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Home > Encyclopedia > Dimethylformocarbothialdine

Dimethylformocarbothialdine

Dimethylformocarbothialdine structure

Dimethylformocarbothialdine 

structure
  • CAS No:

    533-74-4

  • Formula:

    C5H10N2S2

  • Chemical Name:

    Dimethylformocarbothialdine

  • Synonyms:

    2H-1,3,5-Thiadiazine-2-thione,tetrahydro-3,5-dimethyl-;Tetrahydro-3,5-dimethyl-2H-1,3,5-thiadiazine-2-thione;Crag 85W;N 521;Crag 974;UCC 974;Dazomet;Dimethylformocarbothialdine;3,5-Dimethyltetrahydro-2H-1,3,5-thiadiazine-2-thione;3,5-Dimethyltetrahydro-1,3,5-2H-thiadiazine-2-thione;3,5-Dimethyltetrahydro-1,3,5-thiadiazine-2-thione;3,5-Dimethyl-2-thionotetrahydro-1,3,5-thiadiazine;DMTT;Mylone;Nalcon 243;Stauffer N 521;Tetrahydro-2H-3,5-dimethyl-1,3,5-thiadiazine-2-thione;Thiazon;Thiazone;2-Thio-3,5-dimethyltetrahydro-1,3,5-thiadiazine;Mylone 85;Basamid P;Basamid G;Nefusan;Basamid;Basamid-Puder;Tetrahydro-3,5-dimethyl-2H-1,3,5-thiodiazin-2-thione;Fennosan B 100;D 35;Tetrahydro-3,5-dimethyl-1,3,5-thiadiazin-2-thione;Busan;Nalco 5787;Busan 1058;Nuosept S;NSC 4737;Metasol D 3TA;AMA 424;Basamid Granular;3,5-Dimethyl-1,3,5-thiadiazinane-2-thione;55146-10-6;1135442-80-6

  • Categories:

    Agrochemicals  >  Fungicides

Description

White crystalline solid. Nearly odorless.


Dazomet appears as white crystals or off-white powder. Pungent, acrid odor. (NTP, 1992)|WHITE OR COLOURLESS CRYSTALS.


Dazomet appears as white crystals or off-white powder. Pungent, acrid odor. (NTP, 1992)|Dazomet is a dithiocarbamic ester that is 1,3,5-thiadiazinane with a thione moiety at position 2 and in which the hydrogens attached to the nitrogens are replaced by methyl groups. A fungicide, herbicide and nematicide, it is used prior to sowing or planting for the control of soil fungi, nematodes, bacteria and germinating weeds, and as fumigant for poultry litter and eggs to control Salmonella. It is a non-ozone-depleting alternative to methyl bromide. It has a role as a herbicide, a nematicide, an antibacterial agent and an antifungal agrochemical. It is a dithiocarbamic ester and a thiadiazinane.

Dimethylformocarbothialdine Basic Attributes

162.28

162.28

208-576-7

S7419CG4W5

0786

4737

3077|2588

DTXSID7024902

Colorless crystals|Needles from benzene

2934999039

Characteristics

63.9

1.4

Dazomet appears as white crystals or off-white powder. Pungent, acrid odor. (NTP, 1992)

1.30 g/cm3 @ Temp: 20 °C

106-107 °C

222.3±50.0 °C at 760 mmHg

156 °C

1.656

H2O: <0.1 g/100 mL at 18 ºC;Solubility in water, g/100ml at 20°C: 0.3

0-6°C

3.7 x 10 -4 Pa (25 °C)

Oral-Rat LD50: 320 mg/kg; Oral-Mouse LD50: 180 mg/kg

Combustion produces toxic chloride and sulfur oxide gases

Weakly pungent

2.66e-10 atm-m3/mole|Henry's Law constant = 2.66X10-10 atm-cu m/mole at 25 °C

pKa = 6.29 (est)

Decomposes above 102 °C.|Stable at temperatures up to 35 °C. Sensitive to temperatures >50 °C and to moisture. In the presence of moisture, degrades to methyl isothiocyanate, formaldehyde, hydrogen sulfide, and methylamine.|Technical: Solid, crystalline, white-slightly gray|Hydroxyl radical reaction rate constant = 2.85X10-10 cu m/molec-sec at 25 °C (est)

Insoluble in water. Slowly hydrolyzed.

