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首页> 外文期刊>Journal of Agricultural and Food Chemistry >Synthesis, Crystal Structure, and Biological Activity of 4-Methyl-1,2,3-thiadiazole-Containing 1,2,4-Triazolo[3,4-b][1,3,4]thiadiazoles
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Synthesis, Crystal Structure, and Biological Activity of 4-Methyl-1,2,3-thiadiazole-Containing 1,2,4-Triazolo[3,4-b][1,3,4]thiadiazoles

机译：含4-甲基-1,2,3-噻二唑的1,2,4-三唑[3,4-b] [1,3,4]噻二唑的合成，晶体结构和生物活性

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摘要

Heterocyclic compounds play an important role as the main sources of lead molecules of agrochemi-cals. Synthesis and biological activity of thiadtazole-containing 1,2,4-triazolo[3,4-b][1,3,4]-thiadiazoles were seldom reported. To find novel lead compounds with various biological activities, a series of 6-substituted-3-(4-methyl-1,2,3-thiadiazolyl)[1,2,4]triazolo[3,4-b][1,3,4]thiadizoles were rationally designed and synthesized according to the principle of combinations of bioactive substructures by the condensation of 3-(4-methyl-1,2,3-thiadiazolyl)-4-amino-1,2,4-triazole-5-thione with various carboxylic acids and phosphorus oxychloride. All newly synthesized compounds were identified by proton nuclear magnetic resonance (~1H NMR), infrared spectroscopy (IR), electroionization mass spectrometry (EI/MS), and elementary analysis. The crystal structure of 3-(4-methyl-1,2,3-thiadiazolyl)-6-(4-methylphenyl)-[1,2,4]triazolo[3,4-b][1,3,4Jthiadizole was determined by X-ray diffraction crystallography. In this crystal, two intermolecular hydrogen bonds (N2···H-C12 and N3···H-C13), a weak intermolecular interaction (S···S), and the weak pπ-pπ intermolecular interaction were observed. Fungicide screening indicated that all of the target compounds showed certain extent of growth inhibition against fungi tested. 3-(4-Methyl-1,2,3-thiadiazolyl)-6-n-propyl[1,2,4]triazolo[3,4-b)][1,3,4]thiadizole and 3-(4-methyl-1,2,3-thiadia-zolyl)-6-trichloromethyl[1,2,4]triazolo[3,4-b][1,3,4]thiadizole were found to have potential wide spectrum of fungicide activity. The median effective concentrations (EC_(50)) detected for 3-(4-methyl-1,2,3-thiadiazolyl)-6-trichloromethyl[1,2,4]triazolo[3,4-b][1,3,4]thiadizole to six fungi were from 7.28 μmol/L against Pellicularia sasakii (Shirai) to 42.49 μmol/L against Alternate solani. The results indicated that thiadiazole-containing 1,2,4-triazolo[3,4-b][1,3,4]-thiadiazoles were potential fungicide lead compounds.
机译：杂环化合物作为农用化学物质中铅分子的主要来源发挥着重要作用。很少报道含噻唑的1,2,4-三唑[3,4-b] [1,3,4]-噻二唑的合成和生物活性。为了找到具有各种生物活性的新型先导化合物，需要一系列6-取代的3-（4-甲基-1,2,3-噻二唑基）[1,2,4]三唑[3,4-b] [1，根据生物活性亚结构的组合原理，通过3-（4-甲基-1,2,3-噻二唑基）-4-氨基-1,2,4-三唑的缩合，合理设计和合成了3,4]噻二唑-5-硫酮与各种羧酸和三氯氧化磷。所有新合成的化合物均通过质子核磁共振（〜1H NMR），红外光谱（IR），电离质谱（EI / MS）和元素分析鉴定。 3-（4-甲基-1,2,3-噻二唑基）-6-（4-甲基苯基）-[1,2,4]三唑[3,4-b] [1,3,4J噻二唑的晶体结构为通过X射线衍射晶体学测定。在该晶体中，观察到两个分子间氢键（N2···H-C12和N3···H-C13），弱的分子间相互作用（S···S）和弱的pπ-pπ分子间相互作用。杀菌剂筛选表明，所有目标化合物均对测试的真菌显示出一定程度的生长抑制作用。 3-（4-甲基-1,2,3-噻二唑基）-6-正丙基[1,2,4]三唑[3,4-b）] [1,3,4]噻唑和3-（4 -甲基-1,2,3-噻二唑--6）-三氯甲基[1,2,4]三唑[3,4-b] [1,3,4]噻唑具有潜在的广谱杀真菌活性。检测到3-（4-甲基-1,2,3-噻二唑基）-6-三氯甲基[1,2,4]三唑[3,4-b] [1,3]的中位有效浓度（EC_（50）） ，4]噻二唑对六种真菌的抗药性是从7.28μmol/ L（对Sasakii Sashikii（Shirai））到42.49μmol/ L（对备用茄尼）。结果表明，含噻二唑的1,2,4-三唑并[3,4-b] [1,3,4]-噻二唑是潜在的杀菌剂先导化合物。

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