Bifenox
5-(2,4-Dichlorphenoxy)-2-nitrobenzoic acid methyl ester;Bifenox
CAS: 42576-02-3
Molecular Formula: C14H9Cl2NO5
Bifenox - Names and Identifiers
| Name | 5-(2,4-Dichlorphenoxy)-2-nitrobenzoic acid methyl ester Bifenox |
| Synonyms | FOX MC 79 MODOWN Plodown Bifenox BIFENOX MC-4379 bifenox (bsi,iso,ansi,wssa) METHYL 5-(2,4-DICHLOROPHENOXY)-2-NITROBENZOATE methyl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate 5-(2,4-Dichlorphenoxy)-2-nitrobenzoic acid methyl ester |
| CAS | 42576-02-3 |
| EINECS | 255-894-7 |
| InChI | InChI=1/C14H9Cl2NO5/c1-21-14(18)10-7-9(3-4-12(10)17(19)20)22-13-5-2-8(15)6-11(13)16/h2-7H,1H3 |
Bifenox - Physico-chemical Properties
| Molecular Formula | C14H9Cl2NO5 |
| Molar Mass | 342.13 |
| Density | 1.5715 (rough estimate) |
| Melting Point | 84-86° |
| Boling Point | 421.0±45.0 °C(Predicted) |
| Flash Point | 208.4°C |
| Water Solubility | 0.5mg/L(temperature not stated) |
| Vapor Presure | 2.7E-07mmHg at 25°C |
| Appearance | neat |
| Merck | 13,1214 |
| BRN | 2170169 |
| Storage Condition | Keep in dark place,Sealed in dry,Room Temperature |
| Refractive Index | 1.7350 (estimate) |
| Physical and Chemical Properties | This product is yellow or light brown crystal. m. P. 84~86 ℃, decomposition temperature 290 ℃, relative density 1.155, vapor pressure 2 x 10-4pa. At 25 ° C, the solubility in ethanol is less than 5%, 40% in acetone, 30% in xylene, 35% to 40% in chlorobenzene, 4% in benzene, and 0.36mg/L in water. Stable to light, the half-life in soil was 7 ~ 14d. |
| Use | Used as pharmaceutical, pesticide intermediates |
Bifenox - Risk and Safety
| Hazard Symbols | N - Dangerous for the environment |
| Risk Codes | 50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. |
| Safety Description | 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 3077 9/PG 3 |
| WGK Germany | 2 |
| RTECS | DG7890000 |
| HS Code | 29189900 |
| Toxicity | LD50 orally in rats, mice: >6400, 4556 mg/kg; LC50 in pheasants, wild ducks: >5000 ppm (Kruger) |
Bifenox - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| toxicity | acute oral LD50>6400mg/kg in rats and acute percutaneous LD50>20000mg/kg in rabbits. No severe inhalation toxicity, no eye irritation. High doses of rats and dogs did not produce pathological and histological changes. No teratogenic, carcinogenic and mutagenic effects. Highly toxic to fish and aquatic organisms, rainbow trout LC50>0.18mg/L (96h), carp LC50>1.22mg/L (48h), shrimp LC50 0.065 mg/kg. Low toxicity to bees, acute exposure LD50>1000 μg/mouse. Low toxicity to birds, quail acute oral LD50>5000mg/kg. |
| use | contact type pre-bud soil treatment agent has the characteristics of wide grass killing spectrum, low application amount, strong soil adaptability and no influence of temperature. The agent is absorbed by the weed buds and destroys the photosynthesis of the weed. Suitable for soybean, rice, sorghum, corn, wheat and other crops to control barnyard grass, thousand gold, Commelina communis, amaranth, Polygonum benthi, Chenopodium, Portulaca oleracea, Abutilon, Xanthium sibiricum, duck tongue grass, Alisma, Solanum nigrum, Koch and other weeds. For example, rice is used for transplanting Honda, and 7% granule 240~285g/100m2 or 80% wettable powder 22~25g/100 m2 is used for 4~6 days after transplanting to make poisonous soil for spreading. The shallow water layer is irrigated during application, and the water layer is maintained for 3~4 days after application. The recommended dosage is 1 ~ 2kg active ingredient/hm2. methyl ester is a photosynthesis inhibitor, which can be absorbed by leaves faster, but the conduction speed in plants is slow. It is a pre-bud herbicide and is mainly used for weeding soybeans. It has the advantages of low application amount, wide weeding spectrum, strong adaptability to soil, and not affected by temperature. Acute oral toxicity LD50 rats were greater than 6400mg/kg, and acute transdermal toxicity LD50 rabbits were greater than 20000mg/kg. TLM carp (48h) is 1.22ppm. Used as an intermediate in medicine and pesticide |
