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.
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.
Khrimian
Ashot
A
USDA, ARS, PSI, Chemicals Affecting Insect Behavior Laboratory, Beltsville, Maryland 20705, USA. khrimiaa@ba.ars.usda.gov
Klun
Jerome A
JA
Hijji
Yousef
Y
Baranchikov
Yuri N
YN
Pet'ko
Vladimir M
VM
Mastro
Victor C
VC
Kramer
Matthew H
MH
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*
D012724:Sex Attractants; D003300:Copper; D015032:Zinc