Folpet
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Folpet
structure -
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CAS No:
133-07-3
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Formula:
C9H4Cl3NO2S
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Chemical Name:
Folpet
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Synonyms:
1H-Isoindole-1,3(2H)-dione,2-[(trichloromethyl)thio]-;Phthalimide,N-[(trichloromethyl)thio]-;2-[(Trichloromethyl)thio]-1H-isoindole-1,3(2H)-dione;Folpet;Ftalan;Orthophaltan;Phaltan;Phthaltan;N-[(Trichloromethyl)thio]phthalimide;Spolacid;Phaltane;Fungitrol 11;Faltan;Folpel;Folpan;Vinicoll;Cosan T;Intercide TMP;Folnit;Orthofaltan 50;Sanfol;Trifol;Ryl;Acryptane;Dipet;MCW 296 SC;2-[(Trichloromethyl)sulfanyl]-2,3-dihydro-1H-isoindole-1,3-dione;52306-33-9;1135442-81-7
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CAS No:
Description
Off-White to Pale Yellow SolidChEBI: A member of the class of phthalimides that is phthalimide in which the hydrogen attached to the nitrogen is replaced by a trichloromethylthio group. An agricultural fungicide, it has been used to control mildew, leaf spot, and other diseases in crops sice he 1950s.Folpet is practically insoluble in water. It is a protective leaf fungicide. Its mode of action inhibits normal cell division of a broad spectrum of microorganisms. It is used to control cherry
Folpet appears as white crystals. Used as a fungicide. Insoluble in water.|Solid|WHITE CRYSTALS.|White crystals.
Folpet appears as white crystals. Used as a fungicide. Insoluble in water.|Folpet is a member of the class of phthalimides that is phthalimide in which the hydrogen attached to the nitrogen is replaced by a trichloromethylthio group. An agricultural fungicide, it has been used to control mildew, leaf spot, and other diseases in crops sice the 1950s. It has a role as an antifungal agrochemical. It is an organochlorine compound, an organosulfur compound and a phthalimide fungicide. It derives from a phthalimide.
Folpet Basic Attributes
296.56
296.56
205-088-6
X5NFK36917
0156
3077|2588
DTXSID0021385
Crystals from benzene|Light colored powder|Colorless crystals|White crystals
29309090
Characteristics
62.7
2.85
Folpet appears as white crystals. Used as a fungicide. Insoluble in water.
1.72 at 20 deg C
177 °C
333.8±52.0 °C(Predicted)
155.7±30.7 °C
1.6000 (estimate)
Practically insoluble in water
0-6°C
Vapour pressure, Pa at 20°C:
1.72
Oral-Rat LD50: 7540 mg/kg; Oral-Mouse LD50: 1546 mg/kg
Henry's Law constant = 7.66X10-8 atm-cu m/mol at 25 °C (est)
Yellow powder /Technical folpet 90-95%/|CHEMICALLY RELATED TO CAPTAN|Hydroxyl radical reaction rate constant = 1.57X10-11 cu cm/molec-sec at 25 °C (est)
Insoluble in water. Hydrolyzed in alkaline solution. Hydrolysis products are corrosive to many metals.
Amides and Imides
A halogenated phthalimide.
NON-CORROSIVE; DECOMP PRODUCTS ARE CORROSIVE
Safety Information
III
9
UN30779/PG3
2
20-36-40-43-50
36/37-46-61
TI5685000
Xn,N
The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials
Stable, except under alkaline conditions.
P261-P273-P280-P304 + P340 + P312-P333 + P313-P337 + P313
H317-H319-H332-H351-H400
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity 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 and plant life; and conformance with environmental and public health regulations.|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 permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. 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 be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.|Recommendable method: Incineration. Peer-review: For large amt, incineration in a unit with effluent gas scrubbing is recommendable. (Peer-review conclusions of an IRPTC expert consultation (May 1985))|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. /Residential users/|For more Disposal Methods (Complete) data for FOLPET (10 total), please visit the HSDB record page.
... Incompatible with strongly alkaline material.
