Sex pheromone of the butterbur borer, Ostrinia zaguliaevi

The sex pheromone blend of the butterbur borer, Ostrinia zaguliaevi (Lepidoptera: Pyralidae) was analyzed by means of gas chromatography-electroantennographic detection (GC-EAD), GC-mass spectrometry and a series of wind-tunnel bioassays. Four EAD-active compounds were detected in the female sex pheromone gland extract, and these were identified as tetradecyl acetate (14:OAc), (Z)-9-tetradecenyl acetate (Z9-14:OAc), (E)-11-tetradecenyl acetate (E11-14:OAc) and (Z)-11-tetradecenyl acetate (Z11-14:OAc). The average amounts ± s.d. of the four compounds in a single sex pheromone gland were 7.9±3.7 ng, 10.1±3.2 ng, 1.1±0.5 ng and 11.6±5.1 ng, respectively. In a wind-tunnel bioassay, the ternary blend of Z9-, E11- and Z11-14:OAc at a ratio found in the sex pheromone gland (45:5:50) elicited the same behavioral responses from the males as did virgin females and pheromone gland extract. Removal of any single compound from the ternary blend significantly diminished the pheromonal activity, whereas addition of 14:OAc to the ternary blend had no effect on the males' behavioral responses. Therefore, it was concluded that the sex pheromone blend of O. zaguliaevi is composed of Z9-14:OAc, E11-14:OAc and Z11-14:OAc at a ratio of 45:5:50.     

Geometric isomers of sex pheromone components do not affect attractancy of Conopomorpha cramerella in cocoa plantations

The cocoa pod borer (CPB), Conopomorpha cramerella (Snellen), sex pheromone was previously identified as a blend of (E,Z,Z)‐ and (E,E,Z)‐4,6,10‐hexadecatrienyl acetates and corresponding alcohols. These pheromone components were synthesized by modification of an existing method and the relative attractiveness of synthetic blends that included different levels of non‐target pheromone components and chemical purities was tested in a cocoa field using Delta traps. Male captures were not significantly different among traps baited with pheromone blends containing 5% to 47% (based on four identified pheromone components) of other geometric acetates [(E,Z,E)‐, (Z,Z,Z)‐, (Z,E,Z)‐ and (Z,E,E)‐4,6,10‐hexadecatrienyl acetates], indicating that C. cramerella males did not discriminate among the pheromone components and other geometric isomers in the blends. Therefore, neither antagonistic nor synergistic effects from other pheromone geometric isomers were observed. The modified synthetic pathway offers the prospect of more economical production of CPB sex pheromone. During 17 weeks when C. cramerella monitoring coincided with the main cocoa pod harvest period in 2013–2014, CPB trap catch data from some blends showed a good correlation with the number of pods with C. cramerella infestation symptoms.     

Responses of male winter moths (Operophtera brumata) to their sex attactant (3Z,6Z,9Z)-1,3,6,9 nonadecatetraene and to some structural analogues

Conclusion (3Z,6Z,9Z)-1,3,6,9-nonadecatetraene, the synthetic sex pheromone of the female of O. brumata is highly active in attracting males of this species in the field (Germany and Switzerland). No analogous compounds possessing attractivity to O. brumata males have been found up to now, nor did they show any inhibitory effects to the same species.Therefore (3Z,6Z,9Z)-1,3,6,9-nonadecatetraene (I) can be recommended as a good attractant in the prognosis or monitoring of this lepidopteran pest.     

Identification of components of the female sex pheromone of the potato tuber moth, Scrobipalpopsis solanivora

The sex pheromone produced by virgin female S. solanivora moths has been shown to contain (E)-3-dodecenyl acetate with approximately 2% of the Z isomer by electroantennography and gas chromatography. In the field, traps baited with (E)-3-dodecenyl acetate alone or in combination with 1% or 2% of the Z isomer caught at least as many male S. solanivora moths as those baited with virgin female moths, and there was some evidence that addition of 5% of the Z isomer reduced catches.

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Résumé S. solanivora est l'un des plus importants lépidoptères détruisant les pommes de terre en Amérique Centrale. L'analyse par chromatographie en phase gazeuse (GC) des produits obtenus par lavage de l'ovipositeur de femelles vierges, associée à des électro-anténnogrammes (EAG) a révélé un composé actif unique en EAG. Les durées de rétention pour ce constituant correspondaient à celles des acétates monoinsaturés à 12 carbones, et les analyses sur colonne GC liées avec une phase liquide cristal ont montré un pic principal correspondant à l'acétate (E)-3-dodécénul et un pic secondaire, correspondant à l'isomère Z, et au niveau de 2,5% du pic principal. L'acétate dodécyl a aussi été décelé en quantités variables, approximativement 10% du pic principal.Dans la nature, des pièges contenant de l'acétate (E)-3-dodécényl, seul ou mélangé avec 1 ou 2% de l'isomère Z, ont capturé autant des mâles de S. solanivora que des pièges contenant des femelles vierges, et certaines indications montrent que l'addition de 5% de l'isomère Z réduit les captures.

     

A sex pheromone component novel to the Geometridae identified fromEpirrita autumnata

(Z,Z,Z)-1,3,6,9-Heneicosatetraene was identified as a sex pheromone component ofEpirrita autumnata (Borkhausen), (Lepidoptera: Geometridae). Gas chromatography coupled with electroantennographic detection revealed one active peak from female pheromone gland extracts. The chemical identification of the compound was based on gas chromatography-mass spectrometry, chemical micro-reactions and unambiguous synthesis. In a field test, a rubber septum loaded with 3000 μg of this compound showed highest attraction of maleE. autumnata moths compared to lower doses and the control. The attraction of males to a 300 μg bait was equivalent to that obtained using live virgin females.     

Behaviour of male oriental fruit moth, Grapholita molesta, in overlapping sex pheromone plumes in a wind tunnel

The behaviour of Grapholita molesta (Busck) (Lepidoptera: Tortricidae) males was studied in overlapping sex pheromone plumes in a wind tunnel. The ultimate aim of the study was to assess the effect of different treatments on male behaviour and consider the observed changes within the context of the suggested mechanisms underlying mating disruption. Two baits were placed either in series or parallel using both synthetic pheromone blends and female extracts. One bait, the reference containing (Z)-8-dodecenyl acetate/(E)-8-dodecenyl acetate/(Z)-8-dodecenol in a ratio of 100/6/10 was kept constant at a dose of 100 g of the main component, giving a composition and a release rate close to that of a female. The dose of the other bait varied between 0.1 and 100 times the concentration of the reference and was a mixture of one, two or three pheromone components. Males clearly discriminated between different blends and doses in the overlapping plumes, for regardless if the lures were presented in series or in parallel they followed the complete plume. Complete suppression of the response to the reference was only achieved with 300 g of the optimal three-component blend on the other lure. When tested singly, a bait consisting of Z8-12:OAc/E8-12:OAc/Z8-12:O Hin a 100/0.2/0.4 ratio, attracted a high proportion of the males when placed 75 cm upwind of the male release site, but no males from 150 cm. Our data suggest that complete pheromone blends should be more effective than any incomplete blends in mating disruption formulations for G. molesta.     

Sex pheromones of three small ermine moths found on the European spindle tree

The sex pheromones produced by virgin females of three species of small ermine moths occurring sympatrically on the European spindle tree were analysed by gas chromatography and the synthetic compounds tested against male moths in the laboratory and field. Pheromone gland extracts of Yponomeuta cagnagellus were shown to contain tetradecyl acetate, (E)-11- and (Z)-11-tetradecenyl acetate, tetradecanol, (E)-11- and (Z-11-tetradecenol and hexadecyl acetate in 30/3/100/6/0/7/42) ratio. Wind tunnel bioassays and field tests showed that (E)-11-tetradecenyl acetate primary pheromone components, and that tetradecyl acetate synergised their attractiveness. The alcohols were unimportant in these tests. Analysis of the pheromone gland extracts from Y. irrorellus showed the above components in 68/56/100/9/6/8/17 ratio, and a mixture of these attracted male moths in laboratory and field. Omission of either unsaturated acetate gave unattractive mixtures, and the alcohols were also found to be important for attraction. Pheromone gland extracts from Y. plumbellus were shown to contain the seven components in 46/148/100/20/20/13/25 ratio. Field tests showed that the two monounsaturated acetates are primary pheromone components, and removal of the alcohols had no significant effect. The titre of (Z)-11-tetradecenyl acetate in Y. plumbellus pheromone gland extracts was approximately 0.5 ng per female, one tenth the titre in the other two species. It is concluded that mixtures of three or more pheromone components with specific E/Z ratio are essential for full attraction and contribute towards premating reproductive isolation of the three species. Other factors such as rate of pheromone emission, time of flight and height of flight may also contribute to reproductive isolation.

