Zurück
HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HCID 7204Erstellt: 24. Oktober 2026

MCPA (ISO)

MCPA · MCP · banvelm · MCPA Ester · 2-(4-CHLORO-2-METHYLPHENOXY)ACETIC ACID · 4-CHLORO-2-METHYLCHLOROPHENOXYACETICACID · Rhonox · BH MCPA

https://huagongshe.com/de/chemical/7204

Molekülstruktur von MCPA (ISO)

Identifikatoren & physikalische Daten

CAS No.94-74-6
SummenformelC9H9ClO3
Durchschnittliche Molmasse200,62 g/mol
Monoisotopische Masse200,02402183 g/mol
SMILESCc1cc(Cl)ccc1OCC(=O)O
InChIKeyWHKUVVPPKQRRBV-UHFFFAOYSA-N
PubChem CID7204
ChEMBLCHEMBL394657
ChEBICHEBI:50099
EC No.202-360-6
DTXSIDDTXSID4024195
Lokaler NameMCPA (ISO)

Chemische & physikalische Eigenschaften

XLogP2,6
Polarare Oberfläche (TPSA)46,5
H-Brücken-Donoren1
H-Brücken-Akzeptoren3
Frei drehbare Bindungen3
Schwere Atome13
Formalladung0
Komplexität184
SpringerMaterials PropertiesFusion temperature
PestizidePesticide -> EPA IRISHerbicidesActive substance -> EU Pesticides database: ApprovedPesticides -> Herbicides, ChlorophenoxyHerbicides, Transformation products
LogP (Verteilungskoeffizient)log Kow = 3.252.82.69
Dichte1.56 @ 25 °C/15.5 °CRelative density (water = 1): 1.31.2799 (rough estimate)
Color/FormWhite to light brown solid flakes, crystal powder or liquid.Plates from benzene or tolueneWhite crystalline solid (pure compd)Colorless crystalline solid (pure)
LöslichkeitSolubility: in water 270 g/l, methanol 340 g/l, benzene 1 g/l /2-Methyl-4-chlorophenoxyacetic acid sodium salt/INSOL IN CARBON DISULFIDESOLUBILITY (G/100 ML): ETHER 77, ETHANOL 153, N-HEPTANE 0.5, TOLUENE 6.2, XYLENE 4.9SOL IN CARBON TETRACHLORIDEFree acid insol in water but sodium and amine salts are solubleSol in benzeneFor more Solubility (Complete) data for 2-METHYL-4-CHLOROPHENOXYACETIC ACID (6 total), please visit the HSDB record page.water: insoluble(lit.)1.174g/L(25 ºC)
CorrosivityNon-corrosive
DecompositionWhen heated to decomposition it emits toxic fumes of /hydrogen chloride and nitrogen oxides/.WHEN HEATED TO DECOMP, IT EMITS TOXIC FUMES OF /HYDROGEN CHLORIDE/.
Schmelzpunkt118-119 °CMelting point: 115-117 °C /technical grade MCPA/113-119 °C114-118 °C (lit.)
Dampfdruck0.0000059 [mmHg]5.90X10-6 mm HgVapor pressure, Pa at 20 °C: (negligible)
Henry-KonstanteHenry's Law constant= 4.8X10-10 atm-cu m/mole @ 25 °C9.9×101 mol/(m3Pa) at 25℃, Mabury and Crosby (1996)
Physical DescriptionWhite solid[Hawley] Slightly beige solid[MSDSonline]WHITE CRYSTALLINE POWDER WITH CHARACTERISTIC ODOUR.
Siedepunkt288.02°C (rough estimate)
Brechungsindex1.5230 (estimate)
Flammpunkt2 °C
LagerbedingungenSealed in dry,Room Temperature
AggregatzustandSolid
pKa (Säurekonstante)3.14±0.10(Predicted)
FarbeWhite to Light yellow to Light orange
Merck14,5764
BRN2051752
InChI1S/C9H9ClO3/c1-6-4-7(10)2-3-8(6)13-5-9(11)12/h2-4H,5H2,1H3,(H,11,12)
InChIKeyWHKUVVPPKQRRBV-UHFFFAOYSA-N
SMILESCc1cc(Cl)ccc1OCC(O)=O
CAS Datenbank94-74-6(CAS DataBase Reference)
NIST chemische Informationen[(4-Chloro-o-tolyl)oxy]acetic acid(94-74-6)
EPA chemische InformationenMCPA (94-74-6)

