Dimethyl Disulfide

Other Classes -> Sulfur Compounds

Flammable agents - 3rd degree

Fungicides, Nematicides

Active substance -> EU Pesticides database: Pending

log Kow = 1.77

1.77

1.77

Garlic-like

Sulfurous

Diffuse, intense onion odor

1.065 at 68 °F (NTP, 1992) - Denser than water; will sink

1.0625 g/cu cm at 20 °C

Relative density (water = 1): 1.06

1.058-1.065 (20 °C)

1.065

1.0625 @ 20°C

0.62 mPa.sec at 20 °C

0.58 mm²/s at 20 °C

Yellow liquid

Liquid

Colorles to pale-yellow liquid

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

Insoluble in water

Miscible with ethanol, ethyl ether

Completely miscible with most organic solvents

Very slightly soluble in water; soluble in alcohol and oils

3 mg/mL at 25 °C

Danger

H225: Highly Flammable liquid and vapor [Danger Flammable liquids]

P210, P233, P240, P241, P242, P243, P260, P261, P264, P264+P265, P270, P271, P272, P273, P280, P301+P316, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P308+P316, P316, P319, P321, P330, P333+P317, P337+P317, P362+P364, P370+P378, P391, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for < 0.1% (1 of 1592) of reports.

Danger

H225 (17.7%): Highly Flammable liquid and vapor [Danger Flammable liquids]

Chemical: Disulfide, dimethyl

Regulation (EC) No 1107/2009 (amended)

Disulfide, dimethyl is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Disulfide, dimethyl 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)

Status: Active Update: 22-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/13671

Disulfide, dimethyl: HSNO Approval: HSR001134 Approved with controls

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]:

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.

Highly flammable. Gives off irritating or toxic fumes (or gases) in a fire. Above 10 °C explosive vapour/air mixtures may be formed.

Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]:

· TOXIC; may be fatal if inhaled, ingested or absorbed through skin.

A mild skin irritant, dimethyl disulfide is toxic by inhalation, skin absorption, and ingestion. Workers are warned by the nauseating odor, but those exposed to high concentrations may experience fatigue, dyspnea, and upper respiratory tract irritation. At lethal concentrations, animals suffer severe lung injury and paralysis of respiratory muscles. [CHEMINFO] Showed weak to moderate sensitizing potential in local lymph node assay (LLNA) of mice; [EPA - TSCATS]

Methyl disulfide is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and 2) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part.

Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]:

Use water spray, powder, foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .

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

Rinse mouth. Do NOT induce vomiting. Give nothing to drink. Refer for medical attention .

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

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.

General First Aid:

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Evacuate danger area! Consult an expert! Remove all ignition sources. Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Ventilation. Do NOT wash away into sewer. Do NOT let this chemical enter the environment. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb liquid in sand or inert absorbent. Carefully collect remainder in sealable containers. Store and dispose of according to local regulations.

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.

Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]:

Immediate precautionary measure

For Fiscal Year 1982, dimethyl disulfide was detected, not quantified, in 27 of 46 composites of human adipose tissue as analyzed for EPA's National Human Adipose Tissue Survey (NHATS)(1). Dimethyl disulfide was qualitatively detected in 2 of 10 samples of expired air from humans(2); its presence was considered to be of metabolic origin(2). In an analysis of 387 expired air samples from 54 healthy, non-smoking adults, dimethyl disulfide was detected in 33.1 samples at a mean concentration of 1.94 ng/L(3). Dimethyl disulfide was qualitatively detected in 6 of 12 samples of human milk collected from volunteers in Bayonne, NJ, Jersey City, NJ, Bridgeville, PA, and Baton Rouge, LA(4). Dimethyl disulfide was identified, not quantified, in human urine samples(5).

