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
收稿日期: 2023-11-23
修回日期: 2023-12-25
网络出版日期: 2024-04-25
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
Received date: 2023-11-23
Revised date: 2023-12-25
Online published: 2024-04-25
Supported by
National Key Research and Development Program of China(2022YFD1700302); Key Research and Development Program of Hubei Province(2022BBA0042)
基于课题组前期研究发现的苯并噻唑-嘧啶二酮衍生物, 以氧桥替换硫桥的策略, 设计并合成了一系列未见文献报道的以苯并噻唑为骨架的新型嘧啶二酮类衍生物. 测试了所有化合物在150 g a.i./ha剂量下的温室盆栽除草活性, 结果表明部分化合物对所测试的6种杂草具有较好的除草活性, 特别是2-((6-氟-5-(3-甲基-2,6-二氧亚基-4-(三氟甲基)-3,6-二氢嘧啶-1(2H)-基)苯并[d]噻唑-2-基)氧)乙酸乙酯(9ac), 对供试杂草均具有85%以上的防效, 表现出广谱的除草活性.
关键词： 原卟啉原氧化酶(PPO)抑制剂; 苯并噻唑; 嘧啶二酮; 除草活性; 分子对接
郑佰峰 , 左炀 , 陈琼 , 吴琼友 . 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[J]. 有机化学, 2024 , 44(7) : 2371 -2376 . DOI: 10.6023/cjoc202311025
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.
| [1] | Wang, D. W.; Zhang, H.; Yu, S. Y.; Zhang, R. B.; Liang, L.; Wang, X.; Yang, H. Z.; Xi, Z. J. Agric. Food Chem. 2021, 69, 14115. |
| [2] | Zhang, R. B.; Yu, S. Y.; Liang, L.; Ismail, I.; Wang, D. W.; Li, Y. H.; Xu, H.; Wen, X.; Xi, Z. J. Agric. Food Chem. 2020, 68, 13672. |
| [3] | Zheng, B. F.; Wang, Z. Z.; Dong, J.; Ma, J. Y.; Zuo, Y.; Wu, Q. Y.; Yang, G. F. J. Agric. Food Chem. 2023, 71, 8746. |
| [4] | Dayan, F. E.; Barker, A.; Tranel, P. J. Pest Manage. Sci. 2018, 74, 2226. |
| [5] | Zheng, B. F.; Zuo, Y.; Huang, G. Y.; Wang, Z. Z.; Ma, J. Y.; Wu, Q. Y.; Yang, G. F. J. Agric. Food Chem. 2023, 71, 14221. |
| [6] | Hao, G. F.; Tan, Y.; Xu, W. F.; Cao, R. J.; Xi, Z.; Yang, G. F. J. Agric. Food Chem. 2014, 62, 7209. |
| [7] | Brzezowski, P.; Ksas, B.; Havaux, M.; Grimm, B.; Chazaux, M.; Peltier, G.; Johnson, X.; Alric, J. Commun. Biol. 2019, 2, 159. |
| [8] | Hao, G. F.; Zhan, C. G.; Yang, G. F. Future Med. Chem. 2014, 6, 597. |
| [9] | Wu, Q. Y.; Jiang, L. L.; Zuo, Y.; Wang, Z. F.; Xi, Z.; Yang, G. F. Chem. Biol. Drug Des. 2014, 84, 431. |
| [10] | Zheng, B. F.; Zuo, Y.; Yang, W. Y.; Liu, H.; Wu, Q. Y.; Yang, G. F. J. Agric. Food. Chem. 2024, 72, 10772. |
| [11] | Zhao, L. X.; Peng, J. F.; Liu, F. Y.; Zou, Y. L.; Gao, S.; Fu, Y.; Ye, F. J. Agric. Food Chem. 2022, 70, 1003. |
| [12] | Hao, G. F.; Zuo, Y.; Yang, S. G.; Yang, G. F. Chimia (Aarau) 2011, 65, 961. |
| [13] | Zheng, B. F.; Yan, Y. C.; Fu, C.; Huang, G. Y.; Zhao, L.; Chen, Q.; Qu, R. Y.; Yang, G. F. Front. Agric. Sci. Eng. 2022, 9, 133. |
| [14] | Duke, S. O.; Dayan, F. E. Pest Manage. Sci. 2022, 78, 1303. |
| [15] | Wang, D. W.; Liang, L.; Xue, Z. Y.; Yu, S. Y.; Zhang, R. B.; Wang, X.; Xu, H.; Wen, X.; Xi, Z. J. Agric. Food Chem. 2021, 69, 4081. |
| [16] | Wang, D. W.; Zhang, R. B.; Yu, S. Y.; Liang, L.; Ismail, I.; Li, Y. H.; Xu, H.; Wen, X.; Xi, Z. J. Agric. Food Chem. 2019, 67, 12382. |
| [17] | Lee, W. H.; Kwon, Y. B.; Kim, J. H.; Lee, K. H.; Maezono, S. M. B.; Choi, J. S.; Seu, Y. B. Bioorg. Med. Chem. 2021, 31, 115959. |
| [18] | Wang, D. W.; Zhang, R. B.; Ismail, I.; Xue, Z. Y.; Liang, L.; Yu, S. Y.; Wen, X.; Xi, Z. J. Agric. Food Chem. 2019, 67, 9254. |
| [19] | Zuo, Y.; Wu, Q. Y.; Su, S. W.; Niu, C. W.; Xi, Z.; Yang, G. F. J. Agric. Food Chem. 2016, 64, 552. |
| [20] | Yang, G. F. Adv. Agrochem, 2022, 1, 85. |
| [21] | Hao, G. F.; Zuo, Y.; Yang, S. G.; Chen, Q.; Zhang, Y.; Yin, C. Y.; Niu, C. W.; Xi, Z.; Yang, G. F. J. Agric. Food Chem. 2017, 65, 5581. |
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