(4-クロロ-2-メチルフェノキシ)酢酸

(4-chloro-2-Methylphenoxy)acetic acid

HCID 7204CAS 94-74-6

基本情報

標準SMILES
Cc1cc(Cl)ccc1OCC(=O)O
InChIKey
WHKUVVPPKQRRBV-UHFFFAOYSA-N
分子式
C9H9ClO3
平均分子量
200.62 g/mol
単同位体質量
200.02402183

概要

(4-chloro-2-methylphenoxy)acetic acid is a chlorophenoxyacetic acid that is (4-chlorophenoxy)acetic acid substituted by a methyl group at position 2. It has a role as a synthetic auxin, a phenoxy herbicide and an environmental contaminant. It is a chlorophenoxyacetic acid and a member of monochlorobenzenes. It is a conjugate acid of a (4-chloro-2-methylphenoxy)acetate.

名称と識別子

優先名称
(4-chloro-2-Methylphenoxy)acetic acid
IUPAC
2-(4-chloro-2-methylphenoxy)acetic acid
現地名
(4-クロロ-2-メチルフェノキシ)酢酸
英語名
2-Methyl-4-chlorophenoxyacetic acid
分子式
C9H9ClO3
分子量
200.62

名称と別名

MCPA94-74-62-METHYL-4-CHLOROPHENOXYACETIC ACID(4-Chloro-2-methylphenoxy)acetic acidZelanMephanacEmcepanNetazolRhonoxHerbicide MHedarex MHedonal M
名称をさらに表示
(4-クロロ-2-メチルフェノキシ)酢酸2-メチル-4-クロロフェノキシ酢酸メタキソン4-クロロ-2-メチルフェノキシ酢酸アグロキソンMCPA剤(2-メチル-4-クロロフェニルオキシ)酢酸(2-メチル-4-クロロフェノキシ)酢酸2-(2-メチル-4-クロロフェノキシ)酢酸メトキソン2-(4-クロロ-2-メチルフェノキシ)酢酸[(4-クロロ-2-メチルフェニル)オキシ]酢酸MCPA標準品4クロロ2メチルフェノキシ酢酸(4-クロロ-2-メチルフェノキシ)酢酸 (別名 MCP又はMCPA)4-クロロ-2-メチルフェノキシ酢酸 (MCP)MCPA 4-クロロ-2-メチルフェノキシ酢酸MCPMCP標準物質MCPA酸 STANDARDMCPA酸MCPbanvelmMCPA Ester2-(4-CHLORO-2-METHYLPHENOXY)ACETIC ACID4-CHLORO-2-METHYLCHLOROPHENOXYACETICACIDBH MCPAbanleneplus2-Methyl-4-chlorophenoxyacetic
Okultin MLeuna MBordermasterHornotuhoLinormoneAgroxonChiptoxKrezone

データベース識別子

CAS
94-74-6
PubChem CID
7204
DTXSID
DTXSID4024195
ChEMBL
CHEMBL394657
ChEBI
CHEBI:50099
UNII
D888C394VO
EC Number
202-360-6
Nikkaji
J25.212C

物性

構造計算による物性

XLogP
2.6
極性表面積
46.5 Ų
水素結合供与体数
1
水素結合受容体数
3
回転可能結合数
3
重原子数
13

実験および物理化学的性質

SpringerMaterials PropertiesFusion temperature
Pesticides · 6 件

Pesticide -> EPA IRIS

Herbicides

Active substance -> EU Pesticides database: Approved

Pesticides -> Herbicides, Chlorophenoxy

Herbicides, Transformation products

Pesticide

LogP · 3 件

log Kow = 3.25

2.8

2.69

Density · 2 件

1.56 @ 25 °C/15.5 °C

Relative density (water = 1): 1.3

Color/Form · 4 件

White to light brown solid flakes, crystal powder or liquid.

Plates from benzene or toluene

White crystalline solid (pure compd)

Colorless crystalline solid (pure)

Solubility · 6 件

Solubility: in water 270 g/l, methanol 340 g/l, benzene 1 g/l /2-Methyl-4-chlorophenoxyacetic acid sodium salt/

INSOL IN CARBON DISULFIDE; SOLUBILITY (G/100 ML): ETHER 77, ETHANOL 153, N-HEPTANE 0.5, TOLUENE 6.2, XYLENE 4.9

SOL IN CARBON TETRACHLORIDE

Free acid insol in water but sodium and amine salts are soluble

Sol in benzene

For more Solubility (Complete) data for 2-METHYL-4-CHLOROPHENOXYACETIC ACID (6 total), please visit the HSDB record page.

