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122008-78-0

122008-78-0 Structure

122008-78-0 Structure
IdentificationBack Directory
[Name]

butyl 2-[4-(4-cyano-2-fluoro-phenoxy)phenoxy]propanoate
[CAS]

122008-78-0
[Synonyms]

Cyhalofop
Cyhalofop [iso
Cyhalofop acid
Cyhalofop Solution
Cyhalofop free acid
2-(4-ARYLOXYPHENOXY)PROPIONICACID
butyl 2-[4-(4-cyano-2-fluoro-phenoxy)phenoxy]propanoate
(R)-2-[4-(4-Cyano-2-fluorophenoxy)phenoxy]propionic acid
(2R)-2-[4-(4-Cyano-2-fluorophenoxy)phenoxy]propanoic acid
(R)-( )-2-(4-(2-Fluoro-4-cyanophenoxy)phenoxy)propanoic acid
Propanoic acid, 2-(4-(4-cyano-2-fluorophenoxy)phenoxy)-, (R)-
Propanoic acid, 2-[4-(4-cyano-2-fluorophenoxy)phenoxy]-, (2R)-
[Molecular Formula]

C16H12FNO4
[MDL Number]

MFCD28015762
[MOL File]

122008-78-0.mol
[Molecular Weight]

301.27
Chemical PropertiesBack Directory
[Melting point ]

50 °C
[Boiling point ]

446.0±45.0 °C(Predicted)
[density ]

1.36±0.1 g/cm3(Predicted)
[storage temp. ]

Sealed in dry,2-8°C
[solubility ]

DMSO (Slightly), Methanol (Slightly)
[form ]

Solid
[pka]

3.19±0.10(Predicted)
[color ]

White to Off-White
[Henry's Law Constant]

1.7×105 mol/(m3Pa) at 25℃, Ebert et al. (2023)
Safety DataBack Directory
[Hazard Codes ]

Xn,N
[Risk Statements ]

22-50
[Safety Statements ]

61
Hazard InformationBack Directory
[Description]

Cyhalofop is a post-emergence herbicide, used mainly for rice as the butyl variant. It is moderately soluble in water and non-volatile. It is not expected to be persistent in the environment. The risk of leaching to groundwater is low. It is moderately toxic to honeybees. It hs a low mammalian oral toxicity.
[Uses]

Cyhalofop is used as a pesticide for controlling pests.
[Production Methods]

The production of cyhalofop, usually as its active ester form, cyhalofop-butyl, involves a multi-step organic synthesis beginning with the etherification of 3,4-difluorobenzonitrile and hydroquinone under alkaline conditions to yield the key intermediate 4-(4-cyano-2-fluorophenoxy)phenol. This intermediate is then reacted with (S)-2-(4-methylbenzenesulfonyloxy)butyl propionate in the presence of potassium carbonate and a polar aprotic solvent like dimethyl sulfoxide. The reaction promotes nucleophilic substitution, forming the cyhalofop-butyl ester while minimising unwanted double etherification by-products. The final product is purified through standard techniques such as crystallisation or chromatography.
[Mechanism of action]

Systemic, foliar untake with no soil activity. Acetyl CoA carboxylase inhibitor (ACCase) - distrupts fatty acid biosynthesis and lipid formation.
[Pesticide Type]

Herbicide; Metabolite
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