MESOIONIC IMIDAZOPYRIDINES AS INSECTICIDES

Abstract

Provided are compounds of the formula (I)

##STR00001##

which are suitable for controlling animal pests, including arthropods and in particular insects, arachnids and nematodes, and in which the structural elements R.sup.1, p, T, G and U have the meanings given in the description, as are processes for their preparation and their use as insecticides.

Claims

1. A compound of formula (I) ##STR00151## in which T represents hydrogen, C(R.sup.5a)(R.sup.5b)(R.sup.5c), C.sub.2-C.sub.8-alkenyl, C.sub.3-C.sub.8-alkynyl or C.sub.3-C.sub.8-cycloalkyl, where C.sub.2-C.sub.8-alkenyl, C.sub.3-C.sub.8-alkynyl and C.sub.3-C.sub.8-cycloalkyl may each optionally be mono- to trisubstituted and the substituents independently of one another are selected from the group consisting of halogen and/or may each optionally be monosubstituted and the substituent is selected from the group consisting of cyano, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylsulfonyl, aryl, hetaryl, aryl-C.sub.1-C.sub.6-alkyl and hetaryl-C.sub.1-C.sub.6-alkyl, where aryl, hetaryl, aryl-C.sub.1-C.sub.6-alkyl and hetaryl-C.sub.1-C.sub.6-alkyl for their part may each optionally be mono to trisubstituted and the substituents independently of one another are selected from the group consisting of halogen, cyano, nitro, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy and C.sub.1-C.sub.4-haloalkoxy, or T represents aryl, C.sub.1-C.sub.6-alkylenedioxyaryl, hetaryl, C.sub.3-C.sub.8-heterocyclyl, C.sub.3-C.sub.8-oxoheterocyclyl or C.sub.3-C.sub.8-dioxoheterocyclyl, where the radicals mentioned above may each optionally be mono- to pentasubstituted and the substituents independently of one another are selected from the group consisting of halogen, nitro, amino, cyano, SF.sub.5, SCN, C.sub.1-C.sub.6-alkylamino, di-(C.sub.1-C.sub.6-alkyl)amino, hydroxy, COOH, C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-heterocyclyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.3-C.sub.6-halocycloalkyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.1-C.sub.6-alkyl, 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.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyloxy, cyano-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.3-C.sub.6-alkynyl, SH, C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-alkylcarbonyl, C.sub.3-C.sub.6-cycloalkylcarbonyl, C.sub.2-C.sub.6-alkenylcarbonyl, C.sub.1-C.sub.6-haloalkylcarbonyl, C.sub.1-C.sub.6-alkoxycarbonyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylsulfonyl, C.sub.1-C.sub.6-alkylaminocarbonyl, di-(C.sub.1-C.sub.6)-alkylaminocarbonyl, tri-(C.sub.1-C.sub.6-alkyl)silyl, aryl, hetaryl, heterocyclyl, aryl-C.sub.1-C.sub.6-alkyl and hetaryl-C.sub.1-C.sub.6-alkyl, where aryl, hetaryl, aryl-C.sub.1-C.sub.6-alkyl and hetaryl-C.sub.1-C.sub.6-alkyl for their part may each optionally be mono- to trisubstituted and the substituents independently of one another are selected from the group consisting of halogen, cyano, nitro, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy and C.sub.1-C.sub.4-haloalkoxy, or T represents OR.sup.6, N(R.sup.7a)(R.sup.7b) or N(R.sup.8)N(R.sup.11a)(R.sup.11b) or T represents C(W)R.sup.12, C(O)OR.sup.13 or C(O)NR.sup.14aR.sup.14b W represents O or NOR.sup.15, G represents C(R.sup.9)(R.sup.10), U represents a cycle from the group consisting of U-1 to U-28, X.sup.a represents halogen, nitro, OH, cyano, SCN, SF.sub.5, C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.3-C.sub.6-halocycloalkyl, 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.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyloxy, cyano-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.3-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-alkylcarbonyl, C.sub.3-C.sub.6-cycloalkylcarbonyl, C.sub.2-C.sub.6-alkenylcarbonyl, C.sub.1-C.sub.6-haloalkylcarbonyl, C.sub.1-C.sub.6-alkoxycarbonyl, C.sub.1-C.sub.6-alkoxyimino-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylsulfonyl, C.sub.1-C.sub.6-alkylaminocarbonyl, di-(C.sub.1-C.sub.6)-alkylaminocarbonyl, aryl, hetaryl, aryl-C.sub.1-C.sub.6-alkyl or hetaryl-C.sub.1-C.sub.6-alkyl, where aryl, hetaryl, aryl-C.sub.1-C.sub.6-alkyl and hetaryl-C.sub.1-C.sub.6-alkyl may each be mono- to trisubstituted by halogen, cyano, nitro, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy or C.sub.1-C.sub.4-haloalkoxy, where the ring nitrogen atoms in U-17, U-18, U-19, U-26, U-27 and U-28 are not substituted by halogen, nitro, OH, cyano, SCN, SF.sub.5, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-alkylsulfinyl or C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyloxy, n represents 0, 1, 2 or 3, R.sup.1 in each case represents hydrogen, halogen, cyano, nitro, SF.sub.5, SCN, amino, C.sub.1-C.sub.6-alkylamino, di-(C.sub.1-C.sub.6)-alkylamino, hydroxy, COOH, C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.3-C.sub.6-halocycloalkyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.1-C.sub.6-alkyl, 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.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyloxy, cyano-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkenyloxy, C.sub.3-C.sub.6-alkynyl, C.sub.3-C.sub.6-alkynyloxy, SH, C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylthio, C.sub.1-C.sub.6-haloalkylsulfinyl, C.sub.1-C.sub.6-haloalkylsulfonyl, C.sub.1-C.sub.6-alkylcarbonyl, C.sub.3-C.sub.6-cycloalkylcarbonyl, C.sub.1-C.sub.6-haloalkylcarbonyl, C.sub.1-C.sub.6-alkoxyimino-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxycarbonyl, C.sub.1-C.sub.6-alkylaminocarbonyl, di-(C.sub.1-C.sub.6)-alkylaminocarbonyl, aryl, hetaryl, aryl-C.sub.1-C.sub.6-alkyl or hetaryl-C.sub.1-C.sub.6-alkyl, where aryl, hetaryl, aryl-C.sub.1-C.sub.6-alkyl and hetaryl-C.sub.1-C.sub.6-alkyl may each optionally be mono- or polysubstituted and the substituents independently of one another are selected from the group consisting of halogen, cyano, nitro, hydroxy, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, 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 and C.sub.1-C.sub.6-alkylthio, or two radicals R.sup.1 together form a 5- or 6-membered aliphatic, aromatic, heteroaromatic or heterocyclic ring which may optionally contain 1 to 2 atoms from the group consisting of O, S and N and which may optionally be mono- or polysubstituted, where the substituents independently of one another are selected from the group consisting of halogen and C.sub.1-C.sub.4-alkyl, p represents 0, 1, 2 or 3, R.sup.5a and R.sup.5b independently of one another represent hydrogen, halogen, cyano, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl or C.sub.1-C.sub.6-alkoxy, R.sup.5c represents hydrogen, fluorine, chlorine, bromine, cyano, C.sub.1-C.sub.6-alkoxycarbonyl, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy, C.sub.3-C.sub.8-cycloalkyl, C.sub.2-C.sub.6-alkenyl or C.sub.2-C.sub.6-alkynyl, where C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy, C.sub.3-C.sub.8-cycloalkyl, C.sub.2-C.sub.6-alkenyl and C.sub.2-C.sub.6-alkynyl may each optionally be mono to pentasubstituted and the substituents independently of one another are selected from the group consisting of halogen and/or may each optionally be monosubstituted and the substituent is selected from the group consisting of nitro, cyano, C.sub.1-C.sub.6-haloalkyl, 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-alkylthio, C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylsulfonyl, C.sub.1-C.sub.6-alkylcarbonylamino, C.sub.1-C.sub.6-alkylaminocarbonyl, di-(C.sub.1-C.sub.6-alkyl)aminocarbonyl, C.sub.1-C.sub.6-alkylcarbonyl, C.sub.1-C.sub.6-alkoxycarbonyl, C.sub.1-C.sub.6-alkoximino-C.sub.1-C.sub.6-alkyl, aryl, hetaryl and heterocyclyl, where aryl, hetaryl and heterocyclyl for their part may each optionally be mono- to trisubstituted and the substituents independently of one another are selected from the group consisting of halogen, nitro, cyano, C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.3-C.sub.6-halocycloalkyl, 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.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyloxy, cyano-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.3-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-alkylcarbonyl, C.sub.3-C.sub.6-cycloalkylcarbonyl, C.sub.2-C.sub.6-alkenylcarbonyl, C.sub.1-C.sub.6-haloalkylcarbonyl, C.sub.1-C.sub.6-alkoxycarbonyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylsulfonyl, C.sub.1-C.sub.6-alkylaminocarbonyl, di-(C.sub.1-C.sub.6)-alkylaminocarbonyl, C.sub.1-C.sub.6-alkylcarbonylamino, aryl and hetaryl, where aryl and hetaryl for their part may each optionally be mono- or polysubstituted and the substituents independently of one another are selected from the group consisting of halogen, cyano, nitro, hydroxy, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-haloalkoxy and C.sub.1-C.sub.6-alkylthio, or R.sup.5c represents aryl, C-bound hetaryl, N-bound hetaryl, C.sub.3-C.sub.8-heterocyclyl, C.sub.3-C.sub.8-oxoheterocyclyl or C.sub.3-C.sub.8-dioxoheterocyclyl, where the radicals mentioned above may each optionally be mono- to pentasubstituted and the substituents independently of one another are selected from the group consisting of halogen, nitro, amino, cyano, SF.sub.5, SCN, C.sub.1-C.sub.6-alkylamino, di-(C.sub.1-C.sub.6-alkyl)amino, hydroxy, COOH, C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.3-C.sub.6-halocycloalkyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.1-C.sub.6-alkyl, 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.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyloxy, cyano-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.3-C.sub.6-alkynyl, SH, C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-alkylcarbonyl, C.sub.3-C.sub.6-cycloalkylcarbonyl, C.sub.2-C.sub.6-alkenylcarbonyl, C.sub.1-C.sub.6-haloalkylcarbonyl, C.sub.1-C.sub.6-alkoxycarbonyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylsulfonyl, C.sub.1-C.sub.6-alkylaminocarbonyl, di-(C.sub.1-C.sub.6-alkyl)aminocarbonyl, C.sub.1-C.sub.6-alkylcarbonylamino, tri-(C.sub.1-C.sub.6-alkyl)silyl, aryl, hetaryl, heterocyclyl, aryl-C.sub.1-C.sub.6-alkyl and hetaryl-C.sub.1-C.sub.6-alkyl, where aryl, hetaryl, aryl-C.sub.1-C.sub.6-alkyl and hetaryl-C.sub.1-C.sub.6-alkyl for their part may each optionally be mono- to trisubstituted and the substituents independently of one another are selected from the group consisting of halogen, cyano, nitro, hydroxy, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy and C.sub.1-C.sub.6-haloalkoxy or C.sub.1-C.sub.6-alkylthio, R.sup.6 and R.sup.13 represent hydrogen, or represent C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl, heterocyclyl, aryl, hetaryl, aryl-C.sub.1-C.sub.6-alkyl or hetaryl-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-oxoheterocyclyl or C.sub.3-C.sub.6-dioxoheterocyclyl, where the radicals mentioned above may each optionally be mono- to trisubstituted and the substituents independently of one another are selected from the group consisting of halogen, and/or may each optionally be monosubstituted and the substituent is selected from the group consisting of nitro, cyano, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, 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-alkylthio, C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-alkylcarbonyl, C.sub.1-C.sub.6-alkoxyimino-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkylcarbonyl, C.sub.2-C.sub.6-alkenylcarbonyl, C.sub.1-C.sub.6-haloalkylcarbonyl, C.sub.1-C.sub.6-alkoxycarbonyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylsulfonyl, C.sub.1-C.sub.6-alkylaminocarbonyl, di-(C.sub.1-C.sub.6)-alkylaminocarbonyl, aryl and hetaryl, where aryl and hetaryl for their part may each optionally be mono- to trisubstituted and the substituents independently of one another are selected from the group consisting of halogen, cyano, nitro, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy and C.sub.1-C.sub.4-haloalkoxy, R.sup.7a, R.sup.11a and R.sup.14a independently of one another represent hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxycarbonyl, C.sub.1-C.sub.6-alkylcarbonyl or C.sub.1-C.sub.6-alkylsulfonyl, R.sup.7b, R.sup.11b and R.sup.14b independently of one another represent hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl or C.sub.3-C.sub.6-heterocyclyl, where C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl and C.sub.3-C.sub.6-heterocyclyl may each optionally be mono- to pentasubstituted and the substituents independently of one another are selected from the group consisting of halogen, and/or may each optionally be monosubstituted and the substituent is selected from the group consisting of nitro, cyano, hydroxy, 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-alkylthio, C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, aryl, hetaryl, heterocyclyl and oxoheterocyclyl, where aryl, C.sub.3-C.sub.6-cycloalkyl, hetaryl, heterocyclyl and oxoheterocyclyl for their part may each optionally be mono- to trisubstituted and the substituents independently of one another are selected from the group consisting of halogen, nitro, cyano, C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.3-C.sub.6-halocycloalkyl, 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.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyloxy, cyano-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.3-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-alkylcarbonyl, C.sub.3-C.sub.6-cycloalkylcarbonyl, C.sub.2-C.sub.6-alkenylcarbonyl, C.sub.1-C.sub.6-haloalkylcarbonyl, C.sub.1-C.sub.6-alkoxycarbonyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylsulfonyl, C.sub.1-C.sub.6-alkylaminocarbonyl, di-(C.sub.1-C.sub.6)-alkylaminocarbonyl, C.sub.1-C.sub.6-alkylcarbonylamino, aryl and hetaryl, where aryl and hetaryl for their part may each optionally be mono- or polysubstituted and the substituents independently of one another are selected from the group consisting of halogen, cyano, nitro, hydroxy, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-haloalkoxy and C.sub.1-C.sub.6-alkylthio, or R.sup.7b, R.sup.11b and R.sup.14b independently of one another represent aryl or hetaryl, where the radicals mentioned above may each optionally be mono- to trisubstituted and the substituents independently of one another are selected from the group consisting of halogen, nitro, amino, cyano, SF.sub.5, SCN, C.sub.1-C.sub.6-alkylamino, di-(C.sub.1-C.sub.6)-alkylamino, hydroxy, COOH, C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.3-C.sub.6-halocycloalkyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.1-C.sub.6-alkyl, 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.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyloxy, cyano-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.3-C.sub.6-alkynyl, SH, C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-alkylcarbonyl, C.sub.3-C.sub.6-cycloalkylcarbonyl, C.sub.2-C.sub.6-alkenylcarbonyl, C.sub.1-C.sub.6-haloalkylcarbonyl, C.sub.1-C.sub.6-alkoxycarbonyl, C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylsulfonyl, C.sub.1-C.sub.6-alkylaminocarbonyl, di-(C.sub.1-C.sub.6)-alkylaminocarbonyl and tri-(C.sub.1-C.sub.6-alkyl)silyl, or R.sup.7a and R.sup.7b may be attached to one another via two to six carbon atoms and form a ring which may optionally additionally contain a further atom from the group consisting of O, S and N and which may optionally be mono- to tetrasubstituted and where the substituents independently of one another are selected from the group consisting of C.sub.1-C.sub.2-alkyl, halogen, cyano, amino and C.sub.1-C.sub.2-alkoxy, or R.sup.11a and R.sup.11b may be attached to one another via two to six carbon atoms and form a ring which may optionally additionally contain a further atom from the group consisting of O, S and N and which may optionally be mono- to tetrasubstituted and where the substituents independently of one another are selected from the group consisting of C.sub.1-C.sub.2-alkyl, halogen, cyano, amino and C.sub.1-C.sub.2-alkoxy, or R.sup.14a and R.sup.14b may be attached to one another via two to six carbon atoms and form a ring which may optionally additionally contain a further atom from the group consisting of O, S and N and which may optionally be mono- to tetrasubstituted and where the substituents independently of one another are selected from the group consisting of C.sub.1-C.sub.2-alkyl, halogen, cyano, amino and C.sub.1-C.sub.2-alkoxy, R.sup.8 represents hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxycarbonyl or C.sub.1-C.sub.6-alkylcarbonyl, R.sup.9 represents hydrogen, fluorine, chlorine, C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl or C.sub.1-C.sub.4-haloalkyl, R.sup.10 represents hydrogen, fluorine, chlorine or C.sub.1-C.sub.4-alkyl, and R.sup.12 represents hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl or C.sub.3-C.sub.6-heterocyclyl, where C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl and C.sub.3-C.sub.6-heterocyclyl may each optionally be mono- to pentasubstituted and the substituents independently of one another are selected from the group consisting of halogen, and/or may each optionally be monosubstituted and the substituent is selected from the group consisting of nitro, cyano, 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-alkylthio, C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, aryl, hetaryl, heterocyclyl and oxoheterocyclyl, where aryl, hetaryl, heterocyclyl and oxoheterocyclyl for their part may each optionally be mono to trisubstituted and the substituents independently of one another are selected from the group consisting of halogen, nitro, cyano, C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.3-C.sub.6-halocycloalkyl, 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.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyloxy, cyano-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.3-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-alkylcarbonyl, C.sub.3-C.sub.6-cycloalkylcarbonyl, C.sub.2-C.sub.6-alkenylcarbonyl, C.sub.1-C.sub.6-haloalkylcarbonyl, C.sub.1-C.sub.6-alkoxycarbonyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylsulfonyl, C.sub.1-C.sub.6-alkylaminocarbonyl, di-(C.sub.1-C.sub.6)-alkylaminocarbonyl, C.sub.1-C.sub.6-alkylcarbonylamino, aryl and hetaryl, where aryl and hetaryl for their part may each optionally be mono- or polysubstituted and the substituents independently of one another are selected from the group consisting of halogen, cyano, nitro, hydroxy, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-haloalkoxy and C.sub.1-C.sub.6-alkylthio, or R.sup.12 represents aryl or hetaryl, where the radicals mentioned above may each optionally be mono to trisubstituted and the substituents independently of one another are selected from the group consisting of halogen, nitro, amino, cyano, SF.sub.5, SCN, C.sub.1-C.sub.6-alkylamino, di-(C.sub.1-C.sub.6)-alkylamino, hydroxy, COOH, C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.3-C.sub.6-halocycloalkyl, C.sub.3-C.sub.6-halocycloalkyl-C.sub.1-C.sub.6-alkyl, 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.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyloxy, cyano-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.3-C.sub.6-alkynyl, SH, C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-alkylcarbonyl, C.sub.3-C.sub.6-cycloalkylcarbonyl, C.sub.2-C.sub.6-alkenylcarbonyl, C.sub.1-C.sub.6-haloalkylcarbonyl, C.sub.1-C.sub.6-alkoxycarbonyl, C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylsulfonyl, C.sub.1-C.sub.6-alkylaminocarbonyl, di-(C.sub.1-C.sub.6)-alkylaminocarbonyl and tri-(C.sub.1-C.sub.6-alkyl)silyl, R.sup.15 represents hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl or C.sub.3-C.sub.6-heterocyclyl, where C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl and C.sub.3-C.sub.6-heterocyclyl may each optionally be mono- to pentasubstituted and the substituents independently of one another are selected from the group consisting of halogen, and/or may each optionally be monosubstituted and the substituent is selected from the group consisting of nitro, cyano, 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-alkylthio, C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, aryl, hetaryl, heterocyclyl and oxoheterocyclyl, where aryl, hetaryl, heterocyclyl and oxoheterocyclyl for their part may each optionally be mono to trisubstituted and the substituents independently of one another are selected from the group consisting of halogen, nitro, cyano, C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.3-C.sub.6-halocycloalkyl, 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.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyloxy, cyano-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.3-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-alkylcarbonyl, C.sub.3-C.sub.6-cycloalkylcarbonyl, C.sub.2-C.sub.6-alkenylcarbonyl, C.sub.1-C.sub.6-haloalkylcarbonyl, C.sub.1-C.sub.6-alkoxycarbonyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylsulfonyl, C.sub.1-C.sub.6-alkylaminocarbonyl, di-(C.sub.1-C.sub.6)-alkylaminocarbonyl, C.sub.1-C.sub.6-alkylcarbonylamino, aryl and hetaryl, where aryl and hetaryl for their part may each optionally be mono- or polysubstituted and the substituents independently of one another are selected from the group consisting of halogen, cyano, nitro, hydroxy, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-haloalkoxy and C.sub.1-C.sub.6-alkylthio.

2. The compound according to claim 1, in which T represents hydrogen, C(R.sup.5a)(R.sup.5b)(R.sup.5c), C.sub.2-C.sub.6-alkenyl, C.sub.3-C.sub.6-alkynyl or C.sub.3-C.sub.6-cycloalkyl, where C.sub.2-C.sub.6-alkenyl, C.sub.3-C.sub.6-alkynyl and C.sub.3-C.sub.6-cycloalkyl may each optionally be mono- to trisubstituted and the substituents independently of one another are selected from the group consisting of halogen, and/or may each optionally be monosubstituted and the substituent is selected from the group consisting of cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-alkylthio, C.sub.1-C.sub.4-alkylsulfinyl and C.sub.1-C.sub.4-alkylsulfonyl, or T represents aryl, C.sub.1-C.sub.6-alkylenedioxyphenyl, hetaryl or C.sub.3-C.sub.6-heterocyclyl, where the radicals mentioned above may each optionally be mono- to pentasubstituted and the substituents independently of one another are selected from the group consisting of halogen, nitro, cyano, C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-heterocyclyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.2-C.sub.4-alkenyl, C.sub.3-C.sub.4-alkynyl, C.sub.1-C.sub.4-alkylthio, C.sub.1-C.sub.4-alkylsulfinyl, C.sub.1-C.sub.4-alkylcarbonyl, C.sub.3-C.sub.6-cycloalkylcarbonyl, C.sub.2-C.sub.4-alkenylcarbonyl, C.sub.1-C.sub.4-haloalkylcarbonyl, C.sub.1-C.sub.4-alkoxycarbonyl, C.sub.1-C.sub.4-alkylsulfonyl, C.sub.1-C.sub.4-haloalkylsulfonyl, aryl, hetaryl, heterocyclyl, aryl-C.sub.1-C.sub.6-alkyl and hetaryl-C.sub.1-C.sub.6-alkyl, where aryl, hetaryl, aryl-C.sub.1-C.sub.6-alkyl and hetaryl-C.sub.1-C.sub.6-alkyl for their part may each be mono- to trisubstituted and the substituents independently of one another are selected from the group consisting of halogen, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy and C.sub.1-C.sub.4-haloalkoxy, or T represents OR.sup.6, N(R.sup.7a)(R.sup.7b) or N(R.sup.8)N(R.sup.11a)(R.sup.11b) or T represents C(W)R.sup.12, C(O)OR.sup.13 or C(O)NR.sup.14aR.sup.14b W represents O or NOR.sup.15, G represents C(R.sup.9)(R.sup.10), U represents a cycle from the group consisting of U-1, U-2, U-5, U-6, U-9, U-10, U-20 and U-23, X.sup.a represents halogen, nitro, cyano, SF.sub.5, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, 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-alkyl, cyano-C.sub.1-C.sub.4-alkyl, C.sub.2-C.sub.4-alkenyl, C.sub.3-C.sub.4-alkynyl, C.sub.1-C.sub.4-alkylthio, C.sub.1-C.sub.4-alkylcarbonyl, C.sub.1-C.sub.4-alkoxycarbonyl, C.sub.1-C.sub.4-alkoxyimino-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkylsulfinyl, C.sub.1-C.sub.4-alkylsulfonyl, C.sub.1-C.sub.4-haloalkylsulfonyl, phenyl, pyridyl, phenyl-C.sub.1-C.sub.4-alkyl or pyridyl-C.sub.1-C.sub.4-alkyl, where phenyl, pyridyl, phenyl-C.sub.1-C.sub.4-alkyl and pyridyl-C.sub.1-C.sub.4-alkyl may each be mono- to trisubstituted by halogen, cyano, nitro, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy or C.sub.1-C.sub.4-haloalkoxy, n represents 0, 1, 2 or 3, R.sup.1 represents hydrogen, halogen, cyano, C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.4-haloalkyl, 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-alkyl, C.sub.2-C.sub.4-alkenyl, C.sub.2-C.sub.4-alkenyloxy, C.sub.3-C.sub.4-alkynyl, C.sub.3-C.sub.4-alkynyloxy, C.sub.1-C.sub.4-alkylthio, C.sub.1-C.sub.4-alkylsulfinyl, C.sub.1-C.sub.4-alkylsulfonyl, C.sub.1-C.sub.4-alkoxyimino-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxycarbonyl, aryl or hetaryl, p represents 1 or 2, R.sup.5a and R.sup.5b independently of one another represent hydrogen, halogen, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl or C.sub.1-C.sub.4-alkoxy, R.sup.5c represents hydrogen, fluorine, chlorine, bromine, cyano, C.sub.1-C.sub.4-alkoxycarbonyl, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy, C.sub.3-C.sub.6-cycloalkyl, C.sub.2-C.sub.6-alkenyl or C.sub.2-C.sub.6-alkynyl, where C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy, C.sub.3-C.sub.6-cycloalkyl, C.sub.2-C.sub.6-alkenyl and C.sub.2-C.sub.6-alkynyl may each optionally be mono to pentasubstituted and the substituents independently of one another are selected from the group consisting of halogen, and/or may each optionally be monosubstituted and the substituent is selected from the group consisting of nitro, cyano, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-alkylcarbonyl, C.sub.1-C.sub.4-alkoxycarbonyl and hetaryl, where hetaryl for its part may be monosubstituted and the substituents are selected from the group consisting of C.sub.1-C.sub.4-alkyl and halogen, or R.sup.5c represents aryl or C-bound hetaryl, where the radicals mentioned above may each optionally be mono- to pentasubstituted and the substituents independently of one another are selected from the group consisting of halogen, nitro, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-alkoxycarbonyl, C.sub.1-C.sub.4-alkylthio, C.sub.1-C.sub.4-alkylsulfinyl and C.sub.1-C.sub.4-alkylsulfonyl, or R.sup.5c represents Y, Y represents one of the radicals Y-1 to Y-23, ##STR00152## ##STR00153## ##STR00154## X.sup.b represents halogen, nitro, cyano, C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.3-C.sub.6-halocycloalkyl, 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.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyloxy, cyano-C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.3-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-alkylcarbonyl, C.sub.3-C.sub.6-cycloalkylcarbonyl, C.sub.2-C.sub.6-alkenylcarbonyl, C.sub.1-C.sub.6-haloalkylcarbonyl, C.sub.1-C.sub.6-alkoxycarbonyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-haloalkylsulfonyl, C.sub.1-C.sub.6-alkylaminocarbonyl, di-(C.sub.1-C.sub.6)-alkylaminocarbonyl, C.sub.1-C.sub.6-alkylcarbonylamino, aryl or hetaryl, where aryl and hetaryl for their part may each optionally be mono- to trisubstituted and the substituents independently of one another are selected from the group consisting of halogen, cyano, nitro, hydroxy, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-haloalkoxy and C.sub.1-C.sub.6-alkylthio and where the ring nitrogen atoms in Y-13, Y-14 and Y-16 are not substituted by halogen, nitro, cyano, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy or C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyloxy, m represents 0, 1 or 2, R.sup.6 and R.sup.13 independently of one another represent hydrogen, or represent C.sub.1-C.sub.4-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-heterocyclyl, C.sub.3-C.sub.6-oxoheterocyclyl, C.sub.3-C.sub.6-dioxoheterocyclyl, phenyl, pyridyl, phenyl-C.sub.1-C.sub.4-alkyl or pyridyl-C.sub.1-C.sub.4-alkyl, where the radicals mentioned above may each optionally be mono- to trisubstituted and the substituents independently of one another are selected from the group consisting of halogen, and/or may each optionally be monosubstituted and the substituent is selected from the group consisting of nitro, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, 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-alkylthio, C.sub.1-C.sub.4-alkylsulfinyl, C.sub.1-C.sub.4-alkylsulfonyl, C.sub.1-C.sub.4-alkoxycarbonyl, aryl and hetaryl, where aryl and hetaryl for their part may each optionally be mono- to trisubstituted and the substituents independently of one another are selected from the group consisting of halogen, cyano, nitro, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy and C.sub.1-C.sub.4-haloalkoxy, R.sup.7a, R.sup.11a and R.sup.14a independently of one another represent hydrogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxycarbonyl or C.sub.1-C.sub.6-alkylcarbonyl, R.sup.7b, R.sup.11b and R.sup.14b independently of one another represent hydrogen, or independently of one another represent C.sub.1-C.sub.6-alkyl or C.sub.3-C.sub.6-cycloalkyl, where the radicals mentioned above may each optionally be mono- to trisubstituted and the substituents independently of one another are selected from the group consisting of halogen, and/or may optionally be monosubstituted and the substituent is selected from the group consisting of cyano, nitro, hydroxy and C.sub.1-C.sub.4-alkoxy, C.sub.3-C.sub.6-cycloalkyl, aryl and hetaryl, where aryl, C.sub.3-C.sub.6-cycloalkyl and hetaryl for their part may be mono- to trisubstituted and the substituents independently of one another are selected from the group consisting of halogen, nitro, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy and C.sub.1-C.sub.4-haloalkoxy, or R.sup.7b, R.sup.11b and R.sup.14b independently of one another represent aryl or hetaryl, where the radicals mentioned above may each optionally be mono- to trisubstituted and the substituents independently of one another are selected from the group consisting of halogen, nitro, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-alkylthio, C.sub.1-C.sub.4-alkylsulfinyl and C.sub.1-C.sub.4-alkylsulfonyl, or R.sup.7a and R.sup.7b may be attached to one another via two to six carbon atoms and form a ring which may optionally additionally contain a further atom from the group consisting of O, S and N and which may optionally be mono- to tetrasubstituted and where the substituents independently of one another are selected from the group consisting of C.sub.1-C.sub.2-alkyl, fluorine, chlorine, bromine and C.sub.1-C.sub.2-alkoxy, or R.sup.11a and R.sup.11b may be attached to one another via two to six carbon atoms and form a ring which may optionally additionally contain a further atom from the group consisting of O, S and N and which may optionally be mono- to tetrasubstituted and where the substituents independently of one another are selected from the group consisting of C.sub.1-C.sub.2-alkyl, fluorine, chlorine, bromine and C.sub.1-C.sub.2-alkoxy, or R.sup.14a and R.sup.14b may be attached to one another via two to six carbon atoms and form a ring which may optionally additionally contain a further atom from the group consisting of O, S and N and which may optionally be mono- to tetrasubstituted and where the substituents independently of one another are selected from the group consisting of C.sub.1-C.sub.2-alkyl, fluorine, chlorine, bromine and C.sub.1-C.sub.2-alkoxy, R.sup.8 represents hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.6-alkoxycarbonyl or C.sub.1-C.sub.6-alkylcarbonyl, R.sup.9 represents hydrogen, fluorine, chlorine or C.sub.1-C.sub.4-alkyl, R.sup.10 represents hydrogen, and R.sup.12 represents hydrogen, or R.sup.12 represents C.sub.1-C.sub.6-alkyl which may optionally be mono- to pentasubstituted and where the substituents independently of one another are selected from the group consisting of halogen, and/or which may optionally be monosubstituted and where the substituent is selected from the group consisting of nitro, cyano, C.sub.1-C.sub.4-alkoxy and C.sub.1-C.sub.4-haloalkoxy, or R.sup.12 represents aryl or hetaryl, where the radicals mentioned above may each optionally be mono to trisubstituted and the substituents independently of one another are selected from the group consisting of halogen, nitro, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-alkylthio, C.sub.1-C.sub.4-alkylsulfinyl and C.sub.1-C.sub.4-alkylsulfonyl, R.sup.15 represents hydrogen or C.sub.1-C.sub.6-alkyl, where C.sub.1-C.sub.6-alkyl may each optionally be mono- to pentasubstituted and where the substituents independently of one another are selected from the group consisting of halogen, and/or may each optionally be monosubstituted and the substituent is selected from the group consisting of nitro, cyano, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, aryl and hetaryl, where aryl and hetaryl for their part may each optionally be mono- to trisubstituted and the substituents independently of one another are selected from the group consisting of halogen, nitro, cyano, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-alkylcarbonyl, C.sub.1-C.sub.6-haloalkylcarbonyl, C.sub.1-C.sub.6-alkoxycarbonyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylsulfonyl and C.sub.1-C.sub.6-alkylcarbonylamino.

