Chinese Journal of Organic Chemistry >
Synthesis and Biological Activity of 1,2,4-Triazole Thioether Derivatives Containing Pyrazole Moiety
Received date: 2016-07-20
Revised date: 2016-08-25
Online published: 2016-09-01
Supported by
Project supported by the Zhejiang Provincial Science Foundation of China(No. LY16C14007) and the Research Institute Special Program of Department of Science and Technology of Zhejiang Province(No. 2015F50030).
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.
Key words: pyrazole; 1,2,4-triazole; synthesis; fungicidal activity; herbicidal activity
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
[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.
[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.
[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.
[4] Liu, X. H.; Tan, C. X.; Weng, J. Q. Phosphorus Sulfur Silicon Relat. Elem. 2011, 186, 558.
[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.
[6] Zhao, W.; Shen, Z. H.; Xu, T. M.; Peng, W. L.; Liu, X. H. J. Heterocycl. Chem. 2017, doi:10.1002/jhet.2753.
[7] Ma, H. J.; Zhang, J. H.; Xia, X. D.; Kang, J.; Li, J. H. Pest Manage. Sci. 2015, 71, 1189
[8] Shi, Y. J.; Li, Y.; Fang, Y.; Ye, L. Y.; Chen, J.; Dai, H. Chin. J. Org. Chem. 2016, 36, 1431(in Chinese).(石玉军, 李阳, 方源, 叶林玉, 陈佳, 戴红, 有机化学, 2016, 36, 1431.)
[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] 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.
[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.
[12] Yang, M. Y.; Zhao, W.; Liu, X. H.; Tan, C. X.; Weng, J. Q. Chin. J. Struct. Chem. 2015, 34, 203.
[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] Liu, X. H.; Tan, C. X.; Weng, J. Q. Phosphorus Sulfur Silicon Relat. Elem. 2011, 186, 552.
[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.
[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.
[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] 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.
[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] Liu, C. L. Word Pestic. 1997, 19, 24(in Chinese).(刘长令, 农药译丛, 1997, 19, 24.)
[21] Menozzi, G. J. Heterocycl. Chem. 1987, 24, 1669.
[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.
[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.
/
〈 |
|
〉 |