Professional Documents
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ANTIFEEDANTS
Opender Koul
Insect Biopesticide Research Centre
Jalandhar, India
CRC PR E S S
Boca Raton London New York Washington, D.C.
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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© 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.
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© 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
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© 2005 by CRC Press LLC
CONTENTS
1 Introduction........................................................................................................................1
References............................................................................................................................6
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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© 2005 by CRC Press LLC
Isoflavonoids ......................................................................................................................63
Alkaloids............................................................................................................................64
Maytansinoids....................................................................................................................65
Ellagitannins ......................................................................................................................65
Aristolochic Acids .............................................................................................................67
References..........................................................................................................................68
5 Commercialization...........................................................................................................73
References..........................................................................................................................77
7 Bioefficacy Monographs..................................................................................................85
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.
INFOCHEMICALS
PHEROMONES ALLELOCHEMICALS
2. Kairomone
2. (−, +) Pheromone
Benefit to receiver 3. Synomone
4. Apneumone
3. (+, +) Pheromone
Benefit to both 5. Antimone
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:
• 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
Monoterpene Lactones
HERBACIOUS
Sesquiterpenes Non-protein
Aminoacids
Cardiac Glycosides
Cucurbitacins
Limonoids WOODY
Diterpenes
Saponins Quassinoids
Polyacetylenes Coumarins
ANGIOSPERMS
------------------------------------------------------------------------------------------------------------
---------
Ecdysteroids Tannins Cyanogens
Juvenoids
GYMNOSPERMS
FERNS
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
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:
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
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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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
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.
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
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
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).
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
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.
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,
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).
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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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.
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
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
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):
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).
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.
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:
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).
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).
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:
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
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
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
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).
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
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).
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
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).
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.
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:
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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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
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
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.
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
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
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
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).
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)
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
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:
• 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)
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).
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)
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
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
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
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.
O O O
O O
HO
HO
O O O
OAc OH OAc
HO HO AcO
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)
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
O OH OH
OH
O OHC O
R HOH2C OH
CHO
CHO CHO OH
OH CHO
CHO CHO
CH2
OH
O
O CHO
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)
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
OCH3
OCH3
C=O R = CH3
R R
> >
>
>
(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
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
OCH3
O O O
OCH3
O O O O
O O
OCH3
OCH3
O O O R1
RO O
O O O
OCH3 R2
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.
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.
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
OCH3
OH
O 9 O
O O O O
O O
OH O OH O
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:
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
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)
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).
OH
HO O O HO O
COOH
O O OH HO OH HO OH
OH OH OH
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).
HO OH HO OH HO OH HO OH
OH OH OH OH
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
O COOCH3
O COOH
NO2
O
NO2
O O
R OCH3
R = H or R = OH HO OCH3
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).
NO2
N O
O H
O NO2
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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Yano, K. (1986) Relationship between chemical structure of phenylalkynes and their anti-
feedant activity for larvae of a cabbage butterfly. Insect Biochem., 16, 717–719.
Yano, K. (1987) Minor components from growing buds of Artemisia capillaris that act as
insect antifeedants. J. Agric. Food Chem., 35, 889–891.
Yano, K. (1998) Relationship between chemical structure of antifeedants from Artemisia
capillaris buds and their antifeedant activity toward Pieris rapae crucivora larvae.
Recent Res. Develop. Agric. Biol. Chem., 2, 293–305.
Yano, K. and Kamimura, H. (1993) Antifeedant activity toward larvae of Pieris rapae
crucivora of phenol ethers related to methyleugenol isolated from Artemisia capillaris.
Biosci. Biotech. Biochem., 57, 129–130.
Yano, K. and Tanaka, N. (1995) Antifeedant activity toward larvae of Pieris rapae crucivora
of aromatic carbonyl compounds related to capillin isolated from Artemisia capillaris.
Biosci. Biotech. Biochem., 59, 1130–1132.
• 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
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
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.
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.
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
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
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.
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:
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.
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.
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:
H COOH
(1, 2) (1)
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.
(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.
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)
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.
ABYSSININ C27H30O8
(482.53)
M.p. : 278°
O
O
H
CHO
OCH3
H
O
OCOCH3
(1) (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)
2-ACETONAPHTHONE C12H10O
(170.21)
M.p. : 56°
B.p. : 171–173°/17 mm
(1, 2) (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 99.2% instar larvae pre-
test starved for 3 h.
The treatment given
for 2 h.
(2)
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)
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.
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)
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.
HO
O
Cl OAc
(1) (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.
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)
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.
11β-ACETOXY-5α-ISOBUTYRYLOXYSILPHINEN-3-ONE C21H30O5
(362.21)
Oil
O C
O
(1) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(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.
11β-ACETOXY-5α-TIGLOYLOXYSILPHINEN-3-ONE C22H30O5
(374.21)
Oil
OAc
Only spectral data given
O O
(1) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(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.
11β-HYDROXY-5α-ANGELOYLOXYSILPHINEN-3-ONE C20H28O4
(332.44)
Oil
O OAng
(1) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(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.
O OAng
(1, 3) (1, 3)
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.
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.
12-α-ACETOXYFRAXINELLONE C16H18O5
(290.32)
M.p. : 102–104°C
O
O
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.
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.
H
OAc
COOH
(1) (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.
OAc
COOH
(1) (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.
5α-ACETOXYSILPHINEN-3-ONE C17H24O3
(276.37)
Oil
O OAc
(1) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(1) Reina, M., Nold, M., Santana, O., Orihuela, J.C., and Gonzalez-Coloma, A. (2002) J. Nat. Prod., 65, 448.
21-ACETOXYTOONACILID C33H40O12
(628.67) [α]20
D : +47.5° (CHCl3)
O
O
OAc
AcO OAc
O
CH2
O
COOCH3
(1) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
6-ACETOXYTOONACILIN C33H40O11
(612.67)
M.p. : 215°
AcO
O
H2C
O OAc
COOCH3
(1) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(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.
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)
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)
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)
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.
12-O-ACETYLAZEDARACHIN–B C34H44O12
(644.71)
D : −55° (MeOH)
[α]22
O
OAc
O
HO
O O
AcO
OH
OCO
(1, 2) (1)
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.
1-O-ACETYL-3-DEACETYL-1- C28H36O8
DETIGLOYLSALANNIN (500.56)
Only spectral data given
AcO COOCH3
O
HO
H
O
(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.
1-O-ACETYL-1-DETIGLOYLSALANNIN C31H40O9
(556.65)
Only spectral data given
COOCH3
AcO
AcO O
H
O
(1) (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.
O
H
O
H H
CH3COO H
COO
O
OCOCH3
OCOCH3
(1) (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.
ACETYLISOMONTANOLIDE C24H32O8
(448.51)
M.p. : 134°
OOC
OOCCH3
(1, 2) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
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)
(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.
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)
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.
(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.
6-ACETYLNIMBANDIOL C28H34O8
(498.57)
M.p. : 178°
O
O
HO
OAc
(1) (1)
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)
3-O-ACETYLOHCHINOLAL C36H46O11
(654.75)
Amorphous powder
O O [α]D : +62°(CH3OH)
COOCH3
O
O
AcO
CHO
OAc
(1) (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.
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
(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.
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.
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)
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.
ACETYLVISMINONE–B C23H24O6
(396.44)
M.p. : 115–120° (dec.)
O OH O
OCH3
AcO
(1, 2) (1, 2)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(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.
ACROPTILLIN C19H23O7Cl
(398.84)
M.p. : 197–199°
Cl
HO OOC
OH
O
CH2
O
(1, 2, 3) (1, 2, 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.
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.
AFLAVAZOLE C28H35O2N
(417.59)
M.p. : 156–160° (dec.)
OH
N
H
(1) (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.
(1) TePaske, M.R., Gloer, J.B., Wicklow, D.T., and Dowd, P.F. (1990) J. Org. Chem., 55, 5299.
AGERATRIOL C15H24O3
(252.35)
M.p. : 195°
[α]20
D : +30.5° (CH3OH)
OH OH
CH2
OH
CH2 CH2
(1, 2) (1)
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.
AGINOSIDE C50H82O24
(1067.18)
M.p. : 272–276° (dec.)
O
[α]D29 : –66.7° (CHCl3)
HO
OH
(1, 3) (3)
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%
(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.
AILANTHINONE C25H34O9
(478.54)
M.p. : 227–230°
[α]27
D : +90° (CHCl3)
OH
HO
HO
O
O OCO
O O
(1, 2) (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.
AJUGAREPTANSIN C29H44O10
(552.66)
Amorphous
H
O
COO H
H
H
H
HO
O
OCOCH3
OCOCH3
(1, 2) (1)
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.
AJUGAREPTANSONE–A C29H40O10
(548.63)
M.p. : 177–180°
O
COO
O
OCOCH3
OCOCH3
(1, 2) (1)
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.
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)
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)
(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.
AJUGARIN–I C24H34O7
(434.53)
M.p. : 155–157°
O
H
O
OAc
CH2OAc
(1) (1,2)
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) 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.
AJUGARIN–II C22H36O6
(396.52)
M.p. : 188–189°
H
O
O
OH
CH2OAc
(1) (1,2)
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.
AJUGARIN–III C24H36O8
(452.54)
M.p. : 243–245°
O
H O
HO
HOH2C OAc
CH2OAc
(1) (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.
ALANTOLACTONE C15H20O2
(232.32)
M.p. : 78.5–80.0°
B.p. : 275°
CH2
(1, 2) (1, 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.
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)
ALATOLIDE C19H26O6
(350.41)
M.p. : 59–61°
CH2OH
OCO
CH2
O
CH2OH
O
(1, 2) (1, 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.
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)
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.
ALLIARINOSIDE C10H15O6N
(245.22)
Colorless gum
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.
COOH
H C NH2
CH2NHCOCOOH
(1, 2) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
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)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
Concentration = EC50
value.
(2)
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)
(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.
ANGELICIN C11H6O3
(186.17)
M.p. : 138–139.5°
O O O
(1, 2, 3) (1, 2)
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)
(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.
8α-ANGELOYLOXYCOSTUNOLIDE C20H26O4
(330.42)
Only spectral data given
O
CH2
O
(1) (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) Goren, N., Tahtasakal, E., Pezzuto, J.M., Cordell, G.A., Schwarz, B., and Proksch, P. (1994) Phytochemistry,
36, 389.
5α-ANGELOYLOXYSILPHINEN-3-ONE C20H28O3
(316.42)
Oil
O O
(1) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(1) Reina, M., Nold, M., Santana, O., Orihuela, J.C., and Gonzalez-Coloma, A. (2002) J. Nat. Prod., 65, 448.
ANGULATUEOID–G C33H36O9
(552.62)
Only spectral data given
O
OH
O
H
O OH
O
OAc
(1) (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.
ANGUSTONE–A C25H26O6
(422.48)
M.p. : 159–160°
HO O
OH O
HO OH
(1, 2) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
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.
ANGUSTONE–B C25H24O6
(420.46)
M.p. : 160–161°
HO O
OH O
HO O
(1, 2) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(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.
ANGUSTONE–C C25H24O6
(420.46)
M.p. : 170–180°
O O
OH O
HO OH
(1, 2) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(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.
ANTHOTHECOL C28H32O7
(480.56)
M.p. : 225°
[α]20
D : –63° (CHCl3)
O
AcO
O O
OH
(1, 2) (1, 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.
(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.
COOH
NH2
(1) (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.
(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.
ANTHRAQUINONE-2-ALDEHYDE C15H8O3
(236.21)
M.p. : 188–191°
CHO
(1) (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.
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)
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.
(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.
ARCHANGELOLIDE C29H40O10
(548.63)
M.p. : 109–112°
OOC
O
OAc
(1, 2) (3)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
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)
(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.
ARCTOLIDE C17H20O6
(320.34)
M.p. : 144–145°
AcO O
OH O
CH2
CH2
(1, 2) (1, 2)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
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)
(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.
ARECOLINE C8H13O2N
(155.19)
B.p. : 209°
n20
D : 1.4302
COO
(1, 2, 3) (1, 2)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
ARGOPHYLLIN–A C20H28O7
(380.44)
M. p.: 190–192°
O
O
OH
HO CH2
O
(1, 2) (1, 2, 3)
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
COOH
O
NO2
O
OCH3
(1) (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)
(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.
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)
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.
ARTEMISININ C15H22O5
(282.34)
M. p.: 156–157°
[α]17
D : 66.3° (neat)
O
H
O
O
O
H
O
(1, 2) (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)
COOH
HO
HO
HO
(1, 2) (2)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(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.
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)
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)
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.
ATROPINE C17H23O3N
(289.38)
M.p. : 114–116°
N
CH2OH
OOCCH
(1, 2, 3) (1, 2)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
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)
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)
(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.
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)
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.
AZADIRACHTIN–A (Cont.)
SOURCE:
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
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.
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)
(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.
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.
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.
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)
(16) Reed, D.K., Warthen, J.D. Jr., Uebel, E.C., and Reed, G.L. (1982) J. Econ. Entomol., 75, 1109.
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)
(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.
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.
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)
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.
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.
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%
(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.
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)
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.
AZADIRACHTIN–D C34H44O14
(676.71)
Only spectral data given
O
O
OH
AcO
H
O
(1) (1,3)
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)
(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.
AZADIRACHTIN–H C33H42O14
(662.68)
M.p. : 258–261°
O
O
AcO OH
H
H3COOC O
(1) (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)
(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.
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)
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.
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)
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.
AZADIRADIONE C28H34O5
(450.57)
M.p. : 168°
[α]20
D : +35.5° (CHCl3)
O
O OAc
(1) (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.
AZADIRONE C28H36O4
(436.59)
Amorphous
O OAc
(1) (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.
