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.

Keywords

antifeedant; pine weevil; Hylobius abietis; structure-activity; SAR; phenylpropanoid; phenylpropanoate; phenylacrylate

Published in

Journal of Chemical Ecology
2008, Volume: 34, number: 3, pages: 339-352
Publisher: SPRINGER

SLU Authors

• Nordlander, Göran

  • Department of Ecology, Swedish University of Agricultural Sciences
    

• Nordenhem, Henrik

  • Department of Ecology, Swedish University of Agricultural Sciences
    

UKÄ Subject classification

Environmental Sciences related to Agriculture and Land-use
Forest Science


Publication identifier

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

Permanent link to this page (URI)

https://res.slu.se/id/publ/18547