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77458-01-6

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77458-01-6 Usage

Uses

Pyraclofos is used to control Lepidoptera, Coleoptera, mites and nematodes in fruit, vegetables, ornamentals and forestry. It has also been used in a human health application to control filarial worms.

Metabolic pathway

Pyraclofos is apparently subjected in insects to a metabolic activation to yield a more active acetylcholinesterase inhibitor which is possibly a thiooxidized metabolite. The compound is very rapidly degraded in mammals to inactive metabolites via P-O-aryl, P-O-alkyl and P-S-alkyl cleavage which explains its favourable selective toxicity. In both mammals and plants the principal degradative route is via P-O-aryl cleavage to give 1-(4-chlorophenyl)-4-hydroxypyrazolwe hich is rapidly conjugated.

Metabolism

Pyraclofos is metabolized to an active AChE inhibitor, probably by the oxidation of the sulfur atom in the phosphorothiolate linkage. The half-life in soil is 3–38 d, depending on soil type.

Toxicity evaluation

The acute oral LD50 for rats is 237 mg/kg. The inhalation LC50 for rats is 1.69 mg/L air. NOEL (2 yr) for rats is 0.10–0.12 mg/kg diet (0.005–0.006 mg/kg/d). Pyraclofos administered to rats is rapidly degraded, and more than 90% of the dose is excreted principally in the urine within 24 h. The degradation routes are cleavages of the P?S, P?O-alkyl, and P?O-aryl bonds in both animals and plants.

Degradation

The DT50 for hydrolysis in water at pH 7 (25 °C) was 29 days (PM).

Check Digit Verification of cas no

The CAS Registry Mumber 77458-01-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,7,4,5 and 8 respectively; the second part has 2 digits, 0 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 77458-01:
(7*7)+(6*7)+(5*4)+(4*5)+(3*8)+(2*0)+(1*1)=156
156 % 10 = 6
So 77458-01-6 is a valid CAS Registry Number.
InChI:InChI=1/C14H18ClN2O3PS/c1-3-9-22-21(18,19-4-2)20-14-10-16-17(11-14)13-7-5-12(15)6-8-13/h5-8,10-11H,3-4,9H2,1-2H3

77458-01-6SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name pyraclofos

1.2 Other means of identification

Product number -
Other names (RS)-[O-1-(4-chlorophenyl)pyrazol-4-yl O-ethyl S-propyl phosphorothioate]

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:77458-01-6 SDS

77458-01-6Synthetic route

sodium O-ethyl-O-[1-(4-chlorophenyl)pyrazol-4-yl]phosphorothiolate
96381-04-3

sodium O-ethyl-O-[1-(4-chlorophenyl)pyrazol-4-yl]phosphorothiolate

propyl bromide
106-94-5

propyl bromide

(RS)-O-1-(4-chlorophenyl)pyrazol-4-yl O-ethyl S-propyl phosphorothioate
77458-01-6

(RS)-O-1-(4-chlorophenyl)pyrazol-4-yl O-ethyl S-propyl phosphorothioate

Conditions
ConditionsYield
In ethanol; toluene
O-[1-(4-chlorophenyl)pyrazol-4-yl]-O,O-diethyl phosphite
84260-11-7

O-[1-(4-chlorophenyl)pyrazol-4-yl]-O,O-diethyl phosphite

Dipropyl disulfide
629-19-6

Dipropyl disulfide

(RS)-O-1-(4-chlorophenyl)pyrazol-4-yl O-ethyl S-propyl phosphorothioate
77458-01-6

(RS)-O-1-(4-chlorophenyl)pyrazol-4-yl O-ethyl S-propyl phosphorothioate

Conditions
ConditionsYield
With sodium hydroxide; sulfuryl dichloride In toluene
1-(4-chlorophenyl)-1H-pyrazol-4-ol
77458-30-1

1-(4-chlorophenyl)-1H-pyrazol-4-ol

O-ethyl-S-propyl phosphorochloridate
7651-98-1

O-ethyl-S-propyl phosphorochloridate

(RS)-O-1-(4-chlorophenyl)pyrazol-4-yl O-ethyl S-propyl phosphorothioate
77458-01-6

(RS)-O-1-(4-chlorophenyl)pyrazol-4-yl O-ethyl S-propyl phosphorothioate

Conditions
ConditionsYield
With triethylamine In acetonitrile

77458-01-6Downstream Products

77458-01-6Relevant articles and documents

Pyrazol-4-yl phosphites

-

, (2008/06/13)

A 4-pyrazolyl phosphorous acid ester of the following formula, STR1 (R is a lower alkyl group; Y is a phenyl group which may optionally be substituted by a halogen, halogens, a lower alkyl group or a halogen and a lower alkyl group.) which is produced by reacting corresponding 4-hydroxylpyrazole compound with a trialkyl phosphite. The ester gives 4-pyrazolyl phosphorothioate by the reaction with an alkylsulfenyl halide.

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