The method reported previously (Part I) was employed to prepare a variety of novel 6-acylsalicylates as key intermediates. 6-Acylpyrimidin-2-yl salicylates (2-acyl-6-[(4,6-disubstituted pyrimidin-2-y1)oxylbenzoate derivatives: Type l), the closely related phthalide compounds (3-alkyl-7-[(4,6-dimethoxypyrimidin-2-yl)oxy]phthalide derivatives : Type 2) and the ketal derivatives of 2-acyl-6-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoates (Type 3) were synthesized and their herbicidal activities measured. Methyl 2-acetyl-6-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoate gave excellent control of barnyard grass with a promising profile as a prototype rice herbicide.
: The previously evaluated prototype, methyl 6-acetyl-2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoate, was modiÐed by the introduction of an oximino group. Further extensive synthetic modiÐcations were then made to the 6-alkyl moiety (R1), the ester moiety (R2), the alkoxyimino moiety (R3), the bridge-atom (X) and the 4,6-disubstituted-pyrimidine moiety (A, B, Z). StructureÈ activity relationships of the synthesized compounds were studied by examining their herbicidal activity against Barnyard grass (Echinochloa oryzicola) in paddy rice at various growth stages, including pre-emergence. The novel herbicide methyl 2-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-[1-(methoxyimino)ethyl]benzoate, (KIH-6127) was found to be the most e †ective compound. The commercial development of this compound is currently in progress.
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