Metabolic fate of [¹⁴C]diuron and [¹⁴C]linuron in wheat (Triticum aestivum) and radish (Raphanus sativus)

Abstract

Metabolism of xenobiotics in plants usually occurs in three phases, phase I (primary metabolism), phase II (conjugation processes), and phase III (storage). The uptake and metabolism of [(14)C]diuron and [(14)C]linuron were investigated in wheat and radish. Seeds were sown in quartz sand and irrigated with a nutrient solution of either radioactive herbicide. Plants were harvested after two weeks, and metabolites were extracted and then analyzed by radio-reverse-high-performance liquid chromatography (HPLC). Uptake of the two molecules was higher in radish compared to wheat. Translocation of parent compounds and related metabolites from roots to aerial plant parts was important, especially for radish. A large proportion of extractable residues were found in radish whereas nonextractable residues amounted to 30% in wheat, mainly associated with roots. Chemical structure of metabolites was thereafter identified by acid, alkaline, and enzymatic hydrolyses followed by electrospray ionization mass spectrometry (ESI-MS) and proton nuclear magnetic resonance spectroscopy ((1)H NMR). This study highlighted the presence of diuron and linuron metabolites conjugated to sugars in addition to N-demethylation and N-demethoxylation products.