Pheromone chirality of Asian palm weevils, Rhynchophorus ferrugineus (Oliv) and R-vulneratus (Panz) (Coleoptera: Curculionidae)
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| Authors: | Perez, AL; Hallett, RH; Gries, R; Gries, G; Oehlschlager, AC; Borden, JH |
| Year: | 1996 |
| Journal: | Journal of Chemical Ecology 22: 357-368 |
| Title: | Pheromone chirality of Asian palm weevils, Rhynchophorus ferrugineus (Oliv) and R-vulneratus (Panz) (Coleoptera: Curculionidae) |
| Abstract: | Production of 4-methyl-5-nonanol, and 4-methyl-5-nonanone by two sympatric Asian palm weevils, Rhynchophorus ferrugineus (Oliv.) and R. vulneratus (Pant.) 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 the S,S stereoisomer of 4-methyl-5-nonanol was EAD active and was produced by both R. ferrugineus and R. 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 between R. ferrugineus and R. vulneratus pheromones suggests that synonomy of both weevils should be considered unless other pre- or postzygotic reproductive isolating mechanisms are disclosed in future studies. |
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