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Résumé L'analyse a porté sur les phéromones sexuelles de 3 Yponomeutidae, trouvés en sympatrie sur le fusain. Des expériences sur le comportement de Y. cagnagellus ont montré que la fraction acétate de tétradécyl de la phéromone synergise les fractions connues antérieurement: (E)-11- et (Z)-11-acétates de tétradécényl, lorsque les proportions sont 37/2/100. L'analyse en chromatographie gazeuse d'extraits de glandes à phéromone de Y. irrorellus a mis en évidence, dans les proportions approximatives suivantes 68/56/100/9/6/8/7, de l'acétate de tétradécyl, des (E)-11 et (Z)-11 acétates de tétradécényl, du tétradécanol, des (E)-11 et (Z)-11-tétradécénols, et de l'acétate d'hexadécyl. Un mélange de ces composés a provoqué un vol intégral contre le vent des mâles dans un tunnel à vent et a attiré les mâles dans la nature.L'analyse des extrait de glandes à phéromone de Y. plumbellus a donné de l'acétate de tétradécyl, du (E)-11-acétate de tétradécényl et du (Z)-11-acétate de tétradécényl, dans les proportions: 50/150/100. Une étude par élimination dans la nature a montré que les acétates non saturés étaient les composés fondamentaux de la phéromone. La teneur en (Z)-11-acétate de tétradécényl de la glande à phéromone de Y. plumbellus était d'environ 0.5 ng par femelle, soit approximativement le dixième de celle observée chez les deux autres espèces.Une très faible attraction croisée a été trouvée avec des phéromones totalement synthétisées. Lorsque l'acétate de (E)-11-tétradécényl a été enlevé des phéromones de Y. irrorellus et Y. plumbellus, le reliquat a attiré des nombres significatifs de Y. cagnagellus. Nous en concluons que des mélanges de trois composés ou plus, avec des proportions spécifiques des isomères (E) et (Z), sont indispensables pour une activité complète et pour maintenir un isolement reproductif précopulatoire entre les espèces.

     

Identification and functional characterization of sex pheromone receptors in beet armyworm Spodoptera exigua (Hübner)

In moths, males can detect a distinct blend of several pheromone components by specialized olfactory receptor neurons (ORNs) on the antennae. Four candidate pheromone receptors (PR) with seven transmembrane domains were identified by homology cloning from the antennae of Spodoptera exigua (Sexi). Phylogenetic analyses reveal that all four odorant receptors (OR) belong to pheromone receptor subtypes. Expression patterns revealed that PRs were male-specific in the antenna except for SexiOR11, which was female antenna-biased. Functional analyses of these PRs were conducted using heterologous expression in Xenopus oocytes. SexiOR13 and SexiOR16 were all broadly activated by multiple pheromone components. SexiOR13 responded robustly to the critical pheromone component, Z9, E12-14:OAc and the minor pheromone component, Z9-14:OAc at a concentration of 10^?4 M. Dose-response studies indicate that SexiOR13 was approximately 4 times more sensitive to Z9,E12-14:OAc (EC50 = 3.158 × 10^?6 M) compared to Z9-14:OAc (EC50 = 1.203 × 10^?5 M). While, SexiOR16 responded robustly to the secondary pheromone component Z9-14:OH with high sensitivity (EC50 = 9.690 × 10^?7 M). However, similar tests of the five pheromones with SexiOR6 and SexiOR11 failed to elicit any response. These results provide basic knowledge to further advance research on the molecular mechanisms of pheromone reception.     

