Fenitrothion Fenitrothion
Structural formula
| Business number | 03EL |
|---|---|
| Molecular formula | C9H12NO5PS |
| Molecular weight | 277.23 |
| label |
Fenitrothion, Fenitrothion, Quick pest control, sumisong, Sumithion, Sumethasone, O,O-dimethyl-O-(3-methyl-4-nitrophenyl)phosphorothioate, Accothion, Faithion, Metathione, O,O-Dimethyl-O-(3-methyl-4-nitrophenyl)phosphorothioate, Organophosphorus pesticides, Acaricide |
Numbering system
CAS number:122-14-5
MDL number:MFCD00055407
EINECS number:204-524-2
RTECS number:TG0350000
BRN number:8983553
PubChem number:24868985
Physical property data
1. Characteristics: The pure product is a light yellow oily liquid, the industrial product is brownish-yellow and has a slight garlic smell. [1]
2. Melting point (℃): 3.4[2]
3. Boiling point (℃): 140 ~145 (0.013kPa)[3]
4. Relative density (water=1): 1.32[4]
5. Saturated vapor pressure (kPa): 0.01 (140℃)[5]
6. Octanol/water partition coefficient: 3.38[6]
7. Solubility: Insoluble in water, soluble in most organic solvents such as ethanol, ether, benzene, toluene and so on. [7]
Toxicological data
1. Acute toxicity[8]
LD50: 250mg/kg (rat oral); 2500mg/kg (rat oral Skin)
LC50: 378mg/m3 (rat inhalation, 4h)
2. Irritation No information available yet
3. Mutagenicity [9] Microbial mutagenicity: Salmonella typhimurium 500μg/dish. Sister chromatid exchange: human embryonic cells 55.4mg/L. Cytogenetic analysis: human lymphocytes 40mg/L.
Ecological data
1. Ecotoxicity[10]
LC50: 12mg/L (96h) (carp, static); 3.8~4.3mg/ L (96h) (bluegill, static); 4.8mg/L (96h) (fathead minnow, static); 3.2~2.4mg/L (96h) (rainbow trout, static); 0.0092mg/L (3h ) (Water flea)
2. Biodegradability No information available
3. Non-biodegradability[11] At 20°C, when the pH value is 5, 7, and 9, the hydrolysis half-life is 247.5, 86.1, and 4.3d respectively (theoretical)
4. Bioconcentration Sex [12] BCF: 8~53.6 (carp, exposure concentration 20ppb, exposure time 8 weeks); 1.5~101.7 (carp, exposure concentration 2ppb, exposure time 8 weeks)
5. Other harmful effects[13] This substance is harmful to the environment, and special attention should be paid to crustaceans and bees. Bioaccumulation occurs in food chains important to humans, especially in fish.
Molecular structure data
1. Molar refractive index: 66.55
2. Molar volume (cm3/mol): 202.7
3. Isotonic specific volume (90.2K ): 549.7
4. Surface tension (dyne/cm): 54.0
5. Dielectric constant:
6. Dipole moment (10-24cm3):
7. Polarizability: 26.38
Compute chemical data
1. Reference value for hydrophobic parameter calculation (XlogP): None
2. Number of hydrogen bond donors: 0
3. Number of hydrogen bond acceptors: 6
4. Number of rotatable chemical bonds: 4
5. Number of tautomers: none
6. Topological molecule polar surface area 106
7. Number of heavy atoms: 17
8. Surface charge: 0
9. Complexity: 313
10. Number of isotope atoms: 0
11. Determine the number of atomic stereocenters: 0
12. Uncertain number of atomic stereocenters: 0
13. Determine the number of chemical bond stereocenters: 0
14. Number of uncertain chemical bond stereocenters: 0
15. Number of covalent bond units: 1
Properties and stability
1. Stability[14] Stable
2. Incompatible substances[15] Strong oxidants, strong alkalis
3. Conditions to avoid contact[16] Heating
4. Polymerization hazard[17] No polymerization
5. Decomposition products[18] Phosphorus oxide , nitrogen oxides
Storage method
Storage Precautions[19] Store in a cool, well-ventilated dedicated warehouse. Implement the system of “dual people to send and receive, and double to keep”. Keep away from fire and heat sources. Keep container tightly sealed. They should be stored separately from oxidants and alkalis, and avoid mixed storage. Equipped with the appropriate variety and quantity of fire equipment. The storage area should be equipped with emergency release equipment and suitable containment materials.
