METSULFURON METHYL
Metsulfuron methyl
CAS: 74223-64-6
Molecular Formula: C14H15N5O6S
METSULFURON METHYL - Names and Identifiers
METSULFURON METHYL - Physico-chemical Properties
| Molecular Formula | C14H15N5O6S |
| Molar Mass | 381.36 |
| Density | 1.4561 (rough estimate) |
| Melting Point | 158°C |
| Boling Point | 181°C (rough estimate) |
| Flash Point | 345.2°C |
| Water Solubility | 27mg/L(temperature not stated) |
| Solubility | DMSO (Slightly), Methanol (Slightly, Heated) |
| Vapor Presure | 1.23E-17mmHg at 25°C |
| Appearance | neat |
| Color | White to Off-White |
| BRN | 587472 |
| pKa | 2.55±0.10(Predicted) |
| Storage Condition | 0-6°C |
| Refractive Index | 1.6460 (estimate) |
| Physical and Chemical Properties | Melting Point: 158°C |
| Use | For the control of annual and perennial broad-leaved weeds in wheat fields |
METSULFURON 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 | UN3077 9/PG 3 |
| WGK Germany | 2 |
| RTECS | DH3563000 |
| HS Code | 29339900 |
| Toxicity | LD50 in male and female rats, in male and female rabbits (mg/kg): >5000, >2000 orally; LC50 (96 hour) in American perch, rainbow trout: 150 ppm; LD50 in wild ducks: 2510 mg/kg (Lefebvre) |
METSULFURON METHYL - Upstream Downstream Industry
| Raw Materials | Methyl alcohol Sodium sulfide Sulfuric acid Sodium hydroxide Dicyandiamide Hydrochloric acid Acetyl Chloride |
METSULFURON METHYL - Reference Information
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| sulfonylurea herbicide | metsulfuron-methyl is a highly effective sulfonylurea herbicide, by the United States DuPont in 1980 after the development of a highly efficient varieties after chlorsulfuron, its activity is higher than the chlorsulfuron 3 times. The mechanism of action of metsulfuron-methyl is similar to that of chlorsulfuron, which is absorbed by the rhizomes and leaves of plants, rapidly conducts in vivo, inhibits the activity of acetolactate synthase (ALS), and causes the biosynthesis of valine and isoleucine to be blocked, this results in growth inhibition and death. After absorption by resistant crop wheat, the hydroxylation of the benzene ring is carried out in vivo, and the hydroxylated product rapidly forms a conjugate with glucose, thereby losing activity. metsulfuron-methyl is the most active sulfonylurea herbicide. It is suitable for all kinds of soil, and the pre-seedling soil treatment or post-seedling stem and leaf spray is mainly used to control most broad-leaved weeds in wheat fields, and also has a significant inhibitory effect on gramineous weeds. The shallow mixed soil after spraying could improve the control effect of weed under drought condition. Due to the poor activity of metsulfuron-methyl on the pig, watch-off, Kentucky and so on, a mixed preparation of Finesse with chlorsulfuron was prepared. Its influence on the post-operation and its application technology are still under study. Degradation in soil: metsulfuron-methyl in soil by hydrolysis and microbial degradation and disappear, Half-Life of 4 weeks, in acid soil due to rapid hydrolysis, so slightly faster decomposition; its duration in the soil is shorter than that of chlorsulfuron, with effective doses of 2 and 8g per hectare, and no residue can be detected after 7 and 44 weeks, therefore, the safety of post-crop is higher than that of chlorsulfuron. metsulfuron-methyl has a long growth period and should not be used in sensitive crops such as tea, corn, cotton and tobacco. 120 days after application in wheat field in neutral soil, sowing rape, cotton, soybean and cucumber will cause Phytotoxicity, and the phytotoxicity in alkaline soil is more serious. Therefore, it is limited to the Yangtze River basin and its south, acid soil (pH<7), rice and wheat rotation area of wheat field. |
| toxicity | Acute oral and percutaneous LD50>5000mg/kg, acute inhalation LC50>5mg/L (4H), Rabbit acute percutaneous LD50>2000mg/kg. There was no irritation response to rabbit eyes and skin. Subacute tests showed no lethal and histopathological effects. Rats fed 2 years test no effect of the dose of 50mg/kg. There are also reports in the literature that Ames test has no mutagenic effect, and it is speculated that it may have mutagenic effect on somatic cells, and further research is recommended. Rainbow trout LC50>150mg/L. |
| Use | ultra-efficient sulfonylurea herbicide, branched chain amino acid synthesis inhibitor. It has the characteristics of high efficiency, broad spectrum and internal absorption. The dosage of effective components per hectare is 4.5~7.5g, which is used to control a variety of broad-leaved weeds in cereal field, and can be absorbed and transported upward and downward through roots and leaves. On the grass, ryegrass, Polygonum, Changchun mange, roots, spinach, beauty, wild sesame, buckwheat, etc have activity. The effect on the pig is not good. The increase of the dosage can cause slight yellowing and stunting of crops, but does not affect the yield. Medrol is a sulfonylurea herbicide with ultra-low dosage for controlling middle and broad-leaved weeds in cereals. It can be transferred up and down in plants and used as a pre-and post-malt herbicide. used to control annual and perennial broad-leaved weeds in wheat field |
