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Synthesis and Fungicidal Activities of Heterocyclic Compounds Having alfa-Methoxyimino-2-phenoxymethylbenzyl Group
Hiroyuki KAI, Tsuneo ICHIBA, Akira TAKASE and Michio MASUKO
J. Pestic. Sci.
25, 24-30 (2000)
A series of (alfa-methoxyimino-2-phenoxymethylbenzyl)heterocycle derivatives were synthesized and their fungicidal activities were assessed. Studies of the structure-activity relationships revealed the strongest fungicidal activity when the heterocycle moiety was comprised of 1-methyl-2-imidazolyl and 1,3,4-oxadiazol-2-yl groups. When the benzene ring on the phenoxymethyl moiety was substituted with 2-methyl, 2,5-dimethyl or 4-chloro-2-methyl, good fungicidal activity was obtained. Between the two geometrical isomers at the oxime moiety, the E-isomers of imidazole and oxadiazole derivatives were more active than the Z-isomers. Among the compounds examined, (E)-2-[2-(4-chloro-2-methylphenoxy-methyl)-y-methoxyiminobenzyl]-1-methylimidazole (27) showed a potent activity against cucumber powdery mildew and cucumber gray mold.
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