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Novel lipophilic analogues from 2,4-D and Propanil herbicides: Biological activity and kinetic studies.
Chem Phys Lipids. 2020 Jul 02; 231:104947.CP

Abstract

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.

Authors+Show Affiliations

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.Grupo de Catálise e Cinética, Universidade Federal do Paraná, Curitiba, PR, Brazil.Laboratório de Ressonância Magnética Nuclear, Departamento de Química, Universidade Federal do Paraná, Curitiba, PR, Brazil.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.Laboratory of Asymmetric Synthesis, Instituto de Química de Recursos Naturales, Universidad de Talca, Talca, 3460000, Chile.Instituto de Ciencias Químicas Aplicadas, Universidad Autónoma de Chile, Talca, 3467987, Chile.Grupo de Catálise e Cinética, Universidade Federal do Paraná, Curitiba, PR, Brazil.Laboratório de Ressonância Magnética Nuclear, Departamento de Química, Universidade Federal do Paraná, Curitiba, PR, Brazil. Electronic address: carolinedoca@ufpr.br.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

32622838

Citation

Porciuncula, Larissa M., et al. "Novel Lipophilic Analogues From 2,4-D and Propanil Herbicides: Biological Activity and Kinetic Studies." Chemistry and Physics of Lipids, vol. 231, 2020, p. 104947.
Porciuncula LM, Teixeira AR, Santos MFC, et al. Novel lipophilic analogues from 2,4-D and Propanil herbicides: Biological activity and kinetic studies. Chem Phys Lipids. 2020;231:104947.
Porciuncula, L. M., Teixeira, A. R., Santos, M. F. C., D'Oca, M. G. M., Santos, L. S., Nachtigall, F. M., Orth, E. S., & D'Oca, C. R. M. (2020). Novel lipophilic analogues from 2,4-D and Propanil herbicides: Biological activity and kinetic studies. Chemistry and Physics of Lipids, 231, 104947. https://doi.org/10.1016/j.chemphyslip.2020.104947
Porciuncula LM, et al. Novel Lipophilic Analogues From 2,4-D and Propanil Herbicides: Biological Activity and Kinetic Studies. Chem Phys Lipids. 2020 Jul 2;231:104947. PubMed PMID: 32622838.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Novel lipophilic analogues from 2,4-D and Propanil herbicides: Biological activity and kinetic studies. AU - Porciuncula,Larissa M, AU - Teixeira,Alex R, AU - Santos,Maria F C, AU - D'Oca,Marcelo G M, AU - Santos,Leonardo S, AU - Nachtigall,Fabiane M, AU - Orth,Elisa S, AU - D'Oca,Caroline R M, Y1 - 2020/07/02/ PY - 2020/05/26/received PY - 2020/06/29/revised PY - 2020/06/30/accepted PY - 2020/7/6/pubmed PY - 2020/7/6/medline PY - 2020/7/6/entrez KW - 2,4-D KW - Fatty acids KW - Organochlorides herbicides KW - Propanil KW - Renewable resources SP - 104947 EP - 104947 JF - Chemistry and physics of lipids JO - Chem. Phys. Lipids VL - 231 N2 - 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. SN - 1873-2941 UR - https://www.unboundmedicine.com/medline/citation/32622838/Novel_lipophilic_analogues_from_2,4-D_and_Propanil_herbicides:_Biological_activity_and_kinetic_studies L2 - https://linkinghub.elsevier.com/retrieve/pii/S0009-3084(20)30078-5 DB - PRIME DP - Unbound Medicine ER -
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