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Dichlorophen

Dichlorophen structure

Dichlorophen 

structure
  • CAS No:

    97-23-4

  • Formula:

    C13H10Cl2O2

  • Chemical Name:

    Dichlorophen

  • Synonyms:

    Phenol,2,2′-methylenebis[4-chloro-;2,2′-Methylenebis[4-chlorophenol];G 4;Anthiphen;Bis(5-chloro-2-hydroxyphenyl)methane;Bis(2-hydroxy-5-chlorophenyl)methane;DDDM;DDM;Dicestal;5,5′-Dichloro-2,2′-dihydroxydiphenylmethane;Dichlorophen B;Dichlorophen;Dichlorophene;Dichlorphen;Didroxan;Didroxane;2,2′-Dihydroxy-5,5′-dichlorodiphenylmethane;Diphentane 70;Korium;Panacide;Prevental;Preventol GDC;Taeniatol;Teniathane;Teniatol;Diphenthane 70;Preventol GD;Dichlorophene 10;Di(5-Chloro-2-hydroxyphenyl)methane;Hyosan;Plath-Lyse;Bis(chlorohydroxyphenyl)methane;Gefir;G 4 Pure;G 4 Technical;Fungicide GM;Fungicide M;Dichlorofen;Antifen;Difentan;Teniotol;Gingivit;Cordocel;Halenol;Vermithana;Embephen;Palacel;Preventol;Sindar G 4;Sandocide;Giv Gard G 4-40;NSC 38642;NSC 39467;Diclorofen;M 213 (biocide);M 213;4,4′-Dichloro-2,2′-methylenediphenol;Xanbac;8017-86-5;1135443-66-1

  • Categories:

    Cosmetic Ingredient  >  Antimicrobials

Description

Dichlorophen is an anticestodal agent.


Dichlorophene appears as 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.


Dichlorophene appears as 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.|Dichlorophen is a diarylmethane and a bridged diphenyl fungicide.|Dichlorophen is an antimicrobial agent shown to exert activity against cestodes, protozoa, fungi, and bacteria. It is often combined with toluene to remove parasites including ascarids, tapeworm, and hookworm from dogs and cats.|Dichlorophen is a nontoxic laxative vermicide of chlorinated phenol compound. Dichlorophen is used as a veterinary fungicide, anthelmintic, and anti-protozoan, as well as an ingredient in antimicrobial soaps and shampoos. This agent probably acts by increasing the clearing of intestinal contents, thereby eradicating tapeworm infections from the intestines.|Nontoxic laxative vermicide effective for taenia infestation. It tends to produce colic and nausea. It is also used as a veterinary fungicide, anthelmintic, and antiprotozoan. (From Merck, 11th ed.)

Dichlorophen Basic Attributes

269.12

269.12

1884514

202-567-1

T1J0JOU64O

757391|39467|38642

DTXSID6021824

C47485

Colorless crystals

P - Antiparasitic products, insecticides and repellents

2908199022

Characteristics

40.5

4.26

Dichlorophene appears as 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.

1.4±0.1 g/cm3

177-178 °C

418.7±40.0 °C at 760 mmHg

207.0±27.3 °C

1.650

H2O: <0.1 g/100 mL at 22 ºC;soluble in methanol, ether

Safe Storage of Pesticides. Always store pesticides in their original containers, complete with labels that list ingredients, directions for use, and first aid steps in case of accidental poisoning. Never store pesticides in cabinets with or near food, animal feed, or medical supplies. Do not store pesticides in places where flooding is possible or in places where they might spill or leak into wells, drains, ground water, or surface water.

1.3 x 10 -5 Pa (25 °C)

Oral-Rat LD50: 1506 mg/kg; Oral-Mouse LD50: 1000 mg/kg

Combustion produces toxic chloride gas

Odorless

Henry's Law constant = 1.2X10-12 atm-cu m/mole at 25 °C (est)

pKa1 = 7.60; pKa2 = 11.6

147.4 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Slight phenolic smell, light tan powder /Technical grade/|Hydroxyl radical reaction rate constant = 2.5X10-11 cu cm/molec-sec at 25 °C (est)

Slowly oxidized in air. Insoluble in water.

