ACTIVE COMPOUND COMBINATIONS

Abstract

The present invention relates to active compound combinations comprising at least one triazole derivative of formula (I)

##STR00001##

as defined in claim 1 as well as at least one further fungicide, to compositions comprising such compound combination, and to the use thereof as biologically active agents, especially for control of harmful microorganisms in crop protection and in the protection of materials and as plant growth regulators.

Claims

1. An active compound combination comprising (A) at least one triazole derivative of formula (I) ##STR00273## wherein R.sup.1 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.8-cycloalkyl, C.sub.3-C.sub.8-cycloalkyl-C.sub.1-C.sub.4-alkyl, phenyl, phenyl-C.sub.1-C.sub.4-alkyl, phenyl-C.sub.2-C.sub.4-alkenyl or phenyl-C.sub.2-C.sub.4-alkynyl; R.sup.2 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.8-cycloalkyl, C.sub.3-C.sub.8-cycloalkyl-C.sub.1-C.sub.4-alkyl, phenyl, phenyl-C.sub.1-C.sub.4-alkyl, phenyl-C.sub.1-C.sub.4-alkenyl or phenyl-C.sub.2-C.sub.4-alkynyl, wherein the aliphatic moieties, excluding cycloalkyl moieties, of R.sup.1 and/or R.sup.2 may carry 1, 2, 3 or up to the maximum possible number of identical or different groups R.sup.a which independently of one another are selected from halogen, CN, nitro, phenyl, C.sub.1-C.sub.4-alkoxy and C.sub.1-C.sub.4-halogenalkoxy, wherein the phenyl may be substituted by 1, 2, 3, 4 or 5 substituents selected from halogen, CN, nitro, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-halogenalkyl, C.sub.1-C.sub.4-halogenalkoxy, and wherein the cycloalkyl and/or phenyl moieties of R.sup.1 and/or R.sup.2 may carry 1, 2, 3, 4, 5 or up to the maximum number of identical or different groups R.sup.b which independently of one another are selected from halogen, CN, nitro, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-halogenalkyl and C.sub.1-C.sub.4-halogenalkoxy; each R.sup.4 represents independently of one another halogen, CN, nitro, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-halogenalkoxy, C.sub.1-C.sub.4-alkylcarbonyl, hydroxy-substituted C.sub.1-C.sub.4-alkyl or pentafluoro-.sup.6-sulfanyl; m is an integer and is 0, 1, 2, 3, 4 or 5; Y represents a 6-membered aromatic heterocycle containing 1 or 2 nitrogen atom(s) as heteroatom(s) selected from ##STR00274## wherein Y is connected to the O of formula (I) via the bonds identified with U and Y is connected to the CR.sup.1(OR.sup.2) moiety of formula (I) via the bonds identified with V and wherein R represents hydrogen, C.sub.1-C.sub.2-halogenalkyl, C.sub.1-C.sub.2-halogenalkoxy, C.sub.1-C.sub.2-alkylcarbonyl or halogen; each R.sup.3 represents independently of one another halogen, CN, nitro, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenalkyl, C.sub.1-C.sub.4-alkoxy or C.sub.1-C.sub.4-halogenalkoxy; n is an integer and is 0, 1 or 2; or a salt or N-oxide thereof, and (B) at least one further active compound selected from the following groups (1) inhibitors of the ergosterol synthesis, (2) inhibitors of the respiratory chain at complex I or II, (3) inhibitors of the respiratory chain at complex III, (4) inhibitors of the mitosis and cell division, (5) compounds capable of having a multisite action, (6) compounds capable of inducing a host defense, (7) inhibitors of the amino acid and/or protein biosynthesis, (8) inhibitors of the ATP production, (9) inhibitors of the cell wall synthesis, (10) inhibitors of the lipid and membrane synthesis, (11) inhibitors of the melanine biosynthesis, (12) inhibitors of the nucleic acid synthesis, (13) inhibitors of the signal transduction, (14) compounds capable of acting as uncoupler, (15) other fungicides.

2. The active compound combination according to claim 1, wherein the triazole derivative of formula (I) is a triazole derivative of formula (I), wherein each R.sup.4 represents independently of one another halogen, CN, nitro, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-halogenalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-halogenalkoxy or pentafluoro-.sup.6-sulfanyl; and/or R represents hydrogen, C.sub.1-C.sub.2-halogenalkyl or halogen, or a salt or N-oxide thereof.

3. The active compound combination according to claim 1, wherein the triazole derivative of formula (I) is a triazole derivative of formula (I), wherein Y represents a 6-membered aromatic heterocycle containing 1 or 2 nitrogen atom(s) as heteroatom(s) selected from ##STR00275## wherein Y is connected to the O of formula (I) via the bonds identified with U and Y is connected to the CR.sup.1(OR.sup.2) moiety of formula (I) via the bonds identified with V, or a salt or N-oxide thereof.

4. The active compound combination according to claim 1, wherein the triazole derivative of formula (I) is a triazole derivative of formula (I), wherein R.sup.1 represents hydrogen, C.sub.1-C.sub.4-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, cyclopropyl, phenyl, benzyl, phenylethenyl or phenylethinyl; R.sup.2 represents hydrogen, C.sub.1-C.sub.4-alkyl, allyl, propargyl or benzyl, wherein the aliphatic moieties, excluding cycloalkyl moieties, of R.sup.1 and/or R.sup.2 may carry 1, 2, 3 or up to the maximum possible number of identical or different groups R.sup.e which independently of one another are selected from halogen, CN, nitro, phenyl, C.sub.1-C.sub.4-alkoxy and C.sub.1-C.sub.4-halogenalkoxy, wherein the phenyl may be substituted by 1, 2, 3, 4 or 5 substituents selected independently of one another from halogen; CN; nitro; C.sub.1-C.sub.4-alkyl; C.sub.1-C.sub.4-alkoxy; C.sub.1-C.sub.4-halogenalkyl; C.sub.1-C.sub.4-halogenalkoxy, and wherein the cycloalkyl and/or phenyl moieties of R.sup.1 and/or R.sup.2 may carry 1, 2, 3, 4, 5 or up to the maximum number of identical or different groups R.sup.b which independently of one another are selected from halogen, CN, nitro, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-halogenalkyl and C.sub.1-C.sub.4-halogenalkoxy; each R.sup.4 represents independently of one another CF.sub.3, OCF.sub.3, Br, Cl or pentafluoro-.sup.6-sulfanyl; m is 1, 2 or 3; Y represents ##STR00276## wherein Y is connected to the O of formula (I) via the bonds identified with U and Y is connected to the CR.sup.1(OR.sup.2) moiety of formula (I) via the bonds identified with V or a salt or N-oxide thereof.

5. The active compound combination according to claim 1, wherein the triazole derivative of formula (I) is a triazole derivative of formula (I), wherein R.sup.1 represents hydrogen, C.sub.1-C.sub.4-alkyl or cyclopropyl; R.sup.2 represents hydrogen; R.sup.4 represents CF.sub.3, OCF.sub.3, Br, Cl or pentafluoro-.sup.6-sulfanyl; m is 1; Y represents ##STR00277## wherein Y is connected to the O of formula (I) via the bonds identified with U and Y is connected to the CR.sup.1(OR.sup.2) moiety of formula (I) via the bonds identified with V and R represents C.sub.1-halogenalkyl; n is 0; or a salt or N-oxide thereof.

6. The active compound combination according to claim 1, wherein the triazole derivative of formula (I) is a triazole derivative of formula (I), wherein R.sup.4 represents Cl or Br in the 4-position of the phenyl moiety of formula (I); or a salt or N-oxide thereof.

7. The active combination according to claim 1, wherein the triazole derivative of formula (I) is selected from the group consisting of (I.01) 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (I.59) 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (I.81) 1-[6-(4-bromophenoxy)-2-(trifluoromethyl)pyridin-3-yl]-1-cyclopropyl-2-(1H-1,2,4-triazol-1-yl)ethanol and (I.91) 1-[6-(4-chlorophenoxy)-2-(trifluoromethyl)pyridin-3-yl]-1-cyclopropyl-2-(1H-1,2,4-triazol-1-yl)ethanol.

8. The active compound combination according to claim 1, wherein the further active compound is selected from the group consisting of (1.001) cyproconazole, (1.002) difenoconazole, (1.003) epoxiconazole, (1.004) fenhexamid, (1.005) fenpropidin, (1.006) fenpropimorph, (1.007) fenpyrazamine, (1.008) fluquinconazole, (1.009) flutriafol, (1.010) imazalil, (1.011) imazalil sulfate, (1.012) ipconazole, (1.013) metconazole, (1.014) myclobutanil, (1.015) paclobutrazol, (1.016) prochloraz, (1.017) propiconazole, (1.018) prothioconazole, (1.019) Pyrisoxazole, (1.020) spiroxamine, (1.021) tebuconazole, (1.022) tetraconazole, (1.023) triadimenol, (1.024) tridemorph, (1.025) triticonazole, (1.026) (1R,2S,5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (1.027) (1S,2R,5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (1.028) (2R)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.029) (2R)-2-(1-chlorocyclopropyl)-4-[(1 S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.030) (2R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazole-1-yl)propan-2-ol, (1.031) (2S)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.032) (2S)-2-(1-chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.033) (2S)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.034) (R)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.035) (S)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.036) [3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.037) 1-({(2R,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4-triazole, (1.038) 1-({(2S,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4-triazole, (1.039) 1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate, (1.040) 1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate, (1.041) 1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate, (1.042) 2-[(2R,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.043) 2-[(2R,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.044) 2-[(2R,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.045) 2-[(2R,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.046) 2-[(2S,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.047) 2-[(2S,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.048) 2-[(2S,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.049) 2-[(2S,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.050) 2-[1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.051) 2-[2-chloro-4-(2,4-dichlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.052) 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.053) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.054) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)pentan-2-ol, (1.055) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.056) 2-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.057) 2-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.058) 2-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-fluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.059) 5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (1.060) 5-(allylsulfanyl)-1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (1.061) 5-(allylsulfanyl)-1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (1.062) 5-(allylsulfanyl)-1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (1.063) N-(2,5-dimethyl-4-{[3-(1,1,2,2-tetrafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide, (1.064) N-(2,5-dimethyl-4-{[3-(2,2,2-trifluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide, (1.065) N-(2,5-dimethyl-4-{[3-(2,2,3,3-tetrafluoropropoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide, (1.066) N-(2,5-dimethyl-4-{[3-(pentafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide, (1.067) N-(2,5-dimethyl-4-{3-[(1,1,2,2-tetrafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, (1.068) N-(2,5-dimethyl-4-{3-[(2,2,2-trifluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, (1.069) N-(2,5-dimethyl-4-{3-[(2,2,3,3-tetrafluoropropyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, (1.070) N-(2,5-dimethyl-4-{3-[(pentafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, (1.071) N-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylimidoformamide, (1.072) N-(4-{[3-(difluoromethoxy)phenyl]sulfanyl}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide, (1.073) N-(4-{3-[(difluoromethyl)sulfanyl]phenoxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide, (1.074) N-[5-bromo-6-(2,3-dihydro-1H-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylimidoformamide, (1.075) N-{4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide, (1.076) N-{5-bromo-6-[(1R)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1.077) N-{5-bromo-6-[(1 S)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1.078) N-{5-bromo-6-[(cis-4-isopropycyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1.079) N-{5-bromo-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1.080) N-{5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1.081) Mefentrifluconazole, (1.082) Ipfentrifluconazole, (2.001) benzovindiflupyr, (2.002) bixafen, (2.003) boscalid, (2.004) carboxin, (2.005) fluopyram, (2.006) flutolanil, (2.007) fluxapyroxad, (2.008) furametpyr, (2.009) Isofetamid, (2.010) isopyrazam (anti-epimeric enantiomer 1R,4S,9S), (2.011) isopyrazam (anti-epimeric enantiomer 1S,4R,9R), (2.012) isopyrazam (anti-epimeric racemate 1RS,4SR,9SR), (2.013) isopyrazam (mixture of syn-epimeric racemate 1RS,4SR,9RS and anti-epimeric racemate 1RS,4SR,9SR), (2.014) isopyrazam (syn-epimeric enantiomer 1R,4S,9R), (2.015) isopyrazam (syn-epimeric enantiomer 1S,4R,9S), (2.016) isopyrazam (syn-epimeric racemate 1RS,4SR,9RS), (2.017) penflufen, (2.018) penthiopyrad, (2.019) pydiflumetofen, (2.020) Pyraziflumid, (2.021) sedaxane, (2.022) 1,3-dimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide, (2.023) 1,3-dimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (2.024) 1,3-dimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (2.025) 1-methyl-3-(trifluoromethyl)-N-[2-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide, (2.026) 2-fluoro-6-(trifluoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)benzamide, (2.027) 3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide, (2.028) 3-(difluoromethyl)-1-methyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (2.029) 3-(difluoromethyl)-1-methyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (2.030) 3-(difluoromethyl)-N-(7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1-methyl-1H-pyrazole-4-carboxamide, (2.031) 3-(difluoromethyl)-N-[(3R)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide, (2.032) 3-(difluoromethyl)-N-[(3S)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide, (2.033) 5,8-difluoro-N-[2-(2-fluoro-4-{[4-(trifluoromethyl)pyridin-2-yl]oxy}phenyl)ethyl]quinazolin-4-amine, (2.034) N-(2-cyclopentyl-5-fluorobenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.035) N-(2-tert-butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.036) N-(2-tert-butylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.037) N-(5-chloro-2-ethylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.038) N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.039) N-[(1R,4S)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.040) N-[(1 S,4R)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.041) N-[1-(2,4-dichlorophenyl)-1-methoxypropan-2-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.042) N-[2-chloro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.043) N-[3-chloro-2-fluoro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.044) N-[5-chloro-2-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.045) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-N-[5-methyl-2-(trifluoromethyl)benzyl]-1H-pyrazole-4-carboxamide, (2.046) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-fluoro-6-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.047) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropyl-5-methylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.048) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carbothioamide, (2.049) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.050) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(5-fluoro-2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.051) N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-4,5-dimethylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.052) N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-fluorobenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.053) N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-methylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.054) N-cyclopropyl-N-(2-cyclopropyl-5-fluorobenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.055) N-cyclopropyl-N-(2-cyclopropyl-5-methylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.056) N-cyclopropyl-N-(2-cyclopropylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (3.001) ametoctradin, (3.002) amisulbrom, (3.003) azoxystrobin, (3.004) coumethoxystrobin, (3.005) coumoxystrobin, (3.006) cyazofamid, (3.007) dimoxystrobin, (3.008) enoxastrobin, (3.009) famoxadone, (3.010) fenamidone, (3.011) flufenoxystrobin, (3.012) fluoxastrobin, (3.013) kresoxim-methyl, (3.014) metominostrobin, (3.015) orysastrobin, (3.016) picoxystrobin, (3.017) pyraclostrobin, (3.018) pyrametostrobin, (3.019) pyraoxystrobin, (3.020) trifloxystrobin, (3.021) (2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-phenylvinyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide, (3.022) (2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide, (3.023) (2R)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (3.024) (2S)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (3.025) (3S,6S,7R,8R)-8-benzyl-3-[({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl 2-methylpropanoate, (3.026) 2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (3.027) N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-formamido-2-hydroxybenzamide, (3.028) (2E,3Z)-5-{[1-(4-chloro-2-fluorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide, (3.029) methyl {5-[3-(2,4-dimethylphenyl)-1H-pyrazol-1-yl]-2-methylbenzyl}carbamate, (4.001) carbendazim, (4.002) diethofencarb, (4.003) ethaboxam, (4.004) fluopicolide, (4.005) pencycuron, (4.006) thiabendazole, (4.007) thiophanate-methyl, (4.008) zoxamide, (4.009) 3-chloro-4-(2,6-difluorophenyl)-6-methyl-5-phenylpyridazine, (4.010) 3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine, (4.011) 3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6-trifluorophenyl)pyridazine, (4.012) 4-(2-bromo-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.013) 4-(2-bromo-4-fluorophenyl)-N-(2-bromo-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.014) 4-(2-bromo-4-fluorophenyl)-N-(2-bromophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.015) 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.016) 4-(2-bromo-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.017) 4-(2-bromo-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.018) 4-(2-chloro-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.019) 4-(2-chloro-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.020) 4-(2-chloro-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.021) 4-(2-chloro-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.022) 4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-dimethylpyridazine, (4.023) N-(2-bromo-6-fluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.024) N-(2-bromophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.025) N-(4-chloro-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (5.001) bordeaux mixture, (5.002) captafol, (5.003) captan, (5.004) chlorothalonil, (5.005) copper hydroxide, (5.006) copper naphthenate, (5.007) copper oxide, (5.008) copper oxychloride, (5.009) copper (2+) sulfate, (5.010) dithianon, (5.011) dodine, (5.012) folpet, (5.013) mancozeb, (5.014) maneb, (5.015) metiram, (5.016) metiram zinc, (5.017) oxine-copper, (5.018) propineb, (5.019) sulfur and sulfur preparations including calcium polysulfide, (5.020) thiram, (5.021) zineb, (5.022) ziram, (5.023) 6-ethyl-5,7-dioxo-6,7-dihydro-5H-pyrrolo[3,4:5,6][1,4]dithiino[2,3-c][1,2]thiazole-3-carbonitrile, (6.001) acibenzolar-S-methyl, (6.002) isotianil, (6.003) probenazole, (6.004) tiadinil, (7.001) cyprodinil, (7.002) kasugamycin, (7.003) kasugamycin hydrochloride hydrate, (7.004) oxytetracycline, (7.005) pyrimethanil, (7.006) 3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinolone, (8.001) silthiofam, (9.001) benthiavalicarb, (9.002) dimethomorph, (9.003) flumorph, (9.004) iprovalicarb, (9.005) mandipropamid, (9.006) pyrimorph, (9.007) valifenalate, (9.008) (2E)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one, (9.009) (2Z)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one, (10.001) propamocarb, (10.002) propamocarb hydrochloride, (10.003) tolclofos-methyl, (11.001) tricyclazole, (11.002) 2,2,2-trifluoroethyl {3-methyl-1-[(4-methylbenzoyl)amino]butan-2-yl}carbamate, (12.001) benalaxyl, (12.002) benalaxyl-M (kiralaxyl), (12.003) metalaxyl, (12.004) metalaxyl-M (mefenoxam), (13.001) fludioxonil, (13.002) iprodione, (13.003) procymidone, (13.004) proquinazid, (13.005) quinoxyfen, (13.006) vinclozolin, (14.001) fluazinam, (14.002) meptyldinocap, (15.001) Abscisic acid, (15.002) benthiazole, (15.003) bethoxazin, (15.004) capsimycin, (15.005) carvone, (15.006) chinomethionat, (15.007) cufraneb, (15.008) cyflufenamid, (15.009) cymoxanil, (15.010) cyprosulfamide, (15.011) flutianil, (15.012) fosetyl-aluminium, (15.013) fosetyl-calcium, (15.014) fosetyl-sodium, (15.015) methyl isothiocyanate, (15.016) metrafenone, (15.017) mildiomycin, (15.018) natamycin, (15.019) nickel dimethyldithiocarbamate, (15.020) nitrothal-isopropyl, (15.021) oxamocarb, (15.022) Oxathiapiprolin, (15.023) oxyfenthiin, (15.024) pentachlorophenol and salts, (15.025) phosphorous acid and its salts, (15.026) propamocarb-fosetylate, (15.027) pyriofenone (chlazafenone), (15.028) tebufloquin, (15.029) tecloftalam, (15.030) tolnifanide, (15.031) 1-(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone, (15.032) 1-(4-{4-[(5S)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone, (15.033) 2-(6-benzylpyridin-2-yl)quinazoline, (15.034) 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c]dipyrrole-1,3,5,7(2H,6H)-tetrone, (15.035) 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-(prop-2-yl}-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl)-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, (15.036) 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-chloro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, (15.037) 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-fluoro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, (15.038) 2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline, (15.039) 2-{(5R)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl methanesulfonate, (15.040) 2-{(5S)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl methanesulfonate, (15.041) 2-{2-[(7,8-difluoro-2-methylquinolin-3-yl)oxy]-6-fluorophenyl}propan-2-ol, (15.042) 2-{2-fluoro-6-[(8-fluoro-2-methylquinolin-3-yl)oxy]phenyl}propan-2-ol, (15.043) 2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl methanesulfonate, (15.044) 2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenyl methanesulfonate, (15.045) 2-phenylphenol and salts, (15.046) 3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline, (15.047) 3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline, (15.048) 4-amino-5-fluoropyrimidin-2-ol (tautomeric form: 4-amino-5-fluoropyrimidin-2(1H)-one), (15.049) 4-oxo-4-[(2-phenylethyl)amino]butanoic acid, (15.050) 5-amino-1,3,4-thiadiazole-2-thiol, (15.051) 5-chloro-N-phenyl-N-(prop-2-yn-1-yl)thiophene-2-sulfonohydrazide, (15.052) 5-fluoro-2-[(4-fluorobenzyl)oxy]pyrimidin-4-amine, (15.053) 5-fluoro-2-[(4-methylbenzyl)oxy]pyrimidin-4-amine, (15.054) 9-fluoro-2,2-dimethyl-5-(quinolin-3-yl)-2,3-dihydro-1,4-benzoxazepine, (15.055) but-3-yn-1-yl {6-[({[(Z)-(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate, (15.056) ethyl (2Z)-3-amino-2-cyano-3-phenylacrylate, (15.057) phenazine-1-carboxylic acid, (15.058) propyl 3,4,5-trihydroxybenzoate, (15.059) quinolin-8-ol, (15.060) quinolin-8-ol sulfate (2:1), (15.061) tert-butyl {6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate, and (15.062) 5-fluoro-4-imino-3-methyl-1-[(4-methylphenyl)sulfonyl]-3,4-dihydropyrimidin-2(1H)-one.

9. The active compound combination according to claim 1, wherein the further active compound is selected from the group consisting of (1.012) ipconazole, (1.018) prothioconazole, (1.020) spiroxamine, (1.021) tebuconazole, (2.002) bixafen, (2.005) fluopyram, (2.017) penflufen, (2.027) 3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide, (2.038) N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (3.020) trifloxystrobin, (3.025) (3S,6S,7R,8R)-8-benzyl-3-[({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)-amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl 2-methylpropanoate, (4.005) pencycuron, (5.004) chlorothalonil, (5.013) mancozeb, (5.018) propineb, (12.003) metalaxyl, (12.004) metalaxyl-M (mefenoxam), (13.001) fludioxonil, (13.004) proquinazid, (15.008) cyflufenamid, and (15.047) 3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinolone.

10. Composition for controlling one or more harmful microorganisms, optionally phytopathogenic harmful fungi, in crop protection and/Qr in protection of one or more materials, comprising a content of the active compound combination according to claim 1, in addition to at least one extender and/or surfactant.

11. Method for controlling one or more harmful microorganisms, phytopathogenic harmful fungi, in crop protection and/or in protection of one or more materials, comprising applying the active compound combination according to claim 1 or a composition thereof to the harmful microorganisms and/or a habitat thereof.

12. A product comprising an active compound combination according to claim 1 or a composition thereof for control of one or more harmful microorganisms, optionally phytopathogenic harmful fungi, in crop protection and/r in protection of one or more materials.

13. A product comprising an active compound combination according to claim 1 or a composition thereof for treatment of a transgenic plant.

14. A product comprising an active compound combination according to claim 1 or a composition thereof for treatment of seed, optionally seed of a transgenic plant.

