Synthesis and Herbicidal Activity of Novel β-Methoxyacrylate Derivatives Containing a Substituted Phenylpyridine Moiety

doi:10.1007/s40242-019-9128-z

Abstract

Abstract: In this paper, a series of new β-methoxyacrylate derivatives containing a substituted phenylpyridine moiety was synthesized and bioassayed. The structures of all compounds were confirmed by nuclear magnetic resonance(NMR) and high-resolution mass spectrometry(HRMS). Preliminary bioassays demonstrated that compound 8d showed more than 95% inhibition against Brassica juncea and Chenopodium serotinum at 37.5 g a.i./10⁴ m², when compared with the positive control halauxifen-methyl at 150 g a.i./10⁴ m². The present work demonstrated that compound 8d exhibited the more promising herbicidal activity and may serve as a new herbicidal agent for herbicide.

Key words: β-Methoxyacrylate, Phenylpyridine, Herbicidal activity

CAO Yangyang, CAI Zengfei, ZHANG Wenliang, DU Xiaohua. Synthesis and Herbicidal Activity of Novel β-Methoxyacrylate Derivatives Containing a Substituted Phenylpyridine Moiety[J]. Chemical Research in Chinese Universities, 2019, 35(6): 1008-1011.

References

[1] Sauter H., Steglich W., Anke T., Angew. Chem. Int. Ed., 1999, 38, 1328
[2] Bartlett D. W., Clough J. M., Godfrey C. R. A., Godwin J. R., Hall A. A., Heaney S. P., Maund S. J., Pestic. Outlook, 2001, 12, 143
[3] Bartlett D. W., Clough J. M., Godwin J. R., Hall A. A., Hamer M., Parr-Dobrzanski B., Pest Manage. Sci., 2002, 58, 649
[4] Fisher N., Meunier B., Pest Manage. Sci., 2005, 61, 973
[5] Gisi U., Sierotzki H., Cook A., McCaffery A., Pest Manage. Sci., 2002, 58, 859
[6] Sierotzki H., Parisi S., Steinfeld U., Tenzer I., Poirey S., Gisi U., Pest Manage. Sci., 2000, 56, 833
[7] Beautement K., Clough J. M., de Fraine P. J., Godfrey C. R. A., Pestic. Sci., 1991, 31, 499
[8] Zhao P. L., Liu C. L., Huang W., Wang Y. Z., Yang G. F., J. Agric. Food Chem., 2007, 55, 5697
[9] Liu A. P., Wang X. G., Ou X. M., Huang M. Z., Chen C., Liu S. D., Huang L., Liu X. P., Zhang C. L., Zheng Y. Q., Ren Y. G., He L., Yao J. R., J. Agric. Food Chem., 2008, 56, 6562
[10] Zhao P. L., Wang F., Zhang M. Z., Liu Z. M., Huang W., Yang G. F., J. Agric. Food Chem., 2008, 56, 10767
[11] Chai B. S., Liu C. L., Li H. C., Liu S. W., Xu Y., Song Y. Q., Chang J. B., Chin. Chem. Lett., 2014, 25, 137
[12] Chen J., Shi J., Yu L., Liu D. Y., Gan X. H., Song B. A., J. Agric. Food Chem., 2018, 66, 5335
[13] Chai B. S., Wang S. Y., Yu W. Q., Li H. C., Song C. J., Xu Y., Liu C. L., Chang J. B., Bioorg. Med. Chem. Lett., 2013, 23, 3505
[14] Lee S., Kwon O. S., Lee C. S., Won M., Ban H. S., Ra C. S., Bioorg. Med. Chem. Lett., 2017, 27, 3026
[15] Alzeer J., Chollet J., Heinze-Krauss I., Hubschwerlen C., Matile H., Ridley R. G., J. Med. Chem., 2000, 43, 560
[16] Debona D., Nascimento K. J. T., Gomes J. G. O., Aucique-Perez C. E., Rodrigues F. A., Pestic. Biochem. Physiol., 2016, 130, 8
[17] Herms S., Seehaus K., Koehle H., Conrath U., Plant Physiol., 2002, 130, 120
[18] Becker W. F., Jagow V. G., Anke T., Steglich W., FEBS Lett., 1981, 132, 329
[19] Zhao P. L., Wang L., Zhu X. L., Huang X. Q., Zhan C. G., Wu J. W., Yang G. F., J. Am. Chem. Soc., 2010, 132, 185
[20] Hao G. F., Wang F., Li H., Zhu X. L., Yang W. C., Huang L. S., Wu J. W., Berry E. A., Yang G. F., J. Am. Chem. Soc., 2012, 134, 11168
[21] Hao G. F., Yang S. G., Huang W., Wang L., Shen Y. Q., Tu W. L., Li H., Huang L. S., Wu J. W., Berry E. A., Yang G. F., Sci. Rep., 2015, 5, 13471
[22] Cao Y. Y., Mao D. J., Wang W. W., Du X. H., J. Agric. Food Chem., 2017, 65, 6114
[23] Cao Y. Y., Wang W. W., Du X. H., Chin. J. Struct. Chem., 2019, 38, 1123
[24] Wu Q. Y., Wang G. D., Huang S. W., Lin L., Yang G. F., Molecules, 2010, 13, 9024
[25] Liu Y. Y., Lv K. Z., Li Y., Nan Q. L., Xu J. Y., Sci. Rep., 2018, 8, 7822