SULFENTRAZONE

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

The Uses of SULFENTRAZONE

Herbicide.

The Uses of SULFENTRAZONE

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.

Trade name

AUTHORITY® Sulfentrazone; CANOPY XL®; COVER®; F6285®; FMC® 97285; GAUNTLET®; SPARTAN®; SULFENTRAZONE® (F6285) 4F; SULFENTRAZONE® (F6285) 75DF

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.