Butachlor

Structural formula
	Simplified structural formula - 1: 1 mixture of two atropisomers
General
Surname	Butachlor
other names	N - (butoxymethyl) -2-chloro-2 ', 6'-diethylacetanilide; N -butoxymethyl-2-chloro- N - (2,6-diethylphenyl) acetamide;
Molecular formula	C 17 H 26 ClNO 2
Brief description	yellow to purple liquid with a slightly sweet odor
External identifiers / databases
EC number	245-477-8
ECHA InfoCard	100,041,328
PubChem	31677
Wikidata	Q411950
properties
Molar mass	311.85 g mol −1
Physical state	liquid
boiling point	157 ° C (7.00 hPa)
Vapor pressure	<0.001 hPa (25 ° C)
solubility	practically insoluble in water: 20 mg l −1 (20 ° C); soluble in most organic solvents including diethyl ether, acetone, benzene, ethanol, ethyl acetate and hexane;
safety instructions
H and P phrases	H: 302-400
	P: 273
Toxicological data	1,740 mg kg −1 ( LD 50 , rat , oral ) ; 3,470 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 .

Butachlor is a mixture of two atropisomeric chemical compounds from the group of acetanilides , which was introduced as a herbicide by Monsanto in 1969 .

Extraction and presentation

Butachlor can be prepared by reacting chloroacetic acid chloride with the azomethine of 2,6-diethylaniline and formaldehyde , followed by treatment with n -butanol .

properties

Butachlor is a light yellow liquid with a slightly sweet odor that is sparingly soluble in water. It is stable to UV light and hydrolysis in the pH range of 3, 6 and 9. It decomposes at temperatures of 165 ° C and above.

use

Butachlor is used as a selective, systemic herbicide against grass and broad-leaved weeds. Butachlor is the most important herbicide in rice cultivation.

Admission

Butachlor has not been included in the list of active ingredients for pesticides permitted in the European Union . In Germany, Austria and Switzerland, no pesticides with this active ingredient are permitted.

Trade names

Machete, Butanex, Butataf, Dhanuchlor, Farmachlor, Hiltaklor, Trapp, Wiper, Rasayanchlor, Butenachlor.

Individual evidence

↑ ^a ^b ^c ^d Entry on butachlor. In: Römpp Online . Georg Thieme Verlag, accessed on May 22, 2014.
↑ ^a ^b ^c ^d ^e ^f ^g ^h data sheet butachlor at Sigma-Aldrich , accessed on May 20, 2017 ( PDF ).
↑ ^a ^b ^c ^d Entry on butachlor in the Hazardous Substances Data Bank , accessed October 8, 2012.
↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1401-8 , pp. 14 ( limited preview in Google Book search).
↑ ^a ^b Terry R. Roberts, David H. Hutson, Philip W. Lee, Peter H. Nicholls: Metabolic Pathways of Agrochemicals: Part 1: Herbicides and Plant Growth ... Royal Society of Chemistry, 1998, ISBN 0-85404- 494-9 , pp. 194 ( limited preview in Google Book search).
↑ Rice Field Herbicide Butachlor Is Toxic to Taiwanese Frog Tadpoles
↑ Regulation (EC) No. 2076/2002 (PDF) of the Commission of November 20, 2002.
↑ General Directorate Health and Food Safety of the European Commission: Entry on butachlor in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; Retrieved February 25, 2016.

[roempp-1] Entry on butachlor. In: Römpp Online . Georg Thieme Verlag, accessed on May 22, 2014.

[Sigma-2] ↑ ^a ^b ^c ^d ^e ^f ^g ^h data sheet butachlor at Sigma-Aldrich , accessed on May 20, 2017 ( PDF ).

[HSDB-3] Entry on butachlor in the Hazardous Substances Data Bank , accessed October 8, 2012.

[Thomas_A._Unger-4] Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1401-8 , pp. 14 ( limited preview in Google Book search).

[Terry_R._Roberts,_David_H._Hutson,_Philip_W._Lee,_Peter_H._Nicholls-5] Terry R. Roberts, David H. Hutson, Philip W. Lee, Peter H. Nicholls: Metabolic Pathways of Agrochemicals: Part 1: Herbicides and Plant Growth ... Royal Society of Chemistry, 1998, ISBN 0-85404- 494-9 , pp. 194 ( limited preview in Google Book search).

[6] Rice Field Herbicide Butachlor Is Toxic to Taiwanese Frog Tadpoles

[7] Regulation (EC) No. 2076/2002 (PDF) of the Commission of November 20, 2002.

[PSM-8] General Directorate Health and Food Safety of the European Commission: Entry on butachlor in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; Retrieved February 25, 2016.