2-Chloro-N-[(4,6-diméthoxy-2-pyrimidinyl)carbamoyl]imidazo[1,2-a]pyridine-3-sulfonamide
Imazosulfuron
CAS: 122548-33-8
Molecular Formula: C14H13ClN6O5S
2-Chloro-N-[(4,6-diméthoxy-2-pyrimidinyl)carbamoyl]imidazo[1,2-a]pyridine-3-sulfonamide - Names and Identifiers
2-Chloro-N-[(4,6-diméthoxy-2-pyrimidinyl)carbamoyl]imidazo[1,2-a]pyridine-3-sulfonamide - Physico-chemical Properties
| Molecular Formula | C14H13ClN6O5S |
| Molar Mass | 412.81 |
| Density | d25 1.574 |
| Melting Point | 183-184° (dec) |
| Appearance | neat |
| pKa | 4.0(at 25℃) |
| Storage Condition | 0-6°C |
| Refractive Index | 1.715 |
| Physical and Chemical Properties | Pure white crystals. m.p.183 ~ 184 ℃ (decomposition), relative density 1.574 (25 ℃), vapor pressure 4.52 × 10-2Pa (25 ℃), dissociation constant pka4. The solubility in organic solvent at 25 ℃ is: dichloromethane 12.8g/L, acetone 7.6g/L, acetonitrile 2.5g/L, ethyl acetate 2.2g/L, xylene 400mg/L; in water solubility of 308mg/L (pH = 7), 67mg/L (pH = 6.1), 5mg/L (pH = 5.1). The distribution coefficient was 0.05. |
2-Chloro-N-[(4,6-diméthoxy-2-pyrimidinyl)carbamoyl]imidazo[1,2-a]pyridine-3-sulfonamide - Risk and Safety
| WGK Germany | 1 |
| HS Code | 29350090 |
2-Chloro-N-[(4,6-diméthoxy-2-pyrimidinyl)carbamoyl]imidazo[1,2-a]pyridine-3-sulfonamide - Nature
Open Data Verified Data
pure white crystals. Melting point 183~184 ℃ (decomposition), relative density (25 ℃) is 1. 574, vapor pressure (25 ℃) is 4.52 × 10-2PA. Dissociation constant pK. = 4. The solubility in organic solvents at 25 °c is: dichloromethane 12. 8g/L, acetone 7. 6g/L, acetonitrile 2.5g/L, ethyl acetate 2. 2G/L, xylene 400mg/L; Solubility in water is 3. 8mg/L (pH 7), 67mg/L (pH 6.1), 5mg/L (pH -5.1), octanol/water distribution coefficient is 0. 05.
Last Update：2024-01-02 23:10:35
2-Chloro-N-[(4,6-diméthoxy-2-pyrimidinyl)carbamoyl]imidazo[1,2-a]pyridine-3-sulfonamide - Preparation Method
Open Data Verified Data
first, 2 monochloro imidazo [1,2-a] pyridine-3-sulfonamide is prepared, then the mixture of the compound and triethylamine is added to dichloromethane, and the reaction is carried out Dropwise with phenyl chloroformate, methanesulfonic acid and 2-amino -4,6-= methoxypyrimidine were added sequentially to continue the reaction, and imidazosulfuron was obtained by treatment.
Last Update：2022-01-01 10:12:51
2-Chloro-N-[(4,6-diméthoxy-2-pyrimidinyl)carbamoyl]imidazo[1,2-a]pyridine-3-sulfonamide - Use
Open Data Verified Data
used as herbicide. Through the root absorption, transport to the whole plant, the key enzyme of branched chain amino acid biosynthesis-acetolactate synthase, has a strong inhibitory effect. It can inhibit the growth of the tip buds of weeds, prevent the growth and development of roots or seedlings, and make them die gradually. Can control most of the annual and perennial broadleaved weeds and Cyperaceae weeds, such as cow felt, Arrowhead, cyperus, cress, Humulus scandens, can also control malignant weeds, such as wild arrowheads.
Last Update：2022-01-01 10:12:52
2-Chloro-N-[(4,6-diméthoxy-2-pyrimidinyl)carbamoyl]imidazo[1,2-a]pyridine-3-sulfonamide - Reference Information
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| toxicity | low toxicity to fish and mammals. |
| use | is absorbed by the root and then transported to the whole plant, which has a strong inhibitory effect on acetolactate synthase (ALS), a key enzyme in branched chain amino acid biosynthesis. Inhibit the growth of weed tip buds and prevent the growth and development of roots or seedlings, thus causing them to gradually die. It can be used before budding or 10~15 days after rice transplantation to control most annual weeds including barnyard grass and perennial weeds such as cow felt, firefly, sedge, cress, dwarf sagitar and so on. The recommended usage is 30g/hm2. Mixing with other herbicides can enhance the control effect on barnyard grass. |
| production method | preparation of 2-imino -1,2-dihydropyridine -1-acetic acid 50.2g chloroacetic acid is dissolved in 80mL of water and 20mL of ethanol, 75mL triethylamine is added at 10~15 ℃, then 50g of 2-aminopyridine is added, the temperature is raised to 75~80 ℃, the reaction is carried out for 5h, and 100mL of ethanol is added, ice water is cooled, filtered and washed to obtain 64.6g of product with 80% yield. Preparation of 2-chlorimidazo [1,2-α] pyridine 45.7g of the previous product is suspended in 120mL toluene, heated to 105~110 ℃, then added dropwise 93.1g of phosphorus oxychloride, added for 1h, refluxed for 5h, cooled, and poured into ice water. The organic layer is separated, and the water layer is neutralized with sodium hydroxide solution (30~45 ℃), I .e. solid is precipitated, 42g of product is obtained by washing and drying with water, and the yield is 91.7%. Preparation of 2-chlorimidazo [1,2-α] pyridine -3-sulfonyl. Dissolve 15.3g of the second step product in 75mL dichloroethane, add 14.3g of 98.5% chlorosulfonic acid dropwise under stirring, refluxing for 5h, cooling to 20 ℃, dropping 12.1g of triethylamine, and heating refluxing for 3h. After cooling, 200mL of ice water is injected to separate the organic layer, and 24.7g of the product is obtained after negative pressure evaporation to remove dichloroethane, with a yield of 97.6%. Preparation of 2-chlorimidazo [1,2-α] pyridine -3-sulfonamide Under cooling, a solution consisting of 4.6g of step 3 product and 60mL of acetonitrile is added to 60mL of ammonia water, stirred and reacted for 2h at room temperature, acetonitrile is distilled under reduced pressure, the crystals formed are filtered and collected, washed with water and dried to obtain 3.8g of the product with 89.6% yield. Synthesis of imidazosulfuron A mixture consisting of 10g (0.043mol) of the 4th step product and 8.85g of triethylamine (0.0866mol) was added to 200mL of dichloromethane, and then 6.78g (0.0433mol) of phenyl chloroformate was added dropwise at 20~25 ℃. The reaction was continued for 30min, and 4.2g (0.0433mol) methanesulfonic acid and 6.72g (0.0433mol) phenyl chloroformate were added in sequence. The reaction was continued for 30min, 4.2g (0.0433mol) methanesulfonic acid and 6.72g (0.0433mol) 2-amino -4,6-dimethoxypyrimidine were added in sequence, heated and refluxed for 5h, dissolved under reduced pressure after the reaction, 50mL acetonitrile was added to the residue, filtered, and washed with acetonitrile and water respectively to obtain 15.62g of the target product with a yield of 87.9%. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 19:05:10
![2-Chloro-N-[(4,6-diméthoxy-2-pyrimidinyl)carbamoyl]imidazo[1,2-a]pyridine-3-sulfonamide](http://res.chembk.com/assets/str/2d/1/12/122548-33-8.png)
Supplier List
Product Name: Imazosulfuron Visit Supplier Webpage Request for quotation
CAS: 122548-33-8
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
CAS: 122548-33-8
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
Product Name: Imazosulfuron Visit Supplier Webpage Request for quotation
CAS: 122548-33-8
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
CAS: 122548-33-8
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
View History