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

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