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(2E,6Z,9Z)-2,6,9-Pentadecatrienal as a Male-Produced Aggregation-Sex Pheromone of the Cerambycid Beetle Elaphidion mucronatum

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Abstract

An increasing body of evidence suggests that the volatile pheromones of cerambycid beetles are much more diverse in structure than previously hypothesized. Here, we describe the identification, synthesis, and field testing of (2E,6Z,9Z)-2,6,9-pentadecatrienal as a male-produced aggregation-sex pheromone of the cerambycid Elaphidion mucronatum (Say) (subfamily Cerambycinae, tribe Elaphidiini). This novel structure is unlike any previously described cerambycid pheromone, and in field bioassays attracted only this species. Males produced about 9 μg of pheromone per 24 h period, and, in field trials, lures loaded with 10, 25, and 100 mg of synthetic pheromone attracted beetles of both sexes, whereas lures loaded with 1 mg of pheromone or less were not significantly attractive. Other typical cerambycine pheromones such as 3-hydroxy-2-hexanone, syn-2,3-hexanediol, and anti-2,3-hexanediol were not attractive to E. mucronatum, and when combined with (2E,6Z,9Z)-2,6,9-pentadecatrienal, the former two compounds appeared to inhibit attraction. Unexpectedly, adults of the cerambycine Xylotrechus colonus (F.) were attracted in significant numbers to a blend of 3-hydroxyhexan-2-one and (2E,6Z,9Z)-2,6,9-pentadecatrienal, even though there is no evidence that this species produces the latter compound. From timed pheromone trap catches, adults of E. mucronatum were determined to be active from dusk until shortly after midnight.

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Acknowledgements

We thank Kate Johnson for technical assistance in the field, and Steve Buck and James Ellis of the University of Illinois Committee on Natural Areas for access to field sites. JGM thanks Lars Skattebǿl (Dept. of Chemistry, University of Oslo) for the gift of a sample of (2E,6Z,9Z,12Z)-2,6,9,12-pentadecatetraenol. We appreciate funding support from The Alphawood Foundation of Chicago (to LMH) and from the USDA National Institute of Food and Agriculture (award # 2015-67013-23173 to LMH and JGM).

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  1. Robert F. Mitchell

    Present address: Department of Biology, University of Wisconsin Oshkosh, Oshkosh, WI, 54901, USA

Authors and Affiliations

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

    Jocelyn G. Millar

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

    Robert F. Mitchell, Linnea R. Meier, Todd D. Johnson, Judith A. Mongold-Diers & Lawrence M. Hanks

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  1. Jocelyn G. Millar
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Correspondence to Jocelyn G. Millar.

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Millar, J.G., Mitchell, R.F., Meier, L.R. et al. (2E,6Z,9Z)-2,6,9-Pentadecatrienal as a Male-Produced Aggregation-Sex Pheromone of the Cerambycid Beetle Elaphidion mucronatum . J Chem Ecol 43, 1056–1065 (2017). https://doi.org/10.1007/s10886-017-0905-1

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