Absorption, Distribution and Excretion
In varying degrees, organochlorines are absorbed from the gut and also by the lung and across the skin. /Soild Organochlorines/
The results of dermal penetration studies with rhesus monkeys indicate that butachlor is poorly absorbed through the skin. ... Employing a 6-hr topical exposure period, only 0.02 % of the dose was systemically absorbed during exposure to a granular formulation, and 5 % of the dose was absorbed when an EC (emulsifiable concentrate) formulation was applied.
Approximately 85 % of an orally administered dose is eliminated in 48 hr; 60 % of the excretedmaterial is found in the feces and 40 % in urine.
... Following a 24-hr exposure, an average butachlor quantity of approximately 5.00% of the applied dose (1.01 micrograms) was absorbed by the skin. The mean peak penetration rate was 0.7% of the applied dose per hour. The skin retained 1.40 to 8.10% of the applied butachlor.

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Metabolism / Metabolites
HERBICIDAL ACTIVITY OF ESTERS, NITRILES, AMINES (&, OF COURSE, SALTS) APPEARS SIMILAR IF NOT IDENTICAL TO PARENT ACID. THIS IS APPARENTLY DUE TO PRESENCE OF HYDROLYTIC ENZYMES IN PLANTS & IN SOIL MICROORGANISMS THAT CONVERT THESE DERIVATIVES TO PARENT ACID. /SRP: UNSPECIFIED SALT OR ESTER OF 2,4-D/
BEAN, BLUEGRASS, & CORN WERE EXPOSED TO 2,4-D. CHROMATOGRAPHIC ANALYSES INDICATED THAT ALL 3 PLANTS METABOLIZED 2,4-D. THE MAJOR METABOLITE APPEARED TO BE 4-HYDROXY-2,5-DICHLOROPHENOXYACETIC ACID ... & MINOR METABOLITE ... 4-HYDROXY-2,3-DICHLOROPHENOXYACETIC ACID. ... ESSENTIALLY ALL 2,4-D ABSORBED BY BLUEGRASS OR CORN WAS RAPIDLY CONJUGATED. THIS REACTION WAS SLOWER IN BEANS. SOME SIDE CHAIN OXIDATION ALSO OCCURRED. ... 4-HYDROXY-2,3-DICHLOROPHENOXYACETATE ... /WAS/ DETECTED IN WILD BUCKWHEAT, WILD OAT, & YELLOW FOXTAIL ONLY. 2-CHLORO-4-HYDROXYPHENOXYACETIC ACID WAS FOUND IN THE THREE FOREGOING SPECIES & LEAFY SPURGE. /SRP: UNSPECIFIED SALT OR ESTER OF 2,4-D/
AFTER FEEDING 2,4-D TO SHEEP & CATTLE, ANALYSIS OF MUSCLE, FAT, LIVER & KIDNEY SHOWED PRESENCE OF 2,4-DICHLOROPHENOL. /SRP: UNSPECIFIED SALT OR ESTER OF 2,4-D/
SOYBEAN ROOT CALLUS CULTURES METABOLIZED 2,4-D. METABOLITES IDENTIFIED INCLUDED 2,4-D-GLUTAMIC ACID & 2,4-D-ASPARTIC ACID CONJUGATES; OTHER NOT IDENTIFIED 2,4-D AMINO ACID CONJUGATES; 2,5-DICHLORO-4-HYDROXYPHENOXYACETIC ACID (4-OH-2,5-D); AND 5-OH-2,4-D ... IN A COMPARISON OF 2,4-D METABOLISM BY SOYBEAN CALLUS, SOYBEAN PLANT AND CORN PLANTS, NO QUALITATIVE DIFFERENCES WERE OBSERVED. HYDROXY CMPD, MAINLY AS GLUCOSIDES, WERE IDENTIFIED AS 5-OH-2,4-D, 4-OH-2,3-D, AND 4-OH-2,5-D. AMINO ACID CONJUGATES WERE IDENTIFIED AS 2,4-D CONJUGATES OF ASPARTIC ACID, GLUTAMIC ACID, ALANINE, VALINE, PHENYLALANINE, TRYPTOPHAN AND LEUCINE. THERE WERE SOME DATA THAT SUGGESTED THE PRESENCE OF AMINO ACID CONJUGATES OF RING HYDROXYLATED 2,4-D. /SRP: UNSPECIFIED SALT OR ESTER OF 2,4-D/
For more Metabolism/Metabolites (Complete) data for 2,4-D, ALKANOLAMINE SALTS (6 total), please visit the HSDB record page.
... Butachlor ... yielded 20-60 mol% formaldehyde on incubation with the mouse liver microsomal mixed function oxidase system under standard conditions.
The metabolism of butachlor was studied in rat liver and kidney homogenates. In vitro incubation of butachlor with liver fractions (S9, microsome and cytosolic fractions) formed a considerable amount of butachlor glutathione conjugate, while the conjugating activity was not efficient for the kidney S9 fraction. There is a sex difference in the distribution of glutathione S-transferase in the liver. ... More enzyme activity was detected in the female liver microsome, while this is not the case in its cytosolic fraction. Further biotransformation of butachlor glutathione conjugate to mercapturate was not observed in the liver S9 fraction. This metabolite was further transformed to butachlor acetyl cysteine conjugate in the presence of acetyl CoA, but to butachlor cysteine conjugate in the absence of acetyl CoA.
Butachlor metabolism in rats is complex due to extensive biliary excretion, intestinal microbial metabolism, and enterohepatic circulation of metabolites. Metabolism in rats follows three major pathways: initial conjugation with glutathione followed by mercapturic acid pathway metabolism; cytochrome P-450-mediated hydroxylation of the aromatic ring, its ethyl groups and the N- butoxymethylene group; and cleavage of the amide bonds via aryl amidase to form 2,6-diethyl aniline, which is further oxidized to 4-amino-3,5-diethylphenol.
... Butachlor is metabolized to CDEPA to a much greater extent by rat liver microsomes (0.045 nmol/min/mg) than by human liver microsomes (< 0.001 nmol/min/mg).
Butachlor has known human metabolites that include 2-Chloro-N-(2,6-diethylphenyl)acetamide.
In varying degrees, butachlor absorbed from the gut and also by the lung and across the skin. Butachlor metabolism is complex due to extensive biliary excretion, intestinal microbial metabolism, and enterohepatic circulation of metabolites. Metabolism in rats follows three major pathways: initial conjugation with glutathione (via glutathione S-transferases) followed by mercapturic acid pathway metabolism; cytochrome P-450-mediated hydroxylation of the aromatic ring, its ethyl groups and the N- butoxymethylene group; and cleavage of the amide bonds via aryl amidase to form 2,6-diethyl aniline, which is further oxidized to 4-amino-3,5-diethylphenol. (T80, A572)