AZEDARACHIN–A C33H44O11
(616.70)
Amorphous powder
O
[α]22
D : –10° (CH3OH)
OH
O
HO
O O
AcO
OH
OCO
(1) (1)
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.
AZEDARACHIN–B C32H42O11
(602.68)
Amorphous powder
O
[α]D : –22° (CH3OH)
OH
O
HO
O O
AcO OH
OCO
(1) (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.
AZEDARACHIN–C C32H42O10
(586.68)
O Only spectral data given
O
HO
O O
AcO OH
OCO
(1) (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.
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.
AZEDARALIDE C15H16O4
(260.11)
Yellowish powder
CH2OH
(1) (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.
BAKKENOLIDE–A C15H22O2
(234.34)
M.p. : 80.5–80.6°
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
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.
BENZALDEHYDE C7H6O
(106.12)
M.p. : –26°
B.p. : 179°
CHO n20
D : 1.5456
(1) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
Concentration = EC50
value.
(2)
(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.
p-BENZOQUINONE C6H4O2
(108.10)
M.p. : 115.7° (117°)
d20
4 : 1.32
(1, 2) (1)
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)
(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.
[α]22
D : +24.05° (Pyridine)
OH
HO
O
O OCO
H OH
O O
(1, 2) (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
(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.
[α]25
D : –21.7° (CHCl3)
CH2OAc
AcO OBz
OAc
O
HO OAc
(1) (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.
[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.
[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.
B.p. : 204.7°/760 mm
CH2OH n20
D : 1.045
d15
15 : 1.05
(1) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
Concentration = EC50
value.
(2)
(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.
BERBERINE C20H18O4N
(336.37)
No data given
O
O
+
N
CH 3O
OCH3
(1, 2) (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
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)
N
O
H H
O
O
O
(1) (1)
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.
[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)
( – assayed as MeCl)
BILOBALIDE C15H18O8
(326.30)
M.p. : >300°
[α]20
D : –66.6° (Acetone)
O O
O O
OH
O
OH
O
(1, 2) (1)
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.
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)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
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)
(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.
(6S)-2,10-BISABOLADIEN-1-ONE C15H24O
(220.18)
Oil
(1) (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
(1) Reina, M., Nold, M., Santana, O., Orihuela, J.C., and Gonzalez-Coloma, A. (2002) J. Nat. Prod., 65, 448.
BISABOLANGELONE C15H20O3
(248.32)
M.p. : 148–149°
O
H
(1, 2) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
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.
N
NCONH Cl
Cl
(1, 2) (1)
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)
(1) Mulder, R., Wellinga, K., and van Daalen, J.J. (1975) Naturwissenschaften, 62, 531.
(2) Tamaki, G. (1976) J. Econ. Entomol., 63, 644.
BORNEOL C10H18O
(154.25)
M.p. : 208–209°
B.p. : 212°
HO
(1, 2) (2)
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)
(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.
B.p. : 103°/14 mm
AcO
(1, 2) (1, 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)
(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.
Br
COOH
(1, 2) (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 52.7% after 6 days of of 10–13 mg body
treatment exposure. weight
(2)
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)
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.
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)
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)
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.
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)
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)
(1) Blaney, W.M., Simmonds, M.S.J., Ley, S.V., Anderson, J.C., and Toogood, P.L. (1990) Entomol. Exp. Appl.,
55, 149.
HOOC
Br
(1) (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)
(1) Scheffrahn, R.H. and Rust, M.K. (1983) J. Chem. Ecol., 9, 39.
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)
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%
COOH
Br
(1, 2) (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 53.5% after 6 days of of 10–13 mg body
treatment exposure. weight.
(2)
(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.
BRUCEANOL–A C28H30O11
(542.54)
M.p. : 174–177°
HO COOCH3
HO
O
O OCO
H
O O
(1, 2) (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.
(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.
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)
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.
(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.
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)
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.
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)
(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.
BRUCEINE–A C26H34O11
(522.55)
M.p. : 267–270°
HO COOCH3
O
O OCO
H
HO O O
H
(1, 2) (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.
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)
(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.
BRUCEINE–B C23H28O11
(480.47)
M.p. : 264–268°
HO COOCH3
O
O OCOCH3
H
HO O O
H
(1, 2) (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)
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.
BRUCEINE–C C28H36O12
(564.58)
M.p. : 175–180°
HO COOCH3
OH
O
O OCO
HO O O
H
(1, 2) (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.
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.
BRUCEINE–D C20H26O9
(410.42)
M.p. : 285–290°
HO
HO
O
O OH
H OH
O O
H
(1, 2) (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.
(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.
BUCHANINOSIDE C32H42O11
(602.68)
M.p. : 259°
O
[α]D : –44.6° (CHCl3)
O
H3CO
OH OAc
O
O
OH
O O
(1) (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.
BUDDLEIN–A C20H22O7
(374.39)
M.p. : 106–108°
O
O
O
CH2
HO
O
(1, 2) (1)
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.
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)
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)
(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.
H3COOC O O
OCO
(1) (1)
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.
COOH
CH CH
OH
OH
(1, 2) (1)
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)
CAFFEINE C8H10O2N4
(194.19)
M.p. : 235° (anhyd.)
178° (subl.)
O [α]15
D : +2°
N
N
N
O N
(1, 2) (1)
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)
CAMELLIDIN–II C53H84O24
(1105.23)
M.p. : 211–212°
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)
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.
CANIN C15H18O5
(278.30)
M.p. : 245–246°
[α]23
D : –30.5° (EtOH)
H CH2
O
(1, 2) (1,2)
ACTIVITY PROFILE
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.
(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.
N
HO H
O
OH
OH
OH
(1) (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.
CH3O H
N
N
HO H
O
OH
OCH3
OH
(1, 2) (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 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.
CAPILLARIN C13H10O2
(198.22)
M.p. : 124°
(1, 2, 3) (1, 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) 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.
CAPILLENE C12H10
(154.21)
Oil
d20
0 : 0.977
(1, 2) (1)
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)
CAPILLIN C12H8O
(168.19)
M.p. : 79.5–80.5°
(1) (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)
[α]20
D : +62.3° (H2O)
n20
D : 1.4995
O
d20
4 : 0.9608
CH2
(1, 2) (2)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
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)
(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.
[α]20
D : +69.1° (H2O)
O n18
D : 1.4999
CH2
(1, 2) (1, 2)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
β-CARYOPHYLLENE C15H24
(204.36)
B.p. : 129–130°/14 mm
H2C
[α]15
D : –5.2° (benzene)
(1, 2) (1)
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.
6,7-EPOXY-3(15)-CARYOPHYLLENE C15H24O
(220.34)
Oil
H
H
O
CH2
(1) (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
(1) Reina, M., Nold, M., Santana, O., Orihuela, J.C., and Gonzalez-Coloma, A. (2002) J. Nat. Prod., 65, 448.
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)
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.
H H
AcO
H
O CH2
OAc
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.
CARYOPTINOL C24H34O8
(450.53)
M.p. : 219–220°
H H
HO
O CH2
OAc
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.
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.
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)
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.
CEDRELONE C26H30O5
O
(422.52)
M.p. : 209–214°
[α]30
D : –65° (CHCl3)
O O
OH (1, 2) (1, 2)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
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.
O O
OAc
(1, 2) (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 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%
(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.
O O
OH
(1, 2) (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 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%
(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.
O O
OAc
(1, 2) (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 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%
(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.
O O
OCH3
(1, 2) (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%
(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.
O O
OCH3
(1, 2) (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 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%
(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.
CELANGULIN C32H40O14
(648.66)
Amorphous powder
OAc
OAc O
O
CH2
AcO OAc
HO O
OAc (1) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(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.
α-CHACONINE C45H73O14N
(solanidine) (852.07)
M.p. : 243°
2.Rham - glu - O
(1, 2) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
CHALCONE C17H16O5
2′,4′-DIHYDROXY-4,6′-DIMETHOXY (300.29)
M.p. : 194–195°
OH
H3CO OCH3
OH O
(1) (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.
CHALCONE C18H18O5
2′-HYDROXY-4,4′,6′-TRIMETHOXY (314.32)
M.p. : 113°
OCH3
H3CO OCH3
OH O
(1) (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.
CHALCONE C19H20O5
4,2′,4′,6′-TETRAMETHOXY (328.35)
M.p. : 119–121°
OCH3
H3CO OCH3
OCH3 O
(1) (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.
CHALCONE C16H14O5
4,4′,6′-TRIHYDROXY-2′-METHOXY (286.27)
M.p. : 248°
OH
HO OCH3
OH O
(1) (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.
CHAMAEDROXIDE C20H22O7
(374.39)
M.p. : 255–257°
O
[α]20
D : +37.1° (Pyridine)
HO O
O
O
O
(1, 2) (1)
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.
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)
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.
CHAPARRINONE C20H26O7
(378.42)
M.p. : 238–242°
HO
HO
O
H
O
O O
(1, 2, 3) (1, 2, 4)
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.
HOOC O COOH
(1) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(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.
H C OOC
COO C H
COOH
HO
OH
(1, 2) (1)
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%
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)
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)
OH
Cl
HO COOCH3
O
O OCO
A
H
HO O O
H
(1) (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
(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.
OH
HO COOCH3
O
O OCO
A
H
HO O Cl
O
H
(1) (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
(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.
[α]26
D : –35.2° (H2O)
OH
OOCCH = CH
COOH
OH OH
OH
(1, 2) (1, 2)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
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)
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.
CH3O
O
CH2Cl
O
O O
CH2
(1) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
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)
(1) Nawrot, J., Harmatha, J., Kostova, I., and Ognyanov, I. (1982) Biochem. Syst. Ecol., 17, 55.
8′-CHLOROROTENONE C22H20O6Cl
(427.86)
No physical data given
OCH3
CH3O
O
O
O O
C CH2Cl
H
CH2
(1) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
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)
(1) Nawrot, J., Harmatha, J., Kostova, I., and Ognyanov, I. (1982) Biochem. Syst. Ecol., 17, 55-57.
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)
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).
CINNAMALDEHYDE C9H8O
(132.15)
B.p. : 210°/250 mm
d20
4 : 1.0497
CHO
n20
D : 1.61949
(1, 2, 3) (1, 2)
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)
CINNAMAMIDE C9H9ON
(147.18)
M.p. : 147°
H2N
(1, 2) (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)
B.p. : 300°
COOH
(1, 2) (1)
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)
(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.
CINNAMONITRILE C9H7N
(129.16)
M.p. : 20–21°
B.p. : 134°/12 mm
N
(1, 2) (1)
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)
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)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
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
(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.
6-CINNAMOYL-5-HYDROXY-2, C20H17O3
2-DIMETHYLCHROMAN (305.39)
No physical data given
O OH
(1) (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.
[α]20
D : +42° (neat)
H
O
N
N O
H
(1, 2) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
B.p. : 72.6°/1 mm
OH n20 : 1.58190
D
(1, 2) (1)
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)
CINNZEYLANINE C22H34O8
(426.50)
M.p. : 265–267°
[α]27
D : +45° (CH3OH)
α- OAc
OH
HO HO
O
OH
HO
(1, 2) (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 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.
CINNZEYLANOL C20H32O7
(384.46)
M.p. : 125–127°
[α]15
D : +18° (CH3OH)
α - OH
OH
HO HO
O
OH
HO
(1, 2) (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 assay index = 7.28 instar larvae for one
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. 96.
β - OH
OH
HO HO
O
OH
HO
(1) (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.
CINNZEYLANONE C20H30O7
(382.45)
Only spectral data given
O
OH
HO HO
O
OH
HO
(1) (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)
(1) Gonzalez-Coloma, A., Terrero, D., Parales, A., Escoubas, P., and Fraga, B.M. (1996) J. Agric. Food Chem.,
44, 296.
CITROLIN C26H28O6
(436.50)
M.p. : 305°
O
O O O
(1, 2) (1)
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)
COOH
(1, 2) (1)
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.
HO O
O OCH3
(1, 2) (1)
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.
CLERODENDRIN–A C31H42O12
(606.66)
M.p. : 164–165°
HO
CCOO
O CH2
OAc
OAc
OAc (1) (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.
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)
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.
CLERODIN C24H34O7
(434.53)
M.p. : 161–162°
O (164–165°)
[α]30
D : –37.6° (EtOH)
O CH2
OAc
OAc (1)
(1, 4)
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)
(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.
H H
O
H
O CH2
OAc
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.
(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.
CNICIN C20H26O7
(378.42)
M.p. : 143°
OH [α]20
D : +158° (EtOH)
OH
OCO
CH2
CH2
O
CH2OH
O
(1, 2) (1, 2)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
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)
(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.
CORONOPILIN C15H20O4
(264.32)
M.p. : 177–178°
[α]21
D : –30.2° (EtOH)
OH
O O CH2
(1, 2) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
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)
COOH
OH
(1, 2) (1)
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)
COOH
OH
(1, 2) (1, 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)
COUMESTROL C15H8O5
(268.22)
M.p. : 385°
OH
HO O
(1) (1)
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.
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)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(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.
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)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(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.
CUCURBITACIN–E C32H44O8
(556. 69)
M.p. : 234°
O [α]20
D : –64.3° (CHCl3)
OH
OAc
O
OH
HO
(1, 2) (1, 2)
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.
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.
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.
CYPERAQUINONE C14H10O4
(242.23)
M.p. : 182–183°
O O
(1) (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.
CYTISINE C11H14ON2
(sophorine/ulexine) (190. 24)
M.p. : 155°
B.p. : 218°/2 mm
[α]17
D : –119° (H2O)
NH
(1, 2) (1,3)
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)
(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.
