC Press LLC


880 Opender Koul

SPARTEINE C15H26N2
(234.39)
B.p. : 173–174°/8 mm

[α]21
D : –16.4° (EtOH)

H
H
N

N
H
H

(1, 2)
(1, 2)

SOURCE: Compound evaluated as a sulphate salt (3)


Lupinus polyphyllus Lindl., lupine (Fabaceae) (4)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Entomoscelis americana Leaf disk 1 mM Feeding deterrence = 1. Treatment to 7- to


Brown dip test 42.9% 20-h-old 4th instar
(Red turnip beetle) 10 mM Feeding deterrence = larvae.
100% (3)

2. Choristoneura fumiferana Paper 2.1 × 103 M Feeding deterrence = 2. Treatment to 6th


(Clemens) penicillin Not active instar larvae.
(Spruce budworm) disk assay (4)

3. Acyrthosiphon pisum (Harris) Artificial 0.00011 ± Feeding deterrence = 3. Treatment to


(Pea aphid) diet feeding 0.00005% 50.0% aphids at random.
(5)

4. Phormia regina (Meigen) Sucrose 10 mM Feeding deterrence = 4. Treatment to 2-,


(Blowfly) solution 91.0% after 6 h 4-, and 6-day-old
feeding adults after 24 h
starvation.
(6)

LD50 (mouse): 26 mg/kg (ivn.) (7)

(1) Clemo, G.R., Leitch, G.C., and Raper, R. (1931) Ber., 64, 1520.
(2) Clemo, G.R., Raper, R., and Short, W.S. (1949) J. Chem. Soc., 663.
(3) Mitchell, B.K. and Sutcliffe, J.F. (1984) Physiol. Entomol., 9, 57.
(4) Bentley, M.D., Leonard, D.E., Reynolds, E.K., Leach, S., Beck, A.B., and Murakoshi, I. (1984) Ann. Entomol.
Soc. Am., 77, 398.
(5) Dreyer, D.L., Jones, K.C., and Molyneux, R.J. (1985) J. Chem. Ecol., 11, 1045.
(6) Blades, D. and Mitchell, B.K. (1986) Entomol. Exp. Appl., 41, 299.
(7) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC


Insect Antifeedants 881

SPECIONIN C20H26O8
(394.42)
Oil

[α]D : –30.7° (CHCl3)

HO COO

OC2H5

O
O

CH2OH OC2H5

(1, 2) (1, 2)

SOURCE: Catalpa speciosa Warder ex Barney, catalpa (Bignoniaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Choristoneura fumiferana Artificial diet 50–100 ppm Feeding deterrence = Treatment to larvae.
(Clemens) feeding 100% (1)
(Spruce budworm)

(1) Chang, C.C. and Nakanishi, K. (1983) J. Chem. Soc. Chem. Commun., 605.
(2) Vander Eycken, E., Bruyn, A. de, vander Eycken, J., Gallant, P., and Vandewalle, M. (1986) Tetrahedron, 19,
5385.

© 2005 by CRC Press LLC


882 Opender Koul

SPECIOSIDE C24H28O12
(508.48)
M.p. : 244–245°
OH
[α]21
D : –203° (MeOH)

OOC
H

O
O
H
HO
O
HO O

HO
OH
OH (1) (1)

SOURCE: Catalpa speciosa Warder ex Barney, catalpa (Bignoniaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Lymantria dispar (L.) Artificial diet 1.0 mg/ml Feeding deterrence = Treatment to 3rd
(Gypsy moth) feeding 27.0% instar larvae.
(1)

(1) El-Naggar, S.F. and Doskotch, R.W. (1980) J. Nat. Prod., 43, 524.

© 2005 by CRC Press LLC


Insect Antifeedants 883

cis – SPIROENOL ETHER C13H12O2


(Mycosinol) (200.23)
M.p. : 48.5–49.5°

[α]D : –45.3° (EtOH)

(1, 2) (1, 2)

SOURCE: Chrysanthemum coronarium L., Japanese chrysanthemum (Asteraceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Bombyx mori (L.) Artificial diet 4 µg/g Feeding deterrence = Treatment to male 5th
(Silkworm) feeding 100% instar larvae.
(2)

(1) Bholmann, F., Arndt, C., Boronowski, H., Keine, K., and Herbst, P. (1964) Chem. Ber., 97, 1179.
(2) Tada, M. and Chiba, K. (1984) Agric. Biol. Chem., 48, 1367.

© 2005 by CRC Press LLC


884 Opender Koul

25 RS-SPIROST-5EN-3β-OL,3-O C51H83O22
[α-L-RHAMNOPYRANOSYL] (1048.20)
M.p. : 276–279° (dec.)
[β-D-GLUCOPYRANOSYL,β-D-GLUCOPYRANOSYL]
O
-13-D-GLUCOPYRANOSIDE

OH

OH OH
O
O O O

OH O
OH
OH
O
OH
O O
OH
HO
OH
HO OH
(1) (1)

SOURCE: Balanites roxburghii Planch, date (Zygophyllaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Diacresia obliqua (Walker) Leaf disk test 500 ppm Feeding deterrence = Treatment to larvae.
(Hairy caterpillar) 68.0% (1)

(1) Jain, D.C. (1987) Phytochemistry, 26, 2223.

© 2005 by CRC Press LLC


Insect Antifeedants 885

STEARIC ACID C18H36O2


(284.48)
M.p. : 69.7°

B.p. : 386°
O OH

(1, 2) (1)

SOURCE: Pinus lambertiana Dougl., sugar pine (Pinaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Incisitermes minor (Hagen) Paper towel 0.25 mg/cm2 Feeding deterrence = Treatment to
(Western drywood termite) disk test 73.9% after 7-day immature termites of
exposure 10–13 mg body
weight.
0.05 mg/cm2 Feeding deterrence = (2)
30.0% after 6-day
exposure

LD50 (rats): 21.5 ± 1.8 mg/kg (i.v.) (3)

(1) Dictionary of Natural Products (1994) Chapman & Hall, London.


(2) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39.
(3) Oro, L. and Wretlind, A. (1961) Acta Pharmacol. Toxicol., 18, 141.

© 2005 by CRC Press LLC


886 Opender Koul

STEMOFOLINE C22H29O5N
(387.46)
M.p. : 87–89°

[α]D : +273° (MeOH)

OCH3

O O
O
O

(1, 2) (2)

SOURCE: Stemona collinsae Craib (Stemonaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Plutella xylostella (L.) Leaf disk test 10 µg/cm2 Feeding deterrence = Treatment to 3rd
(Diamondback moth) 100% instar larvae for
4 days.
(1)

(1) Jiwajinda, S., Hirai, N., Watanabe, K. Santisopasri, V., Chuengsamarnyart, N., Koshimizu, K., and Ohigashi,
H. (2001) Phytochemistry, 56, 693.
(2) Irie, H., Masaki, N., Ohno, K., Osaki, K., Taga, T., and Uyeo, S. (1970) Chem. Commun., 1066.

© 2005 by CRC Press LLC


Insect Antifeedants 887

16,17-DIDEHYDRO-16(E) – STEMOFOLINE C22H27O5N


(385.44)
M.p. : 172–174°

[α]18
D : +230° (MeOH)

OCH3

O O
O
O

(1) (1)

SOURCE: Stemona collinsae Craib (Stemonaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Plutella xylostella (L.) Leaf disk test 2.5 µg/cm2 Feeding deterrence = Treatment to 3rd
(Diamondback moth) 100% instar larvae for
4 days.
(1)

(1) Jiwajinda, S., Hirai, N., Watanabe, K. Santisopasri, V., Chuengsamarnyart, N., Koshimizu, K., and Ohigashi,
H. (2001) Phytochemistry, 56, 693.

© 2005 by CRC Press LLC


888 Opender Koul

STIGMAST-7-EN-3-OL C29H50O
(414.71)
M.p. : 145–146°
(151–151.5°)

[α]30
D : +9.1 (CHCl3)

HO

(1) (1, 2)

SOURCE: Wedelia biflora (L.) DC, sami scandent shrub (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Anthonomus grandis Bohem. Agar plug 1.0 mg/plug Feeding deterrence = Treatment to newly
(Boll weevil) bioassay 30.0% emerged boll weevils
in the dark at 80°F
for 4 h.
Plug size:
Diameter = 1.3 cm
Length = 3.6 cm
(1)

(1) Miles, D.H., Chittawong, V., Payne, A.M., Hedin, P.A., and Kokpol, U. (1990) J. Agric. Food Chem., 38, 1591.
(2) (1994) Dictionary of Natural Products, Chapman & Hall, London.

© 2005 by CRC Press LLC


Insect Antifeedants 889

STIZOLIN C15H20O4
(264.32)
M.p. : 184.5–186.5° (dec.)

[α]20
D : –30.46° (CHCl3)

OH

CH2

O
O
O

(1, 2) (1, 2)

SOURCE: Stizolophus balsamita (Lam.) Cass. ex Takht (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Tribolium confusum Duv. Wafer disk 10 mg/ml Feeding deterrence Treatment to larvae.
(Confused flour beetle) test coefficient = 162 Data on 0–200
greater deterrence
scale.
(2)

(1) Mukhametzhanov, M.N., Shreter, A.I., and Pakalns, D. (1970) Khim. Prir. Soedin., 6, 505, (1971), 7, 405.
(2) Nawrot, J., Harmatha, J., and Bloszyk, E. (1986) In E. Donahaye and S. Navarro (eds.), Proc. 4th Int. Conf.
Stored Product Protection, Tel Aviv, Israel, pp. 591–597.

© 2005 by CRC Press LLC


890 Opender Koul

STRYCHNINE C21H22O2N2
(334.42)
M.p. : 270–271°
(275–285°)

[α]18
D : –139° (CHCl3)

N
H
O
O

(1, 2,3) (1, 2)

SOURCE: Commercial sample (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Phormia regina (Meigen) Sucrose 10 mM Feeding deterrence = 1. Treatment to 2-,


(Blowfly) solution 45.0% after 6 h and 4-, and 6-day-old
feeding 49.0% after 24 h adults, starved earlier
for 24 h.
(3)

2. Spodoptera litura (Fab.) Leaf disk 70 µg/1.5 cm2 Feeding deterrence = 2. Treatment to 5th
(Tobacco armyworm) no-choice 60.7% instar larvae, pre-
assay starved for 3 h.

Treatment given for


30 m.
(4)

LD50 (rats): 5.0 mg/kg (oral) (5)

(1) Watson, E.R. and Sen, H.D. (1926) J. Ind. Chem. Soc., 3, 397.
(2) Woodward, R.B., Cava, M.P., Ollis, W.D., Hunger, A., Daeniker, H.U., and Schenker, K. (1954) J. Am. Chem.
Soc., 76, 4749.
(3) Blades, D. and Mitchell, B.K. (1986) Entomol. Exp. Appl., 41, 299.
(4) Passreiter, C.M. and Isman, M.B. (1997) Biochem Syst. Ecol., 25, 371.
(5) Amann, A., Jaeger, K.H., and Jarisch, A. (1943) Arch. Exp. Pathol. Pharmakol., 201, 161.

© 2005 by CRC Press LLC


Insect Antifeedants 891

SUCCINIC ACID C4H6O4


(118.09)
M.p. : 184–185°

B.p. : 235° (dec.)

O OH
OH

(1) (1)

SOURCE: Osmunda japonica (L.) Thunb., flowering fern (Osmundaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Eurema hecabe mandarina Artificial diet 0.8% Feeding deterrence = Treatment to 5th
DeLorza feeding 7.2% stadium larvae.
(Yellow butterfly) (1)
Strong antifeedance

0.4% Feeding deterrence =


18.8%

Strong antifeedance

0.2% Feeding deterrence =


34.1%

Slight antifeedance

LD50 (rats): 8.53 g/kg (oral) (2)

(1) Numata, A., Hokimoto, K., Takemura, T., Katsuno, T., and Yamamoto, K. (1984) Chem. Pharm. Bull., 32, 2815.
(2) Smyth, H.F. Jr., Carpenter, C.P., and Weil, C.S. (1951) Arch. Ind. Hyg. Occup. Med., 4, 119.

© 2005 by CRC Press LLC


892 Opender Koul

18 – SUCCINYLOXYGRINDELIC ACID C24H36O7


(436.54)
[α]D : –55° (CHCl3)

COOH
O

OCOCH2.CH2COOH

(1) (1)

SOURCE: Chrysothamnus nauseosus (Pall.) Britt., rubber rabbitbush (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Schizaphis graminum (Rondani) Artificial diet 0.003% Feeding deterrence = Treatment to aphids
(Wheat aphid) feeding 50.0% at random.

Concentration = EC50
value.
(2)

(1) Rose, A.F. (1980) Phytochemistry, 19, 2689.


(2) Rose, A.F., Jones, K.C., Haddon, W.F., and Dreyer, D.L. (1981) Phytochemistry, 20, 2249.

© 2005 by CRC Press LLC


Insect Antifeedants 893

TAGITININ–A C19H28O7
(368.43)
M.p. : 168–170°

[α]D : –154° (EtOH)


OH

O
O
HO CH2

O
O

(1, 2) (1)

SOURCE: Tithonia diversifolia (Hemsl.) Gray, Mexican sunflower (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Philosamia ricini Hutt. Leaf disk test 1.0% Feeding inhibition = Treatment to 0- to
(Eri silkworm) 96.9% 12-h-old 4th instar
larvae.
0.5% Feeding inhibition =
88.5% EC50 = 0.22%

0.25% Feeding inhibition = Calculated from


53.4% Reference 2.
(2)
0.05% Feeding inhibition =
30.8%

0.02% Feeding inhibition =


28.4%

(1) Pal, R., Kulshreshtha, D.K., and Rastogi, R.P. (1976) Ind. J. Chem., 14B, 259.
(2) Dutta, P., Bhattacharyya, P.R., Rabha, L.C., Bordoloi, D.N., Barua, N.C., Chowdhury, P.K., Sharma, R.P., and
Barua, J.N. (1986) Phytoparasitica, 14, 77.

