Identification of a Novel Moth Sex Pheromone Component from Chilecomadia valdiviana

J Chem Ecol. 2016 Sep;42(9):908-918. doi: 10.1007/s10886-016-0761-4. Epub 2016 Sep 8.

Abstract

Chilecomadia valdiviana (Philippi) (Lepidoptera: Cossidae) is an insect native to Chile. The larval stages feed on the wood of economically important fruit tree species such as apple, pear, olive, cherry, and avocado, and also on eucalyptus. This causes weakening and, in case of severe infestation, death of the tree. We report identification of the sex pheromone produced by females of this species. Hexane extracts of the abdominal glands of virgin females were analyzed by gas chromatography (GC) with electroantennographic detection, GC coupled with mass spectrometry, and GC coupled to infrared spectroscopy. The major pheromone component was identified as (7Z,10Z)-7,10-hexadecadienal (Z7,Z10-16:Ald), and minor components present in the extracts were (Z)-7-hexadecenal and (Z)-9-hexadecenal, hexadecanal, and (9Z,12Z)-9,12-octadecadienal. Structural assignments were carried out by comparison of analytical data of the natural products and their dimethyl disulfide adducts with those of authentic reference samples. In field tests, traps baited with Z7,Z10-16:Ald captured significantly more males than control traps.

Keywords: Carpenter worm; Cossidae; Homoconjugated double bonds; Lepidoptera; Male attractant; Wood-boring insect.

MeSH terms

  • Aldehydes / analysis
  • Aldehydes / metabolism
  • Alkadienes / analysis
  • Alkadienes / metabolism
  • Animals
  • Chromatography, Gas
  • Female
  • Gas Chromatography-Mass Spectrometry
  • Male
  • Moths / chemistry*
  • Moths / metabolism
  • Sex Attractants / analysis*
  • Sex Attractants / metabolism
  • Spectrophotometry, Infrared
  • Trees / parasitology

Substances

  • 9-hexadecenal
  • Aldehydes
  • Alkadienes
  • Sex Attractants
  • (Z,Z)-7,11-hexadecadienal