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

doi:10.6023/cjoc202008014

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (12): 4249-4257.DOI: 10.6023/cjoc202008014 Previous Articles Next Articles

含异噁唑环的新型N-吡啶基吡唑酰胺化合物的合成及生物活性研究

郑丹丹, 倪亚丹, 钱程, 张敏, 张紫婵, 戴红, 周贝贝, 张莉芳

南通大学化学化工学院江苏南通 226019

收稿日期:2020-08-10 修回日期:2020-09-01 发布日期:2020-09-09
通讯作者: 戴红, 张莉芳 E-mail:daihong_2015@aliyun.com;lfzhang@ntu.edu.cn
基金资助:
国家自然科学基金（No.21372135）和南通市科技计划（No.MS12019060）资助项目.

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

College of Chemistry and Chemical Engineering, Nantong University, Nantong, Jiangsu 226019

Received:2020-08-10 Revised:2020-09-01 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).

1. cjoc202008014.pdf(918KB)

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.

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[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.

含异噁唑环的新型N-吡啶基吡唑酰胺化合物的合成及生物活性研究

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

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