기본 정보
- CAS
33629-47-9- 표준 SMILES
CCC(C)Nc1c([N+](=O)[O-])cc(C(C)(C)C)cc1[N+](=O)[O-]- InChIKey
SPNQRCTZKIBOAX-UHFFFAOYSA-N- 분자식
- C14H21N3O4
- 평균 분자량
- 295.33 g/mol
- 단동위원소 질량
- 295.15320615
개요
Butralin is a C-nitro compound.
이름 및 식별자
- 우선 이름
- Butralin
- IUPAC
- N-butan-2-yl-4-tert-butyl-2,6-dinitroaniline
- 영어명
- BUTRALIN
- 분자식
- C14H21N3O4
- 분자량
- 295.33
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- CAS
33629-47-9- PubChem CID
- 36565
- DTXSID
DTXSID3032337- ChEMBL
CHEMBL1256669- ChEBI
CHEBI:81847- UNII
- 5CZK3K1YPB
- EC Number
- 251-607-4
- Nikkaji
- J19.765C
물성
구조 계산 물성
- XLogP
- 5.1
- 극성 표면적
- 104 Ų
- 수소 결합 공여자 수
- 1
- 수소 결합 수용자 수
- 5
- 회전 가능 결합 수
- 4
- 무거운 원자 수
- 21
- 형식 전하
- 0
- 복잡도
- 359
실험 및 물리화학적 성질
Pesticides
Herbicides, Plant Growth Regulators
Active substance -> EU Pesticides database: Not approved
Pesticides -> Herbicides, Nitroaromatic
Environmental transformation -> Pesticides (parent, predecessor)
Pesticide (Butralin) -> USDA PDB
Pesticide
Solubility
Solubility in ethanol 73, methanol 98 and hexane 300 g/L at 25-26 °C. Solubility in dichloroethane 146, benzene 270 and acetone 448 g/100 mL at 24 °C.
In water, 1 mg/L at 25 °C
Decomposition
Decomposes at 265 °C.
When heated to decomposition it emits toxic vapors of /nitrogen oxides/.
Vapor Pressure
0.000013 [mmHg]
1.3X10-5 mm Hg at 25 °C
물리화학적 성질
- 녹는점
- 60 · 60-61°
- 끓는 점
- 0.5 · bp0.5 134-136°
- 밀도
- 1.1489 · 1.1489 (rough estimate)
- 증기압
- 0.001 Pa · 0.001Pa at 25℃
- 굴절률
- 1.57 · 1.5700 (estimate)
- 인화점
- 97 °F · open cup: 97°F (36°C)
- 저장 조건
- 0 · 0-6°C
- 용해도
- 클로로포름 (약간 용해됨), DMSO (약간 용해됨), 메탄올 (약간 용해됨,초음파처리)
- 산도 계수 (pKa)
- -3.5 · -3.50±0.50(Predicted)
- 물리적 상태
- Solid
- 색상
- Yellow to orange
- 수용성
- 308 μg/L · 308μg/L at 25℃
- Merck
- 13 · 13,1531
- BRN
- 2947948 · 2947948
- Henry's Law Constant
- 2 · 2.0×100 mol/(m3Pa) at 25℃, HSDB (2015)
- 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
- InChIKey
- SPNQRCTZKIBOAX-UHFFFAOYSA-N
- SMILES
- CCC(C)Nc1c(cc(cc1[N+]([O-])=O)C(C)(C)C)[N+]([O-])=O
- LogP
- 4.93 at · 4.93 at 23℃
- EPA
- Butralin (33629-47-9)
화학적 성질
Butralin is a yelloworange crystalline solid or liquid. Commercial product is available as an emulsifiable concentrate.
안전 및 규제
GHS 분류
GHS Classification
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.
유해성 정보
Regulatory Information
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
Special Reports
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
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.
안전 및 보호
Storage Conditions
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
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
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
/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.
독성 정보
Ecotoxicity Values
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
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).
Ecotoxicity Excerpts
/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
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
/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.
Environmental Biodegradation
AEROBIC: Butralin is degraded by soil microflora such as Paecilomyces sp; the major biodegradation product is 4-tert butyl 2,6 dinitroanaline(1). 14C-labeled butralin, applied at a concentration of 10 ppm to Chillum silt loam soil incubated at 70% field moisture capacity, was 57% degraded after 6 months; 98% applied 14C was recovered after 2 months(2). Under greenhouse conditions, butralin exhibited half-lives ranging from 21-52 days, with a mean half-life of 40 days(3). 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(3).
ANAEROBIC: In general, greater degradation in soil has been noted for the dinitroaniline compounds under anaerobic conditions than under aerobic(1). 550 grams of soil (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)) were flooded following application of a commercial formulation of butralin at 0.5 ppmw and maintained in a greenhouse at 20-42 °C temperature range(2). A half-life of 24 days was reported when the soil was subjected to flooding conditions while a half-life of 36 days was reported when soil moisture content was maintained at field capacity(2).
Environmental Bioconcentration
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).
Volatilization from Water/Soil
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).
Non-Human Toxicity Excerpts
/LABORATORY ANIMALS: Acute Exposure/ Slightly irritating to skin; moderately irritating to eyes (rabbits).
/LABORATORY ANIMALS: Acute Exposure/ /In LD50 studies with rats dosed by gavage,/ signs included ruffled coats, lethargy, tremors and diarrhea. Necropsy included dark lungs, oily fluid in the stomach and yellowish stains in the intestine and fat, and ocular and nasal secretions.
/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ ...Butralin technical (99% a.i.) was administered in the diet of Sprague-Dawley rats (5/sex/dose) at dose levels of 0, 2, 10, 50, 250 mg/kg/day for 4 weeks. No deaths occurred in any of the experimental groups studied. Butralin stained the urine and tissues in the 50 and 250 mg/kg/day dose group animals. Body weights of the high dose animals were reduced by 22-26%, a difference which is not statistically significant from control animal data. Clinical chemistries, hematology or urinalyses were not carried out. At necropsy, the yellow staining by butralin was seen in the subcutaneous and fatty tissue of the 50 and 250 mg/kg/day dosage group animals. Centrilobular hypertrophy was seen in the high dose group males (3/5) and females (4/5).
/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ In a 90-day subchronic feeding study, butralin technical (99% a.i.) was administered to Sprague- Dawley rats (10/sex/dose) in the diet at dose levels of 0 (G1), 10 (G2), 50 (G3) and 200 (G4) mg/kg/day for 13 weeks. Ten additional animals/sex/dose group from the control and high dose groups were carried for 4 weeks beyond the 13 week exposure period as recovery test groups. Estimated actual dosages to 10.3 mg/kg/day for low-dose animals; 51 mg/kg/day for mid-dose animals; and 202 mg/kg/day for the high-dose animals. There were no mortalities or toxic signs in any of the test animals. Animals in all of the butralin treated groups displayed yellow coloring in the urine and in fat and various tissues at necropsy. The yellow coloring was due to the color of butralin and decreased in the recovery period, persisting only in the high-dose group by the end of the recovery period. Body weight reductions were observed in high-dose males (-17%) and females (-23%) and -14% in mid-dose males. Food consumption was also reduced: -11% for high-dose males, -7% for high-dose females and -9% for mid-dose males. During the recovery period, the high-dose animals gained weight faster than the control animals while consuming about the same amount of food during this 4 week period. There was no effect on water intake which was estimated visually. There were statistically significant alterations in several clinical chemistry values seen primarily in high-dose males and females as statistically significant changes and often as similar changes in mid-dose animals without achieving statistical significance. The following clinical chemistry changes were statistically significant (with p ranging from <0.05 to 0.001): Gamma glutamyl transferase (GGT) was elevated by +100% in mid-dose females and +200% in high-dose females. The GGT elevations reverted to normal by the end of the 4 week recovery period. Total protein and albumin was elevated in high-dose females (+12%) and males (+8%) and also low-dose males (+3%) and males (+6%). Urea was decreased in mid-dose males (-10%) and high-dose males (-13%). Aspartate amino transaminase was decreased in the high dose males (-28%) and mid-dose females (-24%) and males (-24%). Alanine amino transaminase was decreased in females of the low-dose group (-20%), in mid-dose group females (-27%) and in females of the high-dose group (-40%). Total bilirubin was increased in the high-dose females (+66%) and was also elevated after the recovery period. Calcium was increased in the high-dose females (+6%). Glucose was decreased in the high-dose females (-14%). Liver weights were elevated in the mid-dose males (+40%), in the mid-dose females (+11%) and in the high-dose females (+39%). The liver weight elevation persisted only in the high-dose females (+14%) at the end of the 4 week recovery period. Centrilobular hypertrophy of the liver increased from 1/10 in the control males to 3/10, 6/10 and 9/10 in the low-, mid- to high-dose males, respectively, achieving statistical significance only in the high-dose group. Eight of 10 males and 9/10 females in the high-dose group had normal thyroids by the end of the recovery period. Control animals 2/10 males and 2/10 females exhibited minimal hyperplasia (grade +\-) of the thyroid as did 1/10 high dose females by the end of the recovery period (week 17). Other organ weight changes were statistically significant in the adrenals, heart, kidney, and spleen but occurred as isolated findings without corresponding morphological changes. Many of the toxic signs seen in the high dose animals at the end of the 13 week treatment period were reversed or tended toward reversal by the end of the 4 week recovery period. These included changes in body weight, hematology, clinical chemistry, organ weight changes and histopathology. The NOEL for this study was 10 mg/kg/day. The LOEL was the 50 mg/kg/day based on body weight and food consumption reductions; reduced red blood cell counts, hematocrit and hemoglobin; and alterations in liver and thyroid organ weights.
For more Non-Human Toxicity Excerpts (Complete) data for BUTRALIN (15 total), please visit the HSDB record page.
규제 정보
FIFRA Requirements
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.
안전 데이터
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- BW9500000
- ridadr
- 1325
- 독성
- LD50 orally in rats: 2500 mg/kg (McLane)
- HS 번호
- 29214990
- risk_code
- 24-36/37/38-50/53-36-22-63
- hazard_code
- T,N,Xn
- safety_code
- 26-36/37-45-60-61
- 포장분류
- II
- 위험 등급
- 4.1
- Hazard Classifications
- Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Repr. 2
- 스토리지 클래스
- 11 - Combustible Solids
- 유해 물질 데이터
- 33629-47-9(Hazardous Substances Data)
화학 및 산업
약리 정보
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.
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).
용도 및 제조
Uses
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.
Formulations/Preparations
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
응용 분야
용도Herbicide.
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