Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (9): 2788-2797.DOI: 10.6023/cjoc202005031 Previous Articles     Next Articles


雷康a, 李攀a, 周晓芸a, 王世本a, 王学堃a, 冀卢莎a, 柳仁民a, 徐效华b   

  1. a 聊城大学药学院 山东聊城 252000;
    b 南开大学元素有机化学国家重点实验室 天津 300071
  • 收稿日期:2020-05-13 修回日期:2020-06-15 发布日期:2020-07-09
  • 通讯作者: 雷康
  • 基金资助:

Design, Synthesis and Herbicidal Activity of 5-Acylbarbituric Acid Derivatives and Study of Molecular Mode of Action

Lei Kanga, Li Pana, Zhou Xiaoyuna, Wang Shibena, Wang Xuekuna, Ji Lushaa, Liu Renmina, Xu Xiaohuab   

  1. a School of Pharmacy, Liaocheng University, Liaocheng, Shandong 252000;
    b State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin 300071
  • Received:2020-05-13 Revised:2020-06-15 Published:2020-07-09
  • Supported by:
    Project supported by the National Natural Science Foundation of China (Nos. 31701827, 81803360), the China Postdoctoral Science Foundation (No. 2020M671984), the Doctoral Research Startup Foundation of Liaocheng University (No. 318051647), the Innovation and Entrepreneurship Training Program for College Students of Liaocheng University (No. CXCY2020Y179) and the Natural Science Foundation of Shandong Province (Nos. ZR2019PC041, ZR2017BH037).

In an effort to develop novel β-triketone herbicides containing a barbituric acid moiety, a series of 5-acylbarbituric acid derivatives were designed, synthesized, and tested for herbicidal activity. The bioassay results showed that some of the target compounds, such as 5-(2-(2-chloro-4-fluorophenoxy)-1-hydroxyethylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione (BBA-22) and 5-(2-(2-bromo-4-fluorophenoxy)-1-hydroxyethylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione (BBA-27), exhibited excellent herbicidal activity against all tested weeds at a dosage of 1500 g·ha-1. In particular, compound BBA-22 displayed good pre-emergent herbicidal activity against Brassica campestris, Amaranthus retroflexus and Digitaria sanguinalis even at a dosage of 187.5 g·ha-1,surpassing that of a commercial herbicide 2,4-dichlorophenoxyacetic acid (2,4-D). Investigation of the molecular mode of action of compound BBA-22 upon treatment of Arabidopsis thaliana as a model plant revealed that BBA-22 was degraded to the corresponding phenoxyacetic acid, which explains why the herbicidal mechanism is similar to that of auxin-type herbicides. The present study demonstrates that compound BBA-22 is a proherbicide of the corresponding phenoxyacetic acid auxin herbicide and a potential lead compound for further development of novel auxin herbicides.

Key words: β-triketone, 5-acylbarbituric acid, synthesis, herbicide, phenoxyacetic