Thiophanate-Methyl

Pesticide -> EPA IRIS

Fungicides

Active substance -> EU Pesticides database: Not approved

Pesticides -> Fungicides

Environmental transformation -> Pesticides (parent, predecessor)

Fungicides

log Kow = 1.40

1.5

Colorless crystals

Colorless prisms

Colorless crystalline solid

less than 1 mg/mL at 68 °F (NTP, 1992)

Sparingly soluble in most organic solvents at 25 °C (2.9 g/100 mL acetone; 7.8X10-1 g/100 mL methanol; 8.4X10-1 g/100 mL ethyl acetate; 7.3X10-2 g/100 mL dichloromethane; 1.8X10-2 g/100 mL n-octanol; 1.1X10-2 g/100 mL xylene; and 4.7X10-5 g/100 mL n-hexane)

In acetone 58.1, cyclohexanone 43, methanol 29.2, acetonitrile 24.4, ethyl acetate 11.9 (all in g/kg, 23 °C). Slightly soluble in hexane.

Thiophanate methyl is slightly soluble in most organic solvents... .

Soluble in acetone, methanol, chloroform and acetonitrile.

For more Solubility (Complete) data for THIOPHANATE METHYL (6 total), please visit the HSDB record page.

342 °F (Decomposes) (NTP, 1992)

172 °C (decomposes)

MP: 181.5 - 182.5 °C

342 °F

less than 0.0000001 mmHg at 68 °F (NTP, 1992)

0.00000007 [mmHg]

7.13X10-8 mm Hg at 25 °C

<0.0000001 mmHg

Thiophanate-methyl appears as colorless crystals or light brown powder. (NTP, 1992)

Colorless solid; [Merck Index] Colorless or light brown solid; [CAMEO] Colorless crystalline solid; [MSDSonline]

Colorless crystals or light brown powder.

Positive

2.52

2.7

Agilent XCT

Electrospray ionization

formic acid (5.3nM)

Warning

H317: May cause an allergic skin reaction [Warning Sensitization, Skin]

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

Hazard Traits - Reproductive Toxicity

Regulation (EC) No 396/2005 (amended)

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

05/53/EC, Reg. (EU) 2017/1511, Reg. (EU) 2018/1262, Reg. (EU) 2019/1589, Reg. (EU) 2020/1498, Reg. (EU) No 533/2013, Reg. (EU) No 540/2011

REACH registered substance: Thiophanate-methyl (EC: 245-740-7)

Thiophanate methyl: HSNO Approval: HSR003107 Approved with controls

Mildly irritating to skin and eyes; Does not inhibit the cholinesterase enzyme; Effects in high-dose animal studies include convulsions; In chronic feeding studies of mice, thyroxin (T4) levels were low, and TSH levels were high; Causes developmental and reproductive effects at maternotoxic doses; [HSDB] May cause irritation; [CAMEO] May cause skin sensitization; [eChemPortal: ESIS] A skin sensitizer in animal testing; [Reference #1]

USEPA/Office of Prevention, Pesticides and Toxic Substances; Reregistration Eligibility Decision Document - Thiophanate-Methyl (October 2005). The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the U.S.[Available from, as of May 29, 2009: http://www.epa.gov/pesticides/reregistration/status.htm]

California Environmental Protection Agency/Department of Pesticide Regulation; Toxicology Data Review Summary for Thiophanate methyl (23564-05-8).[Available from, as of May 11, 2009: http://www.cdpr.ca.gov/docs/risk/toxsums/toxsumlist.htm]

USEPA, Office of Prevention, Pesticides, and Toxic Substances; Revised HED Human Health Risk Assessment for Thiophanate-methyl (23564-05-8) (April 2002). EPA Docket No.: EPA-HQ-OPP-2004-0265-0010.

U.S. Environmental Protection Agency's Integrated Risk Information System (IRIS) on Thiophanate-methyl (23564-05-8).[Available from the Substance File List, as of May 11, 2009: http://www.epa.gov/iris/index.html]

U409; As stipulated in 40 CFR 261.33, when thiophanate-methyl, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

Tolerances are established for the combined residues of thiophanate-methyl (dimethyl [(1,2-phenylene) bis (iminocarbonothioyl)] bis(carbamate)) and its metabolite methyl 2-benzimidazoyl carbamate (MBC), calculated as thiophanate-methyl in or on the following commodities: [Table#6501]

Tolerances are established for the combined residues of thiophanate-methyl (dimethyl [(1,2-phenylene) bis (iminocarbonothioyl)] bis(carbamate)) and its metabolite methyl 2-benzimidazoyl carbamate (MBC), calculated as thiophanate-methyl in or on the following commodities: [Table#6502]

Tolerances with a regional registration, as defined in 180.1(m), are established for the combined residues of thiophanate-methyl(dimethyl[(1,2- phenylene)bis(iminocarbonothioyl) ]bis(carbamate)) and its metabolite methyl 2-benzimidazoyl carbamate (MBC), calculated as thiophanate-methyl in or on the following commodities: [Table#6503]

The Agency has previously identified and required the submission of the generic (i.e., active ingredient-specific) data required to support reregistration of products containing the active ingredient thiophanate-methyl. The Agency has completed its assessment of the occupational, residential, and ecological risk associated with the use of pesticide products containing the active ingredient thiophanate-methyl, as well as a thiophanate-methyl specific dietary risk assessment. Based on a review of these data and on public comments on the Agency's assessments for the active ingredient thiophanate-methyl, EPA has sufficient information on the human health and ecological effects of thiophanate-methyl to make decisions as part of the tolerance reassessment process under FFDCA and reregistration process under FIFRA, as amended by FQPA. The Agency has determined that thiophanate-methyl products are eligible for reregistration provided that: (i) current data gaps and confirmatory data needs are addressed; (ii) the risk reduction measures outlined in this /Reregistration Eligibility Decision/ document are adopted; and (iii) label amendments are made to reflect these measures. ... Based on its evaluation of thiophanate-methyl, the Agency has determined that thiophanatemethyl products, unless labeled and used as specified in this /Reregistration Eligibility Decision/ document, would present risks inconsistent with FIFRA. Accordingly, should a registrant fail to implement any of the risk mitigation measures identified in this /Reregistration Eligibility Decision/ document, the Agency may take regulatory action to address the risk concerns from use of thiophanate-methyl. If all changes outlined in this /Reregistration Eligibility Decision/ document are incorporated into the product labels, then all current risks for thiophanate-methyl will be adequately mitigated for the purposes of this determination.

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. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern than those on List C, and with List C containing pesticides of greater concern than those on List D. Thiophanate-methyl is found on List B. Case No: 2680; Pesticide type: insecticide, fungicide; 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 RED document.; Active ingredient (AI): dimethyl ((1,2-phenylene)bis(iminocarbonothioyl))bis(carbamate); Data Call-in (DCI) Date(s): 4/12/91, 3/3/95, 10/13/95, 3/6/96; 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.

THIOPHANATE-METHYL is incompatible with strong acids and bases, and with strong reducing agents such as hydrides. Produces flammable gaseous hydrogen with active metals or nitrides. Incompatible with strong oxidizing acids, peroxides. Incompatible with alkaline material. Forms complexes with copper salts (NTP, 1992).

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

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

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. You should then dampen the solid spill material with 60-70% methanol, then transfer the dampened material to a suitable container. Use absorbent paper dampened with methanol to pick up any remaining material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent-wash contaminated surfaces with 60-70% methanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

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. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

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.

Follow manufacturer's instructions for cleaning/maintaining PPE. If no such instructions for washables exist, use detergent and hot water. Keep and wash PPE separately from other laundry.

Discard clothing and other absorbent materials that have been drenched or heavily contaminated with this product's concentrate. Do not reuse them.

For more Preventive Measures (Complete) data for THIOPHANATE METHYL (9 total), please visit the HSDB record page.

Tolerances are established for the combined residues of thiophanate-methyl (dimethyl [(1,2-phenylene) bis (iminocarbonothioyl)] bis(carbamate)) and its metabolite methyl 2-benzimidazoyl carbamate (MBC), calculated as thiophanate-methyl in or on the following commodities: [Table#6498]

Tolerances are established for the combined residues of thiophanate-methyl (dimethyl [(1,2-phenylene) bis (iminocarbonothioyl)] bis(carbamate)) and its metabolite methyl 2-benzimidazoyl carbamate (MBC), calculated as thiophanate-methyl in or on the following commodities: [Table#6499]

Tolerances with a regional registration, as defined in 180.1(m), are established for the combined residues of thiophanate-methyl(dimethyl[(1,2- phenylene)bis(iminocarbonothioyl) ]bis(carbamate)) and its metabolite methyl 2-benzimidazoyl carbamate (MBC), calculated as thiophanate-methyl in or on the following commodities: [Table#6500]

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Handlers mixing, loading and applying the product as a dip must wear: Coveralls over long sleeved shirt and long pants, Chemical-resistant gloves, Chemical resistant footwear plus socks, A chemical resistant apron.

All other mixers and loaders and applicators must wear: Long-sleeved shirt and long pants, Shoes plus socks, Chemical-resistant gloves for all mixers and loaders and for applicators using hand held equipment, and Chemical-resistant apron for mixers, loaders and other handlers exposed to the concentrate.

When handlers use enclosed cabs in a manner that meets the requirements listed in the Worker Protection Standard (WPS) for agricultural pesticides (40 CFR 170.240(d)(4-6), the handler PPE Domestic Animals (Immediately following requirements may be reduced or modified as specified in the WPS.

Water soluble packets when used correctly qualify as a closed mixing/loading system under the Worker Protection Standard for Agricultural Pesticides [40 CFR 170.240(d)(4)]. Mixers and loaders using water soluble packets must wear the personal protective equipment required above for mixers/loaders, and be provided and must have immediately available for use in an emergency, such as a broken package, spill, or equipment breakdown coveralls, and chemical resistant footwear.

Approved respirator. Chemical-resistant gloves. Long-sleeved shirt and long pants. Shoes plus socks.

Rinse dermal exposure with water, irrigate exposed eyes with water, remove the contaminated clothing. Intubate the patients with altered mental status or airway injury. Treat acidosis and seizures. Patients should be treated with activated charcoal after large ingestions of thiophanate-methyl if they can drink the charcoal.

Thiophanate-methyl is likely a human carcinogen. It increases of risk of liver tumours in mice. Thyroid/parathyroid weights were increased The developmental toxicity studies showed the decreased fetal body weight and increases in skeletal variations in the fetuses of rabbits exposed to thiophanate-methyl. It induced histopathological damages in rat thyroid and adrenal glands.

LC50; Species: Colinus virginianus (northern bobwhite, age 14 days) diet >10000 ppm for 8 days

LC50; Species: Anas platyrhynchos (Mallard duck, age 14 days) diet >10000 ppm for 8 days

LD50; Species: Coturnix japonica (Japanese quail) gavage >5.0 g/kg

LD50; Species: Colinus virginianus (northern bobwhite, age 14 days) oral >4640 mg/kg

For more Ecotoxicity Values (Complete) data for THIOPHANATE METHYL (42 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 330(SRC), determined from a log Kow of 1.40(2) and a regression-derived equation(3), indicates that thiophanate methyl is expected to have moderate mobility in soil(SRC). Volatilization of thiophanate methyl from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.2X10-9 atm-cu m/mole(SRC), derived from its vapor pressure, 7.13X10-8 mm Hg(4), and water solubility, 26 mg/L(5). Thiophanate methyl is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Thiophanate-methyl degraded by 90% during a 6-18 week period in soils of various textures(6), suggesting that biodegradation may be a moderate environmental fate process in soil(SRC).

TERRESTRIAL FATE: A half-life of 28 days was estimated for thiophanate-methyl applied to leaves of green house crops(1).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 330(SRC), determined from a log Kow of 1.40(2) and a regression-derived equation(3), indicates that thiophanate methyl is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon an estimated Henry's Law constant of 1.2X10-9 atm-cu m/mole(SRC), derived from its vapor pressure, 7.13X10-8 mm Hg(5), and water solubility, 26 mg/L(6). According to a classification scheme(7), an estimated BCF of 4(SRC),from its log Kow(2) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Thiophanate-methyl was degraded in aqueous solution by irradiation with UV and sunlight to methyl benzimidazole-2-yl carbamate(9). Biodegradation data in aquatic media were not available(SRC, 2009).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), thiophanate methyl, which has a vapor pressure of 7.13X10-8 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase thiophanate methyl 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 5 hours(SRC), calculated from its rate constant of 7.7X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase thiophanate methyl may be removed from the air by wet or dry deposition(SRC). Thiophanate-methyl is stable to sunlight(2), suggesting that the compound is not expected to be susceptible to direct photolysis in sunlight(SRC).

