Synthesis and Fungicidal Activity of N-[4-(4-Fluoro)phenyl-2-piperidin-4-ylthiazol-5-yl]pyrimidin-2-yl-N-phenylamines on Phytophthora capsici

Choi, Won-Sik; Nam, Seok-Woo; Ahn, Eun‐Kyung; Park, Byeoung-Soo; Lee, Sung Eun; Kim, Taejun; Choi, In‐Young

doi:10.3839/jksabc.2010.033

Cited by 7 publications

(10 citation statements)

References 21 publications

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“…. Antifungal activities of the tested compounds were evaluated using the whole plant method in a greenhouse, as previously described [6,8]. Briefly, a serial dilution of test compounds was prepared as 40, 35, 25, 20, and 12.5 mg/L.…”

Section: In Vivo Fungicidal Activitymentioning

confidence: 99%

“…Our previous studies were focused on developing new antifungal compounds to selectively control P. capsici [6,8,9]. Therefore, 4-[5-(2-cyclopropylaminopyrimidin-4-yl)-4-(4chloro-2-fluoro-phenyl)thiazol-2-yl]-1-methylpiperidine (Comp I) is found to show potent antifungal activity towards P. capsici [6,8,9]. With these schemes, Comp I appeared to be suitable for use as a leading compound for further synthesis to control P. capsici as well as mosquito larvae.…”

Section: Journal Of Chemistrymentioning

confidence: 99%

“…To reduce the failure of fungal disease management by the currently used fungicides, new compounds with high efficacy and selectivity against target species are desirable [5]. Several studies on the synthesis of thiazole derivatives have 2 Journal of Chemistry already been published [6], reflecting the growing interest in the chemical and biological significance of this class of compounds [7]. 4-[5-(2-Cyclopropylaminopyrimidin-4-yl)-4-(4-fluorophenyl)-thiazol-2-yl]-1-methylpiperidine and 4-[5-(2-cyclopropylaminopyrimidin-4-yl)-4-(4-chloro-2-fluorophenyl)thiazol-2-yl]-1-methylpiperidine (Comp I) showed potential antifungal activity in vivo [8,9].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Pesticidal Activities of 5-(2-Cyclopropylaminopyrimidin-4-yl)-4-(thiophenyl)thiazole Derivatives

Choi

Nam

Kim

et al. 2015

Journal of Chemistry

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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.

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Section: In Vivo Fungicidal Activitymentioning

confidence: 99%

Section: Journal Of Chemistrymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis and Pesticidal Activities of 5-(2-Cyclopropylaminopyrimidin-4-yl)-4-(thiophenyl)thiazole Derivatives

Choi

Nam

Kim

et al. 2015

Journal of Chemistry

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“…For example, the antifungal activity of commercial pyrimethanil ( Figure 2 ) against Alternaria kikuchiana Tanaka was 100% at 0.1 µg mL −1 [ 9 , 10 , 11 , 12 ]. Compound F (EC 50 = 1.03 µg mL −1 ) exhibited better antifungal activity against Phytophthora capsici than dimethomorph (EC 50 = 4.26 µg mL −1 ) ( Figure 2 ) [ 13 ]. Compound G ( Figure 2 ) with excellent antifungal activity (EC 50 = 0.84 µg mL −1 ) against Phytophthora capsici was discovered in 2011 by Nam et al [ 14 ].…”

Section: Introductionmentioning

confidence: 99%

“…Based on our previous works [ 4 , 5 , 6 , 7 , 8 ] and the literature [ 9 , 10 , 11 , 12 , 13 , 14 ], in order to find new pesticides with powerful insecticidal and antifungal properties, we were interested in introducing pyrimidine group into the benzoylurea backbone to design a series of benzoylpyrimidinylurea derivatives ( Figure 3 ). Therefor target compounds 1 – 38 were synthesized and their insecticidal and antifungal activities were evaluated.…”

Section: Introductionmentioning

confidence: 99%

Investigation of Novel Pesticides with Insecticidal and Antifungal Activities: Design, Synthesis and SAR Studies of Benzoylpyrimidinylurea Derivatives

et al. 2018

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In order to find pesticides with insecticidal and antifungal activities, a series of novel benzoyl pyrimidinylurea derivatives were designed and synthesized. All target compounds were identified by 1H-NMR spectroscopy and HRMS. Insecticidal and antifungal activity of these compounds were evaluated and the structure-activity relationships (SAR) were clearly and comprehensively illustrated. Compound 7, with low toxicity to zebrafish (LC50 = 378.387 µg mL−1) showed 100% inhibition against mosquito (Culex pipiens pallens) at 0.25 µg mL−1. Both compounds 19 and 25 exhibited broad-spectrum fungicidal activity (>50% inhibitory activities against 13 phytopathogenic fungi), which were better than those of the commercial pesticide pyrimethanil (>50% inhibitory activities against eight phytopathogenic fungi). Furthermore, compounds 19 and 25 exhibited protective activity against Sclerotinia sclerotiorum on leaves of Brassica oleracea L. during in vivo experiments.

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Design, synthesis, and fungicidal activity of pyrimidinamine derivatives containing pyridin-2-yloxy moiety

Guan

Liu

et al. 2023

Med Chem Res

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Synthesis and Fungicidal Activity of N-[4-(4-Fluoro)phenyl-2-piperidin-4-ylthiazol-5-yl]pyrimidin-2-yl-N-phenylamines on Phytophthora capsici

Cited by 7 publications

References 21 publications

Synthesis and Pesticidal Activities of 5-(2-Cyclopropylaminopyrimidin-4-yl)-4-(thiophenyl)thiazole Derivatives

Synthesis and Pesticidal Activities of 5-(2-Cyclopropylaminopyrimidin-4-yl)-4-(thiophenyl)thiazole Derivatives

Investigation of Novel Pesticides with Insecticidal and Antifungal Activities: Design, Synthesis and SAR Studies of Benzoylpyrimidinylurea Derivatives

Design, synthesis, and fungicidal activity of pyrimidinamine derivatives containing pyridin-2-yloxy moiety

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