2-(HET)ARYL-SUBSTITUTED FUSED BICYCLIC HETEROCYCLE DERIVATIVES AS PESTICIDES

Abstract

The invention relates to novel compounds of the formula (I)

##STR00001## in which the R.sup.1, R.sup.2a, R.sup.2b, R.sup.3, A.sup.1, A.sup.2, A.sup.3, A.sup.4 and n radicals are each as defined above, to their use as acaricides and/or insecticides for controlling animal pests and to processes and intermediates for their preparation.

Claims

1. Compound of formula (I) ##STR00140## wherein A.sup.1 represents nitrogen, ═N.sup.+—O.sup.− or ═C—R.sup.4, A.sup.2 represents —N—R.sup.5, oxygen or sulphur, A.sup.3 represents oxygen, A.sup.4 represents nitrogen, ═N.sup.+—O.sup.− or ═C—R.sup.4, R.sup.1 represents (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-cyanoalkyl, (C.sub.1-C.sub.6)-hydroxyalkyl, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkoxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkenyloxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-haloalkenyloxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-haloalkenyl, (C.sub.2-C.sub.6)-cyanoalkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.2-C.sub.6)-alkynyloxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-haloalkynyloxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-haloalkynyl, (C.sub.2-C.sub.6)-cyanoalkynyl, (C.sub.3-C.sub.8)-cycloalkyl, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.3-C.sub.8)-cycloalkyl, (C.sub.1-C.sub.6)-alkyl-(C.sub.3-C.sub.8)-cycloalkyl, halo-(C.sub.3-C.sub.8)cycloalkyl, amino, (C.sub.1-C.sub.6)-alkylamino, di-(C.sub.1-C.sub.6)-alkylamino, (C.sub.3-C.sub.8)-cycloalkylamino, (C.sub.1-C.sub.6)-alkylcarbonylamino, (C.sub.1-C.sub.6)-alkylthio-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkylthio-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylsulphinyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkylsulphinyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylsulphonyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkylsulphonyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkylthio-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkylsulphinyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkylsulphonyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylcarbonyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkylcarbonyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxycarbonyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkoxycarbonyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylsulphonylamino, aminosulphonyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylaminosulphonyl-(C.sub.1-C.sub.6)-alkyl, di-(C.sub.1-C.sub.6)-alkylaminosulphonyl-(C.sub.1-C.sub.6)-alkyl, or represents (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.3-C.sub.8)-cycloalkyl, each of which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of aryl, hetaryl and heterocyclyl, where aryl, hetaryl and heterocyclyl may each optionally be mono- or polysubstituted by identical or different substituents from the group consisting of halogen, cyano, nitro, hydroxy, amino, carboxy, carbamoyl, aminosulphonyl, (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-haloalkoxy, (C.sub.1-C.sub.6)-alkylthio, (C.sub.1-C.sub.6)-alkylsulphinyl, (C.sub.1-C.sub.6)-alkylsulphonyl, (C.sub.1-C.sub.6)-alkylsulphimino, (C.sub.1-C.sub.6)-alkylsulphimino-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylsulphimino-(C.sub.2-C.sub.6)-alkylcarbonyl, (C.sub.1-C.sub.6)-alkylsulphoximino, (C.sub.1-C.sub.6)-alkylsulphoximino-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylsulphoximino-(C.sub.2-C.sub.6)alkylcarbonyl, (C.sub.1-C.sub.6)-alkoxycarbonyl, (C.sub.1-C.sub.6)-alkylcarbonyl, (C.sub.3-C.sub.6)-trialkylsilyl and benzyl, or R.sup.1 represents aryl, hetaryl or heterocyclyl, each of which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, cyano, nitro, hydroxy, amino, carboxy, carbamoyl, (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.8)-cycloalkyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-haloalkoxy, (C.sub.1-C.sub.6)-alkylthio, (C.sub.1-C.sub.6)-alkylsulphinyl, (C.sub.1-C.sub.6)-alkylsulphonyl, (C.sub.1-C.sub.6)-alkylsulphimino, (C.sub.1-C.sub.6)-alkylsulphimino-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylsulphimino-(C.sub.2-C.sub.6)-alkylcarbonyl, (C.sub.1-C.sub.6)-alkylsulphoximino, (C.sub.1-C.sub.6)-alkylsulphoximino-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylsulphoximino-(C.sub.2-C.sub.6)-alkylcarbonyl, (C.sub.1-C.sub.6)-alkoxycarbonyl, (C.sub.1-C.sub.6)-alkylcarbonyl, (C.sub.3-C.sub.6)-trialkylsilyl, (═O) (only in the case of heterocyclyl) and (═O).sub.2 (only in the case of heterocyclyl), R.sup.2a, R.sup.3 and R.sup.4 independently of one another represent hydrogen, cyano, halogen, nitro, acetyl, hydroxy, amino, SCN, tri-(C.sub.1-C.sub.6)-alkylsilyl, (C.sub.3-C.sub.8)-cycloalkyl, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.3-C.sub.8)-cycloalkyl, (C.sub.1-C.sub.6)-alkyl-(C.sub.3-C.sub.8)cycloalkyl, halo-(C.sub.3-C.sub.8)cycloalkyl, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-cyanoalkyl, (C.sub.1-C.sub.6)-hydroxyalkyl, hydroxycarbonyl-(C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-alkoxycarbonyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-haloalkenyl, (C.sub.2-C.sub.6)-cyanoalkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.2-C.sub.6)-haloalkynyl, (C.sub.2-C.sub.6)-cyanoalkinyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-haloalkoxy, (C.sub.1-C.sub.6)-cyanoalkoxy, (C.sub.1-C.sub.6)-alkoxycarbonyl-(C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-alkylhydroxyimino, (C.sub.1-C.sub.6)-alkoxyimino, (C.sub.1-C.sub.6)-alkyl-(C.sub.1-C.sub.6)-alkoxyimino, (C.sub.1-C.sub.6)-haloalkyl-(C.sub.1-C.sub.6)-alkoxyimino, (C.sub.1-C.sub.6)-alkylthio, (C.sub.1-C.sub.6)-haloalkylthio, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkylthio, (C.sub.1-C.sub.6)-alkylthio-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylsulphinyl, (C.sub.1-C.sub.6)-haloalkylsulphinyl, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkylsulphinyl, (C.sub.1-C.sub.6)-alkylsulphinyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylsulphonyl, (C.sub.1-C.sub.6)-haloalkylsulphonyl, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkylsulphonyl, (C.sub.1-C.sub.6)-alkylsulphonyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylsulphonyloxy, (C.sub.1-C.sub.6)-alkylcarbonyl, (C.sub.1-C.sub.6)-alkylthiocarbonyl, (C.sub.1-C.sub.6)-haloalkylcarbonyl, (C.sub.1-C.sub.6)-alkylcarbonyloxy, (C.sub.1-C.sub.6)-alkoxycarbonyl, (C.sub.1-C.sub.6)-haloalkoxycarbonyl, aminocarbonyl, (C.sub.1-C.sub.6)-alkylaminocarbonyl, (C.sub.1-C.sub.6)-alkylaminothiocarbonyl, di-(C.sub.1-C.sub.6)-alkylaminocarbonyl, di-(C.sub.1-C.sub.6)-alkylaminothiocarbonyl, (C.sub.2-C.sub.6)-alkenylaminocarbonyl, di-(C.sub.2-C.sub.6)-alkenylaminocarbonyl, (C.sub.3-C.sub.8)-cycloalkylaminocarbonyl, (C.sub.1-C.sub.6)-alkylsulphonylamino, (C.sub.1-C.sub.6)-alkylamino, di-(C.sub.1-C.sub.6)-alkylamino, aminosulphonyl, (C.sub.1-C.sub.6)-alkylaminosulphonyl, di-(C.sub.1-C.sub.6)-alkyl-aminosulphonyl, (C.sub.1-C.sub.6)-alkylsulphoximino, aminothiocarbonyl, (C.sub.1-C.sub.6)-alkylaminothiocarbonyl, di-(C.sub.1-C.sub.6)-alkylaminothiocarbonyl, (C.sub.3-C.sub.8)-cycloalkylamino, NHCO—(C.sub.1-C.sub.6)-alkyl ((C.sub.1-C.sub.6)-alkylcarbonylamino), represent aryl or hetaryl, each of which is optionally mono- or polysubstituted by identical or different substituents, where (in the case of hetaryl) at least one carbonyl group may optionally be present and/or where possible substituents are in each case as follows: cyano, carboxyl, halogen, nitro, acetyl, hydroxy, amino, SCN, tri-(C.sub.1-C.sub.6)-alkylsilyl, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-cyanoalkyl, (C.sub.1-C.sub.6)-hydroxyalkyl, hydroxycarbonyl-(C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-alkoxycarbonyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-haloalkenyl, (C.sub.2-C.sub.6)-cyanoalkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.2-C.sub.6)-haloalkynyl, (C.sub.2-C.sub.6)-cyanoalkynyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-haloalkoxy, (C.sub.1-C.sub.6)-cyanoalkoxy, (C.sub.1-C.sub.6)-alkoxycarbonyl-(C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-alkylhydroxyimino, (C.sub.1-C.sub.6)-alkoxyimino, (C.sub.1-C.sub.6)-alkyl-(C.sub.1-C.sub.6)-alkoxyimino, (C.sub.1-C.sub.6)-haloalkyl-(C.sub.1-C.sub.6)-alkoxyimino, (C.sub.1-C.sub.6)-alkylthio, (C.sub.1-C.sub.6)-haloalkylthio, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkylthio, (C.sub.1-C.sub.6)-alkylthio-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylsulphinyl, (C.sub.1-C.sub.6)-haloalkylsulphinyl, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkylsulphinyl, (C.sub.1-C.sub.6)-alkylsulphinyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylsulphonyl, (C.sub.1-C.sub.6)-haloalkylsulphonyl, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkylsulphonyl, (C.sub.1-C.sub.6)-alkylsulphonyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylsulphonyloxy, (C.sub.1-C.sub.6)-alkylcarbonyl, (C.sub.1-C.sub.6)-haloalkylcarbonyl, (C.sub.1-C.sub.6)-alkylcarbonyloxy, (C.sub.1-C.sub.6)-alkoxycarbonyl, (C.sub.1-C.sub.6)-haloalkoxycarbonyl, aminocarbonyl, (C.sub.1-C.sub.6)-alkylaminocarbonyl, di-(C.sub.1-C.sub.6)-alkylaminocarbonyl, (C.sub.2-C.sub.6)-alkenylaminocarbonyl, di-(C.sub.2-C.sub.6)-alkenylaminocarbonyl, (C.sub.3-C.sub.8)-cycloalkylaminocarbonyl, (C.sub.1-C.sub.6)-alkylsulphonylamino, (C.sub.1-C.sub.6)-alkylamino, di-(C.sub.1-C.sub.6)-alkylamino, aminosulphonyl, (C.sub.1-C.sub.6)-alkylaminosulphonyl, di-(C.sub.1-C.sub.6)-alkylaminosulphonyl, (C.sub.1-C.sub.6)-alkylsulphoximino, aminothiocarbonyl, (C.sub.1-C.sub.6)-alkylaminothiocarbonyl, di-(C.sub.1-C.sub.6)-alkylaminothiocarbonyl, (C.sub.3-C.sub.8)-cycloalkylamino, R.sup.2b represents a saturated, partially saturated or heteroaromatic ring which is optionally mono- or polysubstituted by identical or different substituents, where at least one carbon atom is replaced by a heteroatom, which may in each case contain at least one carbonyl group and/or where possible substituents are in each case as follows: hydrogen, cyano, carboxyl, halogen, nitro, acetyl, hydroxy, amino, SCN, tri-(C.sub.1-C.sub.6)-alkylsilyl, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-cyanoalkyl, (C.sub.1-C.sub.6)-hydroxyalkyl, hydroxycarbonyl-(C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-alkoxycarbonyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-haloalkenyl, (C.sub.2-C.sub.6)-cyanoalkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.2-C.sub.6)-haloalkynyl, (C.sub.2-C.sub.6)-cyanoalkynyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.3-C.sub.6)-cycloalkyl, (C.sub.1-C.sub.4)-alkyl-(C.sub.3-C.sub.6)-cycloalkyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-haloalkoxy, (C.sub.1-C.sub.6)-cyanoalkoxy, (C.sub.1-C.sub.6)-alkoxycarbonyl-(C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-alkoxyimino, —N═C(H)—O(C.sub.1-C.sub.6)-alkyl, —C(H)═N—O(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl-(C.sub.1-C.sub.6)-alkoxyimino, (C.sub.1-C.sub.6)-alkylthio, (C.sub.1-C.sub.6)-haloalkylthio, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkylthio, (C.sub.1-C.sub.6)-alkylthio-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylsulphinyl, (C.sub.1-C.sub.6)-haloalkylsulphinyl, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkylsulphinyl, (C.sub.1-C.sub.6)-alkylsulphinyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylsulphonyl, (C.sub.1-C.sub.6)-haloalkylsulphonyl, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkylsulphonyl, (C.sub.1-C.sub.6)-alkylsulphonyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylsulphonyloxy, (C.sub.1-C.sub.6)-alkylcarbonyl, (C.sub.1-C.sub.6)-haloalkylcarbonyl, (C.sub.1-C.sub.6)-alkylcarbonyloxy, (C.sub.1-C.sub.6)-alkoxycarbonyl, (C.sub.1-C.sub.6)-haloalkoxycarbonyl, aminocarbonyl, (C.sub.1-C.sub.6)-alkylaminocarbonyl, di-(C.sub.1-C.sub.6)-alkylaminocarbonyl, (C.sub.2-C.sub.6)-alkenylaminocarbonyl, di-(C.sub.2-C.sub.6)-alkenylaminocarbonyl, (C.sub.3-C.sub.8)-cycloalkylaminocarbonyl, (C.sub.1-C.sub.6)-alkylsulphonylamino, (C.sub.1-C.sub.6)-alkylamino, di-(C.sub.1-C.sub.6)-alkylamino, aminosulphonyl, (C.sub.1-C.sub.6)-alkylaminosulphonyl, di-(C.sub.1-C.sub.6)alkylaminosulphonyl, (C.sub.1-C.sub.6)-alkylsulphoximino, aminothiocarbonyl, (C.sub.1-C.sub.6)-alkylaminothiocarbonyl, di-(C.sub.1-C.sub.6)-alkylaminothiocarbonyl, (C.sub.3-C.sub.8)-cycloalkylamino, (C.sub.1-C.sub.6)-alkylcarbonylamino, R.sup.5 represents (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-cyanoalkyl, (C.sub.1-C.sub.6)-hydroxyalkyl, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkoxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkenyloxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-haloalkenyloxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-haloalkenyl, (C.sub.2-C.sub.6)-cyanoalkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.2-C.sub.6)-alkynyloxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-haloalkynyloxy-(C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-haloalkynyl, (C.sub.2-C.sub.6)-cyanoalkynyl, (C.sub.3-C.sub.8)-cycloalkyl, (C.sub.3-C.sub.8)-cycloalkyl-(C.sub.3-C.sub.8)-cycloalkyl, (C.sub.1-C.sub.6)-alkyl-(C.sub.3-C.sub.8)-cycloalkyl, halo-(C.sub.3-C.sub.8)cycloalkyl, (C.sub.1-C.sub.6)-alkylthio-(C.sub.1-C.sub.8)-alkyl, (C.sub.1-C.sub.6)-haloalkylthio-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylsulphinyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkylsulphinyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylsulphonyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkylsulphonyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkylthio-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkylsulphinyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy-(C.sub.1-C.sub.6)-alkylsulphonyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylcarbonyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkylcarbonyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxycarbonyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkoxycarbonyl-(C.sub.1-C.sub.6)-alkyl, aminocarbonyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkylamino-(C.sub.1-C.sub.6)-alkyl, di-(C.sub.1-C.sub.6)-alkylamino-(C.sub.1-C.sub.6)-alkyl or (C.sub.3-C.sub.8)-cycloalkylamino-(C.sub.1-C.sub.6)-alkyl, n represents 0, 1 or 2.

