IUPAC reports on pesticides, no. 28: Some aspects of the analysis of residues of dicarboximide fungicides in food

Ambrus, Á.; Buys, M.; Miyamoto, J.; Otto, S.; Smart, N. A.

doi:10.1351/pac199163050747

Cited by 5 publications

(3 citation statements)

References 2 publications

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“…The same compound (6) was also reported to have been obtained from iprodione by its rearrangement in an ethanolic solution (9) or by its chemical transformation in a sterile mineral medium (10). The cyclization of 3-(isopropylcarbamoyl)-5-(3,5-dichlorophenyl) hydantoic acid (2), the metabolism of iprodione in rats (11), the metabolism of iprodione in plants (8), or the reaction of 3-isopropylimidazolidine-2,4-dione with 3,5-dichlorophenylisocyanate (9) also produces 6.…”

Section: Resultsmentioning

confidence: 93%

“…Iprodione is a very useful agricultural chemical, and its residue is commonly found in plums , grapes – , carrots ,, , strawberries , nectarines , cherries , and other produces . This chemical has shown stability problems during analysis when it is in methanol-containing solvents, thereby requiring our laboratory to avoid alcoholic solvents for the extensive iprodione related analytical assays.…”

Section: Introductionmentioning

confidence: 99%

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Effect of Alcohols on the Stability of Iprodione in Solution

Anisuzzaman

Storehalder

Williams

et al. 2007

J. Agric. Food Chem.

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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.

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Section: Resultsmentioning

confidence: 93%

Section: Introductionmentioning

confidence: 99%

Effect of Alcohols on the Stability of Iprodione in Solution

Anisuzzaman

Storehalder

Williams

et al. 2007

J. Agric. Food Chem.

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“…The metabolism and excretion differences of procymidone between rats and humans were illustrated; in contrast to rats, humans extensively metabolized procymidone through glucuronide conjugation and excreted the conjugates in urine [10]. Two metabolites of procymidone in isopropanol and four metabolites in beans and cucumbers were reported [11,12]. To date, the environmental behaviors and metabolites of procymidone in soil have not been systematically studied.…”

Section: Introductionmentioning

confidence: 99%

Environmental Behaviors of Procymidone in Different Types of Chinese Soil

Zhang

et al. 2021

Sustainability

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Procymidone is a widely used fungicide in the prevention and treatment of fungal diseases on many crops in China. Part of the procymidone will enter the soil during the application process. Procymidone may exhibit environmental behavior diversity in different soils. Therefore, it is extremely important to clarify the environmental behavior of procymidone in soil for its environmental safety evaluation. Here, the degradation, adsorption, and mobility behaviors of procymidone in four typical types of Chinese soil were investigated for the first time. The half-lives of procymidone in the soils ranged from 14.3 d to 24.1 d. The degradation rates of procymidone in the soils were promoted by organic matter content, moisture content, and microorganisms. Furthermore, the degradation of procymidone on the soil surface was promoted by light. The desorption rates of procymidone in laterite soil, yellow brown soil, black soil, and chestnut soil were 27.52 ± 0.85%, 16.22 ± 0.78%, 13.67 ± 1.29%, and 7.62 ± 0.06%, respectively, which were contrary to the adsorption ability. The mobility order of procymidone in the soils was: laterite soil > yellow brown soil > black soil > chestnut soil, with the Rf values of 0.28, 0.22, 0.18, and 0.16, respectively. Three degradation products of procymidone were identified by liquid chromatography coupled with quadrupole/time-of-flight mass spectrometry, and the degradation pathway of procymidone in the soil was speculated. The results will provide a theoretical basis for the removal of procymidone in the soil environment.

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Mechanisms of dicarboximide ring opening in aqueous media: Procymidone, vinclozolin and chlozolinate

Villedieu¹,

Calmon²,

Calmon³

1994

Pestic. Sci.

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The hydrolysis kinetics of the dicarboximide fungicides procymidone, vinclozolin and chlozolinate in neutral and alkaline solutions of pH 60 to 13·7 at 25°C have been determined conjointly by ultraviolet spectrophotometry and by high performance liquid chromatography. Under alkaline conditions, the fungicides undergo attack by the hydroxide ion on a specific carbonyl group and the rate of hydrolysis increases proportionally to the hydroxide ion concentration. Procymidone gives quantitatively and irreversibly 2‐(3,5‐dichlorophenylcarba‐moyl)‐l,2‐dimethylcyclopropanecarboxylate. The reaction is not subject to general base catalysis and experimental data are in agreement with a rate‐determining attack by the hydroxide ion. After a rapid hydrolytic loss of the ethoxycarbonyl substituent from chlozolinate, the dicarboximide ring cleavage of the two other fungicides leads, by mechanisms which differ with respect to the type of base catalysis and the rate‐determining step, to the corresponding anilides, producing as intermediates the carbamic acids, which undergo loss of carbon dioxide. The hydrolysis of vinclozolin and chlozolinate yields, respectively, N‐(3,5‐dichloro‐phenyt)‐2‐hydroxy‐2‐methylbut‐3‐enanilide and N‐(3,5‐dichlorophenyl)‐2‐hydroxy‐propanilide.

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IUPAC reports on pesticides, no. 28: Some aspects of the analysis of residues of dicarboximide fungicides in food

Abstract: Abstract

Cited by 5 publications

References 2 publications

Effect of Alcohols on the Stability of Iprodione in Solution

Effect of Alcohols on the Stability of Iprodione in Solution

Environmental Behaviors of Procymidone in Different Types of Chinese Soil

Mechanisms of dicarboximide ring opening in aqueous media: Procymidone, vinclozolin and chlozolinate

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