Synthesis and Biological Evaluation of Novel Anthranilic Diamides Containing N-H/CH3-1H-Pyrazole

doi:10.1007/s40242-020-9037-1

高等学校化学研究 ›› 2020, Vol. 36 ›› Issue (5): 829-834.doi: 10.1007/s40242-020-9037-1

Synthesis and Biological Evaluation of Novel Anthranilic Diamides Containing N-H/CH₃-1H-Pyrazole

ZHANG Xiulan¹, ZHANG Huan¹, LIU Jingbo², XIONG Lixia², LI Zhengming²

1. College of Science, Tianjin University of Science & Technology, Tianjin 300457, P. R. China;
2. State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. China

收稿日期:2019-11-01 修回日期:2019-12-11 出版日期:2020-10-01 发布日期:2020-10-01
通讯作者: LI Zhengming, ZHANG Xiulan E-mail:nkzml@vip.163.com;zxl840327@163.com
基金资助:
Supported by the Scientific Research Program of Tianjin Municipal Education Commission, China(No.2018KJ114).

Synthesis and Biological Evaluation of Novel Anthranilic Diamides Containing N-H/CH₃-1H-Pyrazole

ZHANG Xiulan¹, ZHANG Huan¹, LIU Jingbo², XIONG Lixia², LI Zhengming²

1. College of Science, Tianjin University of Science & Technology, Tianjin 300457, P. R. China;
2. State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. China

Received:2019-11-01 Revised:2019-12-11 Online:2020-10-01 Published:2020-10-01
Contact: LI Zhengming, ZHANG Xiulan E-mail:nkzml@vip.163.com;zxl840327@163.com
Supported by:
Supported by the Scientific Research Program of Tianjin Municipal Education Commission, China(No.2018KJ114).

摘要/Abstract

摘要： In order to systematically study the structure-activity relationship of anthranilic diamides and develop insecticides with simple structure and high efficiency, a series of novel anthranilic diamides containing N-H/CH₃-1H-pyrazole was designed and synthesized. Their chemical structures were characterized by ¹H NMR spectra, high resolution mass spectrometry(HRMS) or ¹³C NMR spectra. The preliminary bioassay results indicated that all title compounds displayed moderate insecticidal activity against oriental armyworm(Mythimna separata) at 200 mg/L and fungicidal activities against six kinds of fungi at 50 mg/L, especially compound 5i showed 50% insecticidal activity at 25 mg/L. In addition, some compounds exhibited certain antitumor activities. It was demonstrated that the introduction of CH₃ group into pyrazole ring was superior to H for the insecticidal activity.

关键词: Anthranilic diamide, Insecticidal activity, Fungicidal activity, Antitumor activity

Abstract: In order to systematically study the structure-activity relationship of anthranilic diamides and develop insecticides with simple structure and high efficiency, a series of novel anthranilic diamides containing N-H/CH₃-1H-pyrazole was designed and synthesized. Their chemical structures were characterized by ¹H NMR spectra, high resolution mass spectrometry(HRMS) or ¹³C NMR spectra. The preliminary bioassay results indicated that all title compounds displayed moderate insecticidal activity against oriental armyworm(Mythimna separata) at 200 mg/L and fungicidal activities against six kinds of fungi at 50 mg/L, especially compound 5i showed 50% insecticidal activity at 25 mg/L. In addition, some compounds exhibited certain antitumor activities. It was demonstrated that the introduction of CH₃ group into pyrazole ring was superior to H for the insecticidal activity.

Key words: Anthranilic diamide, Insecticidal activity, Fungicidal activity, Antitumor activity

ZHANG Xiulan, ZHANG Huan, LIU Jingbo, XIONG Lixia, LI Zhengming. Synthesis and Biological Evaluation of Novel Anthranilic Diamides Containing N-H/CH₃-1H-Pyrazole[J]. 高等学校化学研究, 2020, 36(5): 829-834.

ZHANG Xiulan, ZHANG Huan, LIU Jingbo, XIONG Lixia, LI Zhengming. Synthesis and Biological Evaluation of Novel Anthranilic Diamides Containing N-H/CH₃-1H-Pyrazole[J]. Chemical Research in Chinese Universities, 2020, 36(5): 829-834.

