基本信息
- 标准SMILES
O=C1c2ccccc2C(=O)N1SC(Cl)(Cl)Cl- InChIKey
HKIOYBQGHSTUDB-UHFFFAOYSA-N- 分子式
- C9H4Cl3NO2S
- 平均分子量
- 296.6 g/mol
- 单同位素质量
- 294.90283241
概述
Folpet can cause cancer according to an independent committee of scientific and health experts.
名称与标识
- 首选名称
- Folpet
- IUPAC
- 2-(trichloromethylsulfanyl)isoindole-1,3-dione
- 中文名
- 灭菌丹
- 英文名
- Folpet
- 分子式
- C9H4Cl3NO2S
- 分子量
- 296.56
名称与别名
展开更多名称
数据库标识
- CAS
133-07-3- PubChem CID
- 8607
- DTXSID
DTXSID0021385- ChEMBL
CHEMBL1883819- ChEBI
CHEBI:82019- UNII
- X5NFK36917
- EC Number
- 205-088-6
- Nikkaji
- J2.948C
性质
结构计算性质
- XLogP
- 2.8
- 极性表面积
- 62.7 Ų
- 氢键供体
- 0
- 氢键受体
- 3
- 可旋转键
- 1
- 重原子
- 16
- 形式电荷
- 0
- 复杂度
- 307
实验与物化性质
Pesticides
Pesticide -> EPA IRIS
Agrochemicals -> Pesticide active substances
Active substance -> EU Pesticides database: Approved
Pesticides -> Fungicides
Environmental transformation -> Pesticides (parent, predecessor)
Fungicides
LogP
log Kow = 2.85
2.85
2.85
3.11
Color/Form
Crystals from benzene
Light colored powder
Colorless crystals
White crystals
Solubility
In carbon tetrachloride 6, toluene 26, methanol 3 (all in g/L at 25 °C)
Slightly soluble in organic solvents.
87 g/L chloroform; 22 g/L benzene; 12.5 g/L isopropanol
In water, 0.8 mg/L at room temperature
0.0008 mg/mL at 25 °C
Solubility in water: none
Melting Point
177 °C
177 °C
177 °C
Vapor Pressure
0.00000016 [mmHg]
2.1X10-2 mPa /1.57X10-7 mm Hg/ at 25 °C
Vapor pressure, Pa at 20 °C:
物理化学性质
- 熔点
- 177 · 177-180°C
- 沸点
- 333.8 · 333.8±52.0 °C(Predicted)
- 密度
- 1.5097 · 1.5097 (rough estimate)
- 蒸气压
- 2.1 x · 2.1 x 10-5 Pa (25 °C)
- 折射率
- 1.6 · 1.6000 (estimate)
- 储存条件
- 0 · 0-6°C
- 溶解度
- Chloroform (Slightly), Methanol (Slightly)
- 酸度系数(pKa)
- -3.34 · -3.34±0.20(Predicted)
- 形态
- Solid
- 颜色
- Crystals
- 水溶解性
- practically insoluble
- Merck
- 13 · 13,4250
- BRN
- 193373 · 193373
- Henry's Law Constant
- 1.3 · 1.3×102 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
- 主要应用
- agriculturecleaning productscosmeticsenvironmentalfood and beveragespersonal care
- InChI
- 1S/C9H4Cl3NO2S/c10-9(11,12)16-13-7(14)5-3-1-2-4-6(5)8(13)15/h1-4H
- InChIKey
- HKIOYBQGHSTUDB-UHFFFAOYSA-N
- SMILES
- ClC(Cl)(Cl)SN1C(=O)c2ccccc2C1=O
- LogP
- 2.85 · 2.850
- CAS 数据库
- 133 · 133-07-3(CAS DataBase Reference)
- NIST化学物质信息
- Folpet(133-07-3)
- EPA化学物质信息
- Folpet (133-07-3)
化学性质
纯品为白色结晶。m.p.177℃,蒸气压1.33×10-3Pa (20℃)。微溶于有机溶剂;不溶于水(仅1mg/L)。在干燥条件下较稳定,室温下遇水缓慢水解,遇高温或碱性物质迅速分解。
安全与法规
GHS分类
GHS Classification
Warning
H317: May cause an allergic skin reaction [Warning Sensitization, Skin]
P203, P261, P264+P265, P271, P272, P273, P280, P302+P352, P304+P340, P305+P351+P338, P317, P318, P321, P333+P317, P337+P317, P362+P364, P391, P405, and P501 (click each P-code to see the statement)
Warning
H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]
P203, P261, P264+P265, P271, P272, P273, P280, P302+P352, P304+P340, P305+P351+P338, P317, P318, P321, P333+P317, P337+P317, P362+P364, P391, P405, and P501 (click each P-code to see the statement)
危害信息
Regulatory Information
Chemical: 1H-Isoindole-1,3(2H)-dione, 2-[(trichloromethyl)thio]-
Hazard Traits - Carcinogenicity
Regulation (EC) No 396/2005 (amended)
Folpet is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)
07/5/EC, Reg. (EU) 2020/869, Reg. (EU) 2021/745, Reg. (EU) 2022/708, Reg. (EU) 2023/918, Reg. (EU) 2024/2198, Reg. (EU) No 2019/707, Reg.(EU) No 2018/917, Reg.(EU) No 540/2011
Folpet: HSNO Approval: HSR002854 Approved with controls
Fire Hazards
Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Combustible under specific conditions. Liquid formulations containing organic solvents may be flammable. Gives off irritating or toxic fumes (or gases) in a fire.
Hazards Summary
A skin sensitizer in guinea pigs; Sensitization not reported in humans despite wide-scale use; TLV Basis is liver damage and body weight effects; [ACGIH] The thiophthalimides include captan, captafol, and folpet. No systemic poisonings in humans have been reported. [EPA Pesticides] An eye irritant; May cause skin sensitization; Can be absorbed through skin; [ICSC] Rapidly forms the short-lived and highly reactive metabolite thiophosgene in the presence of thiols in tissue and blood; [Reference #2] Birth defects observed at very high doses in one study of hamsters, although negative results seen in studies of mice, rats, rabbits, and monkeys; [REPROTOX] A severe eye irritant and skin sensitizer; No evidence of toxicity to fertility or reproduction in a 2-generation study of rats, but teratogenic effects observed in rabbits; Not genotoxic in vivo but carcinogenic in mice; [EFSA]
Special Reports
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)
FIFRA Requirements
Tolerances are established for the fungicide folpet (N-(trichloromethylthio)phthalimide) in or on raw agricultural commodities as follows: [Table#4123]
Tolerances with regional registrations as defined in part 180.1(l) are established for the fungicide folpet ( N -(trichloromethylthio)phthalimide) in or on the following raw agricultural commodity: Avocado.
Based on the reviews of the generic data for the active ingredient folpet, the Agency has sufficient information on the health effects of folpet and on its potential for causing adverse effects in fish, wildlife, and the environment. The Agency has determined that folpet products, labeled and used as specified in this Reregistration Eligibility Decision Document, will not pose unreasonable risks of adverse effects to humans or the environment. Therefore, the Agency concludes that products containing folpet for use on Florida avocados and for use in sealants and coatings (such as caulking, paints, and stains) are eligible for reregistration.
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. Folpet 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: 0630; Pesticide type: fungicide; Registration Standard Date: 06/30/87; 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): folpet; Data Call-in (DCI) Date(s): 01/11/93, 10/13/95; AI Status: The producers of the pesticide have made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner.
安全与防护
Fire Fighting
Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Use water spray, powder, foam, carbon dioxide.
First Aid Measures
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).
Rinse mouth. Seek medical attention if you feel unwell.
Fire Fighting Procedures
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/
Storage Conditions
Store in dry place at ambient or lower temperatures.
Store in a cool, dry ventilated place. Protect from excessive heat. Keep locked up. Keep containers tightly closed. Keep only in the original container in ... Keep containers dry. To prevent contamination, store this product away from food or feed. Keep away from heat, fire and sparks.. /Folpan 80 WDG Fungicide/
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. /Residential users/
PRECAUTIONS FOR "CARCINOGENS": Storage site should be as close as practical to lab in which carcinogens are to be used, so that only small quantities required for ... expt need to be carried. Carcinogens should be kept in only one section of cupboard, an explosion-proof refrigerator or freezer (depending on chemicophysical properties ...) that bears appropriate label. An inventory ... should be kept, showing quantity of carcinogen & date it was acquired ... Facilities for dispensing ... should be contiguous to storage area. /Chemical Carcinogens/
Cleanup Methods
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/
Disposal Methods
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.
Spillage Disposal
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.
Preventive Measures
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.
毒理信息
Body Burden
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).
Ecotoxicity Values
LC50; Species: Anas platyrhynchos (Mallard Duck) juvenile; diet >5000 ppm for 8 days
LD50; Species: Anas platyrhynchos (Mallard duck) male, 3-4 month old; oral >2000 mg/kg /purity 92.4%/
LC50; Species: Colinus virginianus (Bobwhite quail) juvenile; diet >5000 ppm for 8 days
LD50; Species: Colinus virginianus (Bobwhite quail) age >16 wk; oral via capsule >2510 mg/kg
For more Ecotoxicity Values (Complete) data for FOLPET (56 total), please visit the HSDB record page.
Environmental Fate
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).
Food Survey Values
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).
Average Daily Intake
Using monitoring data from the FDA's Market Basket Survey during the period of 1988-89, the AVDI in 6-11 month old infants, 14-16 year old males and 60-65 year old females was 0.4, 0.2, and 0.5 ng/kg-body weight/day, respectively(1). Using monitoring data from the FDA's Market Basket Survey during the period of 1989-90, the AVDI in 6-11 month old infants, 14-16 year old males and 60-65 year old females was 0.1, 0.1, and less than 0.1 ng/kg-body weight/day, respectively(2). Using monitoring data from the FDA's Market Basket Survey during the period of 1986-91, the AVDI in 6-11 month old infants, 14-16 year old males and 60-65 year old females was 1.8, 0.7, and 2.0 ng/kg-body weight/day, respectively(3).
Ecotoxicity Excerpts
/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.
Plant Concentrations
In Dade County, FL, five foliar applications of folpet (50WP) at 3 lb ai/acre/application were applied to avocados. Following the final application, triplicate samples of avocados were collected at 1, 3, 7, 14, and 28 days post treatment. Folpet residues at day 1 were 0.101-0.183 ppm and declined to <0.05-0.066 ppm by day 28. The maximum folpet residue (0.356 ppm) was found in the day 3 sample(1).
Signs and Symptoms
Dry skin.
Redness.
法规信息
FIFRA Requirements
Tolerances are established for the fungicide folpet (N-(trichloromethylthio)phthalimide) in or on raw agricultural commodities as follows: [Table#4123]
Tolerances with regional registrations as defined in part 180.1(l) are established for the fungicide folpet ( N -(trichloromethylthio)phthalimide) in or on the following raw agricultural commodity: Avocado.
Based on the reviews of the generic data for the active ingredient folpet, the Agency has sufficient information on the health effects of folpet and on its potential for causing adverse effects in fish, wildlife, and the environment. The Agency has determined that folpet products, labeled and used as specified in this Reregistration Eligibility Decision Document, will not pose unreasonable risks of adverse effects to humans or the environment. Therefore, the Agency concludes that products containing folpet for use on Florida avocados and for use in sealants and coatings (such as caulking, paints, and stains) are eligible for reregistration.
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. Folpet 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: 0630; Pesticide type: fungicide; Registration Standard Date: 06/30/87; 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): folpet; Data Call-in (DCI) Date(s): 01/11/93, 10/13/95; AI Status: The producers of the pesticide have made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner.
