Identification and Synthesis of the Male-produced Sex Pheromone of the Stink Bug, Pellaea stictica

J Chem Ecol. 2015 Sep;41(9):859-68. doi: 10.1007/s10886-015-0621-7. Epub 2015 Aug 30.

Abstract

Stink bugs are major pests of a wide variety of agricultural crops worldwide. The species Pellaea stictica is a Neotropical stink bug found in several South American countries. Chromatographic analyses of volatiles released by adults of this species showed that males produce a sex-specific compound, and bioassays with a Y-tube olfactometer showed that the compound was attractive only to females, confirming that it is a sex pheromone. Gas chromatography coupled to mass spectrometry and Fourier transform infrared analyses of the natural compound and several derivatives suggested that the structure was an alcohol with a saturated carbon chain and several methyl branches. After synthesis of two proposed structures, the pheromone of P. stictica was identified as a novel compound, 2,4,8,13-tetramethyltetradecan-1-ol. Laboratory bioassays showed that the synthesized mixture of stereoisomers of 2,4,8,13-tetramethyltetradecan-1-ol was as attractive to P. stictica females as the natural pheromone.

Keywords: 2,4,8,13-tetramethyltetradecan-1-ol; GC/EAD; Hemiptera; Microderivatization; Pentatomidae; Pheromone synthesis; Semiochemicals.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Fatty Alcohols / analysis
  • Fatty Alcohols / metabolism*
  • Female
  • Gas Chromatography-Mass Spectrometry
  • Hemiptera / chemistry
  • Hemiptera / metabolism*
  • Male
  • Sex Attractants / analysis
  • Sex Attractants / metabolism*
  • Sexual Behavior, Animal

Substances

  • 2,4,8,13-tetramethyltetradecan-1-ol
  • Fatty Alcohols
  • Sex Attractants