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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 6: 1772 - 1778

DOI: https://doi.org/10.6023/cjoc202001028

Synthesis and Bioactivities of Novel Pyrazole Amides Carrying Oxazole Moiety

  • Zhang Min ,
  • Zheng Dandan ,
  • Ni Yadan ,
  • Liang Kai ,
  • Xun Xiao ,
  • Hu Lanping ,
  • Chen Qingwen ,
  • Yang Bing ,
  • Liang Zhipeng ,
  • Ding Ying ,
  • Shi Jian ,
  • Dai Hong
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  • a College of Chemistry and Chemical Engineering, Nantong University, Nantong, Jiangshu 226019;
    b Analysis and Testing Center, Nantong University, Nantong, Jiangshu 226019

Received date: 2020-01-20

  Revised date: 2020-02-27

  Online published: 2020-03-06

Supported by

Project supported by the National Natural Science Foundation of China (No. 21372135) and the Science and Technology Project Fund of Nantong City (No. MS12019060).

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Abstract

In order to find new pyrazole amides with wonderful bioactivities, a series of novel pyrazole amide derivatives were synthesized by introducing substituted oxazole ring into the C-5 position of pyrazole skeleton based on the lead chlorantraniliprole. The aimed compounds were structurally characterized through 1H NMR, 13C NMR and elemental analysis. The preliminary bioassay results exhibited that all the title compounds displayed more than 90% insecticidal activities against Mythimna separata (Walker) at 500 μg/mL. At the dosage of 100 μg/mL, five compounds possessed 90%~100% insecticidal activities against Mythimna separata (Walker), and three compounds exhibited insecticidal property against Aphis craccivora with 90%~100%. Additionally, at the dosage of 500 μg/mL, two compounds possessed insecticidal activity against Tetranychus cinnabarinus with 80%~100%.

Key words： oxazole; pyrazole amide; synthesis; bioactivity

Cite this article

Zhang Min , Zheng Dandan , Ni Yadan , Liang Kai , Xun Xiao , Hu Lanping , Chen Qingwen , Yang Bing , Liang Zhipeng , Ding Ying , Shi Jian , Dai Hong . Synthesis and Bioactivities of Novel Pyrazole Amides Carrying Oxazole Moiety[J]. Chinese Journal of Organic Chemistry, 2020 , 40(6) : 1772 -1778 . DOI: 10.6023/cjoc202001028

