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.
Keywords
Agrilus planipennis
- Buprestidae - Contact pheromone - Methyl-alkane