dimethyl [(1R)-2,2,2-trichloro-1-hydroxyethyl]phosphonate
Trichlorphon
CAS: 52-68-6
Molecular Formula: C4H8Cl3O4P
dimethyl [(1R)-2,2,2-trichloro-1-hydroxyethyl]phosphonate - Names and Identifiers
dimethyl [(1R)-2,2,2-trichloro-1-hydroxyethyl]phosphonate - Physico-chemical Properties
| Molecular Formula | C4H8Cl3O4P |
| Molar Mass | 257.44 |
| Density | 1.73 |
| Melting Point | 77-81 °C |
| Boling Point | 100°C |
| Flash Point | 116.7°C |
| Water Solubility | Slightly soluble. 1-5 g/100 mL at 21 ºC |
| Solubility | Freely soluble in water, very soluble in methylene chloride, freely soluble in acetone and in ethanol (96 per cent). |
| Vapor Presure | 2.1×10-4Pa (20 °C) |
| Appearance | solid |
| Color | Crystals |
| Merck | 13,9696 |
| BRN | 1709434 |
| pKa | 6 (est.) |
| Storage Condition | 2-8°C |
| Refractive Index | 1.3439 |
| Physical and Chemical Properties | Pure product is a slightly aromatic white crystalline powder, industrial products with chloral odor. m. P. 83~84 °c, vapor pressure 1.04 x 10-3Pa (20 °c), volatility 0.11mg/m3, B. p.100 °c/13.33, relative density 1.73 (20 °c), refractive index n20d1.3439. Soluble in benzene, ethanol, chloroform, methanol and other organic solvents, slightly soluble in carbon tetrachloride, insoluble in petroleum ether, 25 ℃, the solubility in water is 154g/L. Stable at room temperature; The aqueous solution is placed for a long time to become acidic, and the water is freed from methyl under acidic conditions to generate a non-toxic demethylated trichlorfon; The water is freed from a molecule of hydrogen chloride under alkaline conditions to generate dichlorvos with greater toxicity. It is slightly corrosive to metals and begins to decompose at 180 °c. |
| Use | High efficiency and low toxicity of organic phosphorus pesticides, mainly used for the control of vegetables, fruit trees, tea, Mulberry, cotton and food crops on the chewing mouth insects |
dimethyl [(1R)-2,2,2-trichloro-1-hydroxyethyl]phosphonate - Risk and Safety
| Risk Codes | R22 - Harmful if swallowed R43 - May cause sensitization by skin contact R50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. |
| Safety Description | S24 - Avoid contact with skin. S37 - Wear suitable gloves. 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. S2 - Keep out of the reach of children. |
| UN IDs | UN 3077 9/PG 3 |
| WGK Germany | 3 |
| RTECS | TA0700000 |
| HS Code | 29319090 |
| Hazard Class | 6.1(b) |
| Packing Group | III |
| Toxicity | LD50 in male, female rats (mg/kg): 630, 560 orally (Gaines) |
dimethyl [(1R)-2,2,2-trichloro-1-hydroxyethyl]phosphonate - Nature
Open Data Verified Data
The Pure product is a white crystalline powder with a slightly aromatic odor. Industrial products with chloral odor. Soluble in benzene, ethanol, chloroform, methanol and other organic solvents, slightly soluble in carbon tetrachloride, insoluble in petroleum ether, 25 ℃, the solubility in water 15. 4G/lOOmL. Stable at room temperature, at 180 degrees began to decompose. The solution will be deteriorated for a long time and will be converted into more toxic dichlorvos in alkaline solution. The conversion process will be accelerated with the increase of alkalinity and temperature. Slight corrosion to metal.
Last Update：2024-01-02 23:10:35
dimethyl [(1R)-2,2,2-trichloro-1-hydroxyethyl]phosphonate - Preparation Method
Open Data Verified Data
hemiacetal was formed by mixing methanol with chloral, and then dimethyl phosphite was obtained by reacting phosphorus trichloride with methanol at low temperature. At higher temperature, chloral and dimethyl phosphite were condensed to form trichlorfon.
Last Update：2022-01-01 10:11:33
dimethyl [(1R)-2,2,2-trichloro-1-hydroxyethyl]phosphonate - Use
Open Data Verified Data
an organophosphorus pesticide. High efficiency, low toxicity, low residue, broad-spectrum pesticides, gastric toxicity, and contact killing effect, but also have osmotic activity. A wide range of agricultural applications, for the prevention and control of cabbage insects, Cotton leaf jumping insects, Mulberry wild silkworm, Phellinus igniarius, Weevil, fruit tree leaf Bee, fruit flies and other pests. Refined trichlorfon can be used for the prevention and control of pigs, cattle, horses, mules livestock in vivo and in vitro parasites, the family and environmental health pests are effective. Can be used for the treatment of schistosomiasis, animal husbandry is a good multi-effect insect repellent. Trichlorfon has the effect of killing and stomach toxicity, osmotic activity. The original powder can be processed into powder, wettable powder, soluble powder and emulsion and other dosage forms, can also be directly prepared aqueous solution or poison bait, for the prevention and treatment of chewing mouthpiece and pricking mouthpiece, forest, horticultural pests, underground pests, etc.
Last Update：2022-01-01 10:11:33
dimethyl [(1R)-2,2,2-trichloro-1-hydroxyethyl]phosphonate - Safety
Open Data Verified Data
The oral LD50 of male rats is 630mg/kg, the LD50 of female rats is 560mg/kg, and the percutaneous LD50 of rats is> 2000mg/kg. The rats were fed with 500mg/kg feed for two years, and no abnormality was found.
