Absorption, Distribution and Excretion
Extensively metabolized and excreted in urine and feces. ...The majority (85%) of applied butralin was excreted in the urine within 48 hr /(in rats)/. None was in the organs after 72 hr.
In a metabolism study, rats were dosed by gavage with butralin (ring labeled) in corn oil at 8 mg/kg/day (low dose levels) for single and multiple dosing and biliary excretion studies and at 800 mg/kg/day (high dose single dosing) and the distribution and excretion of butralin followed over a 7 day period. Low dose results indicate that about 100% of the dosed material was excreted in about 2 days, with 55 to 60% excreted in the feces and 35-45% in urine. The feces contained about 10% unmetabolized butralin. The excretory half life was about 12 hours. Tissues retained only about 1% of the labeled butralin. A similar excretion pattern was seen in the repeat low dose group. High dose administration of butralin took 5-7 days to achieve 100% excretion of butralin in the urine and feces. The excretory half life was between 2 and 4 days. Of the various tissues, fat and liver tended to retain more butralin residues. Females excreted the butralin residues more slowly than males and retained more metabolite in the tissue (especially the liver and fat).

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Metabolism / Metabolites
In a bile excretion study using low dose levels (8 mg butralin/kg), enterohepatic circulation was determined to be a primary pathway for butralin excretion and metabolism. Twelve butralin metabolites were identified in pooled urine, feces and/or bile samples. Metabolites identified at concentrations of 5% to 10% of the administered dose were: 2-methyl- 5(6)[1-(1-carboxy-1-methyl)ethyl]-7(4)-nitrobenzimidazole, 2-methyl- 5(6)[2-(1-hydroxy-2-methyl)propyl]-7(4)-nitrobenzimidazole, 2-methyl-2(4- amino-3,5-dinitrophenyl)propionic acid and 2-methyl-2(4-amino-3,5- dinitrophenyl)propanol-glucuronide. Butralin, the parent chemical, was present at 10% of the administered dose. There were no metabolites at concentrations >10% of the administered dose identified in the study.
...Metabolized in the rat by the primary metabolic processes of N-dealkylation, oxidation and nitro reduction, and by secondary processes of N-acetyl and glucuronic acid conjugation. ...Butralin is ultimately metabolized to carbon dioxide.

Toxicity Data
LC50 (rat) = 50,000 mg/m3/4h

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Non-Human Toxicity Values
LD50 Rat oral 2500 mg/kg
LD50 Rabbit dermal 200 mg/kg
LC50 Rat inhalation 50 g/cu m/ 4 hr
LD50 Rat (male) oral 1170 mg/kg /Technical product/
For more Non-Human Toxicity Values (Complete) data for BUTRALIN (6 total), please visit the HSDB record page.

Butralin is a C-nitro compound.
Butralin is a dinitroaniline herbicide used as a plant growth regulator on flue-cured and air-cured tobacco. In studies using laboratory animals, butralin generally has been shown to be of low acute toxicity. It has been placed in Toxicity Category III for effects via the oral route of exposure and eye irritation, and Toxicity Category IV for the dermal and inhalation routes. The carcinogenicity classification for butralin has been not determined.

C14H21N3O4

295.34

295.153

33629-47-9

36565

Yellow orange crystals

1.2±0.1 g/cm3

381.3±42.0 °C at 760 mmHg

61ºC

184.4±27.9 °C

0.0±0.9 mmHg at 25°C

1.565

5.8

1

5

4

21

359

0

CCC(C)NC1=C(C=C(C=C1[N+](=O)[O-])C(C)(C)C)[N+](=O)[O-]

SPNQRCTZKIBOAX-UHFFFAOYSA-N

InChI=1S/C14H21N3O4/c1-6-9(2)15-13-11(16(18)19)7-10(14(3,4)5)8-12(13)17(20)21/h7-9,15H,6H2,1-5H3

N-butan-2-yl-4-tert-butyl-2,6-dinitroaniline

A 820; Tamex; Butralin

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 (~338.60 mM)

Solubility in Formulation 1: ≥ 2.5 mg/mL (8.47 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

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Solubility in Formulation 2: ≥ 2.5 mg/mL (8.47 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

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