Thiram

HCID 5455CAS 137-26-8

Basic information

Standard SMILES
CN(C)C(=S)SSC(=S)N(C)C
InChIKey
KUAZQDVKQLNFPE-UHFFFAOYSA-N
Molecular formula
C6H12N2S4
Average molar mass
240.4 g/mol
Monoisotopic mass
239.98833309

Names & identifiers

Preferred name
Thiram
IUPAC
dimethylcarbamothioylsulfanyl N,N-dimethylcarbamodithioate
English name
Tetramethylthiuram Disulfide
Molecular formula
C6H12N2S4
Molecular weight
240.43

Names & synonyms

thiramTetramethylthiuram disulfide137-26-8ThiuramTMTDRezifilmPomarsolThirameArasanFernasanNobecutanNormersan
Show more names
1,1’-dithiobis(n,n-dimethylthio-formamidTETRAMETHYLTHIURAM DISULPHIDETNTDtmtcTersan
AapirolPuralinSpotreteThiosanThirasanTetrathiuram disulfideTetramethylthiuramFalitiram

Database identifiers

CAS
137-26-8
PubChem CID
5455
DTXSID
DTXSID5021332
ChEMBL
CHEMBL120563
ChEBI
CHEBI:9495
UNII
0D771IS0FH
EC Number
205-286-2
Nikkaji
J2.949A

Properties

Computed structural properties

XLogP
1.7
Topological polar surface area
121 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
4
Rotatable bonds
3
Heavy atoms
12

Experimental & physicochemical properties

LogP · 2 items

log Kow = 1.73

1.82

OdorCharacteristic odor
Density · 6 items

1.43 at 68 °F (USCG, 1999) - Denser than water; will sink

1.3 g/cu cm

1.3 g/cm³

1.43

1.3 @25 °C

1.29

Color/Form · 2 items

White crystalline powder

Colorless to yellow, crystalline solid. (Note: commercial pesticide product may be dyed blue.)

Solubility · 6 items

less than 1 mg/mL at 72 °F (NTP, 1992)

Solubility in alcohol and in ether less than 0.2%; solubility in acetone 1.2%; in benzene 2.5%.

Sol in carbon disulfide

Solubility in ethanol <10 g/L at 25 °C, acetone 80 g/L at 25 °C, chloroform 230 g/L at 25 °C, hexane 0.04 g/L at 20 °C; dichloromethane 170 g/L at 20 °C, toluene 18 g/L at 20 °C, isopropanol 0.7 g/L at 20 °C.

In water, 30 mg/L at 25 °C

Solubility in water: none

CorrosivityNon-corrosive in the dry state.

Physicochemical properties

Melting point
156 · 156-158 °C(lit.)
Boiling point
129 °C · 129 °C (20 mmHg)
Density
1.43 · 1.43
vapor pressure
8 x · 8 x 10-6 mmHg at 20 °C (NIOSH, 1997)
refractive index
1.55 · 1.5500 (estimate)
Flash point
89 °C · 89°C

Safety & regulation

GHS classification

GHS Classification · 6 items

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral];H315: Causes skin irritation [Warning Skin corrosion/irritation];H317: May cause an allergic skin reaction [Warning Sensitization, Skin];H319: Causes serious eye irritation [Warning Serious eye damage/eye irritation];H332: Harmful if inhaled [Warning Acute toxicity, inhalation];H373 **: May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure];H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard];H410: Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

P260, P261, P264, P264+P265, P270, P271, P272, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Warning

Hazard information

Regulatory Information · 6 items

Chemical: Thioperoxydicarbonic diamide ([(H2N)C(S)]2S2), N,N,N′,N′-tetramethyl-

Hazard Traits - Neurotoxicity;Authoritative List - IRIS Neurotoxicants;Report - if used as a fragrance or flavor ingredient

Regulation (EC) No 396/2005 (amended)

Thioperoxydicarbonic diamide ([(H2N)C(S)]2S2), N,N,N',N'-tetramethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Thioperoxydicarbonic diamide ([(H2N)C(S)]2S2), N,N,N',N'-tetramethyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

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

03/81/EC, Reg. (EU) 2016/2016, Reg. (EU) No 540/2011, Reg. (Eu) 2018/1500, Reg.(EU)2018/524

Other Safety InformationIMAP assessments - Thioperoxydicarbonic diamide ([(H2N)C(S)]2S2), tetramethyl-: Human health tier II assessment
DOT LabelPoison
Fire Hazards · 2 items

Special Hazards of Combustion Products: Toxic and irritating oxides of sulfur are formed. Carbon disulfide may be formed from unburned material. (USCG, 1999)

Combustible. Liquid formulations containing organic solvents may be flammable. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air.

Health Hazards · 1 item

Inhalation of dust may cause respiratory irritation. Liquid irritates eyes and skin and may cause allergic eczema in sensitive individuals. Ingestion causes nausea, vomiting, and diarrhea, all of which may be persistent; paralysis may develop. (USCG, 1999)

Hazards Summary · 1 item

An irritant and a skin sensitizer, thiram is classified as slightly toxic. [EXTOXNET] No increased tumors in chronic studies of rodents; Reproductive endpoints are not generally altered and the fetal animal does not appear to be more sensitive. [ACGIH] The EBCDCs (ethylenebisdithiocarbamates) can cause irritant and allergic contact dermatitis. EBDCs include ferbam, vapam, maneb, mancozeb, zineb, thiram, and ziram. They are also used as rubber accelerators. Ethylene thiourea (ETU), which may contaminate EBCDCs, is carcinogenic and teratogenic in animal experiments. [LaDou, p. 610] ETU is the major metabolite of EBDCs. [Krieger, p. 1690] See the agent, Ethylene thiourea.

Safety & protection

Fire Fighting · 2 items

Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:;SMALL FIRE: Dry chemical, CO2 or water spray.;LARGE FIRE: Water spray, fog or regular foam. If it can be done safely, move undamaged containers away from the area around the fire. Dike runoff from fire control for later disposal. Avoid aiming straight or solid streams directly onto the product.;FIRE INVOLVING TANKS, RAIL TANK CARS OR HIGHWAY TANKS: Fight fire from maximum distance or use unmanned master stream devices or monitor nozzles. Do not get water inside containers. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks in direct contact with flames. For massive fire, use unmanned master stream devices or monitor nozzles; if this is impossible, withdraw from area and let fire burn. (ERG, 2024)

Use water spray, powder, foam, carbon dioxide.

First Aid Measures · 4 items

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Refer for medical attention .

First Aid · 2 items

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)

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

Safe StorageSeparated from acids, strong oxidants and food and feedstuffs. Dry. Keep in a well-ventilated room.
Exposure Control and Personal Protection1.0 [mg/m3], inhalable fraction[German Research Foundation (DFG)]
Fire Fighting Procedures · 2 items

Fire Fighting: Self-contained breathing apparatus with a full facepiece operated in pressure-demand or other positive pressure mode.

If material involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use foam, dry chemical, or carbon dioxide. Use water in flooding quantities as fog. Apply water from as far a distance as possible. Keep run-off water out of sewers and water sources.

Toxicology

Interactions · 5 items

Like most dithiocarbamates, thiram induces accumulation of acetaldehyde in blood of rats receiving ethanol at same time. Its reaction with nitrite at acid pH in stomachs of guinea pigs in vivo gives rise to n-nitrosodimethylamine.

Simultaneous admin of thiram and 10 mg/animal L-cysteine ip from day 5-15 of pregnancy resulted in significant decrease both in severity and in number of embryopathies.

Possible interactions between thiram and some drugs, ie, promethazine, meprobamate, and trihexyphenidyl, acting on the central nervous system were studied in rats by behavioral methods. Promethazine also inhibited orientation hypermotility, open-field behavior, and learning ability of rats only in high doses. A 10 mg/kg dose of thiram induced only a moderate decrease in the behavioral activity. In combination the inhibitory effect significantly increased. Thus, there was a definite synergism between the two. The dose-dependent decrease in the behavioral parameters from meprobamate was enhanced to a great extent by combination with thiram. The rate of interaction (synergism) was less than that seen for promethazine. Pretreatment with thiram before trihexylphenidyl (stimulation at < 40 mg/kg and inhibition at higher dose) resulted in the suspension of psychostimulant-like effect of the drug and enhancement of the inhibition. The pesticide-drug interaction was in all cases dose dependent.

