533-74-4

Basic information

• Product Name: Dazomet
• Synonyms: 3,5-Dimethyl tetrahydro-2-H,1,3,5-thiadiazone-2-thione;3,5-Dimethyl-1,3,5-2H-tetrahydrothiadiazine-2-thione;3,5-Dimethyl-1,3,5-thiadiazinane-2-thione;3,5-Dimethyl-2-thionotetrahydro-1,3,5-thiadiazine;3,5-Dimethylperhydro-1,3,5-thiadiazin-2-thion;3,5-dimethylperhydro-1,3,5-thiadiazin-2-thion[czech,german];3,5-Dimethyl-tetrahydro-1,3,5-2H-thiadiazine-2-thione;3,5-Dimethyltetrahydro-1,3,5-2H-thiadiazine-2-thione
• CAS NO: 533-74-4
• Molecular Formula: C₅H₁₀N₂S₂
• Molecular Weight: 162.28
• EINECS: 208-576-7
• Product Categories: INSECTICIDE
• Mol File: 533-74-4.mol

Chemical Properties

• Melting Point: 104-105°C
• Boiling Point: 222.3 °C at 760 mmHg
• Flash Point: 156 °C
• Appearance: White crystals or off-white powder
• Density: 1.3
• Vapor Pressure: 0.102mmHg at 25°C
• Refractive Index: 1.5005 (estimate)
• Storage Temp.: 0-6°C
• PKA: 4.04±0.20(Predicted)
• Water Solubility: <0.1 g/100 mL at 18℃
• Merck: 13,2854
• BRN: 116039
• CAS DataBase Reference: Dazomet(CAS DataBase Reference)
• NIST Chemistry Reference: Dazomet(533-74-4)
• EPA Substance Registry System: Dazomet(533-74-4)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-36-50/53
• Safety Statements: 15-22-24-60-61
• RIDADR: UN3077 9/PG 3
• WGK Germany: 3
• RTECS: XI2800000
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 533-74-4(Hazardous Substances Data)

Usage

Uses

Used in Agriculture:
Dazomet is used as a soil fungicide, nematocide, and herbicide for the control of soil fungi, nematodes, bacteria, and germinating weeds. It is also used as a soil sterilant and insecticide, as well as a fumigant for poultry litter and eggs to control Salmonella. Dazomet is a non-ozone-depleting alternative to methyl bromide and is used prior to sowing or planting.
Used in Pulp and Paper Industry:
Dazomet is used as a slimicide in the pulp and paper industry to control bacterial and fungal growth. It is also used as a preservative for adhesives.
Used in Preventing Pest Incursion:
Dazomet is used as a fumigant to control brown root rot disease and as a possible agent in preventing pest incursion in agriculture, gardening, and agroforestry.
Dazomet is contained in products such as Busan 1058, Mylone, and Fungicide 974 (Crag). Sensitization to Dazomet has been rarely reported, with one case occurring in a paper-mill worker.

Air & Water Reactions

Insoluble in water. Slowly hydrolyzed.

Reactivity Profile

Dazomet decomposes in water, dilute acids and alcohol.

Fire Hazard

Flash point data for Dazomet are not available; however, Dazomet is probably combustible.

Contact allergens

Dazomet is a biocide used to control bacterial and fungal growth in a pulp and paper system, and also in agriculture for soil disinfection. It is contained in Busan 1058, Mylone, and Fungicide 974 (Crag?). Sensitization, rarely reported, occurred in a paper mill worker.

Safety Profile

Poison bj 7 in ' g estion and intraperitoneal routes. Moderately toxic by skin contact and subcutaneous routes. A severe eye irritant. A mild primary skin irritant and sensitizer. When heated to decomposition it emits very toxic fumes of NOx and SOx

Environmental Fate

Soil. Soil metabolites include formaldehyde, hydrogen sulfide, methylamine and methyl(methylaminomethyl)dithiocarbamic acid (Hartley and Kidd, 1987) which further decomposes to methyl isothiocyanate (Harley and Kidd, 1987; Ashton and Monaco, 1991; Cremlyn, 1991). The rate of decomposition is dependent upon the soil type, temperature and humidity (Cremlyn, 1991).Chemical/Physical. Hydrolyzes in acidic solutions forming carbon disulfide, methylamine and formaldehyde (Hartley and Kidd, 1987; Humburg et al., 1989). These compounds are probably formed following the decomposition of dazomet with alcohol and

Metabolic pathway

Dazomet is a propesticide that decomposes to generate the highly volatile methyl isothiocyanate. The pathways of metabolism of methyl isothiocyanate are described under its own entry. In soil, dazomet degrades mainly via a dithiocarbamic acid which in turn affords methyl isothiocyanate, formaldehyde, hydrogen sulfide and methy lamine.