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)
DATURALACTONE C28H38O7
(486.60)
M.p. : 264–267°
O
H
OH
O
O
OH
(1,2) (1)
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.
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)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(1) Yamasaki, R.B. and Klocke, J.A. (1989) J. Agric. Food Chem., 37, 1118.
O
OH
HO
OH
O
OAc
O
(1, 2, 3) (1, 2)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
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
(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.
6-DEACETYLNIMBIN C28H34O8
(498.57)
M.p. : 208°
COOCH3 O
O
H3COOC OH
(1) (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.
6-DEACETYLNIMBINENE C26H32O6
(440.54)
M.p. : 141°
O
O O
OH
(1, 2) (1)
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)
3-DEACETYLSALANNIN C32H42O8
(554.68)
M.p. : 214–215°
COOCH3 O
O
HO O
H
O
(1, 2) (1, 2)
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)
(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.
HO COOCH3
O
OH
O
O H
O O
H
(1, 2) (1, 3)
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.
(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.
O OH OH
OCH3
OH
(1, 2) (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.
DEACYLADENOSTYLONE C15H22O3
(250.34)
M.p. : 177–178°
(1, 2) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
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
(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.
DEAMINOACYLTAXINE–A C24H34O8
(450.53)
M.p. : 204–206°
AcO
OH
OAc
(1, 2) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
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
(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.
B.p. : 268–270°
n40
D : 1.42855
COOH
(1, 2) (1, 2)
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.
(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.
COO
HO OH
HO
(1) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
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.
COOH
(1) (1)
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)
(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.
14,15-DEHYDROAJUGAREPTANSIN C29H42O10
(550.65)
Only spectral data given
O
O H H
O
O
HO
O CH2
OAc
OAc
(1) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(1) Bremner, P.D., Simmonds, M.S.J., Blaney, W.M., and Veitch, N.C. (1998) Phytochemistry, 47, 1227.
DEMETHYLGROSSAMIDE C35H34O8N2
OH (610.66)
Amorphous powder
OH
NH
O HN
O
OH
O
OH
OCH3
(1) (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.
DEMETHYLHOMOLYCORINE C17H19O4N
(301.34)
M.p. : 213–214°
(138–140°;
270–272°)
H
CH3O
O
HO
(1, 2) (1)
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.
DEMISSINE C50H83O20N
(1018.20)
M.p. : 305–308° (Uncor.)
(1) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
+
NHCOCH2N CH2
(1, 2) (2)
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.
14-DEOXYANDROGRAPHOLIDE C20H30O4
(334.46)
M.p. : 175°
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.
DEOXYEPILIMONOL C26H32O7
(456.51)
M.p. : 300–305°
O O
O
O
OH
(1, 2) (1)
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.
8-DEOXYLACTUCIN C15H16O4
(260.29)
M.p. : 143–148°
H
H
CH2
CH2OH O
(1,2) (2)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
DEOXYLIMONIN C26H30O7
(454.52)
M.p. : 331–336°
O O
O
O
(1,2) (1)
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%
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.
DEOXYLIMONOL C26H33O7
(457.22)
M.p. : 250–252°
O
O
O
O
O
O
OH
(1,2) (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%
DEOXYVASICINE C11H12N2
(172.23)
M.p. : 99–100°
(1) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(1) Saxena, B.P., Tikku, K., Atal, C.K., and Koul, O. (1986) Insect Sci. Applic., 7, 489.
DERRICIN C21H22O3
(322.40)
Physical data not given
O OH
(1,2) (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- 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.
DESACETYLOARCTOLIDE C15H17O5
(277.34)
Only spectral data given
H O
HO O
O
OH
CH2
CH2
(1, 2) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
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
(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.
4-DESOXY-8-EPI-IVANGUSTIN C15H20O2
(232.32)
[α]D24 : +35.2°
O
O
CH2
(1, 2) (1)
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.
1-DETIGLOYL-3-DEACETYLSALANNIN C27H36O7
(472.58)
Only spectral data given
COOCH3
OH O
O
HO
H
O
(1) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(1) Yamasaki, R.B. and Klocke, J.A. (1989) J. Agric. Food Chem., 37, 1118.
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)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(1) Yamasaki, R.B. and Klocke, J.A. (1989) J. Agric. Food Chem., 37, 1118.
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)
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
(1) Blaney, W.M., Simmonds, M.S.J., Ley, S.V., Anderson, J.C., and Toogood, P.L. (1990) Entomol. Exp. App.,
55, 149.
1-DETIGLOYL-3-O-METHYL-3- C28H38O7
DEACETYLSALANNIN (486.61)
Only spectral data given
COOCH3
OH O
O
CH3O
H
O
(1) (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.
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)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(1) Yamasaki, R.B. and Klocke, J.A. (1989) J. Agric. Food Chem., 37, 1118.
DHURRIN C14H17O7N
(311.28)
M.p. : 165°
O C OH
O
OH
CN
OH H
OH
(1) (1)
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.
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.
O
AcO
COO OCO
OOC O
O
OAc OH
(1) (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
(1) Tu, Y.Q., Wu, D.G., Zhou, J., Chen, Y.Z., and Pan, X.F. (1990) J. Nat. Prod., 53, 603.
O O
AcO
COO OOC
OCO
O
OAc OH
(1) (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
(1) Tu, Y.Q., Wu, D.G., Zhou, J., Chen, Y.Z., and Pan, X.F. (1990) J. Nat. Prod., 53, 603.
6α-12-DIACETOXY-1β,2β,9α-TRI C34H42O14
(β-FURANCARBONYLOXY)-4α- (684.65)
HYDROXY-β-DIHYDROAGAROFURAN Amorphous powder
O
O
AcO
COO OOC
O
OOC
O
OAc OH
(1) (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
(1) Tu, Y.Q., Wu, D.G., Zhou, J., Chen, Y.Z., and Pan, X.F. (1990) J. Nat. Prod., 53, 603.
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.
2α,7β-DIACETOXY-15-ISOPIMARENE C24H38O6
3β,8β-DIOL (422.56)
M.p. : 174–176°
OH
AcO CH2
HO OAc
(1) (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.
OH
O
OAc
OAc
(1, 2) (1)
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.
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)
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.
DIACETYLVILASININE C30H40O7
(512.64)
M.p. : 157–158°
AcO
AcO OH
(1) (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)
CH2COOH
H2N C H
CH2NH2
(1, 2) (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)
H H
NH
=
HCF2F2O CH = N.N.(CH3)2N.CO.CNHN = CH OF2CF2CH
(1, 2) (1, 2)
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.
COOH
H C NH2
CH2NH2
(1) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
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)
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
(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.
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)
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.
(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.
O COOCH3
O O OH H
OH
O O
H
O
AcO OH
H
H3COOC O
(1, 2) (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)
(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.
22,23-DIHYDROAZADIRACHTOL C28H37O14
(597.59)
Only spectral data given
COOCH3
OH
HO O OH
O
O
OH
HO
H
H3COOC O
(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.
DIHYDROCARYOPTIN C27H38O9
CH2 (506.59)
M.p. : 198.5–199.5°
H H
O
H
AcO
H
O CH2
OAc
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.
DIHYDROCARYOPTINOL C25H36O8
CH2
(464.55)
M.p. : 204–205°
H H
O
H
HO
O CH2
OAc
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.
DIHYDROCLERODIN–I C24H36O7
(436.54)
M.p. : 169–170°
H H
O
H
O CH2
OAc
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.
DIHYDROCEDRELONE C26H32O5
(424.54)
M.p. : 216°
O O
OH
(1, 2) (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 49.5% instar larvae for 24 h.
test (2)
Calculated from
10 µg/cm2 Feeding inhibition = Reference 2.
70.5%
(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 Krishna Kumari,
G.N. (1995) J. Chem. Ecol., 21, 1586.
O O
OCH3
(1) (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)
Calculated from
10 µg/cm2 Feeding inhibition = Reference 2.
56.5%
(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 Krishna Kumari,
G.N. (1995) J. Chem. Ecol., 21, 1586.
DIHYDROERGOCRYSTINE C35H41O5N5
(611.74)
Only spectral data given
OH
O O
N
NH
N
O O
NH
(1) (1)
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)
DIHYDROERGOTAMINE C33H37O5N5
(583.69)
M.p. : 239°
OH
[α]D20 : –64° (pyridine)
O O
N
N
H N
O O
NH
(1, 2) (1)
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)
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)
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
(1) Blaney, W.M., Simmonds, M.S.J., Ley, S.V., Anderson, J.C., and Toogood, P.L. (1990) Entomol. Exp. Appl.,
55, 149.
DIHYDROISOLONCHOCARPIN C20H20O3
(308.36)
No physical data given
O O
(1) (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.
DIHYDROISOPIMPINELLIN C13H12O5
(248.23)
M.p. : 162–163°
OCH3
O O O
OCH3
(1) (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.
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)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
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.
14,15-DIHYDROJODRELLIN–T C29H40O10
(548.63)
[α]D20 : –24.4° (CHCl3)
OAc
OAc
O
O
O
O
O
O
(1) (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.
DIHYDROKOKUSAGINE C13H11O4N
(245.23)
M.p. : 165–166°
OCH3
O N
O
O
(1) (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)
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.
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)
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.
O COOCH3
O O OH H
OH
O O
OCH3
O
AcO OH
H
H3COOC O
(1) (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.
O COOCH3
O O OH H
OH
O O
SPh
O
AcO OH
H
H3COOC O
(1) (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)
(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′,3′-DIHYDROSALANNIN C34H46O9
(598.73)
Only spectral data given
O
O
O O
O
O
AcO
H
O
(1) (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.
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)
[α]D : –42°
OH
O O
O OH
OH
(1, 2) (1)
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.
DIHYDROXANTHOTOXIN C12H10O4
(218.21)
M.p. : 159–160°
O O O
OCH3
(1) (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)
(1) Yajima, T. and Munakata, K. (1979) Agric. Biol. Chem., 43, 1701.
2′,4′-DIHYDROOXYCHALCONE C15H12O3
(240.26)
M.p. : 149–150°
(142–143°)
HO OH
(1, 2) (1)
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.
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
(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.
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)
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.
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.
OH
O
HO
N
H
HO
(1, 2) (1)
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.
OH
O OH
(1, 2) (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.
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.
DIMBOA C9H9O5N
(211.17)
M.p. : 156–157° (dec.)
H3CO O OH
N O
OH
(1, 2) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(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.
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)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(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.
3,4-DIMETHOXYBENZALDEHYDE C9H10O3
(166.18)
M.p. : 44°
(58°)
B.p. : 172–175°/18 mm
OCH3
OCH3
CHO
(1, 2) (1, 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 72.8% 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.
(3) Opdyke, D.L.J. (1975) Food Cosmet. Toxicol., 13, 923.
B.p. : 172°/12 mm
OCH3 d17
17 : 1.179
OCH3
CH2OH
(1, 2) (1, 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 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.
3,4-DIMETHOXYETHYLBENZENE C11H14O2
(187.22)
Only spectral data given
OCH3
OCH3
CH2
(1, 2) (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.
3,5-DIMETHOXYPHENOL C8H10O3
(154.16)
M.p. : 44.5°
(36–38°)
B.p. : 199°/36 mm
OH
H3CO OCH3
(1) (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 3 h beetles.
(1)
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)
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)
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)
2,3-DIMETHOXYPHENOL C8H10O3
(154.16)
Oil
B.p. : 124–125°/17 mm
OH
OCH3
OCH3
(1, 2) (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 3 h beetles.
(1)
OH B.p. : 166–168°/10 mm
(123–125°/2 mm)
H3CO OCH3
CH2
(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)
3,4-DIMETHOXYPROPYLBENZENE C11H16O2
(180.25)
Only spectral data given
OCH3
OCH3
(1) (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.
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)
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.
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)
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.
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)
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.
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)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(1) Yamasaki, R.B. and Klocke, J.A. (1989) J. Agric. Food Chem., 37, 1118.
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)
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.
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)
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.
4,6-DIMETHYL-3,7-DIPHENYL-2,8- C26H18O4
DIOXO-2H,8H-BENZODIPYRAN (394.43)
M.p. : 278°
O O O O
(1) (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.
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)
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.
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
(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.
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)
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.
DIONCOPHYLLINE–A C24H27O3N
(377.48)
M.p. : 215°
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.
1,5-DIPHENYL-1-PENTANONE C17H18O
(238.31)
Only spectral data given
(1) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(1) Ping, G, Taiping, H., Rong, G., Qui, C., and Shigui, L. (2001) Pest. Manag. Sci., 57, 307.
1,5-DIPHENYL-2-PENTEN-1-ONE C17H16O
(236.31)
Only spectral data given
(1) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(1) Ping, G, Taiping, H., Rong, G., Qui, C., and Shigui, L. (2001) Pest. Manag. Sci., 57, 307.
DIPLOPHYLLOLIDE–A C15H20O2
(232.32)
M.p. : 60–62°
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.
DITHYREANITRILE C13H14ON2S2
(278.40)
M.p. : 135°
S S
CN
(1) (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)
(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.
COOH COOH
H2N C H H2N C H
(1, 2) (1, 2)
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.
DYMALOL C31H54O5
(506.76)
M.p. : 182–184°
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%
(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.
B.p. : 203–205°/1 mm
HOOC
(1, 2, 3) (1, 2)
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.
HOOC
(1, 2) (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)
(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.
HOOC
(1) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
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.
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
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)
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.
ENCECALIN C14H16O3
(232.27)
B.p. : 135–137°/0.11 mm
H3CO O
(1, 2) (1)
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.
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.
ENHYDRIN C23H28O10
(464.47)
M.p. : 185–186°
OOC
OAc
CH2
O
O
(1, 2) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(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.
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)
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.
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.
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.