USEPA/Office of Pesticide Programs; Reregistration Eligibility Decision Document - Folpet, EPA 738-R-99-011 (November 1999). 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 January 26, 2012: http://www.epa.gov/pesticides/reregistration/status.htm]|Toxicology Review: Mutation Research 32 (1): 3 (1975)
Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Some may burn but none ignite readily. Containers may explode when heated. Some may be transported hot. For UN3508, be aware of possible short circuiting as this product is transported in a charged state. (ERG, 2016)|Combustible under specific conditions. Liquid formulations containing organic solvents may be flammable. Gives off irritating or toxic fumes (or gases) in a fire.
|Warning|H317: May cause an allergic skin reaction [Warning Sensitization, Skin]|P201, P202, P261, P264, P271, P272, P273, P280, P281, P302+P352, P304+P312, P304+P340, P305+P351+P338, P308+P313, P312, P321, P333+P313, P337+P313, P363, P391, P405, and P501|H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]|Aggregated GHS information provided by 2576 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Danger|P201, P202, P260, P261, P271, P272, P280, P281, P284, P302+P352, P304+P340, P308+P313, P310, P320, P321, P333+P313, P363, P403+P233, P405, and P501
Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: As an 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, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck 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, 2016)
Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent dust cloud. Avoid inhalation of asbestos dust. SMALL DRY SPILL: With clean shovel, place material into clean, dry container and cover loosely; move containers from spill area. SMALL SPILL: Pick up with sand or other non-combustible absorbent material and place into containers for later disposal. LARGE SPILL: Dike far ahead of liquid spill for later disposal. Cover powder spill with plastic sheet or tarp to minimize spreading. Prevent entry into waterways, sewers, basements or confined areas. (ERG, 2016)
Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. (ERG, 2016)|Protective eyewear.|Applicators and other handlers must wear: Protective eyewear such as safety glasses, goggles, or face shield; Coveralls over a short-sleeved shirt and short pants; Chemical resistant gloves; Chemical-resistant apron when mixing and loading and cleaning equipment; Chemical-resistant headgear for overhead exposure; and Chemical-resistant footwear and socks. /Folpan 80 WDG Fungicide/|PRECAUTIONS FOR "CARCINOGENS": ... Dispensers of liq detergent /should be available./ ... Safety pipettes should be used for all pipetting. ... In animal laboratory, personnel should ... wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. ... Gowns ... /should be/ of distinctive color, this is a reminder that they are not to be worn outside the laboratory. /Chemical Carcinogens/
Extinguishing Media: In case of small fire: foam or dry chemical, carbon dioxide. In case of large fire: water spray, fog or regular foam. /Folpan 80 WDG Fungicide/|Firefighters should wear suitable protective clothing. Self-contained breathing apparatus. Fight fires from a protected location. Dike fire control water for later disposal. /Folpan 80 WDG Fungicide/
Do not contaminate water by cleaning of equipment or disposal of rinsate. /Folpan 80 WDG Fungicide/|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./Residential users/|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. /Residential users/|PRECAUTIONS FOR "CARCINOGENS": A high-efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air ventilated safety cabinets, lab hoods, glove boxes or animal rooms ... Filter housing that is designed so that used filters can be transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal ... The plastic bag should be sealed immediately ... The sealed bag should be labelled properly ... Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured & the bottles properly labelled. Once filled, bottles should be placed in plastic bag, so that outer surface ... is not contaminated ... The plastic bag should also be sealed & labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. The completeness of the cleaning procedures should be considered before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at the end of shift, but should remain at employee's place of work for cleaning.|Use this product only in accordance with its labeling and with the Worker Protection Standard, 40 CFR part 170. /Folpan 80 WDG Fungicide/|Do not enter or allow worker entry into treated areas during the restricted entry interval (REI) of 24 hours. /Folpan 80 WDG Fungicide/|/Restricted-entry interval (REI) of 24 hours./ PPE required for early entry to treated areas that is permitted under the Worker Protection Standard and that involves contact with anything that has been treated such as plants, soil, or water, is: Protective eyewear such as safety glasses, goggles, or face shield; Coveralls over short-sleeved shirt and short pants; Chemical-resistant gloves; and Chemical-resistant footwear plus socks. /Folpan 80 WDG Fungicide/|For more Preventive Measures (Complete) data for FOLPET (22 total), please visit the HSDB record page.
