Names | |
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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 |
KEGG | |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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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 | |
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R-phrases (outdated) | R40, R50/53 |
S-phrases (outdated) | S35, S36/37 |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). | |
verify (what is ?) | |
Infobox references | |
Iprodione is a hydantoin fungicide and nematicide.
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]
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.
An agrochemical or agrichemical, a contraction of agricultural chemical, is a chemical product used in agriculture. In most cases, agrichemical refers to pesticides including insecticides, herbicides, fungicides and nematicides. It may also include synthetic fertilizers, hormones and other chemical growth agents, and concentrated stores of raw animal manure.
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 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-S-methyl is the ISO common name for an organic compound that is used as a fungicide. Unusually, it is not directly toxic to fungi but works by inducing systemic acquired resistance, the natural defence system of plants.
Azoxystrobin is the ISO common name for an organic compound that is used as a fungicide. It is a broad spectrum systemic active ingredient widely used in agriculture to protect crops from fungal diseases. It was first marketed in 1996 using the brand name Amistar and by 1999 it had been registered in 48 countries on more than 50 crops. In the year 2000 it was announced that it had been granted UK Millennium product status.
Cyhalothrin is the ISO common name for an organic compound that, in specific isomeric forms, is used as a pesticide. It is a pyrethroid, a class of synthetic insecticides that mimic the structure and properties of the naturally occurring insecticide pyrethrin which is present in the flowers of Chrysanthemum cinerariifolium. Pyrethroids such as cyhalothrin are often preferred as an active ingredient in agricultural insecticides because they are more cost-effective and longer acting than natural pyrethrins. λ-and γ-cyhalothrin are now used to control insects and spider mites in crops including cotton, cereals, potatoes and vegetables.
Thiamethoxam is a systemic insecticide in the class of neonicotinoids. It has a broad spectrum of activity against many types of insects. Thiamethoxam can be used as a seed dresser.
Epoxiconazole is a fungicide active ingredient from the class of azoles developed to protect crops. In particular, the substance inhibits the metabolism of fungi cells infesting useful plants, and thereby prevents the growth of the mycelia. Epoxiconazole also limits the production of conidia (mitospores). Epoxiconazole was introduced to the market by BASF SE in 1993 and can be found in many products and product mixtures targeting a large number of pathogens in various crops. Crops are, for example, cereals, soybeans, banana, rice, coffee, turnips, and red as well as sugar beets.
Mesotrione is the ISO common name for an organic compound that is used as a selective herbicide, especially in maize. It inhibits the enzyme 4-hydroxyphenylpyruvate dioxygenase (HPPD) and is sold under brand names including Callisto and Tenacity. It was first marketed by Syngenta in 2001.
Pencycuron is a phenylurea fungicide developed by Bayer Crop Science and marketed under the brand name Monceren. It has specific activity against the plant pathogen Rhizoctonia solani for which it was developed.
Fluxapyroxad is a broad-spectrum pyrazole-carboxamide fungicide used on a large variety of commercial crops. It stunts fungus growth by inhibiting the succinate dehydrogenase (SQR) enzyme. Application of fluxapyroxad helps prevent many wilts and other fungal infections from taking hold. As with other systemic pesticides that have a long chemical half-life, there are concerns about keeping fluxapyroxad out of the groundwater, especially when combined with pyraclostrobin. There is also concern that some fungi may develop resistance to fluxapyroxad.
Cyproconazole is an agricultural fungicide of the class of azoles, used on cereal crops, coffee, sugar beet, fruit trees and grapes, on sod farms and golf courses and on wood as a preservative. It was introduced to the market by then Sandoz in 1994.
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.
Fluazifop is the ISO common name for an organic compound that is used as a selective herbicide. The active ingredient is the 2R enantiomer at its chiral centre and this material is known as fluazifop-P when used in that form. More commonly, it is sold as its butyl ester, fluazifop-P butyl with the brand name Fusilade.
Aclonifen is a diphenyl ether herbicide which has been used in agriculture since the 1980s. Its mode of action has been uncertain, with evidence suggesting it might interfere with carotenoid biosynthesis or inhibit the enzyme protoporphyrinogen oxidase (PPO). Both mechanisms could result in the observed whole-plant effect of bleaching and the compound includes chemical features that are known to result in PPO effects, as seen with acifluorfen, for example. In 2020, further research revealed that aclonifen has a different and novel mode of action, targeting solanesyl diphosphate synthase which would also cause bleaching.