S-4-Chloro-N-isoproylcarbamoylmethyl-O,O- dimethylphosphorodithioate
Anilofos
CAS: 64249-01-0
Molecular Formula: C13H19ClNO3PS2
S-4-Chloro-N-isoproylcarbamoylmethyl-O,O- dimethylphosphorodithioate - Names and Identifiers
S-4-Chloro-N-isoproylcarbamoylmethyl-O,O- dimethylphosphorodithioate - Physico-chemical Properties
| Molecular Formula | C13H19ClNO3PS2 |
| Molar Mass | 367.85 |
| Density | 1.322±0.06 g/cm3(Predicted) |
| Melting Point | 50～55℃ |
| Boling Point | 443.6±55.0 °C(Predicted) |
| Flash Point | >100°C |
| Vapor Presure | 4.58E-08mmHg at 25°C |
| Appearance | neat |
| BRN | 2395778 |
| pKa | -0.48±0.50(Predicted) |
| Storage Condition | 0-6°C |
| Refractive Index | 1.592 |
| Physical and Chemical Properties | Pure white needle-like crystals. m.p.51.5 °c, relative density 1.27 (25 °c), vapor pressure 2.2 x 10-3PA (60 °c). At 25 ℃, the solubility is acetone> 100%, toluene> 100%, chloroform> 100%, ethanol> 20%, benzene> 20%, ethyl acetate> 20%, n-hexane 1.2%. The solubility in water was 13.6mg/L. |
S-4-Chloro-N-isoproylcarbamoylmethyl-O,O- dimethylphosphorodithioate - Risk and Safety
| Risk Codes | R22 - Harmful if swallowed R51/53 - 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 |
| WGK Germany | 2 |
| RTECS | TD5185000 |
| Toxicity | LD50 orl-rat: 472 mg/kg PEMNDP 9,36,1991 |
S-4-Chloro-N-isoproylcarbamoylmethyl-O,O- dimethylphosphorodithioate - Upstream Downstream Industry
| Raw Materials | Chloroacetyl chloride |
S-4-Chloro-N-isoproylcarbamoylmethyl-O,O- dimethylphosphorodithioate - Reference Information
| organic phosphorus herbicides | phosphorus, glyphosate and amine phosphorus are three kinds of organic phosphorus herbicides that are widely used in China, it can effectively control the annual Gramineae weeds (Humulus, Aurea, duckbill, papyrika, wheatgrass) and caregrass of rice-wheatgrass. Initially developed by the German Herst company, mainly through the inhibition of glutamine synthetase to inhibit the synthesis of glutamine, thereby destroying the plant's important life process of amino acid biosynthesis in the process of cell division, causes the plant to stop growing, and eventually die, and the phosphorus is absorbed through the roots, coleoptile and young leaves of the plant, usually applied after sowing and pre-emergence of the crop, and can be used for rice, can also be safely applied in cotton, rape, corn, wheat, soybean, peanut, cucumber field, control of annual grass grass weeds and Cyperaceae weeds, such as matsua, green grass, grass, grass, wild oats, gold, water Cyperus, atypical Cyperus, broken rice Cyperus, deer grass, beef felt, etc.; Poor control of broad-leaved weeds. It is sensitive to the application of the drug before the 4-leaf stage in the direct-seeding paddy field, and can be used in the large seedling transplanting field, but not in the small seedling transplanting field. The resistance of dry seedlings to this product is similar to that of butachlor, and the mild injury is generally disappeared after 3 to 4 weeks, and there is no loss of Tiller and yield. Even at a high dose, the water-cultured seedlings are not phytotoxic, and the phytotoxicity is very serious if it is applied before 3d after planting. Similar experiments in the direct-seeding field have proved that the seedlings are applied 10 ~ 14d after seedling, the resistance of crops to phosphorus is poor. The typical symptom of phosphorus injury is that the crop can not germinate, or the growth is inhibited after emergence, and the seedling development is deformed. This product granules were applied in 1cm, 3cm, 6cm water depth of the paddy field, after the application of water layer to maintain 4 ~ 5d, no effect on the control effect. The selective herbicide, which belongs to the endoscopically conductive soil treatment, has a good effect on the shoots of the germinating weeds and a poor effect on the grown weeds. The damaged plant leaves are dark green, shorter, thick and brittle, and the heart leaves are not easy to extract, the growth stops, and finally dies. It is effective in the soil for 20 to 40 days. 30% Sarca phosphate EC. Appearance is brown liquid, with phosphoric acid ester odor, relative density of 1±0.05(20 deg C), room temperature storage stability for 2 years. |
| glyphosate | , belongs to the non-selective absorption conduction type of herbicide treatment of stems and leaves, early 20th century 70s by the company development, pure product is white odorless solid, melting point of 200 ℃, slightly soluble in water, slightly soluble in ethanol, ether, insoluble in commonly used organic solvents. Commonly used in commercial use is its sodium salt, isopropylamine salt or dimethylamine salt water, can be absorbed by the stems and leaves of green plants and transported to other parts and roots, it interferes with the synthesis of phenylalanine and tyrosine in plants, and makes the cell chromosome abnormal, and the underground part loses the ability of regeneration. The agent can only be used for spraying stems and leaves, not for soil treatment, because of the passivation in the soil lost the insecticidal activity. For Orchard, Mulberry, rubber plantation, fire, non-agricultural farmland and farmland before sowing to control the emergence of annual, perennial and dicotyledonous weeds. Low toxicity to human and animal. Rats with acute oral LD50, greater than 4320mg/kg, a dose of 3mg, mild skin irritation, and disappeared within 24 hours. Low toxicity to fish.|
| note | (1) the resistance of dry seedlings to this drug is similar to that of butachlor, mild phytotoxicity generally disappeared in 3~4 weeks, and had no effect on tillering and yield. (2) even at high doses, the water-cultured seedlings are free of phytotoxicity. If the seedlings are applied before 3 days after planting, the phytotoxicity is very serious, 10~14 days after seedling application, the crop resistance to this product is poor. (3) the shayong phosphorus granules were applied in paddy fields with water depths of 1, 3 and 6cm respectively, and the water layer was maintained for 4-5 days after application, which had no effect on the control effect. (4) This product is emulsified oil or mixed with 2,4-drop barrels to spray on the soil with enough water. When it is applied, the Paddy water is discharged, and the water is poured after 24 hours, its herbicidal effect is much improved. |
| toxicity | Acute oral LD50 of male rats is 830mg (original drug)/kg, female rats is 472mg (original drug)/kg, rat acute percutaneous LD50> 2g/kg, a slight stimulation of rabbit skin, the eyes have a certain stimulating effect. Male Japanese quail acute oral ld503360 mg/kg, female Japanese quail 2339mg/kg. Fish poisoning LC50(96 hours): Goldfish 4.6mg/L, rainbow trout 2.8mg/L. |
| synthesis method | 1. Synthesis of N-isopropyl-p-chloroaniline p-chloroaniline and 2-Bromopropane were sequentially added to the reaction kettle, heated and stirred, reacted at a certain temperature for several hours, then cooled, add sodium hydroxide solution to stir and separate into layers, wash the oil layer with water to neutral, extract the water layer with solvent, merge the oil layers, remove the solvent to obtain purple liquid, or extract the colorless liquid under reduced pressure, with the yield of 95% ~ 98%, the purity was 95% ~ 97%. 2. Synthesis of N-Chloroacetyl-N-isopropyl-p-chloroaniline N-isopropyl-p-chloroaniline, solvent and Chloroacetyl Chloride were successively put into the reaction kettle, heated and stirred, after several hours of reaction at a certain temperature, water was added to stir, layer was separated, the oil layer was washed with water for several times, the water layer was extracted with solvent, the oil layer was combined, and the solvent was removed to obtain a light red solid. The yield was 98% and the purity was over 96%. 3. In the reaction kettle, N-Chloroacetyl-N-isopropyl-p-chloroaniline, acid binding agent, solvent, and O,O-dimethyl dithiophosphoric acid were added sequentially, at a certain temperature, the reaction is stirred for several hours. At the end of the reaction, water is added to stir, layer is separated, and the oil layer is washed with water until neutral. After being dissolved, the product of raw material phosphorus is obtained, and the yield is 88% ~ 90%, the purity was 87% ~ 90%. |
| analytical method | (1) liquid chromatography: Column: YWG-NH2 amino column, × 200mm; Mobile phase: isopropanol; N-hexane = 1: 99 (volume ratio); Flow rate: 1.2/min; Detection wavelength: 220 nm; Column temperature: room temperature. (2) gas chromatography: ① column: 5% qf-1chromosorb WAWDMC column, 1m in length, 3mmS (60-80 mesh) stainless steel column. ② carrier gas: nitrogen. ③ reagents: toluene and chloroform (both analytically pure). ④ internal standard: dioctyl phthalate. (5) chromatographic operating conditions. Temperature: Column temperature 180 ℃; Gasification chamber 190~195 ℃; Detection chamber 180 ℃; Flow: nitrogen 56ml/min, hydrogen 31ml/min, air 255ml/min; Sensitivity X attenuation: 12 × 1/16; Paper speed: 1.5/min; Injection volume: 0.4-0.5. |
| Use | systemic organophosphorus herbicide. The medicament is absorbed by the root system and transmitted to the bud or leaf to inhibit the growth of the plant, turn the color to dark green, sometimes decolorize, stop the growth, and finally die. It is used to control monocotyledonous weeds in paddy fields, such as humulus scandens, heterotypic Cyperus papyrifera, broken rice papyrifera, duck tongue grass, tomentosa, herbifera, wheeling grass, etc. In the early stage of drug administration effect is very good, late administration can not be completely controlled. The general dosage of 100 m2 G/2.5 active ingredients, in the first leaf stage of Humulus scandens (4 ~ 8d after transplanting), with emulsifiable concentrate 3G active ingredients/100m2 spray, the sustained effect of 20 ~ 30d, emulsifiable concentrates (3-6g/100 m2) are also effective against weeds on dry land. |
| production method | alkylation reaction 0.376mol of p-chloroaniline and 2-Bromopropane were mixed and heated, and reacted at a certain temperature for several hours, after cooling and mixing with sodium hydroxide solution, the layers were separated into layers, washed with water until neutral, water layer was extracted with solvent, oil layers were merged, and 64g of purplish red liquid was obtained by desolvation to obtain 4-chloro-n-isopropylaniline, the yield was 95% ~ 98%. Or, 4-chloro-n-isopropylaniline is prepared by simultaneous reaction of p-nitrochlorobenzene with acetone and hydrogen. Or with P-chloroaniline and isopropanol in the presence of solid catalyst, 135~140 ℃, 0.67 ~ 0.7MPa under the reaction of 5H. In the chloroacetylation reaction, 0.48mol of the product from the previous step, the solvent and Chloroacetyl Chloride were mixed and heated, and the reaction was carried out at a certain temperature for several hours. Water was added, stirred, left to stand and layered, the oil layer was washed with water, the water layer was extracted, and the oil layer was merged. After being dissolved, light red N-Chloroacetyl-N-isopropyl-p-chloroaniline was 119G, yield 98%. It has also been reported that the reaction is carried out at a lower temperature using pyridine as an acid binding agent. After 0.17mol of N-Chloroacetyl-N-isopropyl-p-chloroaniline, acid binding agent, solvent and O,O-dimethyl dithiophosphoric acid are mixed, the reaction is stirred at a certain temperature for several hours, after being washed with water, 63g of phosphorus product was obtained, and the yield was 88% ~ 90%. |
Last Update：2024-04-10 22:29:15
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Product Name: Anilofos Visit Supplier Webpage Request for quotationCAS: 64249-01-0
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Mobile: 18021002903
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Raw Materials for S-4-Chloro-N-isoproylcarbamoylmethyl-O,O- dimethylphosphorodithioate