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

RTECS #

TC3850000

CAS #

141-66-2
See: NMAM or OSHA Methods

Updated

December 2017

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 Test	Route/Organism/Tissue	Dose	Reference
DNA Damage	other cell types/human	50 µmol/L/24H	FCTOD7 103,253,2017
gene conversion and mitotic recombination	/Saccharomyes cerevisiae	150 mmol/L/24H	IARCCD 10,161,1974
mutation in microorganisms	/Salmonella typhimurium	500 µg/plate (-enzymatic activation step)	JTEHD6 16,403,1985
mutation in microorganisms	/Escherichia coli	2 mmol/L/4H (-enzymatic activation step)	MUREAV 20,7,1973
sister chromatid exchange	ovary/hamster	300 µmol/L	JTEHD6 8,939,1981

Reproductive Effects Data and References

Route/Organism	Dose	Effect	Reference
oral/rat	375 µg/kg (12-14D pregnant)	Reproductive: Effects on newborn: Other postnatal measures or effects	EVMJB9 39,181,1979

Acute Toxicity Data and References

Route/Organism	Dose	Effect	Reference
inhalation/rat	lethal concentration (50 percent kill): 90 mg/m³/4H		PSDTAP 15,239,1974
intraperitoneal/mouse	lethal dose (50 percent kill): 9500 µg/kg		TXAPA9 16,446,1970
intravenous/mouse	lethal dose (50 percent kill): 9900 µg/kg		JPPMAB 19,612,1967
oral/chicken	lethal dose (50 percent kill): 7970 µg/kg	Behavioral: Convulsions or effect on seizure threshold	TXAPA9 7,606,1965
oral/duck	lethal dose (50 percent kill): 4140 µg/kg		TXAPA9 22,556,1972
oral/mouse	lethal dose (50 percent kill): 11 mg/kg		GUCHAZ 6,196,1973
oral/pigeon	lethal dose (50 percent kill): 2 mg/kg		TXAPA9 20,57,1971
oral/quail	lethal dose (50 percent kill): 4 mg/kg		TXAPA9 20,57,1971
oral/rat	lowest published toxic dose: 0.107 mg/kg	Biochemical: Enzyme inhibition, induction, or change in blood or tissue levels: True cholinesterase	NETEEC 33,451,2011
oral/rat	lowest published toxic dose: 1.06 mg/kg	Behavioral: Change in motor activity (specific assay)	NETEEC 33,451,2011
oral/rat	lethal dose (50 percent kill): 13 mg/kg		ARSIM* 20,6,1966
oral/wild bird	lethal dose (50 percent kill): 1 mg/kg		ASTTA8 (680),157,1979
skin/rabbit	lethal dose (50 percent kill): 168 mg/kg		GUCHAZ 6,196,1973
skin/rat	lethal dose (50 percent kill): 42 mg/kg		WRPCA2 9,119,1970
skin/wild bird	lethal dose (50 percent kill): 1300 µg/kg		TXAPA9 26,154,1973
subcutaneous/mouse	lethal dose (50 percent kill): 11500 µg/kg		JPPMAB 19,612,1967
subcutaneous/rat	lethal dose (50 percent kill): 8137 µg/kg		BJPCBM 40,124,1970
unreported route/rat	lethal dose (50 percent kill): 22 mg/kg		30ZDA9 -,314,1971

Other Multiple Dose Data and References

Route/Organism	Dose	Effect	Reference
oral/domestic bird	lowest published toxic dose: 3500 µg/kg/5D- continuous	Behavioral: 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

Organization	Standard	Reference
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 carcinogen	DTLVS* TLV/BEI,2013
TOXICOLOGY REVIEW		RREVAH 46,1,1973
TOXICOLOGY REVIEW		ENTOX* -,306,2005
TOXICOLOGY REVIEW		FEREAC 73,29456,2008
TOXICOLOGY REVIEW		FEREAC 73,52607,2008
TOXICOLOGY REVIEW		HETOEA 26,321,2007

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	Supported	RBREV* -,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-AUSTRALIA	time-weighted average 0.25 mg/m³, JUL2008
Occupational Exposure Limit-AUSTRIA	MAK-TMW 0.25 mg/m³;KZW 0.5 mg/m³, skin, 2007
Occupational Exposure Limit-BELGIUM	time-weighted average 0.25 mg/m³, Skin, MAR2002
Occupational Exposure Limit-DENMARK	time-weighted average 0.25 mg/m³, skin, MAY2011
Occupational Exposure Limit-FINLAND	time-weighted average 0.25 mg/m³, skin, NOV2011
Occupational Exposure Limit-FRANCE	VME 0.25 mg/m³, Skin, FEB2006
Occupational Exposure Limit-ICELAND	time-weighted average 0.25 mg/m³, skin, NOV2011
Occupational Exposure Limit-KOREA	time-weighted average 0.25 mg/m³, skin, 2006
Occupational Exposure Limit-MEXICO	time-weighted average 0.25 mg/m³ (skin), 2004
Occupational Exposure Limit-NEW ZEALAND	time-weighted average 0.25 mg/m³, skin, JAN2002
Occupational Exposure Limit-PERU	time-weighted average 0.05 mg/m³, JUL2005
Occupational Exposure Limit-SWITZERLAND	MAK-week 0.25 mg/m³, skin, JAN2011
Occupational Exposure Limit-THE NETHERLANDS	MAC-TGG 0.25 mg/m³, Skin, 2003

NIOSH Documentation and Surveillance

Organization	Standard	Reference
National Institute for Occupational Safety and Health (NIOSH) Recommended Exposure Level TO DICROTOPHOS-air	10H time-weighted average 0.25 mg/m³ (Sk)	NIOSH* DHHS #95-121,1995

Status in Federal Agencies

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

Page last reviewed: November 16, 2018

Content source: National Institute for Occupational Safety and Health