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

RTECS #
TC4375000
CAS #
6923-22-4
See: NMAM or OSHA Methods
Updated
December 2017
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 TestRoute/Organism/TissueDoseReference
Cytogenetic Analysisleukocyte/human10 nmol/LIJMRAQ 76,912,1982
Cytogenetic Analysislymphocyte/human50 µg/LBECTA6 41,737,1988
Cytogenetic Analysisintraperitoneal/mouse1500 µg/kgIJMRAQ 76,912,1982
Cytogenetic Analysissubcutaneous/mouse5 mg/kgCYTOAN 53,801,1988
Cytogenetic Analysisoral/mouse5 mg/kgCYTOAN 53,801,1988
Cytogenetic Analysisovary/hamster200 mg/LMUREAV 188,241,1987
Cytogenetic Analysisintraperitoneal/chicken5 mg/kgMUREAV 292,231,1993
DNA Damageoral/other fish0.313 ppmFCTOD7 39,361,2001
gene conversion and mitotic recombination/Saccharomyes cerevisiae5 pphNTIS** PB268-647
micronucleus testintraperitoneal/chicken1250 µg/kgMUREAV 292,231,1993
micronucleus testoral/chicken5 mg/kgMUREAV 292,231,1993
micronucleus testintraperitoneal/mouse1500 µg/kgIJMRAQ 76,912,1982
mutation in mammalian somatic cellslymphocyte/mouse750 mg/LNTIS** PB84-138973
mutation in microorganisms/Salmonella typhimurium500 µg/plate (+enzymatic activation step)NTIS** PB84-138973
mutation in microorganisms/Escherichia coli5 mg/plate (-enzymatic activation step)MUREAV 28,405,1975
mutation in microorganisms/Saccharomyes cerevisiae2 pph (+/-enzymatic activation step)NTIS** PB84-138973
sister chromatid exchangelymphocyte/human12500 ng/LBECTA6 41,737,1988
sister chromatid exchangeother cell types/rat25 mg/LMUREAV 188,311,1987
sister chromatid exchangeovary/hamster100 mg/LMUREAV 188,311,1987
sperm morphologyoral/mouse1800 µg/kg/5D- intermittentBECTA6 41,189,1988
sperm morphologyintraperitoneal/mouse12500 µg/kgCYTOAN 53,801,1988
Unscheduled DNA Synthesisfibroblast/human1 mmol/LNTIS** PB268-647

Reproductive Effects Data and References

Route/OrganismDoseEffectReference
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/OrganismDoseEffectReference
In Vitro/Non-mammalian species, fibroblast Inhibitor Concentration Low: 320 µg/L/48HIn Vitro Toxicity Studies: Cell viability (mitochondrial reductase assays): MTT, XTT, MTS, WSTs assays etc.TIVIEQ 29,155,2015
In Vitro/Non-mammalian species, fibroblast Inhibitor Concentration (50 percent kill): 243.80 µg/L/48HIn Vitro Toxicity Studies: Cell viability (mitochondrial reductase assays): MTT, XTT, MTS, WSTs assays etc.TIVIEQ 29,155,2015
In Vitro/Non-mammalian species, fibroblast Inhibitor Concentration Low: 0.1 µg/L/48HIn Vitro Toxicity Studies: Other assaysTIVIEQ 29,155,2015
inhalation/rat lethal concentration (50 percent kill): 63 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): 3800 µg/kgTXAPA9 13,37,1968
intraperitoneal/rat lowest published lethal dose: 20 mg/kgEye: Lacrimation

Lung, Thorax, or Respiration: Dyspnea

Gastrointestinal: Hypermotility, diarrhea
BECTA6 19,47,1978
intratracheal/rat lethal dose (50 percent kill): 4500 µg/kgJJATDK 19,133,1999
intravenous/mouse lethal dose (50 percent kill): 9200 µg/kgJPPMAB 19,612,1967
intravenous/rat lethal dose (50 percent kill): 9200 µg/kgNTIS** PB277-077
oral/chicken lethal dose (50 percent kill): 3540 µg/kgPeripheral 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/kgTXAPA9 22,556,1972
oral/mouse lethal dose (50 percent kill): 15 mg/kgARSIM* 20,21,1966
oral/pigeon lethal dose (50 percent kill): 3 mg/kgTXAPA9 20,57,1971
oral/quail lethal dose (50 percent kill): 4 mg/kgTXAPA9 20,57,1971
oral/rabbit lethal dose (50 percent kill): 45 mg/kgBehavioral: 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/kgFMCHA2 -,C209,1991
oral/rat lowest published toxic dose: 6.4 mg/kgMusculoskeletal: 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/kgBrain 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/kgBiochemical: Enzyme inhibition, induction, or change in blood or tissue levels: True cholinesteraseNETEEC 33,451,2011
oral/rat lowest published toxic dose: 1 mg/kgBehavioral: Change in motor activity (specific assay)NETEEC 33,451,2011
oral/rat lowest published toxic dose: 2 mg/kgBehavioral: Tremor

