Uses
Postemergence herbicide used to control wild garlic and many broad-leaved weeds
in barley and spring wheat.
Definition
ChEBI: A methyl ester resulting from the formal condensation of the carboxy group of thifensulfuron with methanol. It is used as a post-emergence herbicide for the control of grass and broad-leaved weeds.
Production Methods
The production of thifensulfuron-methyl, a sulfonylurea herbicide, involves a multi-step chemical synthesis starting with the construction of a substituted benzene sulfonamide and a triazine ring system. These components are coupled through a sulfonylurea linkage to form the active molecule. The process typically includes steps such as chlorination, amination, and methylation, followed by purification and crystallization to achieve high purity.
Agricultural Uses
Herbicide: A herbicide for postemergence broadleaf weed control
in crops for food such as soybeans and cotton. Not
listed for use in EU countries.
Trade name
ALLY®; BASIS® (rimsulfuron + thifensulfuron
methyl); CANVAS® (thifensulfuron methyl + tribenuron
methyl + metsulfuron-methyl); DPX-M6316®;
EXPRESS®; HARMONY® Extra (thifensulfuron
methyl + tribenuron methyl); INM-6316®; PINNACLE®;
PROSPECT®; RELIANCE® SYNCHRONY®, (chlorimuron-
ethyl + thifensulfuron methyl)
Mechanism of action
Selective, absorbed through foliage, inhibits plant amino acid synthesis - acetohydroxyacid synthase AHAS
Environmental Fate
Chemical/Physical. May hydrolyze in aqueous solutions forming methyl alcohol and
3-(((((4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino)carbonyl)amino)sulfonyl)-2-
thiophenecarboxylic acid.
Metabolic pathway
The hydrolytic degradation of thifensulfuron methyl is
pH dependent and, in alkaline condition, specifically
yields the corresponding free acid. Primary
degradation cleaves the sulfonylurea moiety to give
two typical hydrolyzed products, sulfonamide and
aminotriazine analogs, derived from thifensulfuron
methyl in acidic and neutral conditions. Hydrolysis of
the ester linkage proceeds in mammals, plants, soils, and also chemical hydrolysis, and opening of the
triazine ring occurs to yield the acetyltriuret analog
identified. On the other hand, by hydrolysis, O-
demethylated thifensulfuron methyl undergoes opening
of the triazine ring to give the corresponding
acetyltriuret analog. Under photolytic conditions,
methyl 3-(4-methoxy-6-methyl-1,3,5-triazin-2-
yl)aminothiophene-2-carboxylate is identified.
