ChemicalBook--->CAS DataBase List--->42576-02-3

42576-02-3

42576-02-3 Structure

42576-02-3 Structure
IdentificationMore
[Name]

Bifenox
[CAS]

42576-02-3
[Synonyms]

BIFENOX
FOX
MC-4379
METHYL 5-(2,4-DICHLOROPHENOXY)-2-NITROBENZOATE
MODOWN
MODOWN(R)
TOLKAN
2,4-Dichlorophenyl 3-Methoxycarbonyl-4-nitrophenyl ether
2,4-Dichlorophenyl 3-methoxycarbonyl-4-nitrophenyl ether2246
5-(2,4-Dichlorophenoxy)-2-nitrobenzoic acid methyl ester
5-(2,4-dichlorophenoxy)-2-nitrobenzoicacidmethylester
5-(2,4-dichlorophenoxy)-2-nitro-benzoicacimethylester
Benzoic acid, 5-(2,4-dichlorophenoxy)-2-nitro-, methyl ester
Methyl5-(2,4-didhlorophenoxy)-2-nitroben-zoate
Modown 4 flowable
5-(2,4-Dichlorphenoxy)-2-nitrobenzoic acid methyl ester
BIFENOX PESTANAL, 250 MG (METHYL 5-(2,4-
BIFENOX, 1GM, NEAT
bifenox (bsi,iso,ansi,wssa)
Methyl5-(2,4-dichlorophenoxy)-2-nitrobenzoate(Bifenox)
[EINECS(EC#)]

255-894-7
[Molecular Formula]

C14H9Cl2NO5
[MDL Number]

MFCD00055314
[Molecular Weight]

342.13
[MOL File]

42576-02-3.mol
Chemical PropertiesBack Directory
[Melting point ]

84-86°
[Boiling point ]

421.0±45.0 °C(Predicted)
[density ]

1.5715 (rough estimate)
[refractive index ]

1.7350 (estimate)
[storage temp. ]

0-6°C
[solubility ]

Chloroform (Slightly), Ethyl Acetate (Slightly)
[form ]

neat
[Appearance]

Off-white to light yellow Solid
[Water Solubility ]

0.5mg/L(temperature not stated)
[Merck ]

13,1214
[BRN ]

2170169
[Henry's Law Constant]

9.1×101 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
[Major Application]

agriculture
environmental
[InChI]

1S/C14H9Cl2NO5/c1-21-14(18)10-7-9(3-4-12(10)17(19)20)22-13-5-2-8(15)6-11(13)16/h2-7H,1H3
[InChIKey]

SUSRORUBZHMPCO-UHFFFAOYSA-N
[SMILES]

COC(=O)c1cc(Oc2ccc(Cl)cc2Cl)ccc1[N+]([O-])=O
[LogP]

4.480
[CAS DataBase Reference]

42576-02-3(CAS DataBase Reference)
[NIST Chemistry Reference]

Methyl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate(42576-02-3)
[EPA Substance Registry System]

42576-02-3(EPA Substance)
Safety DataBack Directory
[Hazard Codes ]

N
[Risk Statements ]

R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
[Safety Statements ]

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 9/PG 3
[WGK Germany ]

2
[RTECS ]

DG7890000
[HS Code ]

29189900
[Storage Class]

11 - Combustible Solids
[Hazard Classifications]

Aquatic Acute 1
Aquatic Chronic 1
[Hazardous Substances Data]

42576-02-3(Hazardous Substances Data)
[Toxicity]

LD50 orally in rats, mice: >6400, 4556 mg/kg; LC50 in pheasants, wild ducks: >5000 ppm (Kruger)
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Nitric acid-->Potassium carbonate-->Iron-->Carbon dioxide-->Ferric chloride-->Benzoyl chloride-->1,2-Dichloroethane-->Sulphur-->CHLOROETHANE-->2,4-Dichlorophenol-->Benzotrichloride-->CREAM-->Methyl 5-chloro-2-nitrobenzoate-->Mixed acid-->3-Chlorobenzoyl chloride-->Methyl 3-chlorobenzoate
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

Bifenox(42576-02-3).msds
Hazard InformationBack Directory
[Description]

Bifenox is a herbicide for the control of broadleaved weeds and some grasses. It has a low aqueous solubility, is volatile and would not be expected to leach to groundwater. It would also not be expected to persistent in soil or water systems. It has a low mammalian toxicity and no serious health concerns have been identified. Bifenox is moderately toxic to fish, aquatic invertebrates and earthworms but is highly toxic to algae.
[Uses]

Herbicide.
[Uses]

Selective preemergence or postemergence herbicide used to effectively control a wide variety of broad-leaved weeds (such as bindweed, jimsonweed, kochia, mustards, pigweeds, sesbania, smartweed and velvet-leaf) in tolerant crops (corn, grain sorghum, maize, rice and soybeans).
[Definition]

ChEBI: MC-4379 is a nitrobenzoic acid.
[Production Methods]

Bifenox is synthesised through a multi-step process culminating in an Ullmann condensation reaction. The final step involves reacting the potassium salt of 2,4-dichlorophenol with methyl 2-nitro-5-chlorobenzoic acid to form the herbicidal compound. The precursor, methyl 2-nitro-5-chlorobenzoic acid, is itself produced via a five-step synthesis starting from toluene, involving chlorination, oxidation to benzoic acid, methylation, and nitration.
[Agricultural Uses]

Herbicide: Used to control a variety of broadleaf weeds and grasses in legumes such as soybeans and peanuts, and post-emergent weed control in wheat, barley and sugar beets. Not currently registered in the U.S. However, it is used in 21 European countries and there are 27 global suppliers.
[Trade name]

ALIBI®; FOX®; MODOWN®[C]; MC- 4379®; SABINE®
[Mechanism of action]

Selective, absorbed by foliage, new shoots and roots to inhibit protoporphyrinogen oxidase
[Environmental Fate]

Soil. Bifenox degrades in soil forming 5-(2,4-dichlorophenoxy)-2-nitrobenzoic acid and methyl 5-(2,4-dichlorophenoxy)anthranilate (Hartley and Kidd, 1987; Smith 1988). The average half-life in soils is 7–14 days (Hartley and Kidd, 1987; Humburg et al., 1989)
Plant. Rapidly undergoes ring hydroxylation and subsequent conjugation in rice plants (Ashton and Monaco, 1991).
Photolytic. The UV photolysis (λ = 300 nm) of bifenox in various solvents was studied by Ruzo et al. (1980). In water, 2,4-dichloro-3′-(carboxymethyl)-4′-hydroxydiphenyl ether and 2,4-dichloro-3′-(carboxymethyl)-4′-aminodiphenyl ether were identi
[Pesticide Type]

Herbicide
Spectrum DetailBack Directory
[Spectrum Detail]

Bifenox(42576-02-3)MS
Bifenox(42576-02-3)1HNMR
Bifenox(42576-02-3)13CNMR
Bifenox(42576-02-3)IR1
Bifenox(42576-02-3)IR2
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

42576-02-3(sigmaaldrich)
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