alloxydim
{{Short description|Chemical compound}}
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{{Use mdy dates|date=November 2024}}
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| Name = Alloxydim
| ImageFile = Alloxydim_Structural_Formula_V1.svg
| ImageSize = 200px
| ImageName = Skeletal formula of alloxydim
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| PIN = Methyl 2-hydroxy-6,6-dimethyl-4-oxo-3-[(E)-N-prop-2-enoxy-C-propylcarbonimidoyl]cyclohex-2-ene-1-carboxylate
| OtherNames = {{ubl|Carbodimedon|Zizalon}}
| Section1={{Chembox Identifiers
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| ChEBI = 81949
| SMILES = CCC/C(=N\OCC=C)/C1=C(C(C(CC1=O)(C)C)C(=O)OC)O
| ChemSpiderID = 37860
| PubChem = 135571111
| UNII = 6MJH7893J2
| StdInChI = 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+
| StdInChIKey = ORFLOUYIJLPLPL-WOJGMQOQSA-N
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| ChEMBL = 54789
| CASNo = 55634-91-8
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| EINECS = 259-732-6
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| Section2={{Chembox Properties
| C=17 | H=25 | O=5 | N=1
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| LD50 = {{ubl|2260 mg/kg (rat, oral){{Cite book|title=The Pesticide Manual |volume=9 |date=1991 |page=21 |first1=Charles R. |last1=Worthing |first2=R. J. |last2=Hance |publisher=British Crop Protection Council |isbn=978-0-948404-42-9}}|>4300 mg/m3/4H (rat, inhalation)|>5 g/kg (rat, skin)}}
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Alloxydim is a chemical compound. Its formula is {{chem2|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.{{Cite book |title=Metabolic Pathways of Agrochemicals: Part 1: Herbicides and Plant Growth Regulators |publisher=Royal Society of Chemistry |date=2007 |page=848 |isbn=978-1-84755-138-2 |url=https://books.google.com/books?id=Sm0oDwAAQBAJ&pg=PA848}}
Synthesis
Alloxydim may be produced by a multi-step reaction from mesityl oxide with dimethyl malonate, butyryl chloride, and ethoxyamine.{{Cite book |last=Unger |first=Thomas A. |title=Pesticide Synthesis Handbook |publisher=William Andrew |date=1996 |page=145 |isbn=978-0-8155-1853-2 |url=https://books.google.com/books?id=-9cHDi8OOO4C }}
Uses
Alloxydim is a grass herbicide that acts by inhibiting acetyl-CoA carboxylase.{{PPDB|23|Name=Alloxydim|Date=2024-11-30}} It was developed by Nippon Soda in 1976{{Cite journal |first1=Jitai |last1=Li |first2=Xiaoliang |last2=Li |first3=Xianfeng |last3=Liu |first4=Jiejie |last4=Ma|title=Synthesis of O-benzyl oximes by combination of phase transfer catalysis and ultrasound irradiation |journal=Frontiers of Chemistry in China |volume=4 |issue=1 |date=2009 |pages=58–62 |doi=10.1007/s11458-009-0002-2}}{{Cite book |first=Peter Ulrich |last=Schirmer |title=Modern Crop Protection Compounds: Herbicides |publisher=John Wiley & Sons |date=2012 |page=455 |isbn=978-3-527-32965-6 |url=https://books.google.com/books?id=rZsaM-K2vdMC&pg=PA455}} and used from 1978 to 1992 in Germany.{{Cite book |title=Berichte zu Pflanzenschutzmitteln 2009: Wirkstoffe in Pflanzenschutzmitteln; Zulassungshistorie und Regelungen der Pflanzenschutz-Anwendungsverordnung |publisher=Springer-Verlag |date=2010 |page=8 |language=de |isbn=978-3-0348-0029-7 |url=https://books.google.com/books?id=kLkdBAAAQBAJ&pg=PA8}}