94-74-6

Usage

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

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)

Upstream product

• 7399-57-7 2-Methyl-4-chlor-phenoxyessigsaeureamid 
• 1878-49-5 o-methylphenoxyacetic acid 
• 2698-38-6 ethyl 2-(4-chloro-2-methylphenoxy)acetate 
• 6161-86-0 2-methylphenoxyethanol 
• 2436-73-9 methyl 2-(4-chloro-2-methylphenoxy)acetate 
• 57548-58-0 Sodium; o-tolyloxy-acetate 
• 36220-29-8 2-(4-chloro-2-methylphenoxy)ethanol 
• 1713-11-7 4-chloro-2-methylphenoxyacetic acid isobutyl ester 
• 1713-12-8 n-butyl 4-chloro-2-methylphenoxyacetate 
• 95-48-7 ortho-cresol 
• 79-11-8 chloroacetic acid 
• 1570-64-5 2-methyl-4-chlorophenol 
• 105-36-2 ethyl bromoacetate 
• 105-39-5 chloroacetic acid ethyl ester 

Downstream Products

• 2698-38-6 ethyl 2-(4-chloro-2-methylphenoxy)acetate 
• 6597-79-1 2-methyl-4-chlorophenoxyacetyl chloride 
• 13333-87-4 (2,4-dichloro-6-methyl-phenoxy)-acetic acid 
• 83903-78-0 (4-chloro-2-methyl-phenoxy)-acetic acid-(2-hydroxy-propyl ester) 
• 93799-61-2 (4-Chloro-2-methyl-phenoxy)-acetic acid 2,5-dioxo-pyrrolidin-1-yl ester 
• 2758-48-7 <4-Chlor-2-methyl-5-nitro-phenoxy>-essigsaeure 
• 6777-75-9 (4-chloro-6-methyl-2,3-dinitro-phenoxy)-acetic acid 
• 1570-64-5 2-methyl-4-chlorophenol 
• 30114-33-1 4-chloro-2-methylphenyl formate 
• 162922-16-9 4-hydroxy-2-methylphenoxyacetic acid 
• 67562-39-4 1,2,3,4,6,7,8-heptachlorodibenzofuran 
• 57117-42-7 1,2,3,7,8-pentachlorodibenzofuran 
• 57117-31-4 2,3,4,7,8-pentachlorodibenzofuran 
• 102131-41-9 2,2,5,5-Tetramethyl-2,5-dihydro-1H-pyrrole-3-carboxylic acid {2-[2-(4-chloro-2-methyl-phenoxy)-acetylamino]-ethyl}-amide 

Relevant academic research and scientific papers

Modulation of DNA damage response by targeting ATM kinase using newly synthesized di-phenoxy acetamide (DPA) analogs to induce anti-neoplasia

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.]

Targeting HIF-1α by newly synthesized Indolephenoxyacetamide (IPA) analogs to induce anti-angiogenesis-mediated solid tumor suppression

Background: Hypoxic microenvironment is a common feature of solid tumors, which leads to the promotion of cancer. The transcription factor, HIF-1α, expressed under hypoxic conditions stimulates tumor angiogenesis, favoring HIF-1α as a promising anticancer agent. On the other hand, synthetic Indolephenoxyacetamide derivatives are known for their pharmacological potentiality. With this background here, we have synthesized, characterized, and validated the new IPA (8a–n) analogs for anti-tumor activity. Methods: The new series of IPA (8a–n) were synthesized through a multi-step reaction sequence and characterized based on the different spectroscopic analysis FT-IR, 1H, 13C NMR, mass spectra, and elemental analyses. Cell-based screening of IPA (8a–n) was assessed by MTT assay. Anti-angiogenic efficacy of IPA (8k) validated through CAM, Rat corneal, tube formation and migration assay. The underlying molecular mechanism is validated through zymogram and IB studies. The in vivo anti-tumor activity was measured in the DLA solid tumor model. Results: Screening for anti-proliferative studies inferred, IPA (8k) is a lead molecule with an IC50 value of ?5?μM. Anti-angiogenic assays revealed the angiopreventive activity through inhibition of HIF-1α and modulation downstream regulatory genes, VEGF, MMPs, and P53. The results are confirmative in an in vivo solid tumor model. Conclusion: The IPA (8k) is a potent anti-proliferative molecule with anti-angiogenic activity and specifically targets HIF1α, thereby modulates its downstream regulatory genes both in vitro and in vivo. The study provides scope for new target-specific drug development against HIF-1α for the treatment of solid tumors. Graphic abstract: [Figure not available: see fulltext.].

Method for preparing 2-methyl-4-chlorophenoxyacetic acid through catalytic chlorination of 2-methylphenoxyacetic acid

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.

Continuous preparation method and preparation system of 2-methyl-4-chlorophenoxyacetic acid

The present invention belongs to the technical field of 2-methyl-4-chlorophenoxyacetic acid, specifically relates to a continuous preparation method and preparation system of 2-methyl-4-chlorophenoxyacetic acid. The continuous preparation method of 2-methyl-4-chlorophenoxyacetic acid comprising: the o-cresol and the alkali solution into a salt reaction, to obtain a phenol salt solution; after the chloroacetic acid is added to the phenol salt solution for condensation reaction, the reaction solution is evaporated to obtain o-toluoxyacetate; organic solvent and acid are added to the o-toluoxyacetate, after acidification reaction, the reaction mixture is separated from the intermediate solution; chlorine is introduced into the intermediate solution, and after the chlorination reaction, the product solution is separated After crystal separation and drying of the product solution, 2-methyl-4-chlorophenoxyacetic acid was prepared. By configuring an automated control system through continuous production, human resources can be greatly reduced.

