ACCENT
Nicosulfuron
CAS: 111991-09-4
Molecular Formula: C15H18N6O6S
ACCENT - Names and Identifiers
| Name | Nicosulfuron |
| Synonyms | MU 495 Accetn ACCENT Nisshin ACCENT (TM) Nicosulfuron Accent【pesticide】 sodium (2S)-2-amino-4-carboxybutanoate 2-(4,6-dimethoxypyrimidin-2-ylcarbamoylsulfamoyl)-N,N-dimethylnicotinamide 2-[(4,6-Dimethoxypyrimidin-2-ylcarbamoyl)sulfamoyl]-N,N-dimethylnicotinamide 1-(4,6-Dimethoxypyrimidin-2-yl)-3-(3-dimethylcarbamoyl-2-pyridylsulfonyl)urea 1-(4,6-Dimethoxy-2-pyrimidinyl)-3-[3-(dimethylcarbamoyl)-2-pyridylsulfonyl]urea 2-{[(4,6-dimethoxypyrimidin-2-yl)carbamoyl]sulfamoyl}-N,N-dimethylpyridine-3-carboxamide 1-(4,6-Dimethoxy-2-pyrimidinyl)-3-[3-(dimethylcarbamoyl)-2-pyridylsulfonyl]urea, 2-[(4,6-Dimethoxypyrimidin-2-ylcarbamoyl)sulfamoyl]-N,N-dimethylnicotinamide |
| CAS | 111991-09-4 |
| EINECS | 244-666-2 |
| InChI | InChI:1S/C15H18N6O6S/c1-21(2)13(22)9-6-5-7-16-12(9)28(24,25)20-15(23)19-14-17-10(26-3)8-11(18-14)27-4/h5-8H,1-4H3,(H2,17,18,19,20,23) |
| InChIKey | RTCOGUMHFFWOJV-UHFFFAOYSA-N |
ACCENT - Physico-chemical Properties
| Molecular Formula | C15H18N6O6S |
| Molar Mass | 410.4 |
| Density | 1.4126 (rough estimate) |
| Melting Point | 141-144°C |
| Boling Point | 333.8°C at 760 mmHg |
| Flash Point | 155.7°C |
| Water Solubility | 1.20E+04 mg/L at 25 ℃ |
| Solubility | Water 400 mg/kg(pH buffer, final pH5.01),120 g/kg(pH7 buffer, final pH6.85),39.2 g/kg(pH9 buffer, final pH8.8), solubility in organic solvent (g/kg): acetone 18, acetonitrile 23, chlorine |
| Vapor Presure | 2.55E-05mmHg at 25°C |
| Appearance | White solid |
| pKa | pKa (25°): 4.6 |
| Storage Condition | Sealed in dry,Room Temperature |
| Refractive Index | 1.7000 (estimate) |
| MDL | MFCD00203303 |
| Physical and Chemical Properties | Melting point 141-144°C |
| Use | For the control of single and double leaf weeds in maize field |
ACCENT - Risk and Safety
| Risk Codes | R36/38 - Irritating to eyes and skin. R50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. |
| Safety Description | S24/25 - Avoid contact with skin and eyes. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. |
| UN IDs | UN 3077 9 / PGIII |
| WGK Germany | 1 |
| RTECS | US4615000 |
| HS Code | 29350090 |
ACCENT - Reference
| Reference Show more | 1. [IF=3.545] Yu Liu et al."Polymorphism and molecular conformations of nicosulfuron: structure, properties and desolvation process."Crystengcomm. 2019 Apr;21(17):2790-2798 |
ACCENT - Nature
Open Data Verified Data
pure white crystals. The melting point is 172~173 ℃ (industrial 169~173 ℃), and the solubility (%) is: dichloromethane 16, DMF6.4, chloroform 6.4, acetonitrile 2.3, acetone 1.8, ethanol 0. 45, water 12, hexane <0.002. The distribution coefficient (octanol/water) was 0. 44 (pH 5), 0.017(pH 7), 0.01(pH = 9). It is easy to decompose in dilute aqueous solution and soil environment.
Last Update：2024-01-02 23:10:35
ACCENT - Preparation Method
Open Data Verified Data
with 2-chloronicotinic acid as starting material by amidation, sulfonation, ammoniation to get the intermediate 2-amino sulfonyl-N,N-= methyl pyridine amide, it is reacted with chloroformate and then reacted with 2-amino -4,6-= methoxypyrimidine to obtain nicosulfuron.
Last Update：2022-01-01 10:12:53
ACCENT - Use
Open Data Verified Data
sulfonylurea herbicides are side chain amino acid synthesis inhibitors. It can be used to control annual and perennial grass weeds, Cyperus and some broad-leaved weeds in corn field, and the activity of narrow-leaf weeds is more than that of broad-leaved weeds, which is safe for corn crops.
Last Update：2022-01-01 10:12:54
ACCENT - Safety
Open Data Verified Data
rat, mouse oral LD50>5000mg/kg, rabbit percutaneous DL50>2000mg/kg, rat inhalation LC50>5.47mg/L. Slightly irritating effect on eyes. No allergic to guinea pig skin. Carp LC50 >lOmg/L(96H).
Last Update：2022-01-01 10:12:54
ACCENT - Reference Information
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| action characteristics | nicosulfuron is a systemic herbicide, which can be absorbed by the stems, leaves and roots of plants and conduct rapidly. by inhibiting the activity of acetolactate synthase in plants, it prevents the synthesis of branched-chain amino acids, leucine and isoleucine, thus preventing cell division and stopping the growth of sensitive plants. The symptoms of weed damage are that the heart leaves turn yellow, lose green, and whiten, and then other leaves turn yellow from top to bottom. Generally, weed damage symptoms can be seen 3~4 days after application. Annual weeds die in 1~3 weeks, and perennial broad-leaved weeds under 6 leaves are inhibited, stop growth, and lose their competitiveness with corn. High doses can also kill perennial weeds. |
| control object | barnyard grass, crabgrass, oxen grass, dogtail grass, anti-branch amaranth, purslane, abaletum, field convolvulus, prickles, chicerae, gracilis, wild millet, Solanum nigrum, Elsholtzia, Xanthium, Commelina communis, Blossom Blossom Blossom, Artemisia, Artemisia, Thistle, Wild O. |
| application technology | during the use period, the 2-5 leaf period after corn seedlings, the 2-4 leaf period of annual weeds, and the 6 leaf period of perennial weeds before, most weeds are applied at the same time, which has the best weeding effect and is safe for corn. When the soil moisture and air temperature are suitable, it is beneficial to the absorption and conduction of weeds to chemicals. Long-term drought, low temperature and air relative humidity below 65% should not be applied. Generally, application should be made in the morning and evening when the temperature is low and the wind is small. It is best to increase the surfactant when applying medicine in drought. If there is rain in the near future for a long period of drought, the humidity in the field will improve after the rain, and the pesticide will be applied after the application or irrigation conditions. Although the application time is delayed, the weeding effect will be better than that before the rain. It is best to use fan-shaped nozzle for manual application, apply the nozzle along the ridge, spray one ridge at a time, fix the height, pressure and walking speed of the nozzle, and do not use dynamic application left and right to ensure uniform spraying. Registered crop: corn |
| precautions | 1. different corn varieties have different sensitivity to chemicals, and their safety order is horse tooth type> hard corn> burst corn> sweet corn. Generally, corn is sensitive to the drug before 2-leaf stage and after 10-leaf stage. Sweet corn or burst corn seed production fields and inbred lines are sensitive to this agent and should not be used. 2. No residual damage to wheat, garlic, sunflower, alfalfa, potato, soybean, etc. In grain and vegetable intercropping or rotation areas, the phytotoxicity test of the following vegetables should be done. 3. Corn treated with organophosphorus agents is sensitive to the drug, and the safe use interval between the two agents is 7 days. 4. Rain after 6 hours of application has no obvious effect on the efficacy of the drug, so there is no need to spray again. 5. Avoid direct sunlight and high temperature medication. The medication effect is good before 10: 00 a.m. and after 4: 00 p.m. 6. Place it separately from seeds, seedlings, fertilizers and other pesticides, and try to place it in a low temperature and dry place for sealed storage. |
| toxicity | acute oral LD50>5000 mg/kg in rats and mice, acute percutaneous LD50>2000 mg/kg in rabbits, and acute inhalation LC50>5.47mg/L in rats. It has a slight irritation to the eyes and is not allergic to the skin of guinea pigs. The Ames test was negative. Carp LC50>10mg/L (96h). |
| use | sulfonylurea herbicides inhibit plant acetolactate synthase (branched chain amino acid synthesis inhibitor). It can be used to control annual and perennial gramineous weeds, sedge and some broad-leaved weeds in corn fields. The activity of narrow-leaved weeds exceeds that of broad-leaved weeds and is safe for corn crops. The recommended dosage is 40g/hm2. Inhalable herbicide in corn field Used to control annual single and double-leaf weeds in corn field Herbicide. It is used in rice seedling fields, Honda and direct seeding fields to control annual and perennial broad-leaved weeds and Cyperaceae weeds, and also has a certain inhibitory effect on barnyard grass. |
| Production method | There are 4 synthetic routes for the preparation of 2-aminosulfonyl-N,N-dimethylnicotinamide. Route A, using easily obtained 2-chloronicotinic acid methyl ester as raw material, in acetic acid aqueous solution, with benzothiol, Cl2/C2H5COOH, the pyridine ring 2-position first introduce tert-butyl sulfonamide, and then use tert Butyl amination to generate (II). Then (CH3)2NH is used to convert the methyl ester into amide (III), and debutylated with trifluoroacetic acid to intermediate (IV). Route B, using nicotinic acid as raw material, the acid part is continuously treated with thionyl chloride and dimethylamine, first converted into amide (V), and then in dimethyl sulfoxide solution, with benzyl mercaptan and potassium sulfate Treatment of 2-position chlorine. Route a route B route c route d (a) C6H5CH2SH, K2CO3/dimethyl sulfoxide; Cl2/acetic acid aqueous solution; Tert-butylamine/CH2Cl2 (B)(CH3)2 AlNR1R2/benzene-dichloromethane or R1R2NH/methanol (c) CF3CO2H(d) SOCl2; R1R2 NH/CH2Cl2 (e) C6H5CH2SH, KOH/dioxane (f)Cl2/acetic acid aqueous solution; NH3/dichloromethane (g) SOCl2; r1 NH2/CH2Cl2(h)NaH/dimethylformamide; R2I (I) NaSH, S, liquid alkali (j) hydrogen peroxide, liquid alkali (k) H2NOSO3H, liquid alkali to form 2-benzothiol compound (VI), then chlorine oxidation (VI), and then amination with ammonia, finally forming a key intermediate (IV). Route C, first convert niacin into monomethylamine derivatives, and then introduce a methyl group into dimethylamide derivatives. Route D, using amide (V) as raw material, in sodium hydroxide aqueous solution, sodium sulfide and sulfur reaction, N,N-dimethylaminonicotinoyl -2-sodium polysulfide. Then it was oxidized with an aqueous solution of sodium hydroxide of hydrogen peroxide to obtain sodium N,N-dialkylaminonicotinoyl-2-sulfinate, and then reacted with hydroxylamine-O-sulfonic acid to prepare the key intermediate (IV). D is more reasonable for the above 4 routes. Taking routes B and D as examples, the typical operation process is as follows. Route B at room temperature, 2-chloronicotinic acid (47.3g) is added to thionyl chloride (17.9g), reflux reaction for 2 hours, after the reaction, the excess thionyl chloride is removed under reduced pressure, and then at room temperature, Dichloromethane is added to the residue. Then cool to below 10 ℃ in an ice water bath, introduce dimethylamine gas, and finally after water injection, extraction, drying, desolution, distillation, etc., to obtain the product. Route D A mixture of 2-chloro-N, N-dimethylnicotinamide (55.4g), sodium hydrosulfide 70% (24g), sulfur (9.6g), sodium hydroxide (12g) and water was stirred back for 2h. In the obtained sodium N,N-dimethylnicotinyl -2-(poly) sulfide containing product, 180mL and 18g of 40% sodium hydroxide are added, and then 35% hydrogen peroxide (75.8g) is added dropwise to the mixed solution containing N,N-dimethylnicotinyl -2-sodium sulfinate at 10~20 ℃ for 35min, filtered, washed, and combined filtrates, hydroxylamine-O-sulfonic acid (54.2g) was added at 10 ℃. After the mixed solution is clarified, 40% NaOH (48g) is added dropwise at 10~20 ℃, stirred for 3 hours, and the crude product is filtered with a yield of 76.4%. There are 3 synthetic routes for nicosulfuron. Route E, 2-amino-4, 6-dimethoxypyrimidine in the presence of triethylamine in dichloroethane solvent, reacts with phosgene to form the corresponding isocyanate, and finally with the intermediate product 2-aminosulfonyl-N,N-dimethylnicotinamide. Route F, was prepared by the condensation of 2-aminosulfonyl-N,N-dimethylnicotinamide in an acetonitrile solvent with phenyl pyrimidinyl carbamate. Route G, 2-aminosulfonyl-N,N-dimethylnicotinamide is made into the corresponding phenyl carbamate, and then it is prepared by reacting with dimethoxyaminopyrimidine. The preparation method of route E 2-amino -4, 6-dimethoxypyrimidine is shown in the synthesis of bensulfuron-methyl. Route F Route G |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-10 22:29:15
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