3. The compound according to claim 1, in which T represents hydrogen, C(R.sup.5a)(R.sup.5b)(R.sup.5c), C.sub.2-C.sub.4-alkenyl, C.sub.3-C.sub.4-alkynyl or C.sub.3-C.sub.6-cycloalkyl, where C.sub.2-C.sub.4-alkenyl, C.sub.3-C.sub.4-alkynyl or C.sub.3-C.sub.6-cycloalkyl may each optionally be mono- to trisubstituted and the substituents independently of one another are selected from the group consisting of halogen, and/or may each optionally be monosubstituted and the substituent is selected from the group consisting of cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-alkylthio, C.sub.1-C.sub.4-alkylsulfinyl and C.sub.1-C.sub.4-alkylsulfonyl, or T represents phenyl, C.sub.1-C.sub.4-alkylenedioxyphenyl, naphthyl, furanyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, 1,3-oxazolyl, 1,2-oxazolyl, thiazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyrimidyl, thiophenyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl, benzofuranyl, indolyl, benzothiazolyl, benzoxazolyl, benzimidazolyl, pyrazolopyridinyl, quinolinyl, isoquinolinyl, cinnolinyl, azetidinyl, azolidinyl, azinanyl, oxetanyl, oxolanyl, oxanyl, dioxanyl, thiethanyl, thiolanyl, thianyl, or dihydroisoxazolyl, where the radicals mentioned above may each optionally be mono- to tetrasubstituted and the substituents independently of one another are selected from the group consisting of fluorine and chlorine, and/or may each optionally be mono- to disubstituted and the substituents independently of one another are selected from the group consisting of bromine, nitro, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-alkylthio, C.sub.1-C.sub.4-alkylsulfinyl, C.sub.1-C.sub.4-alkylsulfonyl, C.sub.1-C.sub.4-haloalkylsulfonyl, phenyl, pyridyl and morpholinyl, where in total at most five of the substituents mentioned above are present and where phenyl and pyridyl for their part may each additionally be mono- to trisubstituted and the substituents independently of one another are selected from the group consisting of halogen, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy and C.sub.1-C.sub.4-haloalkoxy, or T represents OR.sup.6, N(R.sup.7a)(R.sup.7b) or N(R.sup.8)N(R.sup.11a)(R.sup.11b) or T represents C(W)R.sup.12, C(O)OR.sup.13, or C(O)NR.sup.14aR.sup.14b, W represents O or NOR.sup.5, G represents C(R.sup.9)(R.sup.10), U represents a cycle from the group consisting of U-2, U-9, U-10 and U-23, X.sup.a represents halogen, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, trifluoromethoxy, methylthio, methylsulfinyl or methylsulfonyl, n represents 0, 1 or 2, R.sup.1 represents hydrogen, fluorine, chlorine, methyl, ethyl, cyclopropyl, phenyl, methoxy or ethoxy, p represents 1 or 2, R.sup.5a and R.sup.5b independently of one another represent hydrogen, halogen, C.sub.1-C.sub.4-alkyl or C.sub.1-C.sub.4-alkoxy, R.sup.5c represents hydrogen, fluorine, chlorine, bromine, C.sub.1-C.sub.4-alkoxycarbonyl, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy or C.sub.3-C.sub.6-cycloalkyl, where C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy and C.sub.3-C.sub.6-cycloalkyl may each optionally be mono- to trisubstituted and the substituents independently of one another are selected from the group consisting of halogen, and/or may each optionally be monosubstituted and the substituent is selected from the group consisting of cyano, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-alkoxycarbonyl, pyrimidyl, 1,2-oxazolyl and pyridyl, where pyridyl for its part may be monosubstituted and the substituents are selected from the group consisting of C.sub.1-C.sub.4-alkyl and halogen, or R.sup.5c represents phenyl or C-bound pyridyl, where the radicals mentioned above may each optionally be mono- to trisubstituted and the substituents independently of one another are selected from the group consisting of halogen, nitro, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-alkoxycarbonyl, C.sub.1-C.sub.4-alkylthio, C.sub.1-C.sub.4-alkylsulfinyl and C.sub.1-C.sub.4-alkylsulfonyl, or R.sup.5c represents Y, Y represents one of the radicals Y-2, Y-3, Y-4, Y-5, Y-6 or Y-7, X.sup.b represents halogen, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, methylaminocarbonyl, methylcarbonylamino, methoxy, ethoxy, trifluoromethoxy, methylthio, ethylthio, methylsulfinyl, methylsulfonyl or methoxycarbonyl, m represents 0, 1 or 2, R.sup.6 and R.sup.13 independently of one another represent hydrogen, or represent C.sub.1-C.sub.4-alkyl, C.sub.2-C.sub.4-alkenyl, C.sub.2-C.sub.4-alkynyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-heterocyclyl or C.sub.3-C.sub.6-dioxoheterocyclyl, where the radicals mentioned above may each optionally be mono- to trisubstituted and the substituents independently of one another are selected from the group consisting of halogen, and/or may each optionally be monosubstituted and the substituent is selected from the group consisting of cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-alkylthio, C.sub.1-C.sub.4-alkylsulfinyl, C.sub.1-C.sub.4-alkylsulfonyl, C.sub.1-C.sub.4-alkoxycarbonyl, phenyl and pyridyl, where phenyl and pyridyl for their part may each be mono- to trisubstituted and the substituents independently of one another are selected from the group consisting of halogen, cyano, nitro, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy and C.sub.1-C.sub.4-haloalkoxy, R.sup.7a, R.sup.11a and R.sup.14a independently of one another represent hydrogen or C.sub.1-C.sub.4-alkyl, R.sup.7b, R.sup.11b and R.sup.14b independently of one another represent hydrogen, or independently of one another represent C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl, where the radicals mentioned above may each optionally be mono- to trisubstituted and the substituents independently of one another are selected from the group consisting of halogen, and/or may optionally be monosubstituted and the substituent is selected from the group consisting of C.sub.3-C.sub.6-cycloalkyl and phenyl, where C.sub.3-C.sub.6-cycloalkyl and phenyl for their part may be mono to trisubstituted and the substituents independently of one another are selected from the group consisting of halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl and C.sub.1-C.sub.4-alkoxy, or R.sup.7b, R.sup.11b and R.sup.14b independently of one another represent phenyl or pyridyl, where the radicals mentioned above may each optionally be mono- to trisubstituted and the substituents independently of one another are selected from the group consisting of halogen, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-alkylthio, C.sub.1-C.sub.4-alkylsulfinyl and C.sub.1-C.sub.4-alkylsulfonyl, or R.sup.7a and R.sup.7b may be attached to one another via two to six carbon atoms and form a ring which may optionally additionally contain a further atom from the group consisting of O, S and N and which may optionally be mono- to trisubstituted and where the substituents independently of one another are selected from the group consisting of methyl, ethyl, fluorine, methoxy and ethoxy, or R.sup.11a and R.sup.11b may be attached to one another via two to six carbon atoms and form a ring which may optionally additionally contain a further atom from the group consisting of O, S and N and which may optionally be mono- to trisubstituted and where the substituents independently of one another are selected from the group consisting of methyl, ethyl, fluorine, methoxy and ethoxy, or R.sup.14a and R.sup.14b may be attached to one another via two to six carbon atoms and form a ring which may optionally additionally contain a further atom from the group consisting of O, S and N and which may optionally be mono- to trisubstituted and where the substituents independently of one another are selected from the group consisting of methyl, ethyl, fluorine, methoxy and ethoxy, R.sup.8 represents hydrogen and methyl, R.sup.9 represents hydrogen or methyl, R.sup.10 represents hydrogen, and R.sup.12 represents hydrogen, or R.sup.12 represents C.sub.1-C.sub.4-alkyl which may optionally be mono- to pentasubstituted and where the substituents independently of one another are selected from the group consisting of halogen, or R.sup.12 represents phenyl which may optionally be mono- to trisubstituted and where the substituents independently of one another are selected from the group consisting of halogen, R.sup.15 represents hydrogen or C.sub.1-C.sub.6-alkyl, where C.sub.1-C.sub.6-alkyl may each optionally be mono- to trisubstituted and the substituents independently of one another are selected from the group consisting of halogen, and/or may each optionally be monosubstituted and the substituent is selected from the group consisting of cyano, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, aryl and hetaryl, where aryl and hetaryl for their part may each optionally be mono- to trisubstituted and the substituents independently of one another are selected from the group consisting of halogen, cyano, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-haloalkyl.

4. The compound according to claim 1, in which T represents hydrogen, C(R.sup.5a)(R.sup.5b)(R.sup.5c), ethenyl, propenyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, where ethenyl, propenyl, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl may each optionally be mono- to trisubstituted and the substituents independently of one another are selected from the group consisting of fluorine and chlorine, and/or may each optionally be monosubstituted and the substituent is selected from the group consisting of cyano, methyl, ethyl, trifluoromethyl and methoxy, or T represents phenyl, pyridyl, pyrimidyl, thiophenyl, furanyl, pyrrolyl, thiazolyl, isothiazolyl, 1,3-oxazolyl, 1,2-oxazolyl, 1,2,4-oxadiazolyl, pyrazolyl, imidazolyl, pyrazolopyridinyl, benzothiazolyl, benzofuranyl, benzoxazolyl, quinolinyl, oxolanyl or dihydroisoxazolyl, where the radicals mentioned above may each optionally be mono- to tetrasubstituted and the substituents independently of one another are selected from the group consisting of fluorine and chlorine, and/or may each optionally be mono- to disubstituted and the substituents independently of one another are selected from the group consisting of bromine, cyano, methyl, ethyl, difluoromethyl, trifluoromethyl, trifluoroethyl, pentafluoroethyl, trifluoropropyl, methoxy, ethoxy, trifluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl, morpholinyl and phenyl, where in total at most five of the substituents mentioned above are present, or T represents OR.sup.6, N(R.sup.7a)(R.sup.7b) or N(R.sup.8)N(R.sup.11a)(R.sup.11b) or T represents C(W)R.sup.12, C(O)OR.sup.13, or C(O)NR.sup.14aR.sup.14b, W represents O or NOR.sup.15, G represents CH.sub.2, U represents U-2, U-9 or U-23, X.sup.a represents chlorine, n represents 0 or 1, R.sup.1 represents hydrogen, methyl, cyclopropyl or phenyl, p represents 1, R.sup.5a and R.sup.5b independently of one another represent hydrogen, fluorine, chlorine, methyl, ethyl, methoxy or ethoxy, R.sup.5c represents hydrogen, fluorine, chlorine, bromine, cyano or methoxycarbonyl, or represents methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclopropyl, methoxy, ethoxy or phenyl, where the radicals mentioned above may each optionally be mono- to trisubstituted and the substituents independently of one another are selected from the group consisting of fluorine and chlorine, and/or may each optionally be monosubstituted and the substituent is selected from the group consisting of cyano, methoxy, methoxycarbonyl, trifluoromethyl, pyrimidinyl, 1,2-oxazolyl, methylpyridyl, fluoropyridyl or chloropyridyl, where in total at most three of the substituents mentioned above are present, or R.sup.5c represents Y, Y represents the radical Y-2, X.sup.b represents fluorine, chlorine, bromine, cyano, methyl, ethyl, methoxy, ethoxy, methylthio, difluoromethyl or trifluoromethyl, m represents 0 or 1, R.sup.6 and R.sup.13 independently of one another represent hydrogen, or represent C.sub.1-C.sub.4-alkyl, C.sub.2-C.sub.4-alkenyl, C.sub.2-C.sub.4-alkynyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, oxanyl or 1,1-dioxothianyl, where the radicals mentioned above may each optionally be mono- to trisubstituted and the substituents independently of one another are selected from the group consisting of fluorine and chlorine, and/or may each optionally be monosubstituted and the substituent is selected from the group consisting of cyano, methyl, methoxy, trifluoromethyl, tetrafluoroethyl, phenyl or R.sup.6 and R.sup.13 represent cyclopropylmethyl or cyclobutylmethyl, or represent phenylmethyl or pyridylmethyl, where the radicals mentioned above may each optionally be mono- to trisubstituted and the substituents independently of one another are selected from the group consisting of fluorine and chlorine, and/or may each optionally be monosubstituted and the substituent is selected from the group consisting of cyano, methyl, methoxy, trifluoromethyl, where in total at most three of the substituents mentioned above are present, R.sup.7a, R.sup.11a and R.sup.14a independently of one another represent hydrogen, ethyl or methyl, R.sup.7b, R.sup.11b and R.sup.14b independently of one another represent hydrogen, C.sub.1-C.sub.4-alkyl, cyclopropyl, benzyl or cyclopropylmethyl, where the radicals mentioned above may each optionally be mono- to trisubstituted and the substituents independently of one another are selected from the group consisting of fluorine and chlorine, or represent phenyl, where the radical mentioned above may optionally be mono- to trisubstituted and the substituents independently of one another are selected from the group consisting of fluorine and chlorine, and/or may optionally be monosubstituted and the substituent is selected from the group consisting of cyano, methyl, methoxy, trifluoromethyl, methylthio, methylsulfinyl and methylsulfonyl, where in total at most three of the substituents mentioned above are present, R.sup.8 represents hydrogen, and R.sup.12 represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl or phenyl, where the radicals mentioned above may each optionally be mono- to trisubstituted and the substituents independently of one another are selected from the group consisting of fluorine and chlorine, and R.sup.15 represents methyl.

5. The compound according to claim 1, comprising a structure according to formula (I-1) ##STR00155##

6. The compound according to claim 1, comprising a structure according to formula (I-1a) ##STR00156##

7. The compound according to claim 1, comprising a structure according to formula (I-1b) ##STR00157##

8. The compound according to claim 1, comprising a structure according to formula (I-1c) ##STR00158##

9. A compound of formula (VII) ##STR00159## in which Y.sup. represents F.sup., Cl.sup., Br.sup., I.sup., NO.sub.3.sup., SO.sub.4.sup., trifluoroacetate or ClO.sub.4.sup., optionally F.sup., Cl.sup., Br.sup., I.sup. or trifluoroacetate.

10. A compound of formula (V) ##STR00160##

11. A formulation, optionally an agrochemical formulation, comprising at least one compound of the formula (I) according to claim 1.

12. The formulation according to claim 11, further comprising at least one extender and/or at least one surface-active substance.

13. The formulation according to claim 11, wherein the compound of formula (I) is in a mixture with at least one further active compound.

14. A method for controlling one or more pests, optionally animal pests, comprising allowing a compound of formula (I) according to claim 1 or a formulation thereof to act on the pests and/or a habitat thereof.

15. The method according to claim 14, wherein the pest is an animal pest and comprises an insect, an arachnid or a nematode, or in that the pest is an insect, an arachnid or a nematode.

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

17. The product according to claim 16, wherein the animal pest comprises an insect, an arachnid or a nematode.

18. The product according to claim 16 in crop protection.

19. The product according to claim 16 in the field of animal health.

20. A method for protecting seed and/or a germinating plant from one or more pests, optionally animal pests, comprising contacting the seed and/or plant with a compound of formula (I) according to claim 1 or with a formulation thereof.

21. The seed obtained by a method according to claim 20.

Description

PREPARATION EXAMPLES

tert-Butyl 2-[(2-chlorothiazol-5-yl)methyl-(2-pyridyl)amino]acetate

[0719] ##STR00027##

[0720] At 0 C., a solution of 3.00 g (13.2 mmol) of N-[(2-chlorothiazol-5-yl)methyl]pyridine-2-amine in 12 ml of DMF was added to a suspension of 1.33 g (33.2 mmol, 60% pure) of sodium hydride in 24 ml of DMF. The mixture was stirred at 0 C. for 1.5 h, a solution of 5.19 g (26.5 mmol) of tert-butyl 2-bromoacetate in 12 ml of DMF was then added dropwise and the mixture was stirred at RT for 16 h. The reaction mixture was stirred into saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The phases were separated and the organic phases were washed with saturated aqueous NaCl solution and concentrated. The residue was purified by column chromatography on silica gel (cyclohexane/ethyl acetate, 1/1). HPLC-MS: log P (HCOOH)=3.59; Mass (M+H.sup.+): 340.0; .sup.1HNMR (D.sub.6-DMSO): 8.16 (dd, 1H), 7.66 (s, 1H), 7.54 (t, 1H), 6.69 (dd, 1H), 6.61 (d, 1H), 4.84 (s, 2H), 4.22 (s, 2H), 1.32 (s, 9H).

2-[(2-Chlorothiazol-5-yl)methyl-(2-pyridyl)amino]acetic Acid (V-1-001)

[0721] ##STR00028##

[0722] 2.72 ml (35.3 mmol) of trifluoroacetic acid were added dropwise to a solution of 600 mg (1.76 mmol) of tert-butyl 2-[(2-chlorothiazol-5-yl)methyl-(2-pyridyl)amino]acetate in 4.8 ml of dichloromethane. The reaction mixture was stirred at 0 C. for 16 h, concentrated and dried azeotropically with toluene. Without further purification, the light-brown residue was reacted further to compounds of the formula (I). HPLC-MS: log P (HCOOH)=1.21; Mass (M+H.sup.+): 284.0; .sup.1HNMR (D.sub.6-DMSO): 8.14 (d, 1H), 7.72-7.70 (m, 2H), 6.85-6.80 (m, 2H), 4.94 (s, 2H), 4.33 (s, 2H). (comment: COOH not visible here.)

1-[(2-Chlorothiazol-5-yl)methyl]-2-(2,2,2-trichloroacetyl)imidazo[1,2-a]pyridin-4-ium-3-olate (I-011)

[0723] ##STR00029##

[0724] First, 3.86 ml (21.1 mmol) of (2,2,2-trichloroacetyl) 2,2,2-trichloroacetate and then, at 0 C., 0.589 ml (4.22 mmol) of triethylamine were added to a solution of 300 mg (1.05 mmol) of 2-[(2-chlorothiazol-5-yl)methyl-(2-pyridyl)amino]acetic acid in 2.0 ml of dichloromethane, and the mixture was stirred at 0 C. for 16 h. The reaction mixture was diluted with dichloromethane and quenched with water and the organic phase was separated off and then concentrated. The residue was purified by column chromatography on silica gel (CH.sub.2Cl.sub.2/MeOH=10/1). HPLC-MS: log P (HCOOH)=2.44; Mass (M+H.sup.+): 410.0; .sup.1HNMR (D.sub.6-DMSO): 8.45 (d, 1H), 8.12 (d, 1H), 8.00 (dd, 1H), 7.89 (s, 1H), 7.19 (t, 1H), 5.91 (s, 2H). 1-[(2-Chlorothiazol-5-yl)methyl]-2-(isopropylcarbamoyl)imidazo[1,2-a]pyridin-4-ium-3-olate (I-025)

##STR00030##

[0725] At RT, 15 l (0.17 mmol) of isopropylamine were added to 60 mg (0.05 mmol) of 1-[(2-chlorothiazol-5-yl)methyl]-2-(2,2,2-trichloroacetyl)imidazo[1,2-a]pyridin-4-ium-3-olate in 8.0 ml of tetrahydrofuran. The reaction mixture was stirred at RT for 16 h and then concentrated and the residue was purified by column chromatography on silica gel (CH.sub.2Cl.sub.2/MeOH=10/1). HPLC-MS: log P (HCOOH)=1.66; Mass (M+H.sup.+): 351.0; .sup.1HNMR (CDCl.sub.3): 8.44 (d, 1H), 8.31 (d, 1H), 7.61 (s, 1H), 7.58 (dd, 1H), 7.42 (d, 1H), 7.05 (dt, 1H), 6.04 (s, 2H), 4.29 (sept, 1H), 1.31 (d, 6H).

2-(2-Chloroacetyl)-1-[(2-chlorothiazol-5-yl)methyl]imidazo[1,2-a]pyridin-4-ium-3-olate (I-005)

[0726] ##STR00031##

[0727] A solution of 90 mg (0.31 mmol) of 2-[(2-chlorothiazol-5-yl)methyl-(2-pyridyl)amino]acetic acid in 1.0 ml of chloroacetic anhydride was cooled to 0 C., and 0.18 ml (1.26 mmol) of triethylamine was added dropwise. The mixture was stirred at 0 C. for 16 h, then diluted with dichloromethane and applied to silica gel. The crude product was then purified by column chromatography on silica gel (CH.sub.2Cl.sub.2/MeOH=10/1). HPLC-MS: log P (HCOOH)=1.58; Mass (M+H.sup.+): 341.9; .sup.1HNMR (D.sub.6-DMSO): 8.43 (d, 1H), 8.09 (d, 1H), 7.92 (dd, 1H), 7.88 (s, 1H), 7.16 (t, 1H), 5.93 (s, 2H), 4.89 (s, 2H).

1-[(2-Chlorothiazol-5-yl)methyl]-2-(2-methoxyacetyl)imidazo[1,2-a]pyridin-4-ium-3-olate (I-010)

[0728] ##STR00032##

[0729] A solution of 50 mg (0.14 mmol) of 2-(2-chloroacetyl)-1-[(2-chlorothiazol-5-yl)methyl]imidazo[1,2-a]pyridin-4-ium-3-olate in 5.0 ml of tetrahydrofuran was cooled to 0 C., and 5.88 ml (0.43 mmol) of a methanolic solution of sodium methoxide were added dropwise. The reaction mixture was stirred for 16 h and allowed to warm to 15 C. during this time. By addition of 1.0 M aqueous hydrochloric acid solution, the pH was adjusted to 7. The mixture was then concentrated and the residue was purified by HPLC (MeCN/H.sub.2O). HPLC-MS: log P (HCOOH)=1.13; Mass (M+H.sup.+): 338.0; .sup.1HNMR (CDCl.sub.3): 8.43 (d, 1H), 7.71 (dd, 1H), 7.61 (s, 1H), 7.39 (d, 1H), 7.03 (t, 1H), 5.89 (s, 2H), 4.77 (s, 2H), 3.56 (s, 3H).

2-[2-(4-Chloropyrazol-1-yl)acetyl]-1-[(2-chlorothiazol-5-yl)methyl]imidazo[1,2-a]pyridin-4-ium-3-olate (I-004)

[0730] ##STR00033##

[0731] A mixture of 23 mg (0.23 mmol) of 4-chloro-1H-pyrazole and 98 mg (0.30 mmol) of caesium carbonate in 1.0 ml of dimethylformamide was added to a solution of 50 mg (0.15 mmol) of 2-(2-chloroacetyl)-1-[(2-chlorothiazol-5-yl)methyl]imidazo[1,2-a]pyridin-4-ium-3-olate in 1.0 ml of dimethylformamide. The reaction mixture was then stirred at 15 C. for 12 h, filtered through Celite and concentrated. The crude product was subsequently purified by HPLC (MeCN/H.sub.2O). HPLC-MS: log P (HCOOH)=1.83; Mass (M+H.sup.+): 408.0; .sup.1HNMR (CDCl.sub.3): 8.46 (d, 1H), 7.75 (t, 1H), 7.56 (s, 2H), 7.51 (s, 1H), 7.38 (d, 1H), 7.07 (t, 1H), 5.84 (s, 2H), 5.58 (s, 2H).

