기본 정보
- 표준 SMILES
CCCCOCN(C(=O)CCl)c1c(CC)cccc1CC- InChIKey
HKPHPIREJKHECO-UHFFFAOYSA-N- 분자식
- C17H26ClNO2
- 평균 분자량
- 311.8 g/mol
- 단동위원소 질량
- 311.16520675
개요
Butachlor is an aromatic amide that is 2-choro-N-(2,6-diethylphenyl)acetamide in which the amide nitrogen has been replaced by a butoxymethyl group.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, a xenobiotic and an environmental contaminant. It is a tertiary carboxamide, an organochlorine compound and an aromatic amide. It is functionally related to a N-phenylacetamide.
이름 및 식별자
- 우선 이름
- Butachlor
- IUPAC
- N-(butoxymethyl)-2-chloro-N-(2,6-diethylphenyl)acetamide
- 현지명
- 부타클로르
- 영어명
- Machette
- 분자식
- C17H26ClNO2
- 분자량
- 311.85
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- CAS
23184-66-9- PubChem CID
- 31677
- DTXSID
DTXSID3034402- ChEMBL
CHEMBL1399036- ChEBI
CHEBI:3230- UNII
- 94NU90OO5K
- EC Number
- 245-477-8
- Nikkaji
- J1.872D
물성
구조 계산 물성
- XLogP
- 4.5
- 극성 표면적
- 29.5 Ų
- 수소 결합 공여자 수
- 0
- 수소 결합 수용자 수
- 2
- 회전 가능 결합 수
- 9
- 무거운 원자 수
- 21
- 형식 전하
- 0
- 복잡도
- 287
실험 및 물리화학적 성질
Pesticides
Herbicides
Active substance -> EU Pesticides database: Not approved
Pesticides -> Herbicides, Chloracetanilide
Pesticide (Butachlor) -> USDA PDB
Pesticide
LogP
log Kow = 4.5
4.5
Color/Form
Amber liquid
Light yellow oil
Solubility
Soluble in most organic solvents, including diethyl ether, acetone, benzene, ethanol, ethyl acetate, and hexane
In water, 20 mg/l at 20 °C
Flash Point
114 °C (open cup); 93 °C (closed cup)
>135 °C (Tag closed cup)
Decomposition
Decomposes at 165 °C.
When heated to decomposition it emits toxic fumes of /hydrogen chloride/ and /nitrous oxides/.
물리화학적 성질
- 녹는점
- -5 °C · <-5°C
- 끓는 점
- 156 °C · 156°C (0.5 torr)
- 밀도
- 430 · d430 1.0695
- 굴절률
- 1.5388 · 1.5388 (estimate)
- 인화점
- 100 °C · 100 °C
- 저장 조건
- 0 · 0-6°C
- 용해도
- 클로로포름(약간 용해됨), 메탄올(약간 용해됨)
- 산도 계수 (pKa)
- 1.2 · 1.20±0.50(Predicted)
- 물리적 상태
- 액체
- 색상
- 연한 노란색-보라색
- 수용성
- 20 mg/L · 20mg/L(20℃)
- BRN
- 2873811 · 2873811
- Henry's Law Constant
- 1.6 · 1.6×102 mol/(m3Pa) at 25℃, Watanabe (1993)
- 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
- InChIKey
- HKPHPIREJKHECO-UHFFFAOYSA-N
- SMILES
- CCCCOCN(C(=O)CCl)c1c(CC)cccc1CC
- NIST
- Butachlor(23184-66-9)
- EPA
- Butachlor (23184-66-9)
화학적 성질
Yellow Oil
안전 및 규제
GHS 분류
GHS Classification
This chemical does not meet GHS hazard criteria for 0.7% (1 of 136) of reports.
Danger
H302 (99.3%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P270, P271, P272, P273, P280, P301+P317, P302+P352, P304+P340, P316, P321, P330, P333+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 136 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Danger
유해성 정보
Hazard Classes and Categories
Acute Tox. 4 (99.3%)
Acute toxicity (Oral) - Category 4
Standard Transportation Number
49 216 72; Organochlorine pesticide (compounds and preparations), solid (poison b) insecticides, nec, other, than agricultural).
