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141-66-2

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Basic Information
CAS No.: 141-66-2
Name: DICROTOPHOS
Molecular Structure:
Molecular Structure of 141-66-2 (DICROTOPHOS)
Formula: C8H16 N O5 P
Molecular Weight: 237.22
Synonyms: Phosphoricacid, (1E)-3-(dimethylamino)-1-methyl-3-oxo-1-propenyl dimethyl ester (9CI);Phosphoric acid, 3-(dimethylamino)-1-methyl-3-oxo-1-propenyl dimethyl ester,(E)-; Phosphoric acid, dimethyl ester, ester with3-hydroxy-N,N-dimethylcrotonamide, (E)- (8CI);3-(Dimethoxyphosphinyloxy)-N,N-dimethyl-cis-crotonamide; 3-Hydroxy-N,N-dimethyl-cis-crotonamidedimethyl phosphate; Bidrin; C 709; Carbicron; Carbomicron; Dicrotophos;Dimethyl 1-dimethylcarbamoyl-1-propen-2-yl phosphate; Dimethyl2-dimethylcarbamoyl-1-methylvinyl phosphate; ENT 24,482; Ektafos; Karbicron;Oleobidrin; SD 3562; trans-Bidrin
EINECS: 205-494-3
Density: 1.176g/cm3
Melting Point: <25℃
Boiling Point: 307.5°Cat760mmHg
Flash Point: 100℃
Solubility: Totally miscible
Hazard Symbols: Cholinesterase inhibitor. TLV: 0.25 mg/m3. Toxic by skin absorption.
Risk Codes: 24-28-50/53
Safety: Poison by ingestion, inhalation, skin contact, subcutaneous, intravenous, and intraperitoneal routes. Mutation data reported. Used to control the coffee borer and certain economically important pests of cotton. When heated to decomposition it emits very toxic fumes of NOx and POx. See also ESTERS.
PSA: 74.88000
LogP: 1.39590
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Chemistry

Empirical Formula: C8H16NO5P
Molecular Weight: 237.1901 g/mol 
EINECS: 205-494-3 
Index of Refraction: 1.456
Density: 1.176 g/cm3
Flash Point: 139.7 °C
Enthalpy of Vaporization: 54.81 kJ/mol
Boiling Point: 307.5 °C at 760 mmHg
Vapour Pressure: 0.000724 mmHg at 25 °C 
Solubility: Water soluble
Appearance: A yellow to brown liquid with a mild ester odor
Structure of Dicrotophos (CAS NO.141-66-2):
                            
Product Categories of Dicrotophos (CAS NO.141-66-2): Pesticides & Metabolites;Alphabetic;Insecticides;Organophorous 
IUPAC Name: [(E)-4-(Dimethylamino)-4-oxobut-2-en-2-yl] dimethyl phosphate
Canonical SMILES: CC(=CC(=O)N(C)C)OP(=O)(OC)OC
Isomeric SMILES: C/C(=C\C(=O)N(C)C)/OP(=O)(OC)OC
InChI: InChI=1S/C8H16NO5P/c1-7(6-8(10)9(2)3)14-15(11,12-4)13-5/h6H,1-5H3/b7-6+
InChIKey: VEENJGZXVHKXNB-VOTSOKGWSA-N

Uses

 Dicrotophos (CAS NO.141-66-2) can be used to control sucking, boring, and chewing pests on rice, cotton, coffee, apples, and other crops. It is effective on ornamentals, trees, and shrubs for aphids, leaf hoppers, and scale insects.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - wild LD50 oral 1mg/kg (1mg/kg)   ASTM Special Technical Publication. Vol. (680), Pg. 157, 1979.
bird - wild LD50 skin 1300ug/kg (1.3mg/kg)   Toxicology and Applied Pharmacology. Vol. 26, Pg. 154, 1973.
chicken LD50 oral 7970ug/kg (7.97mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Toxicology and Applied Pharmacology. Vol. 7, Pg. 606, 1965.
duck LD50 oral 4140ug/kg (4.14mg/kg)   Toxicology and Applied Pharmacology. Vol. 22, Pg. 556, 1972.
mouse LD50 intraperitoneal 9500ug/kg (9.5mg/kg)   Toxicology and Applied Pharmacology. Vol. 16, Pg. 446, 1970.
mouse LD50 intravenous 9900ug/kg (9.9mg/kg)   Journal of Pharmacy and Pharmacology. Vol. 19, Pg. 612, 1967.
mouse LD50 oral 11mg/kg (11mg/kg)   Guide to the Chemicals Used in Crop Protection. Vol. 6, Pg. 196, 1973.
mouse LD50 subcutaneous 11500ug/kg (11.5mg/kg)   Journal of Pharmacy and Pharmacology. Vol. 19, Pg. 612, 1967.
pigeon LD50 oral 2mg/kg (2mg/kg)   Toxicology and Applied Pharmacology. Vol. 20, Pg. 57, 1971.
quail LD50 oral 4mg/kg (4mg/kg)   Toxicology and Applied Pharmacology. Vol. 20, Pg. 57, 1971.
rabbit LD50 skin 168mg/kg (168mg/kg)   Guide to the Chemicals Used in Crop Protection. Vol. 6, Pg. 196, 1973.
rat LC50 inhalation 90mg/m3/4H (90mg/m3)   Proceedings of the European Society for the Study of Drug Toxicity. Vol. 15, Pg. 239, 1974.
rat LD50 oral 13mg/kg (13mg/kg)   Agricultural Research Service, USDA Information Memorandum. Vol. 20, Pg. 6, 1966.
rat LD50 skin 42mg/kg (42mg/kg)   World Review of Pest Control. Vol. 9, Pg. 119, 1970.
rat LD50 subcutaneous 8137ug/kg (8.137mg/kg)   British Journal of Pharmacology. Vol. 40, Pg. 124, 1970.
rat LD50 unreported 22mg/kg (22mg/kg)   "Chemistry of Pesticides," Melnikov, N.N., New York, Springer-Verlag New York, Inc., 1971Vol. -, Pg. 314, 1971.

Consensus Reports

EPA Farm Worker Reentry (39 FR 16888,74). EPA Genetic Toxicology Program. EPA Extremely Hazardous Substances List.

Safety Profile

Poison by ingestion, inhalation, skin contact, subcutaneous, intravenous, and intraperitoneal routes. Mutation data reported. Used to control the COFFEE borer and certain economically important pests of cotton. When heated to decomposition it emits very toxic fumes of NOx and POx. See also ESTERS.
Hazard Codes: DangerousNVeryT+
Risk Statements: 24-28-50/53 
R24:Toxic in contact with skin. 
R28:Very toxic if swallowed. 
R50/53:Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Safety Statements: 28-36/37-45-60-61
S28:After contact with skin, wash immediately with plenty of soap-suds. 
S36/37:Wear suitable protective clothing and gloves. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S60:This material and its container must be disposed of as hazardous waste. 
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.

Standards and Recommendations

OSHA PEL: TWA 0.25 mg/m3 (skin)
ACGIH TLV: TWA 0.05 mg/m3 (skin); Not Classifiable as a Human Carcinogen

Specification

 Dicrotophos ,its cas register number is 141-66-2. It also can be called Bidirl ; O,O-Dimethyl 1-(N,N-dimethylcarbamoyl)-1-propen-2-yl phosphate ; Dimethyl 2-Dimethylcarbamoyl-1-methylvinyl Phosphate ;and (E)-3-(Dimethylamino)-1-methyl-3-oxoprop-1-enyl dimethyl phosphate . It is susceptible to formation of highly toxic and flammable phosphine gas in the presence of strong reducing agents such as hydrides. Partial oxidation by oxidizing agents may result in the release of toxic phosphorus oxides. Dicrotophos (CAS NO.141-66-2) is incompatible with the following: Metals .