Primisulfuron-methyl
Primisulfuron
CAS: 86209-51-0;113036-87-6
Molecular Formula: C15H12F4N4O7S
Primisulfuron-methyl - Names and Identifiers
| Name | Primisulfuron |
| Synonyms | Ciba-Geigy Beacon,Tell Primisulfuron Primisulfuron-methyl Primisulfuron(BSI,draft E-ISO) 2-({[4,6-bis(difluoromethoxy)pyrimidin-2-yl]carbamoyl}sulfamoyl)benzoic acid methyl 2-({[4,6-bis(difluoromethoxy)pyrimidin-2-yl]carbamoyl}sulfamoyl)benzoate |
| CAS | 86209-51-0 113036-87-6 |
| InChI | InChI=1/C15H12F4N4O7S/c1-28-11(24)7-4-2-3-5-8(7)31(26,27)23-15(25)22-14-20-9(29-12(16)17)6-10(21-14)30-13(18)19/h2-6,12-13H,1H3,(H2,20,21,22,23,25) |
Primisulfuron-methyl - Physico-chemical Properties
| Molecular Formula | C15H12F4N4O7S |
| Molar Mass | 468.33 |
| Density | 1.582g/cm3 |
| Melting Point | 203.1° (Maurer); mp 186-188° (Meyer) |
| Flash Point | 203 °C |
| Appearance | morphology neat |
| pKa | 3.78±0.10(Predicted) |
| Storage Condition | 2-8°C |
| Refractive Index | 1.535 |
| Physical and Chemical Properties | Toxicity: low toxicity to human and animal. Rats with acute oral LD50>5050 mg/kg, acute percutaneous LD50>2010 mg/kg. The rabbit eyes and skin no irritation. Low toxicity to birds, fish. No toxicity to bees. |
| Use | Flumineuron is a kind of high efficiency and selective herbicide, which can be absorbed by roots, stems and leaves, and quickly conducted to Meristem. It is safe to corn and can control grass weeds and broad-leaved weeds.It is suitable for controlling gramineous weeds and broad-leaved weeds in corn fields. |
Primisulfuron-methyl - 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 / PGIII |
| WGK Germany | 3 |
| RTECS | DG4436000 |
| Toxicity | LD50 in rats (mg/kg): >4000 orally; >2000 dermally (Maurer) |
Primisulfuron-methyl - Upstream Downstream Industry
Primisulfuron-methyl - Nature
| Merck | 13,7836 |
| BRN | 6673850 |
Last Update：2024-04-10 22:29:15
Primisulfuron-methyl - Uses and synthesis methods
Toxicity
rats acute oral LD50>5050mg/kg, acute percutaneous LD50>2010mg/kg, acute inhalation LC50>4.8mg/L (4h). No sensitization to guinea pig skin, no irritation to rabbit skin and eyes. The subacute non-effective dose in rats is 24.5 mg/kg per day. Trout LC5070mg/L, quail acute oral LD50>2150 mg/kg, safe for bees.
chemical properties
The pure product is a white solid. M. p.203.1 ℃, vapor pressure <1.0 × 10-9Pa (20 ℃). The solubility in water is related to pH value. At 20 ℃, pH value 5 is 1mg/L,pH value 7 is 70mg/L, and pH value 9 is 4.5g/L. Slightly soluble in various organic solvents. The half-life of hydrolysis reaction is pH 3~5 about 10h,pH 7~9 is> 300h, and the half-life in soil is 10~60h. Stable at ≤ 100 ℃.
use
1. Sulfonylurea herbicides are inhibitors of branched chain amino acid synthesis. It is absorbed by the roots and rapidly transferred to the meristem. The absorption rate depends on the growth stage of the plant and is also related to the temperature and humidity of the soil. It is used to control gramineous weeds and broadleaf weeds in corn fields. The dosage is 10~40g active ingredient/hm2. The best application period is corn 3~7 leaf growth period, used before bud.
2. It is a sulfonylurea high-efficiency systemic selective herbicide, suitable for controlling gramineous weeds and broadleaf weeds in corn fields
3. flunuron is a highly efficient systemic selective herbicide of xanthylurea. Can be absorbed by roots, stems and leaves and rapidly transmitted to meristem. It is safe for corn and can control gramineous weeds and broadleaf weeds. It is suitable for controlling gramineous weeds and broadleaf weeds in corn fields.
production method
preparation of 4,6-bis (difluoromethoxy)-2-aminopyrimidine in a pressure kettle, add 21g (0.1mol) of anhydrous 4,6-dihydroxy -2-methylthiopyrimidine disodium salt, 5g R4N + Cl- ,100mL acetonitrile, raise the temperature to 50 ℃, add 50g (0.57mol) of difluoromethane within 10min. After 6h, the pressure was relieved, filtered, the filter residue was washed with acetonitrile, the filtrate was dissolved under reduced pressure, and the molten product was washed with 50mL hot water to prepare 16.0g of 4,6-bis (difluoromethoxy)-2-methylthiopyrimidine with 55.8% yield and 90% purity.
after mixing 5.7g (0.02mol) of the previous product with 100mL glacial acetic acid, the temperature is increased to 80~85 ℃, 30% H2O2 18mL is added dropwise, and the heat preservation reaction is carried out for 2 hours. The reactants are poured into water and dichloromethane is extracted. The organic phase was dissolved and recrystallized with ether to prepare 5.5g of 4,6-bis (difluoromethoxy)-2-methylsulfonylpyrimidine with 96.6% yield. After boiling 5g (0.017mol) of the above product and 100mL of dichloromethane, 25mL 30% ammonia water was added dropwise at room temperature, stirred for 0.5h, and refluxed for 2h. The organic phase was desolted to prepare 4.0g of 4, 6-bis (difluoromethoxy)-2-aminopyrimidine, m.p.68 ~ 70 ℃, and the reaction was quantitatively completed.
4, 6-bis (difluoromethoxy)-2-aminopyrimidine can also be prepared by dimethyl malonate.
Synthesis of fluorimuron-methyl 2-methoxycarbonylbenzenesulfonyl isocyanate reacts with 4, 6-bis (difluoromethoxy)-2-aminopyrimidine to prepare fluorimuron-methyl.
Last Update：2024-04-10 22:29:15
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Raw Materials for Primisulfuron-methyl