INHIBITORS OF INTEGRATED STRESS RESPONSE PATHWAY

The present disclosure relates generally to therapeutic agents that may be useful as inhibitors of Integrated Stress Response (ISR) pathway.

Preparation method of 2-methyl-4-chloro-phenoxyacetic acid

The invention belongs to the technical field of pesticide synthesis, and particularly relates to a 2-methyl-4-chloro-phenoxyacetic acid preparation method, which uses o-methylphenol sodium as a reactant, and uses an organic phase methyl chloroacetate solution as a reaction solvent in a condensation reaction. The method has the advantages that the method is simple; in the condensation reaction, anorganic phase methyl chloroacetate solution is used as a reaction solvent to replace a water phase in the traditional technology; and the organic phase can be continued to the subsequent chlorinationreaction, so that the problems of decomposition of sodium chloroacetate and low reaction yield can be solved, no wastewater can be generated in the production of MCPA sodium salt, the yield can be greatly improved, and the method is a green and environment-friendly synthesis method.

2-methyl-4-chlorophenoxyacetic acid preparation method

The invention provides a 2-methyl-4-chlorophenoxyacetic acid preparation method, which comprises: carrying out a condensation reaction on sodium o-cresolate and sodium chloroacetate under the catalysis of a trimethylamine catalyst to obtain 2-methyl sodium phenoxyacetate, acidifying, and chlorinating to obtain 2-methyl-4-chlorophenoxyacetic acid. According to the present invention, under the catalysis of the trimethylamine catalyst, sodium o-cresolate and sodium chloroacetate can be subjected to the condensation reaction in the near-neutral environment with the temperature of lower than 70 DEGC, such that the main side reaction for hydrolyzing sodium chloroacetate into sodium glycolate is greatly reduced, the produced wastewater contains less o-methylphenol and glycolic acid (or sodium glycolate) so as to easily meet the nationally acceptable emission standards at a low treatment cost, the resource utilization of the waste acid solution can be achieved, the cost of the raw materials and the three-waste treatment cost are reduced, the purity of 2-methyl-4-chlorophenoxyacetic acid is higher than 95%, and the total yield is higher than 93%.

Design and Synthesis of Novel 4-Hydroxyl-3-(2-phenoxyacetyl)-pyran-2-one Derivatives for Use as Herbicides and Evaluation of Their Mode of Action

In order to develop a novel herbicide containing the β-triketone motif, a series of 4-hydroxyl-3-(2-phenoxyacetyl)-pyran-2-one derivatives were designed and synthesized. The bioassay results showed that compound II15 had good pre-emergent herbicidal activity even at a dosage of 187.5 g ha-1. Moreover, compound II15 showed a broader spectrum of weed control when compared with a commercial herbicide 2,4-dichlorophenoxyacetic acid (2,4-D), and displayed good crop safety to Triticum aestivum L. and Zea mays Linn. when applied at 375 g ha-1 under pre-emergence conditions, which indicated its great potential as a herbicide. More importantly, studying the molecular mode of action of compound II15 revealed that the novel triketone structure is a proherbicide of its corresponding phenoxyacetic acid auxin herbicide, which has a herbicidal mechanism similar to that of 2,4-D. The present work indicates that the 4-hydroxyl-3-(2-phenoxyacetyl)-pyran-2-one motif may be a potential lead structure for further development of novel auxin-type herbicides.

Synthetic method of 2-methyl-4-chlorophenoxyacetic acid

The invention discloses a synthetic method of 2-methyl-4-chlorophenoxyacetic acid, and relates to the technical field of organic synthesis. The target product 2-methyl-4-chlorophenoxyacetic acid is prepared by taking o-methylphenol as a raw material, reacting with sodium chloroacetate udner the effect of sodium bicarbonate; neutralizing by hydrochloric acid to obtain a midbody 2-methyl phenoxyacetic acid; finally, chloridizing the midbody 2-methyl phenoxyacetic acid by chlorine. The method applies sodium bicarbonate to replace sodium hydroxide to carry out neutralization, the neutralization reaction is small in heat release and few in side product; the method is good for improving product content and yield; besides, the chorine is applied to chloridize, and methylbenzene is used as the solvent; the generated acid is used as the neutralizing acid of the next batch, thus the massive phenolic wastewater is reduced, and it can meet the requirement of modern green pesticide; carbon dioxideis discharged from the neutralization reaction, the reaction heat is reduced, and the energy consumption is reduced. Compared with an original technique, the reaction technique has obvious advantagesof high yield, few wastes and low energy consumption.

Synthesis method of 2-methyl-4-chlorophenoxyacetic acid

The invention discloses a synthesis method of 2-methyl-4-chlorophenoxyacetic acid, and relates to the technical field of organic synthesis. The synthesis method comprises the following steps that methyl phenoxyacetic acid and methyl ethyl carbonate are added into a reaction kettle, chlorine is introduced for chlorination, and after washing, cooling crystallization, suction filtration and drying are conducted, the target product is obtained. According to the synthesis method of the 2-methyl-4-chlorophenoxyacetic acid, the methyl ethyl carbonate is adopted for replacing dichloroethane, so that by-products are few, and the synthesis method of the 2-methyl-4-chlorophenoxyacetic acid is beneficial for improving the content and the yield of the product; a large amount of waste acid is avoided, and the solvent (methyl ethyl carbonate) is environmentally friendly and non-toxic, and meets the requirements of modern green pesticides; compared with an original technology, a reaction technology has the obvious advantages of high yield, little three-waste and low energy consumption.