Clorofen

1.22 (NTP, 1992) - Denser than water; will sink

1.185 at 58 °C

less than 1 mg/mL at 61 °F (NTP, 1992)

Highly sol in alcohol and other org solvents

In water, 149 mg/L at 25 °C

320 to 324 °F at 3.5 mmHg (NTP, 1992)

160-162 °C at 3.5 mm Hg

119.3 °F (NTP, 1992)

48.5 °C

0.1 mmHg at 68 °F (NTP, 1992)

0.0000506 [mmHg]

1.87X10-7 kPa = 1.4X10-6 mm Hg /extrapolated/

Ortho-benzyl-para-chlorophenol appears as white to light tan or pink flakes or white crystals. Insoluble in water. Slight phenolic odor. (NTP, 1992)

White to light tan or pink solid; [Hawley]

Danger

H315: Causes skin irritation [Warning Skin corrosion/irritation]；H317: May cause an allergic skin reaction [Warning Sensitization, Skin]；H318: Causes serious eye damage [Danger Serious eye damage/eye irritation]；H332: Harmful if inhaled [Warning Acute toxicity, inhalation]；H351: Suspected of causing cancer [Warning Carcinogenicity]；H361f: Suspected of damaging fertility [Warning Reproductive toxicity]；H373: May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]；H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]；H410: Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

P203, P260, P261, P264, P264+P265, P271, P272, P273, P280, P302+P352, P304+P340, P305+P354+P338, P317, P318, P319, P321, P332+P317, P333+P317, P362+P364, P391, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 3.3% (5 of 150) of reports.

Chemical: Phenol, 4-chloro-2-(phenylmethyl)-

Reg. (EC) No 2076/2002

Status: Active Update: 16-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/25019

2-Benzyl-4-chlorophenol: Does not have an individual approval but may be used under an appropriate group standard

SYMPTOMS: Symptoms of exposure to this compound in humans include drowsiness, loss of consciousness, irregular pulse and cyanosis. It may also cause irritation of the skin and mucous membranes. It is corrosive to the eyes, and extremely corrosive to the mouth and throat. Swallowing dusts or solids causes severe and rapid burning of the mouth, throat and digestive tract accompanied by severe pain, vomiting and collapse. It has also caused severe porphyrea cutanea tarda.；ACUTE/CHRONIC HAZARDS: This compound is a highly toxic irritant. It is irritating to the skin and respiratory tract, and corrosive to the eyes. It is also extremely corrosive to the mouth and throat. When heated to decomposition it emits toxic fumes of carbon monoxide, carbon dioxide, chlorine or hydrogen chloride, and other unidentified organic compounds in black smoke. (NTP, 1992)

Emergency medical treatment: see phenol and related agents; A skin irritant; One of the chemicals that can cause toxic vitiligo; [HSDB] Chemical leukoderma is indistinguishable from vitiligo; May occur in workers exposed to hydroquinones, catechols, phenols, or mercaptoamines; [White, p. 285] A mutagen, tumorigen, and mild skin irritant; Causes somnolence and convulsions in lethal-dose studies of mice; [RTECS] A skin, mucous membrane, and respiratory tract irritant; Corrosive to eyes; It has also caused severe porphyria cutanea tarda. [CAMEO] Chemical associated with acquired porphyria include hexachlorobenzene, 2,4-dichlorophenol, 2,4,5-trichlorophenol, 2,3,7,8-tetrachlorodibenzo-p-dioxin, o-benzyl-p-chlorophenol, 2-benzyl-p-dichlorophenol, vinyl chloride, lead, and aluminum; However, recent studies have failed to find an association between 2,3,7,8-tetrachlorodibenzo-p-dioxin and porphyrin levels; [LaDou, p. 266, 519] Corrosive to eyes; Causes kidney injury in chronic animal experiments and is a possible human carcinogen; [Reference #1] An irritant; Effects in high-dose animal studies include convulsions; [MSDSonline]

DHHS/NTP; Toxicology & Carcinogenesis Studies of o-Benzyl-p-chlorophenol in F344/N Rats and B6C3F1 Mice (Gavage Studies) Technical Report Series No. 424 (1994) NIH Publication No. 94-3155

USEPA/Office of Pesticide Programs; Reregistration Eligibility Decision Document - ortho-benzyl-para-chlorophenol. The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the U.S.[Available from, as of February 6, 2006: http://www.epa.gov/pesticides/reregistration/status.htm]

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 2-Benzyl-4-chlorophenol is included on this list.

Residues of the following chemical substances are exempted from the requirement of a tolerance when used in accordance with good manufacturing practice as ingredients in an antimicrobial pesticide formulation, provided that the substance is applied on a semi-permanent or permanent food-contact surface (other than being applied on food packaging) with adequate draining before contact with food. ... (c) The following chemical substances when used as ingredients in an antimicrobial pesticide formulation may be applied to: Food-processing equipment and utensils. 2-Benzyl-4-chlorophenol is included on this list. Limit: When ready for use the end-use concentration is not to exceed 320 ppm.

Based on the reviews of the generic data for the active ingredient of ortho-Benzyl-para-chlorophenol and its salts, the Agency has sufficient information on the health effects of ortho-Benzyl-para-chlorophenol and on its potential for causing adverse effects in fish and wildlife and the environment. The Agency has determined that products containing ortho-Benzyl-parachlorophenol and its salts labeled and used as specified in this Reregistration Eligibility Decision, except the enclosed area fogging application will not pose unreasonable risks or adverse effects to humans or the environment. Therefore, the Agency concludes that all the uses of products containing ortho-Benzyl-parachlorophenol, Potassium -2-benzyl-4-chlorophenate and Sodium 2-benzyl-4- chlorophenate are eligible for reregistration. The Agency is requiring handler exposure data on the fogging application and cannot make an eligibility decision on this method until these data are generated.

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA, as amended in 1988, were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. 2-Benzyl-4-chlorophenol is found on List B. Case No: 2045; Pesticide type: fungicide, antimicrobial; Case Status: RED Approved 09/95; OPP has made a decision that some/all uses of the pesticide are eligible for reregistration, as reflected in a Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): 2-benzyl-4-chlorophenol; Data Call-in (DCI) Date(s): 06/10/91, 11/15/96; AI Status: OPP has completed a Reregistration Eligibility Decision (RED) document for the case/AI.

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. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas.；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. Phenols are very toxic poisons AND corrosive and irritating, so that inducing vomiting may make medical problems worse. IMMEDIATELY call a hospital or poison control center and locate activated charcoal, egg whites, or milk in case the medical advisor recommends administering one of them. If advice from a physician is not readily available and the victim is conscious and not convulsing, give the victim a glass of activated charcoal slurry in water or, if this is not available, a glass of milk, or beaten egg whites and IMMEDIATELY transport victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, assure 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)

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.

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.

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 store this chemical under refrigerated temperatures, and protect it from light. (NTP, 1992)

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.

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.

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:；IMMEDIATE PRECAUTIONARY MEASURE: Isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids.；SPILL: Increase the immediate precautionary measure distance, in the downwind direction, as necessary.；FIRE: If tank, rail tank car or highway tank is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2024)

Residues of the following chemical substances are exempted from the requirement of a tolerance when used in accordance with good manufacturing practice as ingredients in an antimicrobial pesticide formulation, provided that the substance is applied on a semi-permanent or permanent food-contact surface (other than being applied on food packaging) with adequate draining before contact with food. ... (c) The following chemical substances when used as ingredients in an antimicrobial pesticide formulation may be applied to: Food-processing equipment and utensils. 2-Benzyl-4-chlorophenol is included on this list. Limit: When ready for use the end-use concentration is not to exceed 320 ppm.

MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves.；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)

LD50 Colinus virginianus (Bobwhite quail, 6 months old) oral >2510 mg/kg

LC50 Colinus virginianus (Bobwhite quail, 13 days old) dietary >5620 ppm/8 days

LC50 Anas platyrhynchos (Mallard duck, 9 days old) dietary >5620 ppm/8 days

LC50 Lepomis macrochirus (Bluegill) 0.33 ppm/96 hr (95% confidence limit: 0.2-0.4 ppm); static /formulated product/

For more Ecotoxicity Values (Complete) data for O-BENZYL-P-CHLOROPHENOL (6 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), a Koc value of 2,050(2), indicates that o-benzyl-p-chlorophenol is expected to have slight mobility in soil(SRC). Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 2.7X10-9 atm-cu m/mole(SRC) derived from its extrapolated vapor pressure, 1.4X10-6 mm Hg(2), and water solubility, 149 mg/L(2). Volatilization from dry soil surfaces is not expected to be important based on the vapor pressure of this compound(2). Biodegradation of o-benzyl-p-chlorophenol is expected to occur rapidly based on degradation half-lives of 1 to 2 days, in a sewage sludge(2).

AQUATIC FATE: Based on a classification scheme(1), a Koc value of 2,050 (2), indicates that o-benzyl-p-chlorophenol is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected to be an important fate process(3) based upon an estimated Henry's Law constant of 2.7X10-9 atm-cu m/mole(SRC) derived from its extrapolated vapor pressure, 1.4X10-6 mm Hg(2), and water solubility, 149 mg/L(2). According to a classification scheme(4), a BCF of 75 measured in fish(2), suggests bioconcentration in aquatic organisms is moderate(SRC). An aqueous photolysis half-life of approximately 0.7 days(2), indicates photolysis in sunlit surface waters will be an important fate process(SRC). In addition, river die-away studies using non-acclimated river water indicates that the biodegradation half-life of o-benzyl-p-chlorophenol is approximately 1 to 3 days(2,5).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), o-benzyl-p-chlorophenol, which has an extrapolated vapor pressure of 1.4X10-6 mm Hg at 25 °C(2), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase o-benzyl-p-chlorophenol is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be about 22 hours (SRC), calculated from its rate constant of 1.8X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase o-benzyl-p-chlorophenol may be removed from the air by wet and dry deposition(SRC). o-Benzyl-p-chlorophenol has been shown to undergo direct photolysis in aqueous solutions with a half-life of approximately 0.7 days(2), which indicates that direct photolysis in the atmosphere may be possible(SRC).

The CIR Expert Panel concludes that the available data are insufficient to support safety of Dichlorophene or Chlorophene.

Ingredients for which the data are insufficient and their use in cosmetics is not supported

AR binding was observed for clorophene, which were both associated with delays in sexual development and decrements in reproductive performance.

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=120-32-1]

Influent and effluent samples from 11 municipal sewage treatment plants in St. Louis, MO and Dayton, OH, were obtained during November, 1978 and August, 1981 respectively. Influent concentrations averaged 14.8 ug/L o-benzyl-p-chlorophenol with a range of concentrations from <0.1 to 115 ug/L. Effluent concentrations averaged 0.8 ug/L o-benzyl-p-chlorophenol with a range of concentrations from <0.1 to 28 ug/L. Sludge concentrations were an average of 23 mg/kg o-benzyl-p-chlorophenol with a range of concentrations from 13 to 30 mg/kg(1). Municipal wastewater was monitored in Vancouver, BC from June through August 1983; o-benzyl-p-chlorophenol was qualitatively detected in both wastewater and sludge base/neutral extracts(2). o-Benzyl-p-chlorophenol was identified, not quantified, in the effluent of a sewage treatment plant in New Jersey at an unreported date; there were no industrial contributors to this waste site(3).

An experimentally determined Koc of 2050 was obtained by equilibrating aqueous solutions of o-benzyl-p-chlorophenol (at concentrations ranging from 0.5 to 10 mg/L) with four different soils, with organic carbon contents ranging from 0.41 to 1.97%, and then analyzing both soil and water phases for o-benzyl-p-chlorophenol(1). According to a suggested classification scheme(2), this Koc value indicates that o-benzyl-p-chlorophenol is expected to have slight mobility in soil(SRC).

/HUMAN EXPOSURE STUDIES/ /Investigators/ studied two epidemics of hyperbilirubinemia in infants in two hospitals. A total of 10 infants were diagnosed with hyperbilirubinemia between the two hospitals. The infants were exposed to a germicidal phenolic compound that contained 3.5% chlorophene and other ingredients. Serum samples were analyzed for chlorophene and 7/10 infants from the same hospital had positive results that ranged from 360 to 4390 ng/mL.

/SIGNS AND SYMPTOMS/ SYMPTOMATOLOGY: 1. Burning pain in mouth & throat. White necrotic lesions in mouth, esophagus & stomach. Abdominal pain, vomiting...& bloody diarrhea. 2. Pallor, sweating, weakness, headache, dizziness, tinnitus. 3. Shock: weak irregular pulse, hypotension, shallow respirations, cyanosis, and a profound fall in body temperature. 4. Possibly fleeting excitement (delirium), followed by unconsciousness. Convulsions are rarely seen except in children. 5. Stertorous breathing, mucous rales, rhonchi, frothing at nose & mouth ... pulmonary edema are sometimes seen. Characteristic odor of phenol on breath. Scanty, dark-colored or "smoky" urine. 6. If death does not occur promptly, moderately severe renal insufficiency may appear. 7. Death from respiratory, circulatory or cardiac failure. 8. If spilled on skin, pain is followed promptly by numbness. The skin becomes blanched, & a dry opaque eschar forms over the burn. When the eschar sloughs off, a brown stain remains. /Phenol/

/CASE REPORTS/ A cleaning woman who mixed a commercial solution of this disinfectant with hypochlorite bleach suffered a severe attack of porphyrea cutanea tarda, probably because of polychlorinated phenolic derivatives generated in the mixture ... .

/CASE REPORTS/ A 49-year-old subject presented with a 1-year history of an itchy, erythematous, scaly eruption that involved the fingers, finger webs, palms, dorsa of both hands, and patches on the right forearm. Subsequent patch testing with a 1% chlorophene concentration produced a strong positive reaction (++). Control subjects (50) were also patch tested with a 1% chlorophene concentration, of which 3 subjects had mild irritant reactions and 47 had no reaction.

For more Human Toxicity Excerpts (Complete) data for O-BENZYL-P-CHLOROPHENOL (9 total), please visit the HSDB record page.

AEROBIC: Biodegradation rate constants and half-lives of 0.21 to 1.04/days and <1 to 3 days, respectively, were reported in river die away studies using unacclimated river water containing 0.1 mg/L o-benzyl-p-chlorophenol(1). The biodegradation half-life of o-benzyl-p-chlorophenol at an initial concentration of 0.5 mg/L was 1 to 2 days, in a sewage sludge(1). Activated sludge with an initial concentration of 0.5 mg/L o-benzyl-p-chlorophenol had a biodegradation rate constant of 3.88/days and a half life of 0.18 days as measured by DOC loss(1). Ultimate biodegradation to CO2 and H2O using acclimated sewage and 20-30 mg/L o-benzyl-p-chlorophenol, took slightly longer with a half-life of 7 to 23 days(1). o-Benzyl-p-chlorophenol undergoes rapid biodegradation after a short acclimation period in river water; o-benzyl-p-chlorophenol at a concentration of 0.1 mg/L was 78% degraded aerobically after 8 days; first re-spike (0.1 mg/L) on day 8 with 90% removal after 2 days; second re-spike of 0.1 mg/L on day 10 with 100% removal by day 13(2). o-Benzyl-p-chlorophenol, 0.5 mg/L, added to natural domestic sewage was substantially degraded within one day; re-spiked (1.0 mg/L) with nearly 100% removal within one day(2). Acclimated activated sludge mixed liquor in a semicontinuous activated sludge unit (o-benzyl-p-chlorophenol concentration, 2.0 mg/L) gave complete removal of DOC (dissolved organic carbon) in 24 hours. Sludge from a semicontinuous activated sludge unit was used as inoculum (o-benzyl-p-chlorophenol, 20 mg/L); there was a one week lag period followed by CO2 evolution at 60% of the theoretical within 27 days(2). CO2 evolution was used as a test method in this experiment to ensure that degradation was due to microbial action(2).

AEROBIC: In an aerobic, closed bottle screening test containing 10 mg/L of o-benzyl-p-chlorophenol and using activated sludge, 69% of the theoretical BOD was measured over 28 days(1). Using activated sludge from a communal clarification plant in the presence of 28, 100, and 500 mg/L o- benzyl-p-chlorophenol, theoretical BOD removal after 1 day of incubation was 60, 78, and 15%, respectively, after 2 days incubation was 88, 80, and 15%, respectively, and after 5 days incubation was 95, 65, and 28%, respectively, using the Sapromat test method(2). Using industrial activated sludge in the presence of 10, 28, and 100 mg/L o-benzyl-p-chlorophenol, theoretical BOD removal after 1 day of incubation was 100, 66, and 40%, respectively, after 2 days incubation was 90, 100, and 53%, respectively, and after 5 days incubation was 92, 88, and 58% degradation, respectively, using the Sapromat test method(2).

o-Benzyl-p-Chlorophenol

TR-444: One-Year Initiation/Promotion Study of o-Benzyl-p-Chlorophenol (CASRN 120-32-1) in Swiss (CD-1) Mice (Mouse Skin Study) (1995 )

11/17/93

Initiation/Promotion Study

Under the conditions of this 1-year mouse skin initiation/promotion study in Swiss (CD-1) mice, o -benzyl- p -chlorophenol was a cutaneous irritant and a weak skin tumor promoter relative to strong promoters such as TPA. BCP had no activity as an initiator or as a complete carcinogen.

o-Benzyl-p-Chlorophenol

A BCF value of 75 was measured for bluegill sunfish(1). Bluegill sunfish (Lepomis machrochirus) were exposed to 0.057 mg/L o-benzyl-p-chlorophenol for a period of 96 hours followed by a depuration period of 96 hours to determine the ability of the fish to metabolize and eliminate o-benzyl-p-chlorophenol. Depuration rate constants were from 4.67 to 6.94/days with a half-life of 0.14 days(1). The rate constant of o-benzyl-p-chlorophenol uptake in fish ranged from 11.8 to 13.8/days with a half-life of 0.06 days. According to a classification scheme(2), this BCF value suggests that bioconcentration in aquatic organisms is moderate(SRC).