2. Compound of formula (I) according to claim 1 wherein A.sup.1 represents nitrogen, ═N.sup.+—O.sup.− or ═C—R.sup.4, A.sup.2 represents —N—R.sup.5, oxygen or sulphur, A.sup.3 represents oxygen, A.sup.4 represents nitrogen, ═N.sup.+—O.sup.− or ═C—R.sup.4, R.sup.1 represents (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-hydroxyalkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.1-C.sub.4)-cyanoalkyl, (C.sub.1-C.sub.4)-alkoxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkoxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.2-C.sub.4)-alkenyl, (C.sub.2-C.sub.4)-alkenyloxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.2-C.sub.4)-haloalkenyloxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.2-C.sub.4)-haloalkenyl, (C.sub.2-C.sub.4)-cyanoalkenyl, (C.sub.2-C.sub.4)-alkynyl, (C.sub.2-C.sub.4)-alkynyloxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.2-C.sub.4)-haloalkynyloxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.2-C.sub.4)-haloalkynyl, (C.sub.2-C.sub.4)-cyanoalkynyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.3-C.sub.6)-cycloalkyl, (C.sub.1-C.sub.4)-alkyl-(C.sub.3-C.sub.6)-cycloalkyl, halo-(C.sub.3-C.sub.6)-cycloalkyl, (C.sub.1-C.sub.4)-alkylamino, di-(C.sub.1-C.sub.4)-alkylamino, (C.sub.3-C.sub.6)-cycloalkylamino, (C.sub.1-C.sub.4)-alkylcarbonylamino, (C.sub.1-C.sub.4)-alkylthio-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkylthio-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkylsulphinyl-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkylsulphinyl-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkylsulphonyl-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkylcarbonyl-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkylcarbonyl-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkylsulphonylamino, or represents (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkoxy, (C.sub.2-C.sub.4)-alkenyl, (C.sub.2-C.sub.4)-alkynyl, (C.sub.3-C.sub.6)cycloalkyl, each of which is optionally mono- or disubstituted by identical or different substituents from the group consisting of aryl, hetaryl and heterocyclyl, where aryl, hetaryl and heterocyclyl may in each case optionally be mono- or disubstituted by identical or different substituents from the group consisting of halogen, cyano, carbamoyl, aminosulphonyl, (C.sub.1-C.sub.4)-alkyl, (C.sub.3-C.sub.4)-cycloalkyl, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.1-C.sub.4)-haloalkoxy, (C.sub.1-C.sub.4)-alkylthio, (C.sub.1-C.sub.4)-alkylsulphinyl, (C.sub.1-C.sub.4)-alkylsulphonyl, (C.sub.1-C.sub.4)-alkylsulphimino, or R.sup.1 represents aryl, hetaryl or heterocyclyl, each of which is optionally mono- or disubstituted by identical or different substituents from the group consisting of halogen, cyano, carbamoyl, (C.sub.1-C.sub.4)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.1-C.sub.4)-haloalkoxy, (C.sub.1-C.sub.4)-alkylthio, (C.sub.1-C.sub.4)-alkylsulphinyl, (C.sub.1-C.sub.4)-alkylsulphonyl, (C.sub.1-C.sub.4)-alkylsulphimino, (C.sub.1-C.sub.4)-alkylsulphoximino, (C.sub.1-C.sub.4)-alkylcarbonyl, (C.sub.3-C.sub.4)-trialkylsilyl, (═O) (only in the case of heterocyclyl) and (═O).sub.2 (only in the case of heterocyclyl), R.sup.2a, R.sup.3 and R.sup.4 independently of one another represent hydrogen, cyano, halogen, nitro, acetyl, hydroxy, amino, SCN, tri-(C.sub.1-C.sub.4)-alkylsilyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.3-C.sub.6)-cycloalkyl, (C.sub.1-C.sub.4)-alkyl-(C.sub.3-C.sub.6)-cycloalkyl, halo-(C.sub.3-C.sub.6)-cycloalkyl, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.1-C.sub.4)-cyanoalkyl, (C.sub.1-C.sub.4)-hydroxyalkyl, (C.sub.1-C.sub.4)-alkoxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.2-C.sub.4)-alkenyl, (C.sub.2-C.sub.4)-haloalkenyl, (C.sub.2-C.sub.4)-cyanoalkenyl, (C.sub.2-C.sub.4)-alkynyl, (C.sub.2-C.sub.4)-haloalkynyl, (C.sub.2-C.sub.4)-cyanoalkynyl, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-haloalkoxy, (C.sub.1-C.sub.4)-cyanoalkoxy, (C.sub.1-C.sub.4)-alkoxy-(C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-alkylhydroxyimino, (C.sub.1-C.sub.4)-alkoxyimino, (C.sub.1-C.sub.4)-alkyl-(C.sub.1-C.sub.4)-alkoxyimino, (C.sub.1-C.sub.4)-haloalkyl-(C.sub.1-C.sub.4)-alkoxyimino, (C.sub.1-C.sub.4)-alkylthio, (C.sub.1-C.sub.4)-haloalkylthio, (C.sub.1-C.sub.4)-alkylthio-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkylsulphinyl, (C.sub.1-C.sub.4)-haloalkylsulphinyl, (C.sub.1-C.sub.4)-alkylsulphinyl-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkylsulphonyl, (C.sub.1-C.sub.4)-haloalkylsulphonyl, (C.sub.1-C.sub.4)-alkylsulphonyl-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkylsulphonyloxy, (C.sub.1-C.sub.4)-alkylcarbonyl, (C.sub.1-C.sub.4)-haloalkylcarbonyl, aminocarbonyl, aminothiocarbonyl, (C.sub.1-C.sub.4)-alkylaminocarbonyl, di-(C.sub.1-C.sub.4)-alkylaminocarbonyl, (C.sub.1-C.sub.4)-alkylsulphonylamino, (C.sub.1-C.sub.4)-alkylamino, di-(C.sub.1-C.sub.4)-alkylamino, aminosulphonyl, (C.sub.1-C.sub.4)-alkylaminosulphonyl, di-(C.sub.1-C.sub.4)-alkylaminosulphonyl, aminothiocarbonyl, NHCO—(C.sub.1-C.sub.4)-alkyl ((C.sub.1-C.sub.4)-alkylcarbonylamino), represent phenyl or hetaryl, each of which is optionally mono- or disubstituted by identical or different substituents, where (in the case of hetaryl) at least one carbonyl group may optionally be present and/or where possible substituents are in each case as follows: cyano, halogen, nitro, acetyl, amino, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.1-C.sub.4)-cyanoalkyl, (C.sub.1-C.sub.4)-hydroxyalkyl, (C.sub.1-C.sub.4)-alkoxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.2-C.sub.4)-alkenyl, (C.sub.2-C.sub.4)-haloalkenyl, (C.sub.2-C.sub.4)-cyanoalkenyl, (C.sub.2-C.sub.4)-alkynyl, (C.sub.2-C.sub.4)-haloalkynyl, (C.sub.2-C.sub.4)-cyanoalkynyl, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-haloalkoxy, (C.sub.1-C.sub.4)-cyanoalkoxy, (C.sub.1-C.sub.4)-alkoxy-(C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-alkylhydroxyimino, (C.sub.1-C.sub.4)-alkoxyimino, (C.sub.1-C.sub.4)-alkyl-(C.sub.1-C.sub.4)-alkoxyimino, (C.sub.1-C.sub.4)-haloalkyl-(C.sub.1-C.sub.4)-alkoxyimino, (C.sub.1-C.sub.4)-alkylthio, (C.sub.1-C.sub.4)-haloalkylthio, (C.sub.1-C.sub.4)-alkylthio-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkylsulphinyl, (C.sub.1-C.sub.4)-haloalkylsulphinyl, (C.sub.1-C.sub.4)-alkylsulphinyl-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkylsulphonyl, (C.sub.1-C.sub.4)-haloalkylsulphonyl, (C.sub.1-C.sub.4)-alkylsulphonyl-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkylsulphonyloxy, (C.sub.1-C.sub.4)-alkylcarbonyl, (C.sub.1-C.sub.4)-haloalkylcarbonyl, aminocarbonyl, (C.sub.1-C.sub.4)-alkylaminocarbonyl, di-(C.sub.1-C.sub.4)-alkylaminocarbonyl, (C.sub.1-C.sub.4)-alkylsulphonylamino, (C.sub.1-C.sub.4)-alkylamino, di-(C.sub.1-C.sub.4)-alkylamino, aminosulphonyl, (C.sub.1-C.sub.4)-alkylaminosulphonyl, di-(C.sub.1-C.sub.4)-alkylaminosulphonyl, R.sup.2b represents a saturated, partially saturated or heteroaromatic ring which is optionally mono-, di- or trisubstituted by identical or different substituents, where at least one carbon atom is replaced by a heteroatom from the group consisting of N, O and S, which may in each case contain at least one carbonyl group and/or where possible substituents are in each case as follows: cyano, halogen, nitro, acetyl, amino, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.1-C.sub.4)-cyanoalkyl, (C.sub.1-C.sub.4)-hydroxyalkyl, (C.sub.1-C.sub.4)-alkoxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.2-C.sub.4)-alkenyl, (C.sub.2-C.sub.4)-haloalkenyl, (C.sub.2-C.sub.4)-cyanoalkenyl, (C.sub.2-C.sub.4)-alkynyl, (C.sub.2-C.sub.4)-haloalkynyl, (C.sub.2-C.sub.4)-cyanoalkynyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.3-C.sub.6)-cycloalkyl, (C.sub.1-C.sub.4)-alkyl-(C.sub.3-C.sub.6)-cycloalkyl, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-haloalkoxy, (C.sub.1-C.sub.4)-cyanoalkoxy, (C.sub.1-C.sub.4)-alkoxy-(C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-alkoxyimino, —N═C(H)—O(C.sub.1-C.sub.4)-alkyl, —C(H)═N—O(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl-(C.sub.1-C.sub.4)-alkoxyimino, (C.sub.1-C.sub.4)-alkylthio, (C.sub.1-C.sub.4)-haloalkylthio, (C.sub.1-C.sub.4)-alkylthio-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkylsulphinyl, (C.sub.1-C.sub.4)-haloalkylsulphinyl, (C.sub.1-C.sub.4)-alkylsulphinyl-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkylsulphonyl, (C.sub.1-C.sub.4)-haloalkylsulphonyl, (C.sub.1-C.sub.4)-alkylsulphonyl-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkylsulphonyloxy, (C.sub.1-C.sub.4)-alkylcarbonyl, (C.sub.1-C.sub.4)-haloalkylcarbonyl, aminocarbonyl, (C.sub.1-C.sub.4)-alkylaminocarbonyl, di-(C.sub.1-C.sub.4)-alkylaminocarbonyl, (C.sub.1-C.sub.4)-alkylsulphonylamino, (C.sub.1-C.sub.4)-alkylamino, di-(C.sub.1-C.sub.4)-alkylamino, aminosulphonyl, (C.sub.1-C.sub.4)-alkylaminosulphonyl, di-(C.sub.1-C.sub.4)-alkylaminosulphonyl, (C.sub.1-C.sub.4)-alkylcarbonylamino, R.sup.5 represents (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.1-C.sub.4)-cyanoalkyl, (C.sub.1-C.sub.4)-hydroxyalkyl, (C.sub.1-C.sub.4)-alkoxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkoxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.2-C.sub.4)-alkenyl, (C.sub.2-C.sub.4)-alkenyloxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.2-C.sub.4)-haloalkenyloxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.2-C.sub.4)-haloalkenyl, (C.sub.2-C.sub.4)-cyanoalkenyl, (C.sub.2-C.sub.4)-alkynyl, (C.sub.2-C.sub.4)-alkynyloxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.2-C.sub.4)-haloalkynyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.3-C.sub.6)-cycloalkyl, (C.sub.1-C.sub.4)-alkyl-(C.sub.3-C.sub.6)-cycloalkyl, halo-(C.sub.3-C.sub.6)-cycloalkyl, (C.sub.1-C.sub.4)-alkylthio-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkylthio-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkylsulphinyl-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkylsulphinyl-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkylsulphonyl-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkylsulphonyl-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkoxy-(C.sub.1-C.sub.4)-alkylthio-(C.sub.1-C.sub.4)-alkyl or (C.sub.1-C.sub.4)-alkylcarbonyl-(C.sub.1-C.sub.4)-alkyl, n represents 0, 1 or 2.

3. Compound of formula (I) according to claim 1 wherein A.sup.1 represents nitrogen or ═C—R.sup.4, A.sup.2 represents —N—R.sup.5 or oxygen, A.sup.3 represents oxygen, A.sup.4 represents nitrogen or ═C—R.sup.4, R.sup.1 represents (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-hydroxyalkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.2-C.sub.4)-alkenyl, (C.sub.2-C.sub.4)-haloalkenyl, (C.sub.2-C.sub.4)-alkynyl, (C.sub.2-C.sub.4)-haloalkynyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.1-C.sub.4)-alkylthio-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkylsulphinyl-(C.sub.1-C.sub.4)-alkyl or (C.sub.1-C.sub.4)-alkylsulphonyl-(C.sub.1-C.sub.4)-alkyl, R.sup.2a represents hydrogen, cyano, aminocarbonyl, halogen, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.1-C.sub.4)-haloalkoxy, (C.sub.1-C.sub.4)-alkylthio, (C.sub.1-C.sub.4)-alkylsulphinyl, (C.sub.1-C.sub.4)-alkylsulphonyl, (C.sub.1-C.sub.4)-haloalkylthio, (C.sub.1-C.sub.4)-haloalkylsulphinyl or (C.sub.1-C.sub.4)-haloalkylsulphonyl, R.sup.2b represents a 5- or 6-membered saturated, partially saturated or heteroaromatic ring which is optionally mono-, di- or trisubstituted by identical or different substituents, where at least one carbon atom is replaced by a heteroatom from the group consisting of N, O and S, which may in each case contain at least one carbonyl group and/or where possible substituents are in each case as follows: cyano, halogen, nitro, acetyl, amino, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.1-C.sub.4)-cyanoalkyl, (C.sub.1-C.sub.4)-alkoxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.2-C.sub.4)-alkenyl, (C.sub.2-C.sub.4)-haloalkenyl, (C.sub.2-C.sub.4)-alkynyl, (C.sub.2-C.sub.4)haloalkynyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.3-C.sub.6)-cycloalkyl, (C.sub.1-C.sub.4)-alkyl-(C.sub.3-C.sub.6)-cycloalkyl, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-haloalkoxy, (C.sub.1-C.sub.4)-alkoxy-(C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-alkoxyimino, —N═C(H)—O(C.sub.1-C.sub.4)-alkyl, —C(H)═N—O(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkylthio, (C.sub.1-C.sub.4)-haloalkylthio, (C.sub.1-C.sub.4)-alkylthio-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkylsulphinyl, (C.sub.1-C.sub.4)-haloalkylsulphinyl, (C.sub.1-C.sub.4)-alkylsulphinyl-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkylsulphonyl, (C.sub.1-C.sub.4)-haloalkylsulphonyl, (C.sub.1-C.sub.4)-alkylsulphonyl-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkylsulphonyloxy, (C.sub.1-C.sub.4)-alkylcarbonyl, (C.sub.1-C.sub.4)-haloalkylcarbonyl, aminocarbonyl, (C.sub.1-C.sub.4)-alkylaminocarbonyl, di-(C.sub.1-C.sub.4)-alkylaminocarbonyl, (C.sub.1-C.sub.4)-alkylsulphonylamino, (C.sub.1-C.sub.4)-alkylamino, di-(C.sub.1-C.sub.4)-alkylamino, aminosulphonyl, (C.sub.1-C.sub.4)-alkylaminosulphonyl, di-(C.sub.1-C.sub.4)-alkylaminosulphonyl, (C.sub.1-C.sub.4)-alkylcarbonylamino, R.sup.3 represents hydrogen, halogen, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.1-C.sub.4)-haloalkoxy, (C.sub.1-C.sub.4)-alkylthio, (C.sub.1-C.sub.4)-alkylsulphinyl, (C.sub.1-C.sub.4)-alkylsulphonyl, (C.sub.1-C.sub.4)-haloalkylthio, (C.sub.1-C.sub.4)-haloalkylsulphinyl or (C.sub.1-C.sub.4)-haloalkylsulphonyl, R.sup.4 represents hydrogen, halogen, cyano or (C.sub.1-C.sub.4)-alkyl, R.sup.5 represents (C.sub.1-C.sub.4)alkyl or (C.sub.1-C.sub.4)alkoxy-(C.sub.1-C.sub.4)-alkyl, n represents 0, 1 or 2.

4. Compound of formula (I) according to claim 1 wherein A.sup.1 represents nitrogen or ═C—R.sup.4, A.sup.2 represents —N—R.sup.5 or oxygen, A.sup.3 represents oxygen, A.sup.4 represents nitrogen or ═C—H, R.sup.1 represents methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclobutyl, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl or pentafluoroethyl, R.sup.2a represents hydrogen, cyano, methyl, ethyl, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl, pentafluoroethyl, trifluoromethoxy, difluorochloromethoxy, dichlorofluoromethoxy, trifluoromethylthio, trifluoromethylsulphonyl, trifluoromethylsulphinyl, fluorine or chlorine, R.sup.2b represents a 5- or 6-membered saturated, partially saturated or heteroaromatic ring from the group consisting of Q1 to Q104 which is optionally mono-, di- or trisubstituted by identical or different substituents, which may in each case contain at least one carbonyl group and/or where possible substituents are in each case as follows: cyano, (C.sub.1-C.sub.4)-cyanoalkyl, (C.sub.1-C.sub.4)-alkoxy-(C.sub.1-C.sub.4)-alkyl, halogen, amino, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.2-C.sub.4)-alkenyl, (C.sub.2-C.sub.4)-haloalkenyl, (C.sub.2-C.sub.4)-alkynyl, (C.sub.2-C.sub.4)-haloalkynyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.3-C.sub.6)-cycloalkyl, (C.sub.1-C.sub.4)-alkyl-(C.sub.3-C.sub.6)-cycloalkyl, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-haloalkoxy, (C.sub.1-C.sub.4)-alkoxyimino, —C(H)═N—O(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkylthio, (C.sub.1-C.sub.4)-haloalkylthio, (C.sub.1-C.sub.4)-alkylsulphinyl, (C.sub.1-C.sub.4)-haloalkylsulphinyl, (C.sub.1-C.sub.4)-alkylsulphonyl, (C.sub.1-C.sub.4)-haloalkylsulphonyl, (C.sub.1-C.sub.4)-alkylsulphonyloxy, (C.sub.1-C.sub.4)-alkylcarbonyl, (C.sub.1-C.sub.4)-haloalkylcarbonyl, aminocarbonyl, (C.sub.1-C.sub.4)-alkylaminocarbonyl, di-(C.sub.1-C.sub.4)-alkylaminocarbonyl, (C.sub.1-C.sub.4)-alkylsulphonylamino, (C.sub.1-C.sub.4)-alkylamino, di-(C.sub.1-C.sub.4)-alkylamino, aminosulphonyl, (C.sub.1-C.sub.4)-alkylthio-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkylsulphinyl-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkylsulphonyl-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkylaminosulphonyl, di-(C.sub.1-C.sub.4)-alkylaminosulphonyl, (C.sub.1-C.sub.4)-alkylcarbonylamino, ##STR00141## ##STR00142## ##STR00143## ##STR00144## ##STR00145## ##STR00146## ##STR00147## ##STR00148## ##STR00149## ##STR00150## where the bond to the remainder of the molecule is identified by an asterisk *, R.sup.3 represents fluorine, chlorine, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl, pentafluoroethyl, trifluoromethoxy, difluorochloromethoxy, dichlorofluoromethoxy, trifluoromethylthio, trifluoromethylsulphonyl or trifluoromethylsulphinyl, R.sup.4 represents hydrogen, fluorine, chlorine, bromine or cyano, R.sup.5 represents methyl, ethyl, isopropyl, methoxymethyl or methoxyethyl, n represents 0, 1 or 2.

5. Compound of formula (I) according to claim 4 wherein A.sup.1 represents nitrogen, A.sup.2 represents —N—R.sup.5, A.sup.3 represents oxygen, A.sup.4 represents ═C—H, R.sup.1 represents methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or tert-butyl, R.sup.2a represents hydrogen, R.sup.2b represents a 5- or 6-membered saturated, partially saturated or heteroaromatic ring from the group consisting of Q-1, Q-2, Q-3, Q-9, Q-13, Q-14, Q-24, Q-25, Q-26, Q-28, Q-41, Q-42, Q-43, Q-45, Q-46, Q-47, Q-49, Q-51, Q-52, Q-59, Q-73, Q-81, Q-82, Q-83, Q-95, Q-97, Q-99, Q-100, Q-101, Q-102, Q-103, Q-104 which is optionally mono-, di- or trisubstituted by identical or different substituents, possible substituents being in each case: cyano, (C.sub.1-C.sub.4)-cyanoalkyl, (C.sub.1-C.sub.4)-alkoxy-(C.sub.1-C.sub.4)-alkyl, halogen, (C.sub.1-C.sub.4)-alkyl, (C.sub.2-C.sub.4)-alkynyl, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.1-C.sub.4)-alkylthio, (C.sub.1-C.sub.4)-haloalkylthio, (C.sub.1-C.sub.4)-alkylsulphonyl, (C.sub.1-C.sub.4)-alkylthio-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkylsulphinyl-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkylsulphonyl-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkylaminocarbonyl, (C.sub.1-C.sub.4)-alkylcarbonylamino, R.sup.3 represents fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl or pentafluoroethyl, R.sup.5 represents methyl, ethyl or isopropyl, n represents 2.

6. Compound of the formula (I) according to claim 1 A.sup.1 represents nitrogen, A.sup.2 represents —N—R.sup.5, A.sup.3 represents oxygen, A.sup.4 represents ═C—H, R.sup.1 represents methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or tert-butyl, R.sup.2a represents hydrogen, R.sup.2b represents one of the following radicals: ##STR00151## ##STR00152## ##STR00153## ##STR00154## R.sup.3 represents fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl or pentafluoroethyl, R.sup.5 represents methyl, ethyl or isopropyl, n represents 2.

7. Compound of formula (I) according to claim 1 in which A.sup.1 represents nitrogen, A.sup.2 represents —N—R.sup.5, A.sup.3 represents oxygen, A.sup.4 represents ═C—H, R.sup.2a represents hydrogen, R.sup.2b represents one of the following radicals: ##STR00155## ##STR00156## ##STR00157## ##STR00158## n represents 2 and R.sup.1 represents ethyl, R.sup.3 represents trifluoromethyl or pentafluoroethyl, R.sup.5 represents methyl.

8. Agrochemical formulation comprising one or more compounds of formula (I) according to claim 1 and one or more extenders and/or surfactants.

9. Agrochemical formulation according to claim 8, additionally comprising a further agrochemically active compound.

10. Method for controlling animal pests, comprising allowing a compound of formula (I) according to claim 1 or an agrochemical formulation thereof to act on one or more animal pests and/or a habitat thereof.

11. A product comprising a compound of formula (I) according to claim 1 or an agrochemical formulation thereof for controlling animal pests.

