Abstract
In an attempt to find leading thiazole carboxanilides exhibiting fungicidal activities, we designed and synthesized a new series of 2-sulfursubstituted thiazole carboxanilides via the reaction between 2-sulfur substituted thiazole carboxylic acid chlorides and substituted aniline. The fungicidal activities of the title compounds against Rhizoctonia solani were screened and the results were remarkable. The most potent compound 8i, N-[2,6-dichloro-4-(trifluoromethyl)phenyl]-2-methylthio-4-(trifluoromethyl)thiazole-5-carboxamide, was identified. The fungicidal EC50 of compound 8i against Rhizoctonia solani was 1.28 mg/L, being comparable to that of Thifluzamide. The results indicate that compound 8i can be considered as a lead compound for further research.
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References
Mishra C. B., Kumari S., Tiwari M., Eur. J. Med. Chem., 2015, 92, 1
Huang G., Yang J. C., Hui C., Zhang J., Liu C. L., Agrichemicals, 2011, 50(2), 79
Wu Z. L., Ding N., Lin D., Hu A. X., Ye J., Li G. X., Chem. Res. Chinese Universities, 2016, 32(1), 49
Harrison W. A., Kulka M., Certain 2,4-Dimethyl-5-carboxamidothiazoles, US3725427A, 1973
Kulka M., Von S. B., Harrison W., Fungicidal Use of Certain Carboxamidothiazoles, US3709992A, 1973
Kim D. S., Chun S. J., Jeon J. J., Lee S. W., Joe G. H., Pest Manag. Sci., 2004, 60(10), 1007
Alt G. H., Pratt J. K., Phillips W. G., Srouji G. H., Substituted Thiazoles and Their Use as Fungicide, EP371950, 1990
Liu A. P., Ou X. M., Huang M. Z., Wang X. G., Liu X. P., Wang Y. J., Chen C., Yao J. R., Pest Manag. Sci., 2005, 61, 168
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., Zhen Y. Q., Ren Y. G., He L., Yao J. R., J. Agric. Food Chem., 2008, 56, 6564
Liu A. P., Wang X. G., Chen C., Pei H., Mao C. H., Wang Y. J., Liu X. P., Hu Z. B., Huang L., He H. J., Ou X. M., Huang M. Z., Yao J. R., Pest Manag. Sci., 2009, 65, 232
Yu Y. P., Wu D. X., Huang M. Z., He L., Liu X. P., Zuo J. J., Xiang J., Wu D. X., Fine Chemical Intermediates, 2013, 43(1), 15
Wei W., Cheng D. D., Chen W., Liu J. B., Wan Y. Y., Li Y. X., Li Y. H., Yu S. J., Li Z. M., Chem. Res. Chinese Universities, 2016, 32(2), 195
Bliss C., Ann. Appl. Biol., 1935, 22, 158
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Supported by the National Natural Science Foundation of China(Nos.21272062, 21572050).
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Xue, H., Liu, A., Liu, W. et al. Syntheses and fungicidal activities of thiazole-5-carboxanilides bearing thioether group. Chem. Res. Chin. Univ. 32, 781–785 (2016). https://doi.org/10.1007/s40242-016-6153-z
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DOI: https://doi.org/10.1007/s40242-016-6153-z