The Registry of Toxic Effects of Chemical Substances

Phosphoric acid, dimethyl ester, ester with 2 - chloro - N,N - diethyl - 3 - hydroxycrotonamide

RTECS #: TC2800000

CAS #: 13171-21-6

UPDATE: August 2004 MW: 299.72 MF: C10H19ClNO5P


NOTE:

TABLE OF CONTENTS:
  1. SYNONYMS:
  2. MUTATION DATA:
  3. REPRODUCTIVE EFFECTS DATA:
  4. TUMORIGENIC DATA:
  5. ACUTE TOXICITY DATA:
  6. OTHER MULTIPLE DOSE DATA:
  7. REVIEWS:
  8. STANDARDS AND REGULATIONS:
  9. STATUS IN FEDERAL AGENCIES:
  10. REFERENCES:

SYNONYMS:

  1. Apamidon
  2. (2 - Chlor - 3 - diaethylamino - 1 - methyl - 3 - oxo - prop - 1 - en - yl) - dimethyl - phosphat (German)
  3. (2 - Chloor - 3 - diethylamino - 1 - methyl - 3 - oxo - prop - 1 - en - yl) - dimethyl - fosfaat (Dutch)
  4. 2 - Chloro - 2 - diethylcarbamoyl - 1 - methylvinyl dimethylphosphate
  5. 1 - Chloro - diethylcarbamoyl - 1 - propen - 2 - yl dimethyl phosphate
  6. 2 - Chloro - 2 - dimethylcarbamoyl - 1 - methylvinyl dimethyl phosphate
  7. Ciba 570
  8. (2 - Cloro - 3 - dietilamino - 1 - metil - 3 - oxo - prop - 1 - en - il) - dimetil - fosfato (Italian)
  9. Crotonamide, 2 - chloro - N,N - diethyl - 3 - hydroxy - , dimethyl phosphate
  10. Dimecron
  11. Dimecron 100
  12. Dimethyl 2 - chloro - 2 - diethylcarbamoyl - 1 - methylvinyl phosphate
  13. O,O - Dimethyl O - (2 - chloro - 2 - (N,N - diethylcarbamoyl) - 1 - methylvinyl) phosphate
  14. Dimethyl diethylamido - 1 - chlorocrotonyl (2) phosphate
  1. O,O - Dimethyl - O - (1 - methyl - 2 - chlor - 2 - N,N - diaethyl - carbamoyl) - vinyl - phosphat (German)
  2. (O,O - Dimethyl - O - (1 - methyl - 2 - chloro - 2 - diethylcarbamoyl - vinyl) phosphate)
  3. Dimethyl phosphate of 2 - chloro - N,N - diethyl - 3 - hydroxycrotonamide
  4. Dixon
  5. ENT 25515
  6. Fosfamidon (Dutch)
  7. Fosfamidone (Italian)
  8. Foszfamidon (Hungarian)
  9. Merkon
  10. OMS 1325
  11. C 570
  12. NCI - C00588
  13. Phosphamidon
  14. Phosphate de dimethyle et de (2 - chloro - 2 - diethylcarbamoyl - 1 - methyl - vinyle) (French)


SKIN AND EYE IRRITATION DATA AND REFERENCES:

ROUTE/
ORGANISM 		DOSE
EFFECT

 REFERENCE
N/R
 N/R N/R N/R


MUTATION DATA AND REFERENCES:

SYSTEM TEST ROUTE/
ORGANISM/
TISSUE 		DOSE REFERENCE
body fluid assay rat
Salmonella typhimurium 		5,800 µg/kg IJEBA6 24,305,1986
cytogenetic analysis human lymphocyte 1,900 µg/L MUREAV 31,103,1975
cytogenetic analysis human leukocyte 5 µmol/L IJEBA6 18,1145,1980
cytogenetic analysis oral
mouse 		5 mg/kg SOGEBZ 11,1534,1975
cytogenetic analysis intraperitoneal
mouse 		2 mg/kg IJEBA6 18,1145,1980
cytogenetic analysis subcutaneous
mouse 		5 mg/kg TOLED5 37,269,1987
cytogenetic analysis intraperitoneal
rat 		1,500 µg/kg/48 hour- continuous EMMUEG 12,235,1988
DNA damage mouse fibroblast 80 mg/L/24 hour MOCAT* 18,127,2003
host-mediated assay mouse
Salmonella typhimurium 		22,500 µg/kg/3 day- continuous BECTA6 25,277,1980
mutation in microorganisms Salmonella typhimurium 5 µg/plate (+enzymatic activation step) IJEBA6 24,305,1986
mutation in microorganisms Salmonella typhimurium 9 mg/plate (-enzymatic activation step) ENMUDM 5(Suppl 1),3,1983
micronucleus test oral
mouse 		10 mg/kg/24 hour BECTA6 25,277,1980
micronucleus test intraperitoneal
mouse 		4 mg/kg/24 hour IJEBA6 18,1145,1980
sex chromosome loss and nondisjunction oral
Drosophila melanogaster 		79 ppb/2 day- continuous MUREAV 189,277,1987
specific locus test oral
Drosophila melanogaster 		63 ppb/3 day- continuous MUREAV 189,277,1987
sperm morphology intraperitoneal
mouse 		3 mg/kg/4 day- intermittent TOLED5 37,269,1987


REPRODUCTIVE EFFECTS DATA AND REFERENCES:

ROUTE/
ORGANISM 		DOSE
EFFECT

 REFERENCE
oral
mouse 		lowest published toxic dose: 5 mg/kg (7 day pregnant) Reproductive: Effects on fertility: Pre- implantation mortality (e.g., reduction in number of implants per female; total number of implants per corpora lutea)

Reproductive: Effects on fertility: Litter size (e.g., # fetuses per litter; measured before birth)

Reproductive: Effects on embryo or fetus: Fetotoxicity (except death, e.g., stunted fetus) 		TOLED5 42,101,1988
oral
mouse 		lowest published toxic dose: 3,150 µg/kg (1-18 day pregnant) Reproductive: Effects on fertility: Pre- implantation mortality (e.g., reduction in number of implants per female; total number of implants per corpora lutea)

Reproductive: Effects on fertility: Litter size (e.g., # fetuses per litter; measured before birth)

Reproductive: Effects on embryo or fetus: Fetotoxicity (except death, e.g., stunted fetus) 		TCMUD8 9,253,1989
oral
mouse 		lowest published toxic dose: 35 ppm (1-18 day pregnant) Reproductive: Effects on fertility: Pre- implantation mortality (e.g., reduction in number of implants per female; total number of implants per corpora lutea)

Reproductive: Effects on fertility: Litter size (e.g., # fetuses per litter; measured before birth)

Reproductive: Effects on embryo or fetus: Fetotoxicity (except death, e.g., stunted fetus) 		TCMUD8 9,253,1989


TUMORIGENIC DATA AND REFERENCES:

ROUTE/
ORGANISM 		DOSE
EFFECT

 REFERENCE
oral
rat 		lowest published toxic dose: 5,400 mg/kg/80 week- continuous Tumorigenic: Equivocal tumorigenic agent by RTECS criteria

Vascular: Tumors

Endocrine: Thyroid tumors 		NCITR* NCI-TR-16,1979


ACUTE TOXICITY DATA AND REFERENCES:

ROUTE/
ORGANISM 		DOSE
EFFECT

 REFERENCE
inhalation
guinea pig 		lethal concentration (50 percent kill): 1,300 mg/m3/4 hour N/R PSDTAP 15,239,1974
inhalation
mouse 		lethal concentration (50 percent kill): 30 mg/m3/1 hour N/R PSDTAP 15,239,1974
inhalation
rat 		lethal concentration (50 percent kill): 135 mg/m3/4 hour Behavioral: Tremor

Behavioral: Muscle contraction or spasticity

Lung, Thorax, or Respiration: Dyspnea 		EGESAQ 24,173,1980
intraperitoneal
mouse 		lethal dose (50 percent kill): 5,800 µg/kg N/R TXAPA9 13,37,1968
intraperitoneal
rat 		lethal dose (50 percent kill): 8,700 µg/kg N/R PESTD5 17,351,1976
intratracheal
rat 		lethal dose (50 percent kill): 17 mg/kg N/R JJATDK 19,133,1999
intravenous
mouse 		lethal dose (50 percent kill): 6 mg/kg Behavioral: Convulsions or effect on seizure threshold

Lung, Thorax, or Respiration: Other changes 		ATXKA8 18,316,1960
oral
wild bird 		lethal dose (50 percent kill): 1,800 µg/kg N/R TXAPA9 21,315,1972
oral
chicken 		lethal dose : >100 mg/kg Brain and Coverings: Other degenerative changes

Gastrointestinal: Hypermotility, diarrhea

Biochemical: Enzyme inhibition, induction, or change in blood or tissue levels: True cholinesterase 		VHTODE 41,290,1999
oral
duck 		lethal dose (50 percent kill): 3,100 µg/kg N/R DOEAAH 35,25,1979
oral
domestic animal 		lowest published lethal dose: 60 mg/kg Peripheral Nerve and Sensation: Spastic paralysis with/without sensory change

