偶氮桥联的1,3,5-多取代三唑类化合物的合成及抑菌活性

Synthesis and Fungicidal Activity of Bridging Ligand Compounds of Azo with 1,3,5-Substitued Triazole

以1,3,5-三取代-1,2,4-三唑类化合物为原料,在KMn O4或二氯异氰尿酸钠(SDCI)作用下,发生自身氧化偶联反应,合成了16个未见文献报道的偶氮桥联的1,3,5-多取代三唑类化合物.产物结构经1H NMR、13C NMR、IR、HRMS及X射线单晶衍射得以证实,并采用生长速率法对所有化合物进行了离体抑菌活性测试.结果表明:在浓度为50μg/m L时,大部分化合物对所选六种病菌具有一定的抑制活性,其中1,1'-二正丁基-3,3'-二(2''-氯苯基)-5,5'-偶氮二(1,2,4-三唑)(3h)、1,1'-二丙基-3,3'-二(4''-氯苯基)-5,5'-偶氮二(1,2,4-三唑)(3k)对瓜果腐霉菌的抑制率接近三唑酮,而1,1'-二丙基-3,3'-二(2''-氯苯基)-5,5'-偶氮二(1,2,4-三唑)(3g)的抑制率要高于三唑酮.该类化合物反应操作简单、条件温和,对新农药创制及合成具有借鉴意义.

Sixteen bridging ligand compounds of azo with 1,3,5-substitued triazole had been synthesized from 1,3,5-trisubstituted-1,2,4-triazoles by the oxidative coupling reaction using potassium permanganate or sodium dichloroisocyamirate as the oxidant. The structures of the target compounds were determined by 1 H NMR, 13 C NMR, IR, MS, HRMS and X-ray diffraction. They were tested for in vitro fungicidal activities by the mycelium growth rate method. The results indicated that most of the title compounds had a certain inhibitory activity at the concentration of 50 μg/m L. Especially, the inhibition rate of 1,2-bis（1-butyl-3-（2-chlorophenyl）-1 H-1,2,4-triazol-5-yl）diazene（3 h） and 1,2-bis（3-（4-chlorophenyl）-1-propyl-1 H-1,2,4-triazol-5-yl）diazene（3 k） were close to that of triadimefon when against Pythium aphanidermatum, while the inhibition rate of 1,2-bis（3-（2-chlorophenyl）-1-propyl-1 H-1,2,4-triazol-5-yl）diazene（3 g） was higher than that of riadimefon. The reactions of these compounds were simple and mild, which was of reference significance to the creation and synthesis of new pesticides.