LD50; Species: Colinus virginianus (Bobwhite quail) 31 weeks old; oral via capsule 320 mg/kg (95% confidence limit: 250-410 mg/kg)

EC50; Species: Anabaena flosaquae (Blue-Green Algae); Conditions: freshwater, static; Concentration: 320 ug/L for 96 hr (95% confidence limit: 110-900 ug/L); Effect: population abundance /99.6% purity/

EC50; Species: Navicula pelliculosa (Diatom); Conditions: freshwater, static; Concentration: 22000 ug/L for 96 hr (95% confidence limit: 20000-23000 ug/L); Effect: population abundance /99.6% purity/

EC50; Species: Pseudokirchneriella subcapitata (Green Algae); Conditions: freshwater, static; Concentration: 15000 ug/L for 72 hr (95% confidence limit: 11000-20000 ug/L); Effect: population abundance /99.9% purity/

For more Ecotoxicity Values (Complete) data for Dimethyl Disulfide (13 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 40(SRC), determined from a structure estimation method(2), indicates that dimethyl disulfide is expected to have very high mobility in soil(SRC). Volatilization of dimethyl disulfide from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 1.21X10-3 atm-cu m/mole(3). Dimethyl disulfide is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 28.7 mm Hg at 25 °C(4). Methyl disulfide had a 0% theoretical BOD using activated sludge in the Japanese MITI test(5) suggesting that biodegradation is not an important environmental fate process in soil(SRC). However, in a study using anoxic salt marsh sediments, dimethyl disulfide was rapidly reduced by 50% in 1-2 days to methanethiol(6), suggesting that biodegradation under anaerobic conditions is an important environmental fate process(SRC). Dimethyl disulfide absorbs UV light in the environmental spectrum and has been shown to photolyze rapidly, in gas phase, in sunlight(7,8); although photolysis rates on soil have not been measured, the surface half-life (for full sunlight exposure) may be similar to the several hour half-life observed for the gas phase(8). As well as releasing methyl disulfide in the gas phase, soil can also adsorb dimethyl disulfide from the gas phase and act as an environment sink(9); the relative importance of this process is not clear(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 40(SRC), determined from a structure estimation method(2), indicates that dimethyl disulfide is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 1.21X10-3 atm-cu m/mole(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 3.5 hours and 4.1 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 0.3(SRC), from its log Kow of 1.77(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Dimethyl disulfide absorbs UV light in the environmental spectrum and has been shown to photolyze rapidly, in gas phase in sunlight(8-9); although photolysis rates in water have not been measured, the near-surface half-life (for full sunlight exposure) may be similar to the several hour half-life observed in the gas phase(9). The aqueous hydrolysis of dimethyl disulfide at ambient temperatures and pHs <12 is too slow to be an important environmental fate process(10). Under anoxic conditions in salt marsh sediments, the initial concentration of methyl disulfide was reduced by 50% in 1-2 days(11). However, data for aerobic biodegradation indicate dimethyl disulfide is recalcitrant under these conditions(12).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dimethyl disulfide, which has a vapor pressure of 28.7 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase dimethyl disulfide 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 1.6 hours(SRC), calculated from its rate constant of 2.39X10-10 cu cm/molecule-sec at 25 °C(3). Direct photolysis (half-life of 3.2-4.6 hr at full sunlight)(4-5) and reaction with nitrate radicals (half-life of 1.1 hr during night-time hrs)(6) will also contribute to its atmospheric degradation. Physical removal from air can occur through gas phase sorption by soil(7).

Reported found in sour cherry, guava, melon, peach, pineapple, strawberry, cabbage, kohlrabi, onion, garlic, shallot, leek, peas, potato, rutabaga, tomato, parsley, breads, many cheeses, yogurt, milk, eggs, fish, meas, hop oil, beer, Scotch whiskey, cognac, wine grapes, cocoa, coffee, peanut, peanut butter, pecan, potato chips, oats, soybean, beans, mushrooms, trassi, macadamia nut, mango, cauliflower, broccoli, brussels sprouts, rice, radish, sukiyaki, sake, watercress, malt, wort, krill, southern pea, loquat, sapodilla, shrimp, oyster, crab, crayfish, clam, scallops and squid.

Dimethyl disulfide has been identified in processed cassava products(1) and in volatile components of roasted filbert nuts(2), cooked potatoes(3), coffee(4), mature kiwi fruit(5), raw chicken breast(6), Welsh onions and scallions(7), scrambled eggs(8), chickpeas(9), fresh strawberries(10), cooked mutton, chicken, beef and pork volatiles(11), frankfurters(12), and cooked peas(13). dimethyl disulfide was detected in ground and whole musty sorghum(14).

Dimethyl disulfide concentrations of 0.64-2.51 ug/g garlic bulb were detected(1). Dimethyl disulfide was present in the volatiles formed by popping popcorn at 13 to 20 ug/kg(2). Mean dimethyl disulfide concentrations in anchovy, big eyed herring, hair tail viscera, and shrimp paste were 540, 32900, 182, and 224 ng/g, respectively(3). Dimethyl disulfide composed 2.32% of the total volatiles isolated from stir-fried garlic(4). Volatiles in Italian-type dry-cured Parma ham included dimethyl disulfide; at day 3 in the production process no dimethyl disulfide was present, by 485 days dimethyl disulfide concentration was 59 ng dodecane equivalents(5). Volatiles from spoiled Parma ham contained dimethyl disulfide at 36 ng dodecane equivalents(5). Mean dimethyl disulfide concentrations were 114.1, 30.2, and 25.9 ug/kg measured in honey derived form honeydew of Holm-oak, oak and forest, respectively(6).

Dimethyl disulfide was qualitatively detected in 6 of 12 samples of human milk samples collected from volunteers in Bayonne, NJ, Jersey City, NJ, Bridgeville, PA, and Baton Rouge, LA(1). Volatiles from cold-stored cows milk contained dimethyl disulfide at unreported concentrations(2).

Volatile organic compounds emitted from Allium ursinum, planted as ground cover, contained dimethyl disulfide; an average emission rate for this compound was measured as 0.239 ug/g-hr (per unit of ground area 14.6 ug/sq m-hr)(1).

Plants containing dimethyldusulfide(1).[Table#5961]

Cough. Sore throat. Headache. Nausea. Dizziness. Drowsiness.

EASILY ABSORBED! Redness. Further see Inhalation.

Redness. Pain.

See Inhalation.

The average dimethyl disulfide concentration of wastewater effluent collected from the Los Angeles County treatment plant between Nov 1980 and Aug 1981 was 45 ug/L(1). Effluent from a 5-yr old community septic tank contained dimethyl disulfide at 29.7 ug/L(2). Dimethyl disulfide was detected in 3 of 63 wastewater effluents (concentration <100 ppb) collected from chemical manufacturing plants across the US(3). Dimethyl disulfide was detected in 5 of 204 water samples collected from 14 heavily industrialized river basins in the US(4). A dimethyl disulfide concentration of 1.2 mg/L was detected in a leachate collected from a Minnesota municipal solid waste landfill(5). Dimethyl disulfide was detected as a volatile compound in samples of kitchen waste, kitchen waste exudate, stored food exudate, and garden waste, previously collected as municipal waste, at unreported concentrations(6-7). Dimethyl disulfide was detected by headspace analysis in 4 of 4 biodegradable waste samples and 4 of 7 mixed waste samples(8). Dimethyl disulfide was detected in the volatile emissions from laboratory compost(9).

Dimethyl disulfide concentrations in biogas were 0-1020 ppbV in 8 samples taken Nov 2000 to Jun 2002; after gasses were passed through a scrubber, levels were decreased to <1-4 ppbV(1). Atmospheric emissions rates of dimethyl disulfide from 5 wetland plant soils in Florida ranged from <0.03 to 1.5 ug (sulfur basis)/sq m/hr(2); the dimethyl disulfide emitted resulted from biogenic formation(2). The estimated emission rates of dimethyl disulfide to the atmosphere from natural sources has been reported as follows (in million tons sulfur/yr)(3): oceanic: 0-1; salt marsh: 0.13; inland swamps: 0.2; soil and plants: 1; burning of biomass: 0-1; volcanoes and fumaroles: 0.01(3).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of dimethyl disulfide can be estimated to be 40(SRC). According to a classification scheme(2), this estimated Koc value suggests that dimethyl disulfide is expected to have very high mobility in soil. Gas chromatographic studies with various air-dry and moist soils have shown that soil can sorb atmospheric, gas phase dimethyl disulfide(3). In one closed-system test, 17-94% of input dimethyl disulfide was sorbed by the soil in 10 min(3); in a 15-day test, dimethyl disulfide sorption was 101-306 ug sorbed/g soil(3). Soil microbes were found to be important for the gas phase sorption of dimethyl disulfide as 15-day sorption in sterilized soil was only 9-98 ug sorbed/g soil(3).