PRECAUTIONS FOR "CARCINOGENS": Procurement ... of unduly large amt ... should be avoided. To avoid spilling, carcinogens should be transported in securely sealed glass bottles or ampoules, which should themselves be placed inside strong screw-cap or snap-top container that will not open when dropped & will resist attack from the carcinogen. Both bottle & the outside container should be appropriately labelled. ... National post offices, railway companies, road haulage companies & airlines have regulations governing transport of hazardous materials. These authorities should be consulted before ... material is shipped. /Chemical Carcinogens/|PRECAUTIONS FOR "CARCINOGENS": When no regulations exist, the following procedure must be adopted. The carcinogen should be enclosed in a securely sealed, watertight container (primary container), which should be enclosed in a second, unbreakable, leakproof container that will withstand chem attack from the carcinogen (secondary container). The space between primary & secondary container should be filled with absorbent material, which would withstand chem attack from the carcinogen & is sufficient to absorb the entire contents of the primary container in the event of breakage or leakage. Each secondary container should then be enclosed in a strong outer box. The space between the secondary container & the outer box should be filled with an appropriate quantity of shock-absorbent material. Sender should use fastest & most secure form of transport & notify recipient of its departure. If parcel is not received when expected, carrier should be informed so that immediate effort can be made to find it. Traffic schedules should be consulted to avoid ... arrival on weekend or holiday ... /Chemical Carcinogens/
Contact with eyes and skin or inhalation of dust or spray mist can result in local irritation.|May irritate mucosal surfaces.
Personal protection: protective gloves and chemical protection suit. 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.
Provision to contain effluent from fire extinguishing. Store in an area without drain or sewer access. Separated from food and feedstuffs.
A nuisance-causing concentration of airborne particles can be reached quickly when dispersed.
The substance is irritating to the eyes.
Repeated or prolonged contact with skin may cause dermatitis. Repeated or prolonged contact may cause skin sensitization. The substance may have effects on the gastrointestinal tract. Tumours have been detected in experimental animals but may not be relevant to humans.
NO open flames.
AVOID ALL CONTACT!
Use ventilation (not if powder).
Protective gloves. Protective clothing.
Wear safety spectacles.
URBAN/SUBURBAN: Of nine domiciles located in Jacksonville, FL monitored for folpet in indoor and outdoor air during August, 1985, folpet was qualitatively identified in 5 and 4 domiciles, respectively(1). Outdoor air samples taken on two separate days from a household located in an area of high pesticide use contained folpet concentrations of 0.016 and 0.018 ug/cu m, respectively(1). Indoor air samples taken on two separate days from a household located in an area of low pesticide use contained folpet concentrations of 0.0 and 0.082 ug/cu m, respectively(1). Outdoor air samples taken on two separate days from a household located in an area of low pesticide use contained folpet concentrations of 0.0 and 0.021 ug/cu m, respectively(1). Of 232 households located in Jacksonville, FL monitored for indoor air in the summer of 1986, the spring of 1987, and the winter of 1988, folpet was quantitatively identified in 2% (0.5 ng/cu m weighted mean concentration), 1% (0.7 ng/cu m weighted mean concentration), and 3% (0.6 ng/cu m weighted mean concentration) of all households sampled, respectively(2). Of 229 households located in Jacksonville, FL monitored for outdoor air in the summer of 1986, the spring of 1987, and the winter of 1988, folpet was quantitatively identified in 7% (0.3 ng/cu m weighted mean concentration), 2% (0.4 ng/cu m weighted mean concentration), and 0% of all households sampled, respectively(2). Of 120 households located in Springfield/Chicopee, MA monitored for indoor air in the spring of 1987 and the winter of 1988, folpet was quantitatively identified in 2% (0.7 ng/cu m weighted mean concentration) and 0% of all households sampled, respectively(2). Of 118 households located in Springfield/Chicopee, MA monitored for outdoor air in the spring of 1987 and the winter of 1988, folpet was quantitatively identified in 2% (0.5 ng/cu m weighted mean concentration) and 0% of all households sampled, respectively(2).
Folpet was not detected in fifteen animal feed concentrate samples from Karnal (Haryana) India(1).
Toxicity
moderately toxic
LC50 RAT INHALATION GREATER THAN 5.0 MG/L/2 HR /TECHNICAL/|LC50 MOUSE INHALATION GREATER THAN 6.0 MG/L/2 HR /TECHNICAL/|LD50 Rabbit (albino) percutaneous >22,600 mg/kg|LC50 Rat inhalation >1.89 mg/l/4 hr|For more Non-Human Toxicity Values (Complete) data for FOLPET (8 total), please visit the HSDB record page.
/BIRDS and MAMMALS/ Acute oral toxicity in male mallards/: only signs seen were mild ataxia and wings crossed high over back for up to 18 days. Slight weight losses occurred.|/PLANTS/ Non-phytotoxic, except to sweet cherries and the D'Anjou variety of pears. Russetting is possible in sensitive apple varieties if applied early in cropping.
Folpet's production and use as a fungicide-bactericide for vinyls, paints, and enamels(1) may result in its release to the environment through various waste streams(SRC). Its use as an agricultural fungicide(2) will result in its direct release to the environment(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), a Koc range of 7.47 to 21.9(2), indicates that folpet is expected to have very high mobility in soil(SRC). Volatilization of folpet from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 7.7X10-8 atm-cu m/mole(SRC), based upon its vapor pressure, 1.57X10-7 mm Hg(3), and water solubility, 0.8 mg/L(3). Folpet is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Soil metabolism studies report degradation half-lives of 2.4-2.5 days under aerobic conditions and <7-15 days under anaerobic conditions(2), suggesting that biodegradation is an important environmental fate process in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), a Koc range of 7.47 to 21.9(2), indicates that folpet is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 7.7X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 1.57X10-7 mm Hg(4), and water solubility, 0.8 mg/L(4). According to a classification scheme(5), a BCF of range of 19 to 81(2), suggests the potential for bioconcentration in aquatic organisms is low to moderate(SRC). Biodegradation data in water were not available(SRC, 2012).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), folpet, which has a vapor pressure of 1.57X10-7 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase folpet 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 8 hours(SRC), calculated from its rate constant of 1.6X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase folpet may be removed from the air by wet or dry deposition(SRC). The UV spectrum of folpet in hexane shows no absorbance at wavelengths above 300 nm(4), and therefore folpet is not expected to be susceptible to direct photolysis by sunlight(SRC).
... REPORTED TO UNDERGO PHOTODECOMPOSITION ON PLANT SURFACES TO PHTHALIC ACID, CHLORIDE, & INORG SULFUR CMPD. IN PRESENCE OF SULFHYDRYL CMPD, FOLPET DEGRADES RAPIDLY TO SULFUR, PHTHALIMIDE, & HYDROCHLORIC ACID ... .|The rate constant for the vapor-phase reaction of folpet with photochemically-produced hydroxyl radicals has been estimated as 1.6X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 8 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Folpet is reported to hydrolyze slowly in water at room temperature and to hydrolyze rapidly at elevated temperature or in alkaline solutions(2). The hydrolysis half-lives are 2.6 hours, 1.1 hours, and 67 seconds at pH 5,7, and 9, respectively(3). The predominant hydrolysis products of folpet are phthalimide, phthalamic acid and phthalic acid(2,3). No photochemically-induced changes in the degradation rate or product distribution were observed in 0.96 ppm solutions of folpet in aqueous pH 3 buffers irradiated with UV light for 8 hours(3). The UV spectrum of folpet in hexane shows no absorbance at wavelengths above 300 nm(4).
Bioconcentration factors (BCFs) of 19, 61, and 81 were determined for the fillet, whole fish, and viscera, respectively, in bluegill sunfish (Lepomis macrochirus)(1) using radiolabeled folpet at 10 ug/L. These bioconcentration factors are based on total radiolabeled residues and not specifically folpet residues. According to a classification scheme(2), this BCF range, based on total residues, suggests bioconcentration of folpet and its metabolites in aquatic organisms is low to moderate. The accumulated residues were eliminated over 7 days(1).
1.86e+03 L/kg|Koc values of 7.47 to 21.9 have been reported for folpet(1). According to a classification scheme(2), this estimated Koc value suggests that folpet is expected to have very high mobility in soil.
The Henry's Law constant for folpet is estimated as 7.7X10-8 atm-cu m/mole(SRC) derived from its vapor pressure, 1.57X10-7 mm Hg(1), and water solubility, 0.8 mg/L(1). This Henry's Law constant indicates that folpet is expected to be essentially nonvolatile from water and moist soil surfaces(3). Folpet is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).
SURFACE WATER: In a pilot study, folpet was detected in samples from 3 of 12 surface water ecosystems flowing to the Mediterranean Sea. The samples were collected between September 1993 and December 1994 from rivers, lagoons, marshes, drainage canals, and rice fields in agriculturally and industrially developed areas in Spain, France, Italy, and Greece. In most cases, the levels of folpet present were below the detection limits of the study (1-5 ng/L), but it was detected at levels of 1, 2, and 50 ng/L in three systems. The appearance of folpet in these systems correlated with its seasonal application in these regions(1).
6,391 domestic agricultural commodities were tested by surveillance sampling at the U.S. Food and Drugs Administration's Los Angeles District Laboratory from 10/1/81 to 9/30/86. Folpet residues were found in 24, 15, 57, 46, 31, and 28 of 6,391 commodities tested in concentration ranges of 0.05, 0.1, 0.5, 1.0, 2.0, and greater than 2.0 ppm, respectively. 12,044 imported agricultural commodities tested by surveillance sampling at the U.S. Food and Drugs Administration's Los Angeles District Laboratory from 10/1/81 to 9/30/86. Folpet residues were 1, 1, 2, 1, and 13 of the 12,044 commodites tested in concentration ranges of 0.05, 0.1, 0.5, 2.0, and greater than 2.0 ppm, respectively. 177 domestic agricultural commodities were tested by compliance sampling at the U.S. Food and Drug Administration's Los Angeles District Laboratory from 10/1/81 to 9/30/86. Folpet residues were found in 5 and 1 findings in concentration ranges of 0.05 and 0.5 ppm, respectively. 1,239 imported agricultural commodities were tested by compliance sampling at the U.S. Food and Drug Administration's Los Angeles District Laboratory from 10/1/81 to 9/30/86. Folpet residues were found in 1, 1, and 1 of 1,239 commodities tested in concentration ranges of 0.5, 1.0 and 2.0 ppm, respectively(1).|Pesticide residue findings for food products tested by 10 state food laboratories for the U.S. Food and Drug Administration during fiscal year 1988 were 108 findings out of 13,980 samples(1). Pesticide residue findings for food products tested by 10 state food laboratories for the U.S. Food and Drug Administration during fiscal year 1989 were 27 findings out of 13,085 samples(1). Folpet was qualitatively found as residue in samples tested during the Food and Drug Administration pesticide residue monitoring of various food samples during the test period of 1978-1982(2), during the test period of 1983-1986(3), during the test period of 1988-1989(4), and during the test period of 1989-1990(5).|In 1992-1993, domestic and imported pears and tomatoes were tested by the Food and Drug Administration in a statistically based study of pesticide residues. Folpet was not detected in samples of 710 domestic pears, 949 imported pears, and 1219 domestic tomatoes. Folpet was detected in 3 out of 144 samples of imported tomatoes, with a maximum level found of 0.11 ppm(1). In a compilation of monitoring data compiled through the US Food and Drug Administration's Market Basket Studies for the years 1982-1991, folpet was detected in 3 of 234 ready-to-eat food items that were tested. The average levels detected were 10.5 ng/g, 14.0 ng/g, and 225 ng/g in fresh grapes, plums, and strawberries, respectively(2). 109 of 2338 samples of Ontario, Canada-produced fruits and vegetables, collected between 1991 to 1995 contained folpet, at concentrations from <0.01 to >10 ug/g, a 4.7% detection frequency; 4 of the 109 samples where this compound was detected had concentrations of folpet which were sufficient to violate maximum residue limits set by Health Canada(3). Sampling from January 1994 through December 2001 of Sao Paulo, Brazil-produced fruits (1523) and vegetables (700) revealed folpet concentrations from 0.02 to 7.53 mg/kg (mean 0.82 mg/kg); 2 of the 77 samples where this compound was detected had concentrations of folpet which were sufficient to violate maximum residue limits(4).
NIOSH (NOES Survey 1981-1983) has statistically estimated that 10,509 workers (1,422 of these were female) were potentially exposed to folpet in the US(1). The NOES Survey does not include farm workers. Occupational exposure to folpet may occur through inhalation and dermal contact with this compound at workplaces where folpet is produced or used. Monitoring data indicate that the general population may be exposed to folpet via inhalation of ambient air and ingestion of food(SRC).
Of nine domiciles located in Jacksonville, FL monitored for folpet in respiratory air during August, 1985, folpet was qualitatively identified in 4 domiciles(1). Personal exposure air samples taken on two separate days from a household located in an area of high pesticide use contained folpet concentrations of 0.19 and 0.023 ug/cu m, respectively(1). Of 248 households located in Jacksonville, FL monitored for personal air in the summer of 1986, the spring of 1987, and the winter of 1988, folpet was quantitatively identified in 2% (0.4 ng/cu m weighted mean concentration), 2% (0.4 ng/cu m weighted mean concentration), and 2% (0.8 ng/cu m weighted mean concentration) of all households sampled, respectively(2). Of 128 households located in Springfield/Chicopee, MA monitored for personal air in the spring of 1987 and the winter of 1988, folpet was quantitatively identified in 2% (0.7 ng/cu m weighted mean concentration) and less than 1% of all households sampled, respectively(2).
Drug Information
Chemicals that kill or inhibit the growth of fungi in agricultural applications, on wood, plastics, or other materials, in swimming pools, etc. (See all compounds classified as Fungicides, Industrial.)
