*** CHEMICAL IDENTIFICATION ***
RTECS NUMBER : TC3850000
CHEMICAL NAME : Phosphoric acid, dimethyl ester, ester with
(E)-3-hydroxy-N,N-dimethylcrotonamide
CAS REGISTRY NUMBER : 141-66-2
BEILSTEIN REFERENCE NO. : 1880084
LAST UPDATED : 199712
DATA ITEMS CITED : 38
MOLECULAR FORMULA : C8-H16-N-O5-P
MOLECULAR WEIGHT : 237.22
WISWESSER LINE NOTATION : 1OPO&O1&OY1&U1VN1&1 -C
COMPOUND DESCRIPTOR : Agricultural Chemical
Mutagen
SYNONYMS/TRADE NAMES :
* Bidirl
* Bidrin
* C 709
* Carbicron
* Ciba 709
* Crotonamide, 3-hydroxy-N,N-dimethyl-, cis-, dimethyl phosphate
* Crotonamide, 3-hydroxy-N-N-dimethyl-, dimethyl phosphate, cis-
* Crotonamide, 3-hydroxy-N-N-dimethyl-, dimethyl phosphate, (E)-
* Diapadrin
* Dicrotofos
* Dicrotophos
* 3-(Dimethoxyphosphinyloxy)-N,N-dimethyl-cis-crotonamide
* 3-(Dimethoxyphosphinyloxy)-N,N dimethylisocrotonamide
* 3-(Dimethylamino)-1-methyl-3-oxo-1-propenyl dimethyl phosphate
* cis-2-Dimethylcarbamoyl-1-methylvinyl dimethylphosphate
* O,O-Dimethyl-O-(2-dimethyl-carbamoyl-1-methyl-vinyl)phosphat
* 2-Dimethyl cis-2-dimethyl-carbamoyl-1-methylvinyl phosphate
* 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
* 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
* Dimethyl phosphate of 3-hydroxy-N,N-dimethyl-cis-crotonamide
* Dimethyl phosphate ester with 3-hydroxy-N,N-dimethyl-cis-crotonamide
* O,O-Dimetil-O-(1,4-dimetil-3-oxo-4-aza-pent-1-enil)-fosfato
* Ektafos
* ENT 24,482
* 3-Hydroxydimethyl crotonamide dimethyl phosphate
* 3-Hydroxy-N,N-dimethyl-cis-crotonamide dimethyl phosphate
* OMS 253
* Phosphate de dimethyle et de 2-dimethylcarbamoyl 1-methyl vinyle
* Phosphoric acid 3-(dimethylamino)-1-methyl-3-oxo-1-propenyl dimethyl
ester
* Phosphoric acid, dimethyl ester, ester with
cis-3-hydroxy-N,N-dimethylcrotonamide
* Phosphoric acid, dimethyl 1-methyl-N,N-(dimethylamino)-3-oxo-1-propenyl
ester, (E)-
* SD 3562
* Shell SD-3562
*** HEALTH HAZARD DATA ***
** ACUTE TOXICITY DATA **
TYPE OF TEST : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE : Oral
SPECIES OBSERVED : Rodent - rat
DOSE/DURATION : 13 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ARSIM* Agricultural Research Service, USDA Information Memorandum.
(Beltsville, MD 20705) Volume(issue)/page/year: 20,6,1966
TYPE OF TEST : LC50 - Lethal concentration, 50 percent kill
ROUTE OF EXPOSURE : Inhalation
SPECIES OBSERVED : Rodent - rat
DOSE/DURATION : 90 mg/m3/4H
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
PSDTAP Proceedings of the European Society for the Study of Drug Toxicity.
(Princeton, NJ 08540) V.1-15, 1963-74. For publisher information, see
PESTD5. Volume(issue)/page/year: 15,239,1974
TYPE OF TEST : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE : Administration onto the skin
SPECIES OBSERVED : Rodent - rat
DOSE/DURATION : 42 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
WRPCA2 World Review of Pest Control. (London, UK) V.1-10, 1962-71.
Discontinued. Volume(issue)/page/year: 9,119,1970
TYPE OF TEST : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE : Subcutaneous
SPECIES OBSERVED : Rodent - rat
DOSE/DURATION : 8137 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
BJPCBM British Journal of Pharmacology. (Macmillan Press Ltd., Houndmills,
Basingstoke, Hants. RG21 2XS, UK) V.34- 1968- Volume(issue)/page/year:
40,124,1970
TYPE OF TEST : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE : Unreported
SPECIES OBSERVED : Rodent - rat
DOSE/DURATION : 22 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
30ZDA9 "Chemistry of Pesticides," Melnikov, N.N., New York, Springer-Verlag
New York, Inc., 1971 Volume(issue)/page/year: -,314,1971
TYPE OF TEST : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE : Oral
SPECIES OBSERVED : Rodent - mouse
DOSE/DURATION : 11 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
GUCHAZ Guide to the Chemicals Used in Crop Protection. (Information Canada,
171 Slater St., Ottawa, Ont., Canada) Volume(issue)/page/year: 6,196,1973
TYPE OF TEST : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE : Intraperitoneal
SPECIES OBSERVED : Rodent - mouse
DOSE/DURATION : 9500 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E.
First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year:
16,446,1970
TYPE OF TEST : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE : Subcutaneous
SPECIES OBSERVED : Rodent - mouse
DOSE/DURATION : 11500 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
JPPMAB Journal of Pharmacy and Pharmacology. (Pharmaceutical Soc. of Great
Britain, 1 Lambeth High St., London SEI 7JN, UK) V.1- 1949-
Volume(issue)/page/year: 19,612,1967
TYPE OF TEST : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE : Intravenous
SPECIES OBSERVED : Rodent - mouse
DOSE/DURATION : 9900 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
JPPMAB Journal of Pharmacy and Pharmacology. (Pharmaceutical Soc. of Great
Britain, 1 Lambeth High St., London SEI 7JN, UK) V.1- 1949-
Volume(issue)/page/year: 19,612,1967
TYPE OF TEST : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE : Administration onto the skin
SPECIES OBSERVED : Rodent - rabbit
DOSE/DURATION : 168 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
GUCHAZ Guide to the Chemicals Used in Crop Protection. (Information Canada,
171 Slater St., Ottawa, Ont., Canada) Volume(issue)/page/year: 6,196,1973
TYPE OF TEST : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE : Oral
SPECIES OBSERVED : Bird - pigeon
DOSE/DURATION : 2 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E.
First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year:
20,57,1971
TYPE OF TEST : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE : Oral
SPECIES OBSERVED : Bird - chicken
DOSE/DURATION : 7970 ug/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold
REFERENCE :
TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E.
First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year:
7,606,1965
TYPE OF TEST : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE : Oral
SPECIES OBSERVED : Bird - quail
DOSE/DURATION : 4 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E.
First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year:
20,57,1971
TYPE OF TEST : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE : Oral
SPECIES OBSERVED : Bird - duck
DOSE/DURATION : 4140 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E.
First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year:
22,556,1972
TYPE OF TEST : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE : Oral
SPECIES OBSERVED : Bird - wild bird species
DOSE/DURATION : 1 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ASTTA8 ASTM Special Technical Publication. (American Soc. for Testing
Materials, 1916 Race St., Philadelphia, PA 19103) No.1- 1911-
Volume(issue)/page/year: (680),157,1979
TYPE OF TEST : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE : Administration onto the skin
SPECIES OBSERVED : Bird - wild bird species
DOSE/DURATION : 1300 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E.
First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year:
26,154,1973
** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE : Oral
SPECIES OBSERVED : Bird - domestic
DOSE/DURATION : 3500 ug/kg/5D-C
TOXIC EFFECTS :
Behavioral - food intake (animal)
Nutritional and Gross Metabolic - weight loss or decreased weight gain
Related to Chronic Data - death
REFERENCE :
AECTCV Archives of Environmental Contamination and Toxicology.
(Springer-Verlag New York, Inc., Service Center, 44 Hartz Way, Secaucus, NJ
070944) V.1- 1973- Volume(issue)/page/year: 11,617,1982
** MUTATION DATA **
TYPE OF TEST : Mutation in microorganisms
TEST SYSTEM : Bacteria - Salmonella typhimurium
DOSE/DURATION : 500 ug/plate
REFERENCE :
JTEHD6 Journal of Toxicology and Environmental Health. (Hemisphere Pub.,
1025 Vermont Ave., NW, Washington, DC 20005) V.1- 1975/76-
Volume(issue)/page/year: 16,403,1985
TYPE OF TEST : Mutation in microorganisms
TEST SYSTEM : Bacteria - Escherichia coli
DOSE/DURATION : 2 mmol/L/4H
REFERENCE :
MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE
Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 20,7,1973
TYPE OF TEST : Gene conversion and mitotic recombination
TEST SYSTEM : Yeast - Saccharomyces cerevisiae
DOSE/DURATION : 150 mmol/L/24H
REFERENCE :
IARCCD IARC Scientific Publications. (Geneva, Switzerland) No.1-26,
1971-78. For publisher information, see IAPUDO. Volume(issue)/page/year:
10,161,1974
TYPE OF TEST : Sister chromatid exchange
TEST SYSTEM : Rodent - hamster Ovary
DOSE/DURATION : 300 umol/L
REFERENCE :
JTEHD6 Journal of Toxicology and Environmental Health. (Hemisphere Pub.,
1025 Vermont Ave., NW, Washington, DC 20005) V.1- 1975/76-
Volume(issue)/page/year: 8,939,1981
*** REVIEWS ***
ACGIH TLV-Not classifiable as a human carcinogen
DTLVS* The Threshold Limit Values (TLVs) and Biological Exposure Indices
(BEIs) booklet issues by American Conference of Governmental Industrial
Hygienists (ACGIH), Cincinnati, OH, 1996 Volume(issue)/page/year:
TLV/BEI,1997
ACGIH TLV-TWA 0.25 mg/m3 (skin)
DTLVS* The Threshold Limit Values (TLVs) and Biological Exposure Indices
(BEIs) booklet issues by American Conference of Governmental Industrial
Hygienists (ACGIH), Cincinnati, OH, 1996 Volume(issue)/page/year:
TLV/BEI,1997
TOXICOLOGY REVIEW
RREVAH Residue Reviews. (Springer-Verlag New York, Inc., Service Center, 44
Hartz Way, Secaucus, NJ 07094) V.1- 1962- Volume(issue)/page/year:
46,1,1973
*** U.S. STANDARDS AND REGULATIONS ***
EPA FIFRA 1988 PESTICIDE SUBJECT TO REGISTRATION OR RE-REGISTRATION
FEREAC Federal Register. (U.S. Government Printing Office, Supt. of
Documents, Washington, DC 20402) V.1- 1936- Volume(issue)/page/year:
54,7740,1989
*** OCCUPATIONAL EXPOSURE LIMITS ***
OEL-AUSTRALIA:TWA 0.25 mg/m3;Skin JAN 1993
OEL-BELGIUM:TWA 0.25 mg/m3;Skin JAN 1993
OEL-DENMARK:TWA 0.25 mg/m3;Skin JAN 1993
OEL-FINLAND:TWA 0.25 mg/m3 JAN 1993
OEL-FRANCE:TWA 0.25 mg/m3;Skin JAN 1993
OEL-THE NETHERLANDS:TWA 0.25 mg/m3;Skin JAN 1993
OEL-SWITZERLAND:TWA 0.25 mg/m3;Skin JAN 1993
OEL IN BULGARIA, COLOMBIA, JORDAN, KOREA check ACGIH TLV
OEL IN NEW ZEALAND, SINGAPORE, VIETNAM check ACGIH TLV
*** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA ***
NIOSH RECOMMENDED EXPOSURE LEVEL (REL) :
NIOSH REL TO DICROTOPHOS-air:10H TWA 0.25 mg/m3 (Sk)
REFERENCE :
NIOSH* National Institute for Occupational Safety and Health, U.S. Dept. of
Health, Education, and Welfare, Reports and Memoranda.
Volume(issue)/page/year: DHHS #92-100,1992
*** STATUS IN U.S. ***
EPA GENETOX PROGRAM 1988, Positive: S cerevisiae gene conversion
On EPA IRIS database
NIOSH Analytical Method, 1994: Organophosphorus pesticides, 5600
*** END OF RECORD ***