© 2005 by CRC Press LLC


894 Opender Koul

TAGITININ–C C19H24O6
(348.39)
Oil

[α]D : –204° (EtOH)

OH

O O

O CH2 O

(1, 2) (1)

SOURCE: Tithonia diversifolia (Hemsl.) Gray, Mexican sunflower (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Philosamia ricini Hutt. Leaf disk test 1.0% Feeding inhibition = Treatment to 0- to
(Eri silkworm) 97.2% 12–h-old 4th instar
larvae.
0.5% Feeding inhibition =
89.6% EC50 = 0.041%

0.25% Feeding inhibition = Calculated from


81.0% Reference 2.
(2)
0.05% Feeding inhibition =
58.5%

0.02% Feeding inhibition =


33.8%

(1) Pal, R., Kulshreshtha, D.K., and Rastogi, R.P. (1977) Ind. J. Chem., 15B, 208.
(2) Dutta, P., Bhattacharyya, P.R., Rabha, L.C., Bordoloi, D.N., Barua, N.C., Chowdhury, P.K., Sharma, R.P., and
Barua, J.N. (1986) Phytoparasitica, 14, 77.

© 2005 by CRC Press LLC


Insect Antifeedants 895

TANGERETIN C20H20O7
(372.35)
M.p. : 152°

OCH3
OCH3

H3CO O

H3CO

OCH3 O

(1) (1)

SOURCE: Gnaphalium affine D. Don, cud weed (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk 2.8 × 10–7 Feeding inhibition = Treatment to 3rd
(Tobacco armyworm) choice test mol/cm2 50% instar larvae in the
dark for 2 to 5 h.
Concentration = EC50
value.
(1)

(1) Morimoto, M., Kumeda, S., and Komai, K. (2000) J. Agric. Food Chem., 48, 1888.

© 2005 by CRC Press LLC


896 Opender Koul

TANGERETIN (5-DEMETHYL) C19H18O7


(358.33)
M.p. : 175°

OCH3
OCH3

H3CO O

H3CO

OH O

(1) (1)

SOURCE: Gnaphalium affine D. Don, cud weed (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Leaf disk 1.8 × 10–7 Feeding inhibition = Treatment to 3rd
(Tobacco armyworm) choice test mol/cm2 50% instar larvae in the
dark for 2 to 5 h.
Concentration = EC50
value.
(1)

(1) Morimoto, M., Kumeda, S., and Komai, K. (2000) J. Agric. Food Chem., 48, 1888.

© 2005 by CRC Press LLC


Insect Antifeedants 897

TECLEANTHINE C17H15O5N
(313.31)
M.p. : 158°

O OCH3

N O

OCH3

(1, 2) (1, 2)

SOURCE: Teclea trichocarpa Engl., African evergreen techlea (Meliaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera exempta (Walker) Leaf disk 5000 ppm Feeding inhibition = Treatment to 3rd
(Nutgrass armyworm) choice test 100% after 2 h instar larvae.
(2)

(1) Pegel, K.H. and Wright, W.G. (1969) J. Chem. Soc., 2327.
(2) Lwande, W., Gebreyesus, T., Chapaya, A., Macfoy, C., Hassanali, A., and Okech, M. (1983) Insect Sci. Applic.,
4, 393.

© 2005 by CRC Press LLC


898 Opender Koul

TENULIN C17H22O5
(306.36)
M.p. : 196–198°

[α]20
D : –21.7° (EtOH)

O
O O
OH

(1, 2) (1, 2)

SOURCE: Helenium amarum (Raf.) H. Koch, bitterweed (Asteraceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Ostrinia nubilalis (Hubner) Leaf disk test 3 µmol/g Feeding inhibition = Treatment to larvae.
(European corn borer) 72.0%
Data calculated from
Reference 2.
(2)

(1) Herz, W. and Sharma, R.P. (1975) J. Org. Chem., 40, 2557.
(2) Arnason, J.T., Isman, M.B., Philogene, B.J.R., and Waddel, T.G. (1987) J. Nat. Prod., 50, 690.

© 2005 by CRC Press LLC


Insect Antifeedants 899

TENULIN OXIDE C17H22O6


(322.34)
Only spectral data given

H
H

O
H

O
O O
OH

(1) (1)

SOURCE: Helenium amarum (Raf.) H. Koch, bitterweed (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Ostrinia nubilalis (Hubner) Leaf disk test 3 µmol/g Feeding inhibition = Treatment to larvae.
(European corn borer) 77.9%
Data calculated from
Reference 2.
(2)

(1) Herz, W. and Sharma, R.P. (1975) J. Org. Chem., 40, 2557.
(2) Arnason, J.T., Isman, M.B., Philogene, B.J.R., and Waddel, T.G. (1987) J. Nat. Prod., 50, 690.

© 2005 by CRC Press LLC


900 Opender Koul

TEPHROSIN C23H22O7
(410.42)
M.p. : (–) form amorphous
(±) form 198°
OCH3
[α]23
D : –118° (benzene)
OCH3
O
OH

O
O O

(1) (1)

SOURCE: Tephrosia elata Deflers., African tephrosia, also isolated from other species
of Tephrosia (Fabaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera exempta (Walker) Leaf disk test 1 µg/2 cm Feeding inhibition = 1. Treatment to mid
(Nutgrass armyworm) diameter 89.0% 6th instar larvae for
disk 2 h. Larvae pre-
starved for 2 h.
(2)

2. Eldana saccharina Walker Leaf disk test Per 1.8 cm


(Sugar cane borer) diameter
disk:
100 µg Feeding inhibition = 2. Treatment to 5th
94.0% instar larvae for 24 h
in dark. Larvae pre-
10 µg Feeding inhibition = starved for 12 h.
86.0% (2)

1 µg Feeding inhibition =
72.0%

(1) Dev, S. and Koul, O. (1997) Insecticides of Natural Origin, Harwood Academic Publishers, Amsterdam, p. 211.
(2) Bentley, M.D., Hassanali, A., Lwandi, W., Njoroge, P.E.W., Sitayo, E.N.O., and Yatagai, M. (1987) Insect
Sci. Applic., 8, 85.

© 2005 by CRC Press LLC


Insect Antifeedants 901

γ-TERPINENE C10H16
(136.23)
B.p. : 58–62.5°/10 mm

[α]25
D : +36° (neat)

n25
D : 1.4696

(1, 2) (1)

SOURCE: Artemisia capillaris Thumb., wormwood (Asteraceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Pieris rapae crucivora Boisd. Leaf disk test 10–1 mol/L Feeding inhibition = Treatment to 5th
(Cabbage butterfly) 61.0% after 2 h. instar larvae.
(2)

LD50 (rats): 1680 mg/kg (oral) (3)

(1) Briggs, L.H. and Sutherland, M.D. (1948) J. Org. Chem., 13, 1.
(2) Yano, K. (1987) J. Agric. Food Chem., 35, 889.
(3) Opdyke, D.L.J. (1976) Food Cosmet. Toxicol., 14, 873.

© 2005 by CRC Press LLC


902 Opender Koul

2′,3′,22,23-TETRAHYDROAZADIRACHTIN C35H48O16
(724.76)
Only spectral data given

COOCH3
OH OH
O O

O
O
OH H
AcO
H
H3COOC O

(1, 2) (1, 2)

SOURCE: Synthetic (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera littoralis (Boisd.) Glass fiber Treatment to 24- to


(Egyptian cotton leaf worm) disk test: Feeding inhibition = 36-h-old starved final
Choice 1 ppm 79.0% stadium larvae.
No-choice 1 ppm 41.7% Bioassay terminated
after the larvae had
2. Spodoptera frugiperda Glass fiber consumed about 50%
(J.E. Smith) disk test: Feeding inhibition = of one of the disks.
(Fall armyworm) Choice 1 ppm 97.0% (1)
No-choice 1 ppm 44.0%
Deterrence
3. Heliothis virescens (Fab.) Glass fiber calculated from
(Tobacco budworm) disk test: Feeding inhibition = Reference 1 for no-
Choice 1 ppm 98.0% choice assay run for
No-choice 1 ppm 36.0% 8 to 9 h.

4. Helicoverpa armigera Glass fiber 1 ppm Feeding inhibition =


(Hubner) disk choice 64.0%
(Gram pod borer) test

(1) Blaney, W.M., Simmonds, M.S.J., Ley, S.V., Anderson, J.C., and Toogood, P.L. (1990) Entomol. Exp. Appl.,
55, 149.
(2) Ley, S.V., Anderson, J.C., Blaney, W.M., Lidert, Z., Morgan, E.D., Robinson, N.G., Santafianos, D., Simmonds,
M.S.J., and Toogood, P.L. (1989) Tetrahedron Lett., 30, 5175.

© 2005 by CRC Press LLC


Insect Antifeedants 903

TETRAHYDRO-ACETYLISOMONTANOLIDE C24H36O8
(452.51)
Only spectral data given

OCOCH3
H

OCO

H
O OCOCH3

(1, 2) (1)

SOURCE: Synthetic (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius (L.) Wafer disk 1.0% Feeding deterrence 1. Treatment given to
(Grain weevil) test coefficient = 30 adults.

2. Tribolium confusum Duv. Wafer disk 1.0% Feeding deterrence 2. Treatment given to
(Confused flour beetle) test coefficient: both adults and
Adults = 104.0 larvae.
Larvae = 83.0

3. Trogoderma granarium Wafer disk 1.0% Feeding deterrence 3. Treatment given to


Everts test coefficient = 80.0 larvae.
(Khapra beetle)
Neutral value = 0
Absolute feeding
deterrence value =
200
(2)

(1) Holub, M., Motl, O., Samek, Z., and Herout, V. (1972) Collect. Czech. Chem. Commun., 37, 1186.
(2) Nawrot, J., Smitalova, Z., and Holub, M. (1983) Biochem. Syst. Ecol., 11, 243.

© 2005 by CRC Press LLC


904 Opender Koul

TETRAHYDROISOPONGAFLAVONE C21H22O4
(338.40)
M.p. : 167–168°

O O

OCH3 O

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera exempta (Walker) Leaf disk 100 µg/2 cm Feeding inhibition = 1. Treatment to mid
(Nutgrass armyworm) test diameter 25.0% 6th instar larvae for
disk 2 h. Larvae pre-
starved for 2 h.
(1)

2. Eldana saccharina Walker Leaf disk Per 1.8 cm Feeding inhibition = 2. Treatment to 5th
(Sugar cane borer) test diameter 94.0% instar larvae for 24 h
disk: in dark. Larvae pre-
100 µg Feeding inhibition = starved for 12 h.
86.0% (1)

10 µg Feeding inhibition =
87.0%

3. Maruca testulalis (Geyer) Leaf disk Per 2 cm Feeding inhibition = 3. Treatment to late
(Bean pod borer) test diameter 64.0% 5th instar larvae for
disk: 6 h.
100 µg (1)

10 µg

(1) Bentley, M.D., Hassanali, A., Lwandi, W., Njoroge, P.E.W., Sitayo, E.N.O., and Yatagai, M. (1987) Insect
Sci. Applic., 8, 85.

© 2005 by CRC Press LLC


Insect Antifeedants 905

TEUCJAPONIN–A C22H28O7
(404.46)
M.p. : 145–148°
O
[α]20
D : +38.8° (CHCl3)

O
H
O

OAc OH

(1, 2) (1)

SOURCE: Teucrium japonicum Houtt., Japanese germander (Labiatae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Prodenia litura (Fab.) Leaf disk 400 ppm Feeding inhibition = 1. Treatment to early
(Tobacco armyworm) choice test Threshold level, after 3rd instar larvae.
5h (1)

2. Spodoptera littoralis (Boisd.) Glass fiber 100 ppm Feeding inhibition = 2. Treatment to final
(Egyptian cotton leaf worm) disk choice 12.9% stadium larvae
test starved for 4 h.
Treatment never
longer than 18 h so
that never more than
50% of any disk was
consumed.
(2)

(1) Miyase, T., Kawasaki, H., Noro, T., Ueno, A., Fukushima, S., and Takemoto, T. (1981) Chem. Pharm. Bull.,
29, 3561.
(2) Simmonds, M.S.J., Blaney, W.M., Ley, S.V., Savona, G., Bruno, M., and Rodriguez, B. (1989) Phytochemistry,
28, 1069.

© 2005 by CRC Press LLC


906 Opender Koul

TEUCJAPONIN–B C22H28O7
(404.46)
M.p. : 211–213°
O (255–258°)

[α]20
D : +60° (CH2Cl2)

O
H
O

OAc OH

(1, 2) (1)

SOURCE: Teucrium japonicum Houtt., Japanese germander (Labiatae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera littoralis (Boisd.) Glass fiber 100 ppm Feeding inhibition = 1. Treatment to final
(Egyptian cotton leaf worm) disk choice 48.9% stadium larvae
test starved for 4 h.
10 ppm Feeding inhibition = Treatment never
43.0% longer than 18 h so
that never more than
50% of any disk was
consumed.
(2)

2. Helicoverpa armigera Glass fiber 100 ppm Feeding inhibition = 2. Treatment to final
(Hubner) disk choice 29.8% stadium larvae as in
(Gram pod borer) test S. littoralis above.
10 ppm Feeding inhibition = (2)
23.2%

(1) Miyase, T., Kawasaki, H., Noro, T., Ueno, A., Fukushima, S., and Takemoto, T. (1981) Chem. Pharm. Bull.,
29, 3561.
(2) Simmonds, M.S.J., Blaney, W.M., Ley, S.V., Savona, G., Bruno, M., and Rodriguez, B. (1989) Phytochemistry,
28, 1069.

© 2005 by CRC Press LLC


Insect Antifeedants 907

TEUCRIN–A C19H20O6
(344.36)
M.p. : 195–198° (acetate)
O
[α]20
D : +96.2° (CHCl3)
(acetate)

O
H
O

OH

O
(1, 2) (1)

SOURCE: Teucrium chamaedrys L., germander wall (Labiatae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Leptinotarsa decemlineata Leaf disk 1000 ppm Feeding inhibition = Treatment to newly
(Say) choice test 34.0% emerged 4th instar
(Colorado potato beetle) larvae for 4 h in no-
Leaf disk 1000 ppm Feeding inhibition = choice situation and
no-choice 75.0% up to 24 h or until
test 50% of the disks
300 ppm Feeding inhibition = were consumed in
51.0% choice situation.
(2)
100 ppm Feeding inhibition =
35.6%

(1) Fernandez-Gadea, F., Pascual, C., Rodriguez, B., and Savona, G. (1983) Phytochemistry, 22, 723.
(2) Ortego, F., Rodriguez, B., and Castanera, P. (1995) J. Chem. Ecol., 21, 1375.

