Identification of male-produced aggregation pheromone of the curculionid beetle Sternechus subsignatus

J Chem Ecol. 2012 Mar;38(3):272-7. doi: 10.1007/s10886-012-0080-3. Epub 2012 Mar 1.

Abstract

Analyses of the headspace volatiles produced by males and females of Sternechus subsignatus Boheman (Coleoptera: Curculionidae) revealed seven male-specific compounds. The major component was (E)-2-(3,3-dimethylcyclohexylidene)-ethanol, and the minor components were 1-(2'-hydroxyethyl)-1-methyl-2-isopropenylcyclobutane (grandisol), 7-methyl-3-methyleneoct-6-en-1-ol, (Z)-2-(3,3-dimethylcyclohexylidene)-ethanol, (Z)- and (E)-2-(3,3-dimethylcyclohexylidene)-acetaldehyde, and (E)-2-(3,3-dimethylcyclohexylidene) acetic acid. The latter compound is described for the first time as a natural product. Only four of the seven identified compounds showed electrophysiological activity. Enantioselective gas chromatography showed that the natural grandisol is the (1R,2S)-stereoisomer. The major component, (E)-2-(3,3-dimethylcyclohexylidene)-ethanol, attracted S. subsignatus in olfactometer bioassays. Studies are in progress to evaluate the biological activity of the major component and the EAD-active mixture under field conditions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetaldehyde / chemistry
  • Acetaldehyde / metabolism
  • Acetic Acid / chemistry
  • Acetic Acid / metabolism
  • Animals
  • Chromatography, Gas
  • Ethanol / chemistry
  • Ethanol / metabolism
  • Female
  • Male
  • Pheromones / chemistry*
  • Pheromones / metabolism*
  • Stereoisomerism
  • Terpenes / chemistry
  • Terpenes / metabolism
  • Weevils / chemistry
  • Weevils / metabolism*

Substances

  • Pheromones
  • Terpenes
  • Ethanol
  • grandisol
  • Acetaldehyde
  • Acetic Acid