Insecticide resistance may enhance the response to a host-plant volatile kairomone for the codling moth, <Emphasis Type="Italic">Cydia pomonella</Emphasis> (L.)

The behavioral and electroantennographic responses of Cydia pomonella (L.) to the ripe pear volatile ethyl (2E,4Z)-2,4-decadienoate (Et-E,Z-DD), were compared in insecticide-susceptible and -resistant populations originating from southern France. A dose–response relationship to this kairomonal attractant was established for antennal activity and did not reveal differences between susceptible and resistant strains. Conversely, males of the laboratory strains expressing metabolic [cytochrome P450-dependent mixed-function oxidases (mfo)] or physiological (kdr-type mutation of the sodium-channel gene) resistance mechanisms exhibited a significantly higher response to Et-E,Z-DD than those of the susceptible strain in a wind tunnel experiment. No response of the females to this kairomone could be obtained in our wind-tunnel conditions. In apple orchards, mfo-resistant male moths were captured at significantly higher rates in kairomone-baited traps than in traps baited with the sex pheromone of C. pomonella. Such a differential phenomenon was not verified for the kdr-resistant insects, which exhibited a similar response to both the sex pheromone and the kairomonal attractant in apple orchards. Considering the widespread distribution of metabolic resistance in European populations of C. pomonella and the enhanced behavioral response to Et-E,Z-DD in resistant moths, the development of control measures based on this kairomonal compound would be of great interest for the management of insecticide resistance in this species.     

Evidence for a male-produced pheromone in <Emphasis Type="Italic">Tetropium fuscum</Emphasis> (F.) and <Emphasis Type="Italic">Tetropium cinnamopterum</Emphasis> (Kirby) (Coleoptera: Cerambycidae)

(E)-6,10-dimethyl-5,9-undecadien-2-ol (geranyl acetol), termed here fuscol, was identified as a male-produced pheromone emitted by Tetropium fuscum (F.) and Tetropium cinnamopterum Kirby. In field experiments, traps baited with synthetic fuscol alone were not significantly attractive, but the combination of fuscol plus host volatiles (a synthetic blend of monoterpenes plus ethanol) attracted significantly more male and female T. fuscum and female T. cinnamopterum than did host volatiles alone. This is the first homoterpenoid alcohol to be described in the Cerambycidae, and the first pheromone reported from the sub-family Spondylidinae.     

Sex pheromone chemistry and field trapping studies of the elm spanworm Ennomos subsignaria (Hübner) (Lepidoptera:Geometridae)

The elm spanworm, Ennomos subsignaria (Hübner), occurs throughout Canada and the eastern United States and can be a destructive forest pest on a wide range of deciduous trees. Gas chromatography/mass spectrometry (GC/MS) and coupled gas chromatographic–electroantennographic detection (GC/EAD) analysis of pheromone gland extracts, in combination with chemical synthesis and field trapping studies have identified (2S, 3R)-2-((Z)-oct-2′-enyl)-3-nonyl oxirane (hereafter Z6-9S, 10R-epoxy-19:H) as the female-produced sex pheromone. Significantly more male moths were captured between 1–100 μg loadings of this compound on red rubber septa in sticky traps compared to blank (unbaited) traps; catches then declined at higher dosages (500–1000 μg). The other isomeric enantiomer, (2R, 3S)-2-[(Z)-oct-2′-enyl]-3-nonyl oxirane (Z6-9R, 10S-epoxy-19:H), at a 10-μg dosage did not elicit trap capture. The likely precursor to the active epoxide, (Z, Z)-6, 9-nonadecadiene ((Z, Z)-6, 9-19:H), identified in virgin female sex pheromone glands, did not elicit trap capture either, and inhibited trap capture when combined with the active epoxide. Racemic 2-((Z)-oct-2′-enyl)-3-nonyl oxirane showed no significant difference in trap capture compared with Z6-9S, 10R-epoxy-19:H, indicating that the opposite enantiomer was not antagonistic. The addition of the EAD-active diene epoxide enantiomers (2S, 3R)-2-[(Z, Z)-octa-2′, 5′-dienyl]-3-nonyl oxirane or (2R, 3S)-2-[(Z, Z)-octa-2′, 5′-dienyl]-3-nonyl oxirane in admixture with Z6-9S, 10R-epoxy-19:H (at 10% of the latter) did not enhance or decrease trap capture compared to Z6-9S, 10R-epoxy-19:H oxirane alone, so they are not likely pheromone components. This pheromone, impregnated in rubber septa at less than 100-μg dosage, can now be used as a trap bait to develop detection and monitoring strategies for this insect.     

