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Substance Name: Trichlorfon [USAN]
RN: 52-68-6
UNII: DBF2DG4G2K
InChIKey: NFACJZMKEDPNKN-UHFFFAOYSA-N

Note

  • An organochlorophosphate cholinesterase inhibitor that is used as an insecticide for the control of flies and roaches. It is also used in anthelmintic compositions for animals. (From Merck, 11th ed)

Molecular Formula

  • C4-H8-Cl3-O4-P

Molecular Weight

  • 257.4362
 

Classification Codes

Classification Codes

  • Agricultural Chemical
  • Anthelmintic (Veterinary)
  • Anthelmintics
  • Anti-Infective Agents
  • Antiparasitic Agents
  • Cholinergic Agents
  • Cholinesterase Inhibitors
  • Enzyme Inhibitors
  • Human Data
  • Insecticide
  • Insecticides
  • Mutation Data
  • Neurotransmitter Agents
  • Pesticides
  • Reproductive Effect
  • Skin / Eye Irritant
  • Tumor Data

Superlist Classification Codes

  • Overall Carcinogenic Evaluation: Group 3
  • Reportable Quantity (RQ) = 100 lb
  • TWA: 1 mg/m3 inhalable fraction; Not classifiable as a human carcinogen; BEI

Names and Synonyms

Name of Substance

  • Metrifonate [INN]
  • Trichlorfon
  • Trichlorfon [USAN]

MeSH Heading

  • Trichlorfon

Synonyms

  • (+-)-Trichlorfon
  • (2,2,2-Trichloro-1-hydroxyethyl)-phosphonic acid dimethyl ester
  • 1-Hydroxy-2,2,2-trichloro-ethyle phosphonate de dimethyle
  • 1-Hydroxy-2,2,2-trichloro-ethyle phosphonate de dimethyle [French]
  • 1-Hydroxy-2,2,2-trichloroethylphosphonic acid dimethyl ester
  • 4-01-00-03147 (Beilstein Handbook Reference)
  • Aerol 1
  • Aerol 1 (pesticide)
  • Agroforotox
  • AI3-19763
  • Anthon
  • BAY 15922
  • BAY-a 9826
  • BAY-L 1359
  • Bayer 15922
  • Bayer L 13/59
  • Bayer L 1359
  • Bilarcil
  • Bovinox
  • Briten
  • Briton
  • Britten
  • BRN 1709434
  • Caswell No. 385
  • CCRIS 1289
  • Cekufon
  • Chlorak
  • Chlorfos
  • Chlorofos
  • Chloroftalm
  • Chlorophos
  • Chlorophosciclosom
  • Chlorophthalm
  • Chloroxyphos
  • Chlorphos
  • Ciclosom
  • Clorofos
  • Clorofos [Russian]
  • Combot
  • Combot equine
  • Danex
  • Denkaphon
  • DEP (pesticide)
  • DEP (VAN)
  • Depthon
  • DETF
  • Dicontal Fort
  • Dimethoxy-2,2,2-trichloro-1-hydroxy-ethyl phosphine oxide
  • Dimethoxy-2,2,2-trichloro-1-hydroxy-ethyl-phosphine oxide
  • Dimethyl (1-hydroxy-2,2,2-trichloroethyl)phosphonate
  • Dimethyl (2,2,2-trichloro-1-hydroxyethyl)phosphonate
  • Dimethyl 1-hydroxy-2,2,2-trichloroethyl phosphonate
  • Dimethyl 2,2,2-trichloro-1-hydroxyethylphosphonate
  • Dimethyltrichlorohydroxyethyl phosphonate
  • Dimetox
  • Dioxaphos
  • Dipterex
  • Dipterex 50
  • Dipterex SL
  • Dipterex WP 80
  • Diptevur
  • Ditrifon
  • Ditriphon 50
  • Dylox
  • Dyrex
  • Dyvon
  • EINECS 200-149-3
  • ENT 19,763
  • EPA Pesticide Chemical Code 057901
  • Equino-aid
  • Flibol E
  • Fliegenteller
  • Forotox
  • Foschlor
  • Foschlor 25
  • Foschlor R
  • Foschlor R-50
  • Foschlor R-50 (VAN)
  • Foschlorem
  • Foschlorem [Polish]
  • HSDB 881
  • Hypodermacid
  • Khloroftalm
  • Leivasom
  • Loisol
  • Masoten
  • Mazoten
  • Methyl chlorophos
  • Metrifonate
  • Metrifonato
  • Metrifonato [INN-Spanish]
  • Metrifonatum
  • Metrifonatum [INN-Latin]
  • Metriphonate
  • Metriphonatum
  • NCI-C54831
  • Neguvon
  • NSC 8923
  • O,O Dimetil 2,2,2-trichloro 1 hidroxietil fosfonato (Portugese)
  • O,O-Dimethyl (1-hydroxy-2,2,2-trichloroethyl)phosphonate
  • O,O-Dimethyl (1-oxy-2,2,2-trichloroethyl)phosphonate
  • O,O-Dimethyl (2,2,2-trichloro-1-hydroxyethyl)phosphonate
  • O,O-Dimethyl (2,2,2-trichloro-1-hydroxyethyl)phosponate
  • O,O-Dimethyl-(1-hydroxy-2,2,2-trichloraethyl)phosphonsaeure ester
  • O,O-Dimethyl-(1-hydroxy-2,2,2-trichloraethyl)phosphonsaeure ester [German]
  • O,O-Dimethyl-(1-hydroxy-2,2,2-trichloraethyl)phosphosaeure ester
  • O,O-Dimethyl-(1-hydroxy-2,2,2-trichlorathyl)-phosphat
  • O,O-Dimethyl-(1-hydroxy-2,2,2-trichlorathyl)-phosphat [German]
  • O,O-Dimethyl-(2,2,2-trichloor-1-hydroxy-ethyl)-fosfonaat
  • O,O-Dimethyl-(2,2,2-trichloor-1-hydroxy-ethyl)-fosfonaat [Dutch]
  • O,O-Dimethyl-(2,2,2-trichlor-1-hydroxy-aethyl)phosphonat
  • O,O-Dimethyl-(2,2,2-trichlor-1-hydroxy-aethyl)phosphonat [German]
  • O,O-Dimethyl-1-hydroxy-2,2,2-trichloroethylphosphonate
  • O,O-Dimethyl-1-oxy-2,2,2-trichloroethyl phosphonate
  • O,O-Dimetil-(2,2,2-tricloro-1-idrossi-etil)-fosfonato
  • O,O-Dimetil-(2,2,2-tricloro-1-idrossi-etil)-fosfonato [Italian]
  • OMS 800
  • Phoschlor
  • Phoschlor R50
  • Phosphonic acid, (1-hydroxy-2,2,2-trichloroethyl)-, dimethyl ester
  • Phosphonic acid, (2,2,2-trichloro-1-hydroxyethyl)-, dimethyl ester
  • Polfoschlor
  • Proxol
  • Ricifon
  • Ritsifon
  • Satox 20WSC
  • Soldep
  • Sotipox
  • Trichloorfon
  • Trichloorfon [Dutch]
  • Trichlorfon
  • Trichlorfon [BSI:ISO]
  • Trichlorfon [German]
  • Trichlorofon
  • Trichlorophon
  • Trichlorphon
  • Trichlorphon FN
  • Trichlorphon [ISO]
  • Trinex
  • Tugon
  • Tugon fly bait
  • Tugon stable spray
  • UNII-DBF2DG4G2K
  • Vermicide bayer 2349
  • Volfartol
  • Votexit
  • WEC 50
  • Wotexit

Systematic Names

  • Dimethyl(2,2,2-trichloro-1-hydroxyethyl)phosphonate
  • Phosphonic acid, (2,2,2-trichloro-1-hydroxyethyl)-, dimethyl ester
  • Trichlorfon

Superlist Names

  • Phosphonic acid, (2,2,2-trichloro-1-hydroxyethyl)-, dimethyl ester
  • Trichlorfon

Registry Numbers

CAS Registry Number

  • 52-68-6

FDA UNII

  • DBF2DG4G2K

Other Registry Numbers

  • 37333-09-8
  • 50924-44-2
  • 56042-25-2
  • 66758-31-4

System Generated Number

  • 0000052686

Structure Descriptors

InChI

1S/C4H8Cl3O4P/c1-10-12(9,11-2)3(8)4(5,6)7/h3,8H,1-2H3

InChIKey

NFACJZMKEDPNKN-UHFFFAOYSA-N

Smiles

COP(=O)(OC)C(O)C(Cl)(Cl)Cl

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - wild LD50 oral 37mg/kg (37mg/kg)   Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.
cat LD50 oral 97mg/kg (97mg/kg)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 60, 1982.
cat LD50 unreported 98mg/kg (98mg/kg) LUNGS, THORAX, OR RESPIRATION: STRUCTURAL OR FUNCTIONAL CHANGE IN TRACHEA OR BRONCHI

LUNGS, THORAX, OR RESPIRATION: BRONCHIOLAR CONSTRICTION

LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA
Russian Pharmacology and Toxicology Vol. 50, Pg. 61, 1987.
chicken LD50 oral 75mg/kg (75mg/kg)   Environmental Quality and Safety. Vol. 3, Pg. 173, 1974.
chicken LD50 subcutaneous 125mg/kg (125mg/kg) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE) Biochemical Pharmacology. Vol. 12, Pg. 1377, 1963.
dog LD50 intravenous 150mg/kg (150mg/kg) LIVER: OTHER CHANGES

BLOOD: HEMORRHAGE

CARDIAC: OTHER CHANGES
Archives of Toxicology. Vol. 41, Pg. 3, 1978.
dog LD50 oral 400mg/kg (400mg/kg) LIVER: OTHER CHANGES

CARDIAC: OTHER CHANGES

BLOOD: HEMORRHAGE
Archives of Toxicology. Vol. 41, Pg. 3, 1978.
dog LD50 subcutaneous 269mg/kg (269mg/kg) BEHAVIORAL: TREMOR

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS

GASTROINTESTINAL: OTHER CHANGES
Revista do Centro de Ciencias Rurais Vol. 7(1), Pg. 23, 1977.
guinea pig LD50 intraperitoneal 300mg/kg (300mg/kg)   AMA Archives of Industrial Health. Vol. 11, Pg. 53, 1955.
guinea pig LDLo oral 420mg/kg (420mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES Bulletin of the University of Miami School of Medicine and Jackson Memorial Hospital. Vol. 9, Pg. 7, 1955.
hamster LD50 intraperitoneal 1gm/kg (1000mg/kg)   Archives of Toxicology. Vol. 58, Pg. 152, 1986.
human TCLo inhalation 1710ug/m3/90D (1.71mg/m3)   British Journal of Industrial Medicine. Vol. 43, Pg. 414, 1986.
mammal (species unspecified) LD50 skin > 2800mg/kg (2800mg/kg)   Archives of Toxicology. Vol. 41, Pg. 3, 1978.
mammal (species unspecified) LD50 unreported 295mg/kg (295mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 38(8), Pg. 101, 1973.
monkey LD oral > 1gm/kg (1000mg/kg) GASTROINTESTINAL: OTHER CHANGES

SPINAL CORD: OTHER DEGENERATIVE CHANGES

MUSCULOSKELETAL: OTHER CHANGES
Journal of UOEH Vol. 5(Suppl), Pg. 125, 1983.
mouse LD50 intraperitoneal 196mg/kg (196mg/kg)   Toxicology and Applied Pharmacology. Vol. 2, Pg. 495, 1960.
mouse LD50 intravenous 290mg/kg (290mg/kg) BLOOD: HEMORRHAGE

