Atrazine

Structural formula
General
Surname	Atrazine
other names	6-chloro- N -ethyl- N -isopropyl-1,3,5-triazine-2,4-diamine; 6-chloro-4-ethylamino-2-isopropylamino-1,3,5-triazine;
Molecular formula	C 8 H 14 ClN 5
Brief description	white to beige colored, odorless solid
External identifiers / databases
EC number	217-617-8
ECHA InfoCard	100.016.017
PubChem	2256
ChemSpider	2169
DrugBank	DB07392
Wikidata	Q408652
properties
Molar mass	215.69 g · mol -1
Physical state	firmly
density	1.23 g cm −3 (22 ° C)
Melting point	176 ° C
boiling point	205 ° C
solubility	practically insoluble in water (33 mg l −1 at 22 ° C)
safety instructions
H and P phrases	H: 317-373-410
	P: 273-280-501
MAK	In relation to the inhalable fraction: DFG : 1 mg m −3 ; Switzerland: 2 mg m −3 ; Austria: 2 mg m −3 ;
Toxicological data	672 mg kg −1 ( LD 50 , rat , oral ) ; 7500 mg kg −1 ( LD 50 , rabbit , oral ) ; 5.2 mg l −1 (4 h) ( LD 50 , rat , inh. ) ; 0.22–76 mg l −1 ( LC 50 , fish , 96 hours ) ; 0.374–72 mg l −1 ( LC 50 , crustaceans , 48 hours ) ; 4.6–115 mg l −1 ( EC 50 , crustaceans , 48 hours ) ; 0.00453–67.7 mg l −1 ( EC 50 , algae , 72 hours ) ; 0.004–74.5 mg l −1 ( EC 50 , algae , 96 hours ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Atrazine is the common name of a herbicide from the chlorine triazine family . Some trade names are Aatrex, Aktikon, Alazine, Atred, Atranex, Atrataf, Atratol, Azinotox, Crisazina, Farmco Atrazine, G-30027, Gesaprim, Giffex 4L, Malermais, Primatol, Simazat, Weedex, Zeapos and Zeazin.

Manufacturing

Synthesis principle for triazines

Atrazine is made by the stepwise reaction of cyanuric chloride with ethylamine and isopropylamine .

The third chlorine substituent is less easily substitutable. During degradation reactions, the slow hydrolytic degradation begins here ; nucleophilic NH or SH functions of peptides react much faster than water .

properties

Atrazine works by inhibiting photosynthesis in plants. It binds to the quinone Q _B (the third link in the electron transport chain in photosystem II after pheophytin and Q _A ) and thus interrupts the electron transport. It degrades relatively slowly in the environment through hydrolysis .

Hydrolytic degradation of atrazine

Atrazine is harmful to organisms in different ways. Even in very low concentrations, it can disturb the development of male frogs and transform them into hermaphrodites . According to studies by Hayes and other authors, atrazine is not only suspected of reducing testosterone production, but also of stimulating estrogen production and thus promoting the development of breast cancer in humans.

The active ingredient is largely harmless to birds and beneficial insects (e.g. bees ) as well as to soil organisms. Atrazine accumulates only slightly or not at all in the food chain .

use

Where the use of atrazine is still permitted, it is used to control monocotyledon and dicotyledon weeds, especially in maize , as well as asparagus , potato and tomato cultivation .

regulation

EU

The use of atrazine has been banned in the European Union since 2003. The permitted daily dose is 0.02 and the acute reference dose 0.1 milligrams per kilogram of body weight and day.

Germany

In Germany, the use of atrazine has been banned since March 1, 1991. The content of pesticides in the groundwater must not exceed 0.1 µg / l. If the limit value is exceeded, an exception limit value of 3 µg / l applies in the case of a promising rehabilitation plan .

Switzerland

In Switzerland, atrazine was deleted from Appendix 1 ("Active substances approved for use in plant protection products") of the Plant Protection Ordinance at the beginning of 2007 , so that the use of atrazine-containing plant protection products has been prohibited since 2012. Since then, the concentrations found in the groundwater have tended to decline. Its manufacture and export are still legal (as of 2019).

Atrazine use in the USA in 2012

United States

The US Environmental Protection Agency (EPA) last took the view in 2007 that there was insufficient evidence of damage to amphibians. A comprehensive reassessment has been carried out since 2010 on the basis of research results published since 2007. This has to do with the accumulated atrazine finds in the drinking water of the Corn Belt .

Resistances

Among other things, in plants lambsquarters , Common reporting and annual bluegrass are resistance against atrazine and other substances from the class of triazines known. This is based on a point mutation in the psb A gene of the plastid genome , which is the binding protein for Q _B coded. At position 264 of the peptide there was an amino acid exchange from glycine to serine , which greatly reduces the binding affinity of the protein to triazine herbicides.

Historical

On October 31, 1986, about 400 liters of an atrazine preparation ended up in the Rhine via the sewage of the Ciba-Geigy company , which, together with another chemical accident at the Sandoz group near Basel, triggered fish deaths in the Rhine one day later .

