Novel lipophilic analogues from 2,4-D and Propanil herbicides: Biological activity and kinetic studies.

Autor: Porciuncula LM; Laboratorio Kolbe de Síntese Orgânica, Escola de Química e Alimentos, Universidade Federal do Rio Grande, Av. Itália, Km 08, s/n, Rio Grande, RS, Brazil., Teixeira AR; Grupo de Catálise e Cinética, Universidade Federal do Paraná, Curitiba, PR, Brazil., Santos MFC; Laboratório de Ressonância Magnética Nuclear, Departamento de Química, Universidade Federal do Paraná, Curitiba, PR, Brazil., D'Oca MGM; Laboratorio Kolbe de Síntese Orgânica, Escola de Química e Alimentos, Universidade Federal do Rio Grande, Av. Itália, Km 08, s/n, Rio Grande, RS, Brazil., Santos LS; Laboratory of Asymmetric Synthesis, Instituto de Química de Recursos Naturales, Universidad de Talca, Talca, 3460000, Chile., Nachtigall FM; Instituto de Ciencias Químicas Aplicadas, Universidad Autónoma de Chile, Talca, 3467987, Chile., Orth ES; Grupo de Catálise e Cinética, Universidade Federal do Paraná, Curitiba, PR, Brazil., D'Oca CRM; Laboratório de Ressonância Magnética Nuclear, Departamento de Química, Universidade Federal do Paraná, Curitiba, PR, Brazil. Electronic address: carolinedoca@ufpr.br.
Jazyk: angličtina
Zdroj: Chemistry and physics of lipids [Chem Phys Lipids] 2020 Sep; Vol. 231, pp. 104947. Date of Electronic Publication: 2020 Jul 02.
DOI: 10.1016/j.chemphyslip.2020.104947
Abstrakt: This work describes the synthesis of new lipophilic amides and esters analogues of classical organochlorides herbicides by incorporation of long-chains from fatty acids and derivatives. The new fatty esters and amides were synthesized in 96-99% and 80-89% yields, respectively. In general, all compounds tested showed superior in vitro activity than commercial herbicides against growth L. sativa and A. cepa, in ranges 86-100% of germinative inhibition. The target compounds showed, significantly more susceptible towards acid hydrolysis than 2,4-dichlorophenoxyacetic acid (2,4-D). The kinetic and NMR studies showed that the incorporation of lipophilic chains resulted in a decrease in half-life time of new herbicides compounds (1.5 h) than 2,4-D (3 h). These findings suggest the synthesis of new lipophilic herbicides as potential alternative to traditional formulations, by incorporation of long fatty alkyl chains in the molecular structure of 2,4-D, resulting in superior in vitro herbicidal activity, best degradation behavior and more hydrophobic derivatives.
(Copyright © 2020 Elsevier B.V. All rights reserved.)
Databáze: MEDLINE
Externí odkaz: