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

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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.

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Acknowledgments

We thank Peter Reagel, Elizabeth Graham, Joseph Wong, Becca Striman, and Ken Robinson for assistance in field bioassays, Judith Mongold-Diers for assistance in laboratory assays, and the Allerton Park and Retreat Center and the Vermilion County Conservation district for access to field sites. This research was supported by a grant from the Alphawood Foundation, and the United States Department of Agriculture (USDA-NRI Grant number 2009-35302-05047 and USDA-APHIS-PPQ Grant number 10-8100-1422-CA, to LMH and JGM), and was in partial fulfillment of a doctoral degree for RFM from the University of Illinois at Urbana-Champaign.

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  1. Robert F. Mitchell

    Present address: Center for Insect Science, University of Arizona, Tucson, AZ, 85721, USA

Authors and Affiliations

  1. Department of Entomology, University of Illinois at Urbana-Champaign, Urbana, IL, 61801, USA

    Robert F. Mitchell & Lawrence M. Hanks

  2. Department of Entomology, University of California, Riverside, CA, 92521, USA

    Jocelyn G. Millar

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  1. Robert F. Mitchell
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  2. Jocelyn G. Millar
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  3. Lawrence M. Hanks
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Correspondence to Robert F. Mitchell.

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Mitchell, R.F., Millar, J.G. & Hanks, L.M. Blends of (R)-3-hydroxyhexan-2-one and alkan-2-ones identified as potential pheromones produced by three species of cerambycid beetles. Chemoecology 23, 121–127 (2013). https://doi.org/10.1007/s00049-012-0122-x

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