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The recognition of cerambycids as frequent and damaging invaders led to an increase in the interest in the chemical ecology of the group with the identification of pheromones and pheromone-like attractants for well over 100 species. Pheromone components of the Cerambycidae are often phylogenetically conserved, with a single compound serving as a pheromone component for several related species. In the subfamily Lamiinae, the compound 2-(undecyloxy)ethanol (monochamol) has been identified as an aggregation-sex pheromone for several species of the genus Monochamus. In other species, including Monochamus maculosus Haldeman, field trials have demonstrated that monochamol is a pheromone attractant, but at that point it was still unknown as to whether it was a pheromone for this species. Here we report the identification, and laboratory and field trials of a pheromone component produced by adult male M. maculosus. Chemical analyses of headspace volatile collections sampled from field collected beetles of both sexes revealed the presence of one male-specific compound that was identified as 2-(undecyloxy)ethanol. Electroantennography analyses showed that monochamol elicited responses from the antennae of female beetles. Traps baited with monochamol in the field captured M. maculosus adults of both sexes corroborating the identification of monochamol as the sex-aggregation pheromone of this species. The attractivity of monochamol to adult M. maculosus in our field trapping experiment was synergized by the addition of the host volatile α-pinene. [ABSTRACT FROM AUTHOR]

Polydimethylsiloxane (PDMS) tubing is increasingly being used to collect volatile organic compounds (VOCs) from static biological headspace. However, analysis of VOCs collected using PDMS tubing often deploys thermal desorption, where samples are considered as 'one-offs' and cannot be used in multiple experiments. In this study, we developed a static headspace VOC collection method using PDMS tubing which is solvent-based, meaning that VOC extracts can be used multiple times and can be linked to biological activity. Using a synthetic blend containing a range of known semiochemicals (allyl isothiocyanate, (Z)-3-hexen-1-ol, 1-octen-3-one, nonanal, (E)-anethol, (S)-bornyl acetate, (E)-caryophyllene and pentadecane) with differing chemical and physicochemical properties, VOCs were collected in static headspace by exposure to PDMS tubing with differing doses, sampling times and lengths. In a second experiment, VOCs from oranges were collected using PDMS sampling of static headspace versus dynamic headspace collection. VOCs were eluted with diethyl ether and analysed using gas chromatography – flame ionization detector (GC-FID) and coupled GC – mass spectrometry. GC-FID analysis of collected samples showed that longer PDMS tubes captured significantly greater quantities of compounds than shorter tubes, and that sampling duration significantly altered the recovery of all tested compounds. Moreover, greater quantities of compounds were recovered from closed compared to open systems. Finally, analysis of orange headspace VOCs showed no qualitative differences in VOCs recovered compared to dynamic headspace collections, although quantities sampled using PDMS tubing were lower. In summary, extraction of PDMS tubing with diethyl ether solvent captures VOCs from the headspace of synthetic blends and biological samples, and the resulting extracts can be used for multiple experiments linking VOC content to biological activity. [ABSTRACT FROM AUTHOR]

The spined shoulder bug, Podisus maculiventris, is a generalist predator studied for its biocontrol potential. Despite our growing understanding of gland development, the conditions that elicit releases are largely unknown. To determine if male age or gland development affects the chemical composition and release behavior, we dissected adult male bugs and profiled the chemical composition of the male DAG 1, 7, and 14 d post-eclosion. To determine if gland development is related to sexual maturity, we counted the number of sperm present in the seminal vesicles at the same time points. Finally, we measured the diurnal release patterns of different aged males and in various male-female combinations. We observed that newly eclosed adults have under-developed glands and male seminal vesicles contained few sperm. One week post-eclosion the DAG contained previously reported semiochemical compounds and males contained many sperm. Mirroring the trend in reproductive maturation and gland development, the number of semiochemical releases increased with age and the majority of releases followed a scotophase pattern unaffected by sexual composition. These findings link male age to 1) dorsal abdominal gland development 2) release behavior and 3) sexual maturity, which will help our understanding of when these olfactory cues are present for other organisms, like prey, to perceive. Given the results, releasing adults that are at least 1 week post eclosion will maximize the non-consumptive effects of this biocontrol agent. [ABSTRACT FROM AUTHOR]

The beetle family Disteniidae is currently considered to be closely related to the much larger family Cerambycidae, the longhorned beetles. The 300 + species of disteniids are mostly native to tropical and subtropical regions, with the only described North American species north of Mexico being Elytrimitatrix undata (F.). Here we describe the identification and field testing of (1R,4R)-quercivorol as a male-produced aggregation-sex pheromone component for E. undata. This is the first pheromone identified for any species within the family Disteniidae. [ABSTRACT FROM AUTHOR]

Longhorn beetles are ecologically important insects in forest ecosystems as decomposers of woody substrates, microhabitat engineers, and as components of forest food webs. These species can be greatly affected both positively and negatively by modern forestry management practices, and should be monitored accordingly. Through headspace sampling, coupled gas chromatography-electroantennography, gas chromatography-mass spectrometry, and field bioassays, we identified two compounds, 2-methyl-1-butanol and 3-hydroxy-2-hexanone, that constitute aggregation-sex pheromone attractants of three cerambycid species which breed primarily in different types of fresh, recently dead oak wood in Northern Europe: Pyrrhidium sanguineum (L.), Phymatodes alni ssp. alni (L.), and Phymatodes testaceus (L.) (Cerambycinae: Callidiini). Analyses of headspace volatiles collected from live insects indicated that the male-produced aggregation-sex pheromone of P. sanguineum is a 1-15:100 blend of (R)-2-methyl-1-butanol and (R)-3-hydroxy-2-hexanone, whereas the corresponding ratios for P. alni were 70-110:100. In field bioassays, adult P. sanguineum and P. alni were significantly attracted to multiple blends with varying ratios of the two compounds. When tested individually, the compounds were minimally attractive. In contrast, adult P. testaceus exhibited nonspecific attraction to both of the individual compounds and to different blends, despite the hydroxyketone not being part of its pheromone, which consists of (R)-2-methyl-1-butanol alone. Overall, our results suggest that a blend of 50:100 of racemic 2-methyl-1-butanol and 3-hydroxy-2-hexanone is appropriate for parallel, cost-efficient pheromone-based monitoring of all three species. In particular, these species could serve as useful indicators of how modern forestry practices affect a whole guild of saproxylic insects that require ephemeral deadwood substrates for successful breeding.

Silicon (Si) fertilization alleviates biotic stresses in plants. Si enhances plant resistance against phytophagous insects through physical and biochemical mechanisms. In particular, Si modifies jasmonic acid levels and the emissions of herbivore-induced plant volatiles (HIPVs). Here, we investigated whether Si accumulation in the tissues of maize leaves modifies the emissions of constitutive and herbivore-induced plant volatiles, with cascade deterrent effects on oviposition site selection by Spodoptera exigua Hübner (Lepidoptera: Noctuidae). Maize plants were cultivated in a hydroponic system under three Si concentrations, resulting in three groups of plants expressing different Si concentrations in their tissues (0.31 ± 0.04, 4.69 ± 0.49, and 9.56 ± 0.30 g Si. Kg− 1 DW). We collected volatiles from undamaged and caterpillar-infested plants, and found that Si concentration in plant tissues had no significant impact. Jasmonic acid content was high in insect-infested plants, but was similar across all Si treatments. Oviposition site selection bioassays using fertilized S. exigua females showed that Si concentration in plant tissues did not affect the number of eggs laid on Si-treated plants. In conclusion, our study shows that the Si content in maize tissues does not impact the semiochemical interactions with S. exigua. [ABSTRACT FROM AUTHOR]

A diversity of aquatic organisms manage predation risk by avoiding waters activated with conspecific alarm cues, a chemical mixture released from injuries. The sea lamprey (Petromyzon marinus) is a nocturnal migratory species that relies on its alarm cue to navigate around areas of predation risk when moving through river channels. Identification of the cue's chemistry would allow managers to harness this innate behavioral response to guide migrating sea lamprey to traps (invasive population in the Laurentian Great Lakes) or to fish passage devices where dams block migrations in their native range. We pursued isolation of the sea lamprey alarm cue through behaviorally guided fractionation, fractionating the alarm cue into water-soluble and chloroform-soluble fractions, each of which elicited a substantial avoidance response. Recombining the two fractions restored full reactivity, suggesting the alarm cue mixture contains components that exhibit high solubility in water (e.g., nitrogenous compounds), chloroform (e.g., lipids), or perhaps materials that dissolve readily in either solvent. We further screened 13 individual compounds or pure isolates and 6 sub-fractions from the water-soluble fraction and found one of the pure isolates, isoleucine, evoked an avoidance response on its own, but not consistently when found in other mixtures. In a third experiment, we observed no behavioral response after recombining 32 compounds isolated and identified from the water-soluble fraction. These results confirm other suggestions that the process of elucidating alarm cue constituents is challenging. However, we suggest the pursuit is worthwhile given the strong evidence for the utility of alarm cues for use in the conservation and management of fishes and other aquatic organisms. [ABSTRACT FROM AUTHOR]

The black turpentine beetle, Dendroctonus terebrans, is an economically important pest of pines in the Southeastern U.S., with a high potential for invasion to other pine-rich regions. Dendroctonus terebrans attraction to an injured host tree lessens over time as the host material degrades. Likewise, kairomonal volatiles emitted from the host change as constituents of the defensive resin oxidize. Therefore we hypothesized that volatiles associated with a fresh host would be more attractive to D. terebrans than those associated with a dead or dying host. We replicated the natural oxidation process of turpentine, fractionated the distilled products to isolate the oxidized products, and deployed the complex mixtures to measure field attraction based on the amount of oxidation performed. Contrasting with previous studies, our results suggest that D. terebrans attraction is not primarily based on host tree degradation. In a second experiment incorporating Dendroctonus pheromones, we demonstrate D. terebrans has a displacement-dependent response to endo-brevicomin, a pheromone associated with the sympatric southern pine beetle, D. frontalis. This has implications not only for possible interspecific signaling, but also for the role of endo-brevicomin in D. terebrans colonization behavior. The results from this study broaden the understanding of D. terebrans chemical ecology and directly contribute to the development of an effective lure-based monitoring system that will benefit future research and management efforts. This may become important if the species is established outside its native range, as in the closely related red turpentine beetle, Dendroctonus valens, which caused mass pine tree mortality following its introduction to Asia. [ABSTRACT FROM AUTHOR]

The Asian longhorn beetle (ALB), Anoplophora glabripennis (Motschulsky), is a destructive forest pest in its native range, East Asia, or a high-risk invasive species in many other parts of the world. Extensive research has been directed toward the development of ALB management strategies. However, semiochemical-based trap lures, which are one of the effective tools for detecting, monitoring, and potentially assisting in eradicating cerambycids, have not reached operational efficacy for ALB to date, which is probably due to a grossly incomplete understanding of its chemical ecology. Here, we summarize the current progress in ALB chemical ecology including host selection and location, pheromone identification, trapping techniques, olfactory system, and related biology and behavior. We also briefly review the known semiochemicals in the subfamily Lamiinae, particularly the ALB congener, A. chinensis. Based on this knowledge, we highlight a potentially important role of some host-original chemicals, such as sesquiterpenes, in ALB host and mate location, and emphasize the basic studies on the biology and behavior of adult ALB. Last, we formulate suggestions for further research directions that may contribute to a better understanding of ALB chemical ecology and improved lure efficacy. [ABSTRACT FROM AUTHOR]