Female sex pheromone and male behavioral responses of the bombycid moth <Emphasis Type="Italic">Trilocha varians</Emphasis>: comparison with those of the domesticated silkmoth <Emphasis Type="Italic">Bombyx mori</Emphasis>

Analysis of female sex pheromone components and subsequent field trap experiments demonstrated that the bombycid moth Trilocha varians uses a mixture of (E,Z)-10,12-hexadecadienal (bombykal) and (E,Z)-10,12-hexadecadienyl acetate (bombykyl acetate) as a sex pheromone. Both of these components are derivatives of (E,Z)-10,12-hexadecadienol (bombykol), the sex pheromone of the domesticated silkmoth Bombyx mori. This finding prompted us to compare the antennal and behavioral responses of T. varians and B. mori to bombykol, bombykal, and bombykyl acetate in detail. The antennae of T. varians males responded to bombykal and bombykyl acetate but not to bombykol, and males were attracted only when lures contained both bombykal and bombykyl acetate. In contrast, the antennae of B. mori males responded to all the three components. Behavioral analysis showed that B. mori males responded to neither bombykal nor bombykyl acetate. Meanwhile, the wing fluttering response of B. mori males to bombykol was strongly inhibited by bombykal and bombykyl acetate, thereby indicating that bombykal and bombykyl acetate act as behavioral antagonists for B. mori males. T. varians would serve as a reference species for B. mori in future investigations into the molecular mechanisms underlying the evolution of sex pheromone communication systems in bombycid moths.     

A pear-derived kairomone with pheromonal potency that attracts male and female codling moth, Cydia pomonella (L.)

Ethyl (2E, 4Z)-2,4-decadienoate, a pear-derived volatile, is a species-specific, durable, and highly potent attractant to the codling moth (CM), Cydia pomonella (L.), a serious pest of walnuts, apples, and pears worldwide. This kairomone attracts both CM males and virgin and mated females. It is highly attractive to CM in both walnut and apple orchard contexts, but has shown limited effectiveness in a pear orchard context. Rubber septa lures loaded with ethyl (2E, 4Z)-2,4-decadienoate remained attractive for several months under field conditions. At the same low microgram load rates on septa, the combined gender capture of CM in kairomone-baited traps was similar to the capture rate of males in traps baited with codlemone, the major sex pheromone component. The particular attribute of attracting CM females renders this kairomone a novel tool for monitoring population flight and mating-ovipositional status, and potentially a major new weapon for directly controlling CM populations.     

A new C12 alcohol identified as a sex pheromone and a trail-following pheromone in termites: the diene (<Emphasis Type="Italic">Z</Emphasis>,<Emphasis Type="Italic">Z</Emphasis>)-dodeca-3,6-dien-1-ol

