Hydrolysis of Chlorantraniliprole and Cyantraniliprole in Various pH Buffer Solutions

The hydrolysis reactions of [14C]-chlorantraniliprole (CLAP) and cyantraniliprole (CNAP) were investigated in sterile buffer solutions at pH 4, 7, and 9. Both compounds displayed similar degradation reactions. The reactions observed were intramolecular cyclizations and rearrangements instead of the anticipated amide hydrolysis to carboxylic acids. Despite a minor difference in their structures, the degradation rates for the two compounds were substantially different. The reaction rates were examined at multiple temperatures to understand the mechanistic aspects of the underlying transformations. Similarities and differences in the hydrolysis behavior of these compounds in various pH values and temperatures are described.