© 2005 by CRC Press LLC


908 Opender Koul

TEUCVIN C19H20O5
(328.36)
M.p. : 207–208°
O
[α]D : +88.4° (CHCl3)

O
H
O

O
(1, 2) (1)

SOURCE: Teucrium viscidum Blm., germander sticky (Labiatae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Leptinotarsa decemlineata Leaf disk 1000 ppm Feeding inhibition = Treatment to newly
(Say) choice test 25.1% emerged 4th instar
(Colorado potato beetle) larvae for 4 h in no-
300 ppm Feeding inhibition = choice situation and
8.1% up to 24 h or until
50% of the disks
Leaf disk no- 1000 ppm Feeding inhibition = were consumed in
choice test 77.8% choice situation.
(2)
300 ppm Feeding inhibition =
59.4% EC50 = 94 ppm in no-
choice test.
100 ppm Feeding inhibition = (3)
45.6%

(1) Fujita, E., Uchida, T., and Fujita, T. (1974) J. Chem. Soc. Perkin I, 1547.
(2) Ortego, F., Rodriguez, B., and Castanera, P. (1995) J. Chem. Ecol., 21, 1375.
(3) Lopez-Olguin, J., Maria, C.T., Ortego, F., Castanera, P., and Rodriguez, B. (1999) Phytochemistry, 50, 749–753.

© 2005 by CRC Press LLC


Insect Antifeedants 909

TEUFLIDIN C19H20O6
(344.36)
M.p. : 178°
O
[α]20
D : –100° (CHCl3)

O
H
O

HO

O
(1, 2) (1)

SOURCE: Teucrium viscidum Blm., sticky germander (Labiatae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Leptinotarsa decemlineata Leaf disk 1000 ppm Feeding inhibition = Treatment to newly
(Say) choice test 57.5% emerged 4th instar
(Colorado potato beetle) larvae for 4 h in no-
choice situation and
Leaf disk 1000 ppm Feeding inhibition = up to 24 h or until
no-choice 92.9% 50% of the disks
test were consumed in
choice situation.

EC50 = 53 ppm in no-


choice test.
(3)

(1) Fernandez-Gadea, F., Pascual, C., Rodriguez, B., and Savona, G. (1983) Phytochemistry, 22, 723.
(2) Rodriguez, M.C., Barluenga, J., Savona, G., Piozzi, F., Servettaz, O., and Rodriguez, B. (1984) Phytochemistry,
23, 1465.
(3) Lopez-Olguin, J., Maria, C.T., Ortego, F., Castanera, P., and Rodriguez, B. (1999) Phytochemistry, 50, 749–753.

© 2005 by CRC Press LLC


910 Opender Koul

TEUFLIN C19H20O5
(328.36)
M.p. : 153°
O
[α]D : +12° (CHCl3)

O
H
O

(1, 2) (1, 2)

SOURCE: Teucrium chamaedrys L., wall germander (Labiatae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Leptinotarsa decemlineata Leaf disk 1000 ppm Feeding inhibition = Treatment to newly
(Say) choice test 44.1% emerged 4th instar
(Colorado potato beetle) larvae for 4 h in no-
Leaf disk no- 1000 ppm Feeding inhibition = choice situation and
choice test 89.3% up to 24 h or until
50% of the disks
were consumed in
choice situation.

EC50 = 91 ppm in no-


choice test.
(3)

(1) Fernandez-Gadea, F., Pascual, C., Rodriguez, B., and Savona, G. (1983) Phytochemistry, 22, 723.
(2) Rodriguez, M.C., Barluenga, J., Savona, G., Piozzi, F., Servettaz, O., and Rodriguez, B. (1984) Phytochemistry,
23, 1465.
(3) Lopez-Olguin, J., Maria, C.T., Ortego, F., Castanera, P., and Rodriguez, B. (1999) Phytochemistry, 50, 749–753.

© 2005 by CRC Press LLC


Insect Antifeedants 911

TEUMASSILENIN–A C20H30O5
(350.46)
M.p. : 187–190°
O
[α]20
D : +2° (CHCl3/MeOH)

H OH

H
CHO O
OH

(1, 2) (1)

SOURCE: Teucrium massiliense, L., purple germander (Labiatae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Leptinotarsa decemlineata Leaf disk 1000 ppm Feeding inhibition = Treatment to newly
(Say) choice test 88.2% emerged 4th instar
(Colorado potato beetle) larvae pre-starved for
Leaf disk no- 1000 ppm Feeding inhibition = 6 h until 50% of the
choice test 75.6% control disks were
consumed in choice
situation and 75% in
no-choice assay.

Assayed against
Spodoptera exigua as
well, but found
inactive against this
species.
(2)

(1) Fontana, G., Paternostro, M.P., Savona, G., Rodriguez, B., and de la Torre, M.C. (1998) J. Nat. Prod., 61, 1242.
(2) Caballero, C., Castanera, P., Ortego, F., Fontana, G., Pierro, P., Savona, G., and Rodriguez, B. (2001)
Phytochemistry, 58, 249.

© 2005 by CRC Press LLC


912 Opender Koul

TEUMASSILENIN–C C20H30O5
(350.46)
M.p. : 125–127°
O
[α]20
D : –33.4° (CHCl3)

OH

HO
O
OH

(1, 2) (1)

SOURCE: Teucrium massiliense, L., purple germander (Labiatae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Leptinotarsa decemlineata Leaf disk 1000 ppm Feeding inhibition = Treatment to newly
(Say) choice test 73.7% emerged 4th instar
(Colorado potato beetle) larvae, pre-starved
Leaf disk no- 1000 ppm Feeding inhibition = for 6 h until 50% of
choice test 67.6% the control disks
were consumed in
choice situation and
75% in no-choice
assay.

Assayed against
Spodoptera exigua as
well, but found
inactive against this
species.
(2)

(1) Fontana, G., Paternostro, M.P., Savona, G., Rodriguez, B., and de la Torre, M.C. (1998) J. Nat. Prod., 61, 1242.
(2) Caballero, C., Castanera, P., Ortego, F., Fontana, G., Pierro, P., Savona, G., and Rodriguez, B. (2001)
Phytochemistry, 58, 249.

© 2005 by CRC Press LLC


Insect Antifeedants 913

TEUSCOROLIDE C19H18O5
(326.35)
M.p. : 198–200°
O
[α]20
D : +13.5° (CHCl3)

O
H
O

O
(1, 2) (1)

SOURCE: Teucrium scorodonia L., garlic sage (Labiatae) (1, 3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Leptinotarsa decemlineata Leaf disk 1000 ppm Feeding inhibition = Treatment to newly
(Say) choice test 32.9% emerged 4th instar
(Colorado potato beetle) larvae for 4 h in no-
300 ppm Feeding inhibition = choice situation and
25.2% up to 24 h or until
50% of the disks
Leaf disk no- 1000 ppm Feeding inhibition = were consumed in
choice test 39.0% choice situation.
(2)
300 ppm Feeding inhibition =
7.3% EC50 = 394 ppm in
no-choice test.
(3)

(1) Marco, J.L., Rodriguez, B., Savona, G., and Piozzi, F. (1982) Phytochemistry, 21, 2567; (1983), 22, 727.
(2) Ortego, F., Rodriguez, B., and Castanera, P. (1995) J. Chem. Ecol., 21, 1375.
(3) Lopez-Olguin, J., Maria, C.T., Ortego, F., Castanera, P., and Rodriguez, B. (1999) Phytochemistry, 50, 749.

© 2005 by CRC Press LLC


914 Opender Koul

(+)-3-THUJONE C10H16O
(152.23)
B.p. : 40.9°/0.5 mm

[α]25
D : +78.8° (neat)

(1) (1)

SOURCE: Thuja plicata Donn. ex Don, Western red cedar (Cupressaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Pissodes strobi Peck. Agar disk 5 µg/disk Feeding inhibition = Treatment to adult
(White pine weevil) procedure 34.8% within 24 h. weevils.
(2)

LD50 (mice): 87.5 mg/kg (sc.) (3)

(1) Hach, V., Lockhart, R.W., McDonald, E.C., and Cartlidge, D.M. (1971) Can. J. Chem., 49, 1762.
(2) Alfaro, R.I., Pierce, H.D. Jr., Borden, J.H., Oehlschlager, A.C. (1981) J. Chem. Ecol., 7, 39.
(3) Rice, K.C. and Wilson, R.S. (1976) J. Med. Chem., 19, 1054.

© 2005 by CRC Press LLC


Insect Antifeedants 915

3 – TIGLOYLAZADIRACHTOL C33H42O14
(also see Azadirachtin–B) (662.68)
M.p. : 204–206°

[α]20
D : –69.4° (CH2Cl2)
COOCH3
H OH
HO O

O
O

O
O
O OH H
H
H3COOC O

(1, 2) (1)

SOURCE: Azadirachta indica A. Juss., neem (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera littoralis (Boisd.) Glass fiber 1 ppm Feeding inhibition = Treatment to 24- to
(Egyptian cotton leaf worm) disk choice 97.0%. 36-h-old starved final
test stadium larvae.
Glass fiber 1 ppm Feeding inhibition = Bioassay terminated
disk no- 80.6%. after the larvae had
choice test consumed about 50%
2. Spodoptera frugiperda Glass fiber 1 ppm Feeding inhibition = of one of the disks.
(J.E. Smith) disk choice 60.0%. (2)
(Fall armyworm) test
Glass fiber 1 ppm Feeding inhibition = Deterrence
disk no- 66.2%. calculated from
choice test Reference 2 for no-
3. Heliothis virescens (Fab.) Glass fiber 1 ppm Feeding inhibition = choice assay run for
(Tobacco budworm) disk choice 43.0%. 8 to 9 h.
test
4. Helicoverpa armigera Glass fiber 1 ppm Feeding inhibition =
(Hubner) disk choice 41.0%.
(Gram pod borer) test

(1) Klenk, A., Bokel, M., and Kraus, W. (1986) J. Chem. Soc. Chem. Commun., 523.
(2) Blaney, W.M., Simmonds, M.S.J., Ley, S.V., Anderson, J.C., and Toogood, P.L. (1990) Entomol. Exp. Appl.,
55, 149.

© 2005 by CRC Press LLC


916 Opender Koul

6 – TIGLOYL CHAPARRINONE C25H32O9


(476.52)
M.p. : 229°
OH
[α]22
D : +195.7° (neat)
HO
HO
O

O O
H
OCO

(1, 2) (1)

SOURCE: Simaba cuspidata Spruce ex Engl., wasakusili (Scrophulariaceae) (1)


Ailanthus grandis Prain., ailanthus (Simaroubaceae)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Heliothis virescens (Fab.) Leaf disk 12.0 µg/cm2 Feeding inhibition = Treatment to 3rd
(Tobacco budworm) choice test 60–90% after 6 days. instar larvae.
(2)
6.0 µg/cm2 Feeding inhibition =
30–60% after 6 days.

3.0 µg/cm2 Feeding inhibition =


30–60% after 2 days
and 0–30% after 6
days of treatment.

(1) Polonsky, J., Varon, Z., Moretti, C., Pettit, G.R., Herald, C.L., Rideout, J., Saha, S.B., and Khastgir, H.N.
(1980) J. Nat. Prod., 43, 503.
(2) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y., Kiyokawa, H., and Lee, K.H.
(1987) J. Nat. Prod., 50, 442.

© 2005 by CRC Press LLC


Insect Antifeedants 917

13 – TIGLOYLOXYLUPANINE C20H30O3N2
(346.47)
Oil

B.p. : 180–200°/0.001 mm
H

N O
H

O
O

(1, 2) (1)

SOURCE: Synthetic (2)


Also isolated from Lupinus polyphyllus Lindl., lupine (Fabaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Choristoneura fumiferana Paper 1.4 × 103 M Feeding deterrence = Treatment to 6th


(Clemens) penicillin 89.0% instar larvae.
(Spruce budworm) disk assay (2)

(1) Dictionary of Natural Products (1994) Chapman & Hall, London.


(2) Bentley, M.D., Leonard, D.E., Reynolds, E.K., Leach, S., Beck, A.B., and Murakoshi, I. (1984) Ann. Entomol.
Soc. Am., 77, 398.

© 2005 by CRC Press LLC


918 Opender Koul

5α-TIGLOYLOXYSILPHINEN-3-ONE C20H28O3
(316.20)
Oil

[α]D : –67.2° (CHCl3)

O O

(1) (1)

SOURCE: Senecio palmensis Chr.Sm., groundsel (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera littoralis (Boisd.) Choice >200 nmol/cm2 Feeding deterrence = 1. Treatment to 6th
(Egyptian cotton leaf worm) feeding 50.0% instar larvae.
assay

2. Leptinotarsa decemlineata Choice 43.9 nmol/cm2 Feeding deterrence = 2. Treatment to


(Say) feeding 50.0% adults.
(Colorado potato beetle) assay

3. Myzus persicae (Sulzer) Choice 29.1 nmol/cm2 Feeding deterrence = 3. Treatment to


(Green peach aphid) feeding 50.0% apterous adult
assay aphids.

4. Rhopalosiphum padi (L.) Choice 39.8 nmol/cm2 Feeding deterrence = 4. Treatment to


(Cereal aphid) feeding 50.0% apterous adult
assay aphids.

5. Sitobion avenae (Fab.) Choice >100 nmol/cm2 Feeding deterrence = 5. Treatment to


(Grass aphid) feeding 50.0% apterous adult
assay aphids.

6. Diuraphis noxia (Mordvilko) Choice 29.8 nmol/cm2 Feeding deterrence = 6. Treatment to


(Wheat aphid) feeding 50.0% apterous adult
assay aphids.

Concentrations =
EC50 values.
(1)

(1) Reina, M., Nold, M., Santana, O., Orihuela, J.C., and Gonzalez-Coloma, A. (2002) J. Nat. Prod., 65, 448.

© 2005 by CRC Press LLC


Insect Antifeedants 919

TILIROSIDE C30H26O13
(594.53)
OH

M.p. : 269–271°
HO O (267–269°)

[α]24
D : +69.9° (MeOH)

O
OH O

HO OH
O

O
HO

OH
O
(1, 2) (1)

SOURCE: Pteridium aquilinum L. Kuhn, bracken fern (Pteridophyte) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Pieris brassicae (L.) Leaf disk 1.7 × 10 –2 M Feeding deterrence Treatment to 2nd day
(Large white butterfly) no-choice ratio = 3.04 5th instar unstarved
test larvae.
Very effective (2)
deterrence

(1) Vermes, B., Chari, V.M., and Wagner, H. (1981) Helv. Chim. Acta, 64, 1964.
(2) Jones, C.G. and Firn, R.D. (1979) Biochem. Syst. Ecol., 7, 187.

© 2005 by CRC Press LLC


920 Opender Koul

TOMATIDINE C27H45O2N
(415.66)
M.p. : 202–206°
(210–211°)

[α]25
D : +8° (CHCl3)

N
H

HO
H

(1, 2) (1)

SOURCE: Commercial material, commonly occurs in Solanum spp. (Solanaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Choristoneura fumiferana Paper 10–3 M Feeding deterrence = Treatment to 6th


(Clemens) penicillin 64.0% instar larvae.
(Spruce budworm) disk assay (2)
10–4 M Feeding deterrence =
19.0%

(1) Brink, N.G. and Folkers, K. (1951) J. Am. Chem. Soc., 73, 4018.
(2) Bentley, M.D., Leonard, D.E., and Bushway, R.J. (1984) Ann. Entomol. Soc. Am., 77, 401.

© 2005 by CRC Press LLC


Insect Antifeedants 921

TOMATINE C50H83O21N
(1034.20)
M.p. : 263–268° (dec.)

[α]20
D : –18° (pyridine)

N
H

β-lycotetraose-O
H

(1, 2) (1)

SOURCE: Commercial material (2, 3, 4)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Choristoneura fumiferana Paper 10–3 M Feeding deterrence = 1. Treatment to 6th


(Clemens) penicillin 91.0% instar larvae.
(Spruce budworm) disk assay (2)
10–4 M Feeding deterrence =
48.0%

2. Leptinotarsa decemlineata Sensillum 0.2% wet Feeding deterrence = 2. Treatment to adult


(Say) response weight 50.0% beetles.
(Colorado potato beetle) recording
Concentration = EC50
value.
(3)

3. Phormia regina (Meigen) Sucrose 10 mM Feeding deterrence = 3. Treatment to 2-,


(Blowfly) solution 88.0% after 6 hours 4-, and 6-day-old
feeding and 86.0% after adults after 24-hour
24 hours pre-starvation.
(4)

LD (rats): 900–1000 mg/kg (oral) (5)

(1) Kuhn, R., Low, I., and Gauke, A. (1950) Chem Ber., 83, 448.
(2) Bentley, M.D., Leonard, D.E., and Bushway, R.J. (1984) Ann. Entomol. Soc. Am., 77, 401.
(3) Mitchell, B.K. and Harrison, G.D. (1985) J. Chem. Ecol., 11, 73.
(4) Blades, D. and Mitchell, B.K. (1986) Entomol. Exp. Appl., 41, 299.
(5) Wilson, R.H., Poley, G.W., and DeEds, F. (1961) Toxicol. Appl. Pharmacol., 3, 39.

© 2005 by CRC Press LLC


922 Opender Koul

TOONACILIN C31H38O9
(554.64)
M.p. : 118–119°
O
[α]20
D : +69° (CHCl3)
OAc

AcO

O
H
CH2
O

COOCH3

(1) (1)

SOURCE: Toona ciliata M.J. Roem, red cedar (Meliaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Epilachna varivestis Muls. Bean leaf 0.2% Feeding deterrence = Treatment to adult
(Mexican bean beetle) assay 100% beetles.
(2)

(1) Kraus, W., Grimminger, W., and Sawitzki, G. (1978) Angew. Chemie, 17, 452.
(2) Kraus, W. and Grimminger, W. (1980) Nouv. J. De Chim., 4, 651.

© 2005 by CRC Press LLC


Insect Antifeedants 923

TOOSENDANIN C30H38O11
(574.62)
M.p. : 251–252°

OAc O [α]16
D : +4.3° (CHCl3)

O
OH

O O

AcO OH

HO
H

(1,2,3) (1, 2)

SOURCE: Melia toosendan Sieb. et Zucc., Chinese melia (Meliaceae) (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Ostrinia furnacalis (Guenee) Artificial diet 20 ppm Feeding deterrence = 1. Treatment to


(Asiatic corn borer) feeding Significant, larvae.
determined by insect
growth No quantitative data
recorded.
(3)

2. Helicoverpa armigera Artificial diet 56.6 ppm Feeding deterrence = 2. Treatment to 3rd
(Hubner) feeding 50% instar larvae.
(Gram pod borer)
Concentration = FI50
value.
(4)

(1) Shu, G.X. and Liang, X.T. (1980) Acta Chim. Cin., 38, 196.
(2) Ochi, M., Kotsuki, H., Hirotsu, K., and Tokoroyama, T. (1976) Tetrahedron Lett., 2877.
(3) Shin-Foon, C. (1984) Proc. 2nd Int. Neem Conf., Rauischholzhausen, Germany, p. 255.
(4) Koul, O., Multani, J.S., Singh, G., and Wahab, S. (2002) Curr. Sci., 83, 1387.

© 2005 by CRC Press LLC


924 Opender Koul

TR–A C39H54O16
(778.84)
Amorphous
OH

O
H
HCOO O
AcO
H

O OH
H
OAc
O CH2

H
COOC2H5
HO (1) (1)

SOURCE: Trichilia roka (Forsk.) Chiov., East African trichilia (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Agrotis segetum Leaf disk 200 ppm Feeding deterrence = Treatment to larvae.
(Denis & Schiff.) choice test Strong antifeedant
(Turnip cutworm) activity No quantitative data
recorded.
(1)

(1) Nakatani, M., Okamoto, M., Iwashita, T., Mizukawa, K., Naoki, H., and Hase, T. (1984) Heterocycles, 22, 2335.

© 2005 by CRC Press LLC


Insect Antifeedants 925

TR–B C35H44O14
(688.72)
Amorphous
OH
[α]25
D : –18.3° (CHCl3)
O

O
H
HCOO O
AcO
H

O
H OH
O
O CH2

O
O (1) (1, 2)

SOURCE: Trichilia roka (Forsk.) Chiov., East African trichilia (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Agrotis segetum Leaf disk 200 ppm Feeding deterrence = Treatment to larvae.
(Denis & Schiff.) choice test Strong antifeedant
(Turnip cutworm) activity No quantitative data
recorded.
(1)

(1) Nakatani, M., Okamoto, M., Iwashita, T., Mizukawa, K., Naoki, H., and Hase, T. (1984) Heterocycles, 22, 2335.
(2) Gunatikala, A.A.L., Bolzani, V.S., Dagne, E., Hofmann, G.A., Johnson, R.K., McCabe, F.L., Mattern, M.R.,
and Kingston, D.G. (1998) J. Nat. Prod., 61, 179.

© 2005 by CRC Press LLC


926 Opender Koul

TR–C C38H52O16
(764.82)
Amorphous
OH

O
H
HCOO O
AcO
H

O
OH OAc
O CH2

COOCH3
HO (1) (1)

SOURCE: Trichilia roka (Forsk.) Chiov., East African trichilia (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Agrotis segetum Leaf disk 200 ppm Feeding deterrence = Treatment to larvae.
(Denis & Schiff.) choice test Strong antifeedant
(Turnip cutworm) activity No quantitative data
recorded.
(1)

(1) Nakatani, M., Okamoto, M., Iwashita, T., Mizukawa, K., Naoki, H., and Hase, T. (1984) Heterocycles, 22, 2335.

© 2005 by CRC Press LLC


Insect Antifeedants 927

TREWIASINE C37H52O11N3Cl
O (750.28)
M.p. : 182–185°

O [α]23
D : –94° (CHCl3)
N

Cl O O

H3CO O
N

N O
H3CO
OH
OCH3
(1, 2) (1)

SOURCE: Trewia nudiflora Wight, false white teak (Euphorbiaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Acalymma vittatum (Fab.) Leaf disk test 0.5% Feeding deterrence = Treatment to female
(Striped cucumber beetle) 84.6% beetles of same age
(1–2 weeks post-
0.25% Feeding deterrence = eclosion).
91.9%
Data calculated from
0.015% Feeding deterrence = Reference 2.
49.6% (2)

(1) Powell, R.G., Weisleder, D., and Smith, C.R. Jr. (1981) J. Org. Chem., 46, 4398.
(2) Reed, D.K., Kwolek, W.F., and Smith, C.R. Jr. (1983) J. Econ. Entomol., 76, 641.

© 2005 by CRC Press LLC


928 Opender Koul

TRICHILIN–A C35H46O13
(674.74)
M.p. : 191–192° (dec.)

OH O [α]25
D : –36.7° (CHCl3)

O
OH

AcO

O H O

AcO OH

O
H

O (1) (1)

SOURCE: Trichilia roka (Forsk.) Chiov., East African trichilia (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera eridania (Cramer) Leaf disk 300 ppm Feeding deterrence = Treatment to larvae.
(Southern armyworm) choice test 100% Feeding of this
compound over a 10-
day period to the 3rd
instar larvae killed
the insects.
(1)

(1) Nakatani, M., James, J.C., and Nakanishi, K. (1981) J. Am. Chem. Soc., 103, 1228.

© 2005 by CRC Press LLC


Insect Antifeedants 929

TRICHILIN–B C35H46O13
(674.74)
[α]22
D : –10° (neat)

OH O

O
OH

AcO

O H O

AcO OH

O
H

O (1) (1)

SOURCE: Trichilia roka (Forsk.) Chiov., East African trichilia (Meliaceae) (1)
Melia azedarach L., chinaberry (Meliaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera eridania Leaf disk 200 ppm Feeding deterrence = 1. Treatment to 3rd
(Cramer) choice test 100% instar larvae.
(Southern armyworm) (1)

2. Spodoptera exigua (Hubner) Leaf disk 200 ppm Feeding deterrence = 2. Treatment to 3rd
(Beet armyworm) choice test 100% instar larvae.
(2)

(1) Nakatani, M., James, J.C., and Nakanishi, K. (1981) J. Am. Chem. Soc., 103, 1228.
(2) Nakatani, M., Huang, R.C., Okamura, H., Naoki, H., and Iwagawa, T. (1994) Phytochemistry, 36, 39.

© 2005 by CRC Press LLC


930 Opender Koul

TRICHILIN–D C35H46O12
(658.74)
Oil

O [α]22
D : –72.6° (neat)

O
OH

AcO

O H O

AcO OH

O
H

O (1) (1)

SOURCE: Trichilia roka (Forsk.) Chiov., East African trichilia (Meliaceae) (1)
Melia azedarach L., chinaberry (Meliaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera eridania Leaf disk 400 ppm Feeding deterrence = 1. Treatment to 3rd
(Cramer) choice test 100% instar larvae.
(Southern armyworm) (1)

2. Spodoptera exigua (Hubner) Leaf disk 400 ppm Feeding deterrence = 2. Treatment to 3rd
(Beet armyworm) choice test 100% instar larvae.
(2)

(1) Nakatani, M., James, J.C., and Nakanishi, K. (1981) J. Am. Chem. Soc., 103, 1228.
(2) Nakatani, M., Huang, R.C., Okamura, H., Naoki, H., and Iwagawa, T. (1994) Phytochemistry, 36, 39.

© 2005 by CRC Press LLC


Insect Antifeedants 931

TRICHILIN–H C36H46O14
(702.75)
[α]22
D : –20.2° (MeOH)

OAc O

O
OH

AcO

O H O

AcO OH

O
H

O (1) (1)

SOURCE: Melia toosendan Sieb. et Zucc., Chinese melia (Meliaceae) (1)


Melia azedarach L., chinaberry (Meliaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera eridania Leaf disk 400 ppm Feeding deterrence = 1. Treatment to 3rd
(Cramer) choice test or 50.0% instar larvae for
(Southern armyworm) 8 µg/cm2 6–24 hours during
which period 50% of
one of the disks was
consumed.
(1, 2)

2. Spodoptera exigua (Hubner) Leaf disk 400 ppm Feeding deterrence = 2. Treatment to 3rd
(Beet armyworm) choice test or 50.0% instar larvae for
8 µg/cm2 6–24 hours during
which period 50% of
one of the disks was
consumed.
(1, 2)

(1) Zhou, J., Okamura, H., Iwagawa, T., and Nakatani, M. (1996) Phytochemistry, 41, 117.
(2) Nakatani, M., Huang, R.C., Okamura, H., Iwagawa, T., Tadera, K., and Naoki, H. (1995) Tetrahedron, 51,
11736.

© 2005 by CRC Press LLC


932 Opender Koul

TRICHILIN–I C35H46O13
(674.74)
Amorphous powder

O
OAc

O
OH

HO

O H O

AcO OH

O
H

O (1) (1)

SOURCE: Melia toosendan Sieb. et Zucc., Chinese melia (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera eridania (Cramer) Leaf disk 400 ppm Feeding deterrence = Treatment to 3rd
(Southern armyworm) choice test or 50.0% instar larvae for
8 µg/cm2 6–24 hours during
which period 50% of
one of the disks was
consumed.
(1)

(1) Zhou, J., Okamura, H., Iwagawa, T., and Nakatani, M. (1996) Phytochemistry, 41, 117.

© 2005 by CRC Press LLC


Insect Antifeedants 933

TRICHILIN–J C33H44O11
(616.70)
Amorphous powder

O [α]23
D : +20° (MeOH)

O
OH

HO

O H
O

AcO OH

O
H

O (1) (1)

SOURCE: Melia toosendan Sieb. et Zucc., Chinese melia (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera eridania (Cramer) Leaf disk 400 ppm Feeding deterrence = Treatment to 3rd
(Southern armyworm) choice test or 50.0% instar larvae for
8 µg/cm2 6–24 hours during
which period 50% of
one of the disks was
consumed.
(1)

(1) Zhou, J., Okamura, H., Iwagawa, T., and Nakatani, M. (1996) Phytochemistry, 41, 117.

© 2005 by CRC Press LLC


934 Opender Koul

TRICHILIN–K C32H42O11
(602.68)
Amorphous powder

O [α]22
D : –20° (MeOH)

O
OH

HO

O H
O

AcO OH

O
H

O (1) (1)

SOURCE: Melia toosendan Sieb. et Zucc., Chinese melia (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera eridania (Cramer) Leaf disk 400 ppm Feeding deterrence = Treatment to 3rd
(Southern armyworm) choice test or 50.0% instar larvae for
8 µg/cm2 6–24 hours during
which period 50% of
one of the disks was
consumed.
(1)

(1) Zhou, J., Okamura, H., Iwagawa, T., and Nakatani, M. (1996) Phytochemistry, 41, 117.

