Description
Fluazifop-butyl is an obsolete herbicide once used for the pre-emergence control of a wide range of grass weeds in a variety of cropping situations. It has a low aqueous solubility, miscible with many organic solvents and not considered to be volatile. Whilst data is limited, it does not appear to be persistent in soil systems and is not expected to leach to groundwater. Fluazifop-butyl has a low oral acute toxicity for mammals, birds and aquatic invertebrates but is slightly more toxic to bees and fish. The risks to human health are relatively low although it does appear to be a skin and eye irritant.
Chemical Properties
Pale yellow liquid. Odorless.
Chemical Properties
Pale straw-colored, odorless liquid.
Uses
Food additive; herbicide; agricultural chemical.
Uses
Fluazifop-butyl-d9 is the labeled version of Fluazifop-butyl (F407433), which is often found in herbicidal and fungicidal mixture compositions.
Production Methods
Fluazifop-butyl is commercially produced through a multi-step synthesis that centres on esterifying fluazifop acid with n-butanol. The process begins with the preparation of fluazifop acid, which contains a trifluoromethyl-substituted pyridyl ether linked to a phenoxypropionic acid backbone. This acid is then reacted with n-butanol in the presence of a dehydrating agent or acid catalyst to form the butyl ester, fluazifop-butyl. The esterification is typically carried out under reflux conditions in an organic solvent, followed by purification steps such as distillation or recrystallisation to isolate the active ingredient.
Definition
ChEBI: Butyl 2-(4-{[5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoate is a carboxylic ester resulting from the formal condensation of the carboxy group 2-(4-{[5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoic acid with the hydroxy group of butan-1-ol. It is a carboxylic ester, an organofluorine compound, a member of pyridines and an aromatic ether. It is functionally related to a 2-(4-{[5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoic acid and a butan-1-ol.
General Description
A pale straw colored liquid. Selective herbicide.
Air & Water Reactions
Slightly soluble in water.
Reactivity Profile
FLUAZIFOP-BUTYL is a trimethyl phenoxy pyridine ester. May react with acids to liberate heat. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. May generate heat with caustic solutions. Genreates flammable hydrogen with alkali metals and hydrides.
Hazard
Moderately toxic by ingestion.
Agricultural Uses
Herbicide: Fluazifop-butyl is a selective post-emergence herbicide. Its principal uses in California is on rights-of-way,
landscapes, almonds, cotton, and outdoor container nurseries. Not approved for use in EU countries. Not registered for use in the U.S. Used in southeast Asia. There are
18 global suppliers.
Trade name
FUSILADE®[C]; FUSILADE® MAX
(P-butyl); FUSION®; GRASS-B-GONE®; Greencrop;
HACHE UNO SUPER®; HORIZON®; ICI-A0009®;
ONESIDE®; ONESIDE EC®; ORNAMEC®; PP 009®;
SL-236®; TF 1169®; TS-7236®; TORNADO®
Mechanism of action
Selective, systemic, absorbed by leaves. Acetyl CoA carboxylase inhibitor (ACCase) - distrupts fatty acid biosynthesis and lipid formation.
Potential Exposure
Fluazifop-butyl is a selective post emergence aryloxyphenoxypropionate/organofluorine herbi cide. Its principal uses In California is on rights-of-way,
landscapes, almonds, cotton, and outdoor container
nurseries.
Metabolic pathway
Fluazifop butyl as a thin film on glass is
photorearranged by UV irradiation to the isomer
butyl-(RS)-2-[4-hydroxy-3-(5-trifluoromethyl-2-
pyridyl)phenoxy]propionate. Plants of both resistant
and susceptible populations of Digitaria sanguinalis
rapidly hydrolyze 14C-fluazifop butyl to corresponding
acid in leaves, but fluazifop acid is metabolized to
other compounds at a more rapid rate in the resistant
plants. An enhanced metabolism of toxophore,
fluazifop acid is a likely mechanism of resistance in
this population. The plants of putative resistant and
susceptible population of Digitaria sanguinalis (L.)
Scop had survived the application of 212 g/ha
fluazifop-P-butyl in the year of collection.
Waste Disposal
In accordance with
40CFR165, follow recommendations for the disposal of
pesticides and pesticide containers. Containers must be dis posed of properly by following package label directions or
by contacting your local or federal environmental control
agency, or by contacting your regional EPA office.
