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Antifeedants against Hylobius abietis pine weevils: An active compound in extract of bark of Tilia cordata linden
2005 (English)In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 31, no 5, 989-1001 p.Article in journal (Refereed) Published
Abstract [en]

Linden (Tilia cordata) bark was shown to contain an antifeedant effective against the large pine weevil, Hylobius abietis. Soxhlet extraction of inner and outer bark resulted in an extract that showed antifeedant activity in a microfeeding assay. The extract was fractionated by chromatography on silica gel using gradient elution with solvents of increasing polarity. The content of the fractions obtained was monitored by thin layer- and gas chromatography. Fractions of similar chemical composition were merged. Two of the 17 fractions showed antifeedant activity in the microfeeding assay. Nonanoic acid was identified in both of these fractions. Subsequent testing in the microfeeding assay showed that nonanoic acid possessed strong antifeedant activity against H. abietis adults.

Place, publisher, year, edition, pages
2005. Vol. 31, no 5, 989-1001 p.
Keyword [en]
antifeedant, Curculionidae, Coleoptera, deterrent, extract, feeding, fractionation, Hylobius abietis, linden, nonanoic acid, outer bark, pelargonic acid, phloem, pine weevil, soxhlet, Tilia co
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-5598DOI: 10.1007/s10886-005-4243-3ISI: 000230460700002OAI: oai:DiVA.org:kth-5598DiVA: diva2:10016
Note
QC 20110124Available from: 2006-04-11 Created: 2006-04-11 Last updated: 2011-01-24Bibliographically approved
In thesis
1. Isolation, Synthesis and Structure-Activity Relationships of Antifeedants against the Pine Weevil, Hylobius Abietis
Open this publication in new window or tab >>Isolation, Synthesis and Structure-Activity Relationships of Antifeedants against the Pine Weevil, Hylobius Abietis
2006 (English)Doctoral thesis, comprehensive summary (Other scientific)
Abstract [en]

The large pine weevil, Hylobius abietis L., is a major insect pest on conifer seedlings in northern Europe. Due to its feeding newly planted trees get girdled, resulting in high seedling mortality (up to 80%). As a consequence great financial losses to the forest industry occur. Today the seedlings are protected with the pyrethroid insecticide cypermethrin. This insecticide is toxic to aquatic organisms and is, from 2010, prohibited for use in Sweden by the Swedish Chemicals Inspectorate. An alternative to insecticides is to protect the seedlings with antifeedants, compounds that, either through taste or smell or both, deter the weevils from feeding. This thesis describes the search for and the synthesis of such antifeedant compounds.

Bark extracts of several woody species, known to be non-palatable to the weevil, were prepared and found to display antifeedant activity against H. abietis. The major chemical constituents of the extracts were tested for antifeedant activity. Antifeedants such as eugenol, 2-phenylethanol and benzylalcohol, but also feeding stimulants such as β-sitosterol and linoleic acid, were identified. An extract of linden bark, Tilia cordata, was shown to contain nonanoic acid, a highly active antifeedant. Other aliphatic carboxylic acids were also found to display high antifeedant activities against the weevil, both in laboratory and in field tests.

The enantiomers of dihydropinidine, a piperidine alkaloid present in several conifer species, were prepared by dimethylzinc mediated allylation of 2- methyltetrahydropyridine-N-oxide. When tested in micro feeding assays, no difference in antifeedant activity was found for the enantiomers. In a field test high antifeedant activity, comparable with that of the presently used insecticide cypermethrin, was found for (±)-dihydropindine. Other naturally occurring piperidine alkaloids were synthesised and also found to display high antifeedant activities in laboratory tests.

Structure-activity relationships were evaluated for methoxy substituted benzaldehydes, benzoic acids and cinnamic aldehydes, -acids, -esters and -alcohols. While the carboxylic acids were inactive or even feeding stimulants, the aldehydes were the most active antifeedants

Place, publisher, year, edition, pages
Stockholm: KTH, 2006. ix, 53 p.
Series
Trita-IOK, ISSN 1100-7974 ; 2006:101
Keyword
Pine weevil, Hylobius abietis, semiochemicals, antifeedant, feeding deterrent, feeding stimulant, bark extract, carboxylic acid, piperidine alkaloids, structure-activity, cinnamic aldehyde, benzaldehyde
National Category
Organic Chemistry
Identifiers
urn:nbn:se:kth:diva-3919 (URN)91-7178-301-6 (ISBN)
Public defence
2006-04-28, Sal 0102, Åkroken, Mittuniversitetet, Sundsvall, 14:00
Opponent
Supervisors
Note
QC 20110124Available from: 2006-04-11 Created: 2006-04-11 Last updated: 2011-01-24Bibliographically approved

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