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Sex Attractant Pheromone from the Rice Stalk Stink Bug, Tibraca limbativentris Stal

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Abstract

The male-produced sex pheromone from the Brazilian rice stalk stink bug Tibraca limbativentris is reported. Olfactometer bioassays with sexually mature males and females showed that males attracted females, which suggests that males release a sex pheromone. Males were not attracted to either sex, nor were females attractive to conspecific females. Attraction of the females to males was highest at night. The headspace volatiles collected from male and female bugs were analyzed by gas chromatography (GC) and GC–mass spectrometry. Two male-specific compounds were identified as isomers of 1′S-zingiberenol, whereas a series of defensive compounds were identified in extracts from both sexes. Zingiberenol has three chiral centers, and the nonselective syntheses used produced two groups of isomers, zingiberenol I containing four isomers, namely (1RS,4RS,1′R)-4-(1′,5′-dimethylhex-4′-enyl)-1-methylcyclohex-2-en-1-ol, and zingiberenol II containing the other four isomers, namely (1RS,4RS,1′S)-4-(1′,5′-dimethylhex-4′-enyl)-1-methylcyclohex-2-en-1-ol. Both groups of stereoisomers were more attractive than hexane controls. The absolute configuration of the insect-produced pheromonal components remains to be elucidated, but the 1′S stereochemistry was established for at least one of the isomers.

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Acknowledgments

We thank Hélio Moreira dos Santos and Diva Tiburcio for helping with field collecting and laboratory rearing the insects used in this study. This work received financial support from CNPq and Embrapa, and a Rothamsted International Fellowship to MCBM. Rothamsted Research receives grant-aided support from the Biotechnology and Biological Sciences Research Council of the United Kingdom. This research was, also, supported by the International Foundation for Science, Stockholm, Sweden, through a grant to Maria Carolina Blassioli Moraes.

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Authors and Affiliations

  1. Embrapa Genetic Resources and Biotechnology, Cx. Postal: 02372, Cep.: 70849-970, Brasília, DF, Brazil

    Miguel Borges, Raul A. Laumann & Maria C. B. Moraes

  2. USDA-ARS Chemicals Affecting Insect Behavior Laboratory, BARC-West, B-007, Room 301, 10300 Baltimore Avenue, Beltsville, MD, 20705, USA

    Jeffrey R. Aldrich & James E. Oliver

  3. Biological Chemistry Division, Rothamsted Research, Harpenden, Herts, AL5 2JQ, UK

    Michael Birkett & John A. Pickett

  4. Fuji Flavor Co. Ltd., 3-5-8 Midorigaoka, Hamura City, Tokyo, 205-8503, Japan

    Mitsuo Chiba & Yasuhiro Murata

  5. Embrapa Rice and Beans, Cx. Postal: 179, Cep.: 75375-000, Goiânia, GO, Brazil

    José Alexandre Barrigossi

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  1. Miguel Borges
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  2. Michael Birkett
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  3. Jeffrey R. Aldrich
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  10. Maria C. B. Moraes
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Correspondence to Miguel Borges.

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Borges, M., Birkett, M., Aldrich, J.R. et al. Sex Attractant Pheromone from the Rice Stalk Stink Bug, Tibraca limbativentris Stal. J Chem Ecol 32, 2749–2761 (2006). https://doi.org/10.1007/s10886-006-9197-6

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