Chinese Journal of Organic Chemistry >
Synthesis and Herbicidal Activity of 5-(1-Amino-2-phenoxyethylidene)barbituric Acid Derivatives
Received date: 2020-10-30
Revised date: 2020-11-25
Online published: 2021-02-22
Supported by
National Natural Science Foundation of China(31701827); China Postdoctoral Science Foundation(2020M671984); Doctoral Research Startup Foundation of Liaocheng University(318051647); Innovation and Entrepreneurship Training Program for College Students of Liaocheng University(CXCY2020Y179); Natural Science Foundation of Shandong Province(ZR2019PC041); National Natural Science Foundation of China(21675071)
Based on the bioactive enamino diketone skeleton and the structure of our previously reported lead compound 5-acylbarbituric acid I, twenty-six novel 5-(1-amino-2-phenoxyethylidene)barbituric acid derivatives were designed and synthesized. The bioassay results showed that the analog 5-(2-(2-chloro-4-fluorophenoxy)-1-(pentylamino)-ethyli- dene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione (APB-5) displayed excellent post-emergent herbicidal activity, with inhibition 100% against dicotyledonous plants (Brassica campestris, Amaranthus retroflexus), even at a dosage of 187.5 g? ha–1. More importantly, compound APB-5 showed a broad spectrum of weed control and displayed good crop safety toward wheat, maize and millet, when applied at 375 g?ha–1, indicating its remarkable potential as a herbicide. Furthermore, by investigating the phenotypes of Arabidopsis thaliana and analyzing the effect of compound APB-5 on auxin response genes in plants, it was found that compound APB-5 had a herbicidal mechanism similar to auxin-type herbicides, such as 2,4-dichlorophenoxyacetic acid (2,4-D). Taken together, the present work demonstrated that compound APB-5 could serve as a lead structure for further developing novel auxin-type herbicides.
Key words： barbituric acid; enamino diketone; synthesis; herbicidal activity; auxin
Chaochao Wang , Hui Liu , Wei Zhao , Pan Li , Lusha Ji , Renmin Liu , Kang Lei , Xiaohua Xu . Synthesis and Herbicidal Activity of 5-(1-Amino-2-phenoxyethylidene)barbituric Acid Derivatives[J]. Chinese Journal of Organic Chemistry, 2021 , 41(5) : 2063 -2073 . DOI: 10.6023/cjoc202010042
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