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Sex pheromone of the pine sawfly Diprion pini (Hymenoptera : Diprionidae): Chemical identification, synthesis and biological activity

Bergström, G. ; Wassgren, A. B. ; Anderbrant, O. LU ; Fägerhag, J. ; Edlund, H. ; Hedenström, E. ; Högberg, H. E. ; Geri, C. ; Auger, M. A. and Varama, M. , et al. (1995) In Experientia 51(4). p.370-380
Abstract

The main component of the sex pheromone secretion of female Diprion pini L. (Hymenoptera: Diprionidae) from insects collected both in Finland and in France has been identified as a threo-3,7-dimethyl-2-tridecanol (8 ng per female) stereoisomer by GC-MS and synthesis. The secretion also contains lower and higher homologues in small amounts (1-4% of the main component). Combined gas chromatographic-electroantennographic detection showed activity in both natural and esterified extracts (acetates and propionates); the esters of the main component gave the largest responses. The acetates and propionates of the eight stereoisomers of 3,7-dimethyl-2-tridecanol were synthesized from enantiomerically highly enriched (>99% ee) building blocks.... (More)

The main component of the sex pheromone secretion of female Diprion pini L. (Hymenoptera: Diprionidae) from insects collected both in Finland and in France has been identified as a threo-3,7-dimethyl-2-tridecanol (8 ng per female) stereoisomer by GC-MS and synthesis. The secretion also contains lower and higher homologues in small amounts (1-4% of the main component). Combined gas chromatographic-electroantennographic detection showed activity in both natural and esterified extracts (acetates and propionates); the esters of the main component gave the largest responses. The acetates and propionates of the eight stereoisomers of 3,7-dimethyl-2-tridecanol were synthesized from enantiomerically highly enriched (>99% ee) building blocks. The stereochemistry of the main component was established to be (2 S,3 R,7 R)-3,7-dimethyl-2-tridecanol by GC analysis of the natural material. It was purified by liquid chromatography prior to the GC analysis of both its pentafluorobenzoates and its isopropylcarbamates on a non-chiral polar column (ECD) and a chiral column (NPD), respectively. Field tests demonstrated that both the acetate and propionate of the main component (100 μg of each applied on cotton roll dispensers) were active in attracting males, with or without the presence of several of the minor compounds. Experiments with smaller amounts of the acetate and the propionate (1 μg in France and 50 μg in Finland) demonstrated that the propionate was more active than the acetate, and that it also caught more males than a blend of the two compounds.

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organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
3,7-dimethyl-2-tridecanol, chiral analysis, chiral synthesis, Diprion pini, lipase, semiochemicals, sex attractant
in
Experientia
volume
51
issue
4
pages
11 pages
publisher
Birkhäuser
external identifiers
  • scopus:0028897585
ISSN
0014-4754
DOI
10.1007/BF01928898
project
Chemical communication in sawflies
language
English
LU publication?
yes
id
ecf1d532-bdda-4d8c-b398-224e493d8524
date added to LUP
2020-05-20 15:39:33
date last changed
2024-01-02 11:12:15
@article{ecf1d532-bdda-4d8c-b398-224e493d8524,
  abstract     = {{<p>The main component of the sex pheromone secretion of female Diprion pini L. (Hymenoptera: Diprionidae) from insects collected both in Finland and in France has been identified as a threo-3,7-dimethyl-2-tridecanol (8 ng per female) stereoisomer by GC-MS and synthesis. The secretion also contains lower and higher homologues in small amounts (1-4% of the main component). Combined gas chromatographic-electroantennographic detection showed activity in both natural and esterified extracts (acetates and propionates); the esters of the main component gave the largest responses. The acetates and propionates of the eight stereoisomers of 3,7-dimethyl-2-tridecanol were synthesized from enantiomerically highly enriched (&gt;99% ee) building blocks. The stereochemistry of the main component was established to be (2 S,3 R,7 R)-3,7-dimethyl-2-tridecanol by GC analysis of the natural material. It was purified by liquid chromatography prior to the GC analysis of both its pentafluorobenzoates and its isopropylcarbamates on a non-chiral polar column (ECD) and a chiral column (NPD), respectively. Field tests demonstrated that both the acetate and propionate of the main component (100 μg of each applied on cotton roll dispensers) were active in attracting males, with or without the presence of several of the minor compounds. Experiments with smaller amounts of the acetate and the propionate (1 μg in France and 50 μg in Finland) demonstrated that the propionate was more active than the acetate, and that it also caught more males than a blend of the two compounds.</p>}},
  author       = {{Bergström, G. and Wassgren, A. B. and Anderbrant, O. and Fägerhag, J. and Edlund, H. and Hedenström, E. and Högberg, H. E. and Geri, C. and Auger, M. A. and Varama, M. and Hansson, Bill Stefan}},
  issn         = {{0014-4754}},
  keywords     = {{3,7-dimethyl-2-tridecanol; chiral analysis; chiral synthesis; Diprion pini; lipase; semiochemicals; sex attractant}},
  language     = {{eng}},
  month        = {{04}},
  number       = {{4}},
  pages        = {{370--380}},
  publisher    = {{Birkhäuser}},
  series       = {{Experientia}},
  title        = {{Sex pheromone of the pine sawfly Diprion pini (Hymenoptera : Diprionidae): Chemical identification, synthesis and biological activity}},
  url          = {{http://dx.doi.org/10.1007/BF01928898}},
  doi          = {{10.1007/BF01928898}},
  volume       = {{51}},
  year         = {{1995}},
}