An Unstable Monoterpene Alcohol as a Pheromone Component of the Longhorned Beetle Paranoplium gracile (Coleoptera: Cerambycidae).

We report the identification of p-mentha-1,3-dien-8-ol, an unstable monoterpene alcohol, as a male-produced aggregation-sex pheromone component of the cerambycid beetle Paranoplium gracile (Leconte) (subfamily Cerambycinae, tribe Oemini), a species endemic to California. Headspace volatiles from live males contained a blend of nine cyclic terpenoids that were not detected in analogous samples from females. Volatiles produced by male Eudistenia costipennis Fall, also in the tribe Oemini, contained the same suite of nine compounds. Four compounds, dehydro-p-cymene, p-mentha-1,3-dien-8-ol, p,α,α-trimethylbenzyl alcohol, and an unidentified compound were found to elicit responses from antennae of P. gracile females in coupled gas chromatography-electroantennogram detection (GC-EAD) assays, whereas only p-mentha-1,3-dien-8-ol elicited responses from antennae of males. In field assays, p-mentha-1,3-dien-8-ol stabilized with the antioxidant butylated hydroxytoluene (BHT) attracted P. gracile of both sexes, indicating it functions as an aggregation-sex pheromone, as with other pheromones identified from its subfamily, the Cerambycinae. Adding four of the other compounds found in headspace samples to the dienol lure had no effect on attraction. Because of the instability of p-mentha-1,3-dien-8-ol, it seems likely that at least some of the compounds seen in the extracts of volatiles from both species are artefacts, rather than being components of the pheromone.