Avian chemical communication, once largely overlooked, is a growing field that has revealed the important role that olfaction plays in the social lives of some birds. Leach's storm-petrels (Oceanodroma leucorhoa) have a remarkable sense of smell and a strong, musky scent. This long-lived, monogamous seabird relies on olfaction for nest relocation and foraging, but whether they use scent for communication is less well studied. They are nocturnally active at the breeding colony and yet successfully reunite with their mate despite poor night-vision, indicating an important role for non-visual communication. We investigated the chemical profiles of Leach's storm-petrels to determine whether there is socially relevant information encoded in their plumage odor. To capture the compounds comprising their strong scent, we developed a method to study the compounds present in the air surrounding their feathers using headspace stir bar sorptive extraction coupled with gas chromatography-mass spectrometry. We collected feathers from Leach's storm-petrels breeding on Bon Portage Island in Nova Scotia, Canada in both 2015 and 2016. Our method detected 142 commonly occurring compounds. We found interannual differences in chemical profiles between the two sampling years. Males and females had similar chemical profiles, while individuals had distinct chemical signatures across the two years. These findings suggest that the scent of the Leach's storm-petrel provides sociochemical information that could facilitate olfactory recognition of individuals and may inform mate choice decisions. [ABSTRACT FROM AUTHOR]

Female Harmonia axyridis (Coleoptera: Coccinellidae) produce a sex pheromone to attract males. In the present study, we tested two hypotheses: (i) production of sex pheromone in H. axyridis is conditioned by perception of prey in their vicinity, and (ii) virgin females invest in the production of the sex pheromone, while mated females reduce their pheromone emissions. To test the first hypothesis, newly hatched larvae were divided into three groups: those fed with Ephestia kuehniella eggs, those fed with pea aphids, and those exposed to aphid volatile cues but fed with Ephestia eggs. All females produced a pheromone blend of five-components in similar relative proportions, but with contrasting absolute quantities: Females fed with Ephestia eggs produced lower amounts of pheromone (0.5 ± 0.4 ng.female−1), compared to females fed with aphids (44.2 ± 24.4 ng.female−1). The females of the third group produced intermediate concentrations of pheromone (6.0 ± 3.2 ng.female−1). To test the second hypothesis, two groups of lady beetles were made: one group of females was placed in the presence of males, while females of the other group were not. Mated and virgin females produced statistically similar amounts of pheromone (144.1 ± 49.7 ng and 43.7 ± 24.1 ng.female−1, respectively). These results suggest that H. axyridis females initiate pheromone production upon exposure to volatile cues released by their aphids prey. Females continue to release sex pheromone after mating, probably to increase the chance of multiple mating which is known to improve egg fertility. [ABSTRACT FROM AUTHOR]

We describe the identification, synthesis, and field bioassays of a novel aggregation-sex pheromone produced by males of Susuacanga octoguttata (Germar), a South American cerambycid beetle. Analyses of extracts of headspace volatiles produced by adult beetles revealed a sex-specific compound emitted by males which was identified as (Z)-7-hexadecene by microchemical and spectroscopic analyses. The synthesized pheromone was attractive to beetles of both sexes in field trials. This unsaturated hydrocarbon motif is unprecedented among cerambycid pheromones identified to date. During field bioassays, we serendipitously discovered that adults of S. octoguttata trapped in two Brazilian biomes differed considerably in elytral markings, although males from both populations produced (Z)-7-hexadecene as an aggregation-sex pheromone. [ABSTRACT FROM AUTHOR]

(Z)-4-undecenal (Z4-11Al) is the volatile pheromone produced by females of the vinegar fly Drosophila melanogaster. Female flies emit Z4-11Al for species-specific communication and mate-finding. A sensory panel finds that synthetic Z4-11Al has a characteristic flavour, which can be perceived even at the small amounts produced by a single female fly. Since only females produce Z4-11Al, and not males, we can reliably distinguish between single D. melanogaster males and females, according to their scent. Females release Z4-11Al at 2.4 ng/h and we readily sense 1 ng synthetic Z4-11Al in a glass of wine (0.03 nmol/L), while a tenfold concentration is perceived as a loud off-flavour. This corroborates the observation that a glass of wine is spoilt by a single D. melanogaster fly falling into it, which we here show is caused by Z4-11Al. The biological role of Z4-11Al or structurally related aldehydes in humans and the basis for this semiochemical convergence remains yet unclear. [ABSTRACT FROM AUTHOR]

During field screening trials conducted in Brazil in 2015, adults of both sexes of the cerambycid beetles Cotyclytus curvatus (Germar) and Megacyllene acuta (Germar) (subfamily Cerambycinae, tribe Clytini) were significantly attracted to racemic 3-hydroxyhexan-2-one and racemic 2-methylbutan-1-ol, chemicals which previously have been identified as male-produced aggregation-sex pheromones of a number of cerambycid species endemic to other continents. Subsequent analyses of samples of beetle-produced volatiles revealed that males of C. curvatus sex-specifically produce only (R)-3-hydroxyhexan-2-one, whereas males of M. acuta produce the same compound along with lesser amounts of (2S,3S)-2,3-hexanediol and (S)-2-methylbutan-1-ol. Follow-up field trials showed that both sexes of both species were attracted to synthetic reconstructions of their respective pheromones, confirming that males produce aggregation-sex pheromones. The minor pheromone components of M. acuta, (S)-2-methylbutan-1-ol and (2S,3S)-2,3-hexanediol, synergized attraction of that species, but antagonized attraction of C. curvatus to (R)-3-hydroxyhexan-2-one. Beetles of other cerambycine species also were attracted in significant numbers, including Chrysoprasis linearis Bates, Cotyclytus dorsalis (Laporte & Gory), and Megacyllene falsa (Chevrolat). Our results provide further evidence that 3-hydroxyhexan-2-one is a major component of attractant pheromones of numerous cerambycine species world-wide. Our results also highlight our increasing understanding of the crucial role of minor pheromone components in imparting species specificity to cerambycid pheromone blends, as is known to occur in numerous species in other insect families. [ABSTRACT FROM AUTHOR]