15. Seed coated with the active compound combination according to claim 1 or a composition thereof.

Description

EXAMPLES

Preparation Examples of Compounds of Formula (I)

Preparation of Compounds of the Formula (I) According to Process A

Preparation of 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol (I.01)

[0303] ##STR00012##

[0304] A solution of magnesium bromide diethyl etherate (4.8 g, 18.8 mmol) in dichloromethane (20 mL) and diethyl ether (10 mL) was cooled to 0 C., before a solution of 1-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-2-(1,2,4-triazol-1-yl)ethanone (1.80 g, 4.70 mmol) in dichloromethane (10 mL) was added and stirred for 30 min at 0 C. Then methylmagnesium bromide (3.1 mL, 9.4 mmol, 3M solution in ethyl ether) was added, the cooling bath was removed, and the mixture was stirred for 1.5 hours (h) at 21 C. (room temperature, rt), before the mixture was quenched with water, NH.sub.4Cl (saturated aqueous solution), extracted with dichloromethane, dried (over MgSO.sub.4), and concentrated. As the starting ketone and the target alcohol overlap in terms of retention time, the concentrated material (roughly 2 g of a thick colourless oil containing both ketone and alcohol) was dissolved in pyridine (15.0 mL), and treated with methoxylamine hydrochloride (313 mg, 3.75 mmol) at rt for 20 h (to convert the ketone into the corresponding methyl oxime, which has a significantly different retention time). The mixture was then diluted with dichloromethane, filtered over ChemElut, and concentrated. Preparative HPLC gave 319 mg (17% yield over two steps, 99% pure) of the target compound as colourless oil, which solidified upon standing.

[0305] MS (ESI): 398.08 ([M+H].sup.+)

Preparation of 2-[6-(4-chlorophenoxy)-4-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol (I.02)

[0306] ##STR00013##

[0307] A solution of magnesium bromide diethyl etherate (1.2 g, 4.63 mmol) in dichloromethane (10 mL) was cooled to 0 C., before a solution of 1-[6-(4-chlorophenoxy)-4-(trifluoromethyl)-3-pyridyl]-2-(1,2,4-triazol-1-yl)ethanone (443 mg, 1.16 mmol) in dichloromethane (2 mL) was added and stirred for 30 min at 0 C. Then methylmagnesium bromide (0.78 mL, 2.3 mmol, 3M solution in ethyl ether) was added, the cooling bath was removed, and the mixture was stirred for 1 h at rt, before the mixture was quenched with water, extracted with dichloromethane, dried (over MgSO.sub.4), and concentrated. Preparative HPLC gave 126.6 mg (27% yield, 100% pure) of the target compound as a colourless solid.

[0308] MS (ESI): 398.08 ([M+H].sup.+)

Preparation of 1-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-2-(1,2,4-triazol-1-yl)ethanol (I.03)

[0309] ##STR00014##

[0310] To a solution of 1-[6-(4-chlorophenoxy)-4-(trifluoromethyl)-3-pyridyl]-2-(1,2,4-triazol-1-yl)ethanone (800 mg, 1.67 mmol) in dry methanol (25.0 mL) at 5 C. was added sodium borohydride (127 mg, 3.3 mmol), the cooling bath was removed, mixture warmed to rt and stirred for 1 h. The mixture was then quenched with water, diluted with dichloromethane, filtered over ChemElut, and concentrated. Preparative HPLC gave 286 mg (60% yield, 100% pure) of the target compound as a colourless solid.

[0311] MS (ESI): 384.06 ([M+H].sup.+)

Preparation of 1-[6-(4-chlorophenoxy)-4-(trifluoromethyl)-3-pyridyl]-2-(1,2,4-triazol-1-yl)ethanol (I.04)

[0312] ##STR00015##

[0313] To a solution of 1-[6-(4-chlorophenoxy)-4-(trifluoromethyl)-3-pyridyl]-2-(1,2,4-triazol-1-yl)ethanone (518 mg, 1.35 mmol) in dry methanol (5.0 mL) at 5 C. was added sodium borohydride (102 mg, 2.7 mmol), the cooling bath was removed, mixture warmed to rt and stirred for 1 h. The mixture was then quenched with water, diluted with dichloromethane, filtered over ChemElut, and concentrated. Preparative HPLC gave 252 mg (48% yield, 100% pure) of the target compound as a colourless oil, which crystallized upon standing.

[0314] MS (ESI): 384.06 ([M+H].sup.+)

Preparation of Compounds of the Formula (VII) According to Process A

Preparation of 1-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-2-(1,2,4-triazol-1-yl)ethanone (VII.01)

[0315] ##STR00016##

[0316] A mixture of 2-chloro-1-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]ethanone (8.3 g, 23.7 mmol) and 1H-1,2,4-triazole (1.8 g, 26.0 mmol) in acetonitrile (80 mL) was heated to 75 C., before potassium carbonate (3.9 g, 28.5 mmol) was added. The heating was continued for 20 minutes (min) before the mixture was rapidly cooled to room temperature by addition of ice water, extracted with dichloromethane, dried (over MgSO.sub.4), and concentrated. Flash column chromatography (gradient, up to DCM/10% MeOH in DCM=60/40, 254 nm) gave 4.30 g (43% yield, 91% pure) of the target compound as a yellow glass, which was used as such for the next reaction steps. A small quantity was further purified by HPLC to give the target product (100% pure) as a yellow solid.

[0317] MS (ESI): 382.04 ([M+H].sup.+)

Preparation of 1-[6-(4-chlorophenoxy)-4-(trifluoromethyl)-3-pyridyl]-2-(1,2,4-triazol-1-yl)ethanone (VII.02)

[0318] ##STR00017##

[0319] A mixture of 2-chloro-1-[6-(4-chlorophenoxy)-4-(trifluoromethyl)-3-pyridyl]ethanone (3.4 g, 9.71 mmol) and 1H-1,2,4-triazole (0.74 g, 10.6 mmol) in acetonitrile (50 mL) was heated to 75 C., before potassium carbonate (1.6 g, 11.6 mmol) was added. The heating was continued for 20 min before the mixture was rapidly cooled to room temperature by addition of ice water, extracted with dichloromethane, dried (over MgSO.sup.4), and concentrated. Flash column chromatography (gradient, up to DCM/10% MeOH in DCM=70/30, 254 nm) followed by preparative HPLC gave 1.50 g (40% yield, 100% pure) of the target compound as a yellow solid.

[0320] MS (ESI): 382.04 ([M+H].sup.+)

Preparation of Compounds of the Formula (VI) According to Process A

Preparation of 2-chloro-1-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]ethanone (VI.01)

[0321] ##STR00018##

[0322] A mixture of 1-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]ethanone (8.6 g, 27.2 mmol) and benzyltrimethylammonium dichloroiodate (18.9 g, 54.4 mmol) in 1,2-dichloroethane (60 mL) and methanol (20 mL) was heated to 75 C. for 4 h, before the mixture was concentrated, then diluted with ethyl acetate, washed with Na.sub.2S.sub.2O.sub.3 (10% w/w aqueous solution), washed with brine, dried (over MgSO.sub.4), concentrated, and passed over a plug of silica (heptane/ethyl acetate=1/1, 254 nm) to give 8.3 g (83% yield, 96% pure) of the target compound as a pale yellow solid.

[0323] MS (ESI): 348.99 ([M+H].sup.+)

Preparation of 2-chloro-1-[6-(4-chlorophenoxy)-4-(trifluoromethyl)-3-pyridyl]ethanone (VI.02)

[0324] ##STR00019##

[0325] A mixture of 1-[6-(4-chlorophenoxy)-4-(trifluoromethyl)-3-pyridyl]ethanone (3.6 g, 11.4 mmol) and benzyltrimethylammonium dichloroiodate (7.93 g, 22.8 mmol) in 1,2-dichloroethane (30 mL) and methanol (10 mL) was heated to 75 C. for 4 h, before the mixture was concentrated, then diluted with ethyl acetate, washed with Na.sub.2S.sub.2O.sub.3 (10% w/w aqueous solution), washed with brine, dried (over MgSO.sub.4), concentrated, and passed over a plug of silica (heptane/ethyl acetate=85/15, 254 nm) to give 3.4 g (58% yield, 69% pure) of the target compound as a colourless oil, which was used without further purification.

[0326] MS (ESI): 348.99 ([M+H].sup.+)

Preparation of Compounds of the Formula (V) According to Process D

Preparation of 1-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]ethanone (V.01)

[0327] ##STR00020##

[0328] A solution of 6-(4-chlorophenoxy)-N-methoxy-N-methyl-2-(trifluoromethyl)pyridine-3-carboxamide (11.5 g, 31.9 mmol) in THF (150 mL) at 5 C. was treated with methylmagnesium bromide (21.2 mL, 63.7 mmol, 3M solution in diethyl ether). The mixture was then warmed to rt and stirring continued for 4 h at rt, before the reaction was quenched with water, NH.sub.4Cl (saturated aqueous solution), extracted with dichloromethane, dried (over Na.sub.2SO.sub.4), and concentrated to give 8.60 g (82% yield, 96% pure) of the target compound as a pale yellow solid, which was used without further purification.

[0329] MS (ESI): 315.03 ([M+H].sup.+)

Preparation of 1-[6-(4-chlorophenoxy)-4-(trifluoromethyl)-3-pyridyl]ethanone (V.02)

[0330] ##STR00021##

[0331] A solution of 6-(4-chlorophenoxy)-N-methoxy-N-methyl-4-(trifluoromethyl)pyridine-3-carboxamide (6.9 g, 17.4 mmol) in THF (100 mL) at 5 C. was treated with methylmagnesium bromide (11.6 mL, 34.8 mmol, 3M solution in diethyl ether). The mixture was then warmed to rt and stirring continued for 4 h at rt, before the reaction was quenched with water, NH.sub.4Cl (saturated aqueous solution), extracted with dichloromethane, dried (over Na.sub.2SO.sub.4), and concentrated. Flash column chromatography (gradient, up to heptane/ethyl acetate=80/20, 254 nm) gave 3.60 g (61% yield, 94% pure) of the target compound as a colourless oil.

[0332] MS (ESI): 315.03 ([M+H].sup.+)

Preparation of Compounds of the Formula (XVI) According to Process D

Preparation of 6-(4-chlorophenoxy)-N-methoxy-N-methyl-2-(trifluoromethyl)pyridine-3-carboxamide (XVI.01)

[0333] ##STR00022##

[0334] A mixture of 6-chloro-N-methoxy-N-methyl-2-(trifluoromethyl)pyridine-3-carboxamide (9.0 g, 33.5 mmol), 4-chlorophenol (4.3 g, 33.5 mmol), potassium carbonate (11.5 g, 83.7 mmol), copper(I) iodide (638 mg, 3.35 mmol), and N,N,N,N-tetramethylethylenediamine (TMEDA; 1.0 mL, 6.7 mmol) in dimethyl sulfoxide (DMSO; 150 mL) was heated for 3 h at 100 C. The reaction mixture was then cooled to rt, water added, extracted with ethyl acetate, dried (over Na.sub.2SO.sub.4), concentrated and passed over a plug of silica (heptane/ethyl acetate=1/1, 254 nm) to give 7.7 g (58% yield, 91% pure) of the target compound as a yellow oil.

[0335] MS (ESI): 360.05 ([M+H].sup.+)

Preparation of 6-(4-chlorophenoxy)-N-methoxy-N-methyl-4-(trifluoromethyl)pyridine-3-carboxamide (XVI.02)

[0336] ##STR00023##

[0337] A mixture of 6-chloro-N-methoxy-N-methyl-4-(trifluoromethyl)pyridine-3-carboxamide (5.7 g, 21.3 mmol), 4-chlorophenol (2.7 g, 21.3 mmol), potassium carbonate (7.4 g, 53.3 mmol), copper(I) iodide (406 mg, 2.13 mmol), and TMEDA (0.64 mL, 4.26 mmol) in DMSO (100 mL) was heated for 3 h at 100 C. The reaction mixture was then cooled to rt, water added, extracted with ethyl acetate, dried (over Na.sub.2SO.sub.4), concentrated and passed over a plug of silica (heptane/ethyl acetate=1/1, 254 nm) to give 6.59 g (85% yield, 100% pure) of the target compound as a colourless oil.

[0338] MS (ESI): 360.05 ([M+H].sup.+)

Preparation of Compounds of the Formula (I) According to Process B

Preparation of 1-[6-(4-chlorophenoxy)-2-(trifluoromethyl)pyridin-3-yl]-1-cyclopropyl-2-(1H-1,2,4-triazol-1-yl)ethanol (I.91) According to Process B

[0339] ##STR00024##

[0340] Epoxide IX.07 (1.0 g, 2.81 mmol), 1H-1,2,4-triazole (194 mg, 2.81 mmol), sodium hydroxide (40 mg, 0.984 mmol), 0.013 mL water in DMF (10 mL) was heated at 120 C. for 22 h, before water, NH.sub.4Cl (saturated aqueous solution) and CH.sub.2Cl.sub.2 were added. Phases were separated, the aqueous phase was extracted twice with CH.sub.2Cl.sub.2, the combined organic extracts were dried over Na.sub.2SO.sub.4 and concentrated to give, after purification via preparative HPLC, the desired alcohol 1.91 (362 mg, 30%) as a colorless oil.

[0341] MS (ESI): 425.09 ([M+H]+)

Preparation of 6-(4-chlorophenoxy)-3-(2-cyclopropyloxiran-2-yl)-2-(trifluoromethyl)pyridine (IX.07) According to Process B

[0342] ##STR00025##

[0343] To a suspension of trimethylsulfonium iodide (3.1 g, 15.2 mmol) in THF (100 mL) at 0 C. was added potassium tert-butoxide (1.7 g, 15.2 mmol) in one portion, and the mixture was stirred for 5 min. Then, ketone V.41 (4.0 g, 11.7 mmol) in THF (10 mL) was added, the mixture was warmed to room temperature and stirred for 1.5 h. Then water and CH.sub.2Cl.sub.2 were added, the aqueous phase was extracted with CH.sub.2Cl.sub.2, the combined organic extracts were dried over Na.sub.2SO.sub.4 and concentrated, to give, after flash column chromatography, the desired epoxide IX.07 (138 mg, 3%) as a colorless oil.

[0344] MS (ESI): 356.06 ([M+H]+)

Preparation of [6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-cyclopropyl-methanone (V.41) According to Process B

[0345] ##STR00026##

[0346] A mixture of [6-chloro-2-(trifluoromethyl)pyridin-3-yl](cyclopropyl)methanone (6.0 g, 24.0 mmol), 4-chlorophenol (3.1 g, 24.0 mmol), potassium carbonate (8.3 g, 60.1 mmol), copper(I) iodide (458 mg, 2.40 mmol), and N,N,N,N-tetramethylethylenediamine (TMEDA; 0.7 mL, 4.8 mmol) in dimethyl sulfoxide (DMSO; 100 mL) was heated for 2 h at 100 C. The reaction mixture was then cooled to rt, water added, extracted with ethyl acetate, dried (over Na.sub.2SO.sub.4), concentrated and passed over a plug of silica (heptane/ethyl acetate=1/1, 254 nm), and recrystallized from CH.sub.2Cl.sub.2 and diisopropyl ether to give 4.2 g (48% yield, 95% pure) of the target compound V.41 as a colorless solid.

[0347] MS (ESI): 342.04 ([M+H]+)

Preparation of [6-chloro-2-(trifluoromethyl)-3-pyridyl]-cyclopropyl-methanone

[0348] ##STR00027##

[0349] A solution of 6-chloro-2-(trifluoromethyl)pyridine-3-carboxylic acid (6.0 g, 26.6 mmol), thionyl chloride (3.9 mL, 53.2 mmol) and few drops of dimethylformamide in dichloroethane (100 mL) was heated at 85 C. for 4 h, before the mixture was cooled to rt and concentrated. Then dry THF (150 mL) and Fe(acac).sub.3 (470 mg, 1.33 mmol) were added and the solution was cooled to 78 C., before a solution of cyclopropylmagnesium bromide (69 mL, 0.5 M, 34.6 mmol) was added dropwise, keeping the internal temperature below 70 C. After complete addition, the cooling bath was removed and the reaction was allowed to warm to room temperature. The reaction was then quenched with NH.sub.4Cl (saturated aqueous solution) and extracted with CH.sub.2Cl.sub.2, dried over Na.sub.2SO.sub.4 and concentrated. The target compound [6-chloro-2-(trifluoromethyl)pyridin-3-yl](cyclopropyl)methanone (6.0 g, 87% yield) was used in the following step without further purification.

[0350] MS (ESI): 250.02 ([M+H]+)

[0351] The following tables illustrate in a non-limiting manner examples of compounds according to formula (I), (V), (VI), (VII), and (IX).

TABLE-US-00001 TABLE 1 Compounds according to formula (I) [00028] embedded image Ex N Y n R.sup.3 R R.sup.1 R.sup.2 m R.sup.4 LogP I.01 [00029] 0 CF.sub.3 CH.sub.3 H 1 4-Cl 2.88.sup.[a] I.02 (*) [00030] 0 CF.sub.3 CH.sub.3 H 1 4-Cl 2.90.sup.[a] I.03 [00031] 0 CF.sub.3 H H 1 4-Cl 2.70.sup.[a] I.04 [00032] 0 CF.sub.3 H H 1 4-Cl 2.68.sup.[a] I.05 [00033] 0 Cl CH.sub.3 H 0 2.10.sup.[a]; 2.06.sup.[b] I.06 [00034] embedded image 0 Cl CH.sub.3 H 0 2.47.sup.[a]; 2.43.sup.[b] I.07 [00035] 0 Cl CH.sub.3 H 0 2.14.sup.[a]; 2.09.sup.[b] I.08 (*) [00036] 0 Cl CH.sub.3 H 1 4-Cl 2.50.sup.[a] I.09 (*) [00037] 0 Cl CH.sub.3 H 1 4-Cl 2.66.sup.[a] I.10 [00038] 0 Cl H H 2 3-Cl, 4-Cl 2.80.sup.[a] I.11 [00039] 0 Cl H H 2 3-Cl, 4-OCF.sub.3 3.11.sup.[a] I.12 [00040] embedded image 0 Cl H H 1 4-OCF.sub.3 2.73.sup.[a] I.13 [00041] 0 Cl H H 0 1.98.sup.[a] I.14 [00042] 0 Cl H H 1 4-Cl 2.42.sup.[a] I.15 [00043] 0 Cl H H 2 2-Me, 4-Cl 2.75.sup.[a] I.16 [00044] 0 Cl H H 2 3-Cl, 4-Me 2.73.sup.[a] I.17 [00045] 0 Cl H H 1 4-F 2.08.sup.[a] I.18 [00046] 0 Cl H H 2 2-F, 4-F 2.18.sup.[a] I.19 [00047] embedded image 0 Cl H H 1 2-F 2.08.sup.[a] I.20 [00048] 0 Cl H H 3 3-F, 4-F, 5-F 1.65.sup.[a] I.21 [00049] 0 Cl H H 0 1.92.sup.[a] I.22 [00050] 0 Cl H H 0 2.01.sup.[a] I.23 [00051] 0 Cl H H 2 2-Cl, 4-Cl 2.75.sup.[a] I.24 [00052] 0 Cl H H 1 4- (1-hydroxyethyl) 1.48.sup.[a] I.25 [00053] 0 CHF.sub.2 H H 1 4-Cl 2.44.sup.[a] I.26 [00054] embedded image 0 OCF.sub.3 H H 1 4-Cl 2.92.sup.[a] I.27 [00055] 0 Cl CH.sub.3 H 1 4-F 2.28.sup.[a] I.28 [00056] 0 Cl CH.sub.3 H 2 2-Me, 4-Cl 2.94.sup.[a] I.29 [00057] 0 Cl CH.sub.3 H 2 3-Cl, 4-Me 3.00.sup.[a] I.30 [00058] 0 Cl H H 2 2-Cl, 4-OMe 2.32.sup.[a] I.31 [00059] 0 Cl CH.sub.3 H 2 2-Cl, 4-OMe 2.56.sup.[a] I.32 [00060] embedded image 0 Cl CH.sub.3 H 2 3-Cl, 4-Cl 3.09.sup.[a] I.33 [00061] 0 OCF.sub.3 CH.sub.3 H 1 4-Cl 3.29.sup.[a] I.34 [00062] 0 Cl H H 1 4-SF.sub.5 2.90.sup.[a] I.35 [00063] 0 Cl CH.sub.3 H 1 4-SF.sub.5 3.17.sup.[a] I.36 (*) [00064] 0 CF.sub.3 H H 1 4-SF.sub.5 3.15.sup.[a] I.37 [00065] 0 CF.sub.3 CH.sub.3 H 1 4-SF.sub.5 3.33.sup.[a] I.38 [00066] embedded image 0 Cl H H 1 4-CHF.sub.2 2.17.sup.[a] I.39 [00067] 0 Cl CH.sub.3 H 1 4-CHF.sub.2 2.41.sup.[a] I.40 [00068] 0 CF.sub.3 H H 1 4-Br 2.82.sup.[a] I.41 [00069] 0 F H H 1 4-Cl 2.23.sup.[a] I.42 [00070] 0 F CH.sub.3 H 1 4-Cl 2.46.sup.[a] I.43 [00071] 0 CF.sub.3 H H 1 4-OCF.sub.3 3.00.sup.[a] I.44 [00072] embedded image 0 CF.sub.3 CH.sub.3 H 1 4-OCF.sub.3 3.23.sup.[a] I.45 (*) [00073] 0 CF.sub.3 CH.sub.3 H 1 4-Cl 2.84.sup.[a] I.46 (*) [00074] 0 CF.sub.3 CH.sub.3 H 1 4-Cl 2.93.sup.[a] I.47 (*) [00075] 0 CF.sub.3 H H 1 4-CF.sub.3 2.84.sup.[a] I.48 [00076] 0 CF.sub.3 H H 1 4-Br 2.75.sup.[a] I.49 [00077] embedded image 0 CF.sub.3 CH.sub.3 H 1 4-Br 2.96.sup.[a] I.50 [00078] 0 CF.sub.3 CH.sub.3 H 1 4-CF.sub.3 3.11.sup.[a] I.51 (*) [00079] 0 Cl CH.sub.3 H 1 4-Cl 2.62.sup.[a] I.52 (*) [00080] 0 Cl CH.sub.3 H 1 4-Cl 2.62.sup.[a] I.53 (*) [00081] 0 Cl CH.sub.3 H 1 4-Cl 2.53.sup.[a] I.54 (*) [00082] 0 Cl CH.sub.3 H 1 4-Cl 2.53.sup.[a] I.55 [00083] embedded image 0 CF.sub.3 H H 1 4-CHF.sub.2 2.55.sup.[a] I.56 [00084] 0 CF.sub.3 CH.sub.3 H 1 4-CHF.sub.2 2.73.sup.[a] I.57 [00085] 0 CF.sub.3 H H 2 2-F, 4-Cl 2.86.sup.[a] I.58 [00086] 0 CF.sub.3 CH.sub.3 H 2 2-F, 4-Cl 3.02.sup.[a] I.59 (*) [00087] 0 CF.sub.3 CH.sub.3 H 1 4-Br 2.94.sup.[a] I.60 [00088] embedded image 0 CF.sub.3 H H 1 4-SF.sub.5 3.08.sup.[a] I.61 [00089] 0 CF.sub.3 H H 1 4-CF.sub.3 2.84.sup.[a] I.62 [00090] 0 CF.sub.3 CH.sub.3 H 1 4-SF.sub.5 3.25.sup.[a] I.63 [00091] 0 CHF.sub.2 H H 1 4-Br 2.59.sup.[a] I.64 [00092] 0 CHF.sub.2 CH.sub.3 H 1 4-Cl 2.68.sup.[a] I.65 [00093] 0 CF.sub.3 CH.sub.3 H 1 4-CF.sub.3 3.04.sup.[a] I.66 [00094] embedded image 0 CF.sub.3 CH.sub.3 H 2 2-F, 4-Cl 2.80.sup.[a] I.67 [00095] 0 CF.sub.3 CH.sub.3 H 1 4-Cl 2.68.sup.[a] I.68 [00096] 0 Cl H H 1 4-Cl 2.48.sup.[a] I.69 [00097] 0 CF.sub.3 vinyl H 1 4-CF.sub.3 3.33.sup.[a] I.70 [00098] 0 CF.sub.3 H H 2 2-F, 4-Cl 2.78.sup.[a] I.71 [00099] 0 CF.sub.3 cyclo- propyl H 1 4-Cl 3.35.sup.[a] I.72 (*) [00100] embedded image 0 CF.sub.3 H H 1 4-CF.sub.3 2.86.sup.[a] I.73 [00101] 0 CHF.sub.2 H H 1 4-Br 2.50.sup.[a] I.74 [00102] 0 CF.sub.3 H H 1 4-CHF.sub.2 2.49.sup.[a] I.75 [00103] 0 CF.sub.3 CH.sub.3 H 1 4-isopropyl 3.35.sup.[a] I.76 [00104] 0 CF.sub.3 Et H 1 4-CF.sub.3 3.52.sup.[a] I.77 [00105] 0 4-fluoro- phenoxy CH.sub.3 H 1 4-F 3.13.sup.[a] I.78 [00106] embedded image 0 Cl CH.sub.3 H 1 4-CF.sub.3 2.88.sup.[a] I.79 [00107] 0 CF.sub.3 H H 1 4-OCF.sub.3 2.89.sup.[a] I.80 [00108] 0 CF.sub.3 cyclo- propyl H 1 4-Cl 3.32.sup.[a] I.81 (*) [00109] 0 CF.sub.3 cyclo- propyl H 1 4-Br 3.70.sup.[a] I.82 [00110] 0 CHF.sub.2 CH.sub.3 H 1 4-Br 2.78.sup.[a] I.83 (*) [00111] embedded image 0 CF.sub.3 H H 1 4-SF.sub.5 3.11.sup.[a] I.84 (*) [00112] 0 CF.sub.3 cyclo- propyl H 1 4-Br 3.41 .sup.[a] I.85 [00113] 0 CF.sub.3 CF.sub.3 H 1 4-Br 3.48.sup.[a] I.86 (*) [00114] 0 CF.sub.3 H H 1 4-SF.sub.5 3.11.sup.[a] I.87 [00115] 0 CF.sub.3 cyclo- propyl H 1 4-CF.sub.3 3.57.sup.[a] I.88 [00116] embedded image 0 Cl H H 1 4-CF.sub.3 2.64.sup.[a] I.89 [00117] 0 CF.sub.3 CH.sub.3 H 2 2-F, 4-Cl 3.15.sup.[a] I.90 [00118] 0 CF.sub.3 H H 2 2-F, 4-Cl 2.88.sup.[a] I.91 [00119] 0 CF.sub.3 cyclo- propyl H 1 4-Cl 3.26.sup.[a] I.92 (*) [00120] 0 CF.sub.3 H H 1 4-CF.sub.3 2.86.sup.[a] I.93 [00121] 0 CF.sub.3 cyclo- propyl H 1 4-CHF.sub.2 3.13.sup.[a] I.94 [00122] embedded image 0 CHF.sub.2 H H 1 4-Cl 2.13.sup.[a] I.95 [00123] 0 CF.sub.3 CH.sub.3 H 1 4-OCF.sub.3 2.98.sup.[a] I.96 [00124] 0 CF.sub.3 CH.sub.3 H 1 4-Cl 2.68.sup.[a] I.97 [00125] 0 CF.sub.3 cyclo- propyl H 1 4-SF.sub.5 3.80.sup.[a] I.98 [00126] 0 CF.sub.3 butyl H 1 4-Cl 3.87.sup.[a] I.99 (*) [00127] embedded image 0 CF.sub.3 cyclo- propyl H 1 4-Br 3.41.sup.[a] I.100 [00128] 0 CF.sub.3 propyl H 1 4-Cl 3.55.sup.[a] I.101 (*) [00129] 0 CF.sub.3 CH.sub.3 H 1 4-Br 2.94.sup.[a] I.102 (*) [00130] 0 CF.sub.3 CH.sub.3 H 1 4-Br 2.94.sup.[a] I.103 [00131] 0 CF.sub.3 Et H 1 4-Cl 3.19.sup.[a]

[0352] Optical Rotation

[0353] Concentration c is expressed in g/100 mL

[0354] (*) Ex I.45 and I.46 are the 2 enantiomers of Ex I.02

[0355] (*) Ex I.53 and I.54 are the 2 enantiomers of Ex I.08

[0356] Ex I.53: Optical rotation: 35 (c=0.52, DCM, 20 C.)

