Metabolic fate of bioxone in cotton

Abstract

The metabolic fate of the 14C-labeled herbicide, 2-(3,4-dichlorophenyl)-4-methyl-1,2,4-oxadiazolidine-3,5-dione (bioxone), in cotton ( Gossypium hirsutum L. “Acala 4-42-77”) was studied using thin-layer chromatography, autoradiography, and counting. Bioxone- 14C was readily metabolized by cotton tissue to 1-(3,4-dichlorophenyl)-3-methylurea (DCPMU) and 1-(3,4-dichlorophenyl)urea (DCPU). Leaf discs metabolized bioxone- 14C rapidly; 12 hr posttreatment, 65% of the 14C in methanol extracts was in forms other than intact herbicide. Excised leaves treated through the petiole with either heterocyclic ring-labeled or phenyl ring-labeled herbicide contained little bioxone- 14C after 1 day; DCPMU was formed early then decreased with time. DCPU accounted for 55–70% of the 14C in excised leaves 3 days posttreatment. In intact plants treated via the roots, the herbicide was rapidly metabolized in the roots to DCPMU and DCPU; little or no intact herbicide was translocated to the leaves. Little radioactivity accumulated in the roots with time; the radioactivity in the leaves accounted for 80–90% of the methanol-soluble 14C 47 days posttreatment. Most of the 14C in the leaves was recovered as DCPU (50–60%) and unidentified polar metabolite(s) which remained at the origin of the thin-layer plates (30–40%). The percentage of radioactivity which remained in cotton residue after methanol extraction increased with time. Digestion of the plant residues with the proteolytic enzyme pronase indicated that some of the nonextractable 14C may be DCPMU and DCPU complexed with proteins. Similar metabolic patterns were noted after treatment with either heterocyclic ring-labeled or phenyl ring-labeled bioxone- 14C. Generally, bioxone was metabolized to DCPMU which in turn was demethylated to DCPU. The herbicide and DCPMU were 20 times as toxic as DCPU to oat ( Avena sativa L.), a susceptible species.