Synthesis of Glycerol-Derived 4-Alkyl-Substituted 1,2,3-Triazoles and Evaluation of Their Fungicidal, Phytotoxic, and Antiproliferative Activities

Abstract

Herein, the synthesis of nine novel glycerol-derived 4-alkyl-substituted 1,2,3-triazoles, using the Cu I-catalyzed alkyne-azide cycloaddition reaction as the key step, is reported. The triazoles were characterized by infrared and nuclear magnetic resonance (NMR 1 H and 13 C) spectroscopy and mass spectrometry. The nine prepared compounds were evaluated with regard to their phytotoxic, antiproliferative, and fungicidal activities. The fungicidal activity was assessed on Colletotrichum gloeosporioides, the causative agent of papaya anthracnose. All compounds presented high efficiency (comparable to the commercial fungicide tebuconazole) in inhibiting C. gloeosporioides sporulation. The phytotoxicity of the triazoles was assessed against Lactuca sativa. Germination was the less-affected parameter, whereas the most pronounced effects of the triazoles were on the germination speed index and root growth of the L. sativa seedlings. As indicators of antiproliferative activity, the mitotic index was evaluated along with chromosomal and nuclear alterations, all of which were influenced to different degrees by the triazoles. In addition, all derivatives demonstrated aneugenic and clastogenic actions in meristematic cells of L. sativa roots. Therefore, these 4-alkyl-substituted triazoles may represent a scaffold to be explored for the development of new fungicidal agents.

A Recent Overview of 1,2,3-Triazole-Containing Hybrids as Novel Antifungal Agents: Focusing on Synthesis, Mechanism of Action, and Structure-Activity Relationship (SAR)

“…Costa et al [126] explained a new route for synthesizing a series of glycerol-derived 4-alkyl-substituted 1,2,3-triazoles using glycerol as the starting substance. Colletotrichum gloeosporioides, a causal factor of papaya anthracnose, were tested for fungicidal activity.…”

Phytotoxic and cyto-genotoxic activity of essential oil from leaf residues of Eucalyptus urophylla and the hybrid E. urophylla x E. camaldulensis on Lactuca sativa and Sorghum bicolor

“…GP was significantly inhibited, differing even from C+, in lettuce seeds treated with the hybrid oil at a concentration of 3000μg L -1 , with a 17% inhibition compared to C-(Figure 1a). This is the low-sensitive parameter, which is only expressed in the acute phytotoxicity of the test compounds (Aragão et al, 2017;Costa et al, 2019). Therefore, as it is not very sensitive, this variable will be changed when the test agent is very toxic, that is, when it produces acute toxicity.…”

“…The CA observed were: c-metaphase (Figure 5c), chromosomal adhesion (Figure 5d), chromosomal bridge (Figure 5e), missing chromosome (Figure 5f), multipolarity, chromosome delay in telophase and chromosomal fragment. The frequencies of each CA clarify the mechanism of action of the oil, which can be clastogenic or aneugenic (Aragão et al, 2015;Costa et al, 2019;Alves et al, 2018;Fernandes et al, 2009). Research, Society andDevelopment, v. 10, n. 11, e242101119646, 2021 (CC BY 4.0) | ISSN 2525-3409 | DOI: http://dx.doi.org/10.33448/rsd-v10i11.19646 The aneugenic mechanism of action is promoted due to changes in the mitotic machinery of the cell, promoting changes in the mitotic spindle, involving the polymerization and depolymerization of the microtubules.…”

Synthesis and Fungicide Activity onAsperisporium caricaeof Glycerol Derivatives Bearing 1,2,3-Triazole Fragments

“…These derivatives showed efficacy compared to the commercial fungicide tebuconazole. 21,22 Glycerol is a low-cost byproduct obtained from the transesterification of vegetable oils or animal fats. 23 This polyol, also known as propane-1,2,3-triol, is a colorless, odorless, sweet, and viscous liquid, which can be obtained from natural or synthetic sources.…”

“…Structural modifications in its molecule resulted in new substances with promising fungicidal activity. 25,26 Therefore, continuing our efforts toward the search and development of compounds that are more efficient for the control of phytopathogenic fungi, we describe the synthesis of 12 glycerol derivatives containing 1,2,3-triazole moieties (nine of them were not previously reported) and the evaluation of their fungicidal activity against A. caricae.…”