94-74-6 Usage
Description
2-Methyl-4-chlorophenoxyacetic acid, also known as MCPA, is a chlorophenoxyacetic acid derivative that features a methyl group at the 2nd position and a 4-chlorophenoxy substituent. It exists as a colorless crystalline solid and is classified as a systemic post-emergence herbicide. Due to its chemical properties, the free acid form is insoluble in water, while its sodium and amine salts are soluble. MCPA is recognized for its effectiveness in controlling a broad spectrum of broadleaf weeds and is considered a U.S. EPA restricted Use Pesticide (RUP).
Uses
Used in Agricultural Industry:
2-Methyl-4-chlorophenoxyacetic acid is used as a herbicide for controlling broadleaf annual and perennial weeds, such as thistle and dock, in various crops including cereals, flax, rice, vines, peas, and potatoes. It is also utilized in grasslands, forestry applications, and on rights-of-way.
Used in Environmental Management:
MCPA is used as an environmental toxin management tool, being listed on the US EPA Toxic Release Inventory (TRI) list. This indicates its role in controlling the growth of unwanted vegetation that may interfere with environmental, industrial, or residential settings.
Used in Chemical Formulations:
2-Methyl-4-chlorophenoxyacetic acid is used as an active ingredient in various chemical formulations due to its compatibility with many other compounds. It can be found in combination with products such as bentazone, bromoxynil, 2,4-D, dicamba, fenoxaprop, MCPB, mecoprop, thifensulfuron, and tribenuron to enhance their herbicidal effects.
General Description:
2-Methyl-4-chlorophenoxyacetic acid is described as a colorless crystalline solid that is corrosive and practically insoluble in water in its free acid form. It is labeled as MCPA (C369470) and is widely recognized for its use as a herbicide.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
2-Methyl-4-chlorophenoxyacetic acid is a chlorinated benzoic acid derivative. Reacts as a weak acid to neutralize bases, both organic (for example, the amines) and inorganic. May corrode iron, steel, and aluminum parts and containers if moist. Reacts with cyanide salts in the presence of moisture to generate gaseous hydrogen cyanide. May react if moist with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A variety of products is possible. Like other acids, may initiate polymerization reactions or catalyze other reactions. is a chlorinated carboxylic acid herbicide. Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in water. Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions. The pH of solutions of carboxylic acids is therefore less than 7.0. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in 2-Methyl-4-chlorophenoxyacetic acid to corrode or dissolve iron, steel, and aluminum parts and containers. Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. The reaction is slower for dry, solid carboxylic acids. Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions.
Trade name
ACME MCPA AMINE 4?; AGRITOX?;
AGROXONE?; AGROZONE?; AGSCO?; ANICON
KOMBI?; ANICON M?; BANLENE?; BLESEL MC?;
BORDERMASTER?; BROMINAL M & PLUS?;
CAMBILENE?; CHEYENNE?; CHIMAC OXY?;
CHIPTOX?; CHWASTOX?; CORNOX M?; DAKOTA?;
DED WEED?; DICOPUR-M?; DICOTEX?; DOW
MCP AMINE WEED KILLER?; DYVEL?; EH1356
HERBICIDE?; EMCEPAN?; EMPAL?; ENVOY?;
HEDAPUR M 52?; HEDAREX M?; HEDONAL M?;
HERBICIDE M?; HORMOTUHO?; HORNOTUHO?;
KILSEM?; 4 K-2 M?; KVK?; LEGUMEX DB?;
LEUNA M?; LEYSPRAY?; LINORMONE?;
M 40?; 2 M-4C?; 2 M-4KH?; MALERBANE?;
MAYCLENE?; MEPHANAC?; MIDOX?; MXL?;
OKULTIN?; PHENOXYLENE 50?; PHENOXYLENE
PLUS?; PHENOXYLENE SUPER?; RAZOL DOCK
KILLER?; RHOMENE?; RHONOX?; SHAMOX?;
B-SELEKTONON M?; SEPPIC MMD?; TILLER?;
TRIMEC?; U 46?; VACATE?; VESAKONTUHO?;
WEEDAR?; WEEDAR MCPA CONCENTRATE?;
WEEDONE MCPA ESTER?; WEED RHAP?; ZELAN?
