93-65-2

Basic information

• Product Name: 2-(4-Chloro-2-methylphenoxy)propanoic acid
• Synonyms: mecopropd-isomer;Mecoturf;Mecprop;Mepro;N.B. Mecoprop;Propal;propanoicacid,2-(4-chloro-2-methylphenoxy)-;Propionic acid, 2-(2-methyl-4-chlorophenoxy)-
• CAS NO: 93-65-2
• Molecular Formula: C₁₀H₁₁ClO₃
• Molecular Weight: 214.65
• EINECS: 202-264-4
• Product Categories: Organics;Aromatics
• Mol File: 93-65-2.mol

Chemical Properties

• Melting Point: 88-90°C
• Boiling Point: 308.11°C (rough estimate)
• Flash Point: 154.5°C
• Appearance: /
• Density: 1.2413 (rough estimate)
• Vapor Pressure: 6.04E-05mmHg at 25°C
• Refractive Index: 1.5390 (estimate)
• Storage Temp.: APPROX 4°C
• PKA: 3.19±0.10(Predicted)
• Water Solubility: 734 mg l-1
• BRN: 6568283
• CAS DataBase Reference: 2-(4-Chloro-2-methylphenoxy)propanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-Chloro-2-methylphenoxy)propanoic acid(93-65-2)
• EPA Substance Registry System: 2-(4-Chloro-2-methylphenoxy)propanoic acid(93-65-2)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-38-41-50/53
• Safety Statements: 26-37/39-61-60-13
• RIDADR: UN2811 - class 6.1 - PG 3 - EHS - Toxic solids, organic, n.o.s.,
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 93-65-2(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

Herbicide.

General Description

Colorless crystals. Corrosive to metals. Used as an herbicide.

Air & Water Reactions

Soluble in water.

Reactivity Profile

A phenoxy aryloxyalkanoic acid derivative.

Agricultural Uses

Herbicide: A General Use Pesticide, postemergent herbicide, most often used in combination with other pesticides. Most of the production is used on turf, including lawns, sport turf and commercial sod production for control of creeping broadleaf weeds such as clovers, chickweed, ivy, plantain and similar plants. It is also used on wheat, barley and oats. A small percentage is used in noncrop areas such as rights-of-way, drainage ditch banks and forest site preparation.

Trade name

ASSASSIN?; BANVEL P?; BH MECOPROP?; CERIDOR?; CHIPCO?; CHIPCO TURF HERBICIDE MCPP?; CLEAVAL?; CLENECORN?; CLOVOTOX?; COMPITOX EXTRA?; CORNOX PLUS?; CR 205?; CRUSADER?; DOCKLENE?; EXP 419?; GRASLAM?; HARNESS?; HARRIER?; HEDONAL MCPP?; HERRISOL?; HYMEC?; IOTOX?; ISO-CORNOX?; KILPROP?; LIRANOX?; MECOBROM?; MECOMIN D?; MECOPEOP?; MECOPAR?; MECOPEX?; MECOTURF?; MEPRO?; MECHLORPROP?; MECOPROP?; MYLONE?; MUSKETEET?; POST-KITE?; PROPAL?; PROPONEX- PLUS?; RANKOTEX?; RD 4593?; RUNCATEX?; SELOXONE?; SCOTLENE?; SEL-OXONE?; SUPER GREEN AND WEED?; SUPOERTOX?; SWIPE 560 EC?; TARGET?; TERSET?; TETRALEN-PLUS?; TRIESTER II?; TRIMEC 1144 40% SP?; TRIPLET?; U 46?; U 46 KV-ESTER?; VERDONE?; VI-PAR?; VI- PEX?; VIPEX?

Safety Profile

Suspected carcinogen. Poison by ingestion. Moderately toxic by skin contact and intraperitoneal routes. Experimental teratogenic and reproductive effects. Mutation data reported. An herbicide. When heated to decomposition it emits toxic fumes of Cl-

Potential Exposure

It is a chlorophenoxy-herbicide, used to control many broadleaf weeds. A derivative of phenoxy aryloxyalkanoic acid.

Incompatibilities

A weak acid. Incompatible with strong bases and oxidizers.

InChI:InChI=1/C10H11ClO3/c1-6-5-8(11)3-4-9(6)14-7(2)10(12)13/h3-5,7H,1-2H3,(H,12,13)/t7-/m0/s1

Upstream product

• 52106-86-2 sodium 4-chloro-2-methyl-phenolate 
• 535-11-5 Ethyl 2-bromopropionate 
• 1570-64-5 2-methyl-4-chlorophenol 

Downstream Products

• 16484-77-8 (R)-Mecoprop 
• 25333-13-5 (S)-mecoprop 
• 106690-28-2 3-Benzo[1,3]dioxol-5-yl-6-[1-(4-chloro-2-methyl-phenoxy)-ethyl]-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole 
• 106864-97-5 C₁₅H₂₀ClNO₃Si 
• 97534-44-6 (R)-2-methyl-2-(4-chloro-2-methylphenoxy)ethanol 
• 92446-90-7 (S)-(+)-2-methyl-2-(4-chloro-2-methylphenoxy)ethanol 
• 42383-63-1 2-(4-Chlor-2-methylphenoxy)propionsaeureanhydrid 
• 115398-71-5 4-Amino-5-[1-(4-chloro-2-methyl-phenoxy)-ethyl]-4H-[1,2,4]triazole-3-thiol 
• 124497-68-3 3-[1-(4-Chloro-2-methyl-phenoxy)-ethyl]-6-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine 
• 104133-05-3 rac-2-(4-chloro-2-methylphenoxy)propionic acid tetraethylene glycol diester 
• 13740-38-0 2-(4-Chloro-2-methyl-phenoxy)-N-phenyl-propionamide 
• 19095-88-6 sodium (±)-2-(4-chloro-2-methylphenoxy)propionate 
• 27492-80-4 (2-dimethylamino)ethyl (±)-2-(4-chloro-2-methylphenoxy)propionate 

Relevant articles and documents

New Synthesis of Known Herbicides Based on Aryloxyalkanoic Acids

A new version has been proposed for the synthesis of analogs of the known herbicides mecoprop (MCPP) and dichlorprop (2,4-DP) by ozonolysis of chloro derivatives of (pent-3-en-2-yloxy)benzene.

Active substances for increasing the stress defense in plants to abiotic stress, and methods of finding them

The invention relates to a method of finding compounds which increase the tolerance of plants to abiotic stress factors acting on this plant, such as, for example, temperature (such as chill, frost or heat), water (such as dryness, drought or anoxia), or the chemical load (such as lack of or excess of mineral salts, heavy metals, gaseous noxious substances) by increasing the expression of plant-endogenous proteins, and to the use of these compounds for increasing the tolerance in plants to abiotic stress factors.

Herbicides comprising benzoylcyclohexanediones and safeners

Herbicidal compositions are described that comprise active substances from the group of the benzoylcyclohexanediones and also safeners. These herbicidal compositions are especially suitable for use against weed plants in crop plant cultures.

COMBINATIONS OF HERBICIDES AND SAFENERS

There are described herbicidal compositions which comprise at least one herbicidally active compound of the formula (I) and at least one crop-plant-protecting compound as safener. In this formula (I), V is an optionally substituted radical selected from the group consisting of isoxazol-4-yl, pyrazol-4-yl, cyclohexane-1,3-dion-2-yl and 3-oxopropionitril-2-yl and R9 is nitro, amino, halogen or a carbon-containing radical. The group of the safeners contains, for example, 2,4-D, cyometrinil, dicamba, dymron, fenclorim, flurazole, fluxofenim, lactidichlor, MCPA, mecoprop, MG-191, oxabetrinil, methyl diphenylmethoxyacetate, 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea, 1,8-naphthalaic anhydride, 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea, 1-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea, 1-[4-(N-naphthoylsulfamoyl)phenyl]-3,3-dimethylurea, (4-chlorophenoxy)acetic acid, 4-(2,4-dichlorophenoxy)butyric acid, 4-(4-chloro-o-tolyloxy)butyric acid, 4-(4-chlorophenoxy)butyric acid, in each case their acids and esters, N-acylsulfonamides, N-acylsulfamoyl-benzamides, in each case, if appropriate, also in salt form and in each case optionally substituted 1-phenylpyrazoline, 1-phenylpyrazole, 1-phenyl-triazole, 5-phenylisoxazoline and 5-phenylmethylisoxazoline-3-carboxylic esters and 2-(8-quinolinyloxy)acetic acid derivatives.

Solid mixtures based on sulfonylureas and adjuvants

Solid mixtures comprising a) an active compound from the group consisting of the sulfonylureas, and b) an alkylpolyglucoside.

Solid mixtures based on sulfonylureas and adjuvants

A solid ixture comprising a) an active ingredient from the group of the sulfonylureas and b) an alkyl ether of a copolymer of C2-C4-alkylene oxides.

Herbicidal mixtures having a synergistic effect

PCT No. PCT/EP96/03996 Sec. 371 Date Feb. 17, 1998 Sec. 102(e) Date Feb. 17, 1998 PCT Filed Sep. 12, 1996 PCT Pub. No. WO97/10714 PCT Pub. Date Mar. 27, 1997A composition comprising at least one sulfonylurea of the formula I wherein R1 is substituted alkyl; halogen; a group ER6 (E=O, S or NR7); COOR8; NO2; S(O)oR9; SO2NR10R11; or CONR10R11; R2 is hydrogen, alkyl, alkenyl, alkynyl, halogen, alkoxy, haloalkoxy, haloalkyl, alkylsulfonyl, nitro, cyano or alkylthio; R3 is F, CF3, CF2Cl, CF2H, OCF3, OCF2Cl, or, if R1 is CO2CH3 and R2 is simultaneously fluorine, R3 is Cl, or, if R1 is CH2CF3 or CF2CF3, R3 is methyl, or, if R4 is OCF3 or OCF2Cl, R3 is OCF2H or OCF2Br; R4 is alkoxy, alkyl, alkylthio, alkylamino, dialkylamino, halogen, haloalkyl or haloalkoxy; and R5 is hydrogen, alkoxy or alkyl; or an enviromentally compatible salt of I, and an aryloxyalkanoic acid selected from the group consisting of 2,4-D, 2,4-DB, clomeprop, dichlorprop, dichlorprop-P, dichlorprop-P (2,4-DP-P), fenoprop (2,4,5-TP), fluoroxypyr, MCPA, MCPB, mecoprop, mecoprop-P, napropamide, napropanilide, triclopyr, and an enviromentally compatible salt thereof exhibits a synergistic herbicidal effect.

Process for preparing solid, free-flowing water-soluble salts of aryloxy-C1 -C4 -alkanecarboxylic acids

Process for preparing solid, free-flowing water-soluble salts of aryloxy-C1 -C4 -alkanecarboxylic acids by reacting the aryloxy-C1 -C4 -alkanecarboxylic acids with a salt-forming base, the salt formation taking place in the melt in the presence or absence of an entraining agent suitable for the azeotropic removal of water or in solution in the presence of an entraining agent suitable for the azeotropic removal of water and, if appropriate, removing the entraining agent from the reaction mixture during the reaction or subsequently and then isolating the solid salts in a customary manner.

Bituminous roof sealing membranes as major sources of the herbicide (R,S)-mecoprop in roof runoff waters: Potential contamination of groundwater and surface waters

During a field study on the occurrence and behavior of pesticides during artificial infiltration of roof runoff, the herbicide R-mecoprop and its S- enantiomer were detected in roof runoff in much higher concentrations (up to 500 μg/L) than in the corresponding rainwater. We hypothesized in the foregoing paper in this issue that the root protection agent Preventol B 2 in the bituminous sheets, which is a bi-ester of (R,S)-mecoprop (see Figure 1), was the source of these compounds. In this work, the occurrence and variations of (R,S)-mecoprop in the runoff from different flat roofs were investigated. It is shown that concentrations of a few micrograms per liter at an R to S enantiomeric ratio (ER) of 0.8-1.4 can permanently be expected in roof runoff from flat roofs which have Preventol B 2 containing sealing membranes incorporated. The major factors that govern the release of (R,S)- mecoprop are the type of bituminous sheet, the biological activity, and the intensity of the applied rooftop greening. A field study in the Greifensee catchment area revealed that wastewater treatment plants (WWTPs) are a major source of (R,S)-mecoprop which most probably originates from construction materials equipped with Preventol B 2. A comparison of the (R,S)-mecoprop loads from flat roofs and from agricultural applications into surface waters revealed that these loads were in the same order of magnitude. During a field study on the occurrence and behavior of pesticides during artificial infiltration of roof runoff, the herbicide R-mecoprop and its S-enantiomer were detected in roof runoff in much higher concentrations (up to 500 μg/L) than in the corresponding rainwater. We hypothesized in the foregoing paper in this issue that the root protection agent Preventol B 2 in the bituminous sheets, which is a bi-ester of (R,S)-mecoprop (see Figure 1), was the source of these compounds. In this work, the occurrence and variations of (R,S)-mecoprop in the runoff from different flat roofs were investigated. It is shown that concentrations of a few micrograms per liter at an R to S enantiomeric ratio (ER) of 0.8-1.4 can permanently be expected in roof runoff from flat roofs which have Preventol B 2 containing sealing membranes incorporated. The major factors that govern the release of (R,S)-mecoprop are the type of bituminous sheet, the biological activity, and the intensity of the applied rooftop greening. A field study in the Greifensee catchment area revealed that wastewater treatment plants (WWTPs) are a major source of (R,S)-mecoprop which most probably originates from construction materials equipped with Preventol B 2. A comparison of the (R,S)-mecoprop loads from flat roofs and from agricultural applications into surface waters revealed that these loads were in the same order of magnitude.

Herbicidal heterocyclic sulfonylurea compositions safened by herbicidal acids such as 2,4-D below a pH of 5

Disclosed are herbicidal concentrate formulation compositions having reduced grass crop plant phytotoxicity comprising certain sulfonamide or sulfonylurea herbicides in admixture with a herbicidal organic acid from the group consisting of clopyralid, 2,4-D, 2,4-DP, dicamba, dichlorprop-P, fluroxypyr MCPA, MCPP, mecoprop-P, picloram, triclopyr or mixtures of said acids; also disclosed is the preparation of said compositions and the pre- and post-emergent agricultural uses thereof in water diluted form.