Introduction of methyl groups to acetate substituted 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/bf00987825

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Introduction of methyl groups to acetate substituted 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. (1992). Introduction of methyl groups to acetate substituted 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, 18(4), 637-657. doi:10.1007/bf00987825.

Cite as: https://hdl.handle.net/11858/00-001M-0000-0014-5E42-C

Abstract

Methyl-substituted analogs of (Z)-5-decenyl acetate, a phermone component of the turnip moth, Agrotis segetum, have been synthesized and studied by electrophysiological single-sensillum recordings and molecular mechanics calculations [MM2(85)]. The analogs are monomethyl substituted in the 2, 3, 4, and 5 positions and geminally dimethyl substituted in the 2, 3, and 4 positions. The methyl groups have been employed as space probes to study the degree of steric complementarity between the acetate-substituted alkyl chain of the pheromone component and its receptor. The electrophysiological activities, interpreted in terms of a receptor interaction model, indicate significant steric repulsive interactions between the introduced methyl groups and the receptor. This implies a high degree of complementarity between the acetate-substituted alkyl chain of the natural pheromone component and its receptor.