Patent GB-1062123-A (GB)
Title: Cyclic amidines and compositions containing them
IPC: C07D233/16
Filed: 1964-05-21
Abstract: A liquid hydrocarbon fuel has dissolved therein at least one cyclic amidine of the general formula <FORM:1062123/C4-C5/1> wherein R1 is C1-C24 alkyl, phenyl, naphthyl, benzyl, or said aryl groups substituted with one or more alkyl groups contributing a total of not more than 16 carbon atoms; R2 is hydrogen or C1-C24 alkyl; or R1 and R2 together with the nitrogen atom to which they are joined represent a morpholino, thiamorpholino, piperidino or pyrrolidinyl group; X represents ethylene, ethenylene, trimethylene, alkyl- or alkenyl-substituted ethylene having a total of up to 20 carbon atoms, 1,2-cyclohexylene or alkyl-substituted 1,2-cyclohexylene having a total of up to 16 carbon atoms, 1,2-cyclohexenylen or alkyl-substituted 1,2-cyclohexenylene having a total of up to 16 carbon atoms, 3,6-methano-1,2 - cyclohexylene and 3,6 - methano - 1,2 - cyclohexenylene; R3 represents hydrogen, 2-hydroxyethyl, 2 - amino - ethyl, 2- or 3-hydroxypropyl, 2- or 3-aminopropyl, 2- or 3-(2-aminoethyl) aminopropyl, 2- or 3-(2- or 3-aminopropyl) aminipropyl, 2-(3-aminopropyl) aminoethyl, or 2-(2-aminoethyl) aminoethyl; and D represents 1,2-cyclohexylene or a divalent saturated chain of 2 or 3 carbon atoms whose available valencies are satisfied by hydrogen atoms and/or alkyl groups which contribute a total of not more than 12 additional carbon atoms. Specified fuels are gasolines, jet and diesel fuels and furnace oils and a specified additive is tetraethyl lead.ALSO:The invention comprises cyclic amidines of the general formula <FORM:1062123/C2/1> wherein R1 is C1-C24 alkyl, phenyl, naphthyl, benzyl or said aryl groups substituted with one or more alkyl groups contributing a total of not more than 16 carbon atoms; R2 is hydrogen or C1-C24 alkyl; or R1 and R2 together with the nitrogen atom to which they are joined represent a morpholino, thiamorpholino, piperidino, or pyrrolidinyl group; X represents ethylene, ethenylene, trimethylene, alkyl- or alkenyl-substituted ethylene having a total of up to 20 carbon atoms, 1,2-cyclohexylene or alkyl-substituted 1,2-cyclohexylene having a total of up to 16 carbon atoms, 1,2-cyclohexenylene or alkyl-substituted 1,2-cyclohexenylene having a total of up to 16 carbon atoms, 3,6-methano-1,2-cyclohexylene and 3,6 - methano - 1,2 - cyclo-hexenylene; R3 represents hydrogen, 2 - hydroxyethyl, 2-aminoethyl, 2- or 3-hydroxy-propyl, 2- or 3-aminopropyl, 2- or 3-(2-amino-ethyl)aminopropyl, 2- or 3-(2- or 3-amino-propyl)aminopropyl, 2-(3-aminopropyl)amino-ethyl, or 2-(2-aminoethyl)aminoethyl; and D represents 1,2-cyclohexylene or a divalent saturated chain of 2 or 3 carbon atoms whose available valencies are satisfied by hydrogen atoms and/or alkyl groups which contribute a total of not more than 12 additional carbon atoms and acid addition salts thereof.  These amidines may be prepared by reacting at a temperature at which water is split off an amidoacid of the formula <FORM:1062123/C2/2> with an amine of the formula R3NHDNH2 and, if desired, reacting the cyclic amidine so formed with an acid to form the acid addition salt.ALSO:Biocidal compositions comprise a cyclic amidine of the general formula <FORM:1062123/A5-A6/1> wherein R1 is C1-C24 alkyl, phenyl, naphthyl, benzyl, or said aryl groups substituted with one or more alkyl groups contributing a total of not more than 16 carbon atoms; R2 is hydrogen or C1-C24 alkyl; or R1 and R2 together with the nitrogen atom to which they are joined represent a morpholino, thiamorpholino, piperidino, or pyrrolidinyl group; X represents ethylene, ethenylene, trimethylene, alkyl- or alkenylsubstituted ethylene having a total of up to 20 carbon atoms, 1,2-cyclohexylene or alkyl-substituted 1,2-cyclohexylene having a total of up to 16 carbon atoms, 1,2-cyclohexenylene or alkyl-substituted 1,2-cyclohexenylene having a total of up to 16 carbon atoms, 3,6-methano-1,2-cyclohexylene and 3,6-methano -1,2-cyclohexenylene; R3 represents hydrogen, 2-hydroxyethyl, 2-aminoethyl, 2- or 3-hydroxypropyl, 2- or 3-aminopropyl, 2- or 3-(2-aminoethyl) aminopropyl, 2- or 3-(2- or 3-aminopropyl) aminopropyl, 2(3 aminopropyl) aminoethyl or 2(2-aminoethyl) aminoethyl; and D represents 1,2-cyclohexylene as a divalent saturated chain of 2 or 3 carbon atoms whose available valencies are satisfied by hydrogen atoms and/or alkyl groups which contribute a total of not more than 12 additional carbon atoms, or an acid-addition salt thereof, together with a diluent.  The compositions may also contain specified emulsifying agents, wetting agents, spreading agents, dispersing agents and further unspecified pesticides and may be in the form of wettable powders, emulsions, dusts, granular formulations, aerosols or sprays.