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

doi:10.6023/cjoc202005031

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

5-酰基巴比妥酸衍生物的设计、合成及除草活性和分子作用机制研究

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

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 E-mail:leikang@lcu.edu.cn
基金资助:
国家自然科学基金（Nos.31701827，81803360）、中国博士后科学基金（No.2020M671984）、聊城大学博士科研启动基金（No.318051647）、聊城大学大学生创新创业训练（No.CXCY2020Y179）和山东省自然科学基金（Nos.ZR2019PC041，ZR2017BH037）资助项目.

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

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).

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Abstract

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

Cite this article

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.

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5-酰基巴比妥酸衍生物的设计、合成及除草活性和分子作用机制研究

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

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