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  • (Z)-9-dodecen-1-ol acetate  (2)
  • Cydia caryana  (2)
  • 1
    Electronic Resource
    Electronic Resource
    Hickory shuckworm Cydia caryana: electroantennogram and flight tunnel studies of potential sex pheromone components (1987)
    Springer
    Entomologia experimentalis et applicata 44 (1987), S. 23-30 
    Details
    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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  • 2
    Electronic Resource
    Electronic Resource
    Apple ermine moth,Yponomeuta malinellus Zeller Two components of female sex pheromone gland highly effective in field trapping tests (1990)
    Springer
    Journal of chemical ecology 16 (1990), S. 477-486 
    Details
    ISSN: 1573-1561
    Keywords: Lepidoptera ; Yponomeutidae ; Yponomeuta malinellus ; sex pheromone ; apple ermine moth ; (Z)-9-dodecen-1-ol acetate ; (Z)-11-tetradecen-1-ol
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract When electroantennographic responses of maleYponomeuta malinellus Zeller to model compounds were determined at dosages of 0.3–30 ng, the strongest responses were obtained from (Z)-9-dodecen-1-ol acetate (Z9–12∶Ac). Also, strong responses were obtained from (Z)-11-tetradecenal (Z11–14∶A1) and (Z)-11-tetradecen-1-ol (Zl1–14∶OH). At a dosage of 0.3 ng,Z11–14∶A1 produced a stronger response thanZ11–14∶OH, while at a dosage of 30 ng,Z11–14∶OH andZ11–14∶A1 produced equal responses. Gas chromatographic and mass spectral analysis of extracts of female sex pheromone glands showed the presence ofZ9–12∶Ac, tetradecan-1-ol (14∶OH), (E)-11-tetradecen-1-ol (E11–14∶OH),Z11–14∶OH, hexadecan-1-ol, and hexadecan-1-ol acetate in a ratio of 0.6∶200∶37∶100∶140∶35. In field tests,Z9–12∶Ac andZ11–14∶OH together were required for trap catch, and addition ofZ11–14∶A1,E11–14∶OH, 14∶OH, or (Z)-11-tetradecen-1-ol acetate did not increase catch. Ratios in rubber septa of 0.5∶99.5 to 1.5∶98.5 (Z9–12∶ Ac/Z11–14∶OH) captured the most males and captures were statistically equivalent for dosages of 10–1000 μg/rubber septum. Traps baited with the synthetic lure produced better catches than those baited with females.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01021779
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  • 3
    Electronic Resource
    Electronic Resource
    Sex pheromone of hickory shuckwormCydia caryana Development of an effective field Lure (1990)
    Springer
    Journal of chemical ecology 16 (1990), S. 317-324 
    Details
    ISSN: 1573-1561
    Keywords: Sex pheromone ; sex attractant ; Cydia caryana ; Lepidoptera ; Tortricidae ; Olethreutinae ; (Z)-8-dodecen-1-ol acetate ; (E)-9-dodecen-1-ol acetate ; dodecanol acetate ; (E, E)-8 ; 10-dodecadien-1-ol acetate ; (E, Z)-8,10-dodecadien-1-ol acetate
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Extracts of the sex pheromone glands of femaleCydia caryana were evaluated by electroantennography and gas chromatography-mass spectrometry. These studies suggested the following compounds were potential sex pheromone components: (Z)-8- and/or (E)-9-dodecenyl acetate (50 pg/female), dodecyl acetate (40 pg/female), and (E, E)-8,10-dodecadienyl acetate (25 pg/female). In field tests only the diene produced trap catch, and when the other components were added to the diene, trap catch was not increased. When the diene was formulated in red natural rubber septa, only transient and low catches were obtained, but when gray halobutyl isoprene elastomeric septa were used, high and consistent catches were obtained for eight weeks. Catches depended on the ratio of (E, E)-8,10 to (E, Z)-8,10 isomers. High catches were obtained for anEE toEZ ratio of 100 ∶ 0.6, and insignificant catches were obtained when the ratio was 100 ∶ 3. Equivalent catches were obtained for dosages of 50, 100, and 200 μg/septum.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01021767
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  • 4
    Electronic Resource
    Electronic Resource
    Blackheaded fireworm: Laboratory and field studies of its sex pheromone (1987)
    Springer
    Journal of chemical ecology 13 (1987), S. 1235-1242 
    Details
    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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