Synthesis of Novel Glycerol-Derived 1,2,3-Triazoles and Evaluation of Their Fungicide, Phytotoxic and Cytotoxic Activities

Abstract

The synthesis of a series of 1,2,3-triazoles using glycerol as starting material is described. The key step in the preparation of these triazolic derivatives is the copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC), also known as click reaction, between 4-(azidomethyl)-2,2-dimethyl-1,3-dioxolane (<b>3</b>) and different terminal alkynes. The eight prepared derivatives were evaluated with regard to their fungicide, phytotoxic and cytotoxic activities. The fungicidal activity was assessed in vitro against <i>Colletotrichum gloeosporioides</i>, the causative agent of papaya anthracnose. It was found that the compounds 1-(1-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-1<i>H</i>-1,2,3-triazol-4-yl)-cyclo-hexanol (<b>4g</b>) and 2-(1-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-1<i>H</i>-1,2,3-triazol-4-yl)propan-2-ol (<b>4h</b>) demonstrated high efficiency in controlling <i>C. gloeosporioides</i> when compared to the commercial fungicide tebuconazole. The triazoles did not present any phytotoxic effect when evaluated against <i>Lactuca sativa</i>. However, five derivatives were mitodepressive, inducing cell death detected by the presence of condensed nuclei and acted as aneugenic agents in the cell cycle of <i>L. sativa</i>. It is believed that glycerol derivatives bearing 1,2,3-triazole functionalities may represent a promising scaffold to be explored for the development of new agents to control <i>C. gloeosporioides</i>.