title: Identification, Synthesis, and Field Tests of the Sex Pheromone of Margarodes prieskaensis (Jakubski).
abstract: Here, we report the identification and synthesis of the sex pheromone of female Margarodes prieskaensis (Jakubski), and the attractiveness of the synthetic pheromone to males in field trapping tests. Volatile organic compounds were collected from virgin females using a sample enrichment probe (SEP). Analyses by gas chromatography coupled to mass spectrometry revealed the presence of only two constituents. By scaling up the SEP, sufficient of the major constituent was collected for1H and13C nuclear magnetic resonance (NMR) analyses and ancillary NMR techniques. The sex attractant was identified as (2R,4R,6R,8R)-2,4,6,8-tetramethylundecan-1-ol. The enantiomerically pure compound was synthesized from octadecyl (2R,4R,6R,8R)-2,4,6,8-tetramethylundecanoate, a minor component of the uropygial (preen) gland secretion of the domestic goose, Anser domesticus. Field trapping experiments, carried out in vineyards in the Northern Cape Province of South Africa, showed that the synthetic compound was as attractive to winged males of M. prieskaensis as virgin females. The second compound detected was identified as the corresponding acetate, but addition of this did not affect the attractiveness of the major component. We believe this to be the first identification of a sex attractant of the Margarodidae.
authors.affiliation: Department of Chemistry and Polymer Science, Stellenbosch University, Stellenbosch, 7602, South Africa. LECUS@sun.ac.za.
authors.forename: Barend V
authors.initials: BV
authors.lastname: Burger
authors.affiliation: ARC Infruitec-Nietvoorbij, Stellenbosch, 7602, South Africa.
authors.forename: C André
authors.initials: CA
authors.lastname: de Klerk
authors.affiliation: , Elmblick 53, D-3802, Wolfenbüttel, Germany.
authors.forename: Michael
authors.initials: M
authors.lastname: Morr
authors.affiliation: Department of Chemistry and Polymer Science, Stellenbosch University, Stellenbosch, 7602, South Africa.
authors.forename: Wilhelmina J G
authors.initials: WJ
authors.lastname: Burger
mesh_terms: D000818:Animals; D001522:Behavior, Animal; D005260:Female; D006430:Hemiptera / Q000378:metabolism* / Q000502:physiology; D008297:Male; D012724:Sex Attractants / Q000032:analysis / Q000737:chemistry / Q000378:metabolism; D055549:Volatile Organic Compounds / Q000032:analysis / Q000737:chemistry / Q000378:metabolism
chemical_list: D012724:Sex Attractants; D055549:Volatile Organic Compounds
keywords: (2R,4R,6R,8R)-2,4,6,8-tetramethylundecan-1-ol; Bioassay; Headspace analysis; Hemiptera; Margarodes prieskaensis; Margarodidae; SEP; Sample enrichment probe; Sex pheromone; Sternorrhyncha