[0357] Ex I.54: Optical rotation: +52 (c=0.50, DCM, 20 C.)

[0358] (*) Ex I.51 and I.52 are the 2 enantiomers of Ex I.09

[0359] Ex I.51: Optical rotation: 128.2 (c=0.52, DCM, 20 C.)

[0360] Ex I.52: Optical rotation: +133.3 (c=0.51, DCM, 20 C.)

[0361] (*) Ex I.83 and I.86 are the 2 enantiomers of Ex I.36

[0362] Ex I.83: Optical rotation: +10.0 (c=0.50, CDCl.sub.3, 25 C.)

[0363] Ex I.86: Optical rotation: 11.0 (c=0.73, CDCl.sub.3, 25 C.)

[0364] (*) Ex I.72 and I.92 are the 2 enantiomers of Ex I.47

[0365] Ex I.72: Optical rotation: +11.7 (c=0.52, CDCl.sub.3, 25 C.)

[0366] Ex I.92: Optical rotation: 10.4 (c=0.58, CDCl.sub.3, 25 C.)

[0367] (*) Ex I.101 and I.102 are the 2 enantiomers of Ex I.59

[0368] Ex I.101: Optical rotation: +27.5 (c=0.88; MeOH; 20 C.)

[0369] Ex I.102: Optical rotation: 31.5 (c=1.02; MeOH; 20 C.)

[0370] (*) Ex I.84 and I.99 are the 2 enantiomers of Ex I.81

[0371] Ex I.84: Optical rotation: 8 (c=1.00, MeOH, 25 C.)

[0372] Ex I.99: Optical rotation: +7.3 (c=1.10, MeOH, 25 C.)

TABLE-US-00002 TABLE 2 Compounds according to formula (V) [00132] embedded image Ex No Y n R.sup.3 R R.sup.1 m R.sup.4 LogP V.01 [00133] 0 CF.sub.3 CH.sub.3 1 4-Cl 3.80.sup.[a] V.02 [00134] 0 CF.sub.3 CH.sub.3 1 4-Cl 3.89.sup.[a] V.03 [00135] 0 CF.sub.3 CH.sub.3 1 4-SF.sub.5 4.32.sup.[a] V.04 [00136] 0 CF.sub.3 CH.sub.3 1 4-CHF.sub.2 3.62.sup.[a] V.05 [00137] 0 CHF.sub.2 CH.sub.3 1 4-Cl 3.35.sup.[a] V.06 [00138] embedded image 0 OCF.sub.3 CH.sub.3 1 4-Cl 4.37.sup.[a] V.07 [00139] 0 CF.sub.3 CH.sub.3 2 2-F, 4-Cl 4.09.sup.[a] V.08 [00140] 0 Cl CH.sub.3 0 2.94.sup.[a]; 2.86.sup.[b] V.09 [00141] 0 Cl CH.sub.3 1 4-Cl 3.52.sup.[a]; 3.42.sup.[b] V.10 [00142] 0 Cl CH.sub.3 1 4-Cl 3.47.sup.[a]; 3.36.sup.[b] V.11 [00143] embedded image 0 Cl CH.sub.3 2 3-Cl, 4-Cl 4.10.sup.[a] V.12 [00144] 0 Cl CH.sub.3 1 4-F 3.11.sup.[a] V.13 [00145] 0 H CH.sub.3 1 4-Cl 2.73.sup.[a] V.14 [00146] 0 Cl CH.sub.3 1 4-CHF.sub.2 3.15.sup.[a] V.15 [00147] 0 CF.sub.3 CH.sub.3 1 4-OCF.sub.3 4.20.sup.[a] V.16 [00148] 0 CF.sub.3 CH.sub.3 1 4-SF.sub.5 4.09.sup.[a] V.17 [00149] embedded image 0 CF.sub.3 CH.sub.3 1 4-CF.sub.3 3.96.sup.[a] V.18 [00150] 0 Cl CH.sub.3 1 4-CF.sub.3 3.87.sup.[a] V.19 [00151] 0 C(O)CH.sub.3 CH.sub.3 1 4-Cl 3.11.sup.[a] V.20 [00152] 0 CF.sub.3 CH.sub.3 1 4-Br 3.85.sup.[a] V.21 [00153] 0 Cl CH.sub.3 0 2.94.sup.[a]; 2.85.sup.[b] V.22 [00154] 0 Cl CH.sub.3 1 4-Cl 3.51.sup.[a] V.23 [00155] embedded image 0 Cl CH.sub.3 1 4-Cl 3.51.sup.[a] V.24 [00156] 0 F CH.sub.3 1 4-Cl 3.51.sup.[a] V.25 [00157] 0 CF.sub.3 CH.sub.3 1 4-CF.sub.3 4.04.sup.[a] V.26 [00158] 0 Cl CH.sub.3 1 4-Cl 3.45.sup.[a] V.27 [00159] 0 CF.sub.3 CH.sub.3 1 4-Br 3.99.sup.[a] V.28 [00160] 0 Cl CH.sub.3 1 4-OCF.sub.3 3.89.sup.[a] V.29 [00161] embedded image 0 Cl CH.sub.3 2 2-Cl, 4-OCH.sub.3 3.44.sup.[a] V.30 [00162] 0 Cl CH.sub.3 1 4-SF.sub.5 3.99.sup.[a] V.31 [00163] 0 CF.sub.3 CH.sub.3 3 2-F, 4-Cl, 6-F 4.06.sup.[a] V.32 [00164] 0 CF.sub.3 CH.sub.3 1 4-CHF.sub.2 3.26.sup.[a] V.33 [00165] 0 4-chloro- phenoxy CH.sub.3 1 4-Cl 4.36.sup.[a] V.34 [00166] embedded image 0 CHF.sub.2 CH.sub.3 1 4-Br 3.46.sup.[a] V.35 [00167] 0 CF.sub.3 CH.sub.3 1 4-OCF.sub.3 4.04.sup.[a] V.36 [00168] 0 CHF.sub.2 CH.sub.3 1 4-Br 3.74.sup.[a] V.37 [00169] 0 CHF.sub.2 CH.sub.3 1 4-Cl 3.57.sup.[a] V.38 [00170] 0 CF.sub.3 CH.sub.3 2 2-F, 4-Cl 3.87.sup.[a] V.39 [00171] 0 CF.sub.3 cyclopropyl 1 4-CF.sub.3 4.37.sup.[a] V.40 [00172] embedded image 0 CF.sub.3 cyclopropyl 1 4-Br 4.49.sup.[a] V.41 [00173] 0 CF.sub.3 cyclopropyl 1 4-Cl 4.17.sup.[a] V.42 [00174] 0 CF.sub.3 cyclopropyl 1 4-formyl 3.21.sup.[a] V.43 [00175] 0 CF.sub.3 cyclopropyl 1 4-SF.sub.5 4.67.sup.[a] V.44 [00176] 0 CF.sub.3 cyclopropyl 1 4-CHF.sub.2 3.80.sup.[a] V.45 [00177] embedded image 0 CF.sub.3 ethyl 1 4-Cl 4.20.sup.[a] V.46 [00178] 0 CF.sub.3 propyl 1 4-Cl 4.59.sup.[a] V.47 [00179] 0 CF.sub.3 isobutyl 1 4-Cl 4.98.sup.[a] V.48 [00180] 0 CF.sub.3 butyl 1 4-Cl 5.03.sup.[a]

TABLE-US-00003 TABLE 3 Compounds according to formula (VI) [00181] embedded image Ex N Y n R.sup.3 R Hal m R.sup.4 LogP VI.01 [00182] 0 CF.sub.3 Cl 1 4-Cl 4.01.sup.[a] VI.02 [00183] 0 CF.sub.3 Cl 1 4-Cl VI.03 [00184] 0 Cl Cl 0 3.23.sup.[a] VI.04 [00185] 0 Cl Cl 1 4-Cl 3.72.sup.[a] VI.05 [00186] 0 Cl Cl 0 3.28.sup.[a] VI.06 [00187] 0 Cl Cl 1 4-Cl 3.77.sup.[a] VI.07 [00188] embedded image 0 Cl Br 2 3-Cl, 4-Cl 4.58.sup.[a] VI.08 [00189] 0 Cl Cl 1 4-OCF.sub.3 4.09.sup.[a] VI.09 [00190] 0 Cl Cl 1 4-F 3.39.sup.[a] VI.10 [00191] 0 Cl Cl 1 4-Cl 3.78.sup.[a] VI.11 [00192] 0 CHF.sub.2 Cl 1 4-Cl 3.62.sup.[a] VI.12 [00193] 0 OCF.sub.3 Cl 1 4-Cl 4.51.sup.[a] VI.13 [00194] 0 Cl Cl 2 2-Cl, 4-OCH.sub.3 3.71.sup.[a] VI.14 [00195] embedded image 0 CF.sub.3 Br 1 4-Cl 4.29.sup.[a] VI.15 [00196] 0 CF.sub.3 Br 1 4-Br 4.34.sup.[a] VI.16 [00197] 0 Cl Cl 1 4-CHF.sub.2 3.42.sup.[a] VI.17 [00198] 0 Cl Br 1 4-CHF.sub.2 3.57.sup.[a] VI.18 [00199] 0 CF.sub.3 Br 1 4-Br 4.23.sup.[a] VI.19 [00200] 0 CF.sub.3 Cl 1 4-Br 4.11.sup.[a] VI.20 [00201] embedded image 0 F Cl 1 4-Cl 3.69.sup.[a] VI.21 [00202] 0 CF.sub.3 Cl 1 4-OCF.sub.3 4.37.sup.[a] VI.22 [00203] 0 CF.sub.3 Cl 1 4-CF.sub.3 4.21.sup.[a] VI.23 [00204] 0 CF.sub.3 Cl 1 4-Br 4.16.sup.[a] VI.24 [00205] 0 CF.sub.3 Br 2 2-F, 4-Cl 4.34.sup.[a] VI.25 [00206] 0 CF.sub.3 Cl 2 2-F, 4-Cl 4.15.sup.[a] VI.26 [00207] embedded image 0 CF.sub.3 Cl 1 4-CHF.sub.2 3.76.sup.[a] VI.27 [00208] 0 CF.sub.3 Br 1 4-CHF.sub.2 3.99.sup.[a] VI.28 [00209] 0 CF.sub.3 Cl 1 4-CF.sub.3 4.19.sup.[a] VI.29 [00210] 0 CF.sub.3 Cl 1 4-SF.sub.5 4.29.sup.[a] VI.30 [00211] 0 Cl Cl 1 4-SF.sub.5 4.21.sup.[a] VI.31 [00212] 0 CF.sub.3 Cl 3 2-F, 4-Cl, 6-F 4.26.sup.[a] VI.32 [00213] embedded image 0 CF.sub.3 Br 3 2-F, 4-Cl, 6-F 4.18.sup.[a] VI.33 [00214] 0 CF.sub.3 Cl 1 4-OCF.sub.3 4.07.sup.[a] VI.34 [00215] 0 CF.sub.3 Br 1 4-Cl 4.19.sup.[a] VI.35 [00216] 0 CF.sub.3 Cl 2 2-F, 4-Cl 4.11.sup.[a] VI.36 [00217] 0 CF.sub.3 Cl 1 4-CHF.sub.2 3.50.sup.[a]

TABLE-US-00004 TABLE 4 Compounds according to formula (VII) [00218] embedded image Ex N Y n R.sup.3 R m R.sup.4 LogP VII.01 [00219] 0 CF.sub.3 1 4-Cl 2.92.sup.[a] VII.02 [00220] 0 CF.sub.3 1 4-Cl 2.92.sup.[a] VII.03 [00221] 0 Cl 2 3-Cl, 4-Cl 3.06.sup.[a] VII.04 [00222] 0 Cl 2 3-Cl, 4-OCF.sub.3 3.33.sup.[a] VII.05 [00223] 0 Cl 0 2.20.sup.[a] VII.06 [00224] 0 Cl 0 2.21.sup.[a] VII.07 [00225] embedded image 0 Cl 0 2.45.sup.[a] VII.08 [00226] 0 Cl 1 4-OCF.sub.3 2.95.sup.[a] VII.09 [00227] 0 Cl 1 4-Cl 2.66.sup.[a] VII.10 [00228] 0 Cl 2 2-CH.sub.3, 4-Cl 2.94.sup.[a] VII.11 [00229] 0 Cl 2 3-Cl, 4-CH.sub.3 3.02.sup.[a] VII.12 [00230] 0 Cl 1 4-F 2.30.sup.[a] VII.13 [00231] 0 Cl 2 2-F, 4-F 2.41.sup.[a] VII.14 [00232] embedded image 0 Cl 1 2-F 2.28.sup.[a] VII.15 [00233] 0 Cl 3 3-F, 4-F, 5-F 2.66.sup.[a] VII.16 [00234] 0 Cl 2 2-Cl, 4-Cl 3.02.sup.[a] VII.17 [00235] 0 Cl 1 4-C(O)CH.sub.3 1.96.sup.[a] VII.18 [00236] 0 OCF.sub.3 1 4-Cl 3.23.sup.[a] VII.19 [00237] 0 Cl 2 2-Cl, 4-OCH.sub.3 2.58.sup.[a] VII.20 [00238] embedded image 0 Cl 1 4-SF.sub.5 3.11.sup.[a] VII.21 [00239] 0 CF.sub.3 1 4-SF.sub.5 3.35.sup.[a] VII.22 [00240] 0 Cl 1 4-CHF.sub.2 2.39.sup.[a] VII.23 [00241] 0 Cl 1 4-Cl 2.54.sup.[a] VII.24 [00242] 0 CF.sub.3 1 4-Br 2.99.sup.[a] VII.25 [00243] 0 F 1 4-Cl 2.50.sup.[a] VII.26 [00244] 0 CF.sub.3 1 4-OCF.sub.3 3.27.sup.[a] VII.27 [00245] embedded image 0 CF.sub.3 1 4-Br 3.02.sup.[a] VII.28 [00246] 0 CF.sub.3 1 4-CF.sub.3 3.17.sup.[a] VII.29 [00247] 0 CF.sub.3 1 4-CHF.sub.2 2.80.sup.[a] VII.30 [00248] 0 CF.sub.3 2 2-F, 4-Cl 3.06.sup.[a] VII.31 [00249] 0 CF.sub.3 1 4-SF.sub.5 3.23.sup.[a] VII.32 [00250] 0 CF.sub.3 1 4-CF.sub.3 3.04.sup.[a] VII.33 [00251] embedded image 0 CF.sub.3 3 2-F, 4-Cl, 6-F 2.96.sup.[a] VII.34 [00252] 0 CF.sub.3 1 4-isopropyl 3.44.sup.[a] VII.35 [00253] 0 CHF.sub.2 1 4-Br 2.68.sup.[a] VII.36 [00254] 0 CHF.sub.2 1 4-Cl 2.51.sup.[a] VII.37 [00255] 0 CF.sub.3 2 2-F, 4-Cl 2.74.sup.[a] VII.38 [00256] 0 Cl 1 4-Cl 2.60.sup.[a] VII.39 [00257] embedded image 0 CF.sub.3 1 4-OCF.sub.3 2.95.sup.[a] VII.40 [00258] 0 Cl 1 4-CF.sub.3 2.92.sup.[a] VII.41 [00259] 0 CHF.sub.2 1 4-Br 2.61.sup.[a] VII.42 [00260] 0 CF.sub.3 1 4-CHF.sub.2 2.41.sup.[a]

TABLE-US-00005 TABLE 5 Compounds according to formula (IX) [00261] embedded image Ex N Y n R.sup.3 R R.sup.1 m R.sup.4 LogP IX.01 [00262] 0 CF.sub.3 CH.sub.3 1 4-Cl 4.41.sup.[a] IX.02 [00263] 0 Cl CH.sub.3 0 3.40.sup.[a]; 3.38.sup.[b] IX.03 [00264] 0 Cl CH 1 4-Cl 4.06.sup.[a]; 4.00.sup.[b] IX.04 [00265] 0 Cl CH.sub.3 0 3.42.sup.[a]; 3.39.sup.[b] IX.05 [00266] embedded image 0 CF.sub.3 cyclopropyl 1 4-CHF.sub.2 4.49.sup.[a] IX.06 [00267] 0 CF.sub.3 CH.sub.3 1 4-Cl 4.44.sup.[a] IX.07 [00268] 0 CF.sub.3 cyclopropyl 1 4-Cl 4.80.sup.[a] IX.08 [00269] 0 CF.sub.3 cyclopropyl 1 4-Br 5.11.sup.[a] IX.09 [00270] 0 CF.sub.3 cyclopropyl 1 4-SF.sub.5 5.22.sup.[a] IX.10 [00271] embedded image 0 Cl CH.sub.3 1 4-Cl 4.06.sup.[a] IX.11 [00272] 0 CF.sub.3 cyclopropyl 1 4-CF.sub.3 5.00.sup.[a]

[0373] LogP Values:

[0374] Measurement of LogP values was performed according to EEC directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on reversed phase columns with the following methods:

[0375] .sup.[a] LogP value is determined by measurement of LC-UV, in an acidic range, with 0.1% formic acid in water and acetonitrile as eluent (linear gradient from 10% acetonitrile to 95% acetonitrile).

[0376] .sup.[b] LogP value is determined by measurement of LC-UV, in a neutral range, with 0.001 molar ammonium acetate solution in water and acetonitrile as eluent (linear gradient from 10% acetonitrile to 95% acetonitrile).

[0377] .sup.[c] LogP value is determined by measurement of LC-UV, in an acidic range, with 0.1% phosphoric acid in water and acetonitrile as eluent (linear gradient from 10% acetonitrile to 95% acetonitrile).

[0378] If more than one LogP value is available within the same method, all the values are given and separated by +.

[0379] Calibration was done with straight-chain alkan2-ones (with 3 to 16 carbon atoms) with known LogP values (measurement of LogP values using retention times with linear interpolation between successive alkanones). Lambda-max-values were determined using UV-spectra from 200 nm to 400 nm and the peak values of the chromatographic signals.

[0380] NMR-Peak Lists

[0381] 1H-NMR data of selected examples are written in form of 1H-NMR-peak lists. To each signal peak are listed the -value in ppm and the signal intensity in round brackets. Between the -valuesignal intensity pairs are semicolons as delimiters.

[0382] The peak list of an example has therefore the form:

[0383] .sub.1 (intensity.sub.1); .sub.2 (intensity.sub.2); . . . ; .sub.i (intensity.sub.i); . . . ; .sub.n (intensity.sub.n)

[0384] Intensity of sharp signals correlates with the height of the signals in a printed example of a NMR spectrum in cm and shows the real relations of signal intensities. From broad signals several peaks or the middle of the signal and their relative intensity in comparison to the most intensive signal in the spectrum can be shown.

[0385] For calibrating chemical shift for 1H spectra, we use tetramethylsilane and/or the chemical shift of the solvent used, especially in the case of spectra measured in DMSO. Therefore in NMR peak lists, tetramethylsilane peak can occur but not necessarily.

[0386] The 1H-NMR peak lists are similar to classical 1H-NMR prints and contains therefore usually all peaks, which are listed at classical NMR-interpretation.

[0387] Additionally they can show like classical 1H-NMR prints signals of solvents, stereoisomers of the target compounds, which are also object of the invention, and/or peaks of impurities.

[0388] To show compound signals in the delta-range of solvents and/or water the usual peaks of solvents, for example peaks of DMSO in DMSO-D6 and the peak of water are shown in our 1H-NMR peak lists and have usually on average a high intensity.

[0389] The peaks of stereoisomers of the target compounds and/or peaks of impurities have usually on average a lower intensity than the peaks of target compounds (for example with a purity >90%).

[0390] Such stereoisomers and/or impurities can be typical for the specific preparation process. Therefore their peaks can help to recognize the reproduction of our preparation process via side-products-fingerprints.

[0391] An expert, who calculates the peaks of the target compounds with known methods (MestreC, ACD-simulation, but also with empirically evaluated expectation values) can isolate the peaks of the target compounds as needed optionally using additional intensity filters. This isolation would be similar to relevant peak picking at classical 1H-NMR interpretation.

[0392] Further details of NMR-data description with peak lists you find in the publication Citation of NMR Peaklist Data within Patent Applications of the Research Disclosure Database Number 564025.

