Patent GB-1058548-A (GB)
Title: Quaternary salts of aromatic disulphonic acids and their use for combating phytopathogenic microorganisms
IPC: C07D215/10
Filed: 1964-09-10
Abstract: The invention relates to quaternary salts or aromatic disulphonic acids of the general formula <FORM:1058548/C2/1> in which R1 represents an alkyl group containing 10 to 18, preferably 12 to 16 carbon atoms, R2, R3 and R4 each represent an alkyl group containing 1 to 4 carbon atoms and together with the nitrogen atom form a heterocyclic ring system preferably one of pyridine, quinoline or isoquinoline, methylated and/or ethylated at the ring and X-2 is the anion of an aromatic disulphonic acid, preferably of benzene. Compounds claimed per se are bis-(N-dodecyl pyridinium) - benzene - 1 : 3 - disulphonate; bis - (N - hexadecyl pyridinium) - benzene-1 : 3 - disulphonate; bis - (N - dodecyl quinolinium) - benzene - 1 : 3 - disulphonate; bis-(N - dodecyl isoquinolinium) - benzene - 1 : 3-disulphonate; bis - (trimethyl dodecyl ammonium) - benzene - 1 : 3 - disulphonate.  The compounds may be prepared by reacting an alkyl ester of an aromatic disulphonic acid, preferably of benzene, containing 10 to 18, preferably 12 to 16, carbon atoms with (a) a tertiary amine of the general formula <FORM:1058548/C2/2> in which R1, R2 and R3 each represent an alkyl group containing 1 to 4 carbon atoms, or (b) a heterocyclic nitrogen base, preferably one of the group of pyridine, quinoline or isoquinoline or a derivative thereof methylated and/or ethylated in the ring or (c) by reacting a (C1-C4)-alkyl ester of an aromatic disulphonic acid, preferably of benzene, with a tertiary amine of the general formula <FORM:1058548/C2/3> in which R2 and R3 each represent an alkyl group containing 1 to 4 carbon atoms and R4 represents an alkyl group containing 10 to 18, preferably 12 to 16, carbon atoms.  The alkyl ester of the disulphonic acids may be prepared (a) by reacting the corresponding aromatic disulphochloride with the corresponding alcohol in the presence of an acid-binding agent, or (b) by subjecting the corresponding aromatic disulphonic acid dialkyl ester, the alkyl groups containing 1 to 6 carbon atoms, to an ester interchange reaction with an alcohol of the aforesaid kind.  In an example, bis-(N-dodecyl pyridinium) - benzene - 1 : 3 - disulphonate is prepared by heating benzene-1 : 3 - disulphonic acid didodecyl ester with pyridine.  Other examples are given.ALSO:Compositions for combating phytopathogenic micro organisms comprise an active ingredient a quaternary salt of an aromatic disulphonic acid of the general formula <FORM:1058548/A5-A6/1> in which R1 is an alkyl group containing 10 to 18 and preferably 12 to 16 carbon atoms, R2, R3, R4 each represent an alkyl group containing 1 to 4 carbon atoms and together with the nitrogen form a heterocyclic ring system preferably one of pyridine, quinoline or isoquinoline or a lower-alkyl ring-substituted derivative thereof and X-2 is the anion of an aromatic disulphonic acid, preferably of benzene. Specified active ingredients are bis-(N-dodecyl pyridinium) - benzene - 1:3 - disulphonate, bis-(N-hexadecyl pyridinium)-benzene-1:3-disulphonate, bis-(N-dodecyl quinolinium)-benzene-1:3-disulphonate, bis-(N-dodecyl isoquinolinium)-benzene-1:3-disulphonate, bis-(trimethyl dodecyl ammonium)-benzene-1:3-disulphonate.