Patent GB-582205-A (GB)
Title: Improvements in and relating to the manufacture and use of insecticidal compositions
Filed: 1943-12-18
Abstract: Compounds of the general formula R1CH(R2)-CX3, X being chlorine or bromine, R1 being an organic radical containing at least three carbon atoms, R2 being an organic radical containing at least five carbon atoms and R1 or R2 or both containing one or more water-solubilizing groups other than free carboxylic groups or their difficultly soluble salts are prepared by the action of chloral or bromal upon compounds containing a replaceable hydrogen atom and a water-solubilising group, by the treatment, e.g. sulphonation, of the trihalogenoethane compounds described in Specifications 547,871 547,874, 566,386 and 566,387 or by oxidising a corresponding aryl compound having an organic substituent attached to the nucleus through a carbon atom using an oxidising agent such as chromic acid.  According to examples: (1) the sodium salt of a  : a -bis-(4-chloro-3-sulphophenyl)-b  : b  : b -trichloroethane is prepared by stirring a  : a -bis-(4-chlorophenyl)-b  : b  : b -trichloroethane with oleum at a temperature rising to 50-60 DEG  C., cooling the product, pouring it into cold water, adding salt, stirring and filtering off the resulting crystals; (2) the sodium salt of a  : a -bis-(4-methyl-3-sulphophenyl)-b  : b  : b -trichloroethane is prepared from a  : a -bis-(p-tolyl)-b  : b  : b -trichloroethane by a procedure similar to (1); (3) the sodium salt of a  : a -bis-(4-fluro-3-sulphophenyl)-b  : b  : b -trichloroethane is prepared from a  : a -bis - (4 - fluorophenyl) - b  : b  : b  - trichloroethane by a procedure similar to (1); (4) the sodium sulphate-derivative a  : a  - bis - (4 - o  - hydroxy-butylphenyl)-b : b  : b -trichloroethane is prepared by treating a cooled and well-stirred mixture of d -phenylbutanol, chloral and glacial acetic acid with a drop-wise addition of concentrated sulphuric acid, pouring the product into cold water, adding salt and filtering off the resulting precipitate; (5) the sodium salt of a  : a  - bis - (4 - hydroxy - 3 - chlorophenyl) - b  : b  : b -trichloroethane is prepared from o-chlorophenol chloral and concentrated sulphuric acid by a procedure similar to (5); (6) the sodium salt of a  : a  - bis - (4 - carboxymethylphenyl) - b  : b  : b  - trichloroethane is prepared by adding chloral to a stirred solution of phenylacetic acid in concentrated sulphuric acid to produce a  : a -bis - (4 - carboxymethylphenyl) - b  : b  : b  - tri - chloroethan which is then neutralized with sodium carbonate.ALSO:An insecticide comprises an aqueous liquid or a solid inert carrier and a compound of the general formula R1CH(R2)-CX3, where X is chlorine or bromine, R1 is an organic radical containing at least three carbon atoms and R2 is an organic radical containing at least five carbon atoms, and R1 or R2 or both contain one or more water-solubilizing groups other than free carboxylic acids or their difficulty soluble salts.  Suitable water-solubilizing groups include sulphonic acid groups, sulphate groups, carboxylic acid groups in the form of their water-soluble salts and plurality of hydroxyl groups.  These groups may be present in an open chain or ring portion of the molecule.  Specified compounds are the sodium salts of a :a -bis-(4-chloro-3 sulphophenyl) - b  : b  : b  - trichlorethane, a  : a  - bis - (4-methyl-3-sulphophenyl) -b :b :b -trichloroethane, a  : a -bis-(4-fluoro-3-sulphophenyl)-b :b .b -trichloroethane, sulphato - a : a  - bis - (4-o -hydroxy-butylphenyl)-b :b :b -trichloroethane, a :a -bis-(4-hydroxy-3-chlorophenyl)-b :b :b -trichloroethane and a :a -bis - (4 - carboxymethylphenyl) - b :b :b  - trichloroethane.  These water-soluble derivatives may be included in aqueous washing, painting, and spraying preparations. Specifications 547,871, 547,874, 566,386 and 566,387 are referred to.