The metabolism of a new fluorinated fungicide
[N-ethyl-N-methyl-4-(trifluoromethyl)-2-(3,4-dimethoxyphenyl)benzamide] by Acer
pseudoplatanus cells was studied concurrently through
the
use of 19F NMR and with 14C-labeled compound.
Approximately 10 fluorinated compounds were
observed by 19F NMR in the culture; 5 of them were
identified. The detection limit was <1 μM.
Methanol appeared to be a useful solvent as it was able to
dissolve the lipophilic active ingredient
as well as the more polar derivatives. However, the use of
chloroform allowed a better separation
of the NMR signals for the derivatives fairly soluble in this solvent.
The metabolism of the studied
compound mostly occurred through ring demethoxylation and
N-dealkylation. The more lipophilic
derivatives diffused into the culture medium; in contrast, the more
hydrophilic ones remained inside
the cells. This work shows that the sensitivity and high
resolution power of liquid 19F NMR
spectroscopy confirm its potential usefulness to study the metabolism
of xenobiotics.
Keywords: Acer pseudoplatanus L.; 19F NMR; fungicide;
metabolization; plant cells
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