Butralin

295.33

295.33

251-607-4

DTXSID3032337

Yellow orange crystals

2921499012

104

4.93 at 23 deg C

Yellow-orange crystals with a slightly aromatic odour

1.06 at 25 deg C

60 °C

135 °C

open cup:97°F (36°C)

1.565

In water, 1 mg/L at 25 deg C

0-6°C

1.3X10-5 mm Hg at 25 deg C

Oral-Rat LD50: 2500 mg/kg; Inhalation-rat LC50: 50000 mg/m3/4 hours

Combustion produces toxic nitrogen oxide gas

Slightly aromatic odor

Henry's Law constant = 4.9X10-6 atm-cu m/mol at 25 °C

Hydroxyl radical reaction rate constant = 24.2X10-12 cu cm/molec-sec at 25 °C (est)

II

4.1

1325

3

24-36/37/38-50/53-36-22-63

26-36/37-45-60-61

BW9500000

T,N,Xn

The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials

Hydrolytically and photochemically stable. Concentrates are stable on storage under dry conditions >3 years, but should not be stored <-5 deg C or allowed to freeze.

P273-P281-P305 + P351 + P338-P501

H302-H319-H341-H410

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.

Incompatible with strong oxidizing agents.

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]

|Warning|H302 (97.71%): Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P264, P270, P273, P280, P281, P301+P312, P305+P351+P338, P308+P313, P330, P337+P313, P391, P405, and P501|Aggregated GHS information provided by 131 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

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.

/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.

moderately toxic

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.

/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... .

Butralin's production may result in its release to the environment through various waste streams; it's use as an herbicide(1) will result in its direct release to the environment(SRC).

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).

The rate constant for the vapor-phase reaction of butralin with photochemically-produced hydroxyl radicals has been estimated as 24.2X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 5.3 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Butralin is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2). Following 7 days exposure to unfiltered solar radiation in July, 9.0% photodecomposition of 14C-labeled butralin was reported from a starting concentration 1 kg/ha applied to dry soil thin layer plates(4). The soil characteristics were a Hagerstown clay loam (28% sand, 44% silt, 28% clay, 1.9% organic matter, pH 6.3, and cation exchange capacity of 14.7 meq/100 g; 18 g soil were applied to each plate at a thickness of 2 mm(3). Butralin photodegraded in water, when irradiated in sunlight, to the dealkylated nitroso compound (4-tert-butyl-2-dinitroso-6-nitrosoaniline) and minor products including 4-tert-butyl-2,6-dinitroaniline, rate not specified(4). It is, however, less photolabile than other dinitroanilines(4).

An estimated BCF of 1248 was calculated for butralin(SRC), using a log Kow of 4.93(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is very high(SRC), provided the compound is not metabolized by the organism(SRC).

9.55e+03 L/kg|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).

The Henry's Law constant for butralin is estimated as 4.9X10-6 atm-cu m/mole(SRC) derived from its vapor pressure, 1.3X10-5 mm Hg(1), and water solubility, 1 mg/L(2). This Henry's Law constant indicates that butralin is expected to volatilize from water surfaces(3). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(3) is estimated as 13 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is estimated as 99 days(SRC). Butralin's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Butralin is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

Occupational exposure to butralin may occur through dermal contact with this compound at workplaces where butralin is produced or used. The greatest potential for dermal and inhalation exposure to butralin is expected at the manufacturing site and in the field during is application as an herbicide. (SRC)

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).

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.

Skin decontamination. Skin contamination should be treated promptly by washing with soap and water. Contamination of the eyes should be treated immediately by prolonged flushing of the eyes with large amounts of clean water. If dermal or ocular irritation persists, medical attention should be obtained without delay. /Other herbicides/|Gastrointestinal decontamination. Ingestions of these herbicides are likely to be followed by vomiting and diarrhea due to their irritant properties. Management depends on: (1) the best estimate of the quantity ingested, (2) time elapsed since ingestion, and (3) the clinical status of the subject. Activated charcoal is probably effective in limiting irritant effects and reducing absorption of most or all of these herbicides. Aluminum hydroxide antacids may be useful in neutralizing the irritant actions of more acidic agents. Sorbitol should be given to induce catharsis if bowel sounds are present and if spontaneous diarrhea has not already commenced. Dehydration and electrolyte disturbances may be severe enough to require oral or intravenous fluids. ... If large amounts of herbicide have been ingested and the patient is seen within an hour of the ingestion, gastrointestinal decontamination should be considered ... . If the amount of ingested herbicides was small, if effective emesis has already occurred, or if treatment is delayed, administer activated charcoal and sorbitol by mouth. /Other herbicides/|Intravenous fluids. If serious dehydration and electrolyte depletion have occurred as a result of vomiting and diarrhea, monitor blood electrolytes and fluid balance and administer intravenous infusions of glucose, normal saline, Ringer's solution, or Ringer's lactate to restore extracellular fluid volume and electrolytes. Follow this with oral nutrients as soon as fluids can be retained. /Other herbicides/|Supportive measures are ordinarily sufficient for successful management of excessive exposures to these herbicides ... . If the patient's condition deteriorates in spite of good supportive care, the operation of an alternative or additional toxicant should be suspected. /Other herbicides/

/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.

butralin

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

Benzenamine, 4-(1,1-dimethylethyl)-N-(1-methylpropyl)-2,6-dinitro-: ACTIVE

Method: EPA-OSW 8091; Procedure: Nitroaromatics and Cyclic Ketones in Water, Soil, and Waste by GC-ECD or GC-NPD; Analyte: butralin; Matrix: water, soil, and waste matrices; Detection Limit: not provided.

Agrochemicals -> Herbicides, Plant Growth Regulators|Environmental transformation -> Pesticides (parent, predecessor)

Butralin has known environmental transformation products that include DNTBA 4-tert-butyl-2,6-dinitroaniline.