Example I.01

[0393] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.232 (2.4); 8.203 (2.5); 8.041 (5.3); 8.022 (0.4); 7.955 (5.9); 7.645 (0.5); 7.424 (0.8); 7.414 (5.5); 7.406 (1.8); 7.391 (2.1); 7.384 (6.6); 7.373 (0.8); 7.368 (0.4); 7.299 (88.2); 7.188 (0.9); 7.177 (6.9); 7.170 (1.8); 7.155 (1.8); 7.147 (5.0); 7.136 (0.4); 7.031 (3.0); 7.002 (2.7); 6.948 (0.5); 5.424 (0.4); 4.764 (2.2); 4.716 (3.6); 4.702 (5.8); 4.554 (3.5); 4.507 (2.4); 4.197 (1.1); 4.173 (3.5); 4.150 (3.5); 4.126 (1.1); 2.085 (16.0); 1.679 (12.3); 1.579 (44.1); 1.323 (4.5); 1.299 (9.1); 1.275 (4.2); 0.917 (0.3); 0.235 (0.6); 0.108 (9.3); 0.050 (4.1); 0.039 (119.3); 0.028 (4.6); 0.027 (0.3); 0.159 (0.5)

Example I.02

[0394] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.470 (5.6); 8.063 (6.3); 7.956 (6.4); 7.450 (0.6); 7.439 (5.5); 7.432 (2.0); 7.416 (2.1); 7.409 (7.0); 7.398 (0.8); 7.316 (6.6); 7.300 (30.3); 7.138 (0.8); 7.127 (6.8); 7.120 (2.3); 7.105 (1.9); 7.097 (5.7); 7.087 (0.6); 5.340 (0.7); 4.727 (2.5); 4.679 (3.6); 4.480 (3.9); 4.440 (7.0); 1.675 (16.0); 1.587 (17.3); 1.294 (0.7); 0.109 (1.8); 0.051 (1.7); 0.040 (41.5); 0.029 (1.8)

Example I.03

[0395] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.134 (3.3); 8.113 (1.4); 8.084 (1.4); 8.045 (3.4); 7.430 (3.0); 7.423 (1.0); 7.408 (1.1); 7.400 (3.8); 7.390 (0.5); 7.299 (12.4); 7.202 (0.5); 7.192 (3.8); 7.184 (1.2); 7.169 (1.0); 7.162 (3.0); 7.151 (1.7); 7.121 (1.4); 5.551 (0.5); 5.524 (0.5); 4.528 (0.7); 4.520 (0.7); 4.481 (1.0); 4.473 (1.0); 4.312 (1.0); 4.285 (1.0); 4.265 (0.7); 4.238 (0.7); 4.032 (0.9); 1.600 (16.0); 0.108 (1.3); 0.049 (0.6); 0.038 (14.7); 0.027 (0.6)

Example I.04

[0396] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.582 (3.2); 8.159 (4.0); 8.055 (3.9); 7.646 (0.5); 7.452 (3.3); 7.430 (1.2); 7.422 (4.4); 7.412 (0.6); 7.367 (0.6); 7.300 (81.3); 7.259 (3.7); 7.234 (0.4); 7.160 (0.5); 7.149 (4.3); 7.126 (1.2); 7.119 (3.5); 6.949 (0.5); 5.470 (0.8); 5.452 (0.9); 5.340 (16.0); 4.515 (0.8); 4.508 (0.8); 4.469 (1.4); 4.461 (1.4); 4.343 (1.2); 4.315 (1.2); 4.297 (0.8); 4.269 (0.7); 3.835 (2.3); 3.824 (2.3); 1.647 (0.6); 1.607 (0.4); 1.581 (79.0); 1.515 (0.4); 1.351 (0.7); 1.293 (1.5); 0.920 (0.6); 0.900 (0.3); 0.235 (0.6); 0.109 (6.3); 0.051 (3.5); 0.040 (105.0); 0.029 (5.2); 0.006 (0.4); 0.026 (0.4); 0.159 (0.5)

Example I.05

[0397] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): =8.339 (3.2); 8.187 (3.4); 7.953 (2.1); 7.790 (3.1); 7.443 (1.0); 7.438 (0.4); 7.424 (1.8); 7.422 (1.7); 7.407 (0.5); 7.403 (1.5); 7.248 (0.7); 7.246 (0.4); 7.230 (1.1); 7.211 (0.5); 7.147 (3.6); 7.120 (1.6); 7.117 (1.9); 7.112 (0.5); 7.098 (1.6); 7.096 (1.4); 6.002 (2.8); 4.747 (0.9); 4.711 (1.4); 4.597 (1.4); 4.561 (0.9); 3.328 (18.0); 2.891 (16.0); 2.732 (13.3); 2.511 (6.5); 2.507 (13.1); 2.502 (17.3); 2.498 (12.5); 2.493 (5.9); 1.989 (1.1); 1.615 (7.6); 1.175 (0.6); 0.000 (4.4)

Example I.06

[0398] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): =8.367 (6.6); 8.224 (4.5); 8.218 (4.6); 7.808 (6.2); 7.619 (4.5); 7.613 (4.4); 7.491 (0.3); 7.486 (2.3); 7.480 (0.9); 7.473 (0.5); 7.467 (3.6); 7.464 (3.4); 7.459 (0.5); 7.451 (1.1); 7.446 (3.1); 7.440 (0.4); 7.268 (0.8); 7.265 (1.5); 7.263 (0.9); 7.247 (2.4); 7.231 (0.6); 7.228 (1.1); 7.226 (0.6); 7.133 (3.3); 7.130 (4.2); 7.125 (1.1); 7.114 (1.9); 7.111 (3.5); 7.109 (3.0); 7.102 (0.3); 5.809 (7.5); 5.757 (4.9); 4.764 (1.4); 4.729 (3.5); 4.690 (3.7); 4.655 (1.5); 4.038 (0.4); 4.020 (0.4); 3.327 (20.9); 2.525 (0.4); 2.512 (8.5); 2.507 (17.1); 2.503 (22.5); 2.498 (16.1); 2.493 (7.6); 1.989 (1.8); 1.551 (16.0); 1.397 (0.9); 1.193 (0.5); 1.175 (1.0); 1.157 (0.5); 0.000 (6.5)

Example I.07

[0399] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): =8.327 (6.5); 7.985 (3.8); 7.963 (4.1); 7.953 (1.2); 7.785 (6.2); 7.477 (0.3); 7.472 (2.2); 7.467 (0.9); 7.453 (3.6); 7.451 (3.5); 7.437 (1.1); 7.432 (3.0); 7.426 (0.4); 7.275 (1.4); 7.256 (2.3); 7.238 (1.0); 7.162 (3.2); 7.160 (4.0); 7.155 (1.1); 7.141 (3.3); 7.139 (2.9); 7.132 (0.3); 6.917 (4.0); 6.896 (4.0); 6.009 (5.5); 4.776 (2.0); 4.740 (2.7); 4.595 (2.8); 4.560 (2.0); 4.056 (0.6); 4.038 (1.9); 4.020 (1.9); 4.002 (0.6); 3.328 (25.8); 2.891 (9.0); 2.732 (7.3); 2.525 (0.6); 2.511 (11.8); 2.507 (23.5); 2.502 (30.8); 2.498 (22.2); 2.493 (10.6); 1.989 (8.2); 1.612 (16.0); 1.397 (1.9); 1.193 (2.2); 1.175 (4.4); 1.157 (2.2); 0.000 (8.0)

Example I.08

[0400] .sup.1H-NMR (499.9 MHz, d.sub.6-DMSO): =8.369 (6.3); 8.251 (6.6); 7.785 (5.9); 7.614 (4.8); 7.597 (5.6); 7.400 (5.7); 7.382 (4.8); 6.581 (6.6); 6.047 (5.9); 4.777 (2.3); 4.749 (2.9); 4.542 (2.9); 4.514 (2.3); 3.319 (6.7); 2.892 (0.5); 2.733 (0.5); 2.504 (2.7); 1.629 (16.0); 0.000 (0.7)

Example I.09

[0401] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.077 (3.7); 8.049 (3.9); 8.006 (4.7); 7.860 (4.4); 7.378 (0.4); 7.367 (4.5); 7.360 (1.5); 7.345 (1.7); 7.337 (5.5); 7.326 (0.7); 7.269 (2.2); 7.084 (0.6); 7.074 (5.6); 7.066 (1.7); 7.051 (1.5); 7.044 (4.5); 7.033 (0.5); 6.718 (3.9); 6.690 (3.8); 5.300 (0.7); 5.260 (2.0); 5.213 (2.3); 4.991 (1.5); 4.536 (2.4); 4.489 (2.1); 1.744 (0.5); 1.697 (16.0); 0.000 (2.5)

Example I.10

[0402] .sup.1H-NMR (400.1 MHz, CDCl.sub.3): =8.092 (12.5); 7.992 (0.9); 7.963 (15.1); 7.913 (11.8); 7.892 (12.2); 7.861 (0.4); 7.839 (0.4); 7.520 (0.3); 7.476 (14.5); 7.454 (16.0); 7.311 (0.4); 7.288 (15.7); 7.281 (16.1); 7.261 (38.0); 7.045 (9.1); 7.039 (8.5); 7.023 (8.2); 7.017 (7.6); 6.997 (0.4); 6.919 (0.6); 6.900 (13.5); 6.879 (12.9); 5.378 (5.7); 5.372 (6.0); 5.358 (6.3); 5.353 (5.8); 4.603 (5.8); 4.597 (5.8); 4.568 (7.1); 4.562 (6.9); 4.260 (6.5); 4.241 (6.4); 4.225 (5.6); 4.206 (5.3); 4.145 (1.0); 4.127 (2.4); 4.109 (2.4); 4.092 (0.9); 2.952 (3.0); 2.872 (2.7); 2.040 (9.7); 1.331 (0.5); 1.324 (0.5); 1.309 (0.5); 1.284 (0.8); 1.275 (3.2); 1.257 (7.5); 1.239 (2.8); 0.880 (0.6); 0.862 (0.3); 0.070 (5.2); 0.008 (1.3); 0.000 (27.0)

Example I.11

[0403] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.116 (0.6); 8.097 (14.9); 7.990 (16.0); 7.955 (0.5); 7.931 (7.3); 7.930 (7.3); 7.904 (7.8); 7.902 (7.7); 7.608 (0.5); 7.372 (3.9); 7.368 (4.0); 7.342 (5.1); 7.338 (5.1); 7.308 (9.9); 7.299 (10.9); 7.262 (69.8); 7.125 (6.8); 7.116 (6.2); 7.095 (5.4); 7.086 (5.1); 6.946 (0.4); 6.927 (8.4); 6.911 (0.8); 6.900 (8.0); 5.390 (2.4); 5.365 (2.5); 5.302 (14.5); 4.623 (3.7); 4.615 (3.7); 4.576 (4.7); 4.568 (4.7); 4.286 (4.5); 4.260 (4.3); 4.239 (3.6); 4.214 (3.7); 4.185 (2.8); 2.716 (1.6); 2.046 (0.6); 1.584 (3.2); 1.267 (1.0); 1.260 (0.9); 1.253 (1.0); 1.244 (1.8); 1.236 (0.4); 1.221 (0.9); 0.011 (1.7); 0.000 (56.1); 0.011 (2.6)

Example I.12

[0404] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.087 (14.9); 7.953 (16.0); 7.928 (0.3); 7.909 (7.3); 7.908 (7.1); 7.881 (7.7); 7.880 (7.4); 7.276 (5.2); 7.270 (3.8); 7.264 (27.5); 7.248 (10.2); 7.245 (9.9); 7.201 (2.6); 7.191 (19.5); 7.183 (4.9); 7.168 (4.0); 7.160 (8.9); 7.150 (1.1); 7.139 (0.5); 6.883 (8.4); 6.855 (8.1); 5.380 (2.1); 5.354 (2.3); 4.610 (3.5); 4.603 (3.5); 4.564 (4.5); 4.556 (4.4); 4.419 (2.9); 4.407 (2.8); 4.373 (0.3); 4.262 (4.4); 4.236 (4.1); 4.216 (3.4); 4.189 (3.3); 4.155 (0.5); 4.131 (1.3); 4.107 (1.3); 4.083 (0.5); 2.045 (6.0); 1.644 (4.8); 1.283 (1.7); 1.259 (3.5); 1.235 (1.6); 0.071 (1.7); 0.011 (0.6); 0.000 (19.0); 0.011 (0.8)

Example I.13

[0405] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.115 (4.1); 8.089 (14.8); 7.985 (4.0); 7.958 (15.1); 7.889 (2.2); 7.863 (9.8); 7.835 (8.2); 7.442 (9.1); 7.417 (16.0); 7.393 (9.0); 7.291 (5.7); 7.277 (12.3); 7.267 (22.4); 7.264 (25.4); 7.240 (7.6); 7.217 (3.0); 7.156 (17.9); 7.130 (11.9); 6.834 (2.2); 6.807 (10.1); 6.792 (4.5); 6.779 (7.8); 5.381 (6.6); 5.358 (5.6); 4.609 (5.8); 4.562 (7.4); 4.332 (6.4); 4.288 (1.8); 4.261 (6.0); 4.235 (5.4); 4.215 (4.6); 4.188 (3.6); 4.158 (1.4); 4.131 (2.8); 4.107 (2.6); 4.087 (0.9); 2.072 (2.4); 2.058 (5.2); 2.048 (8.8); 2.045 (9.9); 1.718 (0.4); 1.711 (0.4); 1.639 (7.3); 1.352 (0.4); 1.283 (4.6); 1.272 (4.2); 1.262 (7.0); 1.259 (7.6); 1.238 (2.8); 1.235 (3.0); 0.904 (0.4); 0.879 (0.5); 0.859 (0.5); 0.097 (0.6); 0.071 (1.8); 0.027 (3.3); 0.013 (7.3); 0.003 (12.0); 0.000 (13.6)

Example I.14

[0406] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.148 (0.4); 8.140 (0.4); 8.083 (12.1); 7.916 (14.3); 7.903 (7.1); 7.902 (7.0); 7.876 (7.1); 7.874 (7.0); 7.394 (1.2); 7.383 (12.6); 7.376 (4.3); 7.370 (1.7); 7.361 (5.0); 7.353 (16.0); 7.342 (2.3); 7.330 (0.3); 7.266 (13.6); 7.117 (1.7); 7.106 (15.8); 7.099 (4.8); 7.084 (4.7); 7.076 (12.9); 7.065 (1.5); 7.056 (1.0); 6.954 (0.4); 6.926 (0.4); 6.861 (7.7); 6.833 (7.3); 5.365 (1.9); 5.338 (2.0); 4.676 (2.8); 4.663 (2.7); 4.596 (3.2); 4.588 (3.2); 4.550 (4.0); 4.542 (4.0); 4.320 (0.4); 4.234 (3.8); 4.208 (3.7); 4.188 (3.1); 4.161 (3.0); 4.152 (0.6); 4.128 (1.2); 4.104 (1.2); 4.080 (0.4); 2.042 (5.5); 1.729 (1.5); 1.281 (1.6); 1.257 (3.3); 1.234 (1.6); 0.072 (0.6); 0.000 (9.1); 0.011 (0.4)

Example I.15

[0407] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.085 (6.3); 7.972 (6.5); 7.868 (3.0); 7.867 (3.1); 7.840 (3.1); 7.839 (3.3); 7.263 (20.3); 7.219 (1.5); 7.217 (1.5); 7.210 (1.2); 7.208 (1.1); 7.189 (1.9); 7.182 (1.6); 7.180 (1.5); 7.002 (3.7); 6.973 (2.9); 6.789 (3.5); 6.761 (3.4); 5.367 (0.9); 5.356 (0.9); 5.341 (0.9); 4.606 (1.5); 4.599 (1.5); 4.560 (1.9); 4.552 (1.9); 4.265 (1.9); 4.239 (1.8); 4.218 (1.8); 4.210 (2.0); 4.193 (2.4); 2.153 (16.0); 2.046 (0.4); 1.600 (4.1); 1.259 (0.4); 1.254 (0.4); 0.070 (11.1); 0.011 (0.5); 0.000 (13.3); 0.011 (0.6)

Example I.16

[0408] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.089 (6.2); 7.951 (6.5); 7.886 (2.9); 7.885 (3.0); 7.859 (3.0); 7.857 (3.1); 7.264 (12.1); 7.236 (2.6); 7.163 (3.0); 7.155 (3.4); 6.977 (2.0); 6.969 (1.9); 6.949 (1.7); 6.941 (1.6); 6.839 (3.4); 6.811 (3.3); 5.373 (0.9); 5.358 (0.8); 5.346 (0.9); 5.301 (0.6); 4.607 (1.4); 4.599 (1.5); 4.560 (1.8); 4.552 (1.8); 4.405 (1.5); 4.391 (1.5); 4.251 (1.8); 4.224 (1.7); 4.204 (1.4); 4.178 (1.3); 2.379 (16.0); 2.044 (0.4); 1.645 (1.7); 1.259 (0.4); 0.071 (11.6); 0.000 (7.2); 0.011 (0.3)

Example I.17

[0409] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.152 (0.3); 8.143 (0.3); 8.083 (6.0); 7.950 (6.7); 7.877 (3.1); 7.875 (3.0); 7.849 (3.3); 7.847 (3.2); 7.264 (11.5); 7.130 (0.5); 7.125 (0.7); 7.114 (16.0); 7.102 (3.1); 7.096 (7.1); 7.090 (6.9); 7.081 (1.9); 7.070 (0.6); 7.060 (0.5); 7.055 (0.4); 6.939 (0.3); 6.911 (0.3); 6.831 (3.6); 6.803 (3.4); 5.369 (0.9); 5.343 (1.0); 5.301 (0.6); 4.602 (1.5); 4.594 (1.5); 4.555 (1.9); 4.547 (1.9); 4.389 (1.3); 4.375 (1.4); 4.363 (0.5); 4.255 (1.9); 4.228 (1.8); 4.208 (1.5); 4.182 (1.4); 1.643 (1.4); 0.071 (10.5); 0.000 (7.9); 0.011 (0.4)

Example I.18

[0410] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.118 (0.9); 8.109 (1.0); 8.087 (14.8); 7.994 (16.0); 7.902 (8.0); 7.901 (7.6); 7.874 (8.4); 7.873 (8.0); 7.748 (0.5); 7.740 (0.5); 7.719 (0.5); 7.712 (0.5); 7.608 (0.7); 7.292 (0.4); 7.262 (110.9); 7.252 (1.9); 7.244 (1.0); 7.233 (2.8); 7.215 (2.5); 7.203 (4.4); 7.185 (4.3); 7.175 (2.5); 7.157 (2.1); 7.033 (0.9); 7.005 (0.8); 6.996 (2.4); 6.986 (3.0); 6.968 (2.6); 6.958 (3.8); 6.953 (4.3); 6.944 (11.6); 6.934 (3.3); 6.926 (4.3); 6.922 (6.0); 6.917 (12.2); 6.893 (2.2); 6.888 (1.9); 6.883 (1.4); 6.878 (1.4); 5.365 (2.6); 5.346 (2.8); 5.302 (2.2); 5.143 (0.4); 4.600 (3.8); 4.592 (3.9); 4.554 (5.0); 4.546 (5.0); 4.377 (0.6); 4.365 (0.6); 4.340 (0.6); 4.313 (0.7); 4.268 (5.0); 4.242 (4.6); 4.221 (3.8); 4.195 (3.6); 4.098 (0.3); 4.086 (0.4); 4.034 (1.5); 3.735 (0.4); 3.712 (0.5); 2.047 (0.9); 2.011 (0.5); 1.574 (8.0); 1.482 (0.3); 1.284 (0.5); 1.268 (1.2); 1.260 (1.2); 1.254 (1.6); 1.245 (1.9); 1.221 (0.9); 1.151 (0.3); 1.000 (0.3); 0.978 (0.3); 0.070 (43.6); 0.011 (2.7); 0.000 (78.1); 0.011 (3.3); 0.199 (0.3)

Example I.19

[0411] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.588 (0.4); 8.134 (3.1); 8.088 (16.0); 7.974 (15.3); 7.900 (7.7); 7.872 (7.4); 7.746 (1.8); 7.716 (1.6); 7.284 (8.3); 7.274 (19.9); 7.266 (31.0); 7.263 (37.2); 7.228 (21.4); 7.217 (21.2); 7.207 (23.6); 7.027 (2.1); 6.999 (1.8); 6.924 (8.0); 6.896 (7.1); 5.367 (5.2); 5.348 (4.8); 5.301 (2.5); 5.155 (1.4); 5.140 (1.4); 5.130 (1.4); 4.599 (5.1); 4.553 (6.6); 4.417 (0.8); 4.371 (2.3); 4.332 (1.7); 4.307 (1.6); 4.256 (4.9); 4.229 (4.9); 4.208 (4.5); 4.181 (9.4); 3.716 (1.8); 2.045 (0.4); 1.603 (15.3); 1.544 (0.4); 1.258 (1.8); 1.003 (0.3); 0.865 (0.4); 0.074 (37.2); 0.022 (5.6); 0.011 (13.2); 0.003 (19.8); 0.000 (23.5); 0.036 (0.4)

Example I.20

[0412] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.182 (0.5); 8.173 (0.6); 8.096 (14.1); 7.991 (16.0); 7.951 (0.4); 7.934 (7.8); 7.932 (7.6); 7.906 (8.3); 7.904 (8.0); 7.608 (0.4); 7.279 (0.4); 7.263 (80.1); 7.000 (0.5); 6.972 (0.5); 6.927 (9.2); 6.912 (0.8); 6.900 (8.8); 6.878 (1.4); 6.865 (6.7); 6.859 (2.0); 6.845 (7.2); 6.838 (6.9); 6.824 (2.5); 6.818 (6.6); 6.805 (1.4); 6.796 (0.7); 6.792 (0.8); 5.394 (1.5); 5.387 (2.1); 5.382 (2.0); 5.372 (2.5); 5.356 (2.2); 5.348 (1.8); 5.302 (2.4); 4.619 (4.0); 4.611 (3.9); 4.573 (5.1); 4.565 (5.0); 4.396 (0.4); 4.385 (0.4); 4.349 (0.4); 4.282 (4.9); 4.256 (4.6); 4.236 (3.8); 4.210 (3.7); 4.177 (6.6); 4.163 (6.5); 4.133 (0.4); 4.109 (0.4); 3.719 (0.4); 2.046 (1.3); 2.011 (0.4); 1.579 (32.0); 1.284 (0.5); 1.260 (1.3); 1.253 (1.7); 1.236 (0.6); 0.070 (20.4); 0.011 (1.8); 0.000 (54.2); 0.011 (2.3)

Example I.21

[0413] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.328 (11.3); 8.120 (10.1); 8.059 (0.4); 7.965 (11.4); 7.458 (0.8); 7.450 (4.0); 7.443 (1.9); 7.425 (8.2); 7.423 (7.5); 7.415 (1.7); 7.404 (3.2); 7.398 (7.2); 7.390 (1.4); 7.373 (0.4); 7.273 (2.4); 7.269 (4.7); 7.262 (54.0); 7.253 (1.7); 7.250 (2.7); 7.245 (5.6); 7.239 (2.1); 7.224 (1.7); 7.220 (2.4); 7.216 (1.5); 7.205 (0.4); 7.140 (8.0); 7.136 (10.0); 7.129 (2.9); 7.115 (4.9); 7.112 (8.0); 7.108 (6.8); 7.099 (1.1); 6.940 (16.0); 6.911 (0.4); 5.428 (2.3); 5.421 (2.4); 5.401 (2.6); 5.394 (2.5); 4.568 (3.1); 4.560 (3.1); 4.522 (4.3); 4.514 (4.2); 4.307 (4.0); 4.279 (3.8); 4.260 (2.9); 4.233 (2.8); 4.132 (0.8); 4.109 (0.8); 4.085 (0.4); 4.025 (0.7); 3.915 (0.8); 2.046 (3.1); 1.605 (2.2); 1.283 (1.0); 1.260 (2.0); 1.236 (0.9); 0.011 (1.4); 0.000 (38.0); 0.011 (1.2)

Example I.22

[0414] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.179 (15.5); 8.164 (9.7); 8.156 (9.8); 7.834 (14.8); 7.609 (0.3); 7.462 (1.0); 7.454 (4.7); 7.448 (2.4); 7.438 (1.6); 7.430 (9.4); 7.427 (8.6); 7.419 (1.9); 7.408 (3.5); 7.402 (8.1); 7.394 (1.4); 7.339 (12.1); 7.331 (12.0); 7.268 (8.1); 7.263 (59.3); 7.252 (1.7); 7.248 (3.0); 7.243 (6.5); 7.238 (2.4); 7.222 (1.8); 7.219 (2.8); 7.215 (1.7); 7.076 (2.3); 7.071 (8.8); 7.067 (11.3); 7.060 (3.2); 7.046 (5.4); 7.042 (8.9); 7.039 (8.0); 7.030 (1.2); 6.912 (0.4); 5.382 (2.0); 5.371 (2.3); 5.362 (2.8); 5.358 (2.7); 5.352 (2.8); 5.347 (2.8); 5.339 (2.7); 5.328 (2.3); 4.644 (2.8); 4.633 (2.9); 4.597 (6.5); 4.585 (16.0); 4.561 (11.5); 4.532 (6.3); 4.513 (6.0); 4.485 (2.8); 4.466 (2.7); 2.047 (0.8); 1.596 (48.3); 1.260 (0.6); 0.011 (1.7); 0.000 (43.8); 0.011 (1.6)