49 216 73; Organochlorine pesticide (compounds and preparations), solid (poison b) insecticides, agricultural, nec, other than liquid).
State Drinking Water Guidelines
(FL) FLORIDA 259 ug/l
(ME) MAINE 26 ug/l
Shipment Methods and Regulations
No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./
The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.
The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.
Shipping Name/ Number DOT/UN/NA/IMO
UN 2761; Organochlorine pesticides, solid, toxic, not otherwise specified (compounds & preparations)
UN 2762; Organochlorine pesticides, liquid, flammable, toxic, not otherwise specified, flashpoint less than 23 °C (compounds & preparation)
UN 2995; Organochlorine pesticides, liquid, toxic, flammable, not otherwise specified, flashpoint 23 °C or more
UN 2996; Organochlorine pesticides, liquid, toxic, not otherwise specified
For more Shipping Name/ Number DOT/UN/NA/IMO (Complete) data for BUTACHLOR (6 total), please visit the HSDB record page.
안전 및 보호
Fire Fighting Procedures
If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemical or carbon dioxide. /Organochlorine pesticide, liquid/
If material on fire or involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Use "alcohol" foam, dry chemical or carbon dioxide. /Organochlorine pesticides, solid, toxic/
Storage Conditions
Store in cool, dry place away from feed and foodstuffs.
Do not store near heat or open flame.
Cleanup Methods
Environmental considerations: Water spill: Use natural barriers or oil spill control booms to limit spill travel. Use natural deep water pockets, excavated lagoons, or sand bag barriers to trap material at bottom. Remove trapped material with suction hoses. /Organochlorine pesticide, solid, toxic/
Environmental considerations: Land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Cover solids with a plastic sheet to prevent dissolving in rain or fire fighting water. Dike surface flow using solid, sand bags, foamed polyurethane, or foamed concrete. /Organochlorine pesticide, solid, toxic/
Environmental considerations: Air spill: Apply water spray or mist to knock down vapors. /Organochlorine pesticide, liquid/
Environmental considerations: Water spill: Use natural barriers or oil spill control booms to limit spill travel. Remove trapped material with suction hoses. /Organochlorine pesticide, liquid/
Environmental considerations: Land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using solid, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents. /Organochlorine pesticide, liquid/
Disposal Methods
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
Avoid contact with mouth, skin or eyes, washing all parts with plenty of soap and water after handling. Keep away from children. Store in cool, dry place away from feed and foodstuffs.
Personnel protection: Avoid breathing dusts, and fumes from burning material. Keep upwind. ...Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. If contact with the material anticipated, wear appropriate chemical protective clothing. /Organochlorine pesticides, solid, toxic/
Personnel protection: Void breathing vapors. Keep upwind. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Organochlorine pesticide, liquid/
If material not of fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. /Organochlorine pesticides, solid, toxic/
If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Use water spray to knock-down vapors. /Organochlorine pesticide, liquid/
Personal Protective Equipment (PPE)
Rubber gloves, respirator, boots, long sleeved shirt or jacket, long pants.
Personnel protection: ... Wear appropriate chemical protective gloves, boots and goggles. .... /Organochlorine pesticide, liquid; Organochlorine pesticide, solid, toxic/
독성 정보
Treatment
Consider gastric lavage, as well was dilution with milk or water after ingestion. Administer charcoal as a slurry following ingestion; however, activated charcoal should not be given to patients ingesting strong acidic or basic caustic chemicals. In case of inhalation, move patient to fresh air. Monitor for respiratory distress. If cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with inhaled beta2 agonist and oral or parenteral corticosteroids. Irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. Following dermal exposure, remove contaminated clothing and wash exposed area thoroughly with soap and water. Treat dermal irritation or burns with standard topical therapy. Patients developing dermal hypersensitivity reactions may require treatment with systemic or topical corticosteroids or antihistamines. Administer symptomatic treatment as necessary. (T36)
Ecotoxicity Values
LC50 Bluegill sunfish 0.44 mg/L/96 hr /Technical butachlor ; Conditions of bioassay not specified in source examined/
LC50 Rainbow trout 0.52 mg/L/96 hr /Technical butachlor; Conditions of bioassay not specified in source examined/
LC50 Crayfish 26.0 mg/L/96 hr /Technical butachlor; Conditions of bioassay not specified in source examined/
LD50 Bobwhite quail oral >10,000 mg/kg
For more Ecotoxicity Values (Complete) data for BUTACHLOR (13 total), please visit the HSDB record page.
