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Substance Name: Crufomate [USAN:INN:BAN]
RN: 299-86-5
UNII: V82Q65924L
InChIKey: BOFHKBLZOYVHSI-UHFFFAOYSA-N

Note

  • An insecticide used extensively for the control of cattle grubs, cattle lice, and hornflies.

Molecular Formula

  • C12-H19-Cl-N-O3-P

Molecular Weight

  • 291.7131
 

Classification Codes

Classification Codes

  • Agricultural Chemical
  • Anthelmintic (Veterinary)
  • Insecticide
  • Nematocide
  • Out-Dated Pesticide
  • Reproductive Effect

Superlist Classification Code

  • TWA 5 mg/m3; Not classifiable as a human carcinogen; BEI
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Names and Synonyms

Name of Substance

  • Crufomate
  • Crufomate [USAN:INN:BAN]
  • Ruelene

Synonyms

  • 2-Chloro-4-(1,1-dimethylethyl)phenyl methyl methylphosphoramidate
  • 4-06-00-03312 (Beilstein Handbook Reference)
  • 4-t-Butyl-2-chlorophenyl methyl methylphosphoramidate
  • 4-t-Butyl-2-chlorophenylmethyl methyl phosphoramidate
  • 4-tert-Butyl-2-chlorophenyl methyl methylphosphoramidate
  • 4-tert-Butyl-2-chlorophenyl N-methyl O-methylphosphoramidate
  • 4-tert-Butyl-2-chlorophenyl O-methyl methylphosphoroamidate
  • 4-tert. Butyl 2-chlorophenyl methylphosphoramidate de methyle
  • 4-tert. Butyl 2-chlorophenyl methylphosphoramidate de methyle [French]
  • AI3-25602
  • Amidofos
  • Amidophos
  • BRN 2133258
  • Caswell No. 263A
  • Crufomate
  • Crufomate A
  • Crufomate [ANSI]
  • Crufomato
  • Crufomato [INN-Spanish]
  • Crufomatum
  • Crufomatum [INN-Latin]
  • Dowco 132
  • EINECS 206-083-1
  • ENT 25,602-X
  • EPA Pesticide Chemical Code 012101
  • HSDB 1547
  • M-1261
  • Methylphosphoramidic acid 2-chloro-4-(1,1-dimethylethyl)phenyl methyl ester
  • Methylphosphoramidic acid, 4-t-butyl-2-chlorophenyl methyl ester
  • Montrel
  • N,O-Dimethyl-o-(4-tert-butyl-2-chlorophenyl)phosphoramidate
  • NSC 253463
  • O-(4-tert Butyl-2-chloor-fenyl)-O-methyl-fosforzuur-N-methyl-amide
  • O-(4-tert Butyl-2-chloor-fenyl)-O-methyl-fosforzuur-N-methyl-amide [Dutch]
  • O-(4-tert-Butyl-2-chlor-phenyl)-O-methyl-phosphorsaeure-N-methylamid
  • O-(4-tert-Butyl-2-chlor-phenyl)-O-methyl-phosphorsaeure-N-methylamid [German]
  • O-(4-tert-Butyl-2-chlorophenyl) O-methyl N-methylamido phosphate
  • O-(4-Terz.-butil-2-cloro-fenil)-O-metil-fosforammide
  • O-(4-Terz.-butil-2-cloro-fenil)-O-metil-fosforammide [Italian]
  • O-Methyl O-2-chloro-4-tert-butylphenyl N-methylamidophosphate
  • O-Methyl-O-(4-tert-butyl-2-chlorophenyl)methylphosphoramidate
  • Phenol, 4-t-butyl-2-chloro-, ester with methyl methylphosphoramidate
  • Phosphoramidic acid, 4-tert-butyl-2-chlorophenylphosphoramidate
  • Phosphoramidic acid, methyl-, 2-chloro-4-(1,1-dimethylethyl)phenyl methyl ester
  • Phosphoramidic acid, methyl-, 4-tert-butyl-2-chlorophenyl methyl ester
  • Phosphorsaeure-methyl-(2-chlor-4-tert-butyl-phenyl)-diestermethylamid
  • Ruelene
  • Ruelene 25E
  • Ruelene drench
  • Ruerene
  • Rulene
  • UNII-V82Q65924L

Systematic Names

  • Crufomate
  • Phosphoramidic acid methyl-, 2-chloro-4-(1,1-dimethylethyl)phenyl methyl ester
  • Phosphoramidic acid, methyl-, 2-chloro-4-(1,1-dimethylethyl)phenyl methyl ester
  • Phosphoramidic acid, methyl-, 4-tert-butyl-2-chlorophenyl methyl ester

Superlist Names

  • Crufomate
  • Phosphoramidic acid, methyl-, 2-chloro-4-(1,1-dimethylethyl)phenyl methyl ester

Registry Numbers

CAS Registry Number

  • 299-86-5

FDA UNII

  • V82Q65924L

System Generated Number

  • 0000299865

Structure Descriptors

InChI

1S/C12H19ClNO3P/c1-12(2,3)9-6-7-11(10(13)8-9)17-18(15,14-4)16-5/h6-8H,1-5H3,(H,14,15)

InChIKey

BOFHKBLZOYVHSI-UHFFFAOYSA-N

Smiles

CNP(=O)(OC)Oc1ccc(cc1Cl)C(C)(C)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - wild LD50 oral 100mg/kg (100mg/kg)   Toxicology and Applied Pharmacology. Vol. 21, Pg. 315, 1972.
dog LD50 oral 1gm/kg (1000mg/kg)   VM/SAC, Veterinary Medicine and Small Animal Clinician. Vol. 74, Pg. 1119, 1979.
guinea pig LD50 oral 1gm/kg (1000mg/kg) AUTONOMIC NERVOUS SYSTEM: OTHER (DIRECT) PARASYMPATHOMIMETIC

KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Food and Cosmetics Toxicology. Vol. 6, Pg. 185, 1968.
guinea pig LDLo subcutaneous 50mg/kg (50mg/kg)   Stauffer Chemical Co., Product Safety Information Sheets.
mammal (species unspecified) LD50 oral 251mg/kg (251mg/kg) BEHAVIORAL: FOOD INTAKE (ANIMAL)

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Veterinariya. Veterinary Science. Vol. 54(12), Pg. 94, 1978.
rabbit LD50 oral 400mg/kg (400mg/kg)   "Pesticide Index," Frear, E.H., ed., State College, PA, College Science Pub., 1969Vol. 5, Pg. 59, 1976.
rabbit LD50 skin 2gm/kg (2000mg/kg)   Special Publication of the Entomological Society of America. Vol. 78-1, Pg. 37, 1978.
rat LCLo inhalation 12mg/m3/4H (12mg/m3)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 29, 1982.
rat LD50 oral 460mg/kg (460mg/kg)   Toxicology and Applied Pharmacology. Vol. 14, Pg. 515, 1969.
rat LD50 unreported 770mg/kg (770mg/kg)   "Chemistry of Pesticides," Melnikov, N.N., New York, Springer-Verlag New York, Inc., 1971Vol. -, Pg. 317, 1971.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 60 deg C   EXP
log P (octanol-water) 3.42 (none)   EXP
Water Solubility 200 mg/L 25 EXP
Vapor Pressure 3.75E-05 mm Hg 25 EST
Henry's Law Constant 2.46E-09 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 3.43E-11 cm3/molecule-sec 25 EST

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