The capacity of benzoxazolinone metabolization of dicotyledonous species characteristic for the former vegetation classes Secalietea (grain field weed communities) and Chenopodietea (hoed vegetable communities) was estimated by the production of BOA-6-OH, BOA-6-β-O-glucoside, and BOA-N-glucoside. Except for Urtica urens, Galinsoga ciliata, and Polygonum aviculare (Chenopodietea), all species tested were able to synthesize BOA-6-OH, its glucoside, and BOA-N-glucoside, but effectiveness of BOA metabolism differed highly depending on species and plant organ. There was no correlation between bacterial phenoxazinone production and appearance of metabolites in the plants. Bioassays demonstrated that N-glucosylation is more efficient in BOA detoxification than O-glucosylation. The intermediate BOA-6-OH, however, is more harmful than BOA itself. It is therefore assumed that the ability to synthesize BOA-N-glucoside reduces the sensitivity to BOA strikingly. Since the detoxification capacity did not correlate with the taxonomic position, the affiliation of the species tested with the corresponding plant communities was taken into consideration. Evidently, the ecobiochemical potential of species to detoxify benzoxazolinone, regarded as an essential secondary compound in rye and wheat fields, reflects their occurrence in those plant associations. The ability to cope with the compound could be the result of co-evolutionary processes and presents a hidden aspect of allelopathic interaction.