Tuligen
Chlorsulfuron
CAS: 64902-72-3
Molecular Formula: C12H12ClN5O4S
Tuligen - Names and Identifiers
| Name | Chlorsulfuron |
| Synonyms | PRESS telar glean TELAR W-4189 Tuligen dpx 4189 DPX-W-4189 Chlorsulfuron 2-chlorsulfuron N-(2-Chlorophenyl)sulfonyl-N'-(4-methyl-6-methoxy-2-triazinyl)urea 1-(2-chlorophenyl)sulfonyl-3-(4-methoxy-6-methyl-s-triazin-2-yl)urea 2-chloro-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoyl]benzenesulfonamide 2-Chloro-N(((4-methoxy-6-methyl-1,3,5-triazin-2-yl) amino)carbonyl)benzenesulfonamide 2-chloro-n-[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]benzenesulfonamide |
| CAS | 64902-72-3 |
| EINECS | 265-268-5 |
| InChI | InChI=1/C12H12ClN5O4S/c1-7-14-10(17-12(15-7)22-2)16-11(19)18-23(20,21)9-6-4-3-5-8(9)13/h3-6H,1-2H3,(H2,14,15,16,17,18,19) |
Tuligen - Physico-chemical Properties
| Molecular Formula | C12H12ClN5O4S |
| Molar Mass | 357.77 |
| Density | 1.6111 (rough estimate) |
| Melting Point | 174-178°C |
| Appearance | neat |
| Merck | 13,2210 |
| BRN | 577255 |
| pKa | 4.21±0.10(Predicted) |
| Storage Condition | 0-6°C |
| Refractive Index | 1.5630 (estimate) |
| MDL | MFCD00128059 |
| Physical and Chemical Properties | Melting Point 174-178°C |
| Use | It is a selective and ultra-efficient herbicide in wheat field, with wide herbicide spectrum and safety to wheat seedlings |
Tuligen - Risk and Safety
| 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. S36 - Wear suitable protective clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| UN IDs | UN3077 9/PG 3 |
| WGK Germany | 2 |
| RTECS | YS6640000 |
| Toxicity | LD50 in male, female rats (mg/kg): 5545, 6293 orally (Levitt) |
Tuligen - Upstream Downstream Industry
Tuligen - Nature
Open Data Verified Data
pure white crystals, no smell. Melting point 17 4~178 ℃.192 ℃ decomposition, vapor pressure (25 ℃)6.133 X10-4. The solubility was 102g/L in dichloromethane and 100~125mg/L in water at 25 ℃ (pH = 4.1). 27. 9g/L(pH = 7). Unstable under acidic conditions.
Last Update：2024-01-02 23:10:35
Tuligen - Preparation Method
Open Data Verified Data
prepared by addition of O-chlorobenzenesulfonyl isocyanate with 2-amino -4-methoxy -6-methyl -1,3,5-azine. Chlorsulfuron can also be prepared by the addition reaction of O-chlorobenzene sulfonamide with 4-methyl -6-methoxy-s-triazine-2-isocyanate.
Last Update：2022-01-01 10:12:49
Tuligen - Introduction
It is not easy to photolysis.
Last Update：2022-10-16 17:27:42
Tuligen - Use
Open Data Verified Data
low toxicity broad-spectrum wheat field selective herbicide, which is characterized by high activity. In-systemic, ultra-efficient sulfonylurea herbicides. After being absorbed by the weed leaf or root system, the medicament can be transmitted to the whole body of the plant to inhibit the synthesis of branched chain amino acids, valine and leucine by inhibiting the activity of acetolactase, thereby stopping cell division, the plant was lost in green, and died. It is used to control broad-leaved weeds and gramineous weeds in the field of cereal crops, such as pig, hemp, Field Flower, Field Thistle, buckwheat mange, chrysanthemum, as well as dog tail grass, ryegrass, Kentucky bluegrass, root garlic, etc. The effect on wild oat and Solanum nigrum was poor.
Last Update：2022-01-01 10:12:50
Tuligen - Safety
Open Data Verified Data
oral LD50 of male rats. It is 5545mg/kg, 6293mg/kg for females, and rabbit percutaneous LD50>3400mg/kg; Slight irritation to eyes, no irritation to skin. Rats were fed at a dose of 500mg/kg for 90 days, and no pathological changes were found. Rats fed for 2 years test dose-free was 100 mg/kg/day. Mice were 500mg/kg. The teratogenic, carcinogenic and mutagenic effects were not found in animal experiments. Rainbow trout LC50>250mg/kg( 96H), quail LC50>5000mg/kg feed (8d).
Last Update：2022-01-01 10:12:50
Tuligen - Reference Information
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| toxicity | Acute oral LD50 was 5545mg/kg in male rats and 6293mg/kg in female; rabbit acute percutaneous LD50>3400mg/kg. Slight irritation to the eyes, no irritation to the skin. Rats were fed at a dose of 500mg/kg for 90 days, and no pathological changes were found. The dosage of the two-year feeding test was 100mg/kg for rats and 500mg/kg for mice. The teratogenic, carcinogenic and mutagenic effects were not found in animal experiments. Rainbow trout LC50>250mg/kg(96H), quail LC50>5000mg/kg feed (8d). |
| Use | systemic, ultra-efficient sulfonylurea herbicide. After being absorbed by the leaves or roots of weeds, the medicament can be transmitted to the whole body of the plant to inhibit the synthesis of branched chain amino acids, valine and leucine by inhibiting the activity of acetolactase, thereby stopping cell division, the plant was lost in green, and died. Used to control broad-leaved weeds and grass weeds in the field of cereal crops, such as quinoa, Polygonum, amaranth, pig, hemp, field flowers, Thistle, buckwheat Vine, chrysanthemum, as well as green grass, ryegrass, kentucky bluegrass, small root garlic, etc. The effect on wild oat and Solanum nigrum was poor. Pre-or early post-Bud use, generally in the autumn after sowing crop bud or spring weed bud after application of medicine, more appropriate post-Bud foliar treatment. The water was sprayed with 0.15-100 m2 G of active ingredient/L. Mixed with chlorotoluron and Isoproturon, the effect is good. The crops which were sensitive to the post-harvest were corn and rape, etc. The amount of more than 0.6G had a slight effect on the post-harvest rice. Green Yellow Long is a new type of sulfonylurea herbicide developed by DuPont in 1978. It was commercialized in 1981. It is a low toxicity and broad spectrum wheat field selective herbicide, which is characterized by high activity. It is a selective and super-efficient herbicide in wheat field, with wide herbicide spectrum, which is safe to wheat seedlings |
| production method | O-chlorobenzenesulfonyl isocyanate with 2-amino-4-methoxy-6-methyl -1,3, 5-triazine was added. Synthesis of O-chlorobenzenesulfonyl isocyanate (1) synthesis of O-chlorobenzenesulfonyl chloride O-chloroaniline after diazotization is added to the acetic acid solution containing copper chloride and sulfur dioxide to be obtained after reaction. (2) synthesis of O-chlorobenzene sulfonamide from O-chlorobenzene sulfonyl chloride and concentrated ammonia reaction. (3) synthesis of O-chlorophenylsulfonyl isocyanate O-chlorophenylsulfonamide was obtained by reaction with phosgene under n-butyl isocyanate catalyst. 2. Synthesis of 2-amino -4-methoxy -6-methyl -1,3, 5-triazine (1) synthesis of O-methyl -3-amidino isourea hydrochloride copper chloride and dicyandiamide, the reaction of pink copper complex, and hydrogen sulfide reaction. (2)2-amino -4-methoxy -6-methyl -1,3, synthesis of 5-triazine O-methyl -3-amidino isourea hydrochloride was obtained by reaction with acetyl chloride. 3. Synthesis of chlorsulfuron was obtained by the reaction of 2-amino-4-methoxy-6-methyl-1, 3, 5-triazine and O-chlorobenzenesulfonyl isocyanate. preparation of 2-amino -4-methyl -6-methoxy-s-triazine the isourea salt process is as follows: 4.7g of cyanamide (90%) and 4g of water are mixed, ethyleneimine ethyl ester hydrochloride (90%) was added at 10 °c, stirred for 1H, then adjusted to pH 5-6 with sodium hydroxide, stirred at 5-10 °c for 1H, added 10ml water, stirred to separate layers, the oil layer was distilled under reduced pressure to obtain ethyl N-cyanoethylimide in a yield of 91%. Mix 50g of urea, 100g of dimethyl sulfate and 32g of methanol, slowly raise the temperature to 55 ℃, stop heating, automatically rise to 60 ℃, cool properly when reaching 68 ℃, and stop cooling at 83 ℃, the temperature was continuously raised to 113 ° C., then automatically lowered to 105 ° C. And cooled to 50 ° C. To obtain methyl methacrylate sulfate salt with a yield of 93%. Add 1.4g sodium metal in 25ml methanol, cool to -10 °c, add 11.2g methyl isourea methyl sulfate salt (90%), and add 5.6G ethyl N-cyanoethylimide Dropwise at 0~14 °c, the temperature was raised to 20 ° C., and the mixture was stirred for 20H. After post-treatment, 2-amino -4-methoxy -6-methyl-s-triazine was obtained with a yield of 69.3%. Other synthetic methods see preparation of metsulfuron-methyl. Preparation of O-chlorobenzenesulfonyl isocyanate 230ml of concentrated hydrochloric acid, 70ml of water and 121g of O-chloroaniline were mixed and cooled to -5 °c. A 40% sodium nitrite solution was added dropwise, the reaction temperature was 3 ° C. Or lower, and nitrous acid was made to be excessive. At the end of the reaction, excess nitrous acid was destroyed with a little urea, and solid impurities were removed by filtration to complete diazotization of O-chloroaniline. Dissolve 198g of sodium bisulfite in 350ml of water, divide the solution into 2 parts, one of which is put into a reaction flask containing 770ml of concentrated hydrochloric acid and 24g of anhydrous copper sulfate, and then under stirring and cooling, at the same time, another portion of sodium bisulfite solution and diazonium salt solution were dropped, and the reaction temperature was maintained at 0 ° C. After the reaction, the oil layer was separated and washed with water to obtain O-chlorobenzenesulfonyl chloride, with a yield of 88.7% in the last two steps. The O-chlorobenzenesulfonyl chloride was dropped into a reaction flask containing 430ml of concentrated aqueous ammonia, and the bath temperature was controlled at 60 ° C., and the reaction was maintained for 4 hours. Filtration, water and dioxane (5:1) mixed solvent recrystallization, decolorization, O-chlorobenzene sulfonamide, yield 63%. After mixing 19.2g of O-chlorobenzene sulfonamide, 150ml of O-dichlorobenzene and 63.5g of oxalyl chloride, the mixture was refluxed for 9H, The excess oxalyl chloride was distilled off until the reaction temperature rose to 180 ° C., the O-dichlorobenzene was distilled off under reduced pressure, and the O-chlorobenzenesulfonyl isocyanate was distilled off under reduced pressure, with a yield of 57. 3%. Cyanate esters can also be synthesized in the presence of tertiary amines using phosgene instead of oxalyl chloride. Synthesis of chlorsulfuron 0.02mol of 2-amino-4-methyl-6-methoxy in s-triazine and 40ml of anhydrous acetonitrile were mixed by hand, add 0.02mol of O-chlorobenzenesulfonyl chloride isocyanate acetonitrile solution Dropwise at room temperature, and continue to stir at room temperature for 24h. Filter out white powder, wash with acetonitrile and dry to obtain product chlorsulfuron-methyl, the yield was 70%. Chlorsulfuron can also be prepared by the addition reaction of O-chlorobenzene sulfonamide with 4-methyl-6-methoxys-triazine-2-isocyanate. Wherein 4-methyl-6-methoxy-triazine-2-isocyanate is prepared by reacting 2-amino-4-methyl-6-methoxy-triazine with phosgene. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 21:11:58
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Multiple Specifications
Product Name: Carboxin Visit Supplier Webpage Request for quotationCAS: 64902-72-3
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Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
View History
Raw Materials for Tuligen
2-Methylbenzenesulfonamide
Ammonium hydroxide
Sulfuric acid
Sodium hydroxide
Ammonium Bisulfite
Acetyl Chloride
Ammonium hydroxide
Sulfuric acid
Sodium hydroxide
Ammonium Bisulfite
Acetyl Chloride