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Structure–Activity Relationships of Phenylpropanoids as Antifeedants for the Pine Weevil Hylobius abietis

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Abstract

Ethyl cinnamate has been isolated from the bark of Pinus contorta in the search for antifeedants for the pine weevil, Hylobius abietis. Based on this lead compound, a number of structurally related compounds were synthesized and tested. The usability of the Topliss scheme, a flow diagram previously used in numerous structure–activity relationship (SAR) studies, was evaluated in an attempt to find the most potent antifeedants. The scheme was initially followed stepwise; subsequently, all compounds found in the scheme were compared. In total, 51 phenylpropanoids were tested and analyzed for SARs by using arguments from the field of medicinal chemistry (rational drug design). Individual Hansch parameters based on hydrophobicity, steric, and electronic properties were examined. The effects of position and numbers of substituents on the aromatic ring, the effects of conjugation in the molecules, and the effects of the properties of the parent alcohol part of the esters were also evaluated. It proved difficult to find strong SARs derived from single physicochemical descriptors, but our study led to numerous new, potent, phenylpropanoid antifeedants for the pine weevil. Among the most potent were methyl 3-phenylpropanoates monosubstituted with chloro, fluoro, or methyl groups and the 3,4-dichlorinated methyl 3-phenylpropanoate.

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Acknowledgments

We thank The Swedish Research Council for Environment, Agricultural Sciences and Spatial Planning, The Swedish Hylobius Research Program, and The University of Kalmar for supporting this study. Henning Henschel, Abtin Daghigi, Meral Sari, Veronica Siljehav, Konstantin Dubrovinski, Tonja Freisolt, and Magnus Besev were helpful in the syntheses of the test compounds and Claes Hellqvist in processing the bioassay data.

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Authors and Affiliations

  1. School of Pure and Applied Natural Sciences, University of Kalmar, SE-391 82, Kalmar, Sweden

    B. Bohman & C. R. Unelius

  2. Department of Ecology, Swedish University of Agricultural Sciences, P.O. Box 7044, SE-750 07, Uppsala, Sweden

    G. Nordlander & H. Nordenhem

  3. Department of Natural Sciences, Mid Sweden University, SE-851 70, Sundsvall, Sweden

    K. Sunnerheim

  4. KTH Chemistry, Organic Chemistry, Ecological Chemistry Group, Royal Institute of Technology, SE-100 44, Stockholm, Sweden

    A.-K. Borg-Karlson

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  1. B. Bohman
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  2. G. Nordlander
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  3. H. Nordenhem
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  4. K. Sunnerheim
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  5. A.-K. Borg-Karlson
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  6. C. R. Unelius
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Correspondence to C. R. Unelius.

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Bohman, B., Nordlander, G., Nordenhem, H. et al. Structure–Activity Relationships of Phenylpropanoids as Antifeedants for the Pine Weevil Hylobius abietis . J Chem Ecol 34, 339–352 (2008). https://doi.org/10.1007/s10886-008-9435-1

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  • DOI: https://doi.org/10.1007/s10886-008-9435-1

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