Synthesis and spectroscopic characterization of acetyl-Clx (x = 0,1,2 or 3) and nitroso derivatives of carbaryl and three possible metabolites.

Acetyl-Clx (x = 0,1,2 or 3) and nitroso derivatives of carbaryl, 1-naphthol. 5-hydroxycarbaryl, and 1,5-naphthalenediol were synthesized. Compounds were characterized by infrared, mass, and nuclear magnetic resonance spectroscopy. N-chloroacetylation (Cl = 0,1,2, or 3) of carbaryl was readily accomplished through the pyridine-catalyzed reaction of carbaryl with the appropriate acid chlorides. Trichloroacetylation was also possible through the pyridine-catalyzed reaction with the anhydride. N-nitrosation could also be done readily. N-nitroso- and N-trichloroacetyl carbaryl underwent decomposition to carbaryl on exposure to atmosphere moisture and could be maintained in the pure state only with difficulty. The other derivatives were stable under normal storage conditions.