含吡唑1,2,4-三唑噻二嗪衍生物的合成及抑菌活性

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

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%。

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-1Hpyrazole-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]triazolo[3,4-b][1,3,4]thiadiazine derivatives containing pyrazole unit. Their structures were confirmed by1 H 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-triazolo[3,4-b][1,3,4]thiadiazine） to Colletotrichum lagenarium at the concentration of 100 mg/L is 90%.