Verfahren zur Herstellung von neuen, halogenstubstituierten aromatischen Stickstoffheterocyclen

Chlorinated heterocyclic nitrogen compounds are produced by chlorinating an aromatic compound of formula in which X is an alkyl, alkylene, chloroalkyl, or chloroalkylene radical all having 3 to 5 carbon atoms, at least 3 being in a straight chain, Y is an alkyl, chlorocarbonyl or organic acyl radical with up to 5 carbon atoms, Ar is an aryl, alkylaryl, nitroaryl, halogenoaryl, or a cyanoaryl radical with one free position ortho to the nitrogen atom, in a first step at 20 DEG to 60 DEG C. and then, with a gradual increase in temperature, in a second step at 200 DEG to 250 DEG C. The first step may be in an inert organic solvent, e.g. a chlorinated hydrocarbon. The second step may take place under irradiation with ultra-violet light and in the presence of a halogen transfer catalyst, e.g. aluminium chloride or bromide, iron chloride, stannic chloride, boron trifluoride or titanium tetrachloride. Chlorinated quinolines such as heptachloroquinoline are obtained where Ar represents a phenyl radical, Y represents an alkyl or alkenyl radical with up to 3 carbon atoms, a chlorocarbonyl or an acetyl radical, and X represents an n-propyl or isobutyl radical.ALSO:Chlorinated heterocyclic nitrogen compounds, especially chlorinated quinoline are used as herbicides or insecticides. In an example, heptachloroquinoline is used in aqueous dimethyl-formamide containing a non-ionic emulsifier.