Methyl 2-[2-chloro-4-fluoro-5-[(3-oxo-5,6,7,8-tetrahydro-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]sulfanylacetate

Uses

Herbicide.

Definition

ChEBI: Fluthiacet-methyl is a methyl ester resulting from the formal condensation of the carboxy group of fluthiacet with methanol. A proherbicide for fluthiacet, it is used for the control of broad-leaved weeds in crops such as maize and soya. It has a role as an agrochemical, an EC 1.3.3.4 (protoporphyrinogen oxidase) inhibitor and a proherbicide. It is an organic sulfide, a methyl ester, a member of monochlorobenzenes, a member of monofluorobenzenes and a thiadiazolopyridazine. It is functionally related to a fluthiacet.

Metabolic pathway

Fluthiacet methyl is converted to its isomer, urazole, by glutathione S-transferase (GST) and glutathione (GSH) from some plants and rat liver microsomes. Fluthiacet methyl inhibits Protox (protoporphyrinogen oxidase) activity after conversion to the corresponding urazole by GST and GSH. Fluthiacet methyl is chemically converted to urazole with a thiol anion in media by the nucleophilic reaction. It is also suggested that a free acid of urazole, desulfated urazole, and the oxidative ring-cleaved formyl degradation products result from hydrolysis with esterase from soybean seedlings.
When fluthiacet methyl is administered orally to rats in a single dose, 63-85% of the dose is excreted in the feces and 10-23% in the urine, respectively, after 48 h. The main metabolite is the isomer of fluthiacet methyl (urazole) which is also identified in the soil degradation products. Monohydroxylated products on the pyridazine ring are identified as metabolites by rats only.