Fate of carbon-14[-labeled] trifluralin in artificial rumen fluid and in ruminant animals

Gołab, T; Herberg, R. J.; Day, Edgar W.; Raun, A. P.; Holzer, Frank; Probst, G. W.

doi:10.1021/jf60163a030

Cited by 19 publications

(13 citation statements)

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“…Based on the reductive cleavage of trifluralin polar products, previously described by Golab et al (1969), benefin extractable polar products are also assumed to be a mixture of aromatic amine condensation products. The nature of the tightly soil-bound nonextractable radioactivity is unknown.…”

Section: Resultsmentioning

confidence: 99%

“…Subsequent aliquots were removed at V4, V2, 3/4, 1, 1 1/ , 2> 21/2, 3, 4, 5, 6, 7, 8, 9, 10, and 11 hr. These aliquots were extracted according to the procedure of Golab et al (1969), and were subjected to radiochemical, thin-layer, and gas chromatographic analyses.…”

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confidence: 99%

“…Using the same facilities, techniques, and procedures described by Golab et al (1969) for trifluralin, one lactating goat was fed unlabeled benefin for 8 days at 1 ppm incorporated in the ration, labeled benefin for 1 day, and unlabeled benefin again for 14 days. The second goat served as a con- trol and received no benefin throughout the experimental period.…”

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confidence: 99%

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Fate of benefin in soils, plants, artificial rumen fluid, and the ruminant animal

Gołab¹,

Herberg²,

Gramlich³

et al. 1970

J. Agric. Food Chem.

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Benefin, a selective, preemergence, soil-incorporated herbicide, decomposed rapidly in soil under defined anaerobic conditions, with approximately 5% detectable after 16 days; whereas, under defined aerobic conditions, 50% of the originally incorporated benefin was detectable after 120 days and only 12.1 % after 352 days. Identifiable degradation products were the dealkylated, reduced, and oxidized derivatives of benefin, and an unidentified polar mixture. Soil-incorporated 14C-labeled benefin was not readily absorbed into growing peanut plants and alfalfa. Most of the radioactivity absorbed by plants was not extractable. In the extractable portion, the identifiable degradation products were similar to those found in soil. Artificial rumen fluid destroyed benefin rapidly; only 0.1 % of the original benefin remained after 12 hr incubation. Identifiable degradation products were reduced forms of benefin and nonidentifiable polar substances. Radioactivity from 14C-labeled benefin orally administered to the lactating ruminant animal was excreted in the urine (10.8%) and feces (89.1%) within 5 days after ingestion. No radioactivity residue was found in milk.Benefin (a,a,a-trifluoro-2,6-dinitro-Abutyl -Nethyl -ptoluidine) is a chemical analog of trifluralin (a,a,atrifluoro-2,6-dinitro-./V,/V-dipropyl-p-toluidine) possessing similar herbicidal properties, and is marketed under the trade name Balan. It is a selective, soil-incorporated, preemergence herbicide for many agronomic and horticultural crops, some of which may be consumed as forage. The herbicidal spectrum, which complements trifluralin, includes annual grasses and broadleaf weeds. The fate of trifluralin in soils (Probst et al., 1967), plants , and artificial rumen fluid and ruminant animals (Golab et al., 1969) has been extensively investigated. A similar investigation, based on the experimental methodology employed with trifluralin, was undertaken to determine benefin's persistence, pathway of degradation, and the nature of degradation products. MATERIALS AND METHODSGeneral Methods. Labeled Benefin. Benefin, used in this investigation, was a mixture of 14C uniformly ringlabeled and trifluoromethyl-labeled species. Degradation studies conducted in our laboratories, subsequent to this investigation, revealed that the purchased 14C-labeled p-chlorobenzoic acid, used in the synthesis of uniformly ring-labeled trifluralin (Marshall et al., 1966) and benefin, is a mixture of 15% uniformly ring-labeled and 85% carboxyl-labeled pchlorobenzoic acids rather than a single molecular species. Its specific activity was 14.04 pCi per mg (3.12 107 dpm per mg), and radiochemical purity, as determined by thin-layer chromatography using silica gel GF developed with carbon tetrachloride, was greater than 99 %.Labeled benefin used in these experiments, except in the ruminant animal (goat study), was diluted with nonlabeled material. The specific activity of I4C-benefin after dilution was 0.20 ^Ci per mg in the soil, 1.40 pCi per mg in soil with plants, and 0.92 pd per mg in arti...

