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(2,3,4,4-Tetramethylcyclopentyl)Methyl Acetate, a Sex Pheromone from the Obscure Mealybug: First Example of a New Structural Class of Monoterpenes

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Abstract

The sex pheromone of the obscure mealybug, Pseudococcus viburni, consists of (1R*,2R*,3S*)-(2,3,4,4-tetramethylcyclopentyl)methyl acetate, the first example of a new monoterpenoid structural motif in which the two isoprene units forming the carbon skeleton are joined by 2′–2 and 3′–4 connections rather than the usual 1′–4, head-to-tail connections. This highly irregular terpenoid structure, and the irregular terpenoid structures of related mealybug species, suggest that these insects may have unique terpenoid biosynthetic pathways.

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Notes

  1. A recent report (Lavoine-Hannegalle and Casabianca, 2004) suggested that 1,1,2,3-tetramethyl-4-hydroxymethyl-2-cyclopentene might be present as a trace component of lavender oil. However, the identification was based solely on interpretation of a mass spectrum and must be regarded as tentative at best, pending isolation and unequivocal identification by other spectral methods.

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Acknowledgments

This project was funded by the USDA Western Regional IPM Program, the Viticulture Consortium, the California Table Grape Commission, and the California Raisin Marketing Board. We thank Monica Cooper for carrying out the bioassay.

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Authors and Affiliations

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

    Jocelyn G. Millar & J. Steven McElfresh

  2. Department of Plant Pathology, University of California, Riverside, CA, 92521, USA

    Sharon L. Midland

  3. Department of Environmental Science, Policy, and Management, Division of Insect Biology, University of California, Berkeley, CA, 94720, USA

    Kent M. Daane

Authors
  1. Jocelyn G. Millar
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  2. Sharon L. Midland
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  3. J. Steven McElfresh
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  4. Kent M. Daane
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Correspondence to Jocelyn G. Millar.

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†Deceased

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Millar, J.G., Midland, S.L., McElfresh, J.S. et al. (2,3,4,4-Tetramethylcyclopentyl)Methyl Acetate, a Sex Pheromone from the Obscure Mealybug: First Example of a New Structural Class of Monoterpenes. J Chem Ecol 31, 2999–3005 (2005). https://doi.org/10.1007/s10886-005-9320-0

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  • DOI: https://doi.org/10.1007/s10886-005-9320-0

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