Iprodione

{{Chembox

| Watchedfields = changed

| verifiedrevid = 443879220

| ImageFile =Iprodione 200.svg

| ImageSize =

| PIN = 3-(3,5-Dichlorophenyl)-2,4-dioxo-N-(propan-2-yl)imidazolidine-1-carboxamide

| OtherNames =Glycophene
Promidione

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo =36734-19-7

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 34418

| EC_number = 253-178-9

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = C11208

| 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)

| InChIKey = ONUFESLQCSAYKA-UHFFFAOYAC

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = ONUFESLQCSAYKA-UHFFFAOYSA-N

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = S3AYV2A6EU

| PubChem =37517

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 28909

| SMILES = O=C2N(c1cc(Cl)cc(Cl)c1)C(=O)CN2C(=O)NC(C)C

}}

|Section2={{Chembox Properties

| C=13 | H=13 | Cl=2 | N=3 | O=3

| MolarMass =330.16662

| Appearance =White powder

| Density =

| MeltingPtC = 133.4

| BoilingPtC = 164.5

| BoilingPt_notes = (decomposes)

| Solubility =12.2 mg/L at 20 °C FAO, 2004 [http://www.fao.org/fileadmin/templates/agphome/documents/Pests_Pesticides/Specs/Iprodione06.pdf FAO Specifications and Evaluations for Agricultural Pesticides: Iprodione]

| Solvent1 = acetone

| Solubility1 = 342 g/L

| Solvent2 = hexane

| Solubility2 = 0.59 g/L

| Solvent3 = acetonitrile

| Solubility3 = 168 g/L

| Solvent4 = dichloromethane

| Solubility4 = 450 g/L

| Solvent5 = ethyl acetate

| Solubility5 = 225 g/L

|SolubleOther = in toluene: 147 g/L; in octanol: 10 g/L

}}

|Section3={{Chembox Hazards

| GHSPictograms = {{GHS08}}{{GHS09}}

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|351|410}}

| PPhrases = {{P-phrases|201|202|273|281|308+313|391|405|501}}

| MainHazards =Limited evidence of carcinogenic effect

| FlashPt =

| AutoignitionPt =

}}

}}

Iprodione is a hydantoin fungicide and nematicide.

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.

DevGen NV (Now part of Syngenta) discovered that iprodione kills nematodes and filed for patent protection for those uses.Reuters. May 8, 2009 [https://www.reuters.com/article/2009/05/08/idUS193822+08-May-2009+MW20090508 2010 launch of Devgen's nematicide "Enclosure(R)" in the United States] {{webarchive|url=https://web.archive.org/web/20150924141821/http://www.reuters.com/article/2009/05/08/idUS193822+08-May-2009+MW20090508 |date=2015-09-24 }}

Iprodione was approved in the Turkish market under the brand name Devguard for use on tomatoes and cucumbers in 2009,AgroNews Nov. 2, 2009 [http://news.agropages.com/News/NewsDetail---1862.htm Devgens nematicide Devguard receive regulatory approval in Turkey] and was approved in the US as Enclosure for use in commercial peanut production in May 2010.AgroNews. May. 24, 2010 [http://news.agropages.com/News/NewsDetail---2448.htm Devgen launches Enclosure nematicide in U.S.]

Iprodione was approved in Europe in 2010,AgroNews. Sep. 3, 2010 [http://news.agropages.com/News/NewsDetail---2826.htm EU approved iprodione’s use extension] but approval was not renewed in 2017.Regulation (EU) 2017/2091 [http://eur-lex.europa.eu/legal-content/EN/TXT/?qid=1512655318141&uri=CELEX:32017R2091]

References

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