ChemicalBook >> CAS DataBase List >>Omethoate

Omethoate

CAS No.
1113-02-6
Chemical Name:
Omethoate
Synonyms
S6876;s-6876;MODERN;B-45432;FOLIMAT;OMETHOAT;ent25,776;P=O-Rogor;bay 45432;OMETHOATE
CBNumber:
CB6109938
Molecular Formula:
C5H12NO4PS
Molecular Weight:
213.19
MDL Number:
MFCD00055441
MOL File:
1113-02-6.mol
Last updated:2023-05-15 10:43:33

Omethoate Properties

Melting point -27.9°C
Boiling point 135°C
Density 1.3200
vapor pressure 3.3×10-3Pa (20 °C)
Flash point 100 °C
storage temp. 0-6°C
solubility Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
Water Solubility Miscible
pka 14.40±0.46(Predicted)
form liquid
BRN 1785256
Stability Hygroscopic
CAS DataBase Reference 1113-02-6(CAS DataBase Reference)
EWG's Food Scores 6-7
FDA UNII 28U28EWE79
NIST Chemistry Reference Omethoate(1113-02-6)
EPA Substance Registry System Omethoate (1113-02-6)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS06,GHS09
Signal word  Danger
Hazard statements  H300-H311-H400
Precautionary statements  P264-P270-P273-P280-P301+P310-P302+P352+P312
Hazard Codes  T+;N,N,T+,T
Risk 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
HS Code  29309090
Toxicity LD50 oral in rabbit: 50mg/kg

Omethoate Chemical Properties,Uses,Production

Uses

Omethoate is a systemic insecticide used for the control of (mostly) sucking insects and mites in a wide variety of crops.

Uses

Insecticidal, acaricidal, and fungicidal combinations of carboxamides and other pesticides.

Definition

ChEBI: Omethoate is an organic thiophosphate and an organothiophosphate insecticide. It has a role as an EC 3.1.1.7 (acetylcholinesterase) inhibitor, an acaricide and an agrochemical. It is functionally related to a N-methyl-2-sulfanylacetamide.

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.

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).

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.

96-30-0
23754-87-2
1113-02-6
Synthesis of Omethoate from 2-Chloro-N-methylacetamide and sodium O,O-dimethyl thiophosphate
Omethoate E.C.,penetrating omethoatge B-45432 O,O-dimethyl S-methylcarbamoylmethyl phosphorothioate,omethoate (ISO) Omethoate Standard 2-(dimethoxyphosphorylthio)-N-methyl-acetamide 2-dimethoxyphosphorylsulfanyl-N-methylacetamide 2-dimethoxyphosphorylsulfanyl-N-methyl-ethanamide Folimat Dimethoate-met Omethoate Solution, 100ppm 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 Dimethoate PO isologue Dimethoate-met dimethoateoxygenanalog dimethoatepoisologue dimethoxane(omethoate) Dimethyl-S-(N-methyl-carbamoyl-methyl)phosphorothiolate ENT 25,776 ent25,776 Folimat 4E imethoate oxon O,O-Dimethyl S-(2-(methylamino)-2-oxoethyl)phosphorothioate O,O-Dimethyl S-(N-methylcarbamoylmethyl) phosphorothiolate O,O-Dimethyl S-(N-methylcarbamoylmethyl) thiophosphate o,o-Dimethyl S-[2-(methylamino)-2-oxoethyl] thiophosphate o,o-dimethylphosphorothioates-esterwith2-mercapto-n-methylacetamide O,O-Dimethyl-S-((N-methyl-carbamoyl)-methyl)-monothiofosfaat o,o-dimethyls-(2-(methylamino)-2-oxoethyl)phosphorothioate O,O-Dimethyl-S-(2-oxo-3-azabutyl)-monothiophosphate O,O-Dimethyl-S-(N-methylaminoformylmethyl)phosphorothioate o,o-dimethyl-s-(n-methyl-carbamoyl)-methyl-monothiophosphat O,O-Dimethyl-S-(N-methyl-carbamoyl)-methyl-monothiophosphate o,o-dimethyls-(n-methylcarbamoylmethyl)phosphorothiolate o,o-dimethyl-s-(n-methyl-carbamoyl-methyl)-thiolphosphat O,O-Dimethyl-S-(N-methyl-carbamoyl-methyl)-thiolphosphate o,o-dimethyls-(n-methylcarbamoylmethyl)thiophosphate O,O-Dimethyl-S-[2-(methylamino)-2-oxoethyl]phosphorothioate O,O-Dimetil-S-(N-metil-carbamoil)-metil-monotiofosfato O-Analog of dimethoate o-analogofdimethoate P=O-Rogor Phosphorothioic acid, O,O-dimethyl ester, S-ester with 2-mercapto-N-methylacetamide Phosphorothioicacid,esters,O,O-dimethyl-S-[2(methylamino)-2-oxoethyl]ester phosphorothioicacid,o,o-dimethylester,s-esterwith2-mercapto-n-methylaceta PO-Dimethoate S6876 s-6876 Thiophosphate de O,O-dimethyle et de S-(N-methylcarbamoyl) methyle thiophosphatedeo,o-dimethyleetdes-(n-methylcarbamoyl)methyle bay 45432 FOLIMAT