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

  • Baifeng Zheng ,
  • Yang Zuo ,
  • Qiong Chen ,
  • Qiongyou Wu
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  • State National Key Laboratory of Green Pesticide, Central China Normal University, Wuhan 430079

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)

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.

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 . DOI: 10.6023/cjoc202311025

References

[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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