Example I.23

[0415] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.088 (15.2); 8.032 (0.6); 8.001 (16.0); 7.950 (0.4); 7.908 (7.7); 7.906 (7.9); 7.880 (8.1); 7.878 (8.5); 7.844 (0.6); 7.763 (0.4); 7.608 (1.1); 7.490 (10.6); 7.482 (11.6); 7.433 (0.4); 7.405 (0.4); 7.334 (0.7); 7.319 (6.0); 7.311 (5.6); 7.290 (9.1); 7.282 (8.8); 7.262 (212.9); 7.215 (0.9); 7.202 (0.8); 7.175 (13.6); 7.147 (9.3); 7.115 (0.5); 7.087 (0.5); 6.969 (0.5); 6.934 (9.1); 6.906 (8.4); 6.879 (0.3); 6.818 (0.4); 5.370 (2.5); 5.346 (2.7); 5.302 (9.4); 4.606 (3.9); 4.599 (3.9); 4.560 (5.1); 4.552 (4.8); 4.281 (4.8); 4.255 (4.5); 4.235 (3.9); 4.209 (3.5); 4.158 (0.9); 4.134 (2.8); 4.110 (3.0); 4.086 (1.1); 3.980 (2.3); 2.174 (0.3); 2.047 (13.9); 1.569 (38.7); 1.473 (0.4); 1.284 (3.8); 1.260 (8.2); 1.237 (3.9); 0.195 (0.5); 0.069 (33.5); 0.057 (1.8); 0.035 (0.6); 0.011 (4.7); 0.000 (141.0); 0.011 (5.6); 0.060 (0.4); 0.200 (0.4)

Example I.24

[0416] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.073 (2.1); 7.905 (2.3); 7.854 (1.0); 7.826 (1.1); 7.416 (1.5); 7.410 (0.6); 7.394 (0.7); 7.388 (1.8); 7.379 (0.3); 7.271 (3.2); 7.117 (2.1); 7.110 (0.7); 7.095 (0.7); 7.088 (1.8); 6.808 (1.2); 6.780 (1.2); 5.352 (0.4); 5.331 (0.4); 5.326 (0.4); 4.931 (0.6); 4.909 (0.6); 4.577 (0.5); 4.569 (0.5); 4.531 (0.6); 4.523 (0.6); 4.239 (0.5); 4.213 (0.5); 4.192 (0.4); 4.166 (0.4); 4.152 (1.1); 4.128 (3.4); 4.104 (3.5); 4.081 (1.2); 2.042 (16.0); 2.031 (0.4); 1.523 (3.9); 1.502 (3.9); 1.281 (4.4); 1.258 (8.9); 1.234 (4.6); 0.072 (5.8); 0.060 (0.3); 0.000 (1.7)

Example I.25

[0417] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.089 (9.2); 8.022 (7.1); 7.994 (7.6); 7.947 (11.2); 7.397 (1.3); 7.386 (12.9); 7.379 (4.6); 7.364 (5.3); 7.357 (16.0); 7.346 (2.2); 7.265 (9.5); 7.113 (1.9); 7.102 (15.8); 7.095 (5.3); 7.080 (4.7); 7.073 (13.0); 7.062 (1.8); 7.042 (5.8); 7.013 (5.5); 6.678 (3.7); 6.496 (7.5); 6.314 (3.8); 5.645 (2.4); 5.619 (2.6); 4.524 (3.1); 4.516 (3.2); 4.477 (4.5); 4.470 (4.5); 4.327 (2.6); 4.287 (4.4); 4.260 (4.1); 4.240 (3.1); 4.213 (2.9); 4.129 (0.7); 4.105 (0.7); 3.953 (1.1); 2.042 (2.9); 1.694 (4.8); 1.281 (1.2); 1.257 (3.9); 1.234 (1.1); 0.879 (0.5); 0.855 (0.4); 0.071 (5.7); 0.000 (9.7)

Example I.26

[0418] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =18.304 (0.4); 16.267 (0.4); 15.166 (0.4); 12.449 (0.4); 8.100 (0.5); 8.057 (13.2); 7.993 (14.6); 7.886 (6.8); 7.858 (7.1); 7.607 (1.0); 7.531 (0.4); 7.382 (1.8); 7.371 (12.6); 7.364 (4.5); 7.349 (4.9); 7.342 (16.0); 7.331 (1.9); 7.300 (0.7); 7.262 (159.5); 7.127 (2.5); 7.116 (15.0); 7.109 (4.3); 7.093 (4.3); 7.086 (11.8); 7.075 (1.3); 7.065 (0.5); 6.910 (0.7); 6.820 (0.5); 6.793 (8.0); 6.766 (7.4); 5.343 (0.5); 5.329 (0.5); 5.313 (1.7); 5.302 (5.4); 5.289 (3.3); 5.279 (2.3); 4.528 (3.4); 4.519 (3.0); 4.481 (4.9); 4.473 (4.6); 4.317 (4.5); 4.292 (4.2); 4.270 (3.0); 4.246 (2.9); 3.929 (6.7); 3.914 (6.2); 2.516 (0.5); 2.221 (0.5); 2.174 (0.7); 1.617 (0.4); 1.553 (141.0); 1.524 (1.1); 1.508 (0.8); 1.477 (0.5); 1.308 (1.2); 1.255 (3.7); 0.896 (0.6); 0.881 (1.1); 0.853 (0.6); 0.196 (0.8); 0.069 (18.0); 0.011 (6.2); 0.000 (185.3); 0.011 (8.4); 0.065 (0.6); 0.199 (0.9); 1.451 (0.4); 3.269 (0.5)

Example I.27

[0419] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.062 (3.3); 8.034 (3.5); 8.007 (4.0); 7.860 (4.2); 7.269 (1.8); 7.088 (13.5); 7.067 (12.6); 6.686 (3.5); 6.658 (3.4); 5.300 (1.5); 5.261 (2.2); 5.214 (2.4); 4.978 (1.7); 4.535 (2.5); 4.488 (2.2); 1.696 (16.0); 1.255 (0.6); 0.000 (0.9)

Example I.28

[0420] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.054 (3.3); 8.026 (3.4); 8.000 (4.4); 7.859 (4.1); 7.317 (0.3); 7.298 (0.4); 7.291 (0.4); 7.266 (3.8); 7.245 (1.5); 7.238 (1.9); 7.199 (1.0); 7.197 (1.0); 7.190 (0.8); 7.189 (0.7); 7.170 (1.2); 7.169 (1.2); 7.162 (1.0); 7.160 (1.0); 6.973 (2.6); 6.945 (2.0); 6.642 (3.4); 6.613 (3.3); 5.713 (0.4); 5.301 (0.7); 5.253 (1.9); 5.206 (2.1); 4.950 (0.5); 4.535 (2.2); 4.488 (2.0); 2.150 (0.5); 2.115 (11.2); 1.697 (16.0); 0.000 (3.9)

Example I.29

[0421] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.067 (3.6); 8.052 (0.6); 8.039 (3.8); 8.023 (0.5); 8.013 (4.3); 7.863 (4.4); 7.268 (2.6); 7.247 (1.6); 7.219 (1.9); 7.141 (2.4); 7.133 (2.5); 6.943 (1.6); 6.935 (1.5); 6.916 (1.3); 6.907 (1.2); 6.702 (0.4); 6.695 (3.8); 6.673 (0.4); 6.667 (3.7); 5.300 (0.4); 5.250 (1.9); 5.203 (2.2); 4.968 (0.9); 4.544 (2.3); 4.497 (2.1); 2.368 (12.5); 1.735 (1.3); 1.697 (16.0); 0.000 (2.4)

Example I.30

[0422] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.089 (4.3); 8.005 (4.2); 7.861 (2.4); 7.833 (2.6); 7.608 (0.4); 7.313 (0.4); 7.262 (51.7); 7.141 (2.3); 7.111 (2.9); 7.012 (3.0); 7.002 (2.6); 6.872 (2.1); 6.863 (1.6); 6.842 (2.9); 6.837 (3.3); 6.809 (2.3); 5.375 (1.3); 5.361 (1.3); 5.350 (1.2); 4.606 (1.4); 4.559 (1.9); 4.280 (1.4); 4.254 (1.4); 4.234 (1.1); 4.209 (1.1); 3.904 (2.9); 3.890 (2.3); 3.828 (16.0); 1.664 (0.4); 1.570 (143.6); 1.293 (0.9); 1.257 (1.8); 0.887 (0.6); 0.856 (0.4); 0.069 (7.1); 0.000 (47.4); 0.032 (0.4)

Example I.31

[0423] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.055 (2.8); 8.027 (2.8); 7.989 (3.8); 7.866 (3.5); 7.263 (46.0); 7.115 (2.3); 7.086 (2.8); 6.993 (2.2); 6.983 (2.6); 6.854 (1.6); 6.844 (1.4); 6.824 (1.3); 6.814 (1.1); 6.687 (2.8); 6.658 (2.7); 5.302 (9.2); 5.246 (1.6); 5.199 (1.9); 4.874 (2.9); 4.532 (2.0); 4.486 (1.7); 3.819 (16.0); 1.692 (10.3); 1.571 (113.0); 1.254 (1.0); 0.069 (8.2); 0.011 (1.2); 0.000 (38.4); 0.011 (1.7)

Example I.32

[0424] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.141 (1.5); 8.116 (3.9); 8.088 (3.3); 8.047 (2.6); 8.024 (4.8); 7.878 (2.7); 7.859 (5.6); 7.489 (1.4); 7.480 (1.4); 7.466 (3.7); 7.452 (1.7); 7.437 (3.3); 7.273 (4.3); 7.269 (4.2); 7.035 (1.5); 7.019 (3.0); 7.015 (3.0); 6.990 (2.2); 6.795 (1.5); 6.770 (3.9); 6.758 (1.7); 6.742 (2.8); 5.358 (0.3); 5.324 (0.9); 5.316 (0.8); 5.301 (2.0); 5.238 (2.6); 5.192 (2.9); 5.053 (1.0); 4.581 (1.4); 4.555 (2.9); 4.534 (1.5); 4.523 (1.2); 4.509 (2.6); 2.194 (0.5); 2.187 (0.5); 2.172 (1.2); 1.761 (0.9); 1.724 (7.3); 1.715 (6.9); 1.702 (16.0); 0.000 (0.8)

Example I.33

[0425] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.447 (0.4); 8.418 (0.4); 8.193 (0.5); 8.024 (10.1); 8.011 (0.8); 7.996 (10.5); 7.915 (13.4); 7.865 (13.2); 7.418 (0.5); 7.388 (0.6); 7.365 (1.3); 7.354 (12.7); 7.347 (4.4); 7.332 (4.8); 7.324 (16.3); 7.314 (1.8); 7.268 (5.6); 7.142 (0.6); 7.112 (0.6); 7.097 (1.8); 7.087 (16.0); 7.079 (4.8); 7.064 (4.4); 7.057 (12.9); 7.046 (1.3); 6.954 (0.3); 6.926 (0.3); 6.684 (9.4); 6.656 (9.1); 5.571 (1.1); 4.939 (8.6); 4.819 (5.6); 4.773 (7.0); 4.454 (7.6); 4.407 (6.0); 1.750 (3.6); 1.579 (41.0); 0.000 (4.9)

Example I.34

[0426] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.099 (2.6); 7.999 (2.7); 7.942 (1.3); 7.914 (1.3); 7.817 (2.3); 7.810 (0.7); 7.794 (0.8); 7.786 (2.5); 7.262 (13.8); 7.254 (1.6); 7.223 (1.3); 6.956 (1.5); 6.928 (1.5); 5.396 (0.4); 5.385 (0.3); 5.372 (0.4); 5.302 (0.4); 4.628 (0.6); 4.621 (0.6); 4.582 (0.8); 4.574 (0.8); 4.299 (0.8); 4.274 (0.8); 4.253 (0.6); 4.227 (0.6); 4.157 (1.1); 4.133 (3.6); 4.110 (3.9); 4.086 (1.2); 16.0); 1.575 (3.4); 1.284 (4.3); 1.260 (8.6); 1.236 (4.2); 0.069 (1.6); 0.011 (0.5); 0.000 (16.0); 0.011 (0.7)

Example I.35

[0427] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.234 (1.6); 8.231 (1.7); 8.203 (1.2); 8.143 (4.1); 8.115 (4.3); 8.006 (5.8); 7.872 (5.1); 7.866 (1.8); 7.859 (0.5); 7.842 (0.5); 7.835 (1.5); 7.810 (0.5); 7.799 (4.5); 7.792 (1.5); 7.776 (1.5); 7.769 (5.0); 7.758 (0.5); 7.307 (0.8); 7.277 (0.9); 7.262 (35.5); 7.215 (2.8); 7.185 (2.5); 7.053 (1.2); 7.025 (1.2); 6.818 (4.3); 6.789 (4.1); 5.717 (3.4); 5.302 (15.9); 5.249 (2.5); 4.994 (2.7); 4.537 (2.7); 4.490 (2.4); 2.010 (0.3); 1.713 (16.0); 1.559 (3.1); 1.269 (0.4); 1.254 (0.5); 1.246 (0.5); 0.069 (9.3); 0.057 (0.4); 0.011 (1.2); 0.000 (40.7); 0.011 (1.7)

Example I.36

[0428] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.603 (7.8); 8.160 (9.7); 8.044 (3.2); 8.038 (2.8); 8.024 (2.6); 7.882 (9.0); 7.875 (3.1); 7.858 (3.6); 7.852 (9.8); 7.841 (1.1); 7.327 (9.7); 7.300 (34.9); 7.271 (5.5); 5.496 (1.9); 5.468 (2.0); 5.339 (16.0); 4.526 (2.0); 4.520 (1.9); 4.479 (3.2); 4.473 (3.1); 4.347 (2.3); 4.319 (2.1); 4.300 (1.5); 4.272 (1.4); 4.180 (0.4); 4.157 (0.5); 4.093 (0.4); 4.086 (0.4); 4.079 (0.4); 4.061 (0.4); 4.021 (0.9); 1.596 (11.1); 1.334 (0.4); 1.304 (0.9); 1.292 (1.9); 1.259 (0.4); 0.108 (3.2); 0.039 (35.5); 0.028 (1.8)

Example I.37

[0429] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.500 (5.7); 8.071 (5.5); 7.959 (6.6); 7.881 (0.6); 7.870 (5.8); 7.863 (1.9); 7.847 (1.9); 7.840 (6.5); 7.829 (0.7); 7.378 (6.6); 7.300 (51.6); 7.277 (3.7); 7.247 (3.2); 5.339 (13.2); 4.742 (2.7); 4.694 (3.7); 4.503 (5.4); 4.499 (5.5); 4.451 (2.8); 1.693 (16.0); 1.588 (17.9); 0.108 (0.6); 0.050 (1.8); 0.039 (52.9); 0.028 (2.0)

Example I.38

[0430] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.136 (0.4); 8.047 (0.5); 7.587 (0.3); 7.300 (6.7); 7.285 (0.4); 7.255 (0.3); 6.905 (0.3); 1.603 (16.0); 0.108 (0.7); 0.038 (7.0); 0.028 (0.3)

Example I.39

[0431] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.138 (3.4); 8.109 (4.7); 8.083 (1.3); 8.041 (5.3); 8.014 (2.1); 7.909 (4.9); 7.882 (2.0); 7.598 (3.4); 7.569 (5.2); 7.543 (2.0); 7.307 (9.3); 7.300 (23.3); 7.273 (7.8); 7.250 (4.7); 7.222 (5.3); 7.197 (1.8); 6.892 (1.4); 6.864 (0.6); 6.794 (3.6); 6.766 (4.5); 6.740 (1.2); 6.703 (2.7); 6.677 (1.1); 6.515 (1.4); 6.488 (0.6); 5.339 (4.3); 5.323 (2.9); 5.313 (1.8); 5.297 (1.4); 5.276 (2.9); 5.250 (1.3); 4.990 (4.1); 4.963 (1.9); 4.573 (2.9); 4.545 (1.3); 4.526 (2.7); 4.500 (1.0); 1.745 (16.0); 1.718 (6.5); 1.598 (16.5); 1.571 (7.7); 1.294 (0.7); 1.266 (0.5); 0.108 (3.2); 0.082 (1.2); 0.046 (9.2); 0.039 (22.4); 0.012 (7.1)

Example I.40

[0432] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.131 (4.9); 8.117 (2.0); 8.088 (2.0); 8.033 (5.1); 7.589 (0.4); 7.578 (4.6); 7.571 (1.5); 7.555 (1.5); 7.548 (5.3); 7.538 (0.5); 7.300 (15.7); 7.153 (2.5); 7.141 (5.4); 7.134 (1.7); 7.125 (2.2); 7.119 (1.7); 7.112 (4.6); 7.101 (0.5); 5.549 (0.7); 5.524 (0.7); 4.525 (0.9); 4.517 (1.0); 4.478 (1.4); 4.471 (1.4); 4.308 (1.4); 4.281 (1.4); 4.261 (1.0); 4.234 (1.0); 4.116 (2.3); 4.104 (2.3); 1.609 (16.0); 1.293 (0.5); 0.108 (1.4); 0.049 (0.5); 0.039 (15.0); 0.028 (0.5)

Example I.41

[0433] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.115 (14.5); 8.025 (14.6); 7.948 (3.6); 7.919 (4.4); 7.889 (3.7); 7.646 (0.6); 7.438 (1.2); 7.427 (12.9); 7.420 (4.2); 7.405 (4.6); 7.397 (15.8); 7.386 (1.7); 7.367 (0.6); 7.300 (121.1); 7.270 (0.4); 7.233 (0.5); 7.144 (1.6); 7.133 (16.0); 7.126 (4.7); 7.111 (4.1); 7.103 (12.7); 7.093 (1.2); 6.949 (0.7); 6.828 (5.9); 6.801 (5.5); 5.364 (1.4); 5.350 (1.8); 5.339 (2.9); 5.330 (2.1); 5.315 (1.6); 4.590 (3.1); 4.581 (3.2); 4.543 (4.8); 4.534 (4.8); 4.393 (4.7); 4.368 (4.5); 4.346 (3.1); 4.321 (2.9); 4.000 (8.1); 3.985 (8.0); 1.660 (0.5); 1.594 (134.6); 1.527 (0.7); 1.380 (0.4); 1.342 (0.5); 1.292 (1.1); 0.920 (0.4); 0.234 (0.5); 0.120 (1.1); 0.108 (33.8); 0.049 (3.9); 0.038 (128.9); 0.027 (5.1); 0.008 (0.3); 0.029 (0.6); 0.160 (0.6)

Example I.42

[0434] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.045 (1.5); 8.017 (1.8); 8.011 (1.8); 8.001 (4.0); 7.983 (1.7); 7.921 (3.9); 7.424 (0.5); 7.413 (4.0); 7.406 (1.4); 7.391 (1.5); 7.383 (4.9); 7.372 (0.6); 7.300 (17.2); 7.118 (0.6); 7.107 (4.9); 7.100 (1.5); 7.085 (1.3); 7.078 (4.0); 7.067 (0.4); 6.722 (1.7); 6.717 (1.7); 6.695 (1.6); 6.690 (1.7); 4.855 (2.7); 4.811 (1.4); 4.765 (1.8); 4.496 (2.0); 4.449 (1.5); 2.047 (2.0); 1.607 (16.0); 0.107 (2.0); 0.049 (0.8); 0.038 (18.3); 0.027 (0.8)

Example I.43

[0435] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.591 (11.5); 8.161 (14.7); 8.045 (16.0); 7.646 (0.6); 7.367 (0.5); 7.339 (6.0); 7.308 (11.8); 7.300 (110.2); 7.279 (13.8); 7.242 (2.4); 7.232 (19.4); 7.224 (4.8); 7.209 (3.8); 7.201 (10.4); 7.190 (0.9); 6.949 (0.6); 5.480 (2.5); 5.453 (2.5); 4.518 (2.8); 4.510 (2.9); 4.471 (4.6); 4.463 (4.7); 4.342 (4.6); 4.314 (4.2); 4.295 (2.8); 4.267 (2.8); 3.948 (4.5); 3.938 (4.5); 2.048 (8.9); 1.664 (0.4); 1.597 (53.9); 1.533 (0.3); 1.290 (1.1); 0.234 (0.4); 0.108 (2.3); 0.049 (4.1); 0.038 (119.4); 0.027 (4.2); 0.160 (0.4)

Example I.44

[0436] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.477 (5.7); 8.070 (6.8); 7.958 (7.2); 7.335 (7.2); 7.328 (3.3); 7.325 (3.3); 7.318 (1.7); 7.300 (48.0); 7.220 (1.2); 7.209 (8.8); 7.201 (2.3); 7.186 (1.9); 7.179 (5.0); 7.167 (0.5); 5.340 (4.8); 4.732 (2.5); 4.685 (3.7); 4.484 (4.1); 4.461 (6.6); 4.437 (2.8); 1.680 (16.0); 1.655 (0.6); 1.598 (17.9); 1.307 (0.4); 1.292 (0.4); 1.284 (0.4); 0.108 (1.4); 0.049 (2.3); 0.038 (48.0); 0.027 (1.7)

Example I.45

[0437] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): 15.116 (0.4); 15.105 (0.4); 8.468 (5.5); 8.066 (6.4); 7.957 (6.7); 7.646 (1.0); 7.439 (6.4); 7.431 (2.1); 7.416 (2.3); 7.409 (7.4); 7.398 (1.0); 7.366 (1.1); 7.316 (8.1); 7.300 (198.5); 7.233 (0.5); 7.137 (0.9); 7.126 (7.5); 7.119 (2.0); 7.104 (1.9); 7.097 (6.0); 6.949 (1.1); 5.340 (12.4); 4.727 (2.5); 4.680 (3.7); 4.480 (3.9); 4.433 (9.2); 1.721 (0.4); 1.675 (16.0); 1.593 (225.5); 1.526 (1.0); 1.500 (0.5); 1.466 (0.4); 1.306 (0.9); 1.293 (1.4); 1.260 (0.5); 0.918 (0.5); 0.897 (0.5); 0.234 (0.7); 0.172 (0.4); 0.119 (0.9); 0.108 (28.9); 0.069 (0.5); 0.049 (5.8); 0.038 (187.8); 0.027 (7.4); 0.028 (0.6); 0.159 (0.8)

Example I.46

[0438] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.468 (5.6); 8.067 (6.3); 7.957 (6.9); 7.646 (0.6); 7.449 (0.7); 7.438 (6.5); 7.431 (2.2); 7.416 (2.5); 7.409 (7.8); 7.398 (0.9); 7.366 (0.5); 7.348 (0.3); 7.316 (7.3); 7.300 (94.3); 7.137 (1.0); 7.126 (7.9); 7.119 (2.3); 7.104 (2.3); 7.097 (6.2); 7.086 (0.6); 6.949 (0.4); 5.340 (12.1); 4.726 (2.6); 4.679 (3.6); 4.480 (4.1); 4.434 (7.8); 1.675 (16.0); 1.598 (49.3); 1.307 (0.8); 1.293 (1.2); 1.284 (0.7); 1.261 (0.6); 1.240 (0.4); 0.107 (14.9); 0.096 (0.7); 0.049 (3.9); 0.038 (89.4); 0.027 (3.4); 0.160 (0.3)

Example I.47

[0439] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.600 (7.4); 8.161 (10.0); 8.036 (6.8); 7.756 (5.5); 7.727 (6.4); 7.322 (6.6); 7.314 (10.8); 7.300 (44.3); 5.489 (1.6); 5.462 (1.6); 4.523 (1.8); 4.516 (1.9); 4.476 (3.0); 4.469 (3.0); 4.345 (2.9); 4.317 (2.7); 4.298 (1.8); 4.270 (1.7); 4.059 (1.2); 1.604 (16.0); 1.291 (0.4); 0.108 (2.6); 0.049 (1.5); 0.039 (45.1); 0.028 (1.6)

