Heterocyclic compounds

A compound of the formula ##STR689## in which R.sup.1, R.sup.2, R.sup.5 and R.sup.6 independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, R.sup.3 and R.sup.4 independently represent a hydrogen atom, a hydroxy group or an alkyl group having 1 to 4 carbon atoms,

• Y represents a nitrogen atom or ##STR690## R.sup.9 represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a hydroxy group, an alkoxy group having 1 to 4 carbon atoms, a benzyloxy group, an alkyl group having 1 to 4 carbon atoms which may be substituted by at least one member selected from the class consisting of a fluorine atom, a chlorine atom, a hydroxy group, an alkoxy group having 1 to 2 carbon atoms, alkylthio groups having 1 to 2 carbon atoms, a cyano group, a dimethylamino group, alkylcarbonyl groups having an alkyl with 1 to 2 carbon atoms and alkoxycarbonyl groups having an alkyl with 1 to 2 carbon atoms,
• an alkenyl group having 2 to 3 carbon atoms, a phenyl group,
• an alkylcarbonyl group having an alkyl with 1 to 4 carbon atoms which may be substituted by at least one member selected from the class consisting of a methoxy group, a chlorine atom and a fluorine atom,
• an alkenylcarbonyl group having an alkenyl with 2 to 3 carbon atoms,
• a benzoyl group which may be substituted by at least one member selected from the class consisting of a fluorine atom, a chlorine atom, a bromine atom,
• a methoxy group and a methyl group,
• an alkoxycarbonyl group which may be substituted by a fluorine atom and/or a chlorine atom,
• an alkylthiocarbonyl group having an alkyl with 1 to 4 carbon atoms,
• a phenoxycarbonyl group which may be substituted by at least one member selected from the class consisting of a fluorine atom, a chlorine atom, a bromine atom, a methyl group, a methoxy group and a nitro group,
• a phenylthiocarbonyl group, a benzyloxycarbonyl group,
• a benzoylaminocarbonyl group which may be substituted by at least one member selected from the class consisting of a methyl group, a fluorine atom,
• a chlorine atom and a bromine atom,
• a phenylsulfonylaminocarbonyl group which may be substituted by at least one member selected from the class consisting of a methyl group, a fluorine atom,
• a chlorine atom and a bromine atom,
• an alkylsulfonylaminocarbonyl group having an alkyl with 1 to 4 carbon atoms,
• an alkylthio group having 1 to 4 carbon atoms,
• an alkylsulfonyl group which may be substituted by a fluorine atom and/or a chlorine atom,
• a phentylthio group which may be substituted by at least one member selected from the class consisting of a methyl group, a fluorine atom, a chlorine atom and a bromine atom, or
• a phenylsulfonyl group which may be substituted by at least one member selected from the class consisting of a methyl group, a fluorine atom, a chlorine atom and a bromine atom,
• in addition, R.sup.9 may form a bis-form of the formula (I), via a methylene group,
• R represents a hydrogen atom or a methyl group, and
• Z represents a 5 to 6 membered heterocyclic group, containing one to three hetero atoms selected from the class consisting of an oxygen atom, a sulfur atom and a nitrogen atom, at least one of which is a nitrogen atom, which may be substituted by at least one member selected from the class consisting of a fluorine atom, a chlorine atom, a bromine atom, alkyl groups having 1 to 4 carbon atoms which may be substituted by a fluorine atom and/or a chlorine atom,
• a nitro group, a cyano group,
• alkylsulfinyl groups having 1 to 4 carbon atoms,
• alkylsulfonyl groups having 1 to 4 carbon atoms,
• alkoxy groups having 1 to 4 carbon atoms which may be substituted by a fluorine atom and/or a chlorine atom,
• alkylthio groups having 1 to 4 carbon atoms which may be substituted by a fluorine atom and/or a chlorine atom;
• alkenyl groups having 2 to 3 carbon atoms which may be substituted by a chlorine atom,
• an acetamide group which may be substituted by a fluorine atom and/or a chlorine atom,
• alkoxycarbonyl groups having an alkyl with 1 to 4 carbon atoms, a thiocyanato group,
• alkynyl groups having 2 to 4 carbon atoms,
• an amino group, a methylamino group,
• a dimethylamino group, an acetyl group,
• a formyl group, a carboxy group, a hydroxy group,
• a mercapto group, cycloalkyl groups having 3 to 7 carbon atoms, an oxo group, a thioxo group,
• alkenylthio groups substituted by a fluorine atom, a chlorine atom and/or a bromine atom, alkoxyalkyl groups having 2 to 4 carbon atoms in total,
• alkylaminocarbonyl groups having an alkyl with 1 to 2 carbon atoms,
• dialkylaminocarbonyl groups having an alkyl with 1 to 2 carbon atoms,
• a phenyl group, a phenoxy group and a benzyl group.