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Quinalphos

CAS No.
13593-03-8
Chemical Name:
Quinalphos
Synonyms
6538;KRUSH;SMASH;6538e;s-6538;EKALUX;ECALUX;Savall;Elnalux;HUBELUX
CBNumber:
CB9227349
Molecular Formula:
C12H15N2O3PS
Molecular Weight:
298.3
MDL Number:
MFCD00078719
MOL File:
13593-03-8.mol
Last updated:2023-05-15 10:43:34

Quinalphos Properties

Melting point 31.5°C
Boiling point 142 °C
Density 1.306±0.06 g/cm3(Predicted)
vapor pressure 3.46×10-4 Pa (20 °C)
Flash point 2 °C
storage temp. APPROX 4°C
solubility Chloroform (Slightly), Methanol (Slightly)
pka -1.05±0.30(Predicted)
form Crystalline
Water Solubility 17.8 mg l-1 (22-23 °C)
BRN 754823
Stability Hygroscopic, Moisture sensitive
CAS DataBase Reference 13593-03-8(CAS DataBase Reference)
EWG's Food Scores 3
FDA UNII 26S837727Y
NIST Chemistry Reference Quinalphos(13593-03-8)
EPA Substance Registry System Quinalphos (13593-03-8)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictogramsGHS hazard pictograms
GHS05,GHS06,GHS09
Signal word  Danger
Hazard statements  H300+H330-H311-H318-H410
Precautionary statements  P260-P273-P280-P302+P352+P312-P304+P340+P310-P305+P351+P338
Hazard Codes  T,N,Xn,F
Risk Statements  21-25-50/53-51/53-36-20/21/22-11
Safety Statements  22-36/37-45-60-61-26
RIDADR  2783
WGK Germany  3
RTECS  TF6125000
HazardClass  6.1(a)
PackingGroup  II
HS Code  29339900
Toxicity cat,LD50,oral,75mg/kg (75mg/kg),National Technical Information Service. Vol. OTS0555485,

Quinalphos price More Price(4)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 45651 Quinalphos PESTANAL 13593-03-8 100mg $62.1 2024-03-01 Buy
TRC Q585000 Quinalphos 13593-03-8 5g $1260 2021-12-16 Buy
American Custom Chemicals Corporation PST0000364 OXO,OXO-DIETHYL-OXO-2-QUINOXALINYL PHOSPHOROTHIOATE 98.00% 13593-03-8 5G $1848 2021-12-16 Buy
American Custom Chemicals Corporation PST0000364 OXO,OXO-DIETHYL-OXO-2-QUINOXALINYL PHOSPHOROTHIOATE 98.00% 13593-03-8 1G $1068.38 2021-12-16 Buy
Product number Packaging Price Buy
45651 100mg $62.1 Buy
Q585000 5g $1260 Buy
PST0000364 5G $1848 Buy
PST0000364 1G $1068.38 Buy

Quinalphos Chemical Properties,Uses,Production

Uses

Quinalphos is used to control both chewing and sucking insects and mites in a large number of different crops.

Definition

ChEBI: Quinalphos 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 quinoxalin-2-ol.

Safety Profile

Poison by ingestion, inhalation, skin contact, parenteral, and intraperitoneal routes. Experimental reproductive effects. Mutation data reported. An insecticide. When heated to decomposition it emits very toxic fumes of NOx, POx, and SOx

Metabolic pathway

In methanol solution, quinalphos undergoes photodegradation reactions of isomerization, oxidation, and deesterification, together with other degradation reactions, resulting in several degradation products. However, the photolysis of quinalphos in ethanol solution yields the two products, O,O-diethyl-O-(3- ethoxyquinoxalin-2-yl)phosphorothioate and O,O- diethyl-O-[3(1-hydroxyethyl)-quinoxalin- 2yl]phosphorothioate, both of which are derived from the reaction of the photoexcited quinalphos molecule with the solvent.

Degradation

Quinalphos is susceptible to hydrolysis. The DT50 values at pH 3,6 and 9 were 23,39 and 26 days, respectively (PM). Quinalphos is very susceptible to acid hydrolysis but stable under mildly basic conditions, having a halflife ten times that of parathion at pH 11 (Schmidt, 1972). Quinalphos was degraded in distilled water (pH 6.0), rain water (pH 6.8) and tap water (pH 7.8) with DT50 values of 80,50 and 60 days, respectively (Dureja ef aI., 1988). The photolysis of quinalphos in ethanolic solution irradiated by a medium pressure mercury vapour lamp (λmax 366 nm) with a glass filter to screen out light of <290 nm gave photoproducts principally derived from reaction with the solvent. The main photolysis products were 3-ethoxyand 3-hydroxyethyl-quinoxaline derivatives of quinalphos (not shown in Scheme 1). A minor product of photodegradation was quinalphos oxon (2) (Pusino et al., 1989). When quinalphos was irradiated with a high pressure mercury vapour lamp (λmax 254 nm) in a quartz reactor many more photoproducts were detected, although whether this information is relevant to photodegradation in the environment is debatable since light of wavelength ﹤290 nm is generally absent at the Earth's surface. Using this method of irradiation, Dureja et al. (1988) examined the photolysis of quinalphos in hexane and methanol solution, as a thin film on a glass plate and on the soil surface. Analysis of the photoproducts was by MS and 1H NMR spectroscopy after separation by TLC and GC. The rates of photodecomposition in aqueous solution and on soil surfaces exposed to sunlight were also measured, although in these experiments the nature of the photoproducts were not determined. In methanol solution, three major pathways of photolysis were apparent: (a) de-esterification to afford quinoxolin-2-o1(3), (b) thionethiolo rearangement to O,O-diethyl S-quinoxalin-2-yl phosphorothioate (4), which was not actually detected and was presumably de-esterified to give quinoxoline-2-thiol (5) which dimerised to the disulfide (6) and the sulfide (7), and (c) oxidation of the P=S sulfur to afford the oxon (2) as shown in Scheme 1. In addition, the de-esterification of the phosphorothioate moiety and additional alkyl transfer from quinalphos gave triethyl phosphate (S), O,O,O-triethyl phosphorothioate (9) and O,O,S-triethyl phosphorodithioate (10). A number of other photoproducts were identified which were formed via reaction of the methanol solvent with quinalphos (1) and quinoxolin-2-o1 (3) but because of their non-relevance to photoproducts produced under environmental conditions they are not included in Scheme 1.
Irradiation of quinalphos as a thin film on glass produced quinalphos oxon (2) and quinoxolin-2-o1(3) as the main photoproducts. The products from the soil irradiation experiments were identified as quinalphos oxon (2), the rearranged product O,O-diethyl S-quinoxalin-2-yl phosphorothioate (4), quinoxolin-2-o1(3), quinoxoline-2-thiol(5) and the sulfide (7). Routes for photodegradation of quinalphos in methanol solution, as a thin film and on soil surfaces are shown in Scheme 1. Half-lives for the photodecomposition of quinalphos by sunlight in water varied from 23 to 30 days and on soil surfaces from 2 to 5 days.

2524-04-1
1196-57-2
13593-03-8
Synthesis of Quinalphos from Diethyl chlorothiophosphate and 2-Quinoxalinone
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