A number of 2-(substituted phenoxymethyl)phenyl-2-methoxy iminoacetamides were synthesized and their fungicidal activities were examined. The strength of activities and fungicidal spectra varied markedly depending upon the substituents on the benzene ring of the 2-phenoxymethyl group of phenylacetamide moiety. Incorporation of either one or two substituent(s) at 2-, 3-, 4-and/or 5-positions on the benzene ring resulted in an increase of fungicidal activity compared to the unsubstituted compound. However, introduction of a bulky substituent at the 2-position or simultaneous substitution at 2-and 6-positions resulted in decrease of activity. When 2-and 4-, or 2-and 5-positions of the benzene ring were substituted with chlorine and/or methyl groups, in addition to the 2, 5-difluoro derivative (30), the activities were excellent against wheat powdery mildew, cucumber powdery mildew, cucumber gray mold and cucumber downy mildew. Between the two geometrical isomers, the E-form was much stronger than the Z-form.
A number of 2-methoxyimino-N-methyl-2-[2-(substituted 2-pyridyloxymethyl)phenyl] acetamides were synthesized and their fungicidal activities were examined. The activities and fungicidal spectra of the derivatives varied markedly depending upon the substituents on the pyridine ring. Incorporation of either one or two substituent(s) at the 3-, 5-and/or 6-positions of the pyridine ring resulted in increases in fungicidal activity compared with the unsubstituted compound. Among the 2-pyridyl derivatives synthesized in this study, 3-CF3-5-C1, 5-CF3-3-C1 and 3-CF3-6-C1 derivatives exhibited the strongest preventive and curative activities against wide range of diseases. 3, 5, 6-Tri-substituted derivatives demonstrated strong preventive and curative activities against cucumber and wheat powdery mildew, however, they exhibited excellent preventive but weak curative activities against cucumber downy mildew. Between the two geometrical isomers, the E-form exhibited stronger activity than the Z-form.
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