Proposed Biodegradation Pathways by nLaccase and BNNS-Arg@Lac. For ATR biodegradation, we observed the distinct pathways during nlaccase and BNNS-Arg@Lac catalyzed reactions (Figure ). In nlaccase group, after 4 h, ATR (C8H14ClN5) was presumably oxidized to C8H13ClN5OH and C8H13ClN5OH was further oxidized to C8H12ClN5(OH)2 at 12 h. At 8 h, we tentatively identified another intermediate (C8H14N5OH) generated from the dechlorination reaction. Then this intermediate was oxidized to another two products: C3N3(OH)3 and C3N3H3O3. After 12 h, no significant products were generated in nlaccase group. In contrast, ATR degradation by BNNS-Arg@Lac and nlaccase in synthetic agricultural wastewater, sampling at 0, 12, and 24 h. in BNNS-Arg@Lac group, at 4 h, a dechlorination product, C8H14N5OH, was putatively identified and then oxidization products C3N3(OH)3 and C3N3H3O3 emerged in 8-h samples. At 12 h, smaller molecules: C4N2H6O3 and C2N2H3O2 were tentatively identified as products. More products, such as C4H12N4OCl were putatively identified at the first 4 h and C5H8ClN5 appeared at 8 h and then was oxidized to C5H6ClN4OH. The end product profiles at 24 h illustrated that the BNNS-Arg@Lac group resulted in the production of a greater number of smaller compounds compared to using only nlaccase. This difference in compound composition may explain why samples subjected to 24-hour BNNS-Arg@Lac catalysis exhibited lower toxicity towards chlorophyll a synthesis in C. vulgaris (Figure ). Two models were proposed by molecular docking (see supporting information and Figure ). ATR binding affinity with nlaccase was -5.3 kcal/mol. Because of the software limitation, the graphene-like nanosheet was used as the best representation of BNNSs. After the docking, ATR binding affinity with the immobilized laccase was increased to -10.3 kcal/mol. The modeling result indicated that the change in enzyme structure might be responsible for the different ATR degradation outcomes.