A study with (14)C-folpet 50 WP in rats indicated a systemic absorption of 0.27% per hour (6.5% in 24 hr). This calculation was based on a least square analysis of 24 hr urinary excretion at dose levels of 49, 460, and 4800 ug/sq cm (13.2, 3.5, and 1.3% respectively ), matching the excretion to the approximate dermal exposure of 2400 ug/sq cm, based on the 50WP formulation concentration. There was rapid uptake of folpet into the skin and 95 and 94% for dose levels 4800 and 460 ug/sq cm, respectively, were retained there at 24 Hr. The amount still in the skin after 24 hr for the low dose was approximately 85% of the applied dose.|In a comparative metabolic fate and biochemical effects study, both rats and mice each received a single oral gavage dose of (14)C-labeled folpet. Two hours after dosing, the majority of the radioactivity in the contents of the gastrointestinal tract at the high dose was in the stomach as unchanged folpet. ... Unchanged folpet was present in the cecum of mice, but not rats, at the highest dose indicating that this dose was close to the animal's maximum capacity to degrade folpet. The pulse dose passed through the gastrointestinal tract of the mouse more rapidly than did the dose in rats. ... Radioactivity was rapidly excreted by all routes with most of the dose of (14)C eliminated within 24 hours.|An oral metabolism study was conducted in Sprague Dawley rats. Folpet was readily and extensively absorbed and rapidly excreted in the urine. There was no accumulation of folpet detected during the 5 days after dosing. The major fecal metabolite was phthalamic acid|A dermal absorption study in rats indicates folpet is minimally absorbed. An absorption of 2.7% over 72 hours exposure was determined for folpet.|For more Absorption, Distribution and Excretion (Complete) data for FOLPET (7 total), please visit the HSDB record page.
It is reported that in rodents treated orally, folpet is rapidly degraded to phthalimide and thiophosgene (via thiocarbonyl chloride). Studies of metabolism in vitro with human blood revealed that folpet is rapidly degraded to phthalimide, with a calculated half-life of 4.9 s. Thiophosgene is rapidly detoxified by reaction with cysteine or glutathione, for example, and is ultimately rapidly excreted.|... Folpet is extensively altered in mammalian and avian systems through a combination of enzymatic as well as nonenzymatic chemical reactions. Two complemetry processes, hydrolysis and thiol interactions, initially split the fungicide into /its/ imide ring and trichloromethylthio complex. Subsequent reactions, some of which may be enzymatic, produce a series of imide-based degradates and thiophosgene-mediated products. The reactions are rapid and nearly all material is eliminated from the animal within 24-48 hr; there is no accumulation of either imide or side chain.|Following dosing of /livestock with/ (14)C-benzene-labeled folpet, most of the radioactivity was excreted in urine and feces. ... Analysis of radioactivity in tissue and milk samples showed the presence of phthalamic acid and phthalimide. The results of the ruminant metabolism study suggest that folpet is degraded by loss of the one carbon trichloromethyl moiety. This part of the molecule becomes extensively metabolized and the radiolabeled carbon becomes incorporated into thiazolidine and natural products. The remaining phenyl labeled part of the molecule is mostly metabolized to phthalimide and phthalamic acid.|In a comparative metabolic fate and biochemical effects study, both rats and mice each received a single oral gavage dose of (14)C-labeled folpet. ... No breakdown of the compound by cleavage of the trichloromethylthio side chain (where the (14)C label was positioned) was apparent in either the rat or mouse. The contents of sections of the intestinal tract contained primarily reaction products of thiophosgene. ... The metabolites identified in the contents of the intestine and in the walls were glutathione conjugates of thiophosgene, partially degraded derivatives of the conjugate, thiazolidine and a disulfonic acid.|For more Metabolism/Metabolites (Complete) data for FOLPET (7 total), please visit the HSDB record page.
... Calculated half-life of 4.9 seconds.
Both folpet and captan appear to exert toxicity via the reaction of thiophosgene with the gastrointestinal tract. A more thorough review has been conducted on the mechanistic studies submitted for the related fungicide, captan. For captan, the Agency has concluded that thiophosgene is most likely implicated in the duodenal tumors, although its exact mode of action is unclear and a genotoxic component cannot be ruled out.
Major impurities are unreacted phthalimide (4.5%), water & calcium carbonate (up to 2.5% each), & sulfur ... .
Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Inhalation of material may be harmful. Contact may cause burns to skin and eyes. Inhalation of Asbestos dust may have a damaging effect on the lungs. Fire may produce irritating, corrosive and/or toxic gases. Some liquids produce vapors that may cause dizziness or suffocation. Runoff from fire control may cause pollution. (ERG, 2016)|Carcinogens
Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. (ERG, 2016)
Fresh air, rest. Refer for medical attention.
Remove contaminated clothes. Rinse and then wash skin with water and soap. Seek medical attention if you feel unwell.
Rinse with plenty of water for several minutes (remove contact lenses if easily possible).
Skin decontamination: Skin contamination should he treated promptly by washing with soap and water. Contamination of the eyes should be treated immediately by prolonged flushing of the eyes with large amounts of clean water. If dermal or ocular irritation persists, medical attention should be, obtained without delay. /Herbicides/|Gastrointestinal decontamination: Ingestion of these herbicides are likely to be followed by vomiting and diarrhea due to their irritant properties. Management depends on: (1) the best estimate of the quantity ingested, (2) time elapsed since ingestion, and (3) the clinical status of the subject. Activated charcoal is probably effective in limiting irritant effects and reducing absorption of most or all of these herbicides. Aluminum hydroxide antacids may be useful in neutralizing the irritant actions of more acidic agents. Sorbitol should be given to induce catharsis if bowel sounds are present and if diarrhea has not already commenced. Dehydration and electrolyte may be severe enough to require oral or intravenous fluids. There are no specific antidotes for poisoning by these herbicides. In the case of suicidal ingestions, particularly, the possibility must always be kept in mind that multiple toxic substances may have been swallowed. If large amounts of herbicide have been ingested and the patient is seen an hour of the ingestion, gastrointestinal decontamination should be considered. If the amount of ingested herbicides was small, if effective emesis has already occurred, or if treatment is delayed, administer activated charcoal and sorbitol mouth. /Herbicides/|Intravenous fluids: If serious dehydration and electrolyte depletion have occurred as a result of vomiting and diarrhea, monitor blood electrolytes and fluid balance and administer intravenous infusions of glucose, normal saline, Ringer's solution, or Ringer's lactate to restore extracellular fluid volume and electrolytes. Follow this with oral nutrients as soon as fluids can be retained. /Herbicides/|/SRP:/ Immediate first aid: Remove patient from contact with the material. Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Dithiocarbamates and Related Compounds/|For more Antidote and Emergency Treatment (Complete) data for FOLPET (6 total), please visit the HSDB record page.
/HUMAN EXPOSURE STUDIES/ A survey of the irritant and sensitizing potential of pesticides was conducted, in order to determine the frequency of irritant and allergic reactions due to exposure to pesticides that are widely used in Italy. Thirty six pesticide preparations were used in patch tests on 652 patients, 377 of whom were males, at a dermatological clinic in Perugia, Italy. A total of 274 subjects had contact dermatitis on their hands. Ninety two were current and 11 were former agricultural workers. Concn of pesticide used in the tests ranged from 0.05 to 2% and the reactions were read at 48 and 72 hr. Allergic reactions were seen in 46 subjects. These resulted primarily from the fungicides, captan, folpet, and difolatan. The observed allergic reactions in 24 subjects were considered relevant to their contact dermatitis. Sixty six subjects showed irritant reactions. Current and former agricultural workers had a significantly greater sensitivity to pesticides compared to the other patients. It was concluded that sensitivity to pesticides is rather uncommon, and that allergic reactions induced by pesticides are almost always due to fungicides.|/SIGNS AND SYMPTOMS/ Short term exposure effects of folpet: skin absorption; irritation of the eyes and respiratory tract. Long term exposure effects: dermatitis; skin sensitization; may have effects on the GI tract, thyroid, lymphatic and blood forming tissues, kidneys and muscles; may cause genetic damage and retarded development of the newborn.|/CASE REPORTS/ A case report of multiple sensitization due to occupational exposure to bis-dithiocarbamate and thiophthalimide pesticides was presented. A 45 year old female agricultural worker complained of a 2 month history of eczema of the fingers of her right hand which improved when she stopped work. Patch tests with the GIRDCA standard series and a pesticides series revealed positive reactions to carbamate mix, captan, captafol, maneb, and folpet, at 2 and 3 days. The subject said that she had used several pesticides over the year without wearing gloves, although glove use was recommended on the labels of the products. The dermatitis completely resolved when the patient stopped using pesticides. ... In this patient, the development of multiple sensitization was probably favored by habitual use of pesticides without the use of gloves.|/SURVEILLANCE/ Folpet was involved in 6 cases of human poisoning between 1967 and 1975, according to EPA Pesticide Episode Review system ... .|For more Human Toxicity Excerpts (Complete) data for FOLPET (6 total), please visit the HSDB record page.
folpet
The substance can be absorbed into the body by inhalation.
