Synthesis and evaluation of esters obtained from phenols and phenoxyacetic acid with significant phytotoxic and cytogenotoxic activities.

Autor: Pinheiro PF; Department of Chemistry, Federal University of Viçosa, Avenida Peter Henry Rolfs, s/n, Viçosa, MG, 36570-900, Brazil., Martins GS; Departament of Biology, Federal University of the Espírito Santo, Alto Universitário, s/n, Alegre, ES, 29500-000, Brazil., Gonçalves PM; Department of Chemistry and Physics, Federal University of the Espírito Santo, Alto Universitário, s/n, Alegre, ES, 29500-000, Brazil., Vasconcelos LC; Departament of Biology, Federal University of the Espírito Santo, Alto Universitário, s/n, Alegre, ES, 29500-000, Brazil., Dos Santos Bergamin A; Departament of Biology, Federal University of the Espírito Santo, Alto Universitário, s/n, Alegre, ES, 29500-000, Brazil., Scotá MB; Departament of Biology, Federal University of the Espírito Santo, Avenida Fernando Ferraria 514, Goiabeiras, Vitória, ES, 29075-910, Brazil., de Resende Santo IS; Department of Chemistry, Federal University of Viçosa, Avenida Peter Henry Rolfs, s/n, Viçosa, MG, 36570-900, Brazil., Pereira UA; Montes Claros Regional Campus, Institute of Agricultural Sciences, Federal University of Minas Gerais, Avenida Universitária 1000, Bairro Universitário, Montes Claros, MG, 39404-547, Brazil., Praça-Fontes MM; Departament of Biology, Federal University of the Espírito Santo, Alto Universitário, s/n, Alegre, ES, 29500-000, Brazil. milenemiranda@yahoo.com.br.
Jazyk: angličtina
Zdroj: Environmental science and pollution research international [Environ Sci Pollut Res Int] 2024 Oct; Vol. 31 (50), pp. 60023-60040. Date of Electronic Publication: 2024 Oct 04.
DOI: 10.1007/s11356-024-35222-5
Abstrakt: There is a growing demand for herbicides that are more effective than conventional ones yet less harmful to ecosystems. In light of this, this study aimed to synthesize esters from phenols and phenoxyacetic acid, using compounds with known phytotoxic potential as starting materials. Phenoxyacetic acid was first synthesized and then utilized in the synthesis of seven esters through Steglich esterification, employing N,N'-dicyclohexylcarboimide and N,N-dimethylpyridin-4-amine in the presence of phenols (thymol, vanillin, eugenol, carvacrol, guaiacol, p-cresol, and β-naphthol), yielding esters 1-7. All synthesized compounds were characterized using mass spectrometry, 1 H, and 13 C NMR. These compounds were tested for phytotoxicity to evaluate their effects on the germination and root development of Sorghum bicolor and Lactuca sativa seeds, and for the induction of alterations in the mitotic cycle of meristematic cells of L. sativa roots. Esters 1, 3, 4, and 5 exhibited the most significant phytotoxic activity in both L. sativa and S. bicolor. Alterations in the mitotic index and frequency of chromosomal alterations in L. sativa roots revealed the cytotoxic, genotoxic effects, and the aneugenic mode of action of the tested molecules. These findings suggest that these compounds could serve as inspiration for the synthesis of new semi-synthetic herbicides.
(© 2024. The Author(s), under exclusive licence to Springer-Verlag GmbH Germany, part of Springer Nature.)
Databáze: MEDLINE
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