Citation: Dai Hong, Liang Kai, Zhou Qian, Ni Yadan, Qian Cheng, Qian Hongwei, Li Ling, Shi Yujun, Liang Zhipeng, Shi Jian, Gao Lei, Wu Xinxing. Synthesis and Biological Activities of Novel Pyrazole Amide Compounds Containing Substituted Oxazole Unit[J]. Chinese Journal of Organic Chemistry, ;2020, 40(12): 4350-4356. doi: 10.6023/cjoc202007029 shu

Synthesis and Biological Activities of Novel Pyrazole Amide Compounds Containing Substituted Oxazole Unit

Dai Hong ^a ,
Liang Kai ^a ,
Zhou Qian ^a ,
Ni Yadan ^a ,
Qian Cheng ^a ,
Qian Hongwei ^a ,
Li Ling ^a ,
Shi Yujun ^a ,
Liang Zhipeng ^b ,
Shi Jian ^b ,
Gao Lei ^a ,
Wu Xinxing ^a,,

a.
College of Chemistry and Chemical Engineering, Nantong University, Nantong, Jiangsu 226019
b.
Analysis and Testing Center, Nantong University, Nantong, Jiangsu 226019

Corresponding author: Wu Xinxing, wuxinxng@163.com
Received Date: 9 July 2020
Revised Date: 28 July 2020
Available Online: 30 July 2020
Fund Project: Project supported by the National Natural Science Foundation of China (No. 21372135), the Science and Technology Project Fund of Nantong City (No. MS12019060) and the Program of High-Level Talents of Nantong University (No. 03083031)the Program of High-Level Talents of Nantong University 03083031the National Natural Science Foundation of China 21372135the Science and Technology Project Fund of Nantong City MS12019060

Figures(3)

In search of new pyrazole amide derivatives with wonderful bioactivities, fifteen novel pyrazole amide compounds were designed and synthesized by introducing substituted oxazole unit into pyrazole amide skeleton based on the lead compound tebufenpyrad. The structures of the title compounds were confirmed by ¹H NMR, ¹³C NMR and elemental analysis. The preliminary bioassay data exhibited that most of target compounds had more than 90% insecticidal activities against Oriental armyworm at the concentration of 500 μg/mL. At the concentration of 500 μg/mL, one compound displayed 100% mortality rate against Aphis medicaginis. In addition, two compounds showed 30% insecticidal activity against Tetranychus cinnabarinus at the concentration of 500 μg/mL.
- oxazole,
- pyrazole amide,
- synthesis,
- biological activity
1. [1]
  Phatangare, K. R.; Borse, B. N.; Padalkar, V. S.; Patil, V. S.; Gupta, V. D.; Umape, P. G.; Sekar, N. J. Chem. Sci. 2013, 125, 141. doi: 10.1007/s12039-012-0324-3
2. [2]
  Liu, S. H.; Ling, Y.; Yang, X. L. Chin. J. Struct. Chem. 2013, 32, 931.
3. [3]
  Divya, K. R. G.; Sowmya, D. V.; Durgamma, S.; Tharanath, V.; Gopal, D. V. S.; Kumar, M. V. J.; Rao, C. A.; Padmaja, A.; Padmavathi, V. Med. Chem. Res. 2017, 26, 2568. doi: 10.1007/s00044-017-1956-0
4. [4]
  Zhang, D. W.; Guo, J. M.; Zhang, M.; Liu, X.; Ba, M. Y.; Tao, X. Y.; Yu, L. Y.; Guo, Y.; Da, J. G. J. Nat. Prod. 2017, 80, 3242.
5. [5]
  Sangi, D. P.; Meira, Y. G.; Moreira, N. M.; Lopes, T. A.; Leite, M. P.; Pereira-Flores, M. E.; Alvarenga, E. S. Pest. Manage. Sci. 2019, 75, 262. doi: 10.1002/ps.5111
6. [6]
  Singh, I.; Rani, R.; Luxami, V.; Paul, K. Eur. J. Med. Chem. 2019, 166, 267. doi: 10.1016/j.ejmech.2019.01.053
7. [7]
  Chiacchio, M. A.; Lanza, G.; Chiacchio, U.; Giofre, S. V.; Romeo, R.; Iannazzo, D.; Legnani, L. Curr. Med. Chem. 2019, 26, 7337.
8. [8]
  Guo, J. C.; Hao, Y. A.; Ji, X. F.; Wang, Z. W.; Liu, Y. X.; Ma, D. J.; Li, Y. Q.; Pang, H. L.; Ni, J. P.; Wang, Q. M. J. Agric. Food Chem. 2019, 67, 10018. doi: 10.1021/acs.jafc.9b04093
9. [9]
  Wang, M. M.; Zhang, Q. Q.; Yue, K.; Li, Q. S.; Xu, F. B. Chin. J. Org. Chem. 2017, 37, 1774(in Chinese).
10. [10]
  Shi, Y. J.; Du, X. C.; Wang, X. L.; Chen, Q. W.; Li, L.; Dai, H.; Xu, C. Q.; Zhang, J. Y.; Ling, Y. Chin. J. Org. Chem. 2018, 38, 1772(in Chinese).
11. [11]
  Zhou, Qian.; Zheng, D. D.; Shi, Y. J.; Yao, W.; Qian, H. W.; Ding, Y.; Wei, Z. H.; Shen, A. B.; Feng, X.; Shi, J.; Dai, H. Chin. J. Org. Chem. 2018, 38, 3318(in Chinese).
12. [12]
  Liu, Y. Y.; Li, Y.; Chen, N. Q.; Lü, K. Z.; Zhou, C.; Xiong, X. H.; Li, F. S. Molecules 2014, 19, 8140. doi: 10.3390/molecules19068140
13. [13]
  Xiao, J. J.; Liao, M.; Chu, M. J.; Ren, Z. L.; Zhang, X.; Lü, X. H.; Cao, H. Q. Molecules 2015, 20, 807. doi: 10.3390/molecules20010807
14. [14]
  Chen, K.; Liu, Q.; Ni, J. P.; Zhu, H. J.; Li, Y. F.; Wang, Q. Pest. Manage. Sci. 2015, 71, 1503. doi: 10.1002/ps.3954
15. [15]
  Huo, J. Q.; Ma, L. Y.; Zhang, Z.; Fan, Z. J.; Zhang, J. L.; Beryozkina, T. V.; Bakulev, V. A. Chin. Chem. Lett. 2016, 27, 1547. doi: 10.1016/j.cclet.2016.06.019
16. [16]
  Liu, Q.; Zhu, R.; Gao, S.; Ma, S. H.; Tang, H. J.; Yang, J. J.; Diao, Y. M.; Wang, H. L.; Zhu, H. J. Pest. Manage. Sci. 2017, 73, 917. doi: 10.1002/ps.4363
17. [17]
  Iqbal, J.; Ejaz, S. A.; Saeed, A.; Al-Rashida, M. Eur. J. Pharmacol. 2018, 832, 11. doi: 10.1016/j.ejphar.2018.05.011
18. [18]
  Verma, G.; Chashoo, G.; Ali, A.; Khan, M. F.; Akhtar, W.; Ali, I.; Akhtar, M.; Alam, M. M.; Saquiquzzaman, M. Bioorg. Chem. 2018, 77, 106. doi: 10.1016/j.bioorg.2018.01.007
19. [19]
  Deng, X. L.; Zhou, X. M.; Wang, Z. Y.; Rui, C. H.; Yang, X. L. Chin. J. Struct. Chem. 2018, 37, 551.
20. [20]
  Jiang, B. B.; Jin, X. Y.; Dong, Y. W.; Guo, B. B.; Cui, L.; Deng, X. L.; Zhang, L.; Yang, Q.; Li, Y. X.; Yang, X. L.; Smagghe, G. J. Agric. Food Chem. 2020, 68, 6347. doi: 10.1021/acs.jafc.0c00522
21. [21]
  Yang, J. Y.; Tian, Y. R. Modern. Agrochem. 2002, (2), 11(in Chinese). doi: 10.3969/j.issn.1671-5284.2002.02.004
22. [22]
  Fan, W. Z.; Gu, B. Q.; Zhu, W. Q.; Zhang, Y. B. Modern. Agrochem. 2005, (4), 9(in Chinese).
23. [23]
  Chai, B. S.; Lin, D.; Liu, Y. X.; Liu, C. L. Chin. J. Pestic. 2007, 46, 148(in Chinese). doi: 10.3969/j.issn.1006-0413.2007.03.002
24. [24]
  Liu, J. B.; Li, Y. X.; Zhang, X. L.; Hua, X. W.; Wu, C. C.; Wei, W.; Wan, Y. Y.; Cheng, D. D.; Xiong, L. X.; Yang, N.; Song, H. B.; Li, Z. M. J. Agric. Food Chem. 2016, 64, 3697. doi: 10.1021/acs.jafc.6b00380
25. [25]
  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
26. [26]
  Dai, H.; Yao, W.; Fang, Y.; Sun, S. Y.; Shi, Y. J.; Chen, J.; Jiang, G. Q.; Shi, J. Molecules 2017, 22, 2000. doi: 10.3390/molecules22122000
27. [27]
  Wei, F.; Zhao, B. X.; Huang, B.; Zhang, L.; Sun, C. H.; Dong, W. L.; Shin, D. S.; Miao, J. Y. Bioorg. Med. Chem. Lett. 2006, 16, 6342. doi: 10.1016/j.bmcl.2006.09.008
28. [28]
  Wang, X. R.; Lin, X. H.; Xu, X. Q.; Li, W.; Hao, L. J.; Liu, C. C.; Zhao, D. M.; Cheng, M. S. Molecules 2017, 22, 1925. doi: 10.3390/molecules22111925
29. [29]
  Zhu, Y.; Zheng, D. D.; Ni, Y. D.; Li, J. F.; Zhou, H. Y.; Hu, L. P.; Li, L.; Ju, J. F.; Chen, J. Z.; Li, H.; Shi, Y. J.; Dai, H. Chin. J. Org. Chem. 2020, 40, 774(in Chinese).
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