# Mepronil

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Mepronil
> Markdown URL: https://mediated.wiki/source/Mepronil.md
> Source: https://en.wikipedia.org/wiki/Mepronil
> Source revision: 1331478625
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{Chembox
| ImageFile = Mepronil.svg
| ImageSize =
| ImageAlt =
<!-- Names -->
| IUPACName = 2-methyl-''N''-(3-propan-2-yloxyphenyl)benzamide
| OtherNames = KCO-1
<!-- Sections -->
| Section1 = {{Chembox Identifiers
| CASNo = 55814-41-0
| CASNo_Ref = {{cascite|correct|CAS}}
|EINECS = 611-317-4
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = QJK1MXY8DW
| ChEBI = 81823
| ChEMBL = 1615095
| SMILES = CC1=CC=CC=C1C(=O)NC2=CC(=CC=C2)OC(C)C
|  PubChem = 41632
|  ChemSpiderID = 37994
|  StdInChI = 1S/C17H19NO2/c1-12(2)20-15-9-6-8-14(11-15)18-17(19)16-10-5-4-7-13(16)3/h4-12H,1-3H3,(H,18,19)
|  StdInChIKey = BCTQJXQXJVLSIG-UHFFFAOYSA-N
  }}
| Section2 = {{Chembox Properties
|Properties_ref= <ref name=lgc>{{cite web |url=https://assets.lgcstandards.com/sys-master%2Fpdfs%2Fh59%2Fh2e%2F10607206137886%2FSDS_DRE-C14890000_ST-WB-MSDS-5506648-1-1-1.PDF |website=lgcstandards.com |date=2023-11-01 |access-date=2024-05-04 |title=Safety data sheet }}</ref>
| C=17 | H=19 | N=1 | O=2
| Appearance = Off-white powder
| Odor = 
| Density = 1.11 g/cm<sup>3</sup>
| MeltingPtC = 91.4
| MeltingPt_ref = 
| BoilingPt =
|LogP = 3.66
| Solubility = Slightly soluble (12.1 mg/L, 20 °C)
| SolubleOther = 
| Solvent = 
  }}
| Section3 = {{Chembox Hazards
| Hazards_ref=<ref name=pubchem >{{cite web |url=https://pubchem.ncbi.nlm.nih.gov/compound/41632 |title=Mepronil |access-date=2024-05-04}}</ref>
| MainHazards =
| FlashPt =
| AutoignitionPt =
  }}
}}