物理化学的性質

融点
114 · 114-118 °C (lit.)
沸点
288.02 °C · 288.02°C (rough estimate)
比重(密度)
1.2799 · 1.2799 (rough estimate)
屈折率
1.523 · 1.5230 (estimate)
闪点
2 °C · 2 °C
貯蔵温度
Sealed in dry,Room Temperature

化学的性質

化学的特性White, crystalline solid. Free acid insoluble in water but sodium and amine salts are soluble.

安全と法規制

GHS分類

GHS Classification · 6 件

Danger

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P264, P264+P265, P270, P273, P280, P301+P317, P302+P352, P305+P354+P338, P317, P321, P330, P332+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Danger

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P354+P338, P317, P321, P330, P332+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

危険有害性情報

Regulatory Information · 4 件

TP - indicates a substance that is the subject of a proposed TSCA section 4 test rule.

05/57/EC, Reg. (EU) 2017/1511, Reg. (EU) 2018/1262, Reg. (EU) 2019/1589, Reg. (EU) 2021/1449, Reg. (EU) 2022/1480, Reg. (EU) 2023/1757, Reg. (EU) No 540/2011, Reg. (EU) No 762/2013, Reg. (EU)2020/1511

MCPA: HSNO Approval: HSR003327 Approved with controls

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Other Safety InformationIMAP assessments - Acetic acid, (4-chloro-2-methylphenoxy)-: Environment tier I assessment
Fire HazardsNot combustible. Liquid formulations containing organic solvents may be flammable. Gives off irritating or toxic fumes (or gases) in a fire. Risk of fire and explosion if formulations contain flammable/explosive solvents.
Fire PotentialNonflammable
Hazards Summary · 1 件

A skin, eye, and respiratory tract irritant; May be toxic to human reproduction or development, based on animal studies; [ICSC] May cause skin, eye, nose, and throat irritation; Effects in high dose oral studies of rats include histopathological changes to liver, kidneys, and spleen; [HSDB] Based on animal studies, not likely to cause congenital defects; No human data available; [REPROTOX] Chlorophenoxy herbicides are possibly carcinogenic to humans (Group 2B), but No adequate data were available on the carcinogenicity of MCPA. [IARC] See 2,4D.

EC ClassificationSymbol: Xn, N; R: 22-38-41-50/53; S: (2)-26-37-39-60-61

安全と保護具

Fire FightingIn case of fire in the surroundings, use appropriate extinguishing media.
First Aid Measures · 4 件

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .

Rinse with plenty of water (remove contact lenses if easily possible). Refer immediately for medical attention.

Rinse mouth. Give one or two glasses of water to drink. Refer immediately for medical attention.

Safe StorageProvision to contain effluent from fire extinguishing. Separated from strong bases and food and feedstuffs. Store in an area without drain or sewer access. Cool.
Storage Conditions · 2 件

Keep in well-ventilated area.

Do not transport or store near fertilizers, seeds, insecticides, or fungicides.

Disposal Methods · 2 件

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Incineration: Liquids should be atomized into an incinerator equipped with an appropriate effluent gas cleaning device, and combustion maybe improved by mixing with a more flammable solvent (acetone or benzene). Solids should be combined with paper or other flammable material. An alternate procedure is to dissolve the solid in a flammable solvent and spray the solutions into the fire chamber.

Spillage Disposal · 1 件

Personal protection: filter respirator for organic gases and particulates adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into sealable containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

毒性情報

Body Burden · 2 件

2-Methyl-4-chlorophenoxyacetic acid residues were measured in 18 urine samples collected from workers who had been spray applying the herbicide less than 24 hr previous(1); concns of 10-50 ppb were found in 8 samples, concns of 50-150 ppb were found in 5 samples, and concns of 150-500 ppb were found in 5 samples(1). In another monitoring study of farmers and professional spraymen, median urine concns of 0.31-1.7 ug/ml were detected(2).

IN A SUICIDE, SPECIMENS TAKEN AT AUTOPSY CONTAINED THE FOLLOWING CONCENTRATIONS OF MCPA: BLOOD, 230 PPM; LIVER, 146 PPM; HEART, 154 PPM; & BRAIN, 32.8 PPM. IN ANOTHER CASE, THE CONCENTRATIONS IN AUTOPSY SPECIMENS OF BLOOD & URINE WERE 180 & 800 PPM, RESPECTIVELY.

