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Home > Encyclopedia > (4-Chloro-2-methylphenoxy)acetic acid

(4-Chloro-2-methylphenoxy)acetic acid

(4-Chloro-2-methylphenoxy)acetic acid structure

(4-Chloro-2-methylphenoxy)acetic acid 

structure
  • CAS No:

    94-74-6

  • Formula:

    C9H9ClO3

  • Chemical Name:

    (4-Chloro-2-methylphenoxy)acetic acid

  • Synonyms:

    Acetic acid,2-(4-chloro-2-methylphenoxy)-;Acetic acid,[(4-chloro-o-tolyl)oxy]-;Acetic acid,(4-chloro-2-methylphenoxy)-;Acetic acid,(4-chloro-o-toloxy)-;2-(4-Chloro-2-methylphenoxy)acetic acid;Agroxone;(4-Chloro-2-methylphenoxy)acetic acid;Herbicide M;Leuna M;MCP;Methoxone;(2-Methyl-4-chlorophenoxy)acetic acid;Mephanac;Agroxon;Hedonal M;2M4Kh;MCPA;[(4-Chloro-o-tolyl)oxy]acetic acid;2,4-MCPA;Anicon kombi;Anicon M;B-Selektonon M;Dicopur M;Emcepan;Hedapur M 52;Hedarex M;Netazol;Okultin M;2M-4Ch;Metaxon;2M2Kh;Hormoneste;Rhonox;Mecaphar;Agritox 50;Agritox;NSC 2351;MCPA (acid);MCP (herbicide);CMPA;MCPA (herbicide);Chipton;SAN 75;11111-13-0;11111-14-1;50926-55-1;57425-61-3;127289-40-1

  • Categories:

    Agrochemicals  >  Herbicides

Description

White, crystalline solid. Free acid insoluble in water but sodium and amine salts are soluble. MCPA is a colorless crystalline solid


WHITE CRYSTALLINE POWDER WITH CHARACTERISTIC ODOUR.


(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, an environmental contaminant and a phenoxy herbicide. It is a chlorophenoxyacetic acid and a member of monochlorobenzenes.|A powerful herbicide used as a selective weed killer.

(4-Chloro-2-methylphenoxy)acetic acid Basic Attributes

200.62

200.62

202-360-6

D888C394VO

0054

2351

3077|2765

DTXSID4024195

White to light brown solid flakes, crystal powder or liquid.|Plates from benzene or toluene|White crystalline solid (pure compd)|Colorless crystalline solid (pure)

29189900

Characteristics

46.5

2.8

Solid

1.56 g/cm3 @ Temp: 25 °C

118-119 °C

286.74 °C

2 °C

1.552

water: insoluble (lit.)

APPROX 4°C

Vapour pressure, Pa at 20°C: (negligible)

Oral-Rat  LD50: 700 mg/kg; Oral-Mouse LD50: 439 mg/kg

Combustion produces toxic chloride gas

Henry's Law constant= 4.8X10-10 atm-cu m/mole @ 25 °C

pKa= 3.13

146.16 Ų [M-H]-

The acid, pka 3.07, forms water sol alkali metal and amine salts, though precipitation of calcium or magnesium salts may occur with hard water.|Solutions of the alkali metal salts are alkaline in reaction and will corrode aluminum and zinc.

Non-corrosive

Safety Information

III

9

UN 2765

2

22-38-41-36-20/21/22-11-50/53

26-37-39-36-16-61-60-36/37

AG1575000

Xn,F,N

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

Amine salt stable indefinitely. Ester stability depends upon formulations.

P210-P280-P305 + P351 + P338

H225-H302-H312-H319-H332

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.

