Dicofol

Pesticide -> EPA IRIS

Acaricides

Active substance -> EU Pesticides database: Not approved

Agrochemicals -> Pesticide active substances

Active substance -> EU Pesticides database: Not approved

Pesticides -> Organochlorine Pesticides

log Kow = 5.02

4.28

4.93

Solids have slight characteristic odor

Liquid has odor of the solvent (xylene)

greater than 1.1 at 68 °F <0.9 at 20 °C (liquid) (USCG, 1999)

Specific gravity: 1.130 at 20 °C

1.13 g/cm³

Colorless solid

Crystals from petroleum ether

less than 0.1 mg/mL at 72 °F (NTP, 1992)

400 g/L in acetone, ethyl acetate and toluene at 25 °C. 36 g/L in methanol at 25 °C. 30 g/L in hexane and isopropanol at 25 °C

In water, 1.2 mg/L at 24 °C (99% purity)

In water, 0.8 mg/L at 25 °C

Solubility in water: none

75 °F (USCG, 1999)

193 °C

193 °C, 379 °F (open cup)

120 °F (closed cup)

193 °C o.c.

437 °F at 760 mmHg (NTP, 1992)

180 °C at 0.1 mm Hg

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P270, P272, P273, P280, P301+P317, P302+P352, P317, P321, P330, P332+P317, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P270, P272, P273, P280, P301+P317, P302+P352, P317, P321, P330, P332+P317, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Hazard Traits - Bioaccumulation; Environmental Persistence

Regulation (EC) No 1107/2009 (amended)

Dicofol is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)

2008/764/EC

Substance: Dicofol

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Special Hazards of Combustion Products: Irritating hydrogen chloride fumes may form in fire.

Combustible. Liquid formulations containing organic solvents may be flammable. Gives off irritating or toxic fumes (or gases) in a fire.

A skin and eye irritant; May cause kidney and liver injury; May cause CNS effects; [ICSC] May cause skin sensitization; [eChemPortal: ESIS] A skin irritant; May cause skin sensitization; Targets CNS; [MSDSonline]

The major hazards encountered in the use and handling of dicofol stem from its toxicologic properties as an organochlorine pesticide. Contact with dicofol may cause burns to the skin and eyes, possibly severe. Moreover, acute exposure to dicofol may even be fatal, regardless the route (ie, dermal, inhalation, or ingestion). When a potentially serious exposure situation exists, wear a positive-pressure breathing apparatus, and special protective clothing. Also, remove any contaminated clothing and wash skin thoroughly before leaving the exposure site. Dicofol will not ignite easily (flashpoint 120 °F, closed cup), but it will burn with the possible evolution of highly toxic fumes and poisonous gases. For small fires involving dicofol, extinguish with dry chemical, CO2, water spray, or foam, and for large fires, use water spray, or foam. Runoff from fire control water may give off poisonous gases or cause water pollution and should therefore, be diked for later disposal. Containers of dicofol are not required to bear a label, and they may be shipped by all major modes of transportation. However, certain storage precautions do apply. Dicofol should be stored away from alkali, acids or acid fumes, and feed or foodstuffs. Also, storage temperature should not be less than 40 °F. Small spills of dicofol should be carefully shovelled (liquid dicofol is first absorbed by non-combustible material, eg, sand) into a clean, dry container for later disposal). Large land spills are diked or deposited in excavated pits, ponds, or other holding areas (dry spills covered with plastic sheet) for later disposal. For large spills on water, activated carbon should be applied to remove immobilized masses of pollutants and precipitates. Before permanent land disposal of dicofol, consult with environmental regulatory agencies.

European Commission, ESIS; IUCLID Dataset, Dicofol (115-32-2) (2000 CD-ROM edition).[Available from, as of June 3, 2009: http://esis.jrc.ec.europa.eu/]

USEPA/Office of Prevention, Pesticides and Toxic Substances; Reregistration Eligibility Decision Document - Dicofol EPA 738-R-98-018 (November 1998). 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 May 28, 2009: http://www.epa.gov/pesticides/reregistration/status.htm]

WHO; Environ Health Criteria: DDT and its Derivatives (1979). EHC publications are monographs designed for scientists and administrators responsible for the establishment of safety standards and regulations and provide basic scientific risk evaluations of a wide range of chemicals and groups of chemicals.

Bioassay of Dicofol for Possible Carcinogenicity (1978) Technical Rpt Series No. 90 DHEW Pub No. (NIH) 78-1340, U.S. Department of Health Education and Welfare, National Cancer Institute, Bethesda, MD 20014

For more Special Reports (Complete) data for DICOFOL (6 total), please visit the HSDB record page.

Tolerances for the combined residues of the insecticide dicofol, 1,1-bis(4-chlorophenyl)-2,2,2-trichloroethanol and 1-(2-chlorophenyl)-1-(4-chlorophenyl)-2,2,2-trichloroethanol in or on raw agricultural commodities are established as follows: [Table#1766]

Tolerances for the combined residues of the insecticide dicofol, 1,1-bis(4-chlorophenyl)-2,2,2-trichloroethanol, 1-(2-chlorophenyl)-1-(4-chlorophenyl)-2,2,2-trichloroethanol, 1,1-bis(4-chlorophenyl)-2,2-dichloroethanol, and 1-(2-chlorophenyl)-1-(4-chlorophenyl)-2,2-dichloroethanol in or on raw agricultural commodities are established as follows: [Table#1767]

The Agency has determined that dicofol products, labeled and used as specified in this Reregistration Eligibility Decision, may not pose unreasonable risks or adverse effects to humans or the environment, contingent on the results of the dermal toxicity and DFR studies currently being conducted by the registrants. Under the Food Quality Protection Act of 1996, the Agency has determined with a reasonable certainty that no harm will result to infants and children or to the general population from aggregate exposure to dicofol. The Agency concludes that products containing dicofol might be eligible for reregistration for all uses, as specified in this /Reregistration Eligibility Decision document/, contingent upon results of the dermal toxicity and DFR /dislodgeable foliar residue/ studies.

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 continued use. Under this pesticide reregistration program, EPA examines newer health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether the use of the pesticide does not pose unreasonable risk in accordance to newer saftey standards, such as those described in the Food Quality Protection Act of 1996. Dicofol is found on List A, which contains most pesticides that are used on foods and, hence, have a high potential for human exposure. List A consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA '88. Case No: 0021; Pesticide type: insecticide (acaricide); Registration Standard Date: 12/01/83; Case Status: OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): 1,1-Bis(chlorophenyl)-2,2,2-trichloroethanol; Data Call-in (DCI) Date(s): 09/30/91, 03/03/95, 10/13/95; AI Status: The producers of the pesticide has made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner.

DICOFOL is an organochlorine bridged diphenyl. Halogenated aliphatic compounds are moderately or very reactive. Halogenated organics generally become less reactive as more of their hydrogen atoms are replaced with halogen atoms. Halogenated aliphatics are incompatible with strong oxidizing and reducing agents. Also, they are incompatible with many amines, nitrides, azo/diazo compounds, alkali metals, and epoxides. DICOFOL hydrolyzes in alkali. It is slightly corrosive to metals. Contact with steel at elevated temperatures causes formation of toxic gases. (NTP, 1992).

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:

Use water spray, powder, foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Give a slurry of activated charcoal in water to drink. Refer for medical attention .

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.

Store above 40 °F, away from feed, foodstuffs, or any body of water.

... Store in tightly closed containers in a cool, well ventilated area away from alkaline pesticides, strong acids, acid fumes, and steel ...

SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a POTW is acceptable only after review by the governing authority. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must meet Hazardous Material Criteria for disposal.

The non-occupational exposure of dicofol was studied in Jacksonville, FL and Springfield/Chicopee, MA during summer 1986, spring 1987, and winter 1988; sample monitoring consisted of 24 hr personal air samples(1). Personal air concentrations of dicofol for Springfield/Chicopee residents during spring 1987 was 7 ng/cu m; dicofol was not detected in personal summer and winter samples(1).

LC50; Species: Anas platyhynchos (mallard duck, 10 days old) oral 1651 mg/kg for 5 days (95% confidence limit: 1356-2029 mg/kg) /Technical grade/

LC50; Species: Colinus virginianus (bobwhite quail, 14 days old) oral 3010 mg/kg for 5 days (95% confidence limit: 2635-3424 mg/kg) /Technical grade/

LC50; Species: Coturnix japonica (Japanese quail, age 1 day) oral via capsule 905 ppm for 5 days (95% confidence interval: 723-1140 ppm)

LC50; Species: Coturnix japonica (Japanese quail, age 7 days) oral via capsule 1237 ppm for 5 days (95% confidence interval: 979-1578 ppm)

For more Ecotoxicity Values (Complete) data for DICOFOL (29 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 5017 in silty loam(2) to 8383 in sand(3), indicate that dicofol is expected to be immobile in soil(SRC). Volatilization of dicofol from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 2.4X10-7 atm-cu m/mole(SRC), derived from its vapor pressure, 3.98X10-7 mm Hg(3), and water solubility, 0.8 mg/L(3). Dicofol is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). The hydrolysis half-lives for dicofol range from 85 days at pH 5 to 26 min at pH 9 in aqueous solution(2). Photolysis on soil is not an important route of degradation for dicofol, possibly due to binding on the soil and lack of solubility in soil water(4). Biodegradation of dicofol on soil is expected to occur based upon a degradation half-life of 43 days on a silt loam soil(4). The major metabolites were 1,1-(p-chlorophenyl)-2,2-dichloroethanol, p,p'-DCBP, and 3-hydroxy-4,4'-dichlorobenzophenone(4). Volatile residues were 21-22% of the applied and unextractable residues were 10-15% of the applied after 12 months(4).

Tolerances for the combined residues of the insecticide dicofol, 1,1-bis(4-chlorophenyl)-2,2,2-trichloroethanol and 1-(2-chlorophenyl)-1-(4-chlorophenyl)-2,2,2-trichloroethanol in or on raw agricultural commodities are established as follows: [Table#1766]

Tolerances for the combined residues of the insecticide dicofol, 1,1-bis(4-chlorophenyl)-2,2,2-trichloroethanol, 1-(2-chlorophenyl)-1-(4-chlorophenyl)-2,2,2-trichloroethanol, 1,1-bis(4-chlorophenyl)-2,2-dichloroethanol, and 1-(2-chlorophenyl)-1-(4-chlorophenyl)-2,2-dichloroethanol in or on raw agricultural commodities are established as follows: [Table#1767]

The Agency has determined that dicofol products, labeled and used as specified in this Reregistration Eligibility Decision, may not pose unreasonable risks or adverse effects to humans or the environment, contingent on the results of the dermal toxicity and DFR studies currently being conducted by the registrants. Under the Food Quality Protection Act of 1996, the Agency has determined with a reasonable certainty that no harm will result to infants and children or to the general population from aggregate exposure to dicofol. The Agency concludes that products containing dicofol might be eligible for reregistration for all uses, as specified in this /Reregistration Eligibility Decision document/, contingent upon results of the dermal toxicity and DFR /dislodgeable foliar residue/ studies.

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 continued use. Under this pesticide reregistration program, EPA examines newer health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether the use of the pesticide does not pose unreasonable risk in accordance to newer saftey standards, such as those described in the Food Quality Protection Act of 1996. Dicofol is found on List A, which contains most pesticides that are used on foods and, hence, have a high potential for human exposure. List A consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA '88. Case No: 0021; Pesticide type: insecticide (acaricide); Registration Standard Date: 12/01/83; Case Status: OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): 1,1-Bis(chlorophenyl)-2,2,2-trichloroethanol; Data Call-in (DCI) Date(s): 09/30/91, 03/03/95, 10/13/95; AI Status: The producers of the pesticide has made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner.

Despite nearly 4 decades of research on organochlorines, & especially DDT, the biochemical basis of their toxic action is not yet unequivocally established. ... /it has been/ reported that ... dicofol ... inhibited the ATPase associated with oxidative phosphorylation & cation transport in plasma membranes.

/Dicofol/ produces stimulation of axonal transmission of nervous signals, believed to be related to inhibition of ATPases in the central nervous system (CNS). The signs of toxicity are consistent with CNS depression.

The dicofol metabolite dichlorobenzilic acid (DCBA) was measured in the urine of 4 workers involved in the mixing/loading or application of dicofol to citrus crops for 10 consecutive days. Urine samples were obtained over 4 days beginning 6 days after exposure ... The half-life for DCBA excretion in /human/ urine was estimated to be seven days.

DDT in insects (drosophila) is metabolized by dechlorination to form DDE (2,2-bis(p-chlorophenyl)-1,1-dichloroethylene) or by alpha-hydroxylation to form ... Kelthane. /DDT/

Biotransformation of kelthane ... yielded 4,4'-dichlorobenzophenone (DBP), 4,4'-dichlorobenzhydrol (DBH) and DDE (2,2-bis(p-chlorophenyl)-1,1-dichloroethylene).

Yields 2,2-bis(p-chlorophenyl)acetic acid probably in rat. Yields 1,1-dichloro-2,2-bis(p-chlorophenyl)ethylene in rat. /From table/

The mouse has the ability to easily convert dicofol to water-soluble metabolites, eg, 4,4'-dichlorobenzhydrol. (14)C-dicofol and (3)H-dicofol were administered to male mice, then radioactivity was measured in urine. 40.7% (14)C and 49.8% (3)H of the dose was excreted within 24 hr. Metabolites in both systems were separated by gas chromatography and characterized by cleavage with beta-glucosidase and beta-glucuronidase.

For more Metabolism/Metabolites (Complete) data for DICOFOL (9 total), please visit the HSDB record page.

Dicofol can be absorbed via oral, inhahation, and dermal routes. It is distributed primarily to the adipose tissue, as well as the adrenal glands, thyroid, and liver. Metabolism of dicofol produces the metabolites 4,4'-dichloro-benzophenone and 4,4'-dichlorodicofol. Dicofol and its metabolites are excreted mainly in the faeces. (L631, L632)

Retention of kelthane in adipose tissue /of rats/ was more marked in males than in females. The rate of disappearance of kelthane was about 3/4 in male rats and in the females about 2/5 of the stored insecticide over a 13 week period.

In rats fed 10 mg/kg dicofol in the diet for 10 weeks, the concentration in the adipose tissue of females was 31.2 mg/kg & that in males 13.9 mg/kg. After oral administration of radiolabelled dicofol to mice, radioactivity associated with water sol metabolites was detected in the urine.

/Chlorinated insecticides/ may be absorbed through the respiratory & gastrointestinal tracts & through the skin, & whatever its route this absorption is facilitated by oily substances. /Chlorinated insecticides/

Metabolism studies in male and female Sprague Dawley rats used a single oral dose of 50 mg/kg of (14)C-dicofol. The radiolabel was eliminated mainly in the feces and to a lesser extent in the urine. The parent compound was preferentially stored in adipose tissue ...

For more Absorption, Distribution and Excretion (Complete) data for DICOFOL (6 total), please visit the HSDB record page.

Used to control many species of mite on a wide range of crops, such as fruit, vines, ornamentals, vegetables, and field crops; Also used in or around buildings for mite control; [HSDB]

Farming (Pesticides) [Category: Industry]

For dicofol (USEPA/OPP PC Code: 010501) 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./

Acaricide

Control of many species of mite on a wide range of crops, incl fruit, vines, ornamentals, vegetables, and field crops; in or around agricultural and domestic buildings for mite control.

Mites on field crops, fruits, vegetables, and ornamentals.

... Dicofol products contain a number of DDT analogs as manufacturing impurities /which/ include: o,p'- and p,p'-isomers of DDT, DDE, DDD and a substance called extra-chlorine DDT (Cl-DDT).

The content of 1,1-dichloro-2,2-bis(para-chlorophenyl)ethylene (DDE) found in dicofol formulations was calculated to be 1-2%. ... the major impurity was 1,1,1,2-tetrachloro-2,2-bis(4-chlorophenyl)ethane. Up to 18 impurities were reported to be components of various samples of technical dicofol.

(1978) 1.87X10+7 g (PRINCPL CUSTMS DISTS)

(1982) 9.85X10+7 g (PRINCPL CUSTMS DISTS)

1.61X10+6 lb

On cotton, 50%; on citrus, 29%; deciduous fruits/nuts, 13%; ornamentals, 4%; and in home and garden applications, 4%, estimated (1978)

Acaricide for cotton, 75%; acaricide for citrus, 17%; acaricide for vegetables, 8% (1982)

The use of dicofol in U.S. Agriculture has been recorded from 1966 to 1989. Records indicate that dicofol use in 1966, 1971, 1976, 1982, and 1989 was 893,000, 447,000, 810,000, 1,020,000, and 1,500,000 lbs active ingredient/yr, respectively.

In 1992, total pounds of dicofol applied to cotton was 527,705, all citrus 302,464, dry beans 109,230, apples 48,079, grapes 22,230, pecans 17,456, mint 11,394, tomatoes 11,324, strawberries 10,315, watermelons 8,362.

More than 70% of dicofol product sold annually in the U.S. is applied in California, Arizona, Texas, and Florida.