The identification of 4-methyl-3-heptanone from Scolytus scolytus (F.) and S. multistriatus (Marsham). Absolute configuration, laboratory bioassay and electrophysiological studies on S. scolytus

Add time:09/05/2019    Source:sciencedirect.com

The identification of (4S)-4-methyl-3-heptanone among the volatiles produced when male Scolytus scolytus bore into four species of Ulmus is described. The quantity of 4-methyl-3-heptanone found in extracts of volatiles was 12–32% of the total amount of 4-methyl-3-heptanol present.From gas chromatographic analysis and a coupled gas chromatography-single cell recording technique, evidence was also obtained for the production of 4-methyl-3-heptanone by female S. multistriatus boring in two Ulmus species. These are the first reports of 4-methyl-3-heptanone from the order Coleoptera.Electrophysiological studies (electroantennogram and single cell recordings) and a laboratory walking bioassay indicated that (±)-4-methyl-3-heptanone is biologically active towards S. scolytus. Eleven per cent of the olfactory cells recorded from the antennae of male and female S. scolytus responded preferentially to (±)-4-methyl-3-heptanone at low stimulus concentrations. In the laboratory bioassay, addition of specific concentrations of this substance to a mixture of 4-methyl-3-heptanol and (−)-α-cubebene modified the type of response given by both sexes, but a significant increase in the overall response was shown only by female beetles.

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