FLUMICLORAC-PENTYL Chemical Properties

Melting point:

90-91℃

Boiling point:

558.0±50.0 °C(Predicted)

Density 

d20 1.3316

storage temp. 

0-6°C

pka

-2.32±0.20(Predicted)

EPA Substance Registry System

Flumiclorac-pentyl (87546-18-7)

Safety Information

HS Code 

29251900

Toxicity

LD50 in rats (mg/kg): >5000 orally; >2000 dermally (Kamoshita)

FLUMICLORAC-PENTYL Usage And Synthesis

Chemical Properties

Pure product is white powdery solid. Melting point 88.9～90.1℃, relative density 1.33(20℃), vapor pressure 1.0×10-5Pa (25℃), partition coefficient 4.99 (20℃), solubility at 25℃: methanol 47.8g/L, n-octanol 16.0g/L, acetone 590g/L, n-hexane 3.28g/L, water 0.189mg/L, half-life in water 6min (pH=9), 19h (pH=7), 42d (pH=5). 6min (pH=9), 19h (pH=7), 42d (pH=5).

Uses

Flumiclorac-pentyl is a herbicide.

Uses

Herbicide.

Definition

ChEBI: Flumiclorac pentyl is a pyrroline.

Synthesis

Flumiclorac-pentyl is produced via a 5–6 step synthesis that commences with the preparation of the hexahydrophthalic anhydride core through Diels-Alder cycloaddition of maleic anhydride with cis-1,3-butadiene under high-pressure conditions in benzene, followed by ring opening to the diacid and condensation with methylamine in water to form N-methyl-hexahydrophthalimide. This imide is then lithiated and coupled via nucleophilic substitution to 2-chloro-4-fluoro-5-nitrophenyl acetate. Reduction of the nitro group using yields the amine intermediate, which undergoes intramolecular cyclisation with the acetate to form the cyclic imide.

Metabolic pathway

In the feces and urine of rats, more than 90% of administered 14C-flumiclorac pentyl is excreted within 48 h of treatment. Flumiclorac pentyl is rapidly and extensively metabolized. The major fecal metabolites are identified as the sulfonic acid conjugates, and the major urinary metabolite is identified as 5-amino-2- chloro-4-fluorophenoxyacetic acid. The metabolic reactions include cleavage of the ester linkage, cleavage of the imide linkage, hydroxylation and following reduction at the cyclohexene ring of the cyclohexene- 1,2-dicarboxylic acid moiety, and incorporation of a sulfonic acid group into the carbon ? carbon double bond of the 3,4,5,6-tetrahydrophthalimide moiety.

FLUMICLORAC-PENTYL(87546-18-7)Related Product Information

• Clethodim
• 3,4,5,6-Tetrahydrophthalimide
• 4-Fluorophenoxyacetic acid
• FLUMICLORAC-PENTYL
• 1-(3-METHOXYPHENYL)-2,5-DIHYDRO-1H-PYRROLE-2,5-DIONE
• 2-Chloro-4-fluorophenol
• 4'-CHLORO-2'-FLUOROACETANILIDE
• 3-AMINO-2,6-DIMETHYLPYRIDINE
• 3-Amino-4-fluorophenol
• Oxalic acid dihydrate
• Amyl acetate
• Oxalic acid
• N-METHYL-3,4,5,6-TETRAHYDROPHTHALIMIDE
• 1-(3-ETHOXYPHENYL)-1H-PYRROLE-2,5-DIONE
• CHEMBRDG-BB 9031620
• SALOR-INT L497096-1EA
• 1-(2-FLUOROPHENYL)-1H-PYRROLE-2,5-DIONE
• (4-FLUOROPHENOXY) ACETIC ACID ETHYL ESTER