3a,4,7,7a-tetrahydro-2-[(trichloromethyl)thio]-1H-isoindole-1,3(2H)-dione
1,2,3,6-tetrahydro-N-(trichloromethylthio)phthalimide
CAS: 133-06-2
Molecular Formula: C9H8Cl3NO2S
3a,4,7,7a-tetrahydro-2-[(trichloromethyl)thio]-1H-isoindole-1,3(2H)-dione - Names and Identifiers
3a,4,7,7a-tetrahydro-2-[(trichloromethyl)thio]-1H-isoindole-1,3(2H)-dione - Physico-chemical Properties
| Molecular Formula | C9H8Cl3NO2S |
| Molar Mass | 300.59 |
| Density | 1.74 |
| Melting Point | 178°C |
| Boling Point | 314.2°C (rough estimate) |
| Flash Point | 2°C |
| Water Solubility | 3.3 mg l-1 (25 °C) |
| Vapor Presure | 1.0 x 10-5 Pa (25 °C) |
| Appearance | White to white-like powder |
| Color | White, beige |
| Exposure Limit | ACGIH TLV: TWA 5 mg/m3. |
| Merck | 14,1772 |
| BRN | 234872 |
| pKa | -2.68±0.20(Predicted) |
| Storage Condition | Inert atmosphere,Room Temperature |
| Stability | Stable. Incompatible with strong bases, strong oxidizing agents. |
| Refractive Index | 1.6360 (estimate) |
| MDL | MFCD00041811 |
| Physical and Chemical Properties | Melting Point: 178 density: 1.74 water solubility: 0.00033g/100 mL Appearance: white crystals |
| Use | Used as a protective fungicide, foliar spraying or seed dressing can be |
3a,4,7,7a-tetrahydro-2-[(trichloromethyl)thio]-1H-isoindole-1,3(2H)-dione - Risk and Safety
| Risk Codes | R23 - Toxic by inhalation R40 - Limited evidence of a carcinogenic effect R41 - Risk of serious damage to eyes R43 - May cause sensitization by skin contact R50 - Very Toxic to aquatic organisms R36 - Irritating to the eyes R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R11 - Highly Flammable |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S29 - Do not empty into drains. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. S36/37 - Wear suitable protective clothing and gloves. S16 - Keep away from sources of ignition. |
| UN IDs | UN 3077/9099 |
| WGK Germany | 2 |
| RTECS | GW5075000 |
| HS Code | 29309090 |
| Hazard Class | 6.1 |
| Packing Group | III |
| Toxicity | LD50 orally in rats: 9000 mg/kg (Bridges) |
3a,4,7,7a-tetrahydro-2-[(trichloromethyl)thio]-1H-isoindole-1,3(2H)-dione - Introduction
Soluble in chloroform, benzene, ether, insoluble in water, stable to acid, decomposed under the action of strong alkali
Last Update：2022-10-16 17:13:25
3a,4,7,7a-tetrahydro-2-[(trichloromethyl)thio]-1H-isoindole-1,3(2H)-dione - Reference Information
| LogP | 2.57 at 25℃ |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| (IARC) carcinogen classification | 3 (Vol. 30, Sup 7) 1987 |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| application | crabendan, a white crystal, is a commonly used agricultural fungicide, which can be used to prevent and control Botrytis, Fusarium, Fusicoccum and Pythium. It can enhance denitrification and total culture bacteria. Kependan belongs to trichloromethio-based fungicides and is a derivative of phenyldiimide. Kebendan is mainly used as a fungicide. They have a good killing effect on a variety of fruit trees and vegetable diseases, and have little phytotoxicity. Proper use can also stimulate plant growth. Although it has low toxicity to mammals, ruminants, especially sheep, are particularly sensitive to it, and the lethal dose is extremely low. At the same time, it is a suspected carcinogenic pesticide to humans. |
| Preparation | The reaction of butadiene and maleic anhydride produces 1,2,3,4-tetrahydrophthalic anhydride, and then reacts with ammonia to synthesize 1,2,3,4-tetrahydrophenylenediimide, and finally reacts with trichlorothiochloromethane to decedan, namely N-(trichloromethyl thio)-cyclohexane -4-ene -1, 2-dimethylimide. Preparation of 1,2,3,4-tetrahydrophthalimide Preparation of 1,2,3,4-tetrahydrophthalic anhydride Preparation of maleic anhydride and benzene are mixed and heated to dissolve the acid anhydride. When the temperature rises to 70 ℃, butadiene is introduced and reacted at (75±2)℃ until the aeration reaction reaches the end point. Then the material is put into the crystallization tank while it is hot, cooled to room temperature, and filtered, the filter cake is dried at 50~70 ℃ to obtain 1,2,3,4-tetrahydrophthalic anhydride with a content of more than 95%. Preparation of 2.1,2,3, 4-tetrahydrophthalimide Add ammonia water to the reaction bottle, add 1,2,3,4-tetrahydrophthalic anhydride