4-tert-Butyl-N-sec-butyl-2,6-dinitroanilin

Butralin

HCID 36565

Grundinformationen

CAS
33629-47-9
Standard-SMILES
CCC(C)Nc1c([N+](=O)[O-])cc(C(C)(C)C)cc1[N+](=O)[O-]
InChIKey
SPNQRCTZKIBOAX-UHFFFAOYSA-N
Summenformel
C14H21N3O4
Durchschnittliche Molmasse
295,33 g/mol
Monoisotopische Masse
295,15320615

Überblick

Butralin is a C-nitro compound.

Namen und Bezeichner

Bevorzugter Name
Butralin
IUPAC
N-butan-2-yl-4-tert-butyl-2,6-dinitroaniline
Lokaler Name
4-tert-Butyl-N-sec-butyl-2,6-dinitroanilin
Englischer Name
BUTRALIN
Summenformel
C14H21N3O4
Molmasse
295.33

Namen und Synonyme

BUTRALIN33629-47-9DibutalinRutralinTamexAMEXButralineN-sec-Butyl-4-tert-butyl-2,6-dinitroanilineZitsaosolAmchem 70-25AMEX 820DTXSID3032337
Weitere Namen anzeigen
Butalina82072-A34Sector70-314Bamex820AMEXINE
Benzenamine, 4-(1,1-dimethylethyl)-N-(1-methylpropyl)-2,6-dinitro-4-(tert-Butyl)-N-sec-butyl-2,6-dinitroanilineAniline, N-sec-butyl-4-tert-butyl-2,6-dinitro-5CZK3K1YPBA 820N-sec-Butyl-4-tert-butyl-2,6-dinitrobenzamine4-(1,1-Dimethylethyl)-N-(1-methylpropyl)-2,6-dinitrobenzenamineN-(butan-2-yl)-4-tert-butyl-2,6-dinitroaniline

Datenbank-Bezeichner

CAS
33629-47-9
PubChem CID
36565
DTXSID
DTXSID3032337
ChEMBL
CHEMBL1256669
ChEBI
CHEBI:81847
UNII
5CZK3K1YPB
EC Number
251-607-4
Nikkaji
J19.765C

Eigenschaften

Berechnete Struktureigenschaften

XLogP
5,1
Polarare Oberfläche (TPSA)
104 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
5
Frei drehbare Bindungen
4
Schwere Atome
21

Experimentelle und physikochemische Eigenschaften

SpringerMaterials PropertiesFusion temperature
Pesticides · 6 Einträge

Herbicides, Plant Growth Regulators

Active substance -> EU Pesticides database: Not approved

Pesticides -> Herbicides, Nitroaromatic

Environmental transformation -> Pesticides (parent, predecessor)

Pesticide (Butralin) -> USDA PDB

Pesticide

LogPlog Kow = 4.93 at 23 °C
OdorSlightly aromatic odor
Density1.06 at 25 °C
Color/FormYellow orange crystals

Physikochemische Eigenschaften

Schmelzpunkt
60 · 60-61°
Siedepunkt
0.5 · bp0.5 134-136°
Dichte
1.1489 · 1.1489 (rough estimate)
Dampfdruck
0.001 Pa · 0.001Pa at 25℃
Brechungsindex
1.57 · 1.5700 (estimate)
Flammpunkt
97 °F · open cup: 97°F (36°C)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Warning

H302 (95.8%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P264, P264+P265, P270, P273, P280, P301+P317, P305+P351+P338, P318, P330, P337+P317, P391, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 71 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory Information · 3 Einträge

Butralin is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)

2008/819

Status: Active Update: 31-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/25720

Other Safety InformationIMAP assessments - Benzenamine, 4-(1,1-dimethylethyl)-N-(1-methylpropyl)-2,6-dinitro-: Environment tier I assessment
Hazards SummaryAn irritant; May cause CNS depression; Targets the blood; [MSDSonline] Workers should use chemical resistant gloves when mixing and loading; [Reference #1]
Special Reports · 1 Eintrag

USEPA/Office of Pesticide Programs; Reregistration Eligibility Decision Document - Butralin. EPA738-R-97-09 May 1998. The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the U.S.[Available from, as of September 27, 2005: http://www.epa.gov/pesticides/reregistration/status.htm]

FIFRA Requirements · 2 Einträge

The Agency has completed its review ... and has determined that the data are sufficient to support reregistration of all products containing butralin for use on tobacco. The data ... were sufficient to allow the Agency to assess the registered uses of butralin and to determine that butralin can be used without resulting in unreasonable adverse effects to humans and the environment. The Agency therefore finds that all products containing butralin as the active ingredient for the use on tobacco are eligible for reregistration.

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Butralin is found on List B. Case No: 2075; Pesticide type: herbicide; Case Status: RED Approved 9/97; OPP has made a decision that some/all uses of the pesticide are eligible for reregistration, as reflected in a Reregistration Eligibility Decision (RED) document .; Active ingredient (AI): 4-(1,1-Dimethylethyl)-N-(1-methylpropyl)-2,6-dinitrobenzenamine; Data Call-in (DCI) Date(s): 6/7/91, 3/3/95, 10/13/95; AI Status: OPP has completed a Reregistration Eligibility Decision (RED) for the case/AI.

Hazard Classes and CategoriesAcute Tox. 4 (95.8%)

Sicherheit und Schutzausrüstung

Storage Conditions · 1 Eintrag

Safe Storage of Pesticides. Always store pesticides in their original containers, complete with labels that list ingredients, directions for use, and first aid steps in case of accidental poisoning. Never store pesticides in cabinets with or near food, animal feed, or medical supplies. Do not store pesticides in places where flooding is possible or in places where they might spill or leak into wells, drains, ground water, or surface water.

Cleanup Methods · 2 Einträge

If a spill occurs, clean it up promptly. Don't wash it away. Instead, sprinkle the spill with sawdust, vermiculite, or kitty litter. Sweep it into a plastic garbage bag, and dispose of it as directed on the pesticide product label.

After Applying a Pesticide, Indoors or Outdoors. To remove pesticide residues, use a bucket to rinse tools or equipment three times, including any containers or utensils that you used when mixing the pesticide. Then pour the rinsewater into the pesticide sprayer and reuse the solution by applying it according to the pesticide product label directions. After applying any pesticide wash your hands and any other parts of your body that may have come in contact with the pesticide..To prevent tracking pesticides inside, remove or rinse your boots or shoes before entering your home. Wash any clothes that have been exposed to a lot of pesticide separately from your regular wash.

Disposal Methods · 3 Einträge

Safe Disposal of Pesticides. The best way to dispose of small amounts of excess pesticides is to use them - apply them - according to the directions on the label. If you cannot use them, ask your neighbors whether they have a similar pest control problem and can use them. If all of the remaining pesticide cannot be properly used, check with your local solid waste management authority, environmental agency, or health department to find out whether your community has a household hazardous waste collection program or a similar program for getting rid of unwanted, leftover pesticides. These authorities can also inform you of any local requirements for pesticide waste disposal.

Safe Disposal of Pesticides. An empty pesticide container can be as hazardous as a full one because of residues left inside. Never reuse such a container. When empty, a pesticide container should be rinsed carefully three times and the rinsewater thoroughly drained back onto the sprayer or the container previously used to mix the pesticide. Use the rinsewater as a pesticide, following label directions. Replace the cap or closure securely. Dispose of the container according to label instructions. Do not puncture or burn a pressurized container like an aerosol - it could explode. Do cut or puncture other empty pesticide containers made of metal or plastic to prevent someone from reusing them. Wrap the empty container and put it in the trash after you have rinsed it.

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Preventive Measures · 5 Einträge

/For applying the product/ wear the items of protective clothing the label requires: for example, non-absorbent gloves (not leather or fabric), rubber footwear (not canvas or leather), a hat, goggles, or a dust-mist filter. If no specific clothing is listed, gloves, long-sleeved shirts and long pants, and closed shoes are recommended. You can buy protective clothing and equipment at hardware stores or building supply stores.

Indoor Applications. If the label directions permit, leave all windows open and fans operating after the application is completed. If the pesticide product is only effective in an unventilated (sealed) room or house, do not stay there. Put all pets outdoors, and take yourself any your family away from treated areas for at least the length of time prescribed on the label. Apply most surface sprays only to limited areas such as cracks; don't treat entire floors, walls, or ceilings. Don't let pesticides get on any surfaces that are used for food preparation. Wash any surfaces that may have pesticide residue before placing food on them.

Indoor Applications. When using total release foggers to control pests, use no more than the amount needed and to keep foggers away from ignition sources (ovens, stoves, air conditioners, space heaters, and water heaters, for example). Foggers should not be used in small, enclosed places such as closets and cabinets or under tables and counters.

Outdoor Applications. Never apply pesticides outdoors on a windy day (winds higher than 10 mph). Position yourself so that a light breeze does not blow pesticide spray or dust into your face.

