Five-membered nitrogen-containing hetero-cyclic compounds and their use as pest-combating agents

A method of combatting insects and acarids which comprises administering to such insects and acarids or to a habitat thereof an insecticidally and acaricidally effective amount of a five-membered nitrogen-containing heterocyclic compound of the formula ##STR268## in which R.sup.1 represents C.sub.1-7 -alkyl, C.sub.2-7 -alkenyl, C.sub.3-7 -cycloalkyl or C.sub.5-8 -cycloalkenyl, which can be optionally independently substituted by one or more of halogen, C.sub.1-4 -alkoxy, carboxyl, carbalkoxy, or phenyl, phenoxy or phenylthio, it being possible for the phenyl rings to be substituted by halogen or alkyl;

• or
• R.sup.1 furthermore represents phenyl which can be optionally independently substituted by one or more of halogen, nitro, amino, OH, CN, C.sub.1-4 -alkyl, C.sub.1-4 -halogenoalkyl, C.sub.1-4 -alkoxy, methylenedioxy, ethylenedioxy, C.sub.1-4 -halogenoalkoxy, difluoromethylenedioxy or halogen-substituted ethylenedioxy, C.sub.1-4 -alkylthio, C.sub.1-4 -halogenoalkylthio, C.sub.2-8 -alkylsulphonyl, C.sub.1-4 -halogenoalkylsulphonyl, carboxyl, carboxyl, the radical C.sub.1-4 -alkoxy--N.dbd.CH--, or phenyl, phenoxy, Phenylthio which can be optionally substituted by halogen or C.sub.1-4 -alkyl, or represents carboxyalkoxy having 2-4 C atoms, or
• R.sup.1 furthermore represents pyridinyl, pyrimidinyl, triazinyl, isoxazolyl, thiazolyl, oxadiazolyl, imidazolyl, triazolyl, furanyl or thienyl, which can be optionally mono- or polysubstituted by identical or different substituents from amongst halogen, C.sub.1-4 -alkyl, and C.sub.1-4 -alkoxy,
• R.sup.2 represents hydrogen, one equivalent of an alkali metal cation, alkaline earth metal cation or optionally substituted ammonium cation, trialkylsilyl having 1-4 C atoms in the alkyl part, C.sub.1-4 -alkyl, C.sub.1-4 -alkylcarbonyl, phenyl or benzoyl, which can be optionally substituted by one or more of the following radicals (A), the substituents being identical or different:
• (A) represents halogen, nitro, amino, CN, C.sub.1-4 -alkyl, C.sub.1-4 -halogenoalkyl, C.sub.1-4 -alkoxy, C.sub.1-4 -halogenoalkoxy, methylenedioxy, ethylenedioxy or difluoromethylenedioxy, halogen-substituted ethylenedioxy, C.sub.1-4 -alkylthio, C.sub.1-4 -halogenoalkylthio, C.sub.2-8 -alkoxyalkyl, C.sub.2-8 -halogenoalkoxyalkyl, C.sub.1-5 -alkylsulphenyl or phenylsulphenyl, C.sub.1-4 -alkylsulphonyl, C.sub.1-4 -halogenoalkylsulphonyl, carbalkoxy, the radical C.sub.1-4 -alkoxy--N.dbd.CH--, or phenyl, phenoxy or thiophenyl, which can be optionally substituted by halogen or by C.sub.1-4 -alkyl, or represents carboxyalkoxy having 2-4 C atoms, or
• R.sup.2 furthermore represents C.sub.1-4 -alkoxycarbonyl, phenoxycarbonyl which can be optionally substituted by one or more of the radicals (A), C.sub.1-4 -alkylsulphonyl, phenylsulphonyl which can be optionally substituted by one or more of the radicals (A), C.sub.1-4 -alkylaminosulphonyl, C.sub.1-5 -alkylsulphenyl or phenylsulphenyl, di-C.sub.1-4 -alkylaminosulphonyl, phenylaminosulphonyl which can be optionally substituted by one or more of the radicals (A), phenyl-C.sub.1-4 -alkylaminosulphonyl or a radical of the formula ##STR269## wherein R.sup.5 and R.sup.6 independently of one another represent hydrogen, C.sub.1-20 -alkyl, C.sub.3-6 -cycloalkyl, phenyl which can be optionally substituted by one or more of the radicals (A), phenylcarbonyl which can be optionally substituted by one or more of the radicals (A), C.sub.1-10 -alkylcarbonyl, C.sub.1-4 -alkylaminocarbonyl, C.sub.1-10 -alkoxycarbonyl, phenylaminocarbonyl or phenylsulphonyl, which can be optionally substituted by one or more of the radicals (A),
• R.sup.3 represents the radicals stated for R.sup.1, or also CN or the radical COR.sup.4, R.sup.4 represents amino, C.sub.1-8 -alkylamino or di-C.sub.1-8 -alkylamino, which can be optionally substituted by hydroxyl or C.sub.1-4 -alkoxy, phenylamino which can be optionally substituted by one or more of the radicals (A) given above, C.sub.5-6 -cycloalkylamino, a saturated heterocyclic structure having 5-6 C atoms in the ring, or a radical of the formula
• --NHR.sup.7
• wherein
• R.sup.7 represents C.sub.1-4 -alkyl-carbonyl, C.sub.2-4 -alkenylcarbonyl, C.sub.5-8 -cycloalkenylcarbonyl, C.sub.1-4 -alkylamino, phenylamino which can be optionally substituted by one or more of the radicals (A) given above, C.sub.1-4 -alkylaminocarbonylamino ##STR270## phenylaminocarbonylamino ##STR271## which can be optionally substituted by one or more of the radicals (A), C.sub.1-4 -alkylcarbonylamino ##STR272## or benzoylamino which can be optionally substituted by one or more of the radicals (A);
• or
• R.sup.4 furthermore represents a radical of the formula ##STR273## wherein R.sup.8 represents C.sub.1-4 -alkyl, or phenyl which can be optionally substituted by one or more of the radicals (A),
• R.sup.9 represents hydrogen or C.sub.1-4 -alkyl,
• Y represents O and
• X represents SSO and SO.sub.2,
• wherein
• R.sup.10 and R.sup.11 represent C.sub.1-4 -alkyl.