Within the Phylum Echinodermata, the class Asteroidea, commonly known as starfish and sea stars, encompasses a large number of benthos inhabiting genera and species with various feeding modalities including herbivores, carnivores, omnivores and detritivores. The Asteroidea rely on chemosensation throughout their life histories including hunting prey, avoiding or deterring predators, in the formation of spawning aggregations, synchronizing gamete release and targeting appropriate locations for larval settlement. The identities of many of the chemical stimuli that mediate these physiological and behavioural processes remain unresolved even though evidence indicates they play pivotal roles in the functionality of benthic communities. Aspects of chemosensation, as well as putative chemically-mediated behaviours and the molecular mechanisms of chemoreception, within the Asteroidea are reviewed here, with particular reference to the coral reef pest the Crown-of-Thorns starfish Acanthaster planci species complex, in the context of mitigation of population outbreaks. [ABSTRACT FROM AUTHOR]

In this study, we isolated and identified an aggregation-sex pheromone from Monochamus saltuarius, the major insect vector of the pine wood nematode in Korea. Adult males of M. saltuarius produce 2-undecyloxy-1-ethanol, which is known as an aggregation-sex pheromone in other Monochamus species. We performed field experiments to determine the attractiveness of the pheromone and other synergists. More M. saltuarius adult beetles were attracted to traps baited with the pheromone than to unbaited traps. Ethanol and (−)- α-pinene interacted synergistically with the pheromone. Traps baited with the pheromone + (−)- α-pinene +ethanol were more attractive to M. saltuarius adults than traps baited with the pheromone, (−)- α-pinene, or ethanol alone. Ipsenol, ipsdienol, and limonene were also identified as synergists of the aggregation-sex pheromone for M. saltuarius adults. In field experiments, the proportion of females was much higher in the beetles caught in traps than among the beetles emerging from naturally-infested logs in the laboratory. Our results suggest that a combination of aggregation-sex pheromone and synergists could be very effective for monitoring and managing M. saltuarius. [ABSTRACT FROM AUTHOR]

The influence of pheromones on insect physiology and behavior has been thoroughly reported for numerous aspects, such as attraction, gland development, aggregation, mate and kin recognition. Brood pheromone (BP) is released by honey bee larvae to indicate their protein requirements to the colony. Although BP is known to modulate pollen and protein consumption, which in turn can affect physiological and morphological parameters, such as hypopharyngeal gland (HPG) development and ovarian activation, few studies have focused on the effect of BP on nutritional balance. In this study, we exposed newly emerged worker bees for 14 d and found that BP exposure increased protein intake during the first few days, with a peak in consumption at day four following exposure. BP exposure decreased survival of caged honey bees, but did not affect either the size of the HPG acini or ovarian activation stage. The uncoupling of the BP releaser effect, facilitated by working under controlled conditions, and the presence of larvae as stimulating cues are discussed. [ABSTRACT FROM AUTHOR]

Research over the last decade has revealed extensive parsimony among pheromones within the large insect family Cerambycidae, with males of many species producing the same, or very similar aggregation pheromones. Among some species in the subfamily Cerambycinae, interspecific attraction is minimized by temporal segregation, and/or by minor pheromone components that synergize attraction of conspecifics or inhibit attraction of heterospecifics. Less is known about pheromone-based mechanisms of reproductive isolation among species in the largest subfamily, the Lamiinae. Here, we present evidence that the pheromone systems of two sympatric lamiine species consist of synergistic blends of enantiomers of ( E)-6,10-dimethyl-5,9-undecadien-2-ol (fuscumol) and the structurally related ( E)-6,10-dimethyl-5,9-undecadien-2-yl acetate (fuscumol acetate), as a mechanism by which species-specific blends of pheromone components can minimize interspecific attraction. Male Astylidius parvus (LeConte) were found to produce ( R) - and ( S)-fuscumol + ( R)-fuscumol acetate + geranylacetone, whereas males of Lepturges angulatus (LeConte) produced ( R)- and ( S)-fuscumol acetate + geranylacetone. Field experiments confirmed that adult beetles were attracted only by their species-specific blend of the enantiomers of fuscumol and fuscumol acetate, respectively, and not to the individual enantiomers. Because other lamiine species are known to produce single enantiomers or blends of enantiomers of fuscumol and/or fuscumol acetate, synergism between enantiomers, or inhibition by enantiomers, may be a widespread mechanism for forming species-specific pheromone blends in this subfamily. [ABSTRACT FROM AUTHOR]

We report the identification, synthesis, and first field bioassays of a pheromone component with a novel structure produced by adult males of Chlorida festiva (L.) and Chlorida costata Audinet-Serville, longhorn beetle species in the subfamily Cerambycinae. Headspace volatiles from males contained a sex-specific compound that was identified as (6 E,8 Z)-6,8-pentadecadienal. Traps baited with this compound captured adults of both species and sexes, consistent with the aggregation-sex pheromones produced by males of many species in this subfamily. This compound represents a new structural class of cerambycid pheromones, and it is the first pheromone identified from species in the tribe Bothriospilini. [ABSTRACT FROM AUTHOR]

