Patent GB-913932-A (GB)
Title: Iminopyrrolidines
IPC: C07D207/267
Filed: 1959-03-02
Abstract: The invention comprises compounds of the formula <FORM:0913932/IV (b)/1> where R is hydrogen or an organic substituent which is connected to the nitrogen through a carbon atom which is itself attached to no more than two other carbon atoms, said substituent being (a) a hydrocarbon group free of non-aromatic substitution, (b) a hydroxy-substituted saturated aliphatic or cycloaliphatic group, or (c) a group -R5NR6R7 or -R5OR6, where R5 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 monovalent 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 and R4 may be hydrogen, or one of the pairs R1R2, R2R3 or 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 which contribute a total of not more than 4 additional carbon atoms; acid addition salts of these compounds; and their preparation by hydrogenating at up to 250 DEG C., in the presence of a hydrogenation catalyst, a compound of formula <FORM:0913932/IV (b)/2> or <FORM:0913932/IV (b)/3> or a tautomer thereof, X being HO- or R8O-, where R8 is C1-4 alkyl, or RNH-.  Specified catalysts are Raney nickel, Raney cobalt, cobalt with ammonia, nickel with ammonia, cobalt-copper, nickel-cobalt, palladium, platinum, rhodium and ruthenium; carriers may be used.  Examples prepare (1) 3,3,5-trimethyl-2-lauryliminopyrrolidine, (2) 3,3,5-trimethyl-2-cyclohexyliminopyrrolidine, (3) 3,3,5-trimethyl-2-n-butyliminopyrrolidine, (4), (6) and (7) 3,3,5-trimethyl-2-methyliminopyrrolidine, and (5) 3,3,5-trimethyl-2-iminopyrrolidine (and 3,3,5-trimethyl-2-pyrrolidone).  Other products are specified, and suitable starting materials are listed.  Other suitable values for the R groups are also given.  Suitable saltforming acids are listed. Salts are formed with penicillin.  The compounds are pesticides (see Group VI).  Specification 913,931 is referred to.ALSO:Pesticidal compositions comprise a diluent and a compound of formula <FORM:0913932/VI/1> or a salt thereof, where R is hydrogen or an organic substituent which is connected to the nitrogen through a carbon atom which is itself attached to no more than two other carbon atoms, said substituent being (a) a hydrocarbon group free of non-aromatic unsaturation, (b) a hydroxy-substituted saturated aliphatic or cycloaliphatic group, or (c) a group -R5NR6R7 or -R5OR6, where R5 is a divalent saturated aliphatic or cycloaliphatic group, and R6 and R7 are monovalent saturated aliphatic or cycloaliphatic groups, or R7 may be hydrogen; R2 is hydrogen or C1-4 alkyl; 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; or R3, R4 or both the 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 which contribute a total of not more than 4 additional carbon atoms (see Group IV (b)).  Many salt-forming acids are listed. The compositions may be powders, solutions, emulsions or dispersions. Many acid addition salts are specified. Specification 913,931 is referred to.