Name | Iprodione |
Synonyms | Rovral rop500f Iprodione Roval dust 3-(3,5-Dichlorophenyl)-n-Isopropyl-2,4-dioxo-1-Imidazolidinecarboximide 3-(3,5-dimethylphenyl)-N-isopropyl-2,4-dioxo-imidazolidine-1-carboxamide 3-(3,5-dichlorophenyl)-2,4-dioxo-N-(propan-2-yl)imidazolidine-1-carboxamide 3-(3,5-Dichlorophenyl)-N-(1-methylethyl)2,4-dioxo-1-imida zolidinecarboxamide [3-(3,5-Dichlorophenyl)-2,4-dioxoimidazolidinyl]-N-(methylethyl)carboxamide,Iprodione [3-(3,5-Dichlorophenyl)-2,4-dioxoiMidazolidinyl]-N-(Methylethyl)carboxaMide standard solution |
CAS | 36734-19-7 |
EINECS | 253-178-9 |
InChI | InChI=1/C15H19N3O3/c1-9(2)16-14(20)17-8-13(19)18(15(17)21)12-6-10(3)5-11(4)7-12/h5-7,9H,8H2,1-4H3,(H,16,20) |
Molecular Formula | C13H13Cl2N3O3 |
Molar Mass | 330.17 |
Density | 1.6223 (rough estimate) |
Melting Point | 130-134°C(lit.) |
Flash Point | 2°C |
Water Solubility | 0.0013 g/100 mL |
Vapor Presure | 5 x 10-7 Pa (25 °C) |
Appearance | neat |
Merck | 13,5096 |
BRN | 895003 |
pKa | 9.19±0.20(Predicted) |
Storage Condition | Sealed in dry,Room Temperature |
Refractive Index | 1.6140 (estimate) |
Physical and Chemical Properties | Melting point 130-136°C water-soluble 0.0013g/100 mL |
Use | A broad-spectrum protective fungicide |
Risk Codes | R40 - Limited evidence of a carcinogenic effect R50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. R36 - Irritating to the eyes R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R11 - Highly Flammable |
Safety Description | S36/37 - Wear suitable protective clothing and gloves. 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. S36 - Wear suitable protective clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S16 - Keep away from sources of ignition. |
UN IDs | UN 3077 9/PG 3 |
WGK Germany | 3 |
RTECS | NI8870000 |
HS Code | 29332900 |
Toxicity | LD50 in mice, rats (g/kg): 4, 3.5 orally (Lacroix, 1980) |
Raw Materials | 3,5-Dichloroaniline Glycine Isopropylamine |
NIST chemical information | Information provided by: webbook.nist.gov (external link) |
EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
toxicity | acute oral LD502060mg/kg in male rats and 1530 mg/kg in female rats. The acute oral LD50 was 1870mg/kg in male mice and 2670mg/kg in female mice. There are also reports of acute oral LD503500mg/kg in rats and 4000 mg/kg in mice. Rabbit acute percutaneous LD50>10000mg/kg. Large and mouse inhalation LD50>130mg/L. No irritation to eyes and skin. Rats were fed with 1000mg/kg and 2400mg/kg of medicament for 18 months and dogs for 3 months respectively, and no poisoning symptoms were found. No teratogenic, carcinogenic and mutagenic effects were found in animal experiments. Rainbow trout LC50 is 6.7mg/L (96h), carp LC50 is 10mg/, blue gill LC50 is 2.25~6.30mg/L. The LC50 of Daphnia is 3.6mg/L, the oral LD50 of wild ducks is> 10400 mg/kg, and the quail LD50930mg/kg. Bee LD50>400g/bee. |
use | broad spectrum contact fungicide. It also acts on spores, mycelium and sclerotia, inhibiting spore germination and mycelial growth of germs. It is almost impermeable in plants and is a protective fungicide. This agent has a good bactericidal effect on Botrytis cinerea, Nucleus, Alternaria, Sclerotia and Servospora. Prevention and control of tomato early blight starts spraying about 10 days after tomato transplantation, and spraying with 50% wettable powder 11.3~22.5g/100 m2 once every 2 weeks for a total of 3~4 times. To prevent gray mold, start medication before the disease occurs, use 50% wettable powder 5g/100 m2, and spray once every 10~14 days (flowering and fruiting are especially good), a total of 3~4 times, can improve tomato yield and quality. For example, every 100g of seeds are treated with 100~200g of original medicine, which has a control effect on smut caused by Helminthospore and Wheat reticulum smut. Potato seed potatoes were soaked in 4g/L liquid medicine with 50% wettable powder, which was effective against mole disease caused by Rhizoctonia solani. Treatment of scallion and garlic bulbous root can prevent and treat black rot sclerotium disease. With 50% wettable powder of 11.3~15g/100 m2, spraying medicine once at the initial flowering stage and once at the full flowering stage of rape can prevent and control Sclerotinia sclerotiorum. The application of this drug should be used alternately or mixed with other drugs to avoid drug resistance. iprodione is a contact fungicide, which acts on spores and mycelium at the same time, and is caused by Botrytis cinerea, Sclerotinia sclerotiorum, Sclerotinia sclerotiorum, Alternaria, etc. All diseases have control effects. iprodione can also be used as a seed treatment. is a broad-spectrum protective fungicide |
Production method | Add a mixture of 0.019mol of isopropyl isocyanate and 0.054mol of triethylamine to 0.045mol of 3-(3, 5-dichlorophenyl) in a solution of acetamide and 150mol of acetone, heated and refluxed. Cooling, decompressing to remove acetone, the resulting residue is washed with petroleum ether (boiling point 50-70 ℃)250mol, and recrystallized to obtain iprodione. Glycine (NH2CH2COOH) or ester reacts with phenyl 3, 5-dichloroisocyanate to produce 3-(3, 5-dichlorophenyl) acylurea acetic acid (or ester), followed by cyclization to obtain 3-(3, 5-dichlorophenyl) hydantoin, melting point 190 ℃, to be used. A mixture of 4.6g(0.019mol) isopropyl isocyanate and 5.5g(0.054mol) triethylamine was added to 11g(0.045mol) 3-(3, 5-dichlorophenyl) hydantoin and 150mL acetone solution. After heating and refluxing for 30min, cooling, decompressing and desolubbing, the residue was washed with petroleum ether (boiling point 50~70 ℃,250mL), and recrystallized with isopropyl ether to obtain 11g of iprodione with 74.2% yield and 136 ℃ melting point. |
category | pesticide |
toxicity classification | highly toxic |
acute toxicity | oral-rat LD50: 72.8 mg/kg; Oral-mouse LD50: 111 mg/kg |
flammability hazard characteristics | Combustion produces toxic nitrogen oxides and chloride 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 |
toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |