Cycloxydim

Structural formula
	Structural formula without stereochemistry
General
Surname	Cycloxydim
other names	(5 RS ) -2 - [( EZ ) -1- (ethoxyimino) butyl] -3-hydroxy-5 - [(3 RS ) -thian-3-yl] cyclohex-2-en-1-one; 2- [1- (ethoxyimino) butyl] -3-hydroxy-5- (tetrahydro-2 H -thiopyran-3-yl) -2-cyclohexen-1-one;
Molecular formula	C 17 H 27 NO 3 S
Brief description	colorless solid
External identifiers / databases
EC number	405-230-9
ECHA InfoCard	100.100.681
PubChem	91765
Wikidata	Q3008606
properties
Molar mass	325.47 g mol −1
Physical state	firmly
density	1.12 g cm −3 ( bulk density )
Melting point	37 ° C
boiling point	200 ° C (decomposition)
pK s value	4.17 (25 ° C)
solubility	practically insoluble in water (53 mg l −1 at 25 ° C); soluble in acetone, ethanol, hexane and ethyl acetate;
safety instructions
GHS hazard labeling from Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary Caution
H and P phrases	H: 361d
	P: 201-308 + 313
Toxicological data	3940 mg kg −1 ( LD 50 , rat , oral ) ; > 5000 mg kg −1 ( LD 50 , mouse , oral ) ; > 2000 mg kg −1 ( LD 50 , rat , transdermal ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Cycloxydim is a mixture of several isomeric chemical compounds from the group of cyclohexanediones .

properties

Cycloxydim is a colorless solid that is practically insoluble in water. It is unstable in an acidic environment.

use

Cycloxydim is used as a herbicide against grasses. The effect is based on the inhibition of fatty acid biosynthesis, more precisely acetyl-CoA carboxylase (ACCase). It has been approved as a plant protection product in Germany since 1991 .

Corn belongs to the grass family and is therefore susceptible to cycloxydim. However, through mutagenesis , cycloxydim-tolerant maize has been developed. The herbicide is also used in rapeseed, beet, potato, lamb's lettuce, ornamental plants and field beans.

Admission

Cycloxydim has been approved for use as a herbicide in the countries of the European Union since June 1, 2011. The approval expires on May 31, 2023 Template: future / in 5 years, provided that no new approval is granted. In Germany, Austria and Switzerland, plant protection products (e.g. Focus, Focus Plus and Focus Ultra) with this active ingredient are approved.

Web links

EU: Review report for the active substance cycloxydim (PDF; 177 kB), 23 November 2010.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on cycloxidime in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on August 1, 2013.
↑ ^a ^b entry to Cycloxidim in GESTIS Bank of IFA , accessed on August 25, 2016(JavaScript required) .
↑ Entry on cycloxydim (ISO); 2- (N-ethoxybutanimidoyl) -3-hydroxy-5- (tetrahydro-2H-thiopyran-3-yl) cyclohex-2-en-1-one in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on 1. August 2016. Manufacturers or distributors can extend the harmonized classification and labeling .
↑ ^a ^b ^c FAO : Cycloxydim (PDF; 69 kB).
^ ^A ^b Terence Robert Roberts, DH Hutson: Metabolic pathways of agrochemicals . tape 2 . Royal Soc of Chemistry, 1999, ISBN 978-0-85404-499-3 (English, limited preview in Google book search).
↑ Peter Brandt: Reports on Plant Protection Products 2009. Active Ingredients in Plant Protection Products . Approval history and regulations of the Plant Protection Application Ordinance. Springer, 2010, ISBN 978-3-0348-0028-0 , pp. 13 ( limited preview in Google Book search).
↑ DUO system ( Memento from March 4, 2016 in the Internet Archive )
↑ Directive 2011/4 / EU of the Commission of January 20, 2011 amending Council Directive 91/414 / EEC to include the active substance cycloxydim and amending Decision 2008/934 / EC
↑ General Directorate Health and Food Safety of the European Commission: Entry on Cycloxydim in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 13, 2016.

[PPDB-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on cycloxidime in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on August 1, 2013.

[GESTIS-2] try to Cycloxidim in GESTIS Bank of IFA , accessed on August 25, 2016(JavaScript required) .

[CLP_100.100.681-3] Entry on cycloxydim (ISO); 2- (N-ethoxybutanimidoyl) -3-hydroxy-5- (tetrahydro-2H-thiopyran-3-yl) cyclohex-2-en-1-one in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on 1. August 2016. Manufacturers or distributors can extend the harmonized classification and labeling .

[FAO-4] FAO : Cycloxydim (PDF; 69 kB).

[Roberts2-5] A ^b Terence Robert Roberts, DH Hutson: Metabolic pathways of agrochemicals . tape 2 . Royal Soc of Chemistry, 1999, ISBN 978-0-85404-499-3 (English, limited preview in Google book search).

[Peter_Brandt-6] Peter Brandt: Reports on Plant Protection Products 2009. Active Ingredients in Plant Protection Products . Approval history and regulations of the Plant Protection Application Ordinance. Springer, 2010, ISBN 978-3-0348-0028-0 , pp. 13 ( limited preview in Google Book search).

[7] DUO system ( Memento from March 4, 2016 in the Internet Archive )

[8] Directive 2011/4 / EU of the Commission of January 20, 2011 amending Council Directive 91/414 / EEC to include the active substance cycloxydim and amending Decision 2008/934 / EC

[PSM-9] General Directorate Health and Food Safety of the European Commission: Entry on Cycloxydim in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 13, 2016.