Synthesis and Bioactivity Evaluation of Novel N-Pyridylpyrazolemethanamine Derivatives

doi:10.1007/s40242-018-8083-4

Abstract

Abstract: To further explore the structure-activity relationship(SAR) of amide bridge moeity of anthranilic diamides derivatives, a series of N-pyridylpyrazole derivatives was designed, synthesized and their biological activities were evaluated. The chemical structures of novel target compounds were confirmed by ¹H nuclear magnetic resonance (NMR), ¹³C NMR and elemental analyses(EA). Bioassay results of insecticidal activity demonstrated that the target compound 6h displayed 70% lethality rate against oriental armyworms at 200 mg/L. Moreover, most compounds displayed moderate to excellent antifungicidal activities against Fusarium oxysporum f. sp. cucumerinum, Cercospora arachidicola Hori, Botryosphaeria dothidea, Alternaria solani, Gibberella zeae and Phytophthora capsici at 50 mg/L. In particular, compound 6e showed 61.5% and 92.3% inhibition rate against Cercospora arachidicola Hori and Botryosphaeria dothidea, which was superior to the commercial positive control Chlorothalonil. These results will provide a potential clue for exploring novel high-effective agrochemicals.

Key words: Anthranilic diamide, Biological activity, Antifungal agent

HUA Xuewen, WEI Wei, ZHU Liangliang, ZHOU Yunyun. Synthesis and Bioactivity Evaluation of Novel N-Pyridylpyrazolemethanamine Derivatives[J]. Chemical Research in Chinese Universities, 2018, 34(5): 744-750.

References

[1] Marengo J. J., Hidalgo C., Bull R., Biophysical Journal, 1998, 74(3), 1263
[2] Isaacs A. K., Qi S., Sarpong R., Casida J. E., Chemical Research in Toxicology, 2012, 25(8), 1571
[3] Casida J. E., Chemical Research in Toxicology, 2015, 28(4), 560
[4] Gnamm C., Jeanguenat A., Dutton A. C., Grimm C., Kloer D. P., Crossthwaite A. J., Bioorganic & Medicinal Chemistry Letters, 2012, 22(11), 3800
[5] Lahm G. P., Stevenson T. M., Selby T. P., Freudenberger J. H., Cordova D., Flexner L., Bellin C. A., Dubas C. M., Smith B. K., Hughes K. A., Hollingshaus J. G., Clark C. E., Benner E. A., Bioorganic & Medicinal Chemistry Letters, 2007, 17(22), 6274
[6] 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., Bioorganic & Medicinal Chemistry Letters, 2005, 15(22), 4898
[7] Selby T. P., Lahm G. P., Stevenson T. M., Pest Management Science, 2017, 73(4), 658
[8] Selby T. P., Lahm G. P., Stevenson T. M., Hughes K. A., Cordova D., Annan I. B., Barry J. D., Benner E. A., Currie M. J., Pahutski T. F., Bioorganic & Medicinal Chemistry Letters, 2013, 23(23), 6341
[9] Lahm G. P., Cordova D., Barry J. D., Bioorganic & Medicinal Chemistry, 2009, 17(12), 4127
[10] Li Y., Mao M., Li Y., Xiong L., Li Z., Xu J., Physiological Entomology, 2011, 36(3), 230
[11] Forgash A. J., Pesticide Biochemistry and Physiology, 1984, 22(2), 178
[12] Roditakis E., Steinbach D., Moritz G., Vasakis E., Stavrakaki M., Ilias A., Garcia-Vidal L., Martinez-Aguirre M. D. R., Bielza P., Morou E., Silva J. E., Silva W. M., Siqueira Η. A. A., Iqbal S., Troczka B. J., Williamson M. S., Bass C., Tsagkarakou A., Vontas J., Nauen R., Insect Biochemistry and Molecular Biology, 2017, 80, 11
[13] Wu J., Song B. A., Hu D. Y., Yue M., Yang S., Pest Management Science, 2012, 68(5), 801
[14] Chen Y. B., Li J. L., Shao X. S., Xu X. Y., Li Z., Chinese Chemical Letters, 2013, 24(8), 673
[15] Mao M., Li Y., Liu Q., Zhou Y., Zhang X., Xiong L., Li Y., Li Z., Bioorganic & Medicinal Chemistry Letters, 2013, 23(1), 42
[16] Zhou Y., Feng Q., Di F., Liu Q., Wang D., Chen Y., Xiong L., Song H., Li Y., Li Z., Bioorganic & Medicinal Chemistry, 2013, 21(17), 4968
[17] Hua X., Mao W., Fan Z., Ji X., Li F., Zong G., Song H., Li J., Zhou L., Zhou L., Liang X., Wang G., Chen X., Australian Journal of Chemistry, 2014, 67(10), 1491
[18] Mao M. Z., Li Y. X., Zhou Y. Y., Zhang X. L., Liu Q. X., Di F. J., Song H. B., Xiong L. X., Li Y. Q., Li Z. M., Journal of Agricultural and Food Chemistry, 2014, 62(7), 1536
[19] Liu Q., Zhu R., Gao S., Ma S. H., Tang H. J., Yang J. J., Diao Y. M., Wang H. L., Zhu H. J., Pest Management Science, 2017, 73(5), 917
[20] Zhao Y., Li Y., Xiong L., Wang H., Li Z., Chinese Journal of Chemistry, 2012, 30(8), 1748
[21] Kon'Kov K., Bormasheva M., Russian Journal of Organic Chemistry, 2014, 50(11), 1636
[22] Zhang X., Li Y., Ma J., Zhu H., Wang B., Mao M., Xiong L., Li Y., Li Z., Bioorganic & Medicinal Chemistry, 2014, 22(1), 186
[23] Liu J. B., Li Y. X., Zhang X. L., Hua X. W., Wu C. C., Wei W., Wan Y. Y., Cheng D. D., Xiong L. X., Yang N., Song H. B., Li Z. M., Journal of Agricultural and Food Chemistry, 2016, 64(18), 3697
[24] Wang X. J., Tan J., Grozinger K., Betageri R., Kirrane T., Proudfoot J. R., Tetrahedron Letters, 2000, 41(28), 5321
[25] Kang S., Song B., Wu J., He M., Hu D., Jin L., Zeng S., Xue W., Yang S., European Journal of Medicinal Chemistry, 2013, 67, 14
[26] 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., Journal of Agricultural and Food Chemistry, 2013, 61(23), 5483
[27] Zhang J. F., Xu J. Y., Wang B. L., Li Y. X., Xiong L. X., Li Y. Q., Ma Y., Li Z. M., Journal of Agricultural and Food Chemistry, 2012, 60(31), 7565
[28] Liu C., Zhang J., Zhou Y., Wang B., Xiong L., Li Z., Chem. Res. Chinese Universities, 2014, 30(2), 228
[29] Abbott W. S., Journal of Economic Entomology, 1925, 18(2), 265
[30] Hua X., Mao W., Fan Z., Ji X., Li F., Zong G., Song H., Tatiana K., Morzherin Y. Y., Belskaya N. P., Bakulev V. A., Journal of Heterocyclic Chemistry, 2016, 53(3), 865