4-BROMO-2-(4-CHLOROPHENYL)-1-(ETHOXYMETHYL)-5-(TRIFLUOROMETHYL)-1H-PYRROL-3-CARBONITRILE
Chlorfenapyr
CAS: 122453-73-0
Molecular Formula: C15H11BrClF3N2O
4-BROMO-2-(4-CHLOROPHENYL)-1-(ETHOXYMETHYL)-5-(TRIFLUOROMETHYL)-1H-PYRROL-3-CARBONITRILE - Names and Identifiers
| Name | Chlorfenapyr |
| Synonyms | Alert Citrex Pirate PIRATE STALKER Sunfire Intrepid Chlorfenapyr Chlorfenapyr bulk drug 4-bromo-2-(4-chlorophenyl)-1-ethoxymethyl-5-trifluoromethylpyrrole-3-carbonitrile 4-bromo-2-(4-chlorophenyl)-1-ethoxymethyl-5-trifluoromethyl-1H-pyrrole-3-carbonitrile 4-BROMO-2-(4-CHLOROPHENYL)-1-(ETHOXYMETHYL)-5-(TRIFLUOROMETHYL)-1H-PYRROL-3-CARBONITRILE |
| CAS | 122453-73-0 |
| InChI | InChI=1/C15H11BrClF3N2O/c1-2-23-8-22-13(9-3-5-10(17)6-4-9)11(7-21)12(16)14(22)15(18,19)20/h3-6H,2,8H2,1H3 |
| InChIKey | CWFOCCVIPCEQCK-UHFFFAOYSA-N |
4-BROMO-2-(4-CHLOROPHENYL)-1-(ETHOXYMETHYL)-5-(TRIFLUOROMETHYL)-1H-PYRROL-3-CARBONITRILE - Physico-chemical Properties
| Molecular Formula | C15H11BrClF3N2O |
| Molar Mass | 407.61 |
| Density | 1.53±0.1 g/cm3(Predicted) |
| Melting Point | 91-92° |
| Boling Point | 443.5±45.0 °C(Predicted) |
| Flash Point | 222°C |
| Water Solubility | Insoluble in water |
| Vapor Presure | 4.6E-08mmHg at 25°C |
| Appearance | neat |
| Color | White to Almost white |
| BRN | 6940152 |
| pKa | -18.00±0.70(Predicted) |
| Storage Condition | Sealed in dry,2-8°C |
| Refractive Index | 1.559 |
| Physical and Chemical Properties | The neat was a white solid. m.p.91 ~ 92 ℃(100~101 ℃), soluble in acetone, ether, dimethyl sulfoxide, Tetrahydrofuran, acetonitrile, alcohols and other organic solvents, insoluble in water. |
| Use | Structure of the new type of pyrrole insecticide, acaricide. It has excellent control effect on boring, sucking and chewing pests and mites. It is more effective than cypermethrin and cyhalothrin, and its acaricidal activity is stronger than dicofol and tricyclic tin. The medicine has the following characteristics: broad-spectrum insecticide, acaricide; Both stomach poison and contact killing effect; No cross-resistance with other insecticides; Moderate residual activity in crops; in the nutrient solution through the root absorption of selective absorption activity; Moderate oral toxicity to mammals, skin toxicity is low; The effective dosage is low (100g active ingredient/hm2). Its significant insecticidal, acaricidal activity and unique chemical structure have attracted extensive attention and concern. |
4-BROMO-2-(4-CHLOROPHENYL)-1-(ETHOXYMETHYL)-5-(TRIFLUOROMETHYL)-1H-PYRROL-3-CARBONITRILE - Risk and Safety
| Risk Codes | R22 - Harmful if swallowed R23 - Toxic by inhalation R50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. |
| Safety Description | S13 - Keep away from food, drink and animal foodstuffs. 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. |
| UN IDs | UN 2811 |
| WGK Germany | 3 |
| Toxicity | LD50 (single dose) in male, female rats (mg/kg): 223, 459 orally; in rabbits: >2000 dermally (Lovell); LC50 in Japanese carp: 0.5 ppm (Lovell) |
4-BROMO-2-(4-CHLOROPHENYL)-1-(ETHOXYMETHYL)-5-(TRIFLUOROMETHYL)-1H-PYRROL-3-CARBONITRILE - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| introduction | chlorfenapyril, also known as chlorfenapyril, is an aryl pyrrole compound, which has stomach toxicity, certain contact and systemic activity to pests; it is a insecticidal, acaricidal and nematicidal agent successfully developed on the basis of dioxopyrromycin isolated from the metabolites of Streptomyces fungi in 1985 by the American Cyanamide Company. It has excellent control effect on borer and sucking mouthpart pests and mites, with a moderate duration. Its insecticidal mechanism is to block the phosphorylation of mitochondria. |
| action characteristics | chlorfenapyril is transformed into active substance (insecticidal activity) through multifunctional oxidase in insects. Remarks: Multifunctional oxidase mainly interprets pyrethroids, organophosphorus and macrolides. |
| toxicity | acute oral LD50 in rats is 459 mg/kg (female) and 223 mg/kg (male) (662 mg/kg, rat). Acute percutaneous LD50 ≥ 2000mg/kg in rabbits. It has mild irritation to rabbit eyes. Ames showed no mutagenicity by improved test and hamster ovary test. The LC50 of Japanese carp is 0.5mg/L (48h). |
| use | new pyrrole insecticide and acaricide. It has excellent control effect on borer, pricking and chewing pests and mites. It is more effective than cypermethrin and cyhalothrin, and its acaricidal activity is stronger than dicofol and tricyclic tin. The agent has the following characteristics: broad-spectrum insecticides and acaricides; both gastric toxicity and contact killing; no cross resistance with other insecticides; moderate residual activity on crops; selective absorption by roots in nutrient solutions; moderate oral toxicity to mammals, low transdermal toxicity; low effective application amount (100g active ingredient/hm2). Its remarkable insecticidal, acaricidal activity and unique chemical structure have received extensive attention and attention. |
| production method | preparation of 2-(p-chlorophenyl) sarcosine 88g methylamine hydrochloride aqueous solution and 53g NaCN aqueous solution were added to 153g of tetrahydrofuran solution of p-chlorobenzaldehyde. Stir at room temperature for 16h. Extraction with toluene, adding 10mL of pyridine to the toluene layer, followed by 50mL of acetic anhydride. Stir at room temperature, vacuum concentrate the oil and add to a 1:1 mixture of water and hydrochloric acid. Heating reflux for 2h, cooling, dilution with water, neutralization with 50% sodium hydroxide solution to pH 2, solid precipitation. Filtration, air drying, white solid 180g. M. p.208 ~ 213 ℃. Preparation of 2-(p-chlorophenyl)-N-(trifluoroacetyl) sarcosine 27g of 2-(p-chlorophenyl) sarcosine was dissolved in anhydrous toluene, treated with 20mL trifluoroacetic anhydride, stirred for 1h, and concentrated in vacuum to obtain solid residue. Repeated vaporization of the residue with toluene several times to obtain 38.7g of red solid. M. p.117 ~ 118 ℃. 2-(p-chlorophenyl)-1-methyl -5-(trifluoromethyl)-2-pyrroline -3-nitrile was prepared in 7.4g of 2-(p-chlorophenyl)-N-(trifluoromethyl) sarcosine acetonitrile solution, 5.1g of acetic anhydride, 1.6g of acrylonitrile and 10 drops of triethylamine were added, heated under reflux for 5.5h, cooled, and concentrated in vacuum to obtain red oily residue. Filter with silica gel column, wash with n-hexane/ethyl acetate mixture, then wash with dichloromethane and ethyl acetate mixture. The filtrates were combined, concentrated in vacuum, and recrystallized with dichloromethane to obtain a light yellow needle-like solid. M. p.158 ~ 160 ℃. 2-(p-chlorophenyl)-1-methyl -5-(trifluoromethyl) pyrrole -3-nitrile was prepared in 2.87g of 2-(p-chlorophenyl)-1-methyl -5-(trifluoromethyl)-2-pyrroline -3-nitrile chlorobenzene solution, 1.76g of bromine chlorobenzene solution was added, heated to 100 ℃, and reacted for 4~5h. Cool to room temperature, dilute with water, and extract ethyl acetate. Combine the extracts, wash with water, sodium metasulfite and water, dry anhydrous magnesium sulfate, and concentrate in vacuum to obtain light yellow solid residue. Recrystallization with n-pentane/ethyl acetate to obtain light yellow crystal 2.4g,m.p.129.5~130 ℃. 4-Bromo-2-(p-chlorophenyl)-1-methyl -5-(trifluoromethyl) pyrrole -3-nitrile was prepared in a chlorobenzene solution of 2-(p-chlorophenyl)-1-methyl -5-(trifluoromethyl) pyrrole -3-nitrile (5.70g), 3.52g of bromine was added, heated to 80°C, and kept for 20h. After cooling, add 3.52g of bromine and heat to 100 ℃. The reaction mixture is cooled and ethyl acetate is extracted. Combine the extracts, wash with water and sodium metasulfite solution successively, dry anhydrous magnesium sulfate, and concentrate in vacuum to obtain solid residue. The residue was crystallized with ethyl acetate/n-hexane mixed solvent to obtain 6.50g of white solid. M. p.126 ~ 129 ℃. Preparation of 4-bromo-2-(p-chlorophenyl)-1-(bromomethyl)-5-(trifluoromethyl) pyrrole -3-nitrile under stirring, 7.27g of 4-bromo-2-(p-chlorophenyl)-1-methyl -5-(trifluoromethyl) pyrrole -3-nitrile is dissolved in carbon tetrachloride, 3.52g of bromine is added, and heated to a certain temperature, light for 2 ~ 4d, then cold to room temperature, washed with sodium metasulfite aqueous solution, the organic phase is vacuum concentrated, and the residue is recrystallized from n-heptane to obtain a white solid product. M. p.131 ~ 131.5 ℃. Preparation of chlorfenapyril 4.42g of 4-bromo-2-(p-chlorophenyl)-1-(bromomethyl)-5-(trifluoromethyl) pyrrole-3-nitrile was mixed with anhydrous ethanol, treated with an ethanol solution of 0.715g of 21% sodium ethoxide, heated to 80 ℃, and kept for 15-25min. Cooling, dilution with water and ether, separation of organic layer, anhydrous magnesium sulfate drying. Vacuum concentration, n-heptane recrystallization, white solid chlorfenapyril 3.45g. m.p.91~92 ℃. The second preparation method is to prepare 2-(4-chlorophenyl) -5-trifluoromethyloxazolone-3 from the action of trifluoroacetamido-4-chlorobenzoic acid and aldehyde anhydride, and then combine it with α-Chloroacrylonitrile reacts to prepare 2-(4-chlorophenyl)-5-trifluoromethylpyrrole-3-nitrile, and then react with bromine and chloromethyl ether to prepare coside nitrile mites. For details of the synthetic route of chlorfenapyril, please refer to Pesticide, 2003,42(2). |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-10 22:29:15
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