1113-02-6

Basic information

• Product Name: O,O-Dimethyl S-methylcarbamoylmethyl phosphorothioate
• Synonyms: 2-dimethoxyphosphinoylthio-n-methylacetamide;Acetamide, 2-mercapto-N-methyl-, S-ester with O,O-dimethyl phosphorothioate;acetamide,2-mercapto-n-methyl-,s-esterwitho,o-dimethylphosphorothioate;BAYER 45,432;Bayer 45432;bayer45,432;bayers-6876;Dimethoate Oxygen analog
• CAS NO: 1113-02-6
• Molecular Formula: C₅H₁₂NO₄PS
• Molecular Weight: 213.19
• EINECS: 214-197-8
• Product Categories: Agro-Chemicals;INSECTICIDE;AcaricidesMethod Specific;Alpha sort;Baby Food Directives 13/2003 EC&14/2003 ECPesticides&Metabolites;European Community: ISO and DIN;N-PAnalytical Standards;AcaricidesAnalytical Standards;Alphabetic;Insecticides;OPesticides;Organophorous;Pesticides;Pesticides&Metabolites;Agro-Products;Phosphorylating and Phosphitylating Agents;Sulfur & Selenium Compounds
• Mol File: 1113-02-6.mol
• Article Data: 6

Chemical Properties

• Melting Point: -27.9°C
• Boiling Point: 135°C
• Flash Point: 100 °C
• Appearance: /liquid
• Density: 1.3200
• Vapor Pressure: 3.3×10-3Pa (20 °C)
• Refractive Index: 1.474
• Storage Temp.: 0-6°C
• PKA: 14.40±0.46(Predicted)
• Water Solubility: Miscible
• BRN: 1785256
• CAS DataBase Reference: O,O-Dimethyl S-methylcarbamoylmethyl phosphorothioate(CAS DataBase Reference)
• NIST Chemistry Reference: O,O-Dimethyl S-methylcarbamoylmethyl phosphorothioate(1113-02-6)
• EPA Substance Registry System: O,O-Dimethyl S-methylcarbamoylmethyl phosphorothioate(1113-02-6)

Safety Data

• Hazard Codes: T+;N,N,T+,T
• Statements: 21-25-50
• Safety Statements: 1/2-23-36/37-45-61
• RIDADR: 3018
• WGK Germany: 3
• RTECS: TF8050000
• HazardClass: 6.1(a)
• PackingGroup: II
• Hazardous Substances Data: 1113-02-6(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 1113-02-6 differently. You can refer to the following data:
1. Insecticidal, acaricidal, and fungicidal combinations of carboxamides and other pesticides.
2. Omethoate is a systemic insecticide used for the control of (mostly) sucking insects and mites in a wide variety of crops.

Contact allergens

Contact dermatitis from omethoate-dimethoxon is rare.

Metabolic pathway

Omethoate is the P=O analogue (oxon) of dimethoate. Dimethoate is metabolised via oxidative desulfuration to omethoate which is the active anti-acetylcholinesterase metabolite. This biotransformation occurs in all media: hence the metabolic pathways of both compounds have much in common. However, degradative pathways acting directly on dimethoate such as O-demethylation, N-demethylation and hydrolysis of the amide function mean that the balance between activation and degradative metabolism will influence their respective selective toxicities. In mammals there are two main routes of degradation: (i) glutathione transferase mediated O-demethylation (ii) hydrolysis to N-methylthioglycolamide which is S-methylated by S-adenosylmethionine and subsequently thiooxidised. In soil and plants the N-methylthioglycolamide moiety formed from the hydrolysis of omethoate undergoes a complex series of C1, C2 and C3 biotransformations ultimately leading to oxalate and citrate respectively and total degradation to C02. The information reported below is derived largely from an evaluation prepared by the UK MAFF Pesticide Safety Directorate (PSD, 1993).

Metabolism

Orally administered omethoate to rats is rapidly metabolized and excreted in the urine; the main metabolites are O-demethylomethoate and N-methyl-2- methylsulfinylacetamide. O-Demethylation and hydrolysis of the P?S bond are main degradation routes both in mammals and plants. Omethoate is rapidly degraded in soils with DT50 of a few days.

Toxicity evaluation

The acute oral LD50 for rats is about 25 mg/kg. Inhalation LC50 (4 h) for rats is 0.3 mg/L air. ADI is 0.3 μg/kg b.w.