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Biological Half-Life
Biological half-lives after exposure to high and low concentrations were 11.6 and 23.1 days, respectively; [HSDB]
THESE HERBICIDES DO NOT ACCUM IN ANIMALS. THEY ARE NOT EXTENSIVELY METAB BUT ARE ACTIVELY EXCRETED INTO THE URINE ... THEIR PLASMA HALF-LIFE IN MAN IS ABOUT 1 DAY. /CHLOROPHENOXY COMPOUNDS/
... The biological half-lives of the three herbicides on exposure at high and low concentrations were 11.6 and 23.1 days for butachlor,

Toxicity Summary
Binds to nAChRs in nervous systems. Also causes endocrine disruption in humans by binding to and inhibiting the estrogen receptor. (T10, A590)

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Non-Human Toxicity Values
LD50 Rat oral 1740 mg/kg
LD50 Rat oral 2000 mg/kg /Technical butachlor/
LD50 Rabbit dermal >13,000 mg/kg /Technical butachlor/
LD50 Mouse oral 4747 mg/kg
For more Non-Human Toxicity Values (Complete) data for BUTACHLOR (6 total), please visit the HSDB record page.

Butachlor is an aromatic amide that is 2-choro-N-(2,6-diethylphenyl)acetamide in which the amide nitrogen has been replaced by a butoxymethyl group. It has a role as a herbicide, an environmental contaminant and a xenobiotic. It is an aromatic amide, an organochlorine compound and a tertiary carboxamide. It is functionally related to a N-phenylacetamide.
Butachlor is a selective herbicide used worldwide in corn, soybean and other crop cultures. Elevated concentrations of these herbicides and their degradation products have been detected in surface and groundwater. (A252)

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Mechanism of Action
... /CHLOROPHENOXY CMPD INCL 2,4-D ESTERS/ EXERT THEIR HERBICIDAL ACTION BY ACTING AS GROWTH HORMONES IN PLANTS. /CHLOROPHENOXY COMPOUNDS/

C17H26CLNO2

311.85

311.165

23184-66-9

31677

SRP: White, solid powder
Amber liquid
Light yellow oil

1.1±0.1 g/cm3

442.0±45.0 °C at 760 mmHg

<-5ºC

221.1±28.7 °C

0.0±1.1 mmHg at 25°C

1.528

4.51

0

2

9

21

287

0

CCCCOCN(C(=O)CCl)C1=C(CC)C=CC=C1CC

HKPHPIREJKHECO-UHFFFAOYSA-N

InChI=1S/C17H26ClNO2/c1-4-7-11-21-13-19(16(20)12-18)17-14(5-2)9-8-10-15(17)6-3/h8-10H,4-7,11-13H2,1-3H3

N-(butoxymethyl)-2-chloro-N-(2,6-diethylphenyl)acetamide

NSC 221683; BRN 2873811; Butachlor

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.)