1204341-40-1Relevant articles and documents
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
Fan, Zhijin,Yang, Zhikun,Zhang, Haike,Mi,Wang, Huan,Cai, Fei,Zuo, Xlang,Zheng, Qingxiang,Song, Haibin
experimental part, p. 2630 - 2636 (2011/07/07)
Heterocyclic compounds play an important role as the main sources of lead molecules of agrochemicals. Synthesis and biological activity of thiadiazole-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][1,3,4]thiadizole 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-(4Methyl-1,2,3-thiadiazolyl) -6-n-propyl[1,2,4]triazolo[3,4-6][1,3,4]thiadizole and 3-(4-methyl-1,2,3- thiadiazolyl)-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 (EC50) detected for 3-(4-methyl-1,2, 3thiadiazolyl)-6-trichloromethyl[1,2,4]triazolo[3,4-b][1,3,4]thiadizole to six fungi were from 7.28 μmol/L against Pelicularia sasakii (Shirai) to 42.49 μmol/L against Alternaria solan!. The results indicated that thiadiazolecontaining 1,2,4-triazolo[3,4-b][1,3,4]-thiadiazoles were potential fungicide lead compounds.