Folpet
N-(trichloromethylthio)phthalimide
CAS: 133-07-3
Molecular Formula: C9H4Cl3NO2S
Folpet - Names and Identifiers
Folpet - Physico-chemical Properties
| Molecular Formula | C9H4Cl3NO2S |
| Molar Mass | 296.56 |
| Density | 1.5097 (rough estimate) |
| Melting Point | 177-180°C |
| Boling Point | 333.8±52.0 °C(Predicted) |
| Flash Point | 155.7°C |
| Water Solubility | practically insoluble |
| Vapor Presure | 2.1 x 10-5 Pa (25 °C) |
| Appearance | neat |
| Color | Crystals |
| Merck | 13,4250 |
| BRN | 193373 |
| pKa | -3.34±0.20(Predicted) |
| Storage Condition | 0-6°C |
| Refractive Index | 1.6000 (estimate) |
| Physical and Chemical Properties | Pure white crystals. m. P. 177 °c, vapor pressure 1.33 x 10-3Pa (20 °c). Slightly soluble in organic solvents; Insoluble in water (only 1mg/L). In the dry condition is more stable, room temperature water slowly hydrolysis, high temperature or rapid decomposition of alkaline substances. |
| Use | Is a broad-spectrum protective fungicides, mainly used for the prevention and control of grain and oil crops, vegetables, fruit trees and other diseases |
Folpet - Risk and Safety
| Risk Codes | R20 - Harmful by inhalation R36 - Irritating to the eyes R40 - Limited evidence of a carcinogenic effect R43 - May cause sensitization by skin contact R50 - Very Toxic to aquatic organisms |
| Safety Description | S36/37 - Wear suitable protective clothing and gloves. S46 - If swallowed, seek medical advice immediately and show this container or label. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. |
| UN IDs | UN 3077 9/PG 3 |
| WGK Germany | 2 |
| RTECS | TI5685000 |
| HS Code | 29309090 |
| Hazard Class | 9 |
| Packing Group | III |
| Toxicity | LD50 orally in adult male, female rats: >5000 mg/kg (Gaines, Linder) |
Folpet - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| background and overview | organic sulfur fungicide (organosulphur fungicide) is the earliest organic fungicide developed. it has the advantages of high efficiency, broad spectrum and safety. dozens of varieties have been developed by the 1980 s, of which more than a dozen varieties are commonly used, which are fungicides with larger tonnage. From 1930 to 1931, Du Pont Company of the United States and Bayer Company of Germany developed ziram and thiram. In 1943, Rohm & Haas Company of the United States successfully trial-produced zineb. From the 1950s to the 60s, the development, production and application of organosulfur fungicides reached its peak, and many broad-spectrum fungicides were developed, such as maneb, amobam, mancozeb, copper (mancopper), and zinc (zinc). Organic sulfur fungicides are almost all dithiocarbamate fungicides, which are heavy metal salts or esters of dithiocarbamate in chemical structure, but there are also thiocarbamate fungicides, such as thiocarbamate (prothiocarb), sulphonocarbamate (methasulfocarb) and other varieties. Folpet, chemical name N-trichloromethylthiophthalimide, is a broad-spectrum therapeutic and protective organosulfur fungicide. It was promoted by Standard Oil Development Company in 1949. It is a fungicide used for crop diseases and insect pests and is a protective fungicide. It can prevent some diseases of grapes, as well as late blight, powdery mildew, leaf rust, leaf spot disease and other diseases of potatoes and other crops. High toxicity to fish, low toxicity to bees and wildlife. The existing data show that sterilizing Dan can cause bacterial gene mutation and tumor of rodent cells. Sterilization Dan is widely used in industrial and agricultural production. After it was first registered and listed in the United States in 1948, more than 200 kinds of products including sterilization Dan ingredients have been produced and used. With the in-depth research on sterilization pills, since 1987, EP A in the United States has begun to restrict the production and use of sterilization pills and products containing sterilization pills. It is reported in the literature that the side chain of sterilization pills-S-CCI3 is very active, neutral or Under alkaline conditions, it quickly reacts with cysteine and glutathione to form an intermediate product with a short half-life-thiophosgene, which may produce toxicity, but its toxic effects need further study. |
| character | pure product is white crystal with melting point of 177 ℃ and vapor pressure of <1.33mPa at 20 ℃. It is difficult to dissolve in water (1mg/L) at room temperature and slightly soluble in organic solvents. The purity of the original drug is about 90%. It is stable in a dry state, slowly hydrolyzed in water at room temperature, and rapidly hydrolyzed in high temperature or under alkaline conditions. Can not be mixed with alkaline pesticides. This product is non-corrosive, and the hydrolysate is corrosive. |
