Azuki bean weevil

While the unbranched 204-207 clearly originate from the acetate pool, the structure of ( )-3,7-dimethyl-2-octene-l,8-dioic acid, callosobruchusic acid 207, a female produced copulation releasing pheromone of the azuki bean weevil, Callosobruchus chinensis [374] points to a terpenoid structure. The synthetic enantiomers [375] proved to be equally effective in releasing copulation behaviour in males. 

Recently, both enantiomeric forms of callosobruchusic acid (170), a pheromone of the azuki bean weevil, Callosobruchus chinensis L., which induces the male to extrude his genital organ and to attempt copulation, were synthesized by Mori et al.178), applying Evan s alkylation method in natural product synthesis as the key step. Thus, (S)-prolinol propionamide was converted to its enolate (164) by treatment with LDA. 

The diacid corresponding to 114 is callosobruchic acid (115), and forms part of the copulation release pheromone of the azuki bean weevil, Callosobruchus chinensis Both chiral isomers have been synthesized by Mori et al. from methyl geranate epoxide (123). After scission of the epoxide group, the iodide 124 was made conventionally, then the chiral group was introduced using the Evans (R)- or (5)-prolinol propionamide enolate anion (125) (made with lithium diethylamide in tetrahydrofuran on the amide). Removal of the proline group... 

Oshima, K., Honda, H. and Yamamoto, I. (1973) Isolation of an oviposition marker from Azuki bean weevil, Callosobruchus chinensis. Agric. Biol. Chem., 31, 2679-80. 

Matsumoto, H., S. Tebayashi, Y. Kuwahara, S. Matsuyama, T. Suzuki K Fujii. 1994. Identification of taxifolin present in the Azuki bean as an oviposition stimulant of the Azuki bean weevil. J. Pesticide Sci, 19 181-186. 

Umeya, K. (1966) Studies on the comparative ecology of bean weevils. I. On the egg distribution and the oviposition behaviors of three species of bean weevils infesting Azuki bean. Res, Bull. Plant Prot. Japan., 3, 1-11. 

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