Description

PREPARATION EXAMPLES

2-[3-Ethylsulphonyl-6-[4-(trifluoromethyl)pyrazol-1-yl]-2-pyridyl]-3-methyl-6-(trifluoromethyl)-imidazo[4,5-c]pyridine (Ex. 26)

[0572] ##STR00044##

[0573] 100 mg (0.24 mmol) of 2-(6-chloro-3-ethylsulphonyl-2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine were dissolved in 10 ml of acetonitrile, 41 mg of potassium carbonate (0.29 mmol) and 100.8 mg of 4-(trifluoromethyl)-1H-pyrazole (0.74 mmol) were added and the mixture was then stirred at 65° C. for 4 h. The reaction mixture was then filtered through a silica gel cartridge using ethyl acetate. The solvent was distilled off under reduced pressure and the residue was purified by column chromatography using a water/acetonitrile gradient as mobile phase.

[0574] (log P (neutral): 3.34; MH.sup.+: 471; .sup.1H-NMR (400 MHz, D.sub.6-DMSO) δ ppm: 1.23 (t, 3H), 3.83 (q, 2H), 4.00 (s, 3H), 8.16 (s, 1H), 8.33 (s, 1H), 8.35 (d, 1H), 8.68 (d, 1H), 8.98 (s, 1H), 9.35 (s, 1H).

2-(6-Chloro-3-ethylsulphonyl-2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine

[0575] ##STR00045##

[0576] 900 mg (2.41 mmol) of 2-(6-chloro-3-ethylsulphanyl-2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine were dissolved in 50 ml of dichloromethane, 555.6 mg (12.0 mmol) of formic acid and 1.64 g (16.8 mmol) of 35% strength hydrogen peroxide were added at room temperature and the mixture was then stirred at room temperature for 5 h. The mixture was diluted with water and sodium bisulfite solution was added, the mixture was stirred for 1 h and saturated sodium bicarbonate solution was then added. The organic phase was separated off, the aqueous phase was extracted twice with dichloromethane and the combined organic phases were then freed of the solvent under reduced pressure. The residue was purified by column chromatography by means of preparative HPLC using a water/acetonitrile gradient as eluent.

[0577] (log P (neutral): 2.54; MH.sup.+: 405; .sup.1H-NMR (400 MHz, D.sub.6-DMSO) δ ppm: 1.20 (t, 3H), 3.77 (q, 2H), 3.91 (s, 3H), 8.13 (d, 1H), 8.32 (s, 1H), 8.56 (d, 1H), 9.30 (s, 1H).

2-(6-Chloro-3-ethylsulphanyl-2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine

[0578] ##STR00046##

[0579] 4.00 g (10.7 mmol) of 2-(3,6-dichloro-2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine were dissolved in 60 ml of tetrahydrofuran, 446 mg (11.1 mmol) of sodium hydride were added at −5° C. and the mixture was stirred at 0° C. for 30 minutes. 733 mg (11.8 mmol) ethanethiol were then added dropwise over 30 minutes at −5° C., the cooling bath was removed and the mixture was stirred at room temperature for 2 h. The reaction mixture was hydrolyzed with water, the organic phase was separated off and the aqueous phase was extracted twice with ethyl acetate. The organic phases were combined, washed with sodium chloride solution and dried over sodium sulphate, and the solvent was then distilled off under reduced pressure. The residue was purified by trituration with methyl tert-butyl ketone/dichloromethane 25:1.

[0580] (log P (neutral): 3.06; MH.sup.+: 373; .sup.1H-NMR (400 MHz, CD3CN) δ ppm: 1.25 (t, 3H), 2.98 (q, 2H), 3.98 (s, 3H), 7.56 (d, 1H), 7.95 (d, 1H), 8.15 (s, 1H), 9.06 (s, 1H).

2-(3,6-Dichloro-2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine

[0581] ##STR00047##

[0582] 20 g (104.6 mmol) of N.sup.3-methyl-6-(trifluoromethyl)pyridine-3,4-diamine, 25.11 g (130.8 mmol) of 3,6-dichloropyridine-2-carboxylic acid and 20.06 g (104.6 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) were stirred in 200 ml of pyridine at 120° C. for 8 h. The reaction mixture was freed of solvent under reduced pressure, water was added and the mixture was extracted three times with ethyl acetate. The organic phases were combined and dried over sodium sulphate, and the solvent was then distilled off under reduced pressure. The residue was purified by column chromatography using a cyclohexane/ethyl acetate gradient as mobile phase.

[0583] (log P (neutral): 2.81; MH.sup.+: 347; .sup.1H-NMR (400 MHz, D.sub.6-DMSO) δ ppm: 3.99 (s, 3H), 7.89 (d, 1H), 8.32 (s, 1H), 8.35 (d, 1H), 9.28 (s, 1H).

2-[3-Ethylsulphonyl-6-(3-thienyl)-2-pyridyl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine (Ex. 20)

[0584] ##STR00048##

[0585] 100 mg (0.24 mmol) of 2-(6-chloro-3-ethylsulphonyl-2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine, 32 mg (0.24 mmol) of thiophene-3-boronic acid and 29 mg (0.02 mmol) of tetrakis(triphenylphosphine)palladium(0) were initially charged in a mixture of degassed dioxane (3 ml) and degassed sodium carbonate solution (2M, 1.1 ml), and the mixture was stirred at 96° C. for 14 h. The reaction mixture was then cooled to room temperature and concentrated under reduced pressure, and the residue was taken up in water and dichloromethane. The phases were separated, the aqueous phase was extracted three times with dichloromethane and the combined organic phases were dried over sodium sulphate and filtered. The solvent was distilled off under reduced pressure and the residue was purified by column chromatography using a water/acetonitrile gradient as mobile phase.

[0586] log P (neutral): 3.13; MH.sup.+: 453; .sup.1H-NMR (400 MHz, D.sub.6-DMSO) δ ppm: 1.22 (t, 3H), 3.79 (q, 2H), 3.95 (s, 3H), 7.74-7.76 (m, 1H), 7.87-7.88 (m, 1H), 8.31 (s, 1H), 8.40 (d, 1H), 8.52-8.55 (m, 2H), 9.32 (s, 1H).

[0587] In analogy to the examples and according to the above-described preparation processes, the following compounds of the formula (I) can be obtained:

##STR00049##

[0588] where A.sup.3 represents oxygen and the other substituents have the meanings given in the table below, and where the bond from R.sup.2b to the remainder of the molecule is identified by an asterisk *:

TABLE-US-00001 Ex. R.sup.1 n A.sup.4 R.sup.3 A.sup.2 A.sup.1 R.sup.2a R.sup.2b 1 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H morpholin-4-yl [00050] embedded image 2 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H 3-[(trifluoromethyl) sulphanyl]-1H-pyrrol-1-yl [00051] 3 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H 4-(methylsulphonyl)-1H- pyrazol-1-yl [00052] 4 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H 4-(methylcarbamoyl)-1H- pyrazol-1-yl [00053] embedded image 5 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H 3-(methylsulphonyl)-1H- 1,2,4-triazol-1-yl [00054] 6 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H 4-chloro-1H-pyrazol-1-yl [00055] 7 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H 3-(cyanomethyl)-1H- pyrazol-1-yl [00056] 8 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H 3-(difluoromethyl)-1H- pyrazol-1-yl [00057] embedded image 9 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H 3-chloro-1H-pyrazol-1-yl [00058] 10 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H 3-(methoxymethyl)-1H- pyrazol-1-yl [00059] 11 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H 3-acetamido-1H-1,2,4- triazol-1-yl [00060] 12 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H 3-(methylcarbamoyl)-1H- pyrazol-1-yl [00061] embedded image 13 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H 4-cyclopropyl-1H-pyrazol- 1-yl [00062] 14 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H 4-iodo-1H-imidazol-1-yl [00063] 15 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H 3-(methylsulphanyl)-1H- 1,2,4-triazol-1-yl [00064] 16 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H 4-(methylsulphanyl)-1H- pyrazol-1-yl [00065] embedded image 17 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H 2H-1,2,3-triazol-2-yl [00066] 18 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H 3-chloro-1H-1,2,4-triazol- 1-yl [00067] 19 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00068] 20 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H 3-thienyl [00069] embedded image 21 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H 1H-pyrazol-1-yl [00070] 22 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H 3-cyano-1H-pyrazol-1-yl [00071] 23 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H 3-acetamido-1H-pyrazol- 1-yl [00072] 24 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H 4-(trifluoromethyl)-1H- 1,2,3-triazol-1-yl [00073] embedded image 25 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H 3-(trifluoromethyl)-1H- pyrazol-1-yl [00074] 26 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H 4-(trifluoromethyl)-1H- pyrazol-1-yl [00075] 27 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H 4-(trifluoromethyl)-1H- imidazol-1-yl [00076] 28 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H 4-fluoro-1H-pyrazol-1-yl [00077] embedded image 29 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H 3-(methylsulphanyl)-1H- pyrazol-1-yl [00078] 30 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H 4-(trifluoromethyl)-2H- 1,2,3-triazol-2-yl [00079] 31 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H 4-methyl-1H-pyrazol-1-yl [00080] 32 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H 1H-1,2,4-triazol-1-yl [00081] embedded image 33 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H 1H-imidazol-1-yl [00082] 34 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H 3-methyl-1H-pyrazol-1-yl [00083] 35 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H 3-(methylsulphonyl)-1H- pyrazol-1-yl [00084] 36 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00085] embedded image 37 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00086] 38 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00087] 39 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00088] 40 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00089] 41 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00090] 42 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00091] embedded image 43 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00092] 44 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00093] 45 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00094] 46 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00095] 47 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00096] 48 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00097] embedded image 49 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00098] 50 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00099] 51 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00100] 52 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00101] 53 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00102] 54 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00103] embedded image 55 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00104] 56 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00105] 57 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00106] 58 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00107] 59 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00108] 60 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00109] embedded image 61 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00110] 62 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00111] 63 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00112] 64 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00113] 65 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00114] 66 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00115] embedded image 67 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00116] 68 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00117] 69 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00118] 70 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00119] 71 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00120] 72 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00121] embedded image 73 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00122] 74 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00123] 75 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00124] 76 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00125] 77 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00126] 78 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00127] embedded image 79 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00128] 80 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00129] 81 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00130] 82 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00131] 83 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00132] 84 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00133] embedded image 85 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00134] 86 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00135] 87 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00136] 88 C.sub.2H.sub.5 2 CH CF.sub.3 N-methyl N H [00137]

Preparation of Intermediates:

N3-Methyl-6-(1,1,2,2,2-pentafluoroethyl)pyridine-3,4-diamine (II-1)

[0589] ##STR00138##

[0590] Under argon, 70 mmol of a 3 molar dimethyl sulphide/borane solution were added dropwise to a solution of 5 g (13.8 mmol) of benzyl N-[4-amino-6-(1,1,2,2,2-pentafluoroethyl)-3-pyridyl]carbamate in 350 ml of tetrahydrofuran. The reaction mixture was then stirred under reflux for 72 h, cooled and diluted with 100 ml of water. The aqueous phase was extracted three times with in each case 100 ml of ethyl acetate. The combined organic phases were washed with water and dried and the solvent was distilled off under reduced pressure at a water bath temperature of 40-45° C. The residue was purified by column chromatography on silica gel using chloroform/methanol (5:1) as mobile phase.

[0591] (log P (neutral): 1.68; MH.sup.+: 242; .sup.1H-NMR (400 MHz, D.sub.6-DMSO) δ ppm: 2.81 (s, 3H), 5.28 (s, 1H), 5.84 (s, 2H), 6.86 (s, 1H), 7.61 (s, 1H).

Benzyl N-[4-amino-6-(1,1,2,2,2-pentafluoroethyl)-3-pyridyl]carbamate

[0592] ##STR00139##

[0593] With ice bath cooling, 1.8 ml (22 mmol) of pyridine and 0.9 g (5.3 mmol) benzyl chlorocarbonate were added dropwise to a solution of 1.0 g (4.4 mmol) of 6-(1,1,2,2,2-pentafluoroethyl)pyridine-3,4-diamine in 50 ml of dichloromethane. The reaction mixture was then stirred for 2 h and diluted with 50 ml of water. The organic phase was separated off, washed with 0.01 N hydrochloric acid solution and dried, and the solvent was distilled off under reduced pressure. Further purification of the product was by recrystallization from chloroform.

[0594] The log P values are measured according to EEC Directive 79/831 Annex V.A8 by HPLC (high-performance liquid chromatography) on a reversed-phase column (C 18). Temperature: 55° C.

[0595] The LC-MS determination in the acidic range is effected at pH 2.7 using 0.1% aqueous formic acid and acetonitrile (contains 0.1% formic acid) as eluents, linear gradient from 10% acetonitrile to 95% acetonitrile. Called log P (HCOOH) in the table.

[0596] LC-MS determination in the neutral range is effected at pH 7.8 with 0.001 molar aqueous ammonium hydrogencarbonate solution and acetonitrile as eluents; linear gradient from 10% acetonitrile to 95% acetonitrile. Called log P (neutral) in the table.

[0597] Calibration is carried out using unbranched alkan-2-ones (having 3 to 16 carbon atoms) with known log P values (log P values determined on the basis of the retention times by linear interpolation between two successive alkanones).

[0598] The NMR data of selected examples are listed either in conventional form (8 values, multiplet splitting, number of hydrogen atoms) or as NMR peak lists.

[0599] In each case, the solvent in which the NMR spectrum is recorded is stated.

NMR Peak List Method

[0600] The .sup.1H NMR data of selected examples are stated in the form of .sup.1H NMR peak lists. For each signal peak, first the δ value in ppm and then the signal intensity in round brackets are listed. The pairs of δ value-signal intensity numbers for different signal peaks are listed with separation from one another by semicolons.

[0601] The peak list for one example therefore has the form of:

[0602] δ.sub.1 (intensity.sub.1); δ.sub.2 (intensity.sub.2); . . . ; δ.sub.i (intensity.sub.i); . . . ; δ.sub.n (intensity.sub.n)

[0603] The intensity of sharp signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the true ratios of the signal intensities. In the case of broad signals, several peaks or the middle of the signal and the relative intensity thereof may be shown in comparison to the most intense signal in the spectrum.

[0604] Calibration of the chemical shift of .sup.1H NMR spectra is accomplished using tetramethylsilane and/or the chemical shift of the solvent, particularly in the case of spectra which are measured in DMSO. Therefore, the tetramethylsilane peak may but need not occur in NMR peak lists.

[0605] The lists of the .sup.1H NMR peaks are similar to the conventional .sup.1H-NMR printouts and thus usually contain all peaks listed in a conventional NMR interpretation.

[0606] In addition, like conventional .sup.1H NMR printouts, they may show solvent signals, signals of stereoisomers of the target compounds which likewise form part of the subject-matter of the invention, and/or peaks of impurities.

[0607] In the reporting of compound signals within the delta range of solvents and/or water, our lists of .sup.1H NMR peaks show the standard solvent peaks, for example peaks of DMSO in DMSO-D.sub.6 and the peak of water, which usually have a high intensity on average.

[0608] The peaks of stereoisomers of the target compounds and/or peaks of impurities usually have a lower intensity on average than the peaks of the target compounds (for example with a purity of >90%).

[0609] Such stereoisomers and/or impurities may be typical of the particular preparation process. Their peaks can thus help in identifying reproduction of our preparation process with reference to “by-product fingerprints”.

[0610] An expert calculating the peaks of the target compounds by known methods (MestreC, ACD simulation, but also with empirically evaluated expected values) can, if required, isolate the peaks of the target compounds, optionally using additional intensity filters. This isolation would be similar to the peak picking in question in conventional .sup.1H NMR interpretation.

[0611] Further details of .sup.1H NMR peak lists can be found in the Research Disclosure Database Number 564025.

Example 1

[0612] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.249 (4.5); 8.314 (0.3); 8.248 (4.7); 8.084 (2.8); 8.060 (3.0); 7.226 (2.7); 7.203 (2.6); 3.869 (16.0); 3.689 (13.7); 3.609 (1.1); 3.590 (3.5); 3.572 (3.6); 3.554 (1.1); 3.317 (47.0); 2.671 (0.9); 2.501 (131.4); 2.497 (100.7); 2.328 (0.8); 2.073 (0.7); 1.181 (3.7); 1.162 (8.0); 1.144 (3.6); 0.000 (6.2)

Example 2

[0613] .sup.1H-NMR (601.6 MHz, d.sub.6-DMSO): δ=9.306 (4.0); 8.747 (3.1); 8.732 (3.4); 8.320 (4.1); 8.317 (4.7); 8.306 (3.3); 7.891 (1.9); 7.888 (2.1); 7.886 (2.1); 7.883 (1.8); 7.068 (1.7); 7.065 (2.0); 7.062 (2.0); 7.059 (1.7); 6.573 (1.8); 6.568 (3.1); 6.562 (1.7); 3.933 (16.0); 3.823 (1.1); 3.811 (3.6); 3.798 (3.7); 3.786 (1.1); 3.310 (174.1); 2.613 (1.3); 2.519 (4.4); 2.516 (5.6); 2.504 (142.8); 2.501 (192.6); 2.498 (146.6); 2.385 (1.3); 2.072 (2.2); 1.244 (3.9); 1.232 (8.3); 1.220 (3.8); 0.000 (11.0)

Example 3

[0614] .sup.1H-NMR (601.6 MHz, DMF): δ=9.435 (3.6); 9.415 (3.6); 8.865 (1.8); 8.851 (2.0); 8.563 (2.0); 8.549 (1.9); 8.455 (3.5); 8.345 (3.7); 8.023 (4.3); 5.812 (2.5); 4.171 (11.2); 3.952 (2.8); 3.940 (2.9); 3.465 (16.0); 3.436 (0.4); 3.397 (11.4); 2.913 (6.6); 2.742 (6.6); 1.348 (2.9); 1.336 (5.8); 1.324 (3.0); 0.000 (2.7)

Example 4

[0615] .sup.1H-NMR (400.0 MHz, ds-DMSO): δ=9.352 (4.4); 9.154 (5.7); 8.710 (3.2); 8.688 (3.7); 8.410 (3.7); 8.388 (3.3); 8.355 (1.3); 8.340 (5.5); 8.312 (0.4); 8.284 (5.9); 4.084 (0.5); 3.996 (16.0); 3.825 (1.0); 3.807 (3.4); 3.789 (3.4); 3.770 (1.1); 3.326 (136.3); 3.321 (100.4); 2.737 (7.3); 2.726 (7.4); 2.675 (0.7); 2.671 (1.0); 2.506 (121.3); 2.502 (162.4); 2.497 (123.3); 2.328 (1.0); 2.073 (0.6); 1.245 (3.7); 1.227 (8.2); 1.208 (3.7); 1.045 (0.4); 1.030 (0.4); 0.000 (0.7)

Example 5

[0616] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.857 (6.0); 9.367 (3.4); 8.845 (0.4); 8.839 (2.6); 8.817 (2.9); 8.700 (0.5); 8.422 (3.1); 8.400 (2.9); 8.352 (3.6); 8.335 (0.3); 8.313 (0.5); 4.022 (12.7); 3.942 (1.1); 3.926 (0.8); 3.907 (2.7); 3.889 (2.7); 3.871 (0.8); 3.554 (1.1); 3.502 (16.0); 3.321 (114.4); 3.318 (116.9); 2.675 (0.9); 2.670 (1.2); 2.666 (0.9); 2.506 (161.2); 2.501 (209.1); 2.497 (151.5); 2.332 (0.9); 2.328 (1.2); 1.268 (2.9); 1.250 (6.6); 1.232 (3.0); 0.146 (0.4); 0.008 (3.1); 0.000 (86.1); −0.008 (3.2); −0.150 (0.4)

