| Identification | Back Directory | [Name]
SULFENTRAZONE | [CAS]
122836-35-5 | [Synonyms]
f6285
CAPAZ
BORAL
FMC97285
AUTHORITY
SULFENTRAZONE
Sulfentrazone standard
SULFENTRAZONE,FMC 97285
4-triazol-1-yl)phenyl)-5-oxo-1h-2
n-(2,4-dichloro-5-(4-(difluoromethyl)-4,5-dihydro-3-methyl-methanesulfonamid
2′,4′-dichloro-5′-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)methanesulfonanilide
2',4'-dichloro-5'-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl) methanesulfonanilide
Methanesulfonamide, N-2,4-dichloro-5-4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-ylphenyl-
N-(2,4-Dichloro-5-(4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)phenyl)methanesulfonamide
N-(2,4-dichloro-5-(4-(difluoroMethyl)-3-Methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)phenyl)MethanesulfonaMide
N-(2,4-dichloro-5-(4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)phenyl)methanesulfonamide
n-(2,4-dichloro-5-(4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1h-1,2,4-triazol-1-yl)phenyl)-methanesulfonamid | [Molecular Formula]
C11H10Cl2F2N4O3S | [MDL Number]
MFCD00869633 | [MOL File]
122836-35-5.mol | [Molecular Weight]
387.19 |
| Chemical Properties | Back Directory | [Melting point ]
75-78° | [Boiling point ]
468.2±55.0 °C(Predicted) | [density ]
1.21 g/cm3 | [storage temp. ]
0-6°C | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
6.56(at 25℃) | [color ]
Pale Brown to Beige | [Henry's Law Constant]
1.5×107 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) | [InChI]
InChI=1S/C11H10Cl2F2N4O3S/c1-5-16-19(11(20)18(5)10(14)15)9-4-8(17-23(2,21)22)6(12)3-7(9)13/h3-4,10,17H,1-2H3 | [InChIKey]
OORLZFUTLGXMEF-UHFFFAOYSA-N | [SMILES]
CS(NC1=CC(N2C(=O)N(C(F)F)C(C)=N2)=C(Cl)C=C1Cl)(=O)=O | [EPA Substance Registry System]
Methanesulfonamide, N-[2,4-dichloro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl]phenyl]-(122836-35-5) |
| Hazard Information | Back Directory | [Usage]
Sulfentrazone is an herbicide used for controlling sedges in turfgrass. | [Description]
Solubility. In water at 25 ?C: 100 mg/L at pH 6,
800 mg/mL at pH 7, 1,600 mg/mL at pH 7.5; soluble to
some extent in acetone and other polar organic solvents
Pka. 6.56
Stability. Stable | [Chemical Properties]
The pure product is a brownish-yellow solid. Its mp is 121-123°C, relative density is 1.34 (20°C), vapor pressure is 1.3×10-4 Pa (25°C), and dissociation constant pKa is 6.56. It is soluble in most polar organic solvents, including acetone. Its solubility in water at 25°C is 11 mg/L (pH 6), 0.78 (pH 7), and 16 (pH 7.5). Its half-life in soil is 110-280 days. | [Uses]
Herbicide. | [Uses]
Sulfentrazone is an herbicide used for controlling sedges in turfgrass. | [Definition]
ChEBI: Sulfentrazone is a member of the class of triazoles that is 5-oxo-1,2,4-triazole which is substituted at positions 1, 3, and 4 by 2,4-dichloro-5-[(methylsulfonyl)amino]phenyl, methyl, and difluoromethyl groups, respectively. A protoporphyrinogen oxidase inhibitor, it is used as a herbicide to control broad-leaved weeds in soya and tobacco crops. Not approved for use within the European Union. It has a role as an EC 1.3.3.4 (protoporphyrinogen oxidase) inhibitor, a herbicide and an agrochemical. It is a sulfonamide, a dichlorobenzene, an organofluorine compound and a member of triazoles. | [Production Methods]
Sulfentrazone is commercially produced via a multi-step process starting with the chlorination of o-xylene to form 1,2-bis(chloromethyl)-4-chlorobenzene, which undergoes nucleophilic substitution with sodium sulphite to yield the corresponding sulfonate; subsequent diazotization, reduction, and cyclisation with ethyl acetoacetate under acidic conditions form the triazolinone ring, followed by oxidation with hydrogen peroxide to introduce the difluoromethylsulfonyl group, producing the active compound. | [Trade name]
AUTHORITY® Sulfentrazone; CANOPY XL®; COVER®; F6285®; FMC® 97285; GAUNTLET®; SPARTAN®; SULFENTRAZONE® (F6285) 4F; SULFENTRAZONE® (F6285) 75DF | [Mechanism of action]
Absorbed by roots and foliage and translocated. Inhibition of protoporphyrinogen oxidase (PPO) - cell membrane disruption | [Metabolic pathway]
When 14C-sulfentrazone is applied to coffee senna
and sicklepod through the roots, 83% of the parent
compound remains in coffee senna leaf tissue after
9 h exposure and in contrast, sicklepod takes up
relatively less sulfentrazone through the root and
metabolizes sulfentrazone in the foliage more rapidly
than coffee senna. The primary detoxification reaction
appears to be oxidation of the methyl group on the
triazolinone ring, resulting in the formation of the more
polar hydroxymethyl derivative. The aniline analog is
identified as a plant-specific metabolite. The tolerance
of sicklepod to sulfentrazone is primarily due to a
relatively high rate of metabolism of sulfentrazone
compared with coffee senna. When 14C-sulfentrazone
is administered orally to rats, goats, and hens in a
daily diet, administered radioactivity is quantitatively
excreted in the urine, feces, or hen excreta. In all of
the species, unchanged sulfentrazone and two non-conjugated metabolites are found, which are 3-hydroxymethyl and carboxylic acid derivatives, the
latter of which decomposes at high temperature or
acidic pH to give the corresponding desmethyl analog
of sulfentrazone. In rats, a minor reduction metabolite
is detected which is tentatively characterized as the
2,3-dihydro-3-hydroxymethyl derivative. | [Pesticide Type]
Herbicide |
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