Cyantraniliprole
The overall route of degradation of cyantraniliprole was derived from a combination of aerobic soil degradation and anaerobic soil degradation as well as photolysis in moist soil, described in detail in Part A. The degradation process is complex and proceeds along at least two major pathways in dark soil and via a combination of aerobic soil degradation as well as photodegradation in moist soil. The degradation pathways will be referred to as the IN-J9Z38 pathway, IN-JCZ38 pathway, and the photodegradation pathway, in this discussion of degradation processes. Degradation of cyantraniliprole in dark aerobic soil proceeded along two pathways, the IN-J9Z38 pathway and the IN-JCZ38 pathway. Formation of IN-J9Z38 is primarily a hydrolysis controlled dehydration-cyclization reaction. IN-J9Z38 degraded in succession to mainly IN-K5A77 and IN-K5A78, both of which involve hydrolytic conversion of the cyano group into an amide and then to the carboxylic acid. Initial formation of IN-JCZ38 also involves a conversion of the cyano group to an amide, and subsequent transformations involve a combination of demethylation of –CONHCH3 as well further hydrolysis of the amide to a carboxylic acid. The metabolites in the IN-JCZ38 pathway can in principle undergo cyclization of the bridging amide group to form the pyrimidine ring at any stage, hence, conversion of IN-JSE76 to IN-K5A78, and conversion of IN-K5A79 to IN-PLT97 was not only feasible, but was actually observed. Some of these conversions were established via transformations observed when the individual metabolites were investigated in metabolite dosed soil degradation studies. Minor metabolites, IN-K7H19, INM2G98, and IN-DBC80 were also identified, although they were not present in amounts exceeding 5% of the applied amounts in any system, with the exception of the IN-M2G98 metabolite which was observed as a major metabolite in the INK5A79 dosed study. There were numerous additional metabolites, but none of them exceeded 1 to 2% of the total residue and were not identifiable. Formation of CO2 from both radiolabels indicated that the parent compound can be mineralized. Characterization of non-extractable residue also showed significant portion of the material associated with humic and fulvic acid fractions, which infers that small molecules formed may become a part of soil organic matter.