title: Identification and Synthesis of the Male-produced Sex Pheromone of the Stink Bug, Pellaea stictica.
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.
authors: Departamento de Química, Universidade Federal do Paraná, CP 19081, CEP 81531-990, Curitiba, PR, Brazil.
authors: Carla F
authors: CF
authors: Fávaro
authors: Department of Entomology, University of California, Riverside, CA, 92521, USA.
authors: Jocelyn G
authors: JG
authors: Millar
authors: Departamento de Química, Universidade Federal do Paraná, CP 19081, CEP 81531-990, Curitiba, PR, Brazil. pzarbin@ufpr.br.
authors: Paulo H G
authors: PH
authors: Zarbin
mesh_terms: D000818:Animals; D005233:Fatty Alcohols / Q000032:analysis / Q000378:metabolism*; D005260:Female; D008401:Gas Chromatography-Mass Spectrometry; D006430:Hemiptera / Q000737:chemistry / Q000378:metabolism*; D008297:Male; D012724:Sex Attractants / Q000032:analysis / Q000378:metabolism*; D012726:Sexual Behavior, Animal
chemical_list: C000609457:2,4,8,13-tetramethyltetradecan-1-ol; D005233:Fatty Alcohols; D012724:Sex Attractants
keywords: 2,4,8,13-tetramethyltetradecan-1-ol; GC/EAD; Hemiptera; Microderivatization; Pentatomidae; Pheromone synthesis; Semiochemicals