Dichlorophen

Chemical properties

white or off-white powder

Originator

Dichlorophen,Aquapharm

The Uses of Dichlorophen

Dichlorophen exhibits algicidal, bactericidal and fungicidal activities. It is a contact fungicide used to control dollar spots and rots in turf. It is also an anthelminthic used for the treatment of various tapeworms in human and domestic animals.

The Uses of Dichlorophen

anthelmintic

The Uses of Dichlorophen

Agricultural fungicide; antimicrobial; germicide in soaps, shampoos, etc.

What are the applications of Application

Dichlorophen is an effective fungicide against celluloytic fungi

Definition

ChEBI: Dichlorophen is a diarylmethane and a bridged diphenyl fungicide.

Manufacturing Process

2.520 g of sulfuric acid (93%) is stirred and cooled to 0°C. A solution of 552 g of p-chlorophenol in 305 g of methyl alcohol is run into the acid, the temperature being kept below 10°C. The mixture is cooled to -5°C and a solution of 170 g of aqueous formaldehyde solution (37% CH2O in water) in 332 g of methyl alcohol is introduced at a more or less uniform rate over a period of 4 hours. The temperature of the reaction mixture is not allowed to rise above 0°C. After all of the formaldehyde-containing solution has been added, the batch is stirred for 3 hours longer at a temperature of -5°-0°C.
Enough ice is then added to the contents of the reaction chamber in order to reduce the sulfuric acid concentration to 70%. 2,2'-Dihydroxy-5,5'-dichlorodiphenyl methane is extracted from the resulting mixture with a mixture of 1.069 g of isopropyl ether and 1.575 g of toluene. Ice is added until the acid concentration is about 30%. The acid layer is removed and the solvent layer is washed acid-free. Most of the isopropyl ether is removed by atmospheric distillation with a fractionating column, the temperature of the escaping vapors not being permitted to exceed 90°C. From the residue, about 280 g of pure 2,2'-dihydroxy-5,5'-dichloro-diphenyl methane, MP: 177°-178°C, crystallize. The product is filtered, washed with toluene and dried at about 100°C. By concentrating the mother liquor remaining after the foregoing crystallization and filtration, another 225 grams of substantially pure 2,2'- dihydroxy-5,5'-dichloro-diphenyl methane are obtained. This latter crop may be crystallized from toluene in order to convert it into 2,2'-dihydroxy-5,5'- dichlorodiphenyl methane of melting point of 177°-178°C.

Therapeutic Function

Antiseptic, Anthelmintic, Antifungal

General Description

White slightly cream or light pink-colored powder. Melting point 177°C. Slight phenolic odor and a saline phenolic taste. Moderately toxic. Used as a fungicide and bactericide.

Air & Water Reactions

Slowly oxidized in air. Insoluble in water.

Reactivity Profile

Dichlorophen is incompatible with strong oxidizing agents and strong bases . Weakly acidic.

Fire Hazard

Flash point data for Dichlorophen are not available; however, Dichlorophen is probably combustible.

Agricultural Uses

Fungicide, Herbicide, Bactericide, Veterinary medicine: Not currently registered in the U.S. Dichlorophene is a wide-spectrum, non-oxidizing biocide used against all types of algae and bacteria. Widely used to treat fungi, fleas and worm conditions in pet animals and livestock. See U.S. Food and Drug Administration 20 CFR 520.580 and 20 CFR 520.581

Trade name

ANTHIPHEN®; DIPHENTANE 70®; DICHLOROPHEN®; DICHLOROPHEN B®; DICHLOROPHENE 10®; DICHLORPHEN®; DIDROXANE®; DIPHENTHANE 70®; FUNGICIDE F®; FUNGICIDE GM®; FUNGICIDE M®; G 4®; GEFIR®; HYOSAN; KORIUM®; PLATH-LYSE®; PREVENTAL®; PREVENTOL®; PREVENTOL GD®; PREVENTOL GDC®; SUPER MOSSTOX®; TAENIATOL®; TENIATOL®; TENIATHANE®; TRIVEX®; VERMITHANA®; WESPURIL®

Safety Profile

Poison by intravenous route. Moderately toxic by ingestion. A skin and severe eye irritant. Mutation data reported. Can cause cramps and diarrhea. Possibly similar to DDT. An FDA over-the counter drug. An anthelmintic. When heated to decomposition it emits toxic fumes of Cl-.

Metabolic pathway

Limited information is available to describe the degradation and metabolic fate of dichlorophen. A photodegradation study showed that dichlorophen undergoes hydroxydechlorination and dechlorination reactions as the major degradation pathways. Direct conjugation of one or both hydroxyl groups with sulfate and/or glucuronic acid was observed as the major metabolic pathway in the rat.

Purification Methods

Crystallise dichlorophen from toluene. [Beilstein 6 III 5406.]

Degradation

Dichlorophen (1) underwent hydroxydechlorination in acidic solution (pH 5.6) when irradiated under a xenon lamp (280 and 300 nm). 4-Chloro- 4'-hydroxy-2,2'-methylenediphenol(2) was the major product from reactions conducted in the absence of oxygen. A benzoquinone-like tautomer (3) was detected in oxygenated solution. A dechlorination product [4- chloro-2,2'-methylenediphenol(4)] was also observed as a minor product (Mansfield and Richard, 1996). These pathways are shown in Scheme 1.