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 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
In Vitro/Non-mammalian species, fibroblast	Inhibitor Concentration Low: 320 µg/L/48H	In 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/48H	In 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/48H	In Vitro Toxicity Studies: Other assays	TIVIEQ 29,155,2015
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/rat	lowest published toxic dose: 1.8 mg/kg	Behavioral: 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/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
Tank with water/Guppy	lowest published toxic concentration: 0.01 mg/L/90D	Endocrine: 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/90D	Related to Chronic Data: Changes in testicular weight	TXAPA9 263,163,2012

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: 54 mg/kg/30D- intermittent	Gastrointestinal: 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- intermittent	Nutritional 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- 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		RREVAH 46,1,1973
TOXICOLOGY REVIEW		RREVAH 63,1,1976
TOXICOLOGY REVIEW		MUREAV 557,109,2004
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
TOXICOLOGY REVIEW		TXAPA9 258,309,2012
TOXICOLOGY REVIEW		TXAPA9 268,157,2013
TOXICOLOGY REVIEW		TXAPA9 270,39,2013

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

Page last reviewed: November 16, 2018

Content source: National Institute for Occupational Safety and Health