含吡唑1,2,4-三唑噻二嗪衍生物的合成及抑菌活性

1-苯基-3-甲基-5-氯-4-吡唑甲醛与4-氨基-5-取代苯基-1,2,4-三唑-3-硫酮缩合生成4-(1-苯基-3-甲基-5-氯吡唑次甲亚胺基)-5-(取代苯基)-2H-1,2,4-三唑-3(4H)-硫酮,再烷基加成化为新型含吡唑基5,6-2H-1,2,4-三唑3,4-b]1,3,4]噻二嗪衍生物。 化合物结构经¹H NMR、IR以及元素分析确认。 初步生物活性测试结果表明,在100 mg/L浓度下,化合物8a(3-(2-甲基苯基)-6-(5-氯-2-甲基-4-苯基吡唑)-7-(4-硝基苯基)-5H-1,2,4-三唑3,4-b]1,3,4]噻二嗪)对黄瓜炭疽病的抑制率达90%。

Synthesis and Biological Activity of Novel 1,2,4-Triazolothiadiazine Derivatives Containing Pyrazole Unit

A series of 4-(1-phenyl-3-methyl-5-chloro-1H-pyrazolelideneamino)-5-(substituted aryl)-2H-1,2,4-triazole-3(4H)-thiones was synthesized by the condensation reaction of 5-chloro-1-phenyl-3-methyl-1H-pyrazole-4-aldehyde with 4-amino-5-(substituted phenyl-2H-1,2,4-triazole-3(4H)-thione. Alkylation of compound 6 with ethyl-2-chloroacetate or 1-(chloromethyl)-4-nitrobenzene afforded 5,6-2H-1,2,4]triazolo3,4-b]1,3,4]thiadiazine derivatives containing pyrazole unit. Their structures were confirmed by ¹H NMR, IR and elemental analyses. Preliminary bioassay indicates that the anti-fungicidal activity of compound 8a(3-(2-methyphenyl)-6-(5-chloro-2-methyl-4-phenylpyrazole)-7-(4-nitrophenyl)-5H-1,2,4-triazolo3,4-b]1,3,4]thiadiazine) to Colletotrichum lagenarium at the concentration of 100 mg/L is 90%.