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Registry of Toxic Effects of Chemical Substances (RTECS)

Phosphoric acid, dimethyl ester, ester with (E)-3-hydroxy-N,N-dimethylcrotonamide

RTECS #

TC3850000

CAS #

141-66-2

Updated

December 2013

Molecular Weight

237.22

Molecular Formula

C8H16NO5P

Synonyms

2-Dimethyl cis-2-dimethyl-carbamoyl-1-methylvinyl phosphate
3-(Dimethoxyphosphinyloxy)-N,N dimethylisocrotonamide
3-(Dimethoxyphosphinyloxy)-N,N-dimethyl-cis-crotonamide
3-(Dimethylamino)-1-methyl-3-oxo-1-propenyl dimethyl phosphate
3-Hydroxydimethyl crotonamide dimethyl phosphate
3-Hydroxy-N,N-dimethyl-cis-crotonamide dimethyl phosphate
Bidirl
Bidrin
C 709
Carbicron
Ciba 709
cis-2-Dimethylcarbamoyl-1-methylvinyl dimethylphosphate
Crotonamide, 3-hydroxy-N,N-dimethyl-, cis-, dimethyl phosphate
Crotonamide, 3-hydroxy-N-N-dimethyl-, dimethyl phosphate, (E)-
Crotonamide, 3-hydroxy-N-N-dimethyl-, dimethyl phosphate, cis-
Diapadrin
Dicrotofos (Dutch)
Dicrotophos
Dicrotophos (ACGIH)
Dimethyl phosphate ester with 3-hydroxy-N,N-dimethyl-cis-crotonamide
Dimethyl phosphate of 3-hydroxy-N,N-dimethyl-cis-crotonamide
Ektafos
ENT 24,482
O,O-Dimethyl O-(N,N-dimethylcarbamoyl-1-methylvinyl) phosphate
O,O-Dimethyl-O-(1,4-dimethyl-3-oxo-4-aza-pent-1-enyl)fosfaat (Dutch)
O,O-Dimethyl-O-(1,4-dimethyl-3-oxo-4-aza-pent-1-enyl)phosphate
O,O-Dimethyl-O-(1-methyl-2-N,N-dimethyl-carbamoyl)-vinyl-phosphat (German)
O,O-Dimethyl-O-(2-dimethyl-carbamoyl-1-methyl-vinyl)phosphat (German)
O,O-Dimetil-O-(1,4-dimetil-3-oxo-4-aza-pent-1-enil)-fosfato (Italian)
OMS 253
Phosphate de dimethyle et de 2-dimethylcarbamoyl 1-methyl vinyle (French)
Phosphoric acid 3-(dimethylamino)-1-methyl-3-oxo-1-propenyl dimethyl ester
Phosphoric acid, dimethyl 1-methyl-N,N-(dimethylamino)-3-oxo-1-propenyl ester, (E)- (9CI)
Phosphoric acid, dimethyl ester, ester with cis-3-hydroxy-N,N-dimethylcrotonamide
SD 3562
Shell SD-3562

Mutation Data and Reference

System TestRoute/Organism/TissueDoseReference
gene conversion and mitotic recombination/Saccharomyes cerevisiae150 mmol/L/24HIARCCD 10,161,1974
mutation in microorganisms/Salmonella typhimurium500 µg/plate (-enzymatic activation step)JTEHD6 16,403,1985
mutation in microorganisms/Escherichia coli2 mmol/L/4H (-enzymatic activation step)MUREAV 20,7,1973
sister chromatid exchangeovary/hamster300 µmol/LJTEHD6 8,939,1981

Reproductive Effects Data and References

Route/OrganismDoseEffectReference
oral/rat 375 µg/kg (12-14D pregnant)Reproductive: Effects on newborn: Other postnatal measures or effectsEVMJB9 39,181,1979

Acute Toxicity Data and References

Route/OrganismDoseEffectReference
inhalation/rat lethal concentration (50 percent kill): 90 mg/m3/4HPSDTAP 15,239,1974
intraperitoneal/mouse lethal dose (50 percent kill): 9500 µg/kgTXAPA9 16,446,1970
intravenous/mouse lethal dose (50 percent kill): 9900 µg/kgJPPMAB 19,612,1967
oral/chicken lethal dose (50 percent kill): 7970 µg/kgBehavioral: Convulsions or effect on seizure thresholdTXAPA9 7,606,1965
oral/duck lethal dose (50 percent kill): 4140 µg/kgTXAPA9 22,556,1972
oral/mouse lethal dose (50 percent kill): 11 mg/kgGUCHAZ 6,196,1973
oral/pigeon lethal dose (50 percent kill): 2 mg/kgTXAPA9 20,57,1971
oral/quail lethal dose (50 percent kill): 4 mg/kgTXAPA9 20,57,1971
oral/rat lowest published toxic dose: 0.107 mg/kgBiochemical: Enzyme inhibition, induction, or change in blood or tissue levels: True cholinesteraseNETEEC 33,451,2011
oral/rat lowest published toxic dose: 1.06 mg/kgBehavioral: Change in motor activity (specific assay)NETEEC 33,451,2011
oral/rat lethal dose (50 percent kill): 13 mg/kgARSIM* 20,6,1966
oral/wild bird lethal dose (50 percent kill): 1 mg/kgASTTA8 (680),157,1979
skin/rabbit lethal dose (50 percent kill): 168 mg/kgGUCHAZ 6,196,1973
skin/rat lethal dose (50 percent kill): 42 mg/kgWRPCA2 9,119,1970
skin/wild bird lethal dose (50 percent kill): 1300 µg/kgTXAPA9 26,154,1973
subcutaneous/mouse lethal dose (50 percent kill): 11500 µg/kgJPPMAB 19,612,1967
subcutaneous/rat lethal dose (50 percent kill): 8137 µg/kgBJPCBM 40,124,1970
unreported route/rat lethal dose (50 percent kill): 22 mg/kg30ZDA9 -,314,1971

Other Multiple Dose Data and References

Route/OrganismDoseEffectReference
oral/domestic bird lowest published toxic dose: 3500 µg/kg/5D- continuousBehavioral: Food intake (animal)

Nutritional and Gross Metabolic: Weight loss or decreased weight gain

Related to Chronic Data: Death in the "MULTIPLE DOSE" data type field		AECTCV 11,617,1982

Reviews

OrganizationStandardReference
American Conference of Governmental Industrial Hygienists (ACGIH)Threshold Limit Value-time-weighted average 0.05 mg/m3 (inhal, vapor, skin)DTLVS* TLV/BEI,2013
American Conference of Governmental Industrial Hygienists (ACGIH)Threshold Limit Value-Not classifiable as a human carcinogenDTLVS* TLV/BEI,2013
TOXICOLOGY REVIEWRREVAH 46,1,1973
TOXICOLOGY REVIEWENTOX* -,306,2005
TOXICOLOGY REVIEWFEREAC 73,29456,2008
TOXICOLOGY REVIEWFEREAC 73,52607,2008
TOXICOLOGY REVIEWHETOEA 26,321,2007

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 PESTICIDESSupportedRBREV* -,112,1998
Occupational Exposure Limit IN ARGENTINA, BULGARIA, COLOMBIA, JORDAN check ACGIH TLV;
Occupational Exposure Limit IN SINGAPORE, VIETNAM check ACGIH TLV
Occupational Exposure Limit-AUSTRALIAtime-weighted average 0.25 mg/m3, JUL2008
Occupational Exposure Limit-AUSTRIAMAK-TMW 0.25 mg/m3;KZW 0.5 mg/m3, skin, 2007
Occupational Exposure Limit-BELGIUMtime-weighted average 0.25 mg/m3, Skin, MAR2002
Occupational Exposure Limit-DENMARKtime-weighted average 0.25 mg/m3, skin, MAY2011
Occupational Exposure Limit-FINLANDtime-weighted average 0.25 mg/m3, skin, NOV2011
Occupational Exposure Limit-FRANCEVME 0.25 mg/m3, Skin, FEB2006
Occupational Exposure Limit-ICELANDtime-weighted average 0.25 mg/m3, skin, NOV2011
Occupational Exposure Limit-KOREAtime-weighted average 0.25 mg/m3, skin, 2006
Occupational Exposure Limit-MEXICOtime-weighted average 0.25 mg/m3 (skin), 2004
Occupational Exposure Limit-NEW ZEALANDtime-weighted average 0.25 mg/m3, skin, JAN2002
Occupational Exposure Limit-PERUtime-weighted average 0.05 mg/m3, JUL2005
Occupational Exposure Limit-SWITZERLANDMAK-week 0.25 mg/m3, skin, JAN2011
Occupational Exposure Limit-THE NETHERLANDSMAC-TGG 0.25 mg/m3, Skin, 2003

NIOSH Documentation and Surveillance

OrganizationStandardReference
National Institute for Occupational Safety and Health (NIOSH) Recommended Exposure Level TO DICROTOPHOS-air10H time-weighted average 0.25 mg/m3 (Sk)NIOSH* DHHS #95-121,1995

Status in Federal Agencies

OrganizationReference
EPA GENETOX PROGRAM 1988, Positive: S cerevisiae gene conversion
NIOSH Analytical Method, 1994: Organophosphorus pesticides, 5600
On EPA IRIS database

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