Synthesis and Pesticidal Activities of 5-(2-Cyclopropylaminopyrimidin-4-yl)-4-(thiophenyl)thiazole Derivatives
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 leadin...
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| Format: | Article |
| Language: | English |
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Wiley
2015-01-01
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| Series: | Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2015/241793 |
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| author | Won-Sik Choi Seok-Woo Nam Il-Doo Kim Seung-Han Kim Kun-Ho Park In-Kyung Bae Eun-Sil Park Hwang-Ju Jeon Sung-Eun Lee |
| author_facet | Won-Sik Choi Seok-Woo Nam Il-Doo Kim Seung-Han Kim Kun-Ho Park In-Kyung Bae Eun-Sil Park Hwang-Ju Jeon Sung-Eun Lee |
| author_sort | Won-Sik Choi |
| collection | DOAJ |
| description | 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 1H- and 13C-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 LC50 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 EC50 value of the commercial fungicide dimethomorph was 4.26 μM, EC50 of VIII-6 was 0.94 μM. Therefore, thiazole derivatives can be considered as viable candidates for the control of mosquito larvae and plant diseases. |
| format | Article |
| id | doaj-art-a0813a355a7f45dc8731a541ad817833 |
| institution | Kabale University |
| issn | 2090-9063 2090-9071 |
| language | English |
| publishDate | 2015-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Journal of Chemistry |
| spelling | doaj-art-a0813a355a7f45dc8731a541ad8178332025-02-03T01:21:49ZengWileyJournal of Chemistry2090-90632090-90712015-01-01201510.1155/2015/241793241793Synthesis and Pesticidal Activities of 5-(2-Cyclopropylaminopyrimidin-4-yl)-4-(thiophenyl)thiazole DerivativesWon-Sik Choi0Seok-Woo Nam1Il-Doo Kim2Seung-Han Kim3Kun-Ho Park4In-Kyung Bae5Eun-Sil Park6Hwang-Ju Jeon7Sung-Eun Lee8Department of Life Science and Biotechnology, Soonchunhyang University, Asan 336-745, Republic of KoreaDepartment of Life Science and Biotechnology, Soonchunhyang University, Asan 336-745, Republic of KoreaDepartment of Life Science and Biotechnology, Soonchunhyang University, Asan 336-745, Republic of KoreaDepartment of Life Science and Biotechnology, Soonchunhyang University, Asan 336-745, Republic of KoreaDepartment of Chemistry, University of California, Berkeley, CA 94720, USASchool of Applied Biosciences, Kyungpook National University, Daegu 702-701, Republic of KoreaSchool of Applied Biosciences, Kyungpook National University, Daegu 702-701, Republic of KoreaSchool of Applied Biosciences, Kyungpook National University, Daegu 702-701, Republic of KoreaSchool of Applied Biosciences, Kyungpook National University, Daegu 702-701, Republic of KoreaPesticidal 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 1H- and 13C-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 LC50 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 EC50 value of the commercial fungicide dimethomorph was 4.26 μM, EC50 of VIII-6 was 0.94 μM. Therefore, thiazole derivatives can be considered as viable candidates for the control of mosquito larvae and plant diseases.http://dx.doi.org/10.1155/2015/241793 |
| spellingShingle | Won-Sik Choi Seok-Woo Nam Il-Doo Kim Seung-Han Kim Kun-Ho Park In-Kyung Bae Eun-Sil Park Hwang-Ju Jeon Sung-Eun Lee Synthesis and Pesticidal Activities of 5-(2-Cyclopropylaminopyrimidin-4-yl)-4-(thiophenyl)thiazole Derivatives Journal of Chemistry |
| title | Synthesis and Pesticidal Activities of 5-(2-Cyclopropylaminopyrimidin-4-yl)-4-(thiophenyl)thiazole Derivatives |
| title_full | Synthesis and Pesticidal Activities of 5-(2-Cyclopropylaminopyrimidin-4-yl)-4-(thiophenyl)thiazole Derivatives |
| title_fullStr | Synthesis and Pesticidal Activities of 5-(2-Cyclopropylaminopyrimidin-4-yl)-4-(thiophenyl)thiazole Derivatives |
| title_full_unstemmed | Synthesis and Pesticidal Activities of 5-(2-Cyclopropylaminopyrimidin-4-yl)-4-(thiophenyl)thiazole Derivatives |
| title_short | Synthesis and Pesticidal Activities of 5-(2-Cyclopropylaminopyrimidin-4-yl)-4-(thiophenyl)thiazole Derivatives |
| title_sort | synthesis and pesticidal activities of 5 2 cyclopropylaminopyrimidin 4 yl 4 thiophenyl thiazole derivatives |
| url | http://dx.doi.org/10.1155/2015/241793 |
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