Methidathion

Base Information

• Chemical Name: Methidathion
• CAS No.: 950-37-8
• Deprecated CAS: 80210-09-9
• Molecular Formula: C6H11N2O4PS3
• Molecular Weight: 302.336
• European Community (EC) Number: 213-449-4
• ICSC Number: 1659
• UN Number: 2811,2783
• UNII: Y2P145U7KK
• DSSTox Substance ID: DTXSID5020819
• Nikkaji Number: J1.752C
• Wikipedia: Methidathion
• Wikidata: Q411730
• NCI Thesaurus Code: C163672
• Metabolomics Workbench ID: 55034
• ChEMBL ID: CHEMBL226651
• Mol file: 950-37-8.mol

Synonyms:GS 13005;methidathion;metidathion;O,O-dimethyl S-(2-methoxy-1,3,4-thiadiazole-5)-(4H)-onyl-(4)-methylphosphorodithioate;S-(5-methoxy-2-oxo-1,3,4-thiadiazol-3-(2H)-yl) O,O-dimethylphosphorodithioate;S-2,3-dihydro-5-methoxy-2-oxo-1,3,4-thiadiazol-3-ylmethyl O,O-dimethyl phosphorodithioate;Supracide

Chemical Property of Methidathion

Chemical Property:

• Appearance/Colour: Colourless crystals
• Vapor Pressure: 5.28E-05mmHg at 25°C
• Melting Point: 39-40 °C
• Refractive Index: 1.651
• Boiling Point: 347.7 °C at 760 mmHg
• PKA: -4.17±0.40(Predicted)
• Flash Point: 164.1 °C
• PSA: 158.02000
• Density: 1.6 g/cm³
• LogP: 2.17200
• Storage Temp.: 0-6°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: 0.024 g/100 mL
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 6
• Exact Mass: 301.96185735
• Heavy Atom Count: 16
• Complexity: 343
• Transport DOT Label: Poison

Purity/Quality:

97% ^*data from raw suppliers

Methidathion ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+,N
• Hazard Codes: T+;N,N,T+
• Statements: 21-28-50/53-41-26-24
• Safety Statements: 22-28-36/37-45-60-61-39-26

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Pesticides -> Organophosphate Insecticides
• Canonical SMILES: COC1=NN(C(=O)S1)CSP(=S)(OC)OC
• Inhalation Risk: A harmful concentration of airborne particles can be reached quickly when dispersed.
• Effects of Short Term Exposure: Cholinesterase inhibition. The substance may cause effects on the nervous system. This may result in convulsions and respiratory depression. Exposure could cause death. The effects may be delayed. Medical observation is indicated.
• Effects of Long Term Exposure: Cholinesterase inhibition. Cumulative effects are possible. See Acute Hazards/Symptoms.
• Description: Methidation is used as an insecticide. Cross-sensitivity was described to dichlorvos. Methidathion is an organophosphate insecticide that inhibits insect cholinesterase. It reduces cattle lice (L. vituli, D. bovis, and H. eurysternus) infestation by 99.1% when administered topically at a dose of 3.5 mg/kg. Methidathion is selectively toxic to lice over cattle, only inhibiting cattle plasma acetylcholinesterase activity by 20% with no effect on survival when administered topically at a dose of 24 mg/kg. It increases sister chromatid exchange (SCE) in a concentration-dependent manner and induces cell cycle arrest at the M1 phase in V79 cells when used at a concentration of 40 μg/ml. Dietary administration of methidathion (1.4-4.7 mg/kg) increases alanine aminotransferase, aspartate aminotransferase, sorbitol dehydrogenase, and alkaline phosphatase activity, inhibits cholinesterase, and induces chronic liver inflammation in male beagle dogs. It also induces loss of striation and myocytolysis of cardiomyocytes and reduces serum cholinesterase activity in rats when administered orally at a dose of 5 mg/kg.
• Uses: Methidathion is an organophosphate insecticide and was examined for human health and toxicological concerns. Methidathion is used to control a wide range of insects in many different crops.

Technology Process of Methidathion

There total 3 articles about Methidathion which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 5-methoxy-3H-[1,3,4]thiadiazol-2-one (17605-27-5) + potassium O,O-dimethyldithiophosphate (16001-68-6) → methidathion (950-37-8)

Guidance literature:

With sulfuric acid;

DOI:10.1002/hlca.19680510314

Reference yield:

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 5-methoxy-3H-[1,3,4]thiadiazol-2-one (17605-27-5) + O,O-dimethyl phosphorodithioic acid (756-80-9) → methidathion (950-37-8)

Guidance literature:

Multistep reaction; (i) aq. H₂SO₄, (ii) /BRN= 1209228/;

DOI:10.1002/hlca.19740570619

Reference yield:

→ methidathion (950-37-8)

Guidance literature:

3-Hydroxymethylthiadiazol, Dithiophosphorsaeure O,O-dimethylester-K-Salz;

upstream raw materials:

formaldehyd

5-methoxy-3H-[1,3,4]thiadiazol-2-one

potassium O,O-dimethyldithiophosphate

O,O-dimethyl phosphorodithioic acid

Downstream raw materials:

thiophosphoric acid S-(5-methoxy-2-oxo-[1,3,4]thiadiazol-3-ylmethyl) ester O,O'-dimethyl ester

Refernces

• 1、 -. "Nitro- and cyanoguanidines as selective preemergence herbicides and plant defoliants". . . Retrieved 2008/06/13.