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Fate of benefin in soils, plants, artificial rumen fluid, and the ruminant animal

Gołab¹,

Herberg²,

Gramlich³

et al. 1970

J. Agric. Food Chem.

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“…The major metabolic pathway of trifluralin involves nitro reduction, N-dealkylation, cyclization, hydroxylation and conjugation [9] . The product of reduction of both nitro groups was the main metabolite identified in urine and feces of lactating goats [10] .…”

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Pharmacokinetics of Trifluralin in Blood and Heart Tissue of Mice

Zaidenberg¹,

Marra²,

Villagra³

et al. 2009

Chemotherapy

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Background: Trifluralin displays anti-Trypanosoma cruzi activity and a potential therapeutic effect for the treatment of Chagas disease. We assessed peroral and intramuscular trifluralin pharmacokinetics in mouse blood and heart tissue. Methods: A parallel experimental design was used. Healthy adult male CF1 albino mice (n = 108, 25–35 g bw) received a single peroral or intramuscular trifluralin dose (50 mg/kg in peanut oil). Blood and heart tissue samples were taken at set times after intramuscular and peroral trifluralin administration. Feces and tissue samples were taken 12 h after intramuscular trifluralin administration. Trifluralin concentrations in whole blood, feces and tissues were determined by HPLC. Results: After intramuscular and peroral administration, maximum whole blood concentration (C_max) was attained at 30 min and 2.0 h (t_max) (28.2 ± 0.7 and 7.8 ± 0.033 μg/ml; p < 0.05). C_max in heart tissue was attained at 1.0 and 2.0 h (0.6 ± 0.004 and 0.2 ± 0.002 μg/g; p < 0.05). Liver, perirenal and subcutaneous fat concentrations were 55.1, 66.3 and 59.7 ng/mg tissue protein. Peroral and intramuscular penetration ratios determined by comparing heart tissue areas under the curve were 6.3 and 4.0%, respectively. Conclusion: Intramuscular trifluralin could be a new alternative for the treatment of Chagas disease.

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“…The formation of benzimidazole derivatives of dinitramine (A^^-diethyl-ajaja-trifluoro^jSdinitrotoluene-2,4-diamine) in soil has been reported (21). Tri fluralin was degraded in 11 hr in an artificial rumen fluid to two reduction products and several other trace metabolites (10).…”

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confidence: 99%

Soil Enrichment Studies with Trifluralin

Carter¹,

Camper

1975

Weed sci.

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Soil enrichment studies were conducted with trifluralin (α,α,α-trifluoro-2,6-dinitro-N,N-dipropyl-p-toluidine) with and without exogenous carbon and nitrogen. From 72 bacterial isolates obtained, eight representative ones were tentatively identified as members of the genusPseudomonasbased on size, shape, Gram reaction, and reaction on fluorescent and motility agar. Two of these eight isolates exhibited a significant increase in numbers of viable cells when grown in a medium with trifluralin as the only exogenous carbon and nitrogen source. Chromatographic analysis of culture medium extracts revealed the presence of a degradation product which was not present in the herbicide control. The concentration of this unknown was greatest at the 50 mg/L level of trifluralin which also supported the greatest bacterial growth.

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Fate of carbon-14[-labeled] trifluralin in artificial rumen fluid and in ruminant animals

Cited by 19 publications

References 5 publications

Fate of benefin in soils, plants, artificial rumen fluid, and the ruminant animal

Fate of benefin in soils, plants, artificial rumen fluid, and the ruminant animal

Pharmacokinetics of Trifluralin in Blood and Heart Tissue of Mice

Soil Enrichment Studies with Trifluralin

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