![]() | |
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) | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.023.697 |
KEGG | |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
| |
| |
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). |
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]
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]
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]
Oxycarboxin is used to control rust diseases (e.g. soybean rust) at an application rate of 200–400 g/ha. [3] [9]
Oxycarboxin has been commercially available since 1969, when it was introduced under the brand name Plantvax. [2] [10]