Citation: Zhang Yan, Shang Junfeng, Li Huan, Liu Hang, Song Haibin, Wang Baolei, Li Zhengming. Synthesis and Biological Activities of Novel N-(2-(5-(3-Bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl)-1, 3, 4-oxadiazol-2-yl)-4-chloro-6-methylphenyl) Amides[J]. Chinese Journal of Organic Chemistry, ;2020, 40(3): 787-793. doi: 10.6023/cjoc201908024 shu

Synthesis and Biological Activities of Novel N-(2-(5-(3-Bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl)-1, 3, 4-oxadiazol-2-yl)-4-chloro-6-methylphenyl) Amides

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: 16 August 2019
Revised Date: 9 October 2019
Available Online: 7 November 2019
Fund Project: Project supported by the Natural Science Foundation of Tianjin City (No. 17JCYBJC19900), the National Natural Science Foundation of China (No. 21772103) and the National Key Research and Development Program of China (Nos. 2017YFD0200505, 2018YFD0200100)the National Key Research and Development Program of China Nos. 2017YFD0200505Project supported by the Natural Science Foundation of Tianjin City No. 17JCYBJC19900the National Natural Science Foundation of China No. 21772103the National Key Research and Development Program of China 2018YFD0200100

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A series of novel aromatic amide compounds with N-pyridylpyrazole and 1, 3, 4-oxadiazole heterocyclic motifs were successfully synthesized with N-pyridylpyrazole carboxylic acid and 2-amino-3-methylbenzoic acid as the starting materials, via multi-step reactions of nucleophilic addition, cyclization, acylation, etc. The preliminary bioassay tests indicated that most of these compounds have apparent insecticidal activities, among which compounds N-(2-(5-(3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl)-1, 3, 4-oxadiazol-2-yl)-4-chloro-6-methylphenyl)acetamide (8a) and N-(2-(5-(3-bromo-1-(3-chloro-pyridin-2-yl)-1H-pyrazol-5-yl)-1, 3, 4-oxadiazol-2-yl)-4-chloro-6-methylphenyl)-3-chloro-2, 2-dimethylpropanamide (8e) possessed a mortality rate of 70% towards Mythimna separata Walker at the concentration of 200 mg·L^-1. Some of the compounds exhibited good fungicidal activities at 50 mg·L^-1 against Sclerotinia sclerotiorum with the growth inhibitory rates of 54.5%~63.6%, which is more effective than the controls of triadimefon and chlorantraniliprole. Several compounds such as N-(2-(5-(3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl)-1, 3, 4-oxadiazol-2-yl)-4-chloro-6-methylphenyl)pivalamide (8f) and N-(2-(5-(3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl)-1, 3, 4-oxadiazol-2-yl)-4-chloro-6-methylphenyl)-4-fluoroben-zamide (8h) showed moderate fungicidal activity against Physalospora piricola. It is worth noting that compound 8e, which has favorable insecticidal and fungicidal activities towards Mythimna separata Walker and Sclerotinia sclerotiorum respectively, could be used as novel reference structure for new agrochemical innovations.
- N-pyridylpyrazole derivatives,
- 1, 3, 4-oxadiazole,
- synthesis,
- insecticidal activity,
- fungicidal activity
1. [1]
  Oerke E. C., Dehne H. W.Crop Prot., 2004, 23:275. doi: 10.1016/j.cropro.2003.10.001
