Registry of Toxic Effects of Chemical Substances (RTECS)

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

RTECS #

TC4375000

CAS #

6923-22-4

Updated

December 2013

Molecular Weight

223.19

Molecular Formula

C₇H₁₄NO₅P

Synonyms

(E)-Dimethyl 1-methyl-3-(methylamino)-3-oxo-1-propenyl phosphate
3-(Dimethoxyphosphinyloxy)N-methyl-cis-crotonamide
3-Hydroxy-N-methyl-cis-crotonamide dimethyl phosphate
3-Hydroxy-N-methylcrotonamide dimethyl phosphate
Apadrin
Azodrin
Azodrin insecticide
Azodrin-71
Biloborn
Bilobran
C 1414
Ciba 1414
cis-1-Methyl-2-methyl carbamoyl vinyl phosphate
Corophos
Crisodin
Crisodrin
Crotonamide, 3-hydroxy-N-methyl-, dimethylphosphate, (E)-
Dimethyl 1-methyl-2-(methylcarbamoyl)vinyl phosphate, cis
Dimethyl phosphate ester of 3-hydroxy-N-methyl-cis-crotonamide
Dimethyl phosphate ester with (E)-3-hydroxy-N-methylcrotonamide
Dimethyl phosphate of 3-hydroxy-N-methyl-cis-crotonamine
E-Monocrotophos
ENT 27,129
Glore phos 36
Hazodrin
Monocil
Monocil 40
Monocron
Monocrotophos
Monocrotophos (ACGIH)
Monodrin
Monokrotofosz (Hungarian)
Nuvacron
Nuvacron 20
O,O-Dimethyl-O-(1-methyl-2-N-methyl-carbamoyl)-vinyl-phosphat (German)
O,O-Dimethyl-O-(2-N-methylcarbamoyl-1-methyl)-vinyl-phosphat (German)
O,O-Dimethyl-O-(2-N-methylcarbamoyl-1-methyl-vinyl) phosphate
O,O-Dimethyl-O-(2-N-methylcarbamoyl-1-methyl-vinyl)-fosfaat (Dutch)
O,O-Dimetil-O-(2-N-metilcarbamoil-1-metil-vinil)-fosfato (Italian)
OMS 834
Phosphate de dimethyle et de 2-methylcarbamoyl 1-methyl vinyle (French)
Phosphoric acid, dimethyl 1-methyl-3-(methylamino)-3-oxo-1-propenyl ester, (E)-
Phosphoric acid, dimethyl ester, ester with cis-3-hydroxy-N-methylcrotonamide
Pillardrin
Plantdrin
SD 9129
Shell SD 9129
Susvin
Ulvair

Mutation Data and Reference

System Test	Route/Organism/Tissue	Dose	Reference
Cytogenetic Analysis	leukocyte/human	10 nmol/L	IJMRAQ 76,912,1982
Cytogenetic Analysis	lymphocyte/human	50 µg/L	BECTA6 41,737,1988
Cytogenetic Analysis	intraperitoneal/mouse	1500 µg/kg	IJMRAQ 76,912,1982
Cytogenetic Analysis	subcutaneous/mouse	5 mg/kg	CYTOAN 53,801,1988
Cytogenetic Analysis	oral/mouse	5 mg/kg	CYTOAN 53,801,1988
Cytogenetic Analysis	ovary/hamster	200 mg/L	MUREAV 188,241,1987
Cytogenetic Analysis	intraperitoneal/chicken	5 mg/kg	MUREAV 292,231,1993
DNA Damage	oral/other fish	0.313 ppm	FCTOD7 39,361,2001
gene conversion and mitotic recombination	/Saccharomyes cerevisiae	5 pph	NTIS** PB268-647
micronucleus test	intraperitoneal/chicken	1250 µg/kg	MUREAV 292,231,1993
micronucleus test	oral/chicken	5 mg/kg	MUREAV 292,231,1993
micronucleus test	intraperitoneal/mouse	1500 µg/kg	IJMRAQ 76,912,1982
mutation in mammalian somatic cells	lymphocyte/mouse	750 mg/L	NTIS** PB84-138973
mutation in microorganisms	/Salmonella typhimurium	500 µg/plate (+enzymatic activation step)	NTIS** PB84-138973
mutation in microorganisms	/Escherichia coli	5 mg/plate (-enzymatic activation step)	MUREAV 28,405,1975
mutation in microorganisms	/Saccharomyes cerevisiae	2 pph (+/-enzymatic activation step)	NTIS** PB84-138973
sister chromatid exchange	lymphocyte/human	12500 ng/L	BECTA6 41,737,1988
sister chromatid exchange	other cell types/rat	25 mg/L	MUREAV 188,311,1987
sister chromatid exchange	ovary/hamster	100 mg/L	MUREAV 188,311,1987
sperm morphology	oral/mouse	1800 µg/kg/5D- intermittent	BECTA6 41,189,1988
sperm morphology	intraperitoneal/mouse	12500 µg/kg	CYTOAN 53,801,1988
Unscheduled DNA Synthesis	fibroblast/human	1 mmol/L	NTIS** PB268-647

Reproductive Effects Data and References

Route/Organism	Dose	Effect	Reference
oral/rat	16800 µg/kg (14D prior to copulation)	Reproductive: Effects on embryo or fetus: Fetotoxicity (except death, e.g., stunted fetus)	INJPD2 26,126,1994

Acute Toxicity Data and References

Route/Organism	Dose	Effect	Reference
inhalation/rat	lethal concentration (50 percent kill): 63 mg/m³/4H	Behavioral: Tremor Behavioral: Muscle contraction or spasticity Lung, Thorax, or Respiration: Dyspnea	EGESAQ 24,173,1980
intraperitoneal/mouse	lethal dose (50 percent kill): 3800 µg/kg		TXAPA9 13,37,1968
intraperitoneal/rat	lowest published lethal dose: 20 mg/kg	Eye: Lacrimation Lung, Thorax, or Respiration: Dyspnea Gastrointestinal: Hypermotility, diarrhea	BECTA6 19,47,1978
intratracheal/rat	lethal dose (50 percent kill): 4500 µg/kg		JJATDK 19,133,1999
intravenous/mouse	lethal dose (50 percent kill): 9200 µg/kg		JPPMAB 19,612,1967
intravenous/rat	lethal dose (50 percent kill): 9200 µg/kg		NTIS** PB277-077
oral/chicken	lethal dose (50 percent kill): 3540 µg/kg	Peripheral Nerve and Sensation: Flaccid paralysis without anesthesia (usually neuromuscular blockage) Behavioral: Somnolence (general depressed activity) Behavioral: Convulsions or effect on seizure threshold	TXAPA9 11,49,1967
oral/duck	lethal dose (50 percent kill): 3360 µg/kg		TXAPA9 22,556,1972
oral/mouse	lethal dose (50 percent kill): 15 mg/kg		ARSIM* 20,21,1966
oral/pigeon	lethal dose (50 percent kill): 3 mg/kg		TXAPA9 20,57,1971
oral/quail	lethal dose (50 percent kill): 4 mg/kg		TXAPA9 20,57,1971
oral/rabbit	lethal dose (50 percent kill): 45 mg/kg	Behavioral: Convulsions or effect on seizure threshold Lung, Thorax, or Respiration: Respiratory stimulation Gastrointestinal: Hypermotility, diarrhea	NTIS** OTS0556237
oral/rat	lethal dose (50 percent kill): 8 mg/kg		FMCHA2 -,C209,1991
oral/rat	lowest published toxic dose: 6.4 mg/kg	Musculoskeletal: Other changes Biochemical: Enzyme inhibition, induction, or change in blood or tissue levels: True cholinesterase Biochemical: Metabolism (intermediary): Xanthine, purine or nucleotides including urate	TXCYAC 277,6,2010
oral/rat	lowest published toxic dose: 6.4 mg/kg	Brain and Coverings: Other degenerative changes Behavioral: Muscle weakness Biochemical: Enzyme inhibition, induction, or change in blood or tissue levels: True cholinesterase	NRTXDN 33,156,2012
oral/rat	lowest published toxic dose: 0.2 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 mg/kg	Behavioral: Change in motor activity (specific assay)	NETEEC 33,451,2011
oral/rat	lowest published toxic dose: 2 mg/kg	Behavioral: Tremor Behavioral: Change in motor activity (specific assay)	NETEEC 33,451,2011
oral/rat	lowest published toxic dose: 2 mg/kg	Behavioral: Tremor Behavioral: Change in motor activity (specific assay) 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): 800 µg/kg		JTCEEM 6(3),175,1986
skin/duck	lethal dose (50 percent kill): 30 mg/kg		TXAPA9 47,451,1979
skin/rabbit	lethal dose (50 percent kill): 270 mg/kg	Behavioral: Somnolence (general depressed activity) Behavioral: Convulsions or effect on seizure threshold Behavioral: Ataxia	INJPD2 18,102,1986
skin/rat	lethal dose (50 percent kill): 112 mg/kg		WRPCA2 9,119,1970
skin/wild bird	lethal dose (50 percent kill): 4200 µg/kg		TXAPA9 26,154,1973
subcutaneous/mouse	lethal dose (50 percent kill): 8710 µg/kg		JPPMAB 19,612,1967
subcutaneous/rabbit	lowest published toxic dose: 11.12 mg/kg	Musculoskeletal: Other changes Biochemical: Metabolism (intermediary): Effect on inflammation or mediation of inflammation	TXCYAC 191,33,2003
subcutaneous/rat	lethal dose (50 percent kill): 6964 µg/kg		BJPCBM 40,124,1970

Other Multiple Dose Data and References

Route/Organism	Dose	Effect	Reference
intraperitoneal/mammal (species unspecified)	lowest published toxic dose: 48 mg/kg/6D- intermittent	Blood: Changes in spleen Blood: Change in clotting factors Blood: Changes in cell count (unspecified)	HBPTO* 1,775,2001
oral/cattle	lowest published toxic dose: 14 mg/kg/28D- intermittent	Biochemical: Enzyme inhibition, induction, or change in blood or tissue levels: True cholinesterase Biochemical: Enzyme inhibition, induction, or change in blood or tissue levels: Transaminases Related to Chronic Data: Death in the "MULTIPLE DOSE" data type field	PHTOEH 62,290,1988
oral/chicken	lowest published toxic dose: 184 mg/kg/3W- continuous	Nutritional and Gross Metabolic: Weight loss or decreased weight gain Related to Chronic Data: Death in the "MULTIPLE DOSE" data type field	TXAPA9 11,49,1967
oral/chicken	lowest published toxic dose: 19.6 mg/kg/8W- continuous	Musculoskeletal: Other changes Biochemical: Enzyme inhibition, induction, or change in blood or tissue levels: Phosphatases Biochemical: Metabolism (intermediary): Plasma proteins not involving coagulation	TOPADD 32,364,2004
oral/rat	lowest published toxic dose: 34500 µg/kg/30D- intermittent	Autonomic Nervous System: Sympathomimetic Biochemical: Enzyme inhibition, induction, or change in blood or tissue levels: True cholinesterase Biochemical: Enzyme inhibition, induction, or change in blood or tissue levels: Monoamine oxidase	RPZHAW 31,605,1980
oral/rat	lowest published toxic dose: 99 mg/kg/16D- intermittent	Brain and Coverings: Other degenerative changes Biochemical: Enzyme inhibition, induction, or change in blood or tissue levels: Phosphatases Biochemical: Metabolism (intermediary): Other proteins	BECTA6 49,723,1992
oral/rat	lowest published toxic dose: 27 mg/kg/90D- intermittent	Liver: Changes in liver weight Endocrine: Changes in spleen weight Blood: Changes in serum composition (e.g. TP, bilirubin, cholesterol)	BECTA6 44,230,1990
skin/rat	lowest published toxic dose: 2800 mg/kg/28D- intermittent	Behavioral: Food intake (animal) Biochemical: Enzyme inhibition, induction, or change in blood or tissue levels: True cholinesterase	NTIS** OTS0556237

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		MUREAV 557,109,2004
TOXICOLOGY REVIEW		RREVAH 63,1,1976
TOXICOLOGY REVIEW		MUREAV 562,77,2004
TOXICOLOGY REVIEW		MUTAEX 21,93,2006
TOXICOLOGY REVIEW		ENTOX* -,306,2005
TOXICOLOGY REVIEW		NTAPM* -,629,1995
TOXICOLOGY REVIEW		MUREAV 721,27,2011

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* -,134,1998
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, inhal, 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, MAY2011
Occupational Exposure Limit-FRANCE	VME 0.25 mg/m³, FEB2006
Occupational Exposure Limit-HUNGARY	time-weighted average 0.25 mg/m³, Skin, SEP2000
Occupational Exposure Limit-ICELAND	time-weighted average 0.25 mg/m³, NOV2011
Occupational Exposure Limit-KOREA	time-weighted average 0.25 mg/m³, 2006
Occupational Exposure Limit-MEXICO	time-weighted average 0.25 mg/m³, 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, JAN2011
Occupational Exposure Limit-THE NETHERLANDS	MAC-TGG 0.25 mg/m³, 2003

NIOSH Documentation and Surveillance

Organization	Standard	Reference
National Institute for Occupational Safety and Health (NIOSH) Recommended Exposure Level TO MONOCROTOPHOS-air	10H time-weighted average 0.25 mg/m³	NIOSH* DHHS #92-100,1992

Status in Federal Agencies

Organization	Reference
EPA GENETOX PROGRAM 1988, Inconclusive: B subtilis rec assay; E coli polA without S9
EPA GENETOX PROGRAM 1988, Inconclusive: Histidine reversion-Ames test
EPA GENETOX PROGRAM 1988, Negative: D melanogaster Sex-linked lethal; TRP reversion
EPA GENETOX PROGRAM 1988, Positive: In vitro UDS-human fibroblast; S cerevisiae-homozygosis
EPA TSCA Section 8(d) unpublished health/safety studies
EPA TSCA TEST SUBMISSION (TSCATS) DATA BASE, JANUARY 2001
NIOSH Analytical Method, 1994: Organophosphorus pesticides, 5600
On EPA IRIS database

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Page last reviewed:March 7, 2014
Page last updated:February 6, 2017
Content source:
- National Institute for Occupational Safety and Health (NIOSH) Education and Information Division

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