TreatmentTreatment may include washing any areas of contact, GI decontamination if swallowed, administering an IV and forced alkaline diuresis. (L346)
Interactions · 1 件

Probenecid increased the acute toxicity of chlorophenoxyacetic acids (2,4-D, 2,4,5-T and MCPA) in rats. Probenecid increased the brain to plasma ratios of all the three (14)C labelled chlorophenoxyacetic acids. The increase was due only partly to the displacement of chlorophenoxyacids from their binding sites in rat plasma proteins by probenecid. Probenecid did not change significantly the intracerebral distribution pattern of (14)C labelled chlorophenoxyacetic acids.

Target OrgansHepatic
Health Effects · 1 件

Exposure to large amounts of CDDs causes chloracne, a severe skin disease with acne-like lesions that occur mainly on the face and upper body. CDDs may also cause liver damage and induce long-term alterations in glucose metabolism and subtle changes in hormonal levels. In addition, studies have shown that CDDs may disrupt the endocrine system and weaken the immune system, as well as cause reproductive damage and birth defects, central and peripheral nervous system pathology, thyroid disorders, endometriosis, and diabetes. 2,3,7,8-Tetrachlorodibenzo-p-dioxin is also a known human carcinogen. (L177, L178)

Ecotoxicity Values · 4 件

LC50 LEPOMIS MACROCHIRUS (BLUEGILL) MORE THAN 10 MG/L/96 HR @ 24 °C, FINGERLING. STATIC BIOASSAY WITHOUT AERATION, PH 7.2-7.5, WATER HARDNESS 40-50 MG/L AS CALCIUM CARBONATE AND ALKALINITY OF 30-35 MG/L. /LIQUID CONCENTRATE 27.6%/

LC50 Salmo gairdneri (Rainbow trout) 232 mg/l/96 hr /Conditions of bioassay not specified/

TLm Crassostrea virginica (American oyster) 3.13X10+4 ppb/14 day, larvae, static lab bioassay

LC50 Lepomis macrochirus (Bluegill) 1500 ug/l/48 hr /Conditions of bioassay not specified/

法規制情報

FIFRA Requirements · 3 件

Tolerances are established for residues of the herbicide 2-methyl-4-chlorophenoxyacetic acid from application of the herbicide in the acid form or in the form of its sodium, ethanolamine, diethanolamine, triethanolamine, isopropanolamine, diisopropanolamine, triisopropanolamine, or dimethylamine salts or its isooctyl or butoxyethyl esters in or on raw agricultural commodities as follows: alfalfa; alfalfa, hay; barley, grain; barley, straw; clovers; clover, hay; flax, straw; flaxseed; grasses, pasture; grasses, rangeland; grass, canary, annual, seed; grass, canary, annual, straw; grass, hay; lespedeza; lespedeza, hay; oats, forage; oats, grain; oats, straw; peas; peavines; peavines, hay; rice, grain; rice, straw; rye, forage; rye, grain; rye, straw; sorghum, fodder; sorghum, forage; sorghum, grain; trefoils; trefoil, hay; vegetables, seed and pod; vetches; vetch, hay; wheat, forage; wheat, grain; wheat, straw.

Tolerances are established for combined negligible residues (N) of the herbicide 2-methyl-4-chlorophenoxyacetic acid and its metabolite 2-methyl-4-chlorophenol in or on the following raw agicultural commodities: cattle, fat; cattle, mbyp; cattle, meat; goats, fat; goats, mbyp; goats, meat; hogs, fat; hogs, mbyp; hogs, meat; horses, fat; horses, mbyp; horses, meat; milk; sheep, fat; sheep, mbyp; and sheep, meat.

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. 2-methyl-4-chlorophenoxyacetic acid is found on List A, which contains most food use pesticides and consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA, as amended in 1988. Case No: 0017; Pesticide type: Herbicide; Registration Standard Date: 09/12/89; Case Status: OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): 2-methyl-4-chlorophenoxyacetic acid; Data Call-in (DCI) Date(s): 05/12/93, 04/06/94, 03/03/95, 10/13/95; AI Status: The producers of the pesticide has made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner.

