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 (3) 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 Colletotrichum gloeosporioides, the causative agent of papaya anthracnose. It was found that the compounds 1-(1-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-1H-1,2,3-triazol-4-yl)-cyclo-hexanol (4g) and 2-(1-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-1H-1,2,3-triazol-4-yl)propan-2-ol (4h) demonstrated high efficiency in controlling C. gloeosporioides when compared to the commercial fungicide tebuconazole. The triazoles did not present any phytotoxic effect when evaluated against Lactuca sativa. 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 L. sativa. 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 C. gloeosporioides.

Preventive efficiency of Cornelian cherry (Cornus mas L.) fruit extract in diniconazole fungicide-treated Allium cepa L. roots

“…It is considered to be an irreversible chromosomal abnormality and usually result in death of the cells 35 . As it causes unequal separation of chromosomes into the daughter cells 36 , this deviation type is a sign of the aneugenic action of diniconazole. Unequal distribution of chromatin occurrence was induced following diniconazole treatment in Group 4 (Fig.…”

Phytocytotoxicity of volatile constituents of essential oils from Sparattanthelium Mart. species (Hernandiaceae)

“…Another alteration found was chromosome adhesion, characterized by irreversible attachment of chromosomes, which likely leads to cell death. It is an alteration indicative of several mechanisms of action simultaneously, and may be aneugenic, clastogenic and epigenetic 27,61,63 .…”

“…In addition, it causes the cell to have a deformed nuclear membrane, aiming to envelop all the genetic material to it and then the deformation is undone 59 . In c-metaphases, the microtubules are completely inactivated, preventing the spindle formation 61 , 62 , i.e., the mitotic spindle becomes completely inactivated, disorganizing the formation of the equatorial plate, thus impeding or delaying the division of the centromere 61 , 62 . The continued presence of c-metaphases can lead to duplication in the number of chromosomes of these cells.…”

Synthesis and in-vitro biological evaluation of 1,1-diaryl-2-(1,2,3)triazol-1-yl-ethanol derivatives as antifungal compounds flutriafol analogues

“…Although a toxicity evaluation study on the synthesized triazoles was not done, previous reports indicate that 1,2,3-triazoles display low cytotoxicity against diverse cells [19][20][21] which suggest that synthesized triazoles could be also harmless. Future studies about the toxicity of 1,1-diaryl-2-(1,2,3)triazol-1-yl-ethanol derivatives will be done to determine this biological property and to compare to Flutriafol toxicity.…”