Linuron

Structural formula
General
Surname	Linuron
other names	3- (3,4-dichlorophenyl) -1-methoxy-1-methylurea; N - (3,4-dichlorophenyl) - N ′ -methoxy- N ′ -methylurea;
Molecular formula	C 9 H 10 Cl 2 N 2 O 2
Brief description	colorless to white, odorless solid
External identifiers / databases
EC number	206-356-5
ECHA InfoCard	100.005.779
PubChem	9502
Wikidata	Q421476
properties
Molar mass	249.10 g mol −1
Physical state	firmly
density	1.69 g cm −3
Melting point	93-94 ° C
solubility	practically insoluble in water (63.8 mg l −1 at 20 ° C and pH 7)
safety instructions
H and P phrases	H: 302-351-360Df-373-410
	P: 201-260-273-280-308 + 313-391
Toxicological data	1150 mg kg −1 ( LD 50 , rat , oral ) ; 5000 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 .

Linuron is an active ingredient for crop protection and a chemical compound from the group of organic chlorine compounds and urea derivatives .

Extraction and presentation

Linuron can be obtained by reacting 3,4-dichlorophenyl isocyanate with N , O -dimethylhydroxylamine or by reacting hydroxylamine sulfate with 3,4-dichlorophenyl isocyanate and reacting the intermediate product formed with dimethyl sulfate .

properties

Linuron is a flammable, colorless to white, odorless solid that is practically insoluble in water. It is slowly hydrolyzed by acids and bases.

use

Estimated US application rate in 2011

Linuron is used as plant protection agents (selective herbicide used). It is used to control annual grasses and weeds, including cereals, vegetables and soybeans. Linuron works by inhibiting photosynthesis .

The permitted daily dose is 0.003, the acute reference dose is 0.03 and the acceptable user exposure is 0.009 milligrams per kilogram of body weight and day.

Admission

In the European Union, the active ingredient Linuron was approved for use as a herbicide with effect from January 1, 2004.

Due to the classification of the substance as toxic to reproduction , carcinogenic and endocrine disrupting and the risk for users, children and various wild animals, the EU Commission did not renew the approval on February 10, 2017. This regulation had to be transposed into national law by the member states by June 3, 2017; the use-by period must end on June 3, 2018 at the latest.

In Germany, Austria and Switzerland, pesticides containing this active ingredient are no longer permitted.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k Entry on Linuron in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .
↑ Entry on Linuron in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ Thomas A. Unger: Pesticide synthesis handbook . 1996, ISBN 978-0-8155-1401-5 ( page 242 in the Google book search).
^ M. Bahadir, H. Parlar, Michael Spiteller: Springer Umweltlexikon . Springer, 2000, ISBN 978-3-540-63561-1 ( page 709 in the Google book search).
^ Terence Robert Roberts, DH Hutson: Metabolic pathways of agrochemicals, Volume 2 . Royal Soc of Chemistry, 1999, ISBN 978-0-85404-499-3 ( page 744 in Google book search).
↑ ^a ^b Directorate-General for Health and Food Safety of the European Commission: Entry on Linuron in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on December 7, 2019.
↑ Directive 2003/31 / EC of the Commission of April 11, 2003 amending Council Directive 91/414 / EEC to include the active substances 2,4-DB, beta-cyfluthrin, cyfluthrin, iprodione, linuron, maleic hydrazide and pendimethalin .
↑ Implementing Regulation (EU) 2017/244 of the Commission of February 10, 2017 on the non-renewal of the approval for the active ingredient Linuron ... , accessed on December 4, 2017

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k Entry on Linuron in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .

[CLP_100.005.779-2] Entry on Linuron in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .

[Unger-3] Thomas A. Unger: Pesticide synthesis handbook . 1996, ISBN 978-0-8155-1401-5 ( page 242 in the Google book search).

[Springer-4] M. Bahadir, H. Parlar, Michael Spiteller: Springer Umweltlexikon . Springer, 2000, ISBN 978-3-540-63561-1 ( page 709 in the Google book search).

[Roberts2-5] Terence Robert Roberts, DH Hutson: Metabolic pathways of agrochemicals, Volume 2 . Royal Soc of Chemistry, 1999, ISBN 978-0-85404-499-3 ( page 744 in Google book search).

[PSM-6] Directorate-General for Health and Food Safety of the European Commission: Entry on Linuron in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on December 7, 2019.

[7] Directive 2003/31 / EC of the Commission of April 11, 2003 amending Council Directive 91/414 / EEC to include the active substances 2,4-DB, beta-cyfluthrin, cyfluthrin, iprodione, linuron, maleic hydrazide and pendimethalin .

[8] Implementing Regulation (EU) 2017/244 of the Commission of February 10, 2017 on the non-renewal of the approval for the active ingredient Linuron ... , accessed on December 4, 2017