Synthesis and Antifungal Activity of N-(4'-Substituted aromatic pyrimidin-2'-yl)-2-ethoxycarbonyl phenyl Sulfonylurea Derivatives

doi:10.7503/cjcu20121094

Abstract

Abstract:

The innovative research by DuPont’s George Levitt on sulfonylureas had been acknowledged as a milestones in herbicidal chemistry due to the ultralow dosages and ecofriendly characteristics. In order to carry out the systematic research of novel mono- and disubstituted heterocycles within sulfonylurea structures to study the structure-activity relationship(SAR), 14 novel sulfonylurea derivatives containing aromatic substituted moieties at the 4th position of the pyrimidine ring were designed and synthesized based on the commercial herbicide Chlorimuron-ethyl. Their structures were characterized by ¹H NMR and HRMS. The preliminary in vitro bioassay results indicated that most of the title compounds exhibited moderate fungicidal activity against Botrytis cinerea, Sclerotinia sclerotiorum and Rhizoctonia solani at 50 mg/L. Three title compounds 7g, 7h and 7i displayed satisfactory fungicidal activity against them, which are higher than the other compounds. Compounds 7j-7n containing heteroaromatic ring at the 4th position of the pyrimidine ring indicated the moderate fungicidal activity against Sclerotinia sclerotiorum.

Key words: Sulfonylurea, Acetohydroxyacid synthase(AHAS), Monosubstituted aromatic pyrimidine, Antifungal activity

CLC Number:

O626.41

TrendMD:

LIU Zhuo, PAN Li, YU Shu-Jing, LI Zheng-Ming. Synthesis and Antifungal Activity of N-(4'-Substituted aromatic pyrimidin-2'-yl)-2-ethoxycarbonyl phenyl Sulfonylurea Derivatives[J]. Chem. J. Chinese Universities, 2013, 34(8): 1868.

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Synthesis and Antifungal Activity of N-(4'-Substituted aromatic pyrimidin-2'-yl)-2-ethoxycarbonyl phenyl Sulfonylurea Derivatives

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