ChemicalBook Product Catalog Chemical pesticides Insecticides Organophosphorus Pesticides Pyraclofos

Pyraclofos

Pyraclofos Basic information
Product Name:Pyraclofos
Synonyms:(rs)-(o-1-(4-chlorophenyl)pyrazol-4-yl-o-ethyl-s-propylphosphorothioate);phosphorothioicacid,o-(1-(4-chlorophenyl)-1h-pyrazol-4-yl)o-ethyls-propyle;VOLTAGE;VOLTAGE(R);PYRACLOFOS, 50MG, NEAT;pyraclofos (bsi,draft e-iso,draft f-iso);（RS）-O-ethyl-S-propyl-O-[1-(4-chlorophenyl) pyrazol-4-yl] phosphorothioate;OMS3034
CAS:77458-01-6
MF:C14H18ClN2O3PS
MW:360.8
EINECS:
Product Categories:Pyrazoles;Alpha sort;Insecticides;N-PPesticides;OrganophorousAlphabetic;P;Pesticides&Metabolites;PU - PZPesticides
Mol File:77458-01-6.mol
Pyraclofos Structure
Pyraclofos Chemical Properties
Melting point 25°C
Boiling point 164approximate 164℃(0.013hPa)
density 1.27
vapor pressure 1.6×10-6 Pa (20 °C)
storage temp. 0-6°C
form liquid
Water Solubility 33
Specific Gravity1.271 (28℃)
CAS DataBase Reference77458-01-6(CAS DataBase Reference)
EPA Substance Registry SystemPhosphorothioic acid, O-[1-(4-chlorophenyl)-1H-pyrazol- 4-yl] O-ethyl S-propyl ester(77458-01-6)
Safety Information
Hazard Codes Xi,Xn
Risk Statements 22
RIDADR 3018
RTECS TE8346000
HazardClass 6.1(b)
PackingGroup III
HS Code 29331990
Pyraclofos Usage And Synthesis
UsesPyraclofos 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.
DefinitionChEBI: Pyraclofos is an organic thiophosphate, an organothiophosphate insecticide, an organochlorine insecticide, a member of pyrazoles, a member of monochlorobenzenes and an organosulfur compound. It has a role as an EC 3.1.1.7 (acetylcholinesterase) inhibitor and an agrochemical.
Metabolic pathwayPyraclofos 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.
MetabolismPyraclofos 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 evaluationThe 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.
DegradationThe DT50 for hydrolysis in water at pH 7 (25 °C) was 29 days (PM).
Pyraclofos Preparation Products And Raw materials
Raw materialsTriethylamine-->THIOPHOSPHORYL CHLORIDE-->Pyrazole-->Chloroacetone-->Benzophenone hydrazone-->Methylglyoxal
5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one Propyl gallate Ethanol Ethyl formate Metazachlor Pyraclostrobin Ethylbenzene Tris(2-chloroethyl) phosphate Ethylparaben Zolpidem Diphenylthiocarbazide Mefenpyr-diethyl Ethyl acetate Zolpidem tartrate Clindamycin phosphate Ethyl acrylate Propyl butyrate SULPHOSUCCINIC ACID ESTER
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