Chemical: Phenol, 4-chloro-2-(phenylmethyl)-

Reg. (EC) No 2076/2002

Status: Active Update: 16-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/25019

2-Benzyl-4-chlorophenol: Does not have an individual approval but may be used under an appropriate group standard

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 2-Benzyl-4-chlorophenol is included on this list.

Residues of the following chemical substances are exempted from the requirement of a tolerance when used in accordance with good manufacturing practice as ingredients in an antimicrobial pesticide formulation, provided that the substance is applied on a semi-permanent or permanent food-contact surface (other than being applied on food packaging) with adequate draining before contact with food. ... (c) The following chemical substances when used as ingredients in an antimicrobial pesticide formulation may be applied to: Food-processing equipment and utensils. 2-Benzyl-4-chlorophenol is included on this list. Limit: When ready for use the end-use concentration is not to exceed 320 ppm.

Based on the reviews of the generic data for the active ingredient of ortho-Benzyl-para-chlorophenol and its salts, the Agency has sufficient information on the health effects of ortho-Benzyl-para-chlorophenol and on its potential for causing adverse effects in fish and wildlife and the environment. The Agency has determined that products containing ortho-Benzyl-parachlorophenol and its salts labeled and used as specified in this Reregistration Eligibility Decision, except the enclosed area fogging application will not pose unreasonable risks or adverse effects to humans or the environment. Therefore, the Agency concludes that all the uses of products containing ortho-Benzyl-parachlorophenol, Potassium -2-benzyl-4-chlorophenate and Sodium 2-benzyl-4- chlorophenate are eligible for reregistration. The Agency is requiring handler exposure data on the fogging application and cannot make an eligibility decision on this method until these data are generated.

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA, as amended in 1988, were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. 2-Benzyl-4-chlorophenol is found on List B. Case No: 2045; Pesticide type: fungicide, antimicrobial; Case Status: RED Approved 09/95; OPP has made a decision that some/all uses of the pesticide are eligible for reregistration, as reflected in a Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): 2-benzyl-4-chlorophenol; Data Call-in (DCI) Date(s): 06/10/91, 11/15/96; AI Status: OPP has completed a Reregistration Eligibility Decision (RED) document for the case/AI.

Male rats given an oral dose of 69 mg/kg or 206 mg/kg (14)C labeled o-benzyl-p-chlorophenol. ... Excretion of o-benzyl-p-chlorophenol was biphasic with an initial rapid alpha phase with a half life of 8 to 9 hr and slightly slower beta phase estimated to have a half life of 52 to 140 hr. ...

After iv injections of 10 mg/kg, ... feces, or feces and urine combined /were collected/, /investigators/ describe the elimination phase as a single-component model with a half-life of 14 hr.

After iv treatment with 10 mg/kg chlorophene, the major metabolite formed was the glucuronic acid conjugate of the parent compound. The metabolite gradually decreased over a 6-hr period after treatment. The oxidative metabolite increased from 0.5% to 6% of the glucuronide acid conjugates in bile over 6 hr.

In vitro metabolism studies found that about 95% of chlorophene was metabolized by liver supernatant in the presence of NADPH, uridine diphosphoglucuronic acid (UDPGA), and glutathione (GSH). Metabolism varied from 14% to 51% as the parent compound was exposed to various combinations of the cofactors, microsomes, and organ extracts.

/Investigators/ isolated the metabolites of [14C]-chlorophene in urine and feces over a 5-day period. A significant percentage of the radioactive dose was present in the urine and feces from 12 to 24 hr. The majority of metabolites were present as either glucuronide or sulfate ester conjugates in the urine during this time period. Two additional metabolites were also identified, one in which the benzyl aromatic ring had a hydroxyl and a methoxyl substituent (22.9% and 17.6% of the low and high dose, respectively) and the second in which the benzyl aromatic ring had a hydroxyl substituent (12.7% and 29.4% of the low and high dose, respectively). These same metabolites were identified in feces but at a lower concentration. Chlorophene was also identified in the urine as 5.3% and 14.1% of the low and high dose, respectively. However, a larger percentage of [14C]-chlorophene was identified in feces, 21.4% and 22.4% of the low and high dose, respectively.

