Patent GB-1035096-A (GB)
Title: Improvements relating to herbicides
IPC: C07D239/96
Filed: 1962-12-07
Abstract: Novel quaternary ammonium salts of compounds of the general formula <FORM:1035096/C2/1> or the corresponding isomeric formula <FORM:1035096/C2/2> wherein X represents an oxygen or sulphur atom and R1, R2 and R3 are defined in one of paragraphs (A) to (D) below: (A)  R1 represents an alkyl radical containing 1 to 10 carbon atoms, a substituted alkyl radical containing 1 to 8 carbon atoms, an aryl radical containing 5 to 10 carbon atoms, a substituted phenyl radical, an aralkyl radical containing 5 to 13 carbon atoms, a substituted aralkyl radical containing 5 to 13 carbon atoms, an alkenyl radical containing 3 to 8 carbon atoms, an alkynyl radical containing 3 to 8 carbon atoms, a cycloalkyl radical containing 3 to 12 carbon atoms, a cycloalkenyl radical containing 4 to 12 carbon atoms, a substituted cycloalkyl radical in which the cycloalkyl radical contains 3 to 12 carbon atoms, a substituted cycloalkenyl radical in which the cycloalkenyl radical contains 4 to 12 carbon atoms, a cyano radical, a cycloalkyl alkyl radical containing 4 to 13 carbon atoms, a cycloalkenyl alkyl radical containing 5 to 13 carbon atoms, a (substituted cycloalkyl) alkyl radical containing 5 to 14 carbon atoms or a (substituted cycloalkenyl) alkyl radical containing 5 to 14 carbon atoms; R2 represents a chlorine, fluorine, bromine or iodine atom, a methyl radical, an ethyl radical, a propyl radical, a butyl radical, a methoxy radical, an ethoxy radical, a propoxy radical, a butoxy radical, a nitro radical, an alkoxymethyl radical containing 2 to 6 carbon atoms, a hydroxy alkyl radical containing 1 to 6 carbon atoms, an alkenyl radical containing 3 to 6 carbon atoms, a thiocyanato radical, a cyano radical, a mercaptomethyl radical, a methylthiomethyl radical, a phenylthiomethyl radical, an alkylthio radical containing 1 to 4 carbon atoms, a bromomethyl radical, a fluoromethyl radical, a chloromethyl radical or a carboxymethylthiomethyl radical; R3 represents a chlorine or bromine atom, an alkyl radical containing 1 to 5 carbon atoms, a chloroalkyl radical containing 1 to 4 carbon atoms, a bromoalkyl radical containing 1 to 4 carbon atoms, or an alkoxy radical containing 1 to 5 carbon atoms;  (B)  R1 represents a cycloalkyl radical containing 3 to 12 carbon atoms, a substituted cycloalkyl radical in which the cycloalkyl radical contains 3 to 12 carbon atoms, a cycloalkenyl radical containing 4 to 12 carbon atoms, a substituted cycloalkenyl radical in which the cycloalkenyl radical contains 4 to 12 carbon atoms; a cycloalkyl alkyl radical containing 4 to 13 carbon atoms, a (substituted cycloalkyl) alkyl radical containing 5 to 14 carbon atoms, a cycloalkenyl alkyl radical containing 4 to 13 carbon atoms or a (substituted cycloalkenyl) alkyl radical containing 5 to 14 carbon atoms; R2 represents a hydrogen atom; and R3 represents an alkyl radical containing 1 to 5 carbon atoms;  (C)  R1 represents an alkyl radical containing 1 to 10 carbon atoms, a substituted alkyl radical containing 1 to 10 carbon atoms, an aryl radical containing 6 to 14 carbon atoms, a substituted aryl radical containing 6 to 14 carbon atoms, an aralkyl radical containing 7 to 15 carbon atoms, a substituted aralkyl radical containing 7 to 15 carbon atoms, an alkenyl radical containing 3 to 10 carbon atoms, an alkynyl radical containing 3 to 10 carbon atoms, a cycloalkyl radical containing 3 to 12 carbon atoms, a cycloalkenyl radical containing 4 to 12 carbon atoms, a substituted cycloalkyl radical in which the cycloalkyl radical contains 3 to 12 carbon atoms, a substituted cycloalkenyl radical in which the cycloalkenyl radical contains 4 to 12 carbon atoms, a cycloalkyl alkyl radical containing 4 to 13 carbon atoms, a cycloalkenyl alkyl radical containing 5 to 13 carbon atoms, a (substituted cycloalkyl) alkyl radical containing 5 to 14 carbon atoms, a (substituted cycloalkenyl) alkyl radical containing 5 to 14 carbon atoms, a cyano radical, a dialkylamino radical containing 2 to 10 carbon atoms or an alkoxy radical containing 1 to 10 carbon atoms; and R2 and R3 together represent a divalent alkylene radical of formula (CH2)n where n is 3, 4 or 5;  (D)  R1 represents an alkyl radical containing 1 to 10 carbon atoms, a substituted alkyl radical containing 1 to 10 carbon atoms, an aryl radical containing 5 to 14 carbon atoms, an aralkyl radical containing 5 to 15 carbon atoms, a substituted aralkyl radical containing 5 to 15 carbon atoms, an alkenyl radical containing 3 to 10 carbon atoms, an alkynyl radical containing 3 to 10 carbon atoms, a cycloalkyl radical containing 3 to 12 carbon atoms, a cycloalkenyl radical containing 4 to 12 carbon atoms, a substituted cycloalkyl radical in which the cycloalkyl radical contains 3 to 12 carbon atoms, a substituted cycloalkenyl radical in which the cycloalkenyl radical contains 4 to 12 carbon atoms, a cycloalkyl alkyl radical containing 4 