71342-67-1

Basic information

• Product Name: 1-ETHYLIMIDAZOLIDINE-2,4,5-TRIONE 5-(O-METHYLOXIME)
• Synonyms: 1-ETHYLIMIDAZOLIDINE-2,4,5-TRIONE 5-(O-METHYLOXIME);1-Ethylimidazolidine-2,4,5-trione 5-(O-methyloxime) (isomer of AC-005)
• CAS NO: 71342-67-1
• Molecular Formula: C6H9N3O3
• Molecular Weight: 171.155
• Mol File: 71342-67-1.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• Density: 1.42 g/cm³
• Refractive Index: 1.588
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 1-ETHYLIMIDAZOLIDINE-2,4,5-TRIONE 5-(O-METHYLOXIME)(CAS DataBase Reference)
• NIST Chemistry Reference: 1-ETHYLIMIDAZOLIDINE-2,4,5-TRIONE 5-(O-METHYLOXIME)(71342-67-1)
• EPA Substance Registry System: 1-ETHYLIMIDAZOLIDINE-2,4,5-TRIONE 5-(O-METHYLOXIME)(71342-67-1)

Safety Data

• Hazardous Substances Data: 71342-67-1(Hazardous Substances Data)

Usage

Uses

1-Ethylimidazolidine-2,4,5-trione 5-(O-methyloxime) is an intermediate in the synthesis of 3-Ethyl-4-(methoxyamino)-2,5-dioxo-4-imidazolidinecarboxamide (E817920), which is a Cymoxanil (C988995), degradation product, used as a fungicide applied as a seed treatment or as a foliar application to the plants to control late blight.

InChI:InChI=1/C6H9N3O3/c1-3-9-4(8-12-2)5(10)7-6(9)11/h3H2,1-2H3,(H,7,10,11)/b8-4-

Upstream product

• 57966-95-7 cymoxanil 

Relevant articles and documents

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.