Patent GB-1038521-A (GB)
Title: Process and compounds for treating materials against fungal and bacterial infections and protected materials obtained thereby
IPC: A01N35/06
Filed: 1963-01-08
Abstract: Soluble oils are protected against attack by microbes by incorporating therein a compound having one of the formulae <FORM:1038521/C4-C5/1> <FORM:1038521/C4-C5/2> <FORM:1038521/C4-C5/3> or a salt particularly a chlorinated phenol or o-phenyl phenol salt or a quaternary ammonium compound thereof, wherein R1-R14 are each hydrogen or an alkyl or alkenyl group having 1 to 18 carbon atoms, an aralkyl or substituted aralkyl group or cycloalkyl group having up to 9C, except that at least one of R11-R14 is not hydrogen, while R2 can also be hydroxyalkyl having 1-8C, X1-X4 are each hydrogen or an alkyl or alkenyl group having 1-18C, hydroxyalkyl, cycloalkyl having 1-9C, aryl or an aralkyl or substituted aralkyl group, while at least one of the pairs X1 and X2 and X3 and X4 may be part of a saturated heterocyclic ring containing the N atom and which may contain a further hetero atom selected from O, s, and N; and n is 1 to 6. Specified aralkyl groups are phesalkyl and naphthalkyl groups.  The bases may be quaternized with alkylhalides, dialkyl sulphates, aralkyl halides or alkyl p-toluene sulphonates.  Where X1 and X2 or X3 and X4 form part of ring with the N atom it may be a morpholine, piperidine, piperazine, or pyrrolidine ring. Materials treated are soluble oils consisting of petroleum fractions or lard, sperm or rape seed oil, which, petroleum fractions or fatty oils may be chlorinated, sulphurized or sulphonated and emulsifying agents, e.g. amine and sodium soaps of alcohols and polyethoxylated phenols which soluble oils may also contain alcohols, glycols or glycolethers as coupling agents.ALSO:Aqueous media are protected against attack by microbes by incorporating therein a compound having one of the formulae:- <FORM:1038521/C1/1> , <FORM:1038521/C1/2> and <FORM:1038521/C1/3> or a salt, particularly a chlorinated phenol or o-phenyl phenol salt or a quaternary ammonium compound thereof, wherein R1-R14 are each hydrogen or an alkyl or alkenyl group having 1 to 18 carbon atoms, an aralkyl or substituted aralkyl group or cycloalkyl group having up to 9C, except that at least one of R11-R14 is not hydrogen, while R2 can also be hydroxyalkyl having 1-8C, X1-X4 are each hydrogen or an alkyl or alkenyl group having 1-18C, hydroxyalkyl, cycloalkyl having 1-9C, aryl or an aralkyl or substituted aralkyl group, while at least one of the pairs X1 and X2 and X3 and X4 may be part of a saturated heterocyclic ring containing the N atom and which may contain a further hetero atom selected from O, S, and N; and n is 1 to 6.  Specified aralkyl groups are phenalkyl and naphthalkyl groups.  The bases may be quaternized with alkylhalides, dialkyl sulphates, aralkyl halides or alkyl p-toluene sulphonates.  Where X1 and X2 or X3 and X4 form part of a ring with the N atom it may be a morpholine, piperidine, piperazine, or pyrrolidine ring. Materials treated are paper mill waters and oil flood waters.ALSO:Compounds of the formula <FORM:1038521/C2/1> and <FORM:1038521/C2/2> wherein R1 to R14 are each H, alkyl or alkenyl of 1-18 C, or aralkyl or substituted aralkyl or cycloalkyl of up to 9 C, except that at least one of R11-R14 is not hydrogen, while R2 can also be hydroxyalkyl of 1-8 C, X1-X4 are each H, alkyl or alkenyl of 1-18 C, hydroxy alkyl, cycloalkyl of up to 9 C, aryl or aralkyl or substituted aralkyl, while at least one of the pairs X1 and X2, and X3 and X4, may be part of a saturated heterocyclic ring containing the indicated N atom and may contain together with carbon a further hetero atom selected from O, S or N; and n is 1-6, are prepared from secondary amines and ketones and/or aldehydes according to the representative equations  <FORM:1038521/C2/3> Specific compounds obtained include 2,2-bis (dimethylamino methyl) - 3 - hydroxypropionaldehyde, 2,2 - bis - (Di - n - propylaminomethyl) - cyclohexanone, 2,5 - bis (dimethylaminomethyl) - cyclopentanone dihydrochloride, N - piperidino - 2 - benzyl - 2 - dialkylaminomethyl - butanone - 3 (alkyl = methyl, ethyl or propyl), 2-(dibenzylaminomethyl)-6-(dimethylaminomethyl) - cyclohexanone and its hydrochloride.  The 2,4,5-trichlorophenol, o-phenyl phenol, and 2,4,6-trichloro phenol salts of the above amines are prepared by reacting the free base or its hydrochloride with the phenol.  The free bases may be quaternated by reaction with alkylating or aralkylating agents.ALSO:Materials other than plants and other living organisms are protected against attack by microbes by incorporating therein a compound having one of the formulae <FORM:1038521/A5-A6/1> or a salt particularly a chlorinated phenol or o-phenyl phenol salt or a quaternary ammonium compound thereof, wherein R1-R14 are each hydrogen or an alkyl or alkenyl group having 1 to 18 carbon atoms, an aralkyl or substituted aralkyl group or cycloalkyl group having 1 to 9C, except that at least one of R11-R14 is not hydrogen, while R2 can also be hydroxyalkyl having 1-8C, X1-X4 are each hydrogen or an alkyl or alkenyl group having 1-18C, hydroxyalkyl, cycloalkyl having 1-9C, aryl or an aralkyl or substituted aralkyl group, while at least one of the pairs X1 and X2 and X3 and X4, may be part of a saturated heterocyclic ring containing the N atom and which may contain a further hetero atom selected from O, S, and N; and n is 1 to 6. Specified aralkyl groups are phenalkyl and naphthalkyl groups.  The bases may be quaternized with alkyl halides dialkyl sulphates, aralkyl halides or alkyl p-toluene sulphonates.  Where X1 and X2 or X3 and X4 form part of a ring with the N atom it may be a morpholine, piperidine, piperazine, or pyrrolidine ring.  Materials treated are adhesives, paints, waxes, polishes, wood, paper mill waters, oil flood waters, wood and soluble oils consisting of petroleum fractions or lard, sperm or rape seed oil, which petroleum fractions or fatty oils may be chlorinated, sulphurized or sulphonated and emulsifying agents e.g. amine and sodium soaps of alcohols and polyethoxylated phenols which soluble oils may also contain alcohols, glycols or glycol ethers as coupling agents.