Patent GB-913937-A (GB)
Title: Substituted iminopyrrolidines
IPC: C07D209/44
Filed: 1959-03-02
Abstract: The invention comprises compounds of the formula <FORM:0913937/IV (b)/1> and acid addition salts thereof, where R and R5 are organic substituents which are connected to the nitrogen atom through a carbon atom which is itself attached to not more than two other carbon atoms, said substituents being (a) hydrocarbon groups free of non-aromatic unsaturation, (b) hydroxy-substituted aliphatic or cycloaliphatic groups, or (c) groups -R8NR6R7 or -R8OR6, where R8 is a divalent saturated aliphatic or cycloaliphatic group, the carbon atom having the free valency carrying at least one hydrogen atom, and R6 and R7 are saturated aliphatic or cycloaliphatic groups or R7 may be hydrogen; R2 is hydrogen or C1-4 alkyl; and R1, R3 and R4 are hydrocarbon groups free of non-aromatic unsaturation, or R3 or R4 may be hydrogen, or one of the pairs R1R2, R2R3 and R3R4 or both the pairs R1R2 and R3R4 may be joined together to form a cyclopentyl or cyclohexyl group which may contain one or more alkyl substituents and/or a methylene bridge which together contribute a total of not more than four additional carbon atoms; acid addition salts thereof; and their preparation by hydrogenating in the presence of a hydrogenation catalyst at up to 250 DEG C. a compound of formula <FORM:0913937/IV (b)/2> Specified catalysts are Raney nickel, Raney cobalt, cobalt with ammonia, nickel with ammonia, cobalt-copper, nickel-cobalt, palladium, platinum and ruthenium; carriers may be employed. Examples prepare (1) 1-dodecyl-2-dodecylimino-3,3,5-trimethylpyrrolidine, (2) 1-butyl - 2 - butylimino-3,3,5-trimethylpyrrolidine, (3) 1 - benzyl - 2 - benzylimino-3,3,5-trimethylpyrrolidine, and (4) 1-(2-hydroxyethyl)-2 - (2 - hydroxyethylimino) - 3,3,5 - trimethylpyrrolidine.  Other products and starting materials are listed, and suitable values for the R group and suitable salt-forming acids are given.  The products are pesticides (see Group VI).  Specification 913,936 is referred to.ALSO:Pesticidal compositions, e.g. fungicides, comprise a diluent and a compound of formula <FORM:0913937/VI/1> or an acid addition salt thereof, where R and R5 are organic substituents connected to the nitrogen by a carbon atom which is itself attached to not more than two other carbon atoms, said substituents being (a) hydrocarbon groups free of non-aromatic unsaturation, (b) hydroxy-substituted saturated aliphatic or cycloaliphatic groups, or (c) groups -R8NR6R7 or -R8OR6, where R8 is a divalent saturated aliphatic or cycloaliphatic group, the carbon atom having the free valency carrying at least one hydrogen atom, and R6 and R7 are saturated aliphatic or cycloaliphatic groups, or R7 may be hydrogen; R2 is hydrogen or C1-4 alkyl; and R1, R3 and R4 are hydrocarbon groups free of non-aromatic unsaturation, or R3 or R4 may be hydrogen, or one of the pairs R1, R2; R2, R3 and R3, R4, or both pairs R1, R2 and R3, R4 may be joined together to form a cyclopentyl or cyclohexyl group which may contain one or more alkyl substituents and/or a methylene bridge which together contribute a total of not more than four additional carbon atoms (see Group IV (b)).  The compositions may be powders, solutions, emulsions or dispersions.  Many acid addition salts are specified. Specification 913,936 is referred to.