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

Toxikologische Informationen

Ecotoxicity Values · 5 Einträge

LC50 Anas platyrhynchos (Mallard duck, 14 day old) diet >10000 ppm/8 days

LC50 Colinus virginianus (Northern bobwhite, 14 day old) diet >10000 ppm/8 days

LD50 Colinus virginianus (Northern bobwhite, 22 weeks old) oral >2250 mg/kg

LC50 Americamysis bahia (Opossum shrimp) 0.07 ppm/96 hr (95% confidence interval: 0.061-0.079 ppm); flow through /formulated product/

For more Ecotoxicity Values (Complete) data for BUTRALIN (17 total), please visit the HSDB record page.

Environmental Fate · 4 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), a Koc value of 3,400(2), indicates that butralin is expected to have slight mobility in soil(SRC). Volatilization of butralin from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.9X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 1.3X10-5 mm Hg(2), and water solubility, 1 mg/L(3). Butralin is not expected to volatilize from dry soil surfaces(SRC) based its vapor pressure(3). A 57% degradation after 6 months in soils incubated at 70% field moisture capacity(4) suggests that biodegradation is a slow environmental fate process in soil(SRC). Under greenhouse conditions, butralin exhibited half-lives ranging from 21-52 days, with a mean half-life of 40 days(2). Using a Sharkey clay (4% sand, 25% silt, 71% clay, 4.2% organic matter) and Bosket clay loam (20% sand, 60% silt, 20% clay, 1.5% organic matter) soils in greenhouse experiments, butralin, applied at 8 umole/kg to 2,000 g soil, exhibited half-lives of 52 and 29 days, respectively(2).

AQUATIC FATE: Based on a classification scheme(1), a Koc value of 3,400(2) indicates that butralin is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 4.9X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 1.3X10-5 mm Hg(2), and water solubility 1 mg/L(4). Using this Henry's Law constant and an estimation method(2), volatilization half-lives for a model river and model lake are 13 and 99 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 1,200(SRC), from a log Kow of 4.93(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is very high(SRC). Butralin photodegraded in water, when irradiated in sunlight, to the dealkylated nitroso compound (4-tert-butyl-2-dinitroso-6-nitrosoaniline); it is however less photolabile than other dinitroanilines(8). A 57% degradation after 6 months in soils incubated at 70% field moisture capacity(7) and half lives ranging from 21-52 days suggests that biodegradation is a slow environmental fate process in water(SRC).

AQUATIC FATE: A 4-liter aquarium containing butralin-treated Metapeake loam sediment, daphnids, snails, algae, with mosquito fish (Gambusia affinis) added for the final 3 days of the experiment was studied. 14C-labeled butralin concentration was 10 ppm and aquaria were exposed 33 days to natural sunlight(1). Butralin distribution in biota was as follows: 3.21 ppm, algae; 3.71 ppm snail; 0.83 ppm daphnids; and 0.89 ppm mosquito fish(1). The Metapeake loam, treated 7 months earlier with 10 ppm butralin, contained 27% nonextractable radioactivity(1).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), butralin, which has a vapor pressure of 1.3X10-5 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase butralin is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 5.3 hours(SRC), calculated from its rate constant of 24.2X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase butralin may be removed from the air by wet and dry deposition(SRC). Butralin has been reported as stable to photochemical reactions(4).

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Ecotoxicity Excerpts · 1 Eintrag

/BIRDS and MAMMALS/ Technical butralin (purity not identified) did not impair the reproductive ability of mallard ducks, with the exception of increased eggshell cracks, at 80 ppm. Technical butralin, fed to bobwhite quail for a total of 15 weeks, did not impair the reproductive ability at either the 4 or 80 ppm levels. However, these studies are inadequate and the highest tested level (80 ppm) does not adequately represent avian exposure levels expected in the environment... .

Soil Adsorption/Mobility · 1 Eintrag

The Koc of butralin has been reported as 3,400(1). According to a classification scheme(2), this Koc value suggests that butralin is expected to have slight mobility in soil. Butralin was strongly adsorbed by organic matter, as shown by 77, 82, and 78% adsorption of addition of 2.5, 5.0, and 10X10-6 M concentrations, respectively(3). The same concentrations added to montmorillonite resulted in 21, 13, and 9% adsorption, respectively(3). Subsequent desorption studies showed very little desorption from organic matter by either water or 1 N CaCl solution, results being 13.2 and 11.1%, respectively; 91.7 and 68.4% desorption, respectively, was desorbed from montmorillonite(3). Metapeake loam, treated 7 months earlier with 10 ppm butralin, contained 27% nonextractable radioactivity(1).

