2,3-dihydro-2,2-dimethyl-7-benzofuranyl methylcarbamate
Carbofuran
CAS: 1563-66-2
Molecular Formula: C12H15NO3
2,3-dihydro-2,2-dimethyl-7-benzofuranyl methylcarbamate - Names and Identifiers
2,3-dihydro-2,2-dimethyl-7-benzofuranyl methylcarbamate - Physico-chemical Properties
| Molecular Formula | C12H15NO3 |
| Molar Mass | 221.25 |
| Density | 1.18 |
| Melting Point | 150-153°C(lit.) |
| Boling Point | 200°C |
| Flash Point | 143.3°C |
| Water Solubility | Slightly soluble. 0.07 g/100 mL |
| Solubility | Methylene chloride (>200 g/L), 2-propanol (20–50 g/L) (Worthing and Hance, 1991) |
| Vapor Presure | 2 x 10-5 mmHg at 33 °C (quoted, Verschueren, 1983) |
| Appearance | Powder |
| Color | White, brown |
| Exposure Limit | OSHA PEL: TWA 0.1 mg/m3; ACGIH TLV: TWA 0.1 mg/m3. |
| Merck | 13,1813 |
| BRN | 1428746 |
| pKa | 12.28±0.46(Predicted) |
| Storage Condition | 0-6°C |
| Refractive Index | 1.5200 (estimate) |
| Physical and Chemical Properties | Pure white crystals, no smell, m.p.153 ~ 154 ℃; Industrial M.P. 150~152 ℃. The relative density was 1.180, and the vapor pressures were 2.26 × 10-3PA (30 ° C.) and 1.47 × 10-2Pa (50 ° C.). Soluble in a variety of organic solvents, 25 ℃ solubility (mass ratio): acetone 15%, acetonitrile 14%, cyclohexanone 9%, dimethyl formamide 27%, dimethyl sulfoxide 25%, methyl pyrrolidone 30%, insoluble in xylene, petroleum ether, kerosene, water solubility of 700mg/L (25 degrees C). It is stable in neutral and alkaline conditions, and easy to hydrolyze in alkaline medium. The half-aging period is 1600d(25 ℃) at pH 5.2; The half-aging period is 28d(28 ℃) at pH 7; The half-aging period is 7H (26 ℃) at pH 9. Non-corrosive, non-flammable. |
| Use | For broad-spectrum pesticides, with a strong absorption, and contact and stomach poison effect, used to control sugarcane, rice, peanut, cotton and other pests |
2,3-dihydro-2,2-dimethyl-7-benzofuranyl methylcarbamate - Risk and Safety
| Risk Codes | R26/28 - Very toxic by inhalation and if swallowed. R50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. |
| Safety Description | S36/37 - Wear suitable protective clothing and gloves. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 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. S1/2 - Keep locked up and out of the reach of children. |
| UN IDs | UN 2811 6.1/PG 1 |
| WGK Germany | 3 |
| RTECS | FB9450000 |
| HS Code | 29329990 |
| Hazard Class | 6.1(a) |
| Packing Group | I |
| Toxicity | LD50 orally in mice: 2 mg/kg (Fahmy, 1970) |
2,3-dihydro-2,2-dimethyl-7-benzofuranyl methylcarbamate - Upstream Downstream Industry
| Raw Materials | Benzene Furan 2,3-dihydro-2,2-dimethyl-7-benzofuranol Poly(vinyl alcohol) Chlorine Triethylamine Carbon tetrachloride Methylamine |
2,3-dihydro-2,2-dimethyl-7-benzofuranyl methylcarbamate - Introduction
Open Data Unverified Data
overview
carbofuran is also called dafu, carbofuran, and insect mite. The pure product is white crystal with no odor, melting point 153~154 ℃, specific gravity (20 ℃)1.180, vapor pressure 266 at 33 ℃, 6 × 10-5Pa. The solubility in water at 25 ℃ is 700 mg/L, which is soluble in various organic solvents and hardly soluble in xylene, petroleum ether and kerosene. The original drug is light yellowish brown, the content of active ingredients is 90% ~ 95%, the melting point is 147~155 ℃, and it has weak ester odor. It is unstable and non-flammable in alkaline medium, but it can be ignited and has no corrosive effect. It belongs to the carbamate class, which is broad-spectrum, systemic insecticide and acaricide. It has contact killing and stomach toxic effects on pests. Its toxicological mechanism is to inhibit cholinesterase, but unlike other carbamate insecticides, its binding with cholinesterase is irreversible, so it is highly toxic. This medicine can be absorbed by plant roots and can be transported to various parts of the plant. It accumulates more on the leaf surface, especially on the leaf edge, which is less in the fruit. The half-life in soil is 30~60 days. The residual effect period is short when applied to the soil, and the residual effect period is longer when applied to the soil. The effect can be maintained for about 40 days in cotton and sugarcane fields. High toxicity to humans and animals. High toxicity to fish, ducks and geese. The dosage form is 35% seed treatment agent and 3% granule. 35% carbofuran seed treatment agent consists of active ingredients carbofuran and polyvinyl acetate, blue alkaline red, water-soluble adhesive, water and anti-foaming agent. Appearance of purple liquid, easily soluble in water, stable storage at room temperature for more than 2 years. 3% carbofuran granules are composed of active ingredients carbofuran and vinyl polyester, sugar, pigment, sand and water. The appearance is purple, reddish brown or light blue particles. The storage period at room temperature is more than 5 years, but it is easy to decompose when encountering alkali.
application method of carbofuran
(1) prevention and control of pests at cotton seedling stage: use 1.5~2kg of 3% granule per mu, sprinkle it into the ditch at the same time as the seeds, or mix dry cottonseed with 3% granule, and the dosage is 1 part of medicine and 4 parts of cottonseed.
(2) Control of pests in tobacco fields: Control of tobacco pests such as tobacco aphids, root-knot nematodes, cutworms, and mole crickets. When transplanting tobacco seedlings, use 3% granules and sprinkle 1-1.5 grams per hole.
(3) Control of rice field pests: Control of rice borers, planthoppers, thrips, leafhoppers, rice gall midge and other pests, use 1.5-2kg of 3% granules per mu, and 15kg of fine sand, mix well and withdraw to the water surface; Use 2-2.5kg of 3% granules per mu in land rice fields and sow them simultaneously with rice seeds.
(4) Control of pests in soybean fields: Control aphids, bean stem flies and cyst nematodes, etc., use 2.2~4.4kg of 3% granules per mu and sprinkle them in the sowing ditch.
(5) Control of peanut field pests: control of aphids, thrips, mole crickets and root-knot nematodes. 4-5kg of 3% granule per mu is sprinkled in the sowing ditch or between rows during the crop growth period to cover the soil. (6) Precautions for use: First, carbofuran is highly toxic, and safety should be paid attention to when using it; this medicine is not allowed to be diluted and sprayed with water. Second, when used in rice fields, it cannot be mixed with dipteryon and metrine at the same time; when used, dipteryon should be used 4 days before the use of carbofuran or 1 month after the use of carbofuran.
toxicity
according to China's pesticide toxicity classification standard, carbofuran is a highly toxic pesticide. The acute oral LD50 of the original drug in rats is 8~14 mg/kg, and the acute percutaneous LD50 of rabbits is greater than 10200 mg/kg, which has no irritating effect on eyes and skin. No teratogenic, mutagenic and carcinogenic effects on animals within the test dose. There were no abnormalities in the third-generation reproduction test and neurotoxicity test. The two-year feeding test had no effect dose of 25 mg/kg in mice and 20 mg/kg in dogs. Carbofuran is highly toxic to fish, (fish worker) trout 96 hours TLm is 0.28 mg/l. It is non-toxic to bees, but toxic to birds. The LD50 of pheasants is 573 mg/kg. 35% The acute oral LD50 of carbofuran seed treatment agent in rats is 40 mg/kg, and the acute percutaneous LD50 in rabbits is greater than 2000 mg/kg. The acute oral LD50 of 3% carbofuran granules in rats is 437 mg/kg, and the acute percutaneous LD50 of rabbits is greater than 10200 mg/kg. The daily allowable intake (ADI) of human body is 0.01 mg/kg, the maximum residue limit (MPL)(FAO/WHO) is 0.1 μg/g for oil seeds, 0.2 μg/g for brown rice and 0.1 μg/g for peanut kernels.
the acute oral LD50 of rats is 8~14 mg/kg (industrial products are 1.0 mg/kg), the acute percutaneous LD5050 is 19 mg/kg, and the chicken is 9 mg/kg. Trout LC501.5mg/L (0.28 mg/kg) (96h), industrial products to catfish, green strontium fish LC50 is 0.21~0.28mg/L. Rats were fed at a dose of 25mg/kg for 2 years without poisoning. Within the test dose, there was no teratogenic, carcinogenic, and mutagenic effect on animals, and there was no abnormality in the third-generation reproduction test and neurotoxicity test.
use
broad-spectrum, high-efficiency, low-residue, high-toxicity carbamate insecticide, acaricide, nematicide. It has the effects of absorption, contact killing, stomach poison, and has a certain egg killing effect. It has a long active period and generally has a half-life of 30 ~ 60d in the soil. It can be used to control rice stem borers, rice thrips, rice leaf curls, rice planthoppers, rice leafhoppers, rice weevil, corn borer, corn root cutter, cotton aphid, cotton bollworm, soybean aphid, soybean heart worm, mites and nematodes. The general dosage is 6.8~10g active ingredient/100 m2, or 3% granule 225~300g/100 m2. Cotton seeds can be treated with sulfuric acid and then coated with 35% seed coating agent (the effective ingredient is 1% of the dry weight of the seeds) to prevent and control pests such as cotton aphid and cutworm.
carbofuran is a carbamate broad-spectrum internal absorption insecticide, acaricide and nematicide, which can be used for various crops to control more than 300 kinds of pests and nematodes in soil and on the ground. It also has the effect of shortening the growth period of crops, promoting the growth and development of crops and thus effectively increasing crop yields. The toxic method of carbofuran to insects is mainly the effect of internal absorption and insecticidal. The agent is applied to the base part of the soil crop, and the root system is absorbed and transported to the stems and leaves with water to achieve the purpose of insect control; carbofuran also has a contact effect. It is used to control cotton aphids, rice, corn root insects, and is effective against most pests of rice, corn, peanuts and other crops.
It is a broad-spectrum insecticide with strong systemic properties, and has both touch and stomach toxicity effects. It is used to prevent and control sugarcane, rice, peanuts, cotton and other pests.
It has excellent antistatic And corrosion resistance, good dispersion, emulsification, and foaming effects. It can also be used as an additive for the production of napkins and toilet paper.
It is a broad-spectrum insecticide and nematicidal agent, there are contact, stomach poison, and systemic effects
used to control pests of cotton, rice, corn, peanuts, grains, bananas, coffee, sugar beets, tobacco and other crops
carbofuran is a carbamate broad-spectrum internal absorption Insecticidal, acaricidal and nematicide can be used for a variety of crops to control more than 300 kinds of pests and nematodes in the soil and on the ground. It also has the effect of short crop growth period, promoting crop growth and development, thus effectively increasing crop yield. The toxic method of carbofuran to insects is mainly the effect of internal absorption and insecticidal. The medicine is applied to the foundation part of the soil crop. After the root system is absorbed, it goes to the stems and leaves with water to achieve the purpose of insect control. Carbofuran also has a contact effect. It is used to control cotton aphids, rice, corn root insects, and is effective against most pests of crops such as rice, corn, and peanuts.
Production method
It is obtained by condensation of furan phenol and methyl isocyanate.
Starting from the chlorination reaction of o-nitrophenol, isopropene is chlorinated under a certain pressure to produce methyl chloropropene. The chlorination reaction solution is post-processed by pressure filtration and distillation, and the purity of the product can reach 96%. The etherification reaction o-nitrophenol and methyl chloropropene in the presence of sodium carbonate to prepare 2-methylallyl o-nitrophenol ether. The Clayson reaction 2-methylallyl o-nitrophenol ether is heated, and the Clayson reaction is transposed to generate 2-(2-methylallyl)-6-nitrophenol. In the presence of anhydrous magnesium chloride, the Clayson rearrangement product ring synthesizes 2, 3-dihydro-2, 2-dimethyl-7-nitrobenzofuran (commonly known as 7-nitro). The hydrogenation reaction reduces 7-nitro in the presence of palladium/carbon catalyst to produce 2, 3-dihydro-2, 2-dimethyl-7-aminobenzofuran (commonly known as 7-amino). Diazotization reaction 7-amino group is reacted with sodium nitrite aqueous solution and concentrated sulfuric acid to produce 2, 3-dihydro-2, 2-dimethyl-7-benzofuran diazosulfate (commonly known as 7-Diazosulfate). Hydrolysis reaction 7-diazosulfate is hydrolyzed into 2, 3-dihydro-2, 2-dimethyl-7-hydroxybenzofuran (commonly known as 7-hydroxy compound) under the catalytic action of CuSO4. Synthesis of carbofuran The 7-hydroxy compound and methyl isocyanate are synthesized in a solvent in the presence of a small amount of triethylamine. MCC can also be added dropwise to 7-hydroxy compound at 55 ℃ by methylcarbamoyl chloride method with 97% yield. Starting from catechol, this process route is that catechol is heated with methylchloropropene in the presence of K2CO3 · KI in an anhydrous acetone solvent to generate 2-methylallyloxyphenol, and then heated to transpose, Cyclic to obtain 7-hydroxy compound. Carbofuran was then synthesized by the isocyanate method in the presence of triethylamine. The operation procedure is as follows. Preparation of 2-methylallyl oxidized phenol under nitrogen protection, 40 parts (mass) of potassium carbonate and 481 parts (mass) of potassium iodide are slowly added to 322 parts (mass) of catechol and 300 parts (mass) of anhydrous acetone solution that have been stirred and mixed. Heat the obtained substance to reflux temperature and slowly add 262 parts (mass) of methyl chloropropene. The mixture was refluxed for 30h, cooled and let stand for 18h, filtered, the filtrate was concentrated under reduced pressure, the residual oil was extracted with chloroform and washed, dried, concentrated, and the residual oil was distilled under reduced pressure to obtain 213 parts (mass) of 2-methylallyloxyphenol. Preparation of 7-Hydroxyl Compound 131 parts (mass) of 2-methylallyloxyphenol are transposed and cyclized, and an exothermic reaction occurs at 200 ℃, so that the temperature can quickly reach and maintain 275 ℃ to obtain a thick syrup. Distilled under reduced pressure to obtain colorless 2, 2-dimethyl-2, 3-dihydro-7-hydroxybenzofuran (7-hydroxy compound). The synthesis of 16.6 parts (mass) of the 7-hydroxy compound of carbofuran was treated with 5.8 parts (mass) of isocyanate formic acid and 0.1 parts (mass) of triethylamine in 14 parts (mass) of ether, and the mixture was stirred at room temperature to precipitate a white crystalline product. Separation of solid crystals to obtain 17.5 parts of carbofuran.
Last Update：2024-04-09 19:43:38
2,3-dihydro-2,2-dimethyl-7-benzofuranyl methylcarbamate - Introduction
This standard substance is mainly used for measuring instrument calibration, analytical method evaluation and quality control, as well as the content determination and residue detection of corresponding components in related fields such as food, hygiene, environment and agriculture. It can also be used for value traceability or as a standard liquid reserve solution. It is diluted step by step and configured into various standard solutions for work. 1. Sample Preparation This standard substance is made of carbofuran pure product with accurate purity and fixed value as raw material, chromatographic methanol as solvent, and accurately configured by weight-volume method. Carbofuran, English name: Carbofuran,CAS No.: 1563-66-2 2. Traceability and Setting Method This standard substance takes the configuration value as the standard value, and uses high performance liquid chromatography-diode array detector (HPLC-DAD) to compare this batch of standard substances with quality control control samples to verify the preparation value. By using preparation methods, measurement methods and measuring instruments that meet the requirements of metrological characteristics, the traceability of the value of the standard substance is guaranteed. 3. characteristic measure value and uncertainty (see certificate) number name standard value (ug/mL) relative expansion uncertainty (%)(k = 2)BW10222 The uncertainty of the standard value of the 1002 in methanol is mainly composed of raw material purity, weighing, constant volume and uniformity, stability and other uncertainty components. 4. uniformity test and stability inspection According to the JJF1343-2012 [General Principles and Statistical Principles of Standard Substance Setting], random sampling of sub-packed samples is carried out, uniformity test of solution concentration is carried out, and stability inspection is carried out. The results show that the standard material has good uniformity and stability. The standard substance is valid for 30 months from the date of setting the value. The development unit will continue to monitor the stability of the standard substance. If the value changes are found during the validity period, the user will be notified in time. 5. packaging, transportation and storage, use and precautions 1. Packaging: This standard substance is packed in borosilicate glass ampoules, about 1.2 mL/branch. When removing or diluting, the pipette quantity shall prevail. 2. Transportation and storage: ice bag transportation, transportation should avoid extrusion, collision. 3. Use: Balance at room temperature (20±3 ℃) before unsealing, and shake well. Once the ampoule is opened, it should be used immediately and cannot be used as a standard substance after being fused again.
Last Update：2022-10-16 17:14:10
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