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

  • 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

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  • 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.
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    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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