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

Porciuncula, Larissa M.; Teixeira, Alex R.; Santos, Maria F.C.; D’Oca, Marcelo G.M.; Santos, Leonardo S.; Nachtigall, Fabiane M.; Orth, Elisa S.; D’Oca, Caroline R.M.

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

2020

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.

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