© 2005 by CRC Press LLC


Insect Antifeedants 935

TRICHILIN–L C33H44O11
(616.70)
Amorphous powder

O [α]22
D : –14° (MeOH)

O
OH

AcO

O H
O

HO OH

O
H

O (1) (1)

SOURCE: Melia toosendan Sieb. et Zucc., Chinese melia (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera eridania (Cramer) Leaf disk 400 ppm Feeding deterrence = Treatment to 3rd
(Southern armyworm) choice test or 50.0% instar larvae for
8 µg/cm2 6–24 hours during
which period 50% of
one of the disks was
consumed.
(1)

(1) Zhou, J., Okamura, H., Iwagawa, T., and Nakatani, M. (1996) Phytochemistry, 41, 117.

© 2005 by CRC Press LLC


936 Opender Koul

TRICHILININ–B C35H46O9
(610.74)
M.p. : 168–170°

[α]19
D : +56° (MeOH)
O O
OAc

AcO OH

(1) (1)

SOURCE: Melia toosendan Sieb. et Zucc., Chinese melia (Meliaceae) also isolated from M. volkensi (1)
Guerke

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera eridania (Cramer) Leaf disk 1000 ppm Feeding deterrence = Treatment to 3rd
(Southern armyworm) choice test 50.0% instar larvae for
6–24 hours during
which period 50% of
one of the disks was
consumed.
(1)

(1) Zhou, J., Okamura, H., Iwagawa, T., Nakamura, Y., Nakayama, N, Tadera, K., and Nakatani, M. (1995)
Heterocycles, 41, 2795.

© 2005 by CRC Press LLC


Insect Antifeedants 937

TRICHILININ–C C33H44O7
(552.71)
Amorphous powder

[α]19
D : +22° (MeOH)
H O

OAc

O OH

(1) (1)

SOURCE: Melia toosendan Sieb. et Zucc., Chinese melia (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera eridania (Cramer) Leaf disk 1000 ppm Feeding deterrence = Treatment to 3rd
(Southern armyworm) choice test 50.0% instar larvae for
6–24 hours during
which period 50% of
one of the disks was
consumed.
(1)

(1) Zhou, J., Okamura, H., Iwagawa, T., Nakamura, Y., Nakayama, N, Tadera, K., and Nakatani, M. (1995)
Heterocycles, 41, 2795.

© 2005 by CRC Press LLC


938 Opender Koul

TRICHLOROMETHYLPHTHALAZINE C13H11ON2Cl3
(317.60)
Only spectral data given

OC2H5

CCl3

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera eridania (Cramer) Leaf disk 260 ppm Feeding deterrence = Treatment to larvae.
(Southern armyworm) choice test 100%

(1) Rothgery, E.F. and Schroeder, H.A. (1979) U.S. Patent 4139622, 5 pp.

© 2005 by CRC Press LLC


Insect Antifeedants 939

TRI (CYCLOHEXYL) – TRIAZOL-1-YL) TIN C20H35N3Sn


(Peropal) (436.21)
M.p. : 218.8°

N Sn

(1, 2) (1)

SOURCE: Commercial sample (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera littoralis (Boisd.) Leaf disk 0.013% Feeding deterrence = Treatment to


(Egyptian cotton leaf worm) choice test 50.0% 170–190 mg body
weight larvae.
0.11% Feeding deterrence = (2)
95.0%

(1) The Agrochemicals Handbook (1986) Roy. Soc. Chem., U.K.


(2) Ascher, K.R.S. (1980) Naturwissenschaften, 67, 312.

© 2005 by CRC Press LLC


940 Opender Koul

3 – TRIFLUROMETHANE SULFONYL BRUCEANTIN C29H35O13F3S


(680.64)
M.p. : 255–257°

OH

HO COOCH3
O
O OCO

H
SO2F3CO O O

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Heliothis virescens (Fab.) Leaf disk 12.0 µg/cm2 Feeding inhibition = Treatment to 3rd
(Tobacco budworm) choice test 30–60% after 2 days instar larvae.
and 0–30% after 6 (2)
days of treatment.

(1) Lidert, Z., Wing, K., Polonsky, J., Imakura, Y., Okano, M., Tani, S., Lin, Y., Kiyokawa, H., and Lee, K.H.
(1987) J. Nat. Prod., 50, 442.

© 2005 by CRC Press LLC


Insect Antifeedants 941

TRILOBOLIDE C27H38O10
(522.59)
M.p. : 191–192°

[α]20
D : +73.3° (MeOH)
OCOCH3

COO OCO
OH
OH

(1, 2) (1, 2)

SOURCE: Laser trilobum (L.) Borkh., gladich (Apiaceae) (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius (L.) Wafer disk 1.0% Feeding deterrence 1. Treatment given to
(Grain weevil) test coefficient = 98 adults.
(3)

2. Tribolium confusum Duv. Wafer disk 1.0% Feeding deterrence 2. Treatment given to
(Confused flour beetle) test coefficient: both adults and
Adults = 143 larvae.
Larvae = 200 (3)

3. Trogoderma granarium Wafer disk 1.0% Feeding deterrence 3. Treatment given to


Everts test coefficient = 137 larvae.
(Khapra beetle) Neutral value = 0
Absolute feeding
deterrence value =
200
(3)

(1) Holub, M., DeGroote, R., Herout, V., and Sorm, F. (1968) Collect. Czech. Chem. Commun., 33, 2911.
(2) Holub, M., Samek, Z., DeGroote, R., Herout, V., and Sorm, F. (1973) Collect. Czech. Chem. Commun., 38,
1551.
(3) Nawrot, J., Smitalova, Z., and Holub, M. (1983) Biochem. Syst. Ecol., 11, 243.

© 2005 by CRC Press LLC


942 Opender Koul

3,4,5 – TRIMETHOXYPHENOL C9H12O4


(184.19)
M.p. : 148°

OH

H3CO OCH3

OCH3

(1,3) (1, 2)

SOURCE: Synthetic, also occurring naturally in the sap of Antiaris toxicaria Lesch., Javanese upas (1, 3)
tree (Moraceae)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Acalymma vittatum (Fab.) Leaf disk 0.1% Feeding deterrence = Treatment to adult
(Striped cucumber beetle) choice test 100% up to 4 hours beetles.
(1)
0.5% Feeding deterrence =
100% up to 24 hours

(1) Reed, D.K. and Jacobson, M. (1983) Experientia, 39, 378.


(2) Dictionary of Natural Products, (1994) Chapman & Hall, London.
(3) Kiliani, H. (1896) Arch. Pharm., 234, 438.

© 2005 by CRC Press LLC


Insect Antifeedants 943

1-(2,4,6-TRIMETHOXYPHENYL) BUT- C13H16O4


TRANS-2EN-1-ONE (236.27)
M.p. : 95°
(91–92°)
OCH3

H3CO OCH3

(1) (1, 2)

SOURCE: Arachniodes standishii (Moore) Ohwi., Japanese ryomenshida (Fabaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Eurema hecabe mandarina Artificial diet 0.1% Feeding deterrence Treatment to 5th
DeLorza feeding ratio = 36.2% instar larvae.
(Yellow butterfly) (1)
0.01% Feeding deterrence
ratio = 34.3%

0.001% Feeding deterrence


ratio = 81.6%

(1) Numata, A., Katsuno, T., Yamamoto, K., Nishida, T., Takemura, T., and Seto, K. (1984) Chem. Pharm. Bull.,
32, 325.
(2) Chakrabarti, A. and Chakraborty, D.P. (1988) Phytochemistry, 27, 3683.

© 2005 by CRC Press LLC


944 Opender Koul

TULIRINOL C17H22O5
(306.36)
M.p. : 204–206°

[α]23
D : –51° (MeOH)

HO H

H
O

O
OAc
CH2

(1) (1)

SOURCE: Liriodendron tulipifera L., tulip poplar (Magnoliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Lymantria dispar (L.) Leaf disk 50 µg/ml Feeding deterrence = Treatment to larvae.
(Gypsy moth) choice test 31.0% (1)

250 µg/ml Feeding deterrence =


47.0%

(1) Doskotch, R.W., Fairchild, E.H., Huang, C., Wilton, J.H., Beno, M.A., and Christoph, G.G. (1980) J. Org.
Chem., 45, 1441.

© 2005 by CRC Press LLC


Insect Antifeedants 945

TYLOPHORINE C24H27O4N
(393.48)
M.p. : 287–288° (dec.)
OCH3
[α]25
D : –21.45° (CHCl3)

H3CO
H

H3CO

OCH3

(1, 2) (1)

SOURCE: Tylophora asthmatica Wight & Arn, tylophora (Asclepiadaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Artificial diet 2.9 ppm Feeding deterrence = Treatment to larvae
(Tobacco armyworm) feeding 50.0% of 60 to 70 mg body
weight pre-starved
for 4 h.

Concentration = EC50
value.
(2)

(1) Mulchandani, N.B. and Venkatachalam, S.R. (1976) Phytochemistry, 15, 1561.
(2) Verma, G.S., Ramakrishna, V., Mulchandani, N.B., and Chadha, M.S. (1986) Entomol. Exp. Appl., 40, 99.

© 2005 by CRC Press LLC


946 Opender Koul

(±)TYLOPHORININE C23H25O4N
(379.46)
M.p. : 246° (dec.)

H3CO
OH
H

H3CO

OCH3

(1, 2) (1)

SOURCE: Tylophora asthmatica Wight & Arn, tylophora (Asclepiadaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Artificial diet 8.6 ppm Feeding deterrence = Treatment to larvae
(Tobacco armyworm) feeding 50.0% of 60 to 70 mg body
weight pre-starved
for 4 h.

Concentration = EC50
value.
(2)

(1) Govindachari, T.R., Pai, B.R., Prabhakar, S., and Savitri, T.S. (1965) Tetrahedron, 21, 2573.
(2) Verma, G.S., Ramakrishna, V., Mulchandani, N.B., and Chadha, M.S. (1986) Entomol. Exp. Appl., 40, 99.

© 2005 by CRC Press LLC


Insect Antifeedants 947

TYRAMINE – HYDROCHLORIDE C8H11ON-HCl


(173.64)
M.p. : 269° (HCl)

NH2.HCl

OH

(1) (1)

SOURCE: Sample test (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Nilaparvata lugens Stal. Sucrose Feeding deterrence = 1. Treatment to adult


(Brown planthopper) solution 1000 ppm 86.0% females.
feeding 100 ppm 73.0 % (1)
10 ppm 27.0%
FI50 = 36.94 ppm
Feeding deterrence = 2. Treatment to adult
2. Sogatella furcifera (Horvath) Sucrose 1000 ppm 82.0% females.
(Plant hopper) solution 100 ppm 63.0% (1)
feeding 10 ppm 35.0% FI50 = 36.33 ppm

Feeding deterrence = 3. Treatment to adult


3. Laodelphax striatella (Fallen) Sucrose 1000 ppm 80.0% females.
(Planthopper) solution 100 ppm 71.0% (1)
feeding 10 ppm 54.0%

Feeding deterrence = 4. Treatment to adult


4. Nephotettix cincticeps Sucrose 1000 ppm 97.0% females.
(Uhler.) solution 100 ppm 77.0% (1)
(Fruit leafhopper) feeding 10 ppm 42.0% FI50 = 17.7 ppm
FI50 calculated from
Reference 1

LD50 (mice): 229 mg/kg (ivn.) (2)

(1) Kurata, S. and Sogawa, K. (1976) Appl. Ent. Zool., 11, 89.
(2) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC


948 Opender Koul

UGANDENSIDIAL C17H24O5
(308.37)
M.p. : 141–143°
(137–140°)

[α]20
D : –421.5° (CHCl3)
CHO
OH
CHO

H
OAc

(1,3) (1, 2)

SOURCE: Warburgia ugandensis Sprague, African muziga (Canellaceae) (1, 3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera exempta (Walker) Leaf disk >0.1 ppm Feeding inhibition = Treatment to larvae.
(Nutgrass armyworm) choice test Weaker than Quantitative data not
warburganal recorded.
(3)

(1) Brooks, C.J. and Draffan, G.H. (1969) Tetrahedron, 25, 2887.
(2) Canonica, L., Corbella, A., Gariboldi, P., Jommi, G., Krepinsky, J., Ferrari, G., and Casagrande, C. (1969)
Tetrahedron, 25, 3895.
(3) Nakanishi, K. and Kubo, I. (1977) Israel J. Chem., 16, 28.

© 2005 by CRC Press LLC


Insect Antifeedants 949

UNDECANOIC ACID C11H22O2


(186.29)
M.p. : 28.2–28.6°

B.p. : 212.5°/100 mm

OH

(1) (1)

SOURCE: Synthetic (2)


Hibiscus syriacus L., rose-of-sharon (Malvaceae) (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Incisitermes minor (Hagen) Paper towel 0.05 mg/cm2 Feeding inhibition = 1. Treatment to
(Western dry wood termite) disk test 11.6% after 6-day immature termites.
exposure Data calculated from
Reference 2.
(2)

2. Anthonomus grandis Bohem. Plate 100 µg/ Feeding inhibition = 2. Treatment to adult
(Boll weevil) bioassay feeding site About 87.0% after weevils.
3 h and 80.0% after (3)
6 h in males and 84.0
and 78.0% in
females,
respectively.

LD50 (mouse): 140 mg/kg (ivn.) (4)

(1) Cason, J. and Winans, W.R. (1950) J. Org. Chem., 15, 139.
(2) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39.
(3) Bird, T.G., Hedin, P.A., and Burks, M.L. (1987) J. Chem. Ecol., 13, 1087.
(4) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC


950 Opender Koul

10 – UNDECENOIC ACID C11H20O2


(184.28)
M.p. : 24.5°

B.p. : 275°/100 mm

OH

(1, 2) (1)

SOURCE: Synthetic (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Incisitermes minor (Hagen) Paper towel 0.05 mg/cm2 Feeding inhibition = Treatment to
(Western dry wood termite) disk test 12.1% after 6-day immature termites.
exposure (2)

Data calculated from


Reference 2.

LD50 (rats): 2500 mg/kg (oral) (3)

(1) Nogueira, P.L. and Prista, H.R. (1954) Anais. Fac. Farm. Porta., 14, 19.
(2) Scheffrahn, R. H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39.
(3) Opdyke, D.L.J. (1978) Food Cosmet. Toxicol., 16, 883.

© 2005 by CRC Press LLC


Insect Antifeedants 951

UNEDOSIDE C14H20O9
(332.30)
M.p. : 232–234°

OH
H

O
O

H
O - glu

(1) (1)

SOURCE: Canthium euroides (Rubiaceae)


Arbutus unedo L., arbutus (Ericaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera exempta (Walker) Leaf disk 100 ppm Feeding inhibition = 1. Treatment to
(Nutgrass armyworm) choice test 100% larvae.
(2)

2. Epilachna varivestis Mulsant Leaf disk 100 µg/cm2 Feeding inhibition = 2. Treatment to
(Mexican bean beetle) choice test 100% beetles.
(2)

(1) Geisman, T.A., Knaack, W.F. Jr., and Knight, J.O. (1966) Tetrahedron Lett., 1245.
(2) Kubo, I. and Nakanishi, K. (1978) Adv. Pestic. Sci., 2, 284.

© 2005 by CRC Press LLC


952 Opender Koul

URSINIOLIDE–A C22H28O7
(404.46)
M.p. : 140–142°

[α]20
D : –237°

OCO
O

AcO CH2
O

(1, 2) (1)

SOURCE: Ursinia anthemoides (L.) Poiret. (Asteraceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius (L.) Wafer disk 10 mg/cm3 Feeding deterrence 1. Treatment given to
(Grain weevil) test coefficient = 80.2 adults.

2. Tribolium confusum Duv. Wafer disk 10 mg/cm3 Feeding deterrence 2. Treatment given to
(Confused flour beetle) test coefficient both adults and
Adults = 160.2 larvae.
Larvae = 133.4

3. Trogoderma granarium Wafer disk 10 mg/cm3 Feeding deterrence 3. Treatment given to


Everts test coefficient = 96.2 larvae.
(Khapra beetle)
Neutral value = 0
Absolute feeding
deterrence value =
200
(2)

(1) Samek, Z., Holub, M., Rychlewska, U., Grabarczyk, H., and Dordz, B. (1979) Tetrahedron Lett., 28, 2691.
(2) Nawrot, J., Bloszyk, E., Grabarczyk, H. Drozdz, B., Daniewski, W.M., and Holub, M.. (1983) Prace. Nauk.
Inst. Ochr. Roslin, 25, 91.

© 2005 by CRC Press LLC


Insect Antifeedants 953

(+) USNIC ACID C18H16O7


(344.32)
M.p. : 203–204°

[α]D : + 500° (CHCl3)


OH OH O

HO O O

(1, 2) (1, 2)

SOURCE: Usnea lapponica Vain, lichen (Pteridophyta)


U. filipendula Stirton, lichen (Pteridopyhta) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera littoralis (Boisd.) Artificial diet 10 µmol/g Feeding inhibition = Treatment to 3rd
(Egyptian cotton leaf worm) choice test 70.0% instar larvae for 24 h.
Data calculated from
Reference 2.
(2)

LD50 (mice): 838 mg/kg (oral) (3)

(1) Dean, F.M., Halewood, P., Mongkolsuk, S., Robertson, A., and Whalley, W.B. (1953) J. Chem. Soc., 1250.
(2) Emmerich, R., Giez, I., Lange, O.L., and Proksch, P. (1993) Phytochemistry, 33, 1389.
(3) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC


954 Opender Koul

(–) USNIC ACID C18H16O7


(344.32)
M.p. : 203–204°

[α]20
D : –494° (CHCl3)
OH OH O

HO O O

(1, 2) (1, 2)

SOURCE: Cladonia convoluta (Lam.) P. Cout., lichen (Pteridophyta)


C. stellaris (Opiz.) Pouzar et vezda, lichen (Pteridopyhta) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera littoralis (Boisd.) Artificial diet 10 µmol/g Feeding inhibition = Treatment to 3rd
(Egyptian cotton leaf worm) choice test 82.0% instar larvae for 24 h.
Data calculated from
Reference 2.
(2)

(1) Dean, F.M., Halewood, P., Mongkolsuk, S., Robertson, A., and Whalley, W.B. (1953) J. Chem. Soc., 1250.
(2) Emmerich, R., Giez, I., Lange, O.L., and Proksch, P. (1993) Phytochemistry, 33, 1389.

© 2005 by CRC Press LLC


Insect Antifeedants 955

UVIDIN–A C15H24O3
(252.35)
M.p. : 123–124°

[α]20
D : +151.1° (CHCl3)

HO

(1, 2) (1, 2)

SOURCE: Lactarius uvidus Fr., mushroom (Russulaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera littoralis (Boisd.) Leaf disk test 100 ppm Feeding inhibition 1. Treatment to
(Egyptian cotton leaf worm) ratio = 92.4% larvae.
(3)
20 ppm Feeding inhibition
ratio = 23.0%

2. Leptinotarsa decemlineata Leaf disk test 100 ppm Feeding inhibition 2. Treatment to
(Say) ratio = 28.0% beetles.
(Colorado potato beetle) (3)

(1) DeBernardi, M., Mellerio, G., Vidari, G., Vita-Finzi, P., and Fronza, G. (1980) J. Chem. Soc. Perkin Trans.
I, 221.
(2) DeBernardi, M., Mellerio, G., Vidari, G., Vita-Finzi, P., and Fronza, G. (1983) J. Chem. Soc. Perkin Trans.
I, 2739.
(3) Garlaschelli, L., Mellerio, G., Vidari, G., and Vita-Finzi, P. (1994) J. Nat. Prod., 57, 905.

© 2005 by CRC Press LLC


956 Opender Koul

UVIDIN–B C15H24O4
(268.35)
M.p. : 180–181°

[α]20
D : +171° (Me2CO)
HO

HO

(1, 2) (1, 2)

SOURCE: Lactarius uvidus Fr., mushroom (Russulaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera littoralis (Boisd.) Leaf disk test 100 ppm Feeding inhibition 1. Treatment to
(Egyptian cotton leaf worm) ratio = 41.0% larvae.
(3)

2. Leptinotarsa decemlineata Leaf disk test 100 ppm Feeding inhibition 2. Treatment to
(Say) ratio = 6.0% beetles.
(Colorado potato beetle) (3)

(1) DeBernardi, M., Mellerio, G., Vidari, G., Vita-Finzi, P., and Fronza, G. (1980) J. Chem. Soc. Perkin Trans.
I, 221.
(2) DeBernardi, M., Mellerio, G., Vidari, G., Vita-Finzi, P., and Fronza, G. (1983) J. Chem. Soc. Perkin Trans.
I, 2739.
(3) Garlaschelli, L., Mellerio, G., Vidari, G., and Vita-Finzi, P. (1994) J. Nat. Prod., 57, 905.

© 2005 by CRC Press LLC


Insect Antifeedants 957

UVIDIN–A LACTARINATE C33H56O5


(532.80)
Waxy solid
M.p. : 52–53°

[α]20
D : + 101.8° (CHCl3)
OCO

O
O

(1) (1)

SOURCE: Lactarius uvidus Fr., mushroom (Russulaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera littoralis (Boisd.) Leaf disk test 100 ppm Feeding inhibition 1. Treatment to
(Egyptian cotton leaf worm) ratio = 68.0% larvae.
(1)
20 ppm Feeding inhibition
ratio = 7.0%

2. Leptinotarsa decemlineata Leaf disk test 100 ppm Feeding inhibition 2. Treatment to
(Say) ratio = 4.0% beetles.
(Colorado potato beetle) (1)

(1) Garlaschelli, L., Mellerio, G., Vidari, G., and Vita-Finzi, P. (1994) J. Nat. Prod., 57, 905.

© 2005 by CRC Press LLC


958 Opender Koul

VACHANIC ACID C15H24O3


(252.35)
M.p. : 174–176°

[α]20
D : –45.6° (CHCl3)

CH2

HO COOH
H

(1) (1)

SOURCE: Dittrichia viscosa (L.) Grenter, inula (Asteraceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius (L.) Wafer disk 10 mg/cm3 Feeding deterrence 1. Treatment given to
(Grain weevil) test coefficient = 115.1 adults.

2. Tribolium confusum Duv. Wafer disk 10 mg/cm3 Feeding deterrence 2. Treatment given to
(Confused flour beetle) test coefficient both adults and
Adults = 99.0 larvae.
Larvae = 160.3

3. Trogoderma granarium Wafer disk 10 mg/cm3 Feeding deterrence 3. Treatment given to


Everts test coefficient = 18.8 larvae.
(Khapra beetle)
Neutral value = 0
Absolute feeding
deterrence value =
200
(1)

(1) Daniewski, W.M., Kroszczynski, W., Bloszyk, E., Dordz, B., Nawrot, J., Rychlewska, U., Budesinsky, M.,
and Holub, M.. (1986) Collect. Czech. Chem. Commun., 51, 1710.

© 2005 by CRC Press LLC


Insect Antifeedants 959

VASICINE C11H12ON2
(188.23)
M.p. : 212°

[α]14
D : –254° (CHCl3)

OH

(1) (1, 2)

SOURCE: Justicia adhatoda L., vasaka (Acanthaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Aulacophora foveicollis Leaf spray 0.05% Feeding inhibition 1. Treatment to adult


(Lucas) test ratio = 33.0% beetles.
(Red leaf beetle) (1)
0.1% Feeding inhibition
ratio = 56.2%

2. Epilachna vijintioctopunctata Leaf spray 0.05% Feeding inhibition 2. Treatment to


(Fab.) test ratio = 73.3% adults.
(Brinjal beetle) (1)
0.1% Feeding inhibition
ratio = 77.0%

LD50 (rats): 640 mg/kg (oral) (3)

(1) Saxena, B.P., Tikku, K., Atal, C.K., and Koul, O. (1986) Insect Sci. Applic., 7, 489.
(2) Mehta, D.R., Naravane, J.S., and Desai, R.M. (1963) J. Org. Chem., 28, 445.
(3) Lewis, R.J. (1992) Sax’s Dangerous Properties of Industrial Materials, 8th edition, Van Nostrand Reinhold.

© 2005 by CRC Press LLC


960 Opender Koul

VASICINOL C11H12O2N2
(204.23)
M.p. : 272–273°
(260°- dec.)

[α]25
D : +2.5° (AcOH)

HO
N

OH

(1) (1, 2, 3)

SOURCE: Justicia adhatoda L., vasaka (Acanthaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Aulacophora foveicollis Leaf spray 0.05% Feeding inhibition 1. Treatment to adult


(Lucas) test ratio = 37.2% beetles.
(Red leaf beetle) (1)
0.1% Feeding inhibition
ratio = 69.7%

2. Epilachna vijintioctopunctata Leaf spray 0.05% Feeding inhibition 2. Treatment to


(Fab.) test ratio = 35.9% adults.
(Brinjal beetle) (1)
0.1% Feeding inhibition
ratio = 57.7%

(1) Saxena, B.P., Tikku, K., Atal, C.K., and Koul, O. (1986) Insect Sci. Applic., 7, 489.
(2) Spath, E., et al. (1960) Monatsh. Chem., 1150.
(3) Ghosal, S., Ballav, R., Chauhan, P.S., and Mehta, R. (1975) Phytochemistry, 14, 830.

© 2005 by CRC Press LLC


Insect Antifeedants 961

VASICINONE C11H10O2N2
(202.21)
M.p. : 200–201°

[α]D : –129° (CHCl3)

OH

(1) (1, 2)

SOURCE: Justicia adhatoda L., vasaka (Acanthaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Aulacophora foveicollis Leaf spray 0.05% Feeding inhibition 1. Treatment to adult


(Lucas) test ratio = 17.6% beetles.
(Red leaf beetle) (1)
0.1% Feeding inhibition
ratio = 51.8%

2. Epilachna vijintioctopunctata Leaf spray 0.05% Feeding inhibition 2. Treatment to


(Fab.) test ratio = 30.2% adults.
(Brinjal beetle) (1)
0.1% Feeding inhibition
ratio = 56.5%

(1) Saxena, B.P., Tikku, K., Atal, C.K., and Koul, O. (1986) Insect Sci. Applic., 7, 489.
(2) Ghosal, S., Ballav, R., Chauhan, P.S., and Mehta, R. (1975) Phytochemistry, 14, 830.

© 2005 by CRC Press LLC


962 Opender Koul

VERBENONE C10H14O
(150.22)
M.p. : 6.5°

B.p. : 227–228°

[α]18
D : +249.6°

(1, 2) (1, 2)

SOURCE: Commercial sample (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Hylobius pales (Herbst.) Twig dip 10% Feeding inhibition = 1. Treatment to


(Pales weevil) treatment 61.5% 22–65 mg body
choice test weight weevils for
24 h.

Data calculated from


Reference 1.
(1)

2. Hylobius abietis L. Twig dip 10% Feeding inhibition = 2. Treatment to adult


(Pine weevil) assay 45% approx. in weevils for 48 h.
choice situation and Data calculated from
about 38% in no- Reference 3.
choice situation (3)

(1) Salom, S.M., Carlson, J.A., Ang, B.N., Grosman, D.M., and Day, E.R. (1994) J. Entomol. Sci., 29, 407.
(2) Banthorpe, D.V. and Whittaker, D. (1966) Chem. Rev., 66, 643.
(3) Klepzig, K.D. and Schlyter, F. (1999) J. Econ. Entomol., 92, 644.

© 2005 by CRC Press LLC


Insect Antifeedants 963

VESTITOL C16H16O4
(272.30)
M.p. : 156°
(144–145°)

[α]D : +21.6° (MeOH)


HO O

HO OCH3

(1, 2) (1, 2, 3)

SOURCE: Trifolium repens L., grassland huia (Fabaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Heteronychus arator (Fab.) Artificial diet 200 µg/g Feeding inhibition = Treatment to 3rd
(Black beetle) feeding 68.0% instar larvae after
24-h starvation.
100 µg/g Feeding inhibition =
75.0% Data calculated from
Reference 1.
10 µg/g Feeding inhibition = (1)
55.0%

(1) Kurosawa, K., Ollis, W.D., Redman, B.T., Sutherland, I.O., Braga deOliveira, A., Gottlieb, O.R., and Alves,
H.M. (1968) J. Chem. Soc. Chem. Commun., 1263.
(2) Russel, G.B., Sutherland, O.R.W., Christmas, P.E., and Wright, H. (1982) NZ. J. Zool., 9, 145.
(3) Kurosawa, K., Ollis, W.D., Redman, B.T., Sutherland, I.O., and Gottlieb, O.R. (1978) Phytochemistry, 17, 1413.

