Ketone components in the contact sex pheromone of the white-spotted longicorn beetle, Anoplophora malasiaca, and pheromonal activity of synthetic ketones

Two active fractions were found during the isolation of contact sex pheromone of female elytra of the white-spotted longicorn beetle, Anoplophora malasiaca ( Thomson) ( Coleoptera: Cerambycidae), in addition to fraction of hydrocarbons that had previously been identified. One fraction was essential to evoke a series of precopulatory behaviors of males toward a glass dummy when coated together with the hydrocarbon blend. The other fraction enhanced this activity when added to the mixture. From the latter synergistic fraction, we isolated five novel compounds and identified them as 10-heptacosanone, (Z)-18-heptacosen-10-one, (18 Z,21 Z)-heptacosa-18,21-dien-10-one, (18 Z,21 Z,24 Z)-heptacosa- 18,21,24-trien-10-one, and 12-heptacosanone by GC-MS and NMR analyses. A blend of four of these synthetic ketones, without 12-heptacosanone, in the ratio and concentration found in female elytra extract (250 : 400 : 1000 : 180 ng FE-1) showed greater synergistic effect than the natural fraction containing the ketones. This effect was canceled out by further addition of 12-heptacosanone (100 ng FE-1), which was still comparable to the effect of the natural ketone fraction.