Captafol

log Kow = 3.8

3.8

White, solid

Colorless to pale yellow crystals

White, crystalline solid [Note: Available commercially as a wettable powder or in liquid form].

0.0001 % (NIOSH, 2024)

Slightly soluble in most organic solvents; solubility (g/kg): isopropanol 13; benzene 25; toluene 17; xylene 100; acetone 43; methyl ethyl ketone 44; dimethyl sulfoxide 170

In water, 1.4 mg/l @ 20 °C

Solubility in water: none

0.0001%

Decomposes (NIOSH, 2024)

decomposes

Decomposes

When heated to decomposition it emits very toxic fumes of /hydrogen chloride, oxides of nitrogen and oxides of sulfur/.

Rapidly hydrolyzed in acidic and alkaline media. At 50 °C, 50% decomposition occurs in about 3 hr at pH 6.

Decomposes slowly at the melting point.

321 °F (Decomposes) (NIOSH, 2024)

160-161 °C; decomposes slowly at melting point

160 - 161 °C

160-161 °C

321 °F (decomposes)

321 °F (Decomposes)

8e-06 mmHg (NIOSH, 2024)

0.00000001 [mmHg]

8.27X10-9 mm Hg @ 20 °C

0.000008 mmHg

0.000008 mmHg

Captafol is a white crystalline solid with a slight, but pungent odor. Mp: 162 °C. Practically insoluble in water. Only slightly soluble in organic solvents. Technical captafol is a wettable light tan powder that is used as a fungicide. Inhaled dust irritates the respiratory tract. Irritates skin and damages eyes. Acute oral toxicity in humans is low. Not persistent in the environment (decomposes with a half-life of 11 days in the soil). Highly toxic to fish and other aquatic organisms.

White, crystalline solid with a slight, characteristic pungent odor. [fungicide] [Note: Available commercially as a wettable powder or in liquid form.] [NIOSH]

Solid

COLOURLESS CRYSTALLINE POWDER.

White, crystalline solid with a slight, characteristic pungent odor.

White, crystalline solid with a slight, characteristic pungent odor. [fungicide] [Note: Available commercially as a wettable powder or in liquid form.]

Danger

H317: May cause an allergic skin reaction [Warning Sensitization, Skin]；H350: May cause cancer [Danger Carcinogenicity]；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, P261, P272, P273, P280, P302+P352, P318, P321, P333+P317, P362+P364, P391, P405, and P501 (click each P-code to see the statement)

Danger

Hazard Traits - Carcinogenicity；Authoritative List - EC Annex VI CMRs - Cat. 1B; IARC Carcinogens - 2A; NTP RoC - reasonable; Prop 65；Report - regardless of intended function of ingredient in the product

Captafol: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

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.)

IMAP assessments - 1H-Isoindole-1,3(2H)-dione, 3a,4,7,7a-tetrahydro-2-[(1,1,2,2-tetrachloroethyl)thio]-: Human health tier I assessment；IMAP assessments - 1H-Isoindole-1,3(2H)-dione, 3a,4,7,7a-tetrahydro-2-[(1,1,2,2-tetrachloroethyl)thio]-: Environment tier I assessment

Excerpt from NIOSH Pocket Guide for Captafol:；Exposure Routes: Inhalation, skin absorption, ingestion, skin and/or eye contact；Symptoms: Irritation eyes, skin, respiratory system; dermatitis, skin sensitization; conjunctivitis; bronchitis, wheezing; diarrhea, vomiting; liver, kidney injury; high blood pressure; In Animals: teratogenic effects; [potential occupational carcinogen]；Target Organs: Eyes, skin, respiratory system, central nervous system, liver, kidneys, cardiovascular system；Cancer Site: [in animals: tumors at many sites] (NIOSH, 2024)

The thiophthalimides include captan, captafol, and folpet; no systemic poisonings in humans have been reported; [EPA Pesticides] Allergic contact dermatitis in pesticide handlers is most likely due to maneb, carbofuran, carbaryl, captan, folpet, or captafol. [Marks, p. 312] TLV Basis is liver damage, kidney damage and dermal sensitization; A potential respiratory sensitizer; [ACGIH]

Hooper K et al; Regulation of Priority Carcinogens and Reproductive or Developmental Toxicants. Am J Ind Med 22 (6): 793-808 (1992). In this paper, a list of 33 potential priority carcinogens and reproductive/developmental toxicants are presented, including alcoholic beverages, asbestos, benzene, chlorinated solvents, formaldehyde, glycol ethers, lead, tobacco smoke, and toluene.

Saito H et al; In Vitro Cytotoxicity of 45 Pesticides to Goldfish GF-scale (GFS)Cells. Chemosphere 23 (4): 525-38 (1991). The cytotoxicities of 45 pesticides including 18 organophosphates and 7 carbamates to GF-Scale cells, derived from the scale of goldfish (Carassius auratus), were determined with the 24 hr neutral red assay.

Abrams K et al; Pesticide-Related Dermatoses in Agricultural Workers. Occupational Medicine: State of the Art Reviews 6 (3): 463-92 (1991). Literature survey on occupational skin diseases in farm workers due to contact with pesticides.

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. Captafol is found on List A, which contains most food use pesticides and consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA '88. Case No: 0116; Pesticide type: fungicide; Registration Standard Date: 09/30/84; Case Status: No products containing the pesticide are actively registered. Therefore, we are characterizing the case as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI): captafol; AI Status: The active ingredient is no longer contained in any registered products ... "cancelled."

Tolerances are established for residues of the fungicide captafol (cis-N-[(1,1,2,2-tetrachloroethyl)thio]-4-cyclohexene-1,2-dicarboximide) in or on the following food commodities: onion; potato; and tomato.

CAPTAFOL is non-flammable but, on heating, may decompose to generate toxic fumes, such as sulfur oxides, hydrogen sulfide, hydrochloric acid, and phosgene. Stable at room temperature when dry but readily hydrolysed, especially in an alkaline environment. Captafol and mixtures containing high concentrations of captafol may react violently with alkali. Incompatible with acids, acid chlorides, acid anhydrides, and strong oxidizing agents. Sulfhydryl compounds such as glutathione and cysteine cause a rapid chemical decomposition.

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .

Rinse with plenty of water (remove contact lenses if easily possible). Refer for medical attention.

Rinse mouth. Refer for medical attention .

Excerpt from NIOSH Pocket Guide for Captafol:；Eye: IRRIGATE IMMEDIATELY - If this chemical contacts the eyes, immediately wash (irrigate) the eyes with large amounts of water, occasionally lifting the lower and upper lids. Get medical attention immediately.；Skin: SOAP WASH IMMEDIATELY - If this chemical contacts the skin, immediately wash the contaminated skin with soap and water. If this chemical penetrates the clothing, immediately remove the clothing, wash the skin with soap and water, and get medical attention promptly.；Breathing: RESPIRATORY SUPPORT - If a person breathes large amounts of this chemical, move the exposed person to fresh air at once. If breathing has stopped, perform artificial respiration. Keep the affected person warm and at rest. Get medical attention as soon as possible.；Swallow: MEDICAL ATTENTION IMMEDIATELY - If this chemical has been swallowed, get medical attention immediately. (NIOSH, 2024)

(General first aid procedures)；Eye: Irrigate immediately - If this chemical contacts the eyes, immediately wash (irrigate) the eyes with large amounts of water, occasionally lifting the lower and upper lids. Get medical attention immediately.；Skin: Soap wash immediately - If this chemical contacts the skin, immediately wash the contaminated skin with soap and water. If this chemical penetrates the clothing, immediately remove the clothing, wash the skin with soap and water, and get medical attention promptly.；Breathing: Respiratory support；Swallow: Medical attention immediately - If this chemical has been swallowed, get medical attention immediately.

Do NOT wash away into sewer. Sweep spilled substance into containers; if appropriate, moisten first to prevent dusting. Carefully collect remainder, then remove to safe place. (Extra personal protection: P3 filter respirator for toxic particles).

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.

Hydrolysis: The hydrolysis products are not fungicidally active.

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

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.

The worker should immediately wash the skin when it becomes contaminated.

The worker should wash daily at the end of each work shift.

Work clothing that becomes wet or significantly contaminated should be removed or replaced.

For more Preventive Measures (Complete) data for CAPTAFOL (7 total), please visit the HSDB record page.

Urinary

Eyes, skin, respiratory system, central nervous system, liver, kidneys, cardiovascular system

LC50 Gammarus lacustris 0.8 mg/l/96 hr /Conditions of bioassay not specified/

LC50 Pternarcys californica 0.4 mg/l/96 hr /Conditions of bioassay not specified/

LC50 Rainbow trout 0.5 mg/l/96 hr /Conditions of bioassay not specified/

LC50 Goldfish 3.0 mg/l/96 hr /Conditions of bioassay not specified/

For more Ecotoxicity Values (Complete) data for CAPTAFOL (8 total), please visit the HSDB record page.

TERRESTRIAL FATE: The adsorption coefficient, logKom, for difolatan based on soil organic matter has been reported as 3.08(1) and 3.09(2). Based on a relationship Kom = Koc/1.724(3), the Koc for difolatan would be 2073 and 2120, respectively(SRC). According to a classification scheme(4), these Koc values suggests that difolatan is expected to be slightly mobile in soil. Volatilization of difolatan from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 2.7X10-9 atm-cu m/mole(SRC), derived from its vapor pressure,8.27X10-9 mm Hg(5) and water solubility, 1.4 mg/l(6). Difolatan is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(5). In a laboratory experiment, the biodegradation half-life of difolatan in three soils was in the range of 23-55 days(7). The overall half-life of difolatan in soil is about 11 days, independent of soil type or initial concn(8).

AQUATIC FATE: Based on a classification scheme(1), Koc values of 2073 and 2120(SRC), determined from the adsorption coefficients (logKom) for difolatan of 3.08(2) and 3.09(3), and a relationship Kom = Koc/1.724(4), indicates that difolatan is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon a Henry's Law constant of 2.7X10-9 atm-cu m/mole(SRC), derived from its vapor pressure, 8.27X10-9 mm Hg(5), and water solubility, 1.4 mg/l(6). According to a classification scheme(7), an estimated BCF of 170(SRC), from a log Kow of 3.80(6), suggests the potential for bioconcentration in aquatic organisms is high(SRC), provided the compound is not altered physically or chemically after being released to the environment. The half-lives for the hydrolysis of difolatan at pH 3.0, 7.0 and 8.0 were 77.8, 6.54, and 0.72 hours, respectively(5). Hydrolysis is likely to be the predominent pathway of degradation in the aquatic environment(10). Studies on captan, a closely related analog to difolatan, indicated that direct photolysis cannot compete with its rapid hydrolysis(8).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), difolatan, which has a vapor pressure of 8.27X10-9 mm Hg at 25 °C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase difolatan may be removed from the air by wet and dry deposition(SRC).

Difolatan was detected as a residue in U.S. foods during the regulatory monitoring in fiscal years 1978-1986(1-2), fiscal years 1989-1990(3-4), and 1994(6). At a detection limit of 0.002 mg/kg, no difolatan was detected in Ontario-grown vegetables during 1980-1985(5). Difolatan was found in Danish gooseberries (0.11 mg/kg) in 1996 in the Danish National Pesticide Monitoring Program 1995-1996(7). Difolatan was not detected in various infant formulas obtained in the Spanish Mediterranean; detection limits were 2.27 and 10.62 ug/l depending on the method used(8). Difolatan was not found in domestic and imported pears and tomatoes in an 1992-1993 US Food and Drug Administration (US FDA) Incidence/Level Monitoring study(9). Difolatan was found at a maximum concentration of 0.13 ppm in apples in a U.S. FDA regulatory monitoring (1985-1991) of domestic foods that may be eaten by infants and childern(10).

Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.；Nephrotoxin - The chemical is potentially toxic to the kidneys in the occupational setting.；Skin Sensitizer - An agent that can induce an allergic reaction in the skin.；Asthma - Reversible bronchoconstriction (narrowing of bronchioles) initiated by the inhalation of irritating or allergenic agents.；IARC Carcinogen - Class 2: International Agency for Research on Cancer classifies chemicals as probable (2a), or possible (2b) human carcinogens.；NTP Carcinogen - Reasonably anticipated to be a human carcinogen.；ACGIH Carcinogen - Confirmed Animal.

The substance can be absorbed into the body by ingestion.

inhalation, skin absorption, ingestion, skin and/or eye contact

Difolatan was not detected in human milk samples collected from women in rural and small urban locations in the Spanish Mediterranean coastal area during the winter of 1993(1). Detection limits were 2.27 and 10.62 ug/l depending on the method used(1).

IDENTIFICATION: Captafol is a chloroalkyl thio fungicide. A number of formulations are commercially available which include captafol with other pesticides. It is practically insoluble in water and slightly soluble in most organic solvents. The fungicide is a white crystalline solid. The technical grade is a light tan powder with a characteristic odor. It is stable except under strongly alkaline conditions. Captafol is available as dusts, wettable powders and flowable formulations. The formulated product may pose an environmental risk if released into the aquatic environment. Captafol is a protective non-systemic fungicide widely used to control foliage and fruit diseases of tomatoes, coffee berry disease, potato blight, and tapping panel disease of rubber trees. It is also used in the lumber and timber industries to reduce losses from wood rot fungi in logs and wood products. HUMAN EXPOSURE: The acute oral toxicity is low. Skin, eyes and respiratory tract are targets for local irritation and sensitization. Following ingestion of large quantities of captafol, vomiting and diarrhea have been reported. Respiratory sensitization and conjunctivitis are known to have occurred. Systemic disorders including hypertension, hepatic and renal disturbances, usually paralleling the degree of dermatitis, have been reported following captafol exposure. Wheezing due to bronchospasm, contact dermatitis and vomiting and diarrhea are the features of exposure to captafol by inhalation, skin contact and ingestion respectively. Chronic exposure can cause hypertension, depression of liver function, dermatitis, conjunctivitis and anemia.Exposed individuals include farm and timber workers; workers involved in formulation and dispensing pesticides; agricultural spray workers and crop harvesters during disease vector control periods. Inhalation of captafol as spray mists or powders have been reported in an occupational context. ANIMAL STUDIES: Animal feeding studies have shown that most of th

/AQUATIC SPECIES/ Moderately to very highly toxic to freshwater invertebrates.

/OTHER TERRESTRIAL SPECIES/ Not toxic to bees.

/PLANTS/ Under certain conditions, grapes, apples, citrus fruit and roses may be injured /by captafol application/.

Cough. Sore throat. Wheezing. Shortness of breath.

MAY BE ABSORBED! Redness. Rash. Blisters.

Redness. Pain. Itching.

Burning sensation. Abdominal pain.

irritation eyes, skin, respiratory system; dermatitis, skin sensitization; conjunctivitis; bronchitis, wheezing; diarrhea, vomiting; liver, kidney injury; high blood pressure; In Animals: teratogenic effects; [potential occupational carcinogen]

Hazard Traits - Carcinogenicity；Authoritative List - EC Annex VI CMRs - Cat. 1B; IARC Carcinogens - 2A; NTP RoC - reasonable; Prop 65；Report - regardless of intended function of ingredient in the product

Captafol: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

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.)

