{{Chembox | Verifiedfields = | Watchedfields = | verifiedrevid = | Name = Oxycarboxin | ImageFile = Oxycarboxin.svg | PIN = 6-Methyl-4,4-dioxo-''N''-phenyl-3,4-dihydro-2''H''-1,4λ<sup>6</sup>-oxathiine-5-carboxamide | OtherNames = Oxycarboxine; Dcmod; Oxicarboxin, Vitavax sulfone, Plantvax, Carbojet, 5,6-dihydro-2-methyl-1,4-oxathi-ine-3-carboxanilide-4,4-dioxide |Section1={{Chembox Identifiers | CASNo = 5259-88-1 | CASNo_Ref = | PubChem = 21330 | ChemSpiderID = 20048 | ChemSpiderID_Ref = | EINECS = | UNNumber = | DrugBank = | DrugBank_Ref = | KEGG = C10956 | KEGG_Ref = | MeSHName = | ChEBI = 7858 | ChEBI_Ref = | ChEMBL = 1712057 | ChEMBL_Ref = | RTECS = | UNII = NPU5GBN17X | Beilstein = | Gmelin = | 3DMet = | SMILES = CC1=C(S(=O)(=O)CCO1)/C(=N\c2ccccc2)/O | StdInChI = 1S/C12H13NO4S/c1-9-11(18(15,16)8-7-17-9)12(14)13-10-5-3-2-4-6-10/h2-6H,7-8H2,1H3,(H,13,14) | StdInChI_Ref = | StdInChIKey = AMEKQAFGQBKLKX-UHFFFAOYSA-N | StdInChIKey_Ref = }} |Section2={{Chembox Properties | C = 12 | H = 13 | N = 1| O = 4| S = 1 | Density = | MeltingPtC = 120 | BoilingPtK = | LogP = | VaporPressure = | pKa = | pKb = | RefractIndex = | Solubility = moderate | SolubleOther = acetone, DMF, ethanol, and methanol }} |Section3={{Chembox Hazards | ExternalSDS = | GHSPictograms = | GHSSignalWord = | HPhrases = {{HPhrases|}} | PPhrases = {{PPhrases|}} | GHS_ref = | FlashPtC = | ExploLimits = | LD50 = }} |Section4={{Chembox Related | OtherCompounds = Carboxin }} }}
'''Oxycarboxin''' is an organic chemical used in agriculture to protect crops from fungal diseases. It was first marketed by Uniroyal in 1969 under the brand name '''Plantvax'''. The compound is a benzanilide analog which combines a heterocyclic acid with aniline to give an inhibitor of succinate dehydrogenase (SDHI).<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><ref name=Ullmann>{{cite journal|last1=Ackermann|first1=Peter|last2=Margot|first2=Paul|last3=Müller|first3=Franz|title=Fungicides, Agricultural|journal=Ullmann's Encyclopedia of Industrial Chemistry|date=2000|doi=10.1002/14356007.a12_085|isbn=3527306730}}</ref><ref name="SoyResearch">{{cite book |last1=Shanmugasundaram |first1=S.|last2=Yeh|first2=C.C. |last3=Hartman|first3=G.L. |last4=Talekar|first4=N.S. |title=Vegetable Soybean Research Needs for Production and Quality Improvement |date=1991|publisher=Asian Vegetable Research and Development Center|location=Taipei|isbn=9789290580478|pages=86–87|url=http://pdf.usaid.gov/pdf_docs/PNABK804.pdf|archive-url=https://web.archive.org/web/20160206192009/http://pdf.usaid.gov/pdf_docs/PNABK804.pdf|url-status=dead|archive-date=February 6, 2016|accessdate=6 February 2016}}</ref>
==Synthesis== Oxyxarboxin was first made by the oxidation of carboxin, as disclosed in patents filed by Uniroyal.<ref name=US3402241>{{cite patent |country=US |number=3402241 |status=patent |gdate=1968-09-17 |fdate=1965-11-05 |pridate=1965-11-05 |invent1 =von Schmeling, B. |invent2 = Kulka, M. |invent3 = Harrison, W.A. |title=Control of plant fungal and bacterial diseases with 2, 3-dihydro-5-carboximido-6-methyl-1, 4-oxathiin, mono-and di-oxides |assign1=Uniroyal Inc}}</ref> :500px Ethyl 2-chloroacetoacetate is treated with 2-mercaptoethanol and base, followed by cyclisation and water removal under acidic conditions. The resultant ethyl ester of the 1,4-oxathiine heterocycle is then formed into an amide with aniline using standard conditions via the carboxylic acid and acid chloride. This gives carboxin in high overall yield.<ref>{{cite journal |doi=10.1126/science.152.3722.659 |title=Systemic Fungicidal Activity of 1,4-Oxathiin Derivatives |date=1966 |last1=von Schmeling |first1=B. |last2=Kulka |first2=Marshall |journal=Science |volume=152 |issue=3722 |pages=659–660 |pmid=17779512 |bibcode=1966Sci...152..659V |s2cid=27561137 }}</ref> The synthesis is completed by treatment with 30% hydrogen peroxide in acetic acid.<ref name=US3402241/> == Mechanism of action == Carboxin and oxycarboxin act by inhibition of succinate dehydrogenase (SDHI):<ref>{{cite journal |doi=10.1017/S0016672300016098 |title=Three genes determine the carboxin sensitivity of mitochondrial succinate oxidation in ''Aspergillus nidulans'' |date=1975 |last1=Gunatilleke |first1=I. A. U. N. |last2=Arst |first2=H. N. |last3=Scazzocchio |first3=C. |journal=Genetical Research |volume=26 |issue=3 |pages=297–305 |pmid=178574 |doi-access=free }}</ref> they bind to the quinone reduction site of the enzyme complex, preventing ubiquinone from doing so. As a consequence, the tricarboxylic acid cycle and 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 }}</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>
==Uses== Oxycarboxin is used to control rust diseases (e.g. soybean rust) at an application rate of 200–400 g/ha.<ref name="SoyResearch" /><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=624}}</ref>
==History== Oxycarboxin has been commercially available since 1969, when it was introduced under the brand name Plantvax.<ref name=Ullmann /><ref>{{cite web |url=http://sitem.herts.ac.uk/aeru/ppdb/en/Reports/500.htm |title=Oxycarboxin |publisher=University of Hertfordshire |author=Pesticide Properties Database |date=2023-06-15 |access-date=2023-08-07 }}</ref>
==References== {{Reflist}}
Category:Anilides Category:Sulfones Category:Fungicides Category:Heterocyclic compounds with 1 ring