3-phenoxybenzyl (1RS)-cis-trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
Permethrin
CAS: 52645-53-1
Molecular Formula: C21H20Cl2O3
3-phenoxybenzyl (1RS)-cis-trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate - Names and Identifiers
3-phenoxybenzyl (1RS)-cis-trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate - Physico-chemical Properties
| Molecular Formula | C21H20Cl2O3 |
| Molar Mass | 391.29 |
| Density | 1.19 |
| Melting Point | 34-35°C |
| Boling Point | bp0.05 220° |
| Flash Point | 10°C |
| Water Solubility | insoluble |
| Vapor Presure | 7×10-5 Pa (20 °C) |
| Appearance | neat |
| Merck | 13,7257 |
| BRN | 5765325 |
| PH | 6.5 |
| Storage Condition | 0-6°C |
| Stability | Stable. Incompatible with strong oxidising agents. |
| Refractive Index | 1.6500 (estimate) |
| Physical and Chemical Properties | density 1.19 melting point 34-35°C water-soluble insoluble 3-phenoxybenzyl (1RS,3RS;1RS,3SR)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate |
| Use | For high efficiency, low toxicity pesticides, used to control cotton, rice, vegetables, fruit trees, tea and other crop pests, can also control health and livestock pests |
3-phenoxybenzyl (1RS)-cis-trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate - Risk and Safety
| Risk Codes | R20/22 - Harmful by inhalation and 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. R39/23/24/25 - R23/24/25 - Toxic by inhalation, in contact with skin and if swallowed. R11 - Highly Flammable R51/53 - Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. R36 - Irritating to the eyes R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. |
| Safety Description | S13 - Keep away from food, drink and animal foodstuffs. S24 - Avoid contact with skin. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. 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. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S36/37 - Wear suitable protective clothing and gloves. S16 - Keep away from sources of ignition. S7 - Keep container tightly closed. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| UN IDs | UN1230 3/PG 2 |
| WGK Germany | 3 |
| RTECS | GZ1255000 |
| HS Code | 29162090 |
| Toxicity | LD50 orally in female rats: 3801 mg/kg (Metker); LD50 in 8 day old rats, male adult rats (mg/kg): 340.5, 1500.0 orally (Cantalamessa) |
3-phenoxybenzyl (1RS)-cis-trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate - Upstream Downstream Industry
| Raw Materials | Acetic acid 4-Chlorobenzyl cyanide Phenyl ether Sodium metabisulfite Methenamine Isopropanol |
3-phenoxybenzyl (1RS)-cis-trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate - safety
Open Data Verified Data
It should be stored indoors in a well ventilated and cool place, paying attention to fire prevention.
Last Update：2024-01-02 23:10:35
3-phenoxybenzyl (1RS)-cis-trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| (IARC) carcinogen classification | 3 (Vol. 53) 1991 |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| toxicity | the original drug has an acute oral LD50 of 1200~2000 mg/kg in rats, an acute inhalation of LC50>23.5g/m3 (4h), and an acute percutaneous LD50 of rats and rabbits> 2000 mg/kg. It has no irritating effect on rabbit skin and slight irritating effect on eyes. Feeding rats at a dose of 1500mg/kg for 6 months had no effect. Rats have little accumulation in vivo, and no teratogenic, carcinogenic or mutagenic effects have been found in animal experiments. The LC50 of rainbow trout and blue gill is 0.0032mg/L (96h), the acute oral LD50 of quail is 13500 mg/kg, the contact LD50 of bees is 0.1 μg/bee, and the oral LD50 is 0.2 μg/bee. |
| use | has strong touch killing and stomach poison effects, and has the characteristics of strong knockdown and fast insecticidal speed. It is more stable to light, and under the same conditions of use, the development of resistance to pests is also slower, and it is efficient to lepidopteran larvae. It can be used for the control of vegetables, tea, fruit trees, cotton and other crops to prevent rapae, aphids, cotton bollworms, cotton bollworms, cotton aphids, lygus, yellow striped beetle, peach little heart worm, citrus leaf miner, twenty-eight star ladybug, tea geometrid, tea caterpillar, tea moth and other pests, It also has good effects on mosquitoes, flies, fleas, cockroaches, lice and other sanitary pests. For example, to control cotton bollworm and cotton red bollworm, spray 1000~1250 times of 10% emulsifiable concentrate during the egg incubation period to treat bridge-building insects and leaf-rolling insects. Control of cotton aphid in the adult, nymphal period, with 10% emulsifiable concentrate 2000~3000 times spray, resistant cotton aphid and cotton bollworm effect is poor. To control fruit tree pests, spray 5.52kg of water with 10% emulsifiable concentrate 3.75mL/100 m2. To prevent and control sanitary pests, spray 800~1000 times of 10% emulsifiable concentrate. Control of cabbage, peach aphid, diamondback moth, Spodoptera litura, etc. with 10% emulsifiable concentrate 1000~2000 times spray. It is a high-efficiency and low-toxic insecticide. It is used to control cotton, rice, vegetables, fruit trees, tea trees and other crop pests. It can also control sanitary and livestock pests. This product is a high-efficiency and low-toxic insecticide. It is used to control cotton, rice, vegetables, fruit trees, tea trees and other crop pests. It is also used to control sanitary pests and livestock pests. Insecticidal effect is strong, and a very low concentration can cause pest poisoning and death. Most of the effective concentrations for pest control in agriculture are below 100ppm, generally 20-50ppm, and the amount of effective ingredients per mu is generally only 5-10ml. |
| Production method | Synthesis of 1,1, 1-trichloro-4-methyl-4-pentene-2-ol from trichloroacetaldehyde and isobutylene, After translocation, 1,1, 1-trichloro-4-methyl-3-pentene-2-ol is obtained, and then it is condensed and rearranged with triethyl orthoacetate to obtain 3, ethyl 3-dimethyl -4,6, 6-trichloro-5-hexenoate, further cyclized under the action of sodium ethoxide to 2, 2-dimethyl -3-(2, 2-dichlorovinyl) cyclopropane carboxyl ester ethyl ester, saponified into sodium salt, and then reacted with chlorine-3-phenoxybenzyl triethylamine to prepare dichloroethrin. The raw materials and intermediates of the method are easy to obtain, the operating conditions in the process are strict, the product content is generally 60-80%, processed into 3.2% or 10% emulsifiable concentrate, 0.25% powder. The interaction of trichloroacetaldehyde and isobutene to obtain (I)(II) two trichloroenol isomers. The reaction was carried out at low temperature with aluminum trichloride as a catalyst. In the presence of hydrogen chloride, acetonitrile reacts with absolute ethanol to produce iminoethyl ether hydrochloride, which further reacts with absolute ethanol to produce triethyl orthoacetate (III). In the presence of the catalyst p-toluenesulfonic acid, heating to 114~118 ℃, reaction for 3h, so that (I) is converted to (II). The translocation product is reacted with triethyl orthoacetate, the catalyst is isobutyric acid, the reaction temperature is raised from 110 ℃ to 150 ℃ for about 12h, the reaction is carried out at 150~155 ℃ for 7~8h, and the former fraction is evaporated at 0.08MPa pressure to obtain 3,3-dimethyl -4,6,6-trichlorohexene-[5]-ethyl acid (V), accompanied by (VI). (VI) is subjected to a ring-opening reaction in a hydrogen chloride-ethanol solution to obtain (V). (V) In the presence of sodium ethoxide, reaction at 40~45 ℃ for 5h, cyclization to produce 2, 2-dimethyl -3-(2, 2-dichlorovinyl)-cyclopropanecarboxylate (VII), after rectification to obtain higher purity of dichlorochrysanthemum acid ethyl ester. In the presence of lye, (VII) is refluxed for 3h and saponified to obtain the corresponding sodium salt (VIII). (VIII) reacts with m-phenoxybenzyl triethylamine chloride to produce permethrin (IX). The reaction process is as follows: The synthesis of dichlorochrysanthemum acid can be found in the literature [5]. |
| category | flammable liquid |
| toxicity classification | highly toxic |
| acute toxicity | oral-rat LD50: 383 mg/kg; Oral-mouse LD50: 424 mg/kg |
| stimulation data | skin-rabbit 500 mg/24 hours mild |
| explosive hazard characteristics | solvent vapor mixed with air can explode |
| flammability hazard characteristics | solvent flammable |
| storage and transportation characteristics | warehouse ventilation and low temperature drying; separate from oxidant storage and transportation |
| fire extinguishing agent | dry powder, foam, sand |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 21:21:28
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Raw Materials for 3-phenoxybenzyl (1RS)-cis-trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate