o,o-diethyl o-(6-methyl-2-(1-methylethyl)-4-pyrimidinyl) phosophorothioate
Diazinon
CAS: 333-41-5
Molecular Formula: C12H21N2O3PS
o,o-diethyl o-(6-methyl-2-(1-methylethyl)-4-pyrimidinyl) phosophorothioate - Names and Identifiers
o,o-diethyl o-(6-methyl-2-(1-methylethyl)-4-pyrimidinyl) phosophorothioate - Physico-chemical Properties
| Molecular Formula | C12H21N2O3PS |
| Molar Mass | 304.35 |
| Density | 1.117 |
| Melting Point | >120°C (dec.) |
| Boling Point | 306°C |
| Flash Point | 104.4°C |
| Water Solubility | Slightly soluble. 0.004 g/100 mL |
| Vapor Presure | 1.2 x 10-2 Pa (25 °C) |
| Appearance | neat |
| Exposure Limit | OSHA PEL: TWA 0.1 mg/m3; ACGIH TLV: TWA 0.1 mg/m3. |
| Merck | 13,3019 |
| BRN | 273790 |
| pKa | 1.21±0.30(Predicted) |
| Storage Condition | APPROX 4°C |
| Refractive Index | nD20 1.4978-1.4981 |
| MDL | MFCD00036204 |
| Physical and Chemical Properties | Density 1.117 melting point> 120°C (dec.) boiling point 306°C water-soluble easily soluble. 0.004g/100 mL |
| Use | Belongs to non-systemic insecticide, which has good control effect on Lepidoptera, Homoptera and other pests |
o,o-diethyl o-(6-methyl-2-(1-methylethyl)-4-pyrimidinyl) phosophorothioate - Risk and Safety
| Risk Codes | R22 - Harmful if swallowed R50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. R36 - Irritating to the eyes R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R11 - Highly Flammable R51/53 - Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. |
| Safety Description | S24/25 - Avoid contact with skin and eyes. 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. S36 - Wear suitable protective clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S16 - Keep away from sources of ignition. S36/37 - Wear suitable protective clothing and gloves. |
| UN IDs | UN 2783/2810 |
| WGK Germany | 3 |
| RTECS | TF3325000 |
| HS Code | 29335990 |
| Hazard Class | 6.1(b) |
| Packing Group | III |
| Toxicity | LD50 in male, female rats (mg/kg): 250, 285 orally (Gaines) |
o,o-diethyl o-(6-methyl-2-(1-methylethyl)-4-pyrimidinyl) phosophorothioate - Upstream Downstream Industry
| Raw Materials | Methyl acetoacetate isobutyronitrile |
o,o-diethyl o-(6-methyl-2-(1-methylethyl)-4-pyrimidinyl) phosophorothioate - Nature
Open Data Verified Data
The Pure product is colorless and transparent liquid, with slight fragrance; Industrial product is light brown-brown liquid. With acetone, ethanol, xylene miscible, soluble in petroleum ether, room temperature in water solubility of 0.004%. Unstable above 50 ℃, unstable to acid and alkali, and stable to light. In water and dilute acid will be slowly hydrolyzed. Storage of trace moisture can promote its decomposition, into highly toxic tetraethyl thiopyrophosphate.
Last Update：2024-01-02 23:10:35
o,o-diethyl o-(6-methyl-2-(1-methylethyl)-4-pyrimidinyl) phosophorothioate - Preparation Method
Open Data Verified Data
The reaction of methanol, hydrogen chloride and isobutyronitrile to form the corresponding imine Ester hydrochloride; Treated with ammonia to obtain isobutyramidine, under alkaline conditions, isobutyramidine condensation with ethyl acetoacetate, pyrimidine (4-monohydroxy-2-isopropyl-6-methylpyrimidine) was obtained. Pyridinol is heated to reflux in the presence of sodium carbonate in benzene or formazan, and diethyl thiophosphoryl chloride and copper nitrate are added for condensation to give diazinon.
Last Update：2022-01-01 10:11:57
o,o-diethyl o-(6-methyl-2-(1-methylethyl)-4-pyrimidinyl) phosophorothioate - 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. Preparation of 1. Samples This standard substance is made of diazinon pure products with accurate purity and fixed value as raw materials, chromatographic acetone as solvent, and accurately configured by weight-volume method. Diazinon, English name: Diazinon,CAS No.: 333-41-5 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 value and uncertainty (see certificate) number name standard value (ug/mL) relative expansion uncertainty (%)(k = 2)BW10186 The uncertainty of the standard value of diazinon 1003 in acetone 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 24 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 bags should be transported, and extrusion and collision should be avoided during transportation; storage under freezing (-20 ℃) and dark conditions. 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 17:24:41
o,o-diethyl o-(6-methyl-2-(1-methylethyl)-4-pyrimidinyl) phosophorothioate - Use
Open Data Verified Data
A broad-spectrum of organophosphorus insecticides, with contact kill, stomach poison, fumigation, but also have a better acaricidal and egg killing effect. For the control of Apple worms, the effect of the same parathion. It is more effective than parathion in the prevention and treatment of grub or needle worm. In addition to as a general Contact killing agent, but also can be injected into the body of the cow, can kill the larvae of the tumor flies. Less toxic to livestock. Can be processed into wettable powders, emulsions and powders for use. In addition to copper fungicides, alkaline pesticides, can be mixed with most pesticides.
Last Update：2022-01-01 10:11:58
o,o-diethyl o-(6-methyl-2-(1-methylethyl)-4-pyrimidinyl) phosophorothioate - Safety
Open Data Verified Data
The oral LD50 of male and female rats was 2 50mg/kg and 285mg/kg; The percutaneous LD50 of female rats was 455mg/kg, and the inhalation LC50 of mice was 630mg/m3. It has mild irritation to the skin and eyes of rabbits. The non-effective dose of chronic toxicity feeding test was 0. 1 mg/kg per day in rats and 0. 05mg/kg per day in monkeys. In the test dose, no teratogenic, carcinogenic, mutagenic effects on animals. Carp LC50 3. 2mg/L(48h), High toxicity to bees.
Last Update：2022-01-01 10:11:57
o,o-diethyl o-(6-methyl-2-(1-methylethyl)-4-pyrimidinyl) phosophorothioate - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| (IARC) carcinogen classification | 2A (Vol. 112) 2017 |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| toxicity | the original drug has an acute oral LD50 of 285 mg/kg (300~850 mg/kg) in rats and 163 mg/kg in mice. The acute percutaneous LD50 of female rats is 455 mg/kg (rat percutaneous LD502150mg/kg); The acute inhalation LD50 of mice is 630mg/m<3. It has mild irritation to rabbit skin and eyes. The non-effective dose of chronic toxic feeding test in rats was 0.1 mg/kg per day, and that in monkeys was 0.05 mg/kg per day. Under the test dose, it has no teratogenic, carcinogenic and mutagenic effects on animals. The LD50 of carp is 3.2mg/L (48h). Highly toxic to bees. |
| use | broad-spectrum insecticide, which has contact killing, stomach poison, fumigation and certain systemic effects, as well as good acaricidal and egg killing effects. To control rice stem borers and rice leafhoppers, spray 7.5kg of water with 50% emulsifiable concentrate of 15~30g/100 m2, with a control effect of 90% ~ 100%. Control cotton aphid, cotton red bee spider, cotton thrips, cotton leafhopper, with 50% emulsifiable concentrate 7.5~12mL/100 m2, evenly spray water, control effect of 92% ~ 97%. To prevent and control underground pests of mole crickets and scarabs in North China, 75mL of 50% emulsifiable concentrate, 3.75kg of water, 45kg of seed dressing, 7h of stuffing can be used for sowing, or 37kg of wheat seeds can be mixed for sowing, and the seeds can be sown after the liquid medicine is absorbed and slightly dried. To control Pieris rapae and aphid, spray 6-7.5mL/100 m2 of water evenly with 50% emulsifiable concentrate. To prevent and control onion leaf fly, bean seed fly and rice gall midge, spray 7.5~15kg of water evenly with 50% emulsifiable concentrate of 7.5~15mL/100 m2. To prevent and control large black grubs, use 2% granule 0.19kg/100m2 hole application. Be careful not to mix with copper-containing fungicides and dipole. It is a non-systemic insecticide, which has good control effect on Lepidoptera, Homoptera and other pests Non-systemic broad-spectrum insecticide, and has certain acaricidal and nematicidal activities. It is widely used in rice, corn, sugarcane, tobacco, fruit trees, vegetables, pastures, flowers, forests and greenhouses to prevent and control a variety of irritating and leaf-eating pests. It is also used in soil to control underground pests and nematodes, as well as in vitro parasites of livestock and domestic pests such as flies and cockroaches. Calibration instruments and devices; evaluation methods; working standards; quality assurance/quality control; other. |
| Production method | O,O-diethyl thiophosphoryl chloride is prepared for details. The preparation of 2-isopropyl-4-methyl-6-hydroxypyrimidine is prepared by reacting isobutyronitrile with methanol and hydrochloric acid to obtain imine ether hydrochloride, and then reacting with ammonia to obtain isobutyrazidine. Isobutamidine and ethyl acetoacetate are cyclized in the presence of sodium hydroxide to produce 2-isopropyl-4-methyl-6-hydroxypyrimidine. Synthesis of Diazinon 8g 2-isopropyl -4-methyl -6-hydroxypyrimidine, 0.63g SMB, 2.82g sodium hydroxide and 50mL butanone are mixed, stirred for 0.5h at room temperature, slowly raised to 55 ℃, added 9.5g O,O-diethylthiophosphoryl chloride after the material is clarified, raised to 70 ℃, stirred for 0.5h, refluxed for 1h, stirred and cooled, and added 50mL of water, dissolve the precipitated solid, adjust the pH value to 11 with 20% NaOH, stir and delaminate. The water layer is extracted with butanone, the solvents are combined, and the residue is desoluted under reduced pressure. After alkali washing, acid washing, and alkali washing, the residue is washed to neutral, and the water is heated and dehydrated under reduced pressure to obtain 14g of brown transparent liquid with 1.4942 refractive index. The reaction of methanol, hydrogen chloride and isobutyronitrile to form the corresponding amidine hydrochloride; it is treated with ammonia and converted into the corresponding amidine. Then, under alkaline conditions, amidine is condensed with ethyl acetoacetate to obtain pyrimidine (4-hydroxy-2-isopropyl-6-methylpyrimidine). Pyrimidine is heated and refluxed in benzene or toluene in the presence of sodium carbonate, diethyl thiophosphoryl chloride and copper nitrate are added, and diazinon is obtained by condensation. |
| category | pesticide |
| toxicity classification | highly toxic |
| acute toxicity | oral-rat LD50: 66 mg/kg; Oral-mouse LD50: 17 mg/kg |
| stimulation data | skin-rabbit 500 mg moderate; Eye-rabbit 100 mg severe |
| flammability hazard characteristics | thermal decomposition of toxic phosphorus oxide, sulfur oxide, nitrogen oxide gas |
| storage and transportation characteristics | warehouse ventilation and low temperature drying; separate from food raw materials storage and transportation |
| fire extinguishing agent | sand, dry powder, foam |
| occupational standard | TWA 0.1 mg/m3; STEL 0.3 mg/m3 |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 02:00:08
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Raw Materials for o,o-diethyl o-(6-methyl-2-(1-methylethyl)-4-pyrimidinyl) phosophorothioate