Butraline

Structural formula
	Structural formula without stereochemistry
General
Surname	Butraline
other names	N - sec -Butyl-4- tert -butyl-2,6-dinitroaniline; ( RS ) - N - sec -Butyl-4- tert -butyl-2,6-dinitroaniline; Amexine; Tamex;
Molecular formula	C 14 H 21 N 3 O 4
Brief description	yellow-orange crystals
External identifiers / databases
EC number	251-607-4
ECHA InfoCard	100.046.902
PubChem	36565
Wikidata	Q2570341
properties
Molar mass	295.33 g mol −1
Physical state	firmly
Melting point	60-61 ° C
boiling point	134-136 ° C (0.6 mbar)
Vapor pressure	0.0017 mPa (25 ° C)
solubility	practically insoluble in water (1 mg l −1 at 25 ° C); soluble in acetone, benzene, butanone, carbon tetrachloride;
safety instructions
H and P phrases	H: 302-319-341-410
	P: 273-281-305 + 351 + 338-501
Toxicological data	12600 mg kg −1 ( LD 50 , rat , oral ) ; > 2000 mg kg −1 ( LD 50 , rat , oral ) ; 10200 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 .

Butralin is a racemate from the group of dinitroaniline - derivatives which as pre-emergence herbicide is used. It was from 1973 Amchem on the market brought.

Extraction and presentation

Butralin, by chlorination of tert-butylbenzene with and subsequent reaction of nitric acid and sec -butylamine are obtained.

Stereochemistry

Generally speaking, chemical compounds with at least one stereocenter form up to 2 ⁿ stereoisomers . Here n is the number of stereocenters. According to this, there are two stereoisomers of butraline, which have also been confirmed experimentally:

Butraline enantiomers
CAS number: 61709-90-8	CAS number: 61709-89-5

use

Like its related nitralin, butraline is a microtubule inhibitor.

Admission

In Switzerland, Germany and Austria is not a pesticide approved containing butraline. In 2008, the European Union decided not to include the active ingredient in the list of permitted active ingredients because of its harmful effects on health. A trade name for use in the technical area and as a crop protection agent in the USA is Amex 820 .

Individual evidence

↑ ^a ^b ^c Entry on Butralin in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on May 30, 2019.
↑ ^a ^b ^c ^d ^e ^f ^g S.D. Gangolli, Royal Society of Chemistry (Great Britain): The Dictionary of Substances and Their Effects (DOSE): Volume 01 A-B . Royal Society of Chemistry, 1999, ISBN 0-85404-808-1 , pp. 786 ( limited preview in Google Book search).
↑ ^a ^b Butralin data sheet from Sigma-Aldrich , accessed on October 9, 2016 ( PDF ).

↑ Patent application US3991116 : 4-tert-butyl-N-sec-butyl-2,6-dinitroaniline. Applied May 1, 1975 , published November 9, 1976 , Applicant: Amchem Products, Inventor: John Joseph Damiano. ‌

↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 862 ( limited preview in Google Book search).

↑ Paula Y. Bruice: Organic Chemistry: Study compact . Pearson Studium, Munich 2011, ISBN 978-3-86894-102-9 , p. 205.

↑ Elim M. Ulrich, Candice M. Morrison, Michael M. Goldsmith, William T. Foremann: Chiral Pesticides: Identification, Description, and Environmental Implications . In: Reviews of Environmental Contaminations and Toxicology. Springer 2012, Boston, Volume 217, pp. 1–74, DOI: 10.1007 / 978-1-4014-2329-4_1 , see p. 21.

↑ CL Elmore, DE Bayer: Mitotic and structural effects of nitralin and butraline on ryegrass (Lolium perenne L.) root meristems . In: Weed Research . tape 32 , no. 2 , April 1992, pp. 77-86 , doi : 10.1111 / j.1365-3180.1992.tb01864.x ( PDF ).

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

↑ Decision of the Commission of October 20, 2008 (PDF) on the non-inclusion of butraline in Annex I of Council Directive 91/414 / EEC and the revocation of the authorizations for plant protection products containing this substance (2008/819 / EC).

↑ Information from a provider (accessed on December 13, 2013).

[df-1] Entry on Butralin in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on May 30, 2019.

[dose-2] ↑ ^a ^b ^c ^d ^e ^f ^g S.D. Gangolli, Royal Society of Chemistry (Great Britain): The Dictionary of Substances and Their Effects (DOSE): Volume 01 A-B . Royal Society of Chemistry, 1999, ISBN 0-85404-808-1 , pp. 786 ( limited preview in Google Book search).

[Sigma-3] Butralin data sheet from Sigma-Aldrich , accessed on October 9, 2016 ( PDF ).

[4] Patent application US3991116 : 4-tert-butyl-N-sec-butyl-2,6-dinitroaniline. Applied May 1, 1975 , published November 9, 1976 , Applicant: Amchem Products, Inventor: John Joseph Damiano. ‌

[unger-5] Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 862 ( limited preview in Google Book search).

[6] Paula Y. Bruice: Organic Chemistry: Study compact . Pearson Studium, Munich 2011, ISBN 978-3-86894-102-9 , p. 205.

[Ulrich-7] Elim M. Ulrich, Candice M. Morrison, Michael M. Goldsmith, William T. Foremann: Chiral Pesticides: Identification, Description, and Environmental Implications . In: Reviews of Environmental Contaminations and Toxicology. Springer 2012, Boston, Volume 217, pp. 1–74, DOI: 10.1007 / 978-1-4014-2329-4_1 , see p. 21.

[8] CL Elmore, DE Bayer: Mitotic and structural effects of nitralin and butraline on ryegrass (Lolium perenne L.) root meristems . In: Weed Research . tape 32 , no. 2 , April 1992, pp. 77-86 , doi : 10.1111 / j.1365-3180.1992.tb01864.x ( PDF ).

[PSM-9] General Directorate Health and Food Safety of the European Commission: Entry on Butralin in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on February 18, 2016.

[10] Decision of the Commission of October 20, 2008 (PDF) on the non-inclusion of butraline in Annex I of Council Directive 91/414 / EEC and the revocation of the authorizations for plant protection products containing this substance (2008/819 / EC).

[11] Information from a provider (accessed on December 13, 2013).