Sicherheit & Vorschriften

GHS-EinstufungDangerH302: 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)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)
Regulatorische InformationenTP - 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)2020/1511MCPA: HSNO Approval: HSR003327 Approved with controlsThe 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.)
Weitere SicherheitsinformationenIMAP assessments - Acetic acid, (4-chloro-2-methylphenoxy)-: Environment tier I assessment
BrandgefahrenNot 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.
BrandpotenzialNonflammable
GefahrenübersichtA skin, eye, and respiratory tract irritantMay be toxic to human reproduction or development, based on animal studies[ICSC] May cause skin, eye, nose, and throat irritationEffects 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 defectsNo 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.
EG-EinstufungSymbol: Xn, NR: 22-38-41-50/53S: (2)-26-37-39-60-61
UN-EinstufungUN Hazard Class: 9UN Pack Group: III
Special ReportsEXTENSIVE ACUTE & CHRONIC TOXICITY DATA FOR MCPA IN MAMMALS, BIRDS, WILDLIFE, AQUATIC ORGANISMS, AMPHIBIANS, INSECTS & NEMATODES ARE PRESENTED.[BOVEY RWTOXICOLOGY OF PHENOXY HERBICIDES IN ANIMALS AND MAN - GENERAL CONSIDERATIONSIN: THE SCIENCE OF 2,4,5-T AND ASSOCIATED HERBICIDES. (JOHN WILEY & SONS: NY)CHO4: 71 (1980)]
FIFRA-AnforderungenTolerances 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: alfalfaalfalfa, haybarley, grainbarley, strawcloversclover, hayflax, strawflaxseedgrasses, pasturegrasses, rangelandgrass, canary, annual, seedgrass, canary, annual, strawgrass, haylespedezalespedeza, hayoats, forageoats, grainoats, strawpeaspeavinespeavines, hayrice, grainrice, strawrye, foragerye, grainrye, strawsorghum, foddersorghum, foragesorghum, graintrefoilstrefoil, hayvegetables, seed and podvetchesvetch, haywheat, foragewheat, grainwheat, 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, fatcattle, mbypcattle, meatgoats, fatgoats, mbypgoats, meathogs, fathogs, mbyphogs, meathorses, fathorses, mbyphorses, meatmilksheep, fatsheep, mbypand 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: 0017Pesticide type: HerbicideRegistration Standard Date: 09/12/89Case 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 acidData Call-in (DCI) Date(s): 05/12/93, 04/06/94, 03/03/95, 10/13/95AI 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.
Chemical DangersDecomposes on heating. This produces toxic and corrosive fumes including hydrogen chloride and phosgene. The substance is a weak acid. Attacks many metals in the presence of water.
Packaging and LabellingDo not transport with food and feedstuffs.
Hazard Classes and CategoriesAcute Tox. 4 (100%)Acute toxicity - category 4Acute toxicity (Oral) - Category 4Serious eye damage/eye irritation - Category 1Hazardous to the aquatic environment (Acute) - Category 1Acute Tox. 4 *
BrandbekämpfungIn case of fire in the surroundings, use appropriate extinguishing media.
Erste-Hilfe-MaßnahmenFresh 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.
Sichere LagerungProvision to contain effluent from fire extinguishing. Separated from strong bases and food and feedstuffs. Store in an area without drain or sewer access. Cool.
LagerbedingungenKeep in well-ventilated area.Do not transport or store near fertilizers, seeds, insecticides, or fungicides.
EntsorgungsverfahrenSRP: 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.
Verschüttetes entsorgenPersonal 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.
Preventive MeasuresSRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
Eye PreventionWear safety goggles or eye protection in combination with breathing protection if powder.
