Iprodion

Structural formula
General
Surname	Iprodion
other names	3- (3,5-dichlorophenyl) -2,4-dioxo- N -isopropylimidazolidine-1-carboxamide; Glycophen; Rovral;
Molecular formula	C 13 H 13 Cl 2 N 3 O 3
Brief description	colorless and odorless powder
External identifiers / databases
EC number	253-178-9
ECHA InfoCard	100.048.328
PubChem	37517
ChemSpider	34418
Wikidata	Q411542
properties
Molar mass	330.17 g mol −1
Physical state	firmly
Melting point	134 ° C
Vapor pressure	<133 Pa at 20 ° C
solubility	practically insoluble in water (0.013 g l −1 ); soluble in ethanol, methanol, acetonitrile, toluene, benzene, acetone and dimethylformamide;
safety instructions
H and P phrases	H: 351-410
	P: 273-281-501
Toxicological data	3500 mg kg −1 ( LD 50 , rat , oral ) ; 4000 mg kg −1 (oral, mouse) ; > 4400 mg kg −1 (oral, rabbit)
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Iprodione is a chemical compound from the group of dicarboximides and imidazoles . It is used as a fungicide and nematicide in crop protection products. Iprodion was developed by Rhône-Poulenc and launched on the market in 1974.

use

Iprodione is used as a contact fungicide primarily against Botrytis cinerea , but also against Sclerotinia and Alternaria species in vegetables and white stems in oilseed rape. It is also used to dress the seeds .

proof

Iprodione can be detected by capillary gas chromatography with mass spectrometric evaluation.

safety instructions

Iprodione has been classified as likely carcinogenic (Category 1B) and teratogenic (Category 2) since 2016.

Admission

Iprodione was approved as a plant protection product in the European Union since 2004 . However, the approval was withdrawn due to a new evaluation of the active ingredient by the European Food Safety Authority (EFSA) in November 2017. Iprodione may only be used as a pesticide until March 5, 2018. In Switzerland, on the other hand, iprodione is used as an active ingredient in pesticides.

Derivatives

Related pesticides from the dichlorophenyldicarboximide group are:

Chlozolinate C ₁₃ H ₁₁ Cl ₂ NO ₅
Dichlozoline C ₁₁ H ₉ Cl ₂ NO ₃
Isovaledione C ₁₄ H ₁₄ Cl ₂ N ₂ O ₃
Myclozolin C ₁₂ H ₁₁ Cl ₂ NO ₄
Procymidone C ₁₃ H ₁₁ Cl ₂ NO ₂
Vinclozolin C ₁₂ H ₉ Cl ₂ NO ₃

Web links

Maximum residue level regulation. on: gesetze-im-internet.de (PDF file)
C. Baroffio, Fatma Kivrak, W. Heller: Detection of iprodione-resistant Alternaria fungi on carrot seeds. In: Vegetable growing. 6, 2004, p. 5.

