The metabolism of fenazox in tomato plants

Results from investigations on the metabolism of 14C-Fenazox show that in 6-8 weeks old tomato-plants (sort "Harzfeuer") the agent undergoes a biotransformation. After chromatographic separation the structure of the biotransformation products was elucidated by comparison to authentic test substances, by derivatization as well as by means of physico-chemical methods. With that, the following metabolites were identified: non-transformed Fenazox, o-hydroxyazobenzene, o-hydroxyaniline, and p-hydroxyaniline. Probably, the agent is first transformed enzymatically or non-enzymatically into o-hydroxyazobenzene, then follows a reductive cleavage into o-hydroxyaniline and aniline. In its turn, the latter is transformed into o-hydroxy- and p-hydroxyaniline. Experiments in the field of transformation kinetics indicated that the concentration of the applied Fenazox rapidly decreases and that the first transformation product o-hydroxyazobenzene in the beginning increases and then again decreases in its concentration. With increasing application time it comes to an increase of the non-extractable residues.