除草剤フルアジホップの開発

DOI NDLデジタルコレクション 日本農学文献記事索引 Web Site Web Site 被引用文献5件

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タイトル別名
  • Development of a New Herbicide, Fluazifop-butyl
  • ジョソウザイ フルアジホップ ノ カイハツ

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Since the invention of phenoxyacetic acid herbicides with clear activity on broad-leaf plants, the development of a herbicide with reverse selectivity has been a long-pending problem from the practical viewpoint of removing grasses from broad-leaf crops. Based on the results of the long-term studies to improve the unfavorable characters of diphenyl ether herbicides, the authors have successfully developed fluazifop which is capable of killing grasses, including perennials, without damaging broad-leaf crops. Since diphenyl ether herbicides selected as a lead-compound do not translocate in plants but kill only the tissues directly exposed to the herbicides, an oxyalkanoate side-chain characteristic to the phenoxyacetic acid auxin herbicides, which are able to translocate in plant tissues, was introduced to the 3′-position adjacent to the nitro group on the diphenyl ether structure. Thus-prepared esters improved the translocation but not satisfactorily enough for the practical use. Therefore, the following attempts were made for optimization: 1) introduction of a trifluoromethyl group as a substituent on the 4-position, 2) alteration of one of the benzene rings to a pyridine nucleus, 3) elimination of the nitro group on the 4-position which had been regarded indispensable, 4) migration of oxyalkanoate on the 3-position to the 4-position, 5) selection of lactate out of alkanoates to obtain optimum herbicidal activity, and 6) modification of an ester moiety. Thus-prepared fluazifop-butyl, endowed with selectivity of killing grass weeds without damaging broad-leaf crops and with excellent translocatability in plant tissues to the extent of killing the subterranean stems of perennial grasses even in case of foliar treatment, is now marketed for the use in cotton, soybean and beet fields. Structure-activity relationship studies on fluazifop and its related analogs indicated that the trifluoromethylpyridinyloxy group played an important role in the hydrophobicity and total molecule structure to obtain optimum herbicidal activity and in enhancing the systemic activity to let the molecule reach a target organ through plant tissues.

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