The diunsaturated C12 alcohol (Z,Z)-dodeca-3,6-dien-1-ol (dodecadienol) has been characterized by GC-MS and FTIR as a novel releaser pheromone in termites. This alcohol identified in Ancistrotermes pakistanicus (Termitidae, Macrotermitinae) possesses a double pheromonal function which again illustrates the chemical parsimony of termites compared with other social insects. In workers, dodecadienol elicits trail-following at a very low concentration (activity threshold at 0.1 pg/cm of trail); in male alates it induces trail-following at a low concentration (1–10 pg/cm) and sexual attraction at a higher concentration (about 1 ng). Traces of the monounsaturated C12 alcohol (Z)-dodec-3-en-1-ol (dodecenol), known as a trail pheromone of several Macrotermitinae, were also found in the sternal gland extracts of A. pakistanicus, although only dodecadienol was present at the surface of the sternal gland. Workers of A. pakistanicus are not sensitive to dodecenol, but they are as sensitive to dodecatrienol as to dodecadienol. However, in the study area (Vietnam), A. pakistanicus is living in sympatry only with those Macrotermitinae using dodecenol as a trail pheromone, the foraging populations therefore being well isolated through their respective trail pheromones. The presence of three types of unsaturated C12 alcohols as releaser pheromones in the only Macrotermitinae subfamily is discussed, and a possible biosynthetic pathway from linoleic acid is proposed for dodecadienol.     

Anatomical localization and stereoisomeric composition of <Emphasis Type="Italic">Tribolium castaneum</Emphasis> aggregation pheromones

We report that the abdominal epidermis and associated tissues are the predominant sources of male-produced pheromones in the red flour beetle, Tribolium castaneum and, for the first time, describe the stereoisomeric composition of the natural blend of isomers of the aggregation pheromone 4,8-dimethyldecanal (DMD) in this important pest species. Quantitative analyses via gas chromatography–mass spectrometry showed that the average amount of DMD released daily by single feeding males of T. castaneum was 878 ± 72 ng (SE). Analysis of different body parts identified the abdominal epidermis as the major source of aggregation pheromone; the thorax was a minor source, while no DMD was detectable in the head. No internal organs or obvious male-specific glands were associated with pheromone deposition. Complete separation of all four stereoisomers of DMD was achieved following oxidation to the corresponding acid, derivatization with (1R, 2R)- and (1S, 2S)-2-(anthracene-2,3-dicarboximido)cyclohexanol to diastereomeric esters, and their separation on reversed-phase high-performance liquid chromatography at −54°C. Analysis of the hexane eluate from Porapak-Q-collected volatiles from feeding males revealed the presence of all four isomers (4R,8R)/(4R,8S)/(4S,8R)/(4S,8S) at a ratio of approximately 4:4:1:1. A walking orientation bioassay in a wind tunnel with various blends of the four synthetic isomers further indicated that the attractive potency of the reconstituted natural blend of 4:4:1:1 was equivalent to that of the natural pheromone and greater than that of the 1:1 blend of (4R,8R)/(4R,8S) used in commercial lures.     

Sex Pheromone Components of Pink Gypsy Moth, Lymantria mathura

Pheromone extract of female pink gypsy moth, Lymantria mathura, was analyzed by coupled gas chromatographic-electroantennographic detection (GC-EAD) and coupled GC-mass spectrometry (MS), employing fused silica columns coated with DB-5, DB-210, or DB-23 and a custom-made GC column that separated enantiomers of unsaturated epoxides. These analyses revealed (9R,10S)-cis–9,10-epoxy-Z3,Z6-nonadecadiene [termed here (+)-mathuralure] and (9S,10R)-cis–9,10-epoxy-Z3,Z6-nonadecadiene [termed here (–)-mathuralure] at a 1 : 4 ratio as major candidate pheromone components. In field experiments in northern Japan (Morioka, Iwate Prefecture and Bibai, Hokkaido Prefecture), (+)- and (–)-mathuralure at a ratio of 1 : 4, but not 1 : 1 or singly, were attractive to male L. mathura. This is the first demonstration that attraction of male moths required the very same ratio of pheromone enantiomers as produced by conspecific females. Whether L. mathura employ different blend ratios in different geographic areas, and the role of five additional candidate pheromone components identified in this study remains to be investigated. Received: 29 October 1998 / Accepted in revised form: 29 December 1998     

Sexual selection on receptor organ traits: younger females attract males with longer antennae

