Description
Dichlorophen is a nontoxic laxative vermicide of chlorinated phenol compound. It is an anticestodal agent, fungicide, germicide, anti-protozoan and antimicrobial agent. Its efficacy is restricted to Taenia spp, with poor to no activity against Echinococcus spp and Dipylidium caninum. Against these and other species, it may act against the strobilus, leaving the scolex to generate new proglottids. Its mechanism of action is thought to induce the uncoupling of oxidative phosphorylation. Therefore, it can be included as an ingredient in antimicrobial soaps and shampoos. It can be used in combination with toluene for the removal of parasites such as ascarids, hookworms, and tapeworms from dogs and cats. Dichlorophene can be used as a growth regulator in containerized seedlings of pine and spruce to regulate plant growth.
Sources
https://www.sciencedirect.com/topics/agricultural-and-biological-sciences/dichlorophen
https://en.wikipedia.org/wiki/Dichlorophen
https://pubchem.ncbi.nlm.nih.gov/compound/Dichlorophen#section=Top
https://www.tabletwise.com/medicine/dichlorophene/uses-benefits-working
Andersson, B. "Analysis of plant growth regulating substances [incl. dichlorophene]." Annals of Applied Biology 43.2(1982):342-354.
Chemical Properties
white or off-white powder
Originator
Dichlorophen,Aquapharm
Uses
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.
Uses
Agricultural fungicide; antimicrobial; germicide in soaps, shampoos, etc.
Definition
ChEBI: Dichlorophen is a diarylmethane and a bridged diphenyl fungicide.
Production Methods
Dichlorophen is synthesised through a condensation reaction between p-chlorophenol and formaldehyde. In a typical procedure, equimolar amounts of these two reactants are refluxed in a water bath for about three hours. After the reaction, the mixture is added to distilled water and heated to around 80 DegC to remove any residual p-chlorophenol. Once cooled with crushed ice and stirred vigorously, the product precipitates out. This crude product is then purified by recrystallization using toluene, yielding dichlorophen.
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®
Mechanism of action
Contact. It is believed to act by disrupting mitochondrial function and interfering with oxidative phosphorylation in parasites and fungi
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.
Pesticide Type
Fungicide; Algicide; Veterinary substance
