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Research article - Peer-reviewed, 2006

Structure-activity relationships of benzoic acid derivatives as antifeedants for the pine weevil, Hylobius abietis

Unelius CR, Nordlander G, Nordenhem H, Hellqvist C, Legrand S, Borg-Karlson AK

Abstract

Aromatic organic compounds found in the feces of the pine weevil, Hylobius abietis (L.) (Coleoptera: Curculionidae), have been shown to deter feeding behavior in this species, which is a serious pest of planted conifer seedlings in Europe. We evaluated 55 benzoic acid derivatives and a few homologs as antifeedants for H. abietis. Structure-activity relationships were identified by bioassaying related compounds obtained by rational syntheses of functional group analogs and structural isomers. We identified five main criteria of efficiency as antifeedants among the benzoic acid derivatives. By predicting optimal structures for H. abietis antifeedants, we attempted to find a commercial antifeedant to protect conifer seedlings against damage by H. abietis in regenerating forests. New, highly effective antifeedants are methyl 2,4-dimethoxybenzoate, isopropyl 2,4-dimethoxybenzoate, methyl 2-hydroxy-3-methoxybenzoate, methyl (3,5-dimethoxyphenyl)acetate, and methyl (2,5-dimethoxyphenyl)acetate. Of these, methyl 2,4-dimethoxybenzoate and isopropyl 2,4-dimethoxybenzoate have the highest antifeedant indices of all substances tested and are the best candidates for practical applications in order to protect planted seedlings in the field

Published in

Journal of Chemical Ecology
2006, Volume: 32, number: 10, pages: 2191-2203
Publisher: SPRINGER

      SLU Authors

      • Nordenhem, Henrik

        • Department of Entomology, Swedish University of Agricultural Sciences
        • Hellqvist, Claes

          • Department of Entomology, Swedish University of Agricultural Sciences

        UKÄ Subject classification

        Forest Science
        Environmental Sciences related to Agriculture and Land-use

        Publication identifier

        DOI: https://doi.org/10.1007/s10886-006-9139-3

        Permanent link to this page (URI)

        https://res.slu.se/id/publ/9154