Since atrazine and its main breakdown product desethylatrazine also get into the groundwater and can therefore also be detected in drinking water , the use of atrazine has been banned in Germany since March 1, 1991 and in Austria since 1995 . However, it is still widespread in the environment; After the Elbe flood in 2002, for example, it was washed out and was later increasingly detected off Heligoland , for example in mussels and the livers of flounders .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o ^p Entry on atrazine in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .

↑ Entry on Atrazine 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 .

↑ Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values (search for 1912-24-9 or atrazine ), accessed on November 9, 2015.

↑ Federal Law Gazette II No. 254/2018

↑ When frog males lay eggs . In: Spectrum of Science . No. 4 , 2010, ISSN 0170-2971 , p. 12 .

↑ Tyrone B. Hayes et al .: Atrazine induces complete feminization and chemical castration in male African clawed frogs ( Xenopus laevis ). In: Proceedings of the National Academy of Sciences . 107, No. 10, pp. 4612-4617, doi : 10.1073 / pnas.0909519107 .

↑ See the summary in L. N. Vandenberg, T. Colborn, T. B. Hayes et al., Hormones and endocrine-disrupting chemicals: low-dose effects and nonmonotonic dose responses , in: Endocrine Reviews. 33, June 2012, first published March 14, 2012, doi : 10.1210 / er.2011-1050 and the interview with Tyrone Hayes in Democracy Now , February 21, 2014.

↑ G. Gunkel, B. Streit: Mechanisms of bioaccumulation of a herbicide (atrazine, s-triazine) in a freshwater mollusc ( Ancylus fluviatilis Müll.) And a fish ( Coregonus fera Jurine). In: Water Research. 14, No. 11, 1980, pp. 1573-1584, doi : 10.1016 / 0043-1354 (80) 90061-5 .

^ ^A ^b Stefan Häne: Too toxic for Switzerland - but exportable anyway. In: derbund.ch . March 15, 2019, accessed March 16, 2019 .

↑ General Directorate Health and Food Safety of the European Commission: Entry on Atrazine in the EU pesticide database ; Entry in the national registers of plant protection products in Austria and Germany ; accessed on March 14, 2016.

↑ No. 5 of Annex 1 to Section 1 of the Ordinance on Use Bans for Plant Protection Products ; the application is therefore a criminal offense according to § 8 in conjunction with § 69 paragraph 1 number 2, paragraph 6 of the Plant Protection Act

↑ Written inquiry: Drinking water pollution by atrazine in the Opf , p. 4., with answer from Bayr. State Ministry for Environment and Health of March 12, 2013

↑ Abwasserlexikon: Atrazine

↑ Entry in the national directory of plant protection products in Switzerland ; accessed on November 7, 2017.

↑ FOAG : Withdrawn active ingredients from Appendix 1 of the PSMV , as of July 1, 2017.

↑ Plant protection products in groundwater. In: bafu.admin.ch . Retrieved November 4, 2019 .

↑ epa.gov: Atrazine Updates - Amphibians (English)

↑ Michael Hawthorne: Growing concern in the water ( March 25, 2014 memento on the Internet Archive ), Chicago Tribune, April 18, 2010.

↑ LUA NRW: Water Quality Report 1997 Chapter 5 Part 3 ( Memento from May 8, 2014 in the Internet Archive )

Web links

Wiktionary: Atrazine - explanations of meanings, word origins, synonyms, translations

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o ^p Entry on atrazine in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .

[CLP_100.016.017-2] Entry on Atrazine 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 .

[3] Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values (search for 1912-24-9 or atrazine ), accessed on November 9, 2015.

[4] Federal Law Gazette II No. 254/2018

[SpektrumderWissenschaft0410-5] When frog males lay eggs . In: Spectrum of Science . No. 4 , 2010, ISSN 0170-2971 , p. 12 .

[6] Tyrone B. Hayes et al .: Atrazine induces complete feminization and chemical castration in male African clawed frogs ( Xenopus laevis ). In: Proceedings of the National Academy of Sciences . 107, No. 10, pp. 4612-4617, doi : 10.1073 / pnas.0909519107 .

[7] See the summary in L. N. Vandenberg, T. Colborn, T. B. Hayes et al., Hormones and endocrine-disrupting chemicals: low-dose effects and nonmonotonic dose responses , in: Endocrine Reviews. 33, June 2012, first published March 14, 2012, doi : 10.1210 / er.2011-1050 and the interview with Tyrone Hayes in Democracy Now , February 21, 2014.

[GGunkelBStreit-8] G. Gunkel, B. Streit: Mechanisms of bioaccumulation of a herbicide (atrazine, s-triazine) in a freshwater mollusc ( Ancylus fluviatilis Müll.) And a fish ( Coregonus fera Jurine). In: Water Research. 14, No. 11, 1980, pp. 1573-1584, doi : 10.1016 / 0043-1354 (80) 90061-5 .

[derbund-9] A ^b Stefan Häne: Too toxic for Switzerland - but exportable anyway. In: derbund.ch . March 15, 2019, accessed March 16, 2019 .