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Fungicidal Activities of 2-Methoxy-2-[2-(benzylideneamino-oxymethyl)phenyl]-N-methylacetamide Derivatives
Tsuneo ICHIBA, Takami MURASHI, Shinji SUZUKI, Tosikazu OHTSUKA and Michio MASUKO
J. Pestic. Sci.
27, 223-228 (2002)
A number of 2-methoxy-2-(2-substituted phenyl)-N-methylacetamide derivatives were synthesized and their fungicidal activities were examined. Studies on structure-activity relationships revealed strong fungicidal activity when a 休目methylbenzylideneaminooxymethyl group was introduced at the 2-position of the benzene ring of the phenylacetamide moiety. Furthermore, introduction of halogen atom(s), methyl or ethyl group(s), or methoxy or difluoromethoxy group(s) to the 3- and/or 4-position of the benzene ring of the benzylidene moiety resulted in an increase in fungicidal activity. When the 休目position of the benzylideneaminooxymethyl moiety was not substituted with a methyl group, the fungicidal activity was extremely weak. However, the introduction of a 休目methylthio group to this moiety increased the activity against cucumber downy mildew. Among the compounds synthesized in this study, (E)-2-methoxy-N-methyl-2-﹡2-(休目methylthio-4-trifluoromethylbenzylideneaminooxymethyl)phenyl＋acetamide and (E)-2-[2-(4-difluoromethoxy-休目methylthiobenzylideneaminooxymethyl)phenyl]-2-methoxy-N-methylacetamide were very active against cucumber downy mildew. The former compound was also effective in the control of potato late blight.
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