[(R)-cyano-[4-fluoro-3-(phenoxy)phenyl]methyl] (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
beta-cyfluthrin
CAS: 68359-37-5
Molecular Formula: C22H18Cl2FNO3
[(R)-cyano-[4-fluoro-3-(phenoxy)phenyl]methyl] (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate - Names and Identifiers
[(R)-cyano-[4-fluoro-3-(phenoxy)phenyl]methyl] (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate - Physico-chemical Properties
| Molecular Formula | C22H18Cl2FNO3 |
| Molar Mass | 434.29 |
| Density | 1.3336 (estimate) |
| Melting Point | 60°C |
| Boling Point | 496.3±45.0 °C(Predicted) |
| Flash Point | 253.9°C |
| Water Solubility | 0.002-0.003 mg l-1 (20 °C) |
| Vapor Presure | 1-8×10-8 Pa (20 °C) |
| Appearance | neat |
| Merck | 13,2785 |
| BRN | 2788149 |
| Storage Condition | Sealed in dry,Room Temperature |
| Refractive Index | nD23 1.5511 |
| MDL | MFCD00078636 |
| Physical and Chemical Properties | The original drug is brown viscous liquid with relative density of 1.27~1.28, vapor pressure> 1.33 × 10-8Pa at 20 ℃, and volatilization rate of 0.3 μg/m3(40 ℃). Soluble in acetone, ether, toluene, methylene chloride and other organic solvents, slightly soluble in alcohol, insoluble in water. It is stable to acidity and sunlight, and unstable in alkalinity with pH value greater than 7.5. Enantiomer (S,1R-cis-R, 1S-cis-)m. P. 81 ℃, vapor pressure 10 × 10-9Pa (20 ℃), solubility at 20 ℃: toluene, dichloromethane> 200g/L, isopropanol 5~10g/L, hexane 2~5g/L, water 0.005mg/L. Enantiomer (S,1R-anti-R,1S-Anti-) M.P. 106 ℃, vapor pressure 90 × 10-9Pa (20 ℃), solubility at 20 ℃: toluene, dichloromethane> 200g/L, isopropanol 2~5g/L, hexane 1~2G/L, water 0.002mg/L. |
| Use | It is a synthetic pyrethroid insecticide, which has the effect of killing and stomach poison, broad insecticidal spectrum, rapid knockdown and long duration |
[(R)-cyano-[4-fluoro-3-(phenoxy)phenyl]methyl] (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate - Risk and Safety
| Risk Codes | 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. R28 - Very Toxic if swallowed R23 - Toxic by inhalation |
| Safety Description | S1/2 - Keep locked up and out of the reach of children. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. 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. S28 - After contact with skin, wash immediately with plenty of soap-suds. |
| UN IDs | 2588 |
| WGK Germany | 3 |
| RTECS | GZ1253000 |
| HS Code | 29269090 |
| Hazard Class | 6.1(b) |
| Packing Group | III |
| Toxicity | LD50 in male, female rats, male, female mice (mg/kg): 500-800, 1200, 300, 600 orally in Lutrol (Behrenz); LC50 (96 hr) in rainbow trout: 0.0006 mg/l (Hammann) |
[(R)-cyano-[4-fluoro-3-(phenoxy)phenyl]methyl] (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate - Reference
| Reference Show more | 1. [IF=4.845] Nan Chen et al."Involvement of integument-rich CYP4G19 in hydrocarbon biosynthesis and cuticular penetration resistance in Blattella germanica (L.)."Pest Manag Sci. 2020 Jan;76(1):215-226 |
[(R)-cyano-[4-fluoro-3-(phenoxy)phenyl]methyl] (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate - 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) |
| toxicity | rat acute oral LD50 was 590~1270mg/kg; Acute percutaneous LD50>5000mg/kg, acute inhalation of lc501089 mg/m3 (1H). Mild irritation to rabbit eyes, no irritation to the skin. The non-effective dose of subacute oral administration in rats was 300mg/kg. No teratogenic, carcinogenic or mutagenic effects were observed in animal experiments. High toxicity to fish, carp LC50 0.01mg/L, rainbow trout 0.0006mg/L, goldfish 0.0032mg/L (96H). Birds oral LD50 250 ~ 1000mg/kg, quail oral LD50>5000mg/kg. Highly toxic to bees and silkworm. |
| Use | is stable to light and has strong killing and stomach toxicity effects. Lepidoptera a variety of larvae and aphids and other pests have good results, rapid efficacy, long residual effect, suitable for cotton, tobacco, vegetables, soybeans, peanuts, corn and other crops. Such as the control of cotton bollworm, cotton Red Spider, in the egg incubation period, with 5% emulsifiable concentrate 4.5~7.5/100, 7.5 ~ 15kg of water spray. Control of cotton aphid, in the cotton seedling stage, with 5% emulsifiable concentrate 1.5~3mL/100, the water 7.5kg spray. The control of canola, Myzus persicae and canola tube aphid is sprayed with 2000~3000 times of 5% emulsifiable concentrate, and the control of diamondback moth, beet armyworm and Spodoptera litura is sprayed with the same concentration before the third instar larvae are full-onset. To control soybean Borer, in the period of flowering and pod-setting of bean, spray 4.5 of water with 5% emulsifiable concentrate 7.5 ~/100m2, which can also cure soybean aphid. Control of tea geometrid, tea worms, etc., in the 2~3 instar larvae, with 5% emulsifiable concentrate 2000~4000 times liquid spray. Be careful not to use near Mulberry Garden, fish pond, water