Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (6): 1500-1506.DOI: 10.6023/cjoc201710011 Previous Articles     Next Articles



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 发布日期:2018-02-06
  • 通讯作者: 马永强,
  • 基金资助:


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 Published:2018-02-06
  • Contact: 10.6023/cjoc201710011
  • 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).

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