Behavioral: Convulsions or effect on seizure threshold

Kidney, Ureter, and Bladder: Changes in both tubules and glomeruli 		SJVSAE 23,54,1982
oral
mouse 		lethal dose (50 percent kill): 6 mg/kg N/R SPEADM 78-1,28,1978
oral
rat 		lethal dose (50 percent kill): 8 mg/kg N/R 85JCAE -,1138,1986
oral
rabbit 		lethal dose (50 percent kill): 70 mg/kg N/R 85GYAV -,33,1971
subcutaneous
mouse 		lethal dose (50 percent kill): 13,200 µg/kg Peripheral Nerve and Sensation: Fasciculations

Eye: Lacrimation

Lung, Thorax, or Respiration: Dyspnea 		AIPTAK 132,180,1961
subcutaneous
rat 		lethal dose (50 percent kill): 15 mg/kg N/R IPPABX 4,253,1968
skin
duck 		lethal dose (50 percent kill): 26 mg/kg N/R TXAPA9 47,451,1979
skin
rat 		lethal dose (50 percent kill): 125 mg/kg N/R PHJOAV 185,361,1960
skin
rabbit 		lethal dose (50 percent kill): 80 mg/kg N/R 85JCAE -,1138,1986


OTHER MULTIPLE DOSE DATA AND REFERENCES:

ROUTE/
ORGANISM 		DOSE
EFFECT

 REFERENCE
intravenous
rabbit 		lowest published toxic dose: 105 mg/kg/14 day- continuous Biochemical: Enzyme inhibition, induction, or change in blood or tissue levels: True cholinesterase

Related to Chronic Data: Death in the "MULTIPLE DOSE" data type field 		ATXKA8 18,316,1960
oral
mouse 		lowest published toxic dose: 509 mg/kg/60 day- continuous Liver: Other changes

Biochemical: Enzyme inhibition, induction, or change in blood or tissue levels: Phosphatases

Biochemical: Metabolism (intermediary): Other proteins 		BECTA6 37,767,1986
oral
rat 		lowest published toxic dose: 262 mg/kg/21 day- continuous Biochemical: Enzyme inhibition, induction, or change in blood or tissue levels: True cholinesterase

Related to Chronic Data: Death in the "MULTIPLE DOSE" data type field 		ATXKA8 18,316,1960
oral
rat 		lowest published toxic dose: 855 mg/kg/30 day- intermittent Brain and Coverings: Other degenerative changes

Biochemical: Enzyme inhibition, induction, or change in blood or tissue levels: True cholinesterase

Biochemical: Metabolism (intermediary): Amino acids (including renal excretion) 		BCTKAG 13,171,1980
oral
rabbit 		lowest published toxic dose: 32,400 µg/kg/15 day- intermittent Brain and Coverings: Changes in brain weight

Liver: Other changes

Biochemical: Enzyme inhibition, induction, or change in blood or tissue levels: True cholinesterase 		IJEBA6 18,1273,1980
subcutaneous
rat 		lowest published toxic dose: 210 mg/kg/21 day- continuous Biochemical: Enzyme inhibition, induction, or change in blood or tissue levels: True cholinesterase

Related to Chronic Data: Death in the "MULTIPLE DOSE" data type field 		ATXKA8 18,316,1960


REVIEWS:

ORGANIZATION STANDARD
REFERENCE
TOXICOLOGY REVIEW
RREVAH 46,1,1973
TOXICOLOGY REVIEW
DTTIAF 80,485,1973
TOXICOLOGY REVIEW
RREVAH 63,1,1976


STANDARDS AND REGULATIONS:

ORGANIZATION STANDARD
REFERENCE
Environmental Protection Agency (EPA) Federal Insecticide, Fungicide, and Rodenticide Act (FIFRA) 1988 PESTICIDE SUBJECT TO REGISTRATION OR RE-REGISTRATION FEREAC 54,7740,1989
Environmental Protection Agency (EPA) Federal Insecticide, Fungicide, and Rodenticide Act (FIFRA) 1998 STATUS OF PESTICIDES: Cancelled RBREV* -,142,1998


NIOSH DOCUMENTATION AND SURVEILLANCE:

ORGANIZATION STANDARD or SURVEY
REFERENCE
N/R N/R N/R


STATUS IN FEDERAL AGENCIES:

ORGANIZATION
REFERENCE
EPA TSCA TEST SUBMISSION (TSCATS) DATA BASE, JANUARY 2001
NCI Carcinogenesis Bioassay (feed);equivocal evidence:rat NCITR* NCI-TR-16,1979
NCI Carcinogenesis Bioassay (feed);no evidence:mouse NCITR* NCI-TR-16,1979


REFERENCES:

CODEN
REFERENCE
85GYAV "Pflanzenschutz-und Schaedlingsbekaempfungsmittel: Abriss einer Toxikologie und Therapie von Vergiftungen," 2nd ed., Klimmer, O.R., Hattingen, Fed. Rep. Ger., Hundt-Verlag, 1971
85JCAE "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986
AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898-
ATXKA8 Archiv fuer Toxikologie. (Berlin, Fed. Rep. Ger.) V.15-31, 1954-74. For publisher information, see ARTODN.
BCTKAG Bromatologia i Chemia Toksykologiczna. (Ars Polona, POB 1001, 00-068 Warsaw 1, Poland) V.4- 1971-
BECTA6 Bulletin of Environmental Contamination and Toxicology. (Springer-Verlag New York, Inc., Service Center, 44 Hartz Way, Secaucus, NJ 07094) V.1- 1966-
DOEAAH Down to Earth. (Dow Chemical USA, Agricultural Products Dept., Midland, MI 48640) V.1- 1945-
DTTIAF Deutsche Tieraerztliche Wochenschrift. (Hanover, Fed. Rep. Ger.) V.1-77, 1893-1970.
EGESAQ Egeszsegtudomany. (Kultura, POB 149, H-1389 Budapest, Hungary) V.1- 1957-
EMMUEG Environmental and Molecular Mutagenesis. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.10- 1987-
ENMUDM Environmental Mutagenesis. (New York, NY) V.1-9, 1979-87. For publisher information, see EMMUEG.
FEREAC Federal Register. (U.S. Government Printing Office, Supt. of Documents, Washington, DC 20402) V.1- 1936-
IJEBA6 Indian Journal of Experimental Biology. (Publications & Information Directorate, CSIR, Hillside Rd., New Delhi 110 012, India) V.1- 1963-
IPPABX Iugoslavica Physiologica et Pharmacologica Acta. (Jugoslovenska Knjiga, POB 36, YU-11001 Belgrade, Yugoslavia) V.1- 1965-
JJATDK JAT, Journal of Applied Toxicology. (John Wiley & Sons Ltd., Baffins Lane, Chichester, W. Sussex PO19 1UD, UK) V.1- 1981-
MOCAT* Molecular Cancer Therapeutics (Philadelphia, PA : American Association for Cancer Research) V.1- 2001-
MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964-
NCITR* National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD) No.0-205. For publisher information, see NTPTR*.
PESTD5 Proceedings of the European Society of Toxicology. (Amsterdam, Netherlands) V.16-18, 1975-77. Discontinued.
PHJOAV Pharmaceutical Journal. (Pharmaceutical Soc. of Great Britain, 1 Lambeth High St., London, SE1 7JN, UK) V.131- 1933-
PSDTAP Proceedings of the European Society for the Study of Drug Toxicity. (Princeton, NJ 08540) V.1-15, 1963-74. For publisher information, see PESTD5.
RBREV* Status of Pesticides in Registration, Reregistration, and Special Review (Rainbow Report), Special Review and Reregistration Division Office of Pesticide Programs U.S. Environmental Protection Agency, 401 M. Street, S.W., Washington, D.C. 20460, Spring 1998
RREVAH Residue Reviews. (Springer-Verlag New York, Inc., Service Center, 44 Hartz Way, Secaucus, NJ 07094) V.1- 1962-
SJVSAE Sudan Journal of Veterinary Science and Animal Husbandry (Khartoum, Sudan Veterinary Assn.) V.1- Mar. 1960-
SOGEBZ Soviet Genetics. English translation of GNKAA5. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013) V.2- 1966-
SPEADM Special Publication of the Entomological Society of America. (4603 Calvert Rd., College Park, MD 20740)
TCMUD8 Teratogenesis, Carcinogenesis, and Mutagenesis. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1980-
TOLED5 Toxicology Letters. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1977-
TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959-
VHTODE Veterinary and Human Toxicology. (American College of Veterinary and Comparative Toxicology, Publication Office, Comparative Toxicology, Manhattan, KS 66506) V.19- 1977-

Used as an insecticide

RTECS Compound Description:
   Agricultural Chemical
   Tumorigen
   Mutagen
   Reproductive Effector

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