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

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.

2,3-Hexanediols as sex attractants and a female-produced sex pheromone for cerambycid beetles in the prionine genus Tragosoma.

Recent work suggests that closely related cerambycid species often share pheromone components, or even produce pheromone blends of identical composition. However, little is known of the pheromones of species in the subfamily Prioninae. During field bioassays in California, males of three species in the prionine genus Tragosoma were attracted to 2,3-hexanediols, common components of male-produced aggregation pheromones of beetles in the subfamily Cerambycinae. We report here that the female-produced sex pheromone of Tragosoma depsarium "sp. nov. Laplante" is (2R,3R)-2,3-hexanediol, and provide evidence from field bioassays and electroantennography that the female-produced pheromone of both Tragosoma pilosicorne Casey and T. depsarium "harrisi" LeConte may be (2S,3R)-2,3-hexanediol. Sexual dimorphism in the sculpting of the prothorax suggests that the pheromone glands are located in the prothorax of females. This is the second sex attractant pheromone structure identified from the subfamily Prioninae, and our results provide further evidence of pheromonal parsimony within the Cerambycidae, in this case extending across both subfamily and gender lines.

cis-Vaccenyl acetate, a female-produced sex pheromone component of Ortholeptura valida, a longhorned beetle in the subfamily Lepturinae.

We report the identification, synthesis, and field bioassays of a female-produced sex attractant pheromone component of the cerambycid beetle Ortholeptura valida (LeConte). Headspace volatiles from females contained a female-specific compound, (Z)-11-octadecen-1-yl acetate, which elicited a strong response from antennae of adult males in coupled gas chromatography-electroantennogram analyses. In field bioassays, significant numbers of males were collected by traps baited with this compound. The pheromone represents a new structural class of cerambycid pheromones, and is the first pheromone identified for a cerambycid species in the subfamily Lepturinae.