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United States Department of Agriculture

Agricultural Research Service

Title: Activated Zinc Reduction of Enynes to Conjugated Diene Lepidoptera Pheromones, and Field Capture of Siberian Moths with Synthetic Pheromone Mixtures.

item Khrimian, Ashot
item Klun, Jerome
item Hijji, Yousef - MORGAN STATE UNIV
item Baranchikov, Yuri - V.N. SUKACHEV INST
item Pet'ko, Vladimir - V.N. SUKACHEV INST
item Mastro, Victor - USDA APHIS OTIS METHODS D
item Kramer, Matthew

Submitted to: Journal of Agricultural and Food Chemistry
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: August 7, 2002
Publication Date: N/A

Technical Abstract: 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 Lepidopteran 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) which achieved rapid and high yield reduction in methanol-water. The stereoselectivity of semi-hydogenation was 98 %. A process whereby zinc dust was continuously activated throughout the reduction with an acid was also satisfactory (95-98 % cis). Field trapping experiment with the Siberian moth showed that a 1:1 mixture of (Z,E)-5,7-dodecadienol and (Z,E)-5,7-dodecadienal applied to rubber septa and stored for 90 days was both stable and an effective sex attractant for the moth. If septa are used as pheromone dispensers in surveillance and monitoring traps, they should be replaced at least biweekly.

Last Modified: 4/18/2015
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