A contact sex pheromone component of the emerald ash borer Agrilus planipennis Fairmaire (Coleoptera: Buprestidae)

Naturwissenschaften. 2009 May;96(5):601-8. doi: 10.1007/s00114-009-0513-1. Epub 2009 Feb 24.

Abstract

Analyses of the elytral hydrocarbons from male and female emerald ash borer, Agrilus planipennis Fairmaire, that were freshly emerged vs. sexually mature (>10 days old) revealed a female-specific compound, 9-methyl-pentacosane (9-Me-C(25)), only present in sexually mature females. This material was synthesized by the Wittig reaction of 2-decanone with (n-hexadecyl)-triphenylphosphonium bromide followed by catalytic reduction to yield racemic 9-Me C(25), which matched the natural compound by gas chromatography/mass spectrometry (retention time and EI mass spectrum). In field bioassays with freeze-killed sexually mature A. planipennis females, feral males spent significantly more time in contact and attempting copulation with unwashed females than with females that had been washed in n-hexane to remove the cuticular lipids. Hexane-washed females to which 9-Me-C(25) had been reapplied elicited similar contact time and percentage of time attempting copulation as unwashed females, indicating that 9-methyl-pentacosane is a contact sex pheromone component of A. planipennis. This is the first contact sex pheromone identified in the Buprestidae.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Coleoptera / physiology*
  • Female
  • Gas Chromatography-Mass Spectrometry
  • Hydrocarbons / chemistry
  • Hydrocarbons / isolation & purification
  • Male
  • Organophosphorus Compounds / isolation & purification
  • Pheromones / chemistry
  • Pheromones / isolation & purification
  • Pheromones / physiology*
  • Sex Characteristics
  • Sexual Behavior, Animal / physiology
  • Sexual Maturation / physiology
  • Spectrum Analysis

Substances

  • Hydrocarbons
  • Organophosphorus Compounds
  • Pheromones