Reacts with alkalis to form salts

EXTENSIVE ACUTE & CHRONIC TOXICITY DATA FOR MCPA IN MAMMALS, BIRDS, WILDLIFE, AQUATIC ORGANISMS, AMPHIBIANS, INSECTS & NEMATODES ARE PRESENTED.[BOVEY RW; TOXICOLOGY OF PHENOXY HERBICIDES IN ANIMALS AND MAN - GENERAL CONSIDERATIONS; IN: THE SCIENCE OF 2,4,5-T AND ASSOCIATED HERBICIDES. (JOHN WILEY & SONS: NY); CHO4: 71 (1980)]

Not 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.

|Danger|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P273, P280, P301+P312, P302+P352, P305+P351+P338, P310, P321, P330, P332+P313, P362, P391, and P501|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P322, P330, P363, P391, and P501|Aggregated GHS information provided by 216 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Aggregated GHS information provided by 349 companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P201, P202, P260, P264, P270, P271, P281, P284, P301+P312, P304+P340, P305+P351+P338, P308+P313, P309+P311, P310, P314, P320, P330, P332+P313, P337+P313, P403+P233, P405, and P501

In case of fire in the surroundings, use appropriate extinguishing media.

General handling procedure: wear rubber gloves for all handling; extinguishing method: self-contained breathing apparatus, rubber gloves, hats, suits, and boots must be worn.

Nonflammable

SRP: 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.

/SRP: Irritation of skin, eyes, nose, and throat may also occur./

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.

Provision to contain effluent from fire extinguishing. Separated from strong bases and food and feedstuffs. Store in an area without drain or sewer access. Cool.

Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly on spraying or when dispersed, especially if powdered.

The substance is irritating to the skin and respiratory tract. The substance is corrosive to the eyes. The substance may cause effects on the nervous system and heart when ingested in large amounts.

PREVENT DISPERSION OF DUST!

Use local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear safety goggles or eye protection in combination with breathing protection if powder.

2-Methyl-4-chlorophenoxyacetic acid was detected in one of 5 leachates collected from 5 sanitary landfills in Denmark during Feb 1983(1); the concn of the positive sample was 1-10 ppm(1).

In a study conducted between 1975 and 1977, MCPA was not detected in sediment samples collected from streams in 11 agricultural watersheds in Ontario, Canada(1). MCPA residues of 8-52 ppm have been reported for sediments collected from Canadian estuaries(2). In a study of water and sediment of Lake Miedwie in Poland, MCPA was detected in 45 of 60 sediment samples in 1984, at 0.3-24.0 ug/kg, and in 53 of 62 sediment samples in 1985, at 2.0-15.5 ug/kg (3).

URBAN/SUBURBAN: In a study of urban (indoor and outdoor) air samples collected from 14 cities in the US and Canada, MCPA was not detected (detection limit 0.001 mg/cu m) in any of 25 applicator breathing zone samples(1).|INDOOR: In a study of urban (indoor and outdoor) air samples collected from 14 cities in the US and Canada, MCPA was not detected (detection limit 0.001 mg/cu m) in any of the samples collected in the offices, operations rooms or warehouses of three facilities (1).|RURAL/REMOTE: In a study of vapor-phase and suspended particulate samples from a primarily agricultural area in rural North Dakota, MCPA (detection limit 0.3 pg/cu m) was detected in the air on 1 of 6 sampling dates in 1993, at 70 pg/cu m; and was detected on 4 of 7 sampling dates in 1994, at 2.1-12 pg/cu m(1). In a 1993-1996 study of ambient air (vapor plus particulate phases) and precipitation in an agricultural area in southern Manitoba, Canada, MCPA was detected (detection limit 2.1 pg/cu m) in the air at concns up to 13 ng/cu m and ranging from nondetectable to 13,000 pg/cu m; MCPA was mainly found in the vapor phase, with the exception of the maximum detection(2).

Toxicity

moderately toxic

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.

LD50 Rat male oral 700 mg/kg|LD50 Rat oral 800 mg/kg|LD50 Rat male sc 500 mg/kg|LD50 Rat ip 300 mg/kg|For more Non-Human Toxicity Values (Complete) data for 2-METHYL-4-CHLOROPHENOXYACETIC ACID (10 total), please visit the HSDB record page.

MCPA is not known to occur as a natural product(1).

MCPA's use as a herbicide to control broadleaf weeds in agricultural applications(1,2) is expected to result in its direct release to the environment(SRC). Various monitoring studies have shown that field applications of MCPA are subject to runoff (via rainfall) with subsequent transport (relatively small amounts) to streams and ponds(3,4).

TERRESTRIAL 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 soil; the 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).

The rate constant for the vapor-phase reaction of MCPA with photochemically-produced hydroxyl radicals has been estimated as 1.3X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 30 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). MCPA is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2). Photolysis, however, is expected to be an important degradation process. When exposed to summer sunlight or photoreactors simulating sunlight, aqueous solutions of MCPA (buffered to pHs 8-10) photolyzed to 50% of initial MCPA concn in approximately 19-20 days(3). The major photolysis product has been observed as 4-chloro-2-methylphenol, with o-cresol and 4-chloro-2-formylphenol also identified as photolysis products(3,4). The exposure of MCPA in sterilized rice paddy water to sunlight resulted in a 50% MCPA decrease in about 8-9 days, suggesting a possible photosensitized transformation(3). Exposure of aqueous solutions of MCPA in distilled water to Oct sunlight (Davis, CA) resulted in a 14% decomposition of MCPA after 245 hr of exposure(5). The photolysis of MCPA can be sensitized by the formation of sunlight-produced hydroxyl radicals(5) and by photo-oxidants generated by humates(6). Sensitization may increase the photodegradation rate by up to an order of magnitude or more(5,6); the photosensitized rate will vary among natural waters and will depend upon the availability of photocatalytic agents. 4-Chloro-2-methylphenol was identified as the major photolysis product when aqueous MCPA solutions were exposed to simulated sunlight(7); riboflavine and anthraquinone were found to photosensitize MCPA photodegradation(7).

A BCF of 1 was determined for trout at MCPA aqueous concns of 10-100 mg/l and using an exposure period of 10-28 day(1). In a model aquatic ecosystem study, BCFs of <1 were measured in fish and snails for the sodium salt of 2-methyl-4-chlorophenoxyacetic acid(2,3). According to a classification scheme(3), these BCF values suggest the potential for bioconcentration in aquatic organisms is low. MCPA is absorbed through leaves or roots and is readily translocated in plants(4).

53.70 L/kg|MCPA adsorption coefficients (Kd) of 0.7 to 1.0 were measured in three soils (loamy sand and sandy loam types)(1); based upon humus contents of 2.4-3.0%(1),the Koc values of the three soils are approximately 60, 52 and 50, respectively. A similar Kd value of 0.4 was observed in a garden soil(2). Using soil thin-layer chromatography, Rf values of 0.6-1.0 were measured for Chillum silt loam (3.1% organic matter), Lakeland sand loam (0.9% organic matter) and Hagerstown silty clay loam (1.4% organic matter)(3,4); these Rf values classify MCPA as mobile in soil(3,4). When MCPA was applied to a rice field, an observed 70% decrease in MCPA was attributed to losses through soil percolation(5). In a laboratory study of leaching columns with either turf grass soil or two subsoils, most of the applied MCPA (95.4-99.0%) eluted with the first 100-ml fraction of leaching water applied to the columns, indicating that MCPA did not bind to the soils(6). According to a classification scheme(7), these Koc values suggest that MCPA is expected to have high mobility in soil.

The Henry's Law constant for MCPA is 4.80X10-10 atm-cu m/mole(1). This Henry's Law constant indicates that MCPA is expected to be essentially nonvolatile from moist soil and water surfaces(2). MCPA is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 5.90X10-6 mm Hg(3). In a volatilization experiment, however, 90% of MCPA applied to polyethylene surfaces volatilized after 3 days of open exposure to air(4). It should be kept in mind, however, that a polyethylene surface is much different than water or soil in the environment. On soil surfaces, MCPA will likely leach or be taken up by plants fairly rapidly(5,6).