below 50 ℃, gradually raise the temperature to 105~110 ℃, evaporate the remaining free ammonia and water, and then gradually raise the temperature to 230~250 ℃, about 4.5~5h, release the material, cool to 80 ℃, and heat the water to dissolve, cooling crystallization, filtration, drying, 1,2,3, 4-tetrahydrophthalimide. Preparation of N-(Trichloromethyl)-Cyclohexyl -4-ene-1, 2-dimethylimide 1,2,3, 4-tetrahydrophthalimide is added to 5% ~ 6% sodium hydroxide solution precooled to 0 ℃, after complete dissolution, trichlorothiomethane is added and reacted at 0~5 ℃. When the pH value is below 8, the reaction is over, filtration, the filter cake is washed with water to be neutral, and dried to obtain N-(trichloromethyl)-cyclohexyl -4-ene -1, 2-dimethylimide. |
| toxicity | acute oral LD50 of rats is 9000 mg/kg, which has irritating effect on skin and mucosa. No chronic poisoning symptoms occurred in dogs fed with 300mg/kg industrial products daily for 66 weeks, and the non-effective dose for the 2-year feeding test on rats was 1000mg/kg. Animal experiments have found teratogenic and mutagenic effects. |
| use | used as a protective fungicide, foliar spraying or seed dressing can be trichloromethio broad-spectrum protective fungicide, against barley, wheat, oats, rice, corn, cotton, vegetables, fruit trees, melons, tobacco and many other crops have good control effect. It is safe for crops, has no phytotoxicity, and also has the effect of stimulating plant growth. It also has good control effects on rice sheath blight, rice blast, wheat stalk rust, tobacco leaf scab, cotton seedling disease, apple rot, etc. Kebendan is an important variety of organic fungicides, which has good control effects on various diseases of crops such as three wheat, rice, corn, cotton, vegetables, fruit trees, melons, and tobacco. The control effect of Sanmai scab is second only to carbendazim, and it also has good control effect on rice sheath blight, rice blast, wheat straw embroidery, tobacco scab, cotton seedling disease, apple rot, etc. The product is also used for seed dressing to prevent and control cotton seedling diseases. The oral LD50 of rats is 9000mg/kg. It has a stimulating effect on the skin and mucous membranes. |
| Production method | The reaction of butadiene and maleic anhydride to generate 1,2,3,6-tetrahydrophthalic anhydride, and then react with ammonia to synthesize 1,2,3,6-tetrahydrophenylenediimide, and finally react with trichlorothiomethane to obtain carbendan. Preparation of 1,2,3,4-Tetrahydrophthalic anhydride The maleic acid rod and benzene are mixed and heated to dissolve maleic anhydride. When the temperature rises to 70 ℃, butadiene is introduced and reacted at (75±2)℃ until the aeration reaction reaches the end point. Then the material is put into the crystallization tank while it is hot, cooled to room temperature, filtered, and the filter cake is dried at 50~70 ℃ to obtain 1,2,3, 4-tetrahydrophthalic anhydride with a content of more than 95%. Preparation of 1,2,3,4-tetrahydrophthalimide The ammonia water is lengthened in the reaction bottle, and the 1,2,3,4-tetrahydrophthalic anhydride is lengthened below 50 ℃, and the temperature is gradually increased to 105~110 ℃, so that the remaining free ammonia and water are evaporated, and then the temperature is gradually increased to 230~250 ℃, about 5~6h, the material is released, cooled to 80 ℃, and the heated water is dissolved, cooling crystallization, filtration, drying, 1,2,3, 4-tetrahydrophthalimide. Synthesis of Kedendan Add 1,2,3,4-tetrahydrophthalic acid imine to 5% ~ 6% sodium hydroxide solution precooled to 0 ℃, after complete dissolution, add trichlorothiochloromethane, and react at 0~5 ℃. When the pH value is below 8, the reaction is over, filtration, and the filter cake is washed with water to be neutral, dry, and decedan. |
| category | pesticide |
| toxicity classification | low toxicity |
| acute toxicity | oral-rat LD50: 9000 mg/kg; Oral-mouse LD50: 7000 mg/kg |
| flammability hazard characteristics | Combustion produces toxic chlorides, nitrogen oxides and phosphorus oxide gases |
| 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 |
| occupational standard | TWA 5 mg/m3; STEL 15 mg/m3 |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-07-11 11:08:59
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