Example 6

[0617] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.347 (4.7); 8.976 (5.4); 8.695 (3.0); 8.673 (3.4); 8.368 (3.4); 8.346 (3.1); 8.331 (5.0); 8.313 (0.4); 8.160 (5.2); 4.000 (16.0); 3.966 (0.3); 3.864 (1.1); 3.846 (3.7); 3.827 (3.7); 3.809 (1.2); 3.317 (46.5); 3.283 (0.9); 2.671 (0.8); 2.502 (128.0); 2.472 (3.2); 2.468 (3.1); 2.328 (0.8); 1.252 (3.9); 1.234 (8.5); 1.215 (3.9); 0.000 (7.1)

Example 7

[0618] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.333 (4.0); 9.277 (0.6); 8.724 (3.2); 8.717 (3.2); 8.692 (3.4); 8.670 (3.9); 8.358 (0.6); 8.337 (0.9); 8.328 (6.2); 8.314 (1.4); 8.307 (3.6); 7.900 (0.6); 7.878 (0.67); 6.676 (3.2); 6.669 (3.2); 4.317 (0.6); 4.230 (98); 3.988 (3.9); 3.981 (16.0); 3.841 (1.0); 3.823 (3.3); 3.804 (3.4); 3.786 (1.0); 3.316 (98.8); 2.680 (0.5); 2.675 (1.1); 2.671 (1.5); 2.666 (1.1); 2.510 (89.5); 2.506 (172.3); 2.501 (225.6); 2.497 (167.3); 2.492 (83.0); 2.333 (1.1); 2.328 (1.5); 2.324 (1.1); 2.319 (0.6); 1.246 (3.5); 1.227 (8.1); 1.209 (3.5); 0.000 (1.4)

Example 8

[0619] .sup.1H-NMR (400.0 MHz, ds-DMSO): δ=9.340 (4.3); 8.857 (2.5); 8.850 (2.6); 8.726 (3.2); 8.704 (3.7); 8.397 (3.7); 8.375 (3.3); 8.333 (4.6); 8.314 (0.8); 7.366 (1.1); 7.230 (2.6); 7.095 (1.2); 6.952 (2.6); 6.945 (2.5); 3.995 (16.0); 3.973 (0.4); 3.865 (1.0); 3.847 (3.5); 3.828 (3.6); 3.810 (1.1); 3.317 (169.3); 2.675 (1.5); 2.670 (2.0); 2.666 (1.6); 2.506 (236.7); 2.501 (308.1); 2.497 (237.6); 2,332 (1.5); 2.328 (2.0); 2.324 (1.5); 1.252 (3.7); 1.234 (8.2); 1.216 (3.7); 0.146 (2.1); 0.036 (0.4); 0.007 (25.1); 0.000 (412.7); −0.044 (0.5); −0.150 (2.0)

Example 9

[0620] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=20.007 (0.4); 9.336 (4.7); 8.803 (3.6); 8.797 (3.5); 8.694 (0.5); 8.685 (3.0); 8.663 (3.6); 8.329 (5.1); 8.313 (7.2); 8.290 (3.1); 7.682 (0.4); 7.651 (0.8); 7.071 (0.4); 6.830 (3.4); 6.823 (3.6); 5.749 (0.4); 4.393 (0.5); 3.983 (16.0); 3.850 (1.2); 3.831 (3.8); 3.813 (3.7); 3.795 (1.2); 3.510 (0.4); 3.417 (0.6); 3.387 (0.8); 3.317 (1382.9); 3.252 (0.8); 3.239 (0.6); 3.196 (0.4); 2.943 (0.4); 2.888 (0.6); 2.871 (0.5); 2.803 (0.4); 2.751 (0.6); 2.708 (0.7); 2.670 (12.0); 2.612 (1.3); 2.501 (1834.3); 2.377 (0.6); 2.328 (12.1); 2.074 (0.4); 1.420 (6.0); 1.310 (0.4); 1.246 (3.9); 1.228 (8.1); 1.209 (3.8); 0.977 (1.1); 0.961 (1.0); 0.145 (0.7); 0.000 (134.3); −0.149 (0.7); −2.678 (0.4)

Example 10

[0621] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.331 (4.6); 8.684 (3.2); 8.677 (3.3); 8.659 (3.0); 8.637 (3.4); 8.336 (3.8); 8.324 (5.1); 8.314 (3.8); 6.659 (3.3); 6.652 (3.4); 4.520 (10.2); 3.981 (16.0); 3.965 (0.4); 3.834 (1.1); 3.816 (3.6); 3.797 (3.7); 3.779 (1.1); 3.341 (19.6); 3.316 (49.2); 2.670 (1.1); 2.505 (125.2); 2.501 (161.0); 2.497 (125.8); 2.328 (1.0); 1.244 (3.7); 1.225 (8.0); 1.207 (3.6); 0.000 (10.7)

Example 11

[0622] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=10.865 (1.2); 9.392 (6.5); 9.349 (4.2); 8.759 (3.5); 8.737 (3.8); 8.333 (4.5); 8.313 (0.4); 8.188 (3.8); 8.166 (3.6); 4.006 (16.0); 3.913 (0.3); 3.876 (1.0); 3.857 (3.3); 3.839 (3.4); 3.820 (1.0); 3.318 (93.9); 3.298 (0.4); 2.675 (0.5); 2.671 (0.7); 2.666 (0.5); 2.524 (1.8); 2.510 (40.4); 2.506 (79.1); 2.502 (104.5); 2.497 (78.2); 2.493 (39.0); 2.333 (0.5); 2.328 (0.7); 2.324 (0.5); 2.133 (2.9); 1.254 (3.6); 1.236 (8.2); 1.217 (3.6); 0.000 (5.5)

Example 12

[0623] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.340 (4.6); 8.790 (3.2); 8.768 (7.1); 8.761 (3.7); 8.568 (1.3); 8.556 (1.3); 8.544 (0.5); 8.466 (3.5); 8.444 (3.1); 8.332 (4.9); 8.313 (0.4); 6.970 (3.5); 6.963 (3.5); 3.995 (16.0); 3.859 (1.1); 3.840 (3.5); 3.822 (3.6); 3.803 (1.1); 3.320 (108.6); 3.317 (108.4); 2.832 (7.1); 2.821 (7.2); 2.671 (1.2); 2.506 (150.1); 2.502 (197.4); 2.498 (152.7); 2.328 (1.2); 1.259 (3.7); 1.240 (8.2); 1.222 (3.7); 0.000 (0.9)

Example 13

[0624] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.334 (4.8); 8.615 (3.1); 8.593 (3.6); 8.448 (5.5); 8.322 (5.1); 8.296 (3.6); 8.274 (3.2); 7.840 (5.6); 3.971 (16.0); 3.808 (1.1); 3.790 (3.7); 3.771 (3.6); 3.753 (1.1); 3.314 (36.6); 2.670 (0.8); 2.501 (109.5); 2.497 (87.0); 2.328 (0.7); 1.837 (0.3); 1.824 (0.7); 1.815 (0.8); 1.803 (1.4); 1.791 (0.9); 1.782 (0.8); 1.770 (0.4); 1.236 (3.8); 1.217 (8.1); 1.199 (3.7); 0.904 (0.8); 0.893 (2.5); 0.888 (2.7); 0.878 (1.4); 0.872 (2.5); 0.867 (2.5); 0.857 (0.9); 0.661 (1.0); 0.650 (3.0); 0.646 (3.1); 0.638 (2.9); 0.634 (3.0); 0.623 (0.8); 0.000 (4.9)

Example 14

[0625] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.326 (4.3); 9.277 (0.5); 8.708 (3.2); 8.693 (4.0); 8.690 (4.4); 8.687 (4.2); 8.354 (4.0); 8.350 (4.0); 8.339 (3.5); 8.321 (5.0); 7.899 (0.5); 7.878 (0.4); 3.988 (3.0); 3.977 (16.0); 3.857 (1.0); 3.838 (3.4); 3.820 (3.5); 3.801 (1.0); 3.316 (91.8); 2.675 (1.1); 2.670 (1.4); 2.666 (1.1); 2.541 (1.2); 2.510 (89.3); 2.506 (170.5); 2.501 (222.8); 2.497 (166.7); 2.333 (1.1); 2.328 (1.4); 2.324 (1.1); 1.252 (3.8); 1.233 (8.4); 1.215 (3.6); 0.008 (2.3); 0.000 (49.4); −0.008 (2.2)

Example 15

[0626] .sup.1H-NMR (600.1 MHz, DMF): δ=9.653 (6.3); 9.432 (2.9); 9.414 (0.4); 8.851 (3.4); 8.837 (3.7); 8.829 (0.5); 8.814 (0.5); 8.451 (0.5); 8.437 (0.5); 8.374 (0.9); 8.363 (3.6); 8.353 (3.1); 8.352 (3.3); 8.349 (3.9); 8.346 (0.9); 8.345 (0.7); 8.024 (2.3); 4.489 (1.2); 4.204 (2.2); 4.171 (16.0); 4.149 (1.3); 3.986 (0.9); 3.973 (3.3); 3.961 (3.5); 3.949 (1.4); 3.936 (0.4); 3.476 (9.4); 2.921 (1.2); 2.918 (2.5); 2.915 (3.7); 2.912 (2.7); 2.909 (1.4); 2.753 (0.4); 2.751 (1.5); 2.748 (3.0); 2.744 (5.1); 2.742 (19.7); 2.738 (2.6); 2.645 (2.4); 2.149 (0.3); 1.374 (0.6); 1.351 (3.4); 1.347 (0.9); 1.339 (7.8); 1.334 (1.7); 1.326 (3.5); 1.322 (0.8); 0.000 (4.6)

Example 16

[0627] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.339 (2.9); 8.667 (3.7); 8.658 (25); 8.636 (2.7); 8.335 (3.0); 8.328 (3.2); 8.313 (2.9); 8.051 (3.5); 3.988 (11.5); 3.834 (0.7); 3.816 (2.4); 3.797 (2.4); 3.779 (0.7); 3.317 (93.1); 2.675 (0.7); 2.670 (1.0); 2.666 (0.7); 2.510 (60.4); 2.506 (114.2); 2.501 (147.2); 2.497 (108.1); 2.493 (53.7); 2.451 (16.0); 2.439 (0.5); 2.333 (0.7); 2.328 (0.9); 2.324 (0.7); 1.244 (2.6); 1.226 (5.9); 1.208 (2.5); 0.008 (1.6); 0.000 (33.4); −0.008 (1.3)

Example 17

[0628] .sup.1H-NMR (601.6 MHz, DMF): δ=9.432 (0.5); 9.402 (3.0); 9.141 (0.6); 9.138 (0.6); 8.919 (0.5); 8.904 (0.6); 8.861 (3.0); 8.846 (3.6); 8.740 (0.6); 8.726 (05); 8.631 (3.4); 8.617 (3.1); 8.384 (11.6); 8.356 (0.5); 8.355 (0.5); 8.327 (3.3); 8.326 (3.2); 8.123 (0.6); 8.120 (0.6); 8.024 (2.2); 4.175 (2.6); 4.139 (16.0); 3.992 (0.6); 3.980 (0.6); 3.953 (1.0); 3.941 (3.5); 3.929 (3.5); 3.916 (1.1); 3.467 (6.1); 2.921 (1.1); 2.918 (2.3); 2.915 (3.2); 2.912 (2.3); 2.908 (1.1); 2.751 (1.2); 2.748 (2.5); 2.744 (3.5); 2.741 (2.4); 2.738 (1.2); 2.147 (0.5); 1.366 (0.6); 1.354 (1.5); 1.350 (3.6); 1.337 (7.9); 1.325 (3.5); 0.000 (3.1)

Example 18

[0629] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.636 (6.8); 9.357 (4.3); 9.35277 (07); 8778 (33); 8.3); 9277 (07); 778 (3.3); 8.757 (3.7); 8.359 (0.6); 8.343 (4.7); 8.314 (1.2); 8.309 (3.7); 8.288 (3.4); 7.900 (0.6); 7.879 (0.6); 4.009 (16.0); 3.988 (3.2); 3.903 (1.0); 3.884 (3.5); 3.866 (3.5); 3.847 (1.1); 3.317 (75.6); 2.675 (0.7); 2.670 (1.0); 2.666 (0.7); 2.506 (114.6); 2.501 (149.2); 2.497 (112.5); 2.333 (0.7); 2.328 (1.0); 2.324 (0.7); 1.259 (3.7); 1.241 (8.2); 1.222 (3.6); 0.008 (1.8); 0.000 (37.6); −0.008 (1.6)

Example 19

[0630] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.591 (5.7); 9.367 (4.6); 8.761 (3.1); 8.739 (3.6); 8.570 (5.4); 8.442 (3.6); 8.420 (3.2); 8.342 (5.1); 8.314 (0.5); 4.316 (0.9); 4.020 (16.0); 3.988 (0.8); 3.899 (1.1); 3.881 (3.6); 3.862 (3.7); 3.844 (1.2); 3.315 (59.6); 2.670 (1.0); 2.505 (120.9); 2.501 (155.0); 2.497 (121.0); 2.328 (1.1); 1.290 (0.5); 1.260 (3.9); 1242 (8.3); 1.223 (3.8); 0.000 (18.0)

Example 20

[0631] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=10.199 (0.4); 9.318 (4.5); 8.548 (2.7); 8.541 (4.9); 8.520 (3.7); 8.414 (3.5); 8.393 (2.6); 8.312 (5.0); 7.884 (2.0); 7.872 (2.4); 7.761 (1.9); 7.754 (2.0); 7.748 (1.7); 7.741 (1.5); 5.754 (3.1); 3.946 (16.0); 3.818 (1.1); 3.800 (3.7); 3.781 (3.7); 3.763 (1.2); 3.318 (53.3); 2.671 (1.0); 2.506 (119.4); 2.502 (149.0); 2.329 (1.0); 1.240 (3.9); 1.222 (8.2); 1.203 (3.7); 0.000 (4.1)

Example 21

[0632] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.333 (3.8); 9.277 (0.3); 8.725 (2.7); 8.719 (2.7); 8.672 (3.3); 8.650 (3.9); 8.384 (3.8); 8.362 (3.4); 8.337 (0.6); 8.326 (3.9); 8.314 (0.8); 8.012 (3.0); 8.010 (3.0); 7.900 (0.4); 6.691 (2.1); 6.687 (2.3); 6.684 (2.3); 6.680 (2.1); 4.316 (0.5); 3.984 (16.0); 3.833 (1.0); 3.815 (3.3); 3.796 (3.3); 3.778 (1.0); 3.316 (57.1); 2.680 (0.4); 2.675 (0.7); 2.670 (1.0); 2.666 (0.7); 2.510 (60.0); 2.506 (116.8); 2.501 (153.4); 2.497 (113.4); 2.492 (56.4); 2.333 (0.7); 2.328 (1.0); 2.324 (0.7); 1.246 (3.5); 1.228 (8.0); 1.209 (3.4); 0.008 (1.6); 0.000 (36.9); −0.009 (1.5)

Example 22

[0633] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.346 (4.7); 9.011 (3.5); 9.004 (3.4); 8.761 (3.0); 8.739 (3.5); 8.482 (3.5); 8.461 (3.0); 8.338 (5.1); 8.313 (1.4); 7.375 (3.5); 7.368 (3.4); 4.402 (0.4); 4.078 (0.4); 3.997 (16.0); 3.881 (1.1); 3.863 (3.7); 3.844 (3.8); 3.826 (1.2); 3.361 (1.1); 3.318 (598.3); 3.284 (1.3); 3.266 (0.4); 2.670 (4.4); 2.627 (0.3); 2.623 (0.4); 2.606 (0.5); 2.501 (633.5); 2.412 (0.5); 2.328 (4.0); 1.255 (3.9); 1.237 (8.2); 1.219 (3.8); 0.000 (42.1)

Example 23

[0634] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=10.969 (2.7); 9.328 (4.7); 8.659 (3.2); 8.637 (3.5); 8.608 (3.4); 8.601 (3.4); 8.321 (5.1); 8.121 (3.1); 8.099 (2.9); 6.942 (2.3); 6.936 (2.3); 3.976 (16.0); 3.817 (1.0); 3.799 (3.7); 3.780 (3.6); 3.762 (1.1); 3.316 (136.6); 3.289 (0.5); 2.671 (2.2); 2.571 (0.4); 2.505 (287.8); 2.501 (362.4); 2.498 (276.2); 2.328 (2.5); 2.083 (10.5); 1.242 (3.8); 1.224 (8.1); 1.205 (3.7); 0.000 (21.5)

Example 24

[0635] .sup.1H-NMR (601.6 MHz, DMF): δ=9.955 (2.9); 9.953 (2.8); 9.450 (3.3); 9.408 (1.5); 9.007 (1.6); 8.991 (3.0); 8.977 (3.5); 8.956 (1.4); 8.942 (1.6); 8.817 (3.6); 8.802 (3.1); 8.744 (1.6); 8.729 (1.4); 8.370 (3.6); 8.369 (3.4); 8.338 (1.6); 8.337 (1.5); 8.023 (2.4); 4.188 (16.0); 4.142 (7.4); 4.044 (1.1); 4.032 (3.6); 4.020 (3.6); 4.007 (1.1); 3.976 (0.5); 3.964 (1.6); 3.951 (1.6); 3.939 (0.5); 3.468 (3.4); 2.920 (1.2); 2.917 (2.4); 2.914 (3.3); 2.911 (2.3); 2.908 (1.1); 2.750 (1.3); 2.747 (2.5); 2.744 (3.6); 2.741 (2.5); 2.737 (1.2); 1.376 (3.7); 1.363 (8.0); 1.355 (2.0); 1.351 (3.8); 1.343 (3.7); 1.331 (1.6); 0.000 (4.1)

Example 25

[0636] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.346 (4.2); 8.969 (2.0); 8.965 (2.2); 8.745 (3.2); 8.723 (3.7); 8.453 (3.7); 8.431 (3.2); 8.338 (4.5); 7.186 (2.8); 7.180 (2.8); 4.002 (16.0); 3.883 (1.0); 3.864 (3.4); 3.846 (3.5); 3.827 (1.1); 3.318 (38.8); 2.675 (0.4); 2.671 (0.6); 2.667 (0.5); 2.524 (1.6); 2.506 (69.2); 2.502 (93.0); 2.498 (70.9); 2.333 (0.4); 2.329 (0.6); 2.324 (0.4); 1.256 (3.8); 1.237 (8.7); 1.219 (3.8); 1.176 (0.3); 0.008 (0.4); 0.000 (12.1)

Example 26

[0637] .sup.1H-NMR (600.1 MHz, d.sub.6-DMSO): δ=9.388 (1.8); 9.387 (2.5); 9.385 (2.1); 9.355 (3.2); 8.751 (3.8); 8.736 (4.4); 8.479 (3.5); 8.452 (4.1); 8.437 (4.0); 8.342 (3.3); 8.341 (3.5); 4.013 (16.0); 3.874 (0.8); 3.861 (3.0); 3.849 (3.1); 3.837 (0.9); 3.325 (9.3); 2.511 (4.8); 2.508 (11.1); 2.505 (16.0); 2.502 (12.0); 2.499 (5.9); 1.255 (3.4); 1.242 (7.9); 1.230 (3.4); 0.000 (1.3)

Example 27

[0638] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.338 (3.9); 8.934 (3.3); 8.819 (2.8); 8.783 (2.6); 8.761 (3.0); 8.475 (2.9); 8.453 (2.5); 8.331 (4.1); 8.313 (0.4); 3.991 (14.1); 3.876 (1.0); 3.857 (3.2); 3.839 (3.2); 3.821 (1.0); 3.349 (0.5); 3.317 (53.8); 3.282 (0.5); 2.671 (0.8); 2.506 (97.4); 2.502 (120.1); 2.497 (89.9); 2.471 (0.9); 2.466 (1.3); 2.461 (1.4); 2.329 (0.8); 2.073 (16.0); 1.261 (3.4); 1.243 (7.3); 1.224 (3.3); 0.000 (6.5)

Example 28

[0639] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.345 (4.9); 8.863 (2.7); 8.852 (2.7); 8.675 (2.9); 8.653 (3.3); 8.372 (3.3); 8.350 (3.0); 8.328 (5.2); 8.314 (0.7); 8.162 (2.6); 8.152 (2.7); 3.989 (16.0); 3.847 (1.1); 3.830 (3.7); 3.811 (3.8); 3.793 (1.2); 3.316 (94.6); 2.670 (1.7); 2.501 (258.1); 2.328 (1.7); 1.988 (0.4); 1.246 (4.0); 1.228 (8.4); 1.209 (3.9); 0.146 (0.9); 0.000 (175.4); −0.150 (1.0)

Example 29

[0640] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.328 (3.8); 8.712 (3.0); 8.705 (3.0); 8.640 (2.7); 8.618 (3.1); 8.320 (4.0); 8.278 (3.0); 8.256 (2.8); 6.706 (3.0); 6.699 (3.0); 3.972 (13.5); 3.824 (0.9); 3.806 (3.0); 3.788 (3.0); 3.769 (09); 3.316 (61.2); 2.675 (1.0); 2.670 (1.3); 2.616 (16.0); 2.506 (142.2); 2.501 (182.8); 2.497 (140.4); 2.332 (0.9); 2.328 (1.2); 2.324 (0.9); 2.073 (0.6); 1.241 (3.2); 1.223 (6.9); 1.204 (3.1); 0.146 (1.0); 0.008 (11.6); 0.000 (190.1); −0.150 (1.0)

Example 30

[0641] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.833 (0.8); 9.369 (0.9); 9.312 (4.4); 8.988 (4.2); 8.872 (0.7); 8.850 (0.9); 8.837 (3.1); 8.815 (3.8); 8.705 (0.9); 8.683 (0.7); 8.632 (3.9); 8.610 (3.3); 8.354 (1.2); 8.344 (4.7); 8.309 (0.4); 4.019 (3.6); 3.963 (16.0); 3.910 (0.8); 3.892 (0.8); 3.873 (0.3); 3.861 (1.0); 3.842 (3.3); 3.824 (3.3); 3.805 (1.1); 3.494 (0.5); 3.364 (703.3); 3.349 (753.8); 3.343 (459.9); 3.192 (0.4); 2.677 (1.3); 2.673 (1.8); 2.508 (208.5); 2.504 (272.5); 2.500 (210.7); 2.335 (1.3); 2.330 (1.8); 2.073 (0.4); 1.278 (0.9); 1.259 (2.5); 1.254 (4.1); 1.235 (8.7); 1.217 (3.7); 0.000 (6.7)

Example 31

[0642] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.332 (4.5); 9.277 (0.4); 8.627 (3.1); 8.605 (3.6); 8.496 (3.6); 8.337 (0.5); 8.323 (4.7); 8.311 (3.9); 8.288 (3.2); 7.899 (0.4); 7.842 (4.7); 4.316 (0.8); 3.988 (2.3); 3.976 (16.0); 3.817 (1.1); 3.799 (3.6); 3.780 (3.6); 3.762 (1.1); 3.315 (81.0); 2.675 (1.4); 2.670 (1.8); 2.666 (1.4); 2.552 (0.5); 2.505 (211.7); 2.501 (273.1); 2.497 (205.7); 2.452 (0.5); 2.332 (1.4); 2.328 (1.8); 2.324 (1.3); 2.103 (11.8); 1.290 (0.4); 1.241 (3.8); 1.222 (8.1); 1.204 (3.6); 0.146 (1.5); 0.029 (0.4); 0.000 (299.6); −0.008 (15.2); −0.039 (0.3); −0.150 (1.5)

Example 32

[0643] .sup.1H-NMR (600.1 MHz, DMF): δ=9.677 (5.4); 9.437 (2.8); 8.873 (3.3); 8.859 (3.6); 8.485 (5.2); 8.447 (3.6); 8.433 (3.4); 8.356 (3.1); 8.355 (3.1); 8.025 (1.5); 4.183 (16.0); 3.996 (1.0); 3.984 (3.3); 3.972 (3.4); 3.959 (1.0); 3.479 (6.4); 2.921 (0.8); 2.918 (1.6); 2.915 (2.4); 2.912 (1.7); 2.909 (0.8); 2.751 (0.9); 2.748 (1.8); 2.745 (2.7); 2.741 (1.9); 2.738 (0.9); 1.357 (3.4); 1.345 (7.7); 1.332 (3.4); 0.000 (2.5)

Example 33

[0644] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.326 (4.2); 8.739 (3.8); 8.690 (3.1); 8.668 (3.6); 8.358 (3.4); 8.336 (3.1); 8.323 (4.5); 8.313 (0.4); 8.175 (0.6); 8.125 (2.2); 8.122 (3.6); 7.207 (3.2); 3.979 (16.0); 3.846 (1.0); 3.827 (3.4); 3.809 (3.5); 3.790 (1.1); 3.320 (70.0); 2.949 (1.0); 2.675 (0.7); 2.671 (1.0); 2.666 (0.8); 2.524 (2.5); 2.510 (57.1); 2.506 (114.6); 2.501 (155.0); 2.497 (118.1); 2.493 (59.5); 2.333 (0.8); 2.328 (1.0); 2.324 (0.8); 1.368 (0.4); 1.252 (3.6); 1.234 (8.1); 1.215 (3.5); 0.008 (0.7); 0.000 (20.2); −0.008 (0.8)

Example 34

[0645] .sup.1H-NMR (601.6 MHz, DMF): δ=9.403 (3.7); 8.721 (3.1); 8.706 (3.4); 8.688 (2.6); 8.684 (2.6); 8.371 (3.3); 8.356 (3.1); 8.324 (3.9); 8.024 (1.4); 6.531 (2.7); 6.527 (2.7); 4.136 (16.0); 3.919 (1.1); 3.906 (3.7); 3.894 (3.7); 3.882 (1.2); 3.626 (0.7); 3.467 (4.1); 2.920 (0.7); 2.917 (1.4); 2.913 (1.8); 2.910 (1.3); 2.907 (0.7); 2.750 (0.7); 2.747 (1.4); 2.744 (1.9); 2.741 (1.4); 2.738 (0.7); 2.384 (13.2); 2.146 (1.9); 1.785 (0.3); 1.779 (0.8); 1.774 (0.3); 1.409 (1.1); 1.334 (3.8); 1.322 (8.1); 1.310 (3.8); 0.000 (2.0)

Example 35

[0646] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.347 (4.2); 8.967 (3.9); 8.960 (3.9); 8.778 (3.3); 8.756 (3.9); 8.464 (3.9); 8.442 (3.5); 8.341 (4.4); 7.198 (4.0); 7.191 (4.0); 4.002 (16.0); 3.888 (1.0); 3.869 (3.4); 3.851 (3.4); 3.832 (1.1); 3.425 (19.5); 3.316 (40.1); 2.671 (0.5); 2.666 (0.3); 2.510 (27.1); 2.506 (54.7); 2.502 (72.9); 2.497 (54.1); 2.493 (27.3); 2.333 (0.3); 2.328 (0.4); 2.324 (0.3); 1.259 (3.7); 1.240 (8.4); 1.222 (3.7); 0.000 (4.5)

Example 36

[0647] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.369 (4.2); 8.965 (5.4); 8.698 (3.3); 8.676 (3.9); 8.368 (4.0); 8.359 (4.5); 8.346 (3.6); 8.313 (0.5); 8.161 (5.3); 4.000 (16.0); 3.868 (0.9); 3.850 (3.3); 3.831 (34); 3.813 (1.0); 3.319 (149.4); 2.675 (0.7); 2.671 (1.0); 2.666 (0.8); 2.524 (2.2); 2.511 (60.9); 2.506 (127.7); 2.502 (171.3); 2.497 (124.9); 2.493 (61.1); 2.333 (0.7); 2.328 (1.0); 2.324 (0.8); 1.252 (3.6); 1.234 (8.3); 1.216 (3.6); 0.008 (0.9); 0.000 (29.3); −0.009 (1.1)

Example 37

[0648] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.255 (4.3); 8.252 (4.6); 8.139 (2.9); 8.116 (3.2); 7.422 (2.6); 7.399 (2.5); 4.185 (3.4); 4.140 (0.5); 3.908 (16.0); 3.655 (0.9); 3.636 (3.3); 3.618 (3.3); 3.599 (1.0); 3.318 (42.6); 3.241 (3.7); 2.675 (0.4); 2.670 (0.6); 2.666 (0.4); 2.524 (1.4); 2.506 (76.0); 2.501 (100.4); 2.497 (73.0); 2.328 (0.6); 2.324 (0.5); 1.199 (3.6); 1.181 (8.1); 1.163 (3.5); 0.008 (1.4); 0.000 (42.1); −0.008 (1.7)

Example 38

[0649] .sup.1H-NMR (601.6 MHz, d.sub.6-DMSO): δ=9.329 (2.5); 8.645 (2.6); 8.631 (3.0); 8.622 (2.8); 8.335 (2.9); 8.321 (4.9); 8.311 (0.3); 7.961 (3.1); 3.976 (11.9); 3.802 (0.8); 3.790 (2.6); 3.777 (2.6); 3.765 (1.0); 3.643 (5.9); 3.594 (0.4); 3.581 (0.5); 3.552 (0.5); 3.546 (0.6); 3.539 (0.5); 3.528 (0.5); 3.315 (57.5); 3.313 (63.9); 3.311 (61.6); 3.310 (61.3); 2.616 (0.8); 2.613 (1.0); 2.537 (0.4); 2.522 (2.0); 2.519 (2.4); 2.516 (2.4); 2.507 (40.3); 2.504 (89.9); 2.501 (127.5); 2.498 (95.5); 2.495 (46.6); 2.426 (0.4); 2.388 (0.8); 2.385 (1.0); 2.382 (0.8); 2.006 (16.0); 1.233 (2.8); 1.221 (6.1); 1.209 (2.8); 1.043 (0.4); 1.033 (0.4); 0.000 (1.4)

Example 39

[0650] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.325 (0.4); 9.308 (3.9); 9.295 (0.5); 9.276 (0.4); 9.242 (0.5); 8.852 (3.1); 8.830 (3.9); 8.630 (3.7); 8.607 (3.2); 8.581 (0.8); 8.564 (0.6); 8.554 (0.4); 8.541 (0.3); 8.507 (0.5); 8.490 (0.3); 8.456 (0.5); 8.313 (3.9); 8.307 (3.8); 8.293 (0.7); 8.284 (0.9); 8.242 (0.6); 7.346 (3.5); 7.337 (3.7); 6.871 (3.4); 6.863 (3.3); 4.551 (0.9); 4.036 (0.4); 3.988 (0.5); 3.956 (0.6); 3.950 (0.6); 3.934 (16.0); 3.919 (1.1); 3.907 (0.9); 3.898 (1); 33864 (1.6); 3864 (1.0); 3.857 (12); 3824 (0.6); 3.801 (04); 3.787 (1.1); 3769 (3.2); 3.751 (32); 3.739 (1.5); 3.733 (1.1); 3.697 (0.4); 3.526 (0.3); 3.456 (0.3); 3.416 (0.3); 3.400 (0.3); 3.376 (0.5); 3.315 (620.6); 3.260 (0.7); 3.243 (13.9); 3.009 (0.5); 2.997 (1.8); 2.928 (0.7); 2.872 (0.6); 2.845 (1.0); 2.838 (0.7); 2.739 (0.3); 2.708 (0.3); 2.694 (0.4); 2.679 (2.4); 2.675 (5.0); 2.670 (7.1); 2.665 (5.2); 2.661 (2.5); 2.616 (0.4); 2.600 (0.4); 2.577 (0.6); 2.560 (1.0); 2.524 (16.0); 2.519 (23.9); 2.510 (399.2); 2.506 (855.5); 2.501 (1155.7); 2.496 (824.3); 2.492 (385.6); 2.423 (0.4); 2.337 (2.3); 2.332 (4.8); 2.328 (68); 2.323 (4.9); 2.319 (2.5); 2.073 (3.8); 1.284 (0.3); 1.260 (0.6); 1.226 (4.2); 1.208 (8.6); 1.189 (3.9); 1.163 (1.0); 1.144 (1.0); 1.124 (0.5); 0.854 (0.4); 0.146 (5.2); 0.008 (40.5); 0.000 (1308.7); −0.009 (42.9); −0.037 (0.6); −0.142 (0.3); −0.150 (5.3)

Example 40

[0651] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.335 (3.7); 8.740 (3.1); 8.733 (3.2); 8.700 (3.5); 8.678 (4.1); 8.352 (4.0); 8.330 (7.6); 8.313 (0.6); 6.732 (3.4); 6.725 (3.5); 4.707 (5.6); 3.984 (16.0); 3.870 (03); 3.839 (0.9); 3.820 (3.1); 3.802 (3.2); 3.783 (0.9); 3.318 (1.38); 3.158 (0.6); 3.085 (13.1); 2.680 (0.4); 2.675 (0.8); 2.670 (1.2); 2.666 (0.9); 2.661 (0.4); 2.524 (2.7); 2519 (4.1); 2.510 (67.7); 2.506 (144.7); 2.501 (195.2); 2.497 (140.3); 2.492 (66.6); 2.337 (0.4); 2.333 (0.9); 2.328 (1.2); 2.324 (0.9); 2.319 (0.4); 1.245 (3.5); 1.227 (8.1); 1.208 (3.4); 0.146 (0.4); 0.008 (3.2); 0.000 (105.2); −0.009 (3.6); −0.150 (0.4)

Example 41

[0652] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.311 (3.9); 8.591 (12.1); 8.309 (4.2); 4.673 (1.8); 4.654 (3.7); 4.636 (2.0); 3.939 (16.0); 3.907 (0.5); 3.817 (0.9); 3.798 (3.2); 3.780 (3.3); 3.761 (1.0); 3.623 (2.1); 3.604 (4.1); 3.586 (1.9); 3.318 (160.5); 2.675 (0.6); 2.670 (0.8); 2.666 (0.6); 2.524 (1.9); 2.519 (3.0); 2.510 (50.5); 2.506 (107.9); 2.501 (146.3); 2.497 (106.2); 2.492 (51.2); 2.333 (0.6); 2.328 (0.9); 2.324 (0.7); 1.224 (3.6); 1.206 (8.3); 1.187 (3.5); 0.000 (1.7)

Example 42

[0653] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.302 (3.6); 8.535 (1.8); 8.513 (5.6); 8.492 (5.4); 8.469 (2.0); 8.313 (0.8); 8.299 (3.9); 4.416 (1.8); 4.398 (3.1); 4.379 (1.9); 3.927 (16.0); 3.781 (1.0); 3.762 (3.2); 3.743 (3.3); 3.725 (0.9); 3.500 (2.1); 3.482 (3.5); 3.464 (1.9); 3.315 (170.1); 2.680 (0.6); 2.675 (1.0); 2.670 (1.5); 2.666 (1.0); 2.524 (3.7); 2.519 (5.6); 2.510 (87.7); 2.506 (186.8); 2.501 (251.5); 2.497 (179.1); 2.492 (83.4); 2.332 (1.1); 2.328 (1.5); 2.323 (1.0); 1.214 (3.4); 1.196 (8.0); 1.177 (3.4); 0.146 (1.6); 0.017 (0.7); 0.008 (12.5); 0.000 (394.4); −0.009 (14.5); −0.025 (0.6); −0.150 (1.6)

Example 43

[0654] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.309 (4.3); 8.848 (3.4); 8.826 (3.7); 8.328 (4.8); 8.291 (3.8); 8.270 (3.5); 3.944 (16.0); 3.870 (1.0); 3.852 (3.4); 3.833 (3.5); 3.815 (1.1); 3.737 (0.6); 3.438 (18.4); 3.345 (119.9); 3.338 (162.5); 3.328 (133.1); 2.676 (0.8); 2.671 (1.2); 2.667 (0.8); 2.525 (3.2); 2.511 (69.7); 2.507 (147.0); 2.502 (197.6); 2.498 (140.7); 2.493 (66.0); 2.334 (0.8); 2.329 (1); 2.324 (0.8); 1.988 (1.0); 1.299 (0. 4); 1.257 (4.2); 1.238 (9.5); 1.220 (4.0); 1.193 (0.4); 1.175 (0.6); 1.157 (0.4); 1.045 (0.5); 1.030 (0.4); 0.146 (0.4); 0.008 (3.5); 0.000 (92.2); −0.008 (3.4); −0.150 (0.4)

Example 44

[0655] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.286 (4.1); 8.627 (3.2); 8.604 (4.0); 8.372 (3.7); 8.350 (3.2); 8.312 (0.5); 8.280 (4.3); 4.140 (0.4); 3.993 (1.5); 3.975 (2.3); 3.953 (1.8); 3.909 (16.0); 3.721 (1.0); 3.703 (3.3); 3.684 (3.4); 3.666 (1.0); 3.516 (1.8); 3.496 (2.3); 3.476 (1.5); 3.318 (157.5); 2.852 (150.2); 2.676 (0.6); 2.671 (0.7); 2.666 (0.5); 2.524 (1.9); 2.510 (42.2); 2.506 (85.0); 2.502 (111.9); 2.497 (81.4); 2.493 (40.0); 2.333 (0.5); 2.329 (0.7); 2.324 (0.5); 1.204 (3.8); 1.185 (8.1); 1.167 (3.5); 0.008 (0.7); 0.000 (21.3); −0.008 (0.8)

Example 45

[0656] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.335 (3.8); 9.292 (0.7); 8.600 (2.4); 8.578 (2.7); 8.569 (0.7); 8.547 (0.5); 8.356 (4.5); 8.322 (4.2); 8.313 (2.1); 8.297 (2.8); 8.275 (2.3); 8.138 (0.5); 8.117 (0.4); 7.869 (4.2); 3.975 (12.3); 3.907 (2.3); 3.794 (1.5); 3.778 (16.0); 3.758 (3.2); 3.740 (1.1); 3.316 (291.4); 2.670 (3.0); 2.578 (0.7); 2.501 (447.9); 2.497 (409.0); 2.328 (2.9); 1.234 (3.9); 1.216 (7.0); 1.198 (4.2); 1.179 (0.8); 0.000 (3.8)

Example 46

[0657] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.311 (3.7); 8.823 (3.3); 8.801 (3.9); 8.534 (3.8); 8.512 (3.4); 8.333 (3.9); 3.961 (15.9); 3.903 (0.7); 3.867 (0.9); 3.848 (3.3); 3.830 (3.3); 3.811 (1.0); 3.655 (16.0); 3.405 (0.8); 3.316 (82.2); 2.675 (0.6); 2.670 (0.9); 2.666 (0.6); 2.661 (0.3); 2.524 (2.0); 2.519 (3.0); 2.510 (49.6); 2.506 (105.7); 2.501 (142.8); 2.497 (103.8); 2.492 (50.3); 2.333 (0.6); 2.328 (0.8); 2.324 (0.6); 1.250 (3.5); 1.231 (8.1); 1.213 (3.5); 1.180 (0.4); 0.146 (0.5); 0.008 (3.8); 0.000 (124.3); −0.009 (4.4); −0.150 (0.5)

