Patent GB-1035094-A (GB)
Title: Improvements relating to herbicides and novel 3-substituted uracils
IPC: C07D239/22
Filed: 1962-12-07
Abstract: Novel uracil addition compounds of the general formula <FORM:1035094/C2/1> or the corresponding isomeric formula <FORM:1035094/C2/2> wherein NB represents a nitrogenous base having an ionization constant Kb in water of at least 10-9; and R1, R2 and R3 are as 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 carboxy-methyl-thiomethyl radical; and R3 represents a methyl radical;  (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 4 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, a substituted aryl radical containing 6 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 containing 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 mixing equimolar amounts of the base and the uracil, if desired in a solvent. Bases used in examples are ethanolamine, octylamine, ethylenediamine, dodecylamine, cocoadiamine, piperidine, ammonia, methylamine, oleylamine, triethylamine, 2-aminooctanol-1, 2-methylpiperidine, 4-methylpiperidine, triethylenediamine, butylamine, methoxypropylamine, hexamethylenediamine, piperazine and see-butylamine.  The above compounds are herbicides (see Division A5).ALSO:Uracil addition compounds of the general formula <FORM:1035094/A5-A6/1> or the corresponding isomeric formula <FORM:1035094/A5-A6/2> wherein NB represents a nitrogenous base having an ionisation constant Kb in water of at least 10-9; and R1, R2 and R3 are as 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 4 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 carboxy-methylthiomethyl radical; and R3 represents a methyl radical; (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