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.
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Li F. Y., Wang Y. H., Liu J. B., Li Y. X., Li Z. M., Bioorg. Med. Chem., 2019, 27(5), 769
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
Lahm G. P., Selby T. P., Stevenson T. M., Arthropodicidal Anthranilamides, WO03015519(A1), 2003
Alig B., Fischer R., Funke C., Gesing E. R. F., Hense A., Krueger B. W., Loesel P., Arnold C., Anthranilamides, WO2006000336(A2), 2006
Lahm G. P., Novel Anthranilamides Useful for Controlling Invertebrate Pests, WO2006023783 A1, 2006
Jachmann M., Ikegami H., Nokura Y., Hydrazide Compound and Harmful Arthropod-controlling Agent Containing the Same, WO2008126890(A1), 2008
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 Herergo-aromatic and Hetero-cyclic Substituents, WO2007144100(A1), 2007
Strannemalm K., Bbsorbent Product for Men, WO2004004619(A1), 2004
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
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
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
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
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
Zhang Y., Chen Z., Nie J., Zhang F. G., Ma J. A., J. Org. Chem., 2019, 84(11), 7148
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
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
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: https://doi.org/10.1080/10426507.2019.1633530
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
Okada I., Okui S., Takahashi Y., Fukuchi T., Pyrazole Derivative, Insecticidal or Miticidal Composition Containing the Same as the Effective Ingredient, EP289879A1, 1988
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
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
Yang G. H., He J. Z., Duan M. J., Preparation Methods and Application of a Class of Aromatic Amide Compounds (in Chinese), CN108558760A, 2018
Haystead T. A. J., Bodoor K., Hughes P. F., Heat Shock Protein 70(HSP-70) Receptor Ligands, WO2015148714(A1), 2015
Yonetoku Y., Kubota H., Okamoto Y., Ishikawa J., Takeuchi M., Ohta M., Tsukamoto S. I., Bioorg. Med. Chem., 2006, 14(15), 5370
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
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
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
IRAC, EPPO Bulletin, 1990, 20(2), 389
Chen N. C., Bioassay Technology for Pestcides, Beijing Agricultural University Press, Beijing, 1991, 161
Mosmann T., J. Immunol. Meth., 1983, 65(1/2), 55
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Supported by the Scientific Research Program of Tianjin Municipal Education Commission, China (No.2018KJ114).
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Zhang, X., Zhang, H., Liu, J. et al. Synthesis and Biological Evaluation of Novel Anthranilic Diamides Containing N-H/CH3-1H-Pyrazole. Chem. Res. Chin. Univ. 36, 829–834 (2020). https://doi.org/10.1007/s40242-020-9037-1
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DOI: https://doi.org/10.1007/s40242-020-9037-1