Example 47

[0658] .sup.1H-NMR (601.6 MHz, d.sub.6-DMSO): δ=9.327 (2.9); 8.646 (4.0); 8.642 (2.2); 8.631 (2.9); 8.320 (3.1); 8.310 (0.4); 8.302 (2.7); 8.288 (2.7); 6.628 (2.3); 6.624 (2.3); 4.045 (0.3); 4.032 (0.3); 4.015 (0.4); 3.989 (0.5); 3.976 (11.9); 3.957 (0.4); 3.945 (0.4); 3.929 (0.4); 3.907 (0.4); 3891 (0.4); 3.874 (0.4); 3.854 (0.4); 3.839 (0.5); 3.813 (1.1); 3.800 (2.9); 3.794 (7.1); 3.788 (3.2); 3.775 (1.1); 3.765 (0.5); 3.752 (0.4); 3.735 (0.5); 3.705 (0.5); 3.673 (0.5); 3.644 (0.6); 3.593 (0.7); 3.576 (0.7); 3.568 (0.7); 3.560 (0.8); 3.504 (1.0); 3.498 (1.0); 3.487 (1.1); 3.318 (97.0); 3.314 (127.2); 3.311 (112.7); 3.309 (100.1); 3.260 (0.6); 3.229 (0.4); 3.220 (0.4); 3.196 (0.4); 3.178 (0.4); 3123 (0.4); 2.616 (1.2); 2.613 (1.4); 2.610 (1.2); 2.593 (0.4); 2.588 (0.4); 2.580 (0.4); 2.570 (0.5); 2.522 (2.9); 2.519 (3.8); 2.516 (4.0); 2.507 (59.7); 2.504 (132.7); 2.501 (188.2); 2.498 (141.7); 2.495 (69.9); 2.445 (0.7); 2.443 (0.7); 2.416 (0.5); 2.399 (0.5); 2.385 (1.5); 2.382 (1.2); 2.347 (0.3); 2.089 (16.0); 2.071 (0.3); 1.235 (2.8); 1.222 (6.2); 1.210 (2.7); 0.000 (2.0)

Example 48

[0659] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.292 (4.9); 8.717 (0.4); 8.573 (2.0); 8.550 (3.8); 8.511 (3.8); 8.489 (1.9); 8.427 (0.4); 8.406 (0.4); 8.312 (2.4); 8.303 (4.7); 8.224 (0.4); 3.931 (1.7); 3.913 (16.0); 3.823 (1.0); 3.791 (0.3); 3.783 (0.4); 3.757 (1.2); 3.739 (3.6); 3.720 (3.5); 3.702 (1.1); 3.315 (157.9); 3.246 (0.4); 2.670 (3.7); 2.569 (0.5); 2.505 (486.9); 2.501 (620.5); 2.497 (455.2); 2.437 (0.3); 2.374 (1.6); 2.332 (3.6); 2.328 (3.7); 2.165 (14.0); 1.234 (0.8); 1.216 (4.5); 1.197 (8.6); 1.179 (3.7); 0.146 (0.4); 0.000 (63.8); −0.149 (0.4)

Example 49

[0660] .sup.1H-NMR (601.6 MHz, d.sub.6-DMSO): δ=9.333 (4.6); 8.715 (3.3); 8.711 (3.3); 8.680 (2.8); 8.665 (3.0); 8.328 (5.6); 8.318 (3.0); 6.673 (3.3); 6.669 (3.3); 4.318 (2.2); 4.296 (2.8); 4.150 (2.9); 4.128 (2.2); 3.981 (15.1); 3.825 (1.3); 3.813 (3.8); 3.801 (3.8); 3.788 (1.3); 3.314 (71.5); 2.633 (16.0); 2.614 (0.8); 2.501 (75.3); 2.385 (0.5); 1.238 (4.3); 1.226 (8.1); 1.214 (4.1); 0.000 (4.2)

Example 50

[0661] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.332 (3.3); 9.293 (0.9); 9.263 (1.4); 9.214 (0.4); 8.568 (0.8); 8.547 (1.0); 8.537 (3.2); 8.516 (3.6); 8.343 (3.6); 8.313 (2.8); 8.260 (1.6); 8.204 (0.3); 8.139 (1.0); 8.118 (1.8); 8.096 (1.3); 8.042 (3.8); 8.020 (3.4); 7.039 (1.1); 7.016 (1.0); 4.689 (2.9); 4.316 (16.0); 3.907 (4.0); 3.899 (0.3); 3.883 (6.3); 3.857 (0.7); 3.841 (1.4); 3.830 (1.3); 3.784 (0.6); 3.769 (0.8); 3.750 (0.9); 3.613 (0.5); 3.596 (1.4); 3.577 (1.5); 3.555 (1.1); 3.536 (1.2); 3.526 (0.5); 3.521 (1.4); 3.503 (1.2); 3.484 (0.5); 3.451 (0.3); 3.414 (0.4); 3.317 (598.2); 3.217 (0.6); 3.201 (1.2); 3.186 (0.6); 3.070 (0.9); 3.052 (1.1); 3.037 (1.0); 3.019 (0.9); 2.675 (4.0); 2.670 (5.6); 2.666 (4.1); 2.575 (0.4); 2.524 (14.6); 2.519 (23.4); 2.510 (341.9); 2.506 (722.4); 2.501 (970.0); 2.497 (692.6); 2.492 (325.4); 2.439 (0.6); 2.337 (1.8); 2.333 (4.1); 2.328 (5.5); 2.323 (4.1); 2.319 (1.9); 1.308 (3.7); 1.290 (8.0); 1.271 (3.5); 1.233 (0.8); 1.216 (1.0); 1.197 (2.0); 1.179 (2.0); 1.161 (3.3); 1.142 (1.7); 1.122 (0.5); 1.095 (0.3); 0.009 (0.3); 0.000 (11.1); −0.008 (0.5)

Example 51

[0662] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.290 (4.0); 8.760 (3.3); 8.739 (3.8); 8.425 (3.8); 8.403 (3.4); 8.309 (5.8); 4.140 (0.8); 3.932 (15.3); 3.804 (1.1); 3.786 (3.2); 3.768 (3.4); 3.749 (1.0); 3.387 (15.8); 3.323 (680.5); 3.276 (0.7); 3.258 (0.4); 3.210 (0.3); 2.676 (1.7); 2.671 (2.2); 2.667 (1.6); 2.556 (0.5); 2.524 (5.9); 2.511 (138.2); 2.506 (276.9); 2.502 (362.3); 2.497 (263.5); 2.493 (129.9); 2.388 (16.0); 2.329 (2.3); 2.325 (1.6); 2.023 (0.6); 1.242 (3.6); 1.223 (7.9); 1.205 (3.4); 0.008 (2.4); 0.000 (72.5); −0.008 (2.8); −0.150 (0.3)

Example 52

[0663] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.314 (4.5); 8.837 (3.1); 8.815 (3.6); 8.510 (3.6); 8.488 (3.2); 8.337 (4.8); 8314 (0.5); 5.207 (0.8); 5.185 (2.6); 5.162 (2.7); 5.140 (1.0); 4.316 (0.8); 3.968 (16.0); 3.907 (0.4); 3.878 (1.1); 3.859 (3.5); 3.841 (3.5); 3.823 (1.1); 3.317 (175.1); 2.670 (1.6); 2.505 (217.1); 2.501 (278.9); 2.497 (214.0); 2.328 (1.7); 1.290 (0.4); 1.252 (3.8); 1.233 (8.4); 1.215 (3.8); 0.000 (5.4)

Example 53

[0664] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.320 (4.4); 8.614 (3.2); 8.592 (3.7); 8.559 (3.2); 8.553 (3.3); 8.315 (4.8); 8.257 (3.6); 8.234 (3.3); 6.423 (3.5); 6.417 (3.5); 3.960 (16.0); 3.814 (1.1); 3.795 (3.5); 3.776 (3.6); 3.758 (1.1); 3.318 (283.8); 2.675 (1.6); 2.670 (2.1); 2.506 (273.9); 2.501 (348.2); 2.497 (261.4); 2.332 (1.6); 2.328 (2.1); 2.094 (0.3); 2.082 (0.7); 2.073 (0.8); 2.061 (1.4); 2.049 (0.9); 2.040 (0.7); 2.028 (0.4); 1.236 (3.9); 1.218 (8.3); 1.199 (3.7); 1.036 (0.8); 1.025 (2.3); 1.019 (2.7); 1.009 (1.5); 1.004 (2.3); 0.998 (2.4); 0.989 (0.9); 0.846 (1.0); 0.836 (2.8); 0.831 (2.9); 0.824 (2.7); 0.818 (2.8); 0.807 (0.8); 0.146 (1.2); 0.000 (251.1); −0.150 (1.2)

Example 54

[0665] .sup.1H-NMR (600.1 MHz, d.sub.6-DMSO): δ=9.330 (3.4); 8.717 (13.4); 8.680 (7.0); 8.325 (3.8); 8.324 (3.6); 3.967 (16.0); 3.898 (0.4); 3.833 (0.9); 3.821 (3.2); 3.809 (3.3); 3.796 (1.0); 3.336 (112.1); 2.615 (0.4); 2.524 (0.6); 2.521 (0.8); 2.518 (0.8); 2.509 (18.5); 2.506 (39.7); 2.503 (54.3); 2.500 (39.2); 2.497 (18.5); 2.387 (0.3); 2.074 (1.2); 1.233 (3.7); 1.220 (8.0); 1.208 (3.5); 0.000 (0.7)

Example 55

[0666] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.324 (4.2); 8.954 (3.0); 8.933 (3.8); 8.776 (39); 8.755 (3.2); 8.361 (4.4); 8.313 (0.8); 4.000 (0.6); 3.984 (16.0); 3.925 (1.0); 3.906 (3.5); 3.888 (3.6); 3.869 (1.1); 3.773 (0.6); 3.371 (0.3); 3.318 (331.2); 2.891 (0.5); 2.732 (0.4); 2.675 (1.6); 2.670 (2.3); 2.666 (1.6); 2.506 (292.7); 2.501 (386.8); 2.497 (282.1); 2.332 (1.7); 2.328 (2.3); 2.323 (1.6); 1.274 (3.8); 1.255 (8.3); 1.237 (4.1); 1.218 (0.5); 1.199 (0.5); 0.008 (0.6); 0.000 (17.8)

Example 56

[0667] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.313 (4.2); 8.868 (0.5); 8.846 (0.7); 8.838 (3.2); 8.816 (3.6); 8.511 (3.6); 8.489 (3.8); 8.468 (0.6); 8.335 (4.5); 8.313 (0.8); 5.245 (1.3); 5.208 (2.7); 5.171 (1.4); 3.980 (3.3); 3.971 (16.0); 3.877 (1.4); 3.860 (3.6); 3.841 (3.5); 3.823 (1.0); 3.759 (0.5); 3.315 (125.4); 2.675 (1.3); 2.670 (1.7); 2.666 (1.3); 2.506 (228.0); 2.501 (294.9); 2.497 (216.3); 2.332 (1.3); 2.328 (1.8); 2.324 (1.3); 2.116 (0.7); 1.252 (3.7); 1.242 (2.0); 1.234 (8.3); 1.224 (1.2); 1.215 (3.6); 0.000 (6.2)

Example 57

[0668] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.245 (3.9); 8.247 (4.2); 8.246 (4.1); 8.058 (2.8); 8.035 (3.1); 7.249 (2.6); 7.225 (2.5); 4.059 (2.9); 4.053 (3.0); 4.048 (3.3); 4.042 (2.9); 4.035 (3.0); 3.879 (16.0); 3.618 (0.9); 3.599 (3.2); 3.581 (3.3); 3.563 (1.0); 3.320 (186.3); 2.688 (3.1); 2.680 (3.2); 2.675 (3.9); 2.671 (3.8); 2.664 (3.2); 2.524 (1.8); 2.511 (46.8); 2.506 (99.5); 2.502 (134.4); 2.497 (96.8); 2.493 (46.1); 2.333 (0.6); 2.328 (0.8); 2.324 (0.6); 2.073 (4.3); 1.187 (3.4); 1.169 (7.7); 1.151 (3.3); 0.008 (0.4); 0.000 (14.1); −0.008 (0.6)

Example 58

[0669] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.322 (4.9); 9.269 (0.6); 8.761 (2.3); 8.739 (3.8); 8.684 (3.9); 8.662 (2.2); 8.330 (5.2); 8.313 (0.5); 8.288 (0.7); 7.902 (0.4); 7.880 (0.3); 5.753 (0.8); 4.316 (0.9); 4.037 (0.4); 4.019 (0.4); 4.012 (0.3); 3.964 (15.4); 3.833 (2.3); 3.813 (1.8); 3.794 (4.1); 3.776 (3.9); 3.757 (1.4); 3.693 (2.1); 3.500 (0.4); 3.443 (15.7); 3.320 (127.9); 3.091 (0.4); 2.671 (1.7); 2.648 (0.6); 2.615 (0.8); 2.505 (219.7); 2.502 (224.7); 2.463 (5.1); 2.383 (16.0); 2.327 (1.4); 2.086 (0.3); 1.988 (0.5); 1.352 (0.7); 1.335 (0.6); 1.297 (1.2); 1.258 (1.9); 1.235 (7.7); 1.216 (9.1); 1.198 (4.4); 1.175 (0.7); 1.156 (0.5); 0.857 (0.6); 0.854 (0.7); 0.835 (0.5); −0.001 (10.9)

Example 59

[0670] .sup.1H-NMR (601.6 MHz, d.sub.6-DMSO): δ=9.368 (3.6); 8.850 (1.9); 8.843 (2.0); 8.674 (3.3); 8.660 (3.7); 8.369 (3.7); 8.358 (4.3); 8.357 (4.1); 8.354 (3.7); 8.163 (1.8); 8.156 (1.9); 3.990 (16.0); 3.843 (1.0); 3.831 (3.3); 3.818 (3.4); 3.806 (1.0); 3.312 (89.1); 2.613 (0.4); 2.522 (0.6); 2.519 (0.8); 2.516 (0.8); 2.507 (21.2); 2.504 (45.8); 2.501 (63.2); 2.498 (45.4); 2.495 (21.2); 2.385 (0.4); 1.241 (3.7); 1.229 (8.1); 1.217 (3.6); 0.000 (1.8)

Example 60

[0671] .sup.1H-NMR (601.6 MHz, d.sub.6-DMSO): δ=9.330 (3.4); 8.770 (3.9); 8.685 (3.3); 8.671 (3.8); 8.382 (3.7); 8.367 (3.5); 8.323 (3.6); 8.311 (0.4); 8.017 (4.3); 4.454 (5.6); 3.975 (16.0); 3.802 (1.0); 3.790 (3.2); 3.777 (3.3); 3.765 (1.0); 3.310 (51.9); 2.940 (12.9); 2.613 (0.9); 2.522 (1.5); 2.519 (1.8); 2.516 (1.7); 2.507 (41.6); 2.504 (91.4); 2.501 (127.9); 2.498 (92.0); 2.495 (42.4); 2.388 (0.6); 2.385 (0.9); 1.233 (3.6); 1.221 (8.1); 1.208 (3.6); 0.096 (1.2); 0.005 (8.0); 0.000 (294.6); −0.006 (9.5); −0.100 (1.2)

Example 61

[0672] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.302 (4.0); 8.641 (3.5); 8.619 (4.1); 8.347 (4.1); 8.325 (3.8); 8.312 (4.3); 8.310 (4.3); 3.954 (16.0); 3.803 (0.9); 3.784 (3.2); 3.766 (3.3); 3.747 (1.0); 3.318 (120.7); 2.676 (0.5); 2.671 (0.7); 2.666 (0.5); 2.557 (15.6); 2.524 (1.7); 2.511 (36.9); 2.506 (77.6); 2.502 (108.4); 2.497 (80.6); 2.493 (38.6); 2.333 (0.5); 2.329 (0.7); 2.324 (0.5); 2.297 (14.9); 2.073 (0.9); 1.237 (3.5); 1.219 (7.9); 1.200 (3.3); 0.008 (0.4); 0.000 (10.4); −0.009 (0.4)

Example 62

[0673] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.344 (4.6); 8.978 (5.9); 8.695 (3.1); 8.673 (3.6); 8.365 (3.6); 8.343 (3.4); 8.328 (4.9); 8.312 (0.7); 8.152 (5.8); 4.070 (0.6); 4.001 (16.0); 3.864 (1.1); 3.845 (3.5); 3.827 (3.5); 3.808 (1.1); 3.316 (165.7); 2.671 (1.3); 2.506 (147.6); 2.502 (199.6); 2.497 (159.9); 2.328 (1.2); 2.324 (1.0); 1.252 (3.6); 1.234 (7.9); 1.215 (3.6); 0.000 (22.1)

Example 63

[0674] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.341 (4.3); 8.911 (5.9); 8.910 (5.7); 8.685 (3.4); 8.663 (3.9); 8.345 (3.9); 8.330 (4.6); 8.323 (3.9); 8.105 (5.7); 3.997 (16.0); 3.858 (1.0); 3.840 (3.3); 3.821 (3.4); 3.803 (1.0); 3.318 (72.6); 2.675 (0.4); 2.671 (0.5); 2.667 (0.4); 2.524 (1.2); 2.51 (28.0); 2.507 (58.3); 2.502 (81.1); 2.498 (61.6); 2.494 (30.8); 2.334 (0.4); 2.329 (0.5); 2.324 (0.4); 1.250 (3.5); 1.232 (8.0); 1.213 (3.5); 0.000 (1.9)

Example 64

[0675] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.343 (4.4); 9.006 (5.8); 8.697 (3.4); 8.675 (3.9); 8.378 (3.9); 8.356 (3.5); 8.330 (4.6); 8.195 (5.8); 4.265 (7.0); 4.005 (16.0); 3.872 (1.0); 3.854 (3.3); 3.835 (3.4); 3.817 (1.0); 3.319 (143.3); 2.675 (0.5); 2.671 (0.7); 2.666 (0.6); 2.524 (1.8); 2.510 (41.0); 2.506 (85.3); 2.502 (119.2); 2.497 (91.2); 2.493 (46.0); 2.333 (0.5); 2.329 (0.7); 2.324 (0.5); 1.254 (3.5); 1.236 (8.0); 1.217 (3.5); 0.000 (2.9)

Example 65

[0676] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.360 (4.8); 9.340 (4.8); 8.773 (3.2); 8.751 (3.6); 8.420 (3.7); 8.399 (3.3); 8.344 (50); 8.314 (0.5); 4.010 (16.0); 3.900 (1.0); 3.882 (3.5); 3.864 (3.6); 3.845 (1.1); 3.315 (177.0); 2.670 (2.0); 2.505 (228.2); 2.501 (320.6); 2.497 (261.4); 2.328 (1.9); 1.255 (3.6); 1.236 (8.0); 1.218 (3.6); 0.000 (5.0)

Example 67

[0677] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.312 (4.2); 8.765 (3.3); 8.743 (3.9); 430 (39); 8.408 (3.5); 8.327 (4.5); 8313 (0.3); 3.972 (15.8); 3.853 (0.9); 3.835 (3.3); 3.816 (3.4); 3.798 (1.0); 3.317 (69.7); 3.317 (69.7); 2.671 (0.7); 2.667 (0.5); 2.625 (16.0); 2.524 (1.8); 2.511 (38.2); 2.506 (79.2); 2.502 (110.2); 2.497 (84.8); 2.493 (43.2); 2.333 (0.5); 2.329 (0.7); 2.324 (0.5); 2.073 (0.6); 1.251 (3.5); 1.233 (8.0); 1.214 (3.5); 0.000 (9.0); −0.008 (0.4)

Example 68

[0678] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.361 (4.8); 9.309 (4.3); 8.765 (3.3); 8.743 (3.8); 8.437 (3.7); 8.415 (3.3); 8.343 (5.1); 4.012 (16.0); 3.906 (1.1); 3.887 (3.5); 3.869 (3.6); 3.850 (1.1); 3.317 (69.3); 2.671 (0.7); 2.506 (81.4); 2.502 (109.2); 2.329 (0.6); 1.259 (3.8); 1.241 (8.3); 1.223 (3.7); 0.000 (4.9)