1-[(2-Chlorothiazol-5-yl)methyl]-2-formylimidazo[1,2-a]pyridin-4-ium-3-olate (I-015)

[0732] ##STR00034##

[0733] 780 mg (4.93 mmol) of 2-oxopropanoic anhydride were added to a solution of 70 mg (0.24 mmol) of 2-[(2-chlorothiazol-5-yl)methyl-(2-pyridyl)amino]acetic acid in 0.47 ml of dichloromethane. The mixture was subsequently cooled to 0 C., 0.14 ml (0.98 mmol) of triethylamine was added dropwise and the mixture was stirred at 0 C. for 16 h. The dark-blue solution was diluted with dichloromethane, quenched with a few drops of water with vigorous stirring and then concentrated. The crude product was purified by column chromatography on silica gel (CH.sub.2Cl.sub.2/MeOH, 10/1). Instead of the expected reaction product 1-[(2-chlorothiazol-5-yl)methyl]-2-(2-oxopropanoyl)imidazo[1,2-a]pyridin-4-ium-3-olate, the aldehyde (I-015) shown above was obtained. HPLC-MS: log P (HCOOH)=1.01; Mass (M+H.sup.+): 293.9; .sup.1HNMR (D.sub.6-DMSO): 9.47 (s, 1H), 8.42 (d, 1H), 8.04 (d, 1H), 7.91 (dd, 1H), 7.87 (s, 1H), 7.13 (t, 1H), 5.88 (s, 2H).

tert-Butyl 2-[(2-chlorothiazol-5-yl)methyl-(3-methyl-2-pyridyl)amino]acetate

[0734] ##STR00035##

[0735] At 0 C., a solution of 2.00 g (13.2 mmol) of N-[(2-chlorothiazol-5-yl)methyl]-3-methylpyridine-2-amine in 5 ml of DMF was added to a suspension of 0.83 g (20.8 mmol, 60% pure) of sodium hydride in 20 ml of DMF. The mixture was stirred at 0 C. for 1.5 h, a solution of 5.19 g (26.5 mmol) of tert-butyl 2-bromoacetate in 5 ml of DMF was then added dropwise and the resulting mixture was stirred at RT for 16 h. The reaction mixture was stirred into saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The phases were separated and the combined organic phases were washed with saturated aqueous NaCl solution and concentrated. The residue was purified by column chromatography on silica gel (cyclohexane/ethyl acetate, 1/1). HPLC-MS: log P (HCOOH)=4.13; Mass (M+H.sup.+): 353.1; .sup.1HNMR (D.sub.6-DMSO): 8.08 (d, 1H) 7.61 (s, 1H) 7.49 (d, 1H) 6.89 (dd, 1H) 4.62 (s, 2H) 3.89 (s, 2H) 2.23 (s, 3H) 1.31 (s, 9H).

1-[(2-Chlorothiazol-5-yl)methyl]-8-methylimidazo[1,2-a]pyridin-4-ium-3-ol; 2,2,2-trifluoroacetate (VII-1-001)

[0736] ##STR00036##

[0737] 2.72 ml (31.0 mmol) of trifluoroacetic acid were added dropwise to a solution of 550 mg (1.76 mmol) of tert-butyl 2-[(2-chlorothiazol-5-yl)methyl-(2-pyridyl)amino]acetate in 4.0 ml of dichloromethane. The reaction mixture was stirred at 0 C. for 1 h and then at 20 C. for 16 h, concentrated and dried azeotropically with toluene. Without further purification, the light-brown residue was reacted further to compounds of the formula (I). HPLC-MS: log P (HCOOH)=0.75; Mass (M+H.sup.+): 280.0; .sup.1HNMR (D.sub.6-DMSO): 8.43 (d, 1H) 7.61-7.70 (m, 2H) 7.30-7.43 (m, 2H) 5.95 (s, 2H) 2.71 (s, 3H).

1-[(2-Chlorothiazol-5-yl)methyl]-8-methyl-2-(2,2,2-trifluoroacetyl)imidazo[1,2-a]pyridin-4-ium-3-olate (I-024)

[0738] ##STR00037##

[0739] A solution of 160 mg (0.40 mmol) of 1-[(2-chlorothiazol-5-yl)methyl]-8-methylimidazo[1,2-a]pyridin-4-ium-3-ol; 2,2,2-trifluoroacetate in 1.15 ml of trifluoroacetic anhydride was cooled to 0 C., and 0.23 ml (1.62 mmol) of triethylamine was added dropwise. The mixture was stirred at 0 C. for 0.5 h and at 20 C. for 16 h, then diluted with dichloromethane and applied to silica gel. The crude product was then purified by column chromatography on silica gel (CH.sub.2Cl.sub.2/MeOH=10/1). HPLC-MS: log P (HCOOH)=2.07; Mass (M+H.sup.+): 375.0; .sup.1HNMR (D.sub.6-DMSO): 8.36 (d, 1H) 7.83 (d, 1H) 7.64 (s, 1H) 7.16 (dd, 1H) 6.00 (s, 2H) 2.66 (s, 3H).

tert-butyl 2-[(2-chlorothiazol-5-yl)iodo-(3-iodo-2-pyridyl)amino]acetate (IV-2-002)

[0740] ##STR00038##

[0741] At 0 C., a solution of 3.00 g (8.53 mmol) of N-[(2-chlorothiazol-5-yl)methyl]-3-iodo-pyridine-2-amine in 5 ml of DMF was added to a suspension of 0.375 g (9.38 mmol, 60% pure) of sodium hydride in 10 ml of DMF. The mixture was stirred at 0 C. for 1.5 h, a solution of 1.81 g (9.38 mmol) of tert-butyl 2-bromacetate in 5 ml of DMF was then added dropwise and the resulting mixture was stirred at RT for 20 h. The reaction mixture was stirred into saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The phases were separated and the combined organic phases were washed with saturated aqueous NaCl solution and concentrated. The residue was purified by column chromatography on silica gel (cyclohexane/ethyl acetate, 1/1). HPLC-MS: log P (HCOOH)=4.62; Mass (M+H.sup.+): 465.8; .sup.1HNMR (D.sub.6-DMSO): 8.26 (dd, 1H), 8.21 (dd, 1H), 7.61 (s, 1H), 6.77 (dd, 1H), 4.70 (s, 2H), 4.04 (s, 2H), 1.30 (s, 9H).

1-[(2-chlorothiazol-5-yl)methyl]-8-iodoimidazo[1,2-a]pyridin-4-ium-3-ol 2,2,2-trifluoroacetate (VII-1-002)

[0742] ##STR00039##

[0743] 2.00 ml (25.7 mmol) of trifluoroacetic acid were added dropwise to a solution of 600 mg (1.28 mmol) of tert-butyl 2-[(2-chlorothiazol-5-yl)iodo-(2-pyridyl)amino]acetate in 4.0 ml of dichloromethane. The reaction mixture was stirred at 0 C. for 1 h and then at 20 C. for 16 h, concentrated and dried azeotropically with toluene. Without further purification, the light-brown residue was converted further into compounds of the formula (I). HPLC-MS: log P (HCOOH)=1.22; Mass (M+H.sup.+): 391.8.

1-[(2-chlorothiazol-5-yl)methyl]-8-iodo-2-(2,2,2-trifluoroacetyl)imidazo[1,2-a]pyridin-4-ium-3-olate (I-112)

[0744] ##STR00040##

[0745] A solution of 750 mg (1.4 mmol) of 1-[(2-chlorothiazol-5-yl)methyl]-8-iodo-imidazo[1,2-a]pyridin-4-ium-3-ol 2,2,2-trifluoracetate in 4.18 ml of trifluoroacetic anhydride was cooled to 0 C., and 0.83 ml (5.93 mmol) of triethylamine was added dropwise. The mixture was stirred at 0 C. for 0.5 h and at 20 C. for 16 h and then diluted with dichloromethane and applied to silica gel. The crude product was subsequently purified by column chromatography on silica gel (CH.sub.2Cl.sub.2/MeOH=10/1). HPLC-MS: log P (HCOOH)=2.37; Mass (M+H.sup.+): 487.7; .sup.1HNMR (D.sub.6-DMSO): 8.57 (dd, 1H), 8.51 (dd, 1H), 7.57 (s, 1H), 6.97 (t, 1H), 6.31 (s, 2H).

tert-butyl 2-[(2-chlorothiazol-5-yl)cyclopropyl-(3-cyclopropyl-2-pyridyl)amino]acetate (IV-2-003)

[0746] ##STR00041##

[0747] 0.32 g (2.14 mmol) of potassium cyclopropyltrifluoroborate, 0.11 g (1.07 mmol) of bis(triphenylphosphine)palladium chloride and 0.30 g (2.14 mmol) of potassium carbonate were added to a solution of 0.50 g (1.07 mmol) of tert-butyl 2-[(2-chlorothiazol-5-yl)iodo-(3-iodo-2-pyridyl)amino]acetate in 3 ml of toluene and 1 ml of water. The mixture was stirred at 100 C. for 4 h. The reaction mixture was stirred into water and extracted with dichloromethane. The phases were separated and the combined organic phases were washed with saturated aqueous NaCl solution and concentrated. The residue was purified by column chromatography on silica gel (cyclohexane/ethyl acetate, 1/1). HPLC-MS: log P (HCOOH)=4.73; Mass (M+H.sup.+): 380.2;

1-[(2-chlorothiazol-5-yl)methyl]-8-cyclopropylimidazo[1,2-a]pyridin-4-ium-3-ol 2,2,2-trifluoroacetate (VII-1-003)

[0748] ##STR00042##

[0749] 0.72 ml (9.47 mmol) of trifluoroacetic acid was added dropwise to a solution of 180 mg (1.76 mmol) of tert-butyl 2-[(2-chlorothiazol-5-yl)cyclopropyl-(2-pyridyl)amino]acetate in 3.0 ml of dichloromethane. The reaction mixture was stirred at 0 C. for 1 h and then at 20 C. for 16 h, concentrated and dried azeotropically with toluene. Without further purification, the light-brown residue was converted further into compounds of formula (I). HPLC-MS: log P (HCOOH)=1.27; Mass (M+H.sup.+): 306.0.

1-[(2-chlorothiazol-5-yl)methyl]-8-cyclopropyl-2-(2,2,2-trifluoroacetyl)imidazo[1,2-a]pyridin-4-ium-3-olate (I-078)

[0750] ##STR00043##

[0751] A solution of 160 mg (0.40 mmol) of 1-[(2-chlorothiazol-5-yl)methyl]-8-methyl-imidazo[1,2-a]pyridin-4-ium-3-ol 2,2,2-trifluoroacetate in 1.34 ml of trifluoroacetic anhydride was cooled to 0 C., and 0.27 ml (1.90 mmol) of triethylamine was added dropwise. The mixture was stirred at 0 C. for 0.5 h and at 20 C. for 16 h and then diluted with dichloromethane and applied to silica gel. The crude product was then purified by column chromatography on silica gel (CH.sub.2Cl.sub.2/iso-PrOH=10/1). HPLC-MS: log P (HCOOH)=2.48; Mass (M+H.sup.+): 375.0; .sup.1HNMR (D.sub.6-DMSO): 8.35 (d, 1H), 7.80 (d, 1H), 7.62 (s, 1H), 7.14 (t, 1H), 6.30 (s, 2H), 2.25 (m, 1H), 1.04-1.16 (m, 2H), 0.87-1.00 (m, 2H).

1-[(2-chlorothiazol-5-yl)methyl]-8-phenyl-2-(2,2,2-trifluoroacetyl)imidazo[1,2-a]pyridin-4-ium-3-olate (I-109)

[0752] ##STR00044##

[0753] 0.026 g (0.21 mmol) of benzeneboronic acid, 0.020 g (0.02 mmol) of bis(triphenylphosphine)palladium chloride and 0.18 ml (0.35 mmol) of an aqueous 2.0 M solution of sodium bicarbonate were added to a solution of 0.070 g (0.14 mmol) of 1-[(2-chlorothiazol-5-yl)methyl]-8-iodo-2-(2,2,2-trifluoroacetyl)imidazo[1,2-a]pyridin-4-ium-3-olate in 5 ml of dioxane. The mixture was stirred at 100 C. for 16 h. The reaction mixture was stirred into water and extracted with dichloromethane. The phases were separated and the combined organic phases were washed with saturated aqueous NaCl solution and concentrated. The residue was purified by column chromatography on silica gel (cyclohexane/ethyl acetate, 1/1). HPLC-MS: log P (HCOOH)=2.99; Mass (M+H.sup.+): 438.0; .sup.1HNMR (D.sub.6-DMSO): 8.56 (dd, 1H), 7.86 (dd, 1H), 7.52-7.63 (m, 5H), 7.34 (t, 1H), 6.91 (s, 1H), 5.35 (br s, 2H).

1-[(2-chlorothiazol-5-yl)methyl]-2-(2-ethoxy-2-oxoacetyl)imidazo[1,2-a]pyridin-4-ium-3-olate (I-029)

[0754] ##STR00045##

[0755] At 0 C., 221 l of triethylamine (1.58 mmol) and 129 mg of ethyl chlorooxoacetate (0.95 mmol) were added to a solution of 90 mg of 2-[(2-chlorothiazol-5-yl)methyl-(2-pyridyl)amino]acetic acid (0.31 mmol) in dichloromethane (0.45 ml). The reaction mixture was stirred at this temperature for 16 h and then, after warming to RT, freed from the solvent on a rotary evaporator. The residue was dissolved in ethyl acetate and washed with NH.sub.4Cl solution. The organic phase was dried over Na.sub.2SO.sub.4 and concentrated. The residue was purified by column chromatography on silica gel (SiO.sub.2, cyclohexane/ethyl acetate). The product was obtained as a yellow solid.

[0756] HPLC-MS: log P (HCOOH)=1.55; Mass (M+H.sup.+): 366.0; .sup.1HNMR (D.sub.6-DMSO): 8.37 (d, 1H), 8.07 (d, 1H), 7.99-7.95 (m, 1H), 7.88 (s, 1H), 7.16 (t, 1H), 5.87 (s, 2H), 4.28 (q, 2H), 1.29 (t, 3H).

2-(2-chloro-2-oxoacetyl)-1-[(2-chlorothiazol-5-yl)methyl]imidazo[1,2-a]pyridin-4-ium-3-olate (Ih-001)

[0757] ##STR00046##

[0758] At 0 C., 200 mg of 2-[(2-chlorothiazol-5-yl)methyl-(2-pyridyl)amino]acetic acid (0.70 mmol) were added to a solution of 3.52 ml of oxalyl chloride (2.0 M, 7.04 mmol) in dichloromethane (3.00 ml). 196 l of triethylamine (1.41 mmol) were then added dropwise. The mixture was stirred at 0 C. for 3 h and then concentrated, taking care that the temperature did not exceed 30 C. Without further purification, the crude product was converted further (for example into (I-034)).

1-[(2-chlorothiazol-5-yl)methyl]-2-[2-(cyclopropylmethoxy)-2-oxoacetyl]imidazo[1,2-a]pyridin-4-ium-3-olate (I-034)

[0759] ##STR00047##

[0760] At 0 C., 147 l of triethylamine (1.05 mmol) and 0.88 ml of cyclopropylcarbinol (1.76 mmol) were added to a solution of 125 mg of 2-(2-chloro-2-oxoacetyl)-1-[(2-chlorothiazol-5-yl)methyl]imidazo[1,2-a]pyridin-4-ium-3-olate (0.35 mmol) in dichloromethane (5.0 ml). The reaction mixture was stirred at this temperature for 16 h and then, after warming to RT, freed from the solvent on a rotary evaporator. The residue was dissolved in ethyl acetate and washed with NH.sub.4Cl solution. The organic phase was dried over Na.sub.2SO.sub.4 and concentrated. The residue was purified by column chromatography on silica gel (SiO.sub.2, cyclohexane/ethyl acetate). The product was obtained as a yellow solid.

[0761] HPLC-MS: log P (HCOOH)=1.94; Mass (M+H.sup.+): 392.0; .sup.1HNMR (D.sub.6-DMSO): 8.37 (d, 1H), 8.07 (d, 1H), 7.99-7.94 (m, 1H), 7.89 (s, 1H), 7.15 (t, 1H), 5.87 (s, 2H), 4.06 (d, 2H), 1.19-1.14 (m, 1H), 0.57-0.56 (m, 2H), 0.35-0.33 (m, 2H).

(2E)-2-methoxyiminoacetyl Chloride

[0762] ##STR00048##

[0763] 155 l of oxalyl chloride (1.74 mmol) were added to a solution of 180 mg of (2E)-2-methoxyiminoacetic acid (1.74 mmol) in 3.6 ml of dichloromethane. The reaction mixture was stirred at room temperature for 4 h and then concentrated. Without further purification, the crude product was converted further (for example into compound I-059).

1-[(2-chlorothiazol-5-yl)methyl]-2-[(2E)-2-methoxyiminoacetyl]imidazo[1,2-a]pyridin-4-ium-3-olate (I-059)

[0764] ##STR00049##

[0765] At 0 C., 239 mg of (2E)-2-methoxyiminoacetyl chloride (2.37 mmol) were added to a solution of 450 mg of 2-[(2-chlorothiazol-5-yl)methyl-(2-pyridyl)amino]acetic acid hydrochloride (1.58 mmol) in dichloromethane (3.33 ml). The solution was cooled to 15 C., 1.11 ml of triethylamine (7.93 mmol) were added and the mixture was stirred for 1 h. The reaction mixture was freed from the solvent on a rotary evaporator and then purified by column chromatography on silica gel (SiO.sub.2, cyclohexane/ethyl acetate). The desired product was obtained as a bright-yellow solid.

[0766] HPLC-MS: log P (HCOOH)=1.45; Mass (M+H.sup.+): 351.0; .sup.1HNMR (D.sub.6-DMSO): 8.99 (s, 1H), 8.42 (d, 1H), 8.09 (d, 1H), 7.97-7.91 (m, 1H), 7.88 (s, 1H), 7.17-7.14 (m, 1H), 5.95 (s, 2H), 3.97 (s, 3H).

2-(2-bromoacetyl)-1-[(6-chloro-3-pyridyl)methyl]imidazo[1,2-a]pyridin-4-ium-3-olate (I-113)

[0767] ##STR00050##

[0768] At 0 C., 221 l of triethylamine (1.58 mmol) and 285 mg of 2-bromoacetyl bromide (1.42 mmol) were added to a solution of 200 mg of 2-[(2-chlorothiazol-5-yl)methyl-(2-pyridyl)amino]acetic acid (0.71 mmol) in dichloromethane (1.0 ml). The reaction mixture was warmed to room temperature and stirred for 16 h. The mixture was then concentrated on a rotary evaporator and immediately purified by column chromatography on silica gel (SiO.sub.2, cyclohexane/ethyl acetate). The resulting product I-113 could be converted into further compounds of the formula 1 (for example into compound I-084).

2-[2-[(2-chloro-4-pyridyl)methoxy]acetyl]-1-[(6-chloro-3-pyridyl)methyl]imidazo[1,2-a]pyridin-4-ium-3-olate (I-084)

[0769] ##STR00051##

[0770] At 0 C. 290 l of LiHMDS (1.0 M, 0.29 mmol) were added to a solution of 37 mg of (2-chloro-4-pyridyl)methanol (0.26 mmol) in 0.3 ml of tetrahydrofuran and the mixture was stirred at this temperature for 30 min. The resulting LiHMDS solution was then, at 0 C., added to a solution of 50 mg of 2-(2-bromoacetyl)-1-[(6-chloro-3-pyridyl)methyl]imidazo[1,2-a]pyridin-4-ium-3-olate (0.13 mmol) in tetrahydrofuran. The reaction mixture was stirred at this temperature for 3 h. An NH.sub.4Cl solution was then added and the product was extracted with ethyl acetate (3), dried over Na.sub.2SO.sub.4 and concentrated. The crude product was purified by HPLC (H.sub.2O/MeOH).

[0771] HPLC-MS: log P (HCOOH)=1.73; .sup.1HNMR (D.sub.6-DMSO): 8.41-8.33 (m, 3H), 7.93 (d, 1H), 7.85-7.81 (m, 1H), 7.66 (d, 1H), 7.47-7.44 (m, 2H), 7.39 (d, 1H), 7.14-7.11 (m, 1H), 5.86 (s, 2H), 4.72 (s, 2H), 4.65 (s, 2H).

[0772] The compounds according to the invention described in Table 1 below are likewise preferred compounds of the formula (I) according to the invention which are obtained according to or analogously to the Synthesis Examples described above. They are based on the substructure of the formula (I-1).

TABLE-US-00007 TABLE 1 (I-1) [00052] embedded image Example No. Structure I-001 [00053] I-002 [00054] I-003 [00055] I-004 [00056] I-005 [00057] I-006 [00058] I-007 [00059] I-008 [00060] I-009 [00061] I-010 [00062] I-011 [00063] I-012 [00064] I-013 [00065] I-014 [00066] I-015 [00067] I-016 [00068] I-017 [00069] I-018 [00070] I-019 [00071] embedded image I-020 [00072] I-021 [00073] I-022 [00074] I-023 [00075] I-024 [00076] I-025 [00077] I-026 [00078] I-027 [00079] I-028 [00080] I-029 [00081] I-030 [00082] I-031 [00083] I-032 [00084] I-033 [00085] I-034 [00086] I-035 [00087] I-036 [00088] I-037 [00089] I-038 [00090] I-039 [00091] I-040 [00092] embedded image I-041 [00093] I-042 [00094] I-043 [00095] I-044 [00096] I-045 [00097] I-046 [00098] I-047 [00099] I-048 [00100] I-049 [00101] I-050 [00102] I-051 [00103] I-052 [00104] I-053 [00105] I-054 [00106] I-055 [00107] I-056 [00108] I-057 [00109] I-058 [00110] I-059 [00111] I-060 [00112] I-061 [00113] embedded image I-062 [00114] I-063 [00115] I-065 [00116] I-066 [00117] I-068 [00118] I-069 [00119] I-070 [00120] I-071 [00121] I-072 [00122] I-073 [00123] I-074 [00124] I-075 [00125] I-076 [00126] I-077 [00127] I-078 [00128] I-079 [00129] I-080 [00130] I-082 [00131] I-084 [00132] I-085 [00133] I-086 [00134] embedded image I-087 [00135] I-088 [00136] I-089 [00137] I-090 [00138] I-092 [00139] I-093 [00140] I-095 [00141] I-097 [00142] I-098 [00143] I-100 [00144] I-101 [00145] I-103 [00146] I-106 [00147] I-108 [00148] I-109 [00149] I-111 [00150]

[0773] .sup.1H NMR Data of the Compounds According to Table 1

[0774] The determination of the [M+H].sup.+ by LC-MS in the acidic range was carried out at pH 2.7 using the mobile phases acetonitrile (containing 0.1% formic acid) and water; linear gradient from 10% acetonitrile to 95% acetonitrile, instrument: Agilent 1100 LC system, Agilent MSD system, HTS PAL.

[0775] The log P values reported in the tables and preparation examples above were determined in accordance with EEC directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) using a reversed-phase column (C18). Temperature 43 C. The calibration is effected with unbranched alkan-2-ones (having 3 to 16 carbon atoms), for which the log P values are known.

[0776] The determination of the .sup.1H NMR data was effected with a Bruker Avance 400 or Bruker Avance III 600 equipped with a sample flow head (capacity 60 l), with tetramethylsilane as reference (0.0) and the solvents CD.sub.3CN, CDCl.sub.3 or D.sub.6-DMSO.

[0777] The NMR data of selected examples are listed either in conventional form (6 values, multiplet splitting, number of hydrogen atoms) or as NMR peak lists.

[0778] NMR Data of Selected Examples

[0779] NMR Peak List Method

[0780] 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 value in ppm and then the signal intensity in round brackets are listed. The pairs of value-signal intensity numbers for different signal peaks are listed with separation from one another by semicolons.

[0781] The peak list for one example therefore takes the form of:

.sub.1 (intensity.sub.1); .sub.2 (intensity.sub.2); . . . ; .sub.i (intensity.sub.i); . . . ; n (intensity.sub.n)

[0782] 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.

[0783] For calibration of the chemical shift of .sup.1H NMR spectra, we use 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.

[0784] 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.

[0785] In addition, like conventional .sup.1H NMR printouts, they may show solvent signals, signals of stereoisomers of the target compounds which are likewise provided by the invention, and/or peaks of impurities.

[0786] 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.

[0787] 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%).

[0788] 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.

[0789] A person skilled in the art 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.

[0790] Further details of .sup.1H NMR peak lists can be found in the Research Disclosure Database Number 564025. Ignore the box

[0791] NMR Data

[0792] I-001: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0793] =8.9387 (0.3); 8.4487 (2.3); 8.4318 (2.3); 8.3706 (3.2); 8.3649 (3.2); 7.9534 (1.7); 7.9305 (3.1); 7.8888 (1.6); 7.8720 (1.6); 7.8512 (0.9); 7.6724 (1.6); 7.6662 (1.7); 7.6517 (2.0); 7.6454 (2.0); 7.4661 (3.6); 7.4454 (3.0); 7.2406 (0.5); 7.1626 (1.4); 7.1461 (2.5); 7.1300 (1.3); 7.1126 (0.6); 6.9852 (0.5); 5.8288 (8.6); 4.7941 (16.0); 3.9029 (8.1); 3.8080 (1.0); 3.4071 (1.2); 3.3301 (72.2); 3.1688 (2.1); 2.6718 (0.7); 2.6677 (0.5); 2.5072 (96.7); 2.5028 (125.9); 2.4984 (94.8); 2.3297 (0.7); 2.3253 (0.6); 1.9986 (0.7); 1.2342 (1.0); 0.0002 (1.7)

[0794] I-002: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0795] =8.4389 (4.3); 8.4220 (4.4); 8.3710 (5.6); 8.3655 (5.7); 7.9888 (1.0); 7.9653 (3.5); 7.9460 (7.2); 7.9229 (1.4); 7.6885 (2.8); 7.6824 (2.9); 7.6678 (3.4); 7.6617 (3.4); 7.4832 (6.3); 7.4626 (5.3); 7.1770 (2.1); 7.1618 (3.8); 7.1476 (1.9); 7.1447 (1.9); 5.7462 (16.0); 3.9030 (9.0); 3.3276 (168.5); 3.1689 (1.3); 2.6723 (1.1); 2.5027 (207.4); 2.3297 (1.2); 1.2352 (0.8); 1.2133 (0.4); 1.1968 (0.3); 00.0000 (2.3)

[0796] I-003: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0797] =8.4257 (1.6); 8.4088 (1.7); 8.3538 (2.2); 8.3480 (2.3); 7.9101 (1.3); 7.8870 (2.1); 7.8276 (1.0); 7.8107 (1.1); 7.7884 (0.7); 7.6326 (1.1); 7.6267 (1.1); 7.6120 (1.4); 7.6059 (1.4); 7.4510 (2.6); 7.4303 (2.1); 7.1302 (1.0); 7.1136 (1.9); 7.0967 (0.9); 5.8507 (6.4); 3.9033 (3.4); 3.3285 (64.4); 2.6723 (0.4); 2.5074 (59.4); 2.5032 (75.7); 2.4990 (57.4); 2.4248 (16.0); 2.3297 (0.4); 0.0001 (0.9)

[0798] I-004: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0799] =8.4702 (3.3); 8.4533 (3.4); 8.0962 (2.8); 8.0732 (3.8); 7.9963 (9.1); 7.9452 (2.0); 7.9279 (2.1); 7.9075 (1.5); 7.8541 (8.9); 7.5568 (9.2); 7.1881 (2.1); 7.1710 (3.9); 7.1546 (2.0); 5.8935 (10.8); 5.5163 (16.0); 3.9030 (14.4); 3.5087 (0.3); 3.3287 (193.5); 3.2679 (0.3); 3.1756 (0.6); 3.1628 (0.6); 2.6765 (0.9); 2.6720 (1.2); 2.6677 (0.9); 2.5074 (164.0); 2.5030 (214.4); 2.4986 (158.5); 2.3340 (0.8); 2.3296 (1.2); 2.3253 (0.9); 1.3515 (0.4); 1.2983 (0.4); 1.2836 (0.6); 1.2581 (0.4); 1.2347 (1.7); 0.8944 (0.4); 0.8761 (0.8); 0.8627 (0.6); 0.8573 (0.6); 0.0001 (2.4)

[0800] I-005: .sup.1H-NMR (601.6 MHz, d.sub.6-DMSO):

[0801] =8.4301 (2.1); 8.4189 (2.2); 8.0903 (1.9); 8.0749 (2.3); 7.9379 (1.1); 7.9361 (1.1); 7.9266 (1.2); 7.9247 (1.3); 7.9229 (1.2); 7.9208 (1.0); 7.9114 (1.0); 7.9095 (1.0); 7.8791 (5.3); 7.1659 (1.3); 7.1548 (2.4); 7.1435 (1.2); 5.9541 (0.3); 5.9302 (7.8); 4.8252 (16.0); 3.9010 (1.1); 3.3111 (145.7); 2.6157 (0.7); 2.6127 (1.0); 2.6096 (0.7); 2.5219 (2.0); 2.5188 (2.6); 2.5157 (2.9); 2.5068 (60.5); 2.5039 (125.5); 2.5009 (171.6); 2.4979 (130.5); 2.4950 (65.3); 2.3881 (0.7); 2.3851 (1.0); 2.3821 (0.8); 1.9083 (0.5); 0.8763 (0.4); 0.8632 (0.4); 0.0002 (4.0)

[0802] I-006: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0803] =8.4847 (3.4); 8.4678 (3.5); 8.3359 (4.4); 8.3301 (4.5); 7.9460 (2.3); 7.9229 (5.1); 7.9164 (10.2); 7.8909 (2.4); 7.8753 (2.4); 7.8523 (1.2); 7.6556 (2.4); 7.6494 (2.4); 7.6348 (2.9); 7.6286 (2.8); 7.5075 (9.7); 7.4524 (5.2); 7.4317 (4.3); 7.1795 (2.0); 7.1629 (3.7); 7.1464 (1.8); 5.7893 (10.9); 5.4802 (16.0); 4.0886 (0.3); 3.9028 (13.7); 3.3278 (252.4); 3.1753 (1.5); 3.1621 (1.4); 2.6756 (0.8); 2.6713 (1.1); 2.6671 (0.8); 2.5067 (147.5); 2.5023 (189.6); 2.4980 (140.2); 2.3333 (0.8); 2.3292 (1.1); 1.2349 (0.3); 0.0002 (1.8)

[0804] I-007: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0805] =8.4260 (4.0); 8.4090 (4.2); 8.0942 (2.7); 8.0713 (5.5); 8.0381 (2.9); 8.0215 (2.8); 7.9987 (1.4); 7.8801 (10.6); 7.6703 (0.3); 7.1890 (2.4); 7.1723 (4.5); 7.1557 (2.2); 5.8689 (16.0); 4.8464 (0.4); 4.2194 (0.4); 3.9031 (11.9); 3.6153 (0.3); 3.5082 (0.4); 3.3439 (99.4); 3.1694 (2.9); 2.6759 (1.0); 2.6723 (1.3); 2.5075 (178.6); 2.5032 (232.6); 2.4990 (177.6); 2.3300 (1.3); 1.2831 (0.5); 1.2347 (0.5); 1.1793 (0.7); 1.1613 (0.9); 1.1428 (0.4); 0.8760 (0.7); 0.8625 (0.5); 0.0002 (2.5)

[0806] I-008: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0807] =8.4101 (3.7); 8.3934 (3.8); 8.0644 (3.3); 8.0415 (4.1); 7.8935 (9.5); 7.8808 (2.2); 7.8636 (2.4); 7.8413 (1.7); 7.1380 (2.3); 7.1212 (4.3); 7.1043 (2.1); 5.9284 (14.9); 3.9033 (16.0); 3.5088 (0.4); 3.3290 (163.4); 3.1681 (0.4); 2.6724 (1.1); 2.6684 (0.8); 2.5075 (150.7); 2.5033 (194.2); 2.4991 (147.6); 2.4825 (37.7); 2.3299 (1.1); 1.2973 (0.4); 1.2835 (0.7); 1.2335 (0.6); 0.8943 (0.4); 0.8758 (1.1); 0.8616 (0.8); 0.8575 (0.7); 0.0003 (2.1)

[0808] I-009: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0809] =8.4100 (3.2); 8.3931 (3.4); 8.3698 (4.2); 8.3640 (4.3); 7.9380 (2.7); 7.9149 (4.1); 7.8423 (2.0); 7.8254 (2.2); 7.8024 (1.3); 7.6590 (2.2); 7.6528 (2.2); 7.6382 (2.7); 7.6320 (2.7); 7.4616 (5.0); 7.4410 (4.1); 7.1395 (2.0); 7.1228 (3.8); 7.1060 (1.8); 5.8481 (11.7); 4.5157 (16.0); 3.9031 (7.1); 3.3302 (189.0); 3.3053 (34.8); 2.6720 (0.9); 2.6679 (0.7); 2.5072 (120.8); 2.5030 (156.2); 2.4988 (119.0); 2.3298 (0.9); 2.3258 (0.7); 1.2350 (0.6); 0.8755 (0.4); 0.0002 (1.7)

[0810] I-010: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0811] =8.3963 (2.9); 8.3795 (3.0); 8.0854 (2.5); 8.0623 (3.1); 7.8968 (8.9); 7.8783 (2.0); 7.8571 (1.3); 7.1484 (1.8); 7.1315 (3.4); 7.1147 (1.6); 5.9441 (10.7); 4.5623 (16.0); 3.9035 (11.1); 3.3826 (31.8); 3.3292 (161.2); 3.2682 (0.5); 3.1758 (0.8); 3.1629 (0.8); 2.6725 (0.9); 2.6683 (0.7); 2.5075 (125.2); 2.5033 (158.4); 2.4990 (118.0); 2.3341 (0.7); 2.3299 (0.9); 2.3260 (0.7); 1.2988 (0.4); 1.2835 (0.6); 1.2346 (0.4); 0.8943 (0.4); 0.8761 (0.9); 0.8625 (0.6); 0.8576 (0.6); 0.0002 (1.7)

[0812] I-011: .sup.1H-NMR (400.0 MHz, CDCl3):

[0813] =8.4882 (3.6); 8.4714 (3.7); 7.8315 (1.5); 7.8120 (2.3); 7.7928 (1.8); 7.6109 (8.1); 7.4388 (3.4); 7.4160 (3.1); 7.2624 (40.3); 7.0928 (2.3); 7.0759 (4.4); 7.0589 (2.2); 5.8441 (16.0); 5.5704 (0.4); 1.6164 (6.8); 1.5202 (2.5); 0.0002 (1.4)

[0814] I-012: .sup.1H-NMR (601.6 MHz, CDCl3):

[0815] =9.1858 (6.1); 8.6894 (9.3); 8.5068 (3.6); 8.4956 (3.6); 7.8498 (1.9); 7.8477 (1.9); 7.8384 (2.1); 7.8362 (2.3); 7.8347 (2.4); 7.8325 (2.1); 7.8232 (2.2); 7.8211 (2.1); 7.3925 (4.2); 7.3772 (4.0); 7.2632 (17.9); 7.1110 (2.4); 7.1103 (2.3); 7.0998 (4.6); 7.0990 (4.5); 7.0885 (2.3); 7.0877 (2.3); 5.7872 (16.0); 5.2993 (3.5); 1.7868 (0.8); 1.2557 (0.8); 0.0699 (0.4); 0.0052 (0.4); 0.0002 (14.8); 0.0057 (0.5)

[0816] I-013: .sup.1H-NMR (601.6 MHz, d.sub.6-DMSO):

[0817] =19.9637 (0.7); 12.9166 (2.8); 8.3463 (4.4); 8.3352 (4.6); 8.0747 (4.2); 8.0591 (5.1); 7.9523 (4.7); 7.9403 (5.2); 7.9350 (11.7); 7.9117 (2.4); 7.9001 (2.6); 7.8850 (2.0); 7.7779 (7.5); 7.7665 (8.0); 7.7642 (6.6); 7.6541 (0.6); 7.6349 (1.1); 7.6227 (2.7); 7.6103 (1.7); 7.5236 (1.8); 7.5114 (5.9); 7.5011 (7.2); 7.4884 (2.7); 7.4398 (5.8); 7.4269 (9.1); 7.4145 (4.1); 7.1452 (2.9); 7.1343 (5.2); 7.1231 (2.7); 5.9760 (16.0); 5.7500 (12.8); 4.8608 (1.0); 4.3336 (1.2); 3.6150 (2.4); 3.3055 (17.6); 2.8915 (1.0); 2.7327 (0.8); 2.6130 (1.3); 2.5225 (2.6); 2.5192 (3.1); 2.5161 (3.4); 2.5073 (80.7); 2.5044 (171.2); 2.5014 (235.2); 2.4984 (171.2); 2.4957 (83.0); 2.3857 (1.4); 1.4258 (2.6); 1.2354 (0.8); 0.0964 (0.8); 0.0052 (4.8); 0.0002 (156.0); 0.0056 (5.5); 0.0999 (0.7)

[0818] I-014: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0819] =8.4087 (3.2); 8.3919 (3.3); 8.0678 (2.9); 8.0447 (3.8); 7.8960 (8.0); 7.8744 (1.8); 7.8717 (1.9); 7.8575 (2.0); 7.8546 (2.1); 7.8520 (1.8); 7.8487 (1.6); 7.8345 (1.5); 7.8318 (1.5); 7.5757 (0.4); 7.1349 (2.0); 7.1179 (3.8); 7.1011 (1.9); 5.9466 (12.0); 4.5851 (0.4); 4.5701 (0.4); 3.3232 (27.1); 2.9467 (2.3); 2.9281 (7.4); 2.9094 (7.6); 2.8908 (2.5); 2.6766 (0.4); 2.6722 (0.6); 2.6682 (0.5); 2.5076 (77.8); 2.5032 (102.2); 2.4988 (77.8); 2.3345 (0.5); 2.3299 (0.7); 2.3255 (0.5); 2.2210 (0.8); 2.2021 (0.9); 2.1832 (0.4); 1.4516 (1.4); 1.3522 (0.4); 1.2588 (0.6); 1.2338 (4.5); 1.2142 (0.4); 1.1968 (0.5); 1.1787 (0.9); 1.1604 (0.5); 1.1234 (7.8); 1.1048 (16.0); 1.0861 (7.6); 1.0078 (0.9); 0.9970 (0.5); 0.9890 (1.8); 0.9777 (0.4); 0.9702 (0.9); 0.8535 (0.6); 0.8353 (0.4); 0.0002 (8.2)

[0820] I-015: .sup.1H-NMR (600.1 MHz, DMF):

[0821] =9.5875 (3.9); 8.4848 (1.4); 8.4832 (1.0); 8.4736 (1.4); 8.4720 (1.0); 8.1754 (1.4); 8.1600 (1.7); 8.0259 (4.4); 8.0130 (0.9); 8.0110 (0.9); 8.0017 (0.9); 7.9996 (1.0); 7.9978 (0.9); 7.9957 (0.8); 7.9823 (3.4); 7.2366 (0.8); 7.2354 (0.9); 7.2253 (1.6); 7.2241 (1.7); 7.2141 (0.8); 7.2129 (0.8); 6.0259 (6.4); 3.4751 (16.0); 2.9532 (0.3); 2.9228 (2.2); 2.9197 (4.4); 2.9166 (6.2); 2.9135 (4.5); 2.9104 (2.2); 2.7849 (0.3); 2.7518 (2.3); 2.7486 (4.6); 2.7454 (6.6); 2.7422 (4.7); 2.7390 (2.4); 0.0001 (4.6)

[0822] I-016: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0823] =8.4996 (1.9); 8.4854 (3.7); 8.4710 (1.8); 8.3693 (4.8); 8.3523 (4.9); 8.3159 (0.3); 8.1255 (4.5); 8.1024 (5.0); 7.9244 (12.6); 7.7587 (2.4); 7.7559 (2.5); 7.7417 (2.8); 7.7389 (2.8); 7.7359 (2.6); 7.7329 (2.4); 7.7187 (2.3); 7.7158 (2.2); 7.1585 (3.0); 7.1421 (5.4); 7.1257 (2.6); 6.0490 (16.0); 5.7562 (6.1); 3.3217 (86.4); 3.2573 (5.6); 3.2414 (8.8); 3.2257 (5.7); 2.6804 (0.5); 2.6766 (0.8); 2.6720 (1.1); 2.5116 (74.6); 2.5074 (148.3); 2.5029 (193.3); 2.4984 (138.9); 2.4942 (67.7); 2.3338 (0.9); 2.3295 (1.1); 2.3250 (0.8); 1.4550 (0.5); 1.2332 (0.9); 1.0580 (0.7); 1.0459 (1.3); 1.0403 (1.2); 1.0288 (2.2); 1.0203 (1.1); 1.0167 (1.4); 1.0090 (1.4); 0.9975 (0.7); 0.9913 (0.5); 0.4888 (1.8); 0.4782 (5.6); 0.4739 (6.0); 0.4639 (2.9); 0.4581 (5.9); 0.4539 (5.6); 0.4440 (2.2); 0.2706 (2.2); 0.2570 (7.0); 0.2483 (6.1); 0.2448 (6.8); 0.2340 (1.7); 0.1462 (0.6); 0.0079 (4.8); 0.0002 (123.2); 0.0084 (4.6); 0.1498 (0.6)

[0824] I-017: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0825] =8.3869 (3.9); 8.3699 (4.0); 8.2861 (0.9); 8.2748 (2.3); 8.2625 (2.3); 8.2509 (0.9); 8.1162 (3.8); 8.0931 (4.2); 7.9263 (10.0); 7.7498 (2.0); 7.7325 (2.4); 7.7099 (1.9); 7.1497 (2.5); 7.1329 (4.7); 7.1160 (2.3); 6.0495 (14.7); 5.7636 (0.4); 5.7562 (3.2); 3.3248 (101.3); 2.8785 (16.0); 2.8664 (16.0); 2.8474 (0.5); 2.8354 (0.4); 2.6772 (0.5); 2.6727 (0.7); 2.5079 (91.8); 2.5036 (119.8); 2.4993 (89.6); 2.3303 (0.7); 1.4586 (2.1); 1.2336 (1.1); 0.0002 (4.9)

[0826] I-018: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0827] =8.3821 (1.3); 8.3711 (4.8); 8.3545 (4.6); 8.1210 (3.1); 8.0979 (3.5); 7.9260 (8.5); 7.7539 (1.6); 7.7515 (1.6); 7.7370 (1.9); 7.7342 (2.0); 7.7311 (1.8); 7.7140 (1.6); 7.7113 (1.5); 7.1523 (2.0); 7.1360 (3.8); 7.1192 (1.9); 6.0504 (11.7); 3.4007 (1.1); 3.3828 (3.6); 3.3679 (4.2); 3.3651 (4.2); 3.3502 (3.8); 3.3317 (2.2); 3.3231 (40.4); 2.6725 (0.6); 2.6684 (0.4); 2.5121 (39.4); 2.5080 (77.6); 2.5036 (100.5); 2.4991 (72.4); 2.3349 (0.4); 2.3304 (0.6); 1.4554 (0.4); 1.2330 (0.5); 1.1690 (7.6); 1.1510 (16.0); 1.1331 (7.3); 0.0079 (2.2); 0.0002 (59.8); 0.0084 (2.3)

[0828] I-019: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0829] =8.4314 (4.4); 8.4145 (4.5); 8.1087 (3.1); 8.0858 (5.5); 8.0382 (2.8); 8.0358 (2.7); 8.0214 (3.0); 8.0187 (3.0); 7.9984 (1.7); 7.8827 (11.1); 7.1971 (2.7); 7.1803 (5.1); 7.1635 (2.5); 5.8827 (16.0); 5.7574 (2.9); 4.3330 (0.4); 2.6739 (0.4); 2.5095 (57.8); 2.5052 (73.0); 2.5010 (53.1); 2.3314 (0.4); 1.4545 (0.6); 1.3183 (0.7); 0.0079 (0.6); 0.0002 (13.9)

[0830] I-020: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0831] =8.4412 (2.4); 8.4243 (2.6); 8.1177 (0.4); 8.1060 (2.2); 8.0829 (2.8); 7.9505 (1.4); 7.9475 (1.4); 7.9336 (1.5); 7.9306 (1.6); 7.9277 (1.3); 7.9246 (1.1); 7.9108 (1.8); 7.8844 (6.5); 7.1825 (0.4); 7.1750 (1.5); 7.1582 (2.8); 7.1414 (1.4); 5.9309 (8.9); 5.7561 (1.3); 5.5088 (1.3); 4.6589 (3.6); 4.6474 (16.0); 4.2585 (3.9); 4.0395 (1.2); 3.3663 (12.1); 2.6762 (0.5); 2.6718 (0.7); 2.6673 (0.5); 2.5254 (1.8); 2.5117 (44.6); 2.5074 (89.4); 2.5029 (115.9); 2.4984 (82.7); 2.4942 (39.7); 2.3339 (0.5); 2.3297 (0.7); 2.3254 (0.5); 0.0080 (1.4); 0.0002 (40.8); 0.0084 (1.5)

[0832] I-021: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0833] =12.2117 (2.4); 8.4215 (0.5); 8.4049 (0.5); 8.0788 (0.4); 8.0563 (0.5); 7.8665 (1.5); 7.1452 (0.3); 7.1284 (0.6); 5.9334 (1.7); 3.6055 (4.4); 3.5886 (16.0); 3.3227 (9.9); 3.2073 (0.5); 3.1912 (0.9); 3.1739 (0.6); 2.6569 (0.6); 2.6402 (0.9); 2.6239 (0.5); 2.5066 (37.6); 2.5025 (46.7); 2.4989 (34.3); 2.4828 (4.7); 2.4735 (2.3); 2.4695 (2.1); 2.4574 (0.9); 2.4477 (0.5); 0.0002 (5.3)

[0834] I-022: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0835] =8.8109 (1.1); 8.7957 (2.4); 8.7803 (1.2); 8.3741 (2.9); 8.3572 (3.0); 8.1378 (2.7); 8.1147 (3.0); 7.9219 (7.5); 7.7720 (1.4); 7.7697 (1.5); 7.7551 (1.6); 7.7523 (1.7); 7.7494 (1.6); 7.7466 (1.4); 7.7321 (1.4); 7.7296 (1.4); 7.3713 (1.0); 7.3577 (16.0); 7.3511 (7.0); 7.3427 (6.8); 7.3276 (0.8); 7.3223 (1.3); 7.2833 (1.0); 7.2769 (1.4); 7.2694 (1.4); 7.2616 (1.6); 7.2533 (1.0); 7.2468 (0.8); 7.2401 (0.4); 7.1576 (1.8); 7.1407 (3.4); 7.1246 (1.6); 6.0626 (9.5); 5.7568 (9.0); 4.5863 (5.9); 4.5711 (5.9); 3.3252 (45.2); 2.6728 (0.4); 2.6686 (0.3); 2.5083 (57.3); 2.5038 (75.0); 2.4994 (54.2); 2.3306 (0.4); 2.3262 (0.3); 1.2328 (0.6); 0.0002 (6.6)

[0836] I-023: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0837] =8.3872 (4.6); 8.3706 (4.8); 8.0952 (4.1); 8.0707 (7.1); 8.0639 (7.2); 8.0484 (3.9); 8.0284 (4.2); 7.9518 (14.2); 7.9334 (3.3); 7.9108 (2.2); 7.8880 (3.2); 7.8686 (3.9); 7.7054 (2.9); 7.6859 (4.9); 7.6662 (2.2); 7.1592 (3.0); 7.1423 (5.8); 7.1254 (2.9); 5.9760 (16.0); 3.3269 (165.3); 2.6723 (1.0); 2.5034 (175.9); 2.3299 (1.0); 2.0753 (5.0); 1.4350 (0.6); 1.1697 (0.7); 0.0004 (27.7)

[0838] I-024: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0839] =8.3713 (2.5); 8.3549 (2.5); 7.8339 (2.2); 7.8164 (2.3); 7.6387 (6.2); 7.1765 (2.1); 7.1595 (3.9); 7.1425 (2.0); 5.9994 (8.4); 3.3203 (63.8); 3.1032 (0.4); 3.0852 (0.3); 2.6635 (16.0); 2.5062 (148.8); 2.5018 (194.8); 2.4974 (142.3); 2.4225 (0.8); 2.3329 (0.8); 2.3285 (1.1); 2.3241 (0.9); 1.9086 (1.0); 1.2349 (3.8); 1.1934 (1.0); 1.1752 (1.9); 1.1570 (0.9); 1.0449 (2.4); 1.0296 (2.4); 0.8533 (0.3); 0.0078 (0.9); 0.0002 (25.0)

[0840] I-025: .sup.1H-NMR (601.6 MHz, CDCl3):

[0841] =8.4402 (1.3); 8.4289 (1.3); 8.3172 (0.4); 8.3049 (0.4); 7.6136 (3.8); 7.5928 (0.7); 7.5909 (0.7); 7.5815 (0.7); 7.5795 (0.8); 7.5776 (0.9); 7.5757 (0.9); 7.5662 (0.9); 7.5643 (0.9); 7.4291 (1.7); 7.4138 (1.4); 7.2620 (13.9); 7.0644 (0.8); 7.0631 (0.8); 7.0531 (1.6); 7.0518 (1.6); 7.0418 (0.8); 7.0405 (0.8); 6.0346 (6.0); 5.2987 (0.6); 4.3041 (0.4); 4.2932 (0.7); 4.2915 (0.6); 4.2822 (0.6); 4.2804 (0.7); 4.2695 (0.5); 1.3125 (16.0); 1.3016 (15.9); 1.2666 (0.3); 1.2552 (0.4); 1.2196 (0.8); 1.2087 (0.8); 0.0053 (1.0); 0.0002 (35.0); 0.0057 (1.1)

[0842] I-026: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0843] =8.7814 (5.2); 8.7719 (5.5); 8.4635 (4.5); 8.4467 (4.6); 8.3147 (0.6); 8.0876 (4.0); 8.0646 (5.2); 7.9411 (11.6); 7.9158 (3.1); 7.8956 (2.2); 7.8784 (5.3); 7.8660 (5.4); 7.2244 (4.1); 7.2144 (5.3); 7.2024 (3.9); 7.1918 (3.0); 7.1749 (5.6); 7.1580 (2.8); 5.9488 (16.0); 5.7548 (3.8); 3.3229 (74.9); 2.6723 (1.4); 2.5076 (195.4); 2.5034 (245.1); 2.4992 (179.4); 2.3300 (1.3); 1.4204 (0.9); 1.3525 (1.2); 1.3367 (0.4); 1.2992 (2.7); 1.2595 (3.6); 1.2339 (2.6); 0.8539 (0.4); 0.0000 (17.9)

[0844] I-027: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0845] =8.4102 (3.8); 8.4006 (3.8); 8.3505 (4.7); 8.3335 (5.0); 8.3154 (0.7); 8.1181 (4.4); 8.0947 (5.0); 7.9253 (12.4); 7.7560 (2.5); 7.7416 (2.7); 7.7386 (2.8); 7.7358 (2.6); 7.7328 (2.4); 7.7188 (2.4); 7.7158 (2.2); 7.1515 (3.0); 7.1343 (5.4); 7.1185 (2.5); 6.0377 (16.0); 5.7557 (5.3); 3.3199 (131.6); 2.8609 (0.4); 2.8519 (1.3); 2.8423 (2.0); 2.8337 (2.9); 2.8243 (2.9); 2.8157 (2.0); 2.8062 (1.3); 2.7967 (0.6); 2.6756 (1.9); 2.6711 (2.6); 2.6664 (1.9); 2.5241 (7.2); 2.5107 (169.5); 2.5064 (339.8); 2.5019 (442.3); 2.4974 (316.6); 2.4931 (153.0); 2.4010 (0.4); 2.3945 (0.3); 2.3327 (1.9); 2.3286 (2.5); 2.3244 (1.9); 1.4586 (0.5); 1.3507 (0.4); 1.2499 (0.4); 1.2338 (1.0); 0.8319 (0.4); 0.7873 (1.8); 0.7747 (5.1); 0.7700 (6.6); 0.7574 (6.5); 0.7524 (5.3); 0.7405 (2.0); 0.7189 (0.4); 0.5681 (0.3); 0.5573 (0.3); 0.5461 (0.3); 0.5278 (2.2); 0.5162 (5.9); 0.5112 (5.9); 0.5062 (5.6); 0.5013 (5.5); 0.4890 (1.8); 0.1458 (0.6); 0.0079 (5.2); 0.0002 (150.6); 0.0085 (5.7); 0.1502 (0.6)

[0846] I-028: .sup.1H-NMR (601.6 MHz, CDCl.sub.3):

[0847] =8.4712 (0.6); 8.4600 (0.6); 8.3288 (3.4); 8.3176 (3.5); 7.8389 (0.4); 7.8367 (0.4); 7.8331 (0.3); 7.8236 (0.3); 7.7608 (1.6); 7.7588 (1.6); 7.7495 (1.8); 7.7474 (2.0); 7.7456 (2.0); 7.7436 (1.9); 7.7342 (1.8); 7.7322 (1.8); 7.6846 (8.3); 7.6130 (1.5); 7.4314 (0.5); 7.4260 (3.5); 7.4195 (0.8); 7.4107 (3.3); 7.4043 (0.7); 7.3779 (8.0); 7.3773 (8.1); 7.3643 (13.9); 7.2929 (4.9); 7.2804 (4.2); 7.2785 (3.8); 7.2660 (3.2); 7.2602 (50.7); 7.0841 (0.6); 7.0739 (0.8); 7.0626 (0.4); 7.0062 (2.1); 6.9949 (4.1); 6.9838 (2.1); 6.0391 (14.4); 5.8285 (2.8); 5.2983 (16.0); 1.9031 (0.5); 1.5360 (1.2); 1.5296 (1.0); 1.2556 (1.2); 0.0965 (0.5); 0.0052 (3.5); 0.0002 (110.8); 0.0057 (3.9); 0.1000 (0.5)

[0848] I-029: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0849] =8.3842 (3.2); 8.3674 (3.4); 8.0869 (2.6); 8.0638 (3.9); 7.9871 (1.9); 7.9703 (2.1); 7.9681 (2.1); 7.9474 (1.4); 7.8817 (8.2); 7.1653 (2.0); 7.1485 (3.9); 7.1316 (1.9); 5.8664 (11.5); 4.3060 (2.3); 4.2882 (7.3); 4.2703 (7.4); 4.2526 (2.4); 4.0569 (0.8); 4.0390 (2.4); 4.0212 (2.4); 4.0034 (0.8); 3.3228 (14.2); 2.6726 (0.4); 2.5076 (55.8); 2.5035 (72.0); 2.4993 (52.2); 2.3304 (0.4); 1.9902 (9.9); 1.3055 (7.8); 1.2876 (16.0); 1.2699 (7.5); 1.2594 (0.5); 1.2341 (0.4); 1.1937 (2.6); 1.1759 (5.1); 1.1581 (2.5); 0.0001 (2.3)

