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Synthesis and Antifungal Activity of 5-[2-(Alkylamino)pyrimidin-4-yl]-4-phenylthiazol-2-cycloalkylamine Derivatives on Phytophthora capsici
Journal of the Korean Society for Applied Biological Chemistry volume 54, pages 395–402 (2011)
Abstract
Fungicidal activity against phytopathogenic fungi of diarylthiazole compound of N-[4-(4-fluoro) phenyl-2-(N-methyl)piperidin-4-yl-thiazol-5-yl]pyrimidin-2-yl-N-(3-hydroxy-methyl)phenylamine (I) have been determined to be a superior and compound I was used as the leading compounds in this study. Furthermore, the synthesis of this compound was conducted by reacting them with four functional groups, N-cyclopropyl, N-cyclopentyl, N-cyclohexyl, and N-isopropylamine instead of the phenylamine. Also, 2-aminothiazole, 2-(N-ethoxycarbonyl)piperidin-4-yl, and 2-piperidin-4-ylthiazole were introduced as the leads instead of the 2-aminothiazole group of compound I. From this scheme, VIII-1∼VIII-4 and XII-1∼XIV-4 compounds were newly synthesized and their structures were confirmed by 1H-NMR-spectrum. The fungicidal activities of all the synthesized compounds against Phytophthora capsici were examined using the whole plant method. While the EC50 value of the commercial fungicide dimethomorph and I was 4.26 mM and that of N-[4-(4-fluoro phenyl-2-(N-methyl)piperidin-4-yl-thiazol-5-yl]pyrimidin-2-yl-cyclopropylamine (XIV-2) on P. capsici was 0.84 mM. Among the XII-1∼XIV-4 chemicals, XIV-2 showed the most potential antifungal activity in vivo. Therefore, XIV-2 can be considered as a viable candidate for the control of phytopathogenic diseases characterized by P. capsici infection, and further studies will be conducted on the mode of action XIV-2.
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Nam, SW., Choi, IY. & Choi, WS. Synthesis and Antifungal Activity of 5-[2-(Alkylamino)pyrimidin-4-yl]-4-phenylthiazol-2-cycloalkylamine Derivatives on Phytophthora capsici . J. Korean Soc. Appl. Biol. Chem. 54, 395–402 (2011). https://doi.org/10.3839/jksabc.2011.062
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DOI: https://doi.org/10.3839/jksabc.2011.062