Absorption, Distribution and Excretion
…After oral administration of radiolabeled trifluralin (¹⁴C-CF₃ or ¹⁴CN-propyl-; 100 mg/kg body weight) to rats, 80% of the dose was excreted in feces; only 8% was unmetabolized trifluralin. Only 11-14% of the radioactivity was recovered in bile, indicating incomplete absorption. … Four monkeys (2 males, 2 females) were administered 2 mg/kg of radiolabeled trifluralin ethanol solution intravenously or topically to the forearm, and plasma concentrations were measured after 120 hours to determine the area under the curve for the two administration routes. …After 120 hours, the marker was not detected in 2 of the 4 test animals (1 male, 1 female). Since the data from the two animals whose plasma concentrations were undetectable at 120 hours were most consistent, the data from these two animals were used to calculate the AUC. Skin absorption rate was determined by the ratio of the area under the plasma curve (AUC) to the AUC; [(AUC-dermal/(AUC-iv)] x 100 = 2.84%. /Etrifluralin/
Approximately 80% of the ingested compound was excreted in feces, and the remainder in urine/in the rats and dogs studied/.

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Metabolism/Metabolites
Extensive nitroreduction reactions occurred, producing the corresponding amines, which may be a result of gut microbiota metabolism. Absorbed trifluralin was extensively metabolized, mainly through N-dealkylation and nitroreduction, and then excreted in urine.
In a rat metabolism study, (14)C-trifluralin (radiochemical purity >98%) was dissolved in corn oil and administered by gavage to 5 Fischer rats at a dose of 300 mg/kg/day. 344 rats (half male and half female) were used for three consecutive days. Urine samples (mixed) collected 24–48 hours prior to the study were characterized for metabolites. Liquid scintillation counting, silica gel column chromatography, thin-layer chromatography, high-performance liquid chromatography, nuclear magnetic resonance, and mass spectrometry were used to quantitatively analyze urine samples (mixed by sex) collected at 0–24 hours, 24–48 hours, and 48–54 hours. This study aimed to identify the urinary metabolites of trifluralin. No sex differences were found in the metabolic profile. At least 20–30 unbound metabolites and 10–20 bound metabolites were present in the urine, but the parent compound was not detected. This study did not provide information on the percentage of the administered dose excreted in the urine. However, no single metabolite accounted for more than 8–10% of the total radioactivity in the urine, and most metabolites accounted for 1–2% of the total radioactivity. Therefore, the radioactivity levels of almost all metabolites were very low (<5% of the total radioactive dose). In both sexes' urine, F1B… The content of [a specific substance] accounted for 8.2%–8.9% of the total urinary radioactivity, and the content of metabolite F2, namely N-((3-(acetamido)-2-amino-5-(trifluoromethyl))phenyl)acetamide, accounted for 4.0%–5.2%. Metabolite F1B is characterized by the retention of trifluoromethyl, two equivalent aromatic protons, and two nitro groups, but the loss of the propyl group. Ten other metabolites were also identified (accounting for <0.1%–3.7% of the total urinary radioactivity, each compound was found in both amphoteric and amphipathic forms). The partial characteristics of two other metabolites were also determined (accounting for 0.1%–2.6% of the total urinary radioactivity, each compound was found in both amphoteric and amphipathic forms). Four metabolic pathways were identified as follows: (i) oxidative N-dealkylation of one or both propyl groups and hydroxylation of the propyl side chain; (ii) reduction of one or two nitro groups to the corresponding amine; (iii) cyclization to generate various substituted and unsubstituted benzimidazole metabolites; and (iv) [other pathways]. The reactions include acetylation of reducing nitro groups, sulfate conjugation, and glucuronic acid conjugation. The major metabolites found in the urine and feces of treated ruminants were unidentified polar compounds, but also N',N'-dipropyl-3-nitro-5-trifluoromethyl-o-phenylenediamine and N(4)N(4)-dipropyl-α,α,α-trifluorotoluene-3,4,5-triamine. Trifluralin undergoes dealkylation in the rumen (of dairy cows), losing one or two propyl groups; the nitro group is reduced to one or two amino groups. Both types of reactions occur simultaneously, producing trifluoromethyltriaminobenzene. For more complete data on the metabolism/metabolites of trifluralin (6 in total), please visit [insert link here]. HSDB record page.

