Tolylfluanid
Tolylfluanid is degraded in first step via hydrolytic cleavage of the N-S bond yielding dimethylaminosulfo-toluidide (DMST, metabolite II) and probably dichlorofluoromethanesulfenic acid. In further steps DMST is oxidised and/or demethylated via 4-(dimethylaminosulfonylamino)benzoic acid (XI) or methylaminosulfo-toluidide (IX) resulting in 4-(methylaminosulfonylamino)benzoic acid (XII). Final degradation product is CO2. Concerning the dichlorofluoromethylsulfonyl moiety, neither dichlorofluoromethanesulfenic acid nor other intermediates except CO2 have ever been determined. Therefore it has been assumed that the degradation steps of this moiety are too fast for being determined. Dichloromethanesulfenic acid has been postulated to be degraded via acid-katalysed elimination of water, followed by further hydrolytic steps giving probably carbonylsulfid and finally CO2. Another possibility might be an oxidation of dichlorofluoromethanesulfenic acid yielding dichlorofluoromethanesulfonic acid which is also further converted to CO2. The halogen and sulfur atoms are most probably eliminated in the form of inorganic ions.