安全数据
- wgk
- 2
- tsca
- TSCA listed
- 毒性
- LD50 orally in adult male, female rats: >5000 mg/kg (Gaines, Linder)
- RTECS号
- TI5685000
- 包装类别
- III
- 危险等级
- 9
- 存储类别
- 11 - Combustible Solids
- 安全说明
- 36/37-46-61
- 海关编码
- 29309090
- 危险品标志
- Xn,N
- 危险性类别
- Acute Tox. 4 InhalationAquatic Acute 1Carc. 2Eye Irrit. 2Skin Sens. 1
- 危险类别码
- 20-36-40-43-50
- 毒害物质数据
- 133-07-3(Hazardous Substances Data)
- 危险品运输编号
- UN 3077 9/PG 3
毒性防护
毒性大白鼠急性经口毒性LD50>10g/kg,大白鼠急性经皮毒性LD50>22.6g/kg。工业品按10000毫克/千克饲喂大白鼠17个月,未见病变或肿瘤;用含100~ 1000毫克/千克药量食物喂大鼠,连续三代对繁殖无不良影响。对粘膜有刺激作用,其粉尘或雾滴接触到眼睛、皮肤或吸入均能使局部受到刺激。鲤鱼TLm(48小时)为0.21mg/L。ADI 为0.1mg/kg。
急性毒性口服- 大鼠 LD50: 7540 毫克/ 公斤; 口服- 小鼠 LD50: 1546 毫克/ 公斤
包装储运
储运特性库房通风低温干燥; 与食品原料分开储运
灭火剂干粉、泡沫、砂土
化学与工业
药理信息
Mechanism of Action
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.
Metabolism/Metabolites
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.
Absorption, Distribution and Excretion
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.
用途与制造
Uses
Primarily used as an agricultural fungicide, but some industrial uses (paints and plastics); [ACGIH] The thiophthalimides are widely used fungicides on seeds, field crops, and stored produce; [EPA Pesticides] Used as a biocide in paints; [Adams, p. 475] Used in the USA as a pesticide on avocados and as a wood preservative; used in Europe on grapes; [Zainal h, Shane S, Que H. Flopet Permeation Through Nitrile Gloves. Appl Occup Environ Hyg 2003;18:658-668] Used in the US as fungicide for avocados, paints, caulking compounds, and wood treatments; [Reference #2] Used in the EU as fungicide for winter wheat, tomatoes, and wine grapes; [EFSA]
Painting (Pigments, Binders, and Biocides) [Category: Paint]
For Folpet (USEPA/OPP Pesticide Code: 081601) 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./
Broad spectrum contact fungicide that is effective against a fairly wide range of fungi that cause plant diseases. It acts by inhibiting fungal mycelial growth, but does not eradicate established fungal infection.
Folpet is used as a foliar fungicide on grapevines, fruit trees, and vegetables ...
Control of downy mildews, powdery mildews, leaf spot diseases, scab, excoriosis, black rot, white rot, Gleosporium rots, Botrytis, Alternaria, Phythium and Rhizoctonia spp ...
Methods of Manufacturing
Folpet is produced by reaction of the potassium salt of phthalimide with trichloromethanesulfenyl chloride in organic solvents.
Synthesized commerically by the reaction of perchloromethylmercaptan with sodiumphthalimide in a cold aqueous system.
Produced by the reaction of potassium salt of phthalimide with trichloromethansulfenyl chloride in organic solvents.
Formulations/Preparations
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.
Use Classification
Fungicides
Environmental transformation -> Pesticides (parent, predecessor)
FUNGICIDES
General Manufacturing Information
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.
