Identification of a Sex Pheromone Component of Pseudococcus cryptus |
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| Authors: | Tomonori Arai Hajime Sugie Syuntaro Hiradate Shigefumi Kuwahara Noriaki Itagaki Takashi Nakahata |
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| Affiliation: | (1) Department of Citrus Research, Kuchinotsu, National Institute of Fruit Tree Science, Kuchinotsu, Nagasaki, 859-2501, Japan;(2) Department of Apple Research, Morioka, Iwate, 020-0123, Japan;(3) National Institute of Agro-Environmental Sciences, 3-1-3 Kannondai, Tsukuba, Ibaraki, 305-8604, Japan;(4) Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University, 1-1 Tsutsumidori-Amamiyamachi, Aoba-ku, Sendai, 981-8555, Japan |
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| Abstract: | A sex pheromone component of Pseudococcus cryptus has been isolated and identified. The crude pheromone extract obtained by airborne collection was fractionated by liquid chromatography (LC) on Florisil, and further purified by high performance liquid chromatography and preparative Gas Chromatography (GC). The pheromone component was shown to be an ester, the alcohol part of which was identical to the known alcohol moiety of the pheromone of Planococcus citri. The chemical structure was determined to be 3-isopropenyl-2,2-dimethylcyclobutylmethyl 3-methyl-3-butenoate by MS and 1H NMR analyses. The absolute configuration of the pheromone was assigned as (1R,3R) by comparison of the retention time of the alcohol derived from the P. cryptus pheromone with those of the alcohol derived from P. citri pheromone, and a synthetic sample of alcohol enriched in the (1R,3R)-enantiomer, using a chiral GC stationary phase. The structure of the pheromone was confirmed by synthesis, and by bioassays in a glasshouse. |
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| Keywords: | Identification sex pheromone Pseudococcus cryptus (1R 3R)-3-isopropenyl-2 2-dimethylcyclobutylmethyl 3-methyl-3-butenoate |
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