| toxicity | acute oral toxicity LD50>10 g/kg in rats and acute percutaneous toxicity LD50>22.6 g/kg in rats. Industrial products were fed to rats at 10000 mg/kg for 17 months, and no lesions or tumors were found. Rats were fed with food containing 100~1000 mg/kg, and there was no adverse effect on reproduction for three consecutive generations. It has a stimulating effect on the mucous membrane, and its dust or droplets can be exposed to the eyes, skin or inhaled can cause local irritation. Carp TLm(48 hours) was 0.21mg/L. ADI is 0.1 mg/kg. |
| synthesis route | 1. preparation method: 1) synthesis of phthalimide: phthalic anhydride and urea are weighed at 1:0.24 and mixed evenly. The amination kettle is preheated for 10 minutes under 0.5MPa steam heating, the stirrer is started, and the mixture is quickly put into the mixture, so that the reaction reaches a complete "spray" state within 15-20 minutes. After the reaction is completed, water is added quickly, crystals are precipitated in the water, and wet phthalimide is obtained by suction filtration. The yield is 90% ~ 95%. 2) synthesis of trichloromethyl thiohypochlorite: add water, carbon disulfide and concentrated hydrochloric acid into the chlorinator, stir and cool to 28~30 ℃, start to pass chlorine until absorption is complete, react for 2~3 hours, separate the oil layer after reaction, and wash with water to obtain trichloromethyl thiohypochlorite. Yield 80% 3) synthesis of sterilizer: put 5% NaOH solution into condensation kettle, start the stirrer and cool the temperature to -2 ℃, add imine and stir for 15-20 minutes to make imine become sodium salt. Under the condition of maintaining the reaction temperature not higher than 10 ℃, trichloromethyl thiohypochlorite is added dropwise. When the reactant pH8 ~ 9, discharge, filtration, drying, that is, sterilization Dan. 50% yield. 2. Production process flow chart of sterilizer: |
| quality standard | raw powder: white or light yellow powder, active ingredient content/%≥ 90.0, melting point/℃ 160~175, free chlorine content/% ≤ 1.0. |
| uses | this product is effective against powdery mildew (Erysiphe spp.), scastar (Venturia spp.), scutellaria (Glomerella spp.), discochlea (Gloeosporium spp.), monofilament (Sphaerotheca spp.), monocystis (Podos-phaera spp.), frost mold (Peronospora spp.), and Alternospora (Alternaria spp.), Phytophthora (Phytophthora spp.), Botrytis (Botrytis spp.), etc. are all active. It is used to prevent and control various diseases of food crops, vegetables, fruit trees, etc., and has a stimulating effect on the growth of plants. For example, it can control rice blast, rice sheath blight, wheat rust, peanut leaf spot, potato late blight, tobacco anthracnose, etc. Mainly used for spraying: spray liquid medicine at a concentration of about 0.1% to prevent melons, vegetables, grape downy mildew, powdery mildew, potato, tomato early blight, late blight, apple anthracnose, scab, powdery mildew, Strawberry and other gray mold, etc.; about 0.2% concentration of liquid medicine to control wheat powdery mildew, rust, scab and peanut leaf spot, tobacco anthracnose, rice sheath blight, etc. When the dosage is too large, some varieties of pears, sweet cherries, peaches and grapes are prone to phytotoxicity. This product is not suitable for mixing with strong alkaline agents and oils, and can be mixed with most commonly used pesticides. A number of compound preparations have come out, such as Trimifol (compounded with copper salt),Mycodifol (compounded with diphtheran), etc. trichloromethane-based protective fungicides. The main spray prevents and treats various diseases such as grain and oil crops, vegetables, fruit trees, etc., and has a biological stimulating effect on plants. 50% wettable powder is sprayed 300~500 times liquid to prevent and control rice blast. Panicle neck blast is sprayed at the beginning of the disease, and panicle neck rice blast is sprayed once at the beginning of the panicle and once at the full panicle. To control rice sheath blight, spray 200 times of 40% wettable powder. To prevent wheat rust and scab, spray 250 times 40% wettable powder. 50% wettable powder 500 times liquid spray for controlling rape downy mildew. 50% wettable powder 200~250 times liquid spray for prevention and control of peanut leaf spot. In addition, it can also be used to control potato late blight, tomato early blight, cabbage downy mildew, melon downy mildew and powdery mildew, tobacco anthracnose, apple anthracnose, grape downy mildew and powdery mildew, tea cloud leaf blight, wheel spot disease, white star disease, etc. |