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)
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
(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.
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.
(1) Miles, D.H., Chittawong, V., Payne, A.M., Hedin, P.A., and Kokpol, U. (1990) J. Agric. Food Chem., 38, 1591.
3-EPICARYOPTIN C26H36O9
(492.56)
M.p. : 171–172°
O
[α]D : –70° (CHCl3)
H H
AcO
O CH2
OAc
OAc
(1) (1)
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.
3-EPIDIHYDROCARYOPTIN C27H38O9
(506.59)
CH2
M.p. : 161–162°
H H
AcO
O CH2
OAc
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.
[α]25
D : 130° (CHCl3)
O
O
O
O
O
(1) (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%
(1) Matsui, K., Wada, K., and Munakata, K. (1976) Agric. Biol. Chem., 40, 1045.
EPILIMONOL C26H32O8
(472.51)
M.p. : 262–266°
O O
O
O O
OH
(1, 2) (1)
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)
(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.
O
O
O O
O
O O
OAc
(1, 2) (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 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.
(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.
12-EPI-TEUCVIN C19H20O5
(328.36)
M.p. : 197–199°
O
[α]D : +222.6° (CHCl3)
O
O
(1, 2) (1)
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.
14-EPOXYAZADIRADIONE C28H34O6
(466.57)
M.p. : 202–204°
O OAc
(1, 2, 3) (1)
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.
GluO
(1) (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)
(1) Lugemwa, F.N., Huang, F., Bentley, M.D., Mendel, M.J., and Alford, A.R. (1990) J. Agric. Food Chem., 38,
493.
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)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
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.
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)
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)
(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.
ERGONOVINE C19H23O2N3
(325.41)
M.p. : 162–163° (dec.)
(212°, dec.,
HO dimorph.)
O
NH
(1, 2) (1)
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)
α-ERGOSINE C30H37O5N5
(547.65)
M.p. : 228° (dec.)
OH
[α]20
D : –161° (CHCl3)
O
O
N
N N
O O
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%
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)
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.
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)
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.
ERIOCEPHALIN C24H30O9
(462.50)
M.p. : 197–200°
O
[α]20
D : +76.1° (CHCl3)
OAc
OH
O
O
OAc
(1, 2) (1)
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)
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
ERIVANIN C15H22O4
(266.34)
M.p. : 203–205°
[α]20
D : +112° (EtOH)
OH
HO
CH2
O
(1) (1)
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)
(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.
ERMANIN C17H14O6
(314.29)
M.p. : 235°
OH O
OCH3
HO O
OCH3
(1, 2) (1, 2)
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.
ERYTHRO-9,10-DIHYDROXY-1- C20H40O4
OCTADECANOL ACETATE (344.54)
M.p. : 54°
AcO
OH
OH
(1) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(1) Jacobson, M., Crystal, M.M., and Warthen, J.D. Jr. (1981) J. Agric. Food Chem., 29, 591.
H H
O
H
H
HO
COO
O CH2
OAc
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.
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.
(1) Miles, D.H., Chittawong, V., Payne, A.M., Hedin, P.A., and Kokpol, U. (1990) J. Agric. Food Chem., 38, 1591.
EUDESMENE C15H20O2
(232.32)
Oily solid
CH2
HO O
(1) (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.
[α]20
D : + 60.5° (Me2CO)
O
H3CO
H H
OCH3
OCH3
(1) (2)
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.
EUGENOL C10H12O2
(164.20)
M.p. : –9°
n19
D : 1.5439
d25
4 : 1.0620
CH3O
OH
(1, 2) (1)
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)
(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.
EUPATOLIDE C15H20O3
(248.32)
M.p. : 185–188°
[α]22
D : +20° (Acetone)
OH
CH2
O
O
(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 = 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)
(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.
OH
OCH3
(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 = 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)
(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.
OH
(1, 2) (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)
(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.
EUPATORIOPICRIN C20H26O7
(378.42)
M.p. : 157–161°
[α]20
D : +95° (CHCl3)
O
O
CH2
HO OH
O
OH
(1, 2) (1, 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
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)
(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.
EVOXINE C18H21O6N
(347.37)
M.p. : 151–152°
OCH3 [α]22
D : +14.6° (EtOH)
O N O
HO OCH3
OH
(1) (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.
CH3OCO.Sn
(1, 2) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
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)
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)
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)
(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.
B.p. : 249°/13.5 mm
Cl Sn
(1, 2) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
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.
(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.
HO Sn
(1, 2) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
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)
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)
(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.
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.
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.
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)
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.
FLAVONE C19H18O7
5-HYDROXY-3,6,7,8-TETRAMETHOXY (358.33)
M.p. : 98–100°
OCH3
H3CO O
H3CO OCH3
OH O
(1) (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.
FLAVONE C17H14O6
5,6-DIHYDROXY-3,7 DIMETHOXY (314.28)
M.p. : 178°
H3CO O
HO OCH3
OH O
(1) (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.
FORMONONETIN C16H12O4
(268.26)
M.p. : 265–266°
(257–258°)
HO O
O
OCH3
(1) (1)
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.
8′-FORMYLOXYROTENONE C25H22O8
(450.42)
No physical data given
OCH3
H3CO
O
O
O O
CCH2OC OH
H
CH2
(1) (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)
(1) Nawrot, J., Harmatha, J., Kostova, I., and Ognyanov, I. (1989) Biochem. Syst. Ecol., 17, 55.
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)
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.
(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.
FRAXINELLONE C14H16O3
(232.28)
M.p. : 116°C
[α]22
D : –44° (EtOH)
O
(1, 2) (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.
(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.
FRIEDELIN C30H50O
(426.73)
M.p. : 267–269°
(263–263.5°)
[α]14
D : –27.8° (CHCl3)
(1) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(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.
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)
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.
(1) Bentley, M.D., Rajab, M.S., Mendel, M.J., and Alford, A.R. (1990) J. Agric. Food Chem., 38, 1400.
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)
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.
(1) Bentley, M.D., Rajab, M.S., Mendel, M.J., and Alford, A.R. (1990) J. Agric. Food Chem., 38, 1400.
OH O
OH
HO COOH OH
O OH
O O
HO O O
HO OH
HO HO
O O
HO
OH
(1) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(1) Herlt, A.J., Mander, L.N., Pongoh, E., Rumampuk, R.J., and Tarigan, P. (2002) J. Nat. Prod., 65, 115.
OH O
OH
HO COOH OH
O OH
O O
HO O O
HO OH
HO HO
O O
HO
OH
(1) (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%
(1) Herlt, A.J., Mander, L.N., Pongoh, E., Rumampuk, R.J., and Tarigan, P. (2002) J. Nat. Prod., 65, 115.
[α]24
D : –98.8° (MeOH)
H
H3CO O
OH
+ 2-
N CO3
(1) (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)
(1) Numata, A., Takemura, T., Ohabayashi, H., Katsuno, T., Yamamoto, K., Sato, K., and Kobayashi, S. (1983)
Chem. Pharm. Bull., 31, 2146.
HO O
HO OH
OH
(1) (1)
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)
GEDUNIN C28H34O7
(482.57)
M.p. : 157°
(218°)
O
[α]20
D : –44° (CHCl3)
O
O
O OAc
(1, 2) (2,3)
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)
(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.
[α]20
D : –73.3° (Pyridine)
HO
O
OH
O
O
HO
O
OH HO O
OH OH OH
(1) (1)
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.
COOH
OH
HO
(1) (1, 2)
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)
(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.
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
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.
GINKGOLIDE–A C20H24O9
(408.40)
M.p. : 280° (dec.)
O O
OH
OH
O
H
O O H
(1, 2) (1)
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.
GINKGOLIDE–B C20H24O10
(424.40)
M.p. : >280° (dec.)
O O
OH
OH
O
OH
O H
O
(1, 2) (1)
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.
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)
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)
GLAUCARUBINONE C25H34O10
(494.54)
M.p. : 225–228°
(228–230°)
HO
HO
O
O OCO
OH
O O
H
(1, 2) (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)
(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.
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)
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)
GLAUCARUBOLONE C20H26O8
(394.42)
M.p. : 255–258°
HO
HO
O
O OH
O O
(1, 2) (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 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)
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)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(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.
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)
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
(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.
GLYCEOLLIN C20H18O5
(338.36)
Only spectral data given
OH
O
H
OH
O O
(1, 2) (1)
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.
GOSSYPOL C30H30O8
(518.56)
M.p. : 181–183°
CHO OH OH CHO
HO OH
HO OH
(1) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(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.
GRADOLIDE C25H34O7
(446.54)
M.p. : 154°
OH [α]20
D : –50.9°
OOC
OOC
O
(1, 2) (1)
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
(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.
GRAMINE C11H14N2
(174.24)
M.p. : 138–139°
(131–132°)
N
H
(1, 2) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(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.
GRISEOFULVIN C17H17O6Cl
(352.77)
M.p. : 225–226°
[α]17
D : +370° (CHCl3)
OCH3 O OCH3
H3CO O
Cl
(1, 2) (1)
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%
(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.
NH
O HN
O
OCH3 OH
OCH3
(1, 2) (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.
GROSSHEIMIN C15H18O4
(262.31)
M.p. : 205°
CH2 [α]20
D : +137.7° (MeOH)
O OH
CH2
O
(1, 2) (1, 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 = 51–100
(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.
GRAYANOTOXIN–I C22H36O7
(412.51)
M.p. : 260–272°
HO
OH
OH
OH
(1, 2) (1, 2)
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.
GRAYANOTOXIN–III C20H34O6
(370.48)
M.p. : 218°
[α]15
D : –12°
OH
H
OH
HO
OH
OH
OH
(1, 2) (1, 2)
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.
HALOSTACHINE C9H13ON
(151.21)
M.p. : 43–45°
H [α]D : –47°
N
H C OH
(1) (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)
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
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.
HARUNGANIN C30H36O4
(460.61)
M.p. : 190°
OH OH O
OH
(1, 2) (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)
[α]D : –105°
COOH
OH
(1, 2) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
HELENALIN C15H18O4
(262.30)
M.p. : 225–228°
[α]25
D : –102.8° (CHCl3)
O
O
OH
CH2
(1, 2) (1, 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.
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
(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.
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)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
15 – HEPTYLCHAPARRINONE C27H40O7
(476.61)
Only spectral data given
OH
HO
HO
O
O O
H
(1, 2) (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.
(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.
B.p. : 180–183°/1 mm
COOH
(1, 2, 3) (1, 2)
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.
(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.
COO O
O
O
AcO
H
O
(1) (1, 2)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
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.
HEXAMETHYLDITIN C6H18Sn2
(327.59)
B.p. : 182°/760 mm
M.p. : 62–63°/12 mm
Sn Sn
(1) (1, 2)
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)
(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.
HILDECARPIN C17H14O7
(330.29)
[α]D : –244° (MeOH)
HO O
OH
O
H3CO
H
O
O
(1) (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.
HIPPEASTRINE C17H17O7N
(315.32)
M.p. : 214–215°
[α]22
D : +160° (CHCl3)
H
O
OH
O
O
(1, 2) (1, 2)
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%
(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.
HIRSUTOLIDE C19H24O9
(396.39)
Oil
[α]24
D : +36.3° (CHCl3)
O H2C O
HO O
OH
OAc OAc
(1, 2) (1)
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
HISPIDULIN C16H12O6
(300.27)
M.p. : 304–305°
(291–292°)
HO O
OH
H3CO
OH O
(1, 2, 3) (1, 2)
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%
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)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
HOMOERIODICTYOL C16H14O6
(302.28)
M.p. : 224°
[α]20
D : –28.2° (EtOH))
OCH3
OH
HO O
OH O
(1, 2) (1, 2)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
Concentrations =
EC50 values.
(3)
HOMOGYNOLIDE–A C20H28O4
(332.44)
M.p. : 62–65°
H2C O
O
O
(1) (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 = 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
(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.
HOMOGYNOLIDE–B C20H28O4
(332.44)
Oil
H2C O
(1) (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 = 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
(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.
H2SO4.2 H2O
2
OH
(1) (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.
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)
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
(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.
HYDRASTINE C21H21O6N
(383.40)
M.p. : 162–163.5°
N
O
H H
CH3O
O
OCH3
(1, 2) (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.
14-HYDROAJUGAPITIN-2,15-DIONE C29H40O11
(564.63)
O [α]20
D : +1.41° (CHCl3)
O
H
O
H
OCOCH3
(1, 2) (1)
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.
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)
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.
COOH
O
NO2
O
HO OCH3
(1) (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.
11-β-HYDROXY-5α-(ANGELOYLOXY) C20H24O4
SILPHINEN-3-ONE (328.39)
Only spectral data given
OH
O O
(1, 2) (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.
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.
p-HYDROXYBENZALDEHYDE C7H6O2
(122.12)
M.p. : 115–116°
CHO
HO
(1) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
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%
4-HYDROXY-3-ARYLCOUMARYL C15H8O5
QUINONE (268.22)
No physical data given
O O
OH
O
(1) (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)
(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.
COOH
OH
(1) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
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)
6β-HYDROXYEREMOPHILENOLIDE C15H22O3
(250.34)
M.p. : 208°
OH
(1, 2) (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 = − 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
(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.
γ-HYDROXYFERRUGININ–A C30H36O5
(476.61)
Only spectral data given
OH O
OH
OH
OH
(1, 2) (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
(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)
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.
γ-γ-HYDROXYFERRUGININ–A C30H36O6
(492.61)
No physical data given
OH OH O
OH
OH
OH
(1) (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.
7-HYDROXYFLAVONONE C15H10O3
(238.24)
M.p. : 244°
(240°)
HO O
(1, 2) (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.
