Thiofanox

3,3-dimethyl- 1-( methylthio) butanone O-( N- methylcarbamoyl ) oxime

Colorless solid with acrid odor

Fixed

57-58 ° C

• Practically insoluble in water (5.2 g · l-1 at 22 ° C)
• Very soluble in chlorinated and aromatic hydrocarbons and ketones, including non-polar solvents
• Sparingly soluble in polar aliphatic hydrocarbons

Risk

• 8.5 mg · kg -1 ( LD50, rat, oral)
• 39 mg · kg -1 ( LD50, Rabbit, transdermal)

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

Production and representation

Thiofanox can be prepared starting from pinacolone ( 3,3-dimethyl -2-butanone ). Still bromination respond Brompinacolon and ethanethiol to 3,3- dimethyl-1 -methylthio -2-butanone, which is first converted by reaction with hydroxylamine to give the oxime. This is reacted with phosgene to give either Oximchlorformat and then with methylamine or directly with methyl isocyanate.

Properties

Thiofanox is a flammable solid that is practically insoluble in water. The compound decomposes on heating before boiling. It is stable under neutral and acidic conditions but rapidly hydrolysed under alkaline conditions ( pH > 10), Thiofanox sulfoxide and sulfone Thiofanox arise.

Use

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

Thiofanox is not included on the approved list in the European Union pesticide active ingredients. In Germany, Austria and Switzerland, no plant protection products containing this active ingredient are allowed.