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
• Article Data: 14

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

Description

Dazomet is a biocide used to control bacterial and fungal growth in pulp and paper systems, but 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.

Uses

Different sources of media describe the Uses of 533-74-4 differently. You can refer to the following data:
1. Soil fungicide; nematocide; herbicide; insecticide; soil sterilant.
2. Dazomet is a multi-purpose soil fumigant used for the control of nematodes, soil fun@, soil insects and weed seeds. It is also used as a slimicide in pulp and paper manufacture and as a preservative of adhesives.
3. Dazomet is a as fumigant used for the control of brown root rot disease. Dazomet was shown to be a possible agent in preventing pest incursion in agriculture, gardening and agroforestry.
4. Soil fungicide, nematocide, weed killer; slimicide in paper making.

Definition

ChEBI: 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 ontrol 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.

General Description

White crystals or off-white powder. Pungent, acrid odor.

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

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

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.

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.

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.