Amines, Phosphines, and Pyridines

DAZOMET decomposes in water, dilute acids and alcohol. (NTP, 1992)

Non-corrosive in the dry state

Safety Information

III

6

UN30779/PG3

3

22-36-50/53

15-22-24-60-61

XI2800000

Xn,N

The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials

Stable at ambient temperatures if it is kept dry.

P273-P305 + P351 + P338-P501

H302-H319-H410

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

USEPA/Office of Pesticide Programs; Reregistration Eligibility Decision (RED) for Dazomet 114 pp. EPA 738-R-08-007 (July 2008). Available from the Database Query page at http://www.epa.gov/pesticides/reregistration/status.htm as of October 23, 2008.|USDA; Pesticide Background Statements. Vol 3, Nursery Pesticides (1989) NTIS/PB89-226716. This document is a compendium of pesticide background statements that review the available information on the chemistry, toxicology, environmental fate properties, and methods of application of 14 pesticides. ...

Flash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)|Combustible under specific conditions. Gives off irritating or toxic fumes (or gases) in a fire.

|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P273, P280, P301+P312, P305+P351+P338, P330, P337+P313, P391, and P501|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|Aggregated GHS information provided by 455 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P201, P202, P260, P261, P264, P270, P271, P281, P301+P312, P304+P312, P304+P340, P308+P313, P309+P311, P312, P314, P330, P405, and P501|Danger|P201, P202, P260, P264, P270, P273, P281, P301+P312, P308+P313, P309+P311, P314, P330, P391, P405, and P501

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

SMALL SPILLS AND LEAKAGE: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone 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 chemical under ambient temperatures, and protect it from moisture. If possible, it would be prudent to store this compound under inert atmosphere. (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. Splash proof safety goggles should be worn while handling this chemical. Alternatively, a full face respirator, equipped as above, may be used to provide simultaneous eye and respiratory protection. (NTP, 1992)|The Agency is requiring all handlers to wear double layers consisting of coveralls over short-sleeved shirt and short pants with gloves. In addition, handlers will have an option to reduce the dermal protection if application equipment (i.e., enclosed cabs) that provides dermal protection is used.|The Agency is requiring handlers potentially exposed to MITC vapors from dazomet applications to either wear at least a half-face respirator during the handling activity, or follow /a specified/ monitoring program ... .. For some handling tasks ... respirators are required to be worn at all times due to the short duration of the task and the potentially high concentration of MITC exposure. The certified applicator supervising the fumigant application must ensure that any handler who enters the buffer zone (including tractor drivers, loaders, irrigators, tarp cutters, removers, etc.) is either wearing respiratory protection or is following the handler monitoring requirements, with respirators immediately available to each handler.|Long Duration Tasks. For handlers such as applicators supervising or making the application, tractor drivers, tractor co-pilots, shovelers, and tarp cutters, the respiratory requirements include: Mandatory monitoring in the breathing zone of handlers at least once an hour, even if a respirator is worn. Air-purifying respirators must be put on if one of the following occurs: (1) MITC concentrations are = 100 ppb, or (2) Handlers experience sensory irritation. All activities must cease if one of the following occurs: (1) MITC concentrations are = 1000 ppb, or (2) Handlers experience sensory irritation while wearing respirators. In order to remove the respirator or resume work activities:(1) Two air samples for MITC must be taken in the treatment area at least 15 minutes apart. (2) The samples must be less than 100 ppb to remove the respirator and below 1000 ppb for work activity to resume with a respirator. (3) During the collection of samples an air purifying respirator must be worn. Respirators cannot be removed until monitoring indicates that levels have decreased below the triggers listed above, and if handlers are not experiencing eye irritation.|Respiratory Protection - Handlers exposed to MITC vapors from dazomet applications will either wear respirators or follow an air monitoring program. Additional dermal PPE is required for some handler tasks.|For more Personal Protective Equipment (PPE) (Complete) data for DAZOMET (6 total), please visit the HSDB record page.

/To fight fire use/ powder, water spray, foam, carbon dioxide.

Do NOT wash away into sewer. Sweep spilled substance into containers. Carefully collect remainder, then remove to safe place.

EPA has developed a multi-faceted approach to addressing bystander and handler risk for fumigants. This involves label changes, education of fumigant applicators and handlers, monitoring of fumigant air concentrations, and development of additional data to refine risk assessments.|Specific mitigation for bystanders and handlers from soil use of dazomet includes: (1) Maximum Rate Reduction - A change in the maximum application rate will be a reduction from 530 to 425 lbs a.i./A, which will directly reduce the potential risks to both humans and non-target organisms. (2) Restricted Use Pesticide (RUP) Classification - MITC, the byproduct of dazomet, meets the criteria for restricted use based on human hazard criteria and exposure incidents. All soil fumigant products containing dazomet will be RUPs. (3) Buffer Zones - Buffer zones, of varying sizes based on application method, application rate, and application block size, and emission control measures are required. Buffer zones will be in effect from the time the fumigation begins until 48 hours following the application. (4) Posting - EPA is requiring that buffer zones be posted at usual points of entry and along likely routes of approach to the buffer unless (a) a physical barrier such as a fence prevents access to the buffer, or (b) all of the area within 300' of the buffer is under the control of the owner/operator. The posting requirement is intended to prevent passersby from entering a buffer zone.|Posting is recognized as an effective means of informing workers and others about areas where certain hazards and restrictions exist. Current soil fumigant labels require treated areas to be posted, and handlers are required to wear specific PPE when they are in a treated area. For buffer zones to be effective risk mitigation, bystanders, including agricultural workers in nearby areas, need to be informed of the location and timing of the buffer to ensure they do not enter areas designated as part of the buffer zone. In addition to alerting bystanders, posting a buffer zone will help handlers determine where and when they are required to use PPE. ...|Mandatory Good Agricultural Practices (GAPs) must be followed during all soil applications. GAPs specify appropriate weather conditions, injection depth, soil sealing, use of tarps, soil temperature, air temperature, soil moisture, soil preparation, prevention of end row spillage, flushing of drip irrigation lines, and calibration, set-up, repair and maintenance of application equipment.|For more Preventive Measures (Complete) data for DAZOMET (12 total), please visit the HSDB record page.

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

Even dilute soln cause skin irritation ... in humans.|Dust may cause irritation of skin and eyes.|A severe eye irritant. A mild primary skin irritant & sensitizer.

Do NOT wash away into sewer. Sweep spilled substance into covered containers. Carefully collect remainder. Then store and dispose of according to local regulations.

Provision to contain effluent from fire extinguishing. Separated from acids and food and feedstuffs. Cool. Dry. Keep in a well-ventilated room.

Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly when dispersed.

The substance is irritating to the eyes.

Repeated or prolonged contact may cause skin sensitization.

NO open flames.

PREVENT DISPERSION OF DUST! STRICT HYGIENE!

Use local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear safety goggles or eye protection in combination with breathing protection.

Toxicity

moderately toxic

LD50 Mouse, male albino acute oral 650 mg/kg|LD50 Rabbit acute oral 320-620 mg/kg|LD50 Rat oral 320 mg/kg|LC50 Rat inhalation 8400 mg/cu m/4 hr|For more Non-Human Toxicity Values (Complete) data for DAZOMET (12 total), please visit the HSDB record page.

/BIRDS and MAMMALS/ The NOEC /for bobwhite quail/ is 147 mg/kg with observed effects at higher dose(s) including lethargy, anorexia, and reduced mean body weights and feed consumption. Based on these results, dazomet is categorized as moderately toxic to avian species on an acute oral basis.|/BIRDS and MAMMALS/ Avian reproduction studies ... are required for dazomet because birds may be subject to repeated or continuous exposure to the pesticide, especially preceding or during the breeding season. The preferred test species are mallard duck and bobwhite quail. Significant treatment-related effects in the mallard study included reductions in egg production, egg quality, fertility, and embryonic survival at the 1000 ppm level. A significant reduction in hatchling weight was also observed at the 100 ppm level. In the bobwhite quail study, dazomet exposure of 100 ppm significantly reduced the number of hatched to eggs laid and the proportion of live embryos to viable embryos was significantly reduced at all treatment levels. At the 1000 ppm level, egg fertility, embryonic survival, hatchability, and chick survival were adversely affected.|/AQUATIC SPECIES/ Based on the rapid hydrolysis of dazomet, aquatic organisms will likely be exposed only to MITC (methyl isothiocyanate)... .|/AQUATIC SPECIES/ Freshwater fish acute studies for the degradate (MITC) indicate that it is very highly toxic to rainbow trout with 96-hour LC50 values ranging from 0.094 to 0.0512 ppm. MITC is also highly toxic to bluegill sunfish with a reported 96-hour LC50 of 0.142 ppm. Based on the rapid hydrolysis of dazomet, aquatic organisms will likely be exposed only to MITC; consequently, acute risk to freshwater fish species will be assessed using the lowest toxicity value from these studies (rainbow trout LC50 of 0.0512 ppm; static renewal test). /Methyl isothiocyanate/|For more Ecotoxicity Excerpts (Complete) data for DAZOMET (6 total), please visit the HSDB record page.

Dazomet's production may result in its release to the environment through various waste streams; its use as a soil sterilant, nematicide, fungicide, slimicide in pulp and paper manufacture, and as a preservative in adhesives and glues(1) will result in its direct release to the environment(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 52(SRC), determined from a log Kow of 0.63(2) and a regression-derived equation(3), indicates that dazomet is expected to have high mobility in soil, however it is expected to hydrolyze(2) before extensive leaching occurs(SRC). Volatilization of dazomet from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 2.66X10-10 atm-cu m/mole(2). When dazomet is applied to soil, either to the surface or incorporated, it quickly hydrolyzes in the presence of moisture(4). The major degradate is methyl isothiocyanate, but formaldehyde, monomethylamine, hydrogen sulfide and (in acid soils) carbon disulfide, are also formed(4). The half-life of dazomet in soil has been reported as less than 1 day (pH >5)(2). The rate of disappearance was found to be the same in both unamended and sterilized soils(5) and in different soil types(6), indicating that chemical hydrolysis and not biodegradation is the primary removal process. Dazomet is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 2.80X10-6 mm Hg(2).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 52(SRC), determined from a log Kow of 0.63(2) and a regression-derived equation(3), indicates that dazomet is not 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 2.66X10-10 atm-cu m/mole(2). In water, dazomet is expected to rapidly undergo hydrolysis, forming methyl isothiocyanate and formaldehyde(4). Half-lives of 3.6, 2.4, 2.8, and 4.0 hours have been reported at pH values of 4.4, 5.7, 7.0, and 8.0, respectively(5). In salt water (0.15 M), a half-life of 6.1 hours was reported(5). According to a classification scheme(6), an estimated BCF of 2.4(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dazomet, which has a vapor pressure of 2.80X10-6 mm Hg at 20 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase dazomet 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 1.4 hours(SRC), calculated from its rate constant of 2.85X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase dazomet may be removed from the air by wet or dry deposition(SRC). It may undergo hydrolysis during rain events or in clouds(SRC) due to degradation on contact with moisture(2). It has been suggested that dazomet may also undergo direct photolytic degradation and this process may contribute to atmospheric removal(4).

POOR SANDY SOIL WAS TREATED WITH 2000 PPM BASAMID-PULVER (AI DAZOMET). DECOMPOSITION YIELDED METHYLMUSTARD OIL, FORMALDEHYDE & METHYLAMINE, ALSO N,N'-DIMETHYL THIOUREA & 1,3,5-TRIMETHYL-HEXAHYDROTRIAZINETHIONE.|MYLONE WAS LOST AT SIMILAR RATES FROM AUTOCLAVED AND NONSTERILE SOIL. NO SECONDARY AMINE ACCUM WAS NOTED.|THE BREAKDOWN OF DAZOMET TO ACTIVE CMPD IN SOIL IS GREATLY DEPENDENT ON THE MOISTURE CONTENT OF THE SOIL. WHEN IN CONTACT WITH WATER, DAZOMET DECOMP TO METHYL ISOTHIOCYANATE /MIT/, FORMALDEHYDE, HYDROGEN SULFIDE, AND MONOMETHYLAMINE. ...THE RATE OF METHYL ISOTHIOCYANATE FORMATION INCR AS MOISTURE WAS INCR TO 80% OF SATURATION.../AND/ WITH INCR IN TEMP (1 DEG, 10 DEG, & 23 °C) & INCR IN PH (2.3-6.5) BUT FELL OFF FROM PH 6.5-7.7. INCR IN CLAY OR PEAT CONTENT OF SOIL DECR THE RATE OF MIT FORMATION. .../IT WAS/ SPECULATED THAT THE FORMATION OF MIT WAS INDEPENDENT OF SOIL MICROBIAL ACTIVITY.|The rate constant for the vapor-phase reaction of dazomet with photochemically-produced hydroxyl radicals has been estimated as 2.85X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 1.4 hours at an atmospheric concentration of 5X10+5 radicals per cu cm(1). Dazomet reacts rapidly with water to form methyl (methylaminomethyl)dithiocarbamic acid and formaldehyde initially which subsequently form methyl isothiocyanate, hydrogen sulfide, and methyl amine(2). Under acidic conditions, dazomet hydrolyzes to carbon disulfide(3). Although experimental data on the rate of this reaction are not available, hydrolysis in moist soil is rapid(3). In water at pH values of 4.4, 5.7, 7.0, 7.4, 8.0, and 9.4, half-lives of 3.6, 2.4, 2.8, 3.0, 4.2, and 3.3 hours were reported(4). In salt water (0.15 M), a half-life of 6.1 hours was observed(4). While photolysis of dazomet has not been reported, it has been suggested that it will decompose to methylamine, carbon disulfide, and methyl isothiocyanate under the influence of sunlight(5).

