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Metabolism of diclofop‐methyl (methyl‐2‐[4‐(2′,4′‐dichlorophenoxy)phenoxy] propanoate) in cell suspensions of diploid wheat (Triticum monococcum)
Author(s) -
DUSKY J. A.,
DAVIS D. G.,
SHIMABUKURO R. H.
Publication year - 1980
Publication title -
physiologia plantarum
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.351
H-Index - 146
eISSN - 1399-3054
pISSN - 0031-9317
DOI - 10.1111/j.1399-3054.1980.tb02644.x
Subject(s) - metabolite , metabolism , chemistry , methanol , hydrolysis , stereochemistry , ring (chemistry) , conjugated system , cell culture , acetone , conjugate , biochemistry , biology , organic chemistry , mathematical analysis , mathematics , genetics , polymer
The metabolism of the herbicide, diclofop‐methyl (methyl‐2‐[4‐(2′,4′‐dichlorophenoxy)phenoxy]propanoate, in cell suspensions of resistant diploid wheat ( Triticum monococcum L.) was determined 1, 8, and 24 h after treatment with 14 C‐diclofop‐methyl. The 14 C‐labeled products were identified by thin layer chromatographic comparisons to appropriate standards. Eight hours after treatment with 5 μM diclofop‐methyl in 0.8% acetone (neither of which were toxic to the cell suspensions) 87.2% (84.0% methanol soluble, 3.2% methanol insoluble) of the total 14 C recovered (90.4%) was in the cells and 12.8% was in the medium. Major metabolites found in methanol extracts of the cells were diclofop (2‐[4‐(2′,4′‐dichlorophenoxy)phenoxylpropionic acid), diclofop hydroxylated at an undetermined position on the 2,4‐dichlorophenyl ring (ring‐OH diclofop), and conjugates of ring‐OH diclofop. Acid hydrolysis of the conjugated metabolite(s) yielded ring‐OH diclofop and diclofop. Twenty‐four hours after treatment 70–75% of the total 14 C recovered was present as conjugated metabolites. With the exception of ring‐OH diclofop, all metabolites present in the cells were also recovered from the medium. A metabolite found in low concentrations in the medium that yielded diclofop upon hydrolysis was identified as an ester conjugate. Toxic concentrations of diclofop‐methyl (10 and 20μ M ) had no effect on the metabolism of the herbicide, although the rate of uptake was slower than for cells treated with 5 μ M herbicide. The products of diclofop‐methyl metabolism in cell suspensions of T. monococcum were compared to previous data from T. aestivum intact plant metabolism of diclofop‐methyl.