Patent GB-913931-A (GB)
Title: Iminopyrrolines
IPC: C07D209/96
Filed: 1959-03-02
Abstract: The invention comprises compounds of the formula <FORM:0913931/IV (b)/1> or a tautomer thereof of formula <FORM:0913931/IV (b)/2> or <FORM:0913931/IV (b)/3> where R is hydrogen or an organic substituent connected to the nitrogen through a carbon atom which in turn is attached to not more than two other carbon atoms, said substituent being (a) a hydrocarbon group free of acetylenic 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, the carbon atom having the free valency also carrying at least one hydrogen atom, and R6 and R7 are saturated aliphatic or cycloaliphatic groups and R7 can be hydrogen; R2 is hydrogen or C1-4 alkyl group; and R1, R3 and R4 are hydrocarbon groups free of non-aromatic substitution, with the provisos that R3 and R4 may be hydrogen, and that one of the pairs R1R2, R1R3, 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 4 additional carbon atoms.  These compounds are prepared by the reaction between one mole of a cyanoketone <FORM:0913931/IV (b)/4> and one mole of ammonia or an amine RNH2, preferably at 40-250 DEG C. in the presence of an inert organic solvent which forms an azeotrope with water, the water formed in the reaction being removed azeotropically during the reaction. Intermediates of the formula <FORM:0913931/IV (b)/5> are generally formed, and are converted to the desired products by heating. Examples prepare (1) 2,4,4-trimethyl-5-laurylimino-2-pyrroline, (2) 2-methyl-5-laurylimino-2-pyrroline, (3) 2,4,4-trimethyl-5-octadecylimino-2-pyrroline, (4) 2,4,4, - trimethyl-5-cyclohexylimino-2-pyrroline, (5) and (10) 2,4, 4-trimethyl-5-methylimino-2-pyrroline, (6) 2,4,4-trimethyl-5-butylimino-2-pyrroline, (7) and (9) 2,4,4-trimethyl-5-benzylimino-2-pyrroline, and (8) 2,4,4 - trimethyl - 5 - phenylimino-2-pyrroline.  Other products are specified, suitable cyanoketones and amines are listed, and suitable values for the R groups are given.  The compounds of the invention are pesticides (see Group VI).  Specifications 913,932, 913,933, 913,934, 913,935, 913,936, 913,937 and 913,938 are referred to.ALSO:Pesticidal compositions comprise a diluent and one or more compounds of formula <FORM:0913931/VI/1> or a tautomer thereof (see Group IV (b)), where R is hydrogen or an organic substituent connected to the nitrogen through a carbon atom which in turn is attached to not more than two other carbon atoms, said substituent being (a) a hydrocarbon group free of acetylenc unsaturation, (b) a hydroxy-substituted saturated aliphatic or cycloaliphatic group, or (c) a group -R5NR6R7 or -R5OR6, where R5 is a saturated aliphatic or cycloaliphatic group, and R6 and R7 are saturated aliphatic or cycloaliphatic groups or R7 can 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 represent hydrogen, or one of the pairs R1, R2; R1, R3; 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 4 additional carbon atoms (see Group IV (b)).  The compositions may be powders, solutions, emulsions or dispersions.  Specifications 913,932, 913,933, 913,934, 913,935, 913,936, 913,937 and 913,938 are referred to.