有机化学 ›› 2016, Vol. 36 ›› Issue (3): 642-647.DOI: 10.6023/cjoc201508008 上一篇    下一篇

研究简报

新型吡唑基取代的甲磺酰基类化合物的合成及除草活性研究

温彦鹏a, 张爽b, 侯广峰b, 于颖慧a,b, 高金胜a,b   

  1. a 黑龙江大学化学化工与材料学院 哈尔滨 150080;
    b 黑龙江大学农药工程中心 哈尔滨 150080
  • 收稿日期:2015-08-07 修回日期:2015-11-06 发布日期:2015-11-16
  • 通讯作者: 于颖慧, 高金胜 E-mail:yuyinghui@hlju.edu.cn
  • 基金资助:

    国家自然科学基金(No. 21371052)和黑龙江省博士后科研启动基金(No. LBH-Q14138)资助项目.

Syntheses and Herbicidal Activities of New Methylsulfonyl Compounds with Pyrazol Group

Wen Yanpenga, Zhang Shuangb, Hou Guangfengb, Yu Yinghuia,b, Gao Jinshenga,b   

  1. a School of Chemistry and Materials Science, Heilongjiang University, Harbin 150080;
    b Engineering Research Center of Pesticide of Heilongjiang University, Heilongjiang University, Harbin 150080
  • Received:2015-08-07 Revised:2015-11-06 Published:2015-11-16
  • Supported by:

    Project supported by the the National Natural Science Foundation of China (No. 21371052) and the Heilongjiang Postdoctoral Scientific Research Foundation (No. LBH-Q14138).

为获得具有新颖结构和较高药效的新型除草剂, 基于环磺酮的结构, 对环磺酮结构中苯环的间位取代基及环己二酮环进行了修饰替换, 设计了6个新型的含有吡唑基的甲磺酰基类杂环化合物. 以2-甲基-3-氯苯胺起始原料, 经重氮化、乙酰基化、两步氧化、酯化、溴化、亲核取代、氯化、缩合等9步反应最终获得6个目标化合物. 最终产物以及重要中间体的结构采用1H NMR、13C NMR、FTIR、元素分析等方法进行表征与确认. 对该6个化合物的除草活性进行了测试, 结果表明各化合物对芥菜、繁缕、看麦娘、小藜、棒头草均表现出良好的除草效果.

关键词: 吡唑基, 甲磺酰基, 环磺酮, 合成, 反应条件, 除草活性

To obtain new herbicidal candidates with novel structure and high herbicidal activities, six new pyrazol compounds based on the structure of tembotrione were designed and synthesized. The meta substituent of benzene ring and the cyclohexadione ring in the original tembotrione structure are replaced. The six target compounds were achieved with 3-chloro-2-methylaniline as the starting material after nine steps reactions, namely diazotization, acetylization, oxidation, esterization, bromization, nucleophilic substitution, chlorination and condensation reactions. All the structures of target products and their intermediates are characterized and confirmed by 1H NMR, 13C NMR, FTIR and elemental analysis. Herbicidal activity tests are also conducted for the six compounds. The results show that each compound exhibits certain herbicidal activity toward mustard, chickweed, amur foxtail, chenopodium and polypogon fugax.

Key words: pyrazol, methylsulfonyl, tembotrione, synthesis, reaction conditions, herbicidal activities