Citation: Lei Kang, Li Pan, Zhou Xiaoyun, Wang Shiben, Wang Xuekun, Ji Lusha, Liu Renmin, Xu Xiaohua. Design, Synthesis and Herbicidal Activity of 5-Acylbarbituric Acid Derivatives and Study of Molecular Mode of Action[J]. Chinese Journal of Organic Chemistry, ;2020, 40(9): 2788-2797. doi: 10.6023/cjoc202005031 shu

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

Lei Kang ^a,, ,
Li Pan ^a ,
Zhou Xiaoyun ^a ,
Wang Shiben ^a ,
Wang Xuekun ^a ,
Ji Lusha ^a ,
Liu Renmin ^a ,
Xu Xiaohua ^b

a.
School of Pharmacy, Liaocheng University, Liaocheng, Shandong 252000
b.
State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin 300071

Corresponding author: Lei Kang, leikang@lcu.edu.cn
Received Date: 13 May 2020
Revised Date: 15 June 2020
Available Online: 8 July 2020
Fund Project: the Natural Science Foundation of Shandong Province ZR2017BH037the China Postdoctoral Science Foundation 2020M671984the National Natural Science Foundation of China 81803360the National Natural Science Foundation of China 31701827the Natural Science Foundation of Shandong Province ZR2019PC041Project 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)the Doctoral Research Startup Foundation of Liaocheng University 318051647the Innovation and Entrepreneurship Training Program for College Students of Liaocheng University CXCY2020Y179

Figures(7)

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.
- β-triketone,
- 5-acylbarbituric acid,
- synthesis,
- herbicide,
- phenoxyacetic
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