Design, Synthesis and Herbicidal Activity of Novel Benzothiazole-Pyrimidinediones Compounds

doi:10.6023/cjoc202311025

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (7): 2371-2376.DOI: 10.6023/cjoc202311025 Previous Articles Next Articles

新型苯并噻唑-嘧啶二酮类化合物的设计、合成与除草活性研究

郑佰峰, 左炀, 陈琼, 吴琼友^*()

华中师范大学绿色农药全国重点实验室武汉 430079

收稿日期:2023-11-23 修回日期:2023-12-25 发布日期:2024-04-24
基金资助:
国家重点研发计划(2022YFD1700302); 湖北省重点研发计划(2022BBA0042)

Design, Synthesis and Herbicidal Activity of Novel Benzothiazole-Pyrimidinediones Compounds

Baifeng Zheng, Yang Zuo, Qiong Chen, Qiongyou Wu()

State National Key Laboratory of Green Pesticide, Central China Normal University, Wuhan 430079

Received:2023-11-23 Revised:2023-12-25 Published:2024-04-24
Contact: * E-mail: qywu@mail.ccnu.edu.cn
Supported by:
National Key Research and Development Program of China(2022YFD1700302); Key Research and Development Program of Hubei Province(2022BBA0042)

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Abstract

Based on the benzothiazole-pyrimidinedione derivatives discovered in the our previous report, a series of novel pyrimidinedione derivatives with benzothiazole as the scaffold, which have not been reported in the literature, were designed and synthesized by the strategy of replacing sulfur bridge with oxygen bridge. All of the target compounds were evaluated for their herbicidal activity in the greenhouse assay at a dose of 150 g a.i./ha, and the results showed that some compounds exhibited good herbicidal activity against the tested six weeds. In particular, ethyl 2-((6-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoro- methyl)-3,6-dihydropyrimidin-1(2H)-yl)benzo[d]thiazol-2-yl)oxy)acetate (9ac) showed a broad-spectrum herbicidal activity with more than 85% efficacy against the weeds tested.

Key words: protoporphyrinogen oxidase (PPO) inhibitors, benzothiazole, pyrimidinedione, herbicidal activity, molecular docking

Cite this article

Baifeng Zheng, Yang Zuo, Qiong Chen, Qiongyou Wu. Design, Synthesis and Herbicidal Activity of Novel Benzothiazole-Pyrimidinediones Compounds[J]. Chinese Journal of Organic Chemistry, 2024, 44(7): 2371-2376.

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Fig. & Tab. 5

References 21

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Compd.	X	R	苗后除草活性(150 g a.i./ha)
Compd.	X	R	棒头草	菵草	早熟禾	芥菜	小藜	繁缕
9aa	F	CH₃	100	80	80	100	100	100
9ab	F	CH₂CH₃	100	85	80	100	100	100
9ac	F	CH₂COOCH₂CH₃	100	85	90	100	100	100
9ad	F	CH₂COO(CH₂)₃CH₃	60	70	80	100	100	100
9ba	Cl	CH₃	60	60	60	95	95	70
9bb	Cl	CH₂CH₃	40	0	0	50	90	0
9bc	Cl	CH₂COOCH₂CH₃	60	0	0	70	100	0
9bd	Cl	CH(CH₃)COOCH₃	60	0	50	85	85	0
9be	Cl	CH(CH₃)COOCH₂CH₃	60	0	0	75	95	0
9bf	Cl	CH₂COO(CH₂)₃CH₃	30	0	50	75	95	50
9ca	Br	CH₂COOCH₂CH₃	0	0	0	0	85	0
9cb	Br	CH(CH₃)COOCH₃	60	0	0	70	90	0
9cc	Br	CH(CH₃)COOCH₂CH₃	0	0	0	0	85	0
9cd	Br	CH₂COO(CH₂)₃CH₃	0	0	0	0	85	0
噁草酮			90	80	90	90	100	100

Compd.	X	R	苗后除草活性(150 g a.i./ha)
Compd.	X	R	棒头草	菵草	早熟禾	芥菜	小藜	繁缕
9aa	F	CH₃	100	80	80	100	100	100
9ab	F	CH₂CH₃	100	85	80	100	100	100
9ac	F	CH₂COOCH₂CH₃	100	85	90	100	100	100
9ad	F	CH₂COO(CH₂)₃CH₃	60	70	80	100	100	100
9ba	Cl	CH₃	60	60	60	95	95	70
9bb	Cl	CH₂CH₃	40	0	0	50	90	0
9bc	Cl	CH₂COOCH₂CH₃	60	0	0	70	100	0
9bd	Cl	CH(CH₃)COOCH₃	60	0	50	85	85	0
9be	Cl	CH(CH₃)COOCH₂CH₃	60	0	0	75	95	0
9bf	Cl	CH₂COO(CH₂)₃CH₃	30	0	50	75	95	50
9ca	Br	CH₂COOCH₂CH₃	0	0	0	0	85	0
9cb	Br	CH(CH₃)COOCH₃	60	0	0	70	90	0
9cc	Br	CH(CH₃)COOCH₂CH₃	0	0	0	0	85	0
9cd	Br	CH₂COO(CH₂)₃CH₃	0	0	0	0	85	0
噁草酮			90	80	90	90	100	100

新型苯并噻唑-嘧啶二酮类化合物的设计、合成与除草活性研究

Design, Synthesis and Herbicidal Activity of Novel Benzothiazole-Pyrimidinediones Compounds

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