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

Journal of Chemical Ecology
Carla F FávaroPaulo H G Zarbin

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.

References

Apr 28, 2009·Journal of Chemical Ecology·Joshua RodsteinJocelyn G Millar
Jun 14, 2012·Journal of Chemical Ecology·Paulo H G ZarbinMauro A C M Rodrigues
Aug 24, 2012·Journal of Chemical Ecology·Carla F FávaroPaulo H G Zarbin
Apr 3, 2013·Organic Letters·Carla F FávaroPaulo H G Zarbin

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