[0850] I-030: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0851] =10.8412 (1.5); 8.3554 (4.8); 8.3385 (5.0); 8.2434 (4.0); 8.0854 (4.2); 8.0625 (5.6); 7.9361 (14.8); 7.9156 (3.2); 7.8932 (2.2); 7.7911 (11.1); 7.7700 (13.0); 7.5766 (0.4); 7.5048 (14.0); 7.4837 (13.0); 7.3843 (2.1); 7.3633 (1.6); 7.1558 (3.2); 7.1389 (5.9); 7.1221 (2.9); 5.9629 (16.0); 5.7573 (10.0); 4.5838 (0.4); 4.5685 (0.4); 3.9497 (0.5); 3.9362 (0.6); 3.9184 (0.6); 3.9026 (0.6); 3.4243 (0.4); 3.3908 (0.4); 3.3234 (144.6); 3.1131 (0.4); 3.1020 (0.5); 3.0798 (0.7); 3.0702 (0.7); 3.0465 (0.4); 3.0371 (0.4); 2.8205 (0.3); 2.7943 (0.5); 2.7879 (0.5); 2.7839 (0.5); 2.7623 (0.5); 2.7518 (0.5); 2.6713 (1.6); 2.6060 (0.8); 2.5702 (0.8); 2.5066 (219.7); 2.5024 (288.5); 2.4981 (210.4); 2.3292 (1.6); 1.8771 (0.4); 1.8439 (0.4); 1.7077 (0.5); 1.7019 (0.5); 1.6744 (0.4); 1.4322 (0.8); 1.2341 (4.8); 1.1185 (0.6); 1.0536 (0.6); 0.8610 (0.4); 0.8531 (0.7); 0.8434 (0.4); 0.8346 (0.4); 0.0002 (17.9)

[0852] I-031: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0853] =12.0418 (3.6); 8.4355 (4.5); 8.4186 (4.6); 8.0774 (4.1); 8.0544 (5.0); 7.8864 (12.2); 7.8790 (2.8); 7.8648 (2.6); 7.8619 (2.8); 7.8559 (2.1); 7.8417 (2.0); 7.8390 (2.0); 7.1446 (2.8); 7.1281 (5.3); 7.1114 (2.6); 5.9362 (16.0); 3.5450 (0.7); 3.5333 (1.5); 3.5253 (1.7); 3.5137 (3.2); 3.5021 (1.8); 3.4938 (1.6); 3.4820 (0.8); 3.3217 (77.2); 2.6760 (1.0); 2.6713 (1.4); 2.6670 (1.1); 2.5246 (3.6); 2.5111 (89.5); 2.5068 (183.9); 2.5024 (243.9); 2.4979 (175.1); 2.4937 (84.7); 2.3337 (1.0); 2.3293 (1.3); 2.3248 (1.0); 1.7677 (0.3); 1.5205 (0.6); 1.5082 (1.1); 1.5008 (1.4); 1.4974 (1.0); 1.4891 (2.2); 1.4831 (0.9); 1.4772 (1.2); 1.4696 (1.4); 1.4577 (0.7); 1.2333 (0.5); 0.9869 (1.5); 0.9770 (3.6); 0.9697 (6.5); 0.9584 (4.8); 0.9520 (2.2); 0.9258 (0.4); 0.9145 (0.3); 0.8869 (2.1); 0.8800 (4.7); 0.8676 (3.7); 0.8603 (4.9); 0.8518 (3.2); 0.8433 (1.5); 0.8319 (0.8); 0.8186 (2.4); 0.8114 (5.3); 0.8057 (2.5); 0.7988 (2.1); 0.7914 (5.4); 0.7857 (4.4); 0.7793 (5.1); 0.7723 (4.5); 0.7679 (5.9); 0.7603 (2.5); 0.7469 (0.5); 0.0079 (1.6); 0.0002 (47.7); 0.0084 (1.9)

[0854] I-032: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0855] =8.3687 (1.6); 8.3518 (1.7); 8.0926 (1.4); 8.0694 (2.1); 7.9937 (1.0); 7.9908 (1.0); 7.9769 (1.0); 7.9739 (1.0); 7.9710 (0.8); 7.9679 (0.7); 7.9537 (0.7); 7.9509 (0.7); 7.8755 (4.5); 7.1697 (1.0); 7.1529 (1.9); 7.1373 (0.9); 7.1360 (0.9); 5.8713 (5.7); 4.0381 (0.5); 4.0204 (0.5); 3.7975 (16.0); 3.3204 (10.3); 2.6714 (0.4); 2.5246 (0.9); 2.5196 (1.4); 2.5110 (24.4); 2.5067 (51.4); 2.5022 (68.9); 2.4976 (48.9); 2.4932 (23.0); 2.3291 (0.4); 1.9893 (2.1); 1.1928 (0.6); 1.1751 (1.1); 1.1573 (0.5); 0.0079 (1.3); 0.0002 (40.0); 0.0084 (1.4)

[0856] I-033: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0857] =8.3117 (2.6); 8.2954 (2.7); 7.7546 (2.4); 7.7370 (2.5); 7.6666 (6.6); 7.1285 (2.3); 7.1114 (4.2); 7.0943 (2.1); 6.0428 (8.1); 4.2945 (2.1); 4.2767 (6.8); 4.2589 (6.9); 4.2411 (2.2); 4.0387 (0.6); 4.0208 (0.6); 3.3241 (24.4); 2.6646 (16.0); 2.5076 (33.5); 2.5032 (43.9); 2.4988 (31.8); 1.9899 (2.7); 1.3008 (7.4); 1.2830 (15.2); 1.2652 (7.1); 1.1934 (0.8); 1.1757 (1.4); 1.1579 (0.7); 0.0076 (0.7); 0.0002 (18.3); 0.0081 (0.7)

[0858] I-034: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0859] =8.3847 (2.4); 8.3678 (2.4); 8.0869 (1.9); 8.0637 (2.8); 7.9864 (1.4); 7.9841 (1.4); 7.9696 (1.5); 7.9671 (1.5); 7.9466 (1.0); 7.9441 (1.0); 7.8881 (6.1); 7.1615 (1.4); 7.1450 (2.7); 7.1282 (1.4); 5.8674 (7.9); 4.0769 (6.2); 4.0585 (6.5); 4.0385 (1.6); 4.0207 (1.6); 4.0030 (0.5); 3.3211 (10.0); 2.6717 (0.4); 2.5070 (53.9); 2.5026 (70.9); 2.4983 (51.6); 2.3293 (0.4); 2.3250 (0.3); 1.9896 (6.8); 1.3967 (16.0); 1.1933 (2.0); 1.1868 (0.9); 1.1755 (4.0); 1.1674 (1.3); 1.1577 (2.3); 1.1482 (0.8); 1.1359 (0.4); 0.5703 (0.8); 0.5592 (2.7); 0.5548 (2.9); 0.5443 (1.4); 0.5391 (2.8); 0.5348 (2.7); 0.5245 (1.0); 0.3559 (1.0); 0.3451 (3.4); 0.3419 (3.3); 0.3337 (2.9); 0.3298 (3.4); 0.3186 (0.8); 0.0079 (1.0); 0.0002 (28.9); 0.0082 (1.2)

[0860] I-035: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0861] =8.4008 (4.8); 8.3839 (5.0); 8.0849 (4.0); 8.0617 (6.1); 7.9880 (2.8); 7.9856 (2.9); 7.9711 (3.0); 7.9685 (3.1); 7.9626 (2.1); 7.9481 (2.0); 7.9457 (2.0); 7.8823 (13.1); 7.1651 (3.0); 7.1482 (5.8); 7.1314 (2.8); 5.8599 (16.0); 5.1267 (0.6); 5.1082 (2.6); 5.0896 (3.9); 5.0712 (2.6); 5.0527 (0.7); 4.0786 (0.3); 4.0573 (1.0); 4.0393 (2.8); 4.0215 (2.8); 4.0037 (1.0); 3.3237 (26.2); 2.6731 (0.5); 2.6688 (0.4); 2.5263 (1.2); 2.5126 (29.8); 2.5085 (61.9); 2.5041 (83.3); 2.4996 (60.5); 2.4955 (29.7); 2.3862 (0.8); 2.3793 (1.3); 2.3660 (1.7); 2.3610 (2.6); 2.3550 (2.9); 2.3482 (2.6); 2.3413 (3.0); 2.3353 (3.7); 2.3305 (3.0); 2.3170 (1.9); 2.3102 (1.3); 2.2419 (0.9); 2.2352 (0.7); 2.2218 (1.7); 2.2170 (3.3); 2.2105 (2.2); 2.1978 (3.2); 2.1919 (4.0); 2.1860 (2.7); 2.1733 (2.4); 2.1667 (2.8); 2.1490 (0.7); 2.1421 (0.8); 1.9905 (12.1); 1.8305 (0.6); 1.8046 (1.9); 1.7857 (1.2); 1.7793 (2.0); 1.7600 (0.5); 1.7535 (0.7); 1.7477 (0.4); 1.7154 (0.5); 1.6946 (1.2); 1.6902 (1.4); 1.6696 (2.5); 1.6435 (2.0); 1.6233 (0.9); 1.6183 (0.8); 1.3958 (3.1); 1.2338 (0.4); 1.1942 (3.1); 1.1765 (6.2); 1.1586 (3.1); 0.1459 (0.4); 0.0079 (2.8); 0.0001 (83.3); 0.0082 (3.6); 0.1497 (0.4)

[0862] I-036: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0863] =8.3981 (4.8); 8.3811 (5.0); 8.0951 (3.7); 8.0720 (6.1); 8.0133 (2.9); 8.0107 (2.9); 7.9964 (3.1); 7.9938 (3.1); 7.9877 (1.9); 7.9734 (1.9); 7.9708 (1.8); 7.8846 (13.0); 7.1753 (2.9); 7.1584 (5.5); 7.1416 (2.8); 5.8603 (16.0); 5.7568 (2.3); 4.9765 (2.8); 4.9540 (8.8); 4.9315 (9.2); 4.9090 (3.1); 3.3243 (66.5); 2.6775 (0.4); 2.6728 (0.6); 2.6683 (0.5); 2.5259 (1.5); 2.5124 (41.1); 2.5081 (85.9); 2.5036 (114.9); 2.4992 (81.6); 2.4949 (38.6); 2.3347 (0.5); 2.3302 (0.6); 2.3259 (0.5); 1.9900 (0.7); 1.2592 (0.4); 1.2340 (0.5); 1.1763 (0.4); 0.1460 (0.5); 0.0076 (3.7); 0.0001 (107.5); 0.0081 (3.9); 0.1496 (0.5)

[0864] I-037: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0865] =8.4039 (3.7); 8.3870 (3.8); 8.0801 (3.0); 8.0569 (4.4); 7.9794 (2.1); 7.9767 (2.2); 7.9625 (2.3); 7.9596 (2.4); 7.9537 (1.6); 7.9395 (1.5); 7.9366 (1.5); 7.8854 (9.8); 7.1547 (2.2); 7.1379 (4.2); 7.1218 (2.1); 5.8598 (12.1); 4.9750 (1.3); 4.9594 (2.6); 4.9438 (2.6); 4.9279 (1.3); 4.0564 (0.6); 4.0386 (1.9); 4.0208 (1.9); 4.0030 (0.7); 3.3226 (50.6); 2.6763 (0.4); 2.6721 (0.6); 2.6676 (0.5); 2.5252 (1.5); 2.5115 (41.1); 2.5073 (85.9); 2.5029 (115.3); 2.4984 (83.5); 2.4942 (40.5); 2.3342 (0.5); 2.3297 (0.6); 2.3250 (0.5); 1.9896 (8.3); 1.7013 (0.6); 1.6840 (1.1); 1.6665 (2.1); 1.6488 (2.4); 1.6306 (2.1); 1.6259 (1.7); 1.6108 (2.0); 1.6073 (1.8); 1.5920 (2.0); 1.5732 (1.0); 1.5578 (0.6); 1.3966 (1.7); 1.2887 (15.8); 1.2729 (15.7); 1.1934 (2.1); 1.1756 (4.3); 1.1578 (2.1); 0.9303 (7.7); 0.9118 (16.0); 0.8931 (6.8); 0.1459 (0.5); 0.0078 (3.7); 0.0002 (108.3); 0.0084 (4.2); 0.1500 (0.5)

[0866] I-038: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0867] =8.3988 (1.8); 8.3819 (1.8); 8.0779 (1.4); 8.0548 (2.2); 7.9796 (1.0); 7.9771 (1.1); 7.9627 (1.1); 7.9601 (1.1); 7.9397 (0.7); 7.9370 (0.7); 7.8830 (4.7); 7.1565 (1.1); 7.1397 (2.1); 7.1229 (1.0); 5.8567 (6.0); 5.1400 (0.4); 5.1242 (1.2); 5.1086 (1.6); 5.0928 (1.2); 5.0772 (0.4); 4.0562 (0.4); 4.0384 (1.2); 4.0206 (1.2); 4.0028 (0.4); 3.3211 (15.0); 2.6715 (0.3); 2.5248 (0.7); 2.5112 (21.6); 2.5070 (45.8); 2.5026 (62.2); 2.4981 (45.2); 2.4940 (22.1); 2.3295 (0.4); 1.9895 (5.1); 1.3967 (1.0); 1.3079 (16.0); 1.2922 (15.9); 1.1932 (1.3); 1.1754 (2.6); 1.1576 (1.3); 0.0078 (1.4); 0.0001 (45.3); 0.0082 (1.8)

[0868] I-039: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0869] =8.3905 (5.0); 8.3737 (5.1); 8.0847 (3.9); 8.0615 (5.8); 7.9853 (2.8); 7.9826 (2.9); 7.9684 (3.1); 7.9656 (3.2); 7.9596 (2.1); 7.9454 (2.0); 7.9426 (2.0); 7.8825 (12.6); 7.1596 (3.0); 7.1427 (5.6); 7.1257 (2.7); 5.8629 (16.0); 4.3881 (0.4); 4.2201 (13.2); 4.2031 (13.2); 4.0568 (0.6); 4.0389 (1.8); 4.0211 (1.8); 4.0033 (0.6); 3.3595 (0.5); 3.3434 (0.6); 3.3216 (32.3); 2.7060 (0.8); 2.6871 (1.8); 2.6685 (2.7); 2.6511 (1.7); 2.6321 (0.7); 2.5255 (2.0); 2.5117 (54.1); 2.5076 (111.4); 2.5032 (147.6); 2.4987 (106.9); 2.3344 (0.6); 2.3298 (0.8); 2.3254 (0.6); 2.0685 (0.4); 2.0555 (1.5); 2.0367 (3.2); 2.0257 (3.1); 2.0158 (3.2); 2.0078 (2.5); 1.9899 (8.6); 1.9030 (0.8); 1.8867 (1.7); 1.8787 (1.3); 1.8638 (2.7); 1.8560 (2.4); 1.8475 (2.5); 1.8381 (6.5); 1.8322 (5.0); 1.8280 (5.6); 1.8166 (4.6); 1.8052 (2.0); 1.7983 (3.0); 1.7857 (1.2); 1.7766 (2.1); 1.7583 (0.5); 1.7541 (0.4); 1.3160 (0.7); 1.2590 (0.3); 1.2347 (0.3); 1.1937 (2.0); 1.1759 (4.0); 1.1581 (2.0); 0.1461 (0.7); 0.0080 (5.5); 0.0000 (156.7); 0.0083 (6.0); 0.1495 (0.7)

[0870] I-040: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0871] =8.3843 (4.4); 8.3677 (4.5); 8.1028 (3.9); 8.0798 (5.2); 7.9536 (2.6); 7.9367 (3.0); 7.9134 (2.4); 7.9046 (11.6); 7.1517 (2.9); 7.1347 (5.5); 7.1178 (2.7); 5.9243 (15.1); 5.7582 (9.8); 3.3670 (2.6); 3.3529 (2.8); 3.3270 (119.2); 3.2754 (1.8); 3.2579 (4.8); 3.2405 (4.9); 3.2235 (1.8); 2.6738 (0.7); 2.5042 (129.7); 2.3307 (0.8); 1.2356 (0.8); 1.1615 (7.5); 1.1438 (16.0); 1.1261 (7.4); 1.0969 (7.3); 1.0794 (15.6); 1.0617 (7.2); 0.0003 (36.3)

[0872] I-041: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0873] =8.3639 (1.6); 8.3471 (1.7); 8.0983 (1.4); 8.0752 (1.9); 7.9606 (0.9); 7.9579 (0.9); 7.9437 (0.9); 7.9409 (1.0); 7.9380 (0.9); 7.9349 (0.7); 7.9141 (4.4); 7.1604 (1.0); 7.1436 (1.9); 7.1268 (0.9); 5.9160 (5.4); 5.7578 (4.4); 3.3268 (21.8); 2.8974 (15.5); 2.8924 (16.0); 2.5269 (0.4); 2.5134 (10.6); 2.5091 (22.5); 2.5047 (30.6); 2.5002 (22.2); 2.4959 (10.7); 0.0080 (0.3); 0.0002 (11.4); 0.0084 (0.5)

[0874] I-042: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0875] =8.3996 (3.6); 8.3827 (3.8); 8.0967 (2.9); 8.0736 (4.5); 8.0040 (2.0); 8.0012 (2.3); 7.9870 (2.2); 7.9843 (2.4); 7.9783 (1.7); 7.9640 (1.5); 7.9612 (1.5); 7.9447 (2.8); 7.9252 (5.8); 7.9057 (3.6); 7.8885 (9.7); 7.5885 (4.6); 7.5695 (4.1); 7.5173 (4.6); 7.4974 (4.2); 7.1737 (2.2); 7.1569 (4.2); 7.1401 (2.1); 5.8750 (11.4); 5.3317 (16.0); 4.0561 (0.6); 4.0384 (1.8); 4.0205 (1.9); 4.0026 (0.6); 3.3219 (47.6); 2.6757 (0.6); 2.6714 (0.9); 2.6671 (0.7); 2.5248 (2.2); 2.5070 (116.8); 2.5026 (158.7); 2.4982 (119.6); 2.3340 (0.6); 2.3291 (0.9); 2.3248 (0.7); 1.9895 (8.2); 1.1931 (2.1); 1.1753 (4.2); 1.1575 (2.0); 0.1457 (0.3); 0.0078 (2.8); 0.0002 (73.5)

[0876] I-043: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0877] =8.3771 (3.8); 8.3602 (4.0); 8.2278 (2.1); 8.2160 (2.1); 8.2050 (0.8); 8.0878 (3.2); 8.0648 (4.4); 7.9574 (2.1); 7.9546 (2.2); 7.9406 (2.4); 7.9375 (2.5); 7.9347 (2.0); 7.9315 (1.8); 7.9174 (1.8); 7.9146 (1.8); 7.8797 (10.1); 7.1616 (2.2); 7.1462 (4.3); 7.1293 (2.2); 5.9240 (0.6); 5.9040 (12.4); 3.3243 (216.4); 3.1751 (1.4); 3.1620 (1.3); 2.6931 (15.7); 2.6814 (16.0); 2.6710 (2.0); 2.6568 (0.7); 2.5244 (3.5); 2.5110 (81.6); 2.5066 (167.1); 2.5022 (220.3); 2.4977 (157.2); 2.4933 (74.7); 2.3331 (0.8); 2.3290 (1.2); 2.3241 (0.9); 1.2355 (2.4); 0.8540 (0.3); 0.0081 (1.1); 0.0001 (29.9); 0.0083 (1.1)

[0878] I-044: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0879] =8.3489 (2.6); 8.3326 (2.6); 7.6642 (2.4); 7.6468 (2.6); 7.6220 (6.5); 7.5356 (0.9); 7.2912 (0.6); 7.2888 (0.7); 7.2721 (0.6); 7.2051 (0.6); 7.1911 (0.8); 7.1053 (2.4); 7.0883 (4.4); 7.0711 (2.2); 6.1557 (2.3); 6.0859 (0.7); 6.0694 (1.2); 6.0532 (0.6); 5.7565 (2.6); 5.1215 (0.3); 4.3579 (0.7); 4.3442 (0.7); 3.3489 (0.4); 3.3225 (33.2); 2.6889 (16.0); 2.6762 (1.2); 2.6714 (1.4); 2.6668 (1.0); 2.5246 (2.6); 2.5111 (71.4); 2.5067 (149.6); 2.5023 (200.9); 2.4978 (143.8); 2.4934 (69.3); 2.4878 (36.1); 2.4385 (0.4); 2.3915 (0.3); 2.3829 (0.3); 2.3336 (1.0); 2.3291 (1.4); 2.3245 (1.3); 2.3145 (0.6); 2.3079 (0.8); 2.2763 (0.5); 2.2460 (0.4); 2.2187 (0.5); 2.1983 (0.5); 2.1720 (0.5); 2.1480 (2.2); 2.0895 (0.4); 2.0410 (3.4); 2.0203 (0.6); 2.0082 (0.6); 1.9898 (0.5); 1.9523 (5.6); 1.9012 (6.6); 1.8644 (0.8); 1.8543 (0.3); 1.8368 (3.6); 1.7674 (0.5); 1.4790 (0.4); 1.4335 (1.1); 1.4262 (1.2); 1.4088 (1.3); 1.4022 (1.1); 1.3875 (0.9); 1.3809 (1.0); 1.3724 (0.7); 1.3624 (0.7); 1.3516 (1.1); 1.3368 (0.5); 1.2986 (0.6); 1.2589 (1.2); 1.2343 (7.4); 1.1740 (0.4); 0.9901 (0.3); 0.9418 (0.5); 0.8669 (0.4); 0.8535 (1.2); 0.8364 (0.6); 0.0079 (1.0); 0.0002 (32.9); 0.0084 (1.3)

[0880] I-045: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0881] =8.2982 (1.5); 8.2818 (1.6); 7.7631 (1.4); 7.7456 (1.4); 7.6645 (3.9); 7.1370 (1.3); 7.1199 (2.4); 7.1028 (1.2); 6.0486 (4.8); 3.7884 (16.0); 3.6270 (0.4); 3.3276 (28.8); 2.6678 (9.5); 2.5248 (0.8); 2.5072 (43.0); 2.5029 (57.4); 2.4985 (41.6); 2.0752 (1.0); 1.2344 (0.5); 0.0081 (1.6); 0.0001 (44.3); 0.0081 (1.8)

[0882] I-046: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0883] =8.3145 (2.6); 8.2991 (2.2); 7.7530 (2.0); 7.7352 (2.1); 7.6707 (5.7); 7.1250 (2.1); 7.1079 (3.7); 7.0907 (1.9); 6.0352 (6.6); 4.2046 (6.9); 4.1878 (7.0); 3.4028 (0.3); 3.3830 (0.5); 3.3212 (1073.9); 2.6995 (0.5); 2.6792 (2.4); 2.6748 (3.6); 2.6701 (5.5); 2.6622 (16.0); 2.6445 (1.2); 2.6244 (0.5); 2.5236 (10.3); 2.5101 (223.6); 2.5058 (451.4); 2.5013 (596.1); 2.4967 (438.8); 2.4924 (219.4); 2.3326 (2.8); 2.3280 (3.8); 2.3236 (2.8); 2.0734 (1.1); 2.0490 (0.8); 2.0305 (1.8); 2.0236 (1.3); 2.0195 (1.6); 2.0100 (1.7); 2.0020 (1.3); 1.9874 (0.8); 1.8830 (1.0); 1.8756 (0.6); 1.8604 (1.4); 1.8510 (1.1); 1.8415 (1.6); 1.8329 (3.0); 1.8279 (2.6); 1.8239 (2.6); 1.8127 (2.5); 1.7945 (1.5); 1.7806 (0.6); 1.7728 (1.0); 1.3010 (0.4); 1.2851 (0.4); 0.1459 (2.4); 0.0079 (19.1); 0.0002 (518.4); 0.0085 (21.4); 0.1497 (2.3)

[0884] I-047: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0885] =8.3093 (2.6); 8.2928 (2.6); 7.7525 (2.4); 7.7350 (2.5); 7.6719 (6.5); 7.1248 (2.4); 7.1076 (4.4); 7.0905 (2.2); 6.0416 (7.6); 4.0651 (8.2); 4.0469 (8.3); 3.3187 (156.2); 3.0987 (0.3); 2.6635 (16.0); 2.5237 (3.4); 2.5103 (56.5); 2.5059 (112.2); 2.5013 (149.4); 2.4968 (111.8); 2.4924 (56.4); 2.3327 (0.7); 2.3281 (1.0); 2.3236 (0.7); 2.0737 (2.8); 1.3013 (1.2); 1.2856 (1.2); 1.2489 (0.3); 1.2355 (0.5); 1.1908 (0.9); 1.1782 (1.6); 1.1720 (1.5); 1.1596 (1.9); 1.1479 (1.0); 1.1402 (1.3); 1.1335 (0.4); 1.1281 (0.6); 1.1214 (0.4); 0.5658 (1.1); 0.5547 (3.4); 0.5503 (3.6); 0.5397 (1.8); 0.5347 (3.6); 0.5300 (3.4); 0.5199 (1.4); 0.3486 (1.4); 0.3380 (4.1); 0.3342 (4.0); 0.3265 (3.6); 0.3224 (4.3); 0.3112 (1.0); 0.1459 (0.6); 0.0079 (5.6); 0.0002 (139.2); 0.0085 (6.1); 0.0180 (0.5); 0.0217 (0.3); 0.0224 (0.3); 0.0231 (0.3); 0.1498 (0.6)

[0886] I-048: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0887] =8.3990 (3.3); 8.3822 (3.4); 8.2973 (1.3); 8.2834 (2.5); 8.2693 (1.3); 8.0836 (2.8); 8.0604 (3.9); 7.9527 (1.9); 7.9499 (2.0); 7.9359 (2.1); 7.9329 (2.2); 7.9300 (1.8); 7.9269 (1.6); 7.9128 (1.5); 7.9099 (1.5); 7.9007 (0.5); 7.8839 (8.5); 7.1575 (2.0); 7.1407 (3.8); 7.1237 (1.9); 5.9211 (0.7); 5.9039 (10.8); 5.7554 (1.9); 3.3212 (109.9); 3.2221 (1.0); 3.2041 (3.5); 3.1899 (3.9); 3.1861 (4.0); 3.1719 (3.6); 3.1539 (1.1); 2.6756 (0.5); 2.6711 (0.6); 2.6665 (0.5); 2.5241 (2.3); 2.5108 (35.0); 2.5065 (68.8); 2.5020 (91.0); 2.4974 (68.7); 2.4931 (35.3); 2.3333 (0.4); 2.3288 (0.6); 2.3241 (0.4); 1.2351 (0.6); 1.1204 (7.6); 1.1024 (16.0); 1.0843 (7.3); 1.0409 (0.6); 0.1459 (0.4); 0.0078 (3.5); 0.0002 (79.9); 0.0084 (3.7); 0.1497 (0.4)