Shipping

UN3077 Environmentally hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required.

Degradation

Dazomet is rapidly hydrolysed in acidic media to carbon disulfide, formaldehyde and methylamine (PM). DT50 values for hydrolysis were 85, 490 and 110 hours at pH 5,7 and 9, respectively. It is sensitive to oxygen and to light.

InChI:InChI=1/C5H10N2S2/c1-6-3-7(2)5(8)9-4-6/h3-4H2,1-2H3

Synthetic route

N-methyl-N-chloromethylcarbamoyl chloride (50778-91-1) + N-methylcarbamodithioic acid ammonium salt (39680-90-5) → dazomet (533-74-4) + 3,5-Dimethyl-2-thioxo-[1,3,5]thiadiazinan-4-one (78460-59-0)

Conditions	Yield
With triethylamine In acetone 1.)ice-water cooling, 1h 2.)r.t., 2 h;	A 7% B 41%

formaldehyd (50-00-0) + methyl-dithiocarbamic acid; methylamine salt (21160-95-2) → dazomet (533-74-4)

carbon disulfide (75-15-0) + formaldehyd (50-00-0) + methylamine (74-89-5) → dazomet (533-74-4)

Conditions	Yield
(i) EtOH, (ii) /BRN= 1209228/, H2O; Multistep reaction;

1.3.5-trimethyl-trimethylenetriamine → dazomet (533-74-4)

dazomet (533-74-4) + chromium(0) hexacarbonyl (199620-14-9, 13007-92-6) → [Cr(CO)5(3,5-dimethyl-tetrahydro-2H-1,3,5-thiadiazine-2-thione)] (620157-89-3)

Conditions	Yield
In tetrahydrofuran Irradiation (UV/VIS); under dry n2, Schlenk setup, 1:1 mixt. in THF, irradiated for 2 h, evapd. to dryness, dissolved (CH2Cl2); pptd. (ether), washed (ether), dried (vac.), elem. anal.;	79%

dazomet (533-74-4) + cymantrene (12079-65-1) → [Mn(CO)2(C5H5)(3,5-dimethyl-tetrahydro-2H-1,3,5-thiadiazine-2-thione)] (620157-93-9)

Conditions	Yield
In tetrahydrofuran Irradiation (UV/VIS); under dry n2, Schlenk setup, 1:1 mixt. in THF, irradiated for 2 h, evapd. to dryness, dissolved (CH2Cl2); pptd. (ether), washed (ether), dried (vac.), elem. anal.;

dazomet (533-74-4) + molybdenum hexacarbonyl (13939-06-5, 199620-15-0) → [Mo(CO)5(3,5-dimethyl-tetrahydro-2H-1,3,5-thiadiazine-2-thione)] (620157-90-6)

Conditions	Yield
In tetrahydrofuran Irradiation (UV/VIS); under dry n2, Schlenk setup, 1:1 mixt. in THF, irradiated for 2 h, evapd. to dryness, dissolved (CH2Cl2); pptd. (ether), washed (ether), dried (vac.), elem. anal.;

dazomet (533-74-4) + rhenium(I) pentacarbonyl bromide (14220-21-4) → [Re(CO)4Br(3,5-dimethyl-tetrahydro-2H-1,3,5-thiadiazine-2-thione)] (620157-92-8)

Conditions	Yield
In tetrahydrofuran Irradiation (UV/VIS); under dry n2, Schlenk setup, 1:1 mixt. in THF, irradiated for 2 h, evapd. to dryness, dissolved (CH2Cl2); pptd. (ether), washed (ether), dried (vac.), elem. anal.;

dazomet (533-74-4) + tungsten hexacarbonyl (14040-11-0) → [W(CO)5(3,5-dimethyl-tetrahydro-2H-1,3,5-thiadiazine-2-thione)] (620157-91-7)