Synthesis method
1) It is obtained by the condensation of O,O-dimethylphosphorothioate chloride and 4-nitro-m-cresol ([2581-34-2]) under alkaline conditions. Add toluene to the condensation reaction pot, add 4-nitro-m-cresol, sodium carbonate and cuprous chloride under stirring, add O,O-dimethylphosphorothioate chloride at 95-97°C, and react above 90°C 3 hours, then filter, take the toluene layer and wash it with sodium hydroxide solution and water in sequence. After distilling under reduced pressure to recover the toluene, fenitrothionine crude oil is obtained, with a content of 90%. When using the molar ratio of 4-pin-m-cresol:O,O-dimethylthiophosphoryl chloride:sodium carbonate=1:1.1:1, the amount of toluene used is about 3 times that of 4-nitro-m-cresol (weight ), when cuprous chloride is about 2% (weight) of 4-nitro-m-cresol, the yield of fenitrothion is over 95%. The obtained crude oil has an effective ingredient content of not less than 93.0% for high-quality products and ≥85.0% for first-class products. Raw material consumption quota: m-cresol 550kg/t, nitric acid (100%) 860kg/t, phosphorus trichloride (100%) 1240kg/ t, methanol 600kg/t.
2) The preparation of 4-nitro-m-cresol is obtained by nitrosation and oxidation of m-cresol. The nitrosation reaction is to react m-cresol with sodium nitrite aqueous solution in 15′}}~20′}} sulfuric acid, and the temperature is controlled at 10~15(‘0’. The oxidation reaction is to react nitro-m-cresol with dilute Nitric acid is used for oxidation. The acid addition speed is slow at first and then fast. The reaction temperature is 35~38°C. After the addition is completed, it is kept at 44~46°C for 3 hours. After centrifugation, it is washed with water. Bring the pH value to 3~4 to prepare 4-nitro-m-cresol
3) Synthesis of fenitrothion O ,O-dimethylphosphorothioate chloride and nitro-m-cresol. The solvent method is generally used, but the trimethylamine aqueous solution method or the toluene-acetone dual solvent method can also be used. If toluene is used as the solvent, the reaction process uses cuprous chloride as the catalyst, sodium carbonate as the acid binding agent, and the reaction temperature is 90 to 96°C.
Purpose
1. Fenitrothion has good control effects on various crop pests such as rice, soybeans, cotton, fruit trees, vegetables, etc. It is especially effective in preventing and controlling rice borers. Such as giant borers, stem borers, stem borers, rice planthoppers, rice leafhoppers, aphids, red spider mites, cotton bollworms, soybean heartworms, tea worms, etc., apply 50-75g (active ingredient) per acre, and the control effect is Good, but less effective against acaricidal eggs. This product sometimes causes phytotoxicity to cruciferous vegetables.
2. It is a broad-spectrum insecticide with strong contact killing effect and good gastric poisoning effect. It has no systemic or fumigation effect, but has penetration effect in plants. It has special effects on rice borer, rice borer, rice leaf roller, rice bractworm, rice leafhopper, rice planthopper, rice thrips, cotton aphid, cotton bollworm, pink bollworm, blind Stink bugs, cotton thrips, Spodoptera litura, armyworms, sweet potato weevils, tea loopers, pear heartworms, peach heartworms, vegetable borers, pine caterpillars, etc. It is mainly used for rice borers, but can also be used for soybeans, cotton, fruit trees, tea, vegetables, etc. For example, to control rice borers, during the incubation period, use 50%, 18.8 to 22.5 mL of EC per 100 square meters and pour 60 to 75 kg of water, or use 50%, 7.5 to 11.3 mL of EC, 7.5 to 75 kg of water. 9kg spray; to control cotton bollworm, pink bollworm and cotton thrips, use 50%, EC 1000-150 () times liquid spray. It is prone to phytotoxicity in sorghum and rapeseed.
3. It is a highly efficient, low-toxic, broad-spectrum contact insecticide with stomach poisoning and contact killing effects. Used to control rice, wheat, cotton and other crops and fruit pests (such as borers, aphids, red spiders, etc.). It has special effects on rice borers. The effect of spraying with 2000 times liquid to control stem borer, stem borer and giant borer is over 90%. The United Nations World Health Organization approved its use for the prevention and control of malarial mosquitoes in October 1976.
4. Used as an insecticide, it has special effects on rice borer, stem borer, stem borer and leaf curler. [20]
, cotton, fruit trees, tea, vegetables, etc. For example, to control rice borers, during the incubation period, use 50%, 18.8 to 22.5 mL of EC per 100 square meters and pour 60 to 75 kg of water, or use 50%, 7.5 to 11.3 mL of EC, 7.5 to 75 kg of water. 9kg spray; to control cotton bollworm, pink bollworm and cotton thrips, use 50%, EC 1000-150 () times liquid spray. It is prone to phytotoxicity in sorghum and rapeseed.
3. It is a highly efficient, low-toxic, broad-spectrum contact insecticide with stomach poisoning and contact killing effects. Used to control rice, wheat, cotton and other crops and fruit pests (such as borers, aphids, red spiders, etc.). It has special effects on rice borers. The effect of spraying with 2000 times liquid to control stem borer, stem borer and giant borer is over 90%. The United Nations World Health Organization approved its use for the prevention and control of malarial mosquitoes in October 1976.
4. Used as an insecticide, it has special effects on rice borer, stem borer, stem borer and leaf curler. [20]