2′-HYDROXYFORMONONETIN C16H12O5
(284.27)
M.p. : 215–217°
(220–222°)
HO O
O
HO OCH3
(1) (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)
(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.
2′-HYDROXYGENISTEIN C15H10O6
(286.24)
M.p. : 270–273°
HO O
OH O
HO OH
(1, 2) (1)
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.
3-HYDROXYGRANDIOLIDE C15H22O4
(266.34)
M.p. : 65°
CH2 [α]24
D : –25° (CHCl3)
H OH
HO
H
O
(1, 2) (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 = 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
(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.
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)
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.
O OH
H3CO
HO
(1, 2) (1, 2, 3)
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.
[α]20
D : +48.4° (CHCl3)
HO
CH2
H
COOH
(1) (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
(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.
5-HYDROXYISODERRICIN C21H22O4
(7-methyl-grabanin) (338.40)
No physical data given
H3CO O
OH O
(1) (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.
3-HYDROXY-4-METHOXY C10H10O4
CINNAMIC ACID (194.19)
M.p. : 233–234°
(228°)
COOH
OH
OCH3
(1, 2) (1, 3)
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)
1- (4-HYDROXY-3-METHOXYPHENYL) C17H26O3
DECAN-3-ONE (278.39)
M.p. : 27–29°
(31–32°)
H3CO
HO
(1, 2) (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.
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)
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.
(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.
(–)-3′-HYDROXY-4′-METHOXY-7- C17H18O4
HYDROXY-8-METHYLFLAVAN (286.33)
[α]20
D : –31° (CHCl3)
OH
OCH3
HO O
(1) (1)
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%
(1) Numata, A., Takemura, T., Ohbayashi, H., Katsuno, T., Yamamoto, K., Sato, K., and Kobayashi, S. (1983)
Chem. Pharm. Bull., 31, 2146.
n 25
D : 1.5727
CHO
OH
OCH3
(1) (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.
n25
D : 1.5730
CHO
OH
OCH3
(1) (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- (4-HYDROXY-3-METHOXYPHENYL) C17H24O3
DEC-5-EN-3-ONE (276.38)
Oil
H3CO
HO
(1, 2) (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.
OH
O
H3CO
N
H
HO
(1, 2) (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 = 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.
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.
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.
COOH
O
OH
(1) (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)
6-HYDROXYPICRASIN–B C21H28O7
(392.45)
M.p. : 285–290°
O
O
HO O
H
O
H
OH
(1, 2) (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
6-HYDROXYSANDORICIN C31H40O12
(604.65)
M.p. : 250–255° (dec.)
O O
O
O O
O
O
CH2 OH
O
OH
COOCH3
(1) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
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.
2-HYDROXYSENEGANOLIDE C27H35O9
(503.54)
Amorphous powder
O
[α]D : +61° (MeOH)
O O
O
O
O
HO H
OH
O
(1) (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.
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)
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)
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)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
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.
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)
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%
(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.
IMPERATORIN C16H14O4
(270.28)
M.p. : 102°
O O O
(1, 2) (1)
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)
(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.
COOH
(1) (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)
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)
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)
ISOALANTOLACTONE C15H20O2
(232.32)
M.p. : 115°
(109–110°)
O
O
H
CH2
CH2
(1, 2) (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 = 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
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)
Ent-ISOALANTOLACTONE C15H20O2
(232.32)
M.p. : 112–115°
H
CH2 CH2
(1, 2) (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 = 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
(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
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)
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
ISOBERGAPTEN C12H8O4
(216.19)
M.p. : 222°
(217–219°)
OCH3
O O O
(1, 2, 3) (1, 2)
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)
ISOBOLDINE C19H21O4N
(327.38)
M.p. : 127°
H3CO
[α]31
D : +60° (CHCl3)
N
HO
H3CO
OH
(1) (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.
ISOBRUCEIN–A C26H34O11
(522.55)
M.p. : 200–202°
HO COOCH3
OH
O
H
O OCO
O O
H H
(1, 2, 3) (1, 2)
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.
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)
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)
(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.
3β-ISOBUTYRYLOXY-1-1-OXOMELIAC-8 C31H40O8
O
(30)-ENATE (540.65)
M.p. : 211–213°
O
H3COOC
O O
O (1) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(1) Mikolajczak, K.L., Weisleder, D., Parkanyi, L., and Clardy, J. (1988) J. Nat. Prod., 51, 606.
OH
O
COOH
OH
(1) (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 42.6% instar larvae
test for 24 h.
5 µg/cm2 Feeding inhibition = (2)
46.5%
(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 Krishna Kumatri,
G.N. (1995) J. Chem. Ecol., 21, 1585.
(1, 2) (2)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(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.
ISOERIOCEPHALIN C24H30O9
(462.50)
M.p. : 232–234°
O
[α]20
D : –33.1° (CHCl3)
O
OAc
O
O
OH
AcO
(1, 2) (1)
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.
ISOFRUTICOLONE C22H30O6
(390.48)
Oil
AcO OH
(1, 2) (2)
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.
ISOLACTARORUFIN C15H22O4
(266.34)
M.p. : 191°
[α]20
D : +8.4° (CHCl3)
OH O
OH
(1, 2) (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 = 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)
(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.
ISOLONCHOCARPIN C20H18O3
(306.36)
M.p. : 115°
[α]24
D : –125° (CHCl3)
O O
(1, 2) (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- 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.
ISOMONTANOLIDE C22H30O7
(406.47)
M.p. : 174–176°
OH
[α]20
D : –25.2° (CHCl3)
OOC
OAc
(1, 2) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(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.
ISOPETASIN C20H28O3
(316.44)
M.p. : 99–100°
(82–84°)
[α]20
D : +31° (CHCl3)
O
O
(1, 2) (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 = 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
(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.
[α]24
D : 0° (neat)
CH2
COOH
(1, 2) (1)
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
ISOPIMPINELLIN C13H10O5
(246.22)
M.p. : 147–148°
(151°)
OCH3
O O O
OCH3
(1, 2) (1)
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)
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.
ISOPONGAFLAVONE C21H18O4
(334.37)
M.p. : 215–216°
O O
OCH3 O
(1, 2) (1)
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.
ISOPROTOSTEMONINE C23H31O6N
(417.50)
M.p. : 165–167°
O
O N O
O
OCH3
(1) (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.
ISOSILEROLIDE C22H30O6
(390.48)
M.p. : 141–143°
[α]20
D : –138.9° (CHCl3)
OCOCH3
OCO
O
(1, 2) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(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.
ISOTADEONAL C15H22O2
(234.34)
Oil
B.p. : 145–153°/1 mm
CHO
(1) (2)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(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.
ISOTENULIN C17H22O5
(306.36)
M.p. : 160–161°
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.
O
N
OAc
(1) (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.
H
H
H O
O
O
OAc
(1) (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.
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)
(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.
ISOVELLEROL C15H22O2
(234.35)
Only spectral data given
OHC
HOH2C
(1, 2) (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
(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.
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.
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)
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.
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)
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.
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)
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.
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)
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.
JAPONINE C18H17O3N
(295.34)
M.p. : 143°
(145–146°)
H3CO OCH3
(1) (1, 2)
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.
JODRELLIN–A C24H32O8
(448.51)
Oil
OAc
OAc
O
O
O
(1, 2)
(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.
JODRELLIN–B C26H36O8
(476.57)
Oil
[α]20
D : –11.4° (CHCl3)
O
OAc O
O
(1, 2) (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.
JUGLONE C10H6O3
(174.16)
M.p. : 155°
OH O
(1, 2) (1)
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%
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.
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)
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.
OH
(1, 2) (1)
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)
(–)-KAURAN-16α-19-DIOL C20H34O2
(306.49)
M.p. : 200–201°
[α]22
D : –40.5° (EtOH)
OH
CH2OH
(1, 2) (1)
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.
CH2
COOH
(1, 2) (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)
[α]22
D : –236.8° (CHCl3)
OH
HOOC
(1, 2) (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.
COOH
(1) (2)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(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
O
CH3OOC H
HO OAc O
O
O
OH
(1) (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.
KHAYANOLIDE–E C29H35O11
(559.22)
Amorphous powder
O
O
CH3OOC H OH
HO OAc O
O
(1) (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.
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)
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.
B.p. : 180–200°/0.05 mm
OCH3 O
O O
OCH3
(1, 2) (1)
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)
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)
OC2H5
O O
OC2H5 O
(1) (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.
OCH3
O O
OC2H5 O
(1) (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.
KIEVITONE C20H20O6
(356.37)
Only spectral data given
HO O
OH O
HO OH
(1, 2) (1)
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.
KLAINEANONE C20H28O6
(364.44)
M.p. : 253–258°
[α]22
D : –52° (Pyridine)
OH
HO
HO
H
O O
H
(1, 2) (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.
(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.
KOKUSAGINE C13H9O4N
(243.22)
M.p. : 202–203°
OCH3
O N O
(1) (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)
(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.
KOLAVENOL C20H34O
(290.49)
Oil
OH
(1) (1)
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.
LACTARORUFIN–A C15H22O4
(266.34)
M.p. : 156–158°
[α]20
D : +7° (CHCl3)
O
HO OH
(1, 2, 3) (1, 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 = 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
(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.
LACTARORUFIN–B C15H22O5
(282.34)
M.p. : 213°
[α]20
D : +24° (CHCl3)
HOH2C
O
HO OH
(1, 2) (1, 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 = 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
(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.
LACTUPICRIN C23H22O7
(410.42)
M.p. : 132–178°
OOC
OH
CH2
CH2OH O
(1, 2) (1)
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%
[α]22
D : +55° (EtOH)
CH2
COOH
(1, 2) (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.
LASEROLIDE C22H30O6
(390.48)
M.p. : 140–141°
[α]20
D : –234°
OAc
O
O
O
(1, 2) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(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.
OH
(1) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
No quantitative data
given.
(1)
(1) Wiemer, D.F. and Ales, D.C. (1981) J. Org. Chem., 46, 5449.
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)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
B.p. : 225°/100 mm
nD82 : 1.4183
COOH
(1, 2) (1)
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%
(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.
LEDOL C15H26O
(222.37)
M.p. : 105°
B.p. : 282–283°
OH
(1, 2) (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 = 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
(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.
LEPTINE–III
Not well characterized
Unknown structure
Sugar residual not identified
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(1) Mitchel, B.K. and Harrison, G.D. (1985) J. Chem. Ecol., 11, 73.
[α]24
D : –276° (EtOH)
COOH
(1, 2) (1, 2)
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)
(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.
LICOISOFLAVONE–A C20H18O6
(354.36)
M.p. : 111–114°
HO O
OH O
HO OH
(1, 2) (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.
LICOISOFLAVONE–B C20H16O6
(352.34)
M.p. : 185–186°
HO O
OH
OH O
O
(1, 3) (1, 3)
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.
O
OH
O
O O
O O
(1, 2) (1)
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.
(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.
LIMONIN C26H30O8
(470.52)
M.p. : 298°
O
[α]D : –125° (Acetone)
O
O O
O
O O
O
(1, 2) (1)
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)
7. Heliothis zea (Boddie) Leaf disk 60.8 µg/disk Feeding inhibition = 7. Treatment to
(Corn earworm) test 95.0% larvae.
(7)
(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.
O [α]24
D : –193° (Acetone)
O O
O
O O
OH
(1, 2) (1)
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.
LIMONIN-7-METHOXIME C27H33O8N
(499.56)
Amorphous solid
O
[α]25
D : –134.65° (CHCl3)
O
O O
O
O O
OCH3
(1) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(1) Ruberto, G., Renda, A., Tringali, C., Napoli, E.M., and Simmonds, M.S.J. (2002) J. Agric. Food Chem., 50,
6766.
LIMONIN-7-OXIME C26H31O8N
(485.53)
Amorphous solid
O
[α]25
D : –159.46° (CHCl3)
O
O O
O
O O
OH
(1) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(1) Ruberto, G., Renda, A., Tringali, C., Napoli, E.M., and Simmonds, M.S.J. (2002) J. Agric. Food Chem., 50,
6766.
LIMONOL C26H32O8
(472.53)
[α]25
D : –57.28° (CHCl3)
O O
O
O O
OH
(1, 2) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
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.
(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.
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
n20
D : 1.4699
COOH
(1, 2) (1)
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.
B.p. : 230–232°/1 mm
COOH
(1, 2) (1)
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.
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)
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.
LOBATIN–B C20H24O7
(376.40)
Oil
[α]20
D : –11.5° (CHCl3)
O OH
O
O
O
CH2
(1, 2) (3)
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.
LONCHOCARPIN C20H18O3
(306.36)
M.p. : 108°
O OH
(1, 2) (1)
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.
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)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(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.
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)
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)
LUTEOLIN C15H10O6
(286.24)
M.p. : 328–330° (dec.)
OH
OH
HO O
OH O
(1) (1)
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)
LUTEONE C20H18O6
(354.34)
M.p. : 222–223° (dec.)
(225–227°)
HO O
OH O
HO OH
(1) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
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.
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.
H
H3CO O
OH
+
N 1/2 CO32-
(1) (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)
(1) Numata, A., Takemura, T., Ohabayashi, H., Katsuno, T., Yamamoto, K., Sato, K., and Kobayashi, S. (1983)
Chem. Pharm. Bull., 31, 2146.
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)
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)
(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.
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)
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)
(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.
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)
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)
(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.
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)
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)
MALTOL C6H6O3
(126.11)
M.p. : 160–162°
OH
(1) (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.
(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.
n60
D : 1.4342
COOH
(1, 2) (1)
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)
(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.
MARRUBIN C20H28O4
(332.44)
M.p. : 160°
OH O
O
O
(1, 2, 3) (1, 2)
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.