Last Update：2022-01-01 10:11:34
dimethyl [(1R)-2,2,2-trichloro-1-hydroxyethyl]phosphonate - Reference Information
| (IARC) carcinogen classification | 3 (Vol. 30, Sup 7) 1987 |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| introduction | trichlorfon is an organophosphorus insecticide. its essence is toxic. it can only prevent parasitic fish diseases and is ineffective against bacterial viral fish diseases. |
| toxicity | acute oral LD50 of male rats is 630 mg/kg, female is 560 mg/kg; Acute percutaneous LD50 of rats> 2000 mg/kg. Feeding rats with 500mg/kg feed for 2 years, no abnormal phenomenon was found. |
| use | high efficiency, low toxicity, low residue, broad-spectrum insecticide, mainly stomach poison, with contact killing effect and osmotic activity. It can be used for grain, cotton, fruit mulberry, tea tree, tobacco, vegetables, animal husbandry and sanitary pests. Such as armyworm, rice stem borer, rice planthopper, rice bract, cotton red bollworm, weevil, leafhopper, golden steel drill, corn stem borer, vegetable cabbage worm, vegetable borer, Spodoptera litura, etc. 800~1500 times of water is uniformly sprayed with 90% raw powder. Refined trichlorfon can be used to prevent and control parasites in pigs, cattle, horses and snail livestock. Parasite lice on the body surface can be washed with a liquid medicine of 0.5kg of 90% solid to 200~250kg of water. Parasites in pig gastrointestinal tract (such as roundworms, pinworms, etc.) are taken orally with refined trichlorfon 100 mg/kg body weight for veterinary medicine. Trichlorfon can also be used to control sanitary pests such as houseflies, larvae, bed bugs, cockroaches, etc. It is harmful to sorghum, soybean and melon crops. trichlorfon is a high-efficiency and low-toxicity insecticide, which has strong stomach toxicity and contact killing effects, and has fumigation performance. It is most effective against Diptera, Lepidoptera, and Coleoptera pests. It is mainly used to control chewing mouthparts pests on vegetables, fruit trees, tea, mulberry, cotton and food crops, and also to control sanitary pests. It generally does not produce phytotoxicity to a variety of crops, but it is prone to phytotoxicity to sorghum and soybeans. Refined trichlorfon is used as an insect repellent for livestock. Industrial pure trichlorfon is recrystallized with methanol-water to obtain refined trichlorfon, which can be used as an insect repellent and anti-filariasis medicine for livestock. It is mainly used to prevent and control various pests on vegetables, fruit trees, tea, mulberry, cotton and food crops. It can also be used as a sanitary drug and prevent livestock parasites. It is a broad-spectrum insecticide with strong contact killing, stomach poison, fumigation and absorption. It is mainly used for rice, cotton, fruit trees, etc. High-efficiency and low-toxic organophosphorus insecticides, mainly used to control chewing mouthparts pests on vegetables, fruit trees, tea, mulberry, cotton and food crops nickel-plated leveling agent, brightener broad-spectrum insecticide with stomach toxicity and contact killing effects. Standard for analysis of pesticide residues. Calibration instruments and devices; evaluation methods; working standards; quality assurance/quality control; other. |
| Production method | Methanol is esterified with phosphorus trichloride to generate dimethyl phosphite, and then condensed with trichloroacetaldehyde to generate trichlorfon. Raw material consumption quota: 610kg/t of phosphorus trichloride, 740kg/t of chloroacetaldehyde and 470kg/t of methanol. First, mix methanol and chloroacetaldehyde to form hemiacetal (and contain a small amount of acetal). Then at a lower temperature, phosphorus trichloride reacts with methanol to generate dimethyl phosphite (free methanol or methanol in hemiacetal and acetal are easily reacted with phosphorus trichloride), and HCl and CH3Cl are eliminated in time. Finally, at a higher temperature, trichloral and dimethyl phosphite undergo condensation reaction to form trichlorfon. In continuous operation, methanol and chloroacetaldehyde are controlled to be slightly larger than the theoretical quantity, and the mass ratio is phosphorus trichloride. Methanol; Chloroacetaldehyde = 1:(0.73~0.78):(1.12~1.18); The esterification temperature is 40~50 ℃, and the residence time is 10min. The liquid phase temperature of the deacidification liquid is 80 ℃, the condensation temperature is 90~95 ℃, and the residence time is 40~50min. The defluxing temperature is 95~105 ℃ first, after <120 ℃. Trichlorfon production can also be carried out in one-step synthesis and segmentation. That is, one-time feeding produces dimethyl phosphite at low temperature, without separation, and directly generates trichlorfon at high temperature. In the esterification stage, chloroacetaldehyde and methanol are mixed at a temperature not exceeding 50 ℃, cooled to below 5 ℃, phosphorus trichloride is added, and hydrogen chloride and methyl chloride are discharged for recovery and treatment. In the condensation stage, the esterification liquid is further removed from hydrogen chloride by the enemy country, and then the reaction tank is carried out at a temperature of 80~120 ℃ to generate trichlorfon. |
| category | pesticide |
| toxicity classification | highly toxic |
| acute toxicity | abdominal cavity-rat LD50: 160 mg/kg; Oral administration-mouse LD50: 300 mg/kg |
| stimulation data | eyes-rabbit 120 mg/6 days mild |
| flammability hazard characteristics | open flame is combustible; it decomposes toxic phosphorus oxide and chloride gas when heated |
| storage and transportation characteristics | warehouse ventilation and low temperature drying; separate from food raw materials storage and transportation |
| fire extinguishing agent | sand, dry powder, foam |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 20:52:54
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