Straight-chained lepidopteran pheromones are now regulated under a group standard in New Zealand, which is generic for moth pheromone products of similar low risk, under the Hazardous Substances and New Organisms Act (1996). This means that compliant new pheromone products can be developed and commercialized with low regulatory requirements. This encourages innovation and supports fruit industries interested in meeting export phytosanitary standards, while targeting low or nil residues of pesticides. Changes to pheromone blends for reasons such as technical improvements or variations in pest species composition in different crops can be made with minimal regulatory involvement. We illustrate how this system now operates with a four species mating disruption product commercialized in 2012. The odors involved in '4-Play™' consist of a range of components used by codling moth ( Cydia pomonella), lightbrown apple moth ( Epiphyas postvittana), green-headed leafroller ( Planotortrix octo), and brown-headed leafroller ( Ctenopseustis obliquana). The development of 4-Play™ illustrates how mating disruption of insects can support industry goals. [ABSTRACT FROM AUTHOR]

Research since 2004 has shown that the use of volatile attractants and pheromones is widespread in the large beetle family Cerambycidae, with pheromones now identified from more than 100 species, and likely pheromones for many more. The pheromones identified to date from species in the subfamilies Cerambycinae, Spondylidinae, and Lamiinae are all male-produced aggregation-sex pheromones that attract both sexes, whereas all known examples for species in the subfamilies Prioninae and Lepturinae are female-produced sex pheromones that attract only males. Here, we summarize the chemistry of the known pheromones, and the optimal methods for their collection, analysis, and synthesis. Attraction of cerambycids to host plant volatiles, interactions between their pheromones and host plant volatiles, and the implications of pheromone chemistry for invasion biology are discussed. We also describe optimized traps, lures, and operational parameters for practical applications of the pheromones in detection, sampling, and management of cerambycids. [ABSTRACT FROM AUTHOR]

We report the identification of a novel pheromone structure from males of the cerambycid beetle Tylonotus bimaculatus Haldeman (Cerambycinae: Hesperophanini), a species native to eastern North America. Volatiles collected from adult males contained (2 S,4 E)-2-hydroxyoct-4-en-3-one (71 %), (3 R,4 E)-3-hydroxyoct-4-en-2-one (15 %), ( E)-4-octen-2,3-dione (13 %), and 2,3-octanedione (1.5 %). Four independent field bioassays with synthetic compounds confirmed that adults of both sexes were attracted by the racemate of the major component, ( E)-2-hydroxyoct-4-en-3-one. No other cerambycid species were attracted in significant numbers. Attraction of both sexes is consistent with the male-produced pheromones of many other species in the subfamily Cerambycinae, but T. bimaculatus is unusual in having a pheromone chemistry that is so far unique among species in that subfamily. [ABSTRACT FROM AUTHOR]

Social parasites exploit other societies by invading and stealing resources. Some enter protected nests using offensive chemical weaponry made from alkaloid-based venom. We characterized the venoms of three Megalomyrmex thief ant species ( M. mondabora, M. mondaboroides, and M. silvestrii) that parasitize the fungus-growing ants, and developed an ethogram to describe host ant reactions to raiding M. mondaboroides and M. silvestrii parasites. We compared piperidine, pyrrolidine, and pyrolizidine venom alkaloid structures with synthetic samples from previous studies, and describe the novel stereochemistry of trans 2-hexyl-5-[8-oxononyl]-pyrrolidine ( 3) from M. mondabora. We showed that workers of Cyphomyrmex costatus, the host of M. mondaboroides and M. silvestrii, react to a sting by Megalomyrmex parasites mainly with submissive behavior, playing dead or retreating. Host submission also followed brief antennal contact. The behavior of C. costatus ants observed in this study was similar to that of Cyphomyrmex cornutus, host of M. mondabora, suggesting that the alkaloidal venoms with pyrrolidines from M. mondabora, piperidines from M. mondaboroides, and pyrolizidines from M. silvestrii may function similarly as appeasement and repellent allomones against host ants, despite their different chemical structure. With the use of these chemical weapons, the Megalomyrmex thief ants are met with little host resistance and easily exploit host colony resources. [ABSTRACT FROM AUTHOR]

Insect natural enemies use several environmental cues for host/prey finding, and adjust their foraging behavior according to these signals. In insects, such cues are mainly chemical, derived from the host plant or the prey itself. The aphid alarm pheromone, ( E)-β-farnesene (EBF), is believed to be such a cue, because several aphid enemies are able to perceive EBF and show attractant behavior. These studies are, however, based mainly on electroantennogram or olfactometer assays, and often use unnaturally high pheromone concentrations. It is, therefore, unclear if EBF is used to locate prey in the field when only naturally released amounts are present. We monitored the frequencies and durations of plant visits by aphid natural enemies in the field using long-duration camera observations. By placing pheromone releasers emitting no, natural or exaggerated amounts of EBF next to small colonies of pea aphids ( Acyrthosiphon pisum), we analyzed if EBF presence altered long-range foraging behavior of natural enemies. Thirteen potential groups of aphid natural enemies were observed in 720 hr of analyzed video data. There was no effect of EBF on the number of predator visits to an aphid colony, or on predator patch residence times. The number of plant visits increased at exaggerated EBF amounts but not at natural EBF levels. We conclude that while there may be potential for use of high EBF concentrations for agricultural pest management strategies, an ecological role of EBF as a kairomone in a natural context is doubtful. [ABSTRACT FROM AUTHOR]

Pollinophagy is widely documented in the order Thysanoptera, with representative individuals from six of the nine divergent families known to feed on pollen. Various pollens of the genus Pinus increase the development time, fecundity, longevity, and settling preference of Western Flower Thrips (WFT), Frankliniella occidentalis (Pergande) (Thysanoptera: Thripidae). Certain species of flower thrips discriminate among pollen types, but no studies have elucidated the olfactory cues that play a role in their pollen preferences. In this study, the volatile organic compounds emitted by pollens of the genus Pinus were elucidated. Various chemicals from pollen headspace elicited electrophysiological responses from WFT antennae. The compound (S)-(-)-verbenone, identified in pollen headspace, attracted WFT in a 4-arm olfactometer. This compound has potential for use in integrated pest management programs against the pest. We present the hypothesis that this polyphagous insect may have retained ancestral 'relict' olfactory receptors through the course of evolution, to explain this attraction to pine pollen. This attraction has allowed the insect to find and exploit an unusual nutrient source that significantly increases its fitness. The study demonstrates how fossil record analysis and subsequent evolutionary knowledge can aid in explaining possibilities as to why some insects sense and respond to chemicals that would otherwise seem peculiar to their ecology, allowing insight into the evolutionary forces that may shape insect olfactory systems over time. [ABSTRACT FROM AUTHOR]

Gas chromatography/mass spectrometry was used to identify 103 organic compounds from urine, feces, anal glands, and preputial glands of free-ranging African wild dogs, Lycaon pictus. Aliphatic acids were the dominant class of compound in all materials. In addition to aliphatic acids, urine contained dimethyl sulfone, 1,3-propanediol, benzoic acid, 1-methyl-2,4-imidazolidinedione, and squalene as major components: feces contained indole and cholesterol; and both contained 2-piperidone, phenol, 4-methyl phenol, benzeneacetic acid, and benzenepropanoic acid and other compounds. Anal gland secretion was particularly rich in cholesterol and fatty acids, and preputial gland secretion rich in squalene. A large majority of the identified compounds have been reported from other mammals, including species sympatric with African wild dogs. Eleven of the African wild dog components have not been reported previously from mammals and have not been found in sympatric species; one component, 1-methylimidazole-5-carboxaldehyde has not been reported previously as a natural product. In the chemical profiles of their urine, feces, and anal gland secretion African wild dogs differ markedly from other canids. [ABSTRACT FROM AUTHOR]

Pheromones are likely involved in all social activities of social insects including foraging, sexual behavior, defense, nestmate recognition, and caste regulation. Regulation of the number of fertile queens requires communication between reproductive and non-reproductive individuals. Queen-produced pheromones have long been believed to be the main factor inhibiting the differentiation of new reproductive individuals. However, since the discovery more than 50 years ago of the queen honeybee substance that inhibits the queen-rearing behavior of workers, little progress has been made in the chemical identification of inhibitory queen pheromones in other social insects. The recent identification of a termite queen pheromone and subsequent studies have elucidated the multifaceted roles of volatile pheromones, including functions such as a fertility signal, worker attractant, queen-queen communication signal, and antimicrobial agent. The proximate origin and evolutionary parsimony of the termite queen pheromone also are discussed. [ABSTRACT FROM AUTHOR]

This review focuses on the semiochemical interactions between ants and their soil environment. Ants occupy virtually every ecological niche and have evolved mechanisms to not just cope with, but also manipulate soil organisms. The metapleural gland, specific to ants was thought to be the major source of semiochemical antimicrobial compounds targeting general or specific deleterious microbes. The extremely diverse variety of semiochemicals and their sources with antimicrobial activity or potential activity is highlighted. The leaf-cutting ants and fire ant provide the most researched species, in part because they cause significant economic damage. The leaf-cutting ant is particularly interesting because researchers have uncovered unexpected interactions between leaf-cutting ant fungal farm, parasitic fungi, bacteria, yeasts, and ant defensive semiochemicals. These complex relationships highlight the multidimensional aspects of ants and the soil environment in which they live. [ABSTRACT FROM AUTHOR]

The bark beetle Dendroctonus rhizophagus is endemic to northwestern Mexico where it kills immature pines < 3 m tall. We report the first investigation of the chemical ecology of this pest of forest regeneration. We used GC-EAD to assess olfactory sensitivity of this species to volatile compounds from: resin of a major host, Pinus arizonica; mid/hindguts of single, gallery-initiating females; and mate-paired males within galleries of attacked host trees in the field. Antennae of both sexes responded to monoterpenes α-pinene, β-pinene and 3-carene as well as to the beetle-derived oxygenated monoterpenes fenchyl alcohol, myrtenal, cis-verbenol, trans-verbenol, verbenone, and myrtenol. These monoterpenes were quantified from pre-emerged D. rhizophagus adults forced to attack host tissue in the laboratory, and from individuals dissected from naturally-attacked hosts at different stages of colonization. In both bioassays, myrtenol and trans-verbenol were the most abundant volatiles, and trans-verbenol was the only one produced in significantly greater quantities by females than males in a naturally-colonized host. Two field experiments were performed to evaluate behavioral responses of D. rhizophagus to antennally-active monoterpenes. Results show that 3-carene was significantly attractive either alone or in a ternary (1:1:1) combination with α-pinene and β-pinene, whereas neither α-pinene nor β-pinene alone were attractive. None of the beetle-associated oxygenated monoterpenes enhanced the attractiveness of the ternary mixture of monoterpenes, while verbenone either alone or combined with the other five oxygenated terpenes reduced D. rhizophagus attraction to the ternary mixture. The results suggest that attraction of D. rhizophagus to the host tree P. arizonica is mediated especially by 3-carene. There was no conclusive evidence for an aggregation or sex attractant pheromone. [ABSTRACT FROM AUTHOR]

We report the identification, synthesis, and field bioassays of a female-produced sex attractant pheromone for the cerambycid beetle Desmocerus californicus californicus Horn. Headspace volatiles from females contained a sex-specific compound, ( R)-desmolactone [(4 R,9 Z)-hexadec-9-en-4-olide], which elicited strong responses from the antennae of adult males in coupled gas chromatography-electroantennogram analyses. Short syntheses of both enantiomers were developed from commercial chiral synthons. In field bioassays, significant numbers of males were collected in traps baited with ( R)-desmolactone, whereas the ( S)-enantiomer attracted no males. The racemate was less attractive than the pure ( R)-enantiomer, indicating some degree of antagonism by the unnatural enantiomer. This compound is the first example of a new structural class of cerambycid pheromones, and is the second pheromone identified for a species in the subfamily Lepturinae. [ABSTRACT FROM AUTHOR]

