Butoxycarboxim

Structural formula
	Simplified structural formula without stereochemistry
General
Surname	Butoxycarboxim
other names	2-methylsulfonyl- O- ( N -methylcarbamoyl) butanone-3-oxime; 3- (methylsulfonyl) butanone- O -methylcarbamoyloxime; 3- (methylsulfonyl) -2-butanone- O - ((methylamino) carbonyl) oxime;
Molecular formula	C 7 H 14 N 2 O 4 S
Brief description	colorless to yellowish crystals
External identifiers / databases
EC number	252-140-9
ECHA InfoCard	100.047.386
PubChem	61938
ChemSpider	55798
Wikidata	Q27117867
properties
Molar mass	222.27 g mol −1
Physical state	firmly
density	1.21 g cm −3
Melting point	85-89 ° C
boiling point	decomposes when heated
solubility	easily in water (209 g l −1 at 20 ° C)
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 302
	P: no P-phrases
Toxicological data	458 mg kg −1 ( LD 50 , rat , oral ) ; > 11000 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 .

Butoxycarboxim is a synthetic insecticide and acaricide from the active ingredient group of oxime carbamates . It was introduced by Wacker Chemie in 1970 .

Extraction and presentation

Butoxycarboxim can by the oxidation of Butocarboxim with peracetic acid are obtained. Alternatively, it can also be prepared from 3-methylsulfon-2-butanone and hydroxylamine with subsequent reaction with methyl isocyanate .

Butoxycarboxime is also a metabolite in the breakdown of butocarboxime in mammals.

Mode of action

Butoxycarboxim is an insecticide that acts as a contact poison and food poison. The active ingredient is distributed throughout the plant after ingestion via the roots.

Its mode of action is comparable to other carbamate insecticides. By inhibiting the enzyme acetylcholine esterase in the synapses of the nervous system , the transmission of stimuli to the nerves is blocked. The nerves remain permanently in an excited state. The resulting paralysis can lead to respiratory arrest and ultimately to the death of the affected organism.

Areas of application

Butoxycarboxim is mainly used against spider mites and aphids in potted plants . Typical forms of application are cardboard sticks that have been provided with the active ingredient and that are stuck into the ground.

toxicology

Butoxycarboxime is classified as a Class Ib toxin (very dangerous) by the World Health Organization . Symptoms of poisoning with Butoxycarboxim can cause muscle weakness, sweating, dizziness, tiredness, nausea, diarrhea and headache.

Butoxycarboxim is not toxic to fish and bees .

Analytics

The reliable detection and quantification of butoxycarboxime is possible using liquid chromatographic methods. After the chromatographic separation, a mass spectrometer can be used to identify the substance .

Admission

Butoxycarboxim is not approved in the European Union . The maximum residue level for all foods is 0.01 mg / kg.

Trade names

Plant Pin (Wacker)
Bellasol ( BASF )

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on butoxycarboxime in the GESTIS substance database of the IFA , accessed on June 27, 2018(JavaScript required) .

↑ Thomas A. Unger: Pesticide synthesis handbook . Noyes Publications, 1996, ISBN 978-0-8155-1401-5 , pp. 138 ( limited preview in Google Book search).

↑ ^a ^b ^c ^d Paranjape, Kalyani .: The pesticide encyclopedia . CABI, Wallingford, Oxfordshire UK 2014, ISBN 978-1-78064-014-3 ( limited preview in Google Book Search).

^ Entry on Butocarboxim in the Hazardous Substances Data Bank , accessed June 28, 2018.

↑ ^a ^b ^c Entry on butoxycarboxime. In: Römpp Online . Georg Thieme Verlag, accessed on June 27, 2018.

↑ International Program on Chemical Safety., Inter-Organization Program for the Sound Management of Chemicals., World Health Organization .: WHO recommended classification of pesticides by hazard and guidelines to classification 2009. World Health Organization, Geneva 2010, ISBN 978-92- 4154796-3 .

↑ Derick Lucas: Optimizing Sample Preparation for LC / MS / MS of Pesticide Residues in Herbal Teas. (PDF) In: Agilent Technologies, Inc. December 17, 2013, accessed June 28, 2018 .

↑ General Directorate Health and Food Safety of the European Commission: Entry on butoxycarboxime in the EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on June 27, 2018.

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on butoxycarboxime in the GESTIS substance database of the IFA , accessed on June 27, 2018(JavaScript required) .

[Unger-2] Thomas A. Unger: Pesticide synthesis handbook . Noyes Publications, 1996, ISBN 978-0-8155-1401-5 , pp. 138 ( limited preview in Google Book search).

[kalyani-3] Paranjape, Kalyani .: The pesticide encyclopedia . CABI, Wallingford, Oxfordshire UK 2014, ISBN 978-1-78064-014-3 ( limited preview in Google Book Search).

[HSDB-4] Entry on Butocarboxim in the Hazardous Substances Data Bank , accessed June 28, 2018.

[roempp-5] Entry on butoxycarboxime. In: Römpp Online . Georg Thieme Verlag, accessed on June 27, 2018.

[6] International Program on Chemical Safety., Inter-Organization Program for the Sound Management of Chemicals., World Health Organization .: WHO recommended classification of pesticides by hazard and guidelines to classification 2009. World Health Organization, Geneva 2010, ISBN 978-92- 4154796-3 .

[7] Derick Lucas: Optimizing Sample Preparation for LC / MS / MS of Pesticide Residues in Herbal Teas. (PDF) In: Agilent Technologies, Inc. December 17, 2013, accessed June 28, 2018 .