SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 12: 4249 - 4257

DOI: https://doi.org/10.6023/cjoc202008014

Synthesis and Biological Activities of Novel N-Pyridylpyrazole Amide Compounds Carrying Isoxazole Unit

  • Zheng Dandan ,
  • Ni Yadan ,
  • Qian Cheng ,
  • Zhang Min ,
  • Zhang Zichan ,
  • Dai Hong ,
  • Zhou Beibei ,
  • Zhang Lifang
Expand
  • College of Chemistry and Chemical Engineering, Nantong University, Nantong, Jiangsu 226019

Received date: 2020-08-10

  Revised date: 2020-09-01

  Online published: 2020-09-09

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).

Fold

Abstract

A series of new N-pyridylpyrazole amides bearing substituted isoxazole moiety were designed and prepared based on chlorantraniliprole. These compounds were structurally determined through 1H NMR, 13C NMR and elemental analyses. Bioassay results displayed that all designed compounds showed a mortality rate of 100% towards Oriental armyworm at the dosage of 500 μg/mL. At the dosage of 100 μg/mL, the mortality rates of four compounds towards Oriental armyworm were 80%~100%. Two compounds had 40%~50% insecticidal activities towards Oriental armyworm at the concentration of 20 μg/mL. At the concentration of 500 μg/mL, five compounds demonstrated 90%~100% insecticidal activities against Aphis medicaginis. Moreover, at the dosage of 500 μg/mL, two compounds exhibited 70%~80% insecticidal activities against Tetranychus cinnabarinus.

Key words： isoxazole; N-pyridylpyrazole; synthesis; biological activity

Cite this article

Zheng Dandan , Ni Yadan , Qian Cheng , Zhang Min , Zhang Zichan , Dai Hong , Zhou Beibei , Zhang Lifang . Synthesis and Biological Activities of Novel N-Pyridylpyrazole Amide Compounds Carrying Isoxazole Unit[J]. Chinese Journal of Organic Chemistry, 2020 , 40(12) : 4249 -4257 . DOI: 10.6023/cjoc202008014

References

[1] Cui, H. W.; He, Y.; Wang, J. H.; Gao, W.; Liu, T.; Qin, M.; Wang, X.; Gao, C.; Wang, Y.; Liu, M. Y.; Yi, Z. F.; Qiu, W. W. Eur. J. Med. Chem. 2015, 95, 240.
[2] Yu, X. L.; Wei, P.; Wang, Z. W.; Liu, Y. X.; Wang, L. Z.; Wang, Q. M. Pest Manage. Sci. 2016, 72, 371.
[3] Sarlauskas, J.; Peciukaityte-Alksne, M.; Misevicine, L.; Maroziene, A.; Polmickaite, E.; Staniulyte, Z.; Cenas, N.; Anusevicius, Z. Bioorg. Med. Chem. Lett. 2016, 26, 512.
[4] Qu, R. Y.; Yang, J. F.; Liu, Y. C.; Chen, Q.; Hao, G. F.; Niu, C. W.; Xi, Z.; Yang, G. F. Pest Manage. Sci. 2017, 73, 1373.
[5] Facchetti, G.; Rimoldi, I. Bioorg. Med. Chem. Lett. 2019, 29, 1257.
[6] He, B.; Dong, J.; Lin, H. Y.; Wang, M. Y.; Li, X. K.; Zheng, B. F.; Chen, Q.; Hao, G. H.; Yang, W. C.; Yang, G. F. J. Agric. Food Chem. 2019, 67, 10844.
[7] Zhao, B. B.; Zhao, C. W.; Hu, X. H.; Xu, S.; Lan, Z.; Guo, Y. P.; Yang, Z. H.; Zhu, W. F.; Zheng, P. W. Eur. J. Med. Chem. 2020, 185, 111809.
[8] Dong, W. L.; Xu, J. Y.; Xiong, L. X.; Li, Z. M. Molecules 2012, 17, 10414.
[9] Mao, M. Z.; Wang, H. Y.; Wang, W.; Ning, B. K.; Li, Y. X.; Xiong, L. X.; Li, Y. Q.; Li, Z. M. Chin. J. Pestic. 2017, 56, 410(in Chinese). (毛明珍, 王海洋, 王威, 宁斌科, 李玉新, 熊丽霞, 李永强, 李正名, 农药, 2017, 56, 410.)
[10] Mao, M. Z.; Wang, L.; Zhang, X. G.; Zhang, Y. Y.; Zeng, L. Y.; Ning, B. K.; Xiong, L. X.; Li, Z. M. Chin. J. Pestic. 2018, 57, 802(in Chinese). (毛明珍, 王伦, 张晓光, 张媛媛, 曾丽媛, 宁斌科, 熊丽霞, 李正名, 农药, 2018, 57, 802.)
[11] 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.
[12] Chai, B.; Peng, Y. W.; Li, H.C.; Zhang, H.; Liu, C. L. Chin. J. Pestic. 2009, 48, 13(in Chinese). (柴宝山, 彭永武, 李慧超, 张弘, 刘长令, 农药, 2009, 48, 13.)
[13] 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.
[14] 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.
[15] Liu, T. T.; Ni, Y.; Zhong, L. K.; Huang, H. Y.; Hu. W. Q.; Xu. T. M.; Tan, C. X. Chin. J. Org. Chem. 2015, 35, 422(in Chinese). (刘婷婷, 倪芸, 钟良坤, 黄红英, 胡伟群, 许天明, 谭成侠, 有机化学, 2015, 35, 422.)
[16] Wang, X.; Tang, C. H.; Wei, G, L.; Long, J. F. J. Heterocycl. Chem. 2017, 54, 3220.
[17] Bi, F. C.; Song, D.; Zhang, N.; Liu, Z. Y.; Gu, X. J.; Hu, C. Y.; Cai, X. K.; Venter, H.; Ma, S. T. Eur. J. Med. Chem. 2018, 159, 90.
[18] Lei, C.; Geng, L.; Xu, X. Y.; Shao, X. S.; Li, Z. Bioorg. Med. Chem. Lett. 2018, 28, 831.
[19] Aksenov, A. V.; Aksenov, D. A.; Arutiunov, N. A.; Aksenov, N. A.; Aleksandrova, E. V.; Zhao, Z. Z.; Du, L. Q.; Kornienko, A.; Rubin, M. J. Org. Chem. 2019, 84, 7123.
[20] Trivedi, J.; Parveen, A.; Rozy, F.; Mitra, A.; Bal, C.; Mitra, D.; Sharon, A. Eur. J. Med. Chem. 2019, 183, 111699.
[21] Zhang, Y. Y.; Gao, S.; Liu, Y. X.; Wang, C.; Jiang, W.; Zhao, L. X.; Fu, Y.; Ye, F. J. Agric. Food Chem. 2020, 68, 3403.
[22] Ravula, S.; Bobbala, R. R.; Kolli, B. J. Heterocycl. Chem. 2020, 57, 2535.
[23] 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.)
[24] Yang, Z. B.; Zhao, Y.; Li, P.; He, Y. J. J. Heterocycl. Chem. 2019, 56, 3042.
[25] Dai, H.; Ye, L. Y.; Zhuang, H. Y.; Dai, B. J.; Fang, Y.; Shi, Y. J. Molecules 2015, 20, 21870.
[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] Tanaka, A.; Terasawa, T.; Hagihara, H.; Sakuma, Y.; Ishibe, N.; Sawada, M.; Takasugi, H.; Tanaka, H. J. Med. Chem. 1998, 41, 2390.
[28] 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.
Options
Outlines

/

〈 〉