Patent GB-1035095-A (GB)
Title: Improvements relating to herbicides and novel 3-substituted uracils
IPC: C07D239/96
Filed: 1962-12-07
Abstract: Novel uracil-phenol complexes of the formula <FORM:1035095/C2/1> or the corresponding isomeric formula <FORM:1035095/C2/2> wherein Z represents a hydrogen, bromine or chlorine atom, a nitro radical, an alkyl radical containing 1 to 3 carbon atoms or a radical of formula -OR5, where R5 represents an alkyl radical containing 1 to 3 carbon atoms; Y represents a chlorine atom or an alkyl radical containing 1 to 3 carbon atoms; m is 1, 2, 3, 4 or 5; and p, R1, R2, R3 and R4 are as defined in one of paragraphs (A) to (E) below:  (A) p is 1 or 2; 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 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 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, or a cyano radical.  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 alkoxy-methyl 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, alkylthio radical containing 1 to 4 carbon atoms a bromomethyl radical, a fluoromethyl radical, a chloromethyl radical, a methylthiomethyl radical, a phenylthiomethyl radical or a carboxymethylthiomethyl radical; R3 represents a methyl radical; and R4 represents a hydrogen atom;  (B) p is 1 or 2; 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 in which the cycloalkyl alkyl radical contains 4 to 13 carbon atoms, a cycloalkenyl alkyl radical containing 4 to 13 carbon atoms, or a (substituted cycloalkenyl)alkyl radical in which the cycloalkenyl alkyl radical contains 4 to 13 carbon atoms; R2 represents a hydrogen atom; R3 represents an alkyl radical containing 1 to 5 carbon atoms; and R4 represents a hydrogen atom;  (C) p is 1/2 , 1 or 2; 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 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 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 dialkylamino radical containing 2 to 10 carbon atoms, a cyano radical, or an alkoxy radical containing 1 to 10 carbon atoms; and R2 and R3 together form a divalent alkylene radical of formula (CH2)n where n is 3, 4 or 5; and R4 represents a hydrogen atom;  (D) p is 1 or 2; 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 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 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 13 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 dialkylamino radical containing 2 to 10 carbon atoms, a cyano radical 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 thiocyano radical, a cyano radical, a mercaptomethyl radical, an alkylthio radical containing 1 to 4 carbon atoms, a methylthiomethyl radical, a chloromethyl radical, a bromomethyl radical, a fluoromethyl radical, a phenylthiomethyl radical or a carboxymethylthiomethyl radical, with the proviso that when R2 represents a hydrogen atom R1 represents a substituted or unsubstituted cycloalkyl, cycloalkenyl, cycloalkyl alkyl or cycloalkenyl alkyl radical as defined; R3 represents a hydrogen atom; and R4 represents a hydrogen atom;  (E) p is 1/2 , 1 or 2; 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 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 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 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 dialkylamino radical containing 2 to 10 carbon atoms, a cyano radical 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, an alkylthio radical containing 1 to 4 carbon atoms, a bromomethyl radical, a fluoromethyl radical, a chloromethyl radical, a methylthiomethyl radical, a phenylthiomethyl radical or a carboxymethylthiomethyl radical; R3 represents a hydrogen atom or a methyl radical; and R4 represents an alkyl radical containing 1 to 6 carbon atoms, an acyl radical containing 1 to 6 carbon atoms or a substituted acyl radical containing 1 to 6 carbon atoms, are prepared by co-melting the uracil and the phenol in appropriate molar ratios, or by dissolving the components in a non-polar solvent.  These complexes are herbicides (see Division A5).ALSO:Uracil-phenol complexes of the formula:  <FORM:1035095/A5-A6/1> or the corresponding isomeric formula:  <FORM:1035095/A5-A6/2> wherein Z represents a hydrogen, bromine or chlorine atom, a nitro radical, an alkyl radical containing 1 to 3 carbon atoms or a radical of formula -OR5, where R5 represents an alkyl radical containing 1 to 3 carbon atoms; Y represents a chlorine atom or an alkyl radical containing 1 to 3 carbon atoms; m is 1, 2, 3, 4 or 5; and p, R1, R2, R3 and R4 are as defined in one of paragraphs (A) to (E) below.  (A) p is 1 or 2; 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 substituted cycloalkyl radical in which the cycloalkyl radical contains 3 to 12 carbon atoms, a cyclo