Canadian Forest Service Publications

Mayo, P.D., Silk, P.J., Abeysekera, D., and Magee, D.I. 2016. Synthesis of three putative kairomones of the beech leaf-mining weevil, Orchestes fagi (L.). Synthetic Communications 46(13): 1124–1132.

Year: 2016

Issued by: Atlantic Forestry Centre

Catalog ID: 39561

Language: English

CFS Availability: PDF (download)

Available from the Journal's Web site.
DOI: 10.1080/00397911.2016.1185126

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Abstract

The beech leaf-mining weevil, Orchestes fagi (L.), also known as the beech flea weevil, is a common and widespread pest of beech, Fagus sylvatica L., in its native Europe. It now appears to be well established in Nova Scotia, Canada. We report a novel synthesis of 9-geranyl-p-cymene and syntheses of 9-geranyl-α-terpinene and 1,1-dimethyl-3-methylene-2-vinylcyclohexane, making partial use of known methods. All three of these compounds are found in beech leaf volatiles and/or wood and are putative kairomones of the beech leaf-mining weevil.

Plain Language Summary

Three different molecules; namely, 9-geranyl-p-cymene, 9-geranyl-alpha-terpinene, and 1,1-dimethyl-3-methylene-2-vinylcyclohexane, were made in the laboratory using conventional synthetic organic chemistry techniques. There was not much previous work in the chemical literature describing how to make these molecules, so this article should be a valuable contribution to the organic chemistry literature. This article documents in detail the synthesis and spectroscopic properties of these molecules. All three of these compounds are found in the volatiles given off by America beech (Fagus grandifolia) leaves, and hence could potentially attract beech leaf-mining weevil, Orchestes fagi (L.). This insect is an alien invasive in Nova Scotia, and methods for its detection and control are being sought. The chemical characterization of molecules given off by the beech tree raises the possibility of designed a plant volatile-based lure for detection of this insect.