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

Methyl-substituted analogs of (Z)-5-decenyl acetate, a pheromone 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,...

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Bibliographic Details
Published in:Journal of chemical ecology 1992-04, Vol.18 (4), p.637-657
Main Authors: Jonsson, S. (University of Lund, Lund, Sweden), Liljefors, T, Hansson, B.S
Format: Article
Language:English
Subjects:
AGROTIS SEGETUM
Biochemistry. Physiology. Immunology
Biological and medical sciences
CONTROL DE INSECTOS
DOSAGE BIOLOGIQUE
ENSAYO BIOLOGICO
FEROMONAS
Fundamental and applied biological sciences. Psychology
Insecta
Invertebrates
Lepidoptera
LUTTE ANTIINSECTE
Noctuidae
PHEROMONE
Physiology. Development
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Summary:Methyl-substituted analogs of (Z)-5-decenyl acetate, a pheromone 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
ISSN:0098-0331
1573-1561
DOI:10.1007/BF00987825