State Drinking Water Guidelines · 3 件

(FL) FLORIDA 1,000 ug/l

(ME) MAINE 4 ug/l

(MN) MINNESOTA 3 ug/l

Federal Drinking Water GuidelinesEPA 30 ug/L

安全データ

wgk
2
tsca
TSCA listed
rtecs
AG1575000
ridadr
UN 2765
毒性
LD50 orally in rats: 700 mg/kg (Rowe, Hymas)
PRTR法
第一種指定化学物質

化学と産業

薬理情報

Metabolism/Metabolites · 6 件

YIELDS 4-CHLORO-2-HYDROXYMETHYLPHENOXYACETIC ACID & N-(4-CHLORO-2-METHYLPHENOXYACETYL)-L-ASPARTIC ACID IN RAPE & IN CAMPION. YIELDS 4-CHLORO-2-METHYLPHENOXYACETYL-BETA-D-GLUCOSE PROBABLY IN RAPE. /FROM TABLE/

... 2-METHYL-4-CHLOROPHENOL WAS DETECTED IN MILK OF DAIRY COWS & IN KIDNEYS OF SHEEP & CATTLE.

ARTHROBACTER SP AND FLAVOBACTERIUM PEREGRINUM DEGRADED MCPA TO 4-CHLORO-2-METHYLPHENOL. FLAVOBACTERIUM FURTHER OXIDIZED PHENOL TO RELEASE ALL CHLORIDE. ASPERGILLUS NIGER VAN TIEGH ALSO METABOLIZED MCPA TO 4-CHLORO-2-METHYL-5-HYDROXYPHENOXYACETIC ACID.

... GRAM-NEGATIVE SOIL BACTERIUM METABOLIZED MCPA TO 5-CHLORO-O-CRESOL, A COMPOUND BELIEVED TO BE 6-HYDROXY-MCPA & ALPHA-METHYL-GAMMA-CARBOXYMETHYLENE-DELTA ALPHA-BUTENOLIDE.

For more Metabolism/Metabolites (Complete) data for 2-METHYL-4-CHLOROPHENOXYACETIC ACID (6 total), please visit the HSDB record page.

CDDs are absorbed through oral, inhalation, and dermal routes of exposure. CDDs are carried in the plasma by serum lipids and lipoproteins, distributing mainly to the liver and adipose tissue. CDDs are very slowly metabolized by the microsomal monooxygenase system to polar metabolites that can undergo conjugation with glucuronic acid and glutathione. They may increase the rate of their own metabolism by inducing CDDs induce both phase I and phase II enzymes. The major routes of excretion of CDDs are the bile and the feces, though smaller amounts are excreted in the urine and via lactation. (L177)

MeSH Pharmacological ClassificationPesticides used to destroy unwanted vegetation, especially various types of weeds, grasses (POACEAE), and woody plants. Some plants develop HERBICIDE RESISTANCE.
Absorption, Distribution and Excretion · 5 件

... NOT ABSORBED THROUGH SKIN TO ANY APPRECIABLE EXTENT ... . /2,4-D/

(14)C MCPA ... INJECTED IV INTO PREGNANT MICE, WHICH WERE THEN STUDIED BY AUTORADIOGRAPHY AT INTERVALS OF 5 MIN TO 72 HR. DISTRIBUTION PATTERN WAS CHARACTERIZED BY HIGH CONCN IN BLOOD UP TO 4 HR & ACCUMULATION IN VISCERAL YOLK SAC EPITHELIUM UP TO 24 HR AFTER INJECTION. RADIOACTIVE SUBSTANCE PASSED THE PLACENTA, BUT FETAL TISSUES NEVER REACHED CONCN OF THE MATERNAL TISSUES. RADIOACTIVITY WAS ELIMINATED FROM FETUSES & MOTHERS BY 24 HR AFTER INJECTION.

WHEN ADMINISTERED TO RATS BY STOMACH TUBE, THE HIGHEST CONCENTRATIONS OF (14)C MCPA IN THE TISSUES WAS REACHED IN 2-8 HR & THEN DECLINED RAPIDLY. DURING THE FIRST 24 HOURS 92.3% OF THE DOSE WAS DISCOVERED IN URINE & 6.8% IN THE FECES.

ABOUT 50% OF THE TOTAL DOSE WAS DETECTED IN URINE OF 4 VOLUNTEERS WITHIN 48 HR AFTER EACH INGESTED 5 MG OF MCPA. FIVE DAYS AFTER INGESTION, THE CONCENTRATION IN THE URINE WAS BELOW THE DETECTABLE LEVEL OF 0.02 PPM.

For more Absorption, Distribution and Excretion (Complete) data for 2-METHYL-4-CHLOROPHENOXYACETIC ACID (8 total), please visit the HSDB record page.

