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

doi:10.6023/cjoc201710011

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

Articles

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

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,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 Changsheng^a, Zou Yulong^b, Jia Changqing^c, Qin Zhaohai^a, Ma Yongqiang^a

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 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).

1. Synthesis and Fungicidal Activity of Bridging Ligand Compounds of Azo with 1, 3, 5-Substitued Triazole.PDF(1176KB)

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.

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

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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]. Chin. J. Org. Chem., 2018, 38(6): 1500-1506.

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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

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