An estimated BCF of 2.4 was calculated for dazomet(SRC), using a log Kow of 0.63(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). In addition, dazomet is rapidly hydrolyzed in both fresh and salt water(4) and is not expected to be present for sufficient periods of time for bioconcentration(SRC).

10.00 L/kg|The Koc of dazomet is estimated as 52(SRC), using a log Kow of 0.63(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that dazomet is expected to have high mobility in soil; however it is expected to hydrolyze(1) before extensive leaching occurs(SRC).

The Henry's Law constant for dazomet is 2.66X10-10 atm-cu m/mole(1). This Henry's Law constant indicates that dazomet is expected to be essentially nonvolatile from water surfaces(2). Dazomet's Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). Dazomet quickly breaks down in the presence of moisture with the major degradate being methyl isothiocyanate(1,3). Half-lives of less than 1 day and less than 10 hours have been reported for dazomet in soil and water, respectively (pH >5)(1). Dazomet is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 2.80X10-6 mm Hg(1).

Following application to strawberries, no residue of dazomet or its degradation products were detected at >0.01 ppm in the fruit(1).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 25,682 workers (528 of these were female) were potentially exposed to dazomet in the US(1). The NOES Survey does not include farm workers. Occupational exposure to dazomet may occur through inhalation of dust and dermal contact with this compound at workplaces where dazomet is produced or used(SRC).

Drug Information

4. 4= VERY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 50-500 MG/KG, BETWEEN 1 TSP AND 1 OZ FOR 70 KG PERSON (150 LB).

One hr after oral administration to rats, unhydrolyzed mylone was found in stomach. Carbon disulfide equiv to 1-3% of dose was found in stomach and 1.5% of dose was found in exhaled air. After either intravenous or oral administration of mylone to dogs, carbon disulfide was found in exhaled air...|Not readily absorbed by the skin.|In a rat metabolism study, dazomet, metam sodium, and MITC were tested at two dose levels. All three were excreted mainly in urine with small amounts excreted in feces. Three different compounds (MITC, carbon dioxide [CO2], carbon oxide sulfide [COS]/carbon disulfide [CS2]) were found to be excreted in the lungs over a 73 hour collection period. There were no differences between males and females in amounts excreted via the three excretion routes; however, tissue and plasma levels, and plasma area under the curves (AUCs) were consistently higher in females than in males. It should be noted that these differences were approximately 2-fold or less. All three compounds were rapidly absorbed from the GI tract. High uptake was seen in the liver, kidneys, and lung, with the lowest level in testes, brain and eyes. Metabolic profiles detected in urine, liver, and kidneys were basically similar for the three compounds but there were some differences, mainly quantitative in nature.