© 2005 by CRC Press LLC


964 Opender Koul

VINBLASTINE C46H58O9N4
(810.99)
M.p. : 211–216°
OH
[α]26
D : +42° (CHCl3)
N
C2H5

N
N

H3COOC C2H5

H3CO N OCOCH3
H
OH COOCH3

(1, 2) (3)

SOURCE: Catharanthus roseus (L.) G.Don., madagascar periwinkle (Apocynaceae) (4)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera littoralis (Boisd.) Lamellar 0.04% Feeding inhibition = Treatment to larvae.


(Egyptian cotton leaf worm) disk feeding 55.4%
Data calculated from
Reference 4.

Other alkaloids like


catharanthine,
vindoline,
leurocristine, and
ajmalicine were also
evaluated but were
not significantly
active.
(4)

LD50 (mice): 17 mg/kg (i.v.) (5)

(1) Gorman, M., Neuss, N., and Svoboda, G.H. (1959) J. Am. Chem. Soc., 81, 4745.
(2) Moncrief, J.W. and Lipscomb, W.N. (1965) J. Am. Chem. Soc., 87, 4963.
(3) Neuss, N., Gorman, M., Svoboda, G.H., Maciak, G., and Beer, C.T. (1959) J. Am. Chem. Soc., 81, 4754.
(4) Meisner, J., Weissenberg, M., Pelevitch, D., and Aharonson, N. (1981) J. Econ. Entomol., 74, 131.
(5) (1983) Merck Index, p. 1427.

© 2005 by CRC Press LLC


Insect Antifeedants 965

VISMIN C25H28O4
(392.49)
M.p. : 161–164°
(impure)
OH OH O

OH

(1, 2) (1)

SOURCE: Fruits of Vismia spp. (Clusiaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera exempta (Walker) Glass fiber 10–3 M Feeding inhibition = 1. Treatment to last
(Nutgrass armyworm) disk test 61.24% instar larvae.
(1)

2. Heliothis virescens (Fab.) Glass fiber 10–3 M Feeding inhibition = 2. Treatment to last
(Tobacco budworm) disk test 56.56% instar larvae.
(1)

3. Locusta migratoria (L.) Glass fiber 10–3 M Feeding inhibition = 3. Treatment to last
(Migratory locust) disk test 79.22% instar larvae.
(1)

(1) Delle Monache, F., Ferrari, F., Bettolo, G.B.M., and Cuca Suarez, L.E. (1980) Planta Medica, 40, 340.
(2) Simmonds, M.S.J., Blaney, W.M., DelleMonache, F., Mac-Quhae, M.M., and Bettolo, G.B.M. (1985) J. Chem.
Ecol., 11, 1593.

© 2005 by CRC Press LLC


966 Opender Koul

VISMINONE–A C23H26O6
(vismione A) (398.46)
M.p. : 140–141°

[α]D : +54° (CHCl3)

O OH OH

OCH3
OAc

(1, 2) (1)

SOURCE: Vismia baccifera (L.) Tr. and Planch, achiote tigre (Clusiaceae) (1,2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera exempta (Walker) Glass fiber 10–3 M Feeding inhibition = 1. Treatment to last
(Nutgrass armyworm) disk test 51.47% instar larvae.
(2)

2. Heliothis virescens (Fab.) Glass fiber 10–3 M Feeding inhibition = 2. Treatment to last
(Tobacco budworm) disk test 67.47% instar larvae.
(2)

3. Locusta migratoria (L.) Glass fiber 10–3 M Feeding inhibition = 3. Treatment to last
(Migratory locust) disk test 80.14% instar larvae.
(2)

(1) DelleMonache, F., Ferrari, F., Bettolo, G.B.M., Peny, M., Silvio, C., Fedeli, W., Gavuzzo, E., and Vaciago,
A. (1979) Gazz. Chim. Ital., 109, 301.
(2) Simmonds, M.S.J., Blaney, W.M., DelleMonache, F., Mac-Quhae, M.M., and Bettolo, G.B.M. (1985) J. Chem.
Ecol., 11, 1593.

© 2005 by CRC Press LLC


Insect Antifeedants 967

VISMINONE–B C21H22O5
(vismione B) (354.40)
M.p. : 200–202°

[α]D : +24° (CHCl3)

O OH O

OCH3
OH

(1, 2) (1)

SOURCE: Vismia baccifera (L.) Tr. and Planch, achiote tigre (Clusiaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera exempta (Walker) Glass fiber 10–3 M Feeding inhibition = 1. Treatment to last
(Nutgrass armyworm) disk test 69.69% instar larvae.
(2)

2. Heliothis virescens (Fab.) Glass fiber 10–3 M Feeding inhibition = 2. Treatment to last
(Tobacco budworm) disk test 58.98% instar larvae.
(2)

3. Locusta migratoria (L.) Glass fiber 10–3 M Feeding inhibition = 3. Treatment to last
(Migratory locust) disk test 100% instar larvae.
(2)

(1) Pinheiro, R.M., Quhae, M.M., Bettolo, G.B.M., and Monache, F.D. (1984) Phytochemistry, 23,1737.
(2) Simmonds, M.S.J., Blaney, W.M., DelleMonache, F., Mac-Quhae, M.M., and Bettolo, G.B.M. (1985) J. Chem.
Ecol., 11, 1593.

© 2005 by CRC Press LLC


968 Opender Koul

VISNAGIN C13H10O4
(230.22)
M.p. : 144–145°
(138–140°)

O O

OCH3 O

(1, 2) (1, 2)

SOURCE: Pimpinella monica Dalz., pimpinella (Apiaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Artificial diet 62.2 ppm Feeding inhibition = Treatment to 4th
(Tobacco armyworm) assay 50.0% instar larvae pre-
starved for 4 h.
Treatment until 48 h.
Concentration = EC50.
(2)

(1) Spath, E., et al. (1941) Chem. Ber., 74, 1492.


(2) Luthria, D.L., Ramakrishnan, V., and Banerji, A. (1993) J. Nat. Prod., 56, 671.

© 2005 by CRC Press LLC


Insect Antifeedants 969

VITEXIN C21H20O10
(432.38)
M.p. : 269–270° (dec.)

[α]20
D : –14.5° (pyridine)
CH2OH
OH
O
HO
OH O
HO HO

OH O

(1, 2) (1, 2)

SOURCE: Semisynthetic (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Schizaphis graminum Lamellar 0.25% Feeding inhibition = 1. Treatment to


(Rondani) disk feeding 50.0% 50–75 aphids at
(wheat aphid) random for 24 h.
(3)

2. Myzus persicae (Sulzer) Artificial diet 0.1% Feeding inhibition = 2. Treatment to


(green peach aphid) feeding 50.0% 50–75 aphids at
random for 8 h.
(3)

(1) Evans, W.H., McGookin, A., Jurd, L., Robertson, A., and Williamson, W.R.N. (1957) J. Chem. Soc., 3510.
(2) Horowitz, R.M. and Gentili, B. (1964) Chem & Ind., 498.
(3) Dreyer, D.L. and Jones, K.C. (1981) Phytochemistry, 20, 2489.

© 2005 by CRC Press LLC


970 Opender Koul

VOLKENSIN C33H44O9
(584.71)
M.p. : 185–187°

O
OH

O
O

O
AcO OH

(1) (1)

SOURCE: Melia volkensii Gurke, East African melia (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera frugiperda Leaf disk 3.5 µg/cm2 Feeding inhibition = Treatment to 3rd
(J.E. Smith) choice test 50.0% instar larvae for 15 h.
(Fall armyworm) Concentration = EC50.
(1)

(1) Rajab, M.S., Bentley, M.D., Alford, A.R., and Mendel, M.J. (1988) J. Nat. Prod., 51, 168.

© 2005 by CRC Press LLC


Insect Antifeedants 971

VOLKENSIN HYDROXYLACTONE C33H42O9


(582.69)
M.p. : 240–244° (dec.)

O
O

O
O

O
AcO OH

(1) (1)

SOURCE: Melia volkensii Gurke, East African melia (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera frugiperda Leaf disk 6.0 µg/cm2 Feeding inhibition = Treatment to 3rd
(J.E. Smith) choice test 50.0% instar larvae for 15 h.
(Fall armyworm) Concentration = EC50.
(1)

(1) Rajab, M.S., Bentley, M.D., Alford, A.R., and Mendel, M.J. (1988) J. Nat. Prod., 51, 168.

© 2005 by CRC Press LLC


972 Opender Koul

VULPINIC ACID C19H14O5


(322.32)
M.p. : 145–146°

O
OCH3

OH

(1) (1)

SOURCE: Letheria vulpina (L.) Hue, lichen (Pteridophyta) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera littoralis (Boisd.) Artificial diet 10 µmol/g Feeding inhibition = Treatment to 3rd
(Egyptian cotton leaf worm) choice 60.0% instar larvae for 24 h.
feeding
Data calculated from
Reference 1.
(1)

(1) Emmerich, R., Giez, I., Lange, O.L., and Proksch, P. (1993) Phytochemistry, 33, 1389.
(2) Rao, Y.S. (1976) Chem. Rev., 76, 625.

© 2005 by CRC Press LLC


Insect Antifeedants 973

WARBURGANAL C15H22O3
(250.34)
M.p. : 106–107°

[α]22
D : +260° (CHCl3)

CHO
OH
CHO

(1) (1, 2)

SOURCE: Warburgia ugandensis Sprague, African muziga (Canellaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera exempta (Walker) Leaf disk 0.1 ppm Feeding inhibition = 1. Treatment to
(Nutgrass armyworm) choice test Minimum level to larvae.
show inhibition. (2)

2. Spodoptera littoralis (Boisd.) Leaf disk 10 ppm Feeding inhibition = 2. Treatment to


(Egyptian cotton leaf worm) choice test Minimum level to larvae.
show inhibition. (2)

3. Schistocerca gregaria Forsk. Glass fiber 0.01% Feeding inhibition = 3. Treatment to 5th
(Desert locust) disk test 85–90% instar larvae.
(2)

4. Locusta migratoria (L.) Glass fiber 0.01% Feeding inhibition = 4. Treatment to 5th
(Migratory locust) disk test 85–90% instars.
(2)

5. Leptinotarsa decemlineata Leaf disk 5 mM Feeding inhibition = 5. Treatment to


(Say) dual-choice 79.0% larvae of 90–120 mg
(Colorado potato beetle) assay body weight for a
period of 3 h.
(3)

LD50 (mice): 20.4 mg/kg (s.c.) (2)

(1) Kubo, I., Lee, Y., Pettei, M., Pilkiewicz, F, and Nakanishi, K. (1976) J. Chem. Soc. Chem. Commun., 1013.
(2) Nakanishi, K. (1980) In Insect Biology in the Future, Academic Press, pp. 603–611.
(3) Gols, G.J.Z., van Loon, J.J.A., and Messchendorp, L. (1996) Entomol. Exp. Appl., 79, 69.

© 2005 by CRC Press LLC


974 Opender Koul

WILFORINE C43H49O18N
(867.86)
M.p. : 169–170°
OAc
AcO OAc
[α]25
D : + 30° (Acetone)

BzO OAc

O
O
O
OH OAc
O
O

(1, 2) (1)

SOURCE: Maytenus rigida Mart. (Celastraceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Locusta migratoria (L.) Filter paper 5 × 10–5% Feeding deterrence = 1. Treatment to


(Migratory locust) disk test dry weight 50% larvae.
(2)

2. Schistocerca gregaria Filter paper 1 × 10–1% Feeding deterrence = 2. Treatment to


(Forsk.) disk test dry weight 50% larvae.
(Desert locust) (2)

3. Locustana paradalina Filter paper 5 × 10–4% Feeding deterrence = 3. Treatment to


(Walker) disk test dry weight 50% larvae.
(Locust) (2)

4. Helicoverpa zea (Boddie) Wet filter 1 × 10–2% Feeding deterrence = 4. Treatment to


(Corn earworm) paper disk 50% larvae.
test (2)

5. Helicoverpa armigera Wet filter 2 × 10–2% Feeding deterrence = 5. Treatment to


(Hubner) paper disk 50% larvae.
(Grampod borer) test (2)

6. Spodoptera littoralis (Boisd.) Wet filter 1 × 10–3% Feeding deterrence = 6. Treatment to


(Egyptian cotton leaf worm) paper disk 50% larvae.
test (2)

(1) Beroza, M. (1951) J. Am. Chem. Soc., 73, 3656.


(2) Monache, F.D., Bettolo, G.B.M., and Bernays, E.A. (1984) Z. Angew. Entomol., 97, 406.

© 2005 by CRC Press LLC


Insect Antifeedants 975

WITHAFERIN–A C28H38O6
(470.61)
M.p. : 252–253°

CH2OH [α]28
D : + 125° (CHCl3)

O O
H
O

O
OH (1, 2) (1, 2)

SOURCE: Withania somnifera (L.) Dunal., withania (Solanaceae) (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Epilachna varivestis Muls. Leaf residue 0.1% Feeding inhibition = Treatment to 4th
(Mexican bean beetle) test 98.8% instar larvae for 48 h.
Data calculated from
0.05% Feeding inhibition = Reference 3.
57.7% (3)

0.025% Feeding inhibition = FI50 = 0.039%


24.7% Calculated from
Reference 3.

LD50 (mouse): 54 mg/kg (ipr.) (4)

(1) Lavie, D., Glotter, E., and Shvo, Y. (1965) J. Chem. Soc., 7517.
(2) Lavie, D., Glotter, E., and Shvo, Y. (1965) J. Org. Chem., 30, 1774.
(3) Ascher, K.R.S., Schmutterer, H., Glotter, E., and Kirson, I. (1981) Phytoparasitica, 9, 197.
(4) (1994) Dictionary of Natural Products, Chapman & Hall, London.