LIVER: OTHER CHANGES

CARDIAC: OTHER CHANGES
Archives of Toxicology. Vol. 41, Pg. 3, 1978.
mouse LD50 oral 300mg/kg (300mg/kg)   Special Publication of the Entomological Society of America. Vol. 78-1, Pg. 26, 1978.
mouse LD50 skin 1710mg/kg (1710mg/kg)   Yakkyoku. Pharmacy. Vol. 37, Pg. 597, 1986.
mouse LD50 subcutaneous 267mg/kg (267mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 31, Pg. 555, 1981.
mouse LD50 unreported 445mg/kg (445mg/kg)   Pharmaceutical Chemistry Journal Vol. 3, Pg. 508, 1969.
quail LD50 oral 73110ug/kg (73.11mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Hokkaidoritsu Eisei Kenkyushoho. Report of the Hokkaido Institute of Public Health. Vol. 24, Pg. 35, 1974.
rabbit LD skin > 1500mg/kg (1500mg/kg)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 8(10), Pg. 54, 1964.
rabbit LD skin > 1500mg/kg (1500mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, IRRITATIVE: AFTER SYSTEMIC EXPOSURE" Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 8(10), Pg. 54, 1964.
rabbit LD50 intraperitoneal 60mg/kg (60mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS
American Journal of Ophthalmology. Vol. 53, Pg. 512, 1962.
rabbit LD50 oral 160mg/kg (160mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 31, Pg. 555, 1981.
rabbit LDLo intramuscular 500mg/kg (500mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

VASCULAR: OTHER CHANGES

BLOOD: HEMORRHAGE
Medycyna Weterynaryjna. Veterinary Medicine. Vol. 35, Pg. 479, 1979.
rat LC50 inhalation 1300mg/m3 (1300mg/m3)   Archiv fuer Geschwulstforschung. Vol. 48, Pg. 112, 1978.
rat LD50 intramuscular 395mg/kg (395mg/kg) LIVER: OTHER CHANGES

BLOOD: HEMORRHAGE

CARDIAC: OTHER CHANGES
Archives of Toxicology. Vol. 41, Pg. 3, 1978.
rat LD50 intraperitoneal 160mg/kg (160mg/kg)   Advances in Pest Control Research. Vol. 4, Pg. 117, 1961.
rat LD50 oral 450mg/kg (450mg/kg)   United States Patent Document. Vol. #5006545,
rat LD50 skin 2gm/kg (2000mg/kg)   Archiv fuer Geschwulstforschung. Vol. 48, Pg. 112, 1978.
rat LD50 subcutaneous 400mg/kg (400mg/kg)   Journal of Economic Entomology. Vol. 50, Pg. 356, 1957.
rat LD50 unreported 550mg/kg (550mg/kg)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 26(6), Pg. 21, 1982.
women TDLo oral 1mL/kg (1mL/kg) BEHAVIORAL: COMA

AUTONOMIC NERVOUS SYSTEM: OTHER (DIRECT) PARASYMPATHOMIMETIC

BEHAVIORAL: MUSCLE WEAKNESS
Journal of UOEH Vol. 5(Suppl), Pg. 125, 1983.
women TDLo oral 1200uL/kg (1.2mL/kg) SPINAL CORD: OTHER DEGENERATIVE CHANGES

BEHAVIORAL: COMA

AUTONOMIC NERVOUS SYSTEM: OTHER (DIRECT) PARASYMPATHOMIMETIC
Journal of UOEH Vol. 5(Suppl), Pg. 125, 1983.
women TDLo oral 1364uL/kg (1.364mL/kg) AUTONOMIC NERVOUS SYSTEM: GAGLION BLOCK

BEHAVIORAL: GENERAL ANESTHETIC

BEHAVIORAL: SLEEP
Rinsho Shinkeigaku. Clinical Neurology. Vol. 21, Pg. 993, 1981.
women TDLo oral 240mg/kg (240mg/kg) SPINAL CORD: OTHER DEGENERATIVE CHANGES

PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE

BEHAVIORAL: COMA
Journal of UOEH Vol. 5(Suppl), Pg. 125, 1983.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 77 deg C   EXP
log P (octanol-water) 0.51 (none)   EXP
Water Solubility 1.20E+05 mg/L 25 EXP
Vapor Pressure 7.80E-06 mm Hg 20 EXP
Henry's Law Constant 1.70E-11 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 6.36E-12 cm3/molecule-sec 25 EST

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