Safety Profile
Suspected carcinogen.
Poison by subcutaneous and intravenous
routes. Moderately toxic by ingestion.
Human systemic effects by ingestion: blood
pressure decrease and coma. Experimental
teratogenic and reproductive effects.
Mutation data reported. An herbicide. When
heated to decomposition it emits toxic
fumes of Cl-.
Potential Exposure
A potential danger to those involved
in the manufacture, formulation, and application of this
postemergence herbicide, used for control of broadleaf
weeds in agricultural applications.
Environmental Fate
Biological. Cell-free extracts isolated from Pseudomonas sp. in a basal salt medium
degraded MCPA to 4-chloro-o-cresol and glyoxylic acid (Gamar and Gaunt, 1971).Soil. Residual activity in soil is limited to approximately 3–4 months (Hartley and
Kidd, 1987).Plant. The penetration, translocation and metabolism of radiolabeled MCPA in a
cornland weed (Galium aparine) was studied by Leafe (1962). Carbon dioxide was identified
as a metabolite but this could only account 7% of the applied MCPA. Though noPhotolytic. When MCPA in dilute aqueous solution was exposed to summer sunlight
or an indoor photoreactor (l >290 nm), 2-methyl-4-chlorophenol formed as the major
product as well as o-cresol and 4-chloro-2-formylphenol (Soderquist and Crosby, 1975).
Clapés et al. (1986) studied the photodecomposition of aqueous solution of MCPA (120
ppm, pH 5.4, 25°C) in a photoreactor equipped with a high pressure mercury lamp. After three minutes of irradiation, 4-chloro-2-methylphenol formed as an intermediate which
degraded to 2-methylphenol. Both compounds were not detected after 6 minutes of irradiation;
however, 1,4-dihydroxy-2-methylbenzene and 2-methyl-2,5-cyclohexadiene-1,4-
dione formed as major and minor photodecomposition products, respectively. The same
experiment was conducted using simulated sunlight (l <300 nm) in the presence of
riboflavin, a known photosensitizer. 4-Chloro-2-methylphenol and 4-chloro-2-methylbenzyl
formate formed as major and minor photoproducts, respectively (Clapés et al., 1986).
Ozone degraded MCPA in dilute aqueous solution with and without UV light (l >300
nm) (Benoit-Guyod et al., 1986).Chemical/Physical. Reacts with alkalies forming water soluble salts (Hartley and Kidd,
1987). Ozonolysis of MCPA in the dark yielded the following benzenoid intermediates:
4-chloro-2-methylphenol, its formate ester, 5-chlorosalicyaldehyde, 5-chlo
Shipping
UN3345 Phenoxyacetic acid derivative pesticide,
solid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials. UN3077 Environmentally hazardous substances, solid,
n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous
material, Technical Name Required
Purification Methods
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.
Incompatibilities
A weak acid. Compounds of the carboxyl group react with all bases, both inorganic and
organic (i.e., amines) releasing substantial heat, water and a
salt that may be harmful. Incompatible with arsenic compounds (releases hydrogen cyanide gas), diazo compounds,
dithiocarbamates, isocyanates, mercaptans, nitrides, and
sulfides (releasing heat, toxic, and possibly flammable
gases), thiosulfates and dithionites (releasing hydrogen
sulfate and oxides of sulfur). Incompatible with alkalis.
Waste Disposal
Incineration with added flammable solvent; incinerator equipped with fume scrubber.
In accordance with 40CFR165, follow recommendations
for the disposal of pesticides and pesticide containers.
