Azamethiphos

Azamethiphos is an organothiophosphate insecticide. It is a veterinary drug used in Atlantic salmon fish farming to control parasites.[1] It is also used as an insecticide in biocidal products in Europe.[2]

Azamethiphos
Names
Preferred IUPAC name
S-[(6-Chloro-2-oxo[1,3]oxazolo[4,5-b]pyridin-3(2H)-yl)methyl] O,O-dimethyl phosphorothioate
Other names
Azamethifos; Azamethiophos
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.047.827
UNII
  • 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
    Key: VNKBTWQZTQIWDV-UHFFFAOYSA-N
  • InChI=1/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
    Key: VNKBTWQZTQIWDV-UHFFFAOYAD
  • O=P(OC)(OC)SCN1c2ncc(Cl)cc2OC1=O
Properties
C9H10ClN2O5PS
Molar mass 324.67 g·mol−1
Pharmacology
QP53AF17 (WHO)
Legal status
  • AU: S6 (Poison)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Mode of action

Organophosphorus insecticides, such as Azamethiphos, inhibit the action of the enzyme acetylcholinesterase. The acetylcholine, therefore, remains intact allowing the electrical signal to proceed without interruption. This phenomenon leads to overexcitation of the organism and eventually to the death of the insect. [3]

Azamethiphos penetrates through the cuticle or through the cuticle opening of the insect, and also acts by ingestion and absorption through the digestive system.

Registration

In Europe, Azamethiphos is an active substance according to the Biocide Regulation 528/2012, to be used as insecticide.

It is used in several biocidal products in Europe, as insecticide mainly for professional users. It is commonly used against flies in animal housing.

Stability

Azamethiphos is sensitive to hydrolysis, especially at low pH.

Toxicity

Azamethiphos is of moderate acute oral toxicity (LD50 values ranging from 834 mg kg-1 in the rat to 1764 mg kg-1 in the hamster). Acute dermal toxicity is very low (LD50 values of >2020 and >6000 mg kg-1 are reported in the rabbit and an LD50 of >2150 mg kg-1 is reported in the rat).

Azamethiphos is irritant to eyes and skin.

Environmental toxicity

Azamethiphos is very toxic for the environment, with a LC50 on Daphnia magna of 0.33 µg/L.

References
  1. Azamethiphos Archived 2022-01-20 at the Wayback Machine, European Medicines Agency
  2. "Substance Information - ECHA". echa.europa.eu (in French). Retrieved 2023-02-13.
  3. Armosa factsheet on Azamethiphos, February 2022


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