title: Syntheses of (Z,E)-5,7-dodecadienol and (E,Z)-10,12-hexadecadienol, lepidoptera pheromone components, via zinc reduction of enyne precursors. test of pheromone efficacy against the Siberian moth.
abstract: Efficient syntheses of (Z,E)-5,7-dodecadienol, a pheromone component of the Siberian moth, Dendrolimus superans sibiricus, and (E,Z)-10,12-hexadecadienol, a pheromone component of various Lepidoptera pheromones, were accomplished by cis reduction of the corresponding enynols with activated zinc. The most energetic reagent was zinc galvanized with copper and silver (Zn/Cu/Ag) that achieved rapid and high-yield reduction in methanol-water. The stereoselectivity of semi-hydrogenation was > or =98%. A process whereby zinc dust was continuously activated throughout the reduction with an acid was also satisfactory (95-98% cis). Field evaluation of the 1:1 mixture of (Z,E)-5,7-dodecadienol and (Z,E)-5,7-dodecadienal with the Siberian moth in Russia showed that the rubber septa pretreated with compound and stored at -80 degrees C were as effective as freshly treated septa. Moth responses to septa aged in open air indicated that lure effectiveness declined significantly after 2 weeks of aging. Thus, if rubber septa are used as pheromone dispensers in Siberian moth traps monitoring, they should be replaced biweekly with fresh septa for optimal trap effectiveness.
authors.affiliation: USDA, ARS, PSI, Chemicals Affecting Insect Behavior Laboratory, Beltsville, Maryland 20705, USA. khrimiaa@ba.ars.usda.gov
authors.forename: Ashot
authors.initials: A
authors.lastname: Khrimian
authors.forename: Jerome A
authors.initials: JA
authors.lastname: Klun
authors.forename: Yousef
authors.initials: Y
authors.lastname: Hijji
authors.forename: Yuri N
authors.initials: YN
authors.lastname: Baranchikov
authors.forename: Vladimir M
authors.initials: VM
authors.lastname: Pet'ko
authors.forename: Victor C
authors.initials: VC
authors.lastname: Mastro
authors.forename: Matthew H
authors.initials: MH
authors.lastname: Kramer
mesh_terms: D000818:Animals; D003300:Copper; D007536:Isomerism; D009036:Moths / Q000502:physiology*; D010084:Oxidation-Reduction; D010572:Pest Control, Biological; D012724:Sex Attractants / Q000096:biosynthesis* / Q000494:pharmacology; D015032:Zinc / Q000378:metabolism*
chemical_list: D012724:Sex Attractants; D003300:Copper; D015032:Zinc