Oxycarboxin

Last updated
Oxycarboxin
Oxycarboxin.svg
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 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • 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
  • CC1=C(S(=O)(=O)CCO1)/C(=N\c2ccccc2)/O
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 using their brand name Plantvax. The compound is an anilide which combines a heterocyclic acid with aniline to give an inhibitor of succinate dehydrogenase (SDHI). [1] [2] [3]

Contents

Synthesis

Oxyxarboxin was first made by the oxidation of carboxin, as disclosed in patents filed by Uniroyal. [4]

Carboxin synthesis.svg

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]

History

Oxycarboxin has been commercially available since 1969, when it was introduced under the brand name Plantvax. [2] [10]

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References

  1. ↑ Walter, Harald (2016). "Fungicidal Succinate-Dehydrogenase-Inhibiting Carboxamides". In Lamberth, Clemens; Dinges, Jürgen (eds.). Bioactive Carboxylic Compound Classes: Pharmaceuticals and Agrochemicals. Wiley. pp. 405–425. doi:10.1002/9783527693931.ch31. ISBN   9783527339471.
  2. 1 2 Ackermann, Peter; Margot, Paul; Müller, Franz (2000). "Fungicides, Agricultural". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a12_085. ISBN   3527306730.
  3. 1 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.
  4. 1 2 USpatent 3402241,von Schmeling, B.; Kulka, M.& Harrison, W.A.,"Control of plant fungal and bacterial diseases with 2, 3-dihydro-5-carboximido-6-methyl-1, 4-oxathiin, mono-and di-oxides",issued 1968-09-17, assigned to Uniroyal Inc
  5. ↑ von Schmeling, B.; Kulka, Marshall (1966). "Systemic Fungicidal Activity of 1,4-Oxathiin Derivatives". Science. 152 (3722): 659–660. Bibcode:1966Sci...152..659V. doi:10.1126/science.152.3722.659. PMID   17779512. S2CID   27561137.
  6. ↑ Gunatilleke, I. A. U. N.; Arst, H. N.; Scazzocchio, C. (1975). "Three genes determine the carboxin sensitivity of mitochondrial succinate oxidation in Aspergillus nidulans". Genetical Research. 26 (3): 297–305. doi: 10.1017/S0016672300016098 . PMID   178574.
  7. ↑ Oyedotun, Kayode S.; Lemire, Bernard D. (2004). "The Quaternary Structure of the Saccharomyces cerevisiae Succinate Dehydrogenase". Journal of Biological Chemistry. 279 (10): 9424–9431. doi: 10.1074/jbc.M311876200 . PMID   14672929.
  8. ↑ Avenot, Hervé F.; Michailides, Themis J. (2010). "Progress in understanding molecular mechanisms and evolution of resistance to succinate dehydrogenase inhibiting (SDHI) fungicides in phytopathogenic fungi". Crop Protection. 29 (7): 643–651. doi:10.1016/j.cropro.2010.02.019.
  9. ↑ Worthing C.R., ed. (1987). The Pesticide Manual - A World Compendium (Eighth ed.). British Crop Protection Council. p. 624. ISBN   0948404019.
  10. ↑ Pesticide Properties Database (2023-06-15). "Oxycarboxin". University of Hertfordshire. Retrieved 2023-08-07.
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