Inhalation RiskEvaporation at 20 °C is negligiblea harmful concentration of airborne particles can, however, be reached quickly on spraying or when dispersed, especially if powdered.
Skin PreventionProtective gloves. Protective clothing.
Exposure PreventionPREVENT DISPERSION OF DUST!
Allowable TolerancesTolerances 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, 0.1 ppmalfalfa, hay, 0.1 ppmbarley, grain, 0.1 ppm (N)barley, straw, 2 ppmclovers, 0.1 ppmclover, hay, 0.1 ppmflax, straw, 2 ppmflaxseed, 0.1 ppm (N)grasses, pasture, 300 ppmgrasses, rangeland, 300 ppmgrass, canary, annual, seed, 0.1 ppmgrass, canary, annual, straw, 0.1 ppmgrass, hay, 20 ppmlespedeza, 0.1 ppmlespedeza, hay, 0.1 ppmoats, forage, 20 ppmoats, grain, 0.1 ppmoats, straw, 2 ppmpeas, 0.1 ppm (N)peavines, 0.1 ppm (N)peavines, hay, 0.1 ppm (N)rice, grain, 0.1 ppm (N)rice, straw, 2 ppmrye, forage, 20 ppmrye, grain, 0.1 ppm (N)rye, straw, 2 ppmsorghum, fodder, 20 ppmsorghum, forage, 20 ppmsorghum, grain, 0.1 ppmtrefoils, 0.1 ppmtrefoil, hay, 0.1 ppmvegetables, seed and pod, 0.1 ppmvetches, 0.1 ppmvetch, hay, 0.1 ppmwheat, forage, 20 ppmwheat, grain, 0.1 ppm (N)wheat, straw, 2 ppm.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, 0.1 ppm (N)cattle, mbyp, 0.1 ppm (N)cattle, meat, 0.1 ppm (N)goats, fat, 0.1 ppm (N)goats, mbyp, 0.1 ppm (N)goats, meat, 0.1 ppm (N)hogs, fat, 0.1 ppm (N)hogs, mbyp, 0.1 ppm (N)hogs, meat, 0.1 ppm (N)horses, fat, 0.1 ppm (N)horses, mbyp, 0.1 ppm (N)horses, meat, 0.1 ppm (N)milk, 0.1 ppm (N)sheep, fat, 0.1 ppm (N)sheep, mbyp, 0.1 ppm (N)and sheep, meat, 0.1 ppm (N).
Körperbelastung2-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 PPMLIVER, 146 PPMHEART, 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)
WechselwirkungenProbenecid 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.
ZielorganeHepatic
Gesundheitliche AuswirkungenExposure 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)
ÖkotoxizitätswerteLC50 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 bioassayLC50 Lepomis macrochirus (Bluegill) 1500 ug/l/48 hr /Conditions of bioassay not specified/
UmweltverhaltenTERRESTRIAL FATE: Based on a classification scheme(1), a Koc value ranging from the 50 to 62 (2), indicates that MCPA is expected to have high mobility in soil(SRC). Volatilization of MCPA from moist soil surfaces is not expected to be an important fate process(SRC) based on its Henry's Law constant of 4.80X10-10 atm-cu/mole(3). MCPA is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 5.90X10-6 mm Hg(4). The primary degradation process for MCPA in soil is biodegradation(5). A literature review of available laboratory persistence studies of MCPA in soil found soil half-lives ranging from <7 to 41 days with an average of about 2-3 weeks(6). MCPA is susceptible to photodegradation in sunlight(5,7)however, photodegradation at the soil surface is not considered a major degradation pathway since it is applied post-emergence to growing crops, and residues reaching the soil will be protected from sunlight by the crop canopy(5). Under field studies, the resultant average persistence of MCPA at recommended application rates is up to 1 month in moist conditions and up to 6 months under drier climates(8).AQUATIC FATE: Based on a classification scheme(1), a Koc value ranging from 50 to 62(2), indicates that MCPA is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon its Henry's Law constant of 4.80X10-10 atm-cu m/mole(4). According to a classification scheme(5), a BCF of 1(6), suggests the potential for bioconcentration in aquatic organisms is low. Based on degradation studies, it appears that MCPA will biodegrade in water but at a slower rate than in soil. In flooded sediment, the complete degradation of MCPA took 96 wks, but only 48 wks in moist soilthe ratio of relative persistence in moist soil vs. flooded sediment was determined to be 1:2.3(7). The direct photolysis half-life of MCPA in water (at surface conditions under summer sunlight) is about 19-20 days(8).