Alloxydim

Alloxydim

Skeletal formula of alloxydim
Names
Preferred IUPAC name Methyl 2-hydroxy-6,6-dimethyl-4-oxo-3-[(E)-N-prop-2-enoxy-C-propylcarbonimidoyl]cyclohex-2-ene-1-carboxylate
Other names Carbodimedon Zizalon
Identifiers
CAS Number	55634-91-8
3D model (JSmol)	Interactive image
ChEBI	CHEBI:81949
ChEMBL	ChEMBL54789
ChemSpider	37860
ECHA InfoCard	100.054.284
EC Number	259-732-6
PubChem CID	135571111
UNII	6MJH7893J2
CompTox Dashboard (EPA)	DTXSID8047210
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−1
Hazards
Lethal dose or concentration (LD, LC):
LD50 (median dose)	2260 mg/kg (rat, oral) [1] >4300 mg/m3/4H (rat, inhalation) [1] >5 g/kg (rat, skin) [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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. ^[2] Its sodium salt is a hygroscopic, water-soluble colorless solid. ^[3]

Alloxydim's HRAC classification is Group A (Australia and global), or Group 1 (numeric). Group A herbicides inhibit acetyl CoA carboxylase, (ACCase). ^[4]

Synthesis

Alloxydim may be produced by a multi-step reaction from mesityl oxide with dimethyl malonate, butyryl chloride, and ethoxyamine. ^[5]

Uses

Alloxydim is a grass herbicide that acts by inhibiting acetyl-CoA carboxylase. ^[2] It was developed by Nippon Soda in 1976 ^{[6] [7]} and used from 1978 to 1992 in Germany. ^[8]

See also

• Butroxydim
• Sethoxydim
• Clethodim

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. "Classification of Herbicides According to Site of Action". WeedScience. Retrieved August 21, 2025.
5. Unger TA (1996). Pesticide Synthesis Handbook. William Andrew. p. 145. ISBN   978-0-8155-1853-2.
6. 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.
7. Schirmer PU (2012). Modern Crop Protection Compounds: Herbicides. John Wiley & Sons. p. 455. ISBN   978-3-527-32965-6.
8. 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.