Trichlorfon

[dí bǎi chóng]
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An organophosphorus insecticide
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This entry is made by China Science and Technology Information Magazine Participate in editing and review Science Popularization China · Science Encyclopedia authentication.
Dipterex, chemical name O , O -Dimethyl - (2,2,2-trichloro-1-hydroxyethyl) phosphonate, chemical formula C four H eight Cl three O four P, Is a kind of Organophosphorus insecticide , soluble in water and Organic solvent , relatively stable in nature, but hydrolyzed to dichlorvos Its toxicity has increased 10 times. Its toxicity is mainly acute poisoning and less chronic poisoning.
On October 27, 2017, the list of carcinogens released by the International Agency for Research on Cancer of the World Health Organization (WHO) was preliminarily sorted out for reference, and trichlorfon was included in the list of three types of carcinogens. [2]
Chinese name
Trichlorfon
Foreign name
Dipterex;Trichlorfon
Alias
O. O-Dimethyl - (2,2,2-trichloro-1-hydroxyethyl) phosphonate
chemical formula
C four H eight Cl three O four P
molecular weight
two hundred and fifty-seven point four five
CAS login number
52-68-6
EINECS login number
200-149-3
Melting point
77 to 81 ℃
Boiling point
269.4 ℃
Water solubility
Soluble
Density
1.73 g/cm³
Appearance
White crystal
Flash point
116.7 ℃
Application
Insecticide
Security description
S2;S24;S37;S60;S61
Hazard symbol
C;Xi
Hazard description
R34

Physical and chemical properties

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Melting point: 77-81 ℃
Boiling point: 269.4 ℃
Flash point: 116.7 ℃
Density: 1.73g/cm three
Appearance: white crystalline powder
Solubility: soluble in water, chloroform, insoluble in gasoline [1]

Molecular structure data

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Molar refractive index: 46.95
Molar volume (cm three /mol):163.5
Isotonic specific volume (90.2K): 427.2
Surface tension (dyne/cm): 46.6
Polarization (10 -24 cm three ):18.61 [1]

Calculate chemical data

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Reference value for drainage parameter calculation (XlogP): None
Number of hydrogen bond donors: 1
Number of hydrogen bond receptors: 4
Number of rotatable chemical bonds: 3
Number of tautomers: 0
Topological molecular polar surface area: 55.8
Number of heavy atoms: 12
Surface charge: 0
Complexity: 183
Number of isotope atoms: 0
Determine the number of atomic structure centers: 0
Number of uncertain atomic structure centers: 1
Determine the number of chemical bond structure centers: 0
Number of uncertain chemical bond structure centers: 0
Number of covalent bond units: 1 [1]

toxicology data

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1. Acute toxicity
LD fifty : 400~900mg/kg (rat oral); 500mg/kg (rabbit percutaneous).
2. Irritation
Rabbit eyes: 120mg (6d, intermittent), mild irritation.
3. Mutagenicity
Microbial mutagenicity: Salmonella typhimurium 3400 nmol/dish.
Mammalian somatic mutagenicity: mouse lymphocyte 80mg/L.
Sister chromatid exchange: hamster lung 20mg/L.
Out of program DNA synthesis: human fibroblasts 100mg/L.
Cytogenetic analysis: human leukocyte 40mg/L.
4. Teratogenicity
The lowest toxic dose (TDLo) of 1450 mg/kg was orally administered to rats 6~15 days after pregnancy, resulting in developmental malformations of the central nervous system, craniofacial (including nose and tongue) and musculoskeletal system.
The lowest toxic dose (TDLo) of 3g/kg was orally administered to mice 7~16 days after pregnancy, resulting in malformations of the genitourinary system.
5. Carcinogenicity
IARC carcinogenicity review: G3, insufficient evidence of carcinogenicity to humans and animals.
6. Others
The lowest oral toxic dose (TDLo) of rats: 1450 mg/kg (6-15 days of pregnancy), resulting in abnormal development of central nervous system, craniofacial development, and musculoskeletal development. [1]

