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51338-27-3

51338-27-3 Structure

51338-27-3 Structure
IdentificationMore
[Name]

Diclofop-methyl
[CAS]

51338-27-3
[Synonyms]

2-[4-(2',4'-DICHLORO-PHENOXY)PHENOXY]-METHYL-PROPANOATE
DICLOFOP METHYL
DICLOSAN
ELOGRASS
HOE 23408
HOEGRASS
HOE-GRASS(R)
HOELOMOBEED
HOELON
HOELON 3EC(R)
HOELON(R)
HOXAN(R)
ILLOXAN
ILLOXAN(R)
METHYL-2-[4-(2',4'-DICHLOROPHENOXY)-PHENOXY] PROPANOATE
METHYL 2-[4-(2,4-DICHLOROPHENOXY)PHENOXY]PROPIONATE
NOGRASS
(+or-)-methyl2-(4-(2,4-dichlorophenoxy)phenoxy)propionate
2-(4-(2,4-Dichlorophenoxy)phenoxy)-methyl-propionate
2-(4-(2,4-dichlorophenoxy)phenoxy)-propionicacimethylester
[EINECS(EC#)]

257-141-8
[Molecular Formula]

C16H14Cl2O4
[MDL Number]

MFCD00128052
[Molecular Weight]

341.19
[MOL File]

51338-27-3.mol
Chemical PropertiesBack Directory
[Appearance]

A white crystalline solid. Odorless. Can also be commercially available as a clear to dark brown liquid with a typical solvent odor
[Melting point ]

39-41°C
[Boiling point ]

173-175°C (0.1 mbar)
[density ]

1.3
[refractive index ]

1.5300 (estimate)
[storage temp. ]

0-6°C
[form ]

neat
[color ]

White to off-white
[Water Solubility ]

0.005 g/100 mL
[Merck ]

13,3109
[BRN ]

2224754
[Henry's Law Constant]

5.0×100 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
[InChI]

1S/C16H14Cl2O4/c1-10(16(19)20-2)21-12-4-6-13(7-5-12)22-15-8-3-11(17)9-14(15)18/h3-10H,1-2H3
[InChIKey]

BACHBFVBHLGWSL-UHFFFAOYSA-N
[SMILES]

COC(=O)C(C)Oc1ccc(Oc2ccc(Cl)cc2Cl)cc1
[LogP]

4.620
[CAS DataBase Reference]

51338-27-3(CAS DataBase Reference)
[NIST Chemistry Reference]

Propanoic acid, 2-[4-(2,4-dichlorophenoxy)phenoxy]-, methyl ester(51338-27-3)
[EPA Substance Registry System]

51338-27-3(EPA Substance)
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)Environment (GHS09)
GHS07,GHS09
[Signal word ]

Warning
[Hazard statements ]

H302-H317-H410
[Precautionary statements ]

P261-P264-P273-P280-P301+P312-P302+P352
[Hazard Codes ]

Xn;N,N,Xn
[Risk Statements ]

R22:Harmful if swallowed.
R43:May cause sensitization by skin contact.
R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
[Safety Statements ]

S24:Avoid contact with skin .
S37:Wear suitable gloves .
S60:This material and/or its container must be disposed of as hazardous waste .
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
[RIDADR ]

UN 3077
[WGK Germany ]

2
[RTECS ]

UF1180000
[HS Code ]

29189900
[Storage Class]

11 - Combustible Solids
[Hazard Classifications]

Acute Tox. 4 Oral
Aquatic Acute 1
Aquatic Chronic 1
Skin Sens. 1
[Hazardous Substances Data]

51338-27-3(Hazardous Substances Data)
[Toxicity]

dog,LD50,oral,1600mg/kg (1600mg/kg),"Agrochemicals Handbook," with updates, Hartley, D., and H. Kidd, eds., Nottingham, Royal Soc of Chemistry, 1983-86Vol. A138, Pg. 1983,
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Propionic acid-->Nitrofen
Hazard InformationBack Directory
[General Description]

Colorless crystals. Decomposed by either strong acid or base. Used as a selective herbicide.
[Reactivity Profile]

A bridged diphenyl.
[Air & Water Reactions]

Slightly soluble in water (3 mg/l).
[Hazard]

Moderately toxic by ingestion and skin contact. Low toxicity by inhalation.
[Potential Exposure]

Diclofop-methyl is a chlorophenoxy; aryloxyphenoxypropionate acid selective postemergenceherbicide used to control wild oats and annual grassy weeds in grain and vegetable crops: alfalfa, carrots, celery, box, field and French beans, barley, wheat, brassicas, parsnips, peas, potatoes, rapeseed (canola), soy beans, oilseed rape, onions, sugar beets and lettuce. Some uses are classified RUP
[First aid]

If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions) if breathing has stopped, and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Do not induce vomiting when formulations containing petroleum solvents are ingested. Otherwise, give large quantities of water and induce vomiting. Do not make an unconscious person vomit
[Shipping]

UN3345 Phenoxyacetic acid derivative pesticide, solid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials. UN3348 Phenoxyacetic acid derivative pesticide, liquid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous material. UN3077 Environmentally hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required. Note: Commercial product may also be a liquid in a flammable carrier.
[Incompatibilities]

Incompatible with oxidizers, chlorates nitrates, peroxides, sulfuric acid, caustics, ammonia, aliphatic amines, alkanolamines, isocyanates, alkylene oxides, and epichlorohydrin.
[Description]

Diclofop-methyl is a grass weed herbicide. It has a low aqueous solubility, a low risk of leaching to groundwater and is relatively volatile. It is non-persistent in soils but may be persistent in aquatic systems under certain conditions. It is moderately toxic to mammals if ingested and there is some concern that exposure may cause cancer or adverse reproduction / developmental effects. It is moderately toxic to birds, most aquatic organisms, earthworms and honeybees but is not toxic to honeybees.
[Chemical Properties]

A white crystalline solid. Odorless. Can also be commercially available as a clear to dark brown liquid with a typical solvent odor
[Waste Disposal]

In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers. Containers must be disposed of properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office
[Uses]

Herbicide.
[Definition]

ChEBI: Methyl 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoate is a methyl ester resulting from the formal condensation of the carboxylic acid group of 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoic acid with methanol. It is an aromatic ether, a dichlorobenzene, a diether and a methyl ester.
[Production Methods]

The commercial production of diclofop-methyl typically involves a multi-step organic synthesis starting from phenoxyacetic acid derivatives. The key intermediate is diclofop acid, which is synthesised by chlorinating and etherifying specific aromatic compounds to introduce the 2,4-dichlorophenoxy moiety. This acid is then esterified with methanol in the presence of an acid catalyst, commonly sulphuric acid or a similar agent, to form diclofop-methyl, the active herbicidal ester.
[Agricultural Uses]

Herbicide: Some uses are classified as U.S. Restricted Use Pesticide (RUP). Diclofop-methyl is a selective post-emergence herbicide used to control wild oats and annual grassy weeds in grain and vegetable crops: alfalfa, carrots, celery, box, field and french beans, barley, wheat, brassicas, parsnips, peas, potatoes, rapeseed (canola), soy beans, oilseed rape, onions, sugar beets and lettuce.
[Trade name]

DICHLORDIPHENPROP®; HOELON®; HOELON® 3EC; HOE-GRASS®; HOEGRASS®; HOE® 23408; ILOXAN®; ILLOXAN®; ONE SHOT®[C]
[Mechanism of action]

Selective, systemic with contact action. Acetyl CoA carboxylase inhibitor (ACCase) - distrupts fatty acid biosynthesis and lipid formation.
[Environmental Fate]

Biological. From the first-order biotic and abiotic rate constants of diclofop-methyl in estuarine water and sediment/water systems, the estimated biodegradation half-lives were 0.24–12.4 and 0.11–2.2 days, respectively (Walker et al., 1988).
[Metabolic pathway]

Two resistant biotypes of black-grass (Peldon A1 and Lincs. E1 of Alopecurus myosuroides) exhibit moderately enhanced metabolism of 14C-diclofop methyl. Diclofop methyl is hydrolyzed to the corresponding propionic acid which undergoes further degradation to give polar metabolites. The amounts of the metabolites depend on the metabolism activity of the individual biotypes. In wheat, three isomeric hydroxylated metabolites are identified in a major metabolic pathway after acid hydrolysis of the glucoside conjugates.
[Pesticide Type]

Herbicide
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

51338-27-3(sigmaaldrich)
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