The family of cecidomyiid midges (Diptera: Cecidomyiidae) exhibits diversified patterns of life history, behavior, host range, population dynamics and other ecological traits. Those that feed on plants include many important agricultural pests; most cultivated plants are attacked by at least one midge species. Several features of the reproductive biology of cecidomyiid midges point to an important role for chemical communication, with this topic last reviewed comprehensively 12 years ago. Here, we review progress on identification of sex pheromones, chemicals involved in location of host plants, the neurophysiology of reception of volatile chemicals, and application of semiochemicals to management of pest species of cecidomyiid midges that has occurred during the last decade. We hope this review will stimulate and sustain further research in these fields. [ABSTRACT FROM AUTHOR]

Studies were conducted to develop an attractant for the cranberry weevil, Anthonomus musculus, a pest of blueberry and cranberry flower buds and flowers in the northeastern United States. In previous studies, we showed that cinnamyl alcohol, the most abundant blueberry floral volatile, and the green leaf volatiles ( Z)-3-hexenyl acetate and hexyl acetate, emitted from both flowers and flower buds, elicit strong antennal responses from A. musculus. Here, we found that cinnamyl alcohol did not increase capture of A. musculus adults on yellow sticky traps compared with unbaited controls; however, weevils were highly attracted to traps baited with the Anthonomus eugenii Cano aggregation pheromone, indicating that these congeners share common pheromone components. To identify the A. musculus aggregation pheromone, headspace volatiles were collected from adults feeding on blueberry or cranberry flower buds and analyzed by gas chromatography-mass spectrometry. Three male-specific compounds were identified: ( Z)-2-(3,3-dimethyl-cyclohexylidene) ethanol ( Z grandlure II); ( Z)-(3,3-dimethylcyclohexylidene) acetaldehyde (grandlure III); and ( E)-(3,3- dimethylcyclohexylidene) acetaldehyde (grandlure IV). A fourth component, ( E)-3,7-dimethyl-2,6-octadien-1-ol (geraniol), was emitted in similar quantities by males and females. The emission rates of these volatiles were about 2.8, 1.8, 1.3, and 0.9 ng/adult/d, respectively. Field experiments in highbush blueberry (New Jersey) and cranberry (Massachusetts) examined the attraction of A. musculus to traps baited with the male-produced compounds and geraniol presented alone and combined with ( Z)-3-hexenyl acetate and hexyl acetate, and to traps baited with the pheromones of A. eugenii and A. grandis. In both states and crops, traps baited with the A. musculus male-produced compounds attracted the highest number of adults. Addition of the green leaf volatiles did not affect A. musculus attraction to its pheromone but skewed the sex ratio of the captured adults towards females. Although the role of plant volatiles in host-plant location by A. musculus is still unclear, our studies provide the first identification of the primary A. musculus aggregation pheromone components that can be used to monitor this pest in blueberry and cranberry pest management programs. [ABSTRACT FROM AUTHOR]

The male-produced bicyclic acetal endo-brevicomin is a component of the pheromone blend that mediates colonization of host pines by the bark beetle Dendroctonus frontalis Zimmermann. Efforts to identify its behavioral function have been complicated by contrasting reports that it either enhances or reduces attraction of flying beetles. Our studies failed to support the hypothesis that this published variability is due to differences in release rate and/or the enantiomeric composition [i.e., the beetle-produced (+)-enantiomer vs. the racemate] of the endo-brevicomin used in the experiments. In trapping trials within active D. frontalis infestations, racemic and (+)- endo-brevicomin did not differ from each other in behavioral effects when tested at seven different release rates ranging from 0.005 to 3 mg/d. At the highest release rates, racemic and (+)- endo-brevicomin similarly reduced catches in traps baited with an attractant (frontalin and turpentine), but neither enhanced catches at any release rate. Furthermore, the activity of racemic endo-brevicomin baits depended on trap proximity to D. frontalis infestations. Addition of these baits to attractant-baited traps located inside active infestations reduced catches, but they enhanced catches at traps located either 100 or 200 m outside these infestations. The contrasting responses may reflect differences in host-seeking strategies by either aggregated or dispersing D. frontalis, and may be elicited by differing abundance of natural sources of semiochemicals or differing responsiveness of beetles inside vs. outside of infestations. We suspect that much of the published variability in D. frontalis responses to endo-brevicomin is attributable to differing proximity of experimental field sites to infestations. [ABSTRACT FROM AUTHOR]

The pine sawfly Neodiprion sertifer (Geoffroy) uses the acetate or propionate of (2 S,3 S,7 S)-3,7-dimethyl-2-pentadecanol (diprionol) as pheromone components, with the (2 S,3 R,7 R)-isomer being antagonistic, synergistic, or inactive according to the population tested. In this study, we tested the attraction of males to the acetates of three analogs of diprionol, each missing one methyl group, viz. (2 S,7 S)-7-methyl-2-pentadecanol, (2 S,6 S)-2,6-dimethyl-1-tetradecanol, and (2 S,3 S)-3-methyl-2-pentadecanol. None of the analogs alone, or in combination with diprionol acetate, was attractive in Sweden, even at 100 times the amount of diprionol acetate attractive to N. sertifer. In Japan, the acetate of (2 S,3 S)-3-methyl-2-pentadecanol attracted males when tested in amounts 10-20 times higher than the acetate pheromone component. The acetate esters of the (2 S,3 R)-analog and the (2 S,3 R,7 R)-isomer of diprionol also were tested in combination with the pheromone compound (acetate ester). Both compounds caused an almost total trap-catch reduction in Sweden, whereas in Japan they appear to have relatively little effect on trap capture when added to diprionol acetate. Butyrate and iso-butyrate esters of diprionol were unattractive to N. sertifer in Sweden. In summary, there exists geographic variation in N. sertifer in responses to both diprionyl acetate and some of its analogs. [ABSTRACT FROM AUTHOR]

