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Alloxydim

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Chemical compound

Alloxydim
Skeletal formula of alloxydim
Names
Preferred IUPAC name Methyl 2-hydroxy-6,6-dimethyl-4-oxo-3-cyclohex-2-ene-1-carboxylate
Other names
  • Carbodimedon
  • Zizalon
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.054.284 Edit this at Wikidata
EC Number
  • 259-732-6
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C17H25NO5/c1-6-8-11(18-23-9-7-2)13-12(19)10-17(3,4)14(15(13)20)16(21)22-5/h7,14,19H,2,6,8-10H2,1,3-5H3/b18-11+Key: ORFLOUYIJLPLPL-WOJGMQOQSA-N
SMILES
  • CCC/C(=N\OCC=C)/C1=C(C(C(CC1=O)(C)C)C(=O)OC)O
Properties
Chemical formula C17H25NO5
Molar mass 323.389 g·mol
Hazards
Lethal dose or concentration (LD, LC):
LD50 (median dose)
  • 2260 mg/kg (rat, oral)
  • >4300 mg/m3/4H (rat, inhalation)
  • >5 g/kg (rat, skin)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Alloxydim is a chemical compound. Its formula is C17H25NO5. A member of the cyclohexenones, a methyl ester, and an ether, alloxydim is a post-emergence herbicide. Its sodium salt is a hygroscopic, water-soluble colorless solid.

Synthesis

Alloxydim may be produced by a multi-step reaction from mesityl oxide with dimethyl malonate, butyryl chloride, and ethoxyamine.

Uses

Alloxydim is a grass herbicide that acts by inhibiting acetyl-CoA carboxylase. It was developed by Nippon Soda in 1976 and used from 1978 to 1992 in Germany.

See also

References

  1. ^ Worthing CR, Hance RJ (1991). The Pesticide Manual. Vol. 9. British Crop Protection Council. p. 21. ISBN 978-0-948404-42-9.
  2. ^ Alloxydim in the Pesticide Properties DataBase (PPDB), accessed on 2024-11-30.
  3. Metabolic Pathways of Agrochemicals: Part 1: Herbicides and Plant Growth Regulators. Royal Society of Chemistry. 2007. p. 848. ISBN 978-1-84755-138-2.
  4. Unger TA (1996). Pesticide Synthesis Handbook. William Andrew. p. 145. ISBN 978-0-8155-1853-2.
  5. Li J, Li X, Liu X, Ma J (2009). "Synthesis of O-benzyl oximes by combination of phase transfer catalysis and ultrasound irradiation". Frontiers of Chemistry in China. 4 (1): 58–62. doi:10.1007/s11458-009-0002-2.
  6. Schirmer PU (2012). Modern Crop Protection Compounds: Herbicides. John Wiley & Sons. p. 455. ISBN 978-3-527-32965-6.
  7. Berichte zu Pflanzenschutzmitteln 2009: Wirkstoffe in Pflanzenschutzmitteln; Zulassungshistorie und Regelungen der Pflanzenschutz-Anwendungsverordnung (in German). Springer-Verlag. 2010. p. 8. ISBN 978-3-0348-0029-7.
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