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J Chem Ecol

Title:		"Pheromone chirality of asian palm weevils,Rhynchophorus ferrugineus (Oliv.) andR. vulneratus (Panz.) (Coleoptera: Curculionidae)"
Author(s):		Perez AL; Hallett RH; Gries R; Gries G; Cameron Oehlschlager A; Borden JH;
Address:		"Department of Chemistry, Simon Fraser University, V5A 1S6, Burnaby, British Columbia, Canada"
Journal Title:		J Chem Ecol
Year:		1996
Volume:		22
Issue:		2
Page Number:		357 - 368
DOI:		10.1007/BF02055104
ISSN/ISBN:		0098-0331 (Print) 0098-0331 (Linking)
Abstract:		"Production of 4-methyl-5-nonanol, and 4-methyl-5-nonanone by two sympatric Asian palm weevils,Rhynchophorus ferrugineus (Oliv.) andR. vulneratus (Panz.) suggested that enantiospecificity of either compound could impart species specificity of pheromone communication. Weevil-produced, racemic 4-methyl-5-nonanol and 4-methyl-5-nonanone and their stereoselectively synthesized optical isomers were subjected to gas chromatographic-electroantennographic detection (GC-EAD) and GC-mass spectrometry (MS) on a chiral Cyclodex-B column. Only theS,S stereoisomer of 4-methyl-5-nonanol was EAD active and was produced by bothR. ferrugineus andR. vulneratus. Production and EAD activity of (S)-4-methyl-5-nonanone exceeded that of its antipode in both weevils. In field experiments in Java. (4S, 5S)-4-methyl-5-nonanol and the stereoisomeric mixture were equally attractive. The 4R,5R stereoisomer was inactive. The corresponding ketone enantiomers neither enhanced nor reduced attraction to (4S,5S)-4-methyl-5-nonanol. Lack of apparent differences betweenR. ferrugineus andR. vulneratus pheromones suggests that synonomy of both weevils should be considered unless other pre- or postzygotic reproductive isolating mechanisms are disclosed in future studies"
Keywords:
Notes:		"PubMed-not-MEDLINEPerez, A L Hallett, R H Gries, R Gries, G Cameron Oehlschlager, A Borden, J H eng 1996/02/01 J Chem Ecol. 1996 Feb; 22(2):357-68. doi: 10.1007/BF02055104"