有机化学 ›› 2018, Vol. 38 ›› Issue (6): 1500-1506.DOI: 10.6023/cjoc201710011 上一篇    下一篇

研究论文

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

李长胜a, 邹玉龙b, 贾长青c, 覃兆海a, 马永强a   

  1. a 中国农业大学理学院 北京 100193;
    b 牡丹江医学院附属红旗医院 牡丹江 157001;
    c 铜仁职业技术学院 铜仁 554300
  • 收稿日期:2017-10-09 修回日期:2018-01-29 出版日期:2018-06-25 发布日期:2018-02-06
  • 通讯作者: 马永强,E-mail:mayongqiang@cau.edu.cn E-mail:mayongqiang@cau.edu.cn
  • 基金资助:

    国家自然科学基金(No.31272076)和国家科技支撑计划(No.2015BAK45B01)资助项目.

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

Li Changshenga, Zou Yulongb, Jia Changqingc, Qin Zhaohaia, Ma Yongqianga   

  1. a College of Sciences, China Agricultural University, Beijing 100193;
    b Mudanjiang Medical University Affiliated Hongqi Hospital, Mudanjiang 554300;
    c Tongren Polytechnic College, Tongren 554300
  • Received:2017-10-09 Revised:2018-01-29 Online:2018-06-25 Published:2018-02-06
  • Contact: 10.6023/cjoc201710011 E-mail:mayongqiang@cau.edu.cn
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 31272076) and the National Key Technology Support Program of China (No. 2015BAK45B01).

以1,3,5-三取代-1,2,4-三唑类化合物为原料,在KMnO4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50 μg/mL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.

关键词: 三氮唑, 偶氮化合物, 氧化偶联, 抑菌活性

Sixteen bridging ligand compounds of azo with 1,3,5-substitued triazole had been synthesized from 1,3,5-trisub-stituted-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 1H NMR, 13C 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/mL. Especially, the inhibition rate of 1,2-bis(1-butyl-3-(2-chlorophenyl)-1H-1,2,4-triazol-5-yl)diazene (3h) and 1,2-bis(3-(4-chlorophenyl)-1-propyl-1H-1,2,4-triazol-5-yl)diazene (3k) were close to that of triadimefon when against Pythium aphanidermatum, while the inhibition rate of 1,2-bis(3-(2-chlorophenyl)-1-propyl-1H-1,2,4-triazol-5-yl)diazene (3g) 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.

Key words: triazole, azo compounds, oxidative coupling, fungicidal activities