Iprodione: Difference between revisions

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Revision as of 14:31, 9 August 2011 editCheMoBot (talk \| contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:WikiProject_Ch← Previous edit		Latest revision as of 03:21, 4 March 2023 edit undoHtmlzycq (talk \| contribs)Extended confirmed users, IP block exemptions3,917 edits removed Category:Isopropyl compounds; added Category:Isopropylamino compounds using HotCat
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	{{Unreferenced stub\|auto=yes\|date=December 2009}}
	{{Chembox		{{Chembox
			\| Watchedfields = changed
	\| verifiedrevid = ~~443877662~~		\| verifiedrevid = 443879220
	\|ImageFile=Iprodione.~~png~~		\| ImageFile =Iprodione 200.svg
	\|ImageSize=~~200px~~		\| ImageSize =
	\|IUPACName= 3-(3,5-dichlorophenyl)-''N''-isopropyl-2,4-dioxoimidazolidine-1-carboxamide
			\| PIN = 3-(3,5-Dichlorophenyl)-2,4-dioxo-''N''-(propan-2-yl)imidazolidine-1-carboxamide
	\|OtherNames=Glycophene<br>Promidione		\| OtherNames =Glycophene<br>Promidione
	\|Section1= {{Chembox Identifiers		\|Section1={{Chembox Identifiers
⚫	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
			\| CASNo_Ref = {{cascite\|correct\|CAS}}
		⚫	\| CASNo =36734-19-7
		⚫	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
	\| ChemSpiderID = 34418		\| ChemSpiderID = 34418
			\| EC_number = 253-178-9
	\| KEGG_Ref = {{keggcite\|correct\|kegg}}		\| KEGG_Ref = {{keggcite\|correct\|kegg}}
	\| KEGG = C11208		\| KEGG = C11208
Line 17:		Line 20:
	\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}		\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}
	\| StdInChIKey = ONUFESLQCSAYKA-UHFFFAOYSA-N		\| StdInChIKey = ONUFESLQCSAYKA-UHFFFAOYSA-N
	\| ~~CASNo_Ref~~ = {{~~cascite~~\|correct\|~~CAS~~}}		\| UNII_Ref = {{fdacite\|correct\|FDA}}
			\| UNII = S3AYV2A6EU
⚫	\| CASNo=36734-19-7
	\| PubChem=37517		\| PubChem =37517
	\| ChEBI_Ref = {{ebicite\|correct\|EBI}}		\| ChEBI_Ref = {{ebicite\|correct\|EBI}}
	\| ChEBI = 28909		\| ChEBI = 28909
	\| SMILES = O=C2N(c1cc(Cl)cc(Cl)c1)C(=O)CN2C(=O)NC(C)C		\| SMILES = O=C2N(c1cc(Cl)cc(Cl)c1)C(=O)CN2C(=O)NC(C)C
	}}		}}
	\|Section2= {{Chembox Properties		\|Section2={{Chembox Properties
	\|C=13\|H=13\|Cl=2\|N=3\|O=3		\| C=13 \| H=13 \| Cl=2 \| N=3 \| O=3
	\| MolarMass=330.16662		\| MolarMass =330.16662
	\| Appearance=		\| Appearance =White powder
	\| Density=		\| Density =
			\| MeltingPtC = 133.4
	\| MeltingPt=
			\| BoilingPtC = 164.5
	\| BoilingPt=
			\| BoilingPt_notes = (decomposes)
	\| Solubility=
			\| Solubility =12.2 ''mg/L'' at 20 °C <ref name=FAO>FAO, 2004 </ref>
⚫	}}
			\| Solvent1 = acetone
⚫	\|Section3= {{Chembox Hazards
			\| Solubility1 = 342 g/L
	\| MainHazards=
			\| Solvent2 = hexane
	\| FlashPt=
			\| Solubility2 = 0.59 g/L
	\| Autoignition=
			\| Solvent3 = acetonitrile
			\| Solubility3 = 168 g/L
			\| Solvent4 = dichloromethane
			\| Solubility4 = 450 g/L
			\| Solvent5 = ethyl acetate
			\| Solubility5 = 225 g/L
			\|SolubleOther = in ]: 147 g/L; in ]: 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 an ] ].		'''Iprodione''' is a ] ] and ].

	==Application==		==Application==
	~~Iprodion~~ is used on crops affected by ], ], ] 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.		Iprodione is used on crops affected by ], ], ] 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 ]). This chemical was developed originally by Rhône-Poulenc Agrochimie (later Aventis CropScience and in 2002 acquired by Bayer). ] on ~~iprodione~~ ~~are~~ ~~currently~~ ~~expired~~.		It has been marketed under the brand name "Rovral" and "Chipco green" (both brands of ]). 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.<ref name=FAO/>

			] (Now part of ]) discovered that iprodione kills ] and filed for patent protection for those uses.<ref>Reuters. May 8, 2009 {{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 }}</ref>
	In 2010 Iprodione was launched in the United States as a nematicide with the brand name "Enclosure" by the agbiotech company ].

			Iprodione was approved in the Turkish market under the brand name Devguard for use on tomatoes and cucumbers in 2009,<ref>AgroNews Nov. 2, 2009 </ref> and was approved in the US as Enclosure for use in commercial peanut production in May 2010.<ref>AgroNews. May. 24, 2010 </ref>
⚫	]
⚫	]
⚫	]
⚫	]

			Iprodione was approved in Europe in 2010,<ref>AgroNews. Sep. 3, 2010 </ref> but approval was not renewed in 2017.<ref>Regulation (EU) 2017/2091 </ref>
	{{Organic-compound-stub}}

			==References==
	]
			{{reflist}}
	]

			==External links==
			* {{PPDB\|403}}

		⚫	]
		⚫	]
		⚫	]
			]
			]
		⚫	]

Latest revision as of 03:21, 4 March 2023

Iprodione
Names

Preferred IUPAC name 3-(3,5-Dichlorophenyl)-2,4-dioxo-N-(propan-2-yl)imidazolidine-1-carboxamide
Other names Glycophene Promidione
Identifiers
CAS Number	36734-19-7
3D model (JSmol)	Interactive image
ChEBI	CHEBI:28909
ChemSpider	34418
ECHA InfoCard	100.048.328
EC Number	253-178-9
KEGG	C11208
PubChem CID	37517
UNII	S3AYV2A6EU
CompTox Dashboard (EPA)	DTXSID3024154
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
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:
Pictograms
Signal word	Warning
Hazard statements	H351, H410
Precautionary statements	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 , 100 kPa). Y verify (what is ?) Infobox references

Chemical compound

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.

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

Iprodione was approved in Europe in 2010, but approval was not renewed in 2017.

References

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

External links

Iprodione in the Pesticide Properties DataBase (PPDB)

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