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Pyridaphenthion
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Name

Pyridaphenthion

 EINECS 204-298-5
CAS No. 119-12-0 Density 1.3 g/cm3
PSA 104.48000 LogP 3.55940
Solubility 100mg l-1 （20°C） Melting Point 54.5～56.5℃
Formula C14H17N2O4PS Boiling Point 416.2 °C at 760 mmHg
Molecular Weight 340.34 Flash Point 205.5 °C
Transport Information UN 2783 Appearance COA
Safety 26 Risk Codes 11-36-66-67
Molecular Structure Molecular Structure of 119-12-0 (Pyridaphenthion) Hazard Symbols FlammableF, IrritantXi
Synonyms

Phosphorothioicacid, O,O-diethyl ester, O-ester with 6-hydroxy-2-phenyl-3(2H)-pyridazinone(7CI,8CI);3(2H)-Pyridazinone, 6-hydroxy-2-phenyl-, O-ester with O,O-diethylphosphorothioate (8CI);American Cyanamid 12,503;CL 12503;ENT 23,968;O,O-Diethyl O-(2,3-dihydro-3-oxo-2-phenyl-6-pyridazinyl) phosphorothioate;O,O-Diethyl phosphorothioate O-ester with6-hydroxy-2-phenyl-3(2H)-pyridazinone;O-(1,6)-Dihydro-6-oxo-1-phenylpyridazin-3-yl) O,O-diethyl phosphorothioate;Ofunack;Oreste;Pyridafenthion;Phosphorothioic acid,O-(1,6-dihydro-6-oxo-1-phenyl-3-pyridazinyl) O,O-diethyl ester;

 

Pyridaphenthion Chemical Properties

Molecular Formula: C14H17N2O4PS
Molar mass: 340.33 g/mol
EINECS: 204-298-5
Density: 1.3 g/cm3
Flash Point: 205.5 °C
Index of Refraction: 1.588
Boiling Point: 416.2 °C at 760 mmHg
Vapour Pressure: 3.9E-07 mmHg at 25°C
Melting point: 167-172 °C(lit.)
Storage temp: Approx 4°C
Solubility: In ethanol 1.25%, isopropanol 58%, chloroform 67.4%, 101% ethyl ether, methanol 226%, 377% acetone, insoluble in water
Product categories of Pyridaphenthion (119-12-0): Alpha sort;Insecticides;N-PPesticides;Pesticides & Metabolites;Organophorous Alphabetic
Structure of Pyridaphenthion (119-12-0):
              
XLogP3-AA: 3.3
H-Bond Donor: 0
H-Bond Acceptor: 5
Systematic Name: 6-Diethoxyphosphinothioyloxy-2-phenyl-pyridazin-3-one 
SMILES: S=P(OCC)(OCC)O/C2=N/N(c1ccccc1)C(=O)/C=C2 
InChI: InChI=1/C14H17N2O4PS/c1-3-18-21(22,19-4-2)20-13-10-11-14(17)16(15-13)12-8-6-5-7-9-12/h5-11H,3-4H2,1-2H3 
InChIKey: CXJSOEPQXUCJSA-UHFFFAOYAQ 
Std. InChI: InChI=1S/C14H17N2O4PS/c1-3-18-21(22,19-4-2)20-13-10-11-14(17)16(15-13)12-8-6-5-7-9-12/h5-11H,3-4H2,1-2H3 
Std. InChIKey: CXJSOEPQXUCJSA-UHFFFAOYSA-N

Pyridaphenthion Uses

 Pyridaphenthion (119-12-0) can be used for the prevention and control of rice stem borer, yellow rice borer, leafhoppers, planthoppers, cotton red spider, peanut pests' aphids.

Pyridaphenthion Production

1.Diazotization: having the reaction of nitrogen of the Aniline with Sodium nitrite and hydrochloric acid ( the ratio of 1:1.01:2.3 (mol)),and keep Sodium nitrite prepared as 35% ~ 40% aqueous solution, and dropping at the temperature below 5 ℃, to get re - nitrogen salt.
2.Then restore the diazonium salt with excess Sodium sulfite for 30min : ratio of 1.0:2.2 ( Aniline dollars ), Hydrochloric acid and keep the former reaction temperature controlled at 70 ℃; Canada Ph value of hydrochloric acid adjusted to 6 ~ 7, warming back 0.5h.
3.Condensation: having Maleic anhydride and Phenylhydrazine (commonly the Hydrochloric acid aqueous solution) for the reaction of pyridazinone. Phenylhydrazine and the maleic anhydride feed ratio of 1:1 (by aniline dollars), reaction temperature 100 ~ 109 ℃, time of 4h, vacuum operation.

Pyridaphenthion Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 oral > 12gm/kg (12000mg/kg)   Japan Pesticide Information. Vol. (33), Pg. 9, 1977.
dog LD50 skin > 20gm/kg (20000mg/kg)   Japan Pesticide Information. Vol. (33), Pg. 9, 1977.
guinea pig LD50 oral 513mg/kg (513mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION
GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE		 Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 53(11), Pg. 66, 1988.
mouse LD50 intraperitoneal 64mg/kg (64mg/kg)   "Pesticide Index," Frear, E.H., ed., State College, PA, College Science Pub., 1969Vol. 4, Pg. 170, 1969.
mouse LD50 oral 237mg/kg (237mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION

SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"		 Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 53(11), Pg. 66, 1988.
mouse LD50 skin 660mg/kg (660mg/kg)   Japan Pesticide Information. Vol. (33), Pg. 9, 1977.
mouse LD50 subcutaneous 370mg/kg (370mg/kg)   Japan Pesticide Information. Vol. (33), Pg. 9, 1977.
quail LD50 oral 68400ug/kg (68.4mg/kg)   Japan Pesticide Information. Vol. (33), Pg. 9, 1977.
rabbit LD50 oral 4800mg/kg (4800mg/kg)   Japan Pesticide Information. Vol. (33), Pg. 9, 1977.
rabbit LD50 skin > 2gm/kg (2000mg/kg)   Japan Pesticide Information. Vol. (33), Pg. 9, 1977.
rat LC50 inhalation 1100mg/m3/4H (1100mg/m3)   Pesticide Manual. Vol. 9, Pg. 285, 1991.
rat LD50 intraperitoneal 105mg/kg (105mg/kg)   Japan Pesticide Information. Vol. (33), Pg. 9, 1977.
rat LD50 oral 424mg/kg (424mg/kg)   Yakkyoku. Pharmacy. Vol. 37, Pg. 1621, 1986.
rat LD50 skin 2100mg/kg (2100mg/kg)   Farm Chemicals Handbook. Vol. -, Pg. C223, 1991.
rat LD50 subcutaneous 305mg/kg (305mg/kg)   Japan Pesticide Information. Vol. (33), Pg. 9, 1977.

Pyridaphenthion Safety Profile

Poison 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 sucking insects on rice, fruits, vegetables, and cereals.
 

Hazard Codes: F,Xi
Risk Statements:
11:  Highly Flammable
36:  Irritating to the eyes
66:  Repeated exposure may cause skin dryness or cracking
67:  Vapors may cause drowsiness and dizziness

Pyridaphenthion Specification

 Pyridaphenthion (119-12-0) also can be called Pyridafenthion ; American Cyanamid 12503 ; O,O-Diethyl O-(6-oxo-1-phenyl-1,6-dihydro-3-pyridazinyl) phosphorothioate ; O-(1,6-Dihydro-6-oxo-1-phenyl-3-pyridazinyl) O,O-diethyl phosphorothioate and 1,4-Benzoquinone - 1,4-benzenediol (1:1) .

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