References

[1] Guan, A. Y.; Qin, Y. K.; Wang, J. F.; Li, B. J. Fluorine Chem. 2013, 156, 120.
[2] Li, G. Y.; Qian, X. H.; Cui, J. N.; Huang, Q. C.; Zhang, R.; Guan, H. J. Agric. Food Chem. 2006, 54, 125.
[3] Prakash, T. B.; Reddy, G. D.; Padmaja, A.; Padmavathi, V. Eur. J. Med. Chem. 2014, 82, 347.
[4] Ohnmacht, S. A.; Ciancimino, C.; Vignaroli, G.; Gunaratnam, M.; Neidle, S. Bioorg. Med. Chem. Lett. 2013, 23, 5351.
[5] Wang, M. M.; Zhang, Q. Q.; Yue, K.; Li, Q. S.; Xu, F. B. Chin. J. Org. Chem. 2017, 37, 1774(in Chinese). (王梦梦, 张青青, 岳凯, 李庆山, 徐凤波, 有机化学, 2017, 37, 1774.)
[6] Zhou, Q.; 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). (周钱, 郑丹丹, 石玉军, 姚炜, 钱宏炜, 丁颖, 魏中昊, 沈爱宝, 冯霞, 石健, 戴红, 有机化学, 2018, 38, 3318.)
[7] Fu, Y.; Zhang, D.; Kang, T.; Guo, Y. Y.; Chen, W. G.; Gao, S.; Ye, F. Bioorg. Med. Chem. Lett. 2019, 29, 570.
[8] Shi, J. J.; Ren, G. H.; Wu, N. J.; Liu, X. H.; Xu. T. M.; Tan, C. X. Chin. J. Org. Chem. 2017, 37, 2131(in Chinese). (史建俊, 任贵华, 吴宁捷, 刘幸海, 许天明, 谭成侠, 有机化学, 2017, 37, 2131.)
[9] Liu, X. H.; Zhao, W.; Shen, Z. H.; Xing, J. H.; Yuan, J.; Yang, G.; Xu, T. M.; Peng, W. L. Bioorg. Med. Chem. Lett. 2016, 26, 3626.
[10] Liu, X. H.; Zhao, W.; Shen, Z. H.; Xing, J. H.; Xu, T. M.; Peng, W. L. Eur. J. Med. Chem. 2017, 125, 881.
[11] Shi, J. J.; Ren, G. H.; Wu, N. J.; Weng, J. Q.; Xu, T. M.; Liu, X. H.; Tan, C. X. Chin. Chem. Lett. 2017, 28, 1727.
[12] Zhong, L. K.; Jiang, T.; Zhang, F.; Fu, Q.; Liu, X. H.; Xu, T. M.; Ding, C. R.; Chen, J.; Yuan, J.; Tan, C. X. Chin. J. Org. Chem. 2019, 39, 2655(in Chinese). (钟良坤, 江涛, 张帆, 付庆, 刘幸海, 许天明, 丁成荣, 陈杰, 袁静, 谭成侠, 有机化学, 2019, 39, 2655.)
[13] Pirol, S. C.; Caliskan, B.; Durmaz, I.; Atalay, R.; Banoglu, E. Eur. J. Med. Chem. 2014, 87, 140.
[14] Song, H. J.; Liu, Y. X.; Xiong, L. X.; Li, Y. Q.; Yang, N.; Wang, Q. M. J. Agric. Food Chem. 2013, 61, 8730.
[15] Gu, B. Q.; Zhu, W. Q.; Fan, W. Z.; Qian, H.; Liu, J. M.; Zhang, A. Q.; Shen, R. X. Modern Agrochem. 2002, 1, 9(in Chinese). (顾保权, 朱伟清, 范文政, 钱虹, 刘建梅, 张爱庆, 沈荣仙, 现代农药, 2002, 1, 9.)
[16] Fan, W. Z.; Gu, B. Q.; Zhu, W. Q.; Zhang, Y. B. Modern Agrochem. 2005, 4, 9(in Chinese). (范文政, 顾保权, 朱伟清, 张一宾, 现代农药, 2005, 4, 9.)
[17] Zhou, Y. Y.; Wang, B. L.; Di, F. J.; Xiong, L. X.; Yang, N.; Li, Y. Q.; Li, Y. X.; Li, Z. M. Bioorg. Med. Chem. Lett. 2014, 24, 2295.
[18] Kang, S. H.; Song, B. A.; Wu, J.; He, M.; Hu, D. Y.; Jin, L. H.; Zeng, S.; Xue, W.; Yang, S. Eur. J. Med. Chem. 2013, 67, 14.
[19] Zhu, H. W.; Wang, B. L.; Zhang, X. L.; Xiong, L. X.; Yu, S. J.; Li, Z. M. Chem. Res. Chin. Univ. 2014, 30, 409.
[20] 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.
[21] Ding, C. R.; Pan, Y. Y.; Yin, X.; Tan, C. X.; Zhang, G. F. Chin. J. Org. Chem. 2019, 39, 836(in Chinese). (丁成荣, 潘亚运, 殷许, 谭成侠, 张国富, 有机化学, 2019, 39, 836.)
[22] Dai, H.; Yao, W.; Fang, Y.; Sun, S. Y.; Shi, Y. J.; Chen, J.; Jiang, G. Q.; Shi, J. Molecules 2017, 22, 2000.
[23] Huang, P. Q.; Chen, H. Chem. Commun. 2017, 53, 12584..
[24] 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.
[25] 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.
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