75 SP
Acephate
CAS: 30560-19-1
Molecular Formula: C4H10NO3PS
75 SP - Names and Identifiers
75 SP - Physico-chemical Properties
| Molecular Formula | C4H10NO3PS |
| Molar Mass | 183.17 |
| Density | 1.35 |
| Melting Point | 93°C |
| Flash Point | 2°C |
| Water Solubility | readily soluble |
| Vapor Presure | 2.26 x 10-4 Pa (24 °C) |
| Appearance | solid |
| Merck | 13,32 |
| BRN | 1936365 |
| pKa | 11.00±0.46(Predicted) |
| Storage Condition | APPROX 4°C |
| Refractive Index | 1.475 |
| Physical and Chemical Properties | A low toxic organophosphate insecticide with systemic and contact action. The pure product is a white crystal with a melting point of 92-93 °c. Soluble in water, methanol, acetone, slightly soluble in other organic solvents. melting point 93°C |
| Use | It has a good control effect on the pests of vegetables, corn, cotton, rice, soybean, fruit and other crops, such as aphid, mite, leaf hopper, cabbage worm, armyworm, cotton bollworm and so on. |
75 SP - Risk and Safety
| Risk Codes | R22 - Harmful if swallowed R36 - Irritating to the eyes R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R11 - Highly Flammable |
| Safety Description | S2 - Keep out of the reach of children. S36 - Wear suitable protective clothing. S36/37 - Wear suitable protective clothing and gloves. S16 - Keep away from sources of ignition. |
| UN IDs | UN1648 3/PG 2 |
| WGK Germany | 2 |
| RTECS | TB4760000 |
| HS Code | 29299040 |
| Toxicity | LD50 orally in rats: 700 mg/kg (Magee, 1973) |
75 SP - Nature
Open Data Verified Data
pure white crystals. Soluble in water, methanol, acetone and other polar solvents and dichloromethane, dichloroethane and other halogenated alkanes, benzene, toluene, xylene solubility is smaller, less soluble in ether. Unstable in alkaline medium.
Last Update：2024-01-02 23:10:35
75 SP - Preparation Method
Open Data Verified Data
methyl chloride, ammonia, dichloroethane, acetic anhydride, dimethyl sulfate as raw materials. Acephate was prepared by amination, acylation and isomerization. That is, 0,O dimethyl thiophosphoramide is obtained by amination, and 0.0 dimethyl-N-acetyl thiophosphoramide is obtained by acylation, and acephate is obtained by isomerization reaction.
Last Update：2022-01-01 10:11:26
75 SP - Use
Open Data Verified Data
is a broad-spectrum insecticide against rice pests, planthopper, leaf hopper, thrips, armyworm, Chilo suppressalis, Cotton aphids, cotton bollworm, fruit tree of the pear picolea, peach, spodoptera litura, cabbage worm, wheat aphid, armyworm and so on have good control effect.
Last Update：2022-01-01 10:11:27
75 SP - Safety
Open Data Verified Data
rat oral LD50: 700mg/kg.
