Diethylaniline sulfonic acid

Nitroso compounds are formed as intermediates in this reaction. Yields from sulfonic acids, carboxylic acids, and nitro compounds, amongst others, are poor,424 but those from tertiary amines and phenols are often very good,423,426 although naphthols give only the nitroso derivatives for example, yields are 70% from A,iV-diethylaniline,423 96% from phenol,426 98% from o- or 7W-cresol,426 95% from chlorophenol,426 and 75-85% from o-hydroxybenzene-sulfonic acid 428 the diazonium group enters para to the NR2 or OH group. 

An early investigation of alachlor metabolism by a pure culture of fungus showed significant production of 2,6-diethylaniline, which could be further metabolized (42.) More recent research, however, has shown that alachlor is dechlorinated in soil followed by conjugation with glutathione (J. Malik, Monsanto Agricultural Products Co., personal communication). The conjugates are then further metabolized to yield sulfonic and oxanilic acid derivatives of alachlor (22.), which would be very water soluble. 

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