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Substance Name: Phosphamidon [ANSI:BSI:ISO]
RN: 13171-21-6
UNII: 7H857A6N6H
InChIKey: RGCLLPNLLBQHPF-HJWRWDBZSA-N

Note

  • An organophosphate cholinesterase inhibitor that is used as an insecticide.

Molecular Formula

  • C10-H19-Cl-N-O5-P

Molecular Weight

  • 299.689
 

Classification Codes

Classification Codes

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

Superlist Classification Code

  • Threshold Planning Quantity (TPQ) = 100 lb
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Names and Synonyms

Results Name

  • Phosphamidon [ANSI:BSI:ISO]

Name of Substance

  • Phosphamidon
  • Phosphamidon [ANSI:BSI:ISO]

MeSH Heading

  • Phosphamidon

Synonyms

  • (2-Chloor-3-diethylamino-1-methyl-3-oxo-prop-1-en-yl)-dimethyl-fosfaat
  • (2-Chloor-3-diethylamino-1-methyl-3-oxo-prop-1-en-yl)-dimethyl-fosfaat [Dutch]
  • (2-Chlor-3-diaethylamino-1-methyl-3-oxo-prop-1-en-yl)-dimethyl-phosphat
  • (2-Chlor-3-diaethylamino-1-methyl-3-oxo-prop-1-en-yl)-dimethyl-phosphat [German]
  • (2-Cloro-3-dietilamino-1-metil-3-oxo-prop-1-en-il)-dimetil-fosfato
  • (2-Cloro-3-dietilamino-1-metil-3-oxo-prop-1-en-il)-dimetil-fosfato [Italian]
  • (O,O-Dimethyl-O-(1-methyl-2-chloro-2-diethylcarbamoyl-vinyl) phosphate)
  • 1-Chloro-diethylcarbamoyl-1-propen-2-yl dimethyl phosphate
  • 2-Chloro-2-diethylcarbamoyl-1-methylvinyl dimethylphosphate
  • 2-Chloro-2-diethylcarbamyl-1-methylvinyl-dimethyl phosphate
  • 2-Chloro-2-dimethylcarbamoyl-1-methylvinyl dimethyl phosphate
  • 2-Chloro-3-(diethylamino)-1-methyl-3-oxo-1-propenyl dimethyl phosphate
  • 2-Chloro-3-dimethoxyphosphinoyloxy-N,N-diethylbut-2-enamide
  • 2-Chloro-N,N-diethyl-3-hydroxycrotonamide dimethyl phosphate
  • 2-Chloro-N,N-diethyl-3-hydroxycrotonamide ester with dimethyl phosphate
  • AI3-25515
  • Apamidon
  • C 570
  • Caswell No. 661
  • CCRIS 516
  • Ciba 570
  • Crotonamide, 2-chloro-N,N-diethyl-3-hydroxy-, dimethyl phosphate
  • Dimecron
  • Dimecron 100
  • Dimethyl 2-chloro-2-diethylcarbamoyl-1-methylvinyl phosphate
  • Dimethyl diethylamido-1-chlorocrotonyl (2) phosphate
  • Dimethyl phosphate ester with 2-chloro-N,N-diethyl-3-hydroxycrotonamide (8CI)
  • Dimethyl phosphate of 2-chloro-N,N-diethyl-3-hydroxycrotonamide
  • Dixon
  • EINECS 236-116-5
  • ENT 25515
  • EPA Pesticide Chemical Code 018201
  • Famfos
  • Fosfamidon
  • Fosfamidon [Dutch]
  • Fosfamidone
  • Fosfamidone [Italian]
  • Foszfamidon (Hungarian)
  • HSDB 1754
  • Merkon
  • ML 97
  • N,N-Diethyl 2-chloro-3-dimethylphosphate crotonamide
  • NCI-C00588
  • O,O-Dimethyl O-(2-chloro-2-(N,N-diethylcarbamoyl)-1-methylvinyl) phosphate
  • O,O-Dimethyl-O-(1-methyl-2-chlor-2-N,N-diaethyl-carbamoyl)-vinyl-phosphat
  • O,O-Dimethyl-O-(1-methyl-2-chlor-2-N,N-diaethyl-carbamoyl)-vinyl-phosphat [German]
  • OMS 1325
  • OR 1191
  • Phosphamidon
  • Phosphamidon 85 WSC
  • Phosphamidon, cis/trans mixture
  • Phosphamidone
  • Phosphate de dimethyle et de (2-chloro-2-diethylcarbamoyl-1-methyl-vinyle)
  • Phosphate de dimethyle et de (2-chloro-2-diethylcarbamoyl-1-methyl-vinyle) [French]
  • Sundaram 1975
  • UNII-7H857A6N6H

Systematic Names

  • Phosphamidon
  • Phosphoric acid, 2-chloro-3-(diethylamino)-1-methyl-3-oxo-1-propenyl dimethyl ester
  • Phosphoric acid, dimethyl ester, ester with 2-chloro-N,N-diethyl-3-hydroxycrotonamide

Superlist Names

  • Phosphamidon
  • Phosphoric acid, 2-chloro-3-(diethylamino)-1-methyl-3-oxo-1-propenyl dimethyl ester

Registry Numbers

CAS Registry Number

  • 13171-21-6

FDA UNII

  • 7H857A6N6H

System Generated Number

  • 0013171216

Structure Descriptors

InChI

1S/C10H19ClNO5P/c1-6-12(7-2)10(13)9(11)8(3)17-18(14,15-4)16-5/h6-7H2,1-5H3/b9-8-

InChIKey

RGCLLPNLLBQHPF-HJWRWDBZSA-N

Smiles

P(O\C(=C(\C(N(CC)CC)=O)Cl)C)(OC)(OC)=O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - wild LD50 oral 1800ug/kg (1.8mg/kg)   Toxicology and Applied Pharmacology. Vol. 21, Pg. 315, 1972.
chicken LD oral > 100mg/kg (100mg/kg)   Veterinary and Human Toxicology. Vol. 41, Pg. 290, 1999.
chicken LD oral > 100mg/kg (100mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BRAIN AND COVERINGS: OTHER DEGENERATIVE CHANGES
Veterinary and Human Toxicology. Vol. 41, Pg. 290, 1999.
duck LD50 oral 3100ug/kg (3.1mg/kg)   Down to Earth. Vol. 35, Pg. 25, 1979.
duck LD50 skin 26mg/kg (26mg/kg)   Toxicology and Applied Pharmacology. Vol. 47, Pg. 451, 1979.
guinea pig LC50 inhalation 1300mg/m3/4H (1300mg/m3)   Proceedings of the European Society for the Study of Drug Toxicity. Vol. 15, Pg. 239, 1974.
mouse LC50 inhalation 30mg/m3/1H (30mg/m3)   Proceedings of the European Society for the Study of Drug Toxicity. Vol. 15, Pg. 239, 1974.
mouse LD50 intraperitoneal 5800ug/kg (5.8mg/kg)   Toxicology and Applied Pharmacology. Vol. 13, Pg. 37, 1968.
mouse LD50 intravenous 6mg/kg (6mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Archiv fuer Toxikologie. Vol. 18, Pg. 316, 1960.
mouse LD50 oral 6mg/kg (6mg/kg)   Special Publication of the Entomological Society of America. Vol. 78-1, Pg. 28, 1978.
mouse LD50 subcutaneous 13200ug/kg (13.2mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

PERIPHERAL NERVE AND SENSATION: FASCICULATIONS

SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 132, Pg. 180, 1961.
rabbit LD50 oral 70mg/kg (70mg/kg)   "Pflanzenschutz-und Schaedlingsbekaempfungsmittel: Abriss einer Toxikologie und Therapie von Vergiftungen," 2nd ed., Klimmer, O.R., Hattingen, Fed. Rep. Ger., Hundt-Verlag, 1971Vol. -, Pg. 33, 1971.
rabbit LD50 skin 80mg/kg (80mg/kg)   "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 1138, 1986.
rat LC50 inhalation 135mg/m3/4H (135mg/m3) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

BEHAVIORAL: TREMOR
Egeszsegtudomany. Vol. 24, Pg. 173, 1980.
rat LD50 intraperitoneal 8700ug/kg (8.7mg/kg)   Proceedings of the European Society of Toxicology. Vol. 17, Pg. 351, 1976.
rat LD50 intratracheal 17mg/kg (17mg/kg)   JAT, Journal of Applied Toxicology. Vol. 19, Pg. 133, 1999.
rat LD50 oral 8mg/kg (8mg/kg)   "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 1138, 1986.
rat LD50 skin 125mg/kg (125mg/kg)   Pharmaceutical Journal. Vol. 185, Pg. 361, 1960.
rat LD50 subcutaneous 15mg/kg (15mg/kg)   Iugoslavica Physiologica et Pharmacologica Acta. Vol. 4, Pg. 253, 1968.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point -4.50E+01 deg C   EXP
log P (octanol-water) 0.79 (none)   EXP
Water Solubility 1.00E+06 mg/L 25 EXP
Vapor Pressure 1.65E-05 mm Hg 25 EXP
Henry's Law Constant 1.52E-12 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 3.68E-11 cm3/molecule-sec 25 EST

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