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Dazomet
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Name

Dazomet

 EINECS 208-576-7
CAS No. 533-74-4 Density 1.29 g/cm3
PSA 63.87000 LogP 0.67250
Solubility <0.1 g/100 mL at 18 °C in water Melting Point 104-105°C
Formula C5H10N2S2 Boiling Point 222.3 °C at 760 mmHg
Molecular Weight 162.28 Flash Point 88.2 °C
Transport Information UN3077 9/PG 3 Appearance White crystals or off-white powder
Safety 15-22-24-60-61 Risk Codes 22-36-50/53
Molecular Structure Molecular Structure of 533-74-4 (Dazomet) Hazard Symbols HarmfulXn, DangerousN
Synonyms

2-Thio-3,5-dimethyltetrahydro-1,3,5-thiadiazine;3,5-Dimethyl-2-thionotetrahydro-1,3,5-thiadiazine;3,5-Dimethyltetrahydro-1,3,5-thiadiazine-2-thione;Basamid P;Basamid-Puder;Busan 1058;Crag 974;D 35;DMTT;Dimethylformocarbothialdine;Fennosan B 100;Metasol D 3TA;Mylone;Mylone 85;N 521;Nalcon 243;Nefusan;Stauffer N 521;Tetrahydro-3,5-dimethyl-2H-1,3,5-thiodiazin-2-thione;Thiazon;Thiazone;UCC974;

Article Data 19

Dazomet Synthetic route

50778-91-1

N-methyl-N-chloromethylcarbamoyl chloride

39680-90-5

N-methylcarbamodithioic acid ammonium salt

A

533-74-4

dazomet

B

78460-59-0

3,5-Dimethyl-2-thioxo-[1,3,5]thiadiazinan-4-one

Conditions
ConditionsYield
With triethylamine In acetone 1.)ice-water cooling, 1h 2.)r.t., 2 h;A 7%
B 41%
50-00-0

formaldehyd

21160-95-2

methyl-dithiocarbamic acid; methylamine salt

533-74-4

dazomet

75-15-0

carbon disulfide

50-00-0

formaldehyd

74-89-5

methylamine

533-74-4

dazomet

Conditions
ConditionsYield
(i) EtOH, (ii) /BRN= 1209228/, H2O; Multistep reaction;
1.3.5-trimethyl-trimethylenetriamine

1.3.5-trimethyl-trimethylenetriamine

533-74-4

dazomet

533-74-4

dazomet

199620-14-9, 13007-92-6

chromium(0) hexacarbonyl

620157-89-3

[Cr(CO)5(3,5-dimethyl-tetrahydro-2H-1,3,5-thiadiazine-2-thione)]

Conditions
ConditionsYield
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%
533-74-4

dazomet

12079-65-1

cymantrene

620157-93-9

[Mn(CO)2(C5H5)(3,5-dimethyl-tetrahydro-2H-1,3,5-thiadiazine-2-thione)]

Conditions
ConditionsYield
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.;
533-74-4

dazomet

13939-06-5, 199620-15-0

molybdenum hexacarbonyl

620157-90-6

[Mo(CO)5(3,5-dimethyl-tetrahydro-2H-1,3,5-thiadiazine-2-thione)]

Conditions
ConditionsYield
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.;
533-74-4

dazomet

14220-21-4

rhenium(I) pentacarbonyl bromide

620157-92-8

[Re(CO)4Br(3,5-dimethyl-tetrahydro-2H-1,3,5-thiadiazine-2-thione)]

Conditions
ConditionsYield
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.;
533-74-4

dazomet

14040-11-0

tungsten hexacarbonyl

620157-91-7

[W(CO)5(3,5-dimethyl-tetrahydro-2H-1,3,5-thiadiazine-2-thione)]

Conditions
ConditionsYield
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 Chemical Properties

IUPAC Name: 3,5-dimethyl-1,3,5-thiadiazinane-2-thione
The MF of DIMETHYLFORMOCARBOTHIALDINE(533-74-4): C5H10N2S2
The MW of DIMETHYLFORMOCARBOTHIALDINE(533-74-4): 162.28
EINECS: 208-576-7
mp: 104-105 °C
density: 1.3
Fp: 156 °C
storage temp.: 0-6 °C
Water Solubility: <0.1 g/100 mL at 18 °C
Categories: INSECTICIDE
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
The Structure of DIMETHYLFORMOCARBOTHIALDINE(533-74-4):

Dazomet Toxicity Data With Reference

1.   

eye-rbt 500 mg/24H SEV

   28ZPAK    Sbornik Vysledku Toxixologickeho Vysetreni Latek A Pripravku Marhold, J.V.,Institut Pro Vychovu Vedoucicn Pracovniku Chemickeho Prumyclu Praha,Czechoslovakia.: 1972,204.
2.   

orl-rat LD50:320 mg/kg

   TXAPA9    Toxicology and Applied Pharmacology. 9 (1966),521.
3.   

ihl-rat LC50:8400 mg/m3/4H

   PEMNDP    Pesticide Manual. 9 (1991),225.
4.   

skn-rat LD50:2260 mg/kg

   NNGADV    Nippon Noyaku Gakkaishi. 17 ,1992,S327.
5.   

ipr-rat LD50:87 mg/kg

   TXAPA9    Toxicology and Applied Pharmacology. 9 (1966),521.
6.   

orl-mus LD50:180 mg/kg

   TXAPA9    Toxicology and Applied Pharmacology. 9 (1966),521.
7.   

skn-mus LD50:2400 mg/kg

   NNGADV    Nippon Noyaku Gakkaishi. 17 ,1992,S327.
8.   

ipr-mus LDLo:50 mg/kg

   ARZNAD    Arzneimittel-Forschung. Drug Research. 21 (1971),121.
9.   

scu-mus LDLo:500 mg/kg

   AIPTAK    Archives Internationales de Pharmacodynamie et de Therapie. 12 (1904),447.
10.   

ipr-dog LD50:47 mg/kg

   TXAPA9    Toxicology and Applied Pharmacology. 9 (1966),52

Dazomet Consensus Reports

Reported in EPA TSCA Inventory.

Dazomet Safety Profile

Poison by ingestion 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.
Hazard Codes: Xn,N
Risk Statements: 22-36-50/53
22:  Harmful if swallowed 
36:  Irritating to the eyes 
50/53:  Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment  
Safety Statements: 15-22-24-60-61
15:  Keep away from heat 
22:  Do not breathe dust 
24:  Avoid contact with skin 
60:  This material and/or its container must be disposed of as hazardous waste 
61:  Avoid release to the environment. Refer to special instructions safety data sheet 
RIDADR: UN3077 9/PG 3
RTECS: XI2800000
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