AZAMETHIPHOS

Details

Stereochemistry	ACHIRAL
Molecular Formula	C9H10ClN2O5PS
Molecular Weight	324.678
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COP(=O)(OC)SCN1C(=O)OC2=C1N=CC(Cl)=C2

InChI

InChIKey=VNKBTWQZTQIWDV-UHFFFAOYSA-N

InChI=1S/C9H10ClN2O5PS/c1-15-18(14,16-2)19-5-12-8-7(17-9(12)13)3-6(10)4-11-8/h3-4H,5H2,1-2H3

HIDE SMILES / InChI

Molecular Formula	C9H10ClN2O5PS
Molecular Weight	324.678
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27591805 | https://www.ncbi.nlm.nih.gov/pubmed/25893248

Azamethiphos, an organothiophosphate insecticide, initially was used in 1991 for the treatment against sea lice. However, because of reduced sensitivity in 1999, the use of this compound was terminated. Azamethiphos was re-introduced in 2008; it’s the main component of Salmosan, a pesticide presently used for treatment against sea lice. Salmosan is applied as a bath treatment and then released into the surrounding seawater

Approval Year

PubMed

Title	Date	PubMed
Environmental impact on vascular development predicted by high-throughput screening.	2011-11	21788198
Activity profiles of 309 ToxCast™ chemicals evaluated across 292 biochemical targets.	2011-03-28	21251949
Mass spectrometric analyses of organophosphate insecticide oxon protein adducts.	2010-01	20056576
A novel assay reveals the blockade of esterases by piperonyl butoxide.	2008-11	18481337
Albumin binding as a potential biomarker of exposure to moderately low levels of organophosphorus pesticides.	2008-06	18484351
Cholinesterase activities in the scallop Pecten jacobaeus: characterization and effects of exposure to aquatic contaminants.	2008-03-15	18177688
Characterisation of esterases as potential biomarkers of pesticide exposure in the lugworm Arenicola marina (Annelida: Polychaeta).	2008-03	17655990
The effect of repeated exposure to azamethiphos on survival and spawning in the American lobster (Homarus americanus).	2008-03	17590439
Susceptibility to thiamethoxam of Musca domestica from Danish livestock farms.	2008-02	17972302
Differential protein adduction by seven organophosphorus pesticides in both brain and thymus.	2007-04	17615116
Potential role of cholinesterases in the invasive capacity of the freshwater bivalve, Anodonta woodiana (Bivalvia: Unionacea): a comparative study with the indigenous species of the genus, Anodonta sp.	2007-04	17324630
Sublethal impact of short term exposure to the organophosphate pesticide azamethiphos in the marine mollusc Mytilus edulis.	2007-04	17266995
Organophosphate-resistant forms of acetylcholinesterases in two scallops--the Antarctic Adamussium colbecki and the Mediterranean Pecten jacobaeus.	2006-10	16931084
Variation of Musca domestica L. acetylcholinesterase in Danish housefly populations.	2006-08	16718740
Upper susceptibility threshold limits with confidence intervals: a method to identify normal and abnormal population values for laboratory toxicological parameters, based on acetylcholinesterase activities in sea lice.	2006-03	16475215
Glutathione S-transferase and insecticide resistance in laboratory strains and field populations of Musca domestica.	2005-08	16156589
Novel protein targets for organophosphorus pesticides in rat brain.	2005-05	21783511
Genotoxicity testing of some organophosphate insecticides in the Drosophila wing spot test.	2005-03	15680680
Seasonal lethality of the organophosphate pesticide, azamethiphos to female American lobster (Homarus americanus).	2005-03	15590004
Evidence for occurrence of an organophosphate-resistant type of acetylcholinesterase in strains of sea lice (Lepeophtheirus salmonis Krøyer).	2004-12	15578596
Susceptibility of spinosad in Musca domestica (Diptera: Muscidae) field populations.	2004-06	15279289
Characterisation of choline esterases and their tissue and subcellular distribution in mussel (Mytilus edulis).	2004-04	14580806
Safety of azamethiphos in eel, seabass and trout.	2004-02	14643697
Impact of an insecticide resistance strategy for house fly (Diptera: Muscidae) control in intensive animal units in the United Kingdom.	2002-12	12539838
Long-term effectiveness of grain protectants and structural treatments against Liposcelis decolor (Pearman) (Psocoptera: Liposcelididae), a pest of stored products.	2002-12	12476995
Efficacy and safety of azamethiphos for the treatment of pseudodactylogyrosis in the European eel.	2002-04	12000536
Identification and characterization of mutations in housefly (Musca domestica) acetylcholinesterase involved in insecticide resistance.	2001-10-01	11563981
Dispersion and toxicity to non-target aquatic organisms of pesticides used to treat sea lice on salmon in net pen enclosures.	2001-06	11468921
Alkylating potency of azamethiphos.	2001-03	11178640
The status and development of insecticide resistance in Danish populations of the housefly Musca domestica L.	2001-01	11455636

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:04:13 GMT 2025` Edited by `admin` on `Mon Mar 31 18:04:13 GMT 2025`
Record UNII	9440R8149U
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AZAMETHIPHOS

Common Name

English

CGA-18809

Preferred Name

English

AZAMETHIPHOS [MI]

Common Name

English

AZAMETHIPHOS [MART.]

Common Name

English

S-((6-CHLORO-2,3-DIHYDRO-2-OXO-1,3-OXAZOLO-(4,5-B)PYRIDIN-3-YL)METHYL) O,O-DIMETHYL PHOSPHOROTHIOATE.

Common Name

English

OMS NO 1825

Code

English

S-((6-CHLORO-2-OXOOXAZOLO(4,5-B)PYRIDIN-3(2H)-YL)METHYL) O,O-DIMETHYL PHOSPHOROTHIOATE

Systematic Name

English

S-6-CHLORO-2,3-DIHYDRO-2-OXO-1,3-OXAZOLO(4,5-B)PYRIDIN-3-YLMETHYL O,O-DIMETHYL PHOSPHOROTHIOATE

Systematic Name

English

CGA 18809

Code

English

OMS-NO-1825

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C737