2-[[[[(4-Chloro-6-methoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]benzoic acid ethyl ester
Chlorimuron-ethyl
CAS: 90982-32-4
Molecular Formula: C15H15ClN4O6S
2-[[[[(4-Chloro-6-methoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]benzoic acid ethyl ester - Names and Identifiers
| Name | Chlorimuron-ethyl |
| Synonyms | DARBAN DPX-F6025 Classic 75DF Chlorimuron Et Chlorimuron-ethyl Chlorimuron ethyl ester ethyl 2-{[(4-chloro-6-methoxypyrimidin-2-yl)carbamoyl]sulfamoyl}benzoate ethyl2-(((((4-chloro-6-methoxypyrimidin-2-yl)-amino)carbonyl)amino)sulfonyl)b 2-(((((4-chloro-6-methoxy-2-pyrimidinyl)amino)carbonyl)amino)sulfonyl)benzoica Ethyl2-(((((4-chloro-6-methoxypyrimidin-2-yl)amino)carbonyl)amino)sulfonyl)benzoate ethyl2-(((((4-chloro-6-methoxpyrimidin-2-yl)aminol)carbonyl)amino)sulfonyl)benzoate Ethyl 2-[[[[(4-chloro-6-methoxpyrimidin-2-yl)aminol]carbonyl] amino] sulfonyl]benzoate ETHYL-2-[[[[(4-CHLORO-6-METHOXY-2-PYRIMIDINYL)AMINO]CARBONYL]AMINO]-SULFONYL] BENZOATE 2-[[[[(4-Chloro-6-methoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]benzoic acid ethyl ester |
| CAS | 90982-32-4 |
| EINECS | 618-690-2 |
| InChI | InChI=1/C15H15ClN4O6S/c1-3-26-13(21)9-6-4-5-7-10(9)27(23,24)20-15(22)19-14-17-11(16)8-12(18-14)25-2/h4-8H,3H2,1-2H3,(H2,17,18,19,20,22) |
| InChIKey | NSWAMPCUPHPTTC-UHFFFAOYSA-N |
2-[[[[(4-Chloro-6-methoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]benzoic acid ethyl ester - Physico-chemical Properties
| Molecular Formula | C15H15ClN4O6S |
| Molar Mass | 414.82 |
| Density | 1.4727 (rough estimate) |
| Melting Point | 180-182°C |
| Boling Point | 180-182℃ |
| Water Solubility | 1.018mg/L(temperature not stated) |
| Solubility | Freely soluble in aqueous solution |
| Appearance | Solid |
| Color | White to Light Yellow |
| pKa | 3.78±0.10(Predicted) |
| Storage Condition | Inert atmosphere,2-8°C |
| Stability | Unstable in DMSO solution |
| Refractive Index | 1.6100 (estimate) |
| Physical and Chemical Properties | Melting Point: 180-182°C |
| Use | Mainly used for controlling weeds in soybean field |
2-[[[[(4-Chloro-6-methoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]benzoic acid ethyl ester - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36 - Irritating to the eyes |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. |
| UN IDs | UN3077 (solid) |
| RTECS | DG5095000 |
| Toxicity | LD50 in male, female rats (mg/kg): 4102, 4236 orally (Claus) |
2-[[[[(4-Chloro-6-methoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]benzoic acid ethyl ester - Reference Information
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Overview | chlorimuron-methyl is a sulfonylurea herbicide, which is a side chain amino acid synthesis inhibitor, the synthesis of valine and isoleucine is interrupted by inhibition of the synthesis of acetolactase. It is mainly used as a herbicide in soybean fields, and soybean can be metabolized into inactive substances. Chlorimuron is absorbed by the root and bud of a systemic herbicide, which can quickly control the growth of sensitive weeds, the leaves of sensitive plants lose green in 3~5 days, and the growth point is necrotic. In 7~21 days, the growth of sensitive plants is inhibited, and some plants are kept green, but they are stunted and not competitive. |
| physical and chemical properties | pure white solid powder, industrial products for light yellow powder, content of more than 95%, melting point 186 ℃, the density was 1.51 (25 ° C.),pKa4.2, and the vapor pressure was 0.49 × 10 − 7MPa. Soluble in dimethylformamide, 1,4 oxygen six ring, etc., slightly soluble in acetone, ethanol, difficult to dissolve in benzene and other non-polar solvents, water (25 degrees C) solubility of 9mg/L (pH5), 1.2g/L(pH7). Stability: PH 5 in water, DT50 at 25 °c for 7~25 days. |
| preparation method | 2-amino-4, 6-dihydroxypyrimidine was prepared from diethyl malonate, anhydrous ethanol and guanidine carbonate, 2-amino -4, 6-dichloropyrimidine was prepared by refluxing 2-amino -4, 6-dihydroxypyrimidine and phosphorus oxychloride, this compound reacts with sodium methoxide to give 2-amino-4-chloro-6-methoxypyrimidine. Ethanol and saccharin react to obtain O-(ethyl formate) benzenesulfonamide, O-(ethyl formate) benzenesulfonamide, xylene, n-butyl isocyanate and a small amount of 1, 4-diazabicyclo [2.2.2] octane heated to reflux, phosgene is then passed through to obtain O-(ethyl formate) benzenesulfonyl isocyanate. O-(ethyl formate) benzenesulfonamide, 2-amino-4-chloro-6-methoxypyrimidine is reacted to chlorimuron. The reaction formula is as follows: |
| mode of action | in the plant body, the main conduction is from the treatment site (root and Bud), to the growing point to play a role. The leaves of sensitive plants lose green in 3~5 days, the growing point is necrotic, in 7-21 days, the growth of sensitive plants is inhibited, and some plants are kept green, but are dwarf and non competitive. |
| mechanism of action | prevents the activity of acetolactate synthase (ALS) in plants to interrupt valine and isoleucine synthesis. |
| control object | selective control of papyrika, broadleaf weeds and some grass weeds, such as xanthii, portulaca oleracea, Polygonum, Chenopodium album, amaranth, hemp, single dish, Mosla, amaranth, Petunia, Pennisetum, hoof leaf, sage, Cassia, etc, poa pratensis and others also have good control effect, which is poor in control of Solanum nigrum, buckwheat Vine, Thorn, Horse Tang, etc. It is almost ineffective in wild millet, gold, etc, generally 10~20 days. |
| analytical method | high performance liquid chromatography, UV detector-254nm, column: C 18,250 × 4.6 (I. d)mm, mobile phase: Methanol-water-ethyl acetate = 2: 2: 1(v/v), flow rate 1.0/min, retention time 5.9 min. Preparation of solution: weigh 50mg standard sample and sample containing chlorimuron, respectively, and use mobile phase to volume in 100ml volumetric flask. Alternatively, mobile phase methanol-water = 50: 50, flow rate 1.0/min, retention time 9.3min. Alternatively, the mobile phase is methanol-water (adjusted to pH = 3 with phosphoric acid)-tetrahydrofuran = 103: 167: 1.5, a flow rate of 1.0/min, and a retention time of 3.3min. |
| note | (1) conventional spraying equipment is used for spraying equipment, and ultra-low-volume spraying is not recommended, mist Spray or aerial spray. (2) the soil treatment of this agent is safe, and the stem and leaf treatment must be tested in a small area by the Plant Protection Department before use under guidance. (3) in the following cases, should not use this product. ① low-lying waterlogged, saline-alkali land and soil pH ≥ 7 ② continuous low temperature (below 10 ℃), continuous high temperature (above 30 ℃) and rainy weather during the application period. (3) weak seedlings or soybean diseases and insect pests are more. (4) when the soil organic matter exceeds 6%, it is not suitable for soil treatment. (5) the drug has a long period of efficacy, and it is advisable to plant soybean, wheat and barley in the next crop. The use of this product, especially after the treatment of stems and leaves, will have a slight inhibitory effect on soybean, should strengthen the field management. The storage of this product should pay attention to moisture, heat, not mixed with food and feed storage. The shelf life of this product: two years. (2015-11-02) |
| degradation metabolism | soil decomposition, plant absorption. |
| toxicity | Acute oral LD50 was 4102mg/kg in male rats and 4236mg/kg in female rats; rat acute inhalation LC50>5mg/L; Rabbit acute percutaneous LD50>4000mg/kg. Rats fed for 2 years with no effect dose of 250 mg/kg feed. There was no teratogenic phenomenon under the experimental conditions. Rainbow trout LC50>1000mg/L (96H), blue gill fish LD50>100mg/L (96H), Daphnia lc501000 mg/L (48h). Acute wild duck by LD50>2510mg/kg. |
| packaging, storage and transportation | The original medical packaging is packed with woven bags lined with plastic bags, each with a net weight of 25kg;20% wettable powder with plastic aluminum foil packaging bags, each net weight of 4g or 100g, tightly sealed, each 10kg into a calcium plastic box. |
| Use | chlorimuron-methyl is a sulfonylurea herbicide. The mechanism of action is to inhibit the activity of acetolactate synthase in plants and interfere with the synthesis of branched chain amino acids. It is mainly used to weed soybean, control Cyperus, broad-leaved weeds and some grass weeds. After Bud application, dosage <15g/hm2. is a selective pre-and post-emergence herbicide, mainly used for controlling broad-leaved weeds in soybean field mainly used for controlling weeds in soybean field |
| production method | Domestic developed synthetic route 2-amino -4, preparation of 6-dichloropyrimidine dimethyl malonate is subjected to a condensation cyclization reaction with guanidine hydrochloride to form 2-amino -4, 6-dihydroxypyrimidine, which then reacts with phosphorus oxychloride in the presence of triethylamine, 2-amino -4, 6-dichloropyrimidine is produced. Preparation of N-[(4, 6-dichloropyrimidin-2-amino) carbonyl] O-ethoxycarbonylbenzenesulfonamide 2-amino -2, 4-dichloropyrimidine was first isocyanated, 2, 4-dichloropyrimidine-2-isocyanate was formed, and then it was added to the solution of O-ethoxycarbonylbenzenesulfonamide in toluene and heated under reflux for 6H. The yield was 84%, the melting point of the product was 160-162 °c. Synthesis of chlorimuron-methyl the intermediate product in the previous step was dissolved in methanol, and a methanol solution of sodium methoxide was added dropwise at room temperature. The reaction was carried out at room temperature for 3H, and an appropriate amount of water was added into the reaction flask to obtain a transparent solution. With 2mol/L sulfuric acid to adjust the pH value to 2, a white solid, after filtration, washing, drying and other post-treatment to obtain the original drug, the yield was 80%, the original drug m. P. 180~182 ℃. Synthetic Route of foreign production |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 19:05:15
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