Pheromone Gland Extracts Research Articles

The egg parasitoid Telenomus euproctidis (Hymenoptera: Scelionidae) uses sex pheromone released by immobile female tussock moth Orgyia postica (Lepidoptera: Lymantriidae) as kairomone

Egg parasitoids Telenomus euproctidis Wilcox (Hymenoptera: Scelionidae) were attracted to egg masses laid by wingless immobile female Orgyia postica (Lepidoptera: Lymantriidae). Virgin females, a solvent extract of pheromone glands, and a synthetic sex pheromone, (6Z,9Z,11S,12S)-11,12-epoxyhenicosa-6,9-diene (posticlure), also attracted this parasitoid in the field, demonstrating that T. euproctidis uses the sex pheromone of female Org. postica as a kairomone to locate host eggs.

Monoenyl hydrocarbons in female body wax of the yellow peach moth as synergists of aldehyde pheromone components

The non-polar components of female body wax and pheromone gland extracts of the yellow peach moth synergistically enhanced male behavioral responses from close to pheromone sources in wind tunnel tests when mixed with an aldehyde pheromone blend. When the non-polar fractions (NPFs) of female body wax were further separated by column chromatography, synergistic activities were found in the 3 and 50% ether in hexane fractions, and they additively increased male responses. The main components of the first fraction were (Z)-9-tricosene, (Z)-9-pentacosene, (Z)-9-heptacosene, (Z)-9-nonacosene and (Z)-9-hentriacontene. Only (Z)-9-heptacosene showed a significant synergistic effect in enhancing male responses, but the other components had no effect. A mixture of the five monoenyl hydrocarbons lost activity at lower doses than 5 ng. Natural ratios of these hydrocarbons in the female body wax and pheromone gland extracts were similar, but the amount of (Z)-9-heptacosene in the female body wax was significantly higher than in the pheromone gland extracts. We conclude that (Z)-9-heptacosene increases male responses to aldehyde pheromones, and unknown component(s) in the 50% ether in the hexane fraction are required for full synergistic enhancement by the NPFs of the female body wax and the pheromone gland extracts.

Identification and field evaluation of the sex pheromone components of a Korean population of Glossosphecia romanovi

Glossosphecia romanovi (Leech) (Lepidoptera: Sesiidae) is a pest of grape in northeast Asia. We analyzed pheromone gland extracts of female moths and compared attractiveness of various pheromone blends to male moths in the field. Two major components from pheromone gland extracts were identified as (Z,Z)-3,13-octadecadien-1-ol (Z3,Z13-18:OH) and (Z,Z)-3,13-octadecadienyl acetate (Z3,Z13-18:OAc) in a ratio of approximately 9:1. Field tests showed that male G. romanovi were attracted to Z3,Z13-18:OH alone, but the maximum number of males was attracted to the binary blend of Z3,Z13-18:OH and Z3,Z13-18:OAc mimicking the blend found in female extracts. In addition to these components, small amounts of (E,Z)-3,13-octadecadien-1-ol (E3,Z13-18:OH) were detected in the pheromone gland of females, but addition of this component inhibited attraction to the primary binary blend. The blend of Z3,Z13-18:OH and Z3,Z13-18:OAc at the natural ratio should provide a sensitive and effective lure for monitoring populations of this pest.

Pheromone Communication in Nasonia vitripennis: Abdominal Sex Attractant Mediates Site Fidelity of Releasing Males

Males of the parasitic wasp Nasonia vitripennis (Hymenoptera: Pteromalidae) use a substrate-borne sex pheromone to attract virgin females. The pheromone is synthesized in the rectal vesicle and deposited via the anus by dabbing movements of the abdominal tip. The chemicals attracting the females are composed of a mixture (4R,5R- and (4R,5 S)-5-hydroxy-4-decanolides (HDL) being synergized by the trace component 4-methylquinazoline (4-MeQ) which is not attractive for females when offered alone. Here we show that male pheromone deposits are not only attractive to virgin females but also for the releasing males themselves. In an olfactometer bioassay, males were strongly attracted by their own pheromone markings but were unable to discriminate between their own markings and those deposited by other males. Polar fractions of pheromone gland extracts containing the HDLs and 4-MeQ were also highly attractive for males. Bioassays using synthetic pheromones in natural doses revealed that combinations of HDL/4-MeQ and 4-MeQ alone attracted males whereas the HDLs alone were behaviorally inactive. Furthermore, males did not discriminate between HDL/4-MeQ and 4-MeQ alone. We conclude that the trace component 4-MeQ mediates site fidelity of N. vitripennis males at sites previously marked with the abdominal sex pheromone. The use of 4-MeQ to stay at and to return to scent-marked patches rather than marking new ones might be a strategy to economize semiochemical use in N. vitripennis males.

Novel Components of the Sex Pheromones Produced by Emerald Moths: Identification, Synthesis, and Field Evaluation

The subfamily Geometrinae (Lepidoptera: Geometridae) includes many species called emerald moths. Based on our recent finding of novel polyenyl compounds, including a double bond at the 12-position from two geometrine species, Hemithea tritonaria and Thalassodes immissaria intaminata, (6Z,9Z,12Z)-6,9,12-trienes and (3Z,6Z,9Z,12Z)-3,6,9,12-tetraenes with a C(17)-C(20) straight chain were synthesized and analyzed by GC-MS. The 6,9,12-trienes, which were prepared by a double Wittig reaction between two alkanals and an ylide derived from (Z)-1,6-diiodo-3-hexene, characteristically produced fragment ions at m/z 79, 150, and M-98. The 3,6,9,12-tetraenes, which were prepared by a coupling between (Z)-3-alkenal and an ylide derived from (3Z,6Z)-1-iodo-3,6-nonadiene, showed fragment ions at m/z 79, 148, and M-96. These diagnostic ions were useful to distinguish these compounds from other known polyenyl pheromones, such as 4,6,9- and 6,9,11-trienes and 1,3,6,9-tetraenes. With reference to the GC-MS data, pheromone extracts of other species in Geometrinae inhabiting the Iriomote Islands were analyzed, and the 6,9,12-trienes were identified in the pheromone gland extracts of Pamphlebia rubrolimbraria rubrolimbraria and Maxates versicauda microptera. Furthermore, a field evaluation of the synthetic polyenes in a mixed forest of Tokyo revealed the following new male attractants for emerald moths: Idiochlora ussuriaria by a C(17) 6,9,12-triene and Jodis lactearia by a C(20) 3,6,9,12-tetraene, indicating the characteristic chemical structures of Geometrinae pheromones. On the other hand, through reexamination of the pheromone extract of H. tritonaria, (3E,6E)-α-farnesene was identified as an electrophysiologically active component in addition to the C(17) 6,9,12-triene. The binary mixture attracted more males than the single component lure baited with the triene in the Iriomote Islands.

Sex Pheromone Components and Control of the Citrus Pock Caterpillar, Prays endocarpa, Found in the Mekong Delta of Vietnam

The citrus pock caterpillar, Prays endocarpa (Yponomeutidae; Praydinae), is a pest of pomelo (Citrus grandis L.) in Vietnam. Gas chromatography-mass spectrometry analyses of pheromone gland extracts from female moths identified three monoenyl compounds, (Z)-7-tetradecenal (Z7-14:Ald), (Z)-7-tetradecenyl acetate (tentatively identified, Z7-14:OAc), and (Z)-7-tetradecen-1-ol (Z7-14:OH), in a ratio of about 10:3:10. In the field, traps baited with synthetic Z7-14:Ald (0.5 mg) caught male P. endocarpa. The other two compounds, either alone or when added to Z7-14:Ald, did not elicit increases in trap catch (relative to the appropriate treatment). Synthetic Z7-14:Ald was used to monitor and control this species in pomelo orchards in Vinh Long Province. Monitoring revealed that adults were present throughout the year with discernible peaks in December, March, and April. A mass-trapping trial, using 20 traps in a 0.1 ha pomelo orchard, effectively suppressed fruit damage to levels similar to that achieved by an insecticide (Karate 2.5EC). Mating disruption trials, using polyethylene-tube dispensers, each filled with 80 mg of Z7-14:Ald at a rate of 200 or 400 dispensers/ha, also controlled damage by this pest to levels below that achieved by an insecticide treatment. This work demonstrates the potential for pheromone-based control of this pest in Vietnam.

Sex pheromone of the red clover casebearer moth, Coleophora deauratella, an invasive pest of clover in Canada

AbstractThe red clover casebearer, Coleophora deauratella Lienig & Zeller (Lepidoptera: Coleophoridae), is an invasive pest of Trifolium species (Fabaceae) in Canada. We identified candidate sex pheromone components from female pheromone gland extracts using coupled gas chromatographic–electroantennographic analysis detection. Three compounds elicited an electrophysiological response from antennae and were identified as: (Z)‐7‐dodecenyl acetate, (Z)‐5‐dodecenyl acetate, and (Z)‐7‐dodecen‐1‐ol. Field tests of the candidate pheromone components revealed that males were attracted to a binary mixture of (Z)‐7‐dodecenyl acetate and (Z)‐5‐dodecenyl acetate. Male moth trap capture was greatest in traps baited with lures containing 100:10 or 100:20 ratios of these pheromone components, respectively. Trap capture was reduced when (Z)‐5‐dodecenyl acetate was present below 10 or above 20% of (Z)‐7‐dodecenyl acetate. Equal numbers of male moths were captured in traps baited with 10, 100, and 1 000 μg of the attractive binary mixture. These findings allow for the development of a pheromone‐based monitoring system for this invasive pest of clover in Canada.

Female Sex Pheromone ofGlossosphecia romanovi(Lepidoptera: Sesiidae): Identification and Field Attraction

In field screening tests of synthetic pheromone candidates for Japanese sesiid species, a mixture of (3Z,13Z)-octadecadien-1-ol and (3Z,13Z)-octadecadienyl acetate successfully attracted male moths of Glossosphecia romanovi, a harmful pest of vine trees. The GC-EAD and GC-MS analyses of the pheromone gland extract revealed that the female moths produced the alcohol and acetate in a ratio of about 20:1, in addition to three other minor structure-related components.

Female sex pheromone of a lichen moth Eilema japonica (Arctiidae, Lithosiinae): Components and control of production

Seven candidates for components of the female sex pheromone of Eilema japonica (Arctiidae, Lithosiinae) were detected in an extract of pheromone glands with a gas chromatograph–electroantennographic detector. The compounds were identified as (Z,Z)-6,9-icosadiene (D20), (Z,Z)-6,9-henicosadiene (D21), (Z,Z,Z)-3,6,9-henicosatriene (T21), (Z,Z)-6,9-docosadiene (D22), (Z,Z,Z)-3,6,9-docosatriene (T22), (Z,Z)-6,9-tricosadiene (D23), and (Z,Z,Z)-3,6,9-tricosatriene (T23). Assays using synthetic lures in a wind tunnel showed that D21 (proportion, 0.39), T21 (0.08), D22 (0.27), and T22 (0.26) are important for evoking full behavioral responses from the males. Titers of the pheromone components did not show clear temporal fluctuations. Moreover, decapitation of the female moth had no effect on the titers of pheromone components in the pheromone gland, suggesting that cephalic endocrine factors such as pheromone biosynthesis activating neuropeptide (PBAN) are not involved in the control of pheromone biosynthesis in this species.

Synergistic sex pheromone components of the grey‐spotted tussock moth, Orgyia ericae

AbstractThe grey‐spotted tussock moth, Orgyia ericae Germar (Lepidoptera: Lymantriidae), is an important pest of deciduous trees and woody scrublands in northern China. In a field trapping experiment conducted during the flight of the first generation of 2009, synthetic (Z)‐6‐heneicosen‐11‐one, a common Orgyia spp. sex pheromone component, attracted O. ericae males. Gas chromatography‐mass spectrometry analyses (full scan or selected ion‐monitoring mode) of pheromone gland extracts from females revealed the presence of a major, a minor, and a trace component, i.e., (6Z,9Z)‐heneicosa‐6,9‐diene, (6Z,9Z)‐tricosa‐6,9‐diene, and (Z)‐6‐heneicosen‐11‐one, respectively. Field experiments during the flight of the second generation showed that (6Z,9Z)‐tricosa‐6,9‐diene, the minor component, was inactive alone or in any combination with the other two components, whereas (6Z,9Z)‐heneicosa‐6,9‐diene and (Z)‐6‐heneicosen‐11‐one were weakly attractive when tested individually. However, traps baited with a binary blend of (6Z,9Z)‐heneicosa‐6,9‐diene and (Z)‐6‐heneicosen‐11‐one caught seven‐fold more moths than any other treatment (except the ternary blend), indicating a strong synergistic interaction between the two components. The analytical and field trapping data suggested that (6Z,9Z)‐heneicosa‐6,9‐diene and (Z)‐6‐heneicosen‐11‐one are likely the key sex pheromone components of female O. ericae. This synergistic blend will be useful as an efficient monitoring tool, and possible control tool, to combat this economically and ecologically important forest defoliator.