| specification | 50%, 75% wettable powder |
| precautions | 1. Do not mix with oil emulsion, alkaline agent and iron-containing substance or use before and after; 2. It has irritating effect on human and animal mucosa. Do not inhale powder when using it. Wash hands, feet and face with soap after using it. 3. It has mild medicinal damage to pears, grapes, and apples, and significant medicinal damage to soybeans and tomatoes at high concentrations. 4. Store in a cool, ventilated warehouse. Stay away from fire and heat sources. 5. Prevent direct sunlight. The package is sealed. 6. It should be stored separately from oxidants, alkalis and edible chemicals, and should not be mixed. Equipped with corresponding varieties and quantities of fire fighting equipment. 7. The storage area shall be equipped with suitable materials to contain leakage. |
| Main reference materials | [1] Shen Panwen, editor-in-chief Wang Jitao. Compound dictionary. Shanghai: Shanghai Lexicographic Publishing House. 2002. p. 322 [2] Yu zhongbo et al. Study on mutagenicity, carcinogenesis, distortion and mutation detection of sterilizer. 2006.18(6):476-478. [3] Zhou Xin et al. Determination of chlorothalonil, kexandan and sterilan residues in grapes by dispersive liquid phase microextraction-gas chromatography. Analytical chemistry research report. 2009,27(1):41-45. [4] Zhu Yonghe, Wang Zhenrong, Li Buqing, editor-in-chief. Pesticide ceremony. Beijing: China Sanshan Publishing House Agricultural Science and Education Publishing Center. [5] China Agricultural Encyclopedia Editor-in-Chief Committee Pesticide Volume Editorial Committee, China Agricultural Encyclopedia Editorial Department Editorial Department. [6] Wang Daquan Editor-in-Chief. Fine Chemical Production Process Diagram Part II. Beijing: Chemical Industry Press. 1999. [7] Wu Shimin, editor-in-chief of Yin Delin. Concise and Refined Dictionary of the University of Technology. Shenyang: Liaoning Science and Technology Press. 1999. |
| production method | preparation of trichlorosulfur chloromethane mix the prepared 2% hydrochloric acid and metered carbon disulfide, stir to pass chlorine, control the flow rate of chlorine gas, maintain the reaction temperature at about 26 ℃, and control the normal absorption and treatment of the reaction tail gas, which generally takes about 30 hours. Finally, the trichlorosulfur chloride was separated by standing and washed with water for synthetic sterilization. Phthalimide is prepared by co-heating phthalic anhydride and ammonium bicarbonate. During production, phthalic anhydride and ammonium bicarbonate are mixed according to 3:1 (mass ratio), then put into a hot dissolving tank, heated with direct fire, and reacted at 300 ℃ for 10~12h. Because this operation is not easy to control, the reaction is not complete, energy consumption, long reaction period and environmental pollution. Because phthalic anhydride can be added to ammonia to dissolve it to form diammonium salt and evaporate the water. Reheating to a higher temperature for further dehydration to produce imine compounds. The synthesis of sterilization Dan will be 4. 5% of the lye is metered into the condensation reaction pot, the temperature is reduced to -4 ℃, and after excessive phthalimide solution is put in under intense stirring, a certain amount of trichlorosulfur chloride is added evenly, the temperature is controlled at about -2 ℃, the reaction end point pH = 8, and finally the condensate is centrifuged, washed with water, air dried and other post-treatment to prepare sterilization Dan. It is obtained by the reaction of phthalimide and trichlorosulfur chloride. First put 5% sodium hydroxide solution into a condensation pot, stir and cool to -2 ℃, add phthalimide to make it a sodium salt. Under the condition that the reaction temperature is not higher than 10 ℃, trichlorosulfur chloride is added dropwise. When the pH of the reactant reaches 8-9, the material is filtered and dried to obtain the finished product with a yield of 75%-79%. |
| category | pesticide |
| toxicity classification | poisoning |
| acute toxicity | oral-rat LD50: 7540 mg/kg; Oral-mouse LD50: 1546 mg/kg |
| storage and transportation characteristics | warehouse ventilation and low temperature drying; separate from food raw materials storage and transportation |
| fire extinguishing agent | dry powder, foam, sand |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 22:18:34
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