(R)-desmolactone, a female-produced sex pheromone component of the cerambycid beetle Desmocerus californicus californicus (subfamily Lepturinae)

Abstract

We report the identification, synthesis, and field bioassays of a female-produced sex attractant pheromone for the cerambycid beetle Desmocerus californicus californicus Horn. Headspace volatiles from females contained a sex-specific compound, (R)-desmolactone [(4R,9Z)-hexadec-9-en-4-olide], which elicited strong responses from the antennae of adult males in coupled gas chromatography-electroantennogram analyses. Short syntheses of both enantiomers were developed from commercial chiral synthons. In field bioassays, significant numbers of males were collected in traps baited with (R)-desmolactone, whereas the (S)-enantiomer attracted no males. The racemate was less attractive than the pure (R)-enantiomer, indicating some degree of antagonism by the unnatural enantiomer. This compound is the first example of a new structural class of cerambycid pheromones, and is the second pheromone identified for a species in the subfamily Lepturinae.