Methyl disulfide is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and 2) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part.

Chemical analysis of Zapoteca formosa extracts show that a variety of volatile sulfur-containing components, including cyclic polysulfides, are responsible for the distinctive odor of its germinating seeds and young plants. The major sulfur-containing compounds include acetyl djenkolic acid, djenkolic acid, taurine, cystine, benzothiazole, dimethyl disulfide, 2,4-dithiapentane, 2-hydroxyethylmethylsulfide, trithiane, 1,2,4-trithiolane, and 1,2,4,6-tetrathiepane. Decreased amounts of djenkolic acid in seedlings and young plants, as compared to the seed, indicate that this is likely the metabolic precursor of the volatile sulfur components. Germination and radicle elongation assays show that germinating seeds of Zapoteca and mixtures of volatile sulfur-containing compounds are highly phytotoxic to Cucumis sativa, Lactuca sativa, Lycopersicon esculentum, and Acacria farnesiana.

The plant-derived insecticides have introduced a new concept in insecticide research. In response to insect attacks, some plants can release volatile sulfur compounds such as dimethyl disulfide (DMDS) in the atmosphere, which are lethal for the generalist insects. /The authors/ demonstrate that DMDS induced an uncommon complex neurotoxic activity. The studies of in vivo toxicity of DMDS in three insect species and mice indicated a highest bioactivity for insects. Although DMDS did not alter the electrophysiological properties of the cockroach Periplaneta americana giant axon, it affected the synaptic transmission at the presynaptic level resulting in an inhibition of the neurotransmitter release. Whole cell patch-clamp experiments performed on cockroach cultured dorsal unpaired median (DUM) neurons revealed a dose-dependent hyperpolarization induced by DMDS associated with a decrease in the input resistance and the disappearance of action potentials. The hyperpolarization was inhibited by glibenclamide and tolbutamide, and was dependent on intracellular ATP concentration, demonstrating a neurotoxicity via the activation of KATP channels. Finally, the same effects observed with oligomycin, 2,4-dinitrophenol, and KCN together with the studies of DMDS toxicity on isolated mitochondria confirmed an unusual action occurring through an inhibition of the mitochondrial respiratory chain complex IV (cytochrome oxydase). This DMDS-induced inhibition of complex IV subsequently decreased the intracellular ATP concentration, which thereby activated neuronal KATP channels mediating membrane hyperpolarization and reduction of neuronal activity.

