The male-produced sex pheromone of the true bug, Phthia picta, is an unusual hydrocarbon

J Chem Ecol. 2012 Jul;38(7):814-24. doi: 10.1007/s10886-012-0147-1. Epub 2012 Jun 7.

Abstract

Phthia picta is part of a complex of true bugs (Heteroptera) in Brazil that attack tomatoes, being particularly damaging because nymphs and adults feed on both leaves and fruit. Gas chromatography (GC) of aeration extracts of adult males vs. females revealed the presence of a male-specific compound. GC-electroantennographic detector experiments indicated that the antennae of females are highly sensitive to this male-specific compound. GC-mass spectrometry and GC-FTIR analyses suggested a methyl branched hydrocarbon structure for this compound. After synthesis of three different proposed structures, the natural product was indentified as 5,9,17-trimethylhenicosane, which was strongly attractive to females in Y-tube olfactometer bioassays. Analysis of dissected body parts of adults revealed that the pheromone is produced in the lateral accessory glands of the metathoracic scent gland of males only.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animal Communication
  • Animals
  • Female
  • Heteroptera / metabolism*
  • Hydrocarbons / chemistry
  • Male
  • Mass Spectrometry
  • Sex Attractants / chemical synthesis*
  • Sex Attractants / metabolism
  • Sexual Behavior, Animal
  • Spectroscopy, Fourier Transform Infrared

Substances

  • Hydrocarbons
  • Sex Attractants