Ecological data

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1. Ecotoxicity
LC fifty : 1.4mg/L (96h) (rainbow trout); 0.94mg/L (96h) (bluegill sunfish)
EC fifty : 0.00018mg/L (48h) (Daphnia)
2. Biodegradability
Aerobic biodegradation: 24~1080h
Anaerobic biodegradation: 96~4320h
3. Non biodegradable
Maximum optical absorption of photolysis:<200nm
Photooxidation half-life in air: 1~101h
First order hydrolysis half-life: 68h [1]

application

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Pharmacological application

It is effective for digestive tract nematodes and some trematodes. This product can be quickly absorbed regardless of the route of administration, mainly distributed in the liver, kidney, heart, brain and spleen. Metabolism in the body is fast, mainly excreted by urine.
It is a low toxic drug. The amount of treatment is very close to the amount of poisoning. It is easy to be poisoned and may cause shortness of breath in a short time due to chest tightness.
Dichlorvos with stronger toxicity can be decomposed by trichlorfon when encountering alkaline drugs, and the decomposition process accelerates with the increase of alkalinity and temperature, so it is forbidden to detoxify drugs such as sodium bicarbonate when poisoned.

Agricultural application

Used as insecticide. It is applicable to the control of chewing mouthparts pests on rice, wheat, vegetables, tea trees, fruit trees, mulberry trees, cotton and other crops, as well as livestock parasites and health pests; An organophosphorus insecticide. High efficiency, low toxicity, low residue, broad-spectrum insecticides, mainly with stomach toxicity, have both contact and penetration effects. It is widely used in agriculture to control cabbage caterpillar, cotton leaf hopper, mulberry wild silkworm, mulberry yellow, weevil, fruit tree sawfly, fruit fly and other pests. The refined trichlorfon can be used to control the internal and external parasites of pigs, cattle, horses and mules, and is effective for household and environmental health pests. It can be used to treat schistosomiasis, and is a good multi effect insecticide for livestock. Trichlorfon has contact killing, stomach toxicity and osmotic activity. The raw powder can be processed into powder, wettable powder, soluble powder, emulsion and other dosage forms for use, and can also be directly prepared with aqueous solution or made into poison bait to prevent and control agricultural, forestry, horticultural pests, underground pests, etc. of chewing mouthpiece and piercing mouthpiece; Used as insecticide.

Prevention and treatment of fish diseases

Dipterex is a highly effective, low toxic and low residue insecticide. It has a good killing effect on trematodes, nematodes, echinococcus worms parasitized inside and outside the fish body, and cladocera, copepod, clam hookworm larvae and water centipede that harm the fry and eggs. However, trichlorfon can form dichlorvos with greater residual toxicity under weakly alkaline conditions. When the pH value is 8~10, it only takes half an hour for trichlorfon to transform into dichlorvos. Therefore, not only the toxic effects of fish and shrimp should be considered, but also the safety of people and animals should not be ignored. Therefore, the following ten points should be noted when using trichlorfon to control fish diseases:
1. Suit the remedy to the case: 90% of trichlorfon crystals are commonly used to control fish diseases. It can only prevent and cure parasitic fish diseases, but not bacterial viral fish diseases, so you should first diagnose what the disease is, and then apply the right medicine to the case, instead of blindly using drugs. This is important.
2. Master the characteristics of pesticides for dissolution: trichlorfon is easily soluble in water, and it is forbidden to use hot water above 50 ℃ for dissolution. It is better to use fish tank water for dissolution. The trichlorfon aqueous solution is unstable, so it should not be kept for a long time after it is prepared. It should be immediately poured into the fish pond (tank).
3. Master the time of medication: because the pH value of water in the morning is lower than that in the daytime, and the larvae of the anchor head are often concentrated on the surface of the water in the morning, medication should be carried out in the morning, and drugs should not be used when the fish head is floating or just finished.
4. Strictly control the dosage: do not use too much at will, such as 0.3~0.5mg/L anti ring worm, pine alga insect, Zhonghua Sao, anchor head 鳋, etc.
5. Grasp the concentration of water quality for medication: determine the pH value of the pool water before applying trichlorfon, which varies according to the pH value of the pool water, such as 0.5mg/kg for pH 6.5~7, and 0.4mg/kg for pH 8~9.
6. It is not allowed to use trichlorfon for certain aquatic species: it is sensitive to trichlorfon for mandarin fish, perch, pomfret and other fishes and shrimps, and it will also cause death if treated with normal medical dosage. Therefore, trichlorfon pesticide cannot be used, and other drugs should be used instead.
7. Correct mixed use of drugs: it can not only cure diseases and pests, reduce costs, but also significantly overcome and inhibit the development of drug resistance. For example, a mixture of 90% trichlorfon and ferrous sulfate was used to control the occurrence of fish lice in silver carp with 0.5: 2, 0.25 mg/kg. For another example, 90% trichlorfon and facial alkali mixture can kill three generations of ring worm with 1:0.6 and 0.25 mg/kg.
8. Medicine cake can be used to treat worms: For parasites parasitic in fish, trichlorfon should be mixed into food to make medicine cake for prevention and control. For example, 90% trichlorfon and flour can be used to make medicine cake in a ratio of 1:1. After feeding for 3 to 5 days, the tapeworm in Jiujiang can be eradicated. With soybean cake and trichlorfon, a portion of trichlorfon mixed with 300 times of soybean cake powder can be used to make medicine cake for 5 days to kill Capillaria. The treatment colorful can be used as hamburger bait, and the dosage must be controlled.
9. Alternate drug use: To prevent and treat parasitic fish diseases, trichlorfon should not be used alone for a long time, but should be used in rotation with Yingshi Mihuling, B-type Mihuling, etc.
10. Do not mix with alkaline drugs: In addition to the above methods, alkaline substances shall not be added or washed with alkaline water to prevent the formation of more toxic dichlorvos, which may cause poisoning to people and fish. At the same time, trichlorfon can only kill the larvae of the anchor head, but not the adults parasitized on the fish. Therefore, when treating this insect, it is necessary to use twice a month to kill the larvae.
Finally, trichlorfon is divided into agricultural and veterinary use, as well as fishing use. If you don't have the conditions to buy fish, you'd better also use animals.

