含三唑Schiff碱硫醚衍生物的合成及生物活性研究

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

摘要:

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-巯基-4-氨基-5-(2,4-二氯)苯基-1,2,4-三唑4，进而与取代甲醛缩合生成中间体5，最后以乙腈为溶剂，K2CO3为催化剂，中间体5与卤代烃于75℃反应2h合成了8个含三唑Schiff碱硫醚衍生物(6a~6h)，收率69%~78%，其结构经1H NMR、13C NMR、19 F NMR、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%。

Abstract:

Starting from 2,4-dichlorobenzoic acid, 4-amino-5-(2,4-dichlorophenyl)-2H-1,2,4-tria- -zole-3(4H)-thione 4 was afforded in four steps including esterification, hydrazidation, salt formation, cyclization. 5-(2,4-dichlorophenyl)-4-( substituted methyleneamino)-2H-1,2,4-triazole- 3(4H)-thione 5 was then synthesized by the condensation reaction of the intermediate 4 with substituted formaldehyde. Eight schiff base sulfur ether derivatives containing 1,2,4-triazole unit in yield 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 1H NMR, 13C NMR, 19 F NMR, IR and elemental analyses. The preliminary bioassay showed that the antifungal activity of some compounds to P.cubensis at the concentration of 100 mg/L was 100%。