Structure and fungicidal activities of methoxy-iminophenylacetamide derivatives
1999
Ichinari, M. | Masuko, M. | Takenaka, H. | Hasegawa, R. | Ichiba, T. | Hayase, Y. | Takeda, R.
Methoxyiminoacetamides derived from ring-cleaved isoxazole compounds are active against economically important fungal diseases of many crops. Our approach, based upon biorational design, resulted in the production of methoxyiminophenyl-acetamide derivatives similar in their chemical structure and biological performance to a family of strobilurins produced by Basidiomycotina fungi. A number of 2-methoxyimino-2-(2-phenoxy-phenyl)acetamide derivatives were synthesized and their fungicidal activity evaluated from which, (E)-2-methoxymino-N- methyl-2-(2-phenoxyphenyl) acetamide (SSF-126) was selected as a promising candidate blasticide. Further studies revealed that the substitution of a substituted phenoxymethyl group for the phenoxy group contributed to an increase in the fungicidal activity. Mono-, di- or tri-substitutions at 2-, 3-, 4- and/or 5-positions of the benzene ring by halogen or lower alkyl also led to an increase in the activity. However, 2,6-di- or 2,3,6-tri-substituted derivatives were less active against the crop diseases tested. Furthermore, the phenoxymethyl group could be replaced by the 2-pyridyloxymethyl group. Mono- or di-substitutions at 3-, 5-, and/or 6-positions of the pyridine ring by C1 or CF3 resulted in a good control of the crop diseases tested.
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