Lead concentrations in blood and brain were measured in rats exposed to lead via drinking water, 0.25% lead (12 mM), and dithiocarbamate/thiram derivatives administered by gavage singly or in combination for 6 weeks. Diethyldithiocarbamate and dimethyldithiocarbamate were given in doses of 0.2 mmol/kg and thiram and disulfiram in doses of 0.1 mmol/kg twice a week. In rats that received lead + dithiocarbamate/thiram derivatives lead concentrations in blood and brain were significantly increased; disulfiram being most effective in increasing lead levels, followed by thiram, dimethyldithiocarbamate and diethyldithiocarbamate. In blood, lead levels were increased 3-fold and in brain almost 4-fold after treatment with lead + disulfiram compared to treatment with lead alone. When rats were given diethyldithiocarbamate or thiram by gavage (0.1 mmol/kg/day 5 days a week for 2 weeks) after cessation of the lead treatment, there was no increase in blood lead levels but in thiram-treated rats brain lead concentration was increased 2.7-fold. In rats treated with diethyldithiocarbamate ip after cessation of lead treatment, both blood and brain concentration of lead were increased. Apparently, combined exposure of lead and dithiocarbamate/thiram derivative causes a substantial increase in brain levels of lead which are not always reflected in increases of blood lead levels. This interaction effect ought to be taken into consideration when evaluating the health effects of environmental and occupational lead exposure.

For more Interactions (Complete) data for THIRAM (10 total), please visit the HSDB record page.

Target Organs · 2 items

Nervous

Eyes, skin, respiratory system, central nervous system

Ecotoxicity Values · 5 items

LD50 Anas Platyrhynchos (Mallard duck, female 3 month old) oral >2800 mg/kg /sample purity >/=99%/

LD50 Phasianus colchicus (Ring-necked pheasant, male 3-4 months old) oral 673 mg/kg (95% confidence limit: 485-932 mg/kg) /sample purity >/= 99%/

LD50 /Agelaius phoeniceus/ (Redwing blackbird) oral >100 mg/kg

LC50 Cyprinus carpio (carp) 4 mg/l. /Conditions of bioassay not specified/

For more Ecotoxicity Values (Complete) data for THIRAM (32 total), please visit the HSDB record page.

Environmental Fate · 4 items

TERRESTRIAL FATE: Based on a classification scheme(1), a measured Koc value of 676(2) indicates that thiram is expected to have low mobility in soil(SRC). Volatilization of thiram from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 3.26X10-7 atm-cu m/mole(3). Thiram is not expected to volatilize from dry soil surfaces(SRC) based upon an a vapor pressure of 1.72X10-5 mm Hg(2). The rate constant for the photolysis of thiram in soil has been reported to be 0.0346 per day(7). This rate constant corresponds to a half-life of 20 days(SRC). Microbial degradation in soil is expected since thiram has been reported to degrade faster in unsterilized soil than in sterilized soil; however, degradation rates were not specified(4). Half-lives for thiram measured during soil field studies range from 1 day to 15 weeks(5,6).

TERRESTRIAL FATE: Thiram, at a concentration of 180 ppm thoroughly distributed in soil, had a half-life of 1-2 days(1). However, when it was added as a dressing on 0.7 mm glass beads, approximately 10% degradation was observed after 21 days(1). Thiram applied to soil at 100 and 1000 ppm persisted for 4 and >32 weeks, respectively(2). In soil with humus content less than or equal to 1.2%, an initial lag in the decomposition of thiram has been observed(3). Thiram persisted over two months in sandy soil, but disappeared within one week in a compost soil(2). In addition, thiram has been more persistent in sandy soil than laterite and alluvial soils(2). The half-life of thiram applied to bareground and turf plots of sandy loam soil (pH 8.2-9.6) were 27.4 days and 14.4 days, respectively, during terrestrial field studies in California(4). Degradation was biphasic, with rapid initial degradation during the first week followed by much slower degradation(4). Half-lives of thiram applied to bareground (pH 4.1-4.7) and turf plots (pH 4.4-4.5) of sandy loam soil were 36 days and 62.5 days, respectively, during terrestrial field studies in North Carolina(4). In sandy soil humus at pH 3.5, thiram was largely decomposed after 4-5 weeks(5). Thiram decomposed after 14-15 weeks in soil at pH 7.0(5). Persistence of thiram in soil was much greater at 1000 ppm than at 100 ppm in soil(6). However, many of the soil microflora were killed at these concentrations(6).

AQUATIC FATE: Based on a classification scheme(1), a Koc value of 676(2), indicates that thiram is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon a Henry's Law constant of 3.26X10-7 atm-cu m/mole(4). According to a classification scheme(5), BCF values of 1.1-4.4(6) suggest bioconcentration in aquatic organisms is low(SRC). The hydrolysis half-lives measured for thiram at pH 5, pH 7 and pH 9 were 68.5 days, 3.5 days, and 6.9 hours, respectively(7). The rate constant for the photolysis of thiram in water has been reported to be 3.8 per day, which corresponds to a half-life of 4.3 hours(8). Biodegradation is not expected to be an important fate process in water(SRC) based on 2.8% to 30% degradation after 20 days in screening tests using sewage sludge innocula(6,9,10). The half-life of thiram measured during a monitoring study conducted on the Po River in Italy was 15 days(11).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), thiram, which has a vapor pressure of 1.72X10-5 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase thiram 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 1 hour(SRC), calculated from its rate constant of 3.62X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase thiram may be removed from the air by wet and dry deposition(SRC).

Adverse EffectsSkin Sensitizer - An agent that can induce an allergic reaction in the skin.;ACGIH Carcinogen - Not Classifiable.
Exposure Routes · 2 items

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion.

inhalation, ingestion, skin and/or eye contact

Regulatory information

Regulatory Information · 6 items

Chemical: Thioperoxydicarbonic diamide ([(H2N)C(S)]2S2), N,N,N′,N′-tetramethyl-

Hazard Traits - Neurotoxicity;Authoritative List - IRIS Neurotoxicants;Report - if used as a fragrance or flavor ingredient

Regulation (EC) No 396/2005 (amended)

Thioperoxydicarbonic diamide ([(H2N)C(S)]2S2), N,N,N',N'-tetramethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Thioperoxydicarbonic diamide ([(H2N)C(S)]2S2), N,N,N',N'-tetramethyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

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

03/81/EC, Reg. (EU) 2016/2016, Reg. (EU) No 540/2011, Reg. (Eu) 2018/1500, Reg.(EU)2018/524

FDA RequirementsThiram is an indirect food additive for use only as a component of adhesives.
RCRA Requirements · 1 item

U244; As stipulated in 40 CFR 261.33, when thiram, 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).

TSCA Requirements · 1 item

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Thiram is included on this list.

FIFRA Requirements · 3 items

Tolerances for residues of the fungicide thiram (tetramethyl thiuram disulfide) in or on raw agricultural commodities are established as follows: apple, peach, and strawberry.

The Agency has completed its assessment of the dietary, occupational, residential, and ecological risk associated with the use of pesticide products containing the active ingredient thiram. Based on a review of these data and on public comments on the Agency's assessments for the active ingredient thiram, the Agency has sufficient information on the human health and ecological effects of thiram 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 thiram containing products are eligible for reregistration provided that: (i) current data gaps and confirmatory data needs are addressed; (ii) the risk mitigation measures outlined in this document are adopted; and (iii) label amendments are made to reflect these measures.

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Thiram is found on List A, which contains most food use pesticides and consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA, as amended in 1988. Case No: 0122; Pesticide type: fungicide; Registration Standard Date: 06/29/84; 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): Thiram; Data Call-in (DCI) Date(s): 09/16/91, 03/03/95, 10/13/95; AI Status: The producers of the pesticide has made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner.

CERCLA Reportable Quantities · 1 item

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).

Safety data

OEB
B
OEL
TWA: 5 mg/m3
PPE
dust mask type N95 (US), Eyeshields, Faceshields, Gloves
wgk
3
IDLA
100 mg/m3
tsca
TSCA listed

Chemistry & industry

Pharmacology

ATC CodeP - Antiparasitic products, insecticides and repellents;P03 - Ectoparasiticides, incl. scabicides, insecticides and repellents;P03A - Ectoparasiticides, incl. scabicides;P03AA - Sulfur containing products;P03AA05 - Thiram
Mechanism of Action · 3 items

Inhibition of hepatic dehydrogenases results in an acetaldehyde reaction on exposure to ethanol. Other effects may result from the known reactions of dithiocarbamates with metals, sulfhydryl-containing enzymes, or metabolism to reactive metabolites including carbon disulfide.

...Ingestion of the fungicide thiram (125 mg/kg)... /has/ been reported to evoke ovarian atrophy and cessation of egg laying in hens, presumably through inhibition of dopamine beta-hydroxylase.

