| Identification | Back Directory | [Name]
CHLORFENPROP-METHYL | [CAS]
14437-17-3 | [Synonyms]
W-5769
B-57-10
B-7-533
bidisin
bay70533
bayer70533
methachlorphenprop
CHLORFENPROP-METHYL
chlorofenprop-methyl
chlorphenprop-methyl
CHLOROPHENPROP-METHYL
methylalpha,4-dichlorophenylpropanoate
CHLORFENPROP-METHYL PESTANAL (METHYL2-CH
2-chloro-3-(4-chlorophenyl)-methylpropionate
METHYL-2-CHLORO-3-(4-CHLOROPHENYL)-PROPIONATE
3-(4-chlorphenyl)-2-chlorpropionsaeuremethylester
Benzenepropanoic acid, α,4-dichloro-, methyl ester
methylesterkyseliny2-chlor-3-p-chlorfenylpropionove
2-chloro-3-(4-chlorophenyl)propionicacidmethylester
2-chloro-3-(4-chlorophenyl)-propionicacimethylester
chlorfenprop-methyl methyl 2-chloro-3-(4-chlorophenyl)propionate | [EINECS(EC#)]
238-413-5 | [Molecular Formula]
C10H10Cl2O2 | [MDL Number]
MFCD00055268 | [MOL File]
14437-17-3.mol | [Molecular Weight]
233.09 |
| Hazard Information | Back Directory | [Description]
Chorfenprop-methyl is an obsolete herbicide that was mainly used for controlling wild oats in winter cereals. It has a moderate aqueous solubility and is highly volatile. It is highly toxic to aquatic organisms. It is moderately toxic to mammals if ingested and is a recognised irritant. | [Uses]
Chlorophenprop-methyl is used in bacterial fermentation products. | [Definition]
ChEBI: Chlorfenprop-methyl is a member of monochlorobenzenes. | [Production Methods]
The commercial production of chlorfenprop-methyl begins with the preparation of 4-chlorocinnamic acid via a Perkin condensation, where 4-chlorobenzaldehyde is reacted with malonic anhydride in the presence of a base catalyst like pyridine or triethylamine, followed by hydrolysis and decarboxylation to yield the alpha,beta-unsaturated carboxylic acid. This intermediate is then hydrogenated using catalytic hydrogenation with palladium on carbon or Raney nickel in a solvent producing the saturated 3-(4-chlorophenyl)propionic acid. The key alpha-chlorination step involves treating the propionic acid with chlorine gas or N-chlorosuccinimide in an inert solvent under UV irradiation or free-radical initiation, introducing the chlorine at the alpha-position, yielding 2-chloro-3-(4-chlorophenyl)propionic acid. Finally, esterification is performed by reacting the chlorinated acid with methanol in the presence of a strong acid catalyst such as sulphuric acid, or via a Fischer-Speier method under reflux with Dean-Stark azeotropic removal of water, followed by neutralisation, extraction, and distillation to isolate technical-grade chlorfenprop-methyl. | [Mechanism of action]
Selective, basic metabolic processes become inactivated during autolysis | [Pesticide Type]
Herbicide |
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Energy Chemical
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TargetMol
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Carbosynth
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