Methidathion
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Methidathion
structure -
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CAS No:
950-37-8
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Formula:
C6H11N2O4PS3
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Chemical Name:
Methidathion
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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
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CAS No:
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.
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
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%.
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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