[0888] I-049: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0889] =9.0926 (7.6); 8.7626 (16.0); 8.7490 (0.6); 8.4038 (2.9); 8.3869 (3.0); 8.2321 (0.5); 8.2118 (0.6); 8.1772 (0.9); 8.0035 (3.8); 7.9894 (2.6); 7.9661 (5.8); 7.9443 (2.4); 7.9095 (1.7); 7.9069 (1.8); 7.8928 (1.8); 7.8901 (1.9); 7.8839 (1.2); 7.8698 (1.2); 7.8671 (1.2); 7.8464 (1.8); 7.8262 (2.2); 7.7626 (0.4); 7.7434 (0.6); 7.6578 (1.7); 7.6383 (2.9); 7.6188 (1.3); 7.1547 (1.8); 7.1379 (3.4); 7.1212 (1.7); 5.8896 (9.3); 5.7563 (11.3); 3.3222 (13.8); 2.6760 (0.4); 2.6716 (0.6); 2.6672 (0.5); 2.5249 (1.5); 2.5113 (37.7); 2.5070 (78.7); 2.5026 (105.6); 2.4981 (76.8); 2.4937 (37.9); 2.3336 (0.5); 2.3294 (0.6); 2.3252 (0.5); 0.1458 (0.4); 0.0077 (3.2); 0.0001 (97.7); 0.0083 (4.4); 0.1499 (0.5)

[0890] I-050: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0891] =8.3848 (4.5); 8.3680 (4.7); 8.0896 (3.6); 8.0664 (5.5); 7.9923 (2.5); 7.9896 (2.7); 7.9755 (2.7); 7.9726 (2.9); 7.9699 (2.2); 7.9666 (1.9); 7.9524 (1.8); 7.9496 (1.8); 7.8850 (11.8); 7.1672 (2.8); 7.1504 (5.2); 7.1335 (2.5); 5.8649 (14.8); 4.3470 (6.0); 4.3386 (4.8); 4.3354 (6.9); 4.3315 (5.0); 4.3234 (6.4); 4.0565 (1.2); 4.0387 (3.8); 4.0209 (3.8); 4.0031 (1.3); 3.7991 (0.7); 3.6332 (6.3); 3.6252 (4.7); 3.6213 (6.8); 3.6180 (5.1); 3.6096 (5.9); 3.4447 (0.4); 3.3227 (46.6); 3.2711 (54.3); 3.2556 (0.3); 2.6767 (0.4); 2.6722 (0.5); 2.6676 (0.4); 2.5255 (1.3); 2.5120 (30.9); 2.5077 (65.1); 2.5032 (87.7); 2.4987 (63.4); 2.4943 (30.7); 2.3346 (0.3); 2.3298 (0.5); 2.3255 (0.4); 1.9897 (16.0); 1.1935 (4.2); 1.1758 (8.4); 1.1579 (4.1); 0.8882 (0.4); 0.1457 (0.3); 0.0076 (2.6); 0.0004 (76.4); 0.0086 (2.9); 0.1500 (0.3)

[0892] I-051: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0893] =8.3943 (2.4); 8.3774 (2.6); 8.0960 (1.9); 8.0728 (3.0); 8.0065 (1.4); 8.0036 (1.5); 7.9897 (1.5); 7.9867 (1.6); 7.9838 (1.2); 7.9806 (1.0); 7.9665 (1.0); 7.9636 (1.0); 7.8845 (6.6); 7.1738 (1.5); 7.1570 (2.8); 7.1401 (1.4); 6.4935 (0.4); 6.4853 (0.8); 6.4768 (0.4); 6.3582 (0.8); 6.3497 (1.8); 6.3413 (0.9); 6.2227 (0.4); 6.2143 (0.9); 6.2059 (0.5); 5.8638 (7.9); 4.5721 (1.4); 4.5638 (1.5); 4.5346 (3.2); 4.5261 (3.1); 4.4969 (1.7); 4.4884 (1.5); 4.0563 (1.2); 4.0385 (3.7); 4.0207 (3.7); 4.0029 (1.2); 3.3216 (43.2); 2.6763 (0.4); 2.6716 (0.5); 2.6672 (0.4); 2.5249 (1.2); 2.5201 (1.8); 2.5115 (29.0); 2.5071 (62.0); 2.5026 (84.0); 2.4981 (60.9); 2.4937 (29.6); 2.3338 (0.3); 2.3293 (0.5); 2.3249 (0.4); 1.9894 (16.0); 1.3970 (7.4); 1.1933 (4.2); 1.1755 (8.4); 1.1577 (4.1); 0.0079 (2.1); 0.0002 (66.1); 0.0084 (2.6)

[0894] I-052: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0895] =8.4019 (2.0); 8.3850 (2.1); 8.0951 (1.6); 8.0719 (2.5); 7.9940 (1.1); 7.9912 (1.2); 7.9770 (1.2); 7.9742 (1.3); 7.9683 (0.9); 7.9540 (0.8); 7.9512 (0.9); 7.8780 (5.5); 7.3046 (5.2); 7.3018 (5.2); 7.2923 (16.0); 7.2806 (0.8); 7.2428 (0.8); 7.2326 (1.0); 7.2213 (1.2); 7.2153 (0.6); 7.2081 (0.6); 7.1716 (1.3); 7.1548 (2.4); 7.1379 (1.2); 5.8699 (6.4); 4.4554 (2.3); 4.4378 (5.2); 4.4202 (2.4); 4.0388 (0.8); 4.0210 (0.8); 3.3232 (27.3); 3.0251 (2.2); 3.0074 (4.7); 2.9898 (2.1); 2.5256 (0.7); 2.5121 (18.1); 2.5077 (38.6); 2.5032 (52.2); 2.4987 (37.7); 2.4943 (18.2); 1.9896 (3.2); 1.1936 (0.8); 1.1758 (1.7); 1.1580 (0.8); 0.0079 (0.9); 0.0002 (28.2); 0.0085 (1.0)

[0896] I-053: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0897] =8.4099 (3.5); 8.3930 (3.6); 8.0850 (2.8); 8.0619 (4.4); 7.9911 (2.0); 7.9886 (2.1); 7.9742 (2.2); 7.9714 (2.3); 7.9512 (1.4); 7.9487 (1.4); 7.8768 (9.4); 7.4694 (3.0); 7.4654 (4.0); 7.4488 (6.3); 7.4140 (2.0); 7.4095 (2.5); 7.3929 (6.9); 7.3743 (4.8); 7.3666 (3.9); 7.3628 (2.1); 7.3573 (1.1); 7.3496 (2.5); 7.3400 (0.4); 7.3316 (0.6); 7.1688 (2.2); 7.1520 (4.1); 7.1353 (2.0); 5.8603 (11.5); 5.2915 (16.0); 4.0563 (0.4); 4.0385 (1.0); 4.0207 (1.1); 4.0030 (0.3); 3.3240 (158.5); 2.6761 (0.6); 2.6717 (0.9); 2.6674 (0.6); 2.5247 (2.6); 2.5112 (55.5); 2.5071 (112.5); 2.5027 (148.8); 2.4983 (108.1); 2.3334 (0.6); 2.3294 (0.9); 2.3250 (0.6); 1.9892 (4.6); 1.2340 (0.3); 1.1933 (1.2); 1.1755 (2.4); 1.1577 (1.2); 0.0079 (0.6); 0.0002 (16.6)

[0898] I-054: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0899] =8.4081 (4.7); 8.3912 (4.9); 8.0970 (3.7); 8.0738 (5.7); 7.9998 (2.7); 7.9971 (2.8); 7.9830 (2.9); 7.9801 (3.0); 7.9741 (2.0); 7.9599 (2.0); 7.9572 (1.9); 7.8795 (12.5); 7.1713 (2.9); 7.1545 (5.5); 7.1377 (2.7); 5.8682 (16.0); 4.4763 (6.3); 4.4611 (12.6); 4.4458 (6.5); 4.0571 (0.9); 4.0393 (2.8); 4.0216 (2.9); 4.0037 (1.0); 3.3241 (59.2); 2.8514 (0.8); 2.8362 (1.4); 2.8229 (2.6); 2.8079 (4.4); 2.7940 (3.6); 2.7796 (4.5); 2.7647 (2.6); 2.7514 (1.5); 2.7361 (0.8); 2.6774 (0.4); 2.6731 (0.6); 2.6684 (0.4); 2.5262 (1.6); 2.5127 (38.0); 2.5084 (78.0); 2.5040 (103.5); 2.4996 (74.4); 2.4956 (36.1); 2.3350 (0.4); 2.3306 (0.6); 2.3263 (0.4); 1.9903 (12.2); 1.3966 (1.2); 1.2884 (0.6); 1.1942 (3.2); 1.1764 (6.4); 1.1586 (3.2); 0.0002 (5.3)

[0900] I-055: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0901] =8.3799 (3.9); 8.3631 (4.1); 8.0936 (3.1); 8.0704 (4.8); 8.0021 (2.3); 7.9995 (2.3); 7.9853 (2.5); 7.9825 (2.5); 7.9764 (1.6); 7.9622 (1.6); 7.9595 (1.5); 7.8797 (10.5); 7.1741 (2.4); 7.1572 (4.6); 7.1404 (2.3); 5.8653 (12.9); 4.8925 (12.6); 4.8863 (12.6); 4.0567 (1.2); 4.0388 (3.7); 4.0210 (3.7); 4.0032 (1.2); 3.6537 (3.4); 3.6476 (7.0); 3.6416 (3.3); 3.3263 (138.4); 2.6768 (0.4); 2.6725 (0.6); 2.6680 (0.4); 2.5257 (1.6); 2.5122 (38.6); 2.5079 (79.0); 2.5035 (104.6); 2.4990 (74.9); 2.3345 (0.4); 2.3301 (0.6); 2.3257 (0.4); 1.9896 (16.0); 1.3970 (0.4); 1.1938 (4.2); 1.1760 (8.3); 1.1583 (4.1); 0.0002 (4.8)

[0902] I-056: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0903] =8.4171 (5.2); 8.4002 (5.4); 8.1002 (4.0); 8.0770 (6.6); 8.0155 (3.0); 8.0127 (3.2); 7.9987 (3.2); 7.9957 (3.3); 7.9928 (2.5); 7.9896 (2.2); 7.9756 (2.0); 7.9727 (2.1); 7.8846 (14.3); 7.1754 (3.1); 7.1586 (5.8); 7.1417 (2.9); 6.7907 (0.6); 6.7773 (1.4); 6.7634 (0.7); 6.6612 (1.3); 6.6475 (2.9); 6.6337 (1.4); 6.5315 (0.6); 6.5176 (1.4); 6.5036 (0.7); 5.8653 (16.0); 4.8368 (3.3); 4.8023 (7.0); 4.7676 (3.5); 4.0565 (1.1); 4.0387 (3.2); 4.0209 (3.3); 4.0032 (1.1); 3.3219 (87.1); 2.6766 (0.6); 2.6720 (0.9); 2.6675 (0.7); 2.5253 (2.0); 2.5206 (3.1); 2.5119 (50.3); 2.5075 (108.4); 2.5030 (148.4); 2.4984 (108.4); 2.4940 (52.8); 2.3342 (0.6); 2.3296 (0.8); 2.3251 (0.6); 1.9895 (14.8); 1.3969 (7.2); 1.2499 (0.4); 1.2353 (0.6); 1.1938 (3.8); 1.1760 (7.6); 1.1582 (3.7); 0.0002 (4.7)

[0904] I-057: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0905] =8.3882 (3.0); 8.3714 (3.2); 8.0844 (2.4); 8.0613 (3.7); 7.9857 (1.7); 7.9830 (1.9); 7.9688 (1.8); 7.9660 (2.0); 7.9632 (1.5); 7.9599 (1.3); 7.9458 (1.2); 7.9430 (1.3); 7.8770 (8.2); 7.1604 (1.9); 7.1436 (3.5); 7.1267 (1.8); 5.8605 (9.8); 5.4186 (0.7); 5.4155 (0.9); 5.4122 (0.8); 5.4005 (1.5); 5.3971 (1.9); 5.3938 (1.6); 5.3821 (0.8); 5.3791 (1.0); 5.3757 (0.8); 4.7358 (5.0); 4.7177 (4.8); 4.0563 (0.4); 4.0385 (1.4); 4.0207 (1.5); 4.0029 (0.5); 3.3206 (36.0); 2.6761 (0.4); 2.6718 (0.6); 2.6672 (0.4); 2.5250 (1.4); 2.5114 (36.2); 2.5072 (77.2); 2.5027 (105.1); 2.4982 (76.8); 2.4940 (37.8); 2.3341 (0.4); 2.3294 (0.6); 2.3250 (0.4); 1.9893 (6.3); 1.7395 (14.5); 1.7084 (16.0); 1.3971 (2.4); 1.1936 (1.6); 1.1759 (3.2); 1.1580 (1.6); 0.0001 (2.6)

[0906] I-058: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0907] =8.4000 (5.0); 8.3832 (5.1); 8.0851 (4.2); 8.0621 (5.7); 7.9500 (2.6); 7.9473 (2.9); 7.9331 (2.9); 7.9303 (3.2); 7.9277 (2.7); 7.9243 (2.4); 7.9101 (2.2); 7.9074 (2.3); 7.8840 (13.1); 7.7680 (3.8); 7.3949 (3.7); 7.2278 (0.8); 7.1523 (3.2); 7.1354 (5.9); 7.1186 (2.9); 7.1000 (0.8); 6.9722 (0.8); 5.9075 (16.0); 5.7558 (2.3); 3.3255 (18.8); 2.6760 (0.5); 2.6717 (0.7); 2.6673 (0.5); 2.5073 (86.5); 2.5028 (116.0); 2.4984 (86.2); 2.3337 (0.5); 2.3296 (0.6); 2.3251 (0.5); 1.1991 (0.5); 1.1809 (1.0); 1.1627 (0.5); 0.0002 (4.8)

[0908] I-059: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0909] =8.9915 (6.6); 8.4304 (1.6); 8.4135 (1.7); 8.1062 (1.4); 8.0830 (1.8); 7.9697 (0.9); 7.9668 (1.0); 7.9528 (1.0); 7.9498 (1.0); 7.9470 (0.8); 7.9437 (0.8); 7.9297 (0.7); 7.9267 (0.7); 7.9094 (4.4); 7.8751 (0.3); 7.1720 (1.0); 7.1551 (2.0); 7.1382 (1.0); 5.9492 (5.0); 5.8717 (0.4); 4.0559 (0.4); 4.0382 (1.4); 4.0204 (1.4); 4.0026 (0.5); 3.9743 (16.0); 3.7974 (1.2); 3.3200 (53.3); 2.6757 (0.6); 2.6711 (0.8); 2.6665 (0.6); 2.5246 (2.1); 2.5199 (3.2); 2.5111 (48.6); 2.5067 (104.4); 2.5021 (141.9); 2.4976 (102.6); 2.4931 (49.6); 2.3333 (0.6); 2.3288 (0.8); 2.3242 (0.6); 1.9889 (6.4); 1.3075 (0.4); 1.2918 (0.4); 1.1931 (1.7); 1.1753 (3.3); 1.1575 (1.6); 1.0451 (0.9); 1.0299 (0.9); 0.0080 (2.3); 0.0002 (74.0); 0.0084 (2.9)

[0910] I-060: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0911] =8.3776 (2.4); 8.3614 (2.4); 7.8349 (2.3); 7.8173 (2.4); 7.6349 (6.6); 7.1853 (2.4); 7.1681 (4.2); 7.1510 (2.2); 6.0078 (8.0); 3.3194 (116.1); 2.6761 (16.0); 2.6665 (1.9); 2.5242 (3.7); 2.5194 (5.5); 2.5107 (73.0); 2.5063 (149.6); 2.5018 (196.5); 2.4972 (140.2); 2.4927 (67.1); 2.3375 (0.4); 2.3330 (0.8); 2.3285 (1.2); 2.3239 (0.8); 2.3194 (0.4); 1.2354 (0.5); 1.0450 (1.8); 1.0297 (1.8); 0.1459 (0.8); 0.0079 (6.3); 0.0002 (195.8); 0.0085 (6.8); 0.0192 (0.3); 0.1497 (0.8)

[0912] I-061: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0913] =8.3719 (2.4); 8.3556 (2.4); 7.7849 (2.2); 7.7674 (2.3); 7.6393 (6.2); 7.2705 (1.7); 7.1612 (2.3); 7.1441 (4.2); 7.1343 (4.1); 7.1270 (2.3); 6.9981 (2.0); 6.4216 (7.7); 6.2888 (16.0); 6.1561 (8.1); 6.0826 (6.2); 3.3475 (1.5); 3.3315 (1.5); 2.6746 (15.4); 2.5249 (2.6); 2.5202 (3.8); 2.5114 (52.4); 2.5070 (107.9); 2.5025 (142.2); 2.4979 (102.2); 2.4935 (49.4); 2.3337 (0.7); 2.3292 (0.9); 2.3247 (0.7); 1.1295 (0.3); 1.1139 (0.3); 1.0454 (0.7); 1.0302 (0.7); 0.1459 (0.6); 0.0079 (4.6); 0.0002 (143.4); 0.0085 (5.2); 0.1498 (0.6)

[0914] I-062: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0915] =8.3825 (2.4); 8.3662 (2.5); 7.8554 (2.2); 7.8378 (2.4); 7.6508 (0.8); 7.6385 (0.4); 7.6274 (6.4); 7.4807 (1.0); 7.3827 (0.5); 7.1894 (2.3); 7.1723 (4.1); 7.1552 (2.2); 6.0003 (0.5); 5.9753 (8.3); 5.9631 (1.4); 5.2629 (0.6); 5.2209 (0.6); 5.2054 (0.6); 5.1024 (0.5); 4.0384 (0.4); 4.0207 (0.4); 3.7883 (0.5); 3.7731 (0.7); 3.7578 (0.6); 2.7127 (1.7); 2.6688 (16.0); 2.5250 (2.5); 2.5114 (52.2); 2.5071 (105.3); 2.5027 (137.8); 2.4981 (100.1); 2.4938 (49.2); 2.3338 (0.6); 2.3294 (0.8); 2.3249 (0.6); 1.9889 (1.7); 1.1933 (0.4); 1.1755 (1.0); 1.1578 (0.5); 1.0455 (7.7); 1.0303 (7.7); 0.1457 (0.3); 0.0079 (2.8); 0.0002 (83.8); 0.0085 (3.3); 0.1500 (0.4)

[0916] I-063: .sup.1H-NMR (400.2 MHz, d.sub.6-DMSO):

[0917] =8.3833 (2.5); 8.3669 (2.6); 7.8340 (2.4); 7.8164 (2.6); 7.6395 (0.4); 7.6175 (6.4); 7.1924 (2.3); 7.1753 (4.2); 7.1582 (2.4); 7.1375 (0.3); 7.0362 (0.6); 7.0206 (1.3); 7.0052 (0.6); 6.8886 (0.6); 6.0301 (7.8); 6.0024 (0.6); 5.7557 (2.1); 3.3249 (26.9); 2.6762 (16.0); 2.5257 (1.4); 2.5121 (26.2); 2.5080 (51.1); 2.5035 (65.4); 2.4990 (47.0); 2.4948 (23.1); 2.3302 (0.4); 1.3526 (0.3); 1.2309 (0.5); 0.0002 (3.8)

[0918] I-065: .sup.1H-NMR (601.6 MHz, d.sub.6-DMSO):

[0919] =8.3211 (2.6); 8.3106 (2.5); 7.7511 (1.9); 7.7493 (2.7); 7.7396 (1.9); 7.7377 (2.7); 7.7358 (1.7); 7.6601 (7.1); 7.6371 (0.6); 7.1208 (2.8); 7.1094 (5.1); 7.0980 (2.6); 6.8960 (1.5); 6.6919 (0.7); 6.0354 (7.1); 5.1015 (0.4); 5.0885 (1.5); 5.0765 (2.3); 5.0631 (1.5); 5.0519 (0.4); 4.5151 (0.9); 3.9744 (0.7); 3.3052 (68.0); 2.7517 (2.4); 2.7356 (0.5); 2.6624 (16.0); 2.6187 (0.4); 2.6156 (0.9); 2.6126 (1.2); 2.6094 (0.8); 2.6064 (0.4); 2.5375 (0.6); 2.5218 (2.7); 2.5187 (3.3); 2.5156 (3.0); 2.5069 (56.5); 2.5039 (126.1); 2.5008 (181.3); 2.4977 (128.5); 2.4947 (58.9); 2.3911 (0.4); 2.3880 (0.8); 2.3850 (1.1); 2.3819 (0.8); 2.3789 (0.4); 2.3665 (0.6); 2.3618 (1.2); 2.3570 (0.8); 2.3530 (1.1); 2.3500 (1.8); 2.3483 (1.6); 2.3456 (1.8); 2.3410 (1.8); 2.3365 (1.9); 2.3337 (1.8); 2.3321 (2.0); 2.3291 (1.5); 2.3251 (1.0); 2.3203 (1.3); 2.3156 (0.9); 2.2708 (1.5); 2.2181 (0.8); 2.2136 (0.6); 2.2048 (1.0); 2.2015 (2.4); 2.1969 (1.6); 2.1916 (0.7); 2.1887 (2.2); 2.1846 (2.6); 2.1807 (1.9); 2.1723 (1.7); 2.1679 (2.1); 2.1644 (0.9); 2.1560 (0.5); 2.1515 (0.6); 2.0712 (4.7); 1.8152 (0.4); 1.8020 (0.6); 1.7972 (1.2); 1.7925 (0.7); 1.7853 (0.7); 1.7805 (1.3); 1.7791 (1.1); 1.7756 (0.7); 1.7639 (0.5); 1.6929 (0.4); 1.6794 (0.8); 1.6763 (0.8); 1.6657 (0.6); 1.6627 (1.7); 1.6584 (0.8); 1.6490 (0.8); 1.6447 (1.5); 1.6419 (0.5); 1.6312 (0.7); 1.6282 (0.7); 1.3522 (13.5); 1.3355 (2.4); 1.2986 (0.9); 1.2895 (0.3); 1.2593 (1.6); 1.2501 (4.2); 1.2344 (5.7); 1.2288 (8.1); 1.1880 (0.3); 1.0989 (0.3); 0.8629 (0.6); 0.8540 (1.1); 0.8513 (1.5); 0.8396 (0.7); 0.0964 (0.7); 0.0052 (5.0); 0.0002 (210.3); 0.0058 (7.2); 0.1001 (0.8)

[0920] I-066: .sup.1H-NMR (600.1 MHz, CDCl3):

[0921] =8.4319 (0.6); 8.4207 (0.6); 7.7581 (0.4); 7.7565 (0.4); 7.7450 (0.4); 7.6237 (1.5); 7.3753 (0.7); 7.3600 (0.6); 7.2616 (10.8); 7.0346 (0.4); 7.0233 (0.8); 7.0119 (0.4); 5.8240 (2.8); 5.3004 (3.2); 1.6561 (16.0); 1.5743 (4.9); 0.0001 (5.2)

[0922] I-068: .sup.1H-NMR (601.6 MHz, CD3CN):

[0923] =19.9493 (0.6); 8.2388 (3.9); 8.2275 (3.9); 8.1285 (5.4); 8.1264 (6.4); 8.1185 (2.1); 8.1151 (7.6); 8.1124 (5.4); 7.9165 (1.9); 7.9144 (2.0); 7.9051 (2.2); 7.9030 (2.1); 7.9010 (2.3); 7.8990 (2.2); 7.8897 (2.5); 7.8876 (2.2); 7.7347 (9.2); 7.6867 (4.2); 7.6713 (3.7); 7.6142 (0.9); 7.6021 (3.8); 7.5980 (1.1); 7.5925 (2.4); 7.5901 (3.9); 7.5876 (2.0); 7.5766 (5.9); 7.5669 (3.9); 7.5642 (7.5); 7.5555 (1.3); 7.5526 (2.8); 7.5500 (1.8); 7.0842 (2.3); 7.0730 (4.5); 7.0616 (2.3); 5.8859 (16.0); 4.8559 (0.8); 4.0775 (0.9); 4.0657 (2.8); 4.0539 (2.9); 4.0421 (0.9); 3.9597 (1.0); 2.9963 (0.8); 2.8890 (1.1); 2.8750 (0.7); 2.7722 (0.8); 2.1472 (39.4); 2.1451 (38.7); 2.1430 (43.6); 2.1403 (41.1); 2.1369 (45.4); 2.0491 (0.5); 1.9711 (12.2); 1.9547 (1.1); 1.9467 (36.1); 1.9426 (66.0); 1.9385 (89.2); 1.9344 (56.9); 1.9303 (26.9); 1.8238 (0.5); 1.4371 (0.5); 1.2769 (0.5); 1.2156 (3.1); 1.2038 (6.8); 1.1919 (3.2); 0.0002 (21.4)

[0924] I-069: .sup.1H-NMR (600.1 MHz, CDCl3):

[0925] =19.9849 (0.4); 9.0861 (11.7); 8.5025 (3.7); 8.4912 (3.9); 8.2738 (0.4); 8.2666 (0.4); 7.7928 (1.9); 7.7812 (2.5); 7.7682 (2.2); 7.7662 (2.1); 7.6110 (9.0); 7.5673 (0.4); 7.5549 (0.5); 7.5439 (0.4); 7.4675 (1.0); 7.4317 (5.0); 7.4295 (4.8); 7.4141 (4.1); 7.3332 (0.3); 7.3159 (0.3); 7.2602 (551.3); 7.1019 (2.3); 7.0918 (4.4); 7.0834 (3.5); 7.0805 (2.4); 6.7864 (0.5); 6.7746 (0.3); 6.5645 (0.7); 6.5496 (0.6); 5.8936 (16.0); 5.3853 (0.3); 5.3467 (1.0); 5.3423 (1.0); 5.3160 (0.4); 5.2999 (0.6); 4.8761 (2.1); 4.0210 (2.6); 2.2326 (1.0); 2.2196 (1.6); 2.2070 (1.3); 2.0449 (0.5); 2.0152 (1.2); 2.0049 (1.1); 1.6514 (0.7); 1.6386 (0.9); 1.6275 (0.8); 1.6135 (0.4); 1.5393 (477.5); 1.5082 (0.7); 1.4235 (0.4); 1.3707 (0.8); 1.3271 (2.0); 1.3108 (2.8); 1.2861 (2.8); 1.2687 (3.9); 1.2552 (6.2); 1.0639 (0.3); 1.0479 (0.4); 0.8929 (1.8); 0.8813 (3.5); 0.8696 (2.0); 0.8443 (1.2); 0.1657 (0.8); 0.0968 (2.4); 0.0866 (1.6); 0.0689 (172.6); 0.0629 (7.7); 0.0446 (1.0); 0.0051 (25.6); 0.0001 (519.8); 0.0055 (22.6); 0.0308 (0.9); 0.1003 (2.2)

[0926] I-070: .sup.1H-NMR (601.6 MHz, CD3CN):

[0927] =19.1087 (1.6); 16.0800 (1.7); 14.9626 (1.5); 13.9228 (1.8); 8.7844 (3.6); 8.3806 (3.9); 8.3685 (3.1); 7.8498 (2.2); 7.8359 (2.9); 7.8238 (2.6); 7.6815 (8.7); 7.6760 (4.0); 7.6599 (3.7); 7.5916 (4.0); 7.5850 (3.6); 7.1075 (2.4); 7.0955 (4.6); 7.0846 (2.6); 6.6636 (1.6); 5.8913 (16.0); 5.0297 (1.5); 4.0756 (1.6); 4.0654 (4.5); 4.0536 (4.3); 2.1566 (2.0); 2.1259 (185.2); 2.1228 (171.4); 2.0484 (1.6); 1.9705 (18.8); 1.9459 (115.3); 1.9419 (208.2); 1.9378 (283.2); 1.9337 (180.1); 1.9298 (84.8); 1.8233 (2.6); 1.3407 (1.7); 1.3275 (1.7); 1.2154 (4.9); 1.2038 (9.1); 1.1912 (5.2); 0.0003 (57.5)

[0928] I-071: .sup.1H-NMR (400.2 MHz, d.sub.6-DMSO):

