5-(2-CHLORO-4-TRIFLUOROMETHYLPHENOXY)-2-NITROBENZOIC ACID
Acifluorfene
CAS: 50594-66-6
Molecular Formula: C14H7ClF3NO5
5-(2-CHLORO-4-TRIFLUOROMETHYLPHENOXY)-2-NITROBENZOIC ACID - Names and Identifiers
| Name | Acifluorfene |
| Synonyms | PPG-847 ppg-847 MC 10109 Acifluorfen ACIFLUORFEN Acifluorofen TACKLE 2S TM acifluorofen Acifluorfene Carbofluorfen 2-NITRO-5-(2-CHLORO-TRIFLUOROMETHYL PHENOXY)BENZOIC ACID 5-(2-CHLORO-4-TRIFLUOROMETHYLPHENOXY)-2-NITROBENZOIC ACID 5-(2-chloro-α,α,α-trifluoro-p-tolyloxy)-2-nitrobenzoic acid 2-Nitro-5-(2-chloro-4-(trifluoromethyl)phenoxy)benzoic acid 5-[2-Chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoic acid 2-NITRO-5-(2-CHLORO-4-(TRIFLUOROMETHYL)PHENOXY)BENZOIC ACID |
| CAS | 50594-66-6 |
| EINECS | 256-634-5 |
| InChI | InChI=1/C14H7ClF3NO5/c15-10-5-7(14(16,17)18)1-4-12(10)24-8-2-3-11(19(22)23)9(6-8)13(20)21/h1-6H,(H,20,21) |
5-(2-CHLORO-4-TRIFLUOROMETHYLPHENOXY)-2-NITROBENZOIC ACID - Physico-chemical Properties
| Molecular Formula | C14H7ClF3NO5 |
| Molar Mass | 361.66 |
| Density | 1.5676 (estimate) |
| Melting Point | 151.5-157° |
| Boling Point | 422.4±45.0 °C(Predicted) |
| Flash Point | 209.2°C |
| Vapor Presure | 6.89E-08mmHg at 25°C |
| Appearance | neat |
| Merck | 13,111 |
| BRN | 2953865 |
| pKa | 1.93±0.25(Predicted) |
| Storage Condition | 0-6°C |
| Refractive Index | 1.575 |
| Physical and Chemical Properties | This product is a light yellow solid. m. P. 240 °c, relative density 1.546, vapor pressure 0.01 x 10-3 (0.13 x 10-3Pa (20 °c). Solubility: acetone 50% ~ 60%, ethanol 40% ~ 50%, dichloromethane 5%, xylene <1%, in water solubility of 120mg/kg (original). 235 degrees C decomposition, in the pH value of 3~9, 40 degrees Celsius is not hydrolyzed, in the soil Half-Life <60d. Non-corrosive. m. P. 142~160 ℃. |
| Use | It is a contact herbicide, used for early treatment after seedling, can be absorbed by weeds, stems and leaves, and the mode of action is contact killing |
5-(2-CHLORO-4-TRIFLUOROMETHYLPHENOXY)-2-NITROBENZOIC ACID - Risk and Safety
| Risk Codes | R22 - Harmful if swallowed R38 - Irritating to the skin R41 - Risk of serious damage to eyes R50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. |
| Safety Description | S24 - Avoid contact with skin. S39 - Wear 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. |
| UN IDs | UN 3077 |
| WGK Germany | 3 |
| RTECS | DG5643070 |
| HS Code | 29189900 |
5-(2-CHLORO-4-TRIFLUOROMETHYLPHENOXY)-2-NITROBENZOIC ACID - Upstream Downstream Industry
| Raw Materials | Potassium hydroxide benzotrifluoride |
5-(2-CHLORO-4-TRIFLUOROMETHYLPHENOXY)-2-NITROBENZOIC ACID - Nature
Open Data Verified Data
light yellow solid. mp151.5 ~ 157 ℃, the relative density of 1. 546. Solubility at 23-25 °c (g/L): Water 0. 12 (original drug), acetone 500~600, dichloromethane 50, ethanol 400~500, oil <10, xylene <10. 235 degrees C decomposition, in the pH of 3~9, 40 degrees C below the hydrolysis, in the soil Half-Life <60d. Non-corrosive.
Last Update：2024-01-02 23:10:35
5-(2-CHLORO-4-TRIFLUOROMETHYLPHENOXY)-2-NITROBENZOIC ACID - Preparation Method
Open Data Verified Data
- 3-(2-chloro -4-fluoromethylphenoxy) benzoic acid was obtained by reacting 3,4-= chlorotrifluorotoluene with M-Hydroxybenzoic acid in the presence of KOH using dichloromethylsulfoxide as a solvent. The nitration reaction was then carried out in a dichloromethane solvent with potassium nitrate-sulfuric acid to obtain trichosphoran, and then reacted with equimolar NaOH to obtain a sodium salt.
- or from 3,4-= chlorotrifluorotoluene and m-cresol potassium salt, reaction in solvent to produce 3-(2-chloro-4-fluoromethylphenoxy) methyl benzene, then in the catalyst, 3-(2-chloro-4-fluoromethylphenoxy) benzoic acid is obtained in the presence of acetic acid. Trifluorophoric ether was obtained by nitration and reacted with NaOH to form sodium salt.
- can also be from 3 monochloro-4-hydroxytrifluorotoluene and 5 monochloro-2-nitrobenzoic acid in the solvent DMSO, potassium carbonate and nitrogen protection, the reaction was carried out at room temperature to obtain trifluorophoric ether.
Last Update：2022-01-01 10:12:33
5-(2-CHLORO-4-TRIFLUOROMETHYLPHENOXY)-2-NITROBENZOIC ACID - Use
Open Data Verified Data
protoporphyrin oxidase inhibitors. Fluorine-containing diphenyl ether herbicides are contact-selective post-emergence herbicides. It is suitable for the control of annual Broad-leaved weeds and other weeds in soybean, peanut and other crops, such as Portulaca oleracea, duck toe grass, iron amaranth, hemp, millet grass, Solanum nigrum, Xanthium, etc. The preparation should not be used in intercropping or mixed planting of soybean with other crops, and should not be used under abnormal conditions such as drought, waterlogging, salinity or frost. In order to control Gramineae weeds, it can be mixed with trifluralin, heding, pirarubicin and the like.
Last Update：2022-01-01 10:12:34
5-(2-CHLORO-4-TRIFLUOROMETHYLPHENOXY)-2-NITROBENZOIC ACID - Safety
Open Data Verified Data
The oral LD50 of the original drug to rats was 1540mg/kg, and the percutaneous LD50 of rabbits was 3680mg/kg. Moderate irritation to the eyes and skin. Rats acute inhalation LC50>6.9mg/L(4H), rats 2 years feeding Test No effect dose of 180mg/kg. No teratogenic, carcinogenic, mutagenic effect was found in animal test, and no abnormality was found in the third generation reproductive test. The LC50 was 17mg/L(96h) for rainbow trout and 62mg/L(96h) for blue carp. Quail oral LD50 325mg/kg. Safe for bees.
Last Update：2022-01-01 10:12:34
5-(2-CHLORO-4-TRIFLUOROMETHYLPHENOXY)-2-NITROBENZOIC ACID - 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 in male rats is 2025 mg/kg, while that in females is 1370 mg/kg. The acute oral LD50 of male mice is 2050mg/kg, and the female is 1370mg/kg. The acute oral LD50 of the original drug to rats was 1540mg/kg. Acute percutaneous LD50 in rabbits was 3680mg/kg. Moderate irritation to eyes and skin. Acute inhalation of LC50>6.9mg/L (4h) in rats. The 2-year feeding test of rats had no effect of 180mg/kg. The Ames test was negative. No teratogenic, carcinogenic and mutagenic effects were found in animal experiments, and no abnormalities were found in the three generations of reproduction experiments. LC50 was 17mg/L (96h) for trout and 62mg/L (96h) for blue gill. The acute oral LD50 of quail is 325mg/kg. Safe for bees. |
| use | fluorodiphenyl ether herbicides. It is a contact selective post-bud herbicide. It is a protoporphyrin oxidase inhibitor. The agent is mainly absorbed by weed stems and leaves, inhibiting mitochondrial electron conduction, causing stagnation of respiratory system and energy production system, inhibiting cell division and causing weed death. It is suitable for controlling annual broad-leaved weeds and other weeds in soybean, peanut and other crops, such as purslane, Commelina communis, amaranth, Abutilon, corn grass, quinoa, Solanum nigrum, Xanthium, Datura, etc. The recommended dosage for soybean fields is 380~420g/hm2 and 180~320g/hm2. If soybean land is used, generally in soybean 1~3 leaf stage, weed 2~4 leaf stage, with 24% water 7.5mL/100 m2 (such as drought and weeds 3~4 leaf stage need 11.3mL), water spray weed stems and leaves. It should not be mixed with chemical fertilizer. It is a contact herbicide. It is used for early treatment after seedling. It can be absorbed by weeds, stems and leaves. The mode of action is contact killing |
| production method | equimolar 3,4-dichlorotrifluorotoluene and meta-hydroxybenzoic acid are used as raw materials to react with dimethyl sulfoxide as solvent at 138~144 ℃ for 22h in the presence of KOH to generate 3-(2-chloro-4-trifluoromethylphenoxy) benzoic acid. Then in dichloromethane solvent, potassium nitrate-sulfuric acid is used for nitration reaction to produce trifluorocarboxane ether. Then react with equimolar NaOH to make sodium salt. Using m-cresol as raw material, equimolar 3, 4-dichlorotrifluorotoluene and m-cresol potassium salt are reacted in a solvent at 149~155 ℃ to generate 3-(2-chloro-4-trifluoromethylphenoxy) methylbenzene, and then in the presence of catalyst and acetic acid, it is oxidized by air at 94~96 ℃ to obtain 3-(2-chloro-2-trifluoromethylphenoxy) benzoic acid, then nitrated with mixed acid in the presence of solvent and vinegar rod at 45 ℃ to obtain trifluorocarboxane ether, and then reacted with equimolar NaOH to make sodium salt. Using 3-chloro-4-hydroxytrifluorotoluene as raw material, equimolar 3-chloro-4-hydroxytrifluorotoluene and 5-chloro-2-nitrobenzoic acid are protected by solvent DMSO, potassium carbonate and nitrogen. The reaction at room temperature produces trifluorocarboxane ether. |
Last Update：2024-04-09 21:04:16
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Raw Materials for 5-(2-CHLORO-4-TRIFLUOROMETHYLPHENOXY)-2-NITROBENZOIC ACID