三唑衍生物的合成及生物活性研究
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摘要
含氮杂环是一类具有良好生物活性和重要应用价值的化合物,其中唑类杂环化合物由于具有较好的生物活性而备受人们重视。为了寻找新的具有更高活性的三唑杂环类衍生物,本文合成了一系列新型三唑类衍生物,用1~HNMR,IR,元素分析对化合物结构进行了表征,并初步进行了室内生物活性测试,探讨了其结构和生物活性之间的关系。
一、3-取代苯氧甲基-4-氨基-1,2,4-三唑-5-硫酮类席夫碱的合成及生物活性研究
以取代苯氧乙酸与1,3-二氨基硫脲反应合成中间体3-取代苯氧甲基-4-氨基-1,2,4-三唑-5-硫酮。中间体与取代芳香醛缩和,合成了一系列三唑硫酮类席夫碱化合物。化合物结构经1~H NMR,IR,元素分析进行了表征。初步测定了其对三种植物病原菌的杀菌活性,结果表明所合成的大部分化合物对所测菌种有优良的杀菌作用。最后,探讨了其结构和生物活性之间的关系。
二、3,6-二取代-1,2,4-三唑[3,4-b][1,3,4]噻二唑的合成及生物活性研究
取代苯氧乙酸与1,3-二氨基硫脲反应得到中间体3-取代苯氧甲基-4-氨基-1,2,4-三唑-5-硫酮。中间体3-取代苯氧甲基-4-氨基-1,2,4-三唑-5-硫酮与取代苯氧乙酸在脱水剂三氯氧磷作用下,合成了3,6-二取代苯氧甲基-1,2,4-三唑[3,4-b][1,3,4[噻二唑化合物。在脱水剂三氯氧磷存在下,取代苯甲酸与3-取代苯氧甲基-4-氨基-1,2,4-三唑-5-硫酮反应,合成了3-取代苯氧甲基-6-取代苯基-1,2,4-三唑[3,4-b][1,3,4]噻二唑化合物。用1~H NMR,IR,元素分析对所合成化合物结构进行了表征,并初步测定了其对三种植物病原菌的杀菌活性,结果表明此类化合物具有较好的杀菌活性。最后,探讨了其结构和生物活性之间的关系。
Nitrogen heterocyclic ring compounds have important applications and good biological activities.Among of them,researchers give much attention to triazoles for their good biological activities.In order to search for new triazole derivatives with higher biological activities,a series of new triazole derivatives were synthesized.Their structures were confirmed by IR,~1H NMR and elemental analysis.The preliminary biological activities were tested.The relationship between the structures and the fungicidal activities of the compounds has been discussed.
Part one:Synthesis and biological activities of 3-substituted phenoxymethyl-4 -amino-1,2,4-triazol-5-thione Schiff bases
The intermediats 3-substituted phenoxymethyl-4-amino-1,2,4-triazol-5-thiones were synthesized by substituted phenoxyacetic acid and 1,3-diaminothiourea.A series of triazolthione Schiff bases were synthesized by the intermediates 3-substituted phenoxymethyl-4-amino-1,2,4-triazol-5-thiones and substitutied aromatic aldehydes. Their structures have been confirmed by ~1H NMR,IR and elemental analysis.The preliminary biological activities to three vegetable pathogens have been tested.The results showed that most of them exhibited good fungicidal activities.The relationship between the structures and the biological activities has been discussed.
Part two:Synthesis and biological activities of 3,6-disubstituted-1,2,4-triazolo[3,4 -b][1,3,4]thiadiazoles
The intermediates 3-substituted phenoxymethyl-4-amino-1,2,4-triazol-5-thiones were synthesized by substituted phenoxyacetic acid and 1,3-diaminothiourea.In phosphorus oxychloride,3,6-disubstituted phenoxymethyl-1,2,4-triazolo[3,4-b][1, 3,4]thiadiazoles were synthesized by 3-substituted phenoxymethyl-4-amino-1,2,4 -triazol-5-thiones and substituted phenoxyacetic acids.3-substitutied phenoxymethyl-6 -substituted phenyl-1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles were synthesized by substituted benzoic acids and 3-substituted phenoxymethyl-4-amino-1,2,4 -triazol-5-thiones in phosphorus oxychloride.Their structures have been confirmed by ~1H NMR,IR and elemental analysis.The preliminary biological activities to three vegetable pathogens have been tested.The results showed that most of them exhibited good fungicidal activities.The relationship between the structures and the biological activities has been discussed.
一、3-取代苯氧甲基-4-氨基-1,2,4-三唑-5-硫酮类席夫碱的合成及生物活性研究
以取代苯氧乙酸与1,3-二氨基硫脲反应合成中间体3-取代苯氧甲基-4-氨基-1,2,4-三唑-5-硫酮。中间体与取代芳香醛缩和,合成了一系列三唑硫酮类席夫碱化合物。化合物结构经1~H NMR,IR,元素分析进行了表征。初步测定了其对三种植物病原菌的杀菌活性,结果表明所合成的大部分化合物对所测菌种有优良的杀菌作用。最后,探讨了其结构和生物活性之间的关系。
二、3,6-二取代-1,2,4-三唑[3,4-b][1,3,4]噻二唑的合成及生物活性研究
取代苯氧乙酸与1,3-二氨基硫脲反应得到中间体3-取代苯氧甲基-4-氨基-1,2,4-三唑-5-硫酮。中间体3-取代苯氧甲基-4-氨基-1,2,4-三唑-5-硫酮与取代苯氧乙酸在脱水剂三氯氧磷作用下,合成了3,6-二取代苯氧甲基-1,2,4-三唑[3,4-b][1,3,4[噻二唑化合物。在脱水剂三氯氧磷存在下,取代苯甲酸与3-取代苯氧甲基-4-氨基-1,2,4-三唑-5-硫酮反应,合成了3-取代苯氧甲基-6-取代苯基-1,2,4-三唑[3,4-b][1,3,4]噻二唑化合物。用1~H NMR,IR,元素分析对所合成化合物结构进行了表征,并初步测定了其对三种植物病原菌的杀菌活性,结果表明此类化合物具有较好的杀菌活性。最后,探讨了其结构和生物活性之间的关系。
Nitrogen heterocyclic ring compounds have important applications and good biological activities.Among of them,researchers give much attention to triazoles for their good biological activities.In order to search for new triazole derivatives with higher biological activities,a series of new triazole derivatives were synthesized.Their structures were confirmed by IR,~1H NMR and elemental analysis.The preliminary biological activities were tested.The relationship between the structures and the fungicidal activities of the compounds has been discussed.
Part one:Synthesis and biological activities of 3-substituted phenoxymethyl-4 -amino-1,2,4-triazol-5-thione Schiff bases
The intermediats 3-substituted phenoxymethyl-4-amino-1,2,4-triazol-5-thiones were synthesized by substituted phenoxyacetic acid and 1,3-diaminothiourea.A series of triazolthione Schiff bases were synthesized by the intermediates 3-substituted phenoxymethyl-4-amino-1,2,4-triazol-5-thiones and substitutied aromatic aldehydes. Their structures have been confirmed by ~1H NMR,IR and elemental analysis.The preliminary biological activities to three vegetable pathogens have been tested.The results showed that most of them exhibited good fungicidal activities.The relationship between the structures and the biological activities has been discussed.
Part two:Synthesis and biological activities of 3,6-disubstituted-1,2,4-triazolo[3,4 -b][1,3,4]thiadiazoles
The intermediates 3-substituted phenoxymethyl-4-amino-1,2,4-triazol-5-thiones were synthesized by substituted phenoxyacetic acid and 1,3-diaminothiourea.In phosphorus oxychloride,3,6-disubstituted phenoxymethyl-1,2,4-triazolo[3,4-b][1, 3,4]thiadiazoles were synthesized by 3-substituted phenoxymethyl-4-amino-1,2,4 -triazol-5-thiones and substituted phenoxyacetic acids.3-substitutied phenoxymethyl-6 -substituted phenyl-1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles were synthesized by substituted benzoic acids and 3-substituted phenoxymethyl-4-amino-1,2,4 -triazol-5-thiones in phosphorus oxychloride.Their structures have been confirmed by ~1H NMR,IR and elemental analysis.The preliminary biological activities to three vegetable pathogens have been tested.The results showed that most of them exhibited good fungicidal activities.The relationship between the structures and the biological activities has been discussed.
引文
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