用途と製造

Uses · 6 件

Used as a post-emergence herbicide for control of annual and perennial broad leaved weeds in cereals, herbage seed crops, flax, rice, vines, peas, potatoes, asparagus, grassland, turf, orchards, roadsides, forestry, and aquatic areas; [HSDB]

Farming (Pesticides) [Category: Industry]

For 2-Methyl-4-chlorophenoxyacetic acid (USEPA/OPP Pesticide Code: 030501) 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./

MCPA is used as a postemergence herbicide for control of broadleaf weeds in agricultural applications.

HERBICIDE FOR CONTROL OF ANNUAL & PERENNIAL WEEDS

Post-emergence control of annual and perennial broad leaved weeds (including thistles and docks) in cereals (alone or undersown), herbage seed crops, flax, rice, vines, peas, potatoes, asparagus, grassland, turf, under fruit trees, and on roadside verges and embankments. Control of broad-leaved and woody weeds in forestry. Control of aquatic broad leaved weeds.

ImpuritiesThe technical grade might contain 3-40% 6-chloro-2-methylphenoxyacetic acid. The hormone-type herbicide, commercial grade contains 4% of 4-chloro-o-cresol.
U.S. Production(1975) 1.77X10+9 GRAMS (CONSUMPTION)
Consumption Patterns · 2 件

HERBICIDE, OF WHICH APPROXIMATELY 69% IS USED ON WHEAT, 18% ON OTHER GRAINS, & 13% ON RICE (1975)

(1992) Total pounds applied to: wheat and grains (3,445,394); barley (633,976); pasture (225,232); oats (207,439); rice (60,022); field and grass seed (51,260; flax (13,334); dry peas (7,103); rye (6,942); green peas (6,636).

Methods of Manufacturing · 2 件

CHLORINATION OF O-CRESOL FOLLOWED BY REACTION WITH THE SODIUM SALT OF MONOCHLOROACETIC ACID

Ethylmercaptan + 2-methyl-4-chlorophenoxyacetic acid (thioesterification)

Formulations/Preparations · 5 件

USEPA/OPP Pesticide Code 030501; Trade Names: Mephanac; Agroxone; Bordermaster; BH MCPA; Cekherbex; chiptox; DED-Weed; empal; Hedonal M; Hormotuho; Kilsem; M 40; Phenoxylene Plus; Rhomene; Rhonox; Shamrox; Vacate; Fluid 4; weedar; Weedone; Zelan; Dikotex; Hedonal.

TECHNICAL MCPA HAS TYPICAL COMPOSITION OF: MCPA, 94-96%; 2-METHYL-6-CHLOROPHENOXYACETIC ACID, 1.5-3.0%; MIXTURE OF 2-METHYL-4,6-DICHLOROPHENOXYACETIC ACID, 2-METHYLPHENOXYACETIC ACID, 2-CHLOROPHENOXYACETIC ACID, 4-CHLOROPHENOXYACETIC ACID, & 2,6-DIMETHYL-4-CHLOROPHENOXYACETIC 0.5-1.5%; CHLORO-O-CRESOL, 0.5% & WATER, 1.0%.

MCPA IS AVAILABLE AS AMINES, ESTERS, & SODIUM OR POTASSIUM SALTS.

BANVEL M IS MIXTURE OF MCPA & BANVEL. BROMINAL PLUS & BRONATE...ARE MIXTURE OF MCPA & BROMOXYNIL. PHENOXYLENE SUPER IS MIXTURE OF MCPA WITH DICAMBA. BANLENE PLUS, RAZOL DOCK PROPORTIONS.

For more Formulations/Preparations (Complete) data for 2-METHYL-4-CHLOROPHENOXYACETIC ACID (10 total), please visit the HSDB record page.

応用分野

使用Labelled MCPA (C369470). Herbicide.

一般的な説明Colorless plates. Corrosive. Practically insoluble in water. Used as an herbicide.

調製方法 · 1 件

純化方法It is insoluble in H2O (solubility is 0.55g/L at 20o) and recrystallises from *C6H6 or chlorobenzene as plates [J.nsson et al. Acta Chem Scand 6 993 1952]. The S-benzylisothiouronium salt has m 164-165o, and the Cu2+ salt has m 247-249o(dec) [Armarego et al. Nature 183 1176 1959, UV: Duvaux & Grabe Acta Chem Scand 4 806 1950, IR: J.berg Acta Chem Scand 4 798 1950]. [Beilstein 6 IV 1991.] It is a plant growth substance and a herbicide.

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補足説明

定義ChEBI: A chlorophenoxyacetic acid that is (4-chlorophenoxy)acetic acid substituted by a methyl group at position 2.

関連反応

17 件

関連ノート

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