'''Mepronil''' is a fungicide used as a [seed treatment](/source/seed_treatment) or [foliar spray](/source/Pesticide_application) in agriculture to protect crops from fungal diseases. It was first marketed by Kumiai Chemical Industries in 1981 using their brand name '''Basitac'''.<ref name=PPDB>{{cite web |url=http://sitem.herts.ac.uk/aeru/ppdb/en/Reports/438.htm |title=Mepronil |publisher=University of Hertfordshire |author=Pesticide Properties Database }}</ref> The compound is a [benzanilide](/source/benzanilide) which combines [2-methylbenzoic acid](/source/2-methylbenzoic_acid) with the O-[isopropyl](/source/isopropyl) derivative of [3-aminophenol](/source/3-aminophenol) to give an inhibitor of [succinate dehydrogenase](/source/succinate_dehydrogenase) (SDHI).<ref name=BCPC8>{{Cite book |isbn=0948404019 | title = The Pesticide Manual - A World Compendium | edition = Eighth | editor = Worthing C.R. | publisher = British Crop Protection Council | date = 1987 |page=489 }}</ref><ref name=Walter>{{cite book |doi=10.1002/9783527693931.ch31 |chapter=Fungicidal Succinate-Dehydrogenase-Inhibiting Carboxamides |title=Bioactive Carboxylic Compound Classes: Pharmaceuticals and Agrochemicals |year=2016 |last1=Walter |first1=Harald |editor-last1=Lamberth |editor-first1=Clemens |editor-first2=Jürgen |editor-last2= Dinges |publisher=Wiley |pages=405–425 |isbn=9783527339471 }}</ref>
==History==
Inhibition of succinate dehydrogenase, the complex II in the [mitochondrial](/source/mitochondrial) respiration chain, has been known as a fungicidal mechanism of action since the first examples were marketed in the 1960s. The first compound in this class was [carboxin](/source/carboxin), which had a narrow spectrum of useful biological activity, mainly on [basidiomycetes](/source/basidiomycetes) and was used as a [seed treatment](/source/seed_treatment).<ref name=Walter/><ref name=FRAC>{{cite web |url=https://www.frac.info/frac-teams/working-groups/sdhi-fungicides/information |title=History of SDHI-fungicides |website=frac.info |access-date=2024-05-04 }}</ref> Many further examples of this mechanism of action were developed by crop protection companies seeking compounds with improved properties and mepronil was developed owing to its effectiveness as a foliar application  and by seed treatment.<ref name=BCPC8/><ref name=Walter/><ref name=Kawada>{{cite journal |doi=10.1584/jpestics.10.315 |title=Development of a New Fungicide, Mepronil |date=1985 |last1=Kawada |first1=Seigo |last2=Sakamoto |first2=Akira |last3=Shimazaki |first3=Isao |journal=Journal of Pesticide Science |volume=10 |issue=2 |pages=315–324 |doi-access=free }}</ref>
==Synthesis==
Mepronil can be made via the [Schotten–Baumann reaction](/source/Schotten%E2%80%93Baumann_reaction) of 2-methylbenzoyl chloride with 3-isopropoxyaniline.<ref>{{cite patent |country=US |number=3937840 |status=patent |title=Compositions and methods of combatting bacteria and fungi using 2-methylbenzanilide derivatives |pubdate=1976-02-10 |fdate=1974-07-17 |pridate=1975-08-15 |invent1=Chiyomaru, I |invent2=Kawada, S |invent3= Takita, K |assign1=Kumiai Chemical Industry Co Ltd }}</ref><ref>{{cite book |isbn=0815514018 |url=https://books.google.com/books?id=-9cHDi8OOO4C&pg=PA33  | title=Pesticide Synthesis Handbook | last1=Unger | first1=Thomas A. | date=31 December 1996 | publisher=William Andrew |page=33 }}</ref>
== Mechanism of action ==
SDHI of this type act by binding at the quinone reduction site of the enzyme complex, preventing [ubiquinone](/source/ubiquinone) from doing so. As a consequence, the [tricarboxylic acid cycle](/source/tricarboxylic_acid_cycle) and [electron transport chain](/source/electron_transport_chain) cannot function.<ref>{{cite journal |doi=10.1074/jbc.M311876200 |doi-access=free |title=The Quaternary Structure of the Saccharomyces cerevisiae Succinate Dehydrogenase |year=2004 |last1=Oyedotun |first1=Kayode S. |last2=Lemire |first2=Bernard D. |journal=Journal of Biological Chemistry |volume=279 |issue=10 |pages=9424–9431 |pmid=14672929 |bibcode=2004JBiCh.279.9424O }}</ref><ref>{{cite journal |doi=10.1016/j.cropro.2010.02.019 |title=Progress in understanding molecular mechanisms and evolution of resistance to succinate dehydrogenase inhibiting (SDHI) fungicides in phytopathogenic fungi |year=2010 |last1=Avenot |first1=Hervé F. |last2=Michailides |first2=Themis J. |journal=Crop Protection |volume=29 |issue=7 |pages=643–651 |bibcode=2010CrPro..29..643A }}</ref>
== Usage ==
Mepronil has been used since 1981 as a [seed treatment](/source/seed_treatment) to control ''[Rhizoctonia solani](/source/Rhizoctonia_solani)'' on vegetables. It is also used by foliar application to control ''R. solani'' on rice, ''[Gymnosporangium fuscum](/source/Gymnosporangium_fuscum)'' (rust) on pears and ''[Puccinia chrysanthemi](/source/List_of_Puccinia_species)'' on chrysanthemums.<ref name=BCPC8/> As of 2024 it is no longer registered for use, having been superseded by alternative SDHI products.<ref name=PPDB/><ref name=Walter/>
== Resistance management ==
Fungal populations have the ability to develop [resistance](/source/fungicide_resistance) to SDHI inhibitors. This potential can be mitigated by careful [management](/source/Integrated_pest_management). Reports of individual pest species becoming resistant are monitored by manufacturers, regulatory bodies such as the EPA and the [Fungicides Resistance Action Committee](/source/Fungicide) (FRAC).<ref>{{cite web |url=https://www.frac.info/ |title=Fungicides Resistance Action Committee website}}</ref> The risks of resistance developing can be reduced by using a mixture of two or more fungicides which each have activity on relevant pests but with unrelated mechanisms of action. FRAC assigns fungicides into classes so as to facilitate this.<ref name=FRAC/>
==Brands==
Mepronil is the [ISO](/source/International_Organization_for_Standardization) [common name](/source/trivial_name)<ref>{{cite web |url=http://www.bcpcpesticidecompendium.org/mepronil.html |title=Compendium of Pesticide Common Names: Mepronil |publisher=BCPC |access-date=2024-05-04}}</ref> for the active ingredient which is [formulated](/source/Pesticide_formulation) into the branded product sold to end-users. Basitac was the brand name used for Kumiai's products.<ref name=PPDB/>

==References==
{{reflist}}

Category:Fungicides
Category:Benzanilides
Category:Isopropyl compounds
Category:Phenol ethers

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Adapted from the Wikipedia article [Mepronil](https://en.wikipedia.org/wiki/Mepronil) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Mepronil?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.