| Identification | Back Directory | [Name]
Fluthiacet | [CAS]
149253-65-6 | [Synonyms]
Fluthiacet
Acetic acid, 2-[[2-chloro-4-fluoro-5-[(tetrahydro-3-oxo-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]phenyl]thio]- | [Molecular Formula]
C14H13ClFN3O3S2 | [MOL File]
149253-65-6.mol | [Molecular Weight]
389.85 |
| Hazard Information | Back Directory | [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 | [Pesticide Type]
Herbicide |
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