27387-87-7

Basic information

• Product Name: 3-(3,5-dichlorophenyl)imidazolidine-2,4-dione
• Synonyms: 3-(3,5-dichlorophenyl)imidazolidine-2,4-dione;3-(3,5-DICHLOROPHENYL)-2,4-IMIDAZOLIDINEDIONE;Iprodione des-(N-isopropylcarboxamid)
• CAS NO: 27387-87-7
• Molecular Formula: C₉H₆Cl₂N₂O₂
• Molecular Weight: 245.06214
• EINECS: 248-438-3
• Mol File: 27387-87-7.mol
• Article Data: 6

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.561g/cm³
• Refractive Index: 1.621
• CAS DataBase Reference: 3-(3,5-dichlorophenyl)imidazolidine-2,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(3,5-dichlorophenyl)imidazolidine-2,4-dione(27387-87-7)
• EPA Substance Registry System: 3-(3,5-dichlorophenyl)imidazolidine-2,4-dione(27387-87-7)

Safety Data

• Hazardous Substances Data: 27387-87-7(Hazardous Substances Data)

Usage

Uses

3-?(3,?5-?Dichlorophenyl)?imidazolidine-?2,?4-?dione is a degradation product of Iprodione (I745000), a fungicide used in the treatment of crops. Pesticide.

InChI:InChI=1/C9H6Cl2N2O2/c10-5-1-6(11)3-7(2-5)13-8(14)4-12-9(13)15/h1-3H,4H2,(H,12,15)

Upstream product

• 36734-19-7 Iprodione 
• 904752-31-4 ethyl 2-(3-(1,5-dichlorophenylureido))acetate 
• 34893-92-0 3,4-dichlorophenyl isocyanate 
• 62584-33-2 3-(3,5-dichloro-phenyl)-ureidoacetic acid 
• 626-43-7 3,5-Dichloroaniline 
• 56-40-6 glycine 

Downstream Products

• 61610-19-3 3-(3,5-dichloro-phenyl)-1-methanesulfonyl-imidazolidine-2,4-dione 
• 61610-20-6 3-(3,5-dichloro-phenyl)-1-ethanesulfonyl-imidazolidine-2,4-dione 
• 61610-22-8 3-(3,5-dichloro-phenyl)-1-(propane-2-sulfonyl)-imidazolidine-2,4-dione 
• 61610-21-7 3-(3,5-dichloro-phenyl)-1-(propane-1-sulfonyl)-imidazolidine-2,4-dione 
• 61610-24-0 1-isobutylsulfonyl-3-(3,5-dichlorophenyl)-2,4-imidazolidinedione 
• 61610-23-9 1-(butane-1-sulfonyl)-3-(3,5-dichloro-phenyl)-imidazolidine-2,4-dione 
• 61610-25-1 1-(butane-2-sulfonyl)-3-(3,5-dichloro-phenyl)-imidazolidine-2,4-dione 
• 61610-29-5 3-(3,5-dichloro-phenyl)-1-(prop-2-ene-1-sulfonyl)-imidazolidine-2,4-dione 
• 61610-27-3 3-(3,5-dichloro-phenyl)-1-(pentane-1-sulfonyl)-imidazolidine-2,4-dione 
• 61610-35-3 1-(3-chloro-propane-1-sulfonyl)-3-(3,5-dichloro-phenyl)-imidazolidine-2,4-dione 
• 62584-33-2 3-(3,5-dichloro-phenyl)-ureidoacetic acid 
• 36734-19-7 Iprodione 
• 64225-03-2 1-(N-methoxy-N-methylcarbamoyl)-3-(3,5-dichlorophenyl)-hydantoin 