Responses of Mamestra suasa male moths to synthetic pheromone compounds in a wind tunnel

The upwind flight and landing responses of male Mamestra suasa (Den. & Schiff.) (Lepidoptera; Noctuidae) to various synthetic chemicals were studied in a wind tunnel. A mixture of (Z)-11-hexadecenyl acetate (Z11-16: Ac) and (Z)-11-hexadecenal (Z11-16: Ald) elicited upwind flight responses past the midpoint of the wind tunnel, and both components were necessary for landing of the males to occur at the pheromone source point. The best response to the mixtures tested was to a ratio 100:1 (ng) of Z11-16: Ac and Z11-16: Ald (blend B).The addition of (Z)-9-tetradecenyl acetate (Z9-14: Ac) (10 ng) to blend B resulted in a significant decrease of upwind flight and landing responses. The inhibitory effect of this chemical when it is mixed with blend B, and the presence of a specific receptor for this compound in sensilla trichodea of male M. suasa, suggest that Z9-14: Ac is involved in the chemical communication between M. suasa and other sympatric species. The addition of (Z)-11-hexadecenol (Z11-16: OH) (1 or 10 ng) to blend B had no effect on male upwind flight and landing responses. This compound does not seem to be involved in the chemical communication of this species.

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Résumé L'observation et la comptabilisation des vols orientés et des atterrissages des mâles de Mamestra suasa (Den. & Schiff.) (Lepidoptera; Noctuidae) sur une source de phéromone de synthèse ont mis en évidence un mélange attractif appelé mélange B et constitué par 100 ng de Z11-16: Ac et 1 ng de Z11-16: Ald. L'attraction et l'atterrissage sont sous la dépendance du mélange de ces 2 composés. Les variations de leurs proportions relatives affectent les différentes phases du comportement de vol des mâles.L'addition de 10 ng d'acétoxy-1 tetradécène-9 Z (Z9-14: Ac) diminue significativement les proportions de vols orientés et d'atterrissages par rapport aux réponses obtenues avec le mélange B seul. L'effet inhibiteur de cette molécule sur l'attractivité du mélange B et la présence chez M. suasa d'un récepteur spécialisé dans la perception de ce composé suggèrent que le Z9-14: Ac est impliqué dans la communication chimique entre M. suasa et d'autres espèces sympatriques. L'addition d'hexadécènol-11 Z (Z11-16: OH) au mélange B à la dose de 1 ou 10 ng ne modifie pas les réponses des mâles. Ce composé ne semble pas impliqué dans la communication chimique chez M. suasa.

     

Sex attractants for Pexicopia malvella and Platyedra subcinerea, pests of malvaceous ornamentals and cotton

Pexicopia malvella (Hbn.) males were attracted to mixtures containing (Z,E)-7,11-hexadecadienyl acetate and (Z,Z)-7,11-hexadecadienyl acetate, in screening tests, in Hungary. An approximate dose of 40 g 5:1 ZE:ZZ mixture is recommended for practical use as a selective and potent sex attractant. Platyedra subcinerea (Hw.), another gelechiid pest, was attracted best to a 300 g dose of (Z,Z)-7,11-hexadecadienyl acetate.

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Zusammenfassung Die binäre Mischung von (Z,Z)-7,11-hexadekadienylacetat und (Z,E)-7,11-hexadekadienylacetat erwies sich im Freiland als Sexuallockstoff für Männchen von P. malvella (Gelechiidae, Lepidoptera). Die Verhältnisse 1:1, 1:1.4, 1:2.5, 1:5 und 1:10 lockten bedeutende Anzahlen von Männchen, die Komponenten allein waren unwirksam. Die Mischung in Verhältnis 1:5 und bei der Köderbeladung von ungefähr 40 g kann zur praktischen Anwendung als ein spezifisches und effektives Lockstoff empfehlt werden.Männchen von P. subcinerea (= vilella Gelechiidae, Lepidoptera) wurden zu Fallen mit dem Isomer (Z,Z) angelockt. Beste Fangergebnisse wurden mit der Köderbeladung 300 g (Z,Z)-7,11-hexadekadienylacetat erreicht. P. malvella wird in Ungarn als bedeutungsvoller Schädling von Zierpflanzen der Familie Malvaceae gemeldet, und alle beide Arten sind als Baumwolleschädlinge in zentralasiatischen Sovietrepubliken und anderen Ländern in Asien bekannt.

     

(Z)-8-dodecenyl acetate: the major component of the female sex pheromone of Cryptophlebia batrachopa, a Tortricid pest of macadamia in Malawi

Ovipositor washings from virgin female Cryptophlebia batrachopa (Meyrick) (Lepidoptera: Tortricidae) were analysed by gas chromatography (GC) linked to electroantennography (EAG) and by high-resolution GC. The major EAG-active component in ovipositor washings was shown to be (Z)-8-dodecenyl acetate with less than 0.5% of the E isomer. GC analysis of ovipositor washings from C. leucotreta confirmed the presence of approximately equal amounts of (Z)- and (E)-8-dodecenyl acetates (Persoons et al., 1977). When pure (Z)-8-dodecenyl acetate and mixtures containing up to 50% of the E isomer were tested in the field in Malawi where both Cryptophlebia species occurred, C. batrachopa male moths were caught only in traps baited with 10% or less of the E isomer and highest catches were recorded for the pure Z isomer. By contrast C. leucotretra males were caught predominantly by traps baited with more than 10% E isomer and no catches were recorded for the pure Z isomer. (Z)-8-dodecenyl acetate containing 1% of the E isomer was found to attract male moths of Opogona spp.

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Résumé Les produits recueillis par lavages de l'ovipositeur de Cryptophlebia batrachopa Meyr. (Lep. Tortricidae) ont été analysés par chromatographie gazeuse (GC) associée à l'électroantennographie (EAG) et la GC à haute résolution. Le principal constituant actif en EAG provenant des lavages s'est révélé être le (Z)-8-dodécényl acétate avec moins de 0,5% de l'isomère E. L'analyse GC de ces produits de lavage de C. leucotreta ont confirmé la présence d'à peu près les mêmes quantités de (Z) et (E)-8-dodécényl acétates (Persoons et al., 1977). Quand des essais sur le terrain ont été effectués au Malawi, où existent les deux espèces de Cryptophlebia, avec du (Z)-8-dodécényl acétate et des mélanges comprenant jusqu'à 50% de l'isomère E, des mâles de C. batrachopa ont seuls été capturés dans des pièges contenant 10% ou moins de l'isomère E; les captures les plus élevées ont été obtenues avec l'isomère Z pur. A l'opposé, surtout des mâles de C. leucotreta ont été capturés dans des pièges garnis avec plus de 10% d'isomère E, et aucune capture n'a été obtenue avec l'isomère Z pur. Des mâles d'Opogona spp. ont été attirés par du (Z)-8-dodécényl acétate contenant 1% de l'isomère E.

     

Identification of the sex pheromone of Ostrinia palustralis

By means of gas chromatography with electroantennographic detection, gas chromatography-mass spectrometry and a series of bioassays, (E)-11-tetradecenyl acetate (E11-14:OAc) and (Z)-11-tetradecenyl acetate (Z11-14:OAc) at a ratio of 99:1 were identified as female sex pheromone components of Ostrinia palustralis. The average amounts of E11- 14:OAc and Z11-14:OAc in a single sex pheromone gland were 37.2±24.4 ng and 0.3±0.2 ng, respectively. In a wind-tunnel bioassay, the binary blend of E11- and Z11-14:OAc elicited the same male behavioral responses as did virgin females.     

Female sex pheromone of Athetis lepigone (Lepidoptera: Noctuidae): Identification and field evaluation

Athetis lepigone has been recorded in many countries in Europe and Asia, but it had never been documented as an agricultural pest until 2005. For the purpose of using the sex pheromone to control this pest, we conducted a study to identify the sex pheromone of A. lepigone by gas chromatography with an electroantennographic detector (GC‐EAD) and GC coupled with mass spectrometry (GC/MS) analyses. Three pheromone candidates were detected by GC‐EAD analysis in the extracts of the female sex pheromone gland, and two candidates were identified as (Z)‐7‐dodecenyl acetate (Z7‐12:OAc) and (Z)‐9‐tetradecenyl acetate (Z9‐14:OAc) in a ratio of 1:5 by mass spectral analysis of natural pheromone components and dimethyl disulphide adducts. In the field male trapping test, the traps baited with the binary blend captured high number of males, while traps with single component hardly caught males, indicating that the two components are essential for the male attractiveness. In addition, the optimum ratios of Z7‐12:OAc and Z9‐14:OAc were determined as 3:7–7:3, and the best doses for the binary blend (at ratio of 3:7 between Z7‐12:OAc and Z9‐14:OAc) were 0.25–0.5 mg/trap, based on the number of male catches. The identification of a highly attractive sex pheromone will help in developing efficient strategies for monitoring and control of A. lepigone.     

