Metazachlor

Structural formula
1: 1 mixture of both atropisomers
General
Surname	Metazachlor
other names	( RS ) -2-chloro- N - (2,6-dimethylphenyl) - N - (1 H -pyrazol-1-ylmethyl) acetamide Butisane
Molecular formula	C 14 H 16 ClN 3 O
Brief description	colorless, odorless solid technical product: yellow solid with a sweet odor
External identifiers / databases
CAS number 67129-08-2 EC number 266-583-0 ECHA InfoCard 100.060.511 PubChem 49384 Wikidata Q15834927
properties
Molar mass	277.75 g mol −1
Physical state	firmly
density	1.31 g cm −3
Melting point	triclinic metazachlor: 78-83 ° C monoclinic metazachlor: 76 ° C metastable metazachlor: 84 ° C
Vapor pressure	0.093 mPa (20 ° C)
solubility	very sparingly soluble in water (0.43 g l −1 at 20 ° C)
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary Caution H and P phrases H: 317-351-410 P: 273-301 + 312 + 330-391-501
Toxicological data	2150 mg kg −1 ( LD 50 ,  rat ,  oral ) > 6800 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 .

Metazachlor is a 1: 1 mixture of two atropisomeric chemical compounds from the group of chloroacetamides, as well as alachlor and metolachlor . The herbicide works by inhibiting fatty acid synthesis and was brought onto the market by BASF in 1976. Metazachlor was at the center of a legal dispute between Feinchemie Schwebda and BASF .

Extraction and presentation

Metazachlor can be produced by reacting 2,6-dimethylaniline with chloroacetic acid chloride and then with paraformaldehyde , a chlorinating agent and pyrazole .

use

Metazachlor is used as a selective precursor herbicide against grass weeds in cabbage, tobacco, rape and potato cultivation.

Admission

The active ingredient is approved in the EU. In Germany, Austria and Switzerland, pesticide products with the active ingredient metazachlor are approved, such as B. Butisan and Fuego .

Individual evidence

1. ↑ ^{a b c} Entry on metazachlor in the GESTIS substance database of the IFA , accessed on February 16, 2014 (JavaScript required)
2. ↑ Data sheet from Zhejiang Rayfull ( Memento from February 22, 2014 in the Internet Archive )
3. ^ ^{A b c} S. D. Gangolli, Royal Society of Chemistry (Great Britain): The Dictionary of Substances and Their Effects (DOSE): Volume 05 KN . Royal Society of Chemistry, 1999, ISBN 0-85404-828-6 , pp. 275 .
4. ↑ ^{a b c} Patent application EP1342412 : Purely triclinic metazachlor and process for its production. Registered on January 24, 2003 , published on September 26, 2007 , applicant: Feinchemie Schwebda , inventor: Michael Schnell. ‌
5. ↑ Entry on 2-chloro-N- (2,6-dimethylphenyl) -N- (1H-pyrazol-1-ylmethyl) acetamide in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016 . marketer can use the harmonized classification and labeling expand .
6. ↑ Metazachlor data sheet , PESTANAL at Sigma-Aldrich , accessed on December 11, 2016 ( PDF ).
7. ↑ ^{a b} entry on metazachlor. In: Römpp Online . Georg Thieme Verlag, accessed on February 16, 2014.
8. ↑ 2 U 53/06 - Monoclinic Metazachlor in the Düsseldorf archive.
9. ^ BGH, judgment of March 15, 2011 - X ZR 58/08; Federal Patent Court .
10. ↑ ^{a b} Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 35 ( limited preview in Google Book search).
11. ↑ General Directorate Health and Food Safety of the European Commission: Entry on metazachlor in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on February 15, 2016.
12. ↑ Manufacturer's website for Fuego