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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 6: 1638 - 1646

DOI: https://doi.org/10.6023/cjoc202002024

Synthesis and Bioactivities of Novel Pyrazole Oxime Derivatives Containing a N-Pyridylpyrazole Moiety

  • Xun Xiao ,
  • Ni Yadan ,
  • Li Jinfeng ,
  • Ding Ying ,
  • Zhang Min ,
  • Wang Yang ,
  • Hu Lanping ,
  • Zhou Huanyu ,
  • Yang Bing ,
  • Shi Jian ,
  • Gao Lei ,
  • Dai Hong
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  • a College of Chemistry and Chemical Engineering, Nantong University, Nantong, Jiangsu 226019;
    b Analysis and Testing Center, Nantong University, Nantong, Jiangsu 226019

Received date: 2020-02-18

  Revised date: 2020-03-06

  Online published: 2020-03-11

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 search of novel pyrazole oxime compounds with potent bioactivities, twenty pyrazole oxime derivatives were synthesized by introducing N-pyridylpyrazole unit into pyrazole oxime skeleton, based on the lead of fenpyroximate. The title compounds were structurually characterized by 1H NMR, 13C NMR and elemental analysis. The preliminary bioassay showed that all the title compounds had 100% insecticidal activities against Mythimna separata Walker at 500 μg/mL. Five compounds displayed 100% mortality rate towards Mythimna separata Walker at 100 μg/mL. Two compounds both exhibited 40% mortality rate against Mythimna separata Walker at 20 μg/mL. In addition, three compounds had 40~60% insecticidal activities to Aphis medicaginis at 500 μg/mL. It is worthy of noting that 5-(2-bromophenoxy)-1,3-dimethyl-1H-pyrazole-4-carbaldehyde-O-{1-(3-chloropyridin-2-yl)-3-[(6-chloropyridin-3-yl)methoxy]-1H-pyrazole-5-formyl}oxime (10b) and 5-(4-t-butylphen-oxy)-1,3-dimethyl-1H-pyrazole-4-carbaldehyde-O-{1-(3-chloropyridin-2-yl)-3-[(6-chloropyridin-3-yl)methoxy]-1H-pyrazole-5-formyl}oxime (10k) which have potent insecticidal activities against Mythimna separata Walker, can be utilized in insecticide research with further optimization.

Key words： N-pyridylpyrazole; pyrazole oxime; synthesis; bioactivity

Cite this article

Xun Xiao , Ni Yadan , Li Jinfeng , Ding Ying , Zhang Min , Wang Yang , Hu Lanping , Zhou Huanyu , Yang Bing , Shi Jian , Gao Lei , Dai Hong . Synthesis and Bioactivities of Novel Pyrazole Oxime Derivatives Containing a N-Pyridylpyrazole Moiety[J]. Chinese Journal of Organic Chemistry, 2020 , 40(6) : 1638 -1646 . DOI: 10.6023/cjoc202002024

References

[1] Guan, A. Y.; Qin, Y. K.; Wang, J. F.; Li, B. J. Fluorine Chem. 2013, 156, 120.
[2] Prakash, T. B.; Reddy, G. D.; Padmaja, A.; Padmavathi, V. Eur. J. Med. Chem. 2014, 82, 347.
[3] Pember, S. O.; Mejia, G. L.; Price, T. J.; Pasteris, R. J. Bioorg. Med. Chem. Lett. 2016, 26, 2965.
[4] 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.
[5] Wang, B. L.; Shi, Y. X.; Zhang, S. J.; Ma, Y.; Wang, H. X.; Zhang, L. J.; Wei, W.; Liu, X. H.; Li, Y. H.; Li, Z. M. Eur. J. Med. Chem. 2016, 117, 167.
[6] Liu, X. H.; Zhao, W.; Shen, Z. H.; Xing, J. H.; Xu, T. M.; Peng, W. L. Eur. J. Med. Chem. 2017, 125, 881.
[7] 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.
[8] Mabkhot, Y. N.; Alharbi, M. M.; Al-Showiman, S. S.; Ghabbour, H. A.; Kheder, H. A.; Soliman, S. M.; Frey, W. Chem. Cent. J. 2018, 12, 56.
[9] 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, 446.
[10] Fu, Y.; Zhang, D.; Kang, T.; Guo, Y. Y.; Chen, W. G.; Gao, S.; Ye, F. Bioorg. Med. Chem. Lett. 2019, 29, 570.
[11] 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.)
[12] Wu, J.; Song, B. A.; Hu, D. Y.; Yue, M.; Yang, S. Pest Manage. Sci. 2012, 68, 801.
[13] Wang, B. L.; Ma, Y.; Xiong, L. X.; Li, Z. M. Chin. J. Chem. 2012, 30, 815.
[14] Yan, T.; Yu, S.; Liu, P.; Liu, Z.; Wang, B. L.; Xiong, L. X.; Li, Z. M. Chin. J. Chem. 2012, 30, 919.
[15] 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.
[16] Mao, M.; Li, Y.; Liu, Q.; Zhou, Y.; Zhang, X.; Xiong, L. X.; Li, Y. X.; Li, Z. M. Bioorg. Med. Chem. Lett. 2013, 23, 42.
[17] 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.
[18] Hughes, K. A.; Lahm, G. P.; Selby, T. P.; Stevenson, T. M. WO 2004067528, 2004[Chem. Abstr. 2004, 141, 190786].
[19] Wu, Z. B.; Zhou, X.; Ye, Y. Q.; Wang, P. Y.; Yang, S. Chin. Chem. Lett. 2017, 28, 121.
[20] 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.
[21] Zhang, Y.; Zhu, H. W.; Shang, J. F.; Wang, B. L.; Li, Z. M. Chin. J. Org. Chem. 2019, 39, 861(in Chinese). (张燕, 朱洪伟, 尚俊峰, 王宝雷, 李正名, 有机化学, 2019, 39, 861.)
[22] Shang, J. F.; Liu, Q. X.; Wang, B. L.; Li, Z. M. Chin. J. Org. Chem. 2019, 39, 1489(in Chinese). (尚俊峰, 刘巧霞, 王宝雷, 李正名, 有机化学, 2019, 39, 1489.)
[23] Park, H. J.; Lee, K.; Park, S. J.; Ahn, B.; Lee, J. C.; Cho, H. Y.; Lee, K. I. Bioorg. Med. Chem. Lett. 2005, 15, 3307.
[24] Li, Y.; Zhang, H. Q.; Liu, J.; Yang, X. P.; Liu, Z. J. J. Agric. Food Chem. 2006, 54, 3636.
[25] Ouyang, G. P.; Cai, X. J.; Chen, Z.; Song, B. A.; Bhadury, P. S.; Yang, S.; Jin, L. H.; Xue, W.; Hu, D. Y.; Zeng, S. J. Agric. Food Chem. 2008, 56, 10160.
[26] Dai, H.; Chen, J.; Li, G.; Ge, S. S.; Shi, Y. J.; Fang, Y.; Ling, Y. Bioorg. Med. Chem. Lett. 2017, 27, 950.
[27] Swanson, M. B.; Ivancic, W. A.; Saxena, A. M.; Allton, J. D.; O'Brien, G. K.; Suzuki, T.; Nishizawa, H.; Nokata, M. J. Agric. Food Chem. 1995, 43, 513.
[28] Yang, H. Z.; Li, Q. Agrochemicals 2007, 46, 81(in Chinese). (杨会芝, 李庆, 农药, 2007, 46, 81.)
[29] Fu, C. R.; Peng, J.; Ning, Y.; Liu, M.; Shan, P. C.; Liu, J.; Li, Y. Q.; Hu, F. Z.; Zhu, Y. Q.;Yang, H. Z.; Zou, X. M. Pest Manage. Sci. 2014, 70, 1207.
[30] Yang, Y. Z.; Lin, D. Y.; Fu, C. R.; Zou, X. M. Chin. J. Org. Chem. 2015, 35, 100(in Chinese). (杨亚喆, 林大勇, 傅翠蓉, 邹小毛, 有机化学, 2015, 35, 100.)
[31] Shi, Y. J.; Wang, S. L.; He, H. B.; Li, Y.; Li, Y.; Fang, Y.; Dai, H. Chin. J. Org. Chem. 2015, 35, 1785(in Chinese). (石玉军, 王森林, 何海兵, 李钰, 李阳, 方源, 戴红, 有机化学, 2015, 35, 1785.)
[32] 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.
[33] Dai, H.; Ge, S. S.; Li, G.; Chen, J.; Shi, Y. J.; Ye, L. Y.; Ling, Y. Bioorg. Med. Chem. Lett. 2016, 26, 4504.
[34] Dai, H.; Yao, W.; Fang, Y.; Sun, S. Y.; Shi, Y. J.; Chen, J.; Jiang, G. Q.; Shi, J. Molecules 2017, 22, 2000.
[35] 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.)
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