Last Update：2022-01-01 10:11:27
75 SP - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| organophosphorus insecticide | acephate, also known as high phosphorus, was discovered in 1972 by Dr. J.M. Grayson of the United States. It is a kind of high-efficiency and low-toxicity broad-spectrum organophosphorus insecticide, which can be absorbed and transported by plants and has gastric toxicity, contact killing, fumigation and egg killing effects. The stomach toxicity to lepidopteran pests is greater than the contact toxicity, and the contact killing speed to aphids and mites is slow. Generally, the contact toxicity is exerted after 2-3 days after application. The residual period is moderate, and the half-life in the soil is three days. Its mechanism of action is to inhibit cholinesterase in insects. Acephate can last for 10 to 15 days on the leaves, and has good control effect on the main pests of rice, wheat, cotton, corn, vegetables, beans, fruit trees, sugarcane, tobacco, pasture, tea and other crops. Mainly control rice planthopper, leafhopper, thrips, leaf roller, stem borer, cotton weevil, cotton bollworm, fruit tree baby heart worm, cabbage, diamondback moth, yulcetia, and various aphids, armyworms, etc. If mixed with pesticides such as carivine and dimethoate, it has a synergistic effect and can increase the duration. |
| toxicity | acephate is low in toxicity to mammals such as humans and animals. the acute oral LD50 value of industrial products to rats is 886 mg/kg (female) ~ 945 mg/kg (male); The acute oral LD50 value for mice is 361 mg/kg. The minimum lethal dose for piglets and dogs is 681 mg/kg. Acute percutaneous LD50 for rabbits is greater than 2g/kg. Feeding dogs with feed containing 100mg/kg acephate for 2 years, except for a slight decrease in cholinesterase activity, no other obvious effects were found. Rats were fed with feed containing 30~100mg/kg acephate for two years, and no obvious pathological changes were found. No obvious pathological changes were found when rats and rabbits were fed for two years. There were no teratogenic and carcinogenic effects on rats and rabbits. Low toxicity to poultry and fish, acute oral LD50 to male wild ducks is 350 mg/kg; TLm(96 hours)>1g/L for rainbow trout, 2.05g/L for large fin scaly gill sunfish (96 hours), 1.72g/L for black bass (96 hours), 2.23g/L for spotted forktail and 6.65g/L for mosquito-eating fish; TLm(96 hours) of golden needle fish is 9.5g/L, blue gill fish is 2g/L. the acute oral LD50 of 99% industrial products to male rats is 945 mg/kg and that to female is 866 mg/kg. Acute percutaneous LD5050 in rabbits is 104mg/L(48h) and silver carp is 485mg/L(48h). The acute oral LD50 was 350mg/kg for male wild ducks and 852mg/kg for chicks. |
| poisoning and first aid | symptoms of acephate poisoning: mild poisoning: headache, dizziness, nausea, vomiting, hyperhidrosis, weakness, chest tightness, blurred vision, poor appetite, etc. The activity of whole blood cholinesterase generally dropped below 70% of the normal value. Moderate poisoning: In addition to the above symptoms, there are also mild dyspnea, muscle tremor, miosis, trance, unstable walking, sweating, salivation, abdominal pain, diarrhea, etc. In severe cases, coma, convulsions, dyspnea, foaming at the mouth, incontinence, convulsions, respiratory paralysis, etc. Acute poisoning occurs within 12 hours, and those who take it by mistake can get sick immediately. First aid measures: If you accidentally inhale, the patient should be moved to the air circulation. If you accidentally touch the skin or splash into the eyes, rinse with plenty of water for at least 15 minutes. If you take it by mistake, you should immediately bring the drug label to the hospital for treatment. (1) use atropine 1~5 mg subcutaneous or intravenous injection (depending on the severity of poisoning). (2) intravenous injection of 0.4~1.2 grams of phosphonidin (depending on the severity of poisoning). (3) Morphine, theophylline, phenothiazine, reserpine are prohibited. (4) if you take acephate by mistake, you should immediately induce vomiting (only when you are awake), gastric lavage and catharsis. Reference material: Editor-in-Chief Kong Lingqiang. A handbook of knowledge on pesticide management and use. Jinan: Shandong Science and Technology Press. 2009. |
| control of rice and cotton pests | 1. rice pests: (1) control of rice stem borer, apply medicine at the peak of egg incubation, use 40% acephate emulsifiable concentrate 2.5 ~ 3L/hm2, add water to spray; The efficacy period is about 5 days. (2) to control the white spike caused by rice stem borer, the control effect can reach about 95% by using 40% emulsifiable concentrate of 2.5~3L/hm2 from the break of rice to the full spike stage. in the case of serious stem borer, the stem borer rate can be controlled below 0.3%. However, in the case of long occurrence period of borers and irregular heading of rice, the second time should be applied 5 days after the first medicine. Because acephate has no contact toxicity to stem borer mosquito borer, and the efficacy period is short, it has poor control effect on stem borer caused by stem borer and is generally not suitable for use. (3) control of rice leaf roller, rice tillering stage, 2~3 instar larvae of 45~50 head, leaf damage rate of 7% ~ 9%; Booting stage, 2~3 instar larvae of 25~35 head, leaf damage rate of 3% ~ 5%, with 40% acephate emulsifiable concentrate 2 ~ 3L/hm2, 900~1000kg of water spray. (4) Control of rice planthoppers, rice booting heading stage, 2-3 instar nymphs peak period, 1300 head of 100 stump insects; During the milk ripening period, 2-3 instar nymphs peak period and 2100 head of 100 stump insects, 30% emulsifiable concentrate 1.5~2L/hm2 was used to spray 900~1000kg of water. It also has good treatment effect on rice leafhopper and rice thrips. 2. cotton pests: (1) control cotton aphid and red spider, use 40% emulsifiable concentrate 1.5L/hm2 and spray 800~1000kg of water. the control effect increases slowly within 2~3 days after application, and the control effect can reach more than 90% within 5 days after application. The effective control period is 7~10 days. (2) to prevent and control cotton elephant A and cotton bug, spray 800~1000kg of water with 40% acephate emulsifiable concentrate 0.75~1.5L/ hm2 at the initial stage of damage to the two insects. (3) to control cotton bollworm, 40% acephate emulsifiable concentrate 3~4L/hm2 was used during the incubation period of 2~3 generations of eggs, and 1000~1500kg of water was sprayed, with an effective control period of about 7 days. However, the control effect on cotton red bollworm is poor and should not be used. |
| production flow chart of acephate | 1. synthesis of intermediate dimethoxy phosphorothioamide according to the ratio of ingredients, first add chloride and solvent into the reaction kettle, add ammonia water dropwise at the material temperature of 15 ℃ under stirring, raise the temperature to 35-40 ℃, and keep it for 35-40 minutes. Then cool the material to 20~30 ℃ and keep it for 35 minutes. Stand to separate the organic phase. Then de-dissolve (or without desolvation) under reduced pressure to obtain amine, the content is about 90%, the yield is 88% ~ 90%, the moisture 2. synthesis of acylate add solvent amine to the reaction kettle, add acetic anhydride under stirring, reduce the temperature in the kettle to 10 ℃, slowly add concentrated sulfuric acid dropwise, after adding, raise the temperature to 55~60 ℃, and keep for 50 minutes, after the reaction, the temperature is lowered to 10 ℃, ammonia water is added dropwise, and the pH of the neutralization reaction liquid is 7~8 (neutralization temperature> 30 ℃). Then let the material stand and separate the organic phase, and desolicate it at a vacuum of 0.0866MPa to obtain acylate with 90% content, yield (calculated as monochlorine)>82%, moisture 3. isomerization (prepared from acephate) acephate is formed by isomerization of acylate under the catalysis of dimethyl sulfate. After isomerization, brown oily viscous liquid was obtained. Needle crystals were precipitated after standing. The melting point was 70~80 ℃, the content of acephate was 58%, and the yield was 73%. |
| mixed use of acephate and other chemicals | mixed use of acephate and organophosphorus insecticides such as dichlorvos, chlorpyrifos, triazophos, dimethoate, etc., It has obvious synergistic effect and can be used to control cutworms, cabbage worms, rice borers and aphids; mixed with pyrethroid pesticides, it can be used to control vegetable and fruit tree pests. |
| precautions | (1) cannot be mixed with alkaline pesticides. (2) Not suitable for use on mulberry and tea trees. (3) the allowable daily intake (ADI) of acephate per person is 0.02 mg/kg. 40% EC has formulated a safe use standard (national standard number GB4285-84) for the maximum number of times per year and a safe interval of not less than 7 days on vegetables in our country. The application should be carried out according to the usage standards. (4) The drug is flammable. Pay attention to fire prevention and keep away from fire sources during transportation and storage. (5) The symptoms of poisoning are typical symptoms of organophosphorus poisoning, but the duration of the disease is longer and the recovery of cholinesterase is slow. Thoroughly remove poison with alkaline water or clear water. Use atropine or polyphosphate to detoxify, symptomatic treatment, pay attention to prevent brain edema. |
| analytical method | gas chromatography for product and residue analysis. |
| Degradation metabolism | Acephate is mostly hydrolyzed after the P-S bond is hydrolyzed, and methyl mercaptan is partially oxidized. In addition, it can also be hydrolyzed at the N-C bond. |
| allowable residue | the maximum allowable residue on vegetables and citrus is 5 mg/kg(FAO/WHO). |
| use | this product is a broad-spectrum, high-efficiency, low-toxicity, low-residue organophosphorus insecticide, with stomach toxicity, contact killing, internal absorption, and a bin fumigation effect. It is suitable for vegetables, rice, cotton, wheat, fruit trees, rape, tobacco, etc., to prevent and control various vegetable pests, rice leaf roller, rice thrips, rice leaf hoppers, rice planthoppers, Chilo suppressalis, Chilo suppressalis, Chilo suppressalis, fruit tree heart feeding worms, aphids, cotton red bollworm, cotton bollworm, cotton red spider, cotton aphid and more than 100 kinds of pests. For example, to control rapae, young larvae of Plutella xylostella and aphids, spray 800~1200 times 40% emulsifiable concentrate. To control cotton pests, use 40% emulsifiable concentrate 18.8~26mL/100 m2 and spray water evenly. Control rice leaf roller, rice thrips, rice leafhopper and rice planthopper, with 40% emulsifiable concentrate 19~30mL/100 m2, diluted 500~800 times liquid spray. Acephate is a broad-spectrum insecticide, which is effective against rice pests, planthoppers, leafhoppers, thrips, leaf curls, armyworms, cotton aphids, cotton bollworms, and fruit trees. Pear heart-eating worms, peach heart-eating worms, vegetable Plutella, Spodoptera litura, cabbage worm, wheat aphid, armyworm, etc. have good control effects. Generally, the concentration (active ingredient) is 0.05 ~ 0.1%, and the dosage per mu is 50~70g. It has good control effect on various pests of grain, oil, fruit, and vegetable crops such as planthoppers, leaf hoppers, rice leaf hoppers, diamondback moths, aphids, cotton red spiders, etc. Broad-spectrum organophosphorus insecticides, it has a good control effect on major pests of rice, wheat, cotton, vegetables and other crops It has a good control effect on pests of vegetables, corn, cotton, rice, soybeans, fruits and other crops such as aphids, mites, leafhoppers, and cabbage caterpillar., Cotton bollworm, etc. have good control effects. is a broad-spectrum organophosphorus insecticide, mainly used to control cotton bollworm, cotton aphid, etc. |
| production method | the raw materials for producing acephate are methyl chloride, ammonia water, dichloroethane, acetic anhydride and dimethyl sulfate. It is obtained by reaction steps such as amination, acylation, and isomerization. 1. Amination Add methyl chloride and corresponding proportion of dichloroethane into the amination kettle from the high-level metering tank respectively, start stirring and freezing salt water. When the temperature in the kettle drops to 15 ℃, slowly add ammonia water into the kettle from the high-level ammonia metering tank. The temperature in the kettle is controlled at 35-40 ℃ for 35-40min. After dropping ammonia water, adjust the frozen salt water to reduce the temperature in the kettle to 20-23 ℃. Keep the temperature and stir for 30-35min, then add 6L of water, after stirring for 2-3min, stop stirring, pump the material into the amination separator and let it stand and layer, after 30min, put the organic phase into the receiving tank for metering, and the organic phase is the amine with solvent (O,O-dimethyl thiophosphoramide). 2. Acylation (1) Ethylene anhydride method Put the amine with solvent into the acylation kettle from the high-level measuring tank, start stirring, then add acetic anhydride into the acylation kettle from the high-level measuring tank of acetic anhydride, then open the frozen brine, when the temperature in the kettle drops to 10 ℃, slowly add concentrated sulfuric acid into the reaction kettle from the high-level measuring tank, after dropping sulfuric acid, open the air pressure, and discharge the frozen brine in the jacket, heat slowly with steam to raise the temperature in the kettle to 55-60 ℃ for 50min. After the reaction is completed, the temperature in the kettle is reduced to 10 ℃. Chlorine water is added from the ammonia water high-level tank to neutralize the acetic acid generated by the reaction to pH 7-8. During the neutralization process, the temperature should be controlled below 30 ℃. After neutralization, the material is pumped into the separator and left to stand for separation, the lower organic phase is separated into a crude acylate storage tank, and then pumped into a distillation kettle for decompression distillation and desolution (vacuum degree 86.7kPa,70 ℃, 15-20min) to obtain acylate (O,O-dimethyl-N-acetyl thiophosphoramide). (2) acetyl chloride method will be the amine with solvent from the high-level metering tank into the acylation kettle, open the stirring, from the acetyl chloride high-level metering tank to add acetyl chloride. Then slowly raise the temperature in the kettle to 50 ℃, keep the temperature to react for 2 hours, finish the reaction, reduce the temperature in the reaction kettle to 10 ℃, and then slowly add ammonia water from the ammonia water high-level metering tank to neutralize the acid generated by the reaction to pH 7. During the neutralization process, the temperature in the kettle should be controlled below 30 ℃. After neutralization, add appropriate amount of water. The ammonium salt generated in the neutralization process is dissolved, stirred for 2-3min, and the material is pumped to the separator and left to stand for separation. The lower organic phase is separated and pumped into a distillation kettle for decompression and desolution (vacuum degree 86.7kPa,70 ℃, 15-20min) to obtain acylate. Acylation reaction using acetic anhydride or acetyl chloride as acylating agent can achieve better results. 3. Isomerization Put the quantitative acylate into the isomerization kettle from the acylate high-level metering tank, start the stirring, then add the dimethyl sulfate into the isomerization kettle in proportion from the dimethyl sulfate high-level metering tank, slowly raise the temperature to 65-70 ℃, keep the temperature for 2 hours, and discharge the material to obtain acephate crude oil. For every 1t of 50% crude oil produced, the raw materials consumed are: methanol (98%)1953kg, phosphorus trichloride (98%)1660kg, caustic soda (30%)3220kg, dimethyl sulfate (98%)120kg, ammonia water (18%)2450kg, sulfur (98%)315kg, acetic acid (98%)295kg, amine (40%)1700kg, acetic anhydride (69%)490kg, ammonium sulfide (industrial product) 2200kg, dichloroethane (98%)250kg. First isomerization and then acylation First, O,O-dimethylthiophosphonamide is heated and isomerized in the presence of a small amount of dimethyl sulfate to generate O,S-dimethylthiophosphonamide, and then interact with acetic anhydride or acetyl chloride to generate acephate. First acylation and then isomerization First, O,O-dimethylthiophosphonamide is reacted with acylating agents in dichloroethane or benzene solvent. Commonly used acylating agents are glacial acetic acid zinc trichloride, acetic anhydride, Acetyl chloride, ketene, etc. The acylation reaction yields O,O-dimethyl-N-acetylthiophosphonamide, which is then heated isomerized to acephate in the presence of a small amount of dimethyl sulfate. Using a new type of catalyst and a special crystallization solvent, a high-purity original drug can be prepared. The process is: add 200g of methamidophos crude oil to the reaction bottle, start stirring and heating to the reaction temperature, under the action of the catalyst, dropwise addition Acylating agent acetic anhydride, control the reaction temperature, and perform the heat preservation reaction for several hours after the dropwise addition, that is, acephate crude crude crude oil is obtained; then the organic phase and the water phase are separated by neutralization and extraction, the organic phase is purified to obtain acephate refined crude oil; adding solvent A and crystal additives, slowly stirring, cooling, crystallization, filtration, and rinsing to obtain the finished product. After the treatment of the obtained mother liquor, qualified finished products can be recovered, with a total product yield of more than 78% and a content of more than 98.0%. |
| category | pesticide |
| toxicity classification | highly toxic |
| acute toxicity | oral-rat LD50: 700 mg/kg; Oral-mouse LD50: 233 mg/kg |
| flammability hazard characteristics | combustible; combustion produces toxic nitrogen oxides, sulfur oxides and phosphorus oxide smoke |
| storage and transportation characteristics | warehouse ventilation and low temperature drying; Store separately from alkalis and food additives |
| fire extinguishing agent | water, foam, carbon dioxide, sand |
| 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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