usage method

1. Use 8 kg of wheat bran and 0.5 kg of 90% trichlorfon crystal to mix and make poison bait, which can be spread on the seedbed to trap and kill mole cricket and ground tiger larvae.
2. With 1000 times liquid of 90% crystal dipterex, it can spray and kill young larvae such as geometrid, moth, leaf roller, whitefly, leaf wasp, meadow moth, elephant beetle, jasmine leaf moth, leaf miner, moth, thorn moth, lampworm, armyworm, mulberry caterpillar, butterfly, longicorn beetle, etc.
3. The roots of flowers and trees are irrigated with 1000 times solution of 90% trichlorfon crystal, which can control grubs, noctuids, white pocket moths, etc.

matters needing attention

1. It cannot be used together with or at the same time with alkaline drugs. Because "trichlorfon" is an organic phosphorus preparation, if it meets with alkaline drugs or alkaline substances, it will increase toxicity, cause livestock poisoning, and even cause death. Sodium bicarbonate, artificial salt, Jianweisan, sodium salt of various sulfonamides, soft soapy water, hard soapy water, lime water, etc. are alkaline drugs, and should not be used in combination with or at the same time with trichlorfon. In addition, if ordinary water is alkaline hard water, it cannot be used to prepare trichlorfon solution.
2. Do not exceed the therapeutic dose. Because the therapeutic dose of trichlorfon is very close to the toxic dose, a little carelessness will lead to poisoning or even death of livestock due to excessive dose. Therefore, in order to ensure the safety of livestock, it is necessary to accurately determine their weight first, and then accurately calculate the dosage according to their weight. 20~40 mg/kg body weight of cattle, with a maximum dose of 15 g once; Horses, donkeys and mules weigh 30-50 mg per kg, with the maximum dose of 20 g once; 80~100 mg/kg body weight, with a maximum dose of 5 g per time; The maximum dose of sheep is 5 grams per kg of body weight 80~100 mg; Goats are slightly more sensitive than sheep, and the dosage is less, 50~70mg per kilogram of body weight, and the maximum dosage once is 4g.
When taking "trichlorfon" orally, a solution with a concentration of 1%~3% should be prepared. If the concentration is too low, the effect is not good, and if the concentration is too high, the side effects will increase. In order to alleviate its irritation to the stomach of livestock, it should be used in combination with an appropriate amount of starch.
3. Poultry cannot be treated with "trichlorfon". Because "trichlorfon" belongs to organic phosphorus preparation, poultry such as chickens, ducks and geese are particularly sensitive to organic phosphorus preparation for three reasons: first, organic phosphorus preparation can damage the brain of poultry; Second, organic phosphorus preparations can cause neurological disorders in birds after entering the body; Third, the hydrolysis of organic phosphorus preparations by poultry is particularly weak, that is, the natural detoxification ability of organic phosphorus preparations is particularly low. Therefore, in addition to the use of 0.1%~0.15% "trichlorfon" dilute solution to soak the affected part for external use, "trichlorfon" should never be used for internal use of insect repellents for birds.

First aid measures

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Skin contact: Take off the contaminated clothes immediately and wash with plenty of flowing water. Get medical attention.
Eye contact: Lift the eyelid and flush with flowing water or physiological saline. Get medical attention.
Inhalation: quickly leave the site to a place with fresh air. Keep the respiratory tract unobstructed. If breathing is difficult, give oxygen. If breathing stops, perform artificial respiration immediately. Get medical attention.
Ingestion: drink enough warm water to induce vomiting. Gastric lavage. Get medical attention.

Protective measures

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Respiratory system protection: It is recommended to wear a hood type electric air supply filter type dust respirator during production operation or agricultural use.
Eye protection: protection has been made in respiratory system protection.
Body protection: wear work clothes to prevent poison penetration.
Hand protection: wear neoprene gloves.
Other protection: smoking, eating and drinking are prohibited at the work site. After work, take a shower and change clothes. Work clothes are not allowed to be taken to non work places. Store the clothes contaminated by poisons separately and use them after washing. Pay attention to personal hygiene.

Leakage emergency treatment

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Isolate the leakage contaminated area and restrict access. Cut off the ignition source. It is recommended that emergency personnel wear dust masks (full face masks) and gas suits. Do not touch the leakage directly.
Small amount of leakage: avoid raising dust and collect it in a dry, clean and covered container with a clean shovel. A large amount of water can also be used for flushing, and the diluted washing water will be discharged into the waste water system.
Large amount of leakage: collect and recycle or transport to waste disposal site for disposal.

Operation, disposal, storage and transportation

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Precautions for operation: close operation and strengthen ventilation. Operators must be specially trained and strictly abide by the operating procedures. It is recommended that the operator wear a hood type electric air supply filter type dust respirator, anti poison penetration work clothes and neoprene gloves. Keep away from kindling and heat sources, and smoking is strictly prohibited in the workplace. Use explosion-proof ventilation systems and equipment. Avoid dust generation. Avoid contact with oxidants and alkalis. Load and unload gently during transportation to prevent damage to packaging and containers. Fire fighting equipment and leakage emergency treatment equipment of corresponding types and quantities shall be provided. Empty containers may leave harmful substances.
Precautions for storage: store in a cool and ventilated warehouse. Keep away from kindling and heat sources. Packing and sealing. It shall be stored separately from oxidants and alkalis, and mixed storage is strictly prohibited. Equip with corresponding types and quantities of fire-fighting equipment. The storage area shall be equipped with appropriate materials to contain leakage.
Precautions for transportation: Before transportation, check whether the packaging container is complete and sealed. During transportation, ensure that the container does not leak, collapse, fall or damage. It is strictly prohibited to mix with acids, oxidants, food and food additives. During transportation, it shall be protected from sun exposure, rain and high temperature.

security information

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Safety terminology

S2:Keep out of reach of children.
Keep out of the reach of children.
S24:Avoid contact with skin.
Avoid skin contact.
S37:Wear suitable gloves.
Wear appropriate gloves.
S60:This material and/or its container must be disposed of as hazardous waste.
The substance and its container must be disposed of as hazardous waste.
S61:Avoid release to the environment. Refer to special instructions/Safety data sheets.
Avoid releasing into the environment, refer to special instructions/safety receipt instructions.

Risk terminology

R34:Causes burns.
Causes burns.

Related research

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On September 22, 2023, the team of the School of Life Sciences and Technology of China Pharmaceutical University published the title "The attending effects of syndiotic containing Certobacterium somerae and Astragalus polysaccharide against trichlorfon induced hepatotoxicity in crucian carp (Carassius carassius)" on the international authoritative academic journal Journal of Hazardous Materials (IF: 13.6) Research paper. This study is based on the feeding experiment of crucian carp. Through 16S sequencing of intestinal flora, SCFA detection and physiological and biochemical detection, it is found that trichlorfon has hepatotoxicity to crucian carp. Synbiotics can regulate intestinal flora, promote the growth of beneficial bacteria, increase the production of short chain fatty acids, and reduce liver damage caused by trichlorfon, thus providing a new idea for the prevention and control of trichlorfon hepatotoxicity. Baimaike provided microbial 16S sequencing service for this study.