Environmental Fate
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 6700(SRC), determined from a log Kow of 4.5(2) and a regression-derived equation(3), indicates that butachlor is expected to be immobile in soil(SRC). Volatilization of butachlor from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 5.10X10-8 atm-cu m/mole(4). Butachlor is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 2.90X10-6 mm Hg(4). Half-lives for butachlor in soil reported from biodegradation studies range from approximately 1.6 days to 11.4 days(5).
TERRESTRIAL FATE: Field half-lives of butachlor in soil have been measured to be 11 to 18 days, 4 to 8 days, and 10 to 18 days(1). When butachlor was applied to Ray silt and Wabash silty loam soil in Missouri at their normal preplant application time, the field half-lives were 9.4 and 14.4 days, respectively(2). Dissipation followed first order kinetics(2). Despite moist field conditions (near saturation at time of application and 2.25 cm of rain on the 3rd day), <1% of the herbicide was found below 4 cm(2). Therefore leaching does not appear to make a significant contribution to field dissipation. In a field study in Thailand, butachlor applied to cultivated fields containing clay loam and clay soils during the rainy season was detectable by GC for 180 days after application(3). In a study of butachlor persistance in Indian soils using plant bioassays, butachlor persisted for 40 days in a sandy clay loam soil, 60 days in sandy and clayey soils, and lost its activity rapidly in an organic soil(4). Under natural conditions of paddy fields, the half-life of butachlor was determined to be 1.65-2.48 days and 5.79-6.30 days when applied as an emulsion and granules, respectively(5). The half-lives in soil were found to be 2.67-5.33 and 4.95-6.30 days, respectively for these formulations(5). When butachlor was applied to 4 Chinese paddy soils, the half-life ranged from 3.17 to 3.61 days(1). In rice fields, leaching occurred in the silty loam and loamy silt soils, but not in the clay loam and red loam soils where it remained in the upper 5-cm(6). However, no residues were found in the soil profile or ground water after the rice growing season(6).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 6,700(SRC), determined from a log Kow of 4.5(2) and a regression-derived equation(3), indicates that butachlor is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon a Henry's Law constant of 5.10X10-8 atm-cu m/mole(4). According to a classification scheme(5), an estimated BCF of 1500(SRC), from an estimated log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is very high(SRC). Butachlor degraded rapidly when applied to water at the recommended rates; its half-life in water was 1.11-1.12 days(7).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), butachlor, which has a vapor pressure of 2.990X10-6 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase butachlor 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 6.8 hours(SRC), calculated from its rate constant of 5.7X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase butachlor may be removed from the air by wet and dry deposition(SRC). Butachlor does not absorb UV light >290 nm and therefore direct photolysis is not expected(4).
Ecotoxicity Excerpts
/FIELD STUDIES/ The effects of pesticide contamination on the population size and denitrification activity of denitrifying bacteria (DNB) were studied with three types of paddy soil (Huangsong paddy soil, red earth paddy soil and purple paddy soil) treated with carbofuran, carbendazim and butachlor for four weeks. The results showed that the population size of DNB in purple paddy soil, Huangsong paddy soil and red earth paddy soil varied in the range of 59.04 x 10(4)-157.59 x 10(4), 42.89 x 10(4)-108.97 x 10(4) and 32.14 x 10(4)-75.30 x 10(4) cfu.g-1 dried soil, respectively, which was positively related to the quantity of consumed nitrate in paddy soils. The population size and denitrification activity of DNB were increased by adding carbofuran (1 mg.kg-1 dried soil) or butachlor (1 mg.kg-1 dried soil), but decreased significantly by adding 10 mg.kg-1 dried soil of butachlor, 5 mg.kg-1 dried soil of carbofuran, and 10 mg.kg-1 dried soil of carbendazim on 7th d, 14th d and 7th d, respectively.
