Patent GB-1098209-A (GB)
Title: Novel phenazine derivatives, processes for their preparation, and biocidal compositions containing them
Inventor: CROSS BARRINGTON
IPC: C07D241/46
Filed: 1966-09-21
Abstract: Biocidally active detergent compositions comprise a carrier and/or a surface active agent, in association with, as a pesticide, at least one sulphur-containing phenazine of the general formula <FORM:1098209/C4-C5/1> or N-oxides thereof, wherein R1 represents a halogen atom or an alkoxy or alkyl group, R2 represents an alkyl, alkenyl or aryl group, X represents a sulphur atom or a sulphonyl group, and a, b, c and d each represents 0, 1, 2, 3 or 4, provided that a+b is at least 1 and a+c and b+d are both at most 4.  Examples of suitable carriers are silicates, clays, carbon, sulphur, resins, waxes, solid fertilizers, e.g. superphosphates, water, alcohols, ketones, ethers, aromatic hydrocarbons, petroleum fractions, chlorinated hydrocarbons, or mixtures thereof.  The surface active agent may be, for example, sodium or calcium salts of polyacrylic acids, the condensation products of fatty acids or aliphatic amines or amides containing at least 12 carbon atoms per molecule with ethylene oxide and/or propylene oxide; partial esters of the above fatty acids with glycerol, sorbitan, sucrose or pentaerythritol; condensation products of alkyl phenols with ethylene oxide and/or propylene oxide; sulphates or sulphonates of these condensation products; and alkali metal salts of sulphuric acid esters or sulphonic acids containing at least 10 carbon atoms per molecule. Optional additives include protective colloids, sodium polyphosphates, cellulose ethers, stabilizers such as EDTA; other pesticides; and stickers, e.g. non-volatile oils. The compositions may be formulated as wettable powders, dusts, granules, solutions, emulsifiable concentrates and emulsions.ALSO:Novel phenazines of the general formula <FORM:1098209/C2/1> and N-oxides thereof, wherein R1 represents a halogen atom or an alkyl group, R2 represents an alkyl, alkenyl or aryl group, X represents a sulphur atom or a sulphonyl group and a, b, c and d each represents 0, 1, 2, 3 or 4; provided that a+b is at least 1, a+c and b+d are both at most 4, and when b, c and d are 0, R2 does not represent a methyl group when X is a sulphur atom, or a phenyl group when X is a sulphonyl group, are prepared (a), when X is a sulphur atom, by reacting an alkali metal mercaptide, which may be formed in situ by reaction of an alkyl mercaptan and an alkali metal hydroxide, with a halophenazine or halophenazine-N-oxide; (b) when X is a sulphonyl group, by reacting the corresponding thioether with an oxidizing agent. When the product is an N-oxide it may optionally be reduced to the free base form by reaction with an alkali metal dithionite.  The novel phenazines of the above general formula possess acaridical, fungicidal or herbicidal activity.ALSO:Biocidal compositions comprise a carrier and/or a surface active agent, in association with, as active ingredient, at least one sulphur-containing phenazine of the general formula <FORM:1098209/A5-A6/1> or N-oxides thereof, wherein R1 represents a halogen atom or an alkoxy or alkyl group, R2 represents an alkyl, alkenyl or aryl group, X represents a sulphur atom or a sulphonyl group, and a, b, c and d each represents 0, 1, 2, 3 or 4, provided that a+b is at least 1 and a+c and b+d are each at most 4. Examples of suitable carriers are silicates, clays, carbon, sulphur, resins, waxes, solid fertilisers, e.g. superphosphates, water, alcohols, ketones, ethers, aromatic hydrocarbons, petroleum fractions, chlorinated hydrocarbons, or mixtures thereof.  The surface active agent may be, for example, sodium or calcium salts of polyacrylic acids, the condensation products of fatty acids or aliphatic amines or amides containing at least 12 carbon atoms per molecule with ethylene oxide and/or propylene oxide; partial esters of the above fatty acids with glycerol, sorbitan, sucrose or pentaerythritol; condensation products of alkyl phenols with ethylene oxide and/or propylene oxide; sulphates or sulphonates of these condensation products; and alkali metal salts of sulphuric acid esters or sulphonic acids containing at least 10 carbon atoms per molecule.  Optional additives include protective colloids, sodium polyphosphates, cellulose ethers, stabilisers such as EDTA, other pesticides; and stickers, e.g. non-volatile oils.  The compositions may be formulated as wettable powders, dusts, granules, solutions, emulsifiable concentrates and emulsions.