[0929] =8.7606 (11.0); 8.7559 (11.0); 8.4487 (5.0); 8.4462 (3.2); 8.4344 (3.0); 8.4319 (5.1); 8.4294 (3.2); 8.3151 (0.5); 8.1190 (4.1); 8.0959 (5.9); 8.0039 (2.8); 8.0008 (3.0); 7.9870 (3.1); 7.9839 (3.2); 7.9810 (2.4); 7.9778 (2.2); 7.9640 (2.2); 7.9609 (2.2); 7.9332 (13.1); 7.6822 (0.6); 7.6430 (11.4); 7.6384 (11.5); 7.1996 (2.8); 7.1978 (3.1); 7.1827 (5.5); 7.1809 (5.8); 7.1659 (2.7); 7.1640 (2.8); 5.9665 (16.0); 5.7558 (0.6); 4.8384 (0.8); 3.9598 (1.0); 3.3259 (178.1); 2.6812 (0.5); 2.6767 (1.0); 2.6721 (1.4); 2.6675 (1.0); 2.6630 (0.5); 2.5256 (4.2); 2.5209 (6.4); 2.5122 (82.7); 2.5077 (169.2); 2.5031 (222.4); 2.4985 (158.7); 2.4940 (76.0); 2.3391 (0.5); 2.3345 (1.0); 2.3299 (1.4); 2.3253 (1.0); 2.3209 (0.4); 1.9895 (0.7); 1.1758 (0.4); 0.0080 (2.5); 0.0002 (81.2); 0.0085 (2.6)

[0930] I-072: .sup.1H-NMR (400.2 MHz, CD3CN):

[0931] =8.7948 (8.7); 8.3368 (3.2); 8.3199 (3.4); 7.8695 (1.5); 7.8667 (1.4); 7.8523 (1.7); 7.8489 (2.0); 7.8465 (2.2); 7.8436 (2.0); 7.8294 (2.1); 7.8267 (1.9); 7.7368 (7.4); 7.7037 (4.1); 7.6805 (3.1); 7.1046 (2.1); 7.0877 (4.1); 7.0707 (2.1); 5.9357 (16.0); 4.0943 (0.9); 4.0766 (0.9); 2.1782 (70.9); 2.1472 (0.7); 2.1338 (0.4); 1.9983 (4.0); 1.9909 (1.1); 1.9789 (16.2); 1.9728 (30.8); 1.9667 (43.1); 1.9605 (30.8); 1.9544 (16.6); 1.3978 (0.7); 1.3668 (0.4); 1.3106 (0.7); 1.3020 (1.2); 1.2958 (1.0); 1.2478 (1.1); 1.2300 (2.0); 1.2122 (1.0)

[0932] I-073: .sup.1H-NMR (400.2 MHz, CD3CN):

[0933] =8.4836 (10.6); 8.3407 (3.2); 8.3237 (3.2); 7.8511 (1.5); 7.8485 (1.4); 7.8343 (1.7); 7.8283 (2.1); 7.8112 (2.0); 7.8084 (1.8); 7.7195 (7.2); 7.6869 (4.0); 7.6638 (3.0); 7.0989 (2.1); 7.0819 (4.0); 7.0650 (1.9); 5.9104 (16.0); 4.0947 (0.8); 4.0768 (0.7); 2.1666 (268.0); 2.1465 (1.1); 2.1342 (3.8); 1.9981 (3.8); 1.9901 (4.3); 1.9785 (68.4); 1.9723 (125.4); 1.9662 (171.5); 1.9600 (117.5); 1.9539 (59.3); 1.8072 (0.4); 1.8009 (0.7); 1.7950 (1.0); 1.7887 (0.7); 1.7824 (0.4); 1.3024 (0.4); 1.2480 (0.8); 1.2304 (1.6); 1.2124 (0.7)

[0934] I-074: .sup.1H-NMR (400.2 MHz, CD3CN):

[0935] =8.7875 (10.1); 8.4075 (3.2); 8.3906 (3.2); 8.1843 (8.7); 7.8707 (1.5); 7.8674 (1.4); 7.8534 (1.7); 7.8476 (2.2); 7.8304 (2.2); 7.8275 (1.9); 7.7224 (7.3); 7.7076 (4.1); 7.6843 (3.0); 7.1340 (2.0); 7.1173 (3.8); 7.1006 (1.9); 5.9421 (16.0); 4.0946 (0.6); 4.0768 (0.7); 2.5420 (0.5); 2.3041 (0.4); 2.2915 (0.4); 2.2831 (0.4); 2.2661 (0.4); 2.2585 (0.5); 2.2451 (0.7); 2.1777 (478.2); 2.1464 (3.9); 2.1339 (2.2); 2.1280 (1.5); 2.1218 (0.8); 1.9984 (3.4); 1.9907 (5.6); 1.9788 (105.7); 1.9727 (196.2); 1.9665 (269.3); 1.9604 (184.5); 1.9542 (93.1); 1.8069 (0.6); 1.8011 (1.1); 1.7951 (1.6); 1.7888 (1.0); 1.7828 (0.6); 1.3984 (1.5); 1.3662 (0.8); 1.3116 (1.1); 1.3029 (2.1); 1.2481 (0.8); 1.2303 (1.4); 1.2124 (0.7); 1.1115 (0.4); 0.1079 (0.4); 0.0262 (0.3)

[0936] I-075: .sup.1H-NMR (600.1 MHz, d.sub.6-DMSO):

[0937] =8.4565 (2.7); 8.4547 (4.5); 8.4529 (2.8); 8.4453 (2.9); 8.4435 (4.7); 8.4416 (2.8); 8.3141 (0.3); 8.2097 (6.1); 8.2084 (6.3); 8.2038 (6.4); 8.2025 (6.3); 8.0855 (4.4); 8.0701 (5.2); 7.9373 (16.0); 7.9360 (10.5); 7.9343 (7.5); 7.9330 (6.4); 7.9175 (2.6); 7.9154 (2.7); 7.9062 (2.8); 7.9041 (2.9); 7.9022 (2.5); 7.9001 (2.4); 7.8909 (2.4); 7.8888 (2.3); 7.1787 (2.8); 7.1774 (2.8); 7.1675 (5.3); 7.1661 (5.3); 7.1562 (2.7); 7.1549 (2.6); 6.6981 (6.2); 6.6953 (6.1); 6.6922 (6.0); 6.6894 (6.1); 5.9650 (14.6); 5.7543 (3.4); 4.0363 (0.3); 4.0244 (0.3); 3.3184 (98.0); 2.6183 (0.7); 2.6151 (1.0); 2.6121 (0.7); 2.6090 (0.3); 2.5242 (2.3); 2.5211 (2.8); 2.5180 (2.7); 2.5092 (50.5); 2.5062 (111.4); 2.5031 (156.2); 2.5000 (113.4); 2.4970 (53.3); 2.4834 (1.6); 2.3930 (0.3); 2.3901 (0.7); 2.3871 (0.9); 2.3839 (0.7); 2.3808 (0.3); 1.9895 (1.4); 1.3364 (1.2); 1.2992 (0.6); 1.2594 (1.0); 1.2502 (1.8); 1.2333 (0.6); 1.1882 (0.5); 1.1763 (0.9); 1.1645 (0.5); 0.0968 (0.8); 0.0054 (6.7); 0.0001 (226.6); 0.0057 (8.4); 0.0263 (0.4); 0.1003 (0.8)

[0938] I-076: .sup.1H-NMR (400.2 MHz, d.sub.6-DMSO):

[0939] =9.1490 (0.4); 9.1441 (0.4); 9.0984 (10.1); 9.0936 (10.3); 8.5570 (11.2); 8.5522 (11.0); 8.3788 (5.0); 8.3764 (3.3); 8.3620 (5.2); 8.3595 (3.3); 8.3161 (0.3); 8.0974 (4.3); 8.0743 (5.6); 7.9412 (13.6); 7.9357 (3.6); 7.9216 (3.0); 7.9185 (3.1); 7.9157 (2.6); 7.9125 (2.3); 7.8986 (2.3); 7.8955 (2.3); 7.1673 (2.9); 7.1656 (3.2); 7.1505 (5.6); 7.1488 (5.9); 7.1336 (2.8); 7.1318 (2.9); 5.9786 (16.0); 4.0564 (0.5); 4.0387 (1.4); 4.0209 (1.4); 4.0031 (0.5); 3.3230 (37.5); 2.6813 (0.4); 2.6767 (0.7); 2.6721 (1.0); 2.6676 (0.8); 2.6631 (0.4); 2.5256 (3.1); 2.5209 (4.6); 2.5122 (60.2); 2.5078 (123.6); 2.5032 (163.1); 2.4986 (116.5); 2.4941 (55.7); 2.3346 (0.7); 2.3300 (1.0); 2.3254 (0.7); 1.9898 (6.1); 1.3366 (0.4); 1.2591 (0.4); 1.2498 (0.5); 1.2338 (0.4); 1.1936 (1.7); 1.1758 (3.4); 1.1580 (1.6); 1.0458 (2.1); 1.0306 (2.1); 0.0080 (1.7); 0.0002 (53.6); 0.0085 (1.7)

[0940] I-077: H-NMR (400.2 MHz, d.sub.6-DMSO):

[0941] =8.7089 (4.6); 8.6984 (7.8); 8.6879 (4.4); 8.4692 (4.9); 8.4524 (5.1); 8.3143 (0.6); 8.0920 (4.4); 8.0689 (5.8); 7.9484 (2.8); 7.9454 (3.0); 7.9294 (15.8); 7.9226 (2.8); 7.9085 (2.3); 7.9054 (2.2); 7.1978 (3.0); 7.1822 (5.7); 7.1809 (5.7); 7.1654 (2.8); 7.1640 (2.8); 6.8671 (5.0); 6.8622 (5.0); 6.8561 (4.8); 6.8512 (4.8); 5.9380 (16.0); 5.7547 (5.1); 3.3202 (293.3); 2.6757 (1.8); 2.6711 (2.5); 2.6666 (1.8); 2.5244 (8.9); 2.5110 (135.2); 2.5066 (267.8); 2.5020 (363.7); 2.4975 (276.0); 2.4932 (136.3); 2.3335 (1.6); 2.3290 (2.2); 2.3245 (1.6); 1.9889 (0.4); 1.3358 (0.5); 1.2984 (0.5); 1.2589 (0.7); 1.2498 (0.8); 1.2341 (0.8); 1.1755 (0.3); 0.0079 (1.4); 0.0002 (33.7); 0.0084 (1.2)

[0942] I-078: .sup.1H-NMR (400.2 MHz, d.sub.6-DMSO):

[0943] =20.0084 (0.4); 8.5823 (0.4); 8.5632 (0.5); 8.5057 (0.4); 8.3623 (5.2); 8.3458 (5.2); 8.3142 (2.9); 7.8125 (4.8); 7.7944 (5.1); 7.6195 (12.2); 7.5671 (0.8); 7.5545 (0.3); 7.2476 (0.3); 7.2313 (0.4); 7.1811 (0.4); 7.1586 (4.3); 7.1413 (7.4); 7.1240 (4.0); 6.9904 (0.3); 6.9732 (0.5); 6.5210 (0.6); 6.3027 (16.0); 5.7545 (3.6); 3.3190 (1399.0); 3.2065 (0.4); 2.6748 (8.8); 2.6704 (12.2); 2.6659 (9.0); 2.5235 (39.4); 2.5100 (723.2); 2.5057 (1425.4); 2.5012 (1937.0); 2.4968 (1502.8); 2.3326 (9.4); 2.3282 (12.7); 2.3238 (9.6); 2.2993 (1.9); 2.2850 (1.2); 2.2663 (2.1); 2.2510 (3.1); 2.2390 (2.1); 2.2162 (1.1); 2.0874 (0.7); 2.0734 (1.5); 1.9754 (0.5); 1.9195 (0.5); 1.6115 (0.5); 1.4690 (0.6); 1.4501 (0.6); 1.4215 (0.7); 1.3513 (2.5); 1.3364 (1.1); 1.2333 (3.5); 1.1931 (1.1); 1.1270 (2.2); 1.1155 (5.7); 1.1106 (6.3); 1.0952 (5.6); 1.0901 (5.7); 1.0804 (2.5); 1.0635 (0.8); 0.9990 (0.6); 0.9594 (2.5); 0.9448 (7.0); 0.9361 (6.3); 0.9317 (6.3); 0.9201 (1.9); 0.8503 (0.7); 0.7868 (0.4); 0.6794 (0.4); 0.1458 (0.4); 0.0079 (3.8); 0.0002 (84.9); 0.0084 (3.2); 0.1488 (0.4)

[0944] I-079: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0945] =8.7886 (0.7); 8.7756 (0.7); 7.8211 (1.0); 7.8062 (1.0); 5.9867 (0.3); 3.3684 (2.1); 3.1162 (1.1); 3.1040 (1.4); 3.0980 (3.5); 3.0860 (3.7); 3.0798 (3.8); 3.0679 (3.6); 3.0622 (1.5); 3.0497 (1.2); 2.5069 (20.8); 2.5027 (26.8); 2.4984 (19.5); 1.2033 (7.9); 1.1852 (16.0); 1.1669 (7.6); 0.0002 (0.8)

[0946] I-080: .sup.1H-NMR (400.2 MHz, d.sub.6-DMSO):

[0947] =8.7153 (5.7); 8.7123 (6.1); 8.7080 (6.2); 8.7049 (5.9); 8.4250 (5.0); 8.4225 (3.2); 8.4082 (5.2); 8.3159 (0.4); 8.0778 (4.4); 8.0547 (5.8); 7.9420 (13.2); 7.9292 (0.3); 7.9193 (2.8); 7.9163 (2.9); 7.9024 (3.0); 7.8993 (3.1); 7.8965 (2.6); 7.8932 (2.4); 7.8794 (2.3); 7.8763 (2.3); 7.6503 (5.6); 7.6472 (5.7); 7.6376 (6.8); 7.6346 (6.9); 7.5268 (6.3); 7.5194 (6.4); 7.5142 (5.4); 7.5068 (5.1); 7.1745 (2.9); 7.1728 (3.1); 7.1576 (5.5); 7.1559 (5.8); 7.1408 (2.8); 7.1390 (2.8); 5.9555 (16.0); 4.0566 (0.7); 4.0388 (2.2); 4.0210 (2.2); 4.0032 (0.7); 3.3226 (38.4); 2.6812 (0.4); 2.6767 (0.8); 2.6721 (1.1); 2.6675 (0.8); 2.6630 (0.4); 2.5256 (3.6); 2.5209 (5.5); 2.5122 (66.9); 2.5078 (136.2); 2.5032 (179.0); 2.4986 (128.2); 2.4941 (61.6); 2.3393 (0.4); 2.3345 (0.8); 2.3300 (1.1); 2.3255 (0.8); 2.3209 (0.4); 1.9898 (9.7); 1.2498 (0.4); 1.1937 (2.7); 1.1759 (5.4); 1.1581 (2.6); 0.0080 (1.2); 0.0002 (38.8); 0.0085 (1.3)

[0948] I-082: .sup.1H-NMR (400.1 MHz, CDCl3):

[0949] =8.4242 (1.4); 8.4145 (2.7); 8.3979 (1.5); 7.7186 (0.7); 7.6976 (1.1); 7.6788 (0.9); 7.6164 (3.2); 7.5071 (1.2); 7.4882 (1.4); 7.4228 (1.1); 7.4001 (0.9); 7.2644 (8.3); 7.1666 (1.0); 7.1544 (1.1); 7.1480 (1.0); 7.1356 (0.9); 7.0342 (0.9); 7.0171 (1.7); 7.0002 (0.9); 5.9106 (5.0); 4.9156 (5.7); 4.9077 (7.0); 2.4893 (8.8); 1.8501 (0.8); 1.3316 (0.4); 1.2837 (1.3); 1.2528 (16.0); 0.8947 (0.7); 0.8789 (1.4); 0.8615 (0.8); 0.8280 (0.4); 0.0013 (4.8)

[0950] I-084: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

[0951] =8.4143 (4.2); 8.3966 (4.6); 8.3770 (10.0); 8.3641 (5.1); 8.3395 (0.5); 8.3275 (0.5); 7.9368 (3.0); 7.9135 (4.8); 7.8524 (2.7); 7.8357 (3.2); 7.8130 (1.7); 7.6733 (2.9); 7.6528 (3.4); 7.4724 (8.1); 7.4637 (5.9); 7.4425 (4.4); 7.4128 (0.7); 7.3927 (4.3); 7.3801 (4.0); 7.3422 (0.4); 7.3307 (0.4); 7.1442 (2.5); 7.1275 (4.5); 7.1110 (2.2); 5.8580 (12.6); 5.5474 (0.3); 4.7178 (15.7); 4.6478 (16.0); 4.5601 (0.7); 4.5470 (0.7); 4.0354 (0.3); 3.3211 (42.0); 3.2986 (3.5); 2.6681 (0.8); 2.5004 (134.7); 2.3269 (0.9); 1.9876 (1.1); 1.1733 (0.6); 1.1553 (0.4); 0.0016 (13.2)

[0952] I-085: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

[0953] =8.9263 (6.1); 8.3933 (3.6); 8.3765 (3.5); 8.0911 (3.2); 8.0680 (4.0); 7.9036 (9.7); 7.8873 (2.9); 7.8651 (1.8); 7.1508 (2.2); 7.1339 (4.0); 7.1169 (2.0); 6.6837 (6.3); 5.9506 (11.4); 5.7600 (0.6); 4.7510 (16.0); 4.7026 (14.3); 4.6360 (0.6); 3.3333 (60.0); 3.3006 (0.7); 3.1749 (0.9); 3.1620 (0.9); 2.6733 (0.4); 2.5035 (50.9); 1.2316 (2.1); 0.0014 (2.2)

[0954] I-086: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

[0955] =8.3986 (2.5); 8.3804 (5.1); 8.3452 (1.0); 8.3276 (2.2); 8.3151 (2.0); 7.9367 (1.9); 7.9136 (2.9); 7.8418 (1.5); 7.8250 (1.7); 7.8020 (1.0); 7.6733 (1.5); 7.6674 (1.5); 7.6527 (1.8); 7.6467 (1.8); 7.6084 (2.5); 7.5892 (2.8); 7.4611 (3.4); 7.4405 (2.9); 7.2650 (1.6); 7.2533 (2.1); 7.2456 (2.0); 7.2345 (1.8); 7.2245 (0.6); 7.1366 (1.6); 7.1199 (2.8); 7.1030 (1.4); 5.8611 (7.4); 5.7552 (1.6); 4.6624 (10.6); 4.6400 (9.6); 4.5751 (2.3); 4.0551 (0.6); 4.0372 (1.7); 4.0194 (1.7); 4.0016 (0.6); 3.3185 (12.2); 3.1659 (0.7); 2.5306 (0.4); 2.5011 (51.2); 2.3727 (16.0); 2.3278 (0.4); 2.3072 (6.5); 1.9878 (7.0); 1.9084 (0.9); 1.2324 (0.8); 1.1915 (1.8); 1.1737 (3.6); 1.1560 (1.8); 0.0014 (5.4)

[0956] I-087: .sup.1H-NMR (400.1 MHz, CDCl3):

[0957] =8.4536 (1.7); 8.4367 (1.7); 8.3292 (2.1); 8.3239 (2.2); 7.7022 (1.0); 7.6817 (1.2); 7.6617 (1.1); 7.6519 (1.2); 7.6460 (1.2); 7.6312 (1.3); 7.6253 (1.3); 7.3389 (1.9); 7.3159 (1.8); 7.3048 (2.4); 7.2840 (2.1); 7.2614 (20.7); 7.0581 (1.1); 7.0412 (2.1); 7.0242 (1.0); 5.8399 (6.8); 4.8587 (8.9); 4.3056 (0.6); 4.2885 (0.3); 3.8831 (2.3); 3.8663 (4.7); 3.8494 (2.4); 2.7539 (2.4); 2.7371 (4.7); 2.7202 (2.3); 2.3490 (0.4); 1.7539 (0.8); 1.7368 (0.8); 1.7196 (0.8); 1.6997 (0.7); 1.6827 (0.5); 1.6547 (0.4); 1.6374 (0.4); 1.6195 (0.3); 1.4505 (0.4); 1.4266 (0.5); 1.3318 (0.7); 1.3177 (0.8); 1.2988 (1.0); 1.2823 (1.4); 1.2533 (16.0); 0.9790 (0.5); 0.9607 (1.0); 0.9414 (0.6); 0.9195 (0.5); 0.8947 (1.0); 0.8789 (1.6); 0.8615 (0.8); 0.0686 (0.7); 0.0012 (16.9)

[0958] I-088: .sup.1H-NMR (400.1 MHz, MeOD):

[0959] =8.4389 (2.4); 8.4219 (2.4); 7.9317 (6.0); 7.9187 (2.6); 7.8948 (0.5); 7.7987 (4.9); 7.2214 (1.2); 7.2054 (2.0); 7.1912 (1.1); 6.0098 (8.8); 4.9045 (49.4); 4.8166 (9.9); 3.7235 (2.8); 3.7111 (5.1); 3.6982 (3.2); 3.4837 (3.3); 3.4712 (4.8); 3.4590 (2.6); 3.3303 (25.3); 2.0191 (16.0); 1.3165 (1.2)

[0960] I-089: .sup.1H-NMR (400.1 MHz, CDCl3):

[0961] =8.4388 (1.6); 8.4218 (1.6); 7.7507 (0.8); 7.7305 (1.2); 7.7108 (0.9); 7.6121 (3.6); 7.4089 (1.7); 7.3861 (1.5); 7.2625 (11.9); 7.0660 (1.0); 7.0490 (1.8); 7.0322 (0.9); 5.8893 (6.4); 4.8704 (7.9); 3.9258 (2.1); 3.9089 (4.2); 3.8921 (2.2); 2.7897 (2.1); 2.7728 (4.1); 2.7560 (2.0); 1.6273 (2.6); 1.2528 (16.0); 0.8946 (0.6); 0.8787 (1.3); 0.8616 (0.7); 0.0685 (0.6); 0.0016 (6.9)

[0962] I-090: .sup.1H-NMR (400.1 MHz, CDCl3):

[0963] =8.4897 (2.0); 8.4784 (2.1); 8.4257 (2.3); 8.4088 (2.4); 7.7228 (1.1); 7.7024 (1.6); 7.6829 (1.4); 7.6156 (5.7); 7.4923 (1.0); 7.4704 (2.1); 7.4484 (1.3); 7.4099 (2.6); 7.3870 (2.3); 7.3465 (0.9); 7.3358 (1.6); 7.3252 (1.5); 7.3148 (1.3); 7.3039 (0.7); 7.2631 (30.6); 7.0411 (1.5); 7.0241 (2.9); 7.0072 (1.5); 5.9091 (9.4); 5.3480 (0.4); 4.9882 (16.0); 2.2397 (0.4); 2.2211 (0.6); 2.2022 (0.4); 2.0906 (0.6); 2.0107 (4.0); 1.2551 (3.8); 0.8964 (0.4); 0.8805 (1.0); 0.8627 (0.4); 0.0001 (30.2)

[0964] I-092: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

[0965] =8.3969 (6.4); 8.3813 (8.9); 7.9452 (2.7); 7.9222 (4.0); 7.8444 (2.4); 7.8274 (2.8); 7.8046 (1.6); 7.7511 (1.8); 7.7289 (3.1); 7.7049 (2.1); 7.6722 (2.4); 7.6663 (2.4); 7.6519 (3.0); 7.6458 (2.8); 7.4899 (1.5); 7.4790 (2.8); 7.4682 (3.0); 7.4610 (6.6); 7.4408 (4.9); 7.1489 (0.5); 7.1397 (2.4); 7.1228 (4.4); 7.1059 (2.1); 5.8563 (12.2); 4.7171 (10.3); 4.7125 (10.6); 4.6761 (16.0); 4.4855 (0.9); 4.0552 (0.4); 4.0373 (1.3); 4.0197 (1.3); 4.0022 (0.4); 3.3240 (31.6); 3.1644 (0.5); 2.6714 (0.5); 2.5414 (1.9); 2.5021 (78.7); 2.3285 (0.4); 1.9881 (5.4); 1.9097 (1.3); 1.2328 (1.0); 1.1917 (1.4); 1.1740 (2.8); 1.1561 (1.4); 0.0013 (8.6)

[0966] I-093: .sup.1H-NMR (400.1 MHz, CDCl3):

[0967] =8.4282 (3.1); 8.4114 (3.1); 8.3736 (3.6); 8.3608 (3.6); 7.7536 (1.5); 7.7338 (2.1); 7.7138 (1.7); 7.6225 (7.1); 7.4755 (5.2); 7.4187 (3.3); 7.3959 (2.9); 7.3279 (3.0); 7.3153 (2.9); 7.2636 (14.2); 7.0670 (2.0); 7.0500 (3.7); 7.0330 (1.9); 5.9089 (12.3); 5.2996 (4.0); 4.9028 (16.0); 4.7728 (13.6); 3.6435 (0.7); 2.2434 (0.4); 2.2252 (0.5); 2.2045 (0.5); 2.1767 (0.4); 2.0443 (0.3); 1.3313 (0.4); 1.2820 (0.9); 1.2531 (3.9); 0.8785 (0.6); 0.8599 (0.4); 0.8440 (0.3); 0.8292 (0.3); 0.0687 (0.3); 0.0018 (13.7)

[0968] I-095: .sup.1H-NMR (400.1 MHz, CDCl3):

[0969] =9.2044 (3.6); 8.9081 (4.8); 8.4399 (2.5); 8.4231 (2.5); 7.7566 (1.2); 7.7382 (2.0); 7.7170 (1.5); 7.6175 (5.4); 7.4136 (2.7); 7.3907 (2.4); 7.2623 (21.7); 7.0713 (1.5); 7.0541 (2.8); 7.0373 (1.4); 5.9016 (9.6); 5.3474 (0.4); 4.9230 (11.6); 4.7928 (10.8); 3.4898 (1.7); 2.2206 (0.5); 2.2012 (0.4); 2.0921 (0.5); 2.0175 (1.5); 2.0039 (1.5); 1.6541 (0.4); 1.6390 (0.4); 1.6193 (0.4); 1.4243 (0.4); 1.2537 (16.0); 0.9192 (0.4); 0.8949 (1.3); 0.8791 (2.0); 0.8616 (1.1); 0.0689 (0.8); 0.0011 (21.2)

[0970] I-097: .sup.1H-NMR (400.1 MHz, MeOD):

[0971] =9.1072 (7.3); 8.8831 (16.0); 8.4683 (3.6); 8.4511 (3.6); 8.3744 (4.2); 8.3688 (4.1); 7.9039 (1.2); 7.8806 (2.7); 7.8643 (2.9); 7.8396 (5.0); 7.8165 (2.2); 7.7153 (2.3); 7.7092 (2.3); 7.6946 (2.7); 7.6884 (2.6); 7.4318 (5.0); 7.4111 (4.3); 7.2283 (2.1); 7.2116 (3.9); 7.1949 (1.9); 5.9202 (14.3); 4.9296 (0.4); 4.8925 (141.6); 4.8768 (20.8); 4.7284 (16.8); 4.1484 (0.4); 4.1309 (1.0); 4.1124 (1.0); 4.0933 (0.3); 3.5029 (0.7); 3.3693 (2.3); 3.3306 (129.7); 3.1514 (0.7); 2.0341 (4.6); 2.0018 (0.5); 1.3101 (1.2); 1.2790 (1.2); 1.2613 (2.3); 1.2433 (1.2)

[0972] I-098: .sup.1H-NMR (400.1 MHz, CDCl3):