Undiluted chlorophene (2 mL/kg) applied to the skin of rabbits lowered the percent of inorganic sulfates. However, the amount of glucuronate excreted was not affected. Application of 0.2 g/kg chlorophene in cottonseed oil and castor oil soap caused a slight increase in the output of glucuronates, but did not affect excretion of sulfates. The dilutions (1:100 and 1:300) produced no change in the excretion of glucuronates or sulfates.

For more Metabolism/Metabolites (Complete) data for O-BENZYL-P-CHLOROPHENOL (7 total), please visit the HSDB record page.

Chlorophene was applied to the intrascapular region of male Fischer-344 rats at a total dose of 10 mg/kg in dermal studies. Three days after exposure to Chlorophene, 59% of the dose was excreted in the urine and feces. Chlorophene was distributed, as a percent of the total dose, to large intestinal contents (1.58%), small intestinal contents (0.55%), the skin (0.23%), and the skin site (32.33%). Chlorophene was incompletely absorbed through the skin.

Rats /were/ dosed with 10 mg/kg chlorophene /iv/ and three rats each were sacrificed at various time points from 15 min to 72 hr. After iv exposure, 88% of the dose was excreted by 72 hr. After 15 min of treatment, about 30% of the chlorophene dose administered was present in the intestinal contents. Radioactivity was greatest in the kidneys and liver at this same time point and remained the greatest after 72 hr. The relative percent of unmetabolized chlorophene increased with time in the blood and liver over 72 hr. However, in the kidneys, it decreased with time. The skin had significant chlorophene radioactivity, 7.92% of the total dose administered after 15 min, but little remained after 24 hr.

/Investigators/ dosed rats orally with 10, 100, or 1000 mg/kg chlorophene. The relative concentration of chlorophene excreted in the urine and feces was dose dependent. At the low and high dose, feces were the major route of excretion, whereas at the intermediate dose, urinary excretion predominated. However, more than 92% of the radioactive chlorophene was excreted within 3 days by rats in all dose groups. Rats injected with 5, 10, or 25 mg/kg chlorophene in the femoral vein had a dose-related decrease in biliary excretion.

Male Sprague-Dawley rats /were administered/ (3/dose level) a single dose of 69 or 206 mg/kg [14C]-chlorophene. The kidneys and liver had the highest radiochemical concentrations of chlorophene and its metabolites. The combined concentrations of these two organs accounted for 0.16% and 0.13% of the 69 and 206 mg/kg doses, respectively. Approximately 0.23% and 0.18% of the dose was associated with the body fat at the low and high dose, respectively.

For more Absorption, Distribution and Excretion (Complete) data for O-BENZYL-P-CHLOROPHENOL (8 total), please visit the HSDB record page.

CIR ingredient: Chlorophene

Used in household, hospital, and veterinary disinfectants; Also used as a fungicide, herbicide, antimicrobial, and cosmetics preservative; [HSDB] Used as a disinfectant (swimming pool decks, industrial water systems, poultry houses and other farming premises, food processing, and restaurants); [Reference #1]

Using Disinfectants or Biocides [Category: Clean]；Farming (Pesticides) [Category: Industry]

For o-benzyl-p-chlorophenol (USEPA/OPP Pesticide Code: 062201) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Active principle or enhancing agent for disinfectants

Germicide in disinfectant solutions & soap formulations.

(1977) No Data

(1979) No Data

(1977) No Data

(1979) No Data

(1977) PROBABLY GREATER THAN 2.27X10+6 GRAMS

(1979) PROBABLY GREATER THAN 2.27X10+6 GRAMS

Annual production averages less than 4.5X10+6 kg.

(1986) 10 thousand-500 thousand pounds

For more U.S. Production (Complete) data for O-BENZYL-P-CHLOROPHENOL (7 total), please visit the HSDB record page.

Reaction of sodium or potassium phenoxide and benzyl chloride followed by chlorination of the resulting o-benzylphenol; reaction of p-chlorophenol and benzyl chloride.

Klarmann, Gate, US Patent 1,967,825 (to Lehn & Fink); from Na or K phenoxide and benzyl chloride followed by chlorination of resulting o-benzylphenol: Kaiser, German patent 703,955 (1941 to Deutsche Hydrierwerke).