含三唑Schiff碱硫醚衍生物的合成及生物活性

Synthesis and Biological Activity of Schiff Base Sulfur Ether Derivatives Containing 1,2,4-Triazole Unit

以2,4-二氯苯甲酸为起始原料,经酯化、肼解、成盐、闭环合成3-硫酮-4-氨基-5-（2,4-二氯）苯基-1,2,4-三唑（Ⅳ）,然后与取代甲醛缩合生成中间体（Ⅴ）,最后以乙腈为溶剂,K2CO3为催化剂,中间体Ⅴ与卤代烃于75℃反应2 h合成了8个含三唑Schiff碱硫醚衍生物（Ⅵa~Ⅵh）,收率69%~78%,其结构经1HNMR、13CNMR、19FNMR、IR以及元素分析表征。初步生物活性测试结果表明,部分目标化合物对黄瓜霜霉病的抑制率达100%。

Starting from 2,4-dichlorobenzoic acid, 4-amino-5-（ 2,4-dichlorophenyl ） -2H-1,2,4-tria-- zole-3（4H）-thione（ 1V ） was afforded in four steps including esterification, hydrazidation, salification, eyclization. 5-（2,4-dichlorophenyl） -4-（ substituted methyleneamino） -2H-1,2,4-triazole-3 （4H） -thione （V） was then synthesized by the condensation reaction of the intermediate IV with substituted formaldehyde. Eight Sehiff base sulfur ether derivatives containing 1,2,4-triazole unit in yields of 69% - 78 % were synthesized by reaction of 5- （2,4-dichlorophenyl） -4- （ substituted methyleneamino ） -2H- 1,2,4-triazole-3 （4H）-thione with halogenated hydrocarbon using K2CO3 as catalyst in acetonitrile at 75 ℃ for 2 h. The structures were confirmed by 1HNMR,13 CNMR,19 FNMR, IR and elemental analyses. The preliminary bioassay showed that the antifungal activity of some compounds against P. cubensis at the concentration of 100 mg/L was 100%.