INFIQC   05475
INSTITUTO DE INVESTIGACIONES EN FISICO- QUIMICA DE CORDOBA
Unidad Ejecutora - UE
congresos y reuniones científicas
Título:
Reactivity of the insecticide fenitrothion with butylamine and piperidine. Effect of cyclodextrins.
Autor/es:
NATALIA M. ROUGIER; ELBA I. BUJÁN
Lugar:
Riviera Maya
Reunión:
Conferencia; 11º Conferencia Latinoamericana de Fisicoquímica Orgánica; 2011
Institución organizadora:
Sociedad Química de México
Resumen:
Fenitrothion (O,O-dimethyl O-(3-methyl-4-nitrophenyl)-phosphorothioate) (1) is a widely used organophosphorus insecticide and acaricide effective against a wide range of pests. It reacts in water with O- and N-based nucleophiles through different pathways depending on the nucleophile. We have previously studied the reactions of 1 with butylamine (BuNH2)1 and found that demethylfenitrothion (2) was formed as the main product along with 3-methyl-4-nitrophenoxide (3), indicating competition between the SN2(P) and SN2(C) pathways (Scheme 1). The yield of 3 increases with pH and decreases with amine concentration at constant pH, varying from 6% at pH 10.00 to 25% at pH 11.50.1 We present now the results on the reaction of 1 with piperidine (Pip) in water and the effect of the presence of β-cyclodextrin (β-CD) and sucrose on the reactivity and selectivity of the reactions of 1 with BuNH2 and with Pip.