Dimethyl disulfide (DMDS), a plant-derived insecticide, is a promising fumigant as a substitute for methyl bromide. To further understand the mode of action of DMDS, /researchers/ examined its effect on cockroach octopaminergic neurosecretory cells, called dorsal unpaired median (DUM) neurons, using whole-cell patch-clamp technique, calcium imaging and antisense oligonucleotide strategy. At low concentration (1 microM), DMDS modified spontaneous regular spike discharge into clear bursting activity associated with a decrease of the amplitude of the afterhyperpolarization. This effect led us to suspect alterations of calcium-activated potassium currents (IKCa) and [Ca(2+)](i) changes. /Researchers/ showed that DMDS reduced amplitudes of both peak transient and sustained components of the total potassium current. IKCa was confirmed as a target of DMDS by using iberiotoxin, cadmium chloride, and pSlo antisense oligonucleotide. In addition, /they/ showed that DMDS induced [Ca(2+)](i) rise in Fura-2-loaded DUM neurons. Using calcium-free solution, and (R,S)-(3,4-dihydro-6,7-dimethoxy-isoquinoline-1-yl)-2-phenyl-N,N-di-[2-(2,3,4-trimethoxy-phenyl)ethyl]-acetamide (LOE 908) [an inhibitor of transient receptor potential (TRP)gamma], /researchers/ demonstrated that TRPgamma initiated calcium influx. By contrast, omega-conotoxin GVIA (an inhibitor of N-type high-voltage-activated calcium channels), did not affect the DMDS-induced [Ca(2+)](i) rise. Finally, the participation of the calcium-induced calcium release mechanism was investigated using thapsigargin, caffeine, and ryanodine. /This/ study revealed that DMDS-induced elevation in [Ca(2+)](i) modulated IKCa in an unexpected bell-shaped manner via intracellular calcium. In conclusion, DMDS affects multiple targets, which could be an effective way to improve pest control efficacy of fumigation.

The metabolism of methanethiol was studied in rats. The levels of volatile sulfur compounds methanethiol, dimethylsulfide and dimethyldisulfide in the air expired by rats exposed to a noncomatogenic dose of methanethiol through the colon were elevated.

Hydrogen sulfide is formed by the subgingival microbiotas of periodontal pockets. The capacity of these microbiotas to form various volatile sulfur compounds in human serum was studied. Hydrogen sulfide was the predominant volatile sulfur compound. Only traces of dimethyl sulfide and dimethyl disulfide were detected. There was an extensive degradation of the serum proteins. In most of the reaction mixtures hydrogen sulfide reached highly toxic levels.

Used as a chemical intermediate: [CAMEO] Released in Kraft pulping to make paper; Also used as a gas well down hole process aid; Proposed to replace methyl mercaptan as a jet fuel additive; [NTP] Occupational exposure also occurs at sewage treatment plants. It occurs naturally in many foods. [HSDB] Also used as a sulfiding agent in refineries, a solvent for sulfur, to reduce coke deposits in the petrochemical industry, an artificial flavoring agent, and a corrosion inhibitor; [CHEMINFO] Used to flavor animal feeds; [EFSA - FEEDAP] Used as a flavoring agent; [FDA]

Petroleum Production and Refining [Category: Industry]

For methyl disulfide (USEPA/OPP Pesticide Code: 029088) ACTIVE products with label matches. /SRP: Registered for use in the USA but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Fumigant

As a sulfiding agent added to the initial feed of a hydrotreater when the hydrotreating catalyst is present in the form of oxides.

Non-confidential information in the IUR indicated that the industrial processing and uses for the chemical include all other chemical product and preparation manufacturing as intermediates; petroleum refineries as solvents (for cleaning or degreasing); natural gas distribution, oil and gas extraction, petrochemical manufacturing, and petroleum refineries as "other." Non-confidential commercial and consumer uses of this chemical include "other."

2023: 10,000,000 - <50,000,000 lb

Disulfide, dimethyl 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).

Production volumes for non-confidential chemicals reported under the Inventory Update Rule.[Table#5962]

Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: Disulfide, dimethyl. Aggregated National Production Volume: 1 to < 10 million pounds.

Non-confidential 2012 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: Disulfide, dimethyl. National Production Volume: 10,000,000 - 50,000,000 lb/yr.

Paladin Technical (Arkema Inc.), Dimethyl disulfide 99.8%

Paladin (Arkema Inc.), Dimethyl disulfide 98.8%

Paladin EC (Arkema Inc.), Dimethyl disulfide 93.8%

Paladin MUP (Arkema Inc.), Dimethyl disulfide 98.8%

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

All Other Basic Organic Chemical Manufacturing

Disulfide, dimethyl: ACTIVE

The typical marketed Dimethyl-disulfide is 99.5% pure.

Reported uses: alcoholic beverages, baked goods, condiments, relishes, frozen dairy, gelatins, puddings, meat products, nonalcoholic beverages, soft candy, sweet sauce