Degradation

Omethoate was slowly hydrolysed in acidic media but more rapidly under alkaline conditions. The half-lives for hydrolysis at pH 4,7, and 9 were 102 days, 17 days and 28 hours, respectively (PM). Omethoate does not absorb light at wavelengths above 250 nm and it is thus unlikely to be subject to photodecomposition. An aqueous solution of omethoate was irradiated for 14 hours with a high pressure filtered mercury vapour lamp without detectable photolysis occurring (PSD, 1993).

InChI:InChI=1/C5H12NO4PS/c1-6-5(7)4-12-11(8,9-2)10-3/h4H2,1-3H3,(H,6,7)

Upstream product

• 96-30-0 chloroacetylmethylamide 
• 23754-87-2 Natriumsalz des Thiophosphorsaeure-O,O-dimethylesters 
• 57212-78-9 O,O-Dimethyl-S-(methoxycarbonylmethyl)-thiophosphorsaeure 
• 74-89-5 methylamine 
• 60-51-5 Dimethoate 
• 20938-74-3 mercapto-acetic acid methylamide 
• 868-85-9 Dimethyl phosphite 

Downstream Products

• 512-56-1 trimethyl phosphite 
• 152-20-5 O,O,S-trimethyl phosphorothioate 
• 20938-74-3 mercapto-acetic acid methylamide 
• 868-85-9 Dimethyl phosphite 

Relevant articles and documents

Rapid TiO2/SBA-15 synthesis from ilmenite and use in photocatalytic degradation of dimethoate under simulated solar light

SBA-15 mesoporous materials loaded with 8%–42% TiO2 were prepared by post-synthesis hydrolysis using ilmenite as the TiO2 source. X-ray diffraction, high-resolution transmission electron microscopy, nitrogen adsorption–desorption measurements, and Fourier-transform infrared, X-ray photoelectron, Raman, and ultraviolet-visible spectroscopies were used to investigate the TiO2/SBA-15 morphology and crystal structure. The results show that TiO2 was successfully loaded on the mesoporous SBA-15 and the highly ordered two-dimensional hexagonal structure was stable. The photocatalytic performances of the samples in dimethoate degradation under simulated solar light were investigated. The photocatalytic activity initially increased and then decreased with increasing TiO2 loading. The 26% TiO2/SBA-15 sample showed the highest photocatalytic activity and completely degraded dimethoate within 7 h. The catalytic activity of TiO2/SBA-15 was 62% higher than that of pure TiO2. This may be because of a synergistic effect resulting from the adsorption of dimethoate on the mesoporous material. The presence of Ti–O–Si species enhances the TiO2 surface acidity and formation of surface adsorption sites; The adsorption and electron delocalization properties of SBA-15 are the main reasons for the observed enhancement of the pesticide degradation rate. These improves the TiO2/SBA-15 photocatalytic activity. TiO2/SBA-15 maintained high photocatalytic activity and good stability during four cycles, with a dimethoate degradation rate greater than 94%. The byproducts generated during photocatalysis were identified using gas chromatography-mass spectrometry. The photocatalytic degradation of dimethoate followed first-order kinetics. The mechanism of the photocatalytic degradation of dimethoate was investigated.

An improved process for synthesizing pie (by machine translation)

The invention discloses a method for synthesizing pie of the improved process, the method is in the use of the latter amine solution in the process of preparing pie, the prepared pie crude crude oil first dried, then exsolution, prepared crude oil pie. The invention through a plurality of technological improvement, to the maximum extent and improved reaction environment, improves the main reaction process, reduce hydrolysis, of improving the reaction yield, and containing salt compound after treatment is more convenient. The use of the technique of the invention, oxygen can be improved to phosphorus [...] yield 86% or more, and also to increase the purity of 90% or more; and ammonium chloride purity can be up to 99% or more, can be directly used as by-product first class sales, pie can be improved to the total crude yield 79% above; the purity of the crude oil is also improved, greatly improve the overall process, social, economic benefit is enormous. (by machine translation)

A new method for the determination of some organophosphate insecticides

A quick and convenient method has been developed for milligram determination of some organophosphate insecticides. The sample is allowed to react with a calculated excess of (0.1 N) chloramine-T reagent in the presence of glacial acetic acid for 10-15 min at room temperature. After the reaction is over, KI solution (10%) is added and the unreacted reagent is back-titrated with 1 N solution of sodium thiosulfate to starch end-point. The method is applied for the determination of technical preparations of malathion (95%), dimethoate (90%), ethion (95%) and phorate (97%). The results are within the error of ±1.0%.