DCMU

Structural formula
General
Surname	DCMU
other names	3- (3,4-dichlorophenyl) -1,1-dimethylurea; Diuron ® ; Karmex;
Molecular formula	C 9 H 10 Cl 2 N 2 O
Brief description	colorless crystalline solid
External identifiers / databases
EC number	206-354-4
ECHA InfoCard	100.005.778
PubChem	3120
Wikidata	Q425389
properties
Molar mass	233.0945 g · mol -1
Physical state	firmly
Melting point	158-159 ° C
boiling point	Decomposition at> 200 ° C
Vapor pressure	0.0011 m Pa (25 ° C)
solubility	practically insoluble in water (35 mg l −1 at 20 ° C)
safety instructions
H and P phrases	H: 302-351-373-410
	P: 273-301 + 312-330-391-501
MAK	Switzerland: 10 mg m −3 (measured as inhalable dust )
Toxicological data	1020 mg kg −1 ( LD 50 , rat , oral ) ; 3400 mg kg −1 ( LD 50 , rat , oral ) ; > 5000mg 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 .

DCMU is a phenyl urea - derivative , which as a herbicide is used and the photosynthesis inhibits plant.

It was introduced in 1954 by the Bayer company under the trade name Diuron as a weed control agent and is used to completely eradicate plants (broad-spectrum herbicide). It is used to protect wood and masonry and as a coating agent.

effect

DCMU is a selective herbicide that has systemic properties. It is mainly absorbed via the roots of the treated weed plants and transported further in them, so that it accumulates in the upper parts of the plants. The active ingredient inhibits photosynthesis in plants by inhibiting the transport of electrons between photosystem II and plastoquinone (PQ). Thus the electrons from the water splitting do not reach photosystem I (P700). This interrupts the electron transport chain , which is based on the transport of electrons through the electron transport chain from photosystem II to photosystem I. The effect can be measured by the fact that the chlorophylls of the plants show increased fluorescence. The cause of fluorescence is that the light energy absorbed can no longer be converted into chemical energy via the normal path of linear electron transport. The cyclic electron transport (PSI to ferredoxin to PQ to cytochrome b6f complex to PC to PSI), however, is not influenced.

use

Estimated US application rate in 2011

DCMU is used for selective weed control in sugar cane, grain and cotton cultivation as well as in viticulture, under ornamental trees and fruit trees. It is also used (in higher doses) in combination with other herbicides as a total and semitotal herbicide on paths and squares. DCMU is listed in Appendix I of the Plant Protection Directive 91/414 / EC and is therefore an approved active ingredient in Europe.

Together with Amitrol , DCMU was part of the common herbicide Ustinex .

It is also used in the field of material protection. Paints made from paints containing DCMU, e.g. B. facade paints or ship floor paints ( antifouling paints) remain free of algae growth. However, diuron is not effective against other fouling organisms (shellfish).

Admission

Plant protection products with this active ingredient are permitted in Switzerland and some EU countries , but not in Germany and Austria.

toxicity

DCMU is classified as extremely hazardous to the aquatic environment.

The German railway sat diuron one until 1996 to keep track systems plant free. After the suspicion arose that the agent could harm unborn babies and young children in high concentrations, the company decided not to use it. With the Plant Protection Application Ordinance , this application was also legally prohibited. On the basis of a study, the Federal Biological Research Center for Agriculture and Forestry and the Federal Environment Agency examined a relaxation of the ban on use in mid-2000. Since there was no effective alternative, the track system became increasingly weed.

The Federal Ministry of Food, Agriculture and Consumer Protection (BMELV) planned an even more extensive application restriction in its draft to amend the Plant Protection Application Ordinance in 2002. However, a study by the Fresenius Institute believes it is only possible under unfavorable conditions that DCMU can enter the groundwater. DCMU is potentially carcinogenic.

DCMU was included by the EU in 2012 in accordance with Regulation (EC) No. 1907/2006 (REACH) as part of substance evaluation in the Community's ongoing action plan ( CoRAP ). The effects of the substance on human health and the environment are re-evaluated and, if necessary, follow-up measures are initiated. DCMU inclusion was driven by concerns about other exposure / risk-based concerns and widespread use and as a potential endocrine disruptor . The re-evaluation started in 2014 and was carried out by Finland .

Web links

Entry on Diuron in the Consumer Product Information Database

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on Diuron. In: Römpp Online . Georg Thieme Verlag, accessed on March 4, 2014.
↑ ^a ^b ^c ^d ^e Entry on diuron in the GESTIS substance database of the IFA , accessed on July 23, 2016(JavaScript required) .
↑ Entry on Diuron in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values (search for 330-54-1 or DCMU ), accessed on November 2, 2015.
↑ EU Commission: Plant Protection - Assessment and Authorization . see there “Status of the active substances to be reviewed by the EU (Doc. 3010)”, accessed on July 14, 2009.
^ Directorate-General for Health and Food Safety of the European Commission: Entry on Diuron in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 25, 2016.
↑ Notification of re-admission of diuron? . In: Eisenbahn-Revue International , issue 7/2000, ISSN 1421-2811 , p. 291.
↑ Community rolling action plan ( CoRAP ) of the European Chemicals Agency (ECHA): Diuron , accessed on March 26, 2019.Template: CoRAP status / 2014

[Römpp-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on Diuron. In: Römpp Online . Georg Thieme Verlag, accessed on March 4, 2014.

[GESTIS-2] Entry on diuron in the GESTIS substance database of the IFA , accessed on July 23, 2016(JavaScript required) .

[CLP_100.005.778-3] Entry on Diuron in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .

[4] Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values (search for 330-54-1 or DCMU ), accessed on November 2, 2015.

[5] EU Commission: Plant Protection - Assessment and Authorization . see there “Status of the active substances to be reviewed by the EU (Doc. 3010)”, accessed on July 14, 2009.

[6] Directorate-General for Health and Food Safety of the European Commission: Entry on Diuron in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 25, 2016.

[eri-2000-291-7] Notification of re-admission of diuron? . In: Eisenbahn-Revue International , issue 7/2000, ISSN 1421-2811 , p. 291.

[8] Community rolling action plan ( CoRAP ) of the European Chemicals Agency (ECHA): Diuron , accessed on March 26, 2019.Template: CoRAP status / 2014