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Structure-activity relationships of benzoic acid derivates as antifeedants for the pine weevil Hylobius abietis
Dalarna University, School of Technology and Business Studies, Wood Technology.
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2006 (English)In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 32, no 10, p. 2191-2203Article in journal (Refereed) Published
Abstract [en]

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.

Place, publisher, year, edition, pages
Springer , 2006. Vol. 32, no 10, p. 2191-2203
Keywords [en]
Benzoate, Bioassay, Curculionidae, Deterrent, Feces, Feeding, Isopropyl 2, 4-dimethoxybenzoate, Methyl 2, 4-dimethoxybenzoate, Phenylacetate, Reforestation, Seedling protection
Identifiers
URN: urn:nbn:se:du-1902OAI: oai:dalea.du.se:1902DiVA, id: diva2:519637
Available from: 2006-03-07 Created: 2006-03-07 Last updated: 2017-12-07Bibliographically approved

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CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • chicago-author-date
  • chicago-note-bibliography
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf