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

dc.contributor.authorPorciuncula L.M.
dc.contributor.authorTeixeira A.R.
dc.contributor.authorSantos M.F.C.
dc.contributor.authorD'Oca M.G.M.
dc.contributor.authorSantos L.S.
dc.contributor.authorNachtigall F.M.
dc.contributor.authorOrth E.S.
dc.contributor.authorD'Oca C.R.M.
dc.date.accessioned2020-09-02T22:25:54Z
dc.date.available2020-09-02T22:25:54Z
dc.date.issued2020
dc.identifier10.1016/j.chemphyslip.2020.104947
dc.identifier.citation231, , -
dc.identifier.issn00093084
dc.identifier.urihttps://hdl.handle.net/20.500.12728/5833
dc.descriptionThis 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. © 2020 Elsevier B.V.
dc.language.isoen
dc.publisherElsevier Ireland Ltd
dc.subject2,4-D
dc.subjectFatty acids
dc.subjectOrganochlorides herbicides
dc.subjectPropanil
dc.subjectRenewable resources
dc.subject2,4 dichlorophenoxyacetic acid
dc.subjectfatty acid ester
dc.subjectpropanil
dc.subjectsulfuric acid
dc.subjecttriethylamine
dc.subjectacid hydrolysis
dc.subjectaminolysis
dc.subjectArticle
dc.subjectcarbon nuclear magnetic resonance
dc.subjectcatalysis
dc.subjectchemical structure
dc.subjectcontrolled study
dc.subjectesterification
dc.subjectgermination
dc.subjectherbicidal activity
dc.subjecthydrolysis
dc.subjectin vitro study
dc.subjectkinetics
dc.subjectlettuce
dc.subjectlipophilicity
dc.subjectmonocot
dc.subjectonion
dc.subjectplant growth
dc.subjectpriority journal
dc.subjectproton nuclear magnetic resonance
dc.subjectrate constant
dc.subjectreaction analysis
dc.subjectreaction time
dc.subjectstoichiometry
dc.subjectsynthesis
dc.subjectultraviolet visible spectroscopy
dc.titleNovel lipophilic analogues from 2,4-D and Propanil herbicides: Biological activity and kinetic studies
dc.typeArticle


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