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Methidathion

Methidathion structure

Methidathion 

structure
  • CAS No:

    950-37-8

  • Formula:

    C6H11N2O4PS3

  • Chemical Name:

    Methidathion

  • Synonyms:

    Phosphorodithioic acid,S-[(5-methoxy-2-oxo-1,3,4-thiadiazol-3(2H)-yl)methyl] O,O-dimethyl ester;Phosphorodithioic acid,O,O-dimethyl ester,S-ester with 4-(mercaptomethyl)-2-methoxy-Δ2-1,3,4-thiadiazolin-5-one;Geigy 13005;GS 13005;O,O-Dimethyl-S-(2-methoxy-Δ2-1,3,4-thiadiazolin-5-on-4-ylmethyl)dithiophosphate;O,O-Dimethyl-S-(2-methoxy-1,3,4-thiadiazol-5(4H)-onyl-4-methyl) dithiophosphate;O,O-Dimethylphosphorodithioate S-ester with 4-(mercaptomethyl)-2-methoxy-Δ2-1,3,4-thiadiazolin-5-one;Methidathion;Supracide;O,O-Dimethyl S-[2-methoxy-1,3,4-thiadiazol-5(4H)-on-4-ylmethyl] phosphorodithioate;O,O-Dimethyl-S-2-methyloxy-1,3,4-thiodiazol-5-(4H)-onyl-(4)-methyldithiophosphate;Ultracid;S-((2-Methoxy-5-oxo-Δ2-1,3,4-thiadiazolin-4-yl)methyl) O,O-dimethylphosphorodithioate;O,O-Dimethyl phosphorodithioate S-ester with 4-(mercaptomethyl)-2-methoxy-1,3,4-thiadizaolin-5-one;O,O-Dimethyl S-(5-methoxy-1,3,4-thiadiazole-2 (3H)-on-3-ylmethyl) dithiophosphate;O,O-Dimethyl-S-(5-methoxy-1,3,4-thiadiazol-2(3H)-on-3-ylmethyl)dithiophosphate;Geigy GS 13005;O,O-Dimethyl-S-[2-methoxy-1,3,4-thiadiazol-5(4H)-onylmethyl] dithiophosphate;Phosphorodithioic acid O,O′-dimethyl ester S-ester with 4-(mercaptomethyl)-2-methoxy-Δ2-1,3,4-thiadiazolin-5-one;Dithiophosphoric acid O,O′-dimethyl-S-[(2-methoxy-1,3,4-thiadiazol-5(4H)-on-4-yl)methyl] ester;11114-31-1;80210-09-9;160219-68-1

  • Categories:

    Agrochemicals  >  Insecticides

Description

Crystalline solid. Almost insoluble in water; soluble in common organic solvents. Methidathion is a colorless crystalline pesticide at room temperature. It is sparingly soluble in water, but very soluble in octanol, ethanol, xylene, acetone, and cyclohexane. Methidathion is a non-systemic organophosphorous insecticide and acaricide with stomach and contact action. It is used to control a variety of insects and mites on crops and fruit plants. Methidathion is highly toxic to animals and humans.

Methidathion Basic Attributes

302.33

302.33

213-449-4

Characteristics

143

2.2

Methidathion appears as colorless crystals. This material is used as a non-systemic insecticide. (EPA, 1998)

1.51 g/cm3 @ Temp: 20 °C

39-40 °C

347.7±52.0 °C at 760 mmHg

100 °C

1.652

Solubility in water, g/100ml at 20°C: 0.0187

0-6°C

Vapour pressure at 20°C: negligible

LD50 in adult male, female rats (mg/kg): 31, 32 orally (Gaines, Linder)

Organophosphate odor

Safety Information

II

6.1(a)

UN 2811

3

21-28-50/53-41-26-24

22-28-36/37-45-60-61-39-26

TE2100000

T+;N,N,T+

Provision to contain effluent from fire extinguishing. Separated from food and feedstuffs. Well closed. Store in an area without drain or sewer access.

Supracide 2E: Shelf-life of at least 3 to 5 yr when stored in a dry place and minimum storage temp (above 32 deg F) are observed.

P260-P264-P273-P280-P284-P301 + P310

H300 + H310 + H330-H318-H410

Methidathion Use and Manufacturing

Methods of Manufacturing

Preparation of carbonyl hydrazine Add sodium hydroxide, water and methanol to the reaction pot and stir for 2h. Cool down to 23~25℃, add dithiocarbon dropwise, keep it warm for 2h, heat up to (30±2)℃, add hydrazine hydrate and keep warm for 1.5 h. Cool to 0°C and centrifuge to obtain off-white carbonyl hydrazine crystals. Preparation of thiadiazolone Add water and carbonyl hydrazine to the reaction pot, add sulfuric acid to control the temperature 55~60℃, add trichloromethyl chloroformate dropwise, about 2h drop, keep at (60±2)℃ for 2h, cool After centrifugation at 15°C and washing with cold water, pale yellow thiadiazolone crystals were obtained. In the synthesis of phoxim, 75% sulfuric acid, thiadiazolone, solvent A, and catalyst are added to the reaction pot, and the methylthio compound is added at a temperature of 25°C. The temperature is reduced to 20°C, and formaldehyde is added dropwise. The temperature is controlled at 20-25°C. Warm to 40°C for 2h, stand still to separate the waste acid layer, wash with water twice, remove 1/2 solvent A and water below 70°C, cool to 0°C to crystallize, centrifuge to obtain white antifoam The content is 96%~98%, and the mother liquor set is returned to the synthesis of phoxim. The content is 96%~98%, the yield is 42%. In the synthesis of triflumuron, 3-chloromethyl-5-methoxy-2 can also be prepared by reacting 5-methoxy-2-oxo-1, 3, 4-thiodiazepine with formaldehyde and thionyl chloride -Oxo-1, 3, 5-thiodiazepine, and it is prepared by reacting it with O, O-dimethyldithiophosphoric acid. It is reported in the literature that Ciba-Jiaji Company and Israel Yam Company used phosgene method to synthesize thiadiazolone, and the purity of phoxim was 96%~97%.

Uses

Insecticide, acaricide.

Computed Properties

Molecular Weight:302.3
XLogP3:2.4
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:6
Exact Mass:301.96185735
Monoisotopic Mass:301.96185735
Topological Polar Surface Area:143
Heavy Atom Count:16
Complexity:343
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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