/AQUATIC SPECIES/ In the acute toxicity study, experimental groups of /the newt/ Triturus carnifex were exposed to 2.40, 4.80, 9.60 and 19.20 ug/L tap water of thiophanate methyl for 2 days; the LD50 was found to be 9.60 ug/L. To evaluate the effects on the adrenal gland, newts were exposed to a dose of 25% of the LD50 2 days for 8 days. The ultrastructural features of the tissues as well as the serum levels of aldosterone, corticosterone, norepinephrine (NE) and epinephrine (E) were evaluated. The number of secretory vesicles in the chromaffin cells appeared significantly decreased, whereas NE and E serum levels appeared strongly increased. Moreover, corticosterone and aldosterone serum levels appeared significantly reduced. ...

/OTHER TERRESTRIAL SPECIES/ ... The effects /of methyl thiophanate (MT)/ on adrenal glands of Podarcis sicula lizard, the endemic species of Southern Italy living in open country and in cultivated fields /were examined/. ... 1.5% MT/water /was used/ to pollute terraria, food, and water twice a week for 15 and 30 days, and ... adrenal toxicity /was evaluated/ through biochemical (adrenal and pituitary hormone plasma levels) and histological parameters (adrenal gland histopathology). We demonstrated a time-dependent increase of corticosterone plasma levels and a decrease of ACTH plasma levels, a hypertrophy of the steroidogenic tissue, and an enlargement of blood capillaries. Moreover, ... a time-dependent increase of adrenaline plasma levels and adrenaline-producing cells, and an opposite trend of noradrenaline plasma concentrations /was observed/. ... Lymphocyte and macrophage infiltrations, signs of cell degeneration /were also observed/...

/OTHER TERRESTRIAL SPECIES/ ... The sensitivity to methyl thiophanate (TM) of the lizard Podarcis sicula /was tested/ to propose a biological model for monitoring the ecotoxicological effects of this pesticide on terrestrial sentinel species. The data obtained demonstrate that exposition to sub-lethal concentrations of TM leads to hepatocellular morphological changes and glycogen depletion, apoptosis, as well as probable peroxisomal proliferation attested by the increase of acyl-CoA oxidase (AOX). This effect seems to be mediated by the concomitant increase of PPARalpha....

Thiophanate-methyl

Endocrine

8 x 10 ^-2 mg/kg-day

The Koc of thiophanate methyl is estimated as 330(SRC), using a log Kow of 1.40(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that thiophanate methyl is expected to have moderate mobility in soil. Estimated Koc values for the parent compound (Topsin-M) range from 11-21(5).

/SURVEILLANCE/ Among men who treated citrus with thiophanate-methyl as well as emulsified sulfur and calcium polysulfide in Kumamoto Prefecture, the incidence of dermatitis was 30.3, 48.2, and 52.8% in 1972, 1973, and 1974, respectively. The corresponding values for women were 32.3, 56.3, and 64.8%. The areas affected were the abdomen, back, and waist. Symptoms included itching, redness, swelling, dryness, and sometimes sensitized dermatitis. Symptoms frequently appeared 1 wk after exposure. The ocular mucosa was congested. The incidence of positive patch tests was only about 5%. Medical exam revealed some abnormalities of hemoglobin.

/SURVEILLANCE/ The Incident Data System included 2 incidents in 1994. In the first, a male was exposed to thiophanate-methyl that was sprayed on school playing fields. After the spraying, the wind blew the chemical towards his garden and exacerbated his emphysema. In the second incident, a woman was exposed to spray drift from thiophanate-methyl from an adjacent orchard. She experienced eye irritation.

/SURVEILLANCE/ There were 37 cases submitted to the California Pesticide Illness Surveillance Program (1982-1994). In 11 of these cases, thiophanate-methyl was judged to be responsible for the health effects. A total of 5 persons had systemic illnesses that involved skin, eye, or respiratory effects. Three of these cases occurred in 1990 and the workers were diagnosed with chemical bronchitis. A total of three persons had skin illnesses. None of the persons were hospitalized ... The majority of the systemic illnesses occurred due to a crew of workers sprinkling thiophanate-methyl from coffee cans onto seed potatoes that were cut. Symptoms included shortness of breath, chest pains, burning eyes, dizziness, and fatigue. The two eye illnesses occurred due to the workers being exposed to residue from the thiophanate-methyl that blew into their eyes. Symptoms experienced were eye irritation which included swollen and burning eyes.

