Azamethiphos

Azamethiphos Basic information
Description References
Product Name:Azamethiphos
Synonyms:6-Chloro-3-(dimethoxyphosphorylsulfanylmethyl)-[1,3]oxazolo[4,5-b]pyridin-2-one;Phosphorothioic acid, S-[(6-chloro-2-oxooxazolo[4,5-b]pyridin-3(2H)-yl)methyl] O,O-dimethyl ester;Alfracron;GS 40616;O,O-dimethyl-S-[6-chloro-2-oxooxazolo [4,5-b] pyridin-3 (2H)-yl] methyl phosphorothionate;Thiophosphoric acid S-(6-chloro-2-oxo-2,3-dihydrooxazolo[4,5-b]pyridin-3-ylmethyl)O,O-dimethyl ester;Thiophosphoric acid S-[(6-chloro-2-oxooxazolo[4,5-b]pyridin-3(2H)-yl)methyl]O,O-dimethyl ester;Azamethiphos 100ug/ml in Methylene chloride 5ml [35575-96-3]
CAS:35575-96-3
MF:C9H10ClN2O5PS
MW:324.68
EINECS:252-626-0
Product Categories:Agro Products;Agro-Products;Phosphorylating and Phosphitylating Agents;AR to AZPesticides;A;A-BAlphabetic;Pesticide & intermediate;Alpha sort;Insecticides;Organophorous;Pesticides&Metabolites;Alphabetic
Mol File:35575-96-3.mol
Azamethiphos Structure
Azamethiphos Chemical Properties
Melting point 88-93°C
Boiling point 428.8±55.0 °C(Predicted)
density 1.566±0.06 g/cm3(Predicted)
vapor pressure 4.9 x 10-6 Pa (20 °C)
storage temp. Sealed in dry,2-8°C
solubility Chloroform (Slightly), Methanol (Slightly)
Water Solubility 1100 mg l-1 (20 °C)
form Solid
pka0.94±0.20(Predicted)
CAS DataBase Reference35575-96-3(CAS DataBase Reference)
NIST Chemistry ReferencePhosphorothioic acid, s-[(6-chloro-2-oxooxazolo[4,5-b]pyridin-3(2h)-yl)methyl] o,o-dimethyl ester(35575-96-3)
EPA Substance Registry SystemAzamethiphos (35575-96-3)
Safety Information
Hazard Codes Xn
Risk Statements 22-36-40-21-67-36/37/38
Safety Statements 26-36/37-24/25-23
RIDADR UN 1593 6.1/PG 3
WGK Germany 3
RTECS TE8070000
HS Code 29349990
ToxicityLD50 orl-rat: 1180 mg/kg PEMNDP 9,44,91
MSDS Information
ProviderLanguage
Azamethiphos English
Azamethiphos Usage And Synthesis
DescriptionAzamethiphos is an organothiophosphate insecticide. It can be used as a veterinary drug used in the salmon fish farming for controlling parasites such as salmon lice (Lepeophtheirus salmonis), a marine ectoparasitic copepod on salmonid species. Its primary target is on the acetylcholinesterase, a serine hydrolase involved in neurotransmission at cholinergic synapses and neuromuscular junctions.
ReferencesIntorre, L, et al. "Safety of azamethiphos in eel, seabass and trout." Pharmacological Research the Official Journal of the Italian Pharmacological Society 49.2(2004):171. Kaur, K, et al. "Mechanism behind Resistance against the Organophosphate Azamethiphos in Salmon Lice (Lepeophtheirus salmonis). " Plos One 10.4(2015):e0124220.
Chemical Propertieswhite to light yellow crystal powde
UsesAzamethiphos is used to control flies and other insect pests in animal houses and also public hygiene and health pests such as mosquitoes and cockroaches. It has recently been used to control sea lice in salmon.
UsesSynergistic insecticidal and acaricidal organophosphorus compound
DefinitionChEBI: Azamethiphos is an organic thiophosphate, an organothiophosphate insecticide, an organochlorine insecticide and an organochlorine acaricide. It has a role as an EC 3.1.1.7 (acetylcholinesterase) inhibitor and an agrochemical. It is functionally related to an oxazolo[4,5-b]pyridin-2(3H)-one.
Safety ProfileModerately toxic by ingestion andskin contact. When heated to decomposition it emits toxicvapors of NOx, SOx, POx, and Cl- .
Metabolic pathwayAzamethiphos is metabolised in mammals via hydrolysis, followed by opening of the oxazolinone ring and conjugation of the resultant aminopyridinol as the glucuronide and sulfate ester.
MetabolismAzamethiphos is metabolized via the cleavage of phosphorothiolate C?S bond, followed by N-demethylation and opening of the oxazolinone ring and conjugation of the resultant aminochloropyridinol as the glucuronide and sulfate ester.
Toxicity evaluationAcute oral LD50 for rats is 1180 mg/kg. Inhalation LC50 (4 h) for rats is >560 mg/m3 air. ADI is 0.025 mg/kg.
DegradationAzamethiphos is unstable in alkalis and acids. The DT50 values at pH 5,7 and 9 were 800,260 and 4.3 hours, respectively (PM).
Azamethiphos Preparation Products And Raw materials
Raw materialsChlorine-->Sulfur-->Dimethyl sulfide-->formaldehyde-->Dimethyl phosphite-->Oxazole
2,3-Dihydropyrido[2,3-d][1,3]oxazol-2-one O,O-Diethyl O-[p-(Methylsulfinyl)phenyl] phosphorothioate,o,o-diethylo-(4-(methylsulfinyl)phenyl)phosphorothioate[qr ),)-dimethylo,o-[3-methyl-4-(methylthio)phenyl]phosphorothioat Azamethiphos W.P. O,O-Diethyl O-2,5-dichloro-4-bromophenyl-phosphorothioate,o,o-diethylo-2,5-dichloro-4-bromophenyl-phosphorothioat 3-Chloro-5-methoxypyridine Phenol, 2,4,5-trichloro-, O-ester with O,O-dimethyl phosphorothioate 4-THIAZOLEACETIC ACID, ALPHA-[(ACETYLOXY)IMINO]-2-AMINO-, ANHYDRIDE WITH O,O-DIETHYL HYDROGEN PHOSPHOROTHIOATE, (Z)- Azamethiphos o,o-diethyls-(2-eththioethyl)phosphorothioat 2-Amino-3-methoxypyridine O,O-Dimethyl S-1,2-bis(ethoxycarbonyl)ethyl phosphorothioate,Diethyl mercaptosuccinate S-ester with O,O-dimethyl phosphorothioate 2-AMINO-PYRIDIN-3-OL HCL Temephos O-(2-Diethylamino-6-methylpyrimidin-4-yl) O,O-dimethyl phosphorothioate Azamethiphos-D-6 RP-8-[(4-CHLOROPHENYL)THIO]-GUANOSINE-CYCLIC 3',5'-HYDROGEN PHOSPHOROTHIOATE TRIETHYLAMINE 5-Chloro-3-pyridinol

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