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 microg loadings of this compound on red rubber septa in sticky traps compared to blank (unbaited) traps; catches then declined at higher dosages (500-1000 microg). The other isomeric enantiomer, (2R, 3S)-2-[(Z)-oct-2'-enyl]-3-nonyl oxirane (Z6-9R, 10S-epoxy-19:H), at a 10-microg 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-microg dosage, can now be used as a trap bait to develop detection and monitoring strategies for this insect.

Identification and Field Evaluation of the Female Sex Pheromone of the Sand Salix Carpenterworm, Holcocerus arenicola Staudinger (Lepidoptera: Cossidae)

Extracts of female sex pheromone glands of the sand Salix carpenterworm moth, Holcocerus arenicola, a serious pest of desert thicket, were analyzed by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). Based on comparison of retention times and mass spectra of synthetic standards, four compounds were identified as cis-7-tetradecen-1-ol (Z7-14:OH), cis-5-tetradecen-1-yl acetate (Z5-14:OAc), cis-7-tetradecen-1-yl acetate (Z7-14:OAc), and cis-9-hexadecen-1-yl acetate (Z9-16:OAc) with the ratio of 24:39:100:43. Electroantennographic (EAG) analyses of these standard chemicals and their analogues showed that Z7-14:OAc elicited the largest male EAG response, followed by Z5-14:OAc and Z9-16:OAc. In field trials, traps baited with either Z7-14:OAc or Z5-14:OAc captured males while Z7-14:OH-, Z9-16:OAc- or solvent-baited traps caught no males. Z7-14:OAc as a single component was significantly more attractive than Z5-14:OAc alone. The combination of Z7-14:OAc and Z5-14:OAc showed an evidently synergistic effect and attracted much more males than the individual compounds in the field. Addition of Z7-14:OH to the blend of Z7-14:OAc and Z5-14:OAc enhanced slightly the trap catches. We conclude that the major components of the sex pheromone of H. arenicola are Z7-14:OAc and Z5-14:OAc. Currently, a triangle trap baited with the synthetic compounds Z7-14:OAc, Z5-14:OAc, and Z7-14:OH in a 1:0.4:0.25 ratio at 825 microg/trap dosage can be effectively used to monitor the H. arenicola population level and catch the males within the desert regions in China.

Biosynthesis of unusual moth pheromone components involves two different pathways in the navel orangeworm, Amyelois transitella.

The sex pheromone of the navel orangeworm, Amyelois transitella (Walker) (Lepidoptera: Pyralidae), consists of two different types of components, one type including (11Z,13Z)-11,13-hexadecadienal (11Z,13Z-16:Ald) with a terminal functional group containing oxygen, similar to the majority of moth pheromones reported, and another type including the unusual long-chain pentaenes, (3Z,6Z,9Z,12Z,15Z)-3,6,9,12,15-tricosapentaene (3Z,6Z,9Z,12Z,15Z-23:H) and (3Z,6Z,9Z,12Z,15Z)- 3,6,9,12,15-pentacosapentaene (3Z,6Z,9Z,12Z,15Z-25:H). After decapitation of females, the titer of 11Z,13Z-16:Ald in the pheromone gland decreased significantly, whereas the titer of the pentaenes remained unchanged. Injection of a pheromone biosynthesis activating peptide (PBAN) into the abdomens of decapitated females restored the titer of 11Z,13Z-16:Ald and even increased it above that in intact females, whereas the titer of the pentaenes in the pheromone gland was not affected by PBAN injection. In addition to common fatty acids, two likely precursors of 11Z,13Z-16:Ald, i.e., (Z)-11-hexadecenoic and (11Z,13Z)-11,13-hexadecadienoic acid, as well as traces of (Z)-6-hexadecenoic acid, were found in gland extracts. In addition, pheromone gland lipids contained (5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-icosapentaenoic acid, which also was found in extracts of the rest of the abdomen. Deuterium-labeled fatty acids, (16,16,16-D3)-hexadecanoic acid and (Z)-[13,13,14,14,15,15,16,16,16-D9]-11-hexadecenoic acid, were incorporated into 11Z,13Z-16:Ald after topical application to the sex pheromone gland coupled with abdominal injection of PBAN. Deuterium label was incorporated into the C23 and C25 pentaenes after injection of (9Z,12Z,15Z)- [17,17,18,18,18-D5]-9,12,15-octadecatrienoic acid into 1–2 d old female pupae. These labeling results, in conjunction with the composition of fatty acid intermediates found in pheromone gland extracts, support different pathways leading to the two pheromone components. 11Z,13Z-16:Ald is probably produced in the pheromone gland by Δ11 desaturation of palmitic acid to 11Z-16:Acid followed by a second desaturation to form 11Z,13Z-16:Acid and subsequent reduction and oxidation. The production of 3Z,6Z,9Z,12Z,15Z-23:H and 3Z,6Z,9Z,12Z,15Z-25:H may take place outside the pheromone gland, and appears to start from linolenic acid, which is elongated and desaturated to form (5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-icosapentaenoic acid, followed by two or three further elongation steps and finally reductive decarboxylation.