应用领域
用途灭菌丹对白粉菌(Erysiphe spp.)、黑星病菌(Venturia spp.)、小丛壳菌(Glomerella spp.)、盘长孢菌(Gloeosporium spp.)、单丝壳菌(Sphaerotheca spp.)、叉丝单囊壳菌(Podos-phaera spp.)、霜霉菌(Peronospora spp.)、交链孢菌(Alternaria spp.)、疫霉菌(Phytophthora spp.)、葡萄孢菌(Botrytis spp.)等都有活性。用于防治粮食作物、蔬菜、果树等的多种病害,且对植物有刺激生长作用。例如可防治稻瘟病、水稻纹枯病、麦类锈病、花生叶斑病、马铃薯晚疫病、烟草炭疽病等。主要作喷雾使用:按0.1%左右浓度药液喷雾,防治瓜类、蔬菜、葡萄霜霉病、白粉病,马铃薯、番茄早疫病、晚疫病,苹果炭疽病、黑星病、白粉病,草莓等的灰霉病等;0.2%左右浓度药液,防治小麦白粉病、锈病、赤霉病和花生叶斑病、烟草炭疽病、小稻纹枯病等。用药剂量偏大时,梨、甜樱桃、桃和葡萄的一些品种易生药害。本品除不宜与强碱性药剂和油剂混用外,可与多数常用农药混用。已有若干复配制剂问世,如Trimifol(与铜盐复配),Mycodifol(与敌菌丹复配)等。
用途三氯甲烷基类保护性杀菌剂。主要喷雾防治粮油作物、蔬菜、果树等多种病害,且对植物有刺激生物的作用。防治稻瘟病用50%可湿性粉剂300~500倍液喷雾,穗颈瘟在发病始盛期喷药,穗颈稻瘟在始穗期及齐穗期各喷1次。防治水稻纹枯病,用40%可湿性粉剂200倍液喷雾。防治麦类锈病、赤霉病,用40%可湿性粉剂250倍液喷雾。防治油菜霜霉病用50%可湿性粉剂500倍液喷雾。防治花生叶斑病用50%可湿性粉剂200~250倍液喷雾。此外,还可用于防治马铃薯晚疫病、番茄早疫病、白菜霜霉病、瓜类霜霉病和白粉病、烟草炭疽病、苹果炭疽病、葡萄霜霉病和白粉病、茶云纹叶枯病、轮斑病、白星病等。
制备方法
生产方法三氯硫氯甲烷的制备 将配好的2%盐酸和计量的二硫化碳混合,搅拌通氯,控制氯气的流量,使其反应温度维持在26℃左右,并控制反应尾气的正常吸收和处理,一般需30h左右。最后静置分离出三氯硫氯甲烷,经水洗后供合成灭菌丹用。邻苯二甲酰亚胺的制备 由苯酐与碳酸氢铵共热制得。生产时将苯二甲酸酐与碳酸氢铵按3:1 (质量比)混合,后投入热溶罐中,用直接火加热, 于300℃反应10~12h,由于这样操作不易控制,反应也不完全,且耗能,反应周期长,对环境有污染。因可采用将邻苯二甲酸酐加到氨水中溶解,生成二铵盐,把水分蒸出。再加热到较高温度进一步脱水,生成亚胺化合物。灭菌丹的合成 将4。5%的碱液计量加入缩合反应锅中,降温至-4℃,在激烈搅拌下投入过量的邻苯二甲酰亚胺溶液后,均匀滴加一定量的三氯硫氯甲烷,温度控制在-2℃左右,反应终点pH=8,最后缩合物经离心分离,水洗,气流干燥等后处理,制得灭菌丹。
生产方法由邻苯二甲酰亚胺与三氯硫氯甲烷反应而得。先将5%的氢氧化钠溶液放入缩合锅内,搅拌冷却至-2℃,加入邻苯二甲酰亚胺,使其成为钠盐。在维持反应温度不高于10℃的情况下,滴加三氯硫氯甲烷。当反应物pH达8-9时出料过滤,干燥,即得灭菌丹,收率75%-79%。
上下游产品信息
上游原料
试剂价格
- HY-B1878R · 5 mg
- 灭菌丹Faltan (Standard) — 250元
- HY-B1878R · 10 mg
- 灭菌丹Faltan (Standard) — 400元
供应商50 家
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