Thiofanox

Structural formula
General
Surname	Thiofanox
other names	3,3-Dimethyl-1- (methylthio) butanone- O- ( N -methylcarbamoyl) oxime
Molecular formula	C 9 H 18 N 2 O 2 S
Brief description	colorless solid with a pungent odor
External identifiers / databases
EC number	254-346-4
ECHA InfoCard	100,049,388
PubChem	38235
Wikidata	Q1286435
properties
Molar mass	218.32 g mol −1
Physical state	firmly
Melting point	57-58 ° C
solubility	sparingly soluble in water (5.2 g l −1 at 22 ° C); very soluble in chlorinated and aromatic hydrocarbons and ketones, including non-polar solvents; poorly soluble in polar aliphatic hydrocarbons;
safety instructions
H and P phrases	H: 300-310-410
	P: 264-273-280-301 + 310-302 + 350-310
Toxicological data	8.5 mg kg −1 ( LD 50 , rat , oral ) ; 39 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 .

Thiofanox is an active ingredient for crop protection and a chemical compound from the group of carbamates .

Extraction and presentation

Thiofanox can be made from pinacolone ( 3,3-dimethyl-2-butanone ). After bromination , bromopinacolone and ethanethiol react to form 3,3-dimethyl-1-methylthio-2-butanone, which is first converted to the oxime by reaction with hydroxylamine . This is reacted either with phosgene to form oxime chloroformate and then with methylamine or directly with methyl isocyanate .

properties

Thiofanox is a flammable solid that is practically insoluble in water. The compound decomposes when heated before the boiling point is reached. It is stable under neutral and acidic conditions, but hydrolyzes rapidly under alkaline conditions ( pH value > 10), producing thiofanox sulfoxide and thiofanox sulfone.

use

Thiofanox is used as an insecticide and acaricide . The effect is due to inhibition of cholinesterase - enzymes .

Admission

Thiofanox is not on 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 ^c ^d Entry on Thiofanox in the Hazardous Substances Data Bank , accessed on August 30, 2012.
↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on Thiofanox in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
↑ Entry on 3,3-dimethyl-1- (methylthio) butanone-O- (N-methylcarbamoyl) oxime in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can use the harmonized classification and labeling expand .
↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 142 ( 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. 571 ( limited preview in Google Book search).
^ Stanley A. Greene: Sittig's Handbook of Pesticides and Agricultural Chemicals . William Andrew, 2007, ISBN 0-8155-1903-6 , pp. 852 ( limited preview in Google Book search).
↑ 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 Thiofanox in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; Retrieved February 25, 2016.

[HSDB-1] Entry on Thiofanox in the Hazardous Substances Data Bank , accessed on August 30, 2012.

[GESTIS-2] ↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on Thiofanox in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .

[CLP_100.049.388-3] Entry on 3,3-dimethyl-1- (methylthio) butanone-O- (N-methylcarbamoyl) oxime in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can use the harmonized classification and labeling expand .

[Thomas_A._Unger-4] Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 142 ( 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 2: Insecticides and Fungicides . Royal Society of Chemistry, 1999, ISBN 0-85404-499-X , pp. 571 ( limited preview in Google Book search).

[Stanley_A._Greene-6] Stanley A. Greene: Sittig's Handbook of Pesticides and Agricultural Chemicals . William Andrew, 2007, ISBN 0-8155-1903-6 , pp. 852 ( limited preview in Google Book search).

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