Identification of Critical Secondary Components of the Sex Pheromone of the Navel Orangeworm (Lepidoptera: Pyralidae)

We identified a four-component sex pheromone blend that is as attractive or more attractive to male navel orangeworm moths, Amyelois transitella (Walker) (Lepidoptera: Pyralidae), than either unmated females or hexane extracts of pheromone glands of females. The blend consisted of (11Z,13Z)-hexadecadienal; (11Z,13Z)-hexadecadien-1-ol; (11Z,13E)-hexadecadien-1-ol; and a hydrocarbon, (3Z,6Z,9Z,12Z,15Z)-tricosapentaene (C23 pentaene), in ratios of approximately 100:100:5:5. Other minor components of pheromone gland extracts included (11Z,13E)-hexadecadienal; (11E,13Z)-hexadecadienal; (11Z,13Z)-hexadecadien-1-yl acetate; (Z)-11-hexadecenal; hexadecanal; hexadecan-1-ol; and a second pentaene, (3Z,6Z,9Z,12Z,15Z)-pentacosapentaene (C25 pentaene). These minor components did not increase attraction of male navel orangeworm to the basic four-component blend. The use of another, cross-attracted pyralid moth, Pyralisfarinalis L., as a model species was crucial in implicating the C23 pentaene as an important component of the navel orangeworm pheromone blend. The four-component navel orangeworm pheromone blend was optimized using a combination of wind tunnel and field bioassays. Attractiveness of field deployed synthetic pheromone lures decreased rapidly despite incorporation of stabilizers and use of different release devices, suggesting that degradation products antagonize male navel orangeworm responses. Overall, the combination of type I lepidopteran pheromone components consisting of C16 aldehydes and alcohols with type II components consisting of long-chain polyunsaturated hydrocarbons has now been documented in several lepidopteran species and may indicate a paradigm shift in the range of compounds that constitute sex pheromone blends for individual lepidopteran species. This suggests that careful reexamination of pheromone gland contents for both type I and type II compounds may prove fruitful in species that have been studied but for which full attractant blends have eluded identification.

Calling Behavior and Rhythms of Sex Pheromone Production in the Black Cutworm Moth in China

The hourly and daily variation of calling behavior and sex pheromone production by the female black cutworm moth, Agrotis ypsilon (Rottemberg), were investigated. Both calling behavior and titers of five sex pheromone components showed distinct diel rhythms, and peak periods of calling and pheromone titer were synchronous. Females began to call on the first night after eclosion and called mainly during the second half of the scotophase. The percentage of females calling increased in 1 to 3-d-old females and decreased in 3 to 7-d-old females. Females advanced their calling time with increasing age (1 to 7 d). GC-MS analysis of hexane extracts of pheromone glands revealed that the titers of the five sex pheromone components were very low on the first night after eclosion, but increased sharply and peaked on the third night. Titers decreased greatly with increasing age (3 to 7 d), but from the onset of the scotophase to 4.5 h into scotophase, titers remained invariate. However, from 4.5 to 7 h, pheromone titers, especially that of the primary component Z7-12:Ac, increased sharply and peaked. After the peak, the titers decreased greatly at 8 h, and thereafter decreased gradually to the level before 4.5 h. The quantity of each component almost reached zero after lights-on.