Sexual selection theory predicts that female choice may favour the evolution of elaborate male signals. Darwin also suggested that sexual selection can favour elaborate receiver structures in order to better detect sexual signals, an idea that has been largely ignored. We evaluated this unorthodox perspective by documenting the antennal lengths of male Uraba lugens Walker (Lepidoptera: Nolidae) moths that were attracted to experimentally manipulated emissions of female sex pheromone. Either one or two females were placed in field traps for the duration of their adult lives in order to create differences in the quantity of pheromone emissions from the traps. The mean antennal length of males attracted to field traps baited with a single female was longer than that of males attracted to traps baited with two females, a pattern consistent with Darwin’s prediction assuming the latter emits higher pheromone concentrations. Furthermore, younger females attracted males with longer antennae, which may reflect age-specific changes in pheromone emission. These field experiments provide the first direct evidence of an unappreciated role for sexual selection in the evolution of sexual dimorphism in moth antennae and raise the intriguing possibility that females select males with longer antennae through strategic emission of pheromones.     

Sex pheromone of orange wheat blossom midge, Sitodiplosis mosellana

 Pheromone extract of the female orange wheat blossom midge, Sitodiplosis mosellana (Géhin) (SM) (Diptera: Cecidomyiidae), was analyzed by coupled gas chromatographic-electroantennographic detection (GC-EAD) and GC-mass spectrometry (MS), employing fused silica columns coated with DB-5, DB-210, DB-23 or SP-1000. These analyses revealed a single, EAD-active candidate pheromone which was identified as 2,7-nonanediyl dibutyrate. In experiments in wheat fields in Saskatchewan, traps baited with (2S,7S)-2,7-nonanediyl dibutyrate attracted significant numbers of male SM. The presence of other stereoisomers did not adversely affect trap captures. Facile synthesis of stereoisomeric 2,7-nonanediyl dibutyrate will facilitate the development of pheromone-based monitoring or even control of SM populations. Received: 2 March 2000 / Accepted in revised form: 18 August 2000     

A new pheromone of the silkworm moth Bombyx mori

The female silkmoth Bombyx mori L. emits a second pheromone component bombykal (E-10, Z-12-hexade-cadien-1-al) in addition to the well-known sexual attractant bombykol (E-10, Z-12-hexadecadien-1-ol). Bombykal stimulates its own specialized and highly sensitive olfactory cells of the male moth. Surprisingly, the aldehyde inhibits the release of the male's wing-fluttering response to bombykol.     

(<Emphasis Type="Italic">Z</Emphasis>)-9-tricosene identified in rectal gland extracts of <Emphasis Type="Italic">Bactrocera oleae</Emphasis> males: first evidence of a male-produced female attractant in olive fruit fly

It is well-known that Bactrocera oleae (olive fruit fly) females attract conspecific males by using 1,7-dioxaspiro[5,5]undecane (1) as the main component of their sex pheromone, and that 1 is produced in the female rectal gland. Although some authors have claimed that B. oleae males also attract females, to date no male-produced female attractants have been found in this species. In this paper, we report the first identification of a substance unique to males and able to attract females. The findings of the study include the following: (1) females responded in a bioassay to hexane extracts obtained from rectal glands of 15-day-old B. oleae males, (2) the presence of (Z)-9-tricosene (2) was consistently and unambiguously identified in these extracts using gas chromatography (GC) and GC-mass spectrometry methods, (3) in preliminary bioactivity tests, low doses (equivalent to a few males) of chemically and stereoisomerically pure synthetic (Z)-9-tricosene (2) attracted olive fruit fly females. Interestingly, compound 2, commonly called muscalure, is also a well-known component of the house fly (Musca domestica) sex pheromone.     

Sex Pheromone of the Pine Sawfly Macrodiprion nemoralis (Hymenoptera : Diprionidae): Identification of (2S,3R,7R,9S)-3,7,9-Trimethyl-2-tridecanol as the Precursor for the Active Pheromone Acetate

 The main component of the sex pheromone precursor in females of Macrodiprion nemoralis was identified as a threo-3,7,9-trimethyl-2-tridecanol isomer, approximately 800 pg per female, by gas chromatography–mass spectrometry. Comparison of mass spectrometric ion chromatograms showed that the natural compound in the female extract has the same retention time and mass spectrum as one of the two synthetic threo peaks. The acetate of the synthetic 16-isomer mixture caught a large number of males in the field, confirming the structure of the active pheromone. Comparison of gas chromatograms of the natural female extract with the eight synthetic threo stereoisomers showed that the pheromone is the (2S,3R,7R,9S)-stereoisomer of 3,7,9-trimethyl-2-tridecyl acetate. Received: 12 May 1999 / Accepted in revised form: 16 September 1999     

Diel periodicity of pheromone release by females of Planococcus citri and Planococcus ficus and the temporal flight activity of their conspecific males

The diel periodicity of sex pheromone release was monitored in two mealybug species, Planococcus citri and Planococcus ficus (Hemiptera; Pseudococcidae), using sequential SPME/GCMS analysis. A maximal release of 2 ng/h pheromone by 9–12-day-old P. citri females occurred 1–2 h before the beginning of photophase. The highest release of pheromone by P. ficus females was 1–2 ng/2 h of 10–20-day-old females, approximately 2 h after the beginning of photophase. Mating resulted in termination of the pheromone release in both mealybug species. The temporal flight activity of the males was monitored in rearing chambers using pheromone baited delta traps. Males of both P. citri and P. ficus displayed the same flight pattern and began flying at 06:00 hours when the light was turned on, reaching a peak during the first and second hour of the photophase. Our results suggest that other biparental mealybug species display also diel periodicities of maximal pheromone release and response. Direct evaluation of the diel periodicity of the pheromone release by the automatic sequential analysis is convenient and will be very helpful in optimizing the airborne collection and identification of other unknown mealybug pheromones and to study the calling behavior of females. Considering this behavior pattern may help to develop more effective pheromone-based management strategies against mealybugs.     

Attractants from Bartlett pear for codling moth, Cydia pomonella (L.), larvae

The alkyl ethyl and methyl esters of (2E,4Z)-2,4-decadienoic acid found in head-space samples of ripe Bartlett pear (Pyrus communis L.) stimulated a response from neonate larvae of the codling moth (CM), Cydia pomonella (L.), in both static-air Petri-plate and in upwind Y-tube and straight-tube olfactometer bioassays. In comparison with the known CM neonate attractant, (E,E)-!-farnesene, ethyl (2E,4Z)-2,4-decadienoate was attractive at 10-fold and 1,000-fold lower threshold dosages in the Petri-plate and in the Y-tube bioassays, respectively. Methyl (2E,4Z)-2,4-decadienoate was attractive to CM neonates in these bioassays at much higher doses than ethyl (2E,4Z)-2,4-decadienoate. Other principal head-space volatiles from ripe pear fruit and pear leaves, including butyl acetate, hexyl acetate, (Z)-3-hexenyl acetate, and (E)-#-ocimene, were not attractive to CM neonates. The potential uses of these pear kairomones for monitoring and control of CM in walnuts and apple are discussed.     

Evidence for contact sex recognition pheromone of the Asian longhorned beetle,<Emphasis Type="Italic"> Anoplophora glabripennis</Emphasis> (Coleoptera: Cerambycidae)

Field observations of the Asian longhorned beetle (Anoplophora glabripennis) mating behavior in China suggested that a female-produced contact pheromone was almost certainly involved in sex recognition. Gas chromatography–mass spectrometry (GC-MS) analysis of A. glabripennis adults' whole body cuticular extracts indicates that a series of long-chain hydrocarbons comprise the cuticular waxes of both sexes. Although for the most part the GC profiles are similar for the two sexes, five monounsaturated compounds were consistently more abundant in samples from females than in those from males. These compounds were identified as (Z)-9-tricosene, (Z)-9-pentacosene, (Z)-7-pentacosene, (Z)-9-heptacosene, and (Z)-7-heptacosene in the approximate ratio of 1:2:2:8:1, respectively. Antennal and palpi contact to a polypropylene micro-centrifuge tube coated with a synthetic mixture of the five compounds stimulated copulatory behavior in males.Electronic Supplementary Material  Supplementary material is available for this article if you access the article at . A link in the frame on the left on that page takes you directly to the supplementary material.     