| production method | The synthesis procedure is as follows. Preparation of methyl 2-sulfonamidebenzoate 30g of saccharin and 1.2 of methanol were added to the reaction flask, and HCl gas was introduced below 0 °c. After completion of the reaction, excess methanol was distilled off. Ethyl acetate was added to the residue and the unreacted saccharin was filtered off. The ethyl acetate was distilled off and the residue was obtained by recrystallization. Melting point 122-124 °c. Preparation of methyl 2-(sulfonyl isocyanate)-benzoate methyl 2-sulfonyl benzoate 2.2g, xylene 13.4 and catalytic amount of n-butyl isocyanate, and a small amount of 1, 4-diazabicyclo [2,2,2] octane was added to the reaction flask, stirred, and phosgene was added at 120 °c. At the end of the reaction, the temperature was raised to 136 ° C. And then cooled to room temperature. After filtration, the filtrate was dissolved and distilled under reduced pressure to obtain a fraction of 140-150 ° C. (0.267kPa). 3. Preparation of meganuron add 2.4g of 2-amino-4-methoxy-6-methyl-triazine, of methylene chloride and 2-sulfonyl isocyanate methyl benzoate to the reaction flask, the reaction was stirred at room temperature for 16H. After filtration and removal of the solvent from the filtrate, the residue is triturated with chlorobutane to give white crystals of melting point 158-164 °c. Formulated into 20% emulsifiable concentrate, 5% granules. preparation of 2-amino-4-methyl-6-methoxy-1, 3, 5-triazine isourea salt method 7.4g of crude cyanamide was dissolved in 100ml of methanol and cooled, dry hydrogen chloride was introduced and the temperature was controlled to below 25 °c. After 3 days at room temperature, the methanol was removed and dried to obtain O-methylisourea hydrochloride. G of crude cyanamide and 110 ml of raw ethyl acetate were dissolved in mL of acetic anhydride, and heating was stopped while heating to °c. A total of 150 h was required until the distillation temperature was increased to 1.5 °c. N-cyanoethylimine Ester was obtained by post-treatment. 1.15g of sodium metal was added to 42ml of anhydrous methanol, and 5.8g of O-methylisourea hydrochloride was added, shaken for several minutes, and filtered. The filtrate was dropped into a solution of 10ml of methanol and 5.6g of N-cyanoethylimine Ester and stirred at 20~25 °c for 2H, this gives 2-amino -4-methyl -6-methoxy -1,3, 5-triazine. See the preparation of chlorsulfuron for this method. The dicyandiamide method first synthesizes N-cyanoethyleneimine ethyl ester, and then obtains 2-amino -4-methyl -6-methoxy -1,3, 5-triazine by reaction with cyanamide. Dicyanoformamidine salt method N,N-dicyanoformamidine sodium salt was prepared by the interaction of cyanoethyleneimine ester with sodium cyanamide at 40 ℃ for 1H, dry hydrogen chloride was then passed through, the reaction temperature was 5-15 °c, left overnight and treated with sodium hydroxide solution to give 2-amino -4-methyl -6-methoxy -1,3, 5-triazine. Preparation of O-methyl formate benzenesulfonyl isocyanate after 30g of saccharin was mixed with 250ml of methanol, hydrogen chloride gas was introduced below 0 ° C., and excess methanol was distilled off after reaction. The residue was added with ethyl acetate, filtered, distilled off ethyl acetate and recrystallized to give methyl ortho-formate benzenesulfonamide. After mixing 13.4g of the above product, 120 of xylene, a catalytic amount of n-butyl isocyanate and a small amount of 1, 4-diazabicyclo [2,2,2] octane, phosgene was introduced at °c. The reaction temperature was raised to 136 ° C., cooled, filtered, and desolvated to obtain methyl ortho-formate benzenesulfonyl isocyanate. A method for the production of methyl ortho-formate benzenesulfonyl isocyanate by the diphosgene process is described in reference to tribenuron-methyl. Synthesis of metsulfuron-methyl 1.4g of 2-amino-4-methyl-6-methoxy-s-triazine, 30ml of dichloroethane and 2.4g of methyl ortho-formate benzenesulfonyl isocyanate were stirred at room temperature for 16h, filtered, the product was desolvated and received 2.8g of metsulfuron-methyl. Methyl-N-formate methyl-o-formate benzenesulfonamide can also be obtained by reacting methyl-o-formate benzenesulfonamide with methyl chloroformate. It is prepared by reaction with 2-amino -4-methyl -6-methoxy-s-triazine. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-10 22:29:15
Supplier List
Multiple SpecificationsSpot supply
Product Name: Metsulfuron-methyl Visit Supplier Webpage Request for quotationCAS: 74223-64-6
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
Multiple SpecificationsSpot supply
Product Name: Metsulfuron-methyl Visit Supplier Webpage Request for quotationCAS: 74223-64-6
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
View History
Raw Materials for METSULFURON METHYL