Identification and Field Bioassays of the Sex Pheromone of Synanthedon haitangvora

Two major components from pheromone gland extracts of Synanthedon haitangvora females were identified as (Z,Z)-3,13-octadecadienyl acetate (Z3,Z13-18:OAc) and (E,Z)-2,13-octadecadienyl acetate (E2,Z13-18:OAc), and the average ratio of these components was about 1:1. Seven minor components, (Z)-9-hexadecenyl acetate (Z9-16:OAc), (Z)-11-hexadecenyl acetate (Z11-16:OAc), (Z)-9-octadecenyl acetate (Z9-18:OAc), (Z)-13-octadecenyl acetate (Z13-18:OAc), (E,Z)-3,13-octadecadienyl acetate (E3,Z13-18:OAc), (Z,Z)-3,13-octadecadien-1-ol (Z3,Z13-18:OH), and (E,Z)-2,13-octadecadien-1-ol (E2,Z13-18:OH), also were identified from gland extracts. Field tests showed that male S. haitangvora were attracted to Z3,Z13-18:OAc alone, but the maximum number of males was attracted to the binary blend of Z3,Z13-18:OAc and E2,Z13-18:OAc mimicking the blend found in female extracts. The addition of minor components to a 1:1 blend of Z3,Z13-18:OAc and E2,Z13-18:OAc did not increase the numbers of moths captured. The only significant effect of minor components was the strong inhibitory effect of adding Z3,Z13-18:OH to the primary binary blend. Increasing doses of the optimum pheromone blend in the lures from 0.1 to 2.0 mg increased trap catches of male S. haitangvora.

Sex pheromone composition of the cotton caterpillar, Palpita indica (Lepidoptera: Pyralidae), in Korea

This study was conducted to investigate the sex pheromone composition of Palpita (= Diaphania) indica (Saunders) (Lepidoptera: Pyralidae) in Korea. Two sex pheromone components, E11-16:Al and E,E-10,12-16:Al, were identified by GC and GC-EAD analysis of sex pheromone gland extracts. The mean ratios of the two components, E11-16:Al and E,E-10,12-16:Al, were about 6.5:3.5 and 7.5:2.5 in gland extracts and in SPME collection, respectively. In field bioassays, maximum attraction occurred in traps baited with a 7:3 ratio of E11-16:Al and E,E-10,12-16:Al. The head extracts of P. indica stimulated the sex pheromone production of P. indica, as well as Hez-PBAN and PssPT, indicating that a PBAN-like substance exists in the head extracts of P. indica. Whole-mount immunocytochemistry showed that three groups of neurosecretory cells showed PBAN-like immunoreactivity in the SEG of P. indica. The PBAN-like immunoreactivity connected to the Corpora Cardiaca, a neurohemal organ. Also, PBAN-like immunoreactivity was found in the brain and in the thoracic and third/fourth abdominal ganglia. The addition of sex pheromone components of Peridroma saucia to the sex pheromone of P. indica greatly improved the attraction of P. indica males. The mixing of the sex pheromone components of S. exigua did not significantly increase the catches of P. indica, while the sex pheromone of H. armigera completely inhibited the attractiveness.

Sex Pheromone Components of the Female Black Cutworm Moth in China: Identification and Field Trials

The sex pheromone blend of a China strain of the black cutworm moth Agrotis ypsilon (Rottemberg) (Lepidoptera: Noctuidae) was investigated. Chemical analysis of pheromone gland extracts of 3-day-old females showed that individual isolated glands contained only very small amounts of pheromone. The high-resolution gas chromatography combined with mass spectrometry (GC-MS) analysis showed the presence of Cis-7-dodecenyl acetate (Z7-12:Ac, A), Cis-9-tetradecenyl acetate (Z9-14:Ac, B), Cis-11-hexadecenyl acetate (Z11-16:Ac, C), Cis-8-dodecenyl acetate (Z8-12:Ac, E) and Cis-5-decenyl acetate (Z5-10:Ac, D) in biologically active pheromone gland extracts. An extract of one gland from a day 3 female gave the following values for the gland components: 0.245±0.098ng for Z7-12: Ac, 0.080±0.03lng for Z9-14: Ac, 0.089±0.033ng for Z11-16: Ac, 0.085±0.03lng for Z5-10: Ac, 0.105±0.065ng for Z8-12: Ac per female. The percentages of Z7-12:Ac, Z9-14: Ac, Zl1-16: Ac, Z5-10: Ac and Z8-12: Ac in pheromone gland extracts from individual females were (mean±SE) 40.451±13.66, 13.176±5.279, 14.943±5.142, 14.392±6.10 and 17.225±9.792 respectively, and the percentages of Z7-12:Ac, Z9-14:Ac and Zl1-16:Ac were 58.75±9.429, 18.91±7.539 and 22.34±7.209. Field trials indicated that each single component of sex pheromone was non-effective and captured no males. The lures baited with duality compound of AB (3:1) had a certain attraction to males, the mean captured number was 2.6. The attraction ability of the lures baited with ternary compound of ABC (3:1:1) to males added significantly, the mean captured number per trap was 7.40, which was 2.8 times of duality compound of AB (3:1). The contents of sex pheromone could obviously affect its capture ability to males, the mean captured number was the highest at the dosage of 200 μg.

Synthesis and Field Evaluation of the Sex Pheromone of <I>Stenoma catenifer</I> (Lepidoptera: Elachistidae)

Field trials of the sex pheromone of an important and potentially invasive pest of avocados, Persea americana Miller (Lauraceae), Stenoma catenifer Walsingham (Lepidoptera: Elachistidae), were carried out in commercial avocado orchards in Guatemala. The results indicated that the pheromone consists of a single component, (9Z)-9,13-tetradecadien-1-ynal; blends of this compound with a range of ratios of the corresponding alcohol and acetate, or with (6Z,9Z)-tricosadiene, which was present in pheromone gland extracts, were equally or less attractive to male moths than the single component. A range of doses from 10 microg to 1 mg were equally attractive, and lures remained attractive for periods of several weeks. Male moth flight activity peaked between 0230 and 0430 hours. Overall, trap catches were relatively low, similar to what was reported for the congeneric Stenoma cecropia Meyrick, suggesting that this species may use other signals in addition to pheromones during mate location. Nevertheless, the pheromone will be useful for detection of S. catenifer, particularly in areas where there is a risk of the moth invading and establishing due to increased commerce in fresh avocados, and for certifying export orchards as being free of S. catenifer.

Reidentification of pheromone composition of Sparganothis sulfureana (Clemens) and evidence of geographic variation in male responses from two US states

GC-EAD analyses of pheromone gland extracts of calling female Sparganothis sulfureana revealed at least 6 compounds that consistently elicited antennal responses from male antennae. In addition to the major pheromone compound, ( E)-11-tetradecenyl acetate ( E11–14:OAc), which was previously reported, the other compounds were found to be ( E)-9-dodecenyl acetate ( E9–12:OAc), ( Z)-9-dodecenyl acetate ( Z9–12:OAc), ( Z)-9-tetradecenyl acetate ( Z9–14:OAc), ( Z)-11-tetradecenyl acetate ( Z11–14:OAc), and ( E)-11-tetradecenol ( E11–14:OH). Tetradecyl acetate, hexadecyl acetate and hexadecenyl acetates were also present in the extracts, but elicited no EAG response from male antennae. Wind tunnel tests demonstrated that males from New Jersey responded equally well to a blend containing five pheromone components in relative to the pheromone glands of calling females. Different male-response profiles from field-trapping tests conducted in the states of Wisconsin and New Jersey were observed, respectively. Significantly higher numbers of male S. sulfureana were caught in New Jersey in traps baited with the binary blend of E11–14:OAc (30 μg) with 1% of Z11–14:OAc, but males from Wisconsin responded equally well to traps containing blends of E11–14:OAc with 0–10% of Z11–14:OAc. The addition of more than 10% of Z11–14:OAc to the primary pheromone compound reduced male captures significantly in both states. Male catches were doubled by adding E9–12:OAc and E11–14:OH to the most attractive binary blend in both states. The trapping test with caged live virgin female moths showed that males in Wisconsin preferred females from the local population than those from New Jersey. The differences in male responses observed may indicate the existence of pheromone polymorphism in this species.