Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (3): 642-647.DOI: 10.6023/cjoc201508008 Previous Articles     Next Articles



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
  • 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).

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