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Fungicidal activities against phytopathogenic fungi of diarylthiazole compound of 4-[5-(2-cyclopropylaminopyrimidin-4-yl)-4-(4-fluorophenyl)thiazol-5-yl]-1-methylpiperidine (I) have been determined to be excellent and compound I was used as the leading compounds in this study. Furthermore, the compound was synthesized by reacting them with five functional groups, 4-fluoro-3-methylphenyl, 4-fluoro-3-chlorophenyl, 4-chloro-2-fluorophenyl, 4-bromo-3-methylphenyl and 2,4-dichlorophenyl groups instead of 4-fluorophenyl group. Also, 2-amino-, 2-(Nethoxycarbonyl)piperidin-4-yl-, and 2-piperidin-4-yl-thiazole were introduced as the leads instead of 2-Nmethylpiperidine-4-yl-thiazol of compound I. VIII-1~VIII-5 and XIII-1~XV-5 compounds were newly synthesized and their structures were confirmed by 1 H-NMR-spectrum. The fungicidal activities of all the synthesized compounds against Phytophthora capsici were examined using the whole plant method. Among the VIII-1 ~VIII-5 and XIII-1~XV-5 chemicals, XIV-3 showed the most potent antifungal activity in vivo. While the EC 50 and EC90 values of the commercial fungicide dimethomorph and I were 4.26±0.02, 14.72±0.05 and 1.01±0.11, 6.31±0.09 mM, those of 4-[5-(2-cyclopropylaminopyrimidin-4-yl)-4-(4-chloro-2-fluorophenyl)thiazol-5-yl]-1methylpiperidine (XIV-3) was 0.98±0.21 and 5.85±0.05 mM. Therefore, XIV-3 can be considered as a viable candidate for the control of plant diseases caused by P. capsici, and further studies will be conducted on the mode of action XIV-3.

Pesticidal activities of 4-[5-(2-cyclopropylaminopyrimidin-4-yl)-4-(4-chloro-2-fluoro-phenyl)thiazol-2-yl]-1-methylpiperidine, designated as Comp I, have been determined against a mosquito larva, Culex pipiens pallens, and a phytopathogenic fungus, Phytophthora capsici. Comp I was used as the leading compound in this study. The compounds were synthesized by reacting them with two functional groups, 3-thiophenyl and 2-thiophenyl groups, instead of 4-chloro-2-fluorophenyl group in Comp I. Other functional groups such as 2-aminothiazole, 2-(1-methylpiperazin-4-yl)thiazole, and 2-(piperazin-4-yl)thiazole were also introduced instead of 2-methylpiperidin-4-yl-thiazole of Comp I. Compounds designated as XIII-6∼XV-7 were newly synthesized and their structures were confirmed by 1 H-and 13 C-NMR spectroscopy. Mosquito larvicidal activities of all the synthesized compounds against C. pipiens pallens were examined and Comp I among them showed the strongest larvicidal activity as 0.513 mM of LC 50 value. The fungicidal activities of all the synthesized compounds against P. capsici were examined using the whole plant method. Among the XIII-6∼XV-7 chemicals, 5-(2-cyclopropylaminopyrimidin-4-yl)-4-(thiophen-2-yl)thiazol-2-amine (VIII-6) showed the most potent antifungal activity in vivo. While the EC 50 value of the commercial fungicide dimethomorph was 4.26 M, EC 50 of VIII-6 was 0.94 M. Therefore, thiazole derivatives can be considered as viable candidates for the control of mosquito larvae and plant diseases.

2 Kyongbo Pharm요 약 본 연구에서 thyme oil의 주성분인 thymol (1)과 유사한 구조를 갖는 4-isopropyl-3-methylphenol (2), 5-isopropyl-3-methylphenol (3), 4-isopropylphenol (4)과 2-isopropylphenol (5) AbstractTwenty five compounds isopropylmethylphenyl benzenesulfonate derivatives of thymol (1), 4-isopropyl-3-methylphenol (2), 5-isopropyl-3-methylphenol (3), 4-isopropylphenol (4), and 2-isopropylphenol (5) derivatives were synthesized. These compounds were analyzed for their structural confirmation with IR, GC/MS, and 1 H-NMR. Synthetic compounds were tested against phytopathogenic fungi activities such as Pyrcularia grisea, Rhizoctonia solani, Phytophthora infestans, Colletotrichum orbiculare, and Sphaerotheca fusca. 2-Isopropyl-5-methylphenyl o-toluenesulfonate (1a), 2-isopropylphenyl 2,4,5-trichloro-benzenesulfonate (5b) and 2-isopropylphenyl 2-methyl-5-nitrobenzenesulfonate (5e) showed a potent in vivo antifungal activity against Pyrcularia grisea, Phytophthora infestans and Sphaerotheca fusca.