Pyridaphenthion

Pyridaphenthion Basic information
Product Name:Pyridaphenthion
Synonyms:PYRIDAPHENTHION;OFUNACK;ORESTE;3(2H)-Pyridazinone, 6-hydroxy-2-phenyl-, O-ester with O,O-diethyl phosphorothioate;3(2h)-pyridazinone,6-hydroxy-2-phenyl-,o-esterwitho,o-diethylphosphoroth;American cyanamid 12,503;americancyanamid12,503;CL 12503
CAS:119-12-0
MF:C14H17N2O4PS
MW:340.33
EINECS:204-298-5
Product Categories:Alpha sort;Insecticides;N-PPesticides;OrganophorousAlphabetic;P;Pesticides&Metabolites;PU - PZ;INSECTICIDE;intermediate
Mol File:119-12-0.mol
Pyridaphenthion Structure
Pyridaphenthion Chemical Properties
Melting point 54.5~56.5℃
Boiling point 416.2±28.0 °C(Predicted)
density 1.30±0.1 g/cm3(Predicted)
vapor pressure 1.47×10-6 Pa (20 °C)
Fp -4 °C
storage temp. APPROX 4°C
Water Solubility 100mg l-1 (20°C)
form neat
pka-2.09±0.40(Predicted)
BRN 302741
CAS DataBase Reference119-12-0(CAS DataBase Reference)
NIST Chemistry ReferencePhosphorothioic acid, o-(1,6-dihydro-6-oxo-1-phenyl-3-pyridazinyl) o,o-diethyl ester(119-12-0)
EPA Substance Registry SystemPyridaphenthion (119-12-0)
Safety Information
Hazard Codes F,Xi,N,Xn
Risk Statements 11-36-66-67-57-51/53-20/22
Safety Statements 26-61-33-16
RIDADR 2783
WGK Germany 3
RTECS TF2275000
HazardClass 6.1(a)
PackingGroup II
MSDS Information
Pyridaphenthion Usage And Synthesis
DescriptionPyridaphenthion is a pale yellow solid, mp 54.5–56 ?C, vp 0.00147 mPa (20 ?C). Solubility in water is 100 mg/L (20 ?C). It is very soluble in acetone, methanol, and diethyl ether. Log Kow = 3.2.
UsesPyridaphenthion is used to control a wide range of chewing and sucking insects and mites in rice, vegetables, fruit and ornamentals.
DefinitionChEBI: Pyridaphenthion is an organic thiophosphate, an organothiophosphate insecticide and a pyridazinone. It has a role as an EC 3.1.1.7 (acetylcholinesterase) inhibitor and an agrochemical. It is functionally related to a 6-hydroxy-2-phenylpyridazin-3-one.
Safety ProfilePoison by intraperitoneal route. Moderately toxic by ingestion and skin contact. When heated to decomposition it emits very toxic fumes of SOx, POx, and NOx. Used to control chewing and suckmg insects on rice, fruits, vegetables, and cereals.
Metabolic pathwayPyridaphentluon is photolytically transformed into the oxon and phenylmaleic hydrazide. In the mouse its metabolism involves oxidative dearylation, oxidative desulfuration to the oxon, de-ethylation and conjugation of phenylmaleic hydrazide produced as the ultimate product of stage I metabolism and is typical of many phosphorothioates. A marked difference between metabolism in mice and rats was shown, with rats excreting no desethylpyridaphenthion and excreting all of the phenyl-maleic hydrazide in an unconjugated form.
MetabolismMore than 70% of the dose administered to rats and mice was excreted within 24 h in the urine. The major metabolites excreted are phenylmaleic hydrazide and desethyl pyridafenthion-oxon. The half-life in soil is 11–24 d.
DegradationThe photolysis of pyridaphenthion on a glass slide irradiated with both short wavelength UV light and light of wavelength >300 nm was investigated by Tsao et al. (1989). Samples were irradiated for 48 hours at unrecorded light intensity as thin films spread on petri dishes or in solution in water, methanol or hexane under an oxygen atmosphere. The effects of photosensitisers was also assessed in the thin film experiments. The photoproducts were analysed by TLC, GC-MS and 1H NMR spectroscopy. Under thin film conditions pyridaphenthion was photodegraded more quickly with light >300 nm than by 254 um light and was degraded faster as a thin film than in solution. The main photoproducts from the glass surface and aqueous solution were pyridaphenthion oxon (2) and phenylmaleic hydrazide (3) (Scheme 1); the only other products were small amounts of polymers. Photosensitisers accelerated photolysis markedly with the most effective being a plant-derived natural product, cis-dehydromatricaria ester. It is notable that a simple chemical oxidation using 3-chloroperoxybenzoic acid gave the same two products, 2 and 3.
Toxicity evaluationThe acute oral LD50 for rats is 769–850 mg/kg. Inhalation LC50 (4 h) for rats is >1.13 mg/L air.
Pyridaphenthion Preparation Products And Raw materials
Raw materialsMaleic anhydride-->THIOPHOSPHORYL CHLORIDE-->2-tert-Butyl-4,5-dichloro-3-2H-pyridazinone
3-HYDROXY-1-PHENYL-6-PYRIDAZONE PYRIDAPHENTHION SOLUTION 100UG/ML IN TOLUENE 1ML Pyridaphenthion+Methomyl+Fenvalerate,E.C. Pyridaphenthion 3-HYDROXY-1-METHYLPYRIDAZIN-6(1H)-ONE pyridaphenthion-trichlorphon powder,4.5% Pyridaphenthion+Fenvalerate,E.C. Pyridazine Pyrdaphenthion+Triazophos,E.C. PHENYL VALERATE Diphenylthiocarbazide Mefenpyr-diethyl Celiprolol O,O,O-TRIETHYLPHOSPHOROTHIOATE PYRIDAPHENTHION SOLUTION 100UG/ML IN ACETONITRILE 1ML Pyrdaphenthion+Acephate,E.C. SULPHOSUCCINIC ACID ESTER 40% pyridaphenthion-methamidophos,emulsifiable concentrate

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