Journal of Chemical Ecology

, Volume 45, Issue 4, pp 339–347 | Cite as

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

  • R. Maxwell CollignonEmail author
  • Sean Halloran
  • Jacqueline M. Serrano
  • J. Steven McElfresh
  • Jocelyn G. Millar


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.


Cerambycidae Aggregation-sex pheromone Male-produced pheromone Terpenoid p-Mentha-1,3-dien-8-ol α,α,4-Trimethyl-1,3-cyclohexadiene-1-methanol 



We thank Sue Lee and Robert Bonnett for permission to conduct the field experiments at UCR Agricultural Operations, and Dr. Ken Halama for permission to conduct experiments at Emerson Oaks Nature Reserve. We thank Ian Swift for consultation regarding cerambycid biology. We also gratefully acknowledge the financial support for this research provided by the USDA-AFRI-NIFA Predoctoral Fellowship Program to RMC (2016-67011-25097).

Supplementary material

10886_2019_1063_MOESM1_ESM.docx (184 kb)
ESM 1 (DOCX 184 kb)


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© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Department of EntomologyUniversity of CaliforniaRiversideUSA
  2. 2.USDA-ARS, Pacific Basin Ag. Res. CenterHiloUSA

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