to 13 carbon atoms, a cycloalkenyl alkyl radical containing 5 to 13 carbon atoms, a (substituted cycloalkyl) alkyl radical containing 5 to 14 carbon atoms, a (substituted cycloalkenyl) alkyl radical containing 5 to 14 carbon atoms, a cyano radical, a dialkylamino radical containing 2 to 10 carbon atoms or an alkoxy radical containing 1 to 10 carbon atoms; R2 represents a hydrogen, chlorine, fluorine, bromine or iodine atom, a methyl radical, an ethyl radical, a propyl radical, a butyl radical, a methoxy radical, an ethoxy radical, a propoxy radical, a butoxy radical, a nitro radical, an alkoxymethyl radical containing 2 to 6 carbon atoms, a hydroxy alkyl radical containing 1 to 6 carbon atoms, an alkenyl radical containing 3 to 6 carbon atoms, a thiocyanato radical, a cyano radical, a mercaptomethyl radical, a methylthiomethyl radical, a phenylthiomethyl radical, an alkylthio radical containing 1 to 4 carbon atoms, a bromomethyl radical, a fluoromethyl radical, a chloromethyl radical or a carboxymethylthiomethyl radical; with the proviso that when R2 represents a hydrogen atom, R1 represents a cycloalkyl radical containing 3 to 12 carbon atoms, a substituted cycloalkyl radical in which the cycloalkyl radical contains 3 to 12 carbon atoms, a cycloalkenyl radical containing 4 to 12 carbon atoms, a substituted cycloalkenyl radical in which the cycloalkenyl radical contains 4 to 12 carbon atoms, a cycloalkyl alkyl radical containing 4 to 13 carbon atoms, a (substituted cycloalkyl) alkyl radical consaining 5 to 14 carbon atoms, a cycloalkenyl alkyl radical containing 5 to 13 carbon atoms or a (substituted cycloalkenyl) alkyl radical containing 5 to 14 carbon atoms; and R3 represents a hydrogen atom, are prepared by reacting the uracil with an appropriate quaternary ammonium hydroxide, e.g. in a solvent, or by reacting the sodium salt of the uracil with an appropriate quaternary ammonium halide in a solvent such as toluene or xylene, and removing precipitated sodium halide. These compounds are herbicides (see Division A5).ALSO:Quarternary ammonium salts of compounds of the general formula: <FORM:1035096/A5-A6/1> or the corresponding isomeric formula: <FORM:1035096/A5-A6/2> wherein X represents an oxygen or sulphur atom and R1, R2 and R3 are defined in one of paragraphs (A) to (D) below. (A) R1 represents an alkyl radical containing 1 to 10 carbon atoms, a substituted alkyl radical containing 1 to 8 carbon atoms, an aryl radical containing 5 to 10 carbon atoms, a substituted phenyl radical, an aralkyl radical containing 5 to 13 carbon atoms, a substituted aralkyl radical containing 5 to 13 carbon atoms, an alkenyl radical containing 3 to 8 carbon atoms, an alkynyl radical containing 3 to 8 carbon atoms, a cycloalkyl radical containing 3 to 12 carbon atoms, a cycloalkenyl radical containing 4 to 12 carbon atoms, a substituted cycloalkyl radical in which the cycloalkyl radical contains 3 to 12 carbon atoms, a substituted cycloalkenyl radical in which the cycloalkenyl radical contains 4 to 12 carbon atoms, a cyano radical, a cycloalkyl alkyl radical containing 4 to 13 carbon atoms, a cycloalkenyl alkyl radical containing 5 to 13 carbon atoms, a (substituted cycloalkyl) alkyl radical containing 5 to 14 carbon atoms or a (substituted cycloalkenyl) alkyl radical containing 5 to 14 carbon atoms; R2 represents a chlorine, fluorine, bromine or iodine atom, a methyl radical, an ethyl radical, a propyl radical, a butyl radical, a methoxy radical, an ethoxy radical, a propoxy radical, a butoxy radical, a nitro radical, an alkoxymethyl radical containing 2 to 6 carbon atoms, a hydroxy alkyl radical containing 1 to 6 carbon atoms, an alkenyl radical containing 3 to 6 carbon atoms, a thiocyanato radical, a cyano radical, a mercaptomethyl radical, a methylthiomethyl radical, a phenylthiomethyl radical, an alkylthio radical containing 1 to 4 carbon atoms, a bromo-methyl radical, a fluoromethyl radical, a chloromethyl radical or a carboxy-methylthiomethyl radical; R3 represents a chlorine or bromine atom, an alkyl radical containing 1 to 5 carbon atoms, a chloralkyl radical containing 1 to 4 carbon atoms, a bromoalkyl radical containing 1 to 4 carbon atoms, or an alkoxy radical containing 1 to 5 carbon atoms;  (B) R1 represents a cycloalkyl radical containing 3 to 12 carbon atoms, a substituted cycloalkyl radical in which the cycloalkyl radical contains 3 to 12 carbon atoms, a cycloalkenyl radical containing 4 to 12 carbon atoms, a substituted cycloalkenyl radical in which the cycloalkenyl radical contains 4 to 12 carbon atoms; a cycloalkyl alkyl radical containing 4 to 13 carbon atoms, a (substituted cycloalkyl) alkyl radical containing 5 to 14 carbon atoms, a cycloalkenyl alkyl radical containing 4 to 13 carbon atoms or a (substituted cycloalkenyl) alkyl radical containing 5 to 14 carbon atoms; R2 represents a hydrogen atom; and R3 represents an alkyl radical containing 1 to 5 atoms;  (C) R1 represents an alkyl radical containing 1 to 10 carbon atoms, a