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Hickory shuckworm Cydia caryana: electroantennogram and flight tunnel studies of potential sex pheromone components (1987)

Smith, M. T. ; McDonough, L. M. ; Voerman, S. ; [et al.]

Springer

Entomologia experimentalis et applicata 44 (1987), S. 23-30

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ISSN: 1570-7458

Keywords: Lepidoptera ; Tortricidae ; Olethreutinae ; Cydia caryana ; sex pheromone ; electroantennogram ; flight tunnel ; behavior

Source: Springer Online Journal Archives 1860-2000

Topics: Biology

Description / Table of Contents: Résumé Les réponses olfactives antennaires de Cydia caryana, mesurées par électroantennogrammes (EAG), aux alcools et acétates à carbones monounsaturés en positions 12 et 14, ont montré que le système conjugué de double liaison, (E)-8-, (E)-10- du dodecadien-1-ol acétate constitue un composé chimique strutural critique de la phéromone sexuelle de C. caryana. De plus, les acétates: (E)-8-dodecen-1-ol,(Z)-8-dodecen-1-ol,(Z)-9-dodecen-1-ol, et le (Z)-12-tetradecen-1-ol, se sont révélés en AEG comme des composés secondaires de la phéromone. L'étude par AEG de la relation dose-réponse a conduit à l'hypothèse de deux catégories de populations de récepteurs de phéromones. L'analyse comportementale des résponses des papillons mâles dans le tunnel de vol aux composés qui ont provoqués les plus forts AEG, on fait estimer que les acétates (E,E)-8,10-dodécadien-1-ol et (Z)-9-dodecen-1-ol ressemblent (ou sont) les constituants de la phéromone sexuelle de C. caryana; tandis que les (Z)-8-dodecen-1-ol et (E)-10-dodecen-1-ol sont, soit des paraphéromones, soit des constituants mineurs de la phéromone. La signification biologique du (Z)-12-tétradécen-1-ol a été difficile à interprêter avec les expériences en tunnel de vol.

Notes: Abstract Electroantennogram (EAG) measurement of male Cydia caryana moth antennal olfactory response to monounsaturated 12 and 14 carbon alcohols and acetates indicated that the (E)-8-, (E)-10- conjugated double bond system of a dodecadien-1-ol acetate is a critical chemical structural component of the C. caryana sex pheromone. Additionally, EAG measurements implicated (E)-8-dodecen-1-ol acetate, (Z)-8-dodecen-1-ol acetate, (Z)-9-dodecen-1-ol acetate and (Z)-12-tetradecen-1-ol as potential minor pheromonal components. An EAG dosage-response study suggested that there were at least two heterologous populations of pheromone acceptors. Behavioral analysis of male moth response in a flight tunnel to compounds which evoked the stronger EAG responses suggested that (E,E)-8,10-dodecadien-1-ol acetate and (Z)-9-dodecen-1-ol acetate resemble or are C. caryana sex pheromonal components, while (Z)-8-dodecen-1-ol acetate and (E)-10-dodecen-1-ol acetate are either parapheromones or are minor pheromone components. Behavioral significance of (Z)-12-tetradecen-1-ol was difficult to interpret in the flight tunnel.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1007/BF00361305

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Filbertworm sex pheromone (1984)

Davis, H. G. ; McDonough, L. M. ; Burditt, A. K. ; [et al.]

Springer

Journal of chemical ecology 10 (1984), S. 53-61

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ISSN: 1573-1561

Keywords: Melissopus latiferreanus ; Lepidoptera ; Tortricidae ; Olethreutinae ; filbertworm ; sex pheromone ; sex attractant ; (E,E)-8 ; 10-dodecadien-1-ol acetate ; (E,Z)-8,10-dodecadien-1-ol acetate ; conjugated diene isomerization

Source: Springer Online Journal Archives 1860-2000

Topics: Biology , Chemistry and Pharmacology

Notes: Abstract (E,E)- and (E,Z)-8,10-Dodecadien-1-ol acetates were identified in a 1∶4.3 ratio in the extract of abdominal tips of female filbert-worm moths,Melissopus latiferreanus (Walsingham). The identifications were based on electroantennogram (EAG) analysis, gas chromatography, mass spectrometry, ozonolysis, and synthesis. TheE,Z isomer produced the stronger EAG response. In the field tests of various ratios ofE,E∶E,Z, the ratio found in the extract captured the most males. The pureE,E isomer initially was not attractive by itself (〈0.1%E,Z) but became attractive after a few days, presumably because of isomerization. TheE, Z isomer (〈0.1%E,E) was attractive initially, but this compound might have isomerized faster than theE,E isomer. A study of the isomerization showed that regardless of the initial mixture of 8,10-dodecadien-1-ol acetate isomers, almost complete equilibration existed after one month. The equilibrium mixture consisted of 9%Z8,E10, 65%E8,E10, 23%E8,Z10, and 3%Z8,Z10. Concentrations in rubber septa (1∶4 ratio ofE,E toE,Z) of 0.03–3.0 mg/septum produced equivalent trap catches.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1007/BF00987643

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Blackheaded fireworm: Laboratory and field studies of its sex pheromone (1987)

McDonough, L. M. ; Davis, H. G. ; Voerman, S.

Springer

Journal of chemical ecology 13 (1987), S. 1235-1242

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ISSN: 1573-1561

Keywords: Rhopobota naevana (Hübner) ; Rhopobota unipunctana Haworth ; Rhopobota naevana naevana (Hübner) ; blackheaded fireworm ; Lepidoptera ; Tortricidae ; Olethreutinae ; sex pheromone ; sex attractant ; (Z)-11-tetradecen-1-ol ; (Z)-11-tetradecen-1-ol acetate ; (Z)-9-dodecen-1-ol acetate

Source: Springer Online Journal Archives 1860-2000

Topics: Biology , Chemistry and Pharmacology

Notes: Abstract Electroantennogram (EAG) responses of maleRhopobota naevana (Hübner), the blackheaded fireworm, to all of the monoene straightchain 12- and 14-carbon alcohols and acetates implicated (Z)-11-tetradecenl-1-ol (Z11–14∶OH) and its acetate (Z11–14∶Ac) as sex pheromone components.Z11–14∶Ac produced the strongest EAG response of all compounds tested. Gas chromatography-mass spectrometry (GC-MS) analysis of extract of female sex pheromone glands (SPG) confirmed the presence ofZ11–14∶OH (125 pg/female) andZ11–14∶Ac (600 pg/female) (all other monoenes had different retention times). In field tests, traps baited withZ11–14∶OH alone captured males, but traps baited withZ11–14∶Ac alone did not. Traps baited with a combination ofZ11–14∶OH andZ11–14∶Ac in various ratios did not produce better trap catches thanZ11–14∶OH alone. (Z)-9-Dodecen-1-ol acetate (Z9–12∶Ac), reported by others to be a field attractant, did not produce trap catch in our tests, but in combination withZ11–14∶ OH (98∶2 in septa corresponding to 95:5 in vapor,Z11–14∶OH toZ9–12∶AC) produced a sevenfold increase in catch overZ11–14∶OH alone. IfZ9–12∶AC had been present in extract of SPG at 2–5% ofZ11–14∶OH, it would not have been detected in our GC-MS experiment.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1007/BF01020551

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