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The Absolute Configuration of the Sex Pheromone of the Citrophilous Mealybug, Pseudococcus calceolariae

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Abstract

The absolute configuration of the sex pheromone of the citrophilous mealybug, Pseudococcus calceolariae, was determined to be (1R,3R)-[2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropyl]methyl (R)-2-acetoxy-3-methylbutanoate. NMR, derivatization reactions, chiral gas chromatography-mass spectrometry, and comparison with synthetic chiral reference compounds, were used to determine the absolute configuration of this compound. This activity of this compound was further confirmed by testing synthetic stereoisomers of the compound as lures in traps for adult male mealybugs. Traps baited with 1,000 μg of the pheromone compound caught 36 times more males than traps baited with virgin females. A mixture of stereoisomers of the pheromone compound can be used for field trapping without adverse effects on trap catch. A comparison with the structures of other sex pheromones of mealybugs is presented.

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Acknowledgements

This work was supported by the Foundation for Research Science and Technology, FRST (Sustainable Integrated Pest Management in Horticulture, C06X0811) and the Fondo Nacional de Desarrollo Científico y Tecnológico (FONDECYT grant 11060527). We thank Tom Sullivan (New Zealand) and Alda Romero (Chile) for maintaining mealybug colonies and Lyn Cole for assistance with the New Zealand field trials. Financial funding from the Linnaeus University, Kalmar, is gratefully acknowledged.

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Authors and Affiliations

  1. The New Zealand Institute for Plant & Food Research Ltd, Canterbury Research Centre, Lincoln, 7608, New Zealand

    C. Rikard Unelius, Ashraf M. El-Sayed & Andrew Twidle

  2. School of Natural Sciences, Linnaeus University, SE-391 82, Kalmar, Sweden

    C. Rikard Unelius

  3. The New Zealand Institute for Plant & Food Research Ltd, Tennent Drive, Palmerston North, 4474, New Zealand

    Barry Bunn

  4. Facultad de Agronomía e Ingeniería Forestal, Pontificia Universidad Católica de Chile, Santiago, Chile

    Tania Zaviezo

  5. Instituto de Química, Pontificia Universidad Católica de Valparaíso, Valparaíso, Chile

    M. Fernanda Flores & Jan Bergmann

  6. The New Zealand Institute for Plant & Food Research Ltd, Havelock North, Hastings, 4157, New Zealand

    Vaughn Bell

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  1. C. Rikard Unelius
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  2. Ashraf M. El-Sayed
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  3. Andrew Twidle
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  4. Barry Bunn
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  5. Tania Zaviezo
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  8. Jan Bergmann
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Correspondence to C. Rikard Unelius.

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Unelius, C.R., El-Sayed, A.M., Twidle, A. et al. The Absolute Configuration of the Sex Pheromone of the Citrophilous Mealybug, Pseudococcus calceolariae . J Chem Ecol 37, 166–172 (2011). https://doi.org/10.1007/s10886-010-9904-1

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  • DOI: https://doi.org/10.1007/s10886-010-9904-1

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