Thiophanate methyl
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Thiophanate methyl
structure -
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CAS No:
23564-05-8
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Formula:
C12H14N4O4S2
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Chemical Name:
Thiophanate methyl
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Synonyms:
Carbamic acid,N,N′-[1,2-phenylenebis(iminocarbonothioyl)]bis-,C,C′-dimethyl ester;Allophanic acid,4,4′-o-phenylenebis[3-thio-,dimethyl ester;Carbamic acid,[1,2-phenylenebis(iminocarbonothioyl)]bis-,dimethyl ester;Methylthiophanate;Thiophanate methyl;Dimethyl 4,4′-o-phenylenebis(3-thioallophanate);Methylthiofanate;o-Bis(3-methoxycarbonyl-2-thioureido)benzene;NF 44;TD 1771;Topsin M;Topsin NF 44;Thiophanate M;Cercobin M;1,2-Bis[3-(methoxycarbonyl)-2-thioureido]benzene;Methyl topsin;Enovit M;1,2-Bis(methoxycarbonylthioureido)benzene;Pelt 14;BAS 32500F;Cercobin methyl;Pelt 44;Neotopsin;Topsin Methyl;Fungo;Enovit Super;Easout;F 6385;Enovit-methyl;Mildothane;PEI 190;Caligran;Metoben;Enovit M 70;Cercobin M 70;Cycosin;Topsin M 70;Thiopan;Topsin MD;Tops;Rilon;NSC 170811;Roko;Cleary's 3336;3336G;Topsin 500SC;Sunphanate;Topsin WP;Topsin M 70WP;Topsin M 500SC;Senator;Senator 70W;Senator (carbamate);Cercobin FL;Pelt;Pelt (pesticide);Cercobin;Topgin M;50814-12-5;1135443-49-0
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CAS No:
Description
Thiophanate-Methyl is a systematic fungicide[1].
Thiophanate-methyl appears as colorless crystals or light brown powder. (NTP, 1992)|Colorless crystals or light brown powder.
Thiophanate-methyl appears as colorless crystals or light brown powder. (NTP, 1992)|Thiophanate-methyl is a member of the class of thioureas that is the dimethyl ester of (1,2-phenylenedicarbamothioyl)biscarbamic acid. A fungicide effective against a broad spectrum of diseases in fruit, vegetables, turf and other crops including eyespot, scab, powdery mildew and grey mould. It has a role as an antifungal agrochemical. It is a member of thioureas, a carbamate ester, a benzimidazole precursor fungicide and a carbamate fungicide. It derives from a 1,2-phenylenediamine.|Nematocide used in livestock; also has fungicidal properties.
Thiophanate methyl Basic Attributes
342.39
342.39
245-740-7
K4N81R84L8
170811
2757
DTXSID1024338
Colorless crystals|Colorless prisms|Colorless crystalline solid
29309090
Characteristics
165
1.40
1.552 g/cm3
172 °C (decomp)
478.4ºC at 760 mmHg
1.709
In water, 26.6 mg/L at 20 deg C
0-6°C
<1.3 x 10 -5 Pa (25 °C)
Oral-Rat LD50: 6640 mg/kg; Oral-Mouse LD50: 3400 mg/kg
Combustion produces toxic nitrogen oxide and sulfur oxide gas
Henry's Law constant = 1.21X10-9 atm-cu m/mol at 25 °C (est)
pKa = 7.28
173.3 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]|174.24 Ų [M+H]+ [CCS Type: TW]|174.79 Ų [M+H]+
Unique thioallophanate structure|Colorless plates from acetone, decomposes at 194 °C /Thiophanate/|Pale brown color ... begins to decompose at approximately 163 °C /Technical/|Hydroxyl radical reaction rate constant = 7.6X10-11 cu cm/molec-sec at 25 °C (est)
Insoluble in water.
Amides and Imides
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).
Safety Information
UN 3077
3
20-43-50/53-68
36/37-46-60-61
BA3675000
Xn;N,N,Xn
The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials
Stable. Incompatible with strong oxidizing agents, alkalies, copper salts.
P261-P280
H317-H332-H341-H410
Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U409, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.
... Incompatible with alkaline & copper-containing compounds.
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]
Flash point data for this chemical are not available. It is probably combustible. (NTP, 1992)
|Warning|H317: May cause an allergic skin reaction [Warning Sensitization, Skin]|P201, P202, P261, P271, P272, P273, P280, P281, P302+P352, P304+P312, P304+P340, P308+P313, P312, P321, P333+P313, P363, P391, P405, and P501|H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]|Aggregated GHS information provided by 325 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P260, P261, P271, P272, P280, P302+P352, P304+P312, P304+P340, P312, P314, P321, P333+P313, P363, and P501
Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
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. STORAGE PRECAUTIONS: You should store this material at ambient temperatures and keep away from alkaline materials. (NTP, 1992)
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.
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.
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.
Mild skin & eye irritant.
U409; A toxic waste when a discarded commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or manufacturing chemical intermediate.
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).
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).
Toxicity
moderately
LD50 Rat oral 6640 mg/kg|LD50 Rat ip 1140 mg/kg|LD50 Mouse oral 3400 mg/kg|LD50 Mouse ip 790 mg/kg|For more Non-Human Toxicity Values (Complete) data for THIOPHANATE METHYL (21 total), please visit the HSDB record page.
/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's production may result in its release to the environment through various waste streams; its use as a fungicide(1) will result in its direct release to the environment(SRC).
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).
The rate constant for the vapor-phase reaction of thiophanate methyl with photochemically-produced hydroxyl radicals has been estimated as 7.7X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 5 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Thiophanate-methyl is stable in neutral, aqueous solution at room temperature and is stable to air and sunlight(2). However, thiophanate methyl in aqueous solution exhibited absorption maximum at 263 nm, with the range being 220-310 nm; thiophanate-methyl at 20 ppm irradiated in aqueous solution at 25 °C for 48 hrs resulted in 60% formation of methyl benzimidazole-2-yl carbamate (MBC)(3). MBC is more toxic than thiophanate methyl. Degradation was not observed in dark controls. An aqueous solution of thiophanate-methyl applied to plant foliage exposed to sunlight was found to degrade at a similar rate under the same environmental conditions(3).
An estimated BCF of 4 was calculated in fish for thiophanate methyl(SRC), using a log Kow of 1.40(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
1.78e+03 L/kg|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).
The Henry's Law constant for thiophanate methyl is estimated as 1.2X10-9 atm-cu m/mole(SRC) derived from its vapor pressure, 7.13X10-8 mm Hg(1), and water solubility, 26.6 mg/L(2). This Henry's Law constant indicates that thiophanate methyl is expected to be essentially nonvolatile(3). Thiophanate methyl's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may not occur(SRC). Thiophanate methyl is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).
GROUNDWATER: Thiophanate-methyl was detected in 0 of 3 groundwater samples collected in California in 1988(1).
Occupational exposure to thiophanate methyl may occur through inhalation and dermal contact with this compound at workplaces where thiophanate methyl is produced or used. (SRC)|Worker re-entry exposure to pesticides residues in greenhouses is a probable exposure route based upon a study in which thiophanate-methyl was applied to carnations via high-volume spraying at application rates of 150 and 325 g ai/1000 sq m, showing half-lives of 22 and 41 days, respectively(1). Dermal exposure of greenhouse workers to thiophanate-methyl (applied by spraying) on carnations cultured in greenhouses was found to be 64 mg/day (during cutting operations) and 23 mg/day (during sorting and bundling)(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.)|Substances used in the treatment or control of nematode infestations. They are used also in veterinary practice. (See all compounds classified as Antinematodal Agents.)|Agents that kill parasitic worms. They are used therapeutically in the treatment of HELMINTHIASIS in man and animal. (See all compounds classified as Anthelmintics.)
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.
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.
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.
SYMPTOMS: Symptoms of exposure to this compound may include irritation, itching, redness, swelling, and dryness of the skin; congestion; and, sometimes, dermatitis. ACUTE/CHRONIC HAZARDS: This compound may irritate the skin. When heated to decomposition it emits very toxic fumes of NOx and SOx. (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. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)
/SRP:/ Immediate first aid: 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 if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the 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. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/
/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.
Bis-Thioallophanate, Dimethylphenylene
Thiophanate methyl Use and Manufacturing
Preparation of methyl chloroformate Methanol and phosgene synthesize methyl chloroformate at 5-15°C. Since phosgene is easily decomposed when it meets water, it should be dried. If the temperature is too high, dimethyl carbonate is easily produced as a by-product. The preparation of methyl isothiocyanate uses acetone as the solvent, and the reaction between methyl chloroformate and sodium thiocyanate. To control the reaction temperature, if the temperature is too high, the isothiocyanate is easy to decompose, and the lower temperature is not easy to be isomerized, generally 45 ~ 59 ℃ is appropriate. Note that when dropwise adding methyl chloroformate, the temperature is too high, it is easy to bump overflow, 38 ℃ is appropriate. Synthesis of thiophanate-methyl Methyl thiophanate is prepared by addition of o-phenylenediamine and methyl isothiocyanate at 15-40°C. Strictly control the ratio of raw materials to 1:2. For the solvent recovery technology in the production process, please refer to
Broad-spectrum fungicide, widely used in the prevention and control of various diseases of rice, cotton, wheat, rape and other crops; is a high-efficiency, low-toxicity, systemic fungicide, used for the prevention and control of three-wheat scab and cotton seedling diseases , Wheat rust, fruit tree diseases, etc.; this product is a broad-spectrum systemic fungicide that can prevent various diseases of cereals, cotton, fruits, vegetable turf and other crops, such as three wheat scab, cotton seedling diseases, wheat Rust, fruit tree diseases, etc.
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.
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
Method: OSHA PV2058; Procedure: high performance liquid chromatography using an ultraviolet detector; Analyte: thiophanate-methyl; Matrix: air; Detection Limit: 10 ug/cu m.|Method: NIOSH 5606, Issue 1; Procedure: high performance liquid chromatography and ultra violet detector; Analyte: thiophanate-methyl; Matrix: air; Detection Limit: 0.76 ug/sample.|Method: NIOSH 9202, Issue 1; Procedure: high performance liquid chromatography and ultra violet detector; Analyte: thiophanate-methyl; Matrix: handrinse; Detection Limit: 60 ug/sample.|Method: NIOSH 9205, Issue 1; Procedure: high performance liquid chromatography and ultra violet detector; Analyte: thiophanate-methyl; Matrix: dermal patch; Detection Limit: 18.6 ug/sample.|For more Analytic Laboratory Methods (Complete) data for THIOPHANATE METHYL (6 total), please visit the HSDB record page.
Agrochemicals -> Fungicides|Fungicides|Environmental transformation -> Pesticides (parent, predecessor)
Thiophanate-methyl has known environmental transformation products that include allophanate and carbendazim.|Thiophanate-methyl has known environmental transformation products that include 2-AB, AV-1951, CM-0237 (M2), CM-0238 (M1), Carbendazim (MBC), DX-105, Thiophanate-methyl metabolite M10, and allophanate.
Computed Properties
Molecular Weight:342.4
XLogP3:2.6
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:4
Exact Mass:342.04564729
Monoisotopic Mass:342.04564729
Topological Polar Surface Area:165
Heavy Atom Count:22
Complexity:407
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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