アスカリドール類縁体の合成とサツマイモネコブセンチュウおよびイネシンガレセンチュウに対する殺線虫活性

概要

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A series of ascaridole derivatives 1-10 were successfully synthesized and their structures were characterized by ^1H, ^<13>C NMR and high-resolution mass spectroscopy. The nematocidal activities of these compounds were evaluated and the results indicated that these derivatives have better nematocidal activities against Meloidogyne incognita than Aphelenchoides besseyi. Interestingly, cis-isomers of Z-3,6-epidioxy-1-methyl-4-isopropylcyclohexene (2) and Z-3,6-epidioxy-1-methyl-4-isopropenylcyclohexene (4) are more active than their corresponding trans-isomers. Among them, 1,4-epidioxy-4-isopropyl-2-cyclohexenoic acid (8) and 1,4-epidioxy-4-isopropyl-2-cyclohexenecarboxylic acid methyl ester (10) exhibited significant higher nematocidal activities than those of other analogs; therefore the carboxylic acid or carboxyl ester substituent on the ring might be essential for high nematocidal activity. Compared with the toxicity of a commercial nematocide, Oxamyl, these derivatives can be considered effective and promising.
2007-02-20