MEDICARPIN C16H14O4
(270.28)
M.p. : 127.5–128.5°
HO O
O
OCH3
(1) (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.
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)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(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.
MELIACARPININ–A C39H46O14
(738.78)
Data not verified yet
COOCH3
O O OCH3
OH
O
O
AcO OH
(1, 2) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(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.
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)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(1) Nakatani. M., Huang, R.C., Okamura, H., Iwagawa, T., Tadera, K., and Naoki, H. (1995) Tetrahedron, 51,
11731.
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)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(1) Nakatani. M., Huang, R.C., Okamura, H., Iwagawa, T., Tadera, K., and Naoki, H. (1995) Tetrahedron, 51,
11731.
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)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(1) Nakatani. M., Huang, R.C., Okamura, H., Iwagawa, T., Tadera, K., and Naoki, H. (1995) Tetrahedron, 51,
11731.
MELIACARPININ–E C33H44O13
(648.70)
[α]20
D : –10° (MeOH)
COOCH3
O OCH3
HO
OH
O O
O
O
O OH
(1) (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.
MELIANONE C30H46O4
(470.69)
M.p. : 232–233°
O
O
[α]D : –62° (CHCl3)
HO
(1, 2) (1, 2)
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)
MELIANOTRIOL C30H50O5
(490.72)
M.p. : 76–178°
OH
HO
(1) (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.
MELICOPICINE C18H19O5N
(329.35)
M.p. : 133–134°
OCH3 O
H3CO
H3CO N
OCH3
(1, 2) (1)
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)
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)
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.
MELIATOXIN–B1 C35H46O12
(658.74)
M.p. : 140–150° (dec.)
O
AcO
O
O
AcO OH
COO
(1, 2) (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.
o-METHOXYACETOPHENONE C9H10O2
(150.18)
Oil
B.p. : 125–126°/12 mm
OCH3
(1, 2) (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.
m-METHOXYACETOPHENONE C9H10O2
(150.18)
Oil
B.p. : 131°/18 mm
OCH3
(1, 2) (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 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.
p-METHOXYACETOPHENONE C9H10O2
(150.18)
M.p. : 37.5–38.5°
B.p. : 138–139°/15 mm
OCH3
(1) (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.
B.p. : 208–210°/4 mm
H3CO
N
N
H
(1, 2) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
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)
(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.
5-METHOXYISOLONCHOCARPIN C21H20O4
(336.39)
Configuration not
determined
O O
OCH3 O
(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.
7-O-METHYL-8-(3-METHYLBUTADIENYL) C22H23O3
-FLAVANONE (335.40)
No physical data given
CH2
H3CO O
(1) (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.
[α]24
D : +19.5° (EtOH)
HO O
H3CO O
(1) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
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)
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.
3-METHOXYPHENOL C7H8O2
(124.14)
B.p. : 110–115°/0.3 mm
n25
D : 1.5276
OH
OCH3
(1) (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)
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)
5-METHOXYTRYPTAMINE C11H14ON2
(190.24)
M.p. : 121–122°
H3CO
NH2
N
H
(1, 2) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(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.
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)
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.
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.
COOCH3
O
NO2
O
OCH3
(1) (2)
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.
3β-p-METHYLCINNAMATOXYLUP-20-EN- C42H60O4
28-OIC ACID (628.89)
M.p. : 225°
CH2
COOH
COO
(1) (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
(1) Jagadeesh, S.G., Krupadanam, G.L.D., and Srimannarayana, G. (1998) J. Agric. Food. Chem., 46, 2797.
3-O-METHYL-3-DEACETYLSALANNIN C33H44O8
(568.71)
Only spectral data given
O
O
O O
O
O
H3CO
H
O
(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.
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)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(1) Yamasaki, R.B. and Klocke, J.A. (1989) J. Agric. Food Chem., 37, 1118.
n25
D : 1.5000
COOCH3
(1) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(1) Jacobson, M., Crystal, M.M., and Warthen, J.D. Jr. (1981) J. Agric. Food Chem., 29, 591.
O
O
HO
O O
H3COOC
OH
(1) (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.
n25
D : 1.5287
CH2OH
O
O
(1) (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.
nD25 : 1.5368
OH
O
O
(1) (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.
N-METHYL-TRANS-4-HYDROXY-L-PROLINE C6H11O3N
(145.16)
M.p. : 237–241° (dec.)
H H
N
OH H
H COOH
H H
(1) (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.
(CH2)15.CH3
O
N
H
(1) (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.
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)
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.
OH
O
O
N
H
(1) (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.
[α]20
D : –36.9° (CHCl3)
CH2
H
HO COOCH3
(1) (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
(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.
CH2
(1, 2) (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.
10–2 mol/l Feeding inhibition = Treatment duration =
80.0% 2 h.
(2, 3)
COOCH3
HO OH
OH
(1, 2) (1)
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%
(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.
[α]29
D : +5.2° (Me2CO)
(CH2)12COOH
H3C C H
CH2.CH3
(1, 2) (1)
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)
OH
(1, 2) (1)
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)
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.
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.
METHYLISOCEDRELONATE C26H30O6
(458.52)
Only spectral data given
O
COOCH3
HO
(1) (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 42.5% instar larvae for 24 h.
test (2)
5 µg/cm2 Feeding inhibition =
52.5%
(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 Krishna Kumatri,
G.N. (1995) J. Chem. Ecol., 21, 1585.
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.
[α]24
D : + 198° (MeOH)
H
H3CO
O
H3CO
H OCH3
(1) (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.
2-METHYL-6-METHOXY-1,2,3,4- C13H16ON2
TETRAHYDRO-β-CARBOLINE (216.28)
M.p. : 207–208°
H3CO
N
N
H
(1) (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.
3-O-METHYLNIVEUSIN–A C21H28O8
(408.45)
Only spectral data given
O
OH
H3CO O
CH2
OH
O
(1) (1)
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
(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.
M.p. : 39.1°
B.p. : 21.5°/15 mm
H3CO O
(1, 2) (1)
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)
B.p. : 200°/2mm
COOH
H C CH3
CH2 (CH2)14CH3
(1, 2) (1)
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)
(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.
[α]20
D : +4.84°
COOH
H3C (CH2)14H2C C H
CH3
(1, 2) (1)
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)
7-O-METHYLPHASEOLLIN C21H20O4
(336.39)
M.p. : 120–122°
H3CO O
H
O
O
(1) (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.
HO O
H3CO O
(1) (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.
7-O-METHYL-8-PRENYLFLAVANONE C22H24O3
(336.41)
No physical data given
H3CO O
(1) (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.
METHYLSAINFURAN C17H16O5
(300.31)
M.p. : 147–148°
H3CO OCH3
OH
O
OCH3
(1) (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.
Nω-METHYLTRYPTAMINE C11H14O2
(174.25)
M.p. : 90°
(87–88°)
N NH
H
(1, 2, 3) (1, 2)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(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.
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)
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)
(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.
MONOMETHOXYCHALCONE C21H20O4
(4-Methoxylonchocarpin) (336.39)
M.p. : 130°
(109°)
O
OCH3
OH O
(1) (1)
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.
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
Treatment duration =
24 h.
(2)
Treatment duration =
8 h.
(2)
(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.
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.
MUZIGADIAL C15H20O3
(canellal) (248.32)
M.p. : 127–128°
[α]25
D : –193° (CHCl3)
CHO
OH
CHO
H
CH2
(1, 2) (1, 2)
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)
(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.
MYRCENE C10H16
(136.24)
Oil
B.p. : 51–51.5°/8.5 mm
(1, 2) (2)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(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.
MYRICITRIN C21H20O12
(464.38)
M.p. : 194–197°
OH
OH
HO O
OH
OH
O
OH
OH O
O
OH
(1) (1)
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)
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)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
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.
B.p. : 250.5°/100 mm
n70
D : 1.4273
COOH
(1, 2) (1, 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 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)
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.
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.
NAGILACTONE–C C19H22O7
(362.37)
M.p. : 290° (dec.)
O
O
HO OH
H
O
O
(1, 2) (1)
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.
NAGILACTONE–D C18H20O6
(332.35)
M.p. : 265–266° (dec.)
O
O
HO
H
O
O
(1, 2) (1)
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.
1 – NAPHTHALDEHYDE C11H8O
(156.16)
No physical data given
CHO
(1, 2) (1)
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.
2 – NAPHTHALDEHYDE C11H8O
(156.16)
No physical data given
CHO
(1) (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.
NARINGENIN C15H12O5
(272.26)
M.p. : 251°
(227–228°)
OH [α]27
D : –22.5° (MeOH)
HO O
OH O
(1, 2) (1, 2)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
Treatment duration =
24 h.
(3)
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.
[α]25
D : +161.6° (EtOH)
COOH
(1, 3, 4) (1, 2)
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.
NEOADENOSTYLONE C20H24O4
(328.41)
M.p. : 104–109°
[α]24
D : –86° (CHCl3)
O O
(1, 2) (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
(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.
OH
CH2OH
O
HO
O COCH2CH2 OCH3
HO
O
OH OH
HO
OH
OH
(1–4) (1, 2)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
Treatment duration =
24 h.
(4)
Treatment duration =
8 h.
(4)
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)
(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.
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)
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.
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)
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.
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.
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.
NICANDRENONE–1 C28H34O6
(466.57)
M.p. : 117°
O
O
H
O
OH
O
OH
(1, 2) (1)
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)
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.
NIMBANDIOL C26H32O7
(456.53)
M.p. : 121°
OCH3 [α]20
D : +187.9° (CHCl3)
O O
O
HO OH
(1, 2) (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)
NIMBIN C30H36O9
(540.61)
M.p. : 205°
O O
O
H3COOC OAc
(1, 2) (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%
(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.
NIMBINENE C28H34O7
(482.57)
M.p. : 134°
OCH3 [α]20
D : +168° (CHCl3)
O O
O
OAc
(1, 2) (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)
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.
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.
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.
NIMBOLIDIN–F C41H56O12
(740.89)
Amorphous powder
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.
NIMBOLININ–B C35H46O10
(626.74)
Amorphous powder
OH [α]20
D : –55.5° (CHCl3)
O
OAc
AcO OOC
(1, 2) (1)
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)
NOMILIN C28H34O9
(514.57)
Only spectral data given
O
OAc
O
O
O O
O O
(1, 2) (1)
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)
(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.
B.p. : 297–298°/100 mm
HOOC
(1, 2) (1)
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)
NOOTKATONE C15H22O
(218.34)
M.p. : 36–37°
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
(1) Maistrello, L., Handerson, G., and Laine, R.A. (2003) Pest Manag. Sci, 59, 58.
(2) MacLeod, W.D. (1965) Tetrahedron Lett., 4779.
NORDAMNACANTHAL C15H8O5
(268.23)
M.p. : 220°
O OH
CHO
OH
(1, 2) (2)
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,
OBACUNONE C26H30O7
(454.52)
M.p. : 229–230°
O (209–211°)
O
O O
O O
(1, 2) (1, 2)
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%
(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.
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
(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.
1 – OCTADECENE C18H36
(252.49)
M.p. : 17.5°
B.p. : 144–146°/3 mm
n20
D : 1.4448
(1, 2) (1)
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)
COOH
(1, 2) (1)
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)
(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.
B.p. : 124°/10 mm
COOH
(1, 2) (1)
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)
COO
HO OH
OH
(1, 2) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
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.
OHCHINOLIDE–C C37H48O10
(652.78)
Amorphous powder
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.
B.p. : 286°/100 mm
COOH
n18
D : 1.463
(1, 2) (1)
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)
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
ONOPORDOPICRIN C19H24O6
(348.40)
M.p. : 55–56°
[α]20
D : +166.8° (MeOH)
CH2
OCOC.CH2OH
CH2
O
CH2OH
O
(1, 2) (1)
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
(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.
OSMUNDALACTONE C6H8O3
(128.13)
M.p. : 82–82.5°
[α]22
D : –70.6° (H2O)
HO
H
O O
(1, 2) (1)
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.
O-OXALYLHOMOSERINE C6H9O6N
(191.14)
Only spectral data given
O O NH2
HO O O
HO
(1, 2) (1)
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.
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.
[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.
3-OXOGRANDOLIDE C15H20O4
(264.32)
M.p. : 143–144°
CH2 [α]24
D : +50° (CHCl3)
H OH
H
O
(1, 2) (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 = 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
(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.
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)
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.
M.p. : 211–213°
[α]20
D : –169° (MeOH)
CH2
COOH
(1, 2) (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)
B.p. : 268.5°/100 mm
COOH
(1, 3) (1, 2)
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.
(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.
COOH
(1, 2, 3) (1, 2)
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.
PAPAVERINE C20H21O4N
(339.39)
M.p. : 146.5–147.5°
OCH3
OCH3
H3CO
N
H3CO
(1, 2) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(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.
PARTHENIN C15H18O4
(262.31)
M.p. : 163–166°
[α]25
D : +7.02° (CHCl3)
HO
O CH2
O
(1) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(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.
PARTHENOLIDE C15H20O3
(248.32)
M.p. : 116.5–117°
[α]20
D : –81.4° (CHCl3)
CH2
O
O
O
(1, 2) (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
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.
PEDONIN C27H32O9
(500.54)
M.p. : 259–261°
OH O
COOCH3
O O
(1) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(1) Hassanali, A., Bentley, M.D., Salwin, A.M.Z., Williams, D.J., Shephard, R.N., and Chapya, A.W. (1987)
Phytochemistry, 26, 573.
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)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
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.
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)
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.
(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.
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)
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.
(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.
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)
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.
(1) Govindachari, T.R., Krishna Kumari, G.N., and Partho, P.D. (1998) Phytochemistry, 49, 2129.
