Articles

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

  • Li Changsheng ,
  • Zou Yulong ,
  • Jia Changqing ,
  • Qin Zhaohai ,
  • Ma Yongqiang
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  • 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 date: 2017-10-09

  Revised date: 2018-01-29

  Online published: 2018-02-06

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).

Abstract

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.

Cite this article

Li Changsheng , Zou Yulong , Jia Changqing , Qin Zhaohai , Ma Yongqiang . Synthesis and Fungicidal Activity of Bridging Ligand Compounds of Azo with 1, 3, 5-Substitued Triazole[J]. Chinese Journal of Organic Chemistry, 2018 , 38(6) : 1500 -1506 . DOI: 10.6023/cjoc201710011

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