Identification of male-specific chiral compound from the sugarcane weevil Sphenophorus levis

J Chem Ecol. 2003 Feb;29(2):377-86. doi: 10.1023/a:1022634012212.

Abstract

Comparative gas chromatographic analyses of airborne volatiles produced by males and females of the sugarcane weevil Sphenophorus levis, showed one male-specific compound. Gas chromatography-mass spectrometry data indicated an aliphatic alcohol that was identified as 2-methyl-4-octanol. Both optical isomers were synthesized in five steps by employing commercially available (R)- and (S)-2.2-dimethyl-1,3-dioxolane-4-methanol as starting material. Enantiomeric resolution by gas chromatography with a chiral column demonstrated that the natural alcohol possessed the S configuration. Preliminary indoor observations suggested that the alcohol elicited aggregation behavior among adults. The same compound has been previously described as an aggregation pheromone in several other curculionid species.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Chromatography, Gas
  • Coleoptera / chemistry*
  • Female
  • Flight, Animal
  • Male
  • Movement
  • Pheromones / analysis
  • Pheromones / chemistry*
  • Population Dynamics
  • Volatilization

Substances

  • Pheromones