新型含2,4-二氯苯基的1,2,4-三唑喹唑啉衍生物的合成及抑菌活性

以2,4-二氯苯甲酸为起始原料,经酯化、肼解、成盐、闭环、缩合反应合成了4-(取代苯次甲亚胺基)-5-(2,4-二氯苯基)-2H-1,2,4-三唑-3(4H)-硫酮;以2-氨基-3-甲基苯甲酸为原料,经酰化、胺化和取代反应合成了2-(2-氯乙酰氨基)-N-甲基苯甲酰胺。以1%KOH溶液为溶剂,4-(取代苯次甲亚胺基)-5-(2,4-二氯苯基)-2H-1,2,4-三唑-3(4H)-硫酮与2-(2-氯乙酰氨基)-3-甲基-N-甲基苯甲酰胺于50℃反应4 h合成了13个未见文献报道的含2,4-二氯苯基1,2,4-三唑1,3,4-噻二嗪喹唑啉类化合物(9a^9m),收率59%~74%,其结构经1H NMR,13C NMR,19F NMR和MS表征。采用浊度法测试目标化合物对柑橘溃疡病菌(Xac)、烟草青枯病菌(Rs)、水稻百叶枯病菌(Xoo)的抑制活性。结果表明:当浓度为50μg/mL时,部分化合物具有较好的抑菌活性,其中化合物9j和对照药剂噻菌酮和叶枯唑的抑制率相当,对柑橘溃疡病菌的抑制率为56.4%,对水稻百叶枯病菌的抑制率为48.5%,具有进一步优化的潜力。

Synthesis and Antibacterial Activities of Novel Quinazoline Derivatives Containing 1,2,4-triazole and 2,4-Dichlorophenyl Units

Starting from 2,4-dichlorobenzoic acid,4-amino-5-(2,4-dichlorophenyl)-2H-1,2,4--triazole-3(4H)-thione(4)was afforded by esterification,hydrazidation,salt formation,cyclization.5-(2,4-Dichlorophenyl)-4-(substituted benzylideneamino)-2H-1,2,4-triazole-3(4H)-thione(5)was then synthesized by the condensation reaction of 4 with substituted benzaldehyde.Thirteen novel quinazoline derivatives containing 1,2,4-triazole and 2,4-dichlorophenyl units in yield of 59%~74%were synthesized by reaction of the intermediate 5 with 2-(2-chloroacetamido)-N,3-dimethylbenzamide in 1%KOH aqueous solution at 50℃for 4 h.The structures were confirmed by 1H NMR,13C NMR,19F NMR and MS.The preliminary bioassay showed that the antibacterial activity of compound 9j to Xac was 56.4%and 48.5%to X.Oryzae at the concentration of 50μg/mL.