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Identification and Synthesis of the Male-produced Sex Pheromone of the Stink Bug, Pellaea stictica

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Abstract

Stink bugs are major pests of a wide variety of agricultural crops worldwide. The species Pellaea stictica is a Neotropical stink bug found in several South American countries. Chromatographic analyses of volatiles released by adults of this species showed that males produce a sex-specific compound, and bioassays with a Y-tube olfactometer showed that the compound was attractive only to females, confirming that it is a sex pheromone. Gas chromatography coupled to mass spectrometry and Fourier transform infrared analyses of the natural compound and several derivatives suggested that the structure was an alcohol with a saturated carbon chain and several methyl branches. After synthesis of two proposed structures, the pheromone of P. stictica was identified as a novel compound, 2,4,8,13-tetramethyltetradecan-1-ol. Laboratory bioassays showed that the synthesized mixture of stereoisomers of 2,4,8,13-tetramethyltetradecan-1-ol was as attractive to P. stictica females as the natural pheromone.

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Acknowledgments

We thank Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq, Brazil) and Instituto Nacional de Ciências e Tecnologia de Semioquímicos na Agricultura for supporting our research.

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Authors and Affiliations

  1. Departamento de Química, Universidade Federal do Paraná, CP 19081, CEP 81531-990, Curitiba, PR, Brazil

    Carla F. Fávaro & Paulo H. G. Zarbin

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

    Jocelyn G. Millar

Authors
  1. Carla F. Fávaro
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  2. Jocelyn G. Millar
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  3. Paulo H. G. Zarbin
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Corresponding author

Correspondence to Paulo H. G. Zarbin.

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Fávaro, C.F., Millar, J.G. & Zarbin, P.H.G. Identification and Synthesis of the Male-produced Sex Pheromone of the Stink Bug, Pellaea stictica . J Chem Ecol 41, 859–868 (2015). https://doi.org/10.1007/s10886-015-0621-7

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  • DOI: https://doi.org/10.1007/s10886-015-0621-7

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