Blends of (R)-3-hydroxyhexan-2-one and alkan-2-ones identified as potential pheromones produced by three species of cerambycid beetles

Robert F. Mitchell, Jocelyn G. Millar, Lawrence M Hanks

Research output: Contribution to journalArticle

Abstract

We present data indicating that three species of cerambycid beetles (subfamily Cerambycinae) produce the common cerambycine pheromone component (R)-3-hydroxyhexan-2-one as well as an alkan-2-one component, a possible new motif for cerambycid pheromone components. GC/MS analyses of headspace volatiles produced by male beetles indicated that Cyrtophorus verrucosus (Olivier) produced (R)-3-hydroxyhexan-2-one but also nonan-2-one at ~18 % of the hydroxyketone component, whereas Orwellion gibbulum arizonense (Casey) and Parelaphidion aspersum (Haldeman) produced decan-2-one at ~40 and 7 % of the amount of the hydroxyketone, respectively. In field bioassays, adult C. verrucosus were attracted by (R)-3-hydroxyhexan-2-one alone, but attraction was significantly enhanced by nonan-2-one. This effect was lost if the quantity of nonan-2-one exceeded 100 % of the hydroxyketone, suggesting that beetles could discern ratios of the two chemicals and were most strongly attracted to those approximating the blend produced by males. We suggest that nonan-2-one plays a role in the species specificity of the pheromone signal of C. verrucosus, and that decan-2-one plays a similar role in the semiochemical communication of O. g. arizonense and P. aspersum.

Original languageEnglish (US)
Pages (from-to)121-127
Number of pages7
JournalChemoecology
Volume23
Issue number2
DOIs
StatePublished - Jun 1 2013

Fingerprint

Pheromones
Beetles
pheromone
pheromones
beetle
Coleoptera
semiochemical
semiochemicals
Species Specificity
headspace analysis
Bioassay
bioassay
bioassays
Biological Assay
communication
Communication
3-hydroxyhexan-2-one

Keywords

  • Decan-2-one
  • Longhorned beetle
  • Nonan-2-one
  • Reproductive isolation
  • Sex pheromone

ASJC Scopus subject areas

  • Ecology, Evolution, Behavior and Systematics
  • Biochemistry

Cite this

Blends of (R)-3-hydroxyhexan-2-one and alkan-2-ones identified as potential pheromones produced by three species of cerambycid beetles. / Mitchell, Robert F.; Millar, Jocelyn G.; Hanks, Lawrence M.

In: Chemoecology, Vol. 23, No. 2, 01.06.2013, p. 121-127.

Research output: Contribution to journalArticle

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