Trifluralin [a,a,o-Trifluoro-2 ,6-dinitro-N,N-di-n-propyl-p-toluidine ] 
Excretion of radioactivity by rats and dogs was virtually complete 
within three days following administration of a single oral dose of cl4F 
trifluralin--/78% appeared in the feces and 22% in the urine. In addition 
to unchanged trifluralin, a mono amino analog (VI) was found in the feces. 
Three metabolites were identified in the urine. One compound (IV) was 
formed by complete dealkylation; the second (III), by loss of a propyl 
group and reduction of one nitro group; the third (V), by loss of both 
propyl groups and reduction of one nitro group. The probably intermediate 
(II), formed by loss of one propyl group, was observed by gas chromatography 
but never isolated because of the small amounts present. All other compounds 
were isolated. Melting points were obtained for all solids and matched with 
authentic material. Infrared, TLC, and X-ray diffraction were also used to 
identify metabolites (405). 
In vivo studies were conducted with a cow and a goat. The major 
product identified from both urine and feces was compound VII (649). 
In vitro degradation of trifluralin in artificial rumen fluid was 
studied. Use of TLC, GC, and radiochemical procedures revealed a rapid 
destruction of trifluralin. The principal products formed were: 
N2, N*-di-n-propyl-3-nitro-5-trifluoromethyl phenylenediamine (VI) and 
N+, N'-di-n-propyl-a,a,a, -trifluorotoluene-3,4,5-triamine (VII) (553). 
Carrots were grown from seeds in trifluralin treated soil for 110 
days and then harvested. Thin-layer chromatography and radioautography 
of carrot root indicated that a,a,a-trifluoro-2 ,6-dinitro-N-n-propyl-p- 
toluidine (II) was the most prominent metabolite. a,a,a-Trifluoro-2- 
amino-6-nitro-N-n-propyl-p-toluidine (III) and 3,5-dinitro-4-di-n-propyl- 
aminobenzoic acid (X) were also detected (553). 
The metabolism of trifluralin was studied in autoclaved sand by intact 
peanut (Arachis hypogaea L.) and sweet potato (Ipomoea batalas L.) plants and 
crude extracts of these plants. Both intact plants and crude extracts 
degraded trifluralin. With crude extracts of peanuts, the initial degradation 
product was an incompletely dealkylated product (II). This was converted to 
compound III by reduction of one nitro group. Degradation also proceeded by 
reduction of one nitro group to compound VI with subsequent dealkylation to 
compound III. Compounds VII and IX were also observed. Two other metabolites 
were detected but not completely characterized: compound XI, a phenol; and 
compound XII, a dealkylated benzoic acid. Degradation of trifluralin by 
sweet potato extracts followed similar paths; however, the initial degradation 
apparently was the reduced compound VI. Compounds XI and XII were also 
observed (1772). 
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