PERAMINE C12H17ON5
(247.30)
M.p. : 242–243°
(HBr)
O
N
N
NH
N NH2
H
(1, 2) (3)
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.
H3CO
OCH3
(1) (1)
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.
PERLOLINE C20H17O3N2
(333.37)
Only spectral data given
NH
OCH3
OCH3
(1) (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)
PETASITOLIDE–B C20H28O4
(332.44)
M.p. : 146°
[α]20
D : +31.8° (CHCl3)
H
O O
(1, 2) (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 = 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
(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.
PEUCEDANIN C15H14O4
(258.27)
M.p. : 109°
H3CO
O O O
(1, 2, 3) (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)
O
O
(1) (1, 2)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
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%
O
OH
(1, 2) (1)
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.
HO O
HO O
(1, 2) (1)
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)
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.
PHELLOPTERIN C17H16O5
(300.31)
M.p. : 102°
OCH3
O O O
(1, 2) (1)
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.
PHENANTHRIDINE C13H10N
(180.22)
No physical data given
(1) (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.
M.p. : 159–160°
NH2 - HCl
(1) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
Calculated from
Reference 1.
(1)
(1) Kurata, S. and Sogawa, K. (1976) Appl. Ent. Zool., 11, 89.
PHENOL C6H6O
(94.11)
B.p. : 68–71°/0.5 mm
n25
D : 1.5210
OH
(1) (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-PHENYL-4-(2-O-ALKYL-BENZOYL) C20H18O4N2
PYRAZOLE–A (350.37)
M.p. : 105°
COOC2H5
O
N N
(1) (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.
1-PHENYL-4-(2-O-ALKYL-BENZOYL) C21H20O4N2
PYRAZOLE–B (364.40)
M.p. : 118°
COOC2H5
O
N N
(1) (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.
1-PHENYL-4-(2-O-ALKYL-BENZOYL) C20H17O4N2Cl
PYRAZOLE–C (384.82)
M.p. : 120°
COOC2H5
O
Cl
N N
(1) (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.
1-PHENYL-4-(2-O-ALKYL-BENZOYL) C20H17O4N2Br
PYRAZOLE–D (384.82)
M.p. : 111°
COOC2H5
O
Br
N N
(1) (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.
1-PHENYL-4-(2-O-ALKYL-BENZOYL) C22H22O4N2
PYRAZOLE–E (378.43)
M.p. : 114°
COOC2H5
O
N N
(1) (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.
1-PHENYL-1-BUTYNE C10H10
(130.19)
B.p. : 201–203°
n18
D : 1.537
(1, 2, 3) (1, 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) 83.0% instar larvae for 24 h.
(3)
1-PHENYL-1-ETHYNE C8H6
(102.14)
Only spectral data given
CH
(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-PHENYL-1-HEXYNE C12H14
(158.24)
Only spectral data given
(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-PHENYL-2,4-PENTADIYNE C11H8
(140.18)
B.p. : 45–50°/.001 mm
(1, 2) (1)
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.
1-PHENYL-1-PENTYNE C11H12
(144.22)
Only spectral data given
(1) (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)
H3CO
OCH3 O
H3CO OCH3
CH2
(1) (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.
1-PHENYL-1-PROPYNE C9H8
(116.16)
B.p. : 182–183°
n18
D : 1.561
(1, 2, 3) (1, 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) 96.0% after 2 h instar larvae.
(3)
3-(1-PHENYL-1H-PYRAZOL-4YL) C18H12O3N2
BENZOFURAN-2-CARBOXYLIC ACID–A (304.31)
M.p. : 236°
O COOH
(1) (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.
3-(1-PHENYL-1H-PYRAZOL-4YL) C19H14O3N2
BENZOFURAN-2-CARBOXYLIC ACID–B (318.33)
M.p. : 210°
O COOH
(1) (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.
3-(1-PHENYL-1H-PYRAZOL-4YL) C18H11O3N2Cl
BENZOFURAN-2-CARBOXYLIC ACID–C (338.75)
M.p. : 215°
O COOH
Cl
N
(1) (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.
3-(1-PHENYL-1H-PYRAZOL-4YL) C18H11O3N2Br
BENZOFURAN-2-CARBOXYLIC ACID–D (383.20)
M.p. : 223°
O COOH
Br
N
(1) (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.
3-(1-PHENYL-1H-PYRAZOL-4YL) C20H16O3N2
BENZOFURAN-2-CARBOXYLIC ACID–E (332.36)
M.p. : 213°
O COOH
(1) (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.
PHLORETIN C15H14O5
(274.27)
M.p. : 262° (dec.)
OH
HO OH
OH O
(1) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
Concentration = EC50
(2)
Concentration = EC50
(2)
HO OH O
H
H
OH
OH (1) (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.
PHLORIZIN C21H24O10
(436.41)
M.p. : 110°
OH
[α]25
D : –52° (EtOH)
HO OH
HO OH
O
O OH
OH
(1, 2) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
Concentration = EC50
(2)
Concentration = EC50
(2)
COOH
COOH
(1, 2) (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 11.4% of 10 to 13 mg body
weight.
Treatment duration =
6 days.
(2)
(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.
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)
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)
(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.
PICRASIN–B C21H28O6
(376.45)
M.p. : 255–257°
O
O
HO
H
O O
H
H
(1, 2) (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.
PICROTOXININ C15H16O6
(292.29)
M.p. : 209.5°
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.
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)
PIMPINELLIN C13H10O5
(246.22)
M.p. : 119°
OCH3
H3CO
O O O
(1, 2, 3) (1, 2)
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)
PINGUISONE C15H20O2
(232.32)
M.p. : 63–63.5°
[α]25
D : +64.3° (Benzene)
(1, 2) (1)
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%
(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.
[α]25
D : +24.5°
H
N COOH
(1, 2) (1, 2)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(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.
PIPERENONE C22H28O6
(388.46)
M.p. : 86–88°
H3CO
[α]20
D : –129° (MeOH)
H3CO O
OCH3
H3CO
(1) (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%
0.001% No activity
(1) Matsui, K., Wada, K., and Munakata, K. (1976) Agric. Biol. Chem., 40, 1045.
H3CO O
OH
O
O
O
(1, 2) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
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.
PISCIDINOL–C C32H46O8
(558.71)
M.p. : 215°
OH
O O
AcO
HO
O OH
(1, 2, 3) (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)
(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.
PLAGIOCHILINE–A C19H26O6
(350.41)
Oil
AcO O
H
H H
AcO
(1, 2) (1, 2)
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.
PLICTRAN C18H34OSn
(385.16)
M.p. : 195–198°
HO Sn
(1, 2) (1)
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)
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)
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%
(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.
POLHOVOLIDE C23H32O8
(436.50)
M.p. : 98–99°
[α]20
D : –83.5° (CHCl3)
OAc
OAc
O
O
(1, 2) (1)
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
(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.
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)
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)
(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.
O
O
(1) (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.
HO O
(1) (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.
PRIEURIANIN C38H50O16
(762.80)
OH M.p. : 214–218°
COOH
AcO
O
OH
O
O CH2
COOCH3
CH2OAc
(1, 2) (2, 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
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.
COOH
AcO
O
OH
O
O CH2
COOCH3
CH2OAc
(1) (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
(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.
epoxy-PRIEURIANIN C38H50O15
(746.80)
OH [α]D : +24.5° (CHCl3)
COOH
AcO
O
O CH2
COOCH3
CH2OAc
(1, 2) (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
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.
COOH
AcO
O
O CH2
COOCH3
CH2OAc
(1, 2) (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
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.
PRONAMIDE C12H11ONCl2
(256.13)
M.p. : 155–157°
Cl CONHC C CH
Cl
(1) (1)
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)
(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.
COO
OH
HO
OH
(1) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
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)
PROTOCATECHUIC ACID C 7 H 6O 4
(154.12)
M.p. : ~200° (dec.)
(195–196°, anhyd.)
COOH
OH
OH
(1, 2) (1, 3)
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)
PSORALEN C11H6O3
(186.17)
M.p. : 171°
(161–162°, 165°)
O O O
(1, 2) (1, 2)
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.
PTEROSIN–F C14H17OCl
(236.74)
M.p. : 66–67°
Cl
(1, 2) (1, 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.
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)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
PYROGALLOL C6H6O3
(126.11)
M.p. : 133–134°
B.p. : 171.5°/12 mm
OH
HO
OH
(1) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
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)
(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.
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)
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
(1) Blaney, W.M., Simmonds, M.S.J., Ley, S.V., Anderson, J.C., and Toogood, P.L. (1990) Entomol. Exp. Appl.,
55, 149.
QUADRANGOLIDE C15H20O3
(248.32)
M.p. : 118–120°
O
O
CH2
O
(1) (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.
QUASSIN C22H28O6
(388.46)
M.p. : 221–222°
O
O
H3CO
H
O O
(1, 2) (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) 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.
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
Concentration = EC50
value.
(2)
Concentration = EC50
value.
(2)
(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.
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)
ACTIVITY PROFILE
Test Conc. /
Test insect Efficacy Remarks
Method Dose
Concentration = EC50
value.
(3)
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.
QUININE C20H24O2N2
(324.42)
M.p. : 177° (anhydrous)
[α]15
D : –159° (EtOH)
CH2
HO
N
H
H3CO
(1, 2) (1)
ACTIVITY PROFILE
Test Conc. /
Test insect Efficacy Remarks
Method Dose
Treatment duration =
6–24 h.
(2)
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.
REMIROL C14H16O4
(248.28)
M.p. : 76–77°
[α]D25 : +66.5°
O OH
O CH 2
CH3O
(1) (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.
RHODOJAPONIN–III C20H32O6
(368.46)
M.p. : 274° (dec.)
285–287°
OH
H
O OH
OH
OH
OH
(1, 2) (1, 2)
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.
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.
(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.
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)
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)
(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.
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)
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.
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
Concentration = EC50
value.
(2)
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)
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) 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.
RUTAEVIN C26H30O9
(486.52)
M.p. : 300°
O
[α]26
D : –130° (Me2CO)
O
O O
O
O O
OH
(1, 2) (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.
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)
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)
RYANODINE C25H35O9N
(493.55)
M.p. : 219–220°
HO OH
O O
O
OH
HO
NH
(1, 2) (1, 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.
RYANODOL C20H32O8
(400.47)
M.p. : 345–347°
OH
OH
HO OH
O
HO
OH
HO
(1) (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)
(1) Gonzalex-Coloma, A., Terrero, D., Perales, A., Escoubas, P., and Fraga, B.M. (1996) J. Agric. Food Chem.,
44, 296.
SAINFURAN C16H14O5
(286.28)
M.p. : 150–152°
H3CO OH
OH
O
OCH3
(1) (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.
COOH
OH O
O
HO
H
O
(1) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(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.
SALANNIN C34H44O9
(596.72)
M.p. : 167–170°
O O
O
O
AcO
H
O
(1) (2)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
Concentrations
denote protection
levels.
(1)
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)
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.
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)
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)
(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.
O O
O
O
AcO
H
O
(1, 2) (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.
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.
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)
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.
(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.
SALANNOLACTAM–II C34H45O9N
(611.73)
[α]20
D : 126.3° (CH2Cl2)
O
O
O
O NH
O
O
AcO
H
O
(1) (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.
(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.
SALONITENOLIDE C15H20O4
(264.32)
M.p. : 136°
[α]20
D : 199.4° (MeOH)
OH
CH2
O
CH2OH
O
(1, 2) (1, 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 = 51–100
(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.
SAMADERINE–B C19H22O7
(362.38)
M.p. : 235–240°
HO
HO
O O
O
H
(1, 2) (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
(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.
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)
SANDORICIN C31H40O11
(588.65)
M.p. : 215–217°
O
O O
O
O
O
O
CH2 OH
O
COOCH3
(1) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
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.
(1) Powell, R.G., Mikolajczak, K.L., Zilkowski, B.W., Mantus, E.K., Cherry, D., and Clardy, J. (1991) J. Nat.
Prod., 54, 241.
SANTONIN C15H18O3
(246.31)
M.p. : 174–176°
[α]18
D : –173° (EtOH)
O
O
(1, 2) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
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)
(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.
8-β-SARRACINOYLOXYCUMAMBRANOLIDE C20H26O6
(362.42)
M.p. : 129–130°
OH
OH
O
CH2
O
(1, 2) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
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
SCABEQUINONE C15H16O4
(260.29)
M.p. : 108–110°
O O
(1) (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.
SCHKUHRIN–I C22H28O8
(420.46)
M.p. : 59–61°
O
O
CH2
OH
(1) (1, 2)
ACTIVITY PROFILE
Test Conc. /
Test Insectt Efficacy Remarks
Method Dose
(1) Pettei, M.J., Miura, I., Kubo, I., and Nakanishi, K. (1978) Heterocycles, 11, 471.
(2) Dictionary of Natural Products (1994) Chapman & Hall, London.
SCHKUHRIN–II C25H34O9
(478.54)
M.p. : 65–66°
OC H
AcO
CH2OH
O CH2OH
CH2
(1) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(1) Pettei, M.J., Miura, I., Kubo, I., and Nakanishi, K. (1978) Heterocycles, 11, 471.
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
(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
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
(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.
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)
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.
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
(1) Bruno, M., Vassallo, N., and Simmonds, M.S.J. (1999) Phytochemistry, 50, 973.
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)
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.
B.p. : 199°
COOH
(1) (1)
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)
SENECIONINE C18H25O5N
(335.40)
M.p. : 232–233°
C
C H2C C
C C O
H
OH
O C O
H
O CH2
(1, 2) (1, 2)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
OH [α]25
D : +213° (pyridine)
HO
HO
O
O O
H H
OOC
(1, 2)
(1)
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)
(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.
