Patent GB-913936-A (GB)
Title: Substituted iminopyrrolines
IPC: C07D209/44
Filed: 1959-03-02
Abstract: The invention comprises compounds of the formula <FORM:0913936/IV (b)/1> where R and R5 each represent an organic substituent which is connected to the nitrogen through a carbon atom which is itself attached to not more than two other carbon atoms, said substituent being (a) a hydrocarbon group free of acetylenic unsaturation, (b) a hydroxysubstituted saturated aliphatic or cycloaliphatic group, or (c) a group -R8NR6R7 or -R8OR6, where R8 is a divalent saturated aliphatic or cycloaliphatic group, the carbon atom having the free valency also carrying at least one hydrogen atom, R6 and R7 are saturated aliphatic or cycloaliphatic groups or R7 or R 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 carry 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 (i) reacting an amine R5NH2 at 75-300 DEG C. with a compound <FORM:0913936/IV (b)/2> or a tautomer or acid addition salt thereof, or (ii) (when R5 = R) by the reaction of two moles of an amine R5NH2 with one mole of a cyanoketone <FORM:0913936/IV (b)/3> Examples prepare (1) 1-benzyl-5-benzylimino-2,4,4-trimethyl-2-pyrroline, (2) 1-butyl-5-butylimino-2,4,4-trimethyl-2-pyrroline, (3) 1-dodecyl-5-dodecylimino-2,4,4-trimethyl-2-pyrroline, and (4) 1-benzyl-5-butylimino- and 1-butyl-5-benzylimino-2,4,4-trimethyl-2-pyrroline.  Other products and reactants are specified.  A list of suitable salt-forming acids is given.  The compounds of the invention are pesticides (see Group VI).ALSO:Pesticidal compositions, e.g. bactericides and fungicides, comprise a diluent and a compound of formula <FORM:0913936/VI/1> or an acid addition salt thereof; where R and R5 are organic substituents attached to the nitrogen through a carbon atom which is itself attached to not more than two other carbon atoms, said substituents being (a) hydrocarbon groups free of acetylenic 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 also carrying at least one hydrogen atom, and R6 and R7 are aliphatic or cycloaliphatic groups, or R or R-may be hydrogen; R2 is hydrogen or C1-7 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 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 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.