Absorption, Distribution and Excretion
Organochlorine compounds can be absorbed to varying degrees through the intestines, lungs, and skin. /Solid Organochlorine Compounds/
Skin penetration studies in rhesus monkeys showed that butachlor has a very low skin absorption rate. …With a 6-hour local exposure time, only 0.02% of the dose was absorbed systemically when using granules, compared to 5% when using emulsifiable concentrates (ECs).
After oral administration, approximately 85% of the dose was eliminated within 48 hours; 60% was excreted in feces and 40% in urine.
…24 hours after exposure, the skin absorbed an average of approximately 5.00% (1.01 μg) of the applied dose of butachlor. The average peak penetration rate was 0.7% of the hourly applied dose. The skin retained 1.40% to 8.10% of the applied butachlor.

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Metabolisms/Metabolites
The herbicidal activity of esters, nitriles, amines (and of course, salts) is similar to, or even identical to, the parent acid. This is clearly due to the presence of hydrolytic enzymes in plants and soil microorganisms that can convert these derivatives into the parent acid. /SRP: Unspecified salts or esters of 2,4-D/
Legumes, bluegrass, and corn were exposed to 2,4-D. Chromatographic analysis showed that all three 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. …Almost all of the 2,4-D absorbed by bluegrass or corn underwent a rapid conjugation reaction. This reaction was slower in legumes. In addition, some side-chain oxidation reactions occurred. …4-hydroxy-2,3-dichlorophenoxyacetic acid…detected only in wild buckwheat, wild oats, and yellow foxtail grass. 2-Chloro-4-hydroxyphenoxyacetic acid is present in the above three plants and Euphorbia pulcherrima. /SRP: Unspecified salt or ester of 2,4-D/
Analysis of muscle, fat, liver, and kidney after feeding sheep and cattle with 2,4-D indicated the presence of 2,4-dichlorophenol. /SRP: Unspecified salt or ester of 2,4-D/
2,4-D is metabolized in soybean root callus cultures. Identified metabolites include 2,4-D-glutamic acid and 2,4-D-aspartic acid conjugates; other unidentified 2,4-D amino acid conjugates; 2,5-dichloro-4-hydroxyphenoxyacetic acid (4-OH-2,5-D); no qualitative differences were observed when comparing 2,4-D metabolism in soybean callus, soybean plants, and maize plants. Hydroxy-CMPD exists primarily as glucosides, 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. Some data indicate the presence of amino acid conjugates in cyclically hydroxylated 2,4-D. /SRP: Unspecified salts or esters of 2,4-D/
For more complete data on the metabolism/metabolites of 2,4-D and its alkanolamine salts (6 in total), please visit the HSDB record page.
...Butachlor...produces 20-60 mol% formaldehyde upon incubation with a mouse liver microsomal mixed-function oxidase system under standard conditions.
The metabolism of butachlor was studied in mouse liver and kidney homogenates. In vitro incubation of butachlor with liver components (S9, microsomes, and cytoplasm) yielded a large amount of butachlor-glutathione conjugates, while the binding activity in the kidney S9 component was low. The distribution of glutathione S-transferase in the liver showed sex differences. …Higher enzyme activity was detected in female liver microsomes, but not in the cytoplasm. Further bioconversion of butachlor-glutathione conjugates to thiouric acid was not observed in the liver S9 component. This metabolite was further converted to butachlor-acetylcysteine conjugates in the presence of acetyl-CoA, and to butachlor-cysteine conjugates in the absence of acetyl-CoA. The metabolism of butachlor in rats is highly complex due to extensive bile excretion, intestinal microbial metabolism, and enterohepatic circulation of metabolites. Butachlor's metabolism in rats primarily follows three pathways: first, binding to glutathione, followed by metabolism via the thiouric acid pathway; cytochrome P-450-mediated hydroxylation of the aromatic ring, ethyl group, and N-butoxymethylene group; and cleavage of the amide bond by arylamidinase to generate 2,6-diethylaniline, which is further oxidized to 4-amino-3,5-diethylphenol. Butachlor is metabolized to CDEPA to a much higher degree in rat liver microsomes (0.045 nmol/min/mg) than in human liver microsomes (< 0.001 nmol/min/mg). Known human metabolites of butachlor include 2-chloro-N-(2,6-diethylphenyl)acetamide. Butachlor can be absorbed through the intestines, lungs, and skin, with varying degrees of absorption. Due to extensive bile excretion, intestinal microbial metabolism, and enterohepatic circulation of metabolites, the metabolic process of butachlor is highly complex. In rats, the metabolism of this substance follows three main pathways: first, binding to glutathione (via glutathione S-transferase), followed by metabolism via the thiouric acid pathway; cytochrome P-450-mediated hydroxylation of the aromatic ring, ethyl group, and N-butoxymethylene group; and cleavage of the amide bond by arylamidinase to generate 2,6-diethylaniline, which is further oxidized to 4-amino-3,5-diethylphenol. (T80, A572)

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Biological half-life
The biological half-lives after exposure to high and low concentrations are 11.6 days and 23.1 days, respectively; [HSDB]
These herbicides do not accumulate in animals. They are not widely metabolized, but are actively excreted in urine… Their plasma half-life in humans is approximately 1 day. /Chlorophenoxy compounds/
…The biological half-lives of the three herbicides at high and low concentrations are: butachlor 11.6 days, butachlor 23.1 days.

Toxicity Summary
It binds to nAChR in the nervous system. It also causes endocrine disorders in humans by binding to and inhibiting the activity of estrogen receptors. (T10, A590) Non-human Toxicity Values Rats Oral LD50: 1740 mg/kg Rats Oral LD50: 2000 mg/kg /Technical grade butachlor/ Rabbit Dermal LD50: >13,000 mg/kg /Technical grade butachlor/ Mouse Oral LD50: 4747 mg/kg For more non-human toxicity values (complete data) for butachlor (6 out of 6), please visit the HSDB records page.

Butachlor is an aromatic amide, chemically named 2-chloro-N-(2,6-diethylphenyl)acetamide, in which the amide nitrogen atom is replaced by a butoxymethyl group. It is both a herbicide and an environmental pollutant and exogenous substance. Butachlor is an aromatic amide, organochlorine compound, and tertiary amide. Its structure is similar to that of N-phenylacetamide. Butachlor is a selective herbicide widely used worldwide in the cultivation of corn, soybeans, and other crops. High concentrations of this herbicide and its degradation products have been detected in both surface water and groundwater. (A252)

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Mechanism of Action
……/Chlorophenoxy compounds (including 2,4-D esters)/Exercise 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.)