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35575-96-3

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35575-96-3 Usage

Description

Azamethiphos 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.

References

Intorre, 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 Properties

white to light yellow crystal powde

Uses

Azamethiphos 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.

Safety Profile

Moderately toxic by ingestion andskin contact. When heated to decomposition it emits toxicvapors of NOx, SOx, POx, and Cl- .

Metabolic pathway

Azamethiphos 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.

Metabolism

Azamethiphos 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 evaluation

Acute 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.

Degradation

Azamethiphos is unstable in alkalis and acids. The DT50 values at pH 5,7 and 9 were 800,260 and 4.3 hours, respectively (PM).

Check Digit Verification of cas no

The CAS Registry Mumber 35575-96-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,5,5,7 and 5 respectively; the second part has 2 digits, 9 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 35575-96:
(7*3)+(6*5)+(5*5)+(4*7)+(3*5)+(2*9)+(1*6)=143
143 % 10 = 3
So 35575-96-3 is a valid CAS Registry Number.
InChI: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

35575-96-3 Well-known Company Product Price

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  • Alfa Aesar

  • (H66105)  S-[(6-Chloro-2-oxooxazolo[4,5-b]pyridin-3yl)methyl] O,O-dimethyl phosphorothioate, 95%   

  • 35575-96-3

  • 250mg

  • 284.0CNY

  • Detail
  • Alfa Aesar

  • (H66105)  S-[(6-Chloro-2-oxooxazolo[4,5-b]pyridin-3yl)methyl] O,O-dimethyl phosphorothioate, 95%   

  • 35575-96-3

  • 1g

  • 907.0CNY

  • Detail
  • Alfa Aesar

  • (H66105)  S-[(6-Chloro-2-oxooxazolo[4,5-b]pyridin-3yl)methyl] O,O-dimethyl phosphorothioate, 95%   

  • 35575-96-3

  • 5g

  • 3783.0CNY

  • Detail

35575-96-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name azamethiphos

1.2 Other means of identification

Product number -
Other names ALFACRON

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:35575-96-3 SDS

35575-96-3Synthetic route

C7H5ClN2O2S

C7H5ClN2O2S

Dimethyl phosphite
868-85-9

Dimethyl phosphite

S-((6-chloro-2,3-dihydro-2-oxo-1,3-oxazolo[4,5-b]pyridin-3-yl)methyl) O,O-dimethyl phosphorothioate
35575-96-3

S-((6-chloro-2,3-dihydro-2-oxo-1,3-oxazolo[4,5-b]pyridin-3-yl)methyl) O,O-dimethyl phosphorothioate

Conditions
ConditionsYield
With oxygen; caesium carbonate In acetonitrile at 60℃; under 760.051 Torr; for 12h;69%
6-chloro-3-chloromethyl-3H-oxazolo[4,5-b]pyridin-2-one
35570-70-8

6-chloro-3-chloromethyl-3H-oxazolo[4,5-b]pyridin-2-one

ammonium-thio-O,O-dimethylphosphate

ammonium-thio-O,O-dimethylphosphate

S-((6-chloro-2,3-dihydro-2-oxo-1,3-oxazolo[4,5-b]pyridin-3-yl)methyl) O,O-dimethyl phosphorothioate
35575-96-3

S-((6-chloro-2,3-dihydro-2-oxo-1,3-oxazolo[4,5-b]pyridin-3-yl)methyl) O,O-dimethyl phosphorothioate

Conditions
ConditionsYield
In methanol64%
6-chloro-3-chloromethyl-3H-oxazolo[4,5-b]pyridin-2-one
35570-70-8

6-chloro-3-chloromethyl-3H-oxazolo[4,5-b]pyridin-2-one

Ammoniumsalz des O,O'-Dimethyl-thiophosphats
40633-14-5

Ammoniumsalz des O,O'-Dimethyl-thiophosphats

S-((6-chloro-2,3-dihydro-2-oxo-1,3-oxazolo[4,5-b]pyridin-3-yl)methyl) O,O-dimethyl phosphorothioate
35575-96-3

S-((6-chloro-2,3-dihydro-2-oxo-1,3-oxazolo[4,5-b]pyridin-3-yl)methyl) O,O-dimethyl phosphorothioate

Conditions
ConditionsYield
In methanol for 0.0833333h; Heating;
6-chlorooxazole[4,5-b]pyridine-2(3H)-one
35570-68-4

6-chlorooxazole[4,5-b]pyridine-2(3H)-one

S-((6-chloro-2,3-dihydro-2-oxo-1,3-oxazolo[4,5-b]pyridin-3-yl)methyl) O,O-dimethyl phosphorothioate
35575-96-3

S-((6-chloro-2,3-dihydro-2-oxo-1,3-oxazolo[4,5-b]pyridin-3-yl)methyl) O,O-dimethyl phosphorothioate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: H2O
2: SOCl2 / CHCl3
3: methanol / 0.08 h / Heating
View Scheme
6-chloro-3-hydroxymethyl-3H-oxazolo[4,5-b]pyridin-2-one
35570-69-5

6-chloro-3-hydroxymethyl-3H-oxazolo[4,5-b]pyridin-2-one

S-((6-chloro-2,3-dihydro-2-oxo-1,3-oxazolo[4,5-b]pyridin-3-yl)methyl) O,O-dimethyl phosphorothioate
35575-96-3

S-((6-chloro-2,3-dihydro-2-oxo-1,3-oxazolo[4,5-b]pyridin-3-yl)methyl) O,O-dimethyl phosphorothioate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: SOCl2 / CHCl3
2: methanol / 0.08 h / Heating
View Scheme
2-amino-3-hydroxypyridine
16867-03-1

2-amino-3-hydroxypyridine

S-((6-chloro-2,3-dihydro-2-oxo-1,3-oxazolo[4,5-b]pyridin-3-yl)methyl) O,O-dimethyl phosphorothioate
35575-96-3

S-((6-chloro-2,3-dihydro-2-oxo-1,3-oxazolo[4,5-b]pyridin-3-yl)methyl) O,O-dimethyl phosphorothioate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: Py / 1 h / Ambient temperature
2: Cl2 / dimethylformamide / Ambient temperature
3: H2O
4: SOCl2 / CHCl3
5: methanol / 0.08 h / Heating
View Scheme
2,3-dihydro[1,3]oxazolo[4,5-b]pyridin-2-one
60832-72-6

2,3-dihydro[1,3]oxazolo[4,5-b]pyridin-2-one

S-((6-chloro-2,3-dihydro-2-oxo-1,3-oxazolo[4,5-b]pyridin-3-yl)methyl) O,O-dimethyl phosphorothioate
35575-96-3

S-((6-chloro-2,3-dihydro-2-oxo-1,3-oxazolo[4,5-b]pyridin-3-yl)methyl) O,O-dimethyl phosphorothioate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: Cl2 / dimethylformamide / Ambient temperature
2: H2O
3: SOCl2 / CHCl3
4: methanol / 0.08 h / Heating
View Scheme
C7H4Cl3N2O3PS

C7H4Cl3N2O3PS

sodium methylate
124-41-4

sodium methylate

S-((6-chloro-2,3-dihydro-2-oxo-1,3-oxazolo[4,5-b]pyridin-3-yl)methyl) O,O-dimethyl phosphorothioate
35575-96-3

S-((6-chloro-2,3-dihydro-2-oxo-1,3-oxazolo[4,5-b]pyridin-3-yl)methyl) O,O-dimethyl phosphorothioate

Conditions
ConditionsYield
In methanol at 10 - 60℃;183 g
S-((6-chloro-2,3-dihydro-2-oxo-1,3-oxazolo[4,5-b]pyridin-3-yl)methyl) O,O-dimethyl phosphorothioate
35575-96-3

S-((6-chloro-2,3-dihydro-2-oxo-1,3-oxazolo[4,5-b]pyridin-3-yl)methyl) O,O-dimethyl phosphorothioate

C24H16CuN6O10

C24H16CuN6O10

C9H10ClCuN4O11PS

C9H10ClCuN4O11PS

Conditions
ConditionsYield
In methanol pH=7.4;
S-((6-chloro-2,3-dihydro-2-oxo-1,3-oxazolo[4,5-b]pyridin-3-yl)methyl) O,O-dimethyl phosphorothioate
35575-96-3

S-((6-chloro-2,3-dihydro-2-oxo-1,3-oxazolo[4,5-b]pyridin-3-yl)methyl) O,O-dimethyl phosphorothioate

C16H13CuNO3S(2+)

C16H13CuNO3S(2+)

C25H23ClCuN3O8PS2(2+)

C25H23ClCuN3O8PS2(2+)

Conditions
ConditionsYield
With N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid In water pH=7.4; Solvent;

35575-96-3Downstream Products

35575-96-3Relevant articles and documents

A thiophosphate synthetic method of compound and the method in a plurality of pharmaceutical application in the synthesis of (by machine translation)

-

Paragraph 0247; 0248; 0249; 0250, (2017/07/20)

The invention discloses a having the general formula (III) of the thiophosphate synthetic method of compound, the purpose is to provide a novel, condition is simple, easy to industrial production of the thiophosphate synthetic method of compound. The method is to have the general formula (I) of the organophosphorus oxygen apperception compound having the general formula (II) with a mercaptan or phenyl-sulfhydryl apperception compound mixed, under the effects of catalyst, obtained by the reaction of the formula (III) of the thiophosphate compound. The method of the invention, can be cheap efficient synthesis of thiophosphate compounds, in actual production will have extensive application prospect. (by machine translation)

Process for the production of 2-amino-3-hydroxypyridine derivatives

-

, (2008/06/13)

2-Amino-3-hydroxy-5-chloropyridine and 2-amino-3-hydroxy-5-bromopyridine are produced by selective hydrolysis of corresponding 2-amino-3,5-dihalopyridines.

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