1 Synthesis of Novel Glycerol - Derived 1 , 2 , 3 - Triazoles 2 and Evaluation of Their Fungicide , Phytotoxic and 3 Cytotoxic Activities 4

Glycerol is a subproduct of biodiesel production and represents an important problem 26 when generated in large scale. Alternatives that can utilize this unrefined byproduct is of potential 27 interest. It is herein described the synthesis of a series of 1,2,3-triazoles using glycerol as starting 28 material. The key step involved in the preparation of triazolic derivatives corresponded to the 29 Copper(I)-catalyzed Azide-Alkyne Cycloaddition (CuAAC), also known as click reaction, between 30 4-(azidomethyl)-2,2-dimethyl-1,3-dioxolane (3) and different terminal alkynes. The eight prepared 31 derivatives were evaluated with regard to their fungicide, phytotoxic and cytotoxic activities. The 32 fungicide activity was assessed in vitro against Colletotrichum gloeosporioides, the causing agent of 33 papaya anthracnose. It was found that the compounds 1-(1-((2,2-dimethyl-1,3-dioxolan-434 yl)methyl)-1H-1,2,3-triazol-4-yl)cyclohexanol (4g) and 2-(1-((2,2-dimethyl-1,3-dioxolan-435 yl)methyl)-1H-1,2,3-triazol-4-yl)propan-2-ol (4h) demonstrated high efficiency on controlling C. 36 gloeosporioides when compared to the commercial fungicide tebuconazole. The triazoles did not 37 present any phytotoxic effect when evaluated against Lactuca sativa. However, five derivatives were 38 mitodepressive, inducing cell death detected by the presence of condensed nuclei and acted as 39 aneugenic agents in the cell cycle of L. sativa. It is believed that glycerol derivatives bearing 1,2,340 triazole functionalities may represent a scaffold to be explored toward the development of new 41 agents to control C. gloeosporioides. 42