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Biological half-life
Four monkeys (2 males, 2 females) were administered 2 via intravenous injection or topical application to the forearm. A mg/kg dose of radiolabeled trifluralin ethanol solution was administered, and plasma concentrations were measured over 120 hours to determine the area under the curve (AUC) for both administration routes. Two compartments were observed: a half-life of 1.71 hours in the plasma distribution phase and a half-life of 79.1 hours in the terminal plasma disappearance phase. .../Etfluralin/
Salmon juveniles (Salmo salar) were first exposed to high concentrations of trifluralin and then reared in clean water for 12 months. Samples of juveniles were taken at pre-set time intervals for X-ray and chemical analysis. The half-life of trifluralin in salmon juveniles was 40.5 days.

Toxicity Data
LC50 (rat) = 2,800 mg/m³/1h

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Non-human toxicity values
Rats oral LD50 >10,000 mg/kg
Mice oral LD50 500 mg/kg
Rabbit oral LD50 >2000 mg/kg
Dog oral LD50 >2000 mg/kg
For more complete non-human toxicity data for trifluralin (11 in total), please visit the HSDB record page.

Trifluralin is a yellow-orange crystalline solid with a density greater than water. It is insoluble in water and therefore sinks. Its melting point is 48.5-49°C. It is used as a selective pre-emergence herbicide. Trifluralin is a substituted aniline with the structure N,N-dipropylaniline, substituted with nitro groups at positions 2 and 6, and trifluoromethyl groups at position 4. It is an agricultural chemical used as a pre-emergence herbicide. It is both an environmental pollutant and an exogenous substance, herbicide, and agricultural chemical. It is a C-nitro compound, belonging to the (trifluoromethyl)benzene class of compounds, and is also a substituted aniline. Trifluralin is used as a herbicide. Currently, there is no information on the acute (short-term), chronic (long-term), reproductive, developmental, or carcinogenic effects of trifluralin on humans. Dogs fed long-term diets containing trifluralin showed reduced weight gain, and their blood and liver were also affected. Offspring of rodents exposed to trifluralin via gavage (experimentally placing the chemical in the stomach) exhibited skeletal abnormalities and decreased fetal weight. Rats fed with fluroxypyr showed an increased incidence of urinary tract and thyroid tumors. Other studies have not found a statistically significant increase in tumor incidence caused by fluroxypyr. The U.S. Environmental Protection Agency (EPA) has classified fluroxypyr as a Group 7 carcinogen, meaning it is a possible human carcinogen. Fluroxypyr is a commonly used pre-emergence soil-applied herbicide. In 2001, approximately 14 million pounds of fluroxypyr were used in the United States, making it one of the most widely used herbicides. Fluroxypyr is typically applied to the soil to control a variety of annual grasses and broadleaf weeds. It controls weed germination by inhibiting root development through interference with mitosis. Its mode of action is selective, inhibiting both mitosis and cell division. It is a microtubule-destroying pre-emergence herbicide.

C13H16F3N3O4

335.28

335.109

1582-09-8

Trifluralin-d14;347841-79-6

5569

Pink to red solid powder

1.3±0.1 g/cm3

369.1±42.0 °C at 760 mmHg

48.5°C

177.0±27.9 °C

0.0±0.8 mmHg at 25°C

1.528

5.41

0

8

5

23

392

0

ZSDSQXJSNMTJDA-UHFFFAOYSA-N

InChI=1S/C13H16F3N3O4/c1-3-5-17(6-4-2)12-10(18(20)21)7-9(13(14,15)16)8-11(12)19(22)23/h7-8H,3-6H2,1-2H3

2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)aniline

Nitran; Elancolan; Trifluralin

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

DMSO : ≥ 100 mg/mL (~298.26 mM)

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

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Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).

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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline)

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Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).

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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders

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Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

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 (Please use freshly prepared in vivo formulations for optimal results.)