Human Toxicity Excerpts · 1 Eintrag

/EPIDEMIOLOGY STUDIES/ ... Median sensory nerve conduction velocity (SCV) (finger-wrist) in farmers using Delsen (mancozeb, dithiocarbamate fungicide), who showed significant decrease of serum cholinesterase activities, were significantly lower compared with the controls. Sural SCV in farmers using Fastac (alpha-cypermethrin, pyrethroid insecticide) and median motor nerve conduction velocity (MCV) (elbow-wrist) in farmers using Tamex (butralin, dinitroaniline herbicide) were significantly slowed compared with their respective controls. In Delsen (mancozeb, dithiocarbamate) users, the power of postural sway of 0-1 Hz was significantly larger than that in the controls both in the anterior-posterior direction with eyes open and in the right-left direction with eyes closed. The former type of sway was also significantly increased in Tamaron (methamidophos, organophosphorus insecticide) users.

Regulatorische Informationen

FIFRA Requirements · 2 Einträge

The Agency has completed its review ... and has determined that the data are sufficient to support reregistration of all products containing butralin for use on tobacco. The data ... were sufficient to allow the Agency to assess the registered uses of butralin and to determine that butralin can be used without resulting in unreasonable adverse effects to humans and the environment. The Agency therefore finds that all products containing butralin as the active ingredient for the use on tobacco are eligible for reregistration.

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Butralin is found on List B. Case No: 2075; Pesticide type: herbicide; Case Status: RED Approved 9/97; OPP has made a decision that some/all uses of the pesticide are eligible for reregistration, as reflected in a Reregistration Eligibility Decision (RED) document .; Active ingredient (AI): 4-(1,1-Dimethylethyl)-N-(1-methylpropyl)-2,6-dinitrobenzenamine; Data Call-in (DCI) Date(s): 6/7/91, 3/3/95, 10/13/95; AI Status: OPP has completed a Reregistration Eligibility Decision (RED) for the case/AI.

Sicherheitsdaten

wgk
3
tsca
TSCA listed
ridadr
1325
hs_code
29214990
RTECS-Nr.
BW9500000
risk_code
24-36/37/38-50/53-36-22-63

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 2 Einträge

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.

Absorption, Distribution and Excretion · 2 Einträge

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).

Verwendung und Herstellung

Uses · 6 Einträge

A dinitroaniline herbicide used as a plant growth regulator on tobacco (flue-cured and air-cured); No food or feed uses and groundwater contamination not likely; [Reference #1]

Farming (Pesticides) [Category: Industry]

For butralin (USEPA/OPP Pesticide Code: 106501) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Plant growth regulator

Pre-emergence control of annual broad-leaved weeds and grasses in cotton, soya beans, rice, barley, beans, alliums, vines, ornamentals, and orchards of fruit and nut trees; used at 1.12-3.4 kg/ha (depending on soil type). Also used to control suckers on tobacco, at 125 mg/plant.

This is a man-made compound that is used as a pesticide.

Methods of ManufacturingButralin is produced by nitration of tert-butyl-4-chlorobenzene and subsequent reaction with sec-butylamine.
Formulations/Preparations · 5 Einträge

Emulsifiable concentrate

Technical is > or = 98% (without xylene).

Selected products: Tabamex Plus; ...Amex 820; Amexine; Tabamex; Tamex 3; Tabago. Mixtures: Tamex AG (+n-decanol); ...Stifle (+maleic hydrazide potassium salt); Yellow Ribbon (+n-decanol).

Discontinued products mixtures: Linamex (+linuron)

Trade name: Zitsaosol

Use ClassificationEnvironmental transformation -> Pesticides (parent, predecessor)
General Manufacturing InformationBenzenamine, 4-(1,1-dimethylethyl)-N-(1-methylpropyl)-2,6-dinitro-: ACTIVE

Anwendungen

VerwendenHerbicide.

Anbieter75 Anbieter

山东泰诚生物科技有限公司18769832557 18769832557 · [email protected]
艾吉析科技(上海)有限公司17717235263 · [email protected]
山东海舟生物工程有限公司130-0567-0367 13006570367 · [email protected]
广州佳途科技股份有限公司81960175 18933936954 · [email protected]
陕西缔都新材料有限公司029-63373950 17392216152 · [email protected]

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