2-(4-ethoxyphenyl)-2-methylpropyl-3-phenoxybenzyl ether
Ethofenprox
CAS: 80844-07-1
Molecular Formula: C25H28O3
2-(4-ethoxyphenyl)-2-methylpropyl-3-phenoxybenzyl ether - Names and Identifiers
| Name | Ethofenprox |
| Synonyms | mti500 Trebon PUNKASO MTI-500 etofenprox ETOFENPROX ETHOFENPROX Ethofenprox ethophenprox Zoecon RF-316 Ethofenprox TC 2-(4-ethoxyphenyl)-2-methylpropyl 3-phenoxybenzyl ether 2-(4-ethoxyphenyl)-2-methylpropyl-3-phenoxybenzyl ether 1-[[2-(4-ethoxyphenyl)-2-methylpropoxy]methyl]-3-phenoxybenzene 1-{[2-(4-ethoxyphenyl)-2-methylpropoxy]methyl}-3-phenoxybenzene 1-((2-(4-ethoxyphenyl)-2-methylpropoxy)methyl)-3-phenoxybenzene |
| CAS | 80844-07-1 |
| EINECS | 407-980-2 |
| InChI | InChI=1/C25H28O3/c1-4-27-22-15-13-21(14-16-22)25(2,3)19-26-18-20-9-8-12-24(17-20)28-23-10-6-5-7-11-23/h5-17H,4,18-19H2,1-3H3 |
2-(4-ethoxyphenyl)-2-methylpropyl-3-phenoxybenzyl ether - Physico-chemical Properties
| Molecular Formula | C25H28O3 |
| Molar Mass | 376.49 |
| Density | 1.1386 (rough estimate) |
| Melting Point | 36.4-38.0° |
| Boling Point | 445.03°C (rough estimate) |
| Flash Point | 165.1°C |
| Water Solubility | <0.001 mg l-1(25 °C) |
| Vapor Presure | 32×10-3 Pa (100 °C) |
| Appearance | neat |
| Storage Condition | Sealed in dry,Room Temperature |
| Stability | Stable. Incompatible with strong oxidizing agents. |
| Refractive Index | nD20.2 1.5732 |
| Physical and Chemical Properties | Pure white crystals. m.p.36.4 -38 °c, vapor pressure 32 x 10-3Pa (100 °c), 8.0 x 10-3Pa (25 °c), B. p.208 °c/719.8, 100 °c/3.2 x 10-2Pa, relative density 1.157(23 °c). 25 ° C solubility: Chloroform 858g/L, acetone 908g/L, ethyl acetate 875g/L, ethanol 150g/L, methanol 76.6g/L, xylene 84.8g/L, water 1mg/L. The distribution coefficient was 11200000. The chemical properties were stable, and no obvious decomposition was found in 90D storage at 80 C, and the Half-Life was about 6d in soil with pH value of 2.8~11.9. The melting point of industrial products is 34~35. |
| Use | Systemic insecticides, Lepidoptera, Hemiptera, Coleoptera, Diptera and other pests with high efficiency |
2-(4-ethoxyphenyl)-2-methylpropyl-3-phenoxybenzyl ether - Risk and Safety
| UN IDs | UN 3077 9 / PGIII |
| WGK Germany | 2 |
| RTECS | DA0670000 |
| Toxicity | LD50 in rats, mice (mg/kg): >2880, >107200 orally; >2140, >2140 dermally |
2-(4-ethoxyphenyl)-2-methylpropyl-3-phenoxybenzyl ether - 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>4280mg/kg, dog> 5000mg/kg; male rats acute percutaneous LD50>1072mg/kg, female> 2140mg/kg; Male mice acute percutaneous LD50>1072mg/kg, female> 2140mg/kg; rats with acute inhalation of LC50>5.9mg/L (4H). No irritation to skin and eyes. The non-effective doses in the 2-year feeding experiment were 3.7-4.8mg/kg for rats and 3.1-3.6mg/kg for mice. Teratogenic, carcinogenic and mutagenic effects were not found in animal experiments. Carp LD50 5mg/L(48h), wild duck acute oral LD50>2000mg/kg, toxic to bees, silkworm. |
| biological activity | Etofenprox is a non-Ester pyrethroid insecticide. Etofenprox induced toxicity in housefly M. domestica (LD50=23 ng/fly). Formulations containing Etofenprox have been used for the control of agricultural pests. |
| Use | This product has the advantages of wide insecticidal spectrum, high insecticidal activity, fast knock-down speed, long residual effect period, characteristics of crop safety. It has the effects of contact, stomach poison and internal absorption. For the control of Lepidoptera, Hemiptera, Coleoptera, Diptera, Orthoptera and Isoptera pests, such as Brown lice, white-backed planthopper, black leaf cicada, cotton bollworm, pink bollworm, peach aphid, white whitefly, vegetable worm, tea, tea geometrid, tea thorn moth, peach and pear polyposis, citrus leaf moth, tobacco armyworm, diamondback moth, corn borer, Borer, soybean Borer, etc. Not effective against mites. Such as the prevention and control of cotton bollworm and pink bollworm, in the egg incubation period, the young insect cavity into the bud, Boll, with 10% suspension 15~18mL/100m2 of water spray; control of rice planthopper with 0.6~0.9g active ingredients/100m2 of the temperature of the powder on the water spray, or 20% ~ g active ingredients of the emulsifiable concentrate on water spray. The systemic insecticide has high efficiency to Lepidoptera, Hemiptera, Coleoptera, Diptera and other pests |
| production method | preparation method-preparation of isobutyryl chloride 359.5G of isobutyric acid at room temperature (15 ℃) is added dropwise 595g of thionyl chloride, after completion of the dropping, the temperature was raised to 75 ° C. Until no hydrogen chloride was released, the 88-92 ° C. Fraction was collected to obtain 293.0G of product. The residue was added with 100g of pre-fraction and neothionyl chloride, and distilled at atmospheric pressure to obtain 232.3g of 83~86 °c fraction and 106.1g of product at 88~92 °c, giving a total of 399.1g of product, with a content of 98.75% and a yield of 91.7%. Preparation of 1-(4-ethoxyphenyl)-2-methyl-1-propanone 37g of phenylether was mixed with 50ml of carbon disulfide and 48g of anhydrous aluminum trichloride was added in portions under cooling, continue to cool to 2~3 C, dropwise addition of isobutyryl chloride 32.1g, Dropwise then stirred for 1H reaction. The reaction solution was poured into 200ml of ice water, and 100ml of concentrated hydrochloric acid was added with stirring to separate the oil layer. The water layer was extracted with 50ml of benzene for 3 times, the benzene extract was combined with the oil layer, dried, de-benzene and vacuum distilled to obtain 2.5g of product, the yield was 74.4%. Preparation of 1-(4-ethoxyphenyl)-2-bromo-2-methyl-1-propanone the above product 42g with 95ml of anhydrous diethyl ether was added dropwise 8g of bromine at 20 °c for 1.5H, after dropping, the reaction was continued for 30min, 100ml of water was slowly added, and the mixture was stirred and allowed to stand for stratification. The ether layer was washed with water, 30% sodium bisulfite solution, washed with water, dried and deetherified to give 43g of white crystals, m. P. 36-38 °c. Preparation of 2-(4-ethoxyphenyl)-2-methylpropionic acid the above product 239G, methanol 120mL, triethyl orthoformate 478mL, methanesulfonic acid 16mL were incubated at 60 ℃ for 12h, 15% ml of sodium hydroxide was added to pH 12 with stirring and heated under reflux for 3H. Pour into a large beaker, add 250ml of water and 67.7% ml of CCl4, let stand to separate layers, add ml of concentrated hydrochloric acid to the aqueous layer, filter, and vacuum dry to obtain 124g of product, m. P. 81-83 ℃, yield. Preparation of 2-(4-ethoxyphenyl)-2-methylpropanol 83.5g of the above product and 500ml of diethyl ether were slowly dropped into a mixture of 450ml of diethyl ether and 17g of lithium aluminum hydride under anhydrous conditions, after stirring at room temperature for 2H, ethyl acetate was added dropwise. The reaction was continued for 15min after dropping, 4mol/L sulfuric acid 10% ML was added dropwise, the layers were separated, and the ether layer was washed with sodium hydroxide and then washed with water, dried, placed and deetherified to obtain 75g of product. Synthesis of the ether of the product of the previous step of 172g, M-phenoxybenzyl chloride 207.5g, in the presence of sodium hydroxide, tetra-n-butyl ammonium bromide (28.7g) as a phase transfer catalyst, at 80 deg C for 4H, after cooling, add 390ml of water, stir for 20min, extract with toluene, wash the extract with water, dry, desolventilate, vacuum distillation, collect 226~255 ℃/399.9 ~ 633Pa fraction 211.5g, content 95.4%, the yield was 63.4%. Preparation Method di-p-ethoxyphenylacetonitrile is reacted with methyl iodide in the presence of potassium hydroxide, water and trimethylbenzylammonium bromide, the product is hydrolyzed, then reduced with lithium aluminum hydride, and finally in the presence of sodium hydride and acetonitrile, with M-phenoxybenzyl chloride reaction, synthesis of ether. Preparation Method preparation of Tri-tert-butyl acetophenyl Ester P-tert-butyl phenol (0.67mol) reacts with acetic anhydride (0.8mol), refluxing at 140 ℃ for 4H, removing by-product acetic acid and unreacted acetic anhydride, A yellow-brown liquid was obtained with a yield of 95% and a content of 91.2%. Preparation of [4-(2-chloro-1, 1-dimethylethyl) phenyl] Acetate a mixture of 91.2% G of the above product (content) and of carbon tetrachloride was heated to 60 °c. Add 2g of azobisisobutyronitrile and simultaneous chlorine, add a stream of 15g chlorine gas in 1H. After analysis, it was dissolved to 107g of brown-red liquid, and then distilled under reduced pressure to obtain 45g of product, yield 89%, and content 93.2%. Preparation of 1-chloro -2-(4-ethoxyphenyl)-2-methylpropane G (content 94%, 0.415mol) of the above product, 160g (1.04mol) of diethyl sulfate, 85g of flaky potassium hydroxide (content 82%, 1.245mol) were mixed, stirred, heated to 30 ℃, 24g of 20% benzyltriethylammonium chloride (0.0208mol) were added dropwise, and the mixture was added for about 10min, the reaction was stirred vigorously for 6H. After cooling, 88.5 ml of water was added, the solid was dissolved by stirring, and the layers were separated. The organic layer was washed with water, and the low boiling matter was removed under reduced pressure to obtain 89.6% g of yellow liquid product with a content of 89.9% and a yield. Synthesis of the next step product 50g (content 90%, 0.21mol), M-phenoxybenzyl alcohol 51.4g (content 98%, 0.252mol), Flake potassium hydroxide 21.5g (content 82%, 0.315mol), after 120ml of dimethyl sulfoxide was mixed, the mixture was heated to ℃ for 10H under the protection of nitrogen, and desolvated under reduced pressure. 100mL of water and 100mL of benzene were added to the residue, and the mixture was stirred and layered, debenzene was removed under reduced pressure to obtain 94g of brownish-black viscous liquid. 49.4g of ethrin was obtained by high vacuum distillation, with the content of 85.6% and the yield of 53.5%. |
| category | pesticide |
| toxicity grade | low toxicity |
| Acute toxicity | oral-rat LD50: 42800 mg/kg; Oral-mouse LD50: 107000 mg/kg |
| 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 |
Last Update：2024-04-09 15:16:53
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