title: Identification of male-produced aggregation pheromone of the curculionid beetle Sternechus subsignatus.
abstract: Analyses of the headspace volatiles produced by males and females of Sternechus subsignatus Boheman (Coleoptera: Curculionidae) revealed seven male-specific compounds. The major component was (E)-2-(3,3-dimethylcyclohexylidene)-ethanol, and the minor components were 1-(2'-hydroxyethyl)-1-methyl-2-isopropenylcyclobutane (grandisol), 7-methyl-3-methyleneoct-6-en-1-ol, (Z)-2-(3,3-dimethylcyclohexylidene)-ethanol, (Z)- and (E)-2-(3,3-dimethylcyclohexylidene)-acetaldehyde, and (E)-2-(3,3-dimethylcyclohexylidene) acetic acid. The latter compound is described for the first time as a natural product. Only four of the seven identified compounds showed electrophysiological activity. Enantioselective gas chromatography showed that the natural grandisol is the (1R,2S)-stereoisomer. The major component, (E)-2-(3,3-dimethylcyclohexylidene)-ethanol, attracted S. subsignatus in olfactometer bioassays. Studies are in progress to evaluate the biological activity of the major component and the EAD-active mixture under field conditions.
authors.affiliation: Laboratório de Semioquímicos, Departamento de Química, Universidade Federal do Paraná, CP 19081, CEP 81531-990, Curitiba, PR, Brazil.
authors.forename: Bianca G
authors.initials: BG
authors.lastname: Ambrogi
authors.forename: Angela M Palacio
authors.initials: AM
authors.lastname: Cortés
authors.forename: Paulo H G
authors.initials: PH
authors.lastname: Zarbin
mesh_terms: D000079:Acetaldehyde / Q000737:chemistry / Q000378:metabolism; D019342:Acetic Acid / Q000737:chemistry / Q000378:metabolism; D000818:Animals; D002849:Chromatography, Gas; D000431:Ethanol / Q000737:chemistry / Q000378:metabolism; D005260:Female; D008297:Male; D010675:Pheromones / Q000737:chemistry* / Q000378:metabolism*; D013237:Stereoisomerism; D013729:Terpenes / Q000737:chemistry / Q000378:metabolism; D048889:Weevils / Q000737:chemistry / Q000378:metabolism*
chemical_list: D010675:Pheromones; D013729:Terpenes; D000431:Ethanol; C013009:grandisol; D000079:Acetaldehyde; D019342:Acetic Acid