M. T. Smith’s research while affiliated with Oklahoma State University and other places

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.

Electroantennogram (EAG) measurements 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. RÉSUMÉ Etude par électroantennographie et avec tunnel de vol des constituants potentiels des phéromones sexuelles Cydia caryana ( Lépidoptère, Tortricidae, Olethreutinae ). 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‐ dudodecadien‐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‐l***‐ol ressemblent (ou sont) les constituants de la phéromone sexuelle de C. caryana; tandis que les ( Z )‐8‐dodecen‐l***‐ol et ( E )‐10‐dodecen‐l***‐ol sont, soit des paraphéromones, soit des constituants mineurs de la phéromone. La signification biologique du ( Z )‐12‐tétradécen‐l***‐ol a été difficile à interprêter avec les expériences en tunnel de vol.