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. Captafol is found on List A, which contains most food use pesticides and consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA '88. Case No: 0116; Pesticide type: fungicide; Registration Standard Date: 09/30/84; Case Status: No products containing the pesticide are actively registered. Therefore, we are characterizing the case as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI): captafol; AI Status: The active ingredient is no longer contained in any registered products ... "cancelled."

Tolerances are established for residues of the fungicide captafol (cis-N-[(1,1,2,2-tetrachloroethyl)thio]-4-cyclohexene-1,2-dicarboximide) in or on the following food commodities: onion; potato; and tomato.

No unchanged captafol was detected in the blood, tissues, or urine /in rats, dogs, & monkeys/. The major single metabolite, tetrahydrophthalimide, was detected in blood, feces, & urine, but most of the activity in the blood and urine was in the form of more soluble metabolites. No captafol epoxide was detected ... .

In mammals, following oral administration, /and in plants/ captafol is hydrolyzed to tetrahydrophthalimide and dichloroacetic acid. Tetrahydrophthalimide is degraded to tetrahydrophthalimidic acid and further to phthalic acid and ammonia.

When rats, dogs, & monkeys were fed (14)C captafol, almost 80% was excreted within 36 hr, mainly in the urine and none /as/ expired carbon dioxide. ... No unchanged captafol was detected in the blood, tissues, or urine.

Absorbed by skin.

The thiophthalimides are widely used fungicides on seeds, field crops, and stored produce; [EPA Pesticides] Used as an agricultural fungicide in large quantities worldwide; Limited industrial use in paints and plastics; [ACGIH]

Captafol is no longer registered in the U.S. [EPA Pesticides]

Painting (Pigments, Binders, and Biocides) [Category: Paint]；Farming (Pesticides) [Category: Industry]

The active ingredient is no longer contained in any registered products ... "cancelled."

For captafol (USEPA/OPP Pesticide Code: 081702) there are 0 labels match. /SRP: Not registered for current 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./

Fungicide

Captafol is produced by reaction of the sodium salt of tetrahydrophthalimide in benzene with tetrachloroethylsulfenyl chloride.

Reaction of imide, formed by action of ammonia on tetrahydrophthalic anhydride, with 1,1,2,2-tetrachloroethyl sulfenyl chloride.

Ortho difolatan 80 wettable--80% wettable powder used at rates of 2 lb/100 gal (US). Ortho difolatan 4 flowable seed protectant--39% (W) ai used at 4 lb/us gal; difolatan-botran 35-35 seed protectant--tetrachloroethylmercaptocyclohexenedicarboximide 35%, 2,6-dichloro-4-nitroaniline 35%.

It is formulated as ...7.5% dust.

Mycodifol (mixture of difolotan and folpet) fungicide for grapes.

'Captaspor', soluble concentrate (480 g/l); 'Kenofol', 'Ortho Difolatan 80W', wettable powder (800 g ai/kg); 'Ortho Difolatan 4 Flowable', 'Sanspor', soluble concentrate (480 g/l).

For more Formulations/Preparations (Complete) data for CAPTAFOL (9 total), please visit the HSDB record page.

The WHO Recommended Classification of Pesticides by Hazard identifies Captafol (technical grade) as Class IA: extremely hazardous; Main Use: fungicide, other than for seed treatment. According to the PIC /Prior Informed Consent/ Convention, export of /Captafol/ can only take place with the prior informed consent of the importing Party. ...(further information can be found at: http://www.pic.int/).

/It/ may be combined with most commonly used insecticides, fungicides with the exception of strongly alkaline materials, oil sprays.

... Is a protective non-systemic fungicide applied to foliage at about 200 g ai/100 l. The stability of deposits which retain their fungicidal activity has led to spray programs requiring fewer applications per season when applied at higher rates during the dormant season on pome fruits.

USA: Not marketed

N-tetrachloroethyl analog of captan.