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J Agric Food Chem

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"
Author(s):		Khrimian A; Klun JA; Hijji Y; Baranchikov YN; Pet'ko VM; Mastro VC; Kramer MH;
Address:		"USDA, ARS, PSI, Chemicals Affecting Insect Behavior Laboratory, Beltsville, Maryland 20705, USA. khrimiaa@ba.ars.usda.gov"
Journal Title:		J Agric Food Chem
Year:		2002
Volume:		50
Issue:		22
Page Number:		6366 - 6370
DOI:		10.1021/jf020472s
ISSN/ISBN:		0021-8561 (Print) 0021-8561 (Linking)
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"
Keywords:		"Animals Copper Isomerism Moths/*physiology Oxidation-Reduction *Pest Control, Biological Sex Attractants/*biosynthesis/pharmacology Zinc/*metabolism;"
Notes:		"MedlineKhrimian, Ashot Klun, Jerome A Hijji, Yousef Baranchikov, Yuri N Pet'ko, Vladimir M Mastro, Victor C Kramer, Matthew H eng 2002/10/17 J Agric Food Chem. 2002 Oct 23; 50(22):6366-70. doi: 10.1021/jf020472s"