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

• Published in: Chemistry and physics of lipids 2020-09, Vol.231, p.104947-104947, Article 104947
• Main Authors: 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.
• Format: Article
• Language: English
• Subjects: 2,4-D; 2,4-Dichlorophenoxyacetic Acid - chemistry; 2,4-Dichlorophenoxyacetic Acid - pharmacology; Amides - chemical synthesis; Amides - chemistry; Amides - pharmacology; Esters - chemical synthesis; Esters - chemistry; Esters - pharmacology; Fatty acids; Herbicides - chemistry; Herbicides - pharmacology; Hydrophobic and Hydrophilic Interactions; Kinetics; Molecular Structure; Onions - drug effects; Onions - growth & development; Organochlorides herbicides; Oryza - drug effects; Oryza - growth & development; Propanil; Propanil - chemistry; Propanil - pharmacology; Renewable resources
• ISSN: 0009-3084; 1873-2941
• DOI: 10.1016/j.chemphyslip.2020.104947

[Display omitted] •Synthesis of new lipophilic amides and esters analogues of classical organochlorides herbicides.•Lipophilic compounds synthesized showed superior in vitro activity than commercial herbicides.•The kinetic and NMR studies showed a decrease in half-life time of new herbicides compounds compared to 2,4-D. 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.