source and apiculture period. The insecticidal activity of beta-cyfluthrin is more than 1 times higher than that of cyfluthrin, and the effective concentration is 1/2 of that of cyfluthrin. is a synthetic pyrethroid insecticide with contact killing and gastric toxicity, Broad insecticidal spectrum, rapid knockdown, long effective duration used to control pear tree, pear wood lice and other pests has a good killing effect on a variety of lepidopteran larvae, and can also effectively control some underground pests, and some adults have the role of repellent The product insecticidal efficient, a variety of scale larvae have a good effect, but also effective control of some underground pests. The main effect was Contact killing and gastric toxicity, without internal inhalation and fumigation. The insecticidal spectrum is broad, the action is rapid, and the duration is long. With some ovicidal activity, and some adult repellent effect. |
| production method | preparation of 4-fluoro-3-phenoxybenzaldehyde with P-chlorotoluene as raw material and aniline as raw material 3-(2, 2-dichlorovinyl) preparation of -2, 2-dimethylcyclopropanecarboxyl chloride the synthesis of dichloropolyramic acid can be carried out by using a phase model method, a Farkas method, a phase model, a culalactan method, a cyclobutanone method, an NRDC method, and the like. Can be selected according to different needs. In the phase model method (Sagami method), 3-methyl-2-butenol is condensed with Ortho-acetic acid ester in the presence of phosphoric acid as catalyst at 140~160 ℃ to remove one molecule of alcohol, claisen rearrangement was carried out to form methyl 3, 3-dimethyl-pentenoate (methyl valvulate), which was reacted with carbon tetrachloride in the presence of peroxide to Form 3, 3-dimethyl-4, methyl 6,6, 6-tetrachloro hexenoate is then subjected to dehydrochlorination in the presence of sodium methoxide to form methyl dichloro-pyrethrate. The Farkas method uses 1, 1-dichloro-4-methyl-1, 3-pentadiene to react with diazoacetate in the presence of copper powder or other catalysts to produce dichloro-pyretic acid. 1, 1-dichloro-4-methyl -1, 3-pentadiene can use chloral and isobutene, the reaction product is 1,1, 1-trichloro-4-methyl-3-penten-2-ol and 1,1, 1-trichloro-4-methyl-4-penten-2-ol. If AlCl3 is used as the catalyst, the product is mainly the former. Then it reacted with acetic anhydride through acetylation, reduction of zinc powder, and Catalytic isomerization of p-toluenesulfonic acid to obtain 1, 1-dichloro-4-methyl-1, 3-pentadiene containing conjugated double bond. Phase mode-coularley method (Sagami-Kuraray method) this is a combination of the phase mode method and the Farkas method. The cyclobutanone method utilizes a-halocyclobutanone to undergo a favor SKII rearrangement in the presence of an alkaline substance, whereby the ring is reduced to form cis-dichloro-pyretic acid. Α-chlorocyclobutanone is prepared from isobutylene, carbon tetrachloride and acrylic acid. The dihalic acid is produced by the method of cyclobutanone, and the proportion of cis-form is 80% ~ 90%. The NRDC method uses Wittig reagent to react with the corresponding chrysanthemum acid formaldehyde derivatives to obtain the desired chrysanthemum acid derivatives. In this way, the configuration of the original chrysanthemum acid compound can be kept unchanged. The role of dichloro chrysanthemum acid and thionyl chloride, dichloro chrysanthemum acid chloride. Synthesis of cyfluthrin 6.8g of 3-(2, 2-dichloroethylene)-2, 2-dimethylcyclopropanecarboxyl chloride and 6.5g of 4-fluoro-3-phenoxybenzaldehyde, to a mixture of 2.25g of sodium cyanide, 3.5ml of water, 150ml of n-hexane and 0.75g of tetrabutylammonium bromide was added dropwise at 20-25 °c. Then, the reaction mixture was stirred at 20-25 °c for 4H, diluted with 800ml of toluene, and washed twice with 800ml of water. The organic phase was dried over magnesium sulfate and desolved under reduced pressure, the residual solvent was distilled off at 60 ° C./133.3Pa to give 10.8g of cyfluthrin as a viscous oil in a yield of 76%. Can also be 3-phenoxy-4-fluorobenzaldehyde with sodium bisulfite into the corresponding sulfonate, and then with sodium cyanide and 3-(2, 2-dichlorovinyl)-2, cyfluthrin was obtained by reaction with 2-dimethylcyclopropanecarboxyl chloride in a yield of 95%. |
| category | pesticide |
| toxicity grade | high toxicity |
| Acute toxicity | oral-rat LD50: 900 mg/kg; Oral-mouse LD50: 300 mg/kg |
| flammability hazard characteristics | toxic nitrogen oxides, chlorides, and fluorides gases from combustion |
| storage and transportation characteristics | The warehouse is ventilated and dried at low temperature; It is stored and transported separately from food raw materials |
| extinguishing agent | dry powder, foam, sand |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 21:54:55
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