Relevant articles and documents

Preparation method and application of iprodione hapten and antigen

The invention provides a preparation method and application of iprodione hapten and antigen. The iprodione hapten is obtained through the following steps: taking 3,5-dichlorophenyl isocyanate and ethyl glycinate hydrochloride to react to generate ethyl 2-(3-(1,5-dichlorophenylcarbamido)) acetate, hydrolyzing to obtain 2-(3-(1,5-dichlorophenylcarbamido))acetic acid, carrying out ring-forming reaction to obtain 3-(3,5-dichlorophenyl)-2,4-imidazolidindione, reacting with methyl 6-isocyanatocaproate generated by reaction of methyl 6-aminohexanoate hydrochloride and triphosgene, so as to generate methyl 6-(3-(3,5-dichlorophenyl)-2,4-dioxyiminazolealkyl-1-formylamino)caproate; finally, hydrolyzing under an acidic condition. The iprodione antigen is obtained by coupling the iprodione hapten and carrier protein. The antigen prepared by the invention has a specific iprodione antigenic determinant, so that a high-specificity iprodione monoclonal antibody is possibly screened. A generated antibody has high specificity and high sensitivity and can be used for enzyme-linked immunization and rapid determination of test paper.

Preparation of 3 - (3,5-dichlorophenyl) - 2,4-imidazolidinedione method

The invention discloses a method for preparing 3-(3, 5-dichlorophenyl)-2, 4-imidazolidinedione with a structure as shown in a formula (I). The method comprises the following steps: (1) contacting one or a plurality of compounds shown by a formula (III) with compounds shown by a formula (II) under condensation reaction conditions in the presence of a condensation reaction catalyst and an organic solvent to obtain a mixture containing compounds shown by a formula (IV); and (2) directly contacting the mixture containing compounds shown by the formula (IV) with a ring closing reaction catalyst or separating out the compounds shown by the formula (IV) and contacting the compounds with the ring closing reaction catalyst under ring closing reaction conditions. The reaction yield of the method is high, and the intermediate does not need to be separated or purified, so that the steps are simple.

Nephrotoxic and hepatotoxic potential of imidazolidinedione-, oxazolidinedione- and thiazolidinedione-containing analogues of N-(3,5-dichlorophenyl)succinimide (NDPS) in Fischer 344 rats

Nephrotoxicity of the agricultural fungicide N-(3,5-dichlorophenyl)succinimide (NDPS) in rats is believed to involve metabolism on the succinimide ring. To further investigate this hypothesis, we synthesized and tested the following NDPS analogues, which contain other cyclic imide rings and may therefore be metabolized differently than NDPS: 3-(3,5-dichlorophenyl)-2,4-oxazolidinedione (DCPO), 3-(3,5-dichlorophenyl)-2,4-imidazolidinedione (DCPI), 3-(3,5-dichlorophenyl)-1-methyl-2,4-imidazolidinedione (DCPM) and 3-(3,5-dichlorophenyl)-2,4-thiazolidinedione (DCPT). Male Fischer 344 rats were administered DCPO, DCPI, DCPM, DCPT (0.6 or 1.0 mmol/kg, i.p. in corn oil), NDPS (0.6 mmol/kg, i.p. in corn oil) or corn oil (4 ml/kg). As evidenced by diuresis, proteinuria, elevated blood urea nitrogen levels, increased kidney weights and proximal tubular damage, NDPS produced severe nephrotoxicity in the rats. In contrast, DCPO, DCPI, DCPM and DCPT were mild nephrotoxicants. None of the compounds elevated serum alanine transferase activity or liver weights in the rats, however DCPT produced centrilobular necrosis. These experiments confirm that NDPS-induced nephrotoxicity is critically dependent on the presence of the succinimide ring. Furthermore, replacement of the succinimide ring with a thiazolidinedione ring produced a more pronounced effect on the liver than on the kidney. Liver damage has been reported in type II diabetic patients taking troglitazone, rosiglitazone and pioglitazone. Since these compounds also contain a thiazolidinedione ring, DCPT may be useful for investigating the role of this structural feature in hepatotoxicity.