Fu-Hao Zhang , Huan Zhang , Chang-Xing Sun , Peng-Hui Li , Lin Jiang
{"title":"含氨基甲酸酯部分的2-(甲基硫代)-4-甲基嘧啶类羧酰胺的合成及其杀真菌活性","authors":"Fu-Hao Zhang , Huan Zhang , Chang-Xing Sun , Peng-Hui Li , Lin Jiang","doi":"10.1080/10426507.2023.2192934","DOIUrl":null,"url":null,"abstract":"<div><p>A series of 1-[2-(4-methyl-2-(methylthio)pyrimidine-5-carboxamido)phenyl]ethyl-substitutedphenyl carbamates (<strong>3a</strong>–<strong>3i</strong>) were designed and synthesized, using 4-methyl-2-(methylthio)pyrimidine-5-carboxylic acid, (2-aminophenyl)ethan-1-one, and substituted phenyl isocyanates as starting materials. Their structures were characterized by <sup>1</sup>H NMR, <sup>13</sup>C NMR, IR and HRMS. The <em>in vitro</em> fungicidal activities against <em>Sclerotinia sclerotiorum</em> were evaluated, and the result showed that some compounds displayed moderate antifungal activity with >60% inhibitory rates, among which 1-[2-(4-methyl-2-(methylthio)pyrimidine-5-carboxamido)phenyl] ethyl-(2- methyl phenyl)carbamate (<strong>3a</strong>) and 1-[2-(4-methyl-2-(methylthio)pyrimidine-5- carboxamido)phenyl] ethyl-(3-trifluoromethyl phenyl)carbamate (<strong>3g</strong>) held inhibitory rates of 69.5% and 70.3% at 100 mg/L, respectively. Molecular docking study showed that <strong>3g</strong> can form two hydrogen bonds and a cation-π interaction with succinate dehydrogenase.</p></div>","PeriodicalId":20056,"journal":{"name":"Phosphorus, Sulfur, and Silicon and the Related Elements","volume":null,"pages":null},"PeriodicalIF":1.4000,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"1","resultStr":"{\"title\":\"Synthesis and fungicidal activity of 2-(methylthio)-4-methylpyrimidine carboxamides bearing a carbamate moiety\",\"authors\":\"Fu-Hao Zhang , Huan Zhang , Chang-Xing Sun , Peng-Hui Li , Lin Jiang\",\"doi\":\"10.1080/10426507.2023.2192934\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>A series of 1-[2-(4-methyl-2-(methylthio)pyrimidine-5-carboxamido)phenyl]ethyl-substitutedphenyl carbamates (<strong>3a</strong>–<strong>3i</strong>) were designed and synthesized, using 4-methyl-2-(methylthio)pyrimidine-5-carboxylic acid, (2-aminophenyl)ethan-1-one, and substituted phenyl isocyanates as starting materials. Their structures were characterized by <sup>1</sup>H NMR, <sup>13</sup>C NMR, IR and HRMS. The <em>in vitro</em> fungicidal activities against <em>Sclerotinia sclerotiorum</em> were evaluated, and the result showed that some compounds displayed moderate antifungal activity with >60% inhibitory rates, among which 1-[2-(4-methyl-2-(methylthio)pyrimidine-5-carboxamido)phenyl] ethyl-(2- methyl phenyl)carbamate (<strong>3a</strong>) and 1-[2-(4-methyl-2-(methylthio)pyrimidine-5- carboxamido)phenyl] ethyl-(3-trifluoromethyl phenyl)carbamate (<strong>3g</strong>) held inhibitory rates of 69.5% and 70.3% at 100 mg/L, respectively. Molecular docking study showed that <strong>3g</strong> can form two hydrogen bonds and a cation-π interaction with succinate dehydrogenase.</p></div>\",\"PeriodicalId\":20056,\"journal\":{\"name\":\"Phosphorus, Sulfur, and Silicon and the Related Elements\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":1.4000,\"publicationDate\":\"2023-01-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"1\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Phosphorus, Sulfur, and Silicon and the Related Elements\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S1042650723000345\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q4\",\"JCRName\":\"CHEMISTRY, INORGANIC & NUCLEAR\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Phosphorus, Sulfur, and Silicon and the Related Elements","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1042650723000345","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, INORGANIC & NUCLEAR","Score":null,"Total":0}
Synthesis and fungicidal activity of 2-(methylthio)-4-methylpyrimidine carboxamides bearing a carbamate moiety
A series of 1-[2-(4-methyl-2-(methylthio)pyrimidine-5-carboxamido)phenyl]ethyl-substitutedphenyl carbamates (3a–3i) were designed and synthesized, using 4-methyl-2-(methylthio)pyrimidine-5-carboxylic acid, (2-aminophenyl)ethan-1-one, and substituted phenyl isocyanates as starting materials. Their structures were characterized by 1H NMR, 13C NMR, IR and HRMS. The in vitro fungicidal activities against Sclerotinia sclerotiorum were evaluated, and the result showed that some compounds displayed moderate antifungal activity with >60% inhibitory rates, among which 1-[2-(4-methyl-2-(methylthio)pyrimidine-5-carboxamido)phenyl] ethyl-(2- methyl phenyl)carbamate (3a) and 1-[2-(4-methyl-2-(methylthio)pyrimidine-5- carboxamido)phenyl] ethyl-(3-trifluoromethyl phenyl)carbamate (3g) held inhibitory rates of 69.5% and 70.3% at 100 mg/L, respectively. Molecular docking study showed that 3g can form two hydrogen bonds and a cation-π interaction with succinate dehydrogenase.
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Phosphorus, Sulfur, and Silicon and the Related Elements is a monthly publication intended to disseminate current trends and novel methods to those working in the broad and interdisciplinary field of heteroatom chemistry.
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