Related Experiment Video
Updated: Jun 5, 2026
![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)
Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Synthesis and fungicidal activity of novel 1,1-diaryl-2-azolylethanols with a pyridine moiety
Minghui Chen1, Fahong Yin1, Sai Hong1
1College of Science, China Agricultural University, Beijing, 100193, China.
Abstract:
To investigate the effect of pyridine heterocycle on the activity of triazole alcohol fungicides, 31 pyridine-containing 2-azolyl-1,1-diarylmethanol derivatives were designed and synthesized using flutriafol as the lead compound and pyridine diaryl ketone molecular building blocks as the basis. The in vitro fungicidal activity against 10 plant pathogenic fungi was determined, and the results showed that the target compounds exhibited broad-spectrum inhibitory effects on the tested pathogens. Among them, the imidazole-substituted compounds I-24, I-26 and I-27 displayed remarkable fungicidal activity against Sclerotinia sclerotiorum, Phytophthora capsici, Pythium aphanidermatum, Botrytis cinerea and other fungi. The EC₅₀ values of compound I-24 against various pathogens were as low as 3.55 ~ 15.46 μg/mL, and its in vivo curative activity against Botrytis cinerea on tomato fruits was comparable to that of the positive control flutriafol. Structure-activity relationship analysis revealed a positive correlation between the hydrophobicity of the compounds and their fungicidal activity. The replacement of cyclohexyl with benzene ring and the introduction of substituents at the 2-position of the benzene ring exerted a positive effect on the activity. Triazole and imidazole derivatives showed similar overall activity, with some imidazole-substituted compounds exhibiting superior activity. Molecular docking studies further elucidated the binding mechanism of the compounds to the 14α-demethylase of Fusarium graminearum and the reasons for the differences in their biological activities.
Related Concept Videos
Aryldiazonium Salts to Azo Dyes: Diazo Coupling
Antifungal Agents
Preparation of 1° Amines: Azide Synthesis
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Diazonium Group Substitution: –OH and –H
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo, or cyano...
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