Phenols and Cresols

DICHLOROPHENE is incompatible with strong oxidizing agents and strong bases (NTP, 1992). Weakly acidic.

Safety Information

III

9

UN 3077 9/PG 3

3

22-36-50/53

26-60-61

SM0175000

Xn,N

The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials

Stable. Incompatible with strong bases, strong oxidizing agents.

P273-P305 + P351 + P338

H302-H319-H400

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.|Safe Disposal of Pesticides. The best way to dispose of small amounts of excess pesticides is to use them - apply them - according to the directions on the label. If you cannot use them, ask your neighbors whether they have a similar pest control problem and can use them. If all of the remaining pesticide cannot be properly used, check with your local solid waste management authority, environmental agency, or health department to find out whether your community has a household hazardous waste collection program or a similar program for getting rid of unwanted, leftover pesticides. These authorities can also inform you of any local requirements for pesticide waste disposal.|Safe Disposal of Pesticides. An empty pesticide container can be as hazardous as a full one because of residues left inside. Never reuse such a container. When empty, a pesticide container should be rinsed carefully three times and the rinsewater thoroughly drained back onto the sprayer or the container previously used to mix the pesticide. Use the rinsewater as a pesticide, following label directions. Replace the cap or closure securely. Dispose of the container according to label instructions. Do not puncture or burn a pressurized container like an aerosol - it could explode. Do cut or puncture other empty pesticide containers made of metal or plastic to prevent someone from reusing them. Wrap the empty container and put it in the trash after you have rinsed it.

Dichlorophen is listed by the FDA as an over the counter (OTC) ingredient for antifungal and hair growth/loss treatment.|Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: dichlorophen is included in topical antifungal drug products.|Oral dosage form new animal drugs. Dichlorophene and toluene capsules. ... Indications for use: It is used for the removal of ascarids (Toxocara canis and Toxascaris leonina) and hookworms (Ancylostoma caninum and Uncinaria stenocephala) and as an aid in removing tapeworms (Taenia pisiformis, Dipylidium caninum, and Echinococcus granulosus) from dogs and cats.|Oral dosage form new animal drugs. Dichlorophene tablets. Indications for use: it is used /in dogs/ as a aid in the removal of tapeworms (Taenia pisiformis and Dipylidium caninum).

Flash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)

|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P273, P280, P301+P312, P305+P351+P338, P330, P337+P313, P391, and P501|H226 (12.19%): Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P370+P378, P391, P403+P233, P403+P235, P405, and P501|Aggregated GHS information provided by 484 companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Danger|P261, P264, P270, P272, P280, P301+P312, P302+P352, P305+P351+P338, P310, P321, P330, P333+P313, P363, and P501

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992)

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should keep this material in a tightly closed container under an inert atmosphere, and store it at refrigerated temperatures. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

If a spill occurs, clean it up promptly. Don't wash it away. Instead, sprinkle the spill with sawdust, vermiculite, or kitty litter. Sweep it into a plastic garbage bag, and dispose of it as directed on the pesticide product label.|After Applying a Pesticide, Indoors or Outdoors. To remove pesticide residues, use a bucket to rinse tools or equipment three times, including any containers or utensils that you used when mixing the pesticide. Then pour the rinsewater into the pesticide sprayer and reuse the solution by applying it according to the pesticide product label directions. After applying any pesticide wash your hands and any other parts of your body that may have come in contact with the pesticide..To prevent tracking pesticides inside, remove or rinse your boots or shoes before entering your home. Wash any clothes that have been exposed to a lot of pesticide separately from your regular wash.|AEROBIC: Dichlorophene, present at 100 mg/L, reached 0% of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/L and the Japanese MITI test(1). In another study, the initial rate of biodegradation of dichlorophene in sewage began rapidly (10-40 percent reduction after 1.5 days) and then slowed over a period of several days (20-55, 30-60, and 40-60 percent after 2.5, 3.5, and 7 days respectively)(2). Dichlorophene has been classified as a synthetic organic chemical unlikely to be removed during biological sewage treatment, even after prolonged exposure of the biota(3). Using a concentration of 10-20 mg/L, dichlorophene degraded 50 percent (aerobic) in an activated sludge test over a 2 week period(4).

Wear the items of protective clothing the label requires: for example, non-absorbent gloves (not leather or fabric), rubber footwear (not canvas or leather), a hat, goggles, or a dust-mist filter. If no specific clothing is listed, gloves, long-sleeved shirts and long pants, and closed shoes are recommended. You can buy protective clothing and equipment at hardware stores or building supply stores.|Indoor Applications. If the label directions permit, leave all windows open and fans operating after the application is completed. If the pesticide product is only effective in an unventilated (sealed) room or house, do not stay there. Put all pets outdoors, and take yourself any your family away from treated areas for at least the length of time prescribed on the label. Apply most surface sprays only to limited areas such as cracks; don't treat entire floors, walls, or ceilings. Don't let pesticides get on any surfaces that are used for food preparation. Wash any surfaces that may have pesticide residue before placing food on them.|Indoor Applications. When using total release foggers to control pests, use no more than the amount needed and to keep foggers away from ignition sources (ovens, stoves, air conditioners, space heaters, and water heaters, for example). Foggers should not be used in small, enclosed places such as closets and cabinets or under tables and counters.|Outdoor Applications. Never apply pesticides outdoors on a windy day (winds higher than 10 mph). Position yourself so that a light breeze does not blow pesticide spray or dust into your face.

Toxicity

moderately toxic

... A potentiating effect was observed both in vitro and in vivo when phenylmercuric acetate is added to hexachlorophene or dichlorophene.|Mongrel and beagle dogs were sprayed with Dichlorophene as the vehicle (one female and two males) and Dichlorophene plus 0.087% of the insecticide Dursban (two females and three males) once daily, 5 days per week, for a total of 10 applications. ... The eyes, nose, and ear canals were not protected from the spray except for precautions that pet owners would normally perform. No abnormal observations were made during daily observations and physical examinations or during opthalmoscopic examination before and 2 weeks after application of the spray. No mortalities occurred during the study. No significant differences were observed between pretest and final body weights. Hematologic and clinical chemistry data for each dog at 1, 2, and 4 weeks, which included blood urea nitrogen, blood glucose, serum glutamic-oxaloacetic transaminase, serum glutamicpyruvic transaminase, and alkaline phosphatase, were comparable to pretest and control values. Erythrocyte and plasma cholinesterase values did not differ significantly from both vehicle and control animals. Animals that received the Dichlorophene plus Dursban had significantly decreased plasma cholinesterase values from day 1 of the treatment period until 42 days after treatment was stopped. However, the values were not significant 74 days after treatment was stopped.

LD50 Rat (male) oral 1506 mg/kg|LD50 Rat (female) oral 1683 mg/kg|LD50 Mouse oral 1000 mg/kg|LD50 Guinea pig oral 1250 mg/kg|For more Non-Human Toxicity Values (Complete) data for DICHLOROPHENE (6 total), please visit the HSDB record page.

/AQUATIC SPECIES/ 5 ppm of Panacide prolonged the lag phase, decreased the growth rate and final yield of the green alga, Scenedesmus obliquus. Synthesis of nucleic acid remained stationary over the first 2 days. Synthesis of RNA and DNA was slower than in controls. Treatment with 20 ppm completely ended algal growth and resulted in lysis of cells after 72 hr contact. Synthesis of chlorophyll was also affected.

