Iprodione

Iprodione

Names
IUPAC name 3-(3,5-Dichlorophenyl)-N-isopropyl-2,4-dioxoimidazolidine-1-carboxamide
Other names Glycophene Promidione
Identifiers
CAS Number	36734-19-7
ChEBI	CHEBI:28909
ChemSpider	34418
Jmol interactive 3D	Image
KEGG	C11208
PubChem	37517
InChI 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) Key: ONUFESLQCSAYKA-UHFFFAOYSA-N 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
SMILES O=C2N(c1cc(Cl)cc(Cl)c1)C(=O)CN2C(=O)NC(C)C
Properties
Chemical formula	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)
Solubility in water	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
Main hazards	Limited evidence of carcinogenic effect
R-phrases	R40, R50/53
S-phrases	S35, S36/37
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Iprodione is a hydantoin fungicide and nematicide.

Application

Iprodion 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 scrubs 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 discovered that iprodione kills nematodes and filed for patent protection for those uses.^[2] Iprodione was approved in the Turkish market under the brandname Devguard for use on tomatoes and cucumbers in 2009,^[3] was approved in Europe in 2010,^[4] and was approved in the US as Enclosure for use in commercial peanut production in May 2010.^[5]

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
3. AgroNews Nov. 2, 2009 Devgens nematicide Devguard receive regulatory approval in Turkey
4. AgroNews. Sep. 3, 2010 EU approved iprodione’s use extension
5. AgroNews. May. 24, 2010 Devgen launches Enclosure nematicide in U.S.

External Links

• Iprodione in the Pesticide Properties DataBase (PPDB)