Patent GB-463544-A (GB)
Title: Improvements in or relating to the manufacture of products especially suitable for use as vermin destroying and insecticidal agents
IPC: A01N41/02
Filed: 1935-06-28
Abstract: Acids of the formula R--X--R<1>--(Y--SO3H) in which R represents a substituted or unsubstituted hydrocarbon radicle, X the atom or group O, S or SO2, R<1> an alkylene group, and Y denotes O or may be absent, are combined with nicotine, pyridine, piperidine, cetylamine, dimethyldodecylamine, cyclohexylamine or quinoline, or with copper, mercury, arsenic or thallium bases, to form salts which possess vermin-destroying and insecticidal properties.  The salts may also be formed by interaction of salts of the acids with salts of the bases. The products may be used in the form of solutions or emulsions or in admixture with fillers such as talcum.  According to the examples: (1) dodecyl - sulphonethane - sulphonic acid, C12H25.SO2.CH2.CH2.SO3H, is neutralized with cyclohexylamine; the salt is utilized as a parasiticide in dilute aqueous solution; (2) the copper salt of the o -butyl ether of decylsulphuric acid ester, C4H9OC10H20.O.SO3H, is prepared by reacting the sodium salt of the acid with copper sulphate in aqueous solution; its suspension in water is useful for removing vermin from vines; the cyclohexylamine salt of the naphthenyl ether of ethane-sulphonic acid may also be employed.  Reference is also made to the o -lauryl ether of ethane-sulphonic acid, the o -butyl or cyclohexyl ether of decanesulphonic acid, o -phenyl-thiohexane-sulphonic acid and cetyl-thioethane-sulphonic acid as salt-forming components.  Ethers of aliphatic sulphonic acids.--The o -butyl ether of decane-sulphonic acid is obtained by reacting monosodium decane-diol with butyl chloride, esterifying with hydrochloric acid and treating with sodium sulphite.  The o -cyclohexyl ether of this acid, and the o -lauryl and naphthenyl ethers of ethane-sulphonic acid, are analogously prepared.  Thio-aliphatic sulphonic acids.--Cetyl-thioethane-sulphonic acid is prepared by treating ethylene chlorhydrin with sodium hydrogen sulphide, reacting the sodium compound of the product with cetyl chloride, esterifying with hydrochloric acid and treating with sodium sulphite.  The dodecyl compound is prepared in the same way.  o -Phenyl-thiohexane-sulphonic acid is obtained in an analogous manner, after reacting sodium thiophenate with hydroxyhexyl chloride.  Dodecyl - sulphonethane - sulphonic acid is obtained either by oxidizing dodecyl-thioethane-sulphonic acid, e.g. with potassium permanganate, or by reducing dodecyl-sulphonyl chloride with zinc dust and reacting the sodium salt of the resulting sulphinic acid with b -chlorethane-sulphonic acid.  The o -butyl ether of decyl-sulphuric acid ester is prepared by esterifying with sulphuric acid the mono-butyl ether of decane-diol, which is described above.ALSO:Acids of the formula R--X--R<1>--(Y--SO3H), in which R represents a substituted or unsubstituted hydrocarbon radicle, X the atom or group O, S or SO2, R<1> an alkylene group, and Y denotes O or may be absent, are combined with copper, mercury, arsenic or thallium bases to form salts which possess vermin-destroying and insecticidal properties.  The products may also be formed by interaction of salts of the acids with salts of the bases.  According to one example, the copper salt of the w-butyl ether of decyl-sulphuric acid ester, C4H9O.C10H20.O.SO3H, is prepared by reacting the sodium salt of the acid with copper sulphate in aqueous solution.  Reference is also made to dodecyl-sulphonethane-sulphonic acid, the w-lauryl ether of ethane-sulphonic acid, the w-butyl or cyclohexyl ether of decane-sulphonic acid, w-phenylthiohexane-sulphonic acid and cetyl-thioethane-sulphonic acid as salt-forming components.