57012-86-9

Usage

Uses

Used in Agricultural Industry:
1-Ethylimidaazolidine-2,4,5-trione is used as a degradation product in the Agricultural Industry for the development and improvement of fungicides. As a byproduct of Cymoxanil, it contributes to the overall effectiveness of the fungicide in controlling late blight in plants. This helps maintain crop health and productivity, ensuring a stable food supply.

InChI:InChI=1/C5H6N2O3/c1-2-7-4(9)3(8)6-5(7)10/h2H2,1H3,(H,6,8,10)

Upstream product

• 79-37-8 oxalyl dichloride 
• 625-52-5 N-Ethylurea 
• 861071-57-0 N,N'-bis-ethylcarbamoyl-oxalamide 
• 57966-95-7 cymoxanil 
• 623-76-7 N,N'-diethylurea 

Downstream Products

• 1086764-91-1 C₁₁H₁₄N₂O₃ 
• 1207374-55-7 1-[(4,5-dioxo-3-phenyl-2-thioxoimidazolidin-1-yl)methyl]-3-ethyl-imidazolidine-2,4,5-trione 
• 625-52-5 N-Ethylurea 
• 144-62-7 oxalic acid 

Relevant academic research and scientific papers

Synthesis of imidazolidines, saccharins and chromone bearing imidazolidine ring

As a part of a research program related to the synthetic study of pharmacologically and agrochemically interesting imidazolidines, we synthesized imidazolidines 8, 9, 10, saccharins 12, 13 and chromone 17 bearing imidazolidine-2,4,5-trione or 2-thioxoimodazolidine-4,5-dione rings.

Simple synthesis of imidazolidinetrione derivatives having imidazolidine-2,4,5-trione and 2-thioxo-imidazolidine-4,5-dione rings

As a part of a research program related to the synthetic study of pharmacologically and agrochemically important imidazolidines, we chose to identify imidazolidine-2,4,5-trione and imidazolidine-2,4,5-trione or 2-thioxo-imidazolidine-4,5-dione rings as active components for the desired property. We currently report the synthesis of (imidazolidin.-2,4,5-dionyl) methyl-imidazolidine-2,4,5-triones 1, 4,5-dioxo-2-thioxo-imidazolidin-1.-yl- methyl-imidazolidine-2,4,5-triones 2, and 4,5-dioxo-2-thioxo-imidazolidin-1- ylmethyl-imidazolidine-2-thioxo-4,5-dione 3.

Characterization of metabolites of fungicidal cymoxanil in a sensitive strain of Botrytis cinerea

The metabolism of cymoxanil [1-(2-cyano-2-methoxyiminoacetyl)-3-ethyl urea] by a very sensitive strain of Botrytis cinerea toward this fungicide was studied by using [2-14C]-cymoxanil. Labeled cymoxanil was added either in a culture of this strain or in its enzymatic extract. The main metabolites, detected in biological samples, were isolated and identified by mass and NMR spectrometry. Their identification allowed us to show that this strain quickly metabolized cymoxanil according to at least three enzymatic pathways: (i) cyclization leading, after hydrolysis, to ethyl parabanic acid, (ii) reduction giving demethoxylated cymoxanil, and (iii) hydrolysis and reduction followed by acetylation leading to N-acetylcyanoglycine. In a cell-free extract of the same strain, only the first and the second enzymatic reactions, quoted above, occurred. Biological tests showed that, among all the metabolites, only N-acetylcyanoglycine is fungitoxic toward this sensitive strain.

Peroxynitrite reacts with 8-oitropurines to yield 8-oxopurines

Peroxynitrite reacts with 2′-deoxyguanosine to yield several major products, including 8-oxo2′-deoxyguanosine (8-oxodG) and 8-nitroguanine (8-nitroGua). While the terminal products formed during the reaction of 8-oxodG with peroxynitrite have been previously characterized, those formed from 8-nitroGua have not. To identify these products, 9-ethyl-8-nitroxanthine was used as a model for 8-nitroGua, since the former could be easily synthesized in high yield, and facilitated reversed-phase HPLC separation of the resulting products. Using this model substrate, the products formed during the peroxynitrite reaction were identified as the ethyl derivatives of oxaluric acid, 5-iminoimidazolidin-2,4-dione, III, [N-nitro-N'-[2,4-dioxo-imidazolidine-5-ylidene]-urea, V, dehydroallantoin, parabanic acid, cyanuric acid, and uric acid. Upon the basis of the previous studies with 8-oxodG, these products were recognized as those expected to arise from peroxynitrite-mediated uric acid oxidation. Furthermore, the presence of uric acid in the reaction mixture led us to propose a model in which the 8-nitropurine is first converted to the 8-oxopurine which is further oxidized by peroxynitrite to give the observed final products. We have also provided evidence suggesting that the peroxynitrite anion, acting as a nucleophile, might be responsible for the initial conversion of the 8-nitropurine to the 8-oxopurine and that a hydroxyl radical or oxidative process is less likely to explain this conversion.

Pharmaceutical composition containing an imidazolidinetrione derivative or pharmaceutically acceptable salt thereof

Pharmaceutical compositions containing imidazolidinetrione derivatives or pharmaceutically acceptable salts thereof having hypoglycemic and hypolipidemic effects. The compositions comprise as an active ingredient at least one imidazolidinetrione derivative of the formula: STR1 wherein each of R1 and R2, which may be the same or different, is hydrogen, an alkyl group, a cycloalkyl group or STR2 and each of R3 and R4, which may be the same or different, is hydrogen, halogen, a nitro group, a lower alkyl group or a lower alkoxy group.