Alkyl substitution in terminal chain of (Z)-5-decenyl acetate, a pheromone 
component of turnip moth, Agrotis segetum. Synthesis, single-sensillum 
recordings, and structure-activity relationships

Jönsson, S.; Liljefors, T.; Hansson, B. S.

doi:10.1007/bf00994425

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Alkyl substitution in terminal chain of (Z)-5-decenyl acetate, a pheromone component of turnip moth, Agrotis segetum. Synthesis, single-sensillum recordings, and structure-activity relationships

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Jönsson, S., Liljefors, T., & Hansson, B. S. (1991). Alkyl substitution in terminal chain of (Z)-5-decenyl acetate, a pheromone component of turnip moth, Agrotis segetum. Synthesis, single-sensillum recordings, and structure-activity relationships. Journal of Chemical Ecology, 17(1), 103-122. doi:10.1007/bf00994425.

Cite as: https://hdl.handle.net/11858/00-001M-0000-0014-5E48-F

Abstract

Structure-activity relationships for 6-, 7-, 8-, and 9-alkyl substituted analogs of (Z)-5-decenyl acetate, a pheromone component of the turnip moth, Agrotis segetum, have been studied by electrophysiological single-sensillum recordings, and interpreted in terms of a receptor-interaction model. The compounds were prepared by alkenyl cuprate reactions with alpha,beta-unsaturated carbonyl derivatives or alkyl halides. The electrophysiological results indicate steric repulsive interactions between the alkyl groups and the receptor in all the positions studied. This demonstrates a high complementarity between the receptor and the terminal alkyl chain.