One hr after oral administration to rats, unhydrolyzed mylone was found in stomach. Carbon disulfide equiv to 1-3% of dose was found in stomach and 1.5% of dose was found in exhaled air.|Isotopic labeling of metham, methyl isothiocyanate and dazomet with (13)CH3 and (14)CH3 and of metham and methyl isothiocyanate with (13)C S provided the materials for metabolite identification by (13)C NMR and quantitation by HPLC analysis and radiocarbon counting. Rats and mice were treated ip and the metabolites studied at 48 hr. Most of the (14)CH3 label for each cmpd in mice appears in urine (58-80%) or is retained in the body (8-12%), particularly the liver or kidney. The major metabolites in each case from rats are S-(N-methylthiocarbamoyl)glutathione in the bile and S-(N-methylthiocarbamoyl)mercapturic acid in the urine, whereas from mice the mercapturate is a minor metabolite. Methylamine is a major urinary component following treatment with methylamine or dazomet. (rats and mice) or metham (mice) but not with methyl isothiocyanate. Detoxification by conjugation with glutathione appears to involve direct reaction with methyl isothiocyanate, glutathione S-transferase catalyzed reaction for metham, and the intermediate of either methyl isothiocyanate or metham for dazomet.|In a rat metabolism study, dazomet, metam sodium, and MITC were tested at two dose levels. All three were excreted mainly in urine with small amounts excreted in feces. Three different compounds (MITC, carbon dioxide [CO,], carbon oxide sulfide [COSIlcarbon disulfide [CS,]) were found to be excreted in the lungs over a 73 hour collection period. There were no differences between males and females in amounts excreted via the three excretion routes; however, tissue and plasma levels, and plasma area under the curves (AUCs) were consistently higher in females than in males.

SYMPTOMS: This compound is a LACHRYMATOR. Symptoms of exposure to this compound include irritation of the skin and eyes. It also causes sensitization of the skin. Irritation of the nose and mouth may occur. ACUTE/CHRONIC HAZARDS: This compound is a LACHRYMATOR. It is toxic by ingestion and inhalation. It is a severe eye irritant and mild primary skin irritant 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. (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)


Fresh air, rest.


Remove contaminated clothes. Rinse skin with plenty of water or shower.


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

/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/

/SIGNS AND SYMPTOMS/ Even dilute soln cause skin irritation and sensitization in humans.|/SIGNS AND SYMPTOMS/ Not readily absorbed through skin. May cause skin irritation. Inhalation of dusts or powders may result in nonspecific irritation of the upper respiratory tract.|/SIGNS AND SYMPTOMS/ Ingestion may produce symptoms of nonspecific irritation of the GI tract, nausea, vomiting, cramps and diarrhea. In severe cases, CNS depression may result.|/SIGNS AND SYMPTOMS/ ... human exposures to MITC are consistent with exposure to an irritant and include: eye effects--watery, burning, and itchy eyes, blurred vision; skin effects -rash, burns, redness, swelling; systemic effects-nausea, chest pain, scratchy throat, diarrhea, weakness, dizziness, headache, malaise, salivation, vomiting; and respiratory effects-cough, shortness of breath. With respect to respiratory impairment, arguably, eye irritation is less severe compared to other possible effects associated with inhalation exposure to MITC, particularly given the expected reversible nature of the eye irritation effects at lower concentrations. Nonetheless, eye (as well as nose and throat) irritation is uncomfortable and could potentially interfere with everyday tasks or activities. /MITC/|/CASE REPORTS/ A case of allergic contact dermatitis resulting from exposure to dazomet was described. The patient was an English paper mill worker with a 3 mo history of sore, itchy upper and lower eyelids accompanied by erythema and scaling. The reactions usually /resulted/ 4 hr after finishing work and lasted for at least 24 hr. The reactions first appeared after the paper mill changed biocides to Busan-79 and Busan-1058. Patch testing produced negative results for Busan-79, but a moderately strong positive reaction with Busan-1058. Busan-1058 was known to contain 24% dazomet as the active ingredient. Once the paper mill discontinued using dazomet as a biocide, the patient's dermatitis disappeared. ...

Basamide

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

Redness. Pain.

Dimethylformocarbothialdine Use and Manufacturing

Methods of Manufacturing

It uses methylamine, formaldehyde and carbon disulfide as raw materials to synthesize cotton wool.

Uses

Soil fungicide, nematocide, weed killer; slimicide in paper making.

