Synthesis and fungicidal activity of 2-(methylthio)-4-methylpyrimidine carboxamides bearing a carbamate moiety

IF 1.4 4区化学 Q4 CHEMISTRY, INORGANIC & NUCLEAR Phosphorus, Sulfur, and Silicon and the Related Elements Pub Date : 2023-01-01 DOI:10.1080/10426507.2023.2192934

Fu-Hao Zhang , Huan Zhang , Chang-Xing Sun , Peng-Hui Li , Lin Jiang

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引用次数: 1

Abstract

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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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

以4-甲基-2-（甲硫基）嘧啶-5-羧酸、（2-氨基苯基）乙烷-1-酮和取代苯基异氰酸酯为原料，设计并合成了一系列1-[2-（4-甲基-2-）嘧啶-5-甲酰胺基）苯基]乙基取代苯基氨基甲酸酯（3a–3i）。用1H NMR、13C NMR、IR和HRMS对它们的结构进行了表征。对核盘菌的体外杀菌活性进行了评价，结果表明，一些化合物表现出中等的抗真菌活性，>；60%的抑制率，其中1-[2-（4-甲基-2-（甲硫基）嘧啶-5-甲酰胺基）苯基]乙基-（2-甲基苯基）氨基甲酸酯（3a）和1-[2- mg/L。分子对接研究表明，3g可以与琥珀酸脱氢酶形成两个氢键和一个阳离子-π相互作用。

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来源期刊

Phosphorus, Sulfur, and Silicon and the Related Elements 化学-无机化学与核化学

CiteScore

2.60

自引率

7.70%

发文量

103

审稿时长

2.1 months

期刊介绍： 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.