Must be disposed properly by following package label
directions or by contacting your local or federal environmental control agency, or by contacting your regional
EPA office
Check Digit Verification of cas no
The CAS Registry Mumber 94-74-6 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 4 respectively; the second part has 2 digits, 7 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 94-74:
(4*9)+(3*4)+(2*7)+(1*4)=66
66 % 10 = 6
So 94-74-6 is a valid CAS Registry Number.
InChI:InChI=1/C9H9ClO3/c1-6-4-7(10)2-3-8(6)13-5-9(11)12/h2-4H,5H2,1H3,(H,11,12)
94-74-6Relevant articles and documents
Method for preparing 2-methyl-4-chlorophenoxyacetic acid through catalytic chlorination of 2-methylphenoxyacetic acid
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Paragraph 0041; 0044; 0046-0061, (2021/03/13)
The invention relates to a preparation method of 2-methyl-4-chlorophenoxyacetic acid, in particular to a method for preparing 2-methyl-4-chlorophenoxyacetic acid through catalytic chlorination of 2-methylphenoxyacetic acid. The method comprises the following steps: by taking o-methylphenoxyacetic acid (MPA) as a raw material, performing a reaction in the presence of chlorine by virtue of a catalyst, and filtering, so as to obtain the 2-methyl-4-chlorophenoxyacetic acid (MCPA), wherein the catalyst is imidazole ionic liquid. By means of the catalyst, the reaction activity is relatively high, the o-methyl phenoxyacetic acid is subjected to catalytic chlorination reaction, and the 2-methyl-4-chlorophenoxyacetic acid is prepared at a high yield; besides, compared with existing literature reports, the reaction system is simple and convenient to operate, no wastewater is generated in the chlorination step, a high-quality product can be obtained, and large-scale production is facilitated.
Modulation of DNA damage response by targeting ATM kinase using newly synthesized di-phenoxy acetamide (DPA) analogs to induce anti-neoplasia
Al-Ostoot, Fares Hezam,Sherapura, Ankith,Malojirao, Vikas H.,Thirusangu, Prabhu,Al-Muhimeed, Tahani I.,Khanum, Shaukath Ara,Prabhakar
, p. 1344 - 1360 (2021/06/14)
Background: Imbalance and instability in the structure of the DNA have become major characteristics of cancer. In response to DNA damage, DNA damage response (DDR) protein, ataxia telangiectasia mutated (ATM), plays a pivotal role in the modulation of regulatory regions responsible for inhibition of apoptosis, thereby neoplastic progression. Methods: A new series of DPA (7a–t) were synthesized, characterized. Anti-proliferative studies to identify the lead compound were carried out by LDH and MTT assay. Apoptosis/DNA damage was measured through FACS, Annexin-v staining, TUNEL and Comet assay. Elucidation of molecular mechanism through immunoblot and further validation of the drug effect through in vivo approaches. Results: Initial in vitro anti-proliferative screening of Compounds DPA (7a–t) against multiple cancer cell lines identified Compound DPA (7n) as a potent cytotoxic molecule with IC50 value of 4.3?μM. Down the line, in vitro and in vivo evaluation of Compound DPA (7n) inferred that it has apoptotic inducing potentiality. Further, evaluation of molecular mechanism inferred that Compound DPA (7n) effectively modulates ATM phosphorylation only, eventually altering downstream signalling pathways. Conclusions: Compound DPA (7n) emerged as a potent proapoptotic and anti-neoplastic agent by inhibiting ATM kinase activity both in vitro and in vivo. The conferring results ascertain that the drug could be developed as a new ATM kinase inhibitor with anti-cancer capacity. Graphic abstract: [Figure not available: see fulltext.]
INHIBITORS OF INTEGRATED STRESS RESPONSE PATHWAY
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Paragraph 0350, (2020/12/30)
The present disclosure relates generally to therapeutic agents that may be useful as inhibitors of Integrated Stress Response (ISR) pathway.
