Patent GB-764020-A (GB)
Title: Novel copper salts of nonylated aromatic sulphonic acids and fungicidal compositionscontaining them
IPC: C07C309/37
Filed: 1954-12-21
Abstract: The invention comprises copper and cuprammonium salts of nonylated naphthalene sulphonic acids.  The naphthalene nucleus may contain one or more further alkyl substituents such as methyl or ethyl. Compounds specified are cupric and cuprammonium salts of monononyl- and dinonyl - naphthalene sulphonic acids.  The salts are prepared by alkylating naphthalene or an alkyl-substituted naphthalene with a straight chain or branched chain C9 olefine such as propylene trimer or with a C9 alkyl halide, sulphonating the resulting nonylated naphthalene with concentrated sulphuric acid, sulphur trioxide or sulphonyl chloride, and neutralizing the resulting sulphonic acid with an inorganic alkali-metal base.  The alkali-metal sulphonate is then converted to the copper salt by a metathetical reaction with an inorganic copper salt such as copper sulphate or copper nitrate. The cuprammonium salts are prepared by carrying out the metathesis in the presence of aqueous ammonia.  In examples: (1) naphthalene is alkylated with propylene trimer in hexane solution in the presence of aluminium chloride and the product distilled, giving monononyl- and dinonyl-naphthalene, the latter is sulphonated with sulphur trioxide in sulphur dioxide/carbon tetrachloride solution and the product is treated with caustic soda to give an aqueous solution of sodium dinonylnaphthalene sulphonate which is treated with copper sulphate in aqueous isopropanol to yield copper dinonyl-naphthalene sulphonate; (2) copper sulphate in aqueous ammonia is reacted with sodium dinonyl naphthalene sulphonate prepared as in Example (1) to yield cuprammonium dinonyl-naphthalene sulphonate.  The copper and cuprammonium salts are used in fungicidal compositions (see Group VI).ALSO:Fungicidal compositions containing a copper or cuprammonium salt of a nonylated naphthalene sulphonic acid, which may be further substituted in the nucleus by methyl or ethyl groups, are described and claimed.  The salts may be used as dusts, in solution in organic liquids, and in aqueous emulsions, in concentrations of from 0.05 per cent to 5 per cent by weight. Concentrated compositions suitable for forming aqueous emulsions contain 10 per cent-50 per cent of the copper or cuprammonium salt, a hydrocarbon or mineral oil solvent and an emulsifier.  The hydrocarbon solvent may also contain ethers, alcohols and ketones.  A typical concentrate is described as containing 30 per cent by weight of cupric dinonyl naphthalene sulphonate, 40 per cent of xylene, 20 per cent of isophorone or dipentene and/or isopropyl alcohol and 10 per cent of an emulsifier. Examples describe, (3) a concentrate containing 30 per cent cupric dinonyl naphthalene sulphonate, 45 per cent isophorone, 15 per cent hydrocarbon solvent and 10 per cent emulsifier for use in preparing aqueous emulsions, and (4) to (6), similar compositions containing as active ingredient cupric monononyl-, cupric dinonyl-, and cupric ammonium dinonyl-naphthalene sulphonates and a mixture of cupric mono- and di-nonyl naphthalene sulphonates are described.