Field evaluation of female sex pheromone components of the cotton bollworm,Heliothis armigera

(Z)-11-hexadecenal and (Z)-9-hexadecenal were ineffective lures forH. armigera males unless combined. Attraction depended upon perception of a 90%–99% combination of (Z)-11-hexadecenal with 1%–10% (Z)-9-hexadecenal. Increasing the level of (Z)-9-hexadecenal in the mixture to 26.2% reduced catches. Adding 2.3% (Z)-7-hexadecenal to the mixture did not enhance or reduce attraction, while adding 8.7% (Z)-11-hexadecenol significantly reduced male catches. The combination of (Z)-11-hexadecenal and (Z)-9-hexadecenal was effective only when released from rubber dispensers but not from polyethylene vials. A load of 2 mg of the mixture on rubber dispensers effectively attracted males for at least 31 days. TheH. zea lure which contained all the pheromonal components of that species was also effective in attractingH. armigera males. TheH. virescens lure attracted significantly fewerH. armigera males than theH. zea lure.

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Résumé Les (Z)-11-hexadecenal et (Z)-9-hexadecenal sont des attractifs sexuels in efficaces pour les mâles deH. armigera. L'attraction dépend de la perception d'un mélange de 90 à 99% de (Z)-11-hexadecenal avec 1 à 10% (Z)-9-hexadecenal, L'augmentation jusqu'à 26,2% de la teneur en (Z)-9-hexadecenal réduit les captures. L'addition de 2,3% de (Z)-7-hexadecenal au mélange ne modifie pas l'attractivité, tandis que celle de 8,7% de (Z)-11-hexadecenol, réduit significativement les captures de mâles. Le mêlange de (Z)-11-hexadecenal et de (Z)-9-hexadecenal n'a été efficace qu'avec des diffuseurs en caoutchouc, par contre il a été sans effet à partir de récipients de polyéthylène. Une charge de 2 mg de mélange dans des diffuseurs en caoutchouc attire effectivement les mâles pendant ou moins 31 jours. L'attractif sexuel deH. zea qui contient tous les constituants de la phéromone de cette espèce attire aussi efficacement les mâles deH. armigera. Celui deH. virescens attire significativement moins de mâles deH. armigera que l'attractif sexuel deH. zea.

     

Field evaluation of female sex pheromone of the artichoke moth, Gortyna xanthenes

Field responses of Gortyna xanthenes (Germar) males to traps baited with different mixtures of the female sex pheromone components were evaluated in an artichoke field. Catches were compared to those obtained by virgin females and light traps. The best results were achieved by utilizing a mixture of 5 mg Z11-16:Ald + 0.15 mg Z9-16:Ald + 0.15 mg 16:Ald + 0.12 mg Z11-16:OH, which captured only G. xanthenes males 3–5 times more than light traps and ca two times more than one virgin female. Starting from the basic mixture Z11-16:Ald (89–92%) + Z9-16:Ald (2–4%), the addition of 16:Ald (2–4%) and of Z11-16:OH (2–3%) produced an increase of G. xanthenes and a decrease of H, armigera (Hb.) catches. The inhibitory action of Z11-16:OH towards H. armigera males was confirmed.

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Evaluation sur le terrain des constituants de la phéromone sexuelle de la noctuelle de l'artichaut (Gortyna xanthenes)

Résumé Dans un champ d'artichaut de la province de Salerno on a evalué la réponse des mâles de G. xanthenes à mélanges divers des constituants de la phéromone sexuelle produite par la femelle. Les meilleurs résultats ont été obtenus en employant un mélange de 5 mg Z11-16:Ald + 0.15 mg Z9-16:Ald + 0.15 mg 16:Ald + 0.12 mg Z11-16:OH, qui a capturé seulement les mâles de G. xanthenes en mesure 3–5 fois plus élevée que les pièges lumineux et ca. deux fois plus élevée que la femelle vierge. En partant du mélange base Z11-16:Ald (89–92%) + Z9-16:Ald (2–4%), l'addition de 16:Ald (2–4%) et de Z11-16:OH (2–3%) a causé un accroissement des captures de G. xanthenes et une diminution des captures de Heliothis armigera. Cela confirme l'action inhibitoire du Z11-16:OH à l'égard des males de H. armigera.