Signs and Symptoms
CNS excitation, seizures, tremor, ataxia, agitation, nervousness, and amnesia may occur. Kelthane, perthane, methoxychlor, and hexachlorobenzene have little CNS toxicity; in significant overdose CNS depression may occur. Nausea, vomiting, and diarrhea may follow ingestion (T36).
Effluent Concentrations
In a field study in Thailand in which 4.0 kg/ha was applied to cultivated fields containing clay loam soil (8-10% slope) and clay soil (25-28% slope) during the rainy season, the maximum concn of butachlor in runoff was 61.5 and 15.5 ug/L, respectively(1). 52.2% of the butachlor in the runoff was in the water phase(1). The highest amounts of herbicide was lost 1-3 days after application(1).
Soil Adsorption/Mobility
Adsorbed by soil colloids.
The Koc of butachlor is estimated as 6700(SRC), using a log Kow of 4.5(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that butachlor is expected to be immobile in soil(SRC).
규제 정보
State Drinking Water Guidelines
(FL) FLORIDA 259 ug/l
(ME) MAINE 26 ug/l
안전 데이터
- wgk
- 3
- rtecs
- AE1200000
- ridadr
- UN3082 9/PG 3
- 독성
- LD50 orally in rats: 1740 mg/kg (Strateva)
- risk_code
- 22-50/53
- hazard_code
- Xn,N
- safety_code
- 60-61
- 기존화학 물질
- KE-04155
- Hazard Classifications
- Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1
- 스토리지 클래스
- 10 - Combustible liquids
- 유해 물질 데이터
- 23184-66-9(Hazardous Substances Data)
화학 및 산업
약리 정보
Biological Half-Life
Biological half-lives after exposure to high and low concentrations were 11.6 and 23.1 days, respectively; [HSDB]
... The biological half-lives of the three herbicides on exposure at high and low concentrations were 11.6 and 23.1 days for butachlor,
Metabolism/Metabolites
... 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)
MeSH Pharmacological Classification
Substances that increase the risk of NEOPLASMS in humans or animals. Both genotoxic chemicals, which affect DNA directly, and nongenotoxic chemicals, which induce neoplasms by other mechanism, are included.
Pesticides used to destroy unwanted vegetation, especially various types of weeds, grasses (POACEAE), and woody plants. Some plants develop HERBICIDE RESISTANCE.
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.
용도 및 제조
Uses
Used as herbicide for pre-emergence control of most annual grasses and some broadleaf weeds in seeded and transplanted rice grown in Asia, South America, Europe, and Africa; Not marketed in the US; [HSDB] Used in rice and barley; [Krieger, p. 1760]
Not currently registered with the EPA for use in the US; [HSDB]
Farming (Pesticides) [Category: Industry]
For butachlor (USEPA/OPP Pesticide Code: 112301) there are 0 labels match. /SRP: Not registered for current 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./
Selective herbicide
Preemergence control of most annual grasses, certain broadleaf weeds in seeded and transplanted rice grown in certain Asian, South American, European and African countries.
Formulations/Preparations
Emulsifiable concentrate, granules.
Trade names: Machete, Butanex, Butataf, Dhanuchlor, Farmachlor, Hiltaklor, Rasayanchlor, Trapp, Wiper, Ban Weed, Butamach, Butanox, Pilarsete, Vibuta. Mixtures: Bandito (+propanil), Sable (+ propanil), Vitanil (+propanil). Discontinued names mixtures: Delcut (+oxadiazon), Kusakarin (+ pyrazolynate)
Lambast
Amichlor
For more Formulations/Preparations (Complete) data for BUTACHLOR (6 total), please visit the HSDB record page.
응용 분야
용도Butachlor is a pre-emergent chloroacetanalide herbicide. Butachlor is commonly used for weed control in rice as well as cotton, maize, wheat and other crops.
상·하류 제품 정보
상류 원료
하류 제품
공급사50 곳
관련 반응
연결된 노트
불러오는 중…