2. [2]
  Sun N., Shen Z., Zhai Z., Han L., Weng J., Tan C., Liu X.Chin. J. Org. Chem., 2017, 37:2705(in Chinese).
3. [3]
  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.4556
4. [4]
  Zhang Y., Zhu H., Shang J., Wang B., Li Z.Chin. J. Org. Chem., 2019, 39:861(in Chinese).
5. [5]
  Zhan Y., Wang B., Zhang L., Zhang Y., Zhang X., Li Z., Song H.Acta Chim. Sinica, 2015, 11:1173(in Chinese).
6. [6]
  Lahm G. P., Cordova D., Barry J. D.Bioorg. Med. Chem., 2009, 17:4127. doi: 10.1016/j.bmc.2009.01.018
7. [7]
  Selby T. P., Lahm G. P., Stevenson T. M.Pest Manage. Sci., 2017, 73:658. doi: 10.1002/ps.4308
8. [8]
  Clark D. A., Lahm G. P., Smith B. K., Barry J. D., Clagg D. G.Bioorg. Med. Chem., 2008, 16:3163-. doi: 10.1016/j.bmc.2007.12.017
9. [9]
  Liu J.-B., Li F.-Y., Li Y.-X., Zhang X.-L., Hua X.-W., Xiong L.-X., Li Z.-M.Pest Manage. Sci., 2019, 75:1034. doi: 10.1002/ps.5213
10. [10]
  Wu J., Song B.-A., Hu D.-Y., Yue M., Yang S.Pest Manage. Sci., 2012, 68:801. doi: 10.1002/ps.2329
11. [11]
  Mao M., Li Y., Liu Q., Zhou Y., Zhang X., Xiong L., Li Y., Li Z.Bioorg. Med. Chem. Lett., 2013, 23:42. doi: 10.1016/j.bmcl.2012.11.045
12. [12]
  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
13. [13]
  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
14. [14]
  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
15. [15]
  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.4770
16. [16]
  Wang B.-L., Zhu H.-W., Li Z.-M., Zhang X., Yu S.-J., Ma Y., Song H.-B.Pest Manage. Sci., 2019, 75:3273. doi: 10.1002/ps.5449
17. [17]
  Lamberth C., Dinges J.In Bioactive Heterocyclic Compound Classes——Agrochemicals, Eds.: Lamberth C., Dinges J., Wiley- VCH, Weinheim,, 2012, pp. 3~20.
18. [18]
  Whelan M., Chirollo C., Furey A., Cortesi M. L., Anastasio A., Danaher M. J.Agric. Food Chem., 2010, 58:12204. doi: 10.1021/jf102725b
19. [19]
  Noolvi M. N., Patel H. M., Singh N., Gadad A. K., Cameotra S. S., Badiger A.Eur. J. Med. Chem., 2011, 46:4411. doi: 10.1016/j.ejmech.2011.07.012
20. [20]
  Lamberth, C. Pest Manage. Sci., 2013, 69:1106. doi: 10.1002/ps.3615
21. [21]
  Zhang Y., Liu X.-H., Zhan Y.-Z., Zhang L.-Y., Li Z.-M., Li Y.-H., Zhang X., Wang B.-L.Bioorg. Med. Chem. Lett., 2016, 26:4661. doi: 10.1016/j.bmcl.2016.08.059
22. [22]
  Chen J., Gan X., Yi C., Wang S., Yang Y., He F., Hu D., Song B.Chin. J. Chem., 2018, 36:939. doi: 10.1002/cjoc.201800282
23. [23]
  Leiby R. W.J. Heterocycl. Chem., 1984, 21:1825. doi: 10.1002/jhet.5570210650
24. [24]
  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
25. [25]
  Zhou Y., Wei W., Zhu L., Li Y., Li Z.Chem. Biol. Drug Des. 2018, 92:1914. doi: 10.1111/cbdd.13349
26. [26]
  Zhang Y., Li Z., Song H., Wang B.Chin. J. Chem., 2018, 36:635. doi: 10.1002/cjoc.201800110
27. [27]
  Wang B.-L., Zhang L.-Y., Liu X.-H., Ma Y., Zhang Y., Li Z.-M., Zhang X.Bioorg. Med. Chem. Lett., 2017, 27:5457. doi: 10.1016/j.bmcl.2017.10.065
28. [28]
  Zhang Y., Zhan Y.-Z., Ma Y., Hua X.-W., Wei W., Zhang X., Song H.-B., Li Z.-M., Wang B.-L.Chin. Chem. Lett., 2018, 29:441. doi: 10.1016/j.cclet.2017.08.035
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