SENECIPHYLLINE C18H23O5N
(333.38)
M.p. : 217–218° (dec.)
OH [α]17
D : –139° (CHCl3)
CH2 O
O O H
(1, 2) (1)
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)
(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.
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)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(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.
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)
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)
(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.
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.
[α]25
D : –61.9° (CHCl3)
OCOCH3
O
OCOCH3
(1, 2) (2)
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.
2. Trimeresia miranda Butler Leaf disk 0.25% Feeding deterrence = 2. Treatment to 3rd
(Borneo moth) choice test 100% instar larvae.
(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.
[α]25
D : –44.8° (CHCl3)
OCOCH3
O
OH
(1, 2) (2)
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.
2. Trimeresia miranda Butler Leaf disk 0.25% Feeding deterrence = 2. Treatment to 3rd
(Borneo moth) choice test Approx. 70.0% instar larvae.
(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.
SHIROMOOL C15H26O2
(238.37)
M.p. : 72–73°
[α]25
D : +85.5° (CHCl3)
O
OH
(1, 2) (2)
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.
(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.
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)
(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
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.
SILPHINEN-3,5-DIONE C15H20O2
(232.15)
Oil
O O
(1) (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
Concentrations =
EC50 value.
(1)
(1) Reina, M., Nold, M., Santana, O., Orihuela, J.C., and Gonzalez-Coloma, A. (2002) J. Nat. Prod., 65, 448.
SILPHINEN-3,5,11-TRIONE C15H18O3
(246.13)
Oil
O O
(1) (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.
(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.
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)
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%
SIMALIKALACTONE–A C22H32O6
(392.49)
M.p. : 278.5°
HO
O
H3CO
H
O O
(1, 2) (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
(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.
SIMALIKALACTONE–D C25H34O9
(478.54)
M.p. : 228–230°
[α]D : +53°
OH
HO
HO
O
O OCO
H
O O
(1, 2) (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.
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.
(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.
SIMAROLIDE C27H36O9
(504.58)
M.p. : 264–270°
H3CCOO
O
O
HO
H O
O O
(1, 2) (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 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.
COOH
H3CO OCH3
OH
(1, 2, 3) (1, 2)
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.
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)
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.
SOLANIDINE C27H43ON
(397.65)
M.p. : 218–219°
[α]21
D : –29° (CHCl3)
HO
(1, 2) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(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.
α-SOLANINE C45H73O15N
(868.07)
M.p. : 285° (dec.)
[α]20
D : –60° (pyridine)
Rham-glu-gal-O
(1, 2) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
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)
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.
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.
(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.
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)
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.
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)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(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.
SPECIONIN C20H26O8
(394.42)
Oil
HO COO
OC2H5
O
O
CH2OH OC2H5
(1, 2) (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.
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)
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.
(1, 2) (1, 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.
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)
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)
B.p. : 386°
O OH
(1, 2) (1)
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
STEMOFOLINE C22H29O5N
(387.46)
M.p. : 87–89°
OCH3
O O
O
O
(1, 2) (2)
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.
[α]18
D : +230° (MeOH)
OCH3
O O
O
O
(1) (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.
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.
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)
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.
STRYCHNINE C21H22O2N2
(334.42)
M.p. : 270–271°
(275–285°)
[α]18
D : –139° (CHCl3)
N
H
O
O
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
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.
(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.
O OH
OH
(1) (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
Strong antifeedance
Slight antifeedance
(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.
COOH
O
OCOCH2.CH2COOH
(1) (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)
TAGITININ–A C19H28O7
(368.43)
M.p. : 168–170°
O
O
HO CH2
O
O
(1, 2) (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%
(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.
TAGITININ–C C19H24O6
(348.39)
Oil
OH
O O
O CH2 O
(1, 2) (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%
(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.
TANGERETIN C20H20O7
(372.35)
M.p. : 152°
OCH3
OCH3
H3CO O
H3CO
OCH3 O
(1) (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.
OCH3
OCH3
H3CO O
H3CO
OH O
(1) (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.
TECLEANTHINE C17H15O5N
(313.31)
M.p. : 158°
O OCH3
N O
OCH3
(1, 2) (1, 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.
TENULIN C17H22O5
(306.36)
M.p. : 196–198°
[α]20
D : –21.7° (EtOH)
O
O O
OH
(1, 2) (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.
H
H
O
H
O
O O
OH
(1) (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.
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)
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.
γ-TERPINENE C10H16
(136.23)
B.p. : 58–62.5°/10 mm
[α]25
D : +36° (neat)
n25
D : 1.4696
(1, 2) (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) 61.0% after 2 h. instar larvae.
(2)
(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.
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)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(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.
TETRAHYDRO-ACETYLISOMONTANOLIDE C24H36O8
(452.51)
Only spectral data given
OCOCH3
H
OCO
H
O OCOCH3
(1, 2) (1)
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
(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.
TETRAHYDROISOPONGAFLAVONE C21H22O4
(338.40)
M.p. : 167–168°
O O
OCH3 O
(1) (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.
TEUCJAPONIN–A C22H28O7
(404.46)
M.p. : 145–148°
O
[α]20
D : +38.8° (CHCl3)
O
H
O
OAc OH
(1, 2) (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.
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)
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.
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)
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.
TEUCVIN C19H20O5
(328.36)
M.p. : 207–208°
O
[α]D : +88.4° (CHCl3)
O
H
O
O
(1, 2) (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.
TEUFLIDIN C19H20O6
(344.36)
M.p. : 178°
O
[α]20
D : –100° (CHCl3)
O
H
O
HO
O
(1, 2) (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.
(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.
TEUFLIN C19H20O5
(328.36)
M.p. : 153°
O
[α]D : +12° (CHCl3)
O
H
O
(1, 2) (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 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.
(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.
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)
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.
TEUMASSILENIN–C C20H30O5
(350.46)
M.p. : 125–127°
O
[α]20
D : –33.4° (CHCl3)
OH
HO
O
OH
(1, 2) (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 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.
TEUSCOROLIDE C19H18O5
(326.35)
M.p. : 198–200°
O
[α]20
D : +13.5° (CHCl3)
O
H
O
O
(1, 2) (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 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.
(+)-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)
(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.
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)
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.
O O
H
OCO
(1, 2) (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 6 days. instar larvae.
(2)
6.0 µg/cm2 Feeding inhibition =
30–60% after 6 days.
(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.
13 – TIGLOYLOXYLUPANINE C20H30O3N2
(346.47)
Oil
B.p. : 180–200°/0.001 mm
H
N O
H
O
O
(1, 2) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
5α-TIGLOYLOXYSILPHINEN-3-ONE C20H28O3
(316.20)
Oil
O O
(1) (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
Concentrations =
EC50 values.
(1)
(1) Reina, M., Nold, M., Santana, O., Orihuela, J.C., and Gonzalez-Coloma, A. (2002) J. Nat. Prod., 65, 448.
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)
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.
TOMATIDINE C27H45O2N
(415.66)
M.p. : 202–206°
(210–211°)
[α]25
D : +8° (CHCl3)
N
H
HO
H
(1, 2) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(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.
TOMATINE C50H83O21N
(1034.20)
M.p. : 263–268° (dec.)
[α]20
D : –18° (pyridine)
N
H
β-lycotetraose-O
H
(1, 2) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(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.
TOONACILIN C31H38O9
(554.64)
M.p. : 118–119°
O
[α]20
D : +69° (CHCl3)
OAc
AcO
O
H
CH2
O
COOCH3
(1) (1)
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.
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)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
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.
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.
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.
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.
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)
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.
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.
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.
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.
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)
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.
TRICHILIN–I C35H46O13
(674.74)
Amorphous powder
O
OAc
O
OH
HO
O H O
AcO OH
O
H
O (1) (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.
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)
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.
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)
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.
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)
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.
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.
TRICHILININ–C C33H44O7
(552.71)
Amorphous powder
[α]19
D : +22° (MeOH)
H O
OAc
O OH
(1) (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.
TRICHLOROMETHYLPHTHALAZINE C13H11ON2Cl3
(317.60)
Only spectral data given
OC2H5
CCl3
(1) (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.
N Sn
(1, 2) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
OH
HO COOCH3
O
O OCO
H
SO2F3CO O O
(1) (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.
TRILOBOLIDE C27H38O10
(522.59)
M.p. : 191–192°
[α]20
D : +73.3° (MeOH)
OCOCH3
COO OCO
OH
OH
(1, 2) (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 = 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)
(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.
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
H3CO OCH3
(1) (1, 2)
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%
(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.
TULIRINOL C17H22O5
(306.36)
M.p. : 204–206°
[α]23
D : –51° (MeOH)
HO H
H
O
O
OAc
CH2
(1) (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)
(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.
TYLOPHORINE C24H27O4N
(393.48)
M.p. : 287–288° (dec.)
OCH3
[α]25
D : –21.45° (CHCl3)
H3CO
H
H3CO
OCH3
(1, 2) (1)
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.
(±)TYLOPHORININE C23H25O4N
(379.46)
M.p. : 246° (dec.)
H3CO
OH
H
H3CO
OCH3
(1, 2) (1)
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.
NH2.HCl
OH
(1) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(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.
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)
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.
B.p. : 212.5°/100 mm
OH
(1) (1)
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.
(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.
B.p. : 275°/100 mm
OH
(1, 2) (1)
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)
(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.
UNEDOSIDE C14H20O9
(332.30)
M.p. : 232–234°
OH
H
O
O
H
O - glu
(1) (1)
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.
URSINIOLIDE–A C22H28O7
(404.46)
M.p. : 140–142°
[α]20
D : –237°
OCO
O
AcO CH2
O
(1, 2) (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 = 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
(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.
HO O O
(1, 2) (1, 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)
(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.
[α]20
D : –494° (CHCl3)
OH OH O
HO O O
(1, 2) (1, 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.
UVIDIN–A C15H24O3
(252.35)
M.p. : 123–124°
[α]20
D : +151.1° (CHCl3)
HO
(1, 2) (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.
UVIDIN–B C15H24O4
(268.35)
M.p. : 180–181°
[α]20
D : +171° (Me2CO)
HO
HO
(1, 2) (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.
[α]20
D : + 101.8° (CHCl3)
OCO
O
O
(1) (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.
[α]20
D : –45.6° (CHCl3)
CH2
HO COOH
H
(1) (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
(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.
VASICINE C11H12ON2
(188.23)
M.p. : 212°
[α]14
D : –254° (CHCl3)
OH
(1) (1, 2)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(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.
VASICINOL C11H12O2N2
(204.23)
M.p. : 272–273°
(260°- dec.)
[α]25
D : +2.5° (AcOH)
HO
N
OH
(1) (1, 2, 3)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(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.
VASICINONE C11H10O2N2
(202.21)
M.p. : 200–201°
OH
(1) (1, 2)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(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.
VERBENONE C10H14O
(150.22)
M.p. : 6.5°
B.p. : 227–228°
[α]18
D : +249.6°
(1, 2) (1, 2)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(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.
VESTITOL C16H16O4
(272.30)
M.p. : 156°
(144–145°)
HO OCH3
(1, 2) (1, 2, 3)
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.
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)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(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.
VISMIN C25H28O4
(392.49)
M.p. : 161–164°
(impure)
OH OH O
OH
(1, 2) (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.
VISMINONE–A C23H26O6
(vismione A) (398.46)
M.p. : 140–141°
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.
VISMINONE–B C21H22O5
(vismione B) (354.40)
M.p. : 200–202°
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.
VISNAGIN C13H10O4
(230.22)
M.p. : 144–145°
(138–140°)
O O
OCH3 O
(1, 2) (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)
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)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(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.
VOLKENSIN C33H44O9
(584.71)
M.p. : 185–187°
O
OH
O
O
O
AcO OH
(1) (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.
O
O
O
O
O
AcO OH
(1) (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.
O
OCH3
OH
(1) (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.
WARBURGANAL C15H22O3
(250.34)
M.p. : 106–107°
[α]22
D : +260° (CHCl3)
CHO
OH
CHO
(1) (1, 2)
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)
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)
(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.
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)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
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)
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)
(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.
WITHANICANDRIN C28H36O6
(468.59)
M.p. : 267–269°
O
O O
H
O
O
OH
(1, 2) (1)
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)
(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.
WITHANOLIDE–D C28H38O6
(470.61)
M.p. : 253–255°
O O
H
O
O
OH (1, 2, 3) (1, 2)
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)
(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.
WITHANOLIDE–E C28H38O7
(486.60)
M.p. : 167–168°
O O
OH
O
OH
O (1, 2)
(1, 2)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
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.
WITHANOLIDE–S C28H40O8
(504.62)
O O
OH
O
OH
OH
OH
(1, 2) (1)
ACTIVITY PROFILE
Test Conc. /
Test Insect Efficacy Remarks
Method Dose
(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.
XANTHOTOXIN C12H8O4
(216.19)
M.p. : 146°
O O O
OCH3
(1, 2) (2)
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)
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.
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)
(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.
OC2H5
H O O O
(1) (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.
XANTHOXYLETIN C15H14O4
(258.27)
M.p. : 132.5–134°
O O O
OCH3
(1, 2) (1, 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.
XANTHYLETIN C14H12O3
(228.24)
M.p. : 131.5°
(127–129°)
O O O
(1, 2) (2, 3)
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)
(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.
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
(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.
XYLOMOLLIN C12H18O7
(274.27)
M.p. : 138–139°
COOCH3
H
O OCH3
O O
H
OH
(1, 2) (1, 2)
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.
YATEIN C22H24O7
(400.43)
[α]20
D : –28.4° (CHCl3)
H
O
O
O
H
O
H3CO OCH3
OCH3
(1) (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 = 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