Patent GB-632635-A (GB)
Title: Improvements in and relating to the manufacture and use of halogen-containing insecticidal organic compounds and to the treatment of materials therewith
IPC: C07C17/04
Filed: 1944-07-28
Abstract: Insecticidal compounds having the general formula <FORM:0632635/IV (b)/1> are obtained by chlorinating a compound having the general formula <FORM:0632635/IV (b)/2> wherein R and R1 each represent benzene rings which may be substituted by alkyl or alkoxy groups, or by chlorine.  In examples 1 to 3 a  : a -bis-(4-chlorophenyl)-a  : b : b  : b -tetrachlorethane is prepared by bubbling chlorine into carbon tetrachloride solutions of (1) a  : a  - bis - 4 - chlorophenyl - b  : b  - dichlorethylene at boiling point; (2) a  : a - bis-4-chlorophenyl-b  : b  : b -trichloroethane at room temperature; (3) as in (2) but at boiling temperature; (4) and (5) carbon tetrachloride solutions of a  : a -bis-phenyl-b  : b  : b -trichloroethane and a  - a  - bis - p - tolyl - b  : b  : b  - trichloroethane respectively are treated with chlorine at room temperature to obtain (4) a  - a  - bis - phenyl - a  : b  : b  : b - tetrachloroethane and (5) a  - a  - bis-p-tolyl-a  : b  : b  : b -tetrachloroethane.  By direct sulphonation and nitration sulphonated and nitro derivatives respectively may be obtained from the products, e.g. a  : a  - bis - (4 - chloro - 3 - sulpho or nitrophenyl) - a  : b  : b  : b  - tetrachloroethane.  A sample of a  : a -bis-(p-anisyl)-a  : b  : b  : b -tetrachloroethane, submitted under Sect. 2 (5) of the Acts is obtained by bubbling chlorine into a carbon tetrachloride solution of a  : a -bis-(p-anisyl)-b  : b  : b -trichloroethane at room temperature from the tetrachloro compounds thus prepared nitro-substituted derivatives such as a  : a  - bis - (4 - chloro - 3 - nitrophenyl)-a  : b  : b  : b -tetrachlorethane can be made by direct nitration; sulphonated derivatives such as a  : a - bis - (4 - chloro - 3 - sulphophenyl)-a  : b  : b  : b -tetrachorethane can be obtained by direct sulphonation.  The cyano amino and halogen derivatives may also be obtained by reduction, and diazotization followed by the Gattermann reaction. Carboxylic derivatives may be obtained by hydrolysis of the cyano compounds. Specifications 547,871 and 547,874 are referred to.ALSO:Aqueous insecticidal emulsions or solid insecticidal compositions contain a compound having the general formula: <FORM:0632635/VI/1> wherein R and R1 represent benzene rings, substituted or not.  One method of preparation is by dissolving the compound in an organic solvent adding an emulsifying agent and pouring the mixture, while thoroughly stirring, into water; or, in a modified method, the emulsifying agent is added wholly or partly to the water and the organic solution containing none or only part of the emulsifying agent is added thereto.  Another method of preparation is by mixing intimately a compound of the general formula with a solid, finely-divided or porous inert diluent or carrier e.g., an inorganic natural colloid. Alternatively, a solution of the compound is mixed with the solid diluent or carrier and the solvent is then expelled by evaporation. Specifications 547,871 and 547,874 are referred to.