Oxycarboxin
Chemical compound
From Wikipedia, the free encyclopedia
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).[1][2][3]
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| Names | |
|---|---|
| Preferred IUPAC name
6-Methyl-4,4-dioxo-N-phenyl-3,4-dihydro-2H-1,4λ6-oxathiine-5-carboxamide | |
| Other names
Oxycarboxine; Dcmod; Oxicarboxin, Vitavax sulfone, Plantvax, Carbojet, 5,6-dihydro-2-methyl-1,4-oxathi-ine-3-carboxanilide-4,4-dioxide | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.023.697 |
| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C12H13NO4S | |
| Molar mass | 267.30 g·mol−1 |
| Melting point | 120 °C (248 °F; 393 K) |
| moderate | |
| Solubility | acetone, DMF, ethanol, and methanol |
| Related compounds | |
Related compounds |
Carboxin |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis
Oxyxarboxin was first made by the oxidation of carboxin, as disclosed in patents filed by Uniroyal.[4]
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.[5] The synthesis is completed by treatment with 30% hydrogen peroxide in acetic acid.[4]
Mechanism of action
Carboxin and oxycarboxin act by inhibition of succinate dehydrogenase (SDHI):[6] 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.[7][8]
Uses
Oxycarboxin is used to control rust diseases (e.g. soybean rust) at an application rate of 200–400 g/ha.[3][9]