Sethoxydim

Structural formula
	Simplified structural formula without stereochemistry - mixture of several isomers
General
Surname	Sethoxydim
other names	(±) -2- (1- (Ethoxyimino) butyl) -5- (2- (ethylthio) propyl) -3-hydroxy-2-cyclohexen-1-one
Molecular formula	C 17 H 29 NO 3 S
Brief description	odorless solid
External identifiers / databases
EC number	277-682-3
ECHA InfoCard	100.070.600
PubChem	52923
Wikidata	Q15632899
properties
Molar mass	327.49 g mol −1
Physical state	firmly
density	1.043 g cm −3
boiling point	90 ° C (0.04 µbar)
solubility	sparingly soluble in water (4.7 g l −1 at 20 ° C); soluble in most organic solvents such as acetone , benzene , ethyl acetate , n-hexane and methanol ;
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 410
	P: 261-304 + 340 + 312-403 + 233
Toxicological data	3200 mg kg −1 ( LD 50 , rat , oral ) ; 5000 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 .

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

Extraction and presentation

Sethoxydim can be obtained by reacting ethyl mercaptan with crotonal , followed by reaction with acetone , dimethyl malonate , hydrolysis reagents, butyryl chloride and hydroxyethylamine .

properties

Sethoxydim is an odorless liquid / oil that is sparingly soluble in water. It is very unstable in water.

use

Sethoxydim is used as a selective herbicide against annual and perennial grasses. It is applied as a post-emergence herbicide and requires the addition of an oil adjuvant or nonionic surfactant for maximum effectiveness. According to the manufacturer sethoxydim can against Bahia grass ( Paspalum notatum ), blood crabgrass ( Digitaria sanguinalis ), downy brome ( Bromus tectorum ), Elymus repens ( Elytrigia repens ), ryegrass ( Lolium multiflorum ), wild oat ( Avena spp. ) And Panicum ( Panicum spp. ). The effect is based (similar to the herbicide fluazifop-P-butyl ) on the inhibition of the acetyl-CoA-carboxylase , an enzyme for the catalysis of an early step of the fatty acid synthesis of the plants.

In 2002 the substance was not included in the list of plant protection active ingredients approved in the European Union . Plant protection products with the active ingredient sethoxydim are not approved in any EU country, nor are they in Switzerland.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on sethoxydim in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .
↑ ^a ^b ^c ^d Entry on sethoxydim in the Hazardous Substances Data Bank , accessed on February 27, 2013.
↑ Sethoxydim data sheet , analytical standard at Sigma-Aldrich , accessed on January 27, 2019 ( PDF ).
↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 158 ( limited preview in Google Book search).
^ ^A ^b Terence Robert Roberts, David Herd Hutson: Metabolic Pathways of Agrochemicals: Part 1: Herbicides and Plant Growth ... Royal Society of Chemistry, 1998, ISBN 0-85404-494-9 , pp. 233 ( limited preview in Google Book search).
↑ invasive.org: Sethoxydim (PDF; 35 kB).
↑ General Directorate Health and Food Safety of the European Commission: Entry on sethoxydim in the EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on February 18, 2016.

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on sethoxydim in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .

[HSDB-2] Entry on sethoxydim in the Hazardous Substances Data Bank , accessed on February 27, 2013.

[Sigma-3] Sethoxydim data sheet , analytical standard at Sigma-Aldrich , accessed on January 27, 2019 ( PDF ).

[Thomas_A._Unger-4] Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 158 ( limited preview in Google Book search).

[Terence_Robert_Roberts,_David_Herd_Hutson-5] A ^b Terence Robert Roberts, David Herd Hutson: Metabolic Pathways of Agrochemicals: Part 1: Herbicides and Plant Growth ... Royal Society of Chemistry, 1998, ISBN 0-85404-494-9 , pp. 233 ( limited preview in Google Book search).

[invasive.org-6] vasive.org: Sethoxydim (PDF; 35 kB).

[PSM-7] General Directorate Health and Food Safety of the European Commission: Entry on sethoxydim in the EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on February 18, 2016.