Male-produced sex pheromone of the stink bug Edessa meditabunda

J Chem Ecol. 2012 Jul;38(7):825-35. doi: 10.1007/s10886-012-0144-4. Epub 2012 Jun 13.

Abstract

Edessa meditabunda is a secondary pest within the piercing-sucking stink bug complex that attacks soybean crops in Brazil. The behavioral responses of males and females to aeration extracts from conspecifics suggested the presence of a male-produced sex pheromone. Gas chromatographic (GC) analysis of male and female aeration extracts revealed the presence of two male-specific compounds in a ratio of 92:8. Gas chromatographic -electroantennographic detection (GC-EAD) assays indicated that the major component is bioactive for females, supporting the behavioral data. Analysis of the mass and infrared spectra of the male-specific compounds suggested that they were both methyl-branched long-chain methyl esters. On the basis of the mass spectra of the respective hydrocarbons obtained by micro derivatizations, the structures of these methyl esters were proposed to be methyl 4,8,12-trimethylpentadecanoate (major) and methyl 4,8,12-trimethyltetradecanoate (minor). An 11 step synthetic route that was based on a sequence of Grignard reactions, starting from cyclopropyl methyl ketone, was developed to obtain synthetic standards with a 7.9 % overall yield for the major compound and a 9.9 % yield for the minor. The synthetic standards co-eluted with the natural pheromones on three different GC stationary phases. Y-tube olfactometer assays showed that the synthetic standards, including the major compound alone and a mixture of the major and minor compounds in the proportion found in natural extracts, were strongly attractive to females.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animal Communication
  • Animals
  • Female
  • Heteroptera / metabolism*
  • Male
  • Molecular Structure
  • Sex Attractants / chemical synthesis*
  • Sex Attractants / metabolism
  • Sexual Behavior, Animal

Substances

  • Sex Attractants