Citation: Huo Xinyu, Li Wenbin, Zhang Boya, Chen Xiaofei, Zhou Yueting, Zhang Jie, Han Xiaoqiang, Dai Bin. Synthesis and Fungicidal Evaluation of Novel β-Carboline-Benzimidazole and β-Carboline-Benzothiazole Hybrids[J]. Chinese Journal of Organic Chemistry, ;2018, 38(12): 3356-3362. doi: 10.6023/cjoc201805053 shu

Synthesis and Fungicidal Evaluation of Novel β-Carboline-Benzimidazole and β-Carboline-Benzothiazole Hybrids

Huo Xinyu ^a ,
Li Wenbin ^a ,
Zhang Boya ^a ,
Chen Xiaofei ^a ,
Zhou Yueting ^b ,
Zhang Jie ^a,c,, ,
Han Xiaoqiang ^b,, ,
Dai Bin ^a

a.
School of Chemistry and Chemical Engineering, Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, Shihezi University, Shihezi 832003
b.
Key Laboratory at Universities of Xinjiang Uygur Autonomous Region for Oasis Agricultural Pest Management and Plant Protection Resource Utilization, College of Agricultural, Shihezi University, Shihezi 832003
c.
Industrial Technology Research Institute, Xinjiang Production and Construction Corps, Shihezi 832003

Corresponding author: Zhang Jie, zhangjie-xj@163.com Han Xiaoqiang, hanshz@shzu.edu.cn
Received Date: 29 May 2018
Revised Date: 7 July 2018
Available Online: 22 December 2018
Fund Project: the Yangtze River Scholar Research Project of Shihezi University CJXZ201601Project supported by the Scientific Research Innovation Project in Xinjiang Uygur Autonomous Region (No. XJGRI2017045), the National Students Innovation and Entrepreneuship Training Program (No. 201810759055), the Program for Changjiang Scholars and Innovative Research Team in University (No. IRT15R46), and the Yangtze River Scholar Research Project of Shihezi University (No. CJXZ201601)the Scientific Research Innovation Project in Xinjiang Uygur Autonomous Region XJGRI2017045the National Students Innovation and Entrepreneuship Training Program 201810759055the Program for Changjiang Scholars and Innovative Research Team in University IRT15R46

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In order to discover novel compounds with biological activities, new molecular hybrids combining benzimidazole or its bioisostere benzothiazole with β-carboline were synthesized. The benzimidazole or benzothiazole scaffold was linked at position-1 with β-carboline which was further characterized by ¹H NMR, ¹³C NMR and HRMS. All of the target compounds were evaluated in vitro for their antifungal activity against Rhizoctorzia solani, Fusarium oxysporum, Botrytis cinerea Pers., sunflower sclerotinia rot and rape sclerotinia rot by mycelia growth inhibition assay at 50 μg·mL^-1. The preliminary results showed that most compounds exhibit mild inhibiting effect against all the tested strains. Among them, 1-(1H-benzo[d]-imida-zol-2-yl)-9-ethyl-β-carboline (4a), 1-(1H-benzo[d]imidazol-2-yl)-9-benzyl-β-carboline (4c) and 1-(1H-benzo[d]imidazol-2-yl)-9-(3-chlorobenzyl)-β-carboline (4e) showed satisfactory antifungal activity against sunflower sclerotinia rot, 1-(1H-benzo[d]-imidazol-2-yl)-9-ethyl-β-carboline (4a), 1-(1H-benzo[d]imidazol-2-yl)-9-n-butyl-β-carboline (4b), 1-(1H-benzo[d]imidazol-2-yl)-9-benzyl-β-carboline (4c), 1-(1H-benzo[d]imidazol-2-yl)-9-((perfluorophenyl)methyl)-β-carboline (4f), 1-(benzo[d]-thiazol-2-yl)-9-(3-chlorobenzyl)-β-carboline (5e) and 1-(benzo[d]thiazol-2-yl)-9-((perfluorophenyl)methyl)-β-carboline (5f) displayed excellent fungicidal activity against rape sclerotinia rot. Specifically, compound 4c exhibited broad-spectrum fungicidal activity against most of the tested fungi.
- β-carboline,
- benzimidazole,
- benzothiazole,
- antifungal activity
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