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Pheromone of the elm bark beetle Scolytus laevis (Coleoptera: Scolytidae): stereoisomers of 4-methyl-3-heptanol reduce interspecific competition

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Author

  • Olle Anderbrant
  • Donald S. Matteson
  • C. Rikard Unelius
  • Philip S. Pharazyn
  • Ellen M. Santangelo
  • Fredrik Schlyter
  • Göran Birgersson

Summary, in English

Stereoisomers of 4-methyl-3-heptanol (MH) are pheromone components of several Scolytus bark beetles. The elm bark beetle Scolytus laevis (Coleoptera: Scolytidae) has in previous studies been caught in traps baited with commercial MH containing all four stereoisomers, but the lure has been considered a weak attractant. In this study, we addressed the question whether stereospecific responses by S. laevis to stereoisomers of MH might contribute to its niche separation from other sympatric Scolytus species. Using GC-MS, we analyzed extracts of hindguts and abdomens from male and female S. laevis and the sympatric S. triarmatus. We also tested all four MH-stereoisomers individually and in combinations in the field to determine their role for S. laevis. All four stereoisomers were synthesized via a boronic ester method with 1,2-dicyclohexylethanediol as chiral director. In addition, the (3S,4R)-stereoisomer of MH was prepared through enantioselective, lipase-mediated transesterification of a mixture of the four stereoisomers of MH. Females of both species contained small amounts of syn-MH, and males contained trace amounts of anti-MH. The anti stereoisomer (3R,4S)-MH was attractive to male and female S. laevis, whereas the syn stereoisomer (3S,4S)-MH acted as an inhibitor or deterrent and reduced the catch when added to the attractive isomer. The syn isomer is the main aggregation pheromone component of the larger and sympatric S. scolytus and possibly also of S. triarmatus. The avoidance response of S. laevis to the (3S,4S)-stereoisomer may reduce interspecific competition for host trees.

Publishing year

2010

Language

English

Pages

179-187

Publication/Series

Chemoecology

Volume

20

Issue

3

Document type

Journal article

Publisher

Birkhäuser Verlag

Topic

  • Biological Sciences
  • Zoology

Keywords

  • Attractant
  • Semiochemical
  • Chemical analysis
  • Synthesis
  • triarmatus
  • Scolytus
  • Dutch elm disease

Status

Published

Project

  • Olfaction in bark beetles

Research group

  • Pheromone Group

ISBN/ISSN/Other

  • ISSN: 1423-0445