A new lavandulol-related monoterpene in the sex pheromone of the grey pineapple mealybug, Dysmicoccus neobrevipes.

The grey pineapple mealybug, Dysmicoccus neobrevipes, is a serious pest that attacks a variety of crops in tropical regions. Recently, it was recorded on an island in southwestern Japan, suggesting that its distribution is expanding. As a measure against this expansion, a monitoring tool is urgently needed. In this study we determined the structure of the sex pheromone of D. neobrevipes in order to develop an efficient lure for monitoring traps. Volatiles collected from virgin adult females were fractionated by high performance liquid chromatography (HPLC) and gas chromatography, and fractions were tested for attractiveness to males in a laboratory bioassay. A single compound was isolated which was as attractive to males as the crude collections, and this was proposed to be the main, if not the only, component of the female-produced sex pheromone. The structure of this was determined to be (E)-2-isopropyl-5-methylhexa-3,5-dienyl acetate by gas chromatography/mass spectrometry and nuclear magnetic resonance analyses. This compound was synthesized through four steps, and the synthetic chemical was as attractive as the natural product in a greenhouse bioassay. The enantiomers of the synthetic acetate were obtained by enantioselective HPLC fractionation of the corresponding alcohols, and the natural pheromone was shown to be the (+)-isomer. The carbon skeleton of this novel compound is related to lavandulol, a monoterpene with an unusual non-head-to-tail connection of isoprene units that is often found in mealybug pheromones.