Conditions	Yield
In tetrahydrofuran Irradiation (UV/VIS); under dry n2, Schlenk setup, 1:1 mixt. in THF, irradiated for 2 h, evapd. to dryness, dissolved (CH2Cl2); pptd. (ether), washed (ether), dried (vac.), elem. anal.;

Upstream product

• 75-15-0 carbon disulfide 
• 50-00-0 formaldehyd 
• 74-89-5 methylamine 
• 50778-91-1 N-methyl-N-chloromethylcarbamoyl chloride 
• 39680-90-5 N-methylcarbamodithioic acid ammonium salt 
• 21160-95-2 methyl-dithiocarbamic acid; methylamine salt 

Relevant articles and documents

FUNGICIDAL PENFLUFEN MIXTURES

The invention relates to mixtures comprising penflufen, to the use of these mixtures for protecting industrial materials and to a method for treating industrial materials with the penflufen mixtures.

Method for the production of a particle-containing preparation of tetrahydro-3,5-dimethyl-1,3,5-thiadiazin-2-thione

Described is a process for the preparation of a particulate tetrahydro-3,5-dimethyl-1,3,5-thiadiazine-2-thione product by combining a first aqueous solution comprising methylammonium N-methyldithiocarbamate with a second aqueous solution comprising formaldehyde, followed by separation and drying of the resulting solid, which comprises combining the first and the second aqueous solutions in such a way that the ratio between the concentrations of dithiocarbamate functions and of formaldehyde is essentially constant in the reaction mixture over time during the duration of the reaction.

Bromonitrothienyldioxanes

The invention relates to novel 5-bromo-5-nitro-2-thienyl-1,3-dioxanes of the formula (I) in which R1, R2 and R3 are as defined in the description are highly suitable for use as biocides for protecting plants and industrial materials.

3-NITROISOXAZOLES AND THEIR USE IN THE PROTECTION OF MATERIALS

The 3-nitroisoxazoles of the formula (I) in which R1 and R2 are each as defined in the description, some of which are known, are highly suitable for use as biocides for protecting industrial materials.

Thiazines and thiazoles as agents for protecting materials

The novel and known thiazines and thiazoles of the formula (I) in which R1, R2 and n are as defined in the description, are highly suitable for use as biocides for protecting industrial materials.

O-aryl dithiazole dioxides

The invention relates to new O-aryldithiazole dioxides, to two processes for their preparation, and to their use as pesticides in crop protection and in the protection of materials.

Arylthio-dithiazindioxides and their use as pesticides

PCT No. PCT/EP97/07242 Sec. 371 Date Jun. 23, 1999 Sec. 102(e) Date Jun. 23, 1999 PCT Filed Dec. 22, 1997 PCT Pub. No. WO98/29400 PCT Pub. Date Jul. 9, 1998The invention relates to novel S-aryl-dithiazine dioxides, to processes for their preparation and to the use in crop protection and in the protection of materials.

4-Nitro-2-trichloromethylphenylsulfenamides

New 4-nitro-2-trichloromethylphenylsulfenamides having a fungicidal and bactericidal action, processes for their manufacture, fungicides containing these compounds as active ingredients, and a process for combating fungi with these compounds.

Thiolphosphoric acid-S-4-nitro-2-trichloromethylphenyl esters as fungicides

New thiolphosphoric acid-S-4-nitro-2-trichloromethylphenyl esters of the formula STR1 where X denotes oxygen or sulfur, and R1 and R2 are identical or different and each denotes a substituted or unsubstituted aliphatic radical of 1 to 18 carbon atoms or a substituted or unsubstituted alicyclic radical of 5 to 18 carbon atoms, processes for their manufacture, fungicides containing these compounds as active ingredients, their manufacture, and processes for combating fungi with these novel compounds.

Tetrahydro-2-thioxo-2H-1,3,5-thiadiazin-4-ones and their Derivatives Representing a Novel Heterocyclic Ring System

The cyclization reaction between N-substituted dithiocarbamates (1) and N-substituted N-chloromethylcarbamoyl chlorides (2) gives 3,5-disubstituted tetrahydro-2-thioxo-2H-1,3,5-thiadiazin-4-ones (3).In order to decide among the theoretically possible structures 3-5, the compounds 6a,b, containing a thioxo group instead of an oxo group as in 3a,b, as well as the S-oxide derivative of 3a was also established by X-ray structure determination.