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The Male-produced Sex Pheromone of the True Bug, Phthia picta, is an Unusual Hydrocarbon

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Abstract

Phthia picta is part of a complex of true bugs (Heteroptera) in Brazil that attack tomatoes, being particularly damaging because nymphs and adults feed on both leaves and fruit. Gas chromatography (GC) of aeration extracts of adult males vs. females revealed the presence of a male-specific compound. GC-electroantennographic detector experiments indicated that the antennae of females are highly sensitive to this male-specific compound. GC-mass spectrometry and GC-FTIR analyses suggested a methyl branched hydrocarbon structure for this compound. After synthesis of three different proposed structures, the natural product was indentified as 5,9,17-trimethylhenicosane, which was strongly attractive to females in Y-tube olfactometer bioassays. Analysis of dissected body parts of adults revealed that the pheromone is produced in the lateral accessory glands of the metathoracic scent gland of males only.

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Acknowledgments

We thank the Empresa Paranaense de Assistência Técnica Extensão Rural, EMATER – Uraí, PR, Brazil. Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES - Brazil) and Instituto Nacional de Ciências e Tecnologia de Semioquímicos na Agricultura for supporting our research. PHGZ thanks Prof. Dr. Jocelyn G. Millar (UC-Riverside) for discussions on the mass spectra. We are also grateful to Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) for funding the visit of Dr. Jeffrey R. Aldrich to the Federal University of Paraná (visiting researcher; proc.: 401604/2009-8).

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Authors and Affiliations

  1. Departamento de Química, Universidade Federal do Paraná, CP 19081, 81531-980, Curitiba-PR, Brazil

    Rafael A. Soldi, Mauro A. C. M. Rodrigues & Paulo H. G. Zarbin

  2. USDA-ARS, 10300 Baltimore Avenue, Bldg. 007, rm301, BARC-West, Beltsville, MD, 20705, USA

    Jeffrey R. Aldrich

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  1. Rafael A. Soldi
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  2. Mauro A. C. M. Rodrigues
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  3. Jeffrey R. Aldrich
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  4. Paulo H. G. Zarbin
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Correspondence to Paulo H. G. Zarbin.

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Soldi, R.A., Rodrigues, M.A.C.M., Aldrich, J.R. et al. The Male-produced Sex Pheromone of the True Bug, Phthia picta, is an Unusual Hydrocarbon. J Chem Ecol 38, 814–824 (2012). https://doi.org/10.1007/s10886-012-0147-1

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  • DOI: https://doi.org/10.1007/s10886-012-0147-1

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