GROUNDWATER: MCPA was detected in 2 of 237 wells in Ontario, Canada, monitored between 1969 and 1978 at concns of 1.1-10 ppb in one well and 1001-10000 ppb in the other(1); the high concns were the result of spillage(1). During monitoring of 359 Ontario wells between 1979 and 1984, MCPA was detected only twice(2); the detections were the result of spillage(2). In a monitoring study of the Anglican Water region in the United Kingdom (an agricultural area), MCPA was detected in (detection limit of 0.1 ug/l) 0.5% of all samples at concns of 0.12 ug/l(3). MCPA was detected in 0.1% of 725 wells sampled in Minnesota at a levels of 0.33 ug/l(4). MCPA was detected in 2 of 14 wells of a shallow aquifer in 1993, during May and July, and in 1 of 14 wells in June of 1994 in central South Dakota; MCPA was not detected in the 14 wells in 4 of the 6 study years(5).|SURFACE WATER: In a study conducted between 1975 and 1977, MCPA was detected (detection limit of 0.1 ug/l) in 6 of 949 stream water samples collected from 11 agricultural watersheds in Ontario, Canada(1); positive samples coincided with spraying operations(1). Levels of <0.1 to 1.7 ug/l were detected into 2 of 98 water samples collected from 8 agricultural watersheds in Ontario in 1974(2). Water samples were collected at the mouths of the Grand, Saugeen and Thames Rivers in Ontario between Jan 1981 and Dec 1985(3); MCPA was detected in 1 of 100 Grand River samples (0.1 ug/l), 4 of 200 Thames River samples (1.8 ug/l mean concn), and no Saugeen samples(3). In a monitoring study of the Anglican Water region in the United Kingdom (an agricultural area), MCPA was detected in 1% of all samples at concns of <0.1 to 16.9 ug/l (detection limit not specified)(4). In a study of water and sediment of Lake Miedwie in Poland, MCPA was detected in 86 of 88 surface water samples in both 1984 and 1985, ranging from 0.05-1.32 ug/kg and 0.03-0.61 ug/kg, respectively(5).|RAIN/SNOW/FOG: In rain and roof water collected at Gruze, Switzerland, MCPA was detected in 4 of 41 samples, generally in early April through early May, at concns up to 27 ng/l; the total annual load (excluding Nov to Jan) was 800 ng/sq m-yr (1). In a 1993-1996 study of ambient air (vapor plus particulate phases) and precipitation in an agricultural area in southern Manitoba, Canada, MCPA was detected (detection limit 10 pg/l) in precipitation at maximum concns during late May and early June, corresponding with annual local use patterns; similar temporal concn profiles were observed in each of the 4 years(2).

No 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).

... 2-METHYL-4-CHLOROPHENOL WAS DETECTED IN MILK OF DAIRY COWS ... .

The production and formulation of 2-methyl-4-chlorophenoxyacetic acid (and its derivatives) and their use in agricultural applications are potential sources of exposure to both workers and the general population(1). Occupational exposure to 2-methyl-4-chlorophenoxyacetic acid occurs through dermal contact and inhalation of dust and sprays, especially to workers applying the compound as a herbicide(2). In one monitoring study of farmers and spraymen, dermal absorption seemed to be the dominant route of entrance(3); swallowing of spray droplets and inhalation were also possible routes of entrance(3).|Air exposure to 2-methyl-4-chlorophenoxyacetic acid was determined by monitoring 24 farmers and 9 professional spraymen who were spray applying the herbicide(1); air samples were collected in the individual breathing zones during preparation and spraying(1); median concns ranged from 0.004 to 0.015 mg/cu m TWA(1); the highest concn was 0.092 mg/cu m TWA(1).|Occupational exposure to MCPA may occur through inhalation and dermal contact with this compound at workplaces where MCPA is produced or used(SRC). Air exposure to MCPA was determined by monitoring 24 farmers and 9 professional spraymen who were spray applying the herbicide(1); air samples were collected in the individual breathing zones during preparation and spraying(1); median concns ranged from 0.004 to 0.015 mg/cu m TWA(1); the highest concn was 0.092 mg/cu m TWA(1).

