Chinese Journal of Organic Chemistry >
Synthesis and Biological Activities of Novel 3-(((3-Bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl) methylene) amino)-substituted-benzo[d] [1,2,3]triazin-4(3H)-ones
Received date: 2018-08-28
Revised date: 2018-10-22
Online published: 2018-11-12
Supported by
Project supported by the Natural Science Foundation of Tianjin City (No. 17JCYBJC19900), the National Key Research and Development Program of China (No. 2017YFD0200505), and the National Natural Science Foundation of China (No. 21772103).
A series of 3-(((3-bromo-1-(3-chloropyridin-2-yl) -1H-pyrazol-5-yl) methylene) amino) substituted-benzo[d] [1,2,3]-triazin-4(3H) -ones were synthesized successfully with ethyl N-pyridylpyrazole carboxylate and substituted aminobenzoic acids as starting materials, via multi-step reactions of reduction, oxidation, nucleophilic addition, condensation and diazotization. The preliminary bioassay tests indicated that most of these compounds have certain insecticidal activities, among which one compound showed a mortality rate of 70% towards Mythimna separata Walker at the test concentration of 200 mg·L-1, some compounds exhibited favorable fungicidal activities at 50 mg·L-1, particularly two compounds which possessed 92.3% growth inhibitory rate against Physalospora piricola, could be used as new fungicidal leading structures for further investigations on this type of compounds.
Zhang Yan , Zhu Hongwei , Shang Junfeng , Wang Baolei , Li Zhengming . Synthesis and Biological Activities of Novel 3-(((3-Bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl) methylene) amino)-substituted-benzo[d] [1,2,3]triazin-4(3H)-ones[J]. Chinese Journal of Organic Chemistry, 2019 , 39(3) : 861 -866 . DOI: 10.6023/cjoc201808033
[1] Oerke, E. C.; Dehne, H. W. Crop Prot. 2004, 23, 275.
[2] Liu, X.-H.; Fang, Y.-M.; Xie, F.; Zhang, R.-R.; Shen, Z.-H.; Tan, C.-X.; Weng, J.-Q.; Xu, T.-M.; Huang, H.-Y. Pest Manage. Sci. 2017, 73, 1900.
[3] Dai, H.; Ding, Y.; Du, X.; Yao, W.; Chen, Q.; Wang, X.; Zhong, S.; Cao, X.; Shi, Y. Chin. J. Org. Chem. 2018, 38, 1755(in Chinese). (戴红, 丁颖, 杜显超, 姚炜, 陈庆文, 王祥龙, 仲苏林, 曹雄飞, 石玉军, 有机化学, 2018, 38, 1755.)
[4] Lamberth, C.; Dinges, J. In Bioactive Heterocyclic Compound Classes-Agrochemicals, Eds.:Lamberth, C.; Dinges, J., Wiley-VCH, Weinheim, 2012, pp. 3~20.
[5] Lahm, G. P.; Cordova, D.; Barry, J. D. Bioorg. Med. Chem. 2009, 17, 4127.
[6] Wu, Z.-B.; Zhou, X.; Ye, Y.-Q.; Wang, P.-Y.; Yang, S. Chin. Chem. Lett. 2017, 28, 121.
[7] Selby, T. P.; Lahm, G. P.; Stevenson, T. M. Pest Manage. Sci. 2017, 73, 658.
[8] Wu, J.; Song, B.-A.; Hu, D.-Y.; Yue, M.; Yang, S. Pest Manage. Sci. 2012, 68, 801.
[9] Zhang, J.-F.; Xu, J.-Y.; Wang, B.-L.; Li, Y.-X.; Xiong, L.-X.; Li, Y.-Q.; Ma, Y.; Li, Z.-M. J. Agric. Food Chem. 2012, 60, 7565.
[10] Wang, B.; Ma, Y.; Xiong, L.; Li, Z. Chin. J. Chem. 2012, 30, 815.
[11] Wang, B.-L.; Zhu, H.-W.; Ma, Y.; Xiong, L.-X.; Li, Y.-Q.; Zhao, Y.; Zhang, J.-F.; Chen, Y.-W.; Zhou, S.; Li, Z.-M. J. Agric. Food Chem. 2013, 61, 5483.
[12] Yan, T.; Yu, S.; Liu, P.; Liu, Z.; Wang, B.; Xiong, L.; Li, Z. Chin. J. Chem. 2012, 30, 919.
[13] Wang, B.-L.; Zhu, H.-W.; Li, Z.-M.; Wang, L.-Z.; Zhang, X.; Xiong, L.-X.; Song, H.-B. Pest Manage. Sci. 2018, 74, 726.
[14] Wang, G. L.; Chen, X.; Chang, Y. N.; Du, D.; Li, Z.; Xu, X. Y. Chin. Chem. Lett. 2015, 26, 1502.
[15] Ibrahim, T. S.; Rashad, A. A.; Abdel-Samii, Z. K.; El-Feky, S. A.; Abdel-Hamid, M. K.; Barakat, W. Med. Chem. Res. 2012, 21, 4369.
[16] Zhang, J.; Li, P.; Wang, Y.; Zhang, C.; Chen, L.; Tang, X.; He, M.; Xue, W. Chem. J. Chin. Univ. 2018, 39, 1455(in Chinese). (张菊平, 李普, 王一会, 张橙, 陈丽娟, 汤旭, 贺鸣, 薛伟, 高等学校化学学报, 2018, 39, 1455.)
[17] Dong, W.; Xu, J.; Xiong, L.; Liu, X.; Li, Z. Chin. J. Chem. 2009, 27, 579.
[18] Leiby, R. W. J. Heterocycl. Chem. 1984, 21, 1825.
[19] Zhou, Y.; Wang, B.; Di, F.; Xiong, L.; Yang, N.; Li, Y.; Li, Y.; Li, Z. Bioorg. Med. Chem. Lett. 2014, 24, 2295.
[20] Sircar, J. C.; Capiris, T.; Kesten, S. J.; Herzig, D. J. J. Med. Chem. 1981, 24, 735.
[21] Benhammadi, S.; Iraten, S.; Othman, A. A. Orient. J. Chem. 2016, 32, 2567.
[22] Sun, N.; Shen, Z.; Zhai, Z.; Han, L.; Weng, J.; Tan, C.; Liu, X. Chin. J. Org. Chem. 2017, 37, 2705(in Chinese). (孙娜波, 沈钟华, 翟志文, 韩亮, 翁建全, 谭成侠, 刘幸海, 有机化学, 2017, 37, 2705.)
/
| 〈 |
|
〉 |
