Synthesis and field test of three candidates for soybean pod borer's sex pheromone

Nat Prod Commun. 2011 Sep;6(9):1323-6.

Abstract

Three candidates for the soybean pod borer's sex pheromone, dodec-10-en-1-yl acetate (E:Z = 95:5) (9a), (E, E)-dodeca-8, 10-dien-1-yl acetate (9b) and (E)-dodec-8-en-1-yl acetate (9c), were synthesized through the coupling reaction between Grignard reagents and acetates catalyzed by Li2CuCl4. Furthermore, the compounds 9a, 9b, and 9c, when tested in the field, showed that dodec-10-en-1-yl acetate (E:Z = 95:5) (9a) has promise as a lure for male soybean pod borer.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Behavior, Animal / drug effects*
  • Dodecanol / analogs & derivatives*
  • Dodecanol / chemical synthesis
  • Dodecanol / pharmacology
  • Lepidoptera / physiology*
  • Male
  • Molecular Structure
  • Sex Attractants / chemical synthesis*
  • Sex Attractants / pharmacology*

Substances

  • (E)-dodec-8-en-1-yl acetate
  • Sex Attractants
  • dodec-10-en-1-yl acetate
  • dodeca-8,10-dien-1-yl acetate
  • Dodecanol