Alloxydim

Structural formula
	Simplified structural formula without complete stereochemistry
General
Surname	Alloxydim
other names	(1 RS ) -3 - [( E ) -1- (Allyloxyimino) butyl] -4-hydroxy-6,6-dimethyl-2-oxocyclohex-3-ene-carboxylic acid methyl ester; 2,2-Dimethyl-4,6-dioxo-5 - {(1 E ) -1 - [(2-propen-1-yloxy) imino] butyl} cyclohexanecarboxylic acid methyl ester;
Molecular formula	C 17 H 25 NO 5
Brief description	colorless solid (sodium salt)
External identifiers / databases
EC number	259-732-6
ECHA InfoCard	100.054.284
PubChem	135571111
Wikidata	Q27155664
properties
Molar mass	323.39 g mol −1
Physical state	firmly
Melting point	185.5 ° C
Vapor pressure	> 0.133 mPa (25 ° C)
solubility	soluble in water; soluble in organic solvents;
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 332
	P: no P-phrases
Toxicological data	2600 mg kg −1 ( LD 50 , rat , oral ) ; > 2000 mg kg −1 ( LD 50 , rabbit , transdermal ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Alloxydim is a chemical compound from the group of cyclohexanediones .

Extraction and presentation

Alloxydim can be obtained through a multi-stage reaction of mesityl oxide with dimethyl malonate , butyryl chloride and ethoxyamine .

properties

Tautomeric stabilized sodium salt with no complete stereochemistry

As the sodium salt, alloxydim is a very hygroscopic, colorless solid that is soluble in water. In a dry state it is stable at 50 ° C for 30 days. It decomposes in acidic aqueous solution.

use

Alloxydim is used as a systemic, selective grass herbicide . It works by inhibiting acetyl-CoA carboxylase and is not approved in the EU. It was developed by Nippon Soda in 1976 and launched on the market in 1980. In the FRG it was approved from 1978 to 1989, in the GDR from 1980 to 1992.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h data sheet Alloxydim-sodium, PESTANAL at Sigma-Aldrich , accessed on August 10, 2017 ( PDF ).
↑ ^a ^b ^c Springer Environmental Lexicon . Springer-Verlag, 2013, ISBN 978-3-642-56998-2 , pp. 70 ( limited preview in Google Book search).
^ The Pesticide Encyclopedia . CABI, 2014, ISBN 978-1-78064-014-3 , pp. 17 ( limited preview in Google Book search).
↑ Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 978-0-8155-1853-2 , pp. 145 ( limited preview in Google Book search).
↑ Metabolic Pathways of Agrochemicals: Part 1: Herbicides and Plant Growth Regulators . Royal Society of Chemistry, 2007, ISBN 978-1-84755-138-2 , pp. 848 ( limited preview in Google Book search).
↑ Entry on Alloxydim in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on August 10, 2017.
↑ Synthesis of O-benzyl oximes by combination of phase transfer catalysis and ultrasound irradiation . In: Frontiers of Chemistry in China . tape 4 , no. 1 , 2009, ISSN 1673-3495 , p. 58-62 , doi : 10.1007 / s11458-009-0002-2 .
↑ Peter Ulrich Schirmer: Modern Crop Protection Compounds: Herbicides . John Wiley & Sons, 2012, ISBN 978-3-527-32965-6 , pp. 455 ( limited preview in Google Book search).
↑ Reports on Plant Protection Products 2009: Active Ingredients in Plant Protection Products ; Approval history and regulations of the Plant Protection Application Ordinance . Springer-Verlag, 2010, ISBN 978-3-0348-0029-7 , pp. 8 ( limited preview in Google Book search).

[Sigma-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h data sheet Alloxydim-sodium, PESTANAL at Sigma-Aldrich , accessed on August 10, 2017 ( PDF ).

[Springer-2] Springer Environmental Lexicon . Springer-Verlag, 2013, ISBN 978-3-642-56998-2 , pp. 70 ( limited preview in Google Book search).

[3] The Pesticide Encyclopedia . CABI, 2014, ISBN 978-1-78064-014-3 , pp. 17 ( limited preview in Google Book search).

[4] Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 978-0-8155-1853-2 , pp. 145 ( limited preview in Google Book search).

[5] Metabolic Pathways of Agrochemicals: Part 1: Herbicides and Plant Growth Regulators . Royal Society of Chemistry, 2007, ISBN 978-1-84755-138-2 , pp. 848 ( limited preview in Google Book search).

[PPDB-6] Entry on Alloxydim in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on August 10, 2017.

[7] Synthesis of O-benzyl oximes by combination of phase transfer catalysis and ultrasound irradiation . In: Frontiers of Chemistry in China . tape 4 , no. 1 , 2009, ISSN 1673-3495 , p. 58-62 , doi : 10.1007 / s11458-009-0002-2 .

[8] Peter Ulrich Schirmer: Modern Crop Protection Compounds: Herbicides . John Wiley & Sons, 2012, ISBN 978-3-527-32965-6 , pp. 455 ( limited preview in Google Book search).

[9] Reports on Plant Protection Products 2009: Active Ingredients in Plant Protection Products ; Approval history and regulations of the Plant Protection Application Ordinance . Springer-Verlag, 2010, ISBN 978-3-0348-0029-7 , pp. 8 ( limited preview in Google Book search).