参考文献 30

[1]	Li F. Y., Wang Y. H., Liu J. B., Li Y. X., Li Z. M., Bioorg. Med. Chem., 2019, 27(5), 769
[2]	Liu J. B., Li F. Y., Li Y. X., Zhang X. L., Hua X. W., Xiong L. X., Li Z. M., Pest Manag. Sci., 2019, 75(4), 1034
[3]	Lahm G. P., Selby T. P., Stevenson T. M., Arthropodicidal Anthranilamides, WO03015519(A1), 2003
[4]	Alig B., Fischer R., Funke C., Gesing E. R. F., Hense A., Krueger B. W., Loesel P., Arnold C., Anthranilamides, WO2006000336(A2), 2006
[5]	Lahm G. P., Novel Anthranilamides Useful for Controlling Invertebrate Pests, WO2006023783 A1, 2006
[6]	Jachmann M., Ikegami H., Nokura Y., Hydrazide Compound and Harmful Arthropod-controlling Agent Containing the Same, WO2008126890(A1), 2008
[7]	Alig B., Fischer R., Funke C., Gesing E. R. F., Hense A., Malsam O., Drewes M. W., Goergens U., Murata T., Wada K., Arnold C., Sanwald E., Anthranilic Acid Diamide Derivative with Herero-aromatic and Hetero-cyclic Substituents, WO2007144100(A1), 2007
[8]	Strannemalm K., Bbsorbent Product for Men, WO2004004619(A1), 2004
[9]	Le T. G., Kundu A., Ghoshal A., Nguyen N. H., Preston S., Jiao Y. Q., Ruan B. F., Xue L., Huang F., Keiser J., Hofmann A., Chang B. C. H., Garcia-Bustos J., Jabbar A., Wells T. N. C., Palmer M. J., Gasser R. B., Baell J. B., J. Med. Chem., 2018, 61(23), 10875
[10]	Peng W. L., Xing J. H., Zhu B. C., Xu T. M., Dong D. Z., Zheng Z. W., Yuan J., Huang H. Y., Preparation Methods and Application of a Class of Pyrazolamide Derivatives(in Chinese), CN106883176A, 2017
[11]	Zhong L. K., Zhang F., Jiang T., Liu X. H., Xu T. M., Ding C. R., Chen J., Yuan J., Tan C. X., Heterocycles, 2019, 98(5), 637
[12]	Le T. G., Kundu A., Ghoshal A., Nguyen N. H., Preston S., Jiao Y. Q., Ruan B. F., Xue L., Huang F., Keiser J., Hofmann A., Chang B. C. H., Garcia-Bustos J., Wells T. N. C., Palmer M. J., Jabbar A., Gasser R. B., Baell J. B., J. Med. Chem., 2019, 62(7), 3367
[13]	Liu X. H., Zhao W., Shen Z. H., Xing J. H., Xu T. M., Peng W. L., Eur. J. Med. Chem., 2017, 125(15), 881
[14]	Zhang Y., Chen Z., Nie J., Zhang F. G., Ma J. A., J. Org. Chem., 2019, 84(11), 7148
[15]	Wang L. P., Huang X. Y., Wang W., Zheng X. R., Liu K. Y., Zhang Y. Y., Zhang X. G., Zhang J. G., Ning B. K., Preparation Methods and Application of a Class of Biphenyl Compounds(in Chinese), CN109553578A, 2019
[16]	Liu X. H., Qiao L., Zhai Z. W., Cai P. P., Cantrell C. L., Tan C. X., Weng J. Q., Han L., Wu H. K., Pest Manag. Sci., 2019, 75(11), 2892
[17]	Min L. J., Zhai Z. W., Shi Y. X., Han L., Tan C. X., Weng J. Q., Li B. J., Zhang Y. G., Liu X. H., Phosphorus Sulfur Silicon Relat. Elem., 2019, doi:10.1080/10426507.2019.1633530
[18]	Wang H., Zhai Z. W., Shi Y. X., Tan C. X., Weng J. Q., Han L., Li B. J., Liu X. H., Lett. Drug Des. Discov., 2019, 16(7), 785
[19]	Okada I., Okui S., Takahashi Y., Fukuchi T., Pyrazole Derivative, Insecticidal or Miticidal Composition Containing the Same as the Effective Ingredient, EP289879A1, 1988
[20]	Kojima T., Asano Y., Kurasawa O., Hirata Y., Iwamura N., Wong T. T., Saito B., Tanaka Y., Arai R., Yonemori K., Miyamoto Y., Sagiya Y., Yaguchi M., Shibata S., Mizutani A., Sano O., Adachi R., Satomi Y., Hirayama M., Aoyama K., Hiura Y., Kiba A., Kitamura S., Imamura S., Bioorg. Med. Chem., 2018, 26(9), 2452
[21]	Yaguchi M., Shibata S., Satomi Y., Hirayama M., Adachi R., Asano Y., Kojima T., Hirata Y., Mizutani A., Kiba A., Sagiya Y., Biochem. Biophys. Res. Commun., 2017, 484(3), 493
[22]	Yang G. H., He J. Z., Duan M. J., Preparation Methods and Application of a Class of Aromatic Amide Compounds(in Chinese), CN108558760A, 2018
[23]	Haystead T. A. J., Bodoor K., Hughes P. F., Heat Shock Protein 70(HSP-70) Receptor Ligands, WO2015148714(A1), 2015
[24]	Yonetoku Y., Kubota H., Okamoto Y., Ishikawa J., Takeuchi M., Ohta M., Tsukamoto S. I., Bioorg. Med. Chem., 2006, 14(15), 5370
[25]	Lahm G. P., Selby T. P., Freudenberger J. H., Stevenson T. M., Myers B. J., Seburyamo G., Smith B. K., Flexner L., Clark C. E., Cordova D., Bioorg. Med. Chem. Lett., 2005, 15(22), 4898
[26]	Zhou Z. L., Kher S. M., Cai, S. X., Whittemore E. R., Espitia S. A., Hawkinson J. E., Tran M., Woodward R. M., Weber E., Keana J. F. W., Bioorg. Med. Chem., 2003, 11(8), 1769
[27]	Zhang X. L., Li Y. X., Ma J. L., Zhu H. W., Wang B. L., Mao M. Z., Xiong L. X., Li Y. Q., Li Z. M., Bioorg. Med. Chem., 2014, 22(1), 186
[28]	IRAC, EPPO Bulletin, 1990, 20(2), 389
[29]	Chen N. C., Bioassay Technology for Pestcides, Beijing Agricultural University Press, Beijing, 1991, 161
[30]	Mosmann T., J. Immunol. Meth., 1983, 65(1/2), 55

Synthesis and Biological Evaluation of Novel Anthranilic Diamides Containing N-H/CH₃-1H-Pyrazole

Synthesis and Biological Evaluation of Novel Anthranilic Diamides Containing N-H/CH₃-1H-Pyrazole

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