Dichlorophene's production and use as an anthelmintic(1) may result in its release to the environment through various waste streams(SRC). Dichlorophene is listed by the FDA as an over the counter (OTC) ingredient for antifungal and hair growth/loss treatment(2). Its former production and use in pesticide products as an algacide, fungicide, and bactericide(3) resulted in its direct release to the environment(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 4,950(SRC), determined from a log Kow of 4.26(2) and a regression-derived equation(3), indicates that dichlorophene is expected to have slight mobility in soil(SRC). Dichlorophene is a weak acid with pKa of 7.6(4), suggesting it will partially exist as an anion in moist soils. The anionic form of dichlorophene is expected to have greater mobility than the neutral species since anions do not adsorb to soils as strongly as uncharged compounds(5). Volatilization of dichlorophene from moist soil surfaces is not expected to be an important fate process(SRC) since anions do not volatilize and the Henry's Law constant of the neutral species is estimated as 1.2X10-12 atm-cu m/mole(SRC), derived from its vapor pressure, 9.8X10-11 mm Hg(4), and water solubility, 30 mg/L(4). Dichlorophene is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Screening studies using activated sludge and sewage suggest that dichlorophene is biodegradeable under aerobic conditions and low concentrations, but may be toxic to the microorganisms at higher concentrations(6-9).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 4,950(SRC), determined from a log Kow of 4.26(2) and a regression-derived equation(3), indicates that dichlorophene is expected to adsorb to suspended solids and sediment(SRC). Dichlorophene is a weak acid with pKa of 7.6(4), indicating it will partially exist as an anion at environmental pH(SRC). Volatilization from water surfaces will not occur for the anionic species since ions do not volatilize. Volatilization of the neutral species is not expected(3) based upon an estimated Henry's Law constant of 1.2X10-12 atm-cu m/mole(SRC), derived from its vapor pressure, 9.8X10-11 mm Hg(4), and water solubility, 30 mg/L(4). According to a classification scheme(5), BCF values of 26 to 281 measured in carp(6), suggest bioconcentration in aquatic organisms is moderate to high. Screening studies using activated sludge and sewage inoculum suggest that dichlorophene is biodegradeable under aerobic conditions and low concentrations, but may be toxic to the microorganisms at higher concentrations(6-9). Dichlorophene absorbs light greater than 290 nm and has been shown to undergo direct photolysis in aqueous solutions; however, the rate of this reaction was not reported(4,10).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dichlorophene, which has a vapor pressure of 9.8X10-11 mm Hg at 25 °C (2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase dichlorophene may be removed from the air by wet and dry deposition(SRC).

Photolysis of dichlorophene in acidic solution in the presence of oxygen results in loss of one chlorine atom and the formation of 4-chloro-4'hydroxy-2,2'methyldiphenol; in the presence of oxygen, the corresponding benzoquinone is formed(1,2). Irradiation of dichlorophene at pH 9 (under both oxygenated and unoxygenated conditions) also resulted in the formation of 4-chloro-2,2'methyldiphenol and 2-(5-chloro-2-hydroxy-benzyl)-cyclohex-2-ene-1,4-dione(2).

190.55|BCF values of 26 to 84 and 98 to 281 were measured for carp exposed to dichlorophene at concns of 50 ug/L and 5 ug/L, respectively, over an 8 week incubation period(1). According to a classification scheme(2), these BCF values suggest bioconcentration in aquatic organisms is moderate to high(SRC).

The Koc of dichlorophene is estimated as 4,950(SRC), using a log Kow of 4.26(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that dichlorophene is expected to have slight mobility in soil(SRC). Dichlorophene is a weak acid with pKa of 7.6(4), indicating that this compound will partially exist in anionic form in the environment(SRC). The anionic species is expected to have greater mobility in soils than the neutral species since anionic compounds typically adsorb less to soils than neutral compounds(5).

The Henry's Law constant for dichlorophene is estimated as 1.2X10-12 atm-cu m/mole(SRC) derived from its vapor pressure, 9.8X10-11 mm Hg(1), and water solubility, 30 mg/L(1). This Henry's Law constant indicates that dichlorophene is expected to be essentially non-volatile from water and moist soil surfaces(2). Additionally, dichlorophene is a weak acid with pKa of 7.6(1) indicating it will partially exist as an anion at environmental pH, and ionic species do not volatilize. Dichlorophene is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 4,290 workers (2,030 of these are female) are potentially exposed to dichlorophene in the US(1). Occupational exposure to dichlorophene may occur through inhalation of dusts or dermal contact with this compound at workplaces where it is produced or used(SRC). The general population may be exposed to dichlorophene through dermal exposure and ingestion of this compound and dermal contact with consumer products containing this compound(SRC).

