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Journal of Chemical Ecology

, 32:1673 | Cite as

(1S)-1-Ethyl-2-Methylpropyl 3,13-Dimethylpentadecanoate: Major Sex Pheromone Component of Paulownia Bagworm, Clania variegata

  • Regine Gries
  • Grigori Khaskin
  • Zhong-Xing Tan
  • Bo-Guang Zhao
  • G. G. Skip King
  • Aleksander Miroshnychenko
  • Guo-Qiang Lin
  • Marc Rhainds
  • Gerhard GriesEmail author
Article

Abstract

The Paulownia bagworm, Clania variegata Snell. (Lepidoptera: Psychidae), is one of the most significant forest defoliators in China. In gas chromatographic (GC)–electroantennographic detection analyses of pheromone gland extracts of female C. variegata on three GC columns (DB-5, DB-23, DB-210), two compounds (A and B) elicited strong responses from male antennae. The more abundant component B was isolated by high-performance liquid chromatography and identified as 1-ethyl-2-methylpropyl 3,13-dimethylpentadecanoate by transesterification, GC-mass spectrometry (MS), and comparison of its spectral and GC retention characteristics with those of synthetic compounds. In field trapping experiments in China, racemic and (1S)-1-ethyl-2-methylpropyl 3,13-dimethylpentadecanoate [but not the (1R)-stereoisomer] attracted male C. variegata. The absolute configuration of B (a molecule with three chiral centers) and the structure of component A remain to be determined.

Keywords

Paulownia bagworm Clania variegata Psychidae Sex pheromone 1-Ethyl-2-methylpropyl 3,13-dimethylpentadecanoate 

Notes

Acknowledgments

We thank Keith N. Slessor and Jianxiong Li for provision of laboratory space and contributions at a very early stage of this project, Sadao Wakamura for a reference sample, Eberhard Kiehlmann for constructive comments and critical review of the manuscript, Mei-Keng Yang for elemental analyses, Derek Vance Steel, Sharon Oliver, and Renee Picard for word processing, and Bob Birtch for graphical illustrations. The research was supported by grants from the Natural Science Foundation of China (Nos. 333917041 and 39670613), a grant from the China Ministry of Forestry (948 project, 2005-4-19), a Discovery grant from the Natural Sciences and Engineering Research Council of Canada (NSERC) to G.G., and by a NSERC-Industrial Research Chair to G.G. with Phero Tech Inc., SC Johnson Canada, and Global Forest as industrial sponsors.

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Copyright information

© Springer Science + Business Media, Inc. 2006

Authors and Affiliations

  • Regine Gries
    • 1
  • Grigori Khaskin
    • 1
  • Zhong-Xing Tan
    • 2
  • Bo-Guang Zhao
    • 3
  • G. G. Skip King
    • 1
  • Aleksander Miroshnychenko
    • 1
  • Guo-Qiang Lin
    • 2
  • Marc Rhainds
    • 1
    • 4
  • Gerhard Gries
    • 1
    Email author
  1. 1.Department of Biological SciencesSimon Fraser UniversityBurnabyCanada
  2. 2.Shanghai Institute of Organic ChemistryChinese Academy of SciencesShanghaiPeople's Republic of China
  3. 3.Department of Forest ProtectionNanjing Forestry UniversityNanjingPeople's Republic of China
  4. 4.Centre de Recherche en Horticulture, Pavillon de l'EnvirotronUniversité LavalQuébecCanada

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