Reactivity of the insecticide Fenitrothion toward O and N nucleophiles

The reactivity of Fenitrothion toward several O- and N-based nucleophiles, including ambident and [alpha]-nucleophiles, is examined in basic media in water containing 1,4-dioxane. A major [alpha]-effect is observed with HO[O.sup.-], N[H.sub.2]OH, and N[H.sub.2][O.sup.-], thus confirming the participation of the nucleophile in the rate-limiting step of the reaction.