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Registry of Toxic Effects of Chemical Substances (RTECS)

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

RTECS #

TC2800000

CAS #

13171-21-6

Updated

December 2013

Molecular Weight

299.72

Molecular Formula

C10H19ClNO5P

Synonyms

(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 (German)
(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-dimethylcarbamoyl-1-methylvinyl dimethyl phosphate
Apamidon
C 570
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 of 2-chloro-N,N-diethyl-3-hydroxycrotonamide
Dixon
ENT 25515
Fosfamidon (Dutch)
Fosfamidone (Italian)
Foszfamidon (Hungarian)
Merkon
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 (German)
OMS 1325
Phosphamidon
Phosphate de dimethyle et de (2-chloro-2-diethylcarbamoyl-1-methyl-vinyle) (French)

Mutation Data and Reference

System TestRoute/Organism/TissueDoseReference
body fluid assaySalmonella typhimurium/rat5800 µg/kgIJEBA6 24,305,1986
Cytogenetic Analysisintraperitoneal/rat1500 µg/kg/48H-continuousEMMUEG 12,235,1988
Cytogenetic Analysislymphocyte/human1900 µg/LMUREAV 31,103,1975
Cytogenetic Analysisleukocyte/human5 µmol/LIJEBA6 18,1145,1980
Cytogenetic Analysisoral/mouse5 mg/kgSOGEBZ 11,1534,1975
Cytogenetic Analysisintraperitoneal/mouse2 mg/kgIJEBA6 18,1145,1980
Cytogenetic Analysissubcutaneous/mouse5 mg/kgTOLED5 37,269,1987
DNA Damagefibroblast/mouse80 mg/L/24HMOCAT* 18,127,2003
host-mediated assaySalmonella typhimurium/mouse22500 µg/kg/3D-continuousBECTA6 25,277,1980
micronucleus testoral/mouse10 mg/kg/24HBECTA6 25,277,1980
micronucleus testintraperitoneal/mouse4 mg/kg/24HIJEBA6 18,1145,1980
mutation in microorganisms/Salmonella typhimurium5 µg/plate (+enzymatic activation step)IJEBA6 24,305,1986
mutation in microorganisms/Salmonella typhimurium9 mg/plate (-enzymatic activation step)ENMUDM 5(Suppl 1),3,1983
sex chromosome loss and nondisjunctionoral/Drosophila melanogaster79 ppb/2D-continuousMUREAV 189,277,1987
specific locus testoral/Drosophila melanogaster63 ppb/3D-continuousMUREAV 189,277,1987
sperm morphologyintraperitoneal/mouse3 mg/kg/4D- intermittentTOLED5 37,269,1987

Reproductive Effects Data and References

Route/OrganismDoseEffectReference
oral/mouse 5 mg/kg (7D 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 3150 µg/kg (1-18D 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 35 ppm (1-18D 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/OrganismDoseEffectReference
oral/rat lowest published toxic dose: 5400 mg/kg/80W- continuousTumorigenic: Equivocal tumorigenic agent by RTECS criteria

Vascular: Tumors

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

Acute Toxicity Data and References

Route/OrganismDoseEffectReference
inhalation/guinea pig lethal concentration (50 percent kill): 1300 mg/m3/4HPSDTAP 15,239,1974
inhalation/mouse lethal concentration (50 percent kill): 30 mg/m3/1HPSDTAP 15,239,1974
inhalation/rat lethal concentration (50 percent kill): 135 mg/m3/4HBehavioral: Tremor

Behavioral: Muscle contraction or spasticity

Lung, Thorax, or Respiration: Dyspnea
EGESAQ 24,173,1980
intraperitoneal/mouse lethal dose (50 percent kill): 5800 µg/kgTXAPA9 13,37,1968
intraperitoneal/rat lethal dose (50 percent kill): 8700 µg/kgPESTD5 17,351,1976
intratracheal/rat lethal dose (50 percent kill): 17 mg/kgJJATDK 19,133,1999
intravenous/mouse lethal dose (50 percent kill): 6 mg/kgBehavioral: Convulsions or effect on seizure threshold