Identification of sex pheromone components of the pea midge, Contarinia pisi (Diptera: Cecidomyiidae)

 Three components in extract of pheromone glands of female pea midges, Contarinia pisi, were found to be active on male pea midge antennae by coupled gas chromatographic-electroantennographic detection. The EAD active components were identified as 2-acetoxytridecane, (2S,11S)-diacetoxytridecane, and (2S,12S)-diacetoxytridecane. A blend of these compounds proved to be highly attractive to males in windtunnel experiments. Received: 12 November 1998 / Accepted in revised form: 26 january 1999     

Methyl 2-(methylthio)benzoate: the unique sulfur-containing sex pheromone of<Emphasis Type="Italic"> Phyllophaga crinita</Emphasis>

The female-produced sex pheromone of Phyllophaga crinita (Burmeister) (Coleoptera: Scarabaeidae: Melolonthinae; the adult has no common name) is identified as methyl 2-(methylthio)benzoate. This is the first identification of a sulfur-containing, long-distance, female-produced sex attractant from any insect taxa. The root-feeding larvae of this species are serious pests in many crops in Texas and Mexico. In field tests, many P. crinita males were captured in traps baited with the authentic compound. Interestingly, a heteroatom analog, methyl 2-methoxybenzoate, also captured P. crinita males, but only at a dose 10,000 times higher than the lowest tested dose of the authentic pheromone.In memory of M.G. Villani, who died on 15 May 2001. His enthusiasm for soil-dwelling scarab beetles and contributions to their research are greatly missed.     

Iridodial: a powerful attractant for the green lacewing, Chrysopa septempunctata (Neuroptera: Chrysopidae)

The lacewing Chrysopa septempunctata Wesmael is an important, common predator of several insects in China, Japan, Russia, and many parts of Europe. Our field trapping experiments in northeast China showed that males of this green lacewing are strongly attracted to the lacewing pheromone of Chrysopa oculata Say, (1R,2S,5R,8R)-iridodial. The induced plant volatile, methyl salicylate, was unattractive to C. septempunctata by itself at the concentration tested, but synergistic when combined with iridodial where the lacewing population was high. (1R,4aS,7S,7aR)-Nepetalactol and (4aS,7S,7aR)-nepetalactone (aphid sex pheromone components) caught significantly more males of C. septempunctata than did blank control traps, but were inferior to iridodial dispensers, which remained strongly attractive to C. septempunctata males for at least 2.5 months. These results indicate that (1R,2S,5R,8R)-iridodial is a powerful attractant for C. septempunctata, and may have great potential for enhanced biological control of garden, agricultural, and forest insect pests.     

Attraction of two lacewing species to volatiles produced by host plants and aphid prey

It is well documented that host-related odors enable many species of parasitoids and predatory insects to locate their prey and prey habitats. This study reports the first characterization of prey and prey host odor reception in two species of lacewings, Chrysoperla carnea (Say) and Chrysopa oculata L. 2-Phenylethanol, one of the volatiles emitted from their preys host plants (alfalfa and corn) evoked a significant EAG response from antennae of C. carnea. Traps baited with this compound attracted high numbers of adult C. carnea, which were predominantly females. One of the sex pheromone components (1R,4aS,7S,7aR)-nepetalactol of an aphid species, Acyrthosiphon pisum (Harris) attracted only C. oculata adults. Single sensillum recordings showed that the olfactory neurons of C. carnea responded to both 2-phenylethanol and aphid sex pheromone components, but those of C. oculata only responded to the latter.