Iprodione

Iprodione is a hydantoin fungicide and nematicide.

Iprodione
Names
Preferred IUPAC name
3-(3,5-Dichlorophenyl)-2,4-dioxo-N-(propan-2-yl)imidazolidine-1-carboxamide
Other names
Glycophene
Promidione
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.048.328
EC Number
  • 253-178-9
KEGG
UNII
  • InChI=1S/C13H13Cl2N3O3/c1-7(2)16-12(20)17-6-11(19)18(13(17)21)10-4-8(14)3-9(15)5-10/h3-5,7H,6H2,1-2H3,(H,16,20) checkY
    Key: ONUFESLQCSAYKA-UHFFFAOYSA-N checkY
  • InChI=1/C13H13Cl2N3O3/c1-7(2)16-12(20)17-6-11(19)18(13(17)21)10-4-8(14)3-9(15)5-10/h3-5,7H,6H2,1-2H3,(H,16,20)
    Key: ONUFESLQCSAYKA-UHFFFAOYAC
  • O=C2N(c1cc(Cl)cc(Cl)c1)C(=O)CN2C(=O)NC(C)C
Properties
C13H13Cl2N3O3
Molar mass 330.16662
Appearance White powder
Melting point 133.4 °C (272.1 °F; 406.5 K)
Boiling point 164.5 °C (328.1 °F; 437.6 K) (decomposes)
12.2 mg/L at 20 °C [1]
Solubility in toluene: 147 g/L; in octanol: 10 g/L
Solubility in acetone 342 g/L
Solubility in hexane 0.59 g/L
Solubility in acetonitrile 168 g/L
Solubility in dichloromethane 450 g/L
Solubility in ethyl acetate 225 g/L
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Limited evidence of carcinogenic effect
GHS labelling:
GHS08: Health hazardGHS09: Environmental hazard
Warning
H351, H410
P201, P202, P273, P281, P308+P313, P391, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

Application

Iprodione is used on crops affected by Botrytis bunch rot, Brown rot, Sclerotinia and other fungal diseases in plants. It is currently applied in a variety of crops: fruit, vegetables, ornamental trees and shrubs and on lawns. It is a contact fungicide that inhibits the germination of fungal spores and it blocks the growth of the fungal mycelium.

It has been marketed under the brand name "Rovral" and "Chipco green" (both brands of Bayer CropScience). This chemical was developed originally by Rhône-Poulenc Agrochimie (later Aventis CropScience and in 2002 acquired by Bayer). As of 2004 there were no composition patents on iprodione.[1]

DevGen NV (Now part of Syngenta) discovered that iprodione kills nematodes and filed for patent protection for those uses.[2]

Iprodione was approved in the Turkish market under the brand name Devguard for use on tomatoes and cucumbers in 2009,[3] and was approved in the US as Enclosure for use in commercial peanut production in May 2010.[4]

Iprodione was approved in Europe in 2010,[5] but approval was not renewed in 2017.[6]

References
  1. FAO, 2004 FAO Specifications and Evaluations for Agricultural Pesticides: Iprodione
  2. Reuters. May 8, 2009 2010 launch of Devgen's nematicide "Enclosure(R)" in the United States Archived 2015-09-24 at the Wayback Machine
  3. AgroNews Nov. 2, 2009 Devgens nematicide Devguard receive regulatory approval in Turkey
  4. AgroNews. May. 24, 2010 Devgen launches Enclosure nematicide in U.S.
  5. AgroNews. Sep. 3, 2010 EU approved iprodione’s use extension
  6. Regulation (EU) 2017/2091
  • Iprodione in the Pesticide Properties DataBase (PPDB)
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