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Studies of the New Herbicide KIH-6127. Part II. Synthesis and Herbicidal Activity of 6-Acyl Pyrimidin-2-yl Salicylates and Analogues against Barnyard Grass

✍ Scribed by Tamaru, Masatoshi; Takehi, Takayoshi; Masuyama, Naoshi; Hanai, Ryo

Publisher
John Wiley and Sons
Year
1996
Tongue
English
Weight
679 KB
Volume
47
Category
Article
ISSN
1526-498X

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✦ Synopsis

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-[(4,6dimethoxypyrimidin-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-[(4,6dimethoxypyrimidin-2-yl)oxy]benzoate gave excellent control of barnyard grass with a promising profile as a prototype rice herbicide.

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The previously evaluated prototype, methyl 6-acetyl-2-[(4,6dimethoxypyrimidin-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-ato

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A novel synthesis of methyl 6-acetylsalicylate as a key synthetic intermediate for methyl 2-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-[l-(methoxyimino) ethyllbenzoate (KIH-6127) was studied, and directed at 6-substituted pyrimidin-2-yl salicylate herbicides and their analogues. Three synthetic approaches