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Identification, Synthesis, and Field Testing of the Sex Pheromone of the Citrus Leafminer, Phyllocnistis citrella

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Abstract

The citrus leafminer is an important vector of citrus canker in many of the major citrus production areas of the world. (7Z,11Z)-Hexadecadienal was reported as a sex attractant for this insect in the 1980s, based on trap catches during pheromone screening trials in Japan. However, attempts to reproduce this work in other areas of the world have not been successful. We report here that (7Z,11Z)-hexadecadienal is only one component of the pheromone, with the other critical component being the analogous trienal, (7Z,11Z,13E)-hexadecatrienal. Both compounds were identified in the effluvia from live female moths by coupled gas chromatography (GC)-electroantennography using nonpolar and polar GC columns, and the identifications were confirmed by comparisons of mass spectra with those of authentic standards. Stereoisomers of the two compounds, and a number of analogs, were synthesized to confirm the identifications. In field trials, neither compound alone was attractive to male moths, but blends of the two were highly attractive, with thousands of insects being caught per trial. Addition of the isomeric (7Z,11Z,13Z)-hexadecatrienal inhibited attraction to the two-component blend.

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Acknowledgments

We thank Mariana Krugner for technical assistance, and the Citrus Research Board of California for financial support for this project.

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Authors and Affiliations

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

    Jardel A. Moreira, J. Steven McElfresh & Jocelyn G. Millar

Authors
  1. Jardel A. Moreira
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  2. J. Steven McElfresh
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  3. Jocelyn G. Millar
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Correspondence to Jocelyn G. Millar.

Additional information

This paper and the preceding paper (Leal et al.) were submitted within a few days of each other. The editors and the authors agreed that they should be published in tandem.

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Moreira, J.A., McElfresh, J.S. & Millar, J.G. Identification, Synthesis, and Field Testing of the Sex Pheromone of the Citrus Leafminer, Phyllocnistis citrella. J Chem Ecol 32, 169–194 (2006). https://doi.org/10.1007/s10886-006-9359-6

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  • DOI: https://doi.org/10.1007/s10886-006-9359-6

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