| Identification | Back Directory | [Name]
METOXURON | [CAS]
19937-59-8 | [Synonyms]
DEFTOR
DOSAFLO
DOSANEX
INVESTT
Purivel
SULEREX
SAN 7102
Dosagran
SAN 6602
san6915h
san7102h
SAN 6915H
METOXURON
dosanexfl
dosanexmg
Metoxuran
SAN 7102H
methoxuron
Dosanex fl
Dosanex mg
Deftor(TM)
Metoxuron-D6
herbicide6602
Herbicide 6602
metoxuron solution
METOXURON STANDARD
metoxuron (bsi,iso)
METOXURON PESTANAL
Metoxuron @100 μg/mL in MeOH
Metoxuron 250mg [19937-59-8]
METOXURON PESTANAL (3-(3-CHLORO-4-METHO&
3-(3-chloro-4-methoxyphenyl)-1,1-dimethyl-ure
1,1-Dimethyl-3-(3-chloro-4-methoxyphenyl)urea
3-(3-CHLORO-4-METHOXYPHENYL)-1,1-DIMETHYLUREA
n’-(3-chloro-4-methoxyphenyl)-n,n-dimethyl-ure
N’-(3-chloro-4-methoxyphenyl)-N,N-dimethylurea
N'-(3-Chloro-4-methoxyphenyl)-N,N-dimethylurea
N,N-Dimethyl-N'-(4-methoxy-3-chlorophenyl)urea
n,n-dimethyl-n’-(4-methoxy-3-chlorophenyl)urea
N-(3-Chloro-4-methoxyphenyl)-N',N'-dimethylurea
n-(3-chloro-4-methoxyphenyl)-n’,n’-dimethylurea
3-(3-CHLORO-4-SULFOPHENYL)-3-METHYL-5-PYRAZOLONE
Urea, 3-(3-chloro-4-methoxyphenyl)-1,1-dimethyl-
Urea, N'-(3-chloro-4-methoxyphenyl)-N,N-dimethyl-
3-(3-Chlor-4-methoxyphenyl)-1,1-dimethylharnstoff
N-(3-Chloro-4-methoxyphenyl)-N ,N -dimethyl moy
N'-(3-Chlor-4-methoxy-phenyl)-N,N-dimethylharnstoff
n’-(3-chlor-4-methoxy-phenyl)-n,n-dimethylharnstoff
metoxuron 3-(3-chloro-4-methoxyphenyl)-1,1-dimethylurea | [EINECS(EC#)]
243-433-2 | [Molecular Formula]
C10H13ClN2O2 | [MDL Number]
MFCD00055444 | [MOL File]
19937-59-8.mol | [Molecular Weight]
228.68 |
| Chemical Properties | Back Directory | [Melting point ]
124-127 °C | [Boiling point ]
391.6±42.0 °C(Predicted) | [density ]
1.3100 (rough estimate) | [refractive index ]
1.5500 (estimate) | [Fp ]
2 °C | [storage temp. ]
APPROX 4°C
| [solubility ]
Chloroform (Slightly), DMSO (Slightly) | [form ]
Solid | [pka]
13.83±0.70(Predicted) | [color ]
White to Off-White | [Water Solubility ]
678mg/L(23 ºC) | [Henry's Law Constant]
6.9×102 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) | [Major Application]
agriculture
environmental | [InChI]
1S/C10H13ClN2O2/c1-13(2)10(14)12-7-4-5-9(15-3)8(11)6-7/h4-6H,1-3H3,(H,12,14) | [InChIKey]
DSRNRYQBBJQVCW-UHFFFAOYSA-N | [SMILES]
COc1ccc(NC(=O)N(C)C)cc1Cl | [EPA Substance Registry System]
Metoxuron (19937-59-8) |
| Safety Data | Back Directory | [Hazard Codes ]
N,Xn,F | [Risk Statements ]
50/53-36-20/21/22-11 | [Safety Statements ]
60-61-36-26-16-36/37 | [RIDADR ]
UN3077 9/PG 3 | [WGK Germany ]
WGK 2 | [RTECS ]
YS5775000 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral
Aquatic Acute 1
Aquatic Chronic 1 | [Toxicity]
mouse,LD50,oral,2542mg/kg (2542mg/kg),ENDOCRINE: OTHER CHANGESBLOOD: OTHER CHANGES,Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 47(2), Pg. 13, 1982. |
| Hazard Information | Back Directory | [Uses]
Metoxuron is used as a herbicide. | [Definition]
ChEBI: Metoxuron is a member of the class of 3-(3,4-substituted-phenyl)-1,1-dimethylureas that is urea in which one of the nitrogens is substituted by a 3-chloro-4-methoxyphenyl group while the other is substituted by two methyl groups. It is a plant growth regulator and a pre- and post-emergence herbicide used for the control of grasses and broad-leaved weeds in carrots and cereals (e.g. wheat, barley and rye). It has a role as an agrochemical, an environmental contaminant, a herbicide, a xenobiotic, a photosystem-II inhibitor and a plant growth regulator. It is a 3-(3,4-substituted-phenyl)-1,1-dimethylurea, a monomethoxybenzene and a member of monochlorobenzenes. | [Production Methods]
The industrial synthesis of metoxuron begins with the preparation of 3-chloroaniline, which serves as the aromatic base. This compound undergoes condensation with dimethylcarbamoyl chloride or similar methylurea precursors to form the substituted urea backbone. The methoxy group is introduced via methylation of the urea nitrogen using agents like methyl iodide or dimethyl sulphate. The reactions are typically carried out in organic solvents such as acetone or toluene, under controlled temperature and pH conditions to ensure high yield and purity. | [Mechanism of action]
Selective with contact and residual action. Photosynthetic electron transport inhibitor at the photosystem II. | [Metabolic pathway]
Photodegradation of metoxuron with UV irradiation in
the presence of UV-H2O2 and -TiO2 primarily proceeds
with the replacement of the chlorine atom with the
hydroxy group and the attack of OH radicals at the
6-position on the phenyl ring. The principal
photoproducts identified are 3-(4-methoxy-2,5-
paraquinone)-1,1-dimethylurea, hydroxymetoxuron,
3-(3-hydroxy-4-methoxyphenyl)-1,1-dimethylurea,
3-(3-chloro-4-hydroxyphenyl)-1,1-dimethylurea, and
3-(3-chloro-4-methoxyphenyl)-1,1dimethylurea. | [Pesticide Type]
Herbicide |
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