Monoalkenes as Contact Sex Pheromone Components of the Woodwasp Sirex noctilio

A pheromone on the cuticle of females of the woodwasp Sirex noctilio, a recently introduced pest of pines in North America, induces conspecific males to attempt copulation. Dead females washed with hexane did not elicit copulation attempts from males, whereas reapplication of a female hexane body wash onto the cuticle of dead females elicited copulation attempts by 65% of males tested. Analysis of the hexane extract revealed saturated and unsaturated hydrocarbons as major components of the female cuticle. Behavior-guided fractionation of the female body wash led to the identification of three components, (Z)-7-heptacosene, (Z)-7-nonacosene, and (Z)-9-nonacosene, of the sex pheromone of S. noctilio that elicited copulatory responses from males.