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以对氯苯甲酰氯为原料,通过与硫氰酸钾反应生成对氯苯甲酰基异硫氰酸酯,再与芳酰肼进行加成反应,合成了7种对氯苯甲酰基芳酰氨基硫脲:N-对氯苯甲酰基-N’-苯甲酰氨基硫脲(Ⅱ1)、N-对氯苯甲酰基-N’-对羟基苯甲酰氨基硫脲(Ⅱ2)、N-对氯苯甲酰基-N’-对硝基苯甲酰氨基硫脲(Ⅱ3)、N-对氯苯甲酰基-N’-邻甲氧基苯甲酰氨基硫脲(Ⅱ4)、N-对氯苯甲酰基-N’-对氯苯甲酰氨基硫脲(Ⅱ5)、N-对氯苯甲酰基-N’-α-萘乙酰氨基硫脲(Ⅱ6)和N-对氯苯甲酰基-N’-对甲苯甲酰氨基硫脲(Ⅱ7),收率分别为79.8%、84.8%、65.6%、64.6%、88.8%、72.2%和82.6%。产物的结构经元素分析、红外光谱和核磁共振氢谱表征。并对目标化合物进行了杀菌活性测试,初步测试结果表明,该类化合物对枯草杆菌有较强抑制作用,而对大肠杆菌无明显抑制作用。
With p-chlorobenzoyl chloride as raw material, p-chlorobenzoyl isothiocyanate was synthesized by reaction with potassium thiocyanate and then reacted with aroylhydrazide to synthesize 7 kinds of p-chlorobenzoylarylamido Thiourea: N-p-chlorobenzoyl-N’-benzoylaminothiourea (II1), N-p-chlorobenzoyl-N’-p-hydroxybenzyl thiosemicarbazide (II2), N- P-nitrobenzamide thiosemicarbazide (II3), N-p-chlorobenzoyl-N’-o-methoxybenzyl thiosemicarbazide (II4), N-p- Benzoyl-N’-p-chlorobenzoylaminothiourea (II5), N-p-chlorobenzoyl-N’-α-naphthaleneacetamidothiourea (II6) and N-p- P-toluylthiosemicarbazide (II7) with yield of 79.8%, 84.8%, 65.6%, 64.6%, 88.8%, 72.2% and 82.6%, respectively. The structure of the product was characterized by elemental analysis, IR and 1H NMR. The target compounds were tested for bactericidal activity. The preliminary test results showed that these compounds have strong inhibitory effect on Bacillus subtilis and no significant inhibitory effect on Escherichia coli.