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  • The nitropesticide bifenox (methyl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate) is reduced in aprotic media in two reduction steps. The first heterogeneous electron transfer involves the acceptance of one electron leading to the formation of a relatively stable nitro anion radical that was characterized by EPR spectroscopy. The electrochemically generated radical anion eventually decomposes to two stable products. Intramolecular electron transfer coupled with chemical steps leads in the first case to the cleavage of the carboxymethyl group and the formation of the nitropesticide nitrofen ((2,4-dichlorophenyl)(4-nitrophenyl) ether) and in the second case to a trans-esterification process, i.e., an exchange of the methyl group for an alkyl of the supporting electrolyte. Both these final products retain pesticidal activity, which explains the high efficiency of bifenox as a pesticide.
  • The nitropesticide bifenox (methyl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate) is reduced in aprotic media in two reduction steps. The first heterogeneous electron transfer involves the acceptance of one electron leading to the formation of a relatively stable nitro anion radical that was characterized by EPR spectroscopy. The electrochemically generated radical anion eventually decomposes to two stable products. Intramolecular electron transfer coupled with chemical steps leads in the first case to the cleavage of the carboxymethyl group and the formation of the nitropesticide nitrofen ((2,4-dichlorophenyl)(4-nitrophenyl) ether) and in the second case to a trans-esterification process, i.e., an exchange of the methyl group for an alkyl of the supporting electrolyte. Both these final products retain pesticidal activity, which explains the high efficiency of bifenox as a pesticide. (en)
  • Nitropesticid bifenox (methyl 5-(2,4-dichlorofenoxy)-2-nitrobenzoát) je redukován v nevodním prostředí ve dvou krocích. První heterogenní přenos elektronu představuje přijetí jednoho elektronu molekulou za tvorby relativně stabilního nitro anion radikálu, který byl charakterizován pomocí EPR spektroskopie. Konečným produktem rozkladu elektrochemicky generovaného radikálu jsou dva stabilní produkty. Intramolekulární přenos elektronu v spojení s chemickými kroky vede jednak k odštěpení karboxymethylové skupiny a ke vzniku nitropesticidu nitrofen ((2,4-dichlorofenyl)(4-nitronitrofenyl) éter), jednak k transesterifikaci, t.j. výměně methylové skupiny bifenoxu za alkyl základního elektrolytu. Oba tyto konečné produkty si zachovávají pesticidní vlastnosti, co do jisté míry vysvětluje vysokou účinnost pesticidu bifenox. Při negativnějších potenciálech podléhá radikál anion další dvou elektronové redukci. (cs)
Title
  • Decomposition reactions of bifenox anion radical involving intramolecular electron transfer
  • Reakce rozpadu anion radikálu bifenoxu s účastí intramolekulárního přenosu elektronu (cs)
  • Decomposition reactions of bifenox anion radical involving intramolecular electron transfer (en)
skos:prefLabel
  • Decomposition reactions of bifenox anion radical involving intramolecular electron transfer
  • Reakce rozpadu anion radikálu bifenoxu s účastí intramolekulárního přenosu elektronu (cs)
  • Decomposition reactions of bifenox anion radical involving intramolecular electron transfer (en)
skos:notation
  • RIV/61388955:_____/05:00022179!RIV06-AV0-61388955
http://linked.open.../vavai/riv/strany
  • 156;164
http://linked.open...avai/riv/aktivita
http://linked.open...avai/riv/aktivity
  • P(GA203/03/0821), P(GP203/02/P082), P(OC D15.10), Z(AV0Z40400503)
http://linked.open...iv/cisloPeriodika
  • 1-2
http://linked.open...vai/riv/dodaniDat
http://linked.open...aciTvurceVysledku
http://linked.open.../riv/druhVysledku
http://linked.open...iv/duvernostUdaju
http://linked.open...titaPredkladatele
http://linked.open...dnocenehoVysledku
  • 517061
http://linked.open...ai/riv/idVysledku
  • RIV/61388955:_____/05:00022179
http://linked.open...riv/jazykVysledku
http://linked.open.../riv/klicovaSlova
  • bifenox; nitro-group reduction; double-layer effect (en)
http://linked.open.../riv/klicoveSlovo
http://linked.open...odStatuVydavatele
  • CH - Švýcarská konfederace
http://linked.open...ontrolniKodProRIV
  • [A9B104F3982B]
http://linked.open...i/riv/nazevZdroje
  • Journal of the Electroanalytical Chemistry and Journal of Electroanalytical Chemistry and Interfacial Electrochemistry
http://linked.open...in/vavai/riv/obor
http://linked.open...ichTvurcuVysledku
http://linked.open...cetTvurcuVysledku
http://linked.open...vavai/riv/projekt
http://linked.open...UplatneniVysledku
http://linked.open...v/svazekPeriodika
  • 582
http://linked.open...iv/tvurceVysledku
  • Hromadová, Magdaléna
  • Pospíšil, Lubomír
  • Giannarelli, S.
  • Mořkovská, Petra
http://linked.open...n/vavai/riv/zamer
issn
  • 0022-0728
number of pages
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