Patent GB-865735-A (GB)
Title: Process for the production of new aminobenzoic acid derivatives and their use in pest control
Filed: 1958-12-18
Abstract: The invention comprises N-sulphonated aminobenzoic acid arylamides of the general formula: <FORM:0865735/IV (b)/1> wherein A represents a phenyl, phenoxyphenyl or phenylmercaptophenyl radical, which radical is substituted by at least one halogen atom and/or trifluoromethyl group, R1 represents a halogen-substituted lower alkyl radical or a phenyl or phenyalkyl group substituted in the nucleus by halogen and/or trifluoromethyl, R2 represents hydrogen or a lower alkyl radical, Hal represents chlorine or bromine, and n is a whole number from 0 to 4, and wherein the total number of halogen and trifluoromethyl substituents present on the different aromatic rings of the molecule is greater than 2 and preferably at least 4. The invention also comprises the use of the compounds for protecting wool and fur against injurious insects (see Group VIII). the invention further comprises two processes for producing the compounds, viz. (1) by reacting an aminobenzoic acid arylamide with an aryl sulphonyl chloride, and (2) by reacting a N-sulphonyl aminobenzoyl halide with an arylamine; the reactants in either case being so chosen that there are, in all, at least 3 halogen and/or CF3 ring-substituents in the product; or either process may be carried out using similar reactants to give a product containing less than 3 of these substituents, and then reacting the product with chlorine or bromine in order to introduce the necessary number of halogen atoms into the molecule. In Example 1, a solution of 3, 5-dichloroanthranilic acid is treated with phosgene to obtain 3, 5-dichlorisatoic acid anhydride, and the latter is reacted with 3, 4-dichloraniline to give 2-amino-3, 5-dichlorobenzoic acid- 31, 41-dichloranilide.  This is then reacted with 3, 4-dichlorobenzene sulphochloride to obtain 2-(31, 41-dichlorobenzene sulphonamido-3, 5-dichlorobenzoic acid-311, 411-dichloranilide, which is finally treated with dimethyl sulphate in order to replace the hydogen atom of the -NHSO2- radical by CH3. In Example 2, anthranilic acid is reacted with 3, 4-dichlorobenzene sulphochloride to give 2-(31, 41-dichlorobenzene sulphonamido)-benzoic acid, which is converted into the acid chloride by means of phosphorus pentachloride.  The acid chloride is reacted with 2, 4, 5-trichloraniline to obtain 2-(31, 41-dichlorobenzene sulphonamido)-benzoic acid-211, 411, 511-trichloranilide, which is finally subjected to direct chlorination whereby a chlorine atom is introduced into the 5-position of central benzene ring.  In Example 3, a solution of 2, 4, 5-trichloraniline is reacted with 3-nitro-4-chlorobenzoyl chloride to obtain 3-nitro-4-chloro-benzoic-21, 41, 51-trichloranilide which is then subjected to catalytic reduction.  The 3-amino product is then reacted with 3-trifluoromethyl-4-chlorobenzene sulphonyl chloride to obtain 3-(3'trifluoromethyl-41-chlorobenzene sulphonamido-4-chlorobenzoic acid-211, 411, 511-trichloranilide.  An extensive list is given of other compounds which can be produced in an analogous manner to those described in the examples.ALSO:An insecticidal composition, of particular use in protecting wool and fur against injurious moths and beetles, comprises a N-sulphonated aminobenzoic acid arylamide of the general formula <FORM:0865735/VI/1> dissolved or suspended in an inert solvent, if desired in the presence of an emulsifying agent.  In the above formula Ar represents a phenyl, phenoxyphenyl, phenylmercaptophenyl radical, which radical is substituted by at least one halogen atom and/or trifluoromethyl group, R1 represents a halogen-substituted lower alkyl radical or a phenyl or phenylalkyl group substituted in the nucleus by halogen and/or trifluoromethyl, R2 represents hydrogen or a lower alkyl radical, Hal represents chlorine or bromine, and n is a whole number from 0 to 4, and wherein the total number of halogen and trifluoromethyl substituents present on the different aromatic rings of the molecule is greater than 2 and preferably at least 4.  Two processes for producing these compounds are described (see Group IV (b)).  When R2 is a hydrogen atom, the compounds form alkali metal salts of good water-solubility.  Suitable organic solvents for the compounds are the following: propylene glycol, dimethylformamide, and the monomethyl and monoethyl ethers of ethylene glycol.  Specified emulsifying agents are: sulphonated castor oil, sulphite waste liquid, and fatty acid sulphonates.