/GENOTOXICITY/ Flow cytometric technique was used to study the effects of the fungicide Thiophanate-methyl on cell proliferation, micronucleus induction, and apoptosis in human peripheral blood lymphocytes treated in vitro. Most micronuclei induced by Thiophanate-methyl did not reveal any centromeric signal, thus demonstrating clastogenic action of this fungicide. Moreover, it was found that as a function of the concentration of Thiophanate-methyl, cellular proliferation was delayed and the frequency of apoptotic cells was increased.

U409; As stipulated in 40 CFR 261.33, when thiophanate-methyl, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

Tolerances are established for the combined residues of thiophanate-methyl (dimethyl [(1,2-phenylene) bis (iminocarbonothioyl)] bis(carbamate)) and its metabolite methyl 2-benzimidazoyl carbamate (MBC), calculated as thiophanate-methyl in or on the following commodities: [Table#6501]

Tolerances are established for the combined residues of thiophanate-methyl (dimethyl [(1,2-phenylene) bis (iminocarbonothioyl)] bis(carbamate)) and its metabolite methyl 2-benzimidazoyl carbamate (MBC), calculated as thiophanate-methyl in or on the following commodities: [Table#6502]

Tolerances with a regional registration, as defined in 180.1(m), are established for the combined residues of thiophanate-methyl(dimethyl[(1,2- phenylene)bis(iminocarbonothioyl) ]bis(carbamate)) and its metabolite methyl 2-benzimidazoyl carbamate (MBC), calculated as thiophanate-methyl in or on the following commodities: [Table#6503]

The Agency has previously identified and required the submission of the generic (i.e., active ingredient-specific) data required to support reregistration of products containing the active ingredient thiophanate-methyl. The Agency has completed its assessment of the occupational, residential, and ecological risk associated with the use of pesticide products containing the active ingredient thiophanate-methyl, as well as a thiophanate-methyl specific dietary risk assessment. Based on a review of these data and on public comments on the Agency's assessments for the active ingredient thiophanate-methyl, EPA has sufficient information on the human health and ecological effects of thiophanate-methyl to make decisions as part of the tolerance reassessment process under FFDCA and reregistration process under FIFRA, as amended by FQPA. The Agency has determined that thiophanate-methyl products are eligible for reregistration provided that: (i) current data gaps and confirmatory data needs are addressed; (ii) the risk reduction measures outlined in this /Reregistration Eligibility Decision/ document are adopted; and (iii) label amendments are made to reflect these measures. ... Based on its evaluation of thiophanate-methyl, the Agency has determined that thiophanatemethyl products, unless labeled and used as specified in this /Reregistration Eligibility Decision/ document, would present risks inconsistent with FIFRA. Accordingly, should a registrant fail to implement any of the risk mitigation measures identified in this /Reregistration Eligibility Decision/ document, the Agency may take regulatory action to address the risk concerns from use of thiophanate-methyl. If all changes outlined in this /Reregistration Eligibility Decision/ document are incorporated into the product labels, then all current risks for thiophanate-methyl will be adequately mitigated for the purposes of this determination.

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. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern than those on List C, and with List C containing pesticides of greater concern than those on List D. Thiophanate-methyl is found on List B. Case No: 2680; Pesticide type: insecticide, fungicide; 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 RED document.; Active ingredient (AI): dimethyl ((1,2-phenylene)bis(iminocarbonothioyl))bis(carbamate); Data Call-in (DCI) Date(s): 4/12/91, 3/3/95, 10/13/95, 3/6/96; 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.

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 10 lb or 4.54 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

As a class of compounds, thiocarbamates do not produce consistent cholinesterase inhibition patterns. In the rat subchronic toxicity study, serum cholinesterase activity was increased in males by 22-38% relative to controls but decreased in females by 25-28% at >/= 293.2 mg/kg/day. In the rat chronic toxicity/carcinogenicity study, males showed increases in serum ChE at 280.6 mg/kg/day (HDT) at 6 and 12 months (41-42%) whereas at 24 months, it was decreased (-38%). ChE activity in females was slightly decreased (18035%) at 6 and 12 months at >/= 63.5 mg/kg/day ... /thiocarbamates/

In order to characterize the mechanism of thyroid tumorigenesis, a series of short term studies were undertaken to determine whether TM had antithyroid activity. These studies demonstrated that TM caused liver and thyroid enlargement, increased circulating TSH and decreased T3/T4 after 2 to 8 days' treatment with TM at 6000 ppm (equivalent to the HDT in the rat chronic toxicity/carcinogenicity study). Some liver microsomal enzymes, including UDP-glucuronosyltransferase, were increased. The effects on liver and thyroid weight were reversible, but reversibility of the alterations in circulating hormone levels and on microscopic effects were not evaluated. Supplementation of treated animals with T4 prevented thyroid enlargement and increased TSH but did not prevent liver enlargement. TM also appeared to have a mild inhibitory effect on microsomal thyroid peroxidase. These data were considered necessary to adequately support this mechanism.

Studies in mice with four radioactive forms of the molecule (14C in the ring or as the thiourea carbon of the methyl carbon and 35S) showed that the C=S bond was cleaved to a great extent prior to absorption from the gastrointestinal tract. Some of the methyl carbon apparently is metabolized to carbon dioxide. The major urinary metabolites are carbendazim and its 6-hydroxy derivative; these are excreted as O- or N-glucuronides. A compound in which the two =S's of thiophanate-methyl are replaced by =O's is a minor metabolite. Some other metabolites detectable by thin-layer chromatography of radioactive material remain unidentified.

... Primary metabolic changes included hydrolysis of side chain extremities, closure of remaining side chain portions, and oxidation of the phenyl moiety, producing a methyl hydroxybenzimidazolyl carbamate. The primary urinary metabolite was conjugated with sulfate. Fecal residues were largely thiophanate-methyl and a phenyl ring hydroxylated product.

Agents that kill parasitic worms. They are used therapeutically in the treatment of HELMINTHIASIS in man and animal.

Substances used in the treatment or control of nematode infestations. They are used also in veterinary practice.

Chemicals that kill or inhibit the growth of fungi in agricultural applications, on wood, plastics, or other materials, in swimming pools, etc.

Nearly all thiophanate-methyl is eliminated from the body in 24 hr; that left in tissues after 24 hr is largely eliminated within 96 hr.

Thiophanate-methyl was efficiently absorbed, and rapidly excreted. There was evidently some saturability of uptake processes and lengthening of elimination half-life at high dose levels or following sustained low dose exposures. Blood levels diminished quickly, and tissue levels were very low by day 4 (post-exposure) in all cases.

Used as fungicide to control disease (vegetables, fruits, turf, and other crops) and protect wounds (fruit trees); [HSDB] Used as veterinary anthelmintic (nematodes); [Merck Index]

Farming (Pesticides) [Category: Industry]

For thiophanate methyl (USEPA/OPP Pesticide Code: 102001) 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./

Used for plant disease control in vegetables, fruits, & turf.

Fungicide

Wound protectant (fruit trees)

Thiophanate methyl is produced by reaction of o-phenylenediamine and methoxycarbonyl isothiocyanate.

o-Phenylenediamine + potassium thiocyanate + methyl chloroformate (addition/dehydrochlorination)

USEPA/OPP Pesticide Code 102001; Trade Names: Topsin, Cercobin M, Banrot, component of (with 084701), Fungo, TD-1771, NF-44, Enovit methyl.

Thiophanate-methyl formulations include dust, granular, wettable powder, water-dispersible granular, and flowable concentrate, ranging from 1.5% to 90% active ingredient.

Wettable powder, paste, flowable, granule, dust, ULV.

Tops MZ Potato Dee-Piece Treatment Fungicide; Active ingredients 6.00% Mancozeb and 2.50% Thiophanate-methyl

For more Formulations/Preparations (Complete) data for THIOPHANATE METHYL (82 total), please visit the HSDB record page.

Environmental transformation -> Pesticides (parent, predecessor)

Fungicides

The WHO Recommended Classification of Pesticides by Hazard identifies Thiophanate-methyl as unlikely to present an acute hazard in normal use; Main Use: Fungicide (other than seed treatment).

Residential homeowners may use on lawns and ornamentals