Bracon hebetor is a larval ectoparasitoid that utilizes several pests belonging to the family Pyralidae (Lepidoptera) as hosts. In the present study, we analyzed the kairomonal response of this wasp to the male-produced sex pheromone of a host, the greater wax moth Galleria mellonella, an economically important pest of honeybees, Apis mellifera. Coupled gas chromatography-electroantennographic detection (GC-EAD) revealed three compounds in headspace collections from male G. mellonella that elicited responses from B. hebetor antennae: decanal and the previously identified sex pheromone components, nonanal and undecanal. Y-tube olfactometer tests that used naïve, mated wasps showed that females, but not males, were highly attracted to (a) male G. mellonella headspace samples, (b) two synthetic blends of nonanal and undecanal (in ratios matching that found in male moth samples), and (c) the two aldehydes tested individually. Further, female wasps did not discriminate between a blend of aldehydes and male G. mellonella headspace. In dose-response trials that used octanal, nonanal, decanal, and undecanal, no difference in EAG responses of the two sexes was observed, except for undecanal at the second highest dose, for which female antennae showed significantly larger responses than did male antennae. When the two binary blends were tested at different doses, female wasps were significantly attracted to the two highest doses (1 µg and 10 µg), but not to the lowest dose (100 ng). Our results show that females of this economically important parasitoid utilize the male-produced sex pheromone of a host as an indirect cue to guide them to potential oviposition sites. [ABSTRACT FROM AUTHOR]

Infectious diseases affecting livestock and human health that involve vector-borne pathogens are a global problem, unrestricted by borders or boundaries, which may be exacerbated by changing global climate. Thus, the availability of effective tools for control of pathogen vectors is of the utmost importance. The aim of this article is to review, selectively, current knowledge of the chemical ecology of pathogen vectors that affect livestock and human health in the developed and developing world, based on key note lectures presented in a symposium on “The Chemical Ecology of Disease Vectors” at the 25th Annual ISCE meeting in Neuchatel, Switzerland. The focus is on the deployment of semiochemicals for monitoring and control strategies, and discusses briefly future directions that such research should proceed along, bearing in mind the environmental challenges associated with climate change that we will face during the 21st century. [ABSTRACT FROM AUTHOR]

The male-produced sex pheromone from the Brazilian rice stalk stink bug Tibraca limbativentris is reported. Olfactometer bioassays with sexually mature males and females showed that males attracted females, which suggests that males release a sex pheromone. Males were not attracted to either sex, nor were females attractive to conspecific females. Attraction of the females to males was highest at night. The headspace volatiles collected from male and female bugs were analyzed by gas chromatography (GC) and GC–mass spectrometry. Two male-specific compounds were identified as isomers of 1′ S-zingiberenol, whereas a series of defensive compounds were identified in extracts from both sexes. Zingiberenol has three chiral centers, and the nonselective syntheses used produced two groups of isomers, zingiberenol I containing four isomers, namely (1 RS,4 RS,1′ R)-4-(1′,5′-dimethylhex-4′-enyl)-1-methylcyclohex-2-en-1-ol, and zingiberenol II containing the other four isomers, namely (1 RS,4 RS,1′ S)-4-(1′,5′-dimethylhex-4′-enyl)-1-methylcyclohex-2-en-1-ol. Both groups of stereoisomers were more attractive than hexane controls. The absolute configuration of the insect-produced pheromonal components remains to be elucidated, but the 1′ S stereochemistry was established for at least one of the isomers. [ABSTRACT FROM AUTHOR]

Electrophysiological and behavioral responses of the ladybird parasitoid Dinocampus coccinellae to volatiles from the seven-spot ladybird, Coccinella septempunctata, were investigated to identify semiochemicals involved in host location. Coupled gas chromatography–electroantennography (GC-EAG) with D. coccinellae located a small peak of prominent activity in an extract of volatiles from adult C. septempunctata. The active compound was identified by coupled GC-mass spectrometry and by comparison with an authentic sample as the free-base alkaloid precoccinelline, which forms part of the toxic defense of this ladybird. Behavioral studies in an olfactometer showed that D. coccinellae was significantly attracted to the volatile extract and also to the alkaloid. Myrrhine, a stereoisomer of precoccinelline found in low amounts in C. septempunctata and in other ladybird species, was shown to be electrophysiologically active and significantly attractive. Perception of ladybird alkaloids by D. coccinellae is a rare example of toxicants acting as aerially transmitted cues for interactions between the third and fourth trophic levels. [ABSTRACT FROM AUTHOR]

The evaluation of behavioral responses of an organism to a particular stimulus normally implies the design of a bioassay. Measurements of the response in a number of replicates are necessary to perform inferential statistics and therefore accept or reject a hypothesis about the effect of the stimulus on the behavior of the organism under study. In the present article, we address the importance of pseudoreplication in studies of chemical ecology, particularly in laboratory experiments on olfactory responses of insects to semiochemicals in olfactometers and wind tunnels. Pseudoreplication may be caused by lack of independence in the stimulus or the experimental device, the reutilization of test insects, or the use of groups of test insects, without adequate statistical analysis addressing such dependency. Each and all of the cases reviewed ( N = 105) lacked information in at least one of the factors listed above; hence no cases could be said with certainty to be free of pseudoreplication. Forty-nine cases (46.7%) contained explicit information revealing that pseudoreplication existed in terms of one or more of the criteria listed above; in only three of these cases did the authors address statistically the stated dependence of the samples. Pseudoreplication due to different factors ranged from 2% to 30% of the cases, with an average of 13%. The most frequent sources of pseudoreplication were the reuse of the device and the use of groups of test insects. The analysis showed the low importance given to obtaining independent replicates in bioassays involving olfactometric responses of insects to semiochemicals. [ABSTRACT FROM AUTHOR]