Citation: Zhai Zhiwen, Wang Qiao, Shen Zhonghua, Tan Chengxia, Weng Jianquan, Liu Xinghai. Synthesis and Biological Activity of 1, 2, 4-Triazole Thioether Derivatives Containing Pyrazole Moiety[J]. Chinese Journal of Organic Chemistry, ;2017, 37(1): 232-236. doi: 10.6023/cjoc201607031 shu

Synthesis and Biological Activity of 1, 2, 4-Triazole Thioether Derivatives Containing Pyrazole Moiety

College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014

Corresponding author: Liu Xinghai, xhliu@zjut.edu.cn
Received Date: 20 July 2016
Revised Date: 25 August 2016

Fund Project: the Research Institute Special Program of Department of Science and Technology of Zhejiang Province 2015F50030the Zhejiang Provincial Science Foundation of China LY16C14007

Figures(2)

A series of novel 1, 2, 4-triazole derivatives were synthesized from ethyl trifluoroacetoacetate, triethyl orthoformate, methylhydrazine, phenyl isothiocyanate by multi-step reactions.Their structures were characterized by ¹H NMR, ¹³C NMR, HRMS and X-ray diffraction.The target compounds were evaluated for their fungicidal activity and herbicidal activitiy.The results indicated that some of the title compounds displayed certain fungicidal activities against Colletotrichum orbiculare and herbicidal activity against dicotyledons.
- pyrazole,
- 1, 2, 4-triazole,
- synthesis,
- fungicidal activity,
- herbicidal activity
1. [1]
  Liu, X. H.; Zhai, Z. W.; Xu, X. Y.; Yang, M. Y.; Sun, Z. H.; Weng, J. Q.; Tan, C. X.; Chen, J. Bioorg. Med. Chem. Lett. 2015, 25, 5524. doi: 10.1016/j.bmcl.2015.10.064
2. [2]
  Yang, M. Y.; Zhai, Z. W.; Sun, Z. H.; Yu, S. J.; Liu, X. H.; Weng, J. Q.; Tan, C. X.; Zhao, W. G. J. Chem. Res. 2015, 39, 521. doi: 10.3184/174751915X14400874295745
3. [3]
  Liu, X. H.; Sun, Z. H.; Yang, M. Y.; Tan, C. X.; Weng, J. Q.; Zhang, Y. G.; Ma, Y. Chem. Biol. Drug Des. 2014, 84, 342. doi: 10.1111/cbdd.2014.84.issue-3
4. [4]
  Liu, X. H.; Tan, C. X.; Weng, J. Q. Phosphorus Sulfur Silicon Relat. Elem. 2011, 186, 558. doi: 10.1080/10426507.2010.508060
5. [5]
  Liu, X. H.; Zhao, W.; Shen, Z. H.; Xing, J. H.; Yuan, J.; Yang, G.; Xu, T. M.; Peng, W. L. Bioorg. Med. Chem. Lett. 2016, 26, 3626. doi: 10.1016/j.bmcl.2016.06.004
6. [6]
  Zhao, W.; Shen, Z. H.; Xu, T. M.; Peng, W. L.; Liu, X. H. J. Heterocycl. Chem. 2017, doi:10.1002/jhet.2753. doi: 10.1002/jhet.2753
7. [7]
  Ma, H. J.; Zhang, J. H.; Xia, X. D.; Kang, J.; Li, J. H. Pest Manage. Sci. 2015, 71, 1189 doi: 10.1002/ps.2015.71.issue-8
8. [8]
  Shi, Y. J.; Li, Y.; Fang, Y.; Ye, L. Y.; Chen, J.; Dai, H. Chin. J. Org. Chem. 2016, 36, 1431(in Chinese). doi: 10.6023/cjoc201512019
9. [9]
  Mustafa, G.; Zia-ur-Rehman, M.; Khan, I. U.; Ishtiaq, S.; Hussain, S.; Arshad, M. N.; Asiri, A. M. J. Chem. Res. 2016, 3, 167.
10. [10]
  Fujinaga, M.; Yamasaki, T.; Nengaki, N.; Ogawa, M.; Kumata, K.; Shimoda, Y.; Yui, J. J.; Xie, L.; Zhang, Y. D.; Kawamura, K.; Zhang, M. R. Bioorg. Med. Chem. Lett. 2016, 26, 370. doi: 10.1016/j.bmcl.2015.12.008
11. [11]
  Zhang, L. J.; Yang, M. Y.; Sun, Z. H.; Tan, C. X.; Weng, J. Q.; Wu, H. K.; Liu, X. H. Lett. Drug Des. Discovery 2014, 11, 1107. doi: 10.2174/1570180811666140610212731
12. [12]
  Yang, M. Y.; Zhao, W.; Liu, X. H.; Tan, C. X.; Weng, J. Q. Chin. J. Struct. Chem. 2015, 34, 203.
13. [13]
  Sun, Z. H.; Zhai, Z. W.; Yang, M. Y.; Liu, X. H.; Tan, C. X.; Weng, J. Q. Chin. J. Struct. Chem. 2014, 33, 1779.
14. [14]
  Liu, X. H.; Tan, C. X.; Weng, J. Q. Phosphorus Sulfur Silicon Relat. Elem. 2011, 186, 552. doi: 10.1080/10426507.2010.508059
15. [15]
  Liu, X. H.; Wang, Q.; Sun, Z. H.; Wedge, D. E.; Becnel, J. J.; Estep, A. S.; Tan, C. X.; Weng, J. Q. Pest Manage. Sci. 2017, DOI:10.1002/ps.4370. doi: 10.1002/ps.4370
16. [16]
  Zhai, Z. W.; Shi, Y. X.; Yang, M. Y.; Zhao, W.; Sun, Z. H.; Weng, J. Q.; Tan, C. X.; Liu, X. H.; Li, B. J.; Zhang, Y. G. Lett. Drug Des. Discovery 2016, 13, 521. doi: 10.2174/157018081306160618181757
17. [17]
  Shen, Z. H.; Shi, Y. X.; Yang, M. Y.; Sun, Z. H.; Weng, J. Q.; Tan, C. X.; Liu, X. H.; Li, B. J.; Zhao, W. G. Chin. J. Struct. Chem. 2016, 35, 457.
18. [18]
  Liu, X. H.; Pan, L.; Weng, J. Q.; Tan, C. X.; Li, Y. H.; Wang, B. L.; Li, Z. M. Mol. Diversity 2012, 16, 251. doi: 10.1007/s11030-011-9352-z
19. [19]
  Zhai, Z. W.; Shi, Y. X.; Yang, M. Y.; Sun, Z. H.; Weng, J. Q.; Tan, C. X.; Liu, X. H.; Li, B. J.; Zhang, Y. G. Chin. J. Struct. Chem. 2016, 35, 25.
20. [20]
  Liu, C. L. Word Pestic. 1997, 19, 24(in Chinese).
21. [21]
  Menozzi, G. J. Heterocycl. Chem. 1987, 24, 1669. doi: 10.1002/jhet.v24:6
22. [22]
  Yan, S. L.; Yang, M. Y.; Sun, Z. H.; Min, L. J.; Tan, C. X.; Weng, J. Q.; Wu, H. K.; Liu, X. H. Lett. Drug Des. Discovery 2014, 11, 940. doi: 10.2174/1570180811666140423222141
23. [23]
  Liu, X. H.; Weng, J. Q.; Wang, B. L.; Li, Y. H.; Tan, C. X.; Li, Z. M. Res. Chem. Intermed. 2014, 40, 2605. doi: 10.1007/s11164-013-1113-4
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