     

Antagonistic Effect of (Z)-11-Hexadecen-1-ol on the Pheromone-Mediated Flight of Helicoverpa zea (Boddie) (Lepidoptera:Noctuidae)

Flight-tunnel experiments were conducted using Helicoverpa zea males to determine whether or not (Z)-11-hexadecen-1-ol (Z11-16:OH), a compound emitted by another heliothine moth species, Heliothis subflexa, is a behavioral antagonist when admixed with the two-component pheromone blend of H. zea. Males were less likely to fly upwind all the way to the source when 0.3% Z11-16:OH was present in the blend. Even 0.1% Z11-16:OH caused differences in the flight behavior of H. zea males; they steered more off the windline than males responding to the pheromone blend alone, resulting in more oblique track angles. Thus Z11-16:OH appears to act antagonistically, along with another compound, (Z)-11-hexadecen-1-ol acetate (Z11-16:Ac), when it is added to the H. zea pheromone blend.     

Sex pheromone analysis and effective attraction of males of the cabbage webworm,Hellula undalis,inhabiting the Mekong Delta of Vietnam

Hellula undalis is a harmful insect pest of green mustard in the Mekong Delta of Vietnam. In order to establish a tool for a sustainable pest control program, the sex pheromone of H. undalis inhabiting the Mekong Delta was examined. GC-EAD and GC–MS analyses of pheromone gland extracts from the virgin females elucidated three new components, (Z)-11-tetradecenyl acetate (Z11-14:OAc), (Z)-11-hexadecenal (Z11-16:Ald), and (11E,13E)-11,13-hexadecadien-1-ol, in addition to the known pheromone component (11E,13E)-11,13-hexadecadienal (E11,E13-16:Ald). Double bond positions of the two monoenyl components were determined by GC–MS analysis of the pheromone extract treated with dimethyl disulfide. On the other hand, GC–MS analysis of the female body extract detected the unsaturated hydrocarbon (3Z,6Z,9Z)-3,6,9-tricosatriene (Z3,Z6,Z9-23:H). Field examinations of their synthetic compounds indicated the significant role of E11,E13-16:Ald as a major component and a clear synergistic effect of the two monoenyl compounds as a minor component. Although the 3:3:7 mixture of Z11-14:OAc, E11-16:Ald, and E11,E13-16:Ald captured the largest number of males among the tested mixtures, the activity was still quite a bit lower than that of virgin females. However, the 3:3:7:1 mixture, which was prepared by adding a small amount of Z3,Z6,Z9-23:H to the 3:3:7 ternary lure, succeeded in attracting males more powerfully than the females did. This strong synergistic effect was not observed when the triene was added to unmixed E11,E13-16:Ald, indicating important roles of not only the triene but also the two monoenyl compounds as natural pheromone components.     

Sex pheromone components ofMamestra suasa: chemical analysis, electrophysiological activity, wind tunnel activity and field tests in two European countries

(Z)-11-hexadecenyl acetate (Z-11-16:Ac), (Z)-11-hexadecenal (Z-11-16:Ald), (Z)-11-hexadecenol (Z-11-16:OH) and hexadecanyl acetate (16:Ac) were found in pheromone gland extracts of femaleMamestra suasa (Den. et Schiff.) in the relative amounts 100/2/10/5. All four compounds were also present in collections of aiiborne volatiles from calling females in a 100/7/5/5 ratio. No traces of 14 carbon aldehydes or acetates were detected. In gland extracts the presence of methyl hexadecanoate methyl (Z)-9-hexadecenoate and methyl (Z)-11-hexadecenoate was demonstrated by base methanolysis. No methyl tetradecenoates were detected. In EAG tests Z-11-16:Ac gave the best responses, followed by (Z)-9-tetradecenyl acetate (Z-9-14:Ac) Z-11-16:Ald and Z-11-16:OH. In single sensillum recordings large spike amplitude cells in sensilla responded to Z-11-16:Ac, while small spike amplitude cells to both Z-11-16:OH and Z-9-14:Ac. Cells responding to Z-11-16:Ald were found in one out of 60 sensilla tested. In wind tunnel tests 0.1 g of a 10:1 blend of Z-11-16:Ac/Z-11-16:Ald evoked the same responses and at a similar intensity as 3 isolated female pheromone glands did. In field tests a 10:1 blend of Z-11-16:Ac/Z-11-16:Ald caught significant numbers of males in both Bulgaria and Hungary. The addition of 16:Ac to the binary blend did not have any effect, while more than 1% of Z-11-16:OH or 0.1% of Z-9-14:Ac dramatically decreased captures. In comparing different ratios of the, acetate/aldehyde blend at different dose levels, best catches were recorded at the 10:1 ratio and at the highest (1000 g) dose level.

