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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 2016

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
TOXICOLOGY REVIEWTXAPA9 268,157,2013

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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