Absorption, Distribution and Excretion
ROOTS OR SHOOTS OF OATS AND PEAS WERE EXPOSED TO VAPORS OF (14)C-LABELED PROFLURALIN. THE HERBICIDE WAS ABSORBED BY ROOTS AND SHOOTS OF GERMINATING OATS AND PEAS. SOME ROOT-SHOOT TRANSLOCATION WAS OBSERVED IN PEAS, BUT NO SHOOT-ROOT TRANSPORT COULD BE DETECTED IN EITHER PEAS OR OATS. IN PEAS, (14)C FROM ROOT-ABSORBED PROFLURALIN WAS DETECTED IN SHOOTS.
SORGHUM, BARNYARDGRASS, SOYBEAN, AND PALMER AMARANTH WERE TREATED WITH (14)C-LABELED PROFLURALIN IN NUTRIENT SOLN FOR 24 HR @ 26 OR 38 °C. PROFLURALIN ACCUM IN ROOTS TO A GREATER EXTENT AT 16 DEG, WHEREAS METAB WAS GREATEST AT 35 DEG. VERY LITTLE PROFLURALIN WAS TRANSLOCATED TO THE TOPS OF PLANTS. THESE EFFECTS MAY RELATE TO EXCESS TOXICITY OF PROFLURALIN AT 16 DEG IN SPECIES WHICH NORMALLY EXHIBIT RESISTANCE TO THE HERBICIDES.

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Metabolism / Metabolites
PRESENT DATA INDICATE THAT MINUTE QUANTITIES OF POLAR METABOLITES ARE GENERATED IN COTTON AND SOYBEANS.
... IN RAT-LIVER MICROSOMES ... PROFLURALIN WAS METABOLIZED ANALOGOUSLY /TO TRIFLURALIN, BY HYDROXYLATION OF THE PROPYL RESIDUE AND/OR N-DEALKYLATION/ ... THE BENZIMIDAZOLE WAS A METABOLITE.
Profluralin was extensively metabolized in vitro by normal and phenobarbital-induced rat liver microsomes. Metabolites produced indicated that profluralin metabolism involved N-dealkylation, aliphatic hydroxylation, nitro reduction and cyclization. Analyses ... indicated the formation of 2,6-dinitro-N-(n-propan-3-ol)-alpha,alpha,alpha-trifluoro-p-toluidine and the corresponding N-(n-propan-2-ol) analog. N-dealkylation of profluralin gave the des-n-propyl and di-dealkylated analogs and 2-ethyl-7-nitro-5-trifluoromethyl benzimidazole ...
The metabolism of profluralin was studied in rats. Male Sprague-Dawley rats were administered 1 g/kg or 600 mg/kg profluralin by stomach tube. Bulk urine samples were collected from rats given 600 mg/kg profluralin for 2 weeks and analyzed for metabolites using chromatographic methods fluorine-l9 nuclear magnetic resonance spectroscopy and mass spectrometry. Urine samples were collected 4, 13, 56, or 72 hr after dosing from rats given 1 g/kg profluralin to study the time course of metabolite excretion. At least 20 metabolites were detected in the bulk urine samples from their nuclear magnetic resonance chemica1 shifts. A didea1ky1ated monoreduced compound was the major metabolite. A hydroxylamine derivative was the first and major profluralin metabolite observed during the first 4 hr after dosing. 2-Diamino-4-(trifluoromethyl)-6-nitro-benzenamine was the major metabolite at later times. Approximately 10 to 15 percent of the profluralin dose was excreted during the first 72 hours after dosing.

Toxicity Data
LCLo (rat) > 3,970 mg/m3/1h

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Interactions
TOBACCO TISSUE CULTURES WERE USED IN A BIOASSAY SYSTEM FOR DETERMINING THE EFFECT OF PROFLURALIN ON GROWTH. THE MOLAR CONCN REQUIRED TO INHIBIT FRESH WT GAIN BY 50% (I50) WAS DETERMINED. EXOGENOUSLY APPLIED D-ALPHA-TOCOPHEROL ACETATE AT 100 TIMES THE I50 CONCN DECR THE INHIBITION OF TISSUE GROWTH BY PROFLURALIN.

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Non-Human Toxicity Values
LD50 Rat oral about 10,000 mg/kg
LD50 Rat oral 2,700 mg/kg (Tolban 4E)
LD50 Rabbit percutaneous 3,969 mg/kg
LD50 Rat percutaneous greater than 3170 mg/kg
LC50 (4 hr) Rat inhalation >3.0 mg/L (Tolban 4E)

[1]. Stanley Tocker, et al. Asymmetrical triazine salts. US4632694A.

Profluralin is a C-nitro compound.

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Mechanism of Action
CGA-10832 (AT 1X10-6 MOLAR) INHIBITED CYCLIC PHOTOPHOSPHORYLATION OF ISOLATED PEA CHLOROPLASTS AND DECR STATE-3 RESPIRATION OF BOTH ISOLATED BEAN HYPOCOTYLS AND RAT LIVER MITOCHONDRIA.
CGA 10832 PARTIALLY INHIBITED THE PHOTOSYNTHESIS (MEASURED BY OXYGEN EVOLUTION) OF SPINACH LEAF DISCS.

C14H16F3N3O4

347.29

347.109

26399-36-0

33500

Yellow-orange crystals

1.4±0.1 g/cm3

393.3±42.0 °C at 760 mmHg

34℃

191.7±27.9 °C

0.0±0.9 mmHg at 25°C

1.559

5.25

0

8

5

24

449

0

CCCN(CC1CC1)C2=C(C=C(C=C2[N+](=O)[O-])C(F)(F)F)[N+](=O)[O-]

ITVQAKZNYJEWKS-UHFFFAOYSA-N

InChI=1S/C14H16F3N3O4/c1-2-5-18(8-9-3-4-9)13-11(19(21)22)6-10(14(15,16)17)7-12(13)20(23)24/h6-7,9H,2-5,8H2,1H3

N-(cyclopropylmethyl)-2,6-dinitro-N-propyl-4-(trifluoromethyl)aniline

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)

May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples

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.)