Behavioral: Change in motor activity (specific assay)
NETEEC 33,451,2011
oral/rat lowest published toxic dose: 2 mg/kgBehavioral: 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/rat lowest published toxic dose: 1.8 mg/kgBehavioral: Tremor

Endocrine: Hyperglycemia

Biochemical: Enzyme inhibition, induction, or change in blood or tissue levels: Other transferases
TXCYAC 294,9,2012
oral/wild bird lethal dose (50 percent kill): 800 µg/kgJTCEEM 6(3),175,1986
skin/duck lethal dose (50 percent kill): 30 mg/kgTXAPA9 47,451,1979
skin/rabbit lethal dose (50 percent kill): 270 mg/kgBehavioral: 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/kgWRPCA2 9,119,1970
skin/wild bird lethal dose (50 percent kill): 4200 µg/kgTXAPA9 26,154,1973
subcutaneous/mouse lethal dose (50 percent kill): 8710 µg/kgJPPMAB 19,612,1967
subcutaneous/rabbit lowest published toxic dose: 11.12 mg/kgMusculoskeletal: 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/kgBJPCBM 40,124,1970
Tank with water/Guppy lowest published toxic concentration: 0.01 mg/L/90DEndocrine: Estrogenic

Reproductive: Paternal effects: Spermatogenesis (including genetic material, sperm morphology, motility, and count)
TXAPA9 263,163,2012
Tank with water/Guppy lowest published toxic concentration: 0.1 mg/L/90DRelated to Chronic Data: Changes in testicular weightTXAPA9 263,163,2012

Other Multiple Dose Data and References

Route/OrganismDoseEffectReference
intraperitoneal/mammal (species unspecified) lowest published toxic dose: 48 mg/kg/6D- intermittentBlood: 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- intermittentBiochemical: 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- continuousNutritional 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- continuousMusculoskeletal: 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: 54 mg/kg/30D- intermittentGastrointestinal: Decreased motility or constipation

Gastrointestinal: Necrotic changes

Biochemical: Enzyme inhibition, induction, or change in blood or tissue levels: Multiple enzyme effects
FCTOD7 71,236,2014
oral/rat lowest published toxic dose: 7.56 mg/kg/3W- intermittentNutritional and Gross Metabolic: Weight loss or decreased weight gain

Behavioral: Somnolence (general depressed activity)

Endocrine: Hypoglycemia
TXCYAC 307,103,2013
oral/rat lowest published toxic dose: 34500 µg/kg/30D- intermittentAutonomic 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- intermittentBrain 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- intermittentLiver: 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- intermittentBehavioral: Food intake (animal)

Biochemical: Enzyme inhibition, induction, or change in blood or tissue levels: True cholinesterase
NTIS** OTS0556237

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 REVIEWRREVAH 63,1,1976
TOXICOLOGY REVIEWMUREAV 557,109,2004
TOXICOLOGY REVIEWMUREAV 562,77,2004
TOXICOLOGY REVIEWMUTAEX 21,93,2006
TOXICOLOGY REVIEWENTOX* -,306,2005
TOXICOLOGY REVIEWNTAPM* -,629,1995
TOXICOLOGY REVIEWMUREAV 721,27,2011
TOXICOLOGY REVIEWTXAPA9 258,309,2012
TOXICOLOGY REVIEWTXAPA9 268,157,2013
TOXICOLOGY REVIEWTXAPA9 270,39,2013

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* -,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-AUSTRALIAtime-weighted average 0.25 mg/m3, JUL2008
Occupational Exposure Limit-AUSTRIAMAK-TMW 0.25 mg/m3;KZW 0.5 mg/m3, inhal, skin, 2007
Occupational Exposure Limit-BELGIUMtime-weighted average 0.25 mg/m3, Skin, MAR2002
Occupational Exposure Limit-DENMARKtime-weighted average 0.25 mg/m3, MAY2011
Occupational Exposure Limit-FRANCEVME 0.25 mg/m3, FEB2006
Occupational Exposure Limit-HUNGARYtime-weighted average 0.25 mg/m3, Skin, SEP2000
Occupational Exposure Limit-ICELANDtime-weighted average 0.25 mg/m3, NOV2011
Occupational Exposure Limit-KOREAtime-weighted average 0.25 mg/m3, 2006
Occupational Exposure Limit-MEXICOtime-weighted average 0.25 mg/m3, 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, JAN2011
Occupational Exposure Limit-THE NETHERLANDSMAC-TGG 0.25 mg/m3, 2003

NIOSH Documentation and Surveillance

OrganizationStandardReference
National Institute for Occupational Safety and Health (NIOSH) Recommended Exposure Level TO MONOCROTOPHOS-air10H time-weighted average 0.25 mg/m3NIOSH* DHHS #92-100,1992

Status in Federal Agencies

OrganizationReference
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
Page last reviewed: November 16, 2018