SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF N-(4-METHOXYPHENYL)ACETAMIDE AND N-PHENYLACETAMIDE DERIVATIVES

E. S. Sycheva, D. Markina, M. Mukanova, L. Boltayeva, O. Seilkhanov
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Abstract

Particular attention in the cultivation of industrial and agricultural crops is paid to the fight against pathogenic fungi, which not only lead to significant yield losses, but they are also dangerous to humans. The aim of this work is the synthesis of biologically active compounds in the series of aromatic dithiocarbamic acids based on N-(4-methoxyphenyl)acetamide and N-phenylacetamide and the study of their antifungal and antibacterial activities. Results and discussion. Biologically active aromatic sodium dithiocarbamates were synthesized by the reaction of amines (N-(4-methoxyphenyl)acetamide and N-phenylacetamide) with carbon disulfide in the presence of NaOH in ethanol at a temperature of 25°C in 78 and 85% yields. Thioanhydrides were synthesized by the acylation of sodium acetyl(4-methoxyphenyl)carbamodithioate and sodium acetyl(phenyl)carbamodithioate with acid chlorides (benzoic, 3,4-dimethoxybenzoic, 2-bromobenzoic, and 4-nitrobenzoic) in chloroform at a temperature of 25°C. The corresponding derivatives of aromatic thioanhydrides of dithiocarbamic acids were obtained in 49-88% yields. The structure of the synthesized compounds was established on the basis of elemental analysis data, IR spectra, 1Н and 13С NMR spectroscopy. Antifungal and bactericidal properties of the synthesized compounds were studied against phytopathogenic fungi and Fusarium oxysporum and Pectobacterium carotovorum bacteria. Conclusion. According to the test results, it was revealed that sodium acetyl(4-methoxyphenyl)carbamodithioate at a concentration of 0.4% has a high fungicidal activity and completely inhibits the growth of the Fusarium oxysporum phytopathogen. The maximum zone of inhibition (18 mm) of Pectobacterium carotovorum bacteria was at a concentration of 0.4%.
n -(4-甲氧基苯基)乙酰胺及其衍生物的合成及抗菌活性研究
在工业和农业作物的种植中,特别注意与致病真菌作斗争,这不仅导致重大的产量损失,而且对人类也是危险的。本文以N-(4-甲氧基苯基)乙酰胺和N-苯基乙酰胺为基料,合成具有生物活性的芳香二硫代氨基酸类化合物,并研究其抗真菌和抗菌活性。结果和讨论。以氨基(N-(4-甲氧基苯基)乙酰胺和N-苯基乙酰胺)为原料,在乙醇中NaOH存在下,在25℃条件下合成了具有生物活性的芳香型二硫代氨基甲酸钠,收率为78%和85%。以氯仿为原料,在25℃的温度下,乙酰基(4-甲氧基苯基)氨基甲酸乙酯钠和乙酰基(苯基)氨基甲酸乙酯钠与酸性氯化物(苯甲酸、3,4-二甲氧基苯甲酸、2-溴苯甲酸和4-硝基苯甲酸)酰化合成了硫酸酐。二硫代氨基酸的芳香硫酸酐衍生物的收率为49% ~ 88%。根据元素分析数据、红外光谱、1Н和13С核磁共振光谱确定了合成化合物的结构。研究了合成的化合物对植物病原真菌、尖孢镰刀菌和胡萝卜乳杆菌的抑菌抑菌性能。结论。试验结果表明,0.4%浓度的乙酰(4-甲氧基苯基)氨基硫代酸钠具有较高的杀真菌活性,能完全抑制尖孢镰刀菌的生长。当浓度为0.4%时,对胡萝卜乳杆菌的最大抑制区为18 mm。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
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