高等学校化学学报 ›› 2013, Vol. 34 ›› Issue (8): 1868-1872.doi: 10.7503/cjcu20121094

• 有机化学 • 上一篇    下一篇

N-(4'-芳环取代嘧啶基-2'-基)-2-乙氧羰基苯磺酰脲衍生物的合成及抑菌活性

刘卓, 潘里, 于淑晶, 李正名   

  1. 南开大学元素有机化学国家重点实验室, 元素有机化学研究所, 天津 300071
  • 收稿日期:2012-12-04 出版日期:2013-08-10 发布日期:2013-07-19
  • 通讯作者: 李正名,男,教授,博士生导师,中国工程院院士,从事有机化学和农药化学研究.E-mail:nkzml@vip.163.com E-mail:nkzml@vip.163.com
  • 基金资助:

    国家"九七三"计划项目(批准号: 2010CB126106); 国家自然科学基金(批准号: 21272129)和"十二五"国家科技支撑计划项目(批准号: 2011BAE06B05)资助

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

LIU Zhuo, PAN Li, YU Shu-Jing, LI Zheng-Ming   

  1. State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China
  • Received:2012-12-04 Online:2013-08-10 Published:2013-07-19
  • Contact: Zheng-Ming LI E-mail:nkzml@vip.163.com

摘要:

设计合成了14个4位芳环取代的嘧啶磺酰脲衍生物, 其结构均通过1H NMR和高分辨质谱表征确定, 并进行了体外抑菌活性测试. 初步测试结果表明, 在浓度为50 mg/L时, 大部分目标化合物对黄瓜灰霉病、 油菜菌核病和水稻纹枯病表现出一定的抑菌效果, 其中化合物7g, 7h和7i表现出较高的抑菌活性; 但大部分目标化合物对黄瓜枯萎病、 黄瓜褐斑病及苹果轮纹病的抑菌活性与对照药百菌清尚有差距.

关键词: 磺酰脲, 乙酰羟基酸合成酶, 4位芳环取代基嘧啶基, 抑菌活性

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

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