O,S-dimethyl O-[3-methyl-4-(methylsulfanyl)phenyl] phosphorothioate
fenthion
CAS: 55-38-9
Molecular Formula: C10H15O3PS2
O,S-dimethyl O-[3-methyl-4-(methylsulfanyl)phenyl] phosphorothioate - Names and Identifiers
| Name | fenthion |
| Synonyms | FASTER FENCHEM fenthion ENTEX(R) LEBAYCID FENTHION BEILIULIN ENT 25540 LEBAYCID(R) O,O-dimethyl O-(4-methylthio-m-tolyl) phosphorothioate O,S-dimethyl O-[3-methyl-4-(methylsulfanyl)phenyl] phosphorothioate O,O-dimethyl O-[3-methyl-4-(methylsulfanyl)phenyl] phosphorothioate |
| CAS | 55-38-9 |
| EINECS | 200-231-9 |
| InChI | InChI=1/C10H15O3PS2/c1-8-7-9(5-6-10(8)15-3)13-14(11,12-2)16-4/h5-7H,1-4H3 |
O,S-dimethyl O-[3-methyl-4-(methylsulfanyl)phenyl] phosphorothioate - Physico-chemical Properties
| Molecular Formula | C10H15O3PS2 |
| Molar Mass | 278.33 |
| Density | 1.25 |
| Melting Point | 7.5°C |
| Boling Point | 87°C (0.01 mmHg) |
| Flash Point | >100°C |
| Water Solubility | 0.0055 g/100 mL |
| Vapor Presure | 7.4 x 10-4 Pa (20 °C) |
| Appearance | liquid |
| Exposure Limit | OSHA PEL: TWA 0.2 mg/m3; ACGIH TLV: TWA 0.2 mg/m3 |
| Merck | 13,4030 |
| BRN | 1974129 |
| Storage Condition | 2-8°C |
| Stability | Stable. Incompatible with strong oxidizing agents. |
| Refractive Index | nD20 1.5698 |
| Physical and Chemical Properties | Density 1.25 melting point 7.5°C boiling point 87°C (0.01 mmHg) water solubility 0.0055g/100 mL |
| Use | A broad-spectrum, rapid-acting, long-residual insecticide with both contact and systemic properties |
O,S-dimethyl O-[3-methyl-4-(methylsulfanyl)phenyl] phosphorothioate - Risk and Safety
| Risk Codes | R21/22 - Harmful in contact with skin and if swallowed. R23 - Toxic by inhalation R48/25 - R50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. R68 - Possible risk of irreversible effects R67 - Vapors may cause drowsiness and dizziness R65 - Harmful: May cause lung damage if swallowed R38 - Irritating to the skin R11 - Highly Flammable |
| 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. S62 - If swallowed, do not induce vomitting; seek medical advice immediately and show this container or label. |
| UN IDs | UN 2810/3017 |
| WGK Germany | 3 |
| RTECS | TF9625000 |
| HS Code | 29309090 |
| Hazard Class | 6.1(b) |
| Packing Group | III |
| Toxicity | LD50 in male, female rats (mg/kg): 215, 245 orally (Gaines) |
O,S-dimethyl O-[3-methyl-4-(methylsulfanyl)phenyl] phosphorothioate - Upstream Downstream Industry
| Raw Materials | m-Cresol Methyl alcohol |
O,S-dimethyl O-[3-methyl-4-(methylsulfanyl)phenyl] phosphorothioate - Reference Information
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| drug substance toxicity | the toxic insecticide of the genus betisthion is toxic to dogs and poultry, and highly toxic to bees, no chronic toxicity. It has the effect of killing and stomach poison on pests, and has a certain permeability to crops, but has no internal absorption and conduction effect. It has a broad spectrum of insecticidal and rapid action. Suitable for the control of rice, cotton, fruit trees, vegetables, soybean on a variety of pests, the mites are also effective. In the plant body oxidation into sulfoxide and sulfone, insecticidal activity increased. The common pesticide formulation is 50% thiophos EC. |
| Usage | 1. Rice pest control of Chilo suppressalis, Chilo suppressalis per mu with 50% emulsifiable concentrate 75-150 and fine soil 75-100 made poison soil or water 50-spray. Rice leaf hopper and rice straw planthopper can be controlled by spraying at the same dose. 2. Prevention and Control of cotton pests cotton bollworm, pink bollworm per mu with 50% emulsifiable concentrate 50-100, 75-of water spray. This dose can also cure cotton aphid, cotton red spider. 3. Prevention and Control of vegetable insect pests, vegetable aphid per mu with 50% emulsifiable concentrate 50 ml, 30-50kg of water spray. 4. Prevention and Control of fruit tree insect pests of Prunus persicae were sprayed with 50% -2000 times of emulsifiable concentrate. 5. Prevention and Control of soybean pests soybean pod borer, soybean leaf roller per mu with 50% emulsifiable concentrate 50-150 ml, 30-50kg of water spray. |
| toxicity | The acute oral LD50 of male rats was 215mg/kg, and that of female was 245mg/kg. The acute percutaneous LD50 of rats was 300 ~ 500mg/kg. Rats were fed for 60 days with a maximum allowable dose of 10mg/kg. Dogs were fed with a dose of 50mg/kg for 1 year, and their body weight and food intake were not affected. LD50 for fish about 1mg/L (48h). It is highly toxic to beneficial insects such as bees, parasitic wasps and grass Eels (aphid and Lion). |