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La composition de la phéromone sexuelle deMamestra suasa: analyse chimique, étude de l'effet par éléctrophysiologie et à la chambre de vol, et piégeages dans deux pays de l'Europe

Résumé On a trouvé l'acetoxy-1 hexadécene-11 Z (Z-11-16:Ac), le hexadécene-11 Z al-1 (Z-11-16:Ald), le hexadécene-11 Z ol-1 (Z-11-16:OH) et l'acetoxy-1 hexadécene (16:Ac) dans des extraits de glandes phéromona les des femelles deMamestra suasa. La proportion relative des composés était 100/2/10/5. Tous les quatre composés ont été présents aussi dans les collections d'émanations des femelles en stade d'appel, dans la proportion un peu différente de 100/7/5/5. On n'a détecté aucune trace des tétradécenes al-1 ou d'acetoxy-1 tétradécenes. On a démontré la présence de hexadécenoate-1 methyl, hexadécene-9 Z oate-1 methyl et héxadécene-11 Z oate-1 methyl dans des extraits des glandes, par la méthode de base methanolysis. On n'a trouvé pas des tétradéceneoates methyl.En éléctroantennographie, Z-11-16:Ac a donné les meilleurs réponses, suivis par l'acetoxy-1 tétradécene-9 Z (Z-9-14:Ac), Z-11-16:Ald et Z-11-16:OH. Dans des études de single sensillum les cellules à amplitude grande ont répondu à la stimulation avec de Z-11-16:Ac, cependant les cellules à amplitude petite ont répondu à la stimulation avec des deux composés Z-9-14:Ac et Z-11-16:OH. On a trouvé des cellules sensitives à Z-11-16:Ald dans 1 entre 60 sensilla étudiés.À la chambre de vol, le dose de 0.1 g d'un mélange de 10:1 de Z-11-16:Ac/Z-11-16:Ald a provoqué les mêmes réponses et à l'intensité pareille comme 3 glandes phéromonales isolées des femelles.En piégeages sur le champs des males en quantité importante ont été capturé par un mélange de 10:1 de Z-11-16:Ac/Z-11-15:Ald en Bulgarie et Hongrie. L'addition de 16:Ac au mélange binaire n'avait aucun effet, cependant l'addition de plus de 1% de Z-11-16:OH ou 0.1% de Z-9-14:Ac a sérieusement diminué les captûres. En comparant des proportions différentes du mélange de l'acetoxy/aldéhyde dans des doses différentes, on a observé les meilleurs captûres avec de la proportion 10:1 et à la dose la plus haute (1 000 g).

     

Female sex pheromone of a nettle caterpillar,Monema flavescens,in China

Monema flavescens Walker (Lepidoptera: Limacodidae) is a multivoltine, generalist moth whose larvae cause serious damage to many types of trees. Pheromone lures prepared according to a study of a Japanese population were found to be ineffective at attracting M. flavescens nettle caterpillars in China, and some studies have shown intraspecific geographical differences in the composition of sex pheromones. We therefore reexamined the sex pheromone composition of M. flavescens in a Chinese population. In this study, the electroantennographically (EAG) active compounds in an extract from Chinese virgin females of M. flavescens were identified as (E)‐8‐decen‐1‐ol (E8‐10:OH), (Z)‐7,9‐decadien‐1‐ol (Z7,9‐10:OH), (Z)‐9,11‐dodecadien‐1‐ol (Z9,11‐12:OH), and (Z)‐9,11‐dodecadienal (Z9,11‐12:Ald) via coupled gas chromatographic‐electroantennographic detection (GC‐EAD) and coupled GC‐mass spectrometry (MS). Pheromone dimorphism might occur in this species, as this mixture of compounds in Chinese females was different from that of E8‐10:OH and E7,9‐10:OH extracted from Japanese females in previous research. In wind tunnel and field tests, the males were significantly attracted to a blend of the pheromone components E8‐10:OH, Z7,9‐10:OH, and Z9,11‐12:OH in a 100:5:4 ratio. The addition of Z9,11‐12:Ald did not change the male response. The optimized three‐component lure blend may provide a useful tool for monitoring and controlling Chinese populations of M. flavescens.