Production

(1970) 5.53X10+8 GRAMS|(1975) 4.54X10+7 GRAMS (CONSUMPTION)|Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#3392]

31% USED AS AN HERBICIDE ON VARIOUS CROPS; AND 69% IS USED IN OTHER APPLICATIONS, PRIMARILY AS AN INDUSTRIAL SLIMICIDE (1971)

THE TECHNICAL GRADE IS GREATER THAN OR EQUAL TO 98% PURE. ...`BASAMID', GRANULAR (980-1000 G/KG).|Granule, dispersible powder, wettable powder|Granule, greater than or equal to 94% pure|Pelleted/tableted, liquid (soluble concentrate and flowable concentrate) solutions, water soluble packaged solids, ready to use solutions.

2H-1,3,5-Thiadiazine-2-thione, tetrahydro-3,5-dimethyl-: ACTIVE|The WHO Recommended Classification of Pesticides by Hazard identifies Dazomet (technical grade) as Class III: slightly hazardous; Main Use: herbicide.|Dazomet, by virtue of the release of methyl isothiocyanate, is a soil fumigant effective for control of nematodes, germinating weeds and soil fungi, such as: fusarium, pythium, rhizoctonia, and verticillium spp and colletotrichum atramentarium, when incorporated into glasshouse soils at 400-600 kg ai/ha. At these rates it is also effective against millipedes, soil insects and wireworms. It is strongly phytotoxic and treated soils should not be planted until shown to be free of the cmpd and its decomp prod, generally within 8-24 days (depending on soil temp) by the normal germination of cress seed sown on a sample of the treated soil. The granular formulation is also recommended for outdoor use at 200-400 kg/ha depending on soil type; soil temp should be at least 7 °C at a depth of 15 cm, the granules incorporated evenly to a depth of 20-22 cm and surface of the treated soil sealed with polythene, by flooding with water or by compaction with a heavy roller to compact the surface. Cultivation is needed to aid release of the methyl isothiocyanate and the cress test should be applied...|SOIL DISINFECTION WITH DAZOMET (50 G/SQ M) INCREASED PLANT GROWTH AND THE NUMBER OF CUT FLOWERS PRODUCED BY CARNATIONS (DIANTHUS CARYOPHYLLUS) IN GREENHOUSE EXPT.|There are several potential sources in the environment of MITC including metam sodium, metam potassium, and dazomet. In many situations, data have been used that provide results for MITC, but the sources cannot be determined (e.g., levels in ambient air). Following application of dazomet, MITC can volatilize into the atmosphere and be transported off-site. This can lead to exposures to MITC in the general public and to workers following application of dazomet.

Product analysis by HPLC. Residues determined by GLC of a derivative (J.R. Lane, Anal. Methods Pestic., Plant Growth Regul. Food Addit., 1967, 5, 499) or by alkaline hydrolysis to liberate 1,1-dimethylhydrazine which is determined colorimetrically (Anal. Methods Pestic. Plant Growth Regul., 1972, 6, 697; V.P. Lynch, ibid., 1976, 8, 491).|INFRARED ANALYSIS OF PESTICIDE FORMULATIONS IS DESCRIBED.|Hydrolyzed in dilute acid medium to carbon disulfide....absorbed in ethanolic cupric acetate, diethylamine and triethanolamine. The intensity of the color of the resulting diethyldithiocarbamate is measured photometrically at 385 nm.|Method: EPA 1659; Procedure: gas chromatography with a nitrogen-phosphorus detector; Analyte: dazomet; Matrix: municipal and industrial wastewater Detection Limit: 3 ug/L.

A GAS CHROMATOGRAPHIC METHOD UTILIZING DUAL ALKALINE FLAME IONIZATION/FLAME IONIZATION DETECTION SYSTEM WAS USED FOR PESTICIDES SCREENING IN BIOL MATERIAL SUBMITTED FOR FORENSIC EXAM IN CASES OF SUSPECTED POISONINGS.

Agrochemicals -> Fungicides, Herbicides, Nematicides, Soil Treatment|Insecticides, Fungicides, Herbicides|Environmental transformation -> Pesticides (parent, predecessor)

Dazomet has known environmental transformation products that include methyl isothiocyanate.|Dazomet has known environmental transformation products that include MITC, TDL-S, and TDL-SO.

Computed Properties

Molecular Weight:162.3
XLogP3:1.3
Hydrogen Bond Acceptor Count:3
Exact Mass:162.02854067
Monoisotopic Mass:162.02854067
Topological Polar Surface Area:63.9
Heavy Atom Count:9
Complexity:126
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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