Oxycarboxin

Oxycarboxin is an organic compound used as a fungicide.[1][2] It is an anilide.[3]

Oxycarboxin

Names
IUPAC name 6-methyl-4,4-dioxo-N-phenyl-2,3-dihydro-1,4-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
CAS Number	5259-88-1
3D model (JSmol)	Interactive image
ChEBI	CHEBI:7858
ChEMBL	ChEMBL1712057
ChemSpider	20048
ECHA InfoCard	100.023.697
KEGG	C10956
PubChem CID	21330
UNII	NPU5GBN17X
CompTox Dashboard (EPA)	DTXSID8034792
InChI InChI=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) Key: AMEKQAFGQBKLKX-UHFFFAOYSA-N
SMILES CC1=C(S(=O)(=O)CCO1)/C(=N\c2ccccc2)/O
Properties
Chemical formula	C12H13NO4S
Molar mass	267.30 g·mol^−1
Melting point	120 °C (248 °F; 393 K)
Solubility in water	moderate
Solubility	acetone, DMF, ethanol, and methanol
Related compounds
Related compounds	Triforine, Triclopyr
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Uses

Oxycarboxin is used to control rust diseases (e.g. soybean rust).[2]

History

Oxycarboxin has been commercially available since 1966.[1]

Preparation

Oxycarboxin is prepared from acetoacetanilide and 2-mercaptoethanol.[1]

References

1. Ackermann, Peter; Margot, Paul; Müller, Franz (2000). "Fungicides, Agricultural". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a12_085. ISBN 3527306730.
2. Shanmugasundaram, S.; Yeh, C.C.; Hartman, G.L.; Talekar, N.S. (1991). Vegetable Soybean Research Needs for Production and Quality Improvement (PDF). Taipei: Asian Vegetable Research and Development Center. pp. 86–87. ISBN 9789290580478. Retrieved 6 February 2016.
3. PubChem. "Oxycarboxin". PubChem. National Center for Biotechnology Information. Retrieved 2020-12-06.