Example 69

[0679] .sup.1H-NMR (601.6 MHz, CD3CN): δ=9.120 (2.7); 8.549 (2.6); 8.534 (3.8); 8.532 (04); 8.471 (3.8); 8.457 (2.5); 8.189 (2.8); 8.188 (2.8); 4.525 (2.1); 4.522 (0.5); 4.516 (2.8); 4.509 (0.5); 4.506 (2.2); 4.087 (0.5); 3.929 (0.5); 3.918 (1.1); 3.911 (16.0); 3.881 (0.4); 3.758 (1.1); 3.745 (3.6); 3.733 (3.7); 3.721 (1.2); 3.534 (8.5); 3.074 (1.9); 3.064 (2.6); 3.054 (1.9); 2.209 (1.3); 1.997 (2.6); 1.989 (1.0); 1.985 (1.0); 1.981 (6.5); 1.977 (10.8); 1.973 (14.6); 1.969 (9.5); 1.965 (4.8); 1.348 (0.3); 1.306 (3.8); 1.299 (0.7); 1.294 (8.0); 1.287 (0.8); 1.282 (3.7); 1.275 (0.5)

Example 70

[0680] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.340 (4.1); 8.892 (5.6); 8.657 (3.4); 8.635 (3.9); 8.325 (4.3); 8.323 (4.3); 8.313 (1.0); 8.294 (3.9); 8.272 (3.6); 3.988 (16.0); 3.964 (0.4); 3.853 (1.0); 3.834 (3.3); 3.816 (3.4); 3.797 (1.0); 3.554 (0.4); 3.379 (0.3); 3.321 (238.7); 2.675 (1.6); 2.670 (2.2); 2.666 (1.7); 2.573 (0.7); 2.524 (7.0); 2.510 (127.0); 2.506 (259.7); 2.501 (358.0); 2.497 (273.1); 2.493 (137.3); 2.329 (15.3); 1.247 (3.5); 1.228 (7.9); 1.210 (3.4); 0.008 (1.1); 0.000 (31.9); −0.008 (1.3)

Example 71

[0681] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.334 (3.7); 8.875 (3.1); 8.854 (4.0); 8.830 (1.3); 8.829 (1.3); 8.819 (1.4); 8.817 (1.3); 8.815 (1.2); 8.702 (3.9); 8.681 (3.2); 8.452 (1.9); 8.432 (2.1); 8.328 (3.9); 8.313 (0.7); 8.037 (0.9); 8.033 (0.9); 8.018 (1.5); 8.013 (1.5); 7.998 (0.9); 7.994 (0.9); 7.621 (1.0); 7.618 (1.1); 7.609 (1.0); 7.606 (1.1); 7.602 (1.0); 7.599 (0.9); 7.590 (0.9); 7.588 (0.9); 5.754 (2.2); 3.978 (16.0); 3.908 (0.5); 3.862 (1.0); 3.844 (3.3); 3.825 (3.4); 3.807 (1.0); 3.316 (172.2); 2.680 (0.5); 2.675 (1.1); 2.671 (1.5); 2.666 (1.1); 2.541 (2.9); 2.524 (3.5); 2.519 (5.3); 2.511 (83.4); 2.506 (176.1); 2.502 (237.1); 2.497 (171.3); 2.492 (82.3); 2.337 (0.5); 2.333 (1.0); 2.328 (1.4); 2.324 (1.0); 1.254 (3.6); 1.235 (8.4); 1.217 (3.6); 1.198 (0.4); 1.180 (0.4); 0.146 (0.9); 0.008 (6.5); 0.000 (210.7); −0.008 (7.2); −0.150 (0.9)

Example 72

[0682] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.399 (2.5); 9.394 (2.6); 9.322 (4.2); 8.763 (1.7); 8.760 (1.9); 8.752 (1.8); 8.748 (1.8); 8.655 (0.5); 8.634 (7.4); 8.631 (7.3); 8.610 (0.5); 8.596 (1.0); 8.591 (1.4); 8.586 (1.0); 8.576 (1.0); 8.570 (1.5); 8.566 (1.0); 8.321 (4.4); 7.624 (1.3); 7.612 (1.3); 7.604 (1.3); 7.592 (1.2); 5.754 (3.3); 3.975 (16.0); 3.860 (1.0); 3.841 (3.4); 3.823 (3.5); 3.804 (1.0); 3.320 (93.9); 2.675 (0.6); 2.671 (0.9); 2.666 (0.7); 2.541 (1.0); 2.506 (105.6); 2.502 (139.9); 2.497 (105.2); 2.333 (0.6); 2.329 (0.9); 2.324 (0.7); 1.258 (3.8); 1.240 (8.3); 1.221 (3.8); 0.146 (0.5); 0.008 (4.7); 0.000 (102.8); −0.150 (0.5)

Example 73

[0683] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=11.446 (1.0); 9.293 (4.5); 8.324 (3.1); 8.313 (0.3); 8.302 (3.8); 8.292 (4.7); 8.074 (3.4); 8.053 (3.0); 7.715 (2.0); 7.712 (2.0); 7.709 (1.9); 6.915 (1.0); 6.909 (2.0); 6.904 (2.1); 6.898 (1.0); 6.756 (2.0); 6.752 (2.0); 5.754 (1.6); 3.987 (1.0); 3.914 (16.0); 3.748 (1.0); 3.729 (3.5); 3.711 (3.6); 3.693 (1.2); 3.325 (55.7); 3.321 (50.5); 2.675 (0.4); 2.671 (0.5); 2.666 (0.4); 2.541 (2.6); 2.507 (62.0); 2.502 (79.3); 2.498 (56.8); 2.333 (0.3); 2.329 (0.5); 2.324 (0.4); 1.220 (3.7); 1.201 (8.3); 1.183 (3.8); 0.859 (0.4); 0.008 (2.8); 0.000 (54.7); −0.008 (2.0)

Example 74

[0684] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.288 (4.7); 8.349 (2.6); 8.327 (3.4); 8.293 (50); 8.179 (3.3); 8.157 (2.6); 7.114 (2.5); 7.103 (3.7); 7.096 (3.4); 6.218 (1.8); 6.210 (2.4); 6.202 (1.8); 5.754 (2.4); 3.928 (15.8); 3.910 (16.0); 3.750 (1.2); 3.731 (3.6); 3.713 (3.6); 3.694 (1.2); 3.318 (29.0); 2.671 (0.4); 2.542 (1.5); 2.502 (55.4); 2.329 (0.4); 1.226 (3.9); 1.208 (8.1); 1.189 (3.7); 0.000 (34.1)

Example 75

[0685] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.333 (3.6); 8.725 (2.6); 8.718 (2.6); 8.672 (3.3); 8.650 (4.0); 8.384 (3.9); 8.362 (3.5); 8.329 (3.6); 8.327 (3.8); 8.314 (0.5); 8.013 (2.8); 8.010 (2.8); 6.691 (2.0); 6.687 (2.1); 6.684 (2.2); 6.680 (2.1); 5.754 (4.5); 3.984 (16.0); 3.908 (1.2); 3.833 (0.9); 3.815 (3.2); 3.796 (3.3); 3.778 (0.9); 3.316 (49.0); 2.675 (0.5); 2.670 (0.7); 2.666 (0.5); 2541 (0.6); 2.524 (1.6); 2.519 (2.6); 2.510 (42.9); 2.506 (91.9); 2.501 (124.6); 2.497 (89.3); 2.492 (42.1); 2.333 (0.5); 2.328 (0.7); 2.324 (0.5); 1.246 (3.6); 1.228 (8.1); 1.216 (0.7); 1.209 (3.4); 1.198 (0.7); 0.008 (0.7); 0.000 (23.8); −0.009 (0.8)

Example 76

[0686] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.315 (3.5); 8.641 (2.2); 8.638 (2.8); 8.636 (2.4); 8.526 (3.2); 8.505 (3.8); 8.313 (0.4); 8.307 (3.6); 8.305 (3.8); 8.262 (3.5); 8.241 (3.1); 7.885 (2.0); 7.881 (3.4); 7.877 (2.2); 7.197 (2.3); 7.195 (2.6); 7.192 (2.5); 7.190 (2.5); 5.754 (1.8); 3.929 (16.0); 3.803 (0.9); 3.785 (3.2); 3.766 (3.2); 3.748 (1.0); 3.319 (80.3); 2.675 (0.4); 2.671 (0.5); 2.666 (0.4); 2.524 (1.2); 2.520 (2.0); 2.511 (32.0); 2.506 (68.9); 2.502 (93.4); 2.497 (67.1); 2.493 (31.8); 2.333 (0.4); 2.329 (0.5); 2.324 (0.4); 1.233 (3.5); 1.214 (8.0); 1.196 (3.4); 0.008 (0.4); 0.000 (14.1); −0.009 (0.5)

Example 77

[0687] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.311 (4.1); 8.572 (2.4); 8.551 (4.2); 8.494 (4.0); 8.473 (2.4); 8.315 (4.5); 8.229 (3.9); 8.225 (4.1); 7.906 (4.0); 7.902 (4.0); 5.754 (2.9); 3.943 (16.0); 3.829 (1.0); 3.811 (3.4); 3.792 (3.5); 3.774 (1.0); 3.321 (87.4); 2.672 (0.4); 2.525 (1.1); 2.511 (25.6); 2.507 (53.0); 2.502 (71.3); 2.498 (52.2); 2.494 (25.8); 2.329 (0.4); 1.243 (3.6); 1.224 (80); 1.206 (3.5); 0.000 (7.9); −0.008 (0.3)

Example 78

[0688] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=10.196 (0.8); 9.330 (3.8); 8.810 (3.9); 8.806 (2.5); 8.799 (2.5); 8.795 (4.2); 8.704 (0.8); 8.682 (6.0); 8.677 (5.7); 8.656 (0.7); 8.326 (4.0); 8.313 (0.7); 8.181 (4.3); 8.177 (2.7); 8.169 (2.5); 8.165 (4.1); 4.517 (0.4); 3.975 (16.0); 3.871 (1.0); 3.852 (3.4); 3.834 (3.4); 3.815 (1.0); 3.318 (226.9); 2.675 (1.3); 2.670 (1.9); 2.666 (1.4); 2.524 (4.5); 2.510 (108.7); 2.506 (230.6); 2.501 (310.5); 2.497 (222.3); 2.492 (104.7); 2.333 (1.3); 2.328 (1.8); 2.324 (1.4); 2.086 (5.7); 1.258 (3.5); 1.239 (8.1); 1.221 (3.4); 0.000 (3.5)

Example 79

[0689] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.311 (4.1); 8.519 (2.6); 8.498 (4.6); 8.443 (3.7); 8.421 (2.2); 8.316 (4.3); 8.314 (4.5); 8.157 (2.1); 8.147 (2.1); 7.888 (1.8); 7.886 (2.2); 7.875 (1.9); 7.873 (2.3); 7.309 (2.1); 7.300 (2.1); 7.297 (2.2); 7.287 (2.0); 3.946 (16.0); 3.818 (0.9); 3.800 (3.2); 3.781 (3.3); 3.763 (1.0); 3.346 (52.5); 3.336 (38.8); 3.334 (38.9); 3.329 (34.0); 3.245 (0.3); 3.227 (0.4); 3.220 (03); 3215 (0.3); 2.673 (0.4); 2.526 (0.8); 2.521 (1.3); 2.512 (22.5); 2.508 (48.3); 2.503 (65.5); 2.499 (46.9); 2.494 (22.1); 2.330 (0.4); 2.087 (3.6); 1.308 (0.4); 1.299 (0.5); 1.291 (1.0); 1.281 (0.9); 1.273 (1.0); 1.262 (0.5); 1.255 (0.4); 1.242 (3.7); 1.224 (8.5); 1.205 (3.6); 0.000 (0.4)

Example 80

[0690] .sup.1H-NMR (400.0 MHz, ds-DMSO): δ=9.308 (3.6); 8.557 (3.4); 8.535 (3.9); 8.312 (3.8); 8.310 (3.9); 8.221 (3.6); 8.199 (3.3); 8.049 (2.3); 8.048 (2.7); 8.045 (2.7); 8.043 (2.6); 7.467 (2.2); 7.466 (2.4); 7.459 (2.3); 7.457 (2.4); 6.787 (2.2); 6.783 (2.1); 6.779 (2.1); 6.774 (2.1); 3.924 (16.0); 3.791 (0.9); 3.772 (3.2); 3.754 (3.3); 3.735 (1.0); 3.322 (81.1); 2.671 (0.4); 2.525 (1.0); 2.520 (1.5); 2.511 (25.1); 2.507 (54.2); 2.502 (73.7); 2.498 (52.7); 2.493 (24.7); 2.329 (0.4); 2.086 (13.4); 1.228 (3.4); 1.209 (7.8); 1.191 (3.3); 0.000 (0.4)

Example 81

[0691] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.302 (2.8); 8.523 (2.4); 8.501 (3.0); 8.324 (2.8); 8.313 (0.4); 8.303 (4.7); 7.954 (5.4); 7.644 (0.5); 7.632 (0.4); 7.627 (0.8); 7.624 (0.6); 7.615 (0.6); 7.598 (0.6); 7.594 (0.4); 7.574 (0.4); 7.566 (0.5); 7.556 (0.4); 7.551 (0.4); 7.548 (0.5); 3.987 (1.2); 3.969 (0.4); 3.938 (12.0); 3.921 (1.3); 3.891 (13.8); 3.797 (0.7); 3.778 (2.4); 3.760 (2.4); 3.742 (0.7); 3.321 (81.8); 2.675 (0.4); 2.671 (0.6); 2.666 (0.4); 2.524 (1.2); 2.520 (1.9); 2.511 (31.8); 2.507 (69.1); 2.502 (94.3); 2.497 (68.0); 2.493 (32.3); 2.333 (0.4); 2.329 (0.5); 2.324 (0.4); 2.086 (16.0); 1.237 (2.7); 1.218 (6.1); 1.200 (2.6); 1.185 (0.6); 0.000 (0.8)

Example 82

[0692] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.286 (3.9); 8.347 (2.9); 8.325 (3.8); 8.313 (0.5); 8.291 (4.1); 8.177 (3.6); 8.156 (2.8); 7.117 (1.3); 7.113 (2.2); 7.107 (1.4); 7.103 (2.8); 7.094 (2.5); 6.217 (1.8); 6.211 (1.9); 6.207 (1.9); 6.201 (1.8); 5.753 (5.4); 3.926 (16.0); 3.909 (15.8); 3.748 (1.0); 3.729 (3.3); 3.711 (3.3); 3.693 (1.0); 3.317 (102.7); 2.675 (0.6); 2.670 (0.8); 2.666 (0.6); 2.524 (1.8); 2.519 (2.8); 2.510 (49.1); 2.506 (104.4); 2.501 (140.7); 2.497 (100.5); 2.492 (47.6); 2.333 (0.6); 2.328 (0.9); 2.324 (0.6); 1.225 (3.5); 1.206 (8.0); 1.188 (3.4); 0.146 (0.9); 0.008 (6.9); −0.001 (205.1); −0.009 (7.1); −0.150 (0.9)

Example 83

[0693] .sup.1H-NMR (400.0 MHz, ds-DMSO): δ=9.313 (3.7); 8.543 (4.3); 8.451 (3.3); 8.430 (3.9); 8.301 (4.0); 8.299 (4.1); 8.203 (4.7); 8.201 (5.0); 8.158 (3.7); 8.137 (3.3); 7.644 (0.8); 7.632 (0.7); 7.627 (1.5); 7.624 (1.2); 7.615 (1.1); 7.597 (1.3); 7.594 (0.7); 7.574 (0.9); 7.566 (1.0); 7.559 (0.6); 7.557 (0.7); 7.551 (0.8); 7.549 (0.9); 7.537 (0.3); 7.530 (0.4); 5.753 (2.6); 3.922 (16.0); 3.906 (14.7); 3.774 (0.9); 3.756 (3.2); 3.737 (3.3); 3.719 (1.0); 3.330 (76.9); 3.325 (61.7); 2.676 (0.5); 2.671 (0.7); 2.667 (0.5); 2.525 (1.5); 2.520 (2.3); 2511 (38.4); 2.507 (82.6); 2.502 (111.9); 2.498 (80.2); 2.493 (37.9); 2493 (379); 334 (0.5); 2.329 (0.7); 2.324 (0.5); 1.226 (3.5); 1.207 (8.0); 1.189 (3.4); 0.146 (0.6); 0.008 (4.9); 0.000 (150.3); −0.009 (5.1); −0.150 (0.6)

Example 84

[0694] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=13.389 (1.3); 9.311 (4.1); 8.600 (0.4); 8.451 (3.2); 8.430 (3.9); 8.313 (0.5); 8300 (4.4); 8.237 (0.4); 8.210 (3.8); 8.188 (3.2); 3.928 (16.0); 3.778 (0.9); 3.760 (3.3); 3.742 (3.3); 3.723 (1.0); 3.319 (128.4); 2.675 (0.5); 2.671 (0.7); 2.666 (0.5); 2.524 (1.7); 2.511 (37.8); 2.506 (79.9); 2.502 (111.9); 2.497 (83.4); 2.493 (40.0); 2.333 (0.5); 2.329 (0.7); 2.324 (0.5); 1.228 (3.4); 1.209 (7.9); 1.191 (3.3); 0.008 (0.3); 0.000 (10.9); −0.009 (0.4)

Example 85

[0695] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=19.962 (0.3); 14435 (0.14435 (3); 9315 (3.9); 8.697 (1.9); 8.675 (5.4); 8.655 (5.2); 8.634 (1.8); 8.571 (1.1); 8.550 (1.7); 8.494 (1.8); 8.473 (1.2); 8.336 (0.3); 8.322 (3.9); 8.314 (4.7); 8.230 (1.6); 8.226 (1.7); 7.991 (4.0); 7.978 (4.1); 7.906 (1.7); 7.903 (1.6); 7.324 (4.1); 7.311 (3.7); 5.754 (6.0); 3.988 (0.9); 3.962 (16.0); 3.942 (6.8); 3.855 (0.9); 3.837 (3.2); 3.818 (3.4); 3.810 (1.6); 3.801 (1.2); 3.791 (1.6); 3.771 (0.5); 3.316 (650.0); 2.679 (2.5); 2.675 (5.3); 2.670 (7.5); 2.666 (5.4); 2.661 (2.6); 2.554 (0.9); 2.523 (18.3); 2519 (29.8); 2.510 (447.8); 2.506 (945.9); 2.501 (1274.8); 2.497 (917.0); 2.492 (437.5); 2.404 (0.5); 2.394 (0.4); 2.365 (0.4); 2.337 (2.6); 2.332 (5.4); 2.328 (7.4); 2323 (5.4); 2.319 (2.7); 1.419 (0.3); 1.334 (0.5); 1.285 (0.4); 1.264 (0.5); 1.250 (3.9); 1.241 (2.3); 1.232 (9.1); 1.223 (4.0); 1.213 (3.7); 1.204 (1.8); 0.994 (0.3); 0.854 (0.4); 0.826 (0.4); 0.146 (7.4); 0.138 (0.4); 0.025 (0.8); 0.008 (60.1); 0.000 (1746.6); −0.008 (69.7); −0.064 (0.9); −0.085 (0.5); −0.095 (0.4); −0.150 (7.6)

Example 86

[0696] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.309 (4.5); 8.546 (2.6); 8.525 (4.2); 8.458 (4.0); 8.437 (2.5); 8.313 (5.1); 8.079 (3.4); 8.069 (3.5); 7.350 (3.7); 7.339 (3.6); 5.754 (7.4); 3.943 (16.0); 3.828 (1.0); 3.810 (3.5); 3.791 (3.6); 3.773 (1.1); 3.317 (51.7); 2.671 (0.6); 2.506 (77.0); 2502 (103.4); 2.498 (78.9); 2.329 (0.6); 2.324 (0.5); 1.241 (3.6); 1.223 (8.0); 1.204 (3.5); 0.000 (36.4); −0.008 (1.6)

Example 87

[0697] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.321 (6.2); 9.312 (4.6); 8.931 (5.9); 8.605 (1.6); 8.584 (4.9); 8.565 (4.7); 8.543 (1.6); 8.317 (5.0); 7.644 (0.6); 7.626 (1.2); 7.614 (0.9); 7.597 (0.9); 7.574 (0.7); 7.566 (0.8); 7.556 (0.6); 7.548 (0.7); 5755 (0.8); 3.938 (16.0); 3.827 (1.1); 3.808 (3.5); 3.790 (3.5); 3.771 (1.1); 3.316 (99.4); 2.670 (1.7); 2.505 (205.8); 2.501 (278.7); 2.497 (215.7); 2.328 (1.6); 2.324 (1.3); 1.468 (0.7); 1.242 (3.7); 1.224 (8.0); 1.206 (3.6); 0.000 (45.2); −0.008 (1.9)

Example 88

[0698] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): δ=9.308 (4.6); 8.662 (3.1); 8.654 (0.5); 8.641 (3.7); 8.633 (0.5); 8.440 (3.8); 8.432 (0.7); 8.419 (3.2); 8.411 (0.4); 8.314 (5.2); 7.719 (7.3); 7.710 (0.9); 7.438 (0.5); 7.417 (0.6); 7.396 (0.6); 7.331 (0.6); 7.314 (0.8); 7.296 (0.4); 5.755 (7.1); 5.746 (0.8); 3.949 (16.0); 3.851 (1.1); 3.833 (3.6); 3.814 (3.7); 3.796 (1.2); 3.318 (68.1); 3.310 (9.1); 2.675 (0.7); 2.671 (0.8); 2.506 (113.3); 2.502 (135.3); 2.498 (102.2); 2.333 (0.7); 2.329 (0.8); 2.324 (0.6); 1.248 (3.8); 1.229 (8.2); 1.222 (1.8); 1.211 (3.6); 0.000 (20.9); −0.008 (3.0)

Use Examples

[0699] Phaedon cochleariae—Spray Test

[0700] Solvent: 78.0 parts by weight of acetone [0701] 1.5 parts by weight of dimethylformamide

[0702] Emulsifier: alkylaryl polyglycol ether

[0703] To produce a suitable preparation of active compound, 1 part by weight of active compound is dissolved using the stated parts by weight of solvent and made up with water containing an emulsifier concentration of 1000 ppm until the desired concentration is attained. To produce further test concentrations, the preparation is diluted with emulsifier-containing water.