| Use | broad-spectrum, rapid-acting, poisoning organophosphorus insecticides, also effective against mites. It has the effect of killing and stomach poison, strong permeability, certain internal absorption and long residual effect. Can be used for rice, cotton, fruit trees, soybean and other crops to control the Chilo suppressalis, rice borer, rice leaf cicada, Rice bract, Rice longitudinal rolling leaf worm, cotton bollworm, cotton bollworm, cotton aphid, vegetable aphid, fruit tree Borrelia, citrus rust ticks, reticularis, tea poison moth, tea small green leaf hopper, soybean borer and health pests. Such as control of rice pests and cotton bollworm, pink bollworm, with 50% emulsifiable concentrate 11.3~15mL/100m2 on the water spray; Control cotton red spider, cotton aphid, cabbage, vegetable aphid and other pests, spray with 50% emulsifiable concentrate 7.5~11.3mL/100m2 to water; Control cotton red spider, cotton aphid, cabbage insect, vegetable aphid and other pests, spray with 50% emulsifiable concentrate 7.5~11.3mL/100m2 to water; to control soybean pod worm, use 50% emulsifiable concentrate 7.5~11.3/100m 2, spray on water, the effect is more than 80%, or use 3% powder, 225~300kg/100m2 powder; for control of citrus rust ticks and infestations, spray with 50%-fold 1000-fold emulsifiable concentrate. It is mainly used for controlling pests of soybean pod, cotton, fruit tree, vegetable and rice, and also for controlling sanitary pests A broad-spectrum, rapid-acting, pesticide with long residual effect trithiophos is an organic phosphorus insecticide with low toxicity to human and livestock, which is effective to a variety of pests, and mainly plays the role of killing stomach poison, The residual period is long, and the effect on mites is not as good as that of methyl parathion. It is mainly used for controlling soybean heartworm, cotton pests, fruit tree pests, vegetable and rice pests, for controlling mosquitoes, flies, bedbugs, lice, cockroaches also have a good effect. |
| production method | The intermediate p-methylthio-m-cresol is prepared by reacting m-cresol with dimethyl disulfide, O-dimethylthiophosphoryl chloride was reacted to give sesthion. 1. Preparation of methylthio-m-cresol m-cresol (or mixed cresol) and dimethyl disulfide were mixed in a ratio of 2:1 (weight ratio), added to a reaction pot, stirred and cooled to 10-15 ° C., and concentrated sulfuric acid was started to be added dropwise. At about 1H, it was dropped (amount and weight of dimethyl disulfide), and the reaction was continued at 10-15 ° C. For 3H. The mixture was allowed to stand and layered, and the waste acid in the lower layer was discarded. The organic layer was neutralized with 10% sodium carbonate solution and washed with water for pH7-8. The unreacted dimethyl disulfide and cresol were recovered by distillation under reduced pressure, and the remaining material was the intermediate p-methylthio-m-cresol. 2. Preparation of the 20% sodium hydroxide solution is added to the reaction pot, stirred and cooled to 25 deg C, put into the above preparation of the intermediate, and then evenly drop O,O-dimethyl thiophosphoryl chloride at 10-20 deg C, after dropping for about 30-40min, the dosage of the three materials was 1.3:1:1.2 according to the molar ratio. Slowly raise the temperature to 60 ℃, keep the temperature for 2H, and check the change of pH during the reaction, When pH<9, sodium hydroxide solution should be added. After completion of the reaction, the temperature was lowered to 45 ° C., washed with sodium hydroxide solution, and then washed with water, and the mixture was left to separate into layers. The lower organic layer was dewatered under reduced pressure, cooled, and filtered to obtain a crude oil containing 90% of benthio and a yield of 90%. Raw material consumption quota: phosphorus trichloride (97%)1030kg/t, methanol (99%)900kg/t, mixed Cresol (50%)1150kg/t, sulfur powder (95%)280kg/t, sodium sulfide (52%)1240kg/t, dimethyl sulfate (96%)920kg/t. preparation of O,O-dimethylthiophosphoryl chloride see preparation of thiophos. Preparation of 3-methyl-4-methylthiophenol dimethyl disulfide method sulfur powder was uniformly added into sulfide aqueous solution, reacted at 50~60 ℃ for 1H, and then dimethyl sulfate was added dropwise at 35~45 ℃, after completion of the addition, the reaction was continued for a certain period of time. The material was introduced into the distillation kettle for heating and distillation. The resulting dimethyl disulfide was mixed with m-cresol, cooled to 10 ℃, and concentrated sulfuric acid was added dropwise. The reaction temperature was controlled at 10~15 ℃, and the reaction was continued for 5 hours after dropping, 3-methyl-4-methylthiophenol was obtained. Dimethyl sulfoxide method m-cresol and dimethyl sulfoxide mixed, hydrogen chloride into the prepared. Synthesis of trithiophos O,O-dimethyl thiophosphoryl chloride was added into 3-methyl-4-methylthiophenol and sodium hydroxide solution at 10~20 ℃, after the dropwise addition is completed, the temperature is slowly raised to (60±1)℃, and the reaction is carried out at a constant temperature for 2H. The pH value of the reaction solution is regularly checked, and when the pH value is <9, the alkali solution is appropriately added. After completion of the reaction, the post-treatment was carried out to obtain betaphosphorus. |
| category | pesticide |
| toxicity grade | high toxicity |
| Acute toxicity | oral-rat LD50: 180 mg/kg; Oral-mouse LD50: 88.1 mg/kg |
| flammability hazard characteristics | thermal decomposition of toxic phosphorus oxide and sulfur oxide gases |
| storage and transportation characteristics | The warehouse is ventilated and dried at low temperature; It is stored and transported separately from food raw materials |
| fire extinguishing agent | Sand, dry powder, foam |
| Occupational Standard | TWA 0.2 mg/m3 |
| 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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Raw Materials for O,S-dimethyl O-[3-methyl-4-(methylsulfanyl)phenyl] phosphorothioate