Drug Information

Anticestodal Agents; Antifungal Agents; Antiprotozoal Agents; Cathartics|/SRP/: Dichlorophen is primarily effective against the large tapeworms of man & domestic animals. ... Dichlorophen is effective in clearing a large proportion of infections by Taenia saginata. Taenia solium is also susceptible... Available data suggest it may be useful against Diphyllobothrium latum & Hymenolepis mana infections.|Dichlorophen is given orally without preliminary fasting or other prior preparation of the patient. Satisfactory results have been obtained by giving 2-3 g every 8 hr for 3 doses (children, 1-2 g). Alternatively, single dose of 6 g (children, 2-4 g) may be given on each of 2 successive days.|Medication (Vet): Antihelmintic. Targets Cestodes. ... antiprotozoal,... antifungal agent|Anthelmintic agent for Tapeworms in human & vet medicine

...Usually nothing recognizable or only partially disintegrated mature segments can be seen in the stool. This presents difficulty in diagnosing cure, &, therefore, careful follow-up of the patient is required.|...There may be danger of cysticereosis from liberated ova.

3. 3= MODERATELY TOXIC: Probable oral lethal dose (human) 0.5-5 g/kg, between 1 oz & 1 pint (or 1 lb) for 70 kg person (150 lbs).

Agents used to treat tapeworm infestations in man or animals. (See all compounds classified as Anticestodal Agents.)|Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. (See all compounds classified as Antifungal Agents.)|Substances that are destructive to protozoans. (See all compounds classified as Antiprotozoal Agents.)

Following oral administration to the rat, (14)C-dichlorophen was well absorbed with 78% of the dose excreted in the urine and 15% in the feces in 2 days.|/Investigators/ dosed female Wistar albino rats (3/group) orally with 50 mg/kg [14C]-dichlorophene dissolved in propane-1,2-diol. One group of rats was bile-duct cannulated 1 hr after oral administration of [14C]-dichlorophene. An average of 95% [14C]-dichlorophene was excreted in the urine and feces 2 days after dosing. Most (78%) of the biocide was recovered in the urine, and 17% was recovered in the feces.

/Investigators/ dosed female Wistar albino rats (3/group) orally with 50 mg/kg [14C]-dichlorophene dissolved in propane-1,2-diol. ... The following urinary metabolites were identified: 4% dichlorophene; 17% dichlorophene sulfate; 25% dichlorophene monoglucuronide; and 19% dichlorophene diglucuronide. Bile duct-cannulated rats excreted 36% of the dose of [14C]-dichlorophene 1 to 4 hr after dosing. The intestinal contents and the intestinal wall had 32% and 11% [14C]-dichlorophene, respectively, whereas 2% was found in the urine. Only the monoglucuronide metabolite of [14C]-dichlorophene was found in the bile. The investigators suggested that dichlorophene underwent enterohepatic circulation.|/Investigators examined/ the metabolites of dichlorophene from enterohepatic circulation in female Vom strain rats. Female rats were dosed orally with 50 mg/kg [14C]-dichlorophene (5 uCi/kg) and were bile-duct cannulated 1 hr later. Bile and urine were collected for 3 hr. The bile was then infused into the duodenum of another set of cannulated rats, from which bile and urine were collected. This process was repeated with a third set of rats. Five rats were used in each experiment. The only biliary metabolite was the monoglucuronide in all three experiments. In the urine, dichlorophene sulfate and diglucuronide were the major metabolites. Blood from the hepatic portal vein in rats receiving bile contained free dichlorophene and its monoglucuronide.|/After/ orally administered dichlorophene: (1) dichlorophene is absorbed from the gut, is conjugated to the sulfate and monoglucuronide in the gut wall, and passes to the liver where more of these metabolites can be formed; (2) the diglucuronide is formed in the liver or other organs perfused by systemic circulation; (3) the sulfate and diglucuronide are eliminated from the peripheral circulation via the kidneys; (4) the diglucuronide is too water soluble for biliary excretion; however, most of the monoglucuronide undergoes biliary excretion; (5) residual monoglucuronide is metabolized to sulfate and diglucuronide on subsequent passes through the enterohepatic cycle and these are eliminated via the kidneys.