| production method | using benzoyl chloride, chlorine, and 2,4-dichlorophenol as the main raw materials, and performing the following reactions. 1. Preparation of m-chlorobenzoyl chloride 281g of benzoyl chloride, 1.4g of iron powder and 0.56g of sulfur were put into the reaction bottle. Keep the temperature at 20 ℃ and chlorinated for about 2.5h. Then nitrogen is used to remove phosgene and the hydrogen chloride gas generated by the reaction. 2. Preparation of methyl m-chlorobenzoate Methanol was slowly added to the stirred m-chlorobenzoyl chloride (molar ratio of acid chloride: methanol = 1.0:1.1). Esterification reaction is carried out between 25-68 ℃, reflux for 2-3h, a large amount of hydrogen chloride is released during the reaction, and excess methanol is recovered. Preparation of methyl 3.5-chloro-2-nitrobenzoate 853g of methyl m-chlorobenzoate and 500g of 1,2-dichloroethane were added to the reaction bottle, cooled to -10 ℃, and 338g of 95% mixed acid of fuming nitric acid (5.1mol) and 816g of 96% sulfuric acid (8mol) were added dropwise for about 3 hours. The reaction was stirred at -10 ℃ for 2h, then heated to 30 ℃ for 3h. The organic layer is separated, filtered and dried. 4. Preparation of methyl ester weed ether: 189g of solid potassium carbonate (97%) is added into 2,4-dichlorophenol (97%)419g and 960ml of dimethylformamide solvent under stirring, heated and refluxed for 1h, accompanied by carbon dioxide release, about 50% of dimethylformamide is evaporated, and 638g of methyl 5-chloro -2-nitrobenzoate (80%) is added into 95% phenol salt under stirring. After adding, react at 100 ℃ for 3h, add methanol to dissolve the product, cool it, and filter out potassium chloride. The filtrate is cooled and crystallized, with a melting point of 84-86°C. Prepare 10% granules, 21% emulsifiable concentrate and 25% wettable powder. preparation method-hydrolysis reaction: 772g benzyl trichloride and 0.25g ferric trichloride are mixed with hands, the temperature is raised to 120 ℃, then 75g of water is added dropwise at a constant temperature within a certain period of time, and the dropwise continues to stir for 30min to obtain 633g of benzoyl chloride with a yield of 96%. In the chlorination reaction, 281g of benzoyl chloride, 1.4g of iron powder and 0.56g of sulfur are added, and the chlorine reaction is carried out at 20 ℃ for 2.5h to drive away the residual chlorine and hydrogen chloride gas to obtain crude m-chlorobenzoyl chloride with a yield of 70% ~ 80%. In the esterification reaction, methanol is added dropwise to m-chlorobenzoyl chloride in a ratio of 1:1 (mol) and reacted in the range of 25~68 ℃. The reaction process has slight exothermic phenomenon. The feeding speed can be adjusted, the reaction temperature can be controlled, and a large amount of hydrogen chloride escapes during the reaction process. The excess methanol and residual hydrogen chloride gas are removed by vacuum to obtain colorless methyl m-chlorobenzoate liquid with a yield of 98% ~ 99%. In the nitrification reaction, 853g of methyl m-benzoate (purity 94%) and 500g of 1,2-dichloroethane were mixed by hand, cooled to -10 ℃, 338g of 95% fuming nitric acid and 816g of 96% sulfuric acid (mixed acid) were added dropwise within 3h, the reactants were stirred at -10 ℃ for 2h, then stirred at 0~30 ℃ for 3h, and the organic layer (1, 2-dichloroethane), filtered and dried to obtain 829g of methyl 5-chloro-2-nitrobenzoate with 76.9% yield. In the condensation reaction, 1.61mol of solid potassium carbonate was added to 2.49mol of 2,4-dichlorophenol and 960mL DMF solution, and the temperature was raised and refluxed for 1h, accompanied by the escape of carbon dioxide gas. After nearly 1/2 of DMF (water produced by entrainment) solvent was distilled out, 2.37mol of methyl 5-chloro-2-nitrobenzoate was added to phenolate solution at 95 ℃. After adding, react at 100 ℃ for 3h, vacuum evaporate DMF, add 1000mL methanol to dissolve the crude product, cool the large medicine to 65 ℃, filter out KCl, freeze and crystallize the mother liquor, and get 420g of pure methyl carboxylic hermite with 50% yield. Preparation method ii |
| category | pesticide |
| toxicity classification | low toxicity |
| acute toxicity | oral-rat LD50: 6400 mg/kg; Oral-mouse LD50: 4556 mg/kg |
| flammability hazard characteristics | Combustion produces toxic nitrogen oxides and chloride gases |
| storage and transportation characteristics | warehouse ventilation and low temperature drying; separate from food raw materials 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：2024-04-10 22:29:15
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Multiple Specifications
Product Name: Bifenox Visit Supplier Webpage Request for quotationCAS: 42576-02-3
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
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