Citation: 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 shu

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

Collaborative Innovation Center of Chemical Science and Enginneering(Tianjin), State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071

Corresponding author: Wang Baolei, nkwbl@nankai.edu.cn Li Zhengming, nkzml@vip.163.com
Received Date: 28 August 2018
Revised Date: 22 October 2018
Available Online: 11 March 2018
Fund Project: the National Key Research and Development Program of China 2017YFD0200505the National Natural Science Foundation of China 21772103Project 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)the Natural Science Foundation of Tianjin City 17JCYBJC19900

Figures(5)

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.
- N-pyridylpyrazole derivatives,
- benzotriazinone,
- insecticidal activity,
- fungicidal activity,
- structure-activity relationship
1. [1]
  Oerke, E. C.; Dehne, H. W. Crop Prot. 2004, 23, 275. doi: 10.1016/j.cropro.2003.10.001
2. [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. doi: 10.1002/ps.2017.73.issue-9
3. [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).
4. [4]
  Lamberth, C.; Dinges, J. In Bioactive Heterocyclic Compound Classes-Agrochemicals, Eds.: Lamberth, C.; Dinges, J., Wiley-VCH, Weinheim, 2012, pp. 3~20.
5. [5]
  Lahm, G. P.; Cordova, D.; Barry, J. D. Bioorg. Med. Chem. 2009, 17, 4127. doi: 10.1016/j.bmc.2009.01.018
6. [6]
  Wu, Z.-B.; Zhou, X.; Ye, Y.-Q.; Wang, P.-Y.; Yang, S. Chin. Chem. Lett. 2017, 28, 121. doi: 10.1016/j.cclet.2016.06.010
7. [7]
  Selby, T. P.; Lahm, G. P.; Stevenson, T. M. Pest Manage. Sci. 2017, 73, 658. doi: 10.1002/ps.2017.73.issue-4
8. [8]
  Wu, J.; Song, B.-A.; Hu, D.-Y.; Yue, M.; Yang, S. Pest Manage. Sci. 2012, 68, 801. doi: 10.1002/ps.v68.5
9. [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. doi: 10.1021/jf302446c
10. [10]
  Wang, B.; Ma, Y.; Xiong, L.; Li, Z. Chin. J. Chem. 2012, 30, 815. doi: 10.1002/cjoc.201100386
11. [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. doi: 10.1021/jf4012467
12. [12]
  Yan, T.; Yu, S.; Liu, P.; Liu, Z.; Wang, B.; Xiong, L.; Li, Z. Chin. J. Chem. 2012, 30, 919. doi: 10.1002/cjoc.201100347
13. [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. doi: 10.1002/ps.2018.74.issue-3
14. [14]
  Wang, G. L.; Chen, X.; Chang, Y. N.; Du, D.; Li, Z.; Xu, X. Y. Chin. Chem. Lett. 2015, 26, 1502. doi: 10.1016/j.cclet.2015.10.024
15. [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. doi: 10.1007/s00044-012-9975-3
16. [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). doi: 10.7503/cjcu20170785
17. [17]
  Dong, W.; Xu, J.; Xiong, L.; Liu, X.; Li, Z. Chin. J. Chem. 2009, 27, 579. doi: 10.1002/cjoc.v27:3
18. [18]
  Leiby, R. W. J. Heterocycl. Chem. 1984, 21, 1825. doi: 10.1002/jhet.v21:6
19. [19]
  Zhou, Y.; Wang, B.; Di, F.; Xiong, L.; Yang, N.; Li, Y.; Li, Y.; Li, Z. Bioorg. Med. Chem. Lett. 2014, 24, 2295. doi: 10.1016/j.bmcl.2014.03.077
20. [20]
  Sircar, J. C.; Capiris, T.; Kesten, S. J.; Herzig, D. J. J. Med. Chem. 1981, 24, 735. doi: 10.1021/jm00138a019
21. [21]
  Benhammadi, S.; Iraten, S.; Othman, A. A. Orient. J. Chem. 2016, 32, 2567. doi: 10.13005/ojc
22. [22]
  Sun, N.; Shen, Z.; Zhai, Z.; Han, L.; Weng, J.; Tan, C.; Liu, X. Chin. J. Org. Chem. 2017, 37, 2705(in Chinese).
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