© 2005 by CRC Press LLC


976 Opender Koul

WITHANICANDRIN C28H36O6
(468.59)
M.p. : 267–269°

[α]D : + 105° (CHCl3)

O
O O
H
O

O
OH
(1, 2) (1)

SOURCE: Nicandra physaloides (L.) Gaertn., apple-of-Peru (Solanaceae) (1, 2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera littoralis (Boisd.) Styropor 100 ppm Feeding inhibition = 1. Treatment to early
(Egyptian cotton leaf worm) method 6.0% 6th instar larvae for
48 h. Treatment
given in a mixture
with daturalactone.
(2)

2. Epilachna varivestis Muls. Bean leaf test 100 ppm Feeding inhibition = 2. Treatment to 4th
(Mexican bean beetle) 100% instar larvae for 48 h.
(2)
10 ppm Feeding inhibition =
100%

3. Tribolium castaneum Yeast diet 100 ppm Feeding inhibition = 3. Treatment to 0–3
(Herbst.) feeding 44.8% hour old larvae for
(Red flour beetle) 14 days.
(2)

Data calculated from


Reference 2.

(1) Kirson, I., Lavie, D., Subramanian, S.S., Sethi, P.D., and Glotter, E. (1972) J. Chem. Soc. Perkin Trans I, 2109.
(2) Ascher, K.R.S., Eliyahu, M., Glotter, E., Goldman, A., Kirson, I., Abraham, A., Jacobson, M., and Schmutterer,
H. (1987) Phytoparasitica, 15, 15.

© 2005 by CRC Press LLC


Insect Antifeedants 977

WITHANOLIDE–D C28H38O6
(470.61)
M.p. : 253–255°

[α]D : + 80° (CHCl3)


OH

O O
H
O

O
OH (1, 2, 3) (1, 2)

SOURCE: Withania somnifera (L.) Dunal., withania (Solanaceae) (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Epilachna varivestis Muls. Leaf residue 0.1% Feeding inhibition = Treatment to 4th
(Mexican bean beetle) test 77.8% instar larvae for 48 h.
(3)

0.05% Feeding inhibition = FI50 = 0.036%


76.5%
Data calculated from
Reference 3.
0.025% Feeding inhibition =
28.9%

(1) Lavie, D., Kirson, I., and Glotter, E. (1968) Israel J. Chem., 6, 671.
(2) Kirson, I., Glotter, E., Abraham, A., and Lavie, D (1970) Tetrahedron, 26, 2209.
(3) Ascher, K.R.S., Schmutterer, H., Glotter, E., and Kirson, I. (1981) Phytoparasitica, 9, 197.

© 2005 by CRC Press LLC


978 Opender Koul

WITHANOLIDE–E C28H38O7
(486.60)
M.p. : 167–168°

[α]D : + 103.5° (CHCl3)


OH

O O
OH
O

OH

O (1, 2)
(1, 2)

SOURCE: Physalis peruviana L., Peruvian groundcherry (Solanaceae) (3)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera littoralis (Boisd.) Styropor 0.1% Feeding inhibition = 1. Treatment to


(Egyptian cotton leaf worm) method 100% larvae of 170–190
0.005% Feeding inhibition = mg body weight.
95.9% (3)
0.001% Feeding inhibition =
68.2% FI50 = 0.0089%
0.0005% Feeding inhibition = Data calculated from
14.4% Reference 3.

2. Epilachna varivestis Muls. Leaf residue 0.1% Feeding inhibition = 2. Treatment to 4th
(Mexican bean beetle) test 100% instar larvae for 48 h.
(4)
0.05% Feeding inhibition =
100% Data calculated from
Reference 4.

(1) Glotter, E., Abraham, A., Gunzberg, G., and Kirson, I. (1977) J. Chem. Soc. Perkin Trans I, 341.
(2) Kirson, I., Abraham, A., Sethi, P.D., Subramanian, S.S., and Glotter, E. (1976) Phytochemistry, 15, 340.
(3) Ascher, K.R.S., Nemny, N.E., Eliyahu, M., Kirson, I., Abraham, A., and Glotter, E. (1980) Experientia, 36, 998.
(4) Ascher, K.R.S., Schmutterer, H., Glotter, E., and Kirson, I. (1981) Phytoparasitica, 9, 197.

© 2005 by CRC Press LLC


Insect Antifeedants 979

WITHANOLIDE–S C28H40O8
(504.62)

M.p. : 272° (dec.)

[α]D : + 95.5° (MeOH)


OH

O O
OH
O

OH

OH
OH
(1, 2) (1)

SOURCE: Physalis peruviana L., Peruvian groundcherry (Solanaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera littoralis (Boisd.) Styropor 0.1% Feeding inhibition = 1. Treatment to


(Egyptian cotton leaf worm) method 41.1% larvae of 170–190
mg body weight.
(2)
0.01% Feeding inhibition = Data calculated from
44.2% Reference 2.

(1) Glotter, E., Abraham, A., Gunzberg, G., and Kirson, I. (1977) J. Chem. Soc. Perkin Trans I, 341.
(2) Ascher, K.R.S., Nemny, N.E., Eliyahu, M., Kirson, I., Abraham, A., and Glotter, E. (1980) Experientia, 36, 998.

© 2005 by CRC Press LLC


980 Opender Koul

XANTHOTOXIN C12H8O4
(216.19)
M.p. : 146°

O O O

OCH3

(1, 2) (2)

SOURCE: Oryxa japonica Thumb., Japanease kokusagi (Rutaceae) (1)


Also from Angelica silvestris L., angelica (Apiaceae) (4)
Atalantia recemosa Wight and Arn, wild lime (Rutaceae) (5)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Spodoptera litura (Fab.) Leaf disk 100 ppm Feeding inhibition = 1. Treatment to 3rd
(Tobacco armyworm) test 50.0% instar larvae.
(1)
Artificial 31.0 ppm Feeding inhibition = Treatment to 4th
diet 50.0% instar larvae starved
feeding for 4 h. Treatment
duration = 48 h.
(4)

2. Periplaneta americana (L.) Sugar 0.1 mg/1.5 g Feeding inhibition = 2. Treatment to adult
(American cockroach) pellet pellet 54.0% cockroach.
method (3)

3. Blatella germanica (L.) Sugar 0.1 mg/1.5 g Feeding inhibition = 3. Treatment to adult
(German cockroach) pellet pellet 43.0% cockroach.
method (3)

4. Stylopyga rhombifolia Sugar 0.1 mg/1.5 g Feeding inhibition = 4. Treatment to


(Cockroach) pellet pellet 88.0% adults.
method (3)

5. Peridroma saucia (Hubner) Leaf disk 14.25 µg/cm2 Feeding inhibition = 5. Treatment to 5th
(Variegated cutworm) choice test 45.3% instar larvae for 5 h.

57.0 µg/cm2 Feeding inhibition = (4)


97.6

© 2005 by CRC Press LLC


Insect Antifeedants 981

6. Pieris rapae crucivora Leaf disk 5 × 10–7 mol/cm2 Feeding inhibition = 6. Treatment to 5th
Boisd. dual- 28.1% instar larvae pre-
(Cabbage butterfly) choice starved for 3 h.
test
Treatment duration =
2 h.
(6)

LD50 (rats): 791 mg/kg (oral) (7)

(1) Yajima, T., Kato, N., and Munakata, K. (1977) Agric. Biol. Chem., 41, 1263.
(2) Dev, S. and Koul, O. (1997) Insecticides of Natural Origin, Harwood Academic Publishers, Amsterdam, p. 204.
(3) Yajima, T. and Munakata, K. (1979) Agric. Biol. Chem., 43, 1701.
(4) Nawrot, J., Koul, O., Isman, M.B., and Harmatha, J. (1991) J. Appl. Ent., 112, 194.
(5) Luthria, D.L., Ramakrishnan, V., Verma, G.S., Prabhu, B.R., and Banerji, A. (1989) J. Agric. Food Chem.,
37, 1435.
(6) Yano, K. and Tanaka, N. (1995) Biosci. Biotech. Biochem., 59, 1130.
(7) (1981) IARC Monograph, 24, 101.

© 2005 by CRC Press LLC


982 Opender Koul

XANTHOTOXOL ETHYL ETHER C13H10O4


(230.22)
M.p. : 104–106°

OC2H5

H O O O

(1) (1)

SOURCE: Synthetic (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Artificial diet 23.0 ppm Feeding inhibition = Treatment to 4th
(Tobacco armyworm) assay 50.0% instar larvae pre-
starved for 4 h.
Treatment duration =
48 h.

Concentration = EC50
value.
(1)

(1) Luthria, D.L., Ramakrishnan, V., Verma, G.S., Prabhu, B.R., and Banerji, A. (1989) J. Agric. Food Chem.,
37, 1435.

© 2005 by CRC Press LLC


Insect Antifeedants 983

XANTHOXYLETIN C15H14O4
(258.27)
M.p. : 132.5–134°

O O O

OCH3

(1, 2) (1, 2)

SOURCE: Clausena anisata Hook F., samanobere (Rutaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera exempta (Walker) Leaf disk test 100 ppm Feeding inhibition = Treatment to larvae.
(Nutgrass armyworm) Effective deterrent
500 ppm No quantitative data
recorded.

(1) Virkov, J. and Sednnera, P. (1972) Phytochemistry, 11, 2647.


(2) Gebreyesus, T. and Chapya, A. (1983) In Natural Products for Innovative Pest Management, Current Themes
in Tropical Science, T.R. Odhiambo (ed.), Pergamon Press, Oxford, 237–241.

© 2005 by CRC Press LLC


984 Opender Koul

XANTHYLETIN C14H12O3
(228.24)
M.p. : 131.5°
(127–129°)

O O O

(1, 2) (2, 3)

SOURCE: Boenninghausenia albiflora (Hook.) Reichb., flea plant (Rutaceae) (2)


Atalantia racemosa Wight and Arn, wild lime (Rutaceae) (4)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera litura (Fab.) Artificial diet 870 ppm Feeding inhibition = Treatment to 4th
(Tobacco armyworm) assay 50.0% instar larvae pre-
starved for 4 h.
Treatment duration =
48 h.

Concentration = EC50
value.
(2)

Leaf disk test 2500 ppm Feeding inhibition = Treatment to 3rd


100% within 2 h. instar larvae.
Compound termed as
relative antifeedant
as activity retards
after 6 h.
(4)

(1) King, F.E., Housley, J.R., and King, T.J. (1954) J. Chem. Soc., 1392.
(2) Hosozawa, S., Kato, N., Munakata, K., and Chen, Y. (1974) Agric. Biol. Chem., 38, 1045.
(3) Bowden, B.F., Cleaver, L., Ndalut, P.K., Ritchie, E., and Taylor, W.C. (1975) Aust. J. Chem., 28, 1393.
(4) Luthria, D.L., Ramakrishnan, V., Verma, G.S., Prabhu, B.R., and Banerji, A. (1989) J. Agric. Food Chem.,
37, 1435.

© 2005 by CRC Press LLC


Insect Antifeedants 985

XERANTHOLIDE C15H18O3
(246.31)
M.p. : 190–192°
(183°)

[α]20
D : +223.3° (CHCl3)
H

O O

CH2

(1) (1)

SOURCE: Xeranthemum cylindraceum Sibth and Smith, lilac stars (Asteraceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius (L.) Wafer disk 8 mg/cm3 Feeding deterrence 1. Treatment given to
(Grain weevil) test coefficient = 51–100 adults.

2. Tribolium confusum Duv. Wafer disk 8 mg/cm3 Feeding deterrence 2. Treatment given to
(Confused flour beetle) test coefficient both adults and
Adults = 51–100 larvae.
Larvae = 101–150

3. Trogoderma granarium Wafer disk 8 mg/cm3 Feeding deterrence 3. Treatment given to


Everts test coefficient = larvae.
(Khapra beetle) 101–150
Neutral value = 0
Absolute feeding
deterrence value =
200
(2)

(1) Samek, Z., Holub, M., Dordz, B., Grabarczyk, H., and Hladon, B. (1977) Collect. Czech. Chem. Commun.,
42, 2441.
(2) Nawrot, J., Bloszyk, E., Grabarczyk, H., and Drozdz, B. (1982) Prace. Nauk. Inst. Ochr. Roslin, 24, 27.

© 2005 by CRC Press LLC


986 Opender Koul

XYLOMOLLIN C12H18O7
(274.27)
M.p. : 138–139°

COOCH3
H
O OCH3

O O

H
OH

(1, 2) (1, 2)

SOURCE: Xylocarpus molluscensis Roem. (Meliaceae) (1)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

Spodoptera exempta (Walker) Leaf disk 1000 ppm Feeding inhibition = Treatment to 3rd
(Nutgrass armyworm) choice test Effective deterrent instar larvae.
(3)
No quantitative data
given.

(1) Kubo, I., Miura, I., and Nakanishi, K. (1976) J. Am. Chem. Soc., 98, 6704.
(2) Nakane, M., Hutchinson, C.R., van Engen, D., and Clardy, J. (1978) J. Am. Chem. Soc., 100, 7079.
(3) Kubo, I. and Nakanishi, K. (1977) In Host Plant Resistance to Pests, ACS Symp. Ser., 62, 165.

© 2005 by CRC Press LLC


Insect Antifeedants 987

YATEIN C22H24O7
(400.43)
[α]20
D : –28.4° (CHCl3)
H

O
O
O

H
O

H3CO OCH3

OCH3

(1) (1)

SOURCE: Libocedrus yateensis Guill., South incense cedar (Cupressaceae) (2)

ACTIVITY PROFILE

Test Conc. /
Test Insect Efficacy Remarks
Method Dose

1. Sitophilus granarius (L.) Wafer disk 10 mg/ml Feeding deterrence 1. Treatment given to
(Grain weevil) test coefficient = 189 adults.

2. Tribolium confusum Duv. Wafer disk 10 mg/ml Feeding deterrence 2. Treatment given to
(Confused flour beetle) test coefficient both adults and
Adults = 158 larvae.
Larvae = 143

3. Trogoderma granarium Wafer disk 10 mg/ml Feeding deterrence 3. Treatment given to


Everts test coefficient = 177 larvae.
(Khapra beetle)
Neutral value = 0
Absolute feeding
deterrence value =
200
(2)

(1) Erdtman, H. and Harmatha, J. (1979) Phytochemistry, 18, 1495.


(2) Harmatha, J. and Nawrot, J. (1984) Biochem. Syst. Ecol., 12, 95.

© 2005 by CRC Press LLC

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