Butocarboxim

Structural formula
	Four stereoisomers : Racemate of the ( E ) and the ( Z ) isomer
General
Surname	Butocarboxim
other names	6,7-Dimethyl-4-oxa-8-thia-2,5-diazanon-5-en-3-one ( IUPAC ) ; 2-methylthio- O - ( N -methylcarbamoyl) butanone-3-oxime; 3- (methylthio) butanone- O -methylcarbamoyloxime; ( RS , EZ ) -3- (methylthio) butanone- O -methylcarbamoyloxime;
Molecular formula	C 7 H 14 N 2 O 2 S
Brief description	colorless solid
External identifiers / databases
EC number	252-139-3
ECHA InfoCard	100.047.385
PubChem	5368008
ChemSpider	4519434
Wikidata	Q27117865
properties
Molar mass	190.27 g mol −1
Physical state	firmly
density	1.12 g cm −3
Melting point	32-37 ° C
solubility	slightly soluble in water (35 g l −1 at 20 ° C); soluble in most organic solvents;
safety instructions
H and P phrases	H: 226-331-311-301-319-410
	P: 261-273-280-301 + 310-305 + 351 + 338-311
Toxicological data	153 mg kg −1 ( LD 50 , rat , oral ) ; 360 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 .

Butocarboxime is a mixture of four isomeric chemical compounds from the group of carbamates and oximes .

Extraction and presentation

Butocarboxime can be obtained by reacting 2-chloro-3-butanone with methyl mercaptan and then with hydroxylamine hydrochloride and methyl isocyanate .

properties

Butocarboxim is a colorless solid that dissolves in water. It decomposes when heated before the boiling point is reached (from 80 ° C). The technical product consists of about 85 to 90% of the racemic ( E ) isomer and 10 to 15% of the racemic ( Z ) isomer. In the soil it is broken down to butocarboxim sulfoxide and butocarboxim sulfone (butoxycarboxime). In mammals it is converted to butoxycarboxime . The compound is stable to UV light and in solution in the neutral as well as slightly alkaline and acidic range.

use

Butocarboxim is used as an acaricide and an insecticide (mainly used against constant winged animals and spider mites ). The effect is based on the inhibition of acetylcholinesterase .

Admission

Butocarboxim 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.

Individual evidence

↑ ^a ^b butocarboxim data sheet at Sigma-Aldrich , accessed on May 21, 2017 ( PDF ).

↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on Butocarboxim in the GESTIS substance database of the IFA , accessed on January 31, 2020(JavaScript required) .

↑ ^a ^b ^c Joint Meeting on Pesticide Residues (JMPR), Monograph for Butocarboxim , accessed December 9, 2014.

↑ Entry on Butocarboxim 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 .

↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 137 ( 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 2: Insecticides and Fungicides . Royal Society of Chemistry, 1999, ISBN 0-85404-499-X , pp. 553 ( limited preview in Google Book search).

^ Terence Robert Roberts, David Herd Hutson: Metabolic Pathways of Agrochemicals: Part 2, Insecticides and fungicides . Royal Society of Chemistry, 1999, ISBN 0-85404-499-X , pp. 555 ( limited preview in Google Book search).

^ Entry on Butocarboxim in the Hazardous Substances Data Bank , accessed October 9, 2012.

↑ Entry on Butocarboxim in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on July 31, 2013.

↑ 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 Butocarboxim in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; Retrieved February 25, 2016.

[Sigma-1] utocarboxim data sheet at Sigma-Aldrich , accessed on May 21, 2017 ( PDF ).

[GESTIS-2] ↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on Butocarboxim in the GESTIS substance database of the IFA , accessed on January 31, 2020(JavaScript required) .

[inchem.org-3] Joint Meeting on Pesticide Residues (JMPR), Monograph for Butocarboxim , accessed December 9, 2014.

[CLP_100.047.385-4] Entry on Butocarboxim 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 .

[Thomas_A._Unger-5] Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 137 ( limited preview in Google Book search).

[Terry_R._Roberts,_David_H._Hutson,_Philip_W._Lee,_Peter_H._Nicholls-6] Terry R. Roberts, David H. Hutson, Philip W. Lee, Peter H. Nicholls: Metabolic Pathways of Agrochemicals: Part 2: Insecticides and Fungicides . Royal Society of Chemistry, 1999, ISBN 0-85404-499-X , pp. 553 ( limited preview in Google Book search).

[Terence_Robert_Roberts,_David_Herd_Hutson-7] Terence Robert Roberts, David Herd Hutson: Metabolic Pathways of Agrochemicals: Part 2, Insecticides and fungicides . Royal Society of Chemistry, 1999, ISBN 0-85404-499-X , pp. 555 ( limited preview in Google Book search).

[HSDB-8] Entry on Butocarboxim in the Hazardous Substances Data Bank , accessed October 9, 2012.

[herts.ac.uk-9] Entry on Butocarboxim in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on July 31, 2013.

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

[PSM-11] General Directorate Health and Food Safety of the European Commission: Entry on Butocarboxim in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; Retrieved February 25, 2016.