... /It was/ previously demonstrated that Disulfiram impairs the permeability of inner mitochondrial membrane (IMM). In this report, the effect of Disulfiram and its structural analogue thiram (Th) on mitochondrial functions was studied in detail. /It was/ found that mitochondria metabolize thiram disulfide compounds (TDs) in a NAD(P)H- and GSH-dependent manner. At the concentration above characteristic threshold, TDs induced irreversible oxidation of NAD(P)H and glutathione (GSH) pools, collapse of transmembrane potential, and inhibition of oxidative phosphorylation. The presence of Ca(2+) and exhaustion of mitochondrial glutathione (GSH+GSSG) decreased the threshold concentration of TDs. ... TDs induced the mitochondrial permeability transition (MPT).

Metabolism/Metabolites · 5 items

In studies with ruminant animals fed corn treated with thiram, rumen microorganisms degraded thiram to carbon disulfide and probably hydrogen sulfide and dimethylamine. ... some unchanged thiram was also observed in feces /and/ urine.

Pesticides and nitrites in food may be a hazard to man, since many pesticides are secondary or tertiary amines, which form nitroso compounds in the presence of nitrite under conditions resembling those in the human stomach. Compounds were incubated for 4 hours at 37 °C in the presence of excess nitrite at pH 3. Thiram converted to the carcinogen dimethylnitrosamine at a yield of 9%.

The major metabolite in plants is ethylene thiourea, followed by ethylene thiuram monosulfide and presumably ethylene thiuram disulfide and sulfur.

The hepatotoxic effects of thiram metabolism to carbon disulfide were investigated in rats. Male Sprague-Dawley rats were administered 15, 30 or 60 mg/kg thiram ip. Activities of serum glutamic oxaloacetic transaminase and sorbitol dehydrogenase were measured in the blood to assess the extent of liver injury. Detectable amounts of carbon disulfide appeared after 1.5 to 2 hr of treatment; 5 hr were required for complete recovery of carbon disulfide produced from 60 mg/kg thiram. A 2 fold increase in the dose of thiram from 15 to 30 mg/kg resulted in a 10 fold increase in the amount of carbon disulfide in expired air. Increasing the thiram dose 4 times to 60 mg/kg resulted in a 40 fold increase in carbon disulfide production over that from a 15 mg/kg thiram dose. The microsomal inhibitor SKF-525A inhibited the formation of carbon disulfide from thiram; phenobarbital treatment increased the formation of carbon disulfide. Thiram caused a significant loss of cytochrome P450 and benzphetamine-N-demethylase activity at 24 hr following treatment. Five hours after 60 mg/kg thiram treatment, there was an increase in sorbitol dehydrogenase activity 47%; serum glutamic oxaloacetic transaminase activity increased by 41 and 40% during 5 and 24 hr, respectively. /It was/ concluded that carbon disulfide is an in vivo metabolite of thiram and may be responsible for hepatotoxicity.

For more Metabolism/Metabolites (Complete) data for THIRAM (6 total), please visit the HSDB record page.

FDA Pharmacological Classification · 6 items

0D771IS0FH

THIRAM

Established Pharmacologic Class [EPC] - Standardized Chemical Allergen

Physiologic Effects [PE] - Increased Histamine Release

Physiologic Effects [PE] - Cell-mediated Immunity

Chemical Structure [CS] - Allergens

MeSH Pharmacological Classification · 2 items

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

Chemical agents that increase the rate of genetic mutation by interfering with the function of nucleic acids. A clastogen is a specific mutagen that causes breaks in chromosomes.

Absorption, Distribution and Excretion · 3 items

Tetramethylthiuramdisulfide appears to be readily absorbed through the intestinal tract and the lungs and is quickly and widely distributed throughout the body.

In 2 days following its ingestion, bis(dimethylthiocarbamoyl) disulfide (TMTD) is found in the liver and spleen together with its metabolites: amine salt dimethyldithiocarbamic acid (DDCA) and tetramethylthiourea, and in the lungs, carbon disulfide and the amine salt of DDCA. TMTD is known to form N-nitrosodimethylamine by reaction with nitrite in mildly acid solution. TMTD and the amine salt of DDCA are excreted from the body in the urine and feces, and as carbon disulfide via the lungs.

After absorption (respiratory, dermal, gastrointestinal), thiram is distributed in all organs and is mainly excreted unchanged in urine and feces. Some metabolism exists; carbon dioxide is exhaled and dithiocarbamate is excreted in urine.

Uses & manufacturing

Uses · 6 items

Used as a crop fungicide and seed protectant; also used as an animal repellent to protect fruit trees and ornamentals; [EXTOXNET] Used as a fungicide applied to foliage; Also used in seed treatment, as a rodent repellent, a vulcanizing agent, and additive to lubricating oil; [ACGIH]

Farming (Pesticides) [Category: Industry]

For thiram (USEPA/OPP Pesticide Code: 079801) 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./

... Fungicide for large brown patch snowmold and dollar spot on fine turfs.

Wood preservative, mushroom disinfectant.

Primary & secondary accelerators in compounding natural, isobutylene-isoprene, butadiene, styrene-butadiene, synthetic isoprene & nitrile-butadiene rubbers.

U.S. Production · 4 items

2023: 850,000 - <1,000,000 lb;2022: 4,000,000 - <5,500,000 lb;2021: 2,500,000 - <4,000,000 lb;2020: 1,000,000 - <2,500,000 lb

Thioperoxydicarbonic diamide ([(H2N)C(S)]2S2), tetramethyl- is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).[EPA/Office of Pollution Prevention and Toxics; High Production Volume (HPV) Challenge Program. Thioperoxydicarbonic diamide (

(1977) 1.69X10+9 G (SALES ONLY)

(1982) 1.04X10+9 G-MIN CONSUMPTION INCL IMPORT

Consumption Patterns · 4 items

Primary & secondary accelerator for rubbers, approximately 97%; other uses, 3% (1975).

About 97% of thiram utilized in USA is as primary & secondary accelerators in compounding natural, isobutylene-isoprene, butadiene, styrene-butadiene, synthetic isoprene & nitrile-butadiene rubbers.

Based on available data, approximately 165,000 lbs. of thiram are applied to 35,000 acres of strawberries, apples, and peaches annually and up to 631,000 lbs. ai/year are used to treat about 1.3 billion pounds of seed. The seed treatment use in terms of total pounds active ingredient is allocated as follows: cereal grains (73%), cotton seed (12%), large seeded vegetables (7%), soybeans (4%), and small seeded vegetables (3%). The largest foliar markets for thiram in terms of total pounds active ingredient are strawberries (60%), apples (35%), and peaches (3%). The remaining foliar uses are on ornamentals. Most of the foliar usage is in California, Florida, Michigan, New Jersey, New York, Oregon, Pennsylvania, and Washington. In 2003, Pennsylvania applied thiram to 17% of the total acres for peaches (646 acres out of 3,800 acres) based on USDA/NASS data. This is likely to be a sporadic incidence because thiram use was not reported in Pennsylvania in other years. Pennsylvania accounts for only about 3% of the total acres for peaches in the United States, while California, Georgia, and South Carolina together comprise more than 80%. However, Pennsylvania is the only state that shows thiram use on peaches in 2003. Even in 2003 with a relatively higher % acres treated with thiram in Pennsylvania, thiram use on peaches are still less than 3% of the total foliar usage of thiram.

Approximately 53,200 acres in the U.S. were treated with thiram during 1992(1). The estimated annual amounts of thiram applied to apple, strawberry, and peach crop land in the U.S. during 1992 were 139,755 pounds, 117,301 pounds, and 9,320 pounds, respectively(2). Approximately 616,283 ha in the U.K. were treated with thiram during 1992(3).

Consumer UsesPolymerization promoter;Processing aids not otherwise specified
Industry UsesNot Known or Reasonably Ascertainable;Processing aids not otherwise specified;Polymerization promoter;Other
Methods of Manufacturing · 2 items

Thiram is produced by careful oxidation of a N,N-dimethyl dithiocarbamate salt with hydrogen peroxide, chlorine, or air.

... First prepared by oxidation of dimethylamine salt of dimethyldithiocarbamic acid with iodine in ethanolic solution. ... In USA by passing chlorine gas through solution of sodium dimethyldithiocarbamate. In Canada ... from iron oxide, hydrogen peroxide, sodium hydroxide, dimethylamine, and carbon disulfide.

Applications · 8 items

Uses1. Tetramethylthiuram Disulfide belongs to protective fungicides of broad spectrum, with a residual effect period of up to 7d or so. It is mainly used for dealing with seeds and soil and preventing powdery mildew, smut and rice seedlings damping-off of cereal crops. It can also be used for some fruit trees and vegetable diseases. For example, dressing seed with 500g of 50% wettable powder can control rice blast, rice leaf spot, barley and wheat smut. 2. As pesticides, Tetramethylthiuram Disulfide is often referred to as thiram and is mainly used for the treatment of seeds and soil and the prevention and controlling of cereal powdery mildew, smut and vegetable diseases. This product, as the super accelerator of natural rubber, synthetic rubber and latex, is often referred to as accelerator TMTD and is the representative of thiuram vulcanization accelerator, accounting for 85% of the total amount of similar products. Accelerator T is also the super accelerator of natural rubber, diene synthetic rubber, Ⅱ, R and EPDM, with the highest utilization rate of all. The vulcanization promoting force of accelerator T is very strong, but, without the presence of zinc oxide, it is not vulcanized at all. 3. Used for the manufacture of cables, wires, tires and other rubber products. 4. Used as the super accelerator of natural rubber, synthetic rubber and latex. 5. Used as the late effect promoter of natural rubber, butadiene rubber, styrene-butadiene rubber and polyisoprene rubber. 6. Used for the pest control of rice, wheat, tobacco, sugar beet, grapes and other crops, as well as for the seed dressing and soil treatment. 7. Tetramethylthiuram Disulfide is suitable for the manufacture of natural rubber, synthetic rubber and latex, and can also be used as curing agent. This product is the second accelerator of thiazole accelerators, which can be used with other accelerators as the continuous vulcanization accelerator. 8. In rubber industry, Tetramethylthiuram Disulfide can be used as the super-vulcanization accelerator, and aften used with thiazole accelerator. It can also be used in combination with other accelerators as the continuous rubber accelerator. For slowly decomposing out of free sulfur at more than 100 ℃, it can be used as curing agent too. Its products have excellent resistance to aging and heat, so it is applicable to natural rubber, synthetic rubber and is mainly used in the manufacture of tires, tubes, shoes, cables and other industrial products. In agriculture, it can be used as fungicide and insecticide, and it can also be used as lubricant additives. 9. Production methods from dimethylamine, carbon disulfide, ammonia condensation reaction was dimethyl dithiocarbamate, and then by the oxidation of hydrogen peroxide to the finished product.

DescriptionTetramethylthiuram disulfide is a rubber chemieal, an accelerator of vulcanization. It represents the most commonly positive allergen contained in the "thiuram mix". The most frequent occupational categories are the metal industry, homemakers, health services and laboratories, building industries, and shoemakers.

UsesThiram is a protective fungicide applied to foliage to control Botrytis spp. on grapes, soft fruit, lettuce, vegetables and ornamentals. It also controls rust on ornamentals, scab and storage diseases on apple and pear and leaf curl and Monilia on stone fruit. It is used in seed treatments alone or in combination with added insecticides or fungicides to control damping off diseases such as Pythium spp., and other diseases like Fusarium spp. of maize, cotton, cereals, legumes, vegetables and ornamentals.

UsesTetramethylthiuram disulfide is used as fungicide; bacteriostat; pesticide; rubber vulcanization accelerator; scabicide; seed disinfectant; animal repellent; insecticide; lube-oil additive; wood preservative; in antiseptic sprays; in the blending of lubrieant oils; used against Botrytis, rusts and downy mildews; seed dressing against "damping off' and verticillium wilt; ethanol antagonist and deterrent in mixtures of the methyl, ethyl, propyl, and butyl derivatives; antioxidant in polyolefin plastics; peptizing agent in polysulphide elastomers; in soaps and rodent repellents; nut, fruit, and mushroom disinfectant.

Usesantianginal

UsesThiram is an ectoparasiticide. Thiram is used in agriculture to prevent fungal diseases in seed and crops. Thiram has other applications ranging from use as a topical bactericide to animal repellent.

UsesRubber accelerator; vulcanizer; seed disinfectant; fungicide; bacteriostat in soap; animal repellent.

General DescriptionA liquid solution of a white crystalline solid. Primary hazard is to the environment. Immediate steps should be taken to limit spread to the environment. Easily penetrates the soil to contaminates groundwater and waterways.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Shandong chuangyingchemical Co., Ltd.18853181302 · [email protected]
武汉欣扬瑞和化学科技有限公司153-07155313 15307155313 · [email protected]

Additional notes

DefinitionChEBI: An organic disulfide that results from the formal oxidative dimerisation of N,N-dimethyldithiocarbamic acid. It is widely used as a fungicidal seed treatment.

Related reactions

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