0.31 Days

Dichlorophene is usually contaminated with the trimer 4-chloro-2,6-bis(5-chloro-2-hydroxybenzyl)phenol, which results from the synthesis process ... the trimer constitutes 5% to 10% by weight of Dichlorophene.

SYMPTOMS: Symptoms of exposure to this compound include sensitivity dermatitis, photosensitivity and stomatitis. Other symptoms include nausea, vomiting, gastrointestinal colic, diarrhea, urticarial rash and jaundice. Irritation of the skin, eyes, mucous membranes and upper respiratory tract may also occur. It can cause cramps. Symptoms of exposure to related compounds include necrosis of the mucous membranes, cerebral edema, degenerative changes in the liver and kidneys, bladder necrosis, collapse, coma, painless blanching or erythema, possible corrosion, profuse sweating, intense thirst, cyanosis from methemoglobinemia, hyperactivity, stupor, blood pressure fall, hyperpnea, abdominal pain, hemolysis, convulsions and pulmonary edema followed by pneumonia. If death from respiratory failure is not immediate, oliguria or anuria may occur. ACUTE/CHRONIC HAZARDS: This compound is toxic by ingestion. It is an irritant. When heated to decomposition it emits toxic fumes of carbon monoxide, carbon dioxide and hydrogen chloride gas. (NTP, 1992)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Administer activated charcoal ... . Do not use emetics. Cover skin burns with dry, sterile dressings after decontamination ... . Maintain body temperature. /Phenols and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious or in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors for hypotension with a normal fluid volume. Watch for signs of fluid overload ... Administer 1% solution methylene blue if patient is symptomatic with severe hypoxia, cyanosis, and cardiac compromise not responding to oxygen. ... . Treat seizures with diazepam (Valium). ... Use proparacaine hydrochloride to assist eye irrigation ... . /Phenols and related compounds/

/HUMAN EXPOSURE STUDIES/ /Investigators/ photopatch tested 352 subjects because they had a history suggestive of photosensitivity or an eruption involving sun-exposed areas. Most of the subjects with a positive photopatch test were in their fifth to sixth decade of life and none were children. Dichlorophene (1% in white petrolatum) was applied in duplicate by routine patch-testing procedures. Aluminum patches and plastic tape were used. One of the duplicate set was removed and examined at 24 hr. The skin was cleansed and exposed for 30 s through a window glass filter to 3.56 joules/sq cm of long wave UV rays between 320 and 400 nm from a hot quartz contact lamp at 3.4 cm. The irradiated and closed patch test sites were examined 48, 72, 96, and sometimes 120 hr after initial application. There were 13/352 positive photopatch tests to dichlorophene.|/HUMAN EXPOSURE STUDIES/ /Investigators/ photopatch tested 108 men and women patients with a suspected photodermatitis. The photopatch series tested in duplicate included dichlorophene at a concentration of 1% in petrolatum. Photopatch tests were applied to the patient's back, one on either side of the midline. Photopatch tests were removed at day 2 and irradiated with 10 J/sq cm UVA from Philips TL K40 W109 N fluorescent tubes. Readings were performed on days 3 and 4. The diagnoses were as follows: contact allergy if both nonirradiated and irradiated sites were positive; photocontact allergy if only the irradiated site had a positive reaction; and contact allergy associated with photoallergy if both sites were positive but the irradiated site had a stronger reaction than the nonirradiated one. None of the 108 patients had a positive photopatch test to dichlorophene.|/HUMAN EXPOSURE STUDIES/ /Investigators/ described the outbreak of dermatitis in 15 subjects in which eruptions affected the dorsal surfaces of the hands and fingers, which were dry, scaly, and erythematous with a tendency to fissure. One subject had eruptions on the palms and forearms. The standard A1-test were carried out on samples of 2.5% dichlorophene in PMF (not defined). Four of the subjects were sensitive to dichlorophene, reactions varied from 2+ to 3+.|/SIGNS AND SYMPTOMS/ Appreciable proportion of treated patients experience colic, diarrhea, and nausea lasting from 4-6 hr. Vomiting may occur occasionally. Lassitude is another common symptom.|For more Human Toxicity Excerpts (Complete) data for DICHLOROPHENE (16 total), please visit the HSDB record page.

Dichlorophen

Dichlorophen Use and Manufacturing

Methods of Manufacturing

First, add solvent ethanol and catalyst amount of concentrated sulfuric acid to the reaction kettle, then add 277 kg of p-chlorophenol, cool to -10 ~ 0 ℃, start dropping 30 kg of formaldehyde, and react for 6 hours. After the reaction, it was allowed to stand, filtered, and dried to obtain a solid product.

Uses

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

Production

(1979) PROBABLY GREATER THAN 2.27X10+6 GRAMS|(1981) PROBABLY GREATER THAN 2.27X10+6 GRAMS|(1986) 10 thousand-500 thousand pounds[US EPA; Non-confidential Production Volume Information Submitted by Companies for Chemicals Under the 1986-2002 Inventory Update Rule (IUR). Phenol, 2,2'-methylenebis|(1994) 10 thousand-500 thousand pounds[US EPA; Non-confidential Production Volume Information Submitted by Companies for Chemicals Under the 1986-2002 Inventory Update Rule (IUR). Phenol, 2,2'-methylenebis|For more U.S. Production (Complete) data for DICHLOROPHENE (6 total), please visit the HSDB record page.

Dichlorophen is used as such; as 'panacide', an aqueous solution of monosodium salt (400 g/L); or the anthelmintic, 'Antiphen'.|GO4 technical; g-4-40%= 40% solution of monosodium salt.|Dichlorophen (Anthiphen) is not marketed in the United States. It is supplied as scored tablets containing 500 mg of active material.|Selected products: Xanbac D, Fungo, Mascot, Nomix-Chipman Mosskiller, Panacide, Super Mosstox; mixtures: Synergol (+1-naphthylacetic acid + 4-indol-3-ylbutyric acid). Discontinued products: Panaclean.|Grade: Pure and technical

Phenol, 2,2'-methylenebis[4-chloro-: ACTIVE|Chlorinated bisphenol antibacterial & antifungal agents are potent inhibitors of torula yeast (Candida utilis) glucose 6-phosphate dehydrogenase. Several compounds were tested including 2,2'-methylenebis(4,6-dichlorophenol).|Dichlorophen is fungicide & bactericide recommended for the protection of textiles & materials including horticultural benches & equipment against moulds & algae. It is...basis of a preparation against athlete's feet.

Spectrophotometric method. Colorimetric method, using 4-aminoantipyrene with potassium periodate as an oxidizing agent.|The germicide dichlorophene was determined in cosmetics by high performance liquid chromatograhy.|Method: AOAC 972.48; Procedure: spectrophotometric method; Analyte: dichlorophene; Matrix: drugs; Detection Limit: not provided.|A stability indicating, reversed phase high performance liquid chromatographic method for the determination of dichlorophen and a trimer impurity in raw material and veterinary capsules is described. Utility of the method is demonstrated by assay of 3 formulations, showing concentrations of 7.14, 7.90 and 8.4% trimer.

Agrochemicals -> Fungicides, Herbicides|Animal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients|Pharmaceuticals -> Animal Drugs -> Approved in Taiwan|Cosmetics -> Antimicrobial; Deodorant

Computed Properties

Molecular Weight:269.12
XLogP3:4.3
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:268.0057849
Monoisotopic Mass:268.0057849
Topological Polar Surface Area:40.5
Heavy Atom Count:17
Complexity:226
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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