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

RTECS #: TC4375000

CAS #: 6923-22-4


UPDATE: May 2009 MW: 223.19 MF: C7H14NO5P


NOTE:

TABLE OF CONTENTS:
  1. SYNONYMS:
  2. MUTATION DATA:
  3. REPRODUCTIVE EFFECTS DATA:
  4. ACUTE TOXICITY DATA:
  5. OTHER MULTIPLE DOSE DATA:
  6. REVIEWS:
  7. STANDARDS AND REGULATIONS:
  8. NIOSH DOCUMENTATION AND SURVEILLANCE:
  9. STATUS IN FEDERAL AGENCIES:
  10. REFERENCES:

SYNONYMS:

  1. (E) - Dimethyl 1 - methyl - 3 - (methylamino) - 3 - oxo - 1 - propenyl phosphate
  2. 3 - (Dimethoxyphosphinyloxy) N - methyl - cis - crotonamide
  3. 3 - Hydroxy - N - methyl - cis - crotonamide dimethyl phosphate
  4. 3 - Hydroxy - N - methylcrotonamide dimethyl phosphate
  5. Apadrin
  6. Azodrin
  7. Azodrin insecticide
  8. Azodrin - 71
  9. Biloborn
  10. Bilobran
  11. C 1414
  12. Ciba 1414
  13. Corophos
  14. Crisodin
  15. Crisodrin
  16. Crotonamide, 3 - hydroxy - N - methyl - , dimethylphosphate, (E) -
  17. Dimethyl 1 - methyl - 2 - (methylcarbamoyl) vinyl phosphate, cis
  18. Dimethyl phosphate ester of 3 - hydroxy - N - methyl - cis - crotonamide
  19. Dimethyl phosphate ester with (E) - 3 - hydroxy - N - methylcrotonamide
  20. Dimethyl phosphate of 3 - hydroxy - N - methyl - cis - crotonamine
  21. E - Monocrotophos
  22. ENT 27,129
  23. Glore phos 36
  24. Hazodrin
  25. Monocil
  1. Monocil 40
  2. Monocron
  3. Monocrotophos
  4. Monocrotophos (ACGIH)
  5. Monodrin
  6. Monokrotofosz (Hungarian)
  7. Nuvacron
  8. Nuvacron 20
  9. O,O - Dimethyl - O - (1 - methyl - 2 - N - methyl - carbamoyl) - vinyl - phosphat (German)
  10. O,O - Dimethyl - O - (2 - N - methylcarbamoyl - 1 - methyl) - vinyl - phosphat (German)
  11. O,O - Dimethyl - O - (2 - N - methylcarbamoyl - 1 - methyl - vinyl) phosphate
  12. O,O - Dimethyl - O - (2 - N - methylcarbamoyl - 1 - methyl - vinyl) - fosfaat (Dutch)
  13. O,O - Dimetil - O - (2 - N - metilcarbamoil - 1 - metil - vinil) - fosfato (Italian)
  14. OMS 834
  15. Phosphate de dimethyle et de 2 - methylcarbamoyl 1 - methyl vinyle (French)
  16. Phosphoric acid, dimethyl 1 - methyl - 3 - (methylamino) - 3 - oxo - 1 - propenyl ester, (E) -
  17. Phosphoric acid, dimethyl ester, ester with cis - 3 - hydroxy - N - methylcrotonamide
  18. Pillardrin
  19. Plantdrin
  20. SD 9129
  21. Shell SD 9129
  22. Susvin
  23. Ulvair
  24. cis - 1 - Methyl - 2 - methyl carbamoyl vinyl phosphate


SKIN AND EYE IRRITATION DATA AND REFERENCES:

ROUTE/
ORGANISM
DOSE
EFFECT

REFERENCE
N/R
N/R N/R N/R


MUTATION DATA AND REFERENCES:

SYSTEM TEST ROUTE/
ORGANISM/
TISSUE
DOSE REFERENCE
cytogenetic analysis intraperitoneal
chicken
5 mg/kg MUREAV 292,231,1993
cytogenetic analysis hamster ovary 200 mg/L MUREAV 188,241,1987
cytogenetic analysis human leukocyte 10 nmol/L IJMRAQ 76,912,1982
cytogenetic analysis human lymphocyte 50 g/L BECTA6 41,737,1988
cytogenetic analysis intraperitoneal
mouse
1,500 g/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
DNA damage oral
other fish
0.313 ppm FCTOD7 39,361,2001
unscheduled DNA synthesis human fibroblast 1 mmol/L NTIS** PB268-647
mutation in microorganisms Escherichia coli 5 mg/plate (-enzymatic activation step) MUREAV 28,405,1975
mutation in microorganisms Salmonella typhimurium 500 g/plate (+enzymatic activation step) NTIS** PB84-138973
mutation in microorganisms Saccharomyes cerevisiae 2 pph (+/-enzymatic activation step) NTIS** PB84-138973
micronucleus test intraperitoneal
chicken
1,250 g/kg MUREAV 292,231,1993
micronucleus test oral
chicken
5 mg/kg MUREAV 292,231,1993
micronucleus test intraperitoneal
mouse
1,500 g/kg IJMRAQ 76,912,1982
gene conversion and mitotic recombination Saccharomyes cerevisiae 5 pph NTIS** PB268-647
mutation in mammalian somatic cells mouse lymphocyte 750 mg/L NTIS** PB84-138973
sister chromatid exchange hamster ovary 100 mg/L MUREAV 188,311,1987
sister chromatid exchange human lymphocyte 12,500 ng/L BECTA6 41,737,1988
sister chromatid exchange rat other cell types 25 mg/L MUREAV 188,311,1987
sperm morphology oral
mouse
1,800 g/kg/5 day- intermittent BECTA6 41,189,1988
sperm morphology intraperitoneal
mouse
12,500 g/kg CYTOAN 53,801,1988


REPRODUCTIVE EFFECTS DATA AND REFERENCES:

ROUTE/
ORGANISM
DOSE
EFFECT

REFERENCE
oral
rat
lowest published toxic dose: 16,800 g/kg (14 day prior to copulation) Reproductive: Effects on embryo or fetus: Fetotoxicity (except death, e.g., stunted fetus) INJPD2 26,126,1994


TUMORIGENIC DATA AND REFERENCES:

ROUTE/
ORGANISM
DOSE
EFFECT

REFERENCE
N/R
N/R N/R N/R


ACUTE TOXICITY DATA AND REFERENCES:

ROUTE/
ORGANISM
DOSE
EFFECT

REFERENCE
inhalation
rat
lethal concentration (50 percent kill): 63 mg/m3/4 hour Behavioral: Tremor

Behavioral: Muscle contraction or spasticity

Lung, Thorax, or Respiration: Dyspnea
EGESAQ 24,173,1980
intraperitoneal
mouse
lethal dose (50 percent kill): 3,800 g/kg N/R 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): 4,500 g/kg N/R JJATDK 19,133,1999
intravenous
mouse
lethal dose (50 percent kill): 9,200 g/kg N/R JPPMAB 19,612,1967
intravenous
rat
lethal dose (50 percent kill): 9,200 g/kg N/R NTIS** PB277-077
oral
wild bird
lethal dose (50 percent kill): 800 g/kg N/R JTCEEM 6(3),175,1986
oral
chicken
lethal dose (50 percent kill): 3,540 g/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): 3,360 g/kg N/R TXAPA9 22,556,1972
oral
mouse
lethal dose (50 percent kill): 15 mg/kg N/R ARSIM* 20,21,1966
oral
pigeon
lethal dose (50 percent kill): 3 mg/kg N/R TXAPA9 20,57,1971
oral
quail
lethal dose (50 percent kill): 4 mg/kg N/R TXAPA9 20,57,1971
oral
rat
lethal dose (50 percent kill): 8 mg/kg N/R FMCHA2 -,C209,1991
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
subcutaneous
mouse
lethal dose (50 percent kill): 8,710 g/kg N/R JPPMAB 19,612,1967
subcutaneous
rat
lethal dose (50 percent kill): 6,964 g/kg N/R BJPCBM 40,124,1970
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
skin
wild bird
lethal dose (50 percent kill): 4,200 g/kg N/R TXAPA9 26,154,1973
skin
duck
lethal dose (50 percent kill): 30 mg/kg N/R TXAPA9 47,451,1979
skin
rat
lethal dose (50 percent kill): 112 mg/kg N/R WRPCA2 9,119,1970
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


OTHER MULTIPLE DOSE DATA AND REFERENCES:

ROUTE/
ORGANISM
DOSE
EFFECT

REFERENCE
intraperitoneal
mammal (species unspecified)
lowest published toxic dose: 48 mg/kg/6 day- intermittent Blood: Changes in spleen

Blood: Change in clotting factors

Blood: Changes in cell count (unspecified)
HBPTO* 1,775,2001
oral
chicken
lowest published toxic dose: 184 mg/kg/3 week- 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/8 week- 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
cattle
lowest published toxic dose: 14 mg/kg/28 day- 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
rat
lowest published toxic dose: 34,500 g/kg/30 day- 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/16 day- 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/90 day- 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: 2,800 mg/kg/28 day- 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 (inhalable, vapor, skin) DTLVS* TLV/BEI,2007
American Conference of Governmental Industrial Hygienists (ACGIH) Threshold Limit Value Not classifiable as human carcinogen DTLVS* TLV/BEI,2007
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
MUTAEX 21,93,2006


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 - AUSTRALIA time-weighted average 0.25 mg/m3, JUL2008
Occupational Exposure Limit - BELGIUM time-weighted average 0.25 mg/m3, Skin, MAR2002
Occupational Exposure Limit - DENMARK time-weighted average 0.25 mg/m3, OCT 2002
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 - KOREA time-weighted average 0.25 mg/m3, 2006
Occupational Exposure Limit - MEXICO time-weighted average 0.25 mg/m3, 2004
Occupational Exposure Limit - THE NETHERLANDS MAC-TGG 0.25 mg/m3, 2003
Occupational Exposure Limit - NEW ZEALAND time-weighted average 0.25 mg/m3, skin, JAN2002
Occupational Exposure Limit - SWITZERLAND MAK- week 0.25 mg/m3, DEC2006
Occupational Exposure Limit IN ARGENTINA, BULGARIA, COLOMBIA, JORDAN American Conference of Governmental Industrial Hygienists (ACGIH) Threshold Limit Value;

Not classifiable as human carcinogen
Occupational Exposure Limit IN SINGAPORE, VIETNAM American Conference of Governmental Industrial Hygienists (ACGIH) Threshold Limit Value
Not classifiable as human carcinogen


NIOSH DOCUMENTATION AND SURVEILLANCE:

ORGANIZATION STANDARD or SURVEY
REFERENCE

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


STATUS IN FEDERAL AGENCIES:

ORGANIZATION
REFERENCE

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


REFERENCES:

CODEN
REFERENCE

ARSIM* Agricultural Research Service, USDA Information Memorandum. (Beltsville, MD 20705)
BECTA6 Bulletin of Environmental Contamination and Toxicology. (Springer-Verlag New York, Inc., Service Center, 44 Hartz Way, Secaucus, NJ 07094) V.1- 1966-
BJPCBM British Journal of Pharmacology. (Macmillan Press Ltd., Houndmills, Basingstoke, Hants. RG21 2XS, UK) V.34- 1968-
CYTOAN Cytologia. (Japan Pub. Trading Co. (USA), 1255 Howard St., San Francisco, CA 94103) V.1- 1929-
DTLVS* The Threshold Limit Values (TLVs) and Biological Exposure Indices (BEIs) booklet issues by American Conference of Governmental Industrial Hygienists (ACGIH), Cincinnati, OH, 1996
EGESAQ Egeszsegtudomany. (Kultura, POB 149, H-1389 Budapest, Hungary) V.1- 1957-
ENTOX* Encyclopedia of Toxicology: Reference Book, Elsevier, 2005
FCTOD7 Food and Chemical Toxicology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.20- 1982-
FEREAC Federal Register. (U.S. Government Printing Office, Supt. of Documents, Washington, DC 20402) V.1- 1936-
FMCHA2 Farm Chemicals Handbook. (Meister Pub., 37841 Euclid Ave., Willoughy, OH 44094)
HBPTO* Handbook of pesticide toxicology. Robert Krieger ed, Academic press, 2001
IJMRAQ Indian Journal of Medical Research. (Indian Council of Medical Research, Ansari Nagar, New Delhi 110 029, India) V.1- 1913-
INJPD2 Indian Journal of Pharmacology. (Dept. of Pharmacology, Baranas Hindu Univ., Varanasi 221 005, India) V.1- 1968(?)-
JJATDK JAT, Journal of Applied Toxicology. (John Wiley & Sons Ltd., Baffins Lane, Chichester, W. Sussex PO19 1UD, UK) V.1- 1981-
JPPMAB Journal of Pharmacy and Pharmacology. (Pharmaceutical Soc. of Great Britain, 1 Lambeth High St., London SEI 7JN, UK) V.1- 1949-
JTCEEM Journal de Toxicologie Clinique et Experimentale. (SPPIF, B.P.22, F-41353 Vineuil, France) V.5- 1985-
MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964-
MUTAEX Mutagenesis. (Oxford Univ. Press, Pinkhill House, Southfield Road, Eynsham, Oxford OX8 1JJ, UK) V.1- 1986-
NIOSH* National Institute of Occupational Safety and Health, U.S. Dept. of Health, Education, and Welfare, Reports and Memoranda.
NTIS** National Technical Information Service. (Springfield, VA 22161) Formerly U.S. Clearinghouse for Scientific & Technical Information.
PHTOEH Pharmacology and Toxicology (Copenhagen). (Munksgaard International Pub., POB 2148, DK-1016 Copenhagen K, Denmark) V.60- 1987-
RBREV* Status of Pesticides in Registration, Reregistration, and Special Review (Rainbow Report), Special Review and Reregistration Division Office of Pesticide Programs U.S. Environmental Protection Agency, 401 M. Street, S.W., Washington, D.C. 20460, Spring 1998
RPZHAW Roczniki Panstwowego Zakladu Higieny. (Ars Polona, POB 1001, 00-068 Warsaw 1, Poland) V.1- 1950-
RREVAH Residue Reviews. (Springer-Verlag New York, Inc., Service Center, 44 Hartz Way, Secaucus, NJ 07094) V.1- 1962-
TOPADD Toxicologic Pathology. (c/o Dr. F.A. de la Iglesia, Warner-Lambert Co., Pharmaceutical Research Div., POB 1047, Ann Arbor, MI 48106) V.6(3/4)- 1978-
TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959-
TXCYAC Toxicology. (Elsevier Scientific Pub. Ireland, Ltd., POB 85, Limerick, Ireland) V.1- 1973-
WRPCA2 World Review of Pest Control. (London, UK) V.1-10, 1962-71. Discontinued.

Used as an insecticide

RTECS Compound Description:
   Agricultural Chemical
   Mutagen
   Reproductive Effector
   Human Data

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