高等学校化学学报 ›› 2015, Vol. 36 ›› Issue (5): 907-913.doi: 10.7503/cjcu20141121

• 有机化学 • 上一篇    下一篇

2-甲基-6-硝基苯磺酰脲衍生物的合成及生物活性

陈伟, 魏巍, 李玉新, 万莹莹, 刘巧霞, 李永红, 于淑晶, 李正名()   

  1. 南开大学元素有机化学国家重点实验室, 化学化工协同创新中心(天津), 天津300071
  • 收稿日期:2014-12-22 出版日期:2015-05-10 发布日期:2015-04-08
  • 作者简介:联系人简介: 李正名, 男, 博士, 教授, 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
  • 基金资助:
    国家自然科学基金(批准号: 21272129)、 “十二五”国家科技支撑计划项目(批准号: 2011BAE06B05)和高等学校学科创新引智计划(批准号: B06005)资助

Synthesis and Biological Activity of 2-Methyl-6-nitrobenzenesulfonylurea Derivatives

CHEN Wei, WEI Wei, LI Yuxin, WAN Yingying, LIU Qiaoxia, LI Yonghong, YU Shujing, LI Zhengming*()   

  1. State Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering(Tianjin), Nankai University, Tianjin 300071, China
  • Received:2014-12-22 Online:2015-05-10 Published:2015-04-08
  • Contact: LI Zhengming E-mail:nkzml@vip.163.com
  • Supported by:
    † Supported by the National Natural Scinece Foundation of China(No.21272129), the National Key Technologies R&D Program(No.2011BAE06B05) and the Introducing Talents of Discipline to Universities Program of China(No.B06005)

摘要:

设计合成了一系列2-甲基-6-硝基苯磺酰脲衍生物(4a~4p), 通过核磁共振氢谱(1H NMR)和高分辨质谱(HRMS)对其结构进行了确认. 盆栽法除草测试结果表明, 在300 g/ha剂量下, 目标化合物具有优异的芽前或芽后除草活性. 进一步筛选发现, 在75 g/ha剂量下, 化合物4b, 4g, 4h, 4l和4p对油菜、 反枝苋和稗草具有98%以上的除草活性, 与对照药单嘧磺隆(100%)和氯磺隆(≥96.3%)相当. 另外, 部分化合物对真菌也表现出一定的抑制效果, 其中化合物4l对油菜菌核病菌的半最大效应浓度EC50=9.20 mg/L(对照药多菌灵的EC50=5.79 mg/L).

关键词: 磺酰脲, 重氮化, 除草活性, 抑菌活性

Abstract:

In order to search for new compounds with high efficacy herbicidal activity, a series of novel sulfonylurea derivatives was designed and synthesized referring to the commercialization sulfonylurea skeletons: Monosulfuron and Triflulsulfuron-methyl. The title compounds were prepared by multistep synthetic procedures starting from 2-methyl-6-nitroaniline, and their chemical structures were characterized by 1H NMR and HRMS. The bioassay results indicate that some of the title compounds show excellent herbicidal activities at the dosage of 300 g/ha. Further study found that compounds 4b, 4g, 4h, 4l and 4p are as effective as Monosulfuron(100%) and Chlorsulfuron(≥96.3%) against Brassica napus, Amaranthus retroflexus L. and Echinochloa Crusgalli at the dosage of 75 g/ha. Preliminary fungicidal test showed some target compounds also hold good antifungal activity in vitro. Particularly, the EC50 of compound 4l against Sclerotinia sclerotiorum was 9.20 mg/L(Carbendazim, EC50=5.79 mg/L).

Key words: Sulfonylurea, Diazotization, Herbicidal activity, Fungicidal activity

中图分类号: