13593-03-8 Usage
Uses
Used in Agriculture:
Quinalphos is used as an insecticide for controlling chewing and sucking insects as well as mites in a large number of different crops. This helps to protect the crops from damage and ensures a higher yield.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 13593-03-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,5,9 and 3 respectively; the second part has 2 digits, 0 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 13593-03:
(7*1)+(6*3)+(5*5)+(4*9)+(3*3)+(2*0)+(1*3)=98
98 % 10 = 8
So 13593-03-8 is a valid CAS Registry Number.
InChI:InChI=1/C12H15N2O3PS/c1-3-15-18(19,16-4-2)17-12-9-13-10-7-5-6-8-11(10)14-12/h5-9H,3-4H2,1-2H3
13593-03-8Relevant articles and documents
Investigation on the acylation of heterocyclic alcoholate anions with O,O-dialkyl phosphorochloridothioate in water solvent
Ge, Xin,Qian, Chao,Chen, Xinzhi
, p. 739 - 744 (2013)
The acylation of some heterocyclic alcoholate anions with O,O-dialkyl phosphorochloridothioate has been investigated. Higher yields and fewer byproducts were achieved in water at 50 °C by employing an effective phase-transfer catalyst (PTC) (benzyl triethylammonium chloride [BTEAC]), acylation catalyst (AC) (4-dimethylaminopyridine), and surfactant (sodium dodecyl sulfate), under weakly basic (pH 9.5～10) conditions. This reaction can also be applied to synthesize other insecticides with excellent yields.
Concentrates of organophosphorous insecticides
-
, (2008/06/13)
A low volatile organic compound co-solvent system is disclosed for preparing emulsion concentrates of low melting organophosphorous insecticides wherein the bioefficacy of the insecticide active is significantly enhanced. The co-solvent system comprises a water-soluble ethoxylated fatty acid/rosin acid-nonionic surfactant composition.
Insecticidal composition for agricultural and horticultural use
-
, (2008/06/13)
A synergistic insecticidal composition comprising a nitromethylene derivative of the formula STR1 in which X is a lower alkyl group, a lower alkoxy group or a halogen atom, n is 0, 1 or 2, and m is 2 or 3, and an insecticide which is a carboxylic acid ester, carbamate, organophosphate ester or one of a group of specific compounds.
Condensation products
-
, (2008/06/13)
Formamidine compounds of the formula EQU1 or WHEREIN R1 represents a substituted or unsubstituted phenyl radical, R2 represents hydroogen, alkyl, alkenyl or alkinyl and R3 represents acyl their manufacture and their use in pest control.