Dry skin.
Redness.
Folpet Use and Manufacturing
The preparation of chloroform is mixed with 2% hydrochloric acid and metered carbon disulfide, stirring and passing chlorine, controlling the flow rate of chlorine gas to maintain the reaction temperature at about 26 ℃, and controlling the normal absorption and treatment of the reaction tail gas, generally It takes about 30h. Finally, chloroform was separated by standing, and washed with water for synthetic sterilization. The preparation of phthalimide is made by co-heating phthalic anhydride and ammonium bicarbonate. During production, phthalic anhydride and ammonium bicarbonate are mixed in a 3:1 (mass ratio), and then put into a hot melt tank, heated by direct fire, and reacted at 300℃ for 10 to 12 hours. Since this operation is not easy to control, the reaction is not It is complete, consumes energy, has a long reaction period, and pollutes the environment. Because it can be dissolved by adding phthalic anhydride to ammonia water, diammonium salt is formed and the water is distilled off. Reheating to a higher temperature further dehydration, generating imine compounds. For the synthesis of sterilized Dan, 4.5% of the lye is metered into the condensation reaction pot, and the temperature is reduced to -4°C. After an excessive amount of phthalimide solution is added under vigorous stirring, a certain amount of three Chlorosulfur chloride, temperature is controlled at about -2 ℃, the reaction end pH=8, and finally the condensate is centrifuged, washed with water, dried by airflow and other post-treatments to prepare sterilized dan.
Agricultural fungicide.
(1975) 1.82X10+8 G (EST)
APPROX 50% AS A FUNGICIDE FOR DECIDUOUS FRUIT; APPROX 25% AS A FUNGICIDE FOR VEGETABLES; AND APPROX 25% AS A FUNGICIDE FOR ORNAMENTALS (1975)
USEPA/OPP Pesticide Code 081601; Trade Names: Phaltan; Folpan; Folpex.|Dusts, flowable, wettable granule, wettable powder.|Premix Partners: Benalaxyl; benalaxyl-M; Copper hydroxide; Copper sulfate; Cymoxanil; Dimethomorph; Fosetyl-aluminum; Mancozeb; Metalaxyl-M; Oxadixyl; Prochloraz; Propioconazole; Triadimenol; Valifenalate.|Technical grade: 88%. Liquid ready-to-use 0.3 to 0.7%; wettable powder 44 to 50%.|For more Formulations/Preparations (Complete) data for FOLPET (18 total), please visit the HSDB record page.
1H-Isoindole-1,3(2H)-dione, 2-[(trichloromethyl)thio]-: ACTIVE|The WHO Recommended Classification of Pesticides by Hazard identifies folpet as unlikely to present an acute hazard in normal use; Main Use: fungicide, other than for seed treatment.|Incompatible with strongly alkaline materials.
Product analysis by i.r. spectroscopy or by hplc with uv detection. Residues determined by gc ... In soil by gc/ECD.|AOAC Method 977.03. Folpet in pesticide formulations. Liquid chromatography method. Applicable to dry formulations contg folpet as only active ingredients and to folpet combination formulations except those contg propargite or Me parathion.|GC ANALYSIS OF PHALTAN.|Two multiresidue methods, the Mills method and the Luke method, were evaluated for the determination of folpet in selected fruits and vegetables fortified with levels of 0.2-5.9 ppm. The analyte was quantitated by GC with ECD, using a column of 5% SP-2401 on 100-120 mesh Supelcoport. Recovery of folpet ranged from 90-93% by the Mills procedure and from 81 to 106% by the Luke method modified to include additional solvent elution of the optional Florisil column.|For more Analytic Laboratory Methods (Complete) data for FOLPET (10 total), please visit the HSDB record page.
Agrochemicals -> Fungicides|Health Hazards -> Carcinogens|Fungicides|Environmental transformation -> Pesticides (parent, predecessor)|FUNGICIDES
Folpet has known environmental transformation products that include phthalamic acid , phthalic acid, and phthalimide.|Folpet has known environmental transformation products that include Phthalamic acid, Phthalic acid, and Phthalimide.
Computed Properties
Molecular Weight:296.6
XLogP3:2.8
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:294.902833
Monoisotopic Mass:294.902833
Topological Polar Surface Area:62.7
Heavy Atom Count:16
Complexity:307
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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