O,O-diethyl-O-(1-phenyl-1,2,4-triazole-3-yl)thiophosphate
Triazophos
CAS: 24017-47-8
Molecular Formula: C12H16N3O3PS
O,O-diethyl-O-(1-phenyl-1,2,4-triazole-3-yl)thiophosphate - Names and Identifiers
| Name | Triazophos |
| Synonyms | hoe2960 HOE 2960 Hostahion ai3-27764 Hostathion Triazophos HOE 2960 OJ Phentriazophos 1-Phenyl-3-(O,O-diethyl-thionophosphoryl)-1,2,4-triazole O,O-diethyl-O-(1-phenyl-1,2,4-triazole-3-yl)thiophosphate O,O-diethyl O-1-phenyl-1H-1,2,4-triazol-3-yl phosphorothioate O,O-diethyl-O-(1-phenyl-1,2,4-triazole-3-yl)-phosphorothioate O,O-diethyl O-(1-phenyl-1H-1,2,4-triazol-3-yl) phosphorothioate triazophos (ISO) O,O-diethyl-O-1-phenyl-1H,2,4-triazol-3-yl phosphorothioate |
| CAS | 24017-47-8 |
| EINECS | 245-986-5 |
| InChI | InChI=1/C12H16N3O3PS/c1-3-16-19(20,17-4-2)18-12-13-10-15(14-12)11-8-6-5-7-9-11/h5-10H,3-4H2,1-2H3 |
O,O-diethyl-O-(1-phenyl-1,2,4-triazole-3-yl)thiophosphate - Physico-chemical Properties
| Molecular Formula | C12H16N3O3PS |
| Molar Mass | 313.31 |
| Density | 1.247 |
| Melting Point | 0-5°C |
| Boling Point | 260°C |
| Flash Point | 25°C |
| Water Solubility | 30-40 mg/L at 20 ºC |
| Vapor Presure | 3.9×10-4 Pa (30 °C) |
| Appearance | liquid |
| BRN | 682554 |
| pKa | -0.15±0.50(Predicted) |
| Storage Condition | APPROX 4°C |
| Refractive Index | 1.6 |
| MDL | MFCD00055327 |
| Physical and Chemical Properties | Industrial products are yellow liquids. |
| Use | It is a broad-spectrum insecticide and acaricide, and has certain nematicidal effect |
O,O-diethyl-O-(1-phenyl-1,2,4-triazole-3-yl)thiophosphate - Risk and Safety
| Risk Codes | R21 - Harmful in contact with skin R23/25 - Toxic by inhalation and if swallowed. R50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. R38 - Irritating to the skin R10 - Flammable |
| Safety Description | S1/2 - Keep locked up and out of the reach of children. 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. |
| UN IDs | 3018 |
| WGK Germany | 3 |
| RTECS | TF5635000 |
| HS Code | 29339900 |
| Hazard Class | 6.1(a) |
| Packing Group | II |
| Toxicity | LD50 in rats (mg/kg): 82 orally, 1100 dermally (Thier); LD50 in rats (mg/kg): 107 i.p.; in rabbits (mg/kg): 280 dermally (Hay) |
O,O-diethyl-O-(1-phenyl-1,2,4-triazole-3-yl)thiophosphate - Upstream Downstream Industry
| Raw Materials | Diethyl chlorothiophosphate phenyl hydrazine Dichloromethane Toluene Formic acid Urea Octoxinol Trimethylamine Sodium hydroxide Sodium bicarbonate |
O,O-diethyl-O-(1-phenyl-1,2,4-triazole-3-yl)thiophosphate - 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 pure triazophos with accurate purity and fixed value as raw material, chromatographic acetone as solvent, and accurately configured by weight-volume method. Triazophos, English name: Triazophos,CAS number: 24017-47-8 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) This batch of standard substances and quality control control samples are compared 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)BW10196 The uncertainty of the standard value of triazophos 1003 in acetone is mainly composed of raw material purity, weighing, constant volume, 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 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 17:15:11
O,O-diethyl-O-(1-phenyl-1,2,4-triazole-3-yl)thiophosphate - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| use | broad-spectrum organophosphorus insecticide and acaricide have certain nematicidal effects, stomach poison and contact killing effects, and can penetrate into plant tissues, but have no systemic activity. it is harmful to crop pests such as cotton, grain, fruit trees (borer, cotton bollworm, red spider, aphid), it has a significant effect on underground pests, plant nematodes, and forest pine caterpillars, with an active period of more than 2 weeks, and its egg killing effect is obvious, especially for lepidopteran insect eggs. Acute oral toxicity LD50 in rats was 66mg/kg. The preparations include emulsifiable concentrate, granules and ultra-low volume liquid. High-efficiency, broad-spectrum insecticide and acaricide, with gastric toxicity and contact killing effects, can penetrate into plant tissues, but has no systemic activity, and is harmful to crop pests such as cotton, grain, and fruit trees (borers, cotton bollworms, Red spiders, aphids) have good control effects, and also have significant effects on underground pests, plant nematodes, and forest pine caterpillars, with an active period of more than 2 weeks. Broad-spectrum organophosphorus insecticide, acaricide, and a certain nematicidal effect. It has excellent control effects on many important pests on major crops such as grain, cotton, fruit, and vegetables, such as stem borers, rice planthoppers, aphids, red spiders, cotton bollworms, rapae, nematodes, etc.; its egg killing effect is obvious, and its killing effect on lepidopteran insect eggs is particularly prominent. Acute oral toxicity LD50 in rats was 66mg/kg. It is a broad-spectrum insecticide and acaricide, and has a certain nematicidal effect It is used to control aphids, thrips, whiteflies, borers, corn borers, diamondback moths, golden needle worms, cutworms and other agricultural pests. The preparations include emulsifiable concentrate, granules and ultra-low volume liquid. |
| production method | 1. mixing phenylhydrazine hydrochloride and urea, stirring and heating to 150-160 ℃, the reaction produces ammonia to obtain yellow melt. Cooling, washing with water, filtering and recrystallization with alcohol to obtain 1-phenylsemicarbazide (melting point 172 ℃). Stir and heat 1-phenylsemicarbazide, triethyl orthoformate and toluene together, and evaporate the ethanol generated by the reaction until no ethanol is evaporated. After the reaction, cooling, filtering, washing, 1-phenyl -3-hydroxy -1,2, 4-triazole (melting point 269-273 ℃). 1-phenyl -3-hydroxy -1,2, 4-triazole was suspended in acetone, O,O-diethyl thiophosphoryl chloride was added, and triethylamine was added dropwise. After dropping, stir and react at 50 ℃ for 6 hours. Cooling, filtering, filtering out triethylamine hydrochloride. Triazophos brown oil is obtained after the filtrate is recovered from acetone. 2. 33.5g of 96% 1-phenyl -3-hydroxy -1,2, 4-triazole is suspended in 250mL xylene, an appropriate amount of composite catalyst (TEBAT + DMAP) and potassium carbonate are added, stirred for 0.5h, then 30g of O,O-diethyl thiophosphoryl chloride are added dropwise, the reaction temperature is 80 ~ ℃, the reaction time is 4h, the filtrate is cooled, filtered, washed and dried, the yield reached 86%. Literature [5] introduces the use of a BG catalyst with a yield of 91% ~ 96%. Mix phenylhydrazine hydrochloride and urea, stir and heat to 150-160 ℃, and react to produce ammonia to obtain a yellow melt. Cooling, washing with water, filtering and recrystallization with alcohol to obtain 1-phenylsemicarbazide (melting point 172 ℃). Stir and heat 1-phenylsemicarbazide, triethyl orthoformate and toluene together, and evaporate the ethanol generated by the reaction until no ethanol is evaporated. After the reaction, cooling, filtering, washing, 1-phenyl -3-hydroxy -1,2, 4-triazole (melting point 269-273 ℃). 1-phenyl -3-hydroxy -1,2, 4-triazole was suspended in acetone, O,O-diethyl thiophosphoryl chloride was added, and triethylamine was added dropwise. After dropping, stir and react at 50 ℃ for 6 hours. Cooling, filtering, filtering out triethylamine hydrochloride. Triazophos brown oil is obtained after the filtrate is recovered from acetone. preparation of 1-phenyl -3-hydroxy -1,2,4-triazole under stirring, 111g of concentrated hydrochloric acid is added to 108g of phenylhydrazine and 60g of urea in 500mL xylene suspension, heated at 135 ℃ for 2.5h, separated into water, cooled to 90 ℃, first added 135.2g of 85% formic acid, then added 25g of concentrated sulfuric acid, continued to react at 90 ℃ for 6h, cooled, filtered and washed with water, vacuum drying yielded 147.6g of intermediate product with 96% content and 88% yield, m.p. 279~280 ℃ (literature value 278~285 ℃). It can also be prepared by the action of 1-phenylsemicarbazide and formic acid, the temperature is raised to 90 ℃, an appropriate amount of catalyst is added dropwise, and the reaction is refluxed at 90~100 ℃ for 4.5h. Synthesis of Triazophos 33.5g of 96% 1-phenyl -3-hydroxy -1,2, 4-triazole is suspended in 250mL xylene, an appropriate amount of composite catalyst (TEBAT + DMAP) and potassium carbonate are added, stirred for 0.5h, then 30g of O,O-diethyl thiophosphoryl chloride are added dropwise, the reaction temperature is 80 ~ ℃, the reaction time is 4h, the filtrate is cooled, filtered, washed and dried, the yield reached 86%. Literature [5] introduces the use of a BG catalyst with a yield of 91% ~ 96%. |
| toxicity | acute oral LD50 in rats is 82 mg/kg, acute percutaneous LD50 is 1100 mg/kg, and acute oral LD50 in dogs is 320 mg/kg. Feeding dogs with a dose of 100mg/kg of triazophos for 90 days only had some inhibitory effect on cholinesterase activity of dogs. A 2-year feeding test was conducted on rats with no effect of 1mg/kg. LD50 for crucian carp was 8.4mg/L and 1mg/L for carp (both 48h). Toxic to bees. |
| category | pesticide |
| toxicity classification | highly toxic |
| acute toxicity | oral-rat LD50: 57 mg/kg |
| 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 |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 19:05:11
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Raw Materials for O,O-diethyl-O-(1-phenyl-1,2,4-triazole-3-yl)thiophosphate