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Substance Name: Azinphos-methyl [BSI:ISO]
RN: 86-50-0
UNII: 265842EWUV
InChIKey: CJJOSEISRRTUQB-UHFFFAOYSA-N

Note

  • An organothiophosphorus cholinesterase inhibitor. It has been used as an acaricide and as an insecticide.

Molecular Formula

  • C10-H12-N3-O3-P-S2

Molecular Weight

  • 317.3288
 

Classification Codes

Classification Codes

  • Acaricides
  • Agricultural Chemical
  • Cholinergic Agents
  • Cholinesterase Inhibitors
  • Enzyme Inhibitors
  • Insecticide
  • Insecticides
  • Mutation Data
  • Neurotransmitter Agents
  • Pesticides
  • Reproductive Effect
  • Tumor Data

Superlist Classification Codes

  • 2007 CERCLA Priority List, Rank: 135
  • 2011 CERCLA Priority List, Rank: 134
  • Reportable Quantity (RQ) = 1 lb
  • Threshold Planning Quantity (TPQ) = 10/10000 lb
  • TWA (0.2 mg/m3); skin
  • TWA (0.2 mg/m3, vapor and aerosol, should be carefully controlled to levels as low as possible); Skin; Not classifiable as a human carcinogen; Sensitizer; BEI

Names and Synonyms

Results Name

  • Azinphos-methyl [BSI:ISO]

Name of Substance

  • Azinphos-methyl [BSI:ISO]
  • Azinphosmethyl

MeSH Heading

  • Azinphosmethyl

Synonyms

  • 1,2,3-Benzotriazin-4(3H)-one, 3-(mercaptomethyl)-, O,O-dimethyl phosphorodithioate
  • 3-(Mercaptomethyl)-1,2,3-benzotriazin-4(3H)-one O,O-dimethyl phosphorodithioate S-ester
  • 3-Dimethoxyphosphinothioylthiomethyl-1,2,3-benzotriazin-4(3H)-one
  • 4-26-00-00460 (Beilstein Handbook Reference)
  • AI3-23233
  • Azinfos-methyl
  • Azinfos-methyl [Dutch]
  • Azinphos
  • Azinphos methyl
  • Azinphos-methyl
  • Azinphos-metile
  • Azinphos-metile [Italian]
  • BAY 17147
  • BAY 9027
  • Bayer 17147
  • Bayer 9027
  • Benzotriazine derivative of a methyl dithiophosphate
  • Benzotriazinedithiophosphoric acid dimethoxy ester
  • BRN 0280476
  • Carfene
  • Caswell No. 374
  • CCRIS 63
  • Cotneon
  • Cotnion
  • Cotnion methyl
  • Crysthion 2L
  • Crysthyon
  • Dimethyldithiophosphoric acid N-methylbenzazimide ester
  • EINECS 201-676-1
  • ENT 23,233
  • EPA Pesticide Chemical Code 058001
  • EPA Shaughnessy #058001
  • Gusathion
  • Gusathion 25
  • Gusathion K
  • Gusathion M
  • Gusathion methyl
  • Gusathion-20
  • Guthion
  • HSDB 1171
  • Metazintox
  • Methyl guthion
  • Methylazinphos
  • Methylgusathion
  • Metiltriazotion
  • N-Methylbenzazimide, dimethyldithiophosphoric acid ester
  • NCI-C00066
  • O,O-Dimethyl phosphorodithioate S-ester with 3-(mercaptomethyl)-1,2,3-benzotriazin-4(3H)-one (8CI)
  • O,O-Dimethyl S-(3,4-dihydro-4-keto-1,2,3-benzotriazinyl-3-methyl) dithiophosphate
  • O,O-Dimethyl S-(4-oxo-1,2,3-benzotriazino(3)-methyl) thiothionophosphate
  • O,O-Dimethyl S-(4-oxo-1,2,3-benzotriazino(3)-methyl)thiothionophosphate
  • O,O-Dimethyl S-(4-oxo-3H-1,2,3-benzotriazine-3-methyl)phosphorodithioate
  • O,O-Dimethyl S-(4-oxobenzotriazino-3-methyl)phosphorodithioate
  • O,O-Dimethyl S-4-oxo-1,2,3-benzotriazin-3(4H)-ylmethyl phosphorodithioate
  • O,O-Dimethyl-S-((4-oxo-3H-1,2,3-benzotriazin-3-yl)-methyl)-dithiofosfaat
  • O,O-Dimethyl-S-((4-oxo-3H-1,2,3-benzotriazin-3-yl)-methyl)-dithiofosfaat [Dutch]
  • O,O-Dimethyl-S-((4-oxo-3H-1,2,3-benzotriazin-3-yl)-methyl)-dithiophosphat
  • O,O-Dimethyl-S-((4-oxo-3H-1,2,3-benzotriazin-3-yl)-methyl)-dithiophosphat [German]
  • O,O-Dimethyl-S-(1,2,3-benzotriazinyl-4-keto)methyl phosphorodithioate
  • O,O-Dimethyl-S-(4-oxobenzotriazin-3-methyl)-dithiophosphat
  • O,O-Dimethyl-S-(4-oxobenzotriazin-3-methyl)-dithiophosphat [German]
  • O,O-Dimethyl-S-(benzaziminomethyl) dithiophosphate
  • O,O-Dimetil-S-((4-oxo-3H-1,2,3-benzotriazin-3-il)-metil)-ditiofosfato
  • O,O-Dimetil-S-((4-oxo-3H-1,2,3-benzotriazin-3-il)-metil)-ditiofosfato [Italian]
  • Phosphorodithioic acid, O,O-dimethyl ester, S-ester with 3-(mercaptomethyl)-1,2,3-benzotriazin-4(3H)-one
  • Phosphorodithioic acid, O,O-dimethyl S-((4-oxo-1,2,3-benzotriazin-3(4H)-yl)methyl) ester
  • R 1582
  • S-(3,4-Dihydro-4-oxo-benzo(alpha)(1,2,3)triazin-3-ylmethyl) O,O-dimethyl phosphorodithioate
  • S-3,4-Dihydro-4-oxobenzo(d)(1,2,3)triazin-3-ylmethyl O,O-dimethyl phosphorodithioate
  • UNII-265842EWUV

Systematic Names

  • Azinphos-methyl
  • Phosphorodithioic acid, O,O-dimethyl ester, S-ester with 3-(mercaptomethyl)-1,2,3-benzotriazin-4(3H)-one
  • Phosphorodithioic acid, O,O-dimethyl S-((4-oxo-1,2,3-benzotriazin-3(4H)-yl)methyl) ester

Superlist Names

  • Azinphos-methyl
  • Azinphosmethyl
  • Guthion
  • Phosphorodithioic acid, O,O-dimethyl S-((4-oxo-1,2,3-benzotriazin-3(4H)-yl)methyl) ester

Registry Numbers

CAS Registry Number

  • 86-50-0

FDA UNII

  • 265842EWUV

Other Registry Number

  • 54182-73-9

System Generated Number

  • 0000086500

Structure Descriptors

InChI

1S/C10H12N3O3PS2/c1-15-17(18,16-2)19-7-13-10(14)8-5-3-4-6-9(8)11-12-13/h3-6H,7H2,1-2H3

InChIKey

CJJOSEISRRTUQB-UHFFFAOYSA-N

Smiles

COP(=S)(OC)SCn1c(=O)c2ccccc2nn1

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - wild LD50 oral 8500ug/kg (8.5mg/kg)   Toxicology and Applied Pharmacology. Vol. 21, Pg. 315, 1972.
chicken LD50 oral 277mg/kg (277mg/kg) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Toxicology and Applied Pharmacology. Vol. 11, Pg. 49, 1967.
dog LD50 oral 10mg/kg (10mg/kg)   Pesticide Manual. Vol. 9, Pg. 46, 1991.
duck LD50 oral 136mg/kg (136mg/kg)   Down to Earth. Vol. 35, Pg. 25, 1979.
guinea pig LD50 intraperitoneal 40mg/kg (40mg/kg) GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE
Journal of Pharmacology and Experimental Therapeutics. Vol. 119, Pg. 208, 1957.
guinea pig LD50 oral 80mg/kg (80mg/kg)   Pesticide Chemicals Official Compendium, Association of the American Pesticide Control Officials, Inc., 1966. Vol. -, Pg. 570, 1966.
guinea pig LD50 skin > 280mg/kg (280mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: MUSCLE WEAKNESS
Kumamoto Medical Journal. Vol. 12, Pg. 313, 1959.
mouse LD50 intraperitoneal 4mg/kg (4mg/kg)   Proceedings of the Society for Experimental Biology and Medicine. Vol. 129, Pg. 699, 1968.
mouse LD50 oral 8600ug/kg (8.6mg/kg)   Proceedings of the European Society of Toxicology. Vol. 17, Pg. 292, 1976.
mouse LD50 skin 65mg/kg (65mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Kumamoto Medical Journal. Vol. 12, Pg. 313, 1959.
quail LD50 unreported 32200ug/kg (32.2mg/kg)   Farm Chemicals Handbook. Vol. -, Pg. C32, 1991.
rat LC50 inhalation 69mg/m3/1H (69mg/m3)   National Technical Information Service. Vol. PB277-077,
rat LD50 intraperitoneal 4900ug/kg (4.9mg/kg)   Proceedings of the Society for Experimental Biology and Medicine. Vol. 114, Pg. 509, 1963.
rat LD50 intravenous 7500ug/kg (7.5mg/kg)   National Technical Information Service. Vol. PB277-077,
rat LD50 oral 7mg/kg (7mg/kg)   Journal of Pharmacy and Pharmacology. Vol. 13, Pg. 435, 1961.
rat LD50 skin 88mg/kg (88mg/kg)   "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 1182, 1986.
rat LD50 unreported 15mg/kg (15mg/kg)   "Chemistry of Pesticides," Melnikov, N.N., New York, Springer-Verlag New York, Inc., 1971Vol. -, Pg. 371, 1971.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 73 deg C   EXP
log P (octanol-water) 2.75 (none)   EXP
Water Solubility 20.9 mg/L 20 EXP
Vapor Pressure 1.60E-06 mm Hg 20 EXP
Henry's Law Constant 2.39E-08 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.52E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.