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.

Drug Information

Pesticides used to destroy unwanted vegetation, especially various types of weeds, grasses (POACEAE), and woody plants. Some plants develop HERBICIDE RESISTANCE. (See all compounds classified as Herbicides.)

... 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.

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.

The technical grade might contain 3-40% 6-chloro-2-methylphenoxyacetic acid. The hormone-type herbicide, commercial grade contains 4% of 4-chloro-o-cresol.

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.

Treatment is symptomatic and supportive. Oils should not be used as either cathartics or dermal cleansing agents, as they increase absorption. Gastric lavage and use of activated charcoal and sodium sulfate are indicated for ingestion. If dermal exposure occurred, contaminated clothes should be removed, and the skin should be thoroughly cleansed with soap and water. Management of seizures in both children and adults is with Valium or phenobarbital. Respiratory depression and even respiratory arrest especially with concomitant use of Valium and phenobarbital in children, may occur. These drugs preferably should be used only in critical care areas where emergency endotracheal intubation can be performed. ... Epinephrine can not be utilized in patients with organochlorine poisoning, as the organochlorines induce myocardial irritability and ventricular arrhythmias may occur. However, dopamine may be necessary in the event of hypotension unresponsive to fluid administration, and epinephrin may be necessary in the event of cardiopulmonary arrest. ... In a critically ill patient with unknown insecticide exposure, ... Atropine must be used with caution, as it can cause ventricular irritability, especially when a myocardial irritant such as an organochlorine is present. ... Hematologic, hepatic (especially with endrin, which is markedly hepatotoxic), and renal studies as well as cardiopulmonary monitoring should be carried out in acute intoxication from lindane or other organochlorines for at least 48 to 72 hr. Long term hematologic follow-up is necessary for the patient with lindane intoxication. As the carrier for these agents may be xylene or a petroleum distillate, management also must include observation and treatment for these entities. /Organochlorine pesticides/|Bath and shampoo with soap and water to remove chemicals from skin and hair. Obtain medical treatment if irritation persists. Individuals with chronic skin disease or known sensitivity to these herbicides should either avoid using them or take strict precautions to avoid contact (respirator, gloves, etc). FLUSH contaminating chemicals from eyes and copious amounts of clean water for 10-15 minutes. If irritation persists, obtain medical treatment. /Chlorophenoxy compounds/|If any symptoms of illness occur during or following inhalation of spray, remove victim from contact with the material for at least 2-3 days. Allow subsequent contact with chlorophenoxy compounds only if effective respiratory protection is practiced. /Chlorophenoxy compounds/|If substantial amounts of chlorophenoxy compounds have been ingested, spontaneous emesis may occur. If vigorous emesis has not occurred, measures should be taken to empty the stomach and limit GI absorption by gastric intubation, aspiration, and lavage, following placement of a cuffed endotracheal tube. Repeated administration of charcoal at half or more the original dosage every 2-4 hr may be beneficial. If gastric aspiration and lavage is not performed due to delay in treatment, and if the patient is fully alert, administer charcoal and laxative orally. Administer iv fluids to accelerate excretion of the chlorophenoxy compound, and to limit concentration of the toxicant in the kidney. A urine flow of 4-6 ml/min is desirable. Iv saline/dextrose has sufficed to rescue comatose patients who drank 2,4-D and mecoprop several hr before hospital admission. Caution: Monitor urine protein and cells, BUN, serum creatinine, serum electrolytes, and fluid intake/output carefully to insure that renal function remains unimpaired and that fluid overload dose not occur. Forced alkaline diuresis has been used successfully in management of suicidal ingestions of chlorophenoxy compounds. Alkalinizing the urine by including sodium bicarbonate (44-88 mEq per liter) in the iv solution apparently accelerates excretion of 2,4-D dramatically and mecoprop excretion substantially. Urine pH should be maintained in the 7.5-8.8 range. Include potassium chloride as needed to offset increased potassium losses: add 20-40 mEq of potassium chloride to each liter of iv solution. Monitor serum electrolytes carefully. There may possible be some hazard to the kidneys when urine concentrations of toxicant are very high, so integrity of renal function and fluid balance should be monitored carefully as the chlorophenoxy compound is excreted. Hemodialysis is not likely to be of significant benefit in poisonings by chlorophenoxy compounds because of the extensive protein binding of these chemicals. Follow up clinical examination should include electromyographic and nerve conduction studies to detect any neuropathic changes and neuromuscular junction defects. /Chlorophenoxy compounds/

