Uses
Fluthiacet is a herbicide which works on most herbicide resistant weed species through inhibition of the enzyme protoporphyrinogen oxidase in target plants
Definition
ChEBI: Fluthiacet is a thiadiazolopyridazine that is 3-iminotetrahydro[1,3,4]thiadiazolo[3,4-a]pyridazin-1-one in which the exocyclic nitrogen has been substituted by a 5-[(carboxymethyl)thio]-4-chloro-2-fluorophenyl group. A protoporphyrinogen oxidase inhibitor, it is used (usually as the corresponding methyl ester proherbicide, fluthiacet-methyl) for the control of broad-leaved weeds in crops such as maize and soya. It has a role as an EC 1.3.3.4 (protoporphyrinogen oxidase) inhibitor, a herbicide and an agrochemical. It is an organic sulfide, a monocarboxylic acid, a member of monochlorobenzenes, a member of monofluorobenzenes and a thiadiazolopyridazine.
Production Methods
The herbicide fluthiacet is usually produced as the methyl ester via a multi-step chemical synthesis that involves constructing a thiadiazolopyridazine bicyclic system linked to a phenylthioacetate ester. Modern, cleaner industrial processes often employ a three-step synthesis, replacing hazardous materials like phosgene and thiophosgene with safer alternatives such as bis(trichloromethyl) carbonate (BTC) and carbon disulfide. A key step involves the condensation of a specifically substituted phenylthioacetic acid intermediate with a thiadiazolopyridazine dione, typically conducted in a solvent like methanol under reflux conditions. The process also involves the preparation of intermediates, such as 1-[(2-fluoro-4-chloro-5-thiomethylacetate)phenylthiocarbamoyl]-2-methoxycarbonylhexahydropyridazine, followed by ring closure. The resulting crude technical product is then purified through methods such as washing, drying, and recrystallisation to achieve the high purity required for agricultural application.
Mechanism of action
Inhibits protoporphyrinogen-oxidase enzyme leading to cell membrane damage, rapid action
