dimethyl (1E)-1-methyl-3-(methylamino)-3-oxoprop-1-en-1-yl phosphate
Monocrotophos
CAS: 6923-22-4
Molecular Formula: C7H14NO5P
dimethyl (1E)-1-methyl-3-(methylamino)-3-oxoprop-1-en-1-yl phosphate - Names and Identifiers
dimethyl (1E)-1-methyl-3-(methylamino)-3-oxoprop-1-en-1-yl phosphate - Physico-chemical Properties
| Molecular Formula | C7H14NO5P |
| Molar Mass | 223.16 |
| Density | 1.3300 |
| Melting Point | 54-55°C |
| Boling Point | 125°C (0.0005 torr) |
| Flash Point | -18°C |
| Water Solubility | Soluble |
| Vapor Presure | 2.9×10-4 Pa (20 °C) |
| Appearance | solid |
| Exposure Limit | OSHA PEL: TWA 0.25 mg/m3; ACGIH TLV: TWA 0.25 mg/m3. |
| BRN | 8415832 |
| pKa | 13.06±0.46(Predicted) |
| Storage Condition | 0-6°C |
| Refractive Index | 1.449 |
dimethyl (1E)-1-methyl-3-(methylamino)-3-oxoprop-1-en-1-yl phosphate - Risk and Safety
| Risk Codes | R24 - Toxic in contact with skin R26/28 - Very toxic by inhalation and if swallowed. R50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. R68 - Possible risk of irreversible effects R67 - Vapors may cause drowsiness and dizziness R65 - Harmful: May cause lung damage if swallowed R38 - Irritating to the skin R11 - Highly Flammable R36 - Irritating to the eyes R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. |
| Safety Description | S1/2 - Keep locked up and out of the reach of children. 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. S62 - If swallowed, do not induce vomitting; seek medical advice immediately and show this container or label. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S16 - Keep away from sources of ignition. |
| UN IDs | UN 2783 |
| WGK Germany | 3 |
| RTECS | TC4375000 |
| HS Code | 29241200 |
| Hazard Class | 6.1(a) |
| Packing Group | II |
| Toxicity | LD50 in male, female rats (mg/kg): 17, 20 orally; 126, 112 dermally (Gaines) |
dimethyl (1E)-1-methyl-3-(methylamino)-3-oxoprop-1-en-1-yl phosphate - Nature
Open Data Verified Data
pure colorless crystals, soluble in water, methanol, acetone, methylene chloride, ethylene glycol and benzene. The solubility in n-octanol is 25%, toluene is 6%, slightly soluble in ether, slightly soluble in carbon tetrachloride, insoluble in petroleum ether, n-hexane solubility of 0. o5%. Light is more stable, but poor thermal stability. It is more stable in acidic and neutral medium. When pH is 7, the half-aging period is 22d; When pH is 9, it is 4d; When pH is 12, the half-aging period is less than O.lh (30 degrees C). According to the difference of soil organic matter and microbial community, the half-life of monocrotophos in soil was 4~14 days. Corrosive to steel and iron.
Last Update：2024-01-02 23:10:35
dimethyl (1E)-1-methyl-3-(methylamino)-3-oxoprop-1-en-1-yl phosphate - Preparation Method
Open Data Verified Data
from trimethyl phosphite and 2-acetyl -2-chloro acetyl amine by Berkow (Perkow) rearrangement reaction. Trimethyl phosphite can be prepared by transesterification of tribenzoquinone phosphite with methanol or by direct esterification of phosphorus trichloride with methanol in the presence of an acid binding agent. 2-acetyl -2-chloroacetylamine can be first by diketene and methylamine reaction to generate 2-acetyl acetylmethylamine, the latter in the presence of urea, sodium chloride and chlorine gas reaction. The 2-acetyl -2-Chloroacetyl Amine was added to the solvent dichloroethane, and trimethyl phosphite was added at 50~65 °c. After addition, monocrotophos can be obtained by reacting at 90 ℃ for 2H.
Last Update：2022-01-01 10:11:50
dimethyl (1E)-1-methyl-3-(methylamino)-3-oxoprop-1-en-1-yl phosphate - Use
Open Data Verified Data
monocrotophos is an important species of organophosphorus insecticides, with a broad spectrum of insecticides and acaricidal effects. It can be used to control cotton aphid, cotton red spider, cotton bollworm, Cotton Bridge worm, Spodoptera litura, thrips and other pests. The rice pests such as Chilo suppressalis, Chilo suppressalis, rice leaf roller Borer, black tail water cicada, Rice planthopper, fruit tree pests such as Red Spider Hawthorn, Apple leaf moth also have better control effect. Monocrotophos on sorghum and peach to produce damage, should not be used. Toxic to bees, should avoid in the role of the drug in the flowering period.
Last Update：2022-01-01 10:11:50
dimethyl (1E)-1-methyl-3-(methylamino)-3-oxoprop-1-en-1-yl phosphate - Safety
Open Data Verified Data
male rats, female rats oral LD50 17mg/kg, 20mg/kg. Rat percutaneous LD50 was 122mg/kg; Rabbit percutaneous LD50 was 354 ~ 709mg/kg. It has a slight irritating effect on rabbit skin and eyes. The two-year feeding trial showed that the non-effective dose was 1 mg/kg per day for rats and 1.6mg/kg per day for dogs. In the test dose, no carcinogenic, teratogenic and mutagenic effect was found on the tested animals. Rainbow trout LC50 12mg/L( 24h), 7mg/L( 48h), 4.9mg/L(96H), crucian carp LCso >49mg/L(96H). High toxicity to birds, quail acute oral LC50 about 0.7mg/L(7d).
Last Update：2022-01-01 10:11:51
dimethyl (1E)-1-methyl-3-(methylamino)-3-oxoprop-1-en-1-yl phosphate - Reference Information
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| organophosphorus insecticides | monocrotophos is a highly effective systemic organophosphorus insecticide with cis-and trans-isomers, industrial products are a mixture of these two isomers, at room temperature for brown semi-solid, neutral and acidic conditions more stable; Alkaline conditions, easy to decompose, can not be mixed with alkaline substances; more stable to sunlight; Corrosive to iron and brass; Miscible with water, soluble in ethanol, acetone, slightly soluble in xylene and kerosene, insoluble in aliphatic hydrocarbons, with a strong contact kill and stomach poison. Insecticidal spectrum is wide, quick effect is good, the initial period is long, the puncture suction, chewing and mothiness of a variety of pests effectively. Can control the rice borer, Rice longitudinal rolling leaf insect, Rice bract, rice stem, rice leaf hopper, Rice planthopper, resistant aphids, Red Spider, cotton bollworm, cotton bollworm and other pests. The mechanism of action is the inhibition of acetylcholinesterase in insects. Monocrotophos also has a certain egg killing effect, which is suitable for controlling many kinds of pests on cotton, rice, soybean, forest and other crops. Toxicity monocrotophos is highly toxic to birds and other wild animals; Less toxic to fish; Highly toxic to shrimps; Highly toxic to bees; Highly toxic to humans and animals, however, the percutaneous toxicity (toxicity in contact with the skin) is low, and the safety should be paid attention to when using. General use of crop safety, but in the cold region of some varieties of apple, cherry, almond, peach and sorghum have slight damage. |
| production method | from trimethyl phosphite and 2-acetyl-2-chloroacetylamine via Perkow obtained by rearrangement reaction. Trimethyl phosphite can be prepared by transesterification of tribenzoquinone phosphite with methanol or by direct esterification of phosphorus trichloride with methanol in the presence of an acid binding agent. 2-acetyl-2-chloroacetylamine can be prepared by reacting diketene with methylamine to form 2-acetylacetylmethylamine, which is then reacted with chlorine in the presence of urea and sodium chloride. 2-acetyl-2-chloroacetylamine was added to the solvent dichloroethane and trimethyl phosphite was added at 50-65 °c. After addition, monocrotophos was obtained by reaction at 90 ° C. For 2H. |
| category | pesticide |
| toxicity grade | highly toxic |
| Acute toxicity | oral-rat LD50: 8 mg/kg; Oral-mouse LD50: 15 mg/kg |
| flammability hazard characteristics | open flame flammable; Toxic nitrogen oxide and phosphorus oxide gases emitted by heat |
| storage and transportation characteristics | The warehouse is ventilated and dried at low temperature; It is stored and transported separately from food raw materials |
| fire extinguishing agent | Sand, dry powder, foam |
| Occupational Standard | TWA 0.25 mg/m3 |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 21:32:07