Lung, Thorax, or Respiration: Other changes
ATXKA8 18,316,1960
oral/chicken Lethal dose: >100 mg/kgBrain 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/domestic animal lowest published lethal dose: 60 mg/kgPeripheral 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/duck lethal dose (50 percent kill): 3100 µg/kgDOEAAH 35,25,1979
oral/mouse lethal dose (50 percent kill): 6 mg/kgSPEADM 78-1,28,1978
oral/rabbit lethal dose (50 percent kill): 70 mg/kg85GYAV -,33,1971
oral/rat lethal dose (50 percent kill): 8 mg/kg85JCAE -,1138,1986
oral/rat lowest published toxic dose: 0.75 mg/kgBiochemical: Enzyme inhibition, induction, or change in blood or tissue levels: True cholinesteraseNETEEC 33,451,2011
oral/rat lowest published toxic dose: 5 mg/kgBehavioral: Tremor

Behavioral: Change in motor activity (specific assay)
NETEEC 33,451,2011
oral/rat lowest published toxic dose: 5 mg/kgPeripheral Nerve and Sensation: Fasciculations

Behavioral: Tremor

Biochemical: Enzyme inhibition, induction, or change in blood or tissue levels: True cholinesterase
NETEEC 33,451,2011
oral/wild bird lethal dose (50 percent kill): 1800 µg/kgTXAPA9 21,315,1972
skin/duck lethal dose (50 percent kill): 26 mg/kgTXAPA9 47,451,1979
skin/rabbit lethal dose (50 percent kill): 80 mg/kg85JCAE -,1138,1986
skin/rat lethal dose (50 percent kill): 125 mg/kgPHJOAV 185,361,1960
subcutaneous/mouse lethal dose (50 percent kill): 13200 µg/kgPeripheral Nerve and Sensation: Fasciculations

Eye: Lacrimation

Lung, Thorax, or Respiration: Dyspnea
AIPTAK 132,180,1961
subcutaneous/rat lethal dose (50 percent kill): 15 mg/kgIPPABX 4,253,1968

Other Multiple Dose Data and References

Route/OrganismDoseEffectReference
intravenous/rabbit lowest published toxic dose: 105 mg/kg/14D- continuousBiochemical: 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: 78 mg/kg/30D- intermittentEndocrine: Changes in spleen weight

Related to Chronic Data: Changes in ovarian weight

Related to Chronic Data: Changes in uterine weight
PCBPBS 87,204,2007
oral/mouse lowest published toxic dose: 117 mg/kg/30D- intermittentBrain and Coverings: Changes in brain weight

Liver: Changes in liver weight
PCBPBS 87,204,2007
oral/mouse lowest published toxic dose: 509 mg/kg/60D- continuousLiver: Other changes

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

Biochemical: Metabolism (intermediary): Other proteins
BECTA6 37,767,1986
oral/rabbit lowest published toxic dose: 32400 µg/kg/15D- intermittentBrain 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
oral/rat lowest published toxic dose: 262 mg/kg/21D- continuousBiochemical: 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/30D- intermittentBrain 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/rat lowest published toxic dose: 48.72 mg/kg/28D- intermittentImmunological Including Allergic: Decrease in cellular immune response

Immunological Including Allergic: Decrease in humoral immune response

Biochemical: Metabolism (intermediary): Lipids including transport
BJMRDK 41,765,2008
subcutaneous/rat lowest published toxic dose: 210 mg/kg/21D- continuousBiochemical: 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

OrganizationStandardReference
TOXICOLOGY REVIEWRREVAH 46,1,1973
TOXICOLOGY REVIEWDTTIAF 80,485,1973
TOXICOLOGY REVIEWRREVAH 63,1,1976
TOXICOLOGY REVIEWMUTAEX 21,93,2006
TOXICOLOGY REVIEWHTOPA* 1,501,2002
TOXICOLOGY REVIEWTOLED5 190,107,2009
TOXICOLOGY REVIEWMUREAV 721,27,2011

Standards and Regulations

OrganizationStandardReference
Environmental Protection Agency (EPA) Federal Insecticide, Fungicide, and Rodenticide Act (FIFRA) 1988 PESTICIDE SUBJECT TO REGISTRATION OR RE-REGISTRATIONFEREAC 54,7740,1989
Environmental Protection Agency (EPA) Federal Insecticide, Fungicide, and Rodenticide Act (FIFRA) 1998 STATUS OF PESTICIDESCancelledRBREV* -,142,1998
Occupational Exposure Limit-HUNGARYSkin, SEP2000

Status in Federal Agencies

OrganizationReference
EPA TSCA TEST SUBMISSION (TSCATS) DATA BASE, JANUARY 2001
NCI Carcinogenesis Bioassay (feed);equivocal evidence:ratNCITR* NCI-TR-16,1979
NCI Carcinogenesis Bioassay (feed);no evidence:mouseNCITR* NCI-TR-16,1979
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