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), MCPA, which has a vapor pressure of 5.90X10-6 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase MCPA 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 30 hours(SRC), calculated from its rate constant of 1.3X10-11 cu cm/molecule-sec at 25 °C(SRC), determined using a structure estimation method(3). Particulate-phase MCPA may be removed from the air by wet and dry deposition(SRC). Aerial drift from herbicidal spraying operations can transport MCPA to nearby ponds and streams(4). A multi-year study of MCPA in surface water of a small prairie watershed concluded that the aqueous concns of MCPA were related to elevated precipitation and air levels rather than to runoff losses(5). MCPA may undergo direct photolysis since it is photochemically reactive in water(6). Exposure of aqueous solutions of MCPA in distilled water to Oct sunlight in Davis, CA resulted in a 14% decomposition of MCPA after 245 hr of exposure(7).
LebensmitteluntersuchungswerteNo 2-methyl-4-chlorophenoxyacetic acid (MCPA) residues were detected in any food composites collected from July 1, 1969 to June 30, 1976 as part of the FDA's (Food and Drug Administration) Total Diet Study (market basket survey of ready-to-eat US foods)(1). In earlier Total Diet Study analyses (June 1964 to Apr 1969), MCPA was detected in 11 of 1236 food composite samples at levels ranging from a trace to 0.40 ppm(2-5).
Unerwünschte WirkungenOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
ExpositionspfadeThe substance can be absorbed into the body by inhalation of its aerosol, through the skin and by ingestion.
Milk Concentrations... 2-METHYL-4-CHLOROPHENOL WAS DETECTED IN MILK OF DAIRY COWS ... .
ToxizitätsübersichtCDDs cause their toxic effects by binding to the aryl hydrocarbon receptor and subsequently altering the trascription of certain genes. The affinity for the Ah receptor depends on the structure of the specific CDD. The change in gene expression may result from the direct interaction of the Ah receptor and its heterodimer-forming partner, the aryl hydrocarbon receptor nuclear translocator, with gene regulatory elements or the initiation of a phosphorylation/dephosphorylation cascade that subsequently activates other transcription factors. The affected genes include several oncogenes, growth factors, receptors, hormones, and drug-metabolizing enzymes. The change in transcription/translation of these genes is believed to be the cause of most of the toxic effects of CDDs. This includes 2,3,7,8-tetrachlorodibenzo-p-dioxin's carcinogenicity is thought to be the result of its ability to alter the capacity of both exogenous and endogenous substances to damage the DNA by inducing CYP1A1- and CYP1A2-dependent drug-metabolizing enzymes. (L177)
Landesrichtlinien für Trinkwasser(FL) FLORIDA 1,000 ug/l(ME) MAINE 4 ug/l(MN) MINNESOTA 3 ug/l
Bundesrichtlinien für TrinkwasserEPA 30 ug/L
Wassergefährdungsklasse (WGK)2
TSCA-Inventar-StatusTSCA listed
UN-TransportnummerUN 2765
Zollcode29189900
RTECS-Nr.AG1575000
R-Sätze (R)22-38-41-36-20/21/22-11-50/53
ToxizitätLD50 orally in rats: 700 mg/kg (Rowe, Hymas)
GefahrensymboleXn,F,N
Sicherheitshinweise (S)26-37-39-36-16-61-60-36/37
Gefahrenklasse9Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Eye Dam. 1Skin Irrit. 2
VerpackungsgruppeIII
Lagerklasse11 - Combustible Solids
Gefahrstoffdaten94-74-6(Hazardous Substances Data)

Anwendungen & Verwendung

Verwenden

Labelled MCPA (C369470). Herbicide.