Iprodione

Last updated
Iprodione
Iprodione 200.svg
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 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
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) Yes check.svgY
    Key: ONUFESLQCSAYKA-UHFFFAOYSA-N Yes check.svgY
  • 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
AppearanceWhite 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
Main hazards Limited evidence of carcinogenic effect
R-phrases (outdated) R40, R50/53
S-phrases (outdated) S35, S36/37
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)
Infobox references

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.

Contents

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]

Related Research Articles

Pesticide Substance used to destroy pests

Pesticides are substances that are meant to control pests. The term pesticide includes all of the following: herbicide, insecticides nematicide, molluscicide, piscicide, avicide, rodenticide, bactericide, insect repellent, animal repellent, antimicrobial, fungicide, and lampricide. The most common of these are herbicides which account for approximately 80% of all pesticide use. Most pesticides are intended to serve as plant protection products, which in general, protect plants from weeds, fungi, or insects. As an example, the fungus Alternaria solani is used to combat the aquatic weed Salvinia.

A nematicide is a type of chemical pesticide used to kill plant-parasitic nematodes. Nematicides have tended to be broad-spectrum toxicants possessing high volatility or other properties promoting migration through the soil. Aldicarb (Temik), a carbamate insecticide marketed by Bayer CropScience, is an example of a commonly used commercial nematicide. It is important in potato production, where it has been used for control of soil-borne nematodes. Aldicarb is a cholinesterase inhibitor, which prevents the breakdown of acetylcholine in the synapse. In case of severe poisoning, the victim dies of respiratory failure. It is no longer authorised for use in the EU and, in August 2010, Bayer CropScience announced that it planned to discontinue aldicarb by 2014. Human health safety and environmental concerns have resulted in the widespread deregistration of several other agronomically important nematicides. Prior to 1985, the persistent halocarbon DBCP was a widely used nematicide and soil fumigant. However, it was banned from use after being linked to sterility among male workers; the Dow Chemical company was subsequently found liable for more than $600 million in damages.

Agrochemical Any chemical used in agriculture

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Aldicarb Chemical compound (insecticide)

Aldicarb is a carbamate insecticide which is the active substance in the pesticide Temik. It is effective against thrips, aphids, spider mites, lygus, fleahoppers, and leafminers, but is primarily used as a nematicide. Aldicarb is a cholinesterase inhibitor which prevents the breakdown of acetylcholine in the synapse. In case of severe poisoning, the victim dies of respiratory failure.

Biopesticides, a contraction of 'biological pesticides', include several types of pest management intervention: through predatory, parasitic, or chemical relationships. The term has been associated historically with biological pest control – and by implication, the manipulation of living organisms. Regulatory positions can be influenced by public perceptions, thus:

Diquat Chemical compound

Diquat is the ISO common name for an organic dication that, as a salt with counterions such as bromide or chloride is used as a contact herbicide that produces desiccation and defoliation. Diquat is no longer approved for use in the European Union, although its registration in many other countries including the USA is still valid.

Devgen is a Belgium-based multinational agricultural biotechnology company. It uses biotechnology and molecular breeding technologies to develop varieties of food crops. Its technology is marketed by outlicensing or selling seeds in India and South-East Asia. Devgen also develops nematicides.

Acibenzolar-<i>S</i>-methyl Chemical compound

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Azoxystrobin Chemical compound

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Thiamethoxam Chemical compound

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Epoxiconazole Fungicide

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Pencycuron Chemical compound

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Fluxapyroxad Chemical compound

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Cyproconazole Chemical compound

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Fluopyram Chemical compound

Fluopyram is a fungicide and nematicide used in agriculture. It is used to control fungal diseases such as gray mold (Botrytis), powdery mildew, apple scab, Alternaria, Sclerotinia, and Monilinia. It is an inhibitor of succinate dehydrogenase.

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References