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Chem Phys Lipids ; 231: 104947, 2020 09.
Artículo en Inglés | MEDLINE | ID: mdl-32622838

RESUMEN

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.


Asunto(s)
Ácido 2,4-Diclorofenoxiacético/farmacología , Amidas/farmacología , Ésteres/farmacología , Herbicidas/farmacología , Propanil/farmacología , Ácido 2,4-Diclorofenoxiacético/química , Amidas/síntesis química , Amidas/química , Ésteres/síntesis química , Ésteres/química , Herbicidas/química , Interacciones Hidrofóbicas e Hidrofílicas , Cinética , Estructura Molecular , Cebollas/efectos de los fármacos , Cebollas/crecimiento & desarrollo , Oryza/efectos de los fármacos , Oryza/crecimiento & desarrollo , Propanil/química
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