SYMPTOMATOLOGY: 1. FATIGUE, WEAKNESS, ANOREXIA; PERHAPS NAUSEA, VOMITING & DIARRHEA. 2. LETHARGY PROGRESSING TO COMA, WITH CONSTRICTED PUPILS (MIOSIS). 3. FLACCID PARALYSIS ... DESCRIBED IN ONE COMATOSE PATIENT & GRAND MAL CONVULSIONS WITH OPISTHOTONUS IN ANOTHER. /2,4-D/|SYMPTOMATOLOGY: 7. PROGRESSIVE HYPOTENSION WITH DEATH IN PERIPHERAL VASCULAR COLLAPSE, PERHAPS ASSOC WITH ACIDOSIS DUE TO LACTIC ACIDEMIA & OTHER PRODUCTS OF HYPERMETABOLISM. 8. IN NONFATAL POISONING SEVERE & PROTRACTED.../PRC: NEUROPATHY/ WITH PAIN & PARESTHESIAS ... MUSCLE FASCICULATIONS. 8. CHRONIC EXPOSURE MAY LEAD TO CNS DEFECTS IN CONTROL OF MOTOR FUNCTION. /2,4-D/|SYMPTOMATOLOGY: 5. PROGRESSIVE DECLINE IN BLOOD PRESSURE WITH DEATH IN DEEP COMA. ... 6. DISTURBANCES IN BODY TEMP REGULATION MAY BE ENCOUNTERED. ... SEVERE REDUCTION OF BODY TEMP IN COOL OR COLD ENVIRONMENTS. MORE PROBABLY FEBRILE RESPONSES IN WARM ENVIRONMENTS OR DURING EXERCISE. /2,4-D/|... A 61 YR OLD MAN DRANK MCPA ... SHORTLY AFTERWARD, HE VOMITED, HIS SPEECH BECAME SLURRED, HIS FACE BEGAN TO TWITCH, & HIS LIMBS BEGAN TO JERK. ON ARRIVAL AT HOSPITAL, HE WAS DEEPLY UNCONSCIOUS, ALTHOUGH IT WAS ONLY 1.5 HOURS SINCE HE HAD BEEN ASYMPTOMATIC. ... PUPILS WERE CONSTRICTED & ... /DID NOT RESPOND TO LIGHT/. REFLEXES WERE DIMINISHED. THERE WAS GENERALIZED FIBRILLARY TWITCHING OF SKELETAL MUSCLE & CLONIC SPASMS OF LIMBS. ... IN ADDITION TO CNS ABNORMALITIES, & IRRITATION OF UPPER GI TRACT, EVIDENCE OF KIDNEY & LIVER INJURY WERE OBSERVED,AS WELL AS ANEMIA & PNEUMONIA. PROTEINURIA WAS PRESENT DURING 1ST TWO WEEKS. AFTER 1 WK, GLYCOSURIA ... APPEARED & GRADUALLY SUBSIDED ... .|For more Human Toxicity Excerpts (Complete) data for 2-METHYL-4-CHLOROPHENOXYACETIC ACID (10 total), please visit the HSDB record page.

2 Methyl 4 chlorophenoxyacetic Acid

The substance can be absorbed into the body by inhalation of its aerosol, through the skin and by ingestion.

Cough. Sore throat. Headache. Nausea.


Redness. Pain.


Redness. Pain. Burns. Blurred vision.

(4-Chloro-2-methylphenoxy)acetic acid Use and Manufacturing

Methods of Manufacturing

CHLORINATION OF O-CRESOL FOLLOWED BY REACTION WITH THE SODIUM SALT OF MONOCHLOROACETIC ACID|Ethylmercaptan + 2-methyl-4-chlorophenoxyacetic acid (thioesterification)

Uses

Labelled MCPA (C369470). Herbicide.

Production

(1975) 1.77X10+9 GRAMS (CONSUMPTION)

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).

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.

Acetic acid, 2-(4-chloro-2-methylphenoxy)-: ACTIVE|TP - indicates a substance that is the subject of a proposed TSCA section 4 test rule.|Avoid spray drifts onto susceptible plants such as grapes, tomatoes, & cotton.|SELECTIVE FOLIAGE BROADLEAF KILLER, SIMILAR TO 2,4-D. MORE SELECTIVE THAN 2,4-D @ EQUAL RATES ON CEREALS, LEGUMES & FLAX. APPLICATION METHODS: AERIAL & GROUND APPLICATION; LOW-VOLUME SPRAY. RATES: USED @ RATES FROM 0.12 TO 1 LB AI/ACRE. USUAL CARRIER: WATER 2 TO 30 GAL/ACRE.|... Herbicide absorbed by the leaves and roots, with translocation. Concentrates in the meristematic regions, where it inhibits growth.|/MCPA/ is a systemic hormone-type selective herbicide.|For more General Manufacturing Information (Complete) data for 2-METHYL-4-CHLOROPHENOXYACETIC ACID (6 total), please visit the HSDB record page.

ACTIVE INGREDIENTS ARE PRECIPITATED BY HYDROGEN CHLORIDE & EXTRACTED WITH CHLOROFORM. SOLVENT IS EVAPORATED, RESIDUE DISSOLVED IN ACETONE, & ABSORBANCE MEASURED @ CHARACTERISTIC IR WAVELENGTHS.|APPLICABLE TO DETERMINATION OF 2-METHYL-4-CHLOROPHENOXYACETIC ACID IN MUNICIPAL & INDUSTRIAL DISCHARGES BY GC USING ECD OR HALIDE DETECTOR.|HPLC PROCEDURE ALLOWING DIRECT SIMULTANEOUS SEPARATION & DETECTION OF HERBICIDES USED IN RICE CULTIVATION. DETECTION LIMITS OF 0.01-0.03 PPM.|DETERMINATION OF THE PESTICIDES MCPA BY LOW TEMPERATURE PHOSPHORIMETRY, MINIMUM DETECTABLE AMT WAS 0.2 PPM, WITH RANGE OF O.5-50 PPM.|For more Analytic Laboratory Methods (Complete) data for 2-METHYL-4-CHLOROPHENOXYACETIC ACID (8 total), please visit the HSDB record page.

AFTER EXPOSURE, URINE SAMPLES WERE ANALYZED BY HPLC. 0.02 UG/ML WAS BELOW DETECTABLE LEVEL.

Agrochemicals -> Herbicides|Herbicides, Transformation products|Environmental transformation -> Pesticides (parent, predecessor)

MCPA has known environmental transformation products that include 2-methyl-4-chlorophenol and cloxyfonac.

Computed Properties

Molecular Weight:200.62
XLogP3:2.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:200.0240218
Monoisotopic Mass:200.0240218
Topological Polar Surface Area:46.5
Heavy Atom Count:13
Complexity:184
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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