[0704] Discs of Chinese cabbage leaves (Brassica pekinensis) are sprayed with an active compound preparation of the desired concentration and, after drying, populated with larvae of the mustard beetle (Phaedon cochleariae).

[0705] After 7 days, the efficacy in % is determined. 100% means that all the beetle larvae have been killed; 0% means that no beetle larvae have been killed.

[0706] In this test, for example, the following compounds from the preparation examples show an efficacy of 100% at an application rate of 500 g/ha: 2, 3, 4, 5, 6, 8, 9, 11, 13, 14, 15, 16, 17, 18, 19, 22, 23, 25, 26, 27, 29, 30, 32, 33, 35, 36, 38, 39, 40, 42, 46, 47, 49, 49, 50, 52, 53, 55, 56, 59, 60, 71, 73, 75, 78, 81, 83

[0707] In this test, for example, the following compounds from the preparation examples show an efficacy of 83% at an application rate of 500 g/ha: 48, 58, 84

[0708] In this test, for example, the following compounds from the preparation examples show an efficacy of 100% at an application rate of 100 g/ha: 28

[0709] In this test, for example, the following compounds from the preparation examples show an efficacy of 83% at an application rate of 100 g/ha: 72 In this test, for example, the following compounds from the preparation examples show an efficacy of 83% at an application rate of 20 g/ha: 21

Spodoptera frugiperda—Spray Test

[0710] Solvent: 78.0 parts by weight of acetone [0711] 1.5 parts by weight of dimethylformamide

[0712] Emulsifier: alkylaryl polyglycol ether

[0713] To produce a suitable preparation of active compound, 1 part by weight of active compound is dissolved using the stated parts by weight of solvent and made up with water containing an emulsifier concentration of 1000 ppm until the desired concentration is attained. To produce further test concentrations, the preparation is diluted with emulsifier-containing water.

[0714] Leaf discs of maize (Zea mays) are sprayed with an active compound preparation of the desired concentration and, after drying, populated with caterpillars of the armyworm (Spodoptera frugiperda).

[0715] After 7 days, the efficacy in % is determined. 100% means that all the caterpillars have been killed; 0% means that no caterpillars have been killed.

[0716] In this test, for example, the following compounds from the preparation examples show an efficacy of 100% at an application rate of 500 g/ha: 8, 13, 16, 17, 19, 22, 24, 25, 26, 30, 36, 46, 48, 53, 55, 56, 59, 71, 75, 77, 83, 84, 85

[0717] In this test, for example, the following compounds from the preparation examples show an efficacy of 83% at an application rate of 500 g/ha: 15, 81

[0718] In this test, for example, the following compounds from the preparation examples show an efficacy of 100% at an application rate of 100 g/ha: 6, 21, 28

[0719] In this test, for example, the following compounds from the preparation examples show an efficacy of 83% at an application rate of 100 g/ha: 9

Myzus persicae—Spray Test

[0720] Solvent: 78 parts by weight of acetone [0721] 1.5 parts by weight of dimethylformamide

[0722] Emulsifier: alkylaryl polyglycol ether

[0723] To produce a suitable preparation of active compound, 1 part by weight of active compound is dissolved using the stated parts by weight of solvent and made up with water containing an emulsifier concentration of 1000 ppm until the desired concentration is attained. To produce further test concentrations, the preparation is diluted with emulsifier-containing water.

[0724] Discs of Chinese cabbage leaves (Brassica pekinensis) infested by all stages of the green peach aphid (Myzus persicae) are sprayed with an active compound preparation of the desired concentration.

[0725] After 6 days, the efficacy in % is determined. 100% means that all the aphids have been killed; 0% means that no aphids have been killed.

[0726] In this test, for example, the following compounds from the preparation examples show an efficacy of 100% at an application rate of 500 g/ha: 8, 14, 16, 18, 32, 50, 56

[0727] In this test, for example, the following compounds from the preparation examples show an efficacy of 90% at an application rate of 500 g/ha: 2, 3, 4, 5, 10, 12, 15, 17, 19, 23, 29, 30, 33, 35, 40, 42, 49, 52, 53, 55, 72, 73, 81, 83

[0728] In this test, for example, the following compounds from the preparation examples show an efficacy of 90% at an application rate of 20 g/ha: 39

Tetranychus urticae—Spray Test, OP-Resistant

[0729] Solvent: 78.0 parts by weight of acetone [0730] 1.5 parts by weight of dimethylformamide

[0731] Emulsifier: alkylaryl polyglycol ether

[0732] To produce a suitable preparation of active compound, 1 part by weight of active compound is dissolved using the stated parts by weight of solvent and made up with water containing an emulsifier concentration of 1000 ppm until the desired concentration is attained. To produce further test concentrations, the preparation is diluted with emulsifier-containing water.

[0733] Discs of bean leaves (Phaseolus vulgaris) infested with all stages of the greenhouse red spider mite (Tetranychus urticae) are sprayed with an active compound preparation of the desired concentration.

[0734] After 6 days, the efficacy in % is determined. 100% means that all the spider mites have been killed; 0% means that no spider mites have been killed.

[0735] In this test, for example, the following compounds from the preparation examples show an efficacy of 90% at an application rate of 500 g/ha: 5, 33, 40, 49, 80

[0736] In this test, for example, the following compounds from the preparation examples show an efficacy of 90% at an application rate of 100 g/ha: 78, 79

Boophilus microplus—Injection Test

[0737] Solvent: dimethyl sulphoxide

[0738] To produce a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of solvent and the concentrate is diluted with solvent to the desired concentration.

[0739] 1 μl of the active compound solution is injected into the abdomen of 5 engorged adult female cattle ticks (Boophilus microplus). The animals are transferred into dishes and kept in a climate-controlled room.

[0740] Efficacy is assessed after 7 days by laying of fertile eggs. Eggs which are not visibly fertile are stored in a climate-controlled cabinet until the larvae hatch after about 42 days. An efficacy of 100% means that none of the ticks has laid any fertile eggs; 0% means that all the eggs are fertile.

[0741] In this test, for example, the following compounds from the preparation examples show an efficacy of 100% at an application rate of 20 μg/animal: 17

[0742] In this test, for example, the following compounds from the preparation examples show an efficacy of 95% at an application rate of 20 μg/animal: 8, 30

[0743] In this test, for example, the following compounds from the preparation examples show an efficacy of 90% at an application rate of 20 μg/animal: 5, 36, 59

[0744] In this test, for example, the following compounds from the preparation examples show an efficacy of 80% at an application rate of 20 μg/animal: 22, 24, 25, 33

Lucilia cuprina Test

[0745] Solvent: dimethyl sulphoxide

[0746] To produce a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of dimethyl sulphoxide, and the concentrate is diluted with water to the desired concentration.

[0747] About 20 L1 larvae of the Australian sheep blowfly (Lucilia cuprina) are transferred into a test vessel containing minced horsemeat and the active compound preparation of the desired concentration.

[0748] After 2 days, the kill in % is determined. 100% means that all the larvae have been killed; 0% means that no larvae have been killed.

[0749] In this test, for example, the following compounds from the preparation examples show an efficacy of 100% at an application rate of 100 ppm: 2, 3, 4, 6, 8, 10, 11, 13, 14, 17, 18, 19, 20, 22, 23, 24, 25, 26, 28, 30, 35, 36, 53, 59

[0750] In this test, for example, the following compounds from the preparation examples show an efficacy of 95% at an application rate of 100 ppm: 60

[0751] In this test, for example, the following compounds from the preparation examples show an efficacy of 90% at an application rate of 100 ppm: 1

Ctenocephalides felis—Oral Test

[0752] Solvent: dimethyl sulphoxide

[0753] To produce a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of dimethyl sulphoxide. Dilution with citrated cattle blood gives the desired concentration.

[0754] About 20 unfed adult cat fleas (Ctenocephalides felis) are placed into a chamber which is closed at the top and bottom with gauze. A metal cylinder whose bottom end is closed with parafilm is placed onto the chamber. The cylinder contains the blood/active compound preparation, which can be imbibed by the fleas through the parafilm membrane.

[0755] After 2 days, the kill in % is determined. 100% means that all of the fleas have been killed; 0% means that none of the fleas have been killed.

[0756] In this test, for example, the following compounds from the preparation examples show an efficacy of 100% at an application rate of 100 ppm: 2, 3, 4, 11, 14, 18, 19, 22, 25, 33, 35, 36, 53, 59, 60

[0757] In this test, for example, the following compounds from the preparation examples show an efficacy of 98% at an application rate of 100 ppm: 1, 17, 28

[0758] In this test, for example, the following compounds from the preparation examples show an efficacy of 95% at an application rate of 100 ppm: 6, 8, 27

[0759] In this test, for example, the following compounds from the preparation examples show an efficacy of 80% at an application rate of 100 ppm: 13

Musca domestica Test

[0760] Solvent: dimethyl sulphoxide

[0761] To produce a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of dimethyl sulphoxide, and the concentrate is diluted with water to the desired concentration.

[0762] Vessels containing a sponge treated with sugar solution and the active compound preparation of the desired concentration are populated with 10 adult houseflies (Musca domestica).

[0763] After 2 days, the kill in % is determined. 100% means that all of the flies have been killed; 0% means that none of the flies have been killed.

[0764] In this test, for example, the following compounds from the preparation examples show an efficacy of 100% at an application rate of 100 ppm: 8, 13, 19

[0765] In this test, for example, the following compounds from the preparation examples show an efficacy of 95% at an application rate of 100 ppm: 59

[0766] In this test, for example, the following compounds from the preparation examples show an efficacy of 90% at an application rate of 100 ppm: 26

[0767] In this test, for example, the following compounds from the preparation examples show an efficacy of 85% at an application rate of 100 ppm: 36

[0768] In this test, for example, the following compounds from the preparation examples show an efficacy of 80% at an application rate of 100 ppm: 22, 24

[0769] In this test, for example, the following compounds from the preparation examples show an efficacy of 100% at an application rate of 20 ppm: 18

[0770] In this test, for example, the following compounds from the preparation examples show an efficacy of 85% at an application rate of 20 ppm: 17

Ctenocephalides felis—In Vitro Contact Tests with Adult Cat Fleas

[0771] For the coating of the test tubes, 9 mg of active compound are first dissolved in 1 ml of acetone p.a. and then diluted to the desired concentration with acetone p.a. 250 μl of the solution are distributed homogeneously on the inner walls and the base of a 25 ml test tube by turning and rocking on an orbital shaker (rocking rotation at 30 rpm for 2 h). With 900 ppm active compound solution and internal surface 44.7 cm.sup.2, given homogeneous distribution, an area-based dose of 5 μg/cm.sup.2 is achieved.

[0772] After the solvent has evaporated off, the tubes are populated with 5-10 adult cat fleas (Ctenocephalides felis), sealed with a perforated plastic lid and incubated in a horizontal position at room temperature and ambient humidity. After 48 h, efficacy is determined. To this end, the test tubes are stood upright and the fleas are knocked to the base of the tube. Fleas which remain motionless at the base or move in an uncoordinated manner are considered to be dead or moribund.

[0773] A substance shows good efficacy against Ctenocephalides felis if at least 80% efficacy was achieved in this test at an application rate of 5 μg/cm.sup.2. 100% efficacy means that all the fleas were dead or moribund. 0% efficacy means that no fleas were harmed.

[0774] In this test, for example, the following compounds from the preparation examples show an efficacy of 100% at an application rate of 5 μg/cm.sup.2 (500 g/ha): 8, 11, 14, 17, 18, 33

Rhipicephalus sanguineus—In Vitro Contact Tests with Adult Brown Dog Ticks

[0775] For the coating of the test tubes, 9 mg of active compound are first dissolved in 1 ml of acetone p.a. and then diluted to the desired concentration with acetone p.a. 250 μl of the solution are distributed homogeneously on the inner walls and the base of a 25 ml test tube by turning and rocking on an orbital shaker (rocking rotation at 30 rpm for 2 h). With 900 ppm active compound solution and internal surface 44.7 cm.sup.2, given homogeneous distribution, an area-based dose of 5 μg/cm.sup.2 is achieved.

[0776] After the solvent has evaporated off, the tubes are populated with 5-10 adult dog ticks (Rhipicephalus sanguineus), sealed with a perforated plastic lid and incubated in a horizontal position in the dark at room temperature and ambient humidity. After 48 h, efficacy is determined. To this end, the ticks are knocked to the floor of the tube and incubated on a hotplate at 45-50° C. for not more than 5 min. Ticks which remain motionless on the floor or move in such an uncoordinated manner that they are unable to deliberately avoid the heat by climbing upwards are considered to be dead or moribund.

[0777] A substance shows good activity against Rhipicephalus sanguineus if, in this test, an efficacy of at least 80% was achieved at an application rate of 5 μg/cm.sup.2. An efficacy of 100% means that all the ticks were dead or moribund. 0% efficacy means that none of the ticks had been harmed.

[0778] In this test, for example, the following compounds from the preparation examples show an efficacy of 100% at an application rate of 5 μg/cm.sup.2 (500 g/ha): 17

Meloidogyne incognita Test

[0779] Solvent: 125.0 parts by weight of acetone

[0780] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and the concentrate is diluted with water to the desired concentration.

[0781] Vessels are filled with sand, active compound solution, an egg/larvae suspension of the southern root-knot nematode (Meloidogyne incognita) and lettuce seeds. The lettuce seeds germinate and the plants develop. The galls develop on the roots.

[0782] After 14 days, the nematicidal efficacy in % is determined by the formation of galls. 100% means that no galls were found; 0% means that the number of galls on the treated plants corresponds to the untreated control.

[0783] In this test, for example, the following compounds from the preparation examples show an efficacy of 100% at an application rate of 20 ppm: 14, 81

Myzus persicae Spray Test

[0784] Solvent: 7 parts by weight of dimethylformamide

[0785] Emulsifier: alkylaryl polyglycol ether

[0786] To produce a suitable preparation of active compound, 1 part by weight of active compound is dissolved using the stated parts by weight of solvent and made up with water containing an emulsifier concentration of 1000 ppm until the desired concentration is attained. To produce further test concentrations, the preparation is diluted with emulsifier-containing water. If the addition of ammonium salts or/and penetrants is required, these are each added in a concentration of 1000 ppm to the formulation solution.

[0787] Bell pepper plants (Capsicum annuum) severely infested with the green peach aphid (Myzus persicae) are treated by spraying with the active compound preparation in the desired concentration.

[0788] After 6 days, the kill in % is determined. 100% means that all of the aphids have been killed; 0% means that none of the aphids have been killed.

[0789] In this test, for example, the following compounds from the preparation examples show an efficacy of 100% at an application rate of 100 ppm: 11

[0790] In this test, for example, the following compounds from the preparation examples show an efficacy of 95% at an application rate of 100 ppm: 1

Spodoptera frugiperda—Spray Test

[0791] Solvent: 7 parts by weight of dimethylformamide

[0792] Emulsifier: alkylaryl polyglycol ether

[0793] To produce a suitable preparation of active compound, 1 part by weight of active compound is dissolved using the stated parts by weight of solvent and made up with water containing an emulsifier concentration of 1000 ppm until the desired concentration is attained. To produce further test concentrations, the preparation is diluted with emulsifier-containing water. If the addition of ammonium salts or/and penetrants is required, these are each added in a concentration of 1000 ppm to the formulation solution.

[0794] Cotton leaves (Gossypium hirsutum) are sprayed with an active compound formulation of the desired concentration and populated with caterpillars of the armyworm (Spodoptera frugiperda).

[0795] After 7 days, the kill in % is determined. 100% means that all the caterpillars have been killed; 0% means that none of the caterpillars have been killed.

[0796] In this test, for example, the following compounds from the preparation examples show an efficacy of 100% at an application rate of 100 ppm: 14, 32

2-(HET)ARYL-SUBSTITUTED FUSED BICYCLIC HETEROCYCLE DERIVATIVES AS PESTICIDES

Inventors

Cpc classification

Classification Explorer

C07D471/04

CHEMISTRY; METALLURGY

Classification Explorer

C07D213/73

CHEMISTRY; METALLURGY

Classification Explorer

C07D498/04

CHEMISTRY; METALLURGY

Classification Explorer

C07D473/40

CHEMISTRY; METALLURGY

Classification Explorer

C07D487/04

CHEMISTRY; METALLURGY

Classification Explorer

A01N43/90

HUMAN NECESSITIES

Classification Explorer

C07D213/74

CHEMISTRY; METALLURGY

International classification

Classification Explorer

C07D498/04

CHEMISTRY; METALLURGY

Classification Explorer

C07D213/74

CHEMISTRY; METALLURGY

Classification Explorer

C07D487/04

CHEMISTRY; METALLURGY

Classification Explorer

A01N43/90

HUMAN NECESSITIES

Classification Explorer

C07D213/73

CHEMISTRY; METALLURGY

Classification Explorer

C07D471/04

CHEMISTRY; METALLURGY

Classification Explorer

C07D473/40

CHEMISTRY; METALLURGY

Abstract

Claims

Description