[0973] =8.4399 (6.0); 8.4253 (4.5); 8.4085 (4.0); 8.3837 (0.8); 7.8499 (3.0); 7.8297 (3.3); 7.7477 (1.8); 7.7275 (3.0); 7.7091 (2.3); 7.6195 (7.4); 7.4143 (3.6); 7.3914 (3.2); 7.3519 (4.6); 7.3316 (4.3); 7.2653 (11.5); 7.0636 (2.3); 7.0469 (4.0); 7.0302 (2.2); 5.8997 (12.6); 4.8736 (16.0); 4.7434 (15.6); 2.0103 (0.8); 1.8319 (2.0); 1.2533 (7.1); 0.8783 (0.9); 0.8619 (0.6); 0.0017 (9.6)

[0974] I-100: .sup.1H-NMR (400.1 MHz, CDCl3):

[0975] =8.7704 (2.4); 8.4211 (1.2); 8.4065 (1.2); 7.7083 (1.1); 7.6189 (1.7); 7.4224 (1.1); 7.4024 (1.0); 7.2658 (2.9); 7.2180 (1.2); 7.0279 (1.2); 5.9158 (3.3); 5.0743 (3.2); 5.0165 (3.3); 2.0050 (0.4); 1.2517 (16.0); 1.1004 (0.5); 0.8759 (1.9); 0.0685 (0.7); 0.0032 (1.2)

[0976] I-101: .sup.1H-NMR (400.1 MHz, MeOD):

[0977] =8.8113 (9.3); 8.8003 (9.5); 8.4449 (6.7); 8.4282 (7.0); 8.3401 (8.3); 7.9487 (0.4); 7.9366 (0.5); 7.9006 (2.6); 7.8779 (5.0); 7.8610 (4.8); 7.8189 (8.1); 7.7960 (4.5); 7.6925 (4.2); 7.6727 (4.9); 7.4736 (0.6); 7.4496 (3.7); 7.4385 (5.8); 7.4256 (3.7); 7.3995 (7.3); 7.3787 (6.2); 7.2189 (4.1); 7.2023 (7.5); 7.1855 (3.8); 6.6110 (0.3); 6.5898 (0.7); 6.5784 (0.4); 6.5687 (0.6); 5.8779 (16.0); 5.3620 (0.4); 5.0972 (0.3); 4.9903 (17.5); 4.9047 (335.0); 4.7848 (0.4); 4.6462 (1.3); 4.5572 (2.2); 3.5010 (0.5); 3.3296 (76.8); 3.1716 (14.6); 3.1581 (21.7); 3.1436 (16.4); 2.2316 (0.4); 2.2126 (0.7); 2.1938 (0.4); 2.0554 (0.5); 2.0404 (0.4); 1.8390 (3.7); 1.8233 (9.6); 1.8112 (15.6); 1.7983 (12.4); 1.7416 (4.2); 1.7280 (7.6); 1.7156 (7.6); 1.7024 (3.8); 1.6416 (0.4); 1.6195 (0.4); 1.5556 (0.7); 1.5460 (0.3); 1.3166 (3.9); 0.9375 (0.4); 0.9202 (0.9); 0.9033 (0.4)

[0978] I-103: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

[0979] =8.4702 (0.4); 8.4117 (4.2); 8.3945 (4.8); 8.3749 (10.6); 8.3622 (5.9); 7.9321 (3.1); 7.9096 (5.1); 7.8513 (2.8); 7.8324 (3.2); 7.8111 (2.0); 7.6688 (2.8); 7.6507 (3.4); 7.4699 (7.6); 7.4604 (6.3); 7.4395 (4.8); 7.4108 (1.0); 7.3906 (4.2); 7.3782 (4.3); 7.3413 (0.6); 7.1434 (2.5); 7.1268 (4.5); 7.1103 (2.5); 5.8570 (12.9); 5.8086 (0.5); 5.5415 (0.4); 4.7174 (15.8); 4.6468 (16.0); 4.5803 (0.3); 4.5589 (0.8); 4.5458 (0.9); 3.3783 (0.4); 3.3095 (153.5); 2.6667 (1.0); 2.4982 (159.9); 2.3244 (1.0); 1.9860 (0.7); 1.3954 (0.5); 1.2492 (0.4); 1.2326 (1.0); 1.1737 (0.4); 0.8525 (0.7); 0.8360 (0.6); 0.1436 (0.3); 0.0028 (46.9); 0.1513 (0.4)

[0980] I-106: .sup.1H-NMR (600.1 MHz, DMF):

[0981] =8.5040 (1.0); 8.4928 (1.0); 8.2448 (1.0); 8.2293 (1.2); 8.1038 (0.6); 8.1019 (0.6); 8.0925 (0.6); 8.0905 (0.7); 8.0886 (0.6); 8.0865 (0.5); 8.0771 (0.5); 8.0752 (0.5); 8.0252 (2.0); 7.9976 (2.4); 7.2823 (0.6); 7.2813 (0.6); 7.2710 (1.2); 7.2700 (1.2); 7.2597 (0.6); 7.2587 (0.6); 6.0236 (3.9); 5.8150 (3.1); 3.4886 (12.8); 2.9232 (0.9); 2.9202 (1.7); 2.9171 (2.4); 2.9140 (1.7); 2.9109 (0.9); 2.7523 (0.9); 2.7491 (1.8); 2.7459 (2.6); 2.7427 (1.8); 2.7395 (0.9); 2.0141 (0.6); 1.9298 (16.0); 0.0053 (0.8); 0.0001 (19.3); 0.0056 (0.8)

[0982] I-107: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

[0983] =8.4000 (5.0); 8.3832 (5.1); 8.0851 (4.2); 8.0621 (5.7); 7.9500 (2.6); 7.9473 (2.9); 7.9331 (2.9); 7.9303 (3.2); 7.9277 (2.7); 7.9243 (2.4); 7.9101 (2.2); 7.9074 (2.3); 7.8840 (13.1); 7.7680 (3.8); 7.3949 (3.7); 7.2278 (0.8); 7.1523 (3.2); 7.1354 (5.9); 7.1186 (2.9); 7.1000 (0.8); 6.9722 (0.8); 5.9075 (16.0); 5.7558 (2.3); 3.3255 (18.8); 2.6760 (0.5); 2.6717 (0.7); 2.6673 (0.5); 2.5073 (86.5); 2.5028 (116.0); 2.4984 (86.2); 2.3337 (0.5); 2.3296 (0.6); 2.3251 (0.5); 1.1991 (0.5); 1.1809 (1.0); 1.1627 (0.5); 0.0002 (4.8)

[0984] I-108: .sup.1H-NMR (400.2 MHz, d.sub.6-DMSO):

[0985] =8.4083 (2.5); 8.4058 (1.6); 8.3939 (1.7); 8.3915 (2.6); 8.0757 (2.1); 8.0525 (3.0); 7.9785 (1.5); 7.9755 (1.7); 7.9616 (1.7); 7.9586 (1.8); 7.9556 (1.3); 7.9524 (1.2); 7.9386 (1.1); 7.9355 (1.1); 7.8813 (0.7); 7.8733 (6.8); 7.1552 (1.5); 7.1535 (1.6); 7.1446 (0.4); 7.1383 (2.8); 7.1366 (2.9); 7.1215 (1.4); 7.1197 (1.4); 5.9082 (0.4); 5.8882 (0.5); 5.8436 (7.5); 5.7557 (2.6); 3.3341 (2.5); 2.6766 (0.4); 2.6721 (0.6); 2.6675 (0.4); 2.5256 (1.9); 2.5208 (3.0); 2.5122 (36.9); 2.5077 (75.0); 2.5032 (98.5); 2.4986 (70.4); 2.4940 (33.8); 2.3345 (0.4); 2.3300 (0.6); 2.3253 (0.4); 2.0682 (1.0); 1.7606 (0.7); 1.6028 (16.0); 1.5083 (2.5); 1.4983 (1.0); 1.4631 (0.4); 1.3887 (0.8); 1.2889 (0.4); 1.2732 (0.4); 1.2591 (0.4); 1.2499 (0.4); 1.2353 (0.4); 1.0597 (1.1); 1.0420 (3.7); 1.0280 (1.3); 0.9254 (0.4); 0.9118 (0.6); 0.9071 (1.0); 0.8935 (0.8); 0.8889 (0.9); 0.8531 (0.5); 0.8345 (0.9); 0.8157 (0.4); 0.7295 (0.3); 0.7200 (0.5); 0.7111 (2.2); 0.6967 (4.1); 0.6925 (4.4); 0.6776 (1.3); 0.0080 (0.3); 0.0002 (10.4); 0.0085 (0.4)

[0986] I-109: .sup.1H-NMR (400.2 MHz, d.sub.6-DMSO):

[0987] =8.5714 (2.7); 8.5682 (3.0); 8.5548 (2.9); 8.5516 (2.9); 8.3148 (0.6); 8.1161 (0.6); 8.1117 (0.6); 8.1037 (0.7); 8.0992 (0.6); 7.8702 (2.6); 7.8670 (2.8); 7.8525 (2.9); 7.8493 (2.9); 7.6261 (0.3); 7.6092 (0.4); 7.5967 (0.8); 7.5931 (0.7); 7.5832 (1.6); 7.5782 (2.0); 7.5637 (16.0); 7.5514 (2.5); 7.5313 (0.6); 7.5234 (0.4); 7.4952 (0.7); 7.4868 (1.9); 7.4763 (1.1); 7.4743 (1.0); 7.4585 (1.2); 7.4444 (0.3); 7.4223 (0.3); 7.4082 (0.9); 7.4019 (1.5); 7.3992 (1.5); 7.3911 (1.0); 7.3857 (0.7); 7.3820 (1.0); 7.3789 (0.9); 7.3735 (0.6); 7.3552 (3.0); 7.3472 (1.0); 7.3426 (1.2); 7.3379 (4.5); 7.3291 (1.1); 7.3245 (1.1); 7.3208 (2.8); 6.9133 (5.9); 6.8959 (0.4); 6.7413 (0.7); 6.7288 (0.7); 6.7232 (0.7); 6.7107 (0.9); 6.5071 (0.4); 5.7550 (2.2); 5.3510 (2.3); 4.5808 (1.2); 4.5667 (1.1); 3.3194 (51.0); 2.6796 (0.6); 2.6751 (1.3); 2.6706 (1.8); 2.6660 (1.3); 2.6613 (0.6); 2.5408 (1.0); 2.5241 (5.8); 2.5194 (8.8); 2.5107 (98.0); 2.5062 (196.4); 2.5016 (259.6); 2.4970 (189.9); 2.4924 (92.8); 2.3376 (0.6); 2.3330 (1.2); 2.3284 (1.7); 2.3238 (1.2); 2.3194 (0.6); 1.3513 (3.8); 1.3358 (0.5); 1.2981 (0.6); 1.2587 (1.1); 1.2493 (1.2); 1.2342 (3.8); 1.2289 (4.0); 0.8538 (0.6); 0.8513 (0.6); 0.0080 (0.4); 0.0002 (12.3); 0.0085 (0.4)

[0988] I-111: .sup.1H-NMR (400.2 MHz, d.sub.6-DMSO):

[0989] =8.4145 (1.2); 8.3977 (1.2); 8.0805 (0.9); 8.0573 (1.4); 7.9836 (0.7); 7.9808 (0.7); 7.9668 (0.7); 7.9639 (0.7); 7.9609 (0.6); 7.9576 (0.5); 7.9437 (0.5); 7.9408 (0.5); 7.8830 (3.1); 7.1618 (0.7); 7.1449 (1.3); 7.1282 (0.6); 5.8519 (3.5); 4.0386 (0.5); 4.0207 (0.5); 3.6488 (3.8); 3.3246 (2.7); 2.8921 (0.9); 2.7328 (0.7); 2.5251 (0.9); 2.5117 (16.7); 2.5073 (32.4); 2.5028 (41.9); 2.4982 (30.6); 2.4939 (15.0); 1.9893 (2.2); 1.7350 (16.0); 1.6659 (1.6); 1.3972 (0.4); 1.1936 (0.6); 1.1758 (1.2); 1.1580 (0.6); 0.0079 (1.6); 0.0002 (45.3); 0.0085 (1.8)

Use Examples

[0990] The examples which follow demonstrate the insecticidal and acaricidal action of the compounds according to the invention. In these examples, the compounds according to the invention cited relate to the compounds listed in Table 1 with the corresponding reference numerals (No.):

[0991] Ctenocephalides felisIn Vitro Contact Tests with Adult Cat Fleas

[0992] 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 l of the solution are distributed homogeneously on the inner walls and the base of a 25 ml glass tube by turning and rocking on an orbital shaker (rocking rotation at 30 rpm for 2 h). With 900 ppm of active compound solution and internal surface area 44.7 cm.sup.2, given homogeneous distribution, an area-based dose of 5 g/cm.sup.2 is achieved.

[0993] 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 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.

[0994] A substance shows good efficacy against Ctenocephalides felis if at least 80% efficacy was achieved in this test at an application rate of 5 g/cm.sup.2. 100% efficacy means that all the fleas were dead or moribund. 0% efficacy means that no fleas were harmed.

[0995] In this test, for example, the following compounds from the preparation examples showed an efficacy of 100% at an application rate of 5 g/cm.sup.2 (=500 g/ha): I-007, I-008, I-013, I-015, I-019, I-024, I-033

[0996] Rhipicephalus sanguineusIn Vitro Contact Tests with Adults of the Brown Dog Tick

[0997] 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 l of the solution are distributed homogeneously on the inner walls and the base of a 25 ml glass tube by turning and rocking on an orbital shaker (rocking rotation at 30 rpm for 2 h). With 900 ppm of active compound solution and internal surface area 44.7 cm.sup.2, given homogeneous distribution, an area-based dose of 5 g/cm.sup.2 is achieved.

[0998] 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 the dark in a horizontal position at room temperature and ambient humidity. After 48 h, efficacy is determined. To this end, the ticks are knocked to the base of the tube and, incubated on a heating plate at 45-50 C. for a maximum of 5 minutes. Ticks which remain motionless at the base or move in such an uncoordinated manner that they cannot purposely escape the heat by climbing upward are considered to be dead or moribund.

[0999] A substance shows good efficacy against Rhipicephalus sanguineus if at least 80% efficacy was achieved in this test at an application rate of 5 g/cm.sup.2. 100% efficacy means that all the ticks were dead or moribund. 0% efficacy means that no ticks were harmed.

[1000] In this test, for example, the following compounds from the preparation examples showed an efficacy of 100% at an application rate of 5 g/cm.sup.2 (=500 g/ha): I-024, I-038 In this test, for example, the following compounds from the preparation examples showed an efficacy of 80% at an application rate of 5 g/cm.sup.2 (=500 g/ha): 1-038

[1001] Ctenocephalides felisOral Test

[1002] Solvent: dimethyl sulfoxide

[1003] To produce a suitable active compound formulation, 10 mg of active compound are mixed with 0.5 ml of dimethyl sulfoxide. Dilution with citrated cattle blood gives the desired concentration.

[1004] 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 formulation, which can be imbibed by the fleas through the parafilm membrane.

[1005] 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.

[1006] In this test, for example, the following compounds from the preparation examples showed an efficacy of 95% at an application rate of 100 ppm: I-007, I-019, I-033

[1007] In this test, for example, the following compounds from the preparation examples showed an efficacy of 90% at an application rate of 100 ppm: I-024

[1008] In this test, for example, the following compounds from the preparation examples showed an efficacy of 80% at an application rate of 100 ppm: I-038

[1009] Lucilia cuprina Test

[1010] Solvent: dimethyl sulfoxide

[1011] To produce a suitable active compound formulation, 10 mg of active compound are mixed with 0.5 ml of dimethyl sulfoxide, and the concentrate is diluted with water to the desired concentration.

[1012] About 20 L1 larvae of the Australian sheep blowfly (Lucilia cuprina) are transferred into a test vessel containing minced horsemeat and the active compound formulation of the desired concentration.

[1013] 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.

[1014] In this test, for example, the following compounds from the preparation examples showed an efficacy of 100% at an application rate of 100 ppm: I-018, I-024, I-026

[1015] In this test, for example, the following compounds from the preparation examples showed an efficacy of 95% at an application rate of 100 ppm: I-019, I-023, I-037

[1016] In this test, for example, the following compounds from the preparation examples showed an efficacy of 90% at an application rate of 100 ppm: I-038, I-045

[1017] In this test, for example, the following compounds from the preparation examples showed an efficacy of 85% at an application rate of 100 ppm: 1-007

[1018] Musca domestica Test

[1019] Solvent: dimethyl sulfoxide

[1020] To produce a suitable active compound formulation, 10 mg of active compound are mixed with 0.5 ml of dimethyl sulfoxide, and the concentrate is diluted with water to the desired concentration.

[1021] Vessels containing a sponge treated with sugar solution and the active compound formulation of the desired concentration are populated with 10 adult houseflies (Musca domestica).

[1022] 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.

[1023] In this test, for example, the following compounds from the preparation examples showed an efficacy of 100% at an application rate of 100 ppm: I-025, I-033, I-034, I-035, I-037, I-038

[1024] In this test, for example, the following compounds from the preparation examples showed an efficacy of 90% at an application rate of 100 ppm: I-007, I-013

[1025] In this test, for example, the following compounds from the preparation examples showed an efficacy of 85% at an application rate of 100 ppm: I-018

[1026] In this test, for example, the following compounds from the preparation examples showed an efficacy of 80% at an application rate of 100 ppm: I-019

[1027] Diabrotica balteataSpray Test

[1028] Solvent: 78 parts by weight of acetone [1029] 1.5 parts by weight of dimethylformamide

[1030] Emulsifier: alkylaryl polyglycol ether

[1031] To produce a suitable active compound formulation, 1 part by weight of active compound is dissolved with the specified parts by weight of solvent and made up to the desired concentration with water containing an emulsifier concentration of 1000 ppm. To produce further test concentrations, the formulation is diluted with emulsifier-containing water.

[1032] Pre-swollen wheat grains (Triticum aestivum) are incubated in a multiwell plate filled with agar and a little water for one day (5 seed grains per well). The germinated wheat grains are sprayed with an active compound preparation of the desired concentration. Subsequently, each cavity is infected with 10-20 beetle larvae of Diabrotica balteata.

[1033] After 7 days, the efficacy in % is determined. 100% means that all maize plants have grown as in the untreated, uninfected control; 0% means that no maize plant has grown.

[1034] In this test, for example, the following compounds from the preparation examples showed an efficacy of 100% at an application rate of 160 g/well: I-002, I-007, I-008, I-010, I-011, I-015, I-016, I-017, I-018, I-019, I-022, I-023, I-024, I-026, I-030, I-031, I-033, I-037, I-044, I-045, I-046, I-047, I-059

[1035] In this test, for example, the following compounds from the preparation examples showed an efficacy of 80% at an application rate of 160 g/well: I-005, I-013, I-014

[1036] Myzus persicaeOral Test

[1037] Solvent: 100 parts by weight of acetone

[1038] To produce a suitable active compound formulation, 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and made up to the desired concentration with water.

[1039] 50 l of the active compound formulation are transferred into microtitre plates and made up to a final volume of 200 l with 150 l of IPL41 insect medium (33%+15% sugar). Subsequently, the plates are sealed with parafilm, which a mixed population of green peach aphids (Myzus persicae) within a second microtitre plate is able to puncture and imbibe the solution.

[1040] After 5 days, the efficacy in % is determined. 100% means that all the aphids have been killed; 0% means that no aphids have been killed.

[1041] In this test, for example, the following compounds from the preparation examples showed an efficacy of 100% at an application rate of 20 ppm: I-001, I-002, I-003, I-005, I-006, I-007, I-008, I-009, I-010, I-012, I-013, I-018

[1042] In this test, for example, the following compounds from the preparation examples showed an efficacy of 90% at an application rate of 20 ppm: I-004

[1043] In this test, for example, the following compounds from the preparation examples showed an efficacy of 100% at an application rate of 4 ppm: I I-002, I-005, I-007, I-008, I-009, I-010, I-011, I-012, I-013, I-014, I-015, I-017, I-018, I-019, I-020, I-023, I-024, I-025, I-026, I-029, I-030, I-032, I-033, I-034, I-035, I-036, I-037, I-038, I-039, I-044, I-045, I-046, I-047, I-049, I-050, I-051, I-052, I-053, I-054, I-055, I-057, I-059, I-061, I-062, I-063, I-065

[1044] In this test, for example, the following compounds from the preparation examples showed an efficacy of 90% at an application rate of 4 ppm: I-003, I-016, I-031, I-066

[1045] Myzus persicaeSpray Test

[1046] Solvent: 78 parts by weight of acetone [1047] 1.5 parts by weight of dimethylformamide

[1048] Emulsifier: alkylaryl polyglycol ether

[1049] To produce a suitable active compound formulation, 1 part by weight of active compound is dissolved with the specified parts by weight of solvent and made up to the desired concentration with water containing an emulsifier concentration of 1000 ppm. To produce further test concentrations, the formulation is diluted with emulsifier-containing water.

[1050] Discs of Chinese cabbage leaves (Brassica pekinensis) infested by all stages of the green peach aphid (Myzus persicae) are sprayed with an active compound formulation of the desired concentration.

[1051] After 5 days, the efficacy in % is determined. 100% means that all the aphids have been killed; 0% means that no aphids have been killed.

[1052] In this test, for example, the following compounds from the preparation examples showed an efficacy of 100% at an application rate of 500 g/ha: I-002, I-007, I-008, I-010, I-013, I-018, I-019, I-032, I-035, I-037, I-042, I-044, I-045, I-050

[1053] In this test, for example, the following compounds from the preparation examples showed an efficacy of 90% at an application rate of 500 g/ha: I-011, I-015, I-020, I-023, I-024, I-033, I-034, I-036, I-038, I-039, I-040, I-046, I-047, I-049, I-051, I-055, I-057, I-062, I-065, I-066

[1054] In this test, for example, the following compounds from the preparation examples showed an efficacy of 70% at an application rate of 500 g/ha: I-054, I-059

[1055] Nezara viridulaSpray Test

[1056] Solvent: 78.0 parts by weight of acetone [1057] 1.5 parts by weight of dimethylformamide

[1058] Emulsifier: alkylaryl polyglycol ether

[1059] To produce a suitable active compound formulation, 1 part by weight of active compound is dissolved with the specified parts by weight of solvent and made up to the desired concentration with water containing an emulsifier concentration of 1000 ppm. To produce further test concentrations, the formulation is diluted with emulsifier-containing water.

[1060] Barley plants (Hordeum vulgare) infected with larvae of the Southern green shield bug (Nezara viridula) are srayed with an active compound formulation of the desired concentration.

[1061] After 4 days, the efficacy in % is determined. 100% means that all of the shield bugs have been killed; 0% means that none of the shield bugs have been killed.

[1062] In this test, for example, the following compounds from the preparation examples showed an efficacy of 90% at an application rate of 500 g/ha: I-008

[1063] Nilaparvata lugens Test

[1064] Solvent: 78.0 parts by weight of acetone [1065] 1.5 parts by weight of dimethylformamide

[1066] Emulsifier: alkylaryl polyglycol ether

[1067] To produce a suitable active compound formulation, 1 part by weight of active compound is dissolved with the specified parts by weight of solvent and made up to the desired concentration with water containing an emulsifier concentration of 1000 ppm. To produce further test concentrations, the formulation is diluted with emulsifier-containing water.

[1068] Rice plants (Oryza sativa) are sprayed with the active compound formulation of the desired concentration and then infected with the brown planthopper (Nilaparvata lugens).

[1069] After 4 days, the efficacy in % is determined. 100% means that all of the planthoppers have been killed; 0% means that none of the planthoppers have been killed.

[1070] In this test, for example, the following compounds from the preparation examples showed an efficacy of 100% at an application rate of 500 g/ha: I-008

[1071] Phaedon cochleariaeSpray Test

[1072] Solvent: 78.0 parts by weight of acetone [1073] 1.5 parts by weight of dimethylformamide

[1074] Emulsifier: alkylaryl polyglycol ether

[1075] To produce a suitable active compound formulation, 1 part by weight of active compound is dissolved with the specified parts by weight of solvent and made up to the desired concentration with water containing an emulsifier concentration of 1000 ppm. To produce further test concentrations, the formulation is diluted with emulsifier-containing water.

[1076] Discs of Chinese cabbage leaves (Brassica pekinensis) are sprayed with an active compound formulation of the desired concentration and, after drying, populated with larvae of the mustard beetle (Phaedon cochleariae).

[1077] 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.

[1078] In this test, for example, the following compounds from the preparation examples showed an efficacy of 100% at an application rate of 500 g/ha: I-024, I-045, I-046, I-060, I-061, I-062, I-063, I-065

[1079] In this test, for example, the following compounds from the preparation examples showed an efficacy of 83% at an application rate of 500 g/ha: I-044

[1080] Spodoptera frugiperdaSpray Test

[1081] Solvent: 78.0 parts by weight of acetone [1082] 1.5 parts by weight of dimethylformamide

[1083] Emulsifier: alkylaryl polyglycol ether

[1084] To produce a suitable active compound formulation, 1 part by weight of active compound is dissolved with the specified parts by weight of solvent and made up to the desired concentration with water containing an emulsifier concentration of 1000 ppm. To produce further test concentrations, the formulation is diluted with emulsifier-containing water.

[1085] Leaf discs of maize (Zea mays) are sprayed with an active compound formulation of the desired concentration and, after drying, populated with caterpillars of the fall armyworm (Spodoptera frugiperda).

[1086] After 7 days, the efficacy in % is determined. 100% means that all the caterpillars have been killed; 0% means that no caterpillar has been killed.

[1087] In this test, for example, the following compounds from the preparation examples showed an efficacy of 100% at an application rate of 500 g/ha: I-011, I-019, I-060, I-061, I-063

[1088] In this test, for example, the following compounds from the preparation examples showed an efficacy of 83% at an application rate of 500 g/ha: I-024, I-046

[1089] Tetranychus urticaeSpray Test, OP-Resistant

[1090] Solvent: 78.0 parts by weight of acetone [1091] 1.5 parts by weight of dimethylformamide

[1092] Emulsifier: alkylaryl polyglycol ether

[1093] To produce a suitable active compound formulation, 1 part by weight of active compound is dissolved with the specified parts by weight of solvent and made up to the desired concentration with water containing an emulsifier concentration of 1000 ppm. To produce further test concentrations, the formulation is diluted with emulsifier-containing water.

[1094] Discs of bean leaves (Phaseolus vulgaris) infested by all stages of the red spider mite (Tetranychus urticae) are sprayed with an active compound formulation of the desired concentration.

[1095] 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.

[1096] In this test, for example, the following compounds from the preparation examples showed an efficacy of 100% at an application rate of 500 g/ha: I-040

[1097] In this test, for example, the following compounds from the preparation examples showed an efficacy of 90% at an application rate of 500 g/ha: I-037, I-039, I-041, I-050

MESOIONIC IMIDAZOPYRIDINES AS INSECTICIDES

Inventors

Cpc classification

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C07D417/12

CHEMISTRY; METALLURGY

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A61P33/14

HUMAN NECESSITIES

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A01M17/00

HUMAN NECESSITIES

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A01M1/20

HUMAN NECESSITIES

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A01M25/00

HUMAN NECESSITIES

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A01C1/00

HUMAN NECESSITIES

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A01N43/90

HUMAN NECESSITIES

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C07D471/04

CHEMISTRY; METALLURGY

International classification

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A01M17/00

HUMAN NECESSITIES

Classification Explorer

A01M1/20

HUMAN NECESSITIES

Classification Explorer

C07D471/04

CHEMISTRY; METALLURGY

Classification Explorer

A01M25/00

HUMAN NECESSITIES

Classification Explorer

A01C1/00

HUMAN NECESSITIES

Classification Explorer

A01N43/90

HUMAN NECESSITIES

Abstract

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Description