Metoxuron

Structural formula
General
Surname	Metoxuron
other names	3- (3-chloro-4-methoxyphenyl) -1,1-dimethylurea
Molecular formula	C 10 H 13 ClN 2 O 2
Brief description	colorless crystalline substance
External identifiers / databases
EC number	243-433-2
ECHA InfoCard	100,039,470
PubChem	29863
ChemSpider	27749
Wikidata	Q22808428
properties
Molar mass	228.69 g mol −1
Physical state	firmly
density	0.8 g cm −3 (20 ° C)
Melting point	126-127 ° C
boiling point	Decomposes on heating
solubility	very little in water (678 mg l −1 ); Soluble in acetone , diethyl ether , toluene ;
safety instructions
GHS hazard labeling from Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary Caution
H and P phrases	H: 410
	P: 273-501
Toxicological data	1600 mg kg −1 ( LD 50 , rat , 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 .

Metoxuron is an organic compound that belongs to the group of urea derivatives and chlorinated compounds. The substance is used as a herbicide, which was first introduced in 1968 by Sandoz .

presentation

The substance can be prepared starting from 3-chloro-4-methoxyphenyl isocyanate by reacting dimethylamine .

properties

The substance is a selective herbicide against weeds and occasionally weed grasses in the cultivation of carrots and winter cereals . As this, it inhibits the Hill reaction in photosystem II during photosynthesis . The compound has a high toxicity towards aquatic organisms; toxicity has not been described for either bees or humans. No pesticides containing this active ingredient are permitted in the EU . The connection is usually verified by HPLC .

Individual evidence

↑ ^a ^b A. Eben: Urea herbicides (Metoxuron, Monuron, Mono-linuron, Metobromuron, Diuron, Isoproturon, Linuron, Neburon) . In: The MAK Collection for Occupational Health and Safety: Annual Thresholds and Classifications for the Workplace . 2000, doi : 10.1002 / 3527600418.amherbicidd0012 ( Open Access ).
↑ ^a ^b ^c ^d ^e ^f ^g Entry on Metoxuron in the GESTIS substance database of the IFA , accessed on May 3, 2019 (JavaScript required)
↑ ^a ^b Kalyani Paranjape, Vasant Gowariker, VN Krishnamurthy, Sugha Gowariker: The Pesticide Encyclopedia . CABI, 2014, ISBN 978-1-78064-014-3 , pp. 310 ( limited preview in Google Book Search [accessed May 3, 2019]).
↑ Entry on Metoxuron in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on May 3, 2019. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ Metoxuron data sheet from Sigma-Aldrich , accessed on May 3, 2019 ( PDF ).

↑ ^a ^b Entry on Metoxuron. In: Römpp Online . Georg Thieme Verlag, accessed on May 3, 2019.

[Nachweis-1] A. Eben: Urea herbicides (Metoxuron, Monuron, Mono-linuron, Metobromuron, Diuron, Isoproturon, Linuron, Neburon) . In: The MAK Collection for Occupational Health and Safety: Annual Thresholds and Classifications for the Workplace . 2000, doi : 10.1002 / 3527600418.amherbicidd0012 ( Open Access ).

[GESTIS-2] ↑ ^a ^b ^c ^d ^e ^f ^g Entry on Metoxuron in the GESTIS substance database of the IFA , accessed on May 3, 2019 (JavaScript required)

[Synthese-3] Kalyani Paranjape, Vasant Gowariker, VN Krishnamurthy, Sugha Gowariker: The Pesticide Encyclopedia . CABI, 2014, ISBN 978-1-78064-014-3 , pp. 310 ( limited preview in Google Book Search [accessed May 3, 2019]).

[CLP_100.039.470-4] Entry on Metoxuron in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on May 3, 2019. Manufacturers or distributors can expand the harmonized classification and labeling .

[Sigma-5] Metoxuron data sheet from Sigma-Aldrich , accessed on May 3, 2019 ( PDF ).

[Römpp-6] Entry on Metoxuron. In: Römpp Online . Georg Thieme Verlag, accessed on May 3, 2019.