Individual evidence

↑ Marielle Vigourou: Iprodione Pathway Map. In: Biocatalysis / Biodegradation Database. Eawag , August 15, 2011, accessed on January 20, 2012 .
↑ ^a ^b ^c Entry on Iprodione. In: Römpp Online . Georg Thieme Verlag, accessed on January 4, 2015.
↑ ^a ^b ^c ^d ^e Pesticide Information Profile Iprodione. In: Extension Toxicology Network. Cooperative Extension Offices of Cornell University, Michigan State University, Oregon State University, and University of California at Davis, September 1993, accessed January 20, 2012 .
↑ Entry on 3- (3,5-dichlorophenyl) -2,4-dioxo-N-isopropylimidazolidine-1-carboxamide in the GESTIS substance database of the IFA , accessed on February 1, 2016 (JavaScript required)
↑ Entry on 3- (3,5-dichlorophenyl) -2,4-dioxo-N-isopropylimidazolidine-1-carboxamide in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ Data sheet Iprodione from Sigma-Aldrich , accessed on May 14, 2017 ( PDF ).
↑ F. Rouberty, J. Fournier: Capillary gas chromatographic - mass spectrometric determination of iprodione in chicory and leek . In: Chromatographia . tape 41 , no. 11 , December 9, 1995, pp. 693-696 , doi : 10.1007 / BF02267806 .
↑ EFSA Journal 2016; 14 (11): 4609.
↑ Directive 2010/58 / EU of the Commission of 23 August 2010 (PDF) .
↑ Federal Office for Consumer Protection and Food Safety: Revocation of the approval of plant protection products with the active ingredient iprodione on March 5, 2018 , accessed on February 23, 2018.
↑ General Directorate Health and Food Safety of the European Commission: Entry on Iprodione in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on December 6, 2019.
↑ External identifiers or database links for dichlozolin : CAS number: 24201-58-9, EC number: 607-339-9, ECHA InfoCard: 100.119.152 , PubChem : 32253 , ChemSpider : 29909 , Wikidata : Q27155724 .
↑ External identifiers of or database links to isovaledione : CAS number: 70017-93-5, PubChem : 155450 , ChemSpider : 136942 , Wikidata : Q27274072 .
↑ External identifiers or database links for Myclozolin : CAS number: 54864-61-8, EC number: 259-379-8, ECHA InfoCard: 100.053.963 , PubChem : 92350 , ChemSpider : 83373 , Wikidata : Q27155719 .

[1] Marielle Vigourou: Iprodione Pathway Map. In: Biocatalysis / Biodegradation Database. Eawag , August 15, 2011, accessed on January 20, 2012 .

[roempp-2] Entry on Iprodione. In: Römpp Online . Georg Thieme Verlag, accessed on January 4, 2015.

[cornell-3] Pesticide Information Profile Iprodione. In: Extension Toxicology Network. Cooperative Extension Offices of Cornell University, Michigan State University, Oregon State University, and University of California at Davis, September 1993, accessed January 20, 2012 .

[GESTIS-4] Entry on 3- (3,5-dichlorophenyl) -2,4-dioxo-N-isopropylimidazolidine-1-carboxamide in the GESTIS substance database of the IFA , accessed on February 1, 2016 (JavaScript required)

[CLP_100.048.328-5] Entry on 3- (3,5-dichlorophenyl) -2,4-dioxo-N-isopropylimidazolidine-1-carboxamide in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .

[Sigma-6] Data sheet Iprodione from Sigma-Aldrich , accessed on May 14, 2017 ( PDF ).

[7] F. Rouberty, J. Fournier: Capillary gas chromatographic - mass spectrometric determination of iprodione in chicory and leek . In: Chromatographia . tape 41 , no. 11 , December 9, 1995, pp. 693-696 , doi : 10.1007 / BF02267806 .

[8] EFSA Journal 2016; 14 (11): 4609.

[9] Directive 2010/58 / EU of the Commission of 23 August 2010 (PDF) .

[BVL-10] Federal Office for Consumer Protection and Food Safety: Revocation of the approval of plant protection products with the active ingredient iprodione on March 5, 2018 , accessed on February 23, 2018.

[PSM-11] General Directorate Health and Food Safety of the European Commission: Entry on Iprodione in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on December 6, 2019.

[12] External identifiers or database links for dichlozolin : CAS number: 24201-58-9, EC number: 607-339-9, ECHA InfoCard: 100.119.152 , PubChem : 32253 , ChemSpider : 29909 , Wikidata : Q27155724 .

[13] External identifiers of or database links to isovaledione : CAS number: 70017-93-5, PubChem : 155450 , ChemSpider : 136942 , Wikidata : Q27274072 .

[14] External identifiers or database links for Myclozolin : CAS number: 54864-61-8, EC number: 259-379-8, ECHA InfoCard: 100.053.963 , PubChem : 92350 , ChemSpider : 83373 , Wikidata : Q27155719 .