Example I.48

[0440] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.585 (10.3); 8.154 (13.4); 8.011 (12.8); 7.608 (1.2); 7.598 (12.2); 7.591 (3.8); 7.575 (4.0); 7.569 (13.3); 7.558 (1.4); 7.300 (26.5); 7.256 (11.7); 7.105 (1.4); 7.094 (13.6); 7.088 (4.0); 7.072 (3.8); 7.065 (11.9); 7.055 (1.2); 5.467 (2.2); 5.439 (2.2); 4.504 (2.5); 4.497 (2.6); 4.457 (4.2); 4.450 (4.1); 4.328 (4.0); 4.300 (3.7); 4.281 (2.5); 4.253 (2.4); 4.153 (2.2); 2.045 (8.3); 1.632 (16.0); 1.291 (0.4); 0.107 (1.9); 0.048 (1.0); 0.038 (28.3); 0.027 (1.1)

Example I.49

[0441] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.469 (5.6); 8.359 (0.4); 8.327 (0.4); 8.216 (0.9); 8.065 (6.5); 8.024 (1.1); 7.958 (6.8); 7.657 (0.5); 7.646 (0.8); 7.637 (0.8); 7.598 (0.9); 7.588 (6.5); 7.580 (2.2); 7.565 (2.1); 7.558 (7.3); 7.547 (0.8); 7.428 (0.4); 7.389 (0.4); 7.358 (0.6); 7.317 (7.5); 7.300 (122.9); 7.085 (0.8); 7.074 (7.2); 7.067 (2.2); 7.052 (2.1); 7.045 (6.4); 7.034 (0.8); 6.949 (0.6); 5.299 (1.0); 5.281 (1.1); 4.728 (2.5); 4.680 (3.6); 4.480 (3.8); 4.442 (6.4); 4.433 (3.1); 2.944 (0.3); 2.888 (0.4); 2.638 (0.3); 2.579 (0.4); 2.049 (0.5); 1.675 (16.0); 1.655 (3.0); 1.590 (46.1); 1.293 (1.5); 0.918 (0.4); 0.235 (0.5); 0.108 (7.9); 0.050 (5.5); 0.039 (133.6); 0.028 (5.0); 0.160 (0.5)

Example I.50

[0442] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.490 (5.7); 8.071 (6.6); 7.959 (7.1); 7.743 (3.8); 7.715 (4.4); 7.369 (6.6); 7.300 (49.1); 7.271 (3.8); 5.340 (11.7); 4.738 (2.6); 4.690 (3.7); 4.493 (4.7); 4.486 (6.7); 4.445 (2.9); 1.688 (16.0); 1.596 (17.8); 1.293 (1.0); 0.108 (3.1); 0.049 (1.7); 0.038 (47.7); 0.027 (1.9)

Example I.51

[0443] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.112 (4.7); 8.084 (5.0); 8.036 (5.7); 7.905 (5.5); 7.646 (0.6); 7.417 (0.7); 7.407 (5.8); 7.400 (1.9); 7.385 (2.2); 7.377 (7.2); 7.366 (1.5); 7.300 (116.3); 7.289 (2.0); 7.234 (0.5); 7.122 (0.9); 7.112 (7.1); 7.104 (2.1); 7.089 (1.9); 7.082 (5.7); 7.071 (0.6); 6.949 (0.5); 6.755 (5.0); 6.727 (4.8); 5.340 (1.2); 5.320 (2.6); 5.273 (2.9); 4.977 (4.3); 4.564 (3.2); 4.516 (2.8); 1.737 (16.0); 1.735 (15.7); 1.709 (0.4); 1.656 (1.0); 1.589 (156.0); 1.523 (0.7); 1.323 (0.4); 1.293 (2.8); 0.234 (0.4); 0.120 (0.5); 0.108 (7.1); 0.049 (4.7); 0.039 (114.3); 0.028 (4.5); 0.028 (0.6); 0.160 (0.3)

Example I.52

[0444] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =17.800 (0.4); 17.078 (0.4); 12.484 (0.4); 11.639 (0.4); 10.368 (0.4); 8.112 (4.3); 8.084 (4.5); 8.036 (5.6); 7.906 (5.5); 7.646 (1.1); 7.435 (0.4); 7.407 (5.3); 7.400 (1.9); 7.385 (1.9); 7.378 (6.6); 7.367 (1.7); 7.327 (0.6); 7.300 (179.7); 7.233 (0.6); 7.122 (0.7); 7.112 (6.4); 7.105 (2.0); 7.089 (1.6); 7.082 (5.2); 6.949 (0.9); 6.755 (4.5); 6.727 (4.3); 5.811 (0.4); 5.340 (0.7); 5.320 (2.7); 5.274 (2.9); 4.976 (4.2); 4.563 (3.1); 4.517 (2.8); 1.736 (16.0); 1.700 (0.4); 1.671 (0.5); 1.654 (1.4); 1.587 (240.3); 1.521 (1.1); 1.340 (0.4); 1.293 (3.9); 0.893 (0.4); 0.234 (0.8); 0.108 (10.8); 0.050 (5.5); 0.039 (174.0); 0.028 (6.1); 0.028 (0.9); 0.160 (0.7); 1.485 (0.4); 3.388 (0.4)

Example I.53

[0445] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.472 (4.8); 8.023 (3.8); 7.898 (3.5); 7.416 (0.4); 7.405 (3.6); 7.398 (1.2); 7.383 (1.3); 7.375 (4.3); 7.365 (0.5); 7.300 (13.9); 7.097 (0.5); 7.086 (4.3); 7.079 (1.3); 7.064 (1.1); 7.057 (3.5); 7.046 (0.4); 6.913 (4.9); 5.339 (0.5); 5.215 (1.7); 5.168 (1.9); 4.834 (2.2); 4.557 (2.1); 4.510 (1.8); 2.211 (16.0); 1.736 (11.9); 1.613 (3.4); 0.107 (0.8); 0.049 (0.5); 0.038 (13.4); 0.027 (0.5)

Example I.54

[0446] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.472 (4.0); 8.023 (3.1); 7.899 (2.9); 7.405 (3.0); 7.398 (1.0); 7.383 (1.1); 7.376 (3.6); 7.365 (0.4); 7.300 (19.7); 7.097 (0.4); 7.087 (3.6); 7.079 (1.1); 7.064 (1.0); 7.057 (2.9); 6.913 (4.1); 5.339 (0.5); 5.218 (1.4); 5.171 (1.6); 4.830 (2.0); 4.557 (1.7); 4.510 (1.5); 2.220 (0.4); 2.211 (16.0); 1.737 (9.1); 1.602 (8.9); 1.294 (0.5); 0.108 (1.2); 0.049 (0.8); 0.038 (19.1); 0.027 (0.7)

Example I.55

[0447] .sup.1H-NMR (300.2 MHz, d.sub.6-DMSO): =8.537 (11.6); 8.485 (16.0); 7.988 (14.8); 7.706 (8.1); 7.678 (9.3); 7.491 (13.1); 7.426 (0.4); 7.373 (10.4); 7.345 (8.7); 7.287 (3.3); 7.101 (7.2); 6.915 (3.5); 6.216 (6.8); 6.200 (7.0); 5.781 (12.7); 5.229 (2.2); 5.216 (2.6); 5.204 (2.3); 4.494 (1.9); 4.466 (1.8); 4.447 (3.8); 4.420 (3.6); 4.372 (3.8); 4.360 (3.8); 4.325 (1.8); 4.313 (1.6); 3.954 (0.6); 3.351 (40.4); 3.201 (0.4); 3.184 (0.4); 2.531 (6.3); 2.525 (8.2); 2.519 (6.1); 2.012 (0.7); 1.258 (0.4); 1.198 (0.4); 1.079 (0.4); 0.023 (7.0)

Example I.56

[0448] .sup.1H-NMR (400.1 MHz, CDCl.sub.3): =8.441 (5.7); 8.072 (2.9); 7.900 (3.8); 7.581 (3.9); 7.560 (4.3); 7.310 (6.8); 7.264 (3.5); 7.227 (4.8); 7.206 (4.3); 6.808 (1.7); 6.666 (3.5); 6.525 (1.7); 4.666 (2.5); 4.630 (3.4); 4.451 (3.6); 4.416 (2.6); 1.641 (16.0); 0.000 (2.4)

Example I.57

[0449] .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO): =8.476 (11.7); 8.441 (16.0); 7.946 (16.0); 7.681 (4.1); 7.676 (4.3); 7.655 (4.2); 7.650 (4.2); 7.547 (13.2); 7.472 (2.9); 7.450 (7.0); 7.429 (5.3); 7.395 (4.6); 7.391 (4.4); 7.373 (2.6); 7.370 (2.3); 6.165 (6.6); 6.153 (6.8); 5.197 (2.1); 5.187 (2.4); 5.178 (2.1); 4.455 (2.0); 4.434 (1.9); 4.420 (3.6); 4.399 (3.5); 4.348 (3.5); 4.339 (3.5); 4.313 (1.9); 4.304 (1.8); 3.304 (25.8); 2.505 (9.5); 2.500 (12.7); 2.496 (9.4); 0.000 (11.0); 0.008 (0.6)

Example I.58

[0450] .sup.1H-NMR (300.2 MHz, d.sub.6-DMSO): =8.539 (0.4); 8.336 (10.3); 8.315 (7.2); 8.057 (0.4); 7.859 (10.1); 7.702 (2.7); 7.694 (2.7); 7.667 (2.5); 7.660 (2.6); 7.547 (8.9); 7.490 (1.7); 7.461 (4.2); 7.434 (3.8); 7.412 (3.4); 7.410 (3.3); 7.405 (3.0); 7.381 (1.4); 7.373 (1.3); 5.949 (0.7); 5.865 (9.5); 4.565 (0.9); 4.517 (5.2); 4.502 (5.2); 4.455 (1.0); 3.348 (18.9); 2.537 (3.9); 2.531 (7.7); 2.525 (10.3); 2.519 (7.5); 2.513 (3.6); 1.583 (16.0); 0.034 (0.5); 0.023 (11.3); 0.012 (0.5)

Example I.59

[0451] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.231 (3.2); 8.202 (3.3); 8.043 (7.2); 8.005 (0.3); 7.952 (8.0); 7.572 (0.8); 7.561 (7.5); 7.554 (2.3); 7.538 (2.4); 7.531 (8.4); 7.521 (0.9); 7.300 (36.8); 7.137 (0.9); 7.126 (8.6); 7.119 (2.5); 7.104 (2.3); 7.097 (7.4); 7.086 (0.7); 7.033 (3.8); 7.004 (3.6); 5.339 (8.7); 4.761 (2.9); 4.714 (8.4); 4.554 (4.7); 4.506 (3.0); 2.996 (0.6); 2.923 (0.5); 1.678 (16.0); 1.604 (13.6); 1.306 (0.5); 1.292 (1.0); 1.283 (0.6); 0.108 (5.8); 0.049 (1.1); 0.038 (37.9); 0.027 (1.4)

Example I.60

[0452] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.172 (3.7); 8.147 (10.6); 8.063 (8.6); 7.875 (0.9); 7.864 (7.6); 7.857 (2.5); 7.841 (2.6); 7.833 (8.6); 7.823 (1.1); 7.646 (0.8); 7.365 (4.8); 7.334 (4.4); 7.300 (127.8); 7.241 (3.9); 7.213 (3.6); 6.949 (0.8); 5.573 (1.4); 5.547 (1.4); 5.340 (16.0); 4.547 (1.7); 4.539 (1.7); 4.500 (2.7); 4.492 (2.6); 4.330 (2.7); 4.304 (2.6); 4.284 (1.7); 4.257 (1.8); 4.025 (2.6); 1.663 (0.5); 1.596 (86.9); 1.410 (0.3); 1.349 (0.6); 1.321 (0.8); 1.307 (1.2); 1.292 (1.8); 1.284 (1.3); 1.260 (0.6); 0.919 (0.6); 0.892 (0.5); 0.866 (0.4); 0.854 (0.4); 0.233 (0.5); 0.119 (1.1); 0.107 (26.2); 0.095 (1.0); 0.049 (4.5); 0.038 (124.6); 0.027 (4.6); 0.009 (0.4); 0.029 (0.5); 0.160 (0.5)

Example I.61

[0453] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =9.881 (0.4); 8.157 (6.4); 8.144 (15.5); 8.128 (6.6); 8.060 (16.0); 7.736 (8.7); 7.707 (10.2); 7.646 (0.9); 7.373 (9.5); 7.345 (8.3); 7.300 (151.7); 7.233 (0.6); 7.220 (6.7); 7.192 (6.2); 6.949 (0.9); 5.566 (2.2); 5.543 (2.2); 5.340 (1.2); 4.543 (2.9); 4.536 (3.1); 4.497 (4.7); 4.489 (4.4); 4.327 (4.4); 4.300 (4.4); 4.280 (3.2); 4.254 (3.0); 4.024 (5.3); 4.013 (5.2); 2.260 (0.4); 1.727 (0.3); 1.593 (37.5); 1.519 (0.3); 1.441 (0.3); 1.410 (0.7); 1.372 (1.0); 1.324 (2.0); 1.293 (3.9); 1.213 (0.4); 1.207 (0.4); 1.181 (0.3); 0.942 (0.7); 0.919 (1.1); 0.894 (1.0); 0.866 (1.2); 0.234 (0.7); 0.108 (3.3); 0.049 (5.2); 0.038 (165.4); 0.028 (5.9); 0.029 (0.6); 0.159 (0.5)

Example I.62

[0454] .sup.1H-NMR (300.2 MHz, d.sub.6-DMSO): =8.432 (0.5); 8.383 (6.8); 8.339 (0.5); 8.333 (0.4); 8.314 (0.4); 8.264 (0.3); 8.184 (3.3); 8.155 (3.6); 8.045 (6.1); 8.015 (6.8); 7.890 (6.5); 7.537 (0.4); 7.452 (6.0); 7.423 (6.2); 7.381 (3.6); 5.944 (6.6); 5.793 (8.8); 5.756 (0.4); 4.637 (0.3); 4.608 (1.1); 4.558 (5.8); 4.545 (6.1); 4.497 (1.1); 3.363 (10.9); 2.648 (0.4); 2.627 (0.6); 2.535 (23.4); 2.388 (0.4); 1.699 (0.3); 1.599 (16.0); 1.273 (0.6); 0.094 (0.4); 0.032 (10.8)

Example I.63

[0455] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.386 (8.8); 8.163 (0.4); 8.141 (12.3); 8.045 (12.9); 7.646 (0.5); 7.601 (1.4); 7.591 (12.3); 7.584 (4.1); 7.568 (4.1); 7.561 (14.1); 7.550 (1.6); 7.300 (117.8); 7.233 (3.1); 7.201 (9.0); 7.103 (1.4); 7.092 (14.0); 7.085 (4.3); 7.069 (3.9); 7.062 (12.6); 7.051 (6.7); 6.949 (0.6); 6.868 (3.2); 5.410 (2.0); 5.396 (1.8); 5.383 (2.1); 5.340 (16.0); 4.500 (0.9); 4.488 (1.4); 4.453 (5.6); 4.441 (5.7); 4.437 (6.3); 4.409 (4.7); 4.390 (1.0); 4.362 (1.3); 3.956 (8.5); 3.945 (8.5); 2.438 (0.4); 1.592 (49.0); 1.293 (1.3); 0.920 (0.3); 0.234 (0.6); 0.108 (3.4); 0.050 (4.1); 0.039 (124.2); 0.028 (4.4); 0.160 (0.5)

Example I.64

[0456] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.160 (3.6); 8.105 (5.2); 8.006 (5.6); 7.840 (1.4); 7.659 (1.6); 7.654 (1.6); 7.473 (1.5); 7.446 (0.5); 7.435 (4.9); 7.427 (1.6); 7.412 (1.7); 7.405 (6.0); 7.394 (0.6); 7.356 (3.6); 7.300 (14.9); 7.145 (0.7); 7.134 (6.1); 7.126 (1.8); 7.111 (1.6); 7.104 (4.8); 7.093 (0.4); 4.655 (1.8); 4.607 (2.7); 4.592 (2.8); 4.385 (3.2); 4.338 (2.4); 2.047 (1.9); 1.632 (6.3); 1.613 (16.0); 1.291 (0.7); 0.107 (3.4); 0.037 (9.5); 0.026 (0.4)

Example I.65

[0457] .sup.1H-NMR (300.2 MHz, d.sub.6-DMSO): =8.381 (9.7); 8.172 (3.2); 8.143 (3.5); 7.889 (10.0); 7.872 (5.0); 7.843 (5.6); 7.452 (5.3); 7.424 (4.8); 7.376 (4.2); 7.347 (4.0); 5.933 (6.7); 5.902 (0.5); 4.603 (0.9); 4.556 (5.1); 4.541 (5.1); 4.494 (0.9); 3.361 (24.8); 2.547 (3.8); 2.541 (7.9); 2.535 (10.8); 2.529 (7.9); 2.523 (3.7); 2.108 (4.3); 1.598 (16.0); 0.032 (4.5)

Example I.66

[0458] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.258 (3.0); 8.229 (3.2); 8.043 (6.3); 7.951 (7.2); 7.302 (7.9); 7.269 (2.0); 7.261 (3.2); 7.231 (5.6); 7.208 (7.4); 7.203 (3.5); 7.179 (0.8); 7.172 (0.7); 7.136 (3.6); 7.107 (3.4); 4.733 (2.6); 4.702 (4.8); 4.686 (4.4); 4.550 (4.4); 4.503 (2.7); 1.668 (16.0); 1.648 (3.7); 0.109 (0.9); 0.049 (0.4); 0.038 (8.0); 0.028 (0.3)

Example I.67

[0459] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.227 (3.1); 8.198 (3.2); 8.047 (7.0); 7.944 (7.5); 7.423 (0.7); 7.412 (6.6); 7.405 (2.2); 7.390 (2.5); 7.383 (8.3); 7.372 (0.9); 7.301 (7.7); 7.188 (1.0); 7.177 (8.5); 7.169 (2.4); 7.154 (2.2); 7.147 (6.4); 7.136 (0.6); 7.030 (3.7); 7.001 (3.5); 5.338 (1.7); 4.759 (7.7); 4.706 (4.2); 4.554 (4.5); 4.506 (2.9); 1.677 (16.0); 1.660 (2.0); 1.292 (1.8); 0.108 (0.4); 0.038 (7.7)

Example I.68

[0460] .sup.1H-NMR (300.2 MHz, d.sub.6-DMSO): =8.478 (14.2); 8.223 (12.7); 7.975 (14.2); 7.539 (1.1); 7.527 (11.7); 7.520 (3.9); 7.505 (4.6); 7.498 (14.1); 7.486 (1.6); 7.307 (15.3); 7.241 (1.6); 7.230 (14.5); 7.223 (4.3); 7.208 (4.2); 7.200 (11.3); 7.189 (1.2); 6.100 (7.2); 6.084 (7.4); 5.786 (16.0); 5.274 (1.3); 5.256 (3.1); 5.236 (3.3); 5.219 (1.4); 4.445 (0.4); 4.416 (9.4); 4.398 (6.8); 3.353 (42.4); 2.754 (0.3); 2.534 (33.1); 2.528 (43.2); 2.522 (30.5); 1.261 (0.8); 0.037 (1.6); 0.026 (43.6); 0.015 (1.5)

Example I.69

[0461] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.538 (13.2); 8.208 (0.4); 8.143 (0.3); 8.113 (14.6); 8.057 (0.5); 8.026 (0.5); 8.020 (0.3); 8.016 (0.3); 7.934 (16.0); 7.744 (9.4); 7.716 (10.5); 7.670 (0.4); 7.373 (15.2); 7.352 (0.6); 7.302 (20.9); 7.278 (9.0); 6.321 (2.7); 6.286 (3.0); 6.264 (3.1); 6.229 (3.3); 5.507 (0.5); 5.427 (8.8); 5.372 (12.5); 5.338 (8.3); 5.223 (0.5); 5.201 (0.4); 4.816 (10.5); 4.775 (5.7); 4.728 (9.9); 4.619 (9.7); 4.571 (5.4); 1.690 (1.9); 1.294 (1.0); 0.110 (1.3); 0.039 (8.0); 0.028 (0.5)

Example I.70

[0462] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.193 (6.1); 8.164 (6.7); 8.139 (15.6); 8.059 (16.0); 7.646 (0.7); 7.350 (7.0); 7.321 (6.9); 7.300 (146.0); 7.135 (1.4); 7.124 (2.8); 7.113 (14.4); 7.089 (14.0); 7.078 (2.7); 7.067 (1.3); 6.949 (0.8); 5.539 (2.3); 5.514 (2.3); 5.385 (0.4); 4.521 (2.9); 4.513 (3.2); 4.474 (4.6); 4.466 (4.5); 4.306 (4.7); 4.279 (4.4); 4.259 (3.2); 4.232 (2.9); 4.001 (9.0); 3.989 (8.9); 2.282 (0.3); 2.260 (0.3); 2.047 (0.3); 1.590 (65.8); 1.538 (0.3); 1.346 (0.9); 1.305 (1.5); 1.293 (2.2); 0.919 (0.7); 0.896 (0.5); 0.234 (0.7); 0.108 (26.4); 0.049 (5.0); 0.039 (156.4); 0.028 (6.1); 0.160 (0.7)

Example I.71

[0463] .sup.1H-NMR (300.2 MHz, d.sub.6-DMSO): =15.167 (0.3); 13.267 (0.3); 12.426 (0.3); 8.396 (0.5); 8.361 (15.7); 8.236 (0.4); 8.229 (0.6); 8.206 (5.2); 8.177 (5.3); 7.892 (0.3); 7.832 (15.6); 7.548 (1.8); 7.537 (12.2); 7.530 (4.2); 7.515 (4.8); 7.508 (14.8); 7.497 (1.3); 7.315 (0.5); 7.289 (2.2); 7.278 (15.6); 7.270 (5.8); 7.264 (7.6); 7.255 (4.8); 7.248 (12.3); 7.235 (7.0); 6.331 (0.3); 5.297 (14.6); 4.785 (4.0); 4.737 (6.0); 4.580 (5.7); 4.532 (3.9); 4.380 (0.5); 4.152 (1.4); 4.134 (3.9); 4.117 (4.3); 4.099 (1.3); 3.491 (0.4); 3.445 (0.5); 3.419 (0.6); 3.353 (79.3); 3.202 (16.7); 3.185 (16.0); 2.761 (0.4); 2.755 (0.4); 2.534 (37.5); 2.528 (50.5); 2.522 (36.5); 2.297 (0.5); 1.621 (0.7); 1.607 (1.4); 1.597 (1.5); 1.579 (2.6); 1.560 (1.7); 1.534 (0.8); 1.325 (0.4); 1.312 (0.4); 1.263 (1.1); 1.104 (0.6); 1.081 (1.4); 1.057 (0.5); 0.881 (0.4); 0.620 (0.6); 0.607 (1.3); 0.588 (2.1); 0.572 (2.5); 0.557 (2.0); 0.539 (0.8); 0.467 (0.6); 0.436 (1.6); 0.415 (1.8); 0.376 (1.0); 0.352 (1.0); 0.341 (1.4); 0.323 (2.2); 0.312 (2.1); 0.297 (2.5); 0.280 (2.6); 0.266 (2.7); 0.248 (2.2); 0.037 (2.0); 0.026 (51.2); 0.015 (2.4); 0.173 (0.4); 3.527 (0.4)

Example I.72

[0464] .sup.1H-NMR (499.9 MHz, CDCl.sub.3): =8.565 (0.3); 8.115 (0.4); 7.977 (0.4); 7.274 (0.5); 7.261 (1.1); 5.298 (16.0); 1.561 (0.7); 0.000 (0.8)

Example I.73

[0465] .sup.1H-NMR (300.2 MHz, d.sub.6-DMSO): =8.471 (16.0); 8.108 (5.9); 8.079 (6.5); 7.975 (15.7); 7.677 (1.4); 7.666 (13.7); 7.659 (4.1); 7.644 (4.6); 7.637 (14.5); 7.626 (1.5); 7.296 (5.6); 7.267 (5.2); 7.217 (1.7); 7.206 (15.6); 7.199 (4.4); 7.184 (4.4); 7.177 (12.9); 7.165 (1.2); 7.147 (3.0); 6.969 (6.4); 6.790 (3.2); 6.114 (7.2); 6.099 (7.4); 5.785 (1.5); 5.377 (2.2); 5.367 (2.3); 5.355 (2.3); 4.445 (1.4); 4.420 (1.2); 4.400 (4.1); 4.373 (4.3); 4.361 (4.2); 4.347 (4.1); 4.314 (1.4); 4.300 (1.1); 3.349 (65.1); 2.762 (0.4); 2.541 (19.3); 2.535 (40.9); 2.529 (55.5); 2.523 (39.2); 2.517 (17.8); 2.305 (0.3); 1.275 (0.6); 1.264 (0.7); 0.223 (0.4); 0.038 (2.1); 0.027 (63.3); 0.016 (2.0)

Example I.74

[0466] .sup.1H-NMR (300.2 MHz, d.sub.6-DMSO): =8.488 (16.0); 8.298 (5.9); 8.269 (6.4); 7.992 (15.3); 7.710 (8.2); 7.682 (9.6); 7.496 (6.7); 7.467 (6.3); 7.393 (10.8); 7.365 (9.0); 7.291 (3.4); 7.105 (7.4); 6.919 (3.6); 6.209 (7.0); 6.193 (7.3); 5.786 (1.0); 5.286 (2.3); 5.274 (2.5); 4.464 (1.9); 4.437 (1.8); 4.418 (3.9); 4.390 (3.8); 4.343 (3.8); 4.331 (3.9); 4.296 (1.9); 4.284 (1.7); 3.358 (44.1); 3.046 (0.5); 2.534 (9.3); 2.528 (12.2); 2.523 (9.0); 1.262 (0.7); 0.026 (5.7)

Example I.75

[0467] .sup.1H-NMR (499.9 MHz, CDCl.sub.3): =8.113 (1.8); 8.095 (1.9); 8.027 (3.6); 7.890 (3.9); 7.264 (1.9); 7.259 (0.5); 7.254 (3.2); 7.237 (4.0); 7.094 (0.6); 7.088 (4.2); 7.085 (1.7); 7.075 (1.3); 7.071 (3.5); 6.886 (2.2); 6.868 (2.1); 4.684 (1.7); 4.655 (2.3); 4.509 (2.5); 4.481 (1.8); 2.961 (0.3); 2.947 (0.9); 2.933 (1.2); 2.919 (0.9); 2.906 (0.4); 1.634 (9.6); 1.274 (15.8); 1.260 (16.0); 0.000 (1.7)

Example I.76

[0468] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.411 (9.1); 7.994 (11.0); 7.980 (0.5); 7.912 (11.4); 7.742 (6.3); 7.713 (7.2); 7.354 (10.9); 7.302 (12.7); 7.276 (6.1); 4.732 (4.0); 4.684 (13.3); 4.524 (6.3); 4.476 (4.1); 2.196 (0.4); 2.172 (1.4); 2.147 (1.9); 2.123 (2.3); 2.099 (2.0); 2.074 (0.6); 2.042 (2.4); 1.904 (0.5); 1.879 (1.9); 1.855 (2.4); 1.831 (2.0); 1.807 (1.5); 1.783 (0.6); 1.737 (0.9); 1.292 (0.3); 0.924 (7.5); 0.900 (16.0); 0.875 (6.9); 0.109 (0.5); 0.037 (4.4)

Example I.77

[0469] .sup.1H-NMR (499.9 MHz, d.sub.6-DMSO): =8.502 (1.5); 8.378 (1.0); 8.361 (1.0); 8.339 (6.0); 8.009 (1.4); 7.827 (3.4); 7.811 (3.7); 7.799 (5.4); 7.261 (0.6); 7.251 (0.7); 7.242 (0.9); 7.233 (0.9); 7.199 (0.8); 7.188 (1.9); 7.181 (6.8); 7.176 (7.1); 7.171 (5.5); 7.160 (5.0); 7.148 (1.3); 7.140 (2.2); 7.133 (1.6); 7.123 (2.6); 7.115 (2.4); 7.097 (4.9); 7.080 (3.4); 7.073 (0.5); 7.041 (3.6); 7.031 (3.8); 7.023 (2.3); 7.018 (1.2); 7.013 (2.0); 6.835 (1.0); 6.819 (1.0); 6.523 (3.6); 6.506 (3.6); 5.897 (2.7); 5.844 (4.9); 5.754 (3.5); 4.745 (2.2); 4.717 (2.8); 4.564 (2.9); 4.536 (2.2); 3.324 (9.8); 2.502 (4.9); 1.590 (16.0); 1.235 (1.0); 0.000 (1.0)

Example I.78

[0470] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.488 (5.3); 8.039 (2.3); 7.895 (2.8); 7.702 (2.5); 7.674 (2.8); 7.298 (3.4); 7.247 (2.7); 7.219 (2.4); 6.977 (5.9); 5.333 (11.1); 5.205 (1.9); 5.158 (2.2); 4.573 (2.3); 4.526 (2.0); 1.743 (16.0); 1.290 (0.4); 0.034 (3.5)

Example I.79

[0471] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.133 (5.0); 8.099 (1.7); 8.033 (3.9); 8.012 (0.5); 7.325 (1.0); 7.316 (0.7); 7.313 (0.7); 7.300 (15.8); 7.295 (5.1); 7.294 (5.0); 7.285 (2.5); 7.277 (7.1); 7.268 (1.2); 7.256 (0.9); 7.248 (1.3); 7.171 (2.0); 7.142 (1.9); 5.552 (0.8); 5.527 (0.8); 5.339 (16.0); 4.530 (0.8); 4.522 (0.9); 4.483 (1.3); 4.476 (1.3); 4.312 (1.2); 4.285 (1.2); 4.265 (0.8); 4.238 (0.8); 4.156 (0.7); 1.627 (0.9); 1.304 (0.4); 1.293 (0.4); 1.280 (0.4); 0.108 (1.9); 0.049 (0.7); 0.038 (15.8); 0.027 (0.6)

Example I.80

[0472] .sup.1H-NMR (300.2 MHz, d.sub.6-DMSO): =8.362 (11.2); 8.206 (3.8); 8.177 (4.0); 7.832 (11.0); 7.537 (8.6); 7.530 (3.0); 7.515 (3.7); 7.508 (10.5); 7.496 (1.1); 7.288 (1.5); 7.278 (10.9); 7.270 (4.5); 7.265 (5.6); 7.255 (3.7); 7.248 (8.7); 7.236 (5.4); 5.297 (10.6); 4.785 (3.0); 4.738 (4.4); 4.581 (4.4); 4.533 (2.9); 4.396 (0.4); 4.380 (0.8); 4.362 (0.4); 4.152 (1.3); 4.135 (4.1); 4.117 (4.2); 4.100 (1.6); 3.485 (0.7); 3.469 (0.6); 3.462 (0.5); 3.445 (0.6); 3.354 (53.8); 3.202 (16.6); 3.185 (16.0); 2.534 (23.6); 2.528 (30.7); 2.522 (22.1); 1.624 (0.5); 1.595 (1.1); 1.578 (1.9); 1.562 (1.3); 1.534 (0.5); 1.266 (0.5); 1.104 (1.1); 1.081 (2.0); 1.058 (1.0); 0.603 (1.0); 0.589 (1.7); 0.573 (1.8); 0.557 (1.4); 0.468 (0.4); 0.437 (1.2); 0.417 (1.6); 0.376 (0.8); 0.339 (1.1); 0.324 (1.5); 0.312 (1.7); 0.295 (1.9); 0.280 (1.9); 0.266 (2.0); 0.247 (1.5); 0.237 (1.0); 0.026 (30.3)

Example I.81

[0473] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.268 (5.9); 8.239 (6.2); 8.064 (14.1); 7.948 (16.0); 7.560 (1.3); 7.550 (13.2); 7.543 (4.3); 7.527 (4.4); 7.520 (15.2); 7.509 (1.6); 7.302 (2.9); 7.146 (1.7); 7.135 (15.3); 7.128 (4.6); 7.113 (4.2); 7.106 (13.1); 7.095 (1.3); 7.040 (7.2); 7.011 (6.8); 4.833 (5.6); 4.785 (8.3); 4.740 (7.2); 4.609 (8.1); 4.577 (0.4); 4.561 (5.4); 2.028 (0.7); 1.620 (3.7); 1.493 (0.6); 1.469 (1.6); 1.449 (2.6); 1.439 (1.3); 1.427 (1.9); 1.403 (0.8); 0.502 (0.6); 0.495 (0.7); 0.488 (1.0); 0.477 (1.6); 0.466 (1.7); 0.458 (2.8); 0.448 (1.6); 0.441 (1.5); 0.421 (0.6); 0.413 (0.4); 0.403 (0.7); 0.392 (0.8); 0.373 (4.2); 0.359 (10.7); 0.349 (6.0); 0.330 (7.5); 0.320 (2.6); 0.288 (0.4); 0.029 (1.5)

Example I.82

[0474] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.160 (2.5); 8.104 (3.6); 8.011 (3.7); 7.840 (0.9); 7.660 (1.1); 7.654 (1.0); 7.594 (0.3); 7.583 (3.3); 7.576 (1.0); 7.561 (1.1); 7.554 (3.6); 7.543 (0.4); 7.473 (1.0); 7.358 (2.4); 7.300 (13.6); 7.093 (0.4); 7.082 (3.7); 7.075 (1.1); 7.060 (1.0); 7.053 (3.2); 5.339 (4.3); 4.657 (1.2); 4.610 (1.7); 4.571 (2.1); 4.385 (2.1); 4.337 (1.6); 1.613 (16.0); 1.292 (0.4); 0.107 (1.3); 0.038 (9.4); 0.027 (0.4)

Example I.83

[0475] .sup.1H-NMR (499.9 MHz, CDCl.sub.3): =8.567 (0.8); 8.116 (0.9); 7.984 (0.9); 7.836 (0.7); 7.818 (0.8); 7.286 (0.9); 7.260 (2.4); 7.239 (0.6); 5.298 (16.0); 4.110 (0.5); 4.103 (0.6); 2.004 (0.3); 1.556 (2.1); 0.000 (1.8)

Example I.84

[0476] .sup.1H-NMR (499.9 MHz, CDCl.sub.3): =8.238 (6.8); 8.221 (7.0); 8.021 (14.6); 7.923 (15.1); 7.522 (1.4); 7.516 (13.0); 7.512 (5.0); 7.502 (4.8); 7.498 (14.1); 7.492 (1.8); 7.262 (10.7); 7.107 (1.6); 7.101 (14.2); 7.097 (5.2); 7.087 (4.7); 7.083 (13.0); 7.077 (1.6); 7.006 (7.6); 6.988 (7.4); 5.297 (8.4); 4.794 (6.6); 4.765 (8.5); 4.679 (13.5); 4.574 (8.4); 4.545 (6.6); 1.608 (16.0); 1.443 (0.8); 1.429 (2.0); 1.416 (3.2); 1.403 (2.2); 1.389 (0.9); 1.256 (0.5); 0.460 (1.3); 0.449 (2.5); 0.445 (2.6); 0.438 (3.4); 0.427 (2.1); 0.416 (0.3); 0.357 (0.5); 0.344 (2.3); 0.341 (3.5); 0.330 (7.2); 0.328 (7.2); 0.317 (8.1); 0.305 (4.4); 0.302 (4.0); 0.291 (1.9); 0.278 (0.7); 0.000 (9.6)

Example I.85

[0477] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.139 (10.5); 8.067 (3.3); 8.037 (3.5); 7.996 (13.1); 7.583 (1.5); 7.572 (14.3); 7.565 (4.4); 7.550 (4.8); 7.543 (16.0); 7.532 (1.7); 7.300 (15.1); 7.156 (2.0); 7.145 (18.0); 7.140 (11.0); 7.122 (4.9); 7.115 (15.7); 7.111 (8.9); 6.001 (1.1); 5.337 (3.6); 4.954 (1.9); 4.905 (6.2); 4.863 (7.8); 4.815 (2.6); 2.216 (0.4); 2.211 (0.8); 1.723 (0.6); 1.666 (0.8); 1.409 (0.5); 1.372 (0.7); 1.346 (0.7); 1.339 (0.7); 1.321 (1.4); 1.293 (7.8); 1.258 (0.8); 1.216 (0.4); 1.201 (0.4); 1.074 (0.5); 0.966 (0.3); 0.937 (0.8); 0.917 (1.5); 0.892 (1.6); 0.865 (1.6); 0.108 (3.6); 0.048 (0.4); 0.037 (13.4); 0.026 (0.6)

Example I.86

[0478] .sup.1H-NMR (499.9 MHz, CDCl.sub.3): =8.115 (0.4); 7.972 (0.4); 7.817 (0.3); 7.286 (0.3); 7.261 (0.8); 5.299 (16.0); 1.567 (0.5); 0.000 (0.6)

Example I.87

[0479] .sup.1H-NMR (300.2 MHz, d.sub.6-DMSO): =8.371 (10.5); 8.344 (0.6); 8.259 (3.5); 8.230 (3.8); 7.936 (0.4); 7.862 (6.1); 7.836 (16.0); 7.490 (0.7); 7.446 (6.4); 7.418 (5.5); 7.364 (4.7); 7.335 (4.4); 5.326 (10.2); 5.166 (0.6); 4.804 (2.8); 4.756 (4.0); 4.593 (4.0); 4.568 (0.4); 4.545 (2.7); 3.353 (24.0); 2.641 (0.4); 2.618 (0.4); 2.535 (4.9); 2.529 (6.5); 2.523 (4.8); 2.101 (0.3); 1.643 (0.4); 1.624 (1.0); 1.616 (1.2); 1.593 (3.1); 1.573 (5.3); 1.553 (0.7); 1.450 (2.0); 0.640 (0.3); 0.624 (0.9); 0.610 (1.5); 0.593 (1.7); 0.579 (1.3); 0.563 (0.6); 0.482 (0.4); 0.454 (1.1); 0.433 (1.4); 0.420 (1.3); 0.405 (0.9); 0.392 (0.7); 0.368 (0.7); 0.355 (1.1); 0.339 (1.5); 0.327 (1.6); 0.310 (1.7); 0.297 (2.0); 0.284 (2.0); 0.265 (1.6); 0.252 (1.0); 0.025 (4.3)

Example I.88

[0480] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.362 (11.7); 8.154 (10.1); 7.999 (12.2); 7.977 (0.4); 7.728 (7.6); 7.700 (8.7); 7.298 (34.0); 7.289 (8.6); 7.261 (7.2); 7.077 (16.0); 5.483 (2.1); 5.457 (2.2); 5.337 (8.0); 4.623 (3.2); 4.615 (3.1); 4.576 (4.2); 4.568 (4.2); 4.351 (4.0); 4.324 (3.8); 4.305 (2.9); 4.278 (2.9); 4.161 (2.1); 3.992 (0.4); 1.633 (4.5); 1.320 (0.4); 1.292 (1.2); 1.278 (0.5); 0.916 (0.4); 0.889 (0.3); 0.866 (0.4); 0.107 (0.6); 0.047 (1.1); 0.036 (34.2); 0.025 (1.4)

Example I.89

[0481] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.297 (2.9); 8.268 (3.1); 8.053 (7.1); 7.963 (5.5); 7.300 (21.3); 7.237 (3.7); 7.208 (3.5); 7.118 (0.7); 7.107 (1.3); 7.096 (6.9); 7.072 (6.7); 7.061 (1.2); 7.050 (0.6); 4.715 (2.1); 4.667 (3.9); 4.650 (1.7); 4.631 (0.9); 4.552 (4.9); 4.504 (2.8); 1.657 (16.0); 1.612 (2.8); 1.598 (3.3); 1.292 (0.5); 0.107 (5.8); 0.048 (0.5); 0.037 (14.7); 0.026 (0.5)

Example I.90

[0482] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.149 (6.4); 8.131 (15.9); 8.120 (6.6); 8.048 (16.0); 7.646 (0.4); 7.300 (87.7); 7.284 (4.7); 7.277 (5.6); 7.252 (8.6); 7.243 (11.8); 7.223 (22.1); 7.197 (1.5); 7.189 (1.4); 6.949 (0.5); 5.541 (2.3); 5.515 (2.5); 5.339 (1.8); 4.521 (3.1); 4.513 (3.1); 4.474 (4.7); 4.467 (4.5); 4.308 (4.7); 4.281 (4.4); 4.261 (3.1); 4.234 (3.1); 4.034 (5.3); 4.024 (5.2); 1.599 (21.4); 1.350 (0.5); 1.324 (0.7); 1.292 (1.6); 0.922 (0.4); 0.234 (0.4); 0.108 (22.6); 0.096 (0.8); 0.049 (3.4); 0.039 (97.6); 0.028 (3.5); 0.014 (0.4)

Example I.91

[0483] .sup.1H-NMR (300.2 MHz, d.sub.6-DMSO): =8.362 (14.8); 8.344 (1.3); 8.206 (4.9); 8.177 (5.2); 7.964 (0.4); 7.934 (0.4); 7.832 (16.0); 7.548 (1.3); 7.537 (11.7); 7.529 (4.0); 7.514 (4.4); 7.507 (14.2); 7.496 (1.4); 7.288 (1.9); 7.277 (14.8); 7.270 (5.4); 7.264 (7.4); 7.255 (4.5); 7.248 (11.7); 7.235 (6.9); 6.890 (0.4); 6.861 (0.4); 5.297 (14.1); 5.169 (1.0); 4.786 (3.8); 4.738 (5.8); 4.690 (0.5); 4.581 (5.6); 4.533 (3.8); 3.357 (45.4); 2.534 (7.8); 2.528 (10.3); 2.522 (7.4); 2.101 (4.0); 1.623 (0.7); 1.602 (2.5); 1.572 (9.0); 1.553 (1.5); 1.534 (0.8); 1.261 (0.6); 0.621 (0.5); 0.604 (1.3); 0.589 (2.1); 0.572 (2.3); 0.558 (1.7); 0.541 (0.8); 0.465 (0.5); 0.436 (1.5); 0.416 (1.9); 0.404 (1.8); 0.388 (1.3); 0.376 (1.0); 0.353 (1.0); 0.341 (1.4); 0.323 (2.0); 0.312 (2.3); 0.295 (2.4); 0.280 (2.6); 0.267 (2.8); 0.248 (2.1); 0.236 (1.2); 0.036 (0.5); 0.025 (8.6); 0.014 (0.3)

Example I.92

[0484] .sup.1H-NMR (499.9 MHz, CDCl.sub.3): =8.565 (0.8); 8.114 (1.0); 7.975 (1.0); 7.709 (0.7); 7.692 (0.8); 7.274 (1.3); 7.260 (2.9); 5.298 (16.0); 4.440 (0.3); 4.436 (0.3); 4.139 (0.5); 4.132 (0.6); 1.563 (1.7); 0.000 (2.0)

Example I.93

[0485] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.307 (6.4); 8.278 (6.7); 8.167 (0.5); 8.071 (14.1); 8.054 (1.1); 7.969 (16.0); 7.606 (7.5); 7.578 (9.2); 7.342 (10.5); 7.313 (8.5); 7.301 (16.3); 7.272 (0.6); 7.225 (0.8); 7.200 (0.4); 7.084 (7.7); 7.055 (7.4); 6.902 (3.9); 6.714 (7.9); 6.526 (4.0); 5.338 (1.9); 5.338 (1.9); 4.852 (6.2); 4.805 (9.2); 4.747 (14.0); 4.627 (9.0); 4.579 (6.0); 2.995 (6.6); 2.922 (5.7); 2.394 (2.3); 1.660 (13.4); 1.505 (0.7); 1.483 (1.8); 1.461 (2.8); 1.440 (2.0); 1.416 (0.8); 0.513 (1.0); 0.497 (2.0); 0.484 (2.1); 0.476 (2.6); 0.467 (1.7); 0.461 (1.9); 0.437 (0.7); 0.429 (0.4); 0.416 (0.9); 0.407 (0.9); 0.399 (2.6); 0.392 (3.3); 0.371 (8.5); 0.361 (3.5); 0.353 (6.5); 0.343 (6.4); 0.330 (1.9); 0.302 (0.4); 0.110 (1.3); 0.049 (0.5); 0.038 (13.4); 0.027 (0.5)

Example I.94

[0486] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.385 (6.4); 8.140 (8.7); 8.036 (9.1); 7.453 (1.0); 7.442 (8.1); 7.435 (3.0); 7.420 (3.1); 7.412 (10.0); 7.402 (1.3); 7.337 (0.4); 7.328 (0.4); 7.300 (55.7); 7.235 (2.3); 7.199 (6.5); 7.155 (1.3); 7.144 (9.8); 7.137 (3.2); 7.122 (2.9); 7.114 (8.0); 7.103 (1.0); 7.053 (4.1); 6.949 (0.3); 6.871 (2.3); 5.409 (1.4); 5.394 (1.3); 5.381 (1.6); 5.340 (11.4); 4.499 (0.7); 4.487 (1.0); 4.452 (4.0); 4.440 (4.2); 4.434 (4.4); 4.407 (3.3); 4.388 (0.8); 4.360 (1.0); 4.019 (4.2); 4.008 (4.2); 1.607 (16.0); 1.326 (0.4); 1.292 (1.3); 0.108 (4.5); 0.050 (2.7); 0.039 (60.0); 0.028 (2.3)

Example I.95

[0487] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.246 (3.1); 8.217 (3.2); 8.049 (4.1); 7.958 (5.0); 7.647 (0.4); 7.301 (80.0); 7.279 (7.6); 7.271 (3.8); 7.264 (11.9); 7.254 (1.6); 7.242 (1.1); 7.234 (1.8); 7.053 (3.7); 7.023 (3.5); 6.950 (0.5); 5.341 (0.5); 4.770 (2.4); 4.723 (5.7); 4.559 (3.6); 4.512 (2.4); 1.685 (16.0); 1.594 (22.2); 1.294 (1.1); 0.921 (0.4); 0.235 (0.3); 0.109 (9.9); 0.051 (2.6); 0.040 (81.7); 0.029 (2.9); 0.158 (0.4)

Example I.96

[0488] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.220 (2.8); 8.191 (2.9); 8.052 (6.8); 7.941 (6.1); 7.422 (0.6); 7.411 (6.2); 7.404 (2.0); 7.388 (2.2); 7.381 (7.7); 7.370 (0.8); 7.301 (10.0); 7.186 (0.9); 7.176 (8.2); 7.168 (2.3); 7.153 (2.0); 7.146 (6.0); 7.135 (0.6); 7.027 (3.4); 6.998 (3.3); 5.337 (0.7); 4.777 (3.4); 4.770 (1.7); 4.748 (2.2); 4.701 (3.5); 4.553 (4.3); 4.505 (2.7); 1.676 (16.0); 1.290 (1.5); 0.106 (0.7); 0.036 (9.8); 0.025 (0.4)

Example I.97

[0489] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.338 (6.4); 8.309 (6.8); 8.076 (14.5); 7.958 (16.0); 7.848 (1.4); 7.837 (12.2); 7.831 (4.0); 7.813 (4.8); 7.807 (13.6); 7.796 (1.5); 7.364 (8.7); 7.334 (7.7); 7.301 (3.1); 7.138 (7.6); 7.108 (7.2); 4.852 (5.8); 4.804 (9.6); 4.792 (8.1); 4.626 (8.4); 4.579 (5.7); 2.030 (2.1); 1.506 (0.7); 1.483 (1.9); 1.462 (2.9); 1.452 (1.4); 1.441 (2.1); 1.417 (0.8); 0.523 (0.7); 0.516 (0.9); 0.512 (0.9); 0.498 (1.9); 0.489 (2.2); 0.478 (2.8); 0.466 (1.6); 0.456 (1.1); 0.441 (0.6); 0.434 (0.4); 0.423 (0.8); 0.411 (0.9); 0.392 (4.0); 0.378 (9.6); 0.367 (5.8); 0.354 (7.2); 0.348 (6.8); 0.335 (3.0); 0.305 (0.4); 0.031 (1.8)

Example I.98

[0490] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =9.258 (0.4); 8.164 (3.3); 8.134 (3.3); 7.992 (6.9); 7.915 (8.0); 7.419 (0.7); 7.409 (6.7); 7.401 (2.2); 7.386 (2.5); 7.379 (8.4); 7.368 (0.9); 7.301 (5.7); 7.194 (1.1); 7.184 (8.8); 7.176 (2.4); 7.161 (2.3); 7.154 (6.4); 7.143 (0.6); 7.010 (3.8); 6.981 (3.6); 5.337 (16.0); 4.782 (2.9); 4.734 (4.1); 4.560 (4.1); 4.513 (2.8); 3.445 (1.2); 2.182 (0.5); 2.168 (0.7); 2.135 (0.9); 2.127 (1.0); 2.122 (1.0); 2.097 (0.8); 2.081 (0.8); 1.803 (0.7); 1.791 (0.8); 1.763 (1.0); 1.749 (1.1); 1.717 (0.7); 1.703 (0.7); 1.425 (0.5); 1.417 (0.4); 1.403 (0.6); 1.396 (0.7); 1.378 (0.9); 1.363 (0.8); 1.354 (0.8); 1.335 (2.0); 1.311 (3.1); 1.288 (2.7); 1.265 (1.4); 1.240 (0.5); 1.078 (0.5); 1.056 (0.6); 1.034 (1.1); 1.018 (0.7); 1.010 (1.1); 1.001 (0.5); 0.993 (0.6); 0.985 (0.5); 0.978 (0.4); 0.898 (5.8); 0.875 (11.4); 0.850 (4.4); 0.108 (0.5); 0.037 (5.4)

Example I.99

[0491] .sup.1H-NMR (499.9 MHz, CDCl.sub.3): =8.239 (5.8); 8.221 (6.0); 8.021 (12.6); 7.923 (13.1); 7.523 (1.2); 7.516 (11.5); 7.512 (4.0); 7.499 (12.2); 7.492 (1.4); 7.262 (10.7); 7.107 (1.3); 7.101 (12.5); 7.097 (4.1); 7.087 (4.2); 7.083 (11.2); 7.077 (1.3); 7.006 (6.5); 6.988 (6.4); 5.297 (9.6); 4.794 (5.7); 4.765 (7.3); 4.679 (11.7); 4.574 (7.2); 4.545 (5.6); 1.601 (16.0); 1.443 (0.7); 1.429 (1.7); 1.416 (2.7); 1.403 (1.8); 1.389 (0.7); 0.460 (1.1); 0.449 (2.1); 0.445 (2.2); 0.438 (2.9); 0.427 (1.8); 0.357 (0.4); 0.347 (1.8); 0.344 (2.0); 0.341 (2.9); 0.330 (6.1); 0.328 (6.1); 0.317 (7.0); 0.305 (3.7); 0.302 (3.3); 0.291 (1.5); 0.278 (0.6); 0.006 (0.4); 0.000 (9.7)

Example I.100

[0492] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.217 (0.6); 8.157 (5.0); 8.128 (5.0); 8.040 (1.7); 8.017 (10.9); 7.906 (12.1); 7.413 (1.0); 7.402 (9.8); 7.395 (3.3); 7.380 (3.6); 7.372 (12.8); 7.362 (1.4); 7.305 (4.2); 7.198 (0.3); 7.185 (1.4); 7.175 (12.9); 7.167 (3.9); 7.152 (3.2); 7.145 (9.8); 7.134 (0.9); 7.005 (5.8); 6.976 (5.5); 4.760 (4.1); 4.713 (6.5); 4.565 (6.6); 4.518 (4.2); 4.164 (0.6); 4.141 (0.6); 3.446 (0.4); 2.994 (11.4); 2.977 (0.5); 2.916 (10.2); 2.745 (0.4); 2.158 (0.7); 2.144 (0.9); 2.112 (1.4); 2.098 (1.5); 2.077 (2.5); 2.071 (1.5); 2.056 (1.3); 1.778 (0.9); 1.763 (1.2); 1.738 (1.3); 1.732 (1.2); 1.723 (1.6); 1.691 (1.0); 1.676 (1.1); 1.497 (0.3); 1.480 (0.5); 1.473 (0.5); 1.455 (1.1); 1.438 (1.0); 1.431 (1.1); 1.414 (1.3); 1.389 (0.9); 1.373 (0.5); 1.314 (0.7); 1.290 (1.5); 1.267 (0.7); 1.138 (0.4); 1.123 (0.6); 1.114 (0.6); 1.098 (1.1); 1.091 (0.8); 1.074 (1.0); 1.056 (1.0); 1.035 (0.7); 1.031 (0.7); 1.016 (0.5); 1.009 (0.4); 0.995 (0.4); 0.919 (8.2); 0.895 (16.0); 0.870 (6.1); 0.106 (1.1); 0.032 (3.3)

Example I.101

[0493] .sup.1H-NMR (499.9 MHz, CDCl.sub.3): =8.187 (3.1); 8.169 (3.2); 8.001 (6.6); 7.910 (6.8); 7.521 (0.6); 7.514 (6.3); 7.510 (2.1); 7.501 (2.2); 7.497 (6.7); 7.490 (0.8); 7.260 (16.3); 7.088 (0.7); 7.082 (6.8); 7.078 (2.2); 7.068 (2.1); 7.064 (6.2); 7.058 (0.7); 6.989 (3.5); 6.971 (3.4); 5.298 (1.1); 4.707 (2.9); 4.678 (3.8); 4.662 (5.5); 4.508 (4.0); 4.479 (3.0); 1.639 (16.0); 1.559 (8.7); 1.255 (1.5); 0.006 (0.6); 0.000 (16.6)

Example I.102

[0494] .sup.1H-NMR (499.9 MHz, CDCl.sub.3): =8.187 (3.1); 8.169 (3.2); 8.001 (6.6); 7.908 (6.8); 7.521 (0.6); 7.514 (6.2); 7.510 (2.2); 7.501 (2.2); 7.496 (6.7); 7.490 (0.9); 7.260 (13.2); 7.088 (0.7); 7.082 (6.7); 7.078 (2.3); 7.068 (2.2); 7.064 (6.2); 7.058 (0.8); 6.989 (3.5); 6.971 (3.4); 5.298 (1.1); 4.677 (3.9); 4.667 (7.0); 4.508 (4.0); 4.479 (3.0); 1.639 (16.0); 1.562 (10.2); 1.255 (0.4); 0.006 (0.5); 0.000 (13.3)

Example I.103

[0495] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.163 (4.6); 8.133 (4.8); 7.994 (10.3); 7.909 (11.2); 7.419 (0.9); 7.408 (9.5); 7.401 (3.1); 7.386 (3.6); 7.379 (11.9); 7.368 (1.3); 7.304 (5.2); 7.192 (1.4); 7.181 (12.3); 7.174 (3.4); 7.159 (3.2); 7.152 (9.1); 7.141 (0.9); 7.016 (5.5); 6.987 (5.2); 4.821 (2.3); 4.783 (4.3); 4.736 (6.2); 4.568 (6.3); 4.520 (4.1); 4.169 (0.7); 4.146 (0.7); 2.238 (0.4); 2.213 (1.4); 2.188 (2.0); 2.165 (2.3); 2.140 (1.9); 2.116 (0.6); 2.082 (3.1); 1.883 (0.6); 1.859 (1.8); 1.834 (2.4); 1.811 (2.3); 1.786 (2.1); 1.762 (1.1); 1.319 (0.9); 1.295 (1.7); 1.272 (0.8); 0.885 (7.7); 0.861 (16.0); 0.836 (7.1); 0.110 (0.9); 0.037 (2.8)

Example V.01

[0496] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =7.881 (2.8); 7.852 (3.0); 7.449 (0.6); 7.438 (5.9); 7.431 (1.9); 7.415 (2.3); 7.408 (7.3); 7.397 (0.8); 7.299 (5.2); 7.241 (0.5); 7.211 (0.6); 7.201 (0.9); 7.191 (7.6); 7.183 (2.2); 7.168 (2.5); 7.161 (8.8); 7.150 (0.7); 7.133 (3.0); 6.818 (0.5); 6.789 (0.4); 5.338 (0.5); 2.614 (16.0); 2.612 (14.4); 1.606 (0.5); 1.470 (0.9); 0.108 (0.4); 0.038 (6.2)

Example V.02

[0497] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.519 (3.7); 7.478 (0.4); 7.467 (4.5); 7.460 (1.5); 7.445 (1.6); 7.438 (5.4); 7.427 (0.7); 7.330 (4.0); 7.300 (5.5); 7.172 (0.6); 7.161 (5.6); 7.154 (1.7); 7.139 (1.5); 7.131 (4.4); 7.120 (0.5); 2.635 (16.0); 1.595 (6.3); 0.921 (0.3); 0.109 (1.7); 0.039 (6.2)

Example V.03

[0498] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.518 (3.8); 7.912 (0.4); 7.901 (4.0); 7.894 (1.3); 7.878 (1.3); 7.871 (4.5); 7.860 (0.5); 7.695 (0.6); 7.665 (0.6); 7.391 (4.1); 7.323 (2.5); 7.299 (5.3); 7.293 (2.3); 6.908 (0.4); 6.878 (0.3); 5.504 (0.3); 2.651 (16.0); 1.608 (7.9); 1.306 (1.4); 0.942 (0.5); 0.921 (1.6); 0.897 (0.6); 0.109 (1.6); 0.038 (4.8)

Example V.04

[0499] .sup.1H-NMR (300.2 MHz, d.sub.6-DMSO): =8.845 (3.1); 7.724 (1.9); 7.695 (2.3); 7.651 (3.3); 7.435 (2.6); 7.407 (2.1); 7.293 (0.9); 7.107 (1.9); 6.921 (0.9); 3.350 (2.0); 2.640 (16.0); 2.531 (0.5); 2.525 (0.7); 2.519 (0.5); 0.020 (0.8)

Example V.05

[0500] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.098 (1.9); 8.069 (2.0); 7.411 (0.4); 7.400 (4.0); 7.393 (1.6); 7.378 (1.6); 7.371 (5.2); 7.361 (0.8); 7.262 (12.2); 7.225 (1.5); 7.181 (0.6); 7.170 (5.1); 7.162 (1.6); 7.155 (0.6); 7.147 (1.5); 7.140 (3.9); 7.129 (0.5); 7.053 (2.1); 7.044 (3.3); 7.024 (1.9); 6.862 (1.5); 4.158 (0.4); 4.134 (1.1); 4.110 (1.1); 4.087 (0.4); 2.620 (16.0); 2.047 (5.0); 1.562 (9.9); 1.432 (1.4); 1.284 (1.4); 1.260 (2.8); 1.236 (1.4); 0.070 (9.2); 0.057 (0.5); 0.011 (0.5); 0.000 (15.9); 0.011 (0.9)

Example V.06

[0501] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.350 (2.4); 8.322 (2.5); 7.394 (3.2); 7.387 (1.3); 7.372 (1.4); 7.365 (4.3); 7.352 (0.7); 7.263 (7.4); 7.141 (0.8); 7.132 (4.0); 7.125 (1.3); 7.110 (1.4); 7.102 (3.4); 7.092 (0.4); 6.868 (2.5); 6.840 (2.3); 2.682 (0.4); 2.665 (0.6); 2.659 (0.5); 2.617 (16.0); 1.584 (27.0); 1.432 (1.1); 0.070 (4.5); 0.000 (8.6); 0.011 (0.4)

Example V.07

[0502] .sup.1H-NMR (300.2 MHz, d.sub.6-DMSO): =8.832 (3.2); 7.763 (3.4); 7.743 (1.3); 7.735 (1.3); 7.708 (1.2); 7.700 (1.2); 7.550 (0.9); 7.521 (2.1); 7.493 (1.6); 7.448 (1.2); 7.444 (1.2); 7.440 (1.2); 7.436 (1.0); 7.419 (0.6); 7.415 (0.7); 7.411 (0.6); 7.407 (0.6); 3.344 (1.7); 2.641 (16.0); 2.537 (0.5); 2.531 (1.0); 2.525 (1.4); 2.519 (1.0); 2.513 (0.5); 0.021 (2.2)

Example V.08

[0503] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): =8.634 (5.1); 7.482 (1.7); 7.477 (0.7); 7.463 (3.0); 7.446 (1.0); 7.442 (2.4); 7.437 (0.4); 7.307 (5.0); 7.302 (1.4); 7.283 (1.8); 7.264 (0.8); 7.215 (2.6); 7.212 (3.2); 7.193 (2.7); 3.331 (4.3); 2.642 (0.5); 2.595 (16.0); 2.508 (4.1); 2.504 (5.4); 2.499 (4.1); 0.000 (1.0)

Example V.09

[0504] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): =8.628 (5.2); 7.529 (0.4); 7.520 (4.0); 7.515 (1.4); 7.504 (1.5); 7.498 (4.8); 7.490 (0.6); 7.368 (5.1); 7.275 (0.6); 7.267 (4.8); 7.261 (1.6); 7.250 (1.3); 7.244 (4.0); 7.236 (0.4); 3.333 (3.7); 2.598 (16.0); 2.514 (1.8); 2.510 (3.5); 2.505 (4.6); 2.501 (3.5); 2.496 (1.7); 1.186 (0.4); 0.000 (1.2)

Example V.10

[0505] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): =8.299 (2.8); 8.278 (2.9); 7.549 (0.4); 7.540 (3.6); 7.535 (1.3); 7.524 (1.4); 7.518 (4.3); 7.510 (0.5); 7.297 (0.5); 7.289 (4.3); 7.284 (1.4); 7.272 (1.2); 7.267 (3.6); 7.258 (0.4); 7.178 (2.9); 7.157 (2.8); 3.329 (6.4); 2.599 (16.0); 2.508 (7.2); 2.504 (9.2); 2.499 (6.8); 0.000 (1.5)

Example V.11

[0506] .sup.1H-NMR (400.1 MHz, CDCl.sub.3): =8.081 (2.5); 8.060 (2.6); 7.498 (2.1); 7.476 (2.3); 7.312 (2.1); 7.305 (2.2); 7.260 (6.5); 7.067 (1.4); 7.061 (1.3); 7.046 (1.3); 7.039 (1.2); 6.924 (2.7); 6.903 (2.6); 2.695 (16.0); 1.544 (0.4); 1.432 (0.6); 0.070 (1.2); 0.000 (5.1)

Example V.12

[0507] .sup.1H-NMR (300.2 MHz, d.sub.6-DMSO): =8.382 (4.0); 8.369 (0.5); 8.354 (4.2); 8.342 (0.6); 7.808 (0.4); 7.781 (0.3); 7.563 (0.5); 7.552 (5.5); 7.545 (2.3); 7.530 (2.2); 7.523 (7.1); 7.512 (1.0); 7.313 (0.7); 7.302 (6.9); 7.294 (2.6); 7.279 (2.0); 7.272 (5.6); 7.235 (4.5); 7.206 (4.3); 7.184 (0.4); 7.155 (0.4); 5.107 (1.4); 5.081 (16.0); 3.326 (9.1); 2.598 (1.3); 2.508 (5.1); 2.502 (6.9); 2.496 (5.2); 1.247 (1.0); 0.858 (0.8); 0.000 (5.2)

Example V.13

[0508] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.195 (2.5); 8.165 (2.7); 7.438 (3.2); 7.431 (1.1); 7.415 (1.2); 7.409 (4.2); 7.398 (0.5); 7.315 (2.8); 7.284 (2.6); 7.262 (15.9); 7.216 (0.5); 7.205 (4.1); 7.198 (1.3); 7.183 (1.1); 7.176 (3.3); 7.165 (0.4); 7.081 (0.4); 4.240 (1.9); 2.826 (1.9); 2.801 (16.0); 1.549 (14.2); 0.069 (3.3); 0.010 (0.5); 0.000 (18.0); 0.011 (0.9)

Example V.14

[0509] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.127 (2.5); 8.099 (2.7); 7.637 (2.1); 7.608 (2.4); 7.313 (3.1); 7.300 (19.5); 7.284 (2.5); 6.961 (2.7); 6.933 (2.6); 6.911 (1.0); 6.723 (1.9); 6.535 (1.0); 2.740 (16.0); 1.585 (19.8); 1.307 (0.7); 0.921 (0.6); 0.108 (1.3); 0.049 (1.0); 0.039 (17.8); 0.028 (0.9)

Example V.15

[0510] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.524 (3.9); 7.349 (5.7); 7.324 (3.8); 7.313 (1.1); 7.299 (3.9); 7.256 (1.6); 7.245 (6.1); 7.237 (1.6); 7.222 (1.9); 7.215 (3.1); 2.650 (3.2); 2.638 (16.0); 1.636 (2.4); 1.623 (14.4); 1.304 (1.6); 0.940 (0.6); 0.932 (0.6); 0.918 (1.4); 0.895 (0.5); 0.108 (0.5); 0.048 (0.5); 0.036 (3.2)

Example V.16

[0511] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =7.931 (2.8); 7.902 (3.0); 7.885 (0.6); 7.874 (5.5); 7.867 (1.7); 7.851 (1.8); 7.844 (6.2); 7.833 (0.7); 7.368 (3.5); 7.337 (3.1); 7.300 (9.9); 7.253 (3.2); 7.225 (3.0); 2.630 (16.0); 2.628 (14.9); 1.589 (11.0); 0.109 (1.9); 0.049 (0.3); 0.038 (10.2); 0.027 (0.4)

Example V.17

[0512] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =7.918 (2.8); 7.890 (3.0); 7.792 (0.4); 7.745 (3.7); 7.717 (4.3); 7.645 (0.5); 7.618 (0.3); 7.376 (4.1); 7.348 (3.5); 7.300 (15.0); 7.232 (3.3); 7.204 (3.0); 2.627 (16.0); 2.625 (15.1); 1.588 (12.4); 0.109 (2.9); 0.049 (0.5); 0.038 (14.9); 0.027 (0.5)

Example V.18

[0513] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.654 (0.6); 8.527 (3.9); 7.752 (1.9); 7.724 (2.1); 7.491 (0.7); 7.315 (2.0); 7.300 (2.3); 7.287 (1.8); 7.104 (4.2); 2.716 (2.7); 2.692 (16.0); 1.614 (2.8); 0.109 (0.5); 0.037 (2.0)

Example V.19

[0514] .sup.1H-NMR (499.9 MHz, d.sub.6-DMSO): =8.898 (4.8); 8.651 (0.4); 7.631 (0.4); 7.624 (3.7); 7.607 (4.4); 7.600 (0.9); 7.582 (0.5); 7.387 (0.5); 7.380 (4.7); 7.363 (4.1); 7.357 (0.6); 7.152 (5.1); 6.827 (0.5); 3.318 (1.2); 2.696 (16.0); 2.641 (1.6); 2.606 (15.0); 2.507 (0.8); 1.230 (0.3); 0.877 (0.3)

Example V.20

[0515] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =7.882 (2.9); 7.853 (3.1); 7.599 (0.7); 7.588 (6.6); 7.581 (2.1); 7.566 (2.2); 7.558 (7.3); 7.548 (0.7); 7.300 (14.6); 7.165 (3.4); 7.151 (0.9); 7.141 (8.3); 7.118 (2.1); 7.111 (6.4); 7.100 (0.6); 2.615 (16.0); 2.613 (15.2); 1.589 (10.9); 1.345 (0.6); 1.306 (3.4); 0.942 (1.2); 0.921 (4.0); 0.897 (1.5); 0.108 (0.9); 0.049 (0.5); 0.038 (14.0); 0.027 (0.5)

Example V.21

[0516] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): =8.288 (2.9); 8.267 (3.0); 7.500 (1.6); 7.496 (0.8); 7.480 (3.0); 7.461 (2.4); 7.320 (1.1); 7.301 (1.8); 7.283 (0.8); 7.234 (2.6); 7.232 (3.2); 7.213 (2.6); 7.116 (3.1); 7.095 (2.9); 3.331 (5.0); 2.619 (0.8); 2.598 (16.0); 2.508 (5.0); 2.504 (6.5); 2.500 (4.9); 0.000 (1.1)

Example V.22

[0517] .sup.1H-NMR (399.8 MHz, CDCl.sub.3): =8.488 (4.8); 7.405 (3.7); 7.383 (4.1); 7.261 (3.4); 7.098 (4.3); 7.076 (3.6); 7.002 (4.5); 2.642 (16.0); 1.565 (1.2); 1.432 (0.4); 0.001 (3.6)

Example V.23

[0518] .sup.1H-NMR (499.9 MHz, CDCl.sub.3): =8.329 (4.9); 7.430 (0.4); 7.424 (3.6); 7.406 (4.1); 7.400 (0.5); 7.262 (2.5); 7.155 (0.5); 7.148 (4.1); 7.131 (3.6); 7.125 (0.4); 2.684 (16.0); 1.572 (7.9); 0.000 (2.7)

Example V.24

[0519] .sup.1H-NMR (499.9 MHz, CDCl.sub.3): =8.389 (2.5); 8.373 (3.4); 8.371 (3.2); 8.354 (2.6); 8.323 (0.4); 8.306 (0.4); 7.412 (0.9); 7.406 (7.3); 7.402 (2.7); 7.392 (2.9); 7.388 (8.4); 7.382 (1.2); 7.372 (0.4); 7.262 (4.5); 7.247 (0.6); 7.229 (0.6); 7.203 (0.5); 7.185 (0.6); 7.124 (1.1); 7.117 (8.4); 7.113 (3.0); 7.104 (2.7); 7.099 (7.5); 7.093 (1.2); 6.934 (0.6); 6.916 (0.5); 6.884 (0.6); 6.864 (3.2); 6.861 (3.1); 6.847 (3.1); 6.844 (3.1); 6.626 (0.4); 6.610 (0.4); 3.769 (0.4); 3.350 (0.3); 2.734 (0.7); 2.708 (2.3); 2.643 (0.7); 2.618 (15.7); 2.609 (16.0); 2.559 (0.9); 1.580 (11.1); 1.431 (0.7); 1.345 (0.4); 0.000 (4.3)

Example V.25

[0520] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.519 (3.7); 7.775 (2.6); 7.746 (3.0); 7.381 (4.0); 7.341 (2.8); 7.313 (2.6); 7.300 (8.1); 2.675 (0.8); 2.646 (16.0); 1.598 (15.8); 0.108 (1.3); 0.038 (7.2)

Example V.26

[0521] .sup.1H-NMR (299.9 MHz, CDCl.sub.3): =8.066 (2.6); 8.037 (2.6); 7.410 (0.5); 7.399 (3.4); 7.377 (1.6); 7.370 (4.0); 7.257 (6.1); 7.132 (0.6); 7.121 (4.2); 7.098 (1.4); 7.092 (3.2); 6.882 (2.8); 6.854 (2.6); 2.689 (16.0); 1.555 (7.5); 0.005 (5.4)

Example V.27

[0522] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.517 (3.6); 7.627 (0.5); 7.617 (4.6); 7.610 (1.5); 7.594 (1.6); 7.587 (5.0); 7.577 (0.6); 7.330 (4.0); 7.299 (5.4); 7.119 (0.6)); 77.108 (5.2) 1 (1.6); 7.085 (1.5); 7.078 (4.5); 7.068 (0.5); 2.635 (16.0); 1.590 (2.6); 0.109 (0.5); 0.039 (5.4)

Example V.28

[0523] .sup.1H-NMR (300.2 MHz, d.sub.6-DMSO): =8.316 (2.6); 8.288 (2.7); 7.500 (1.5); 7.472 (2.5); 7.404 (0.6); 7.392 (4.5); 7.385 (1.3); 7.370 (0.9); 7.362 (2.6); 7.274 (0.3); 7.206 (2.7); 7.178 (2.6); 3.324 (27.4); 2.667 (0.5); 2.642 (0.3); 2.618 (0.5); 2.601 (16.0); 2.513 (5.3); 2.507 (11.4); 2.501 (16.0); 2.495 (12.0); 2.490 (6.0); 0.000 (9.9)

Example V.29

[0524] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.068 (2.6); 8.040 (2.7); 7.263 (12.9); 7.148 (1.9); 7.118 (2.4); 7.020 (1.9); 7.010 (2.1); 6.882 (1.4); 6.875 (2.9); 6.872 (1.6); 6.852 (1.3); 6.847 (2.8); 6.843 (1.2); 5.302 (5.1); 3.833 (13.6); 2.796 (0.5); 2.709 (0.4); 2.691 (16.0); 2.681 (0.5); 2.048 (0.8); 1.565 (16.4); 1.432 (0.5); 1.261 (0.5); 0.070 (2.6); 0.011 (0.4); 0.000 (11.7); 0.011 (0.5)

Example V.30

[0525] