Phosphorothioic acid O,O-dimethyl O-(3-methyl-4-nitrophenyl) ester
fenitrothion
CAS: 122-14-5
Molecular Formula: C9H12NO5PS
Phosphorothioic acid O,O-dimethyl O-(3-methyl-4-nitrophenyl) ester - Names and Identifiers
Phosphorothioic acid O,O-dimethyl O-(3-methyl-4-nitrophenyl) ester - Physico-chemical Properties
| Molecular Formula | C9H12NO5PS |
| Molar Mass | 277.234 |
| Density | 1.364g/cm3 |
| Melting Point | 3.4℃ |
| Boling Point | 382.504°C at 760 mmHg |
| Flash Point | 185.132°C |
| Water Solubility | 0.003 g/100 mL |
| Vapor Presure | 0mmHg at 25°C |
| Appearance | morphology neat |
| Storage Condition | APPROX 4°C |
| Refractive Index | 1.552 |
| Physical and Chemical Properties | density 1.3227 melting point 3.4°C boiling point 140-145°C (0.05 torr) water solubility 0.003g/100 mL |
| Use | Is a combination of contact and absorption of broad-spectrum, rapid, long residual effect of pesticides |
Phosphorothioic acid O,O-dimethyl O-(3-methyl-4-nitrophenyl) ester - Risk and Safety
| Hazard Symbols | Xn - Harmful N - Dangerous for the environment  |
| Risk Codes | R22 - Harmful if swallowed R50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. |
| Safety Description | S2 - Keep out of the reach of children. 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 | TG0350000 |
| HS Code | 29201900 |
| Hazard Class | 6.1(b) |
| Packing Group | III |
| Toxicity | LD50 orally in rats: 250 mg/kg (Schrader) |
Phosphorothioic acid O,O-dimethyl O-(3-methyl-4-nitrophenyl) ester - Upstream Downstream Industry
Phosphorothioic acid O,O-dimethyl O-(3-methyl-4-nitrophenyl) ester - 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 fenitrothion with accurate purity and fixed value as raw material, chromatographic acetone as solvent, and accurately configured by weight-volume method. Sithion, English name: Fenitrothion,CAS number: 122-14-5 2. traceability and fixed value 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, and 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)BW10228 The uncertainty of the standard value of fenitrothion 1004 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 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 17:12:49
Phosphorothioic acid O,O-dimethyl O-(3-methyl-4-nitrophenyl) ester - Nature
| Specific gravity | 1.328 (20℃) |
| Merck | 13,4003 |
| BRN | 8983553 |
| NIST chemical information | Fenitrothion(122-14-5) |
| EPA chemical information | Fenitrothion (122-14-5) |
Last Update：2024-04-10 22:29:15
Phosphorothioic acid O,O-dimethyl O-(3-methyl-4-nitrophenyl) ester - Uses and synthesis methods
introduction
fenitrothion (cartap) is an organophosphorus insecticide. Sulfthion is stable to light, easy to decompose and fail at high temperature, hydrolysis in alkaline medium, iron, tin, aluminum, copper, etc. will cause the drug to decompose, and it can be stored in glass bottles for a long time. The current preparation method has low content of Sulfthion, many by-products, and serious pollution.
Toxicity
the acute oral LD50 of male rats is 242mg/kg, while that of female rats is 433mg/kg. The acute oral LD50 of mice is 870mg/kg. Acute percutaneous LD50 was 1200mg/kg in rats and 3000mg/kg in mice. The LD50 was 1000mg/kg by subcutaneous injection and 280mg/kg by intraperitoneal injection in mice. It has no carcinogenic or teratogenic effect and has weak mutagenic effect. The LD50 of carp is 8.6mg/L.
chemical properties
pure product is slightly yellow oily liquid; B. p. 118 ℃/6.666Pa, 140~145 ℃/13.33Pa (with decomposition);97 ℃/5.333Pa, relative density 1.3327(25 ℃), refractive index n25D1.5528, viscosity 0.02Pa · s (30 ℃), volatility 0.82mg/m3(20 ℃), vapor pressure 7.999 × 10-4Pa(20 ℃). Soluble in benzene, xylene, ethanol, acetone, ether, chloroform and other organic solvents; The solubility in aliphatic hydrocarbons is low, 7% in petroleum ether and 4% in kerosene. It is insoluble in water, 14mg/L at 30 ℃ (30mg/L is also reported). The acidic conditions are relatively stable, and the half-life of hydrolysis reaction is 14h at 100 ℃. It is unstable in alkaline medium. In 0.01mol/L NaOH, the half-lives of hydrolysis reaction are 272min (30 ℃) and 12min (100 ℃). Stable to light, isomerization reaction may occur during vacuum distillation. Metals such as iron, tin, lead, and copper will cause it to decompose. Industrial products are brownish yellow with a bad smell.
use
1. Broad-spectrum insecticide has strong contact effect, good stomach toxicity, no absorption and fumigation effect, but it has osmotic effect in plants. It has special effects on Chilo suppressalis, and can also control Chilo suppressalis, big borer, rice leaf roller, rice bud early, rice leafhopper, rice planthopper, rice thrips, cotton aphid, cotton bollworm, red bollworm, blind bug, cotton thrips, Spodoptera litura, armyworm, sweet potato elephant beetles, tea inchworm, pear cardiner, peach cardin. Mainly used for rice borers, but also for soybeans, cotton, fruit trees, tea, vegetables, etc. For example, to control rice stem borers, pour 60~75kg of water with 18.8~22.5mL of 50% emulsifiable concentrate per 100 square meters during the incubation period, or spray 7.5~9kg of water with 7.5~11.3mL of 50% emulsifiable concentrate. To control cotton bollworm, red bollworm and cotton thrips, spray 1000~1500 times of 50% emulsifiable concentrate. It is prone to medicinal damage to sorghum and rape.
2, is a broad-spectrum, quick-acting, long-acting insecticide with both contact and systemic properties
3, a contact insecticide, used to control pests such as Chilo suppressalis and red spider
4. carpel has a good control effect on rice, soybean, cotton, fruit trees, vegetables and other crop pests, especially the specific medicine for controlling rice borer. Such as big borer, Chilo suppressalis, Chilo suppressalis, rice planthopper, rice leafhopper, aphids, red spiders, cotton bollworm, soybean heartworm, tea chestworm, etc., apply 50-75g (active ingredient) per mu, control The effect is good, but the effect of killing mite eggs is small. This product sometimes causes phytotoxicity to cruciferous vegetables.
5. Calibration instruments and devices; evaluation methods; working standards; quality assurance/quality control; other.
production method
1. It is obtained by condensation of O,O-dimethyl thiophosphoryl chloride and 4-nitrom-cresol ([2581-34-2]) under alkaline conditions. Toluene is added to the condensation reaction pot, 4-nitrom-cresol, sodium carbonate and cuprous chloride are added under stirring, O,O-dimethyl thiophosphoryl chloride is added at 95-97 ℃, reacted at 90 ℃ for 3h, then filtered, the toluene layer is successively washed with sodium hydroxide solution and water, and toluene is recovered by distillation under reduced pressure to obtain carpel carpel crude oil with 90% content. When the molar ratio of 4-pin m-cresol: O,O-dimethyl thiophosphoryl chloride: sodium carbonate = 1:1.1:1, the amount of toluene is about 3 times (weight) of 4-nitrom-cresol, and cuprous chloride is about 2% (weight) of 4-nitrom-cresol, the yield of carol is more than 95%. The content of active ingredients in the obtained crude oil shall not be less than 93.0%, and the consumption quota of primary products ≥ 85.0% raw materials shall be 550 kg/t m-cresol, 860 kg/t nitric acid (100%), 1240 kg/t trichothion (100%) and 600 kg/t methanol.
2, 4-nitrom-cresol is prepared by nitrosation and oxidation of m-cresol. The nitrosation reaction is to react m-cresol with sodium nitrate aqueous solution in 15% ~ 20% sulfuric acid to control the temperature to 10~15 ℃. The oxidation reaction is to oxidize nitro m-cresol with dilute nitric acid. The acid addition speed is slow first and then fast. The reaction temperature is 35~38 ℃, and the temperature is kept at 44~46 ℃ for 3h. After centrifugal water washing, the pH value is 3~4 to prepare 4-nitro m-cresol.
Preparation of O,O-dimethyl thiophosphoryl chloride
the synthesis speed of O-methyl thiophosphoryl dichloride is very fast. under the condition of excessive alcohol, the reaction can be carried out to the end. the by-product hydrogen chloride is eliminated by negative pressure. the main process parameters are as follows: the feeding ratio is 5:1, the reaction temperature (-5±2)℃, the washing temperature (5±5)℃, the adding amount (washing) is the feeding amount × 0.7, the yield is 95%.
The synthesis of O,O-dimethylthiophosphoryl chloride needs to be carried out in the presence of basicity. The main process parameters of alcohol-alkali production are as follows: feeding ratio is methyl thiophosphoryl dichloride: methanol: alkali = 1:5:1.08, reaction temperature -4~0 ℃, end point pHWFHG9.5 ~ 10, water washing and adding amount is feeding amount × 0.7, yield is 85% ~ 90% based on methyl thiophosphoryl dichloride, and content is 95%.
it is reported in the literature that the synthesis of O,O-dimethyl thiophosphoryl chloride can be carried out in dipolar aprotic solvent. After mixing 84g of methyl thiophosphoryl dichloride (0.5mol), 48g of methanol (1.5mol) and 60g of aprotic solvent, 0.55mol of 30% sodium hydroxide aqueous solution is added dropwise at ≤ 5 ℃ for 60-90min, after dropping, stirring for 15, wash with 120mL of water cooled to 10 ℃ and stand for separation to obtain O,O-dimethyl thiophosphoryl chloride with yield ≥ 90% and purity ≥ 93%. The P2S2 route can also be used to synthesize O,O-dimethyl thiophosphoryl chloride.
Synthesis of fenitrothion O,O-dimethylthiophosphoryl chloride and nitro-m-cresol. Generally, the solvent method is used, and the trimethylamine aqueous solution method or the toluene-acetone double solvent method can also be used. If toluene is used as solvent, the reaction process uses cuprous chloride as catalyst, sodium carbonate as acid binding agent, and the reaction temperature is 90~96 ℃.
category
Pesticides
toxicity classification
High toxicity
acute toxicity
oral-rat LD50: 250 mg/kg; oral-mouse LD50: 229 mg/kg
flammability hazard characteristics
Decomposition of toxic phosphorus oxide, sulfur oxide, nitrogen oxide gas by heating
storage and transportation features
The warehouse is ventilated and dry at low temperature; stored and transported separately from food raw materials
fire extinguishing agent
Sand, dry powder, foam
occupational standards
TWA 1 mg/m3; STEL 1 mg/m3
Last Update：2024-04-10 22:29:15
Phosphorothioic acid O,O-dimethyl O-(3-methyl-4-nitrophenyl) ester - Security information
| toxic substance data | 122-14-5(Hazardous Substances Data) |
Last Update：2024-04-10 22:29:15
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Raw Materials for Phosphorothioic acid O,O-dimethyl O-(3-methyl-4-nitrophenyl) ester
Downstream Products for Phosphorothioic acid O,O-dimethyl O-(3-methyl-4-nitrophenyl) ester