Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (8): 2303-2310.DOI: 10.6023/cjoc201901043 Previous Articles     Next Articles



曲仁渝, 严耀超, 杨景芳, 陈琼, 杨光富   

  1. 华中师范大学化学学院 农药与化学生物学教育部重点实验室 武汉 430079
  • 收稿日期:2019-01-26 修回日期:2019-03-04 发布日期:2019-03-21
  • 通讯作者: 陈琼, 杨光富;
  • 基金资助:


Design, Synthesis and Bioactivity of New Pyrimidyl-salicylate Inhibitors

Qu Renyu, Yan Yaochao, Yang Jingfang, Chen Qiong, Yang Guangfu   

  1. Key Laboratory of Pesticide and Chemical Biology, College of Chemistry, Central China Normal University, Wuhan 430079
  • Received:2019-01-26 Revised:2019-03-04 Published:2019-03-21
  • Contact: 10.6023/cjoc201901043;
  • Supported by:

    Project supported by the National Key Research and Development Program of China (No. 2018YFD0200102) and the National Natural Science Foundation of China (Nos. 21837001. 21772058).

Acetohydroxyacid synthase (AHAS) was one of important herbicidal targets. However, the issue of weed resistance to commercial AHAS inhibitors has become one of the largest obstacles for their application. Therefore, there is a high demand to design new anti-resistance AHAS inhibitors. Herein, based on the reported low resistance AHAS inhibitors, a series of pyrimidyl-salicylates with "double oxygen bridge" utilized the "conformation flexibility analysis" strategy were designed. All the synthesized compounds were characterized by 1H NMR, 13C NMR and HRMS. The bioactivity results showed that most of the derivatives displayed good inhibitory activities against P197L mutant. Especially, 2-((4,6-dimethoxypyrimidin-2-yl)oxy)-6-(2-fluoro-4-nitrophenoxy)-4-methylbenzoic acid (6l) was identified as the most potent anti-resistance AHAS inhibitor. In addition, some compounds showed good weed control for resistant Descurainia sophia (P197L AHAS). Most importantly, 2-((4,6-dimethoxypyrimidin-2-yl)oxy)-6-(2-fluorophenoxy)-4-methylbenzoic acid (6b) showed 80% herbicidal activities against sensitive and resistant Descurainia sophia at the dosage of 150 g ai/ha. These results indicated that this type of compounds worth of the further investigation.

Key words: acetohydroxyacid synthase, anti-resistance, P197L mutant, conformation flexibility, resistant weed