63637-89-8

Usage

Uses

Used in Agricultural Industry:
IPRODIONE is used as a fungicide for protecting crops from fungal diseases. It helps in maintaining the health and productivity of crops by inhibiting the growth of fungi that can cause damage to the plants.
Used in Crop Protection:
IPRODIONE is used as a protective agent in crop protection, ensuring the prevention of fungal infections that can lead to reduced crop yields and quality. Its application helps in maintaining the overall health of the crops and contributes to increased agricultural productivity.

InChI:InChI=1/C13H13Cl2N3O3/c1-7(2)18-11(19)6-17(13(18)21)12(20)16-10-4-8(14)3-9(15)5-10/h3-5,7H,6H2,1-2H3,(H,16,20)

Upstream product

• 36734-19-7 Iprodione 
• 64952-42-7 3-(isopropylcarbamoyl)-5-(3,5-dichlorophenyl)hydantoic acid 

Relevant academic research and scientific papers

Effect of alcohols on the stability of iprodione in solution

Both primary and secondary alcohols degrade iprodione, 3-(3,5- dichlorophenyl)-N-(1-methylethyl)-2,4-dioxo-1-imidazolidine carboxamide. Steric hindrance has been found to have an inverse effect on the rate of its decomposition, and a fully substituted alcohol, such as tert-butanol, does not degrade iprodione due to extreme steric hindrance. The instability of iprodione in alcohol was found to be a function of the structure of the alcohol. The product, N-(3,5-dichlorophenyl)-3-(1-methylethyl)-2,4-dioxo-1-imidazolidine carboxamide, is obtained from all of the reacting alcohols. Confirmation of this structure came from the consideration of its NMR, mass spectral, and elemental analysis data.

Kinetics and Mechanisms of Cyclization in Acidic Media of N-N-glycine to Hydantoins: Iprodione and Its Isomer

N--N-glycine (1) cyclizes quantitatively and irreversibly at 50 deg C in the pH range 0.5-6 by two parallel paths to give iprodione (2) and its isomer 3.Formation of the antifungal agent 2 is characterized by a general base catalysis with carboxylate anions, water, and hydroxide ion (β = 0.38) and a solvent isotope effect of 2.90.These results are consistent with a specific base catalyzed addition of the enolate anion of the ureido group to the carboxylic function of hydantoic acid (pKa1 = 4.25) to givetetrahedral intermediate T- whose general acid catalyzed decomposition is rate limiting.Formation of isomer 3 occurs by a specific base catalyzed cyclization of 1 compatible with a nucleophilic attack of the enolate anion of the ureido moiety on the carboxylic group in the pH range 2-6.Below pH 2 hydantoic acid undergoes a specific acid catalysed and spontaneous hydrolysis involving a nucleophilic attack of the ureido enol on the carboxylic function, protonated or not, respectively.Formation of iprodione is general base catalysed while that of its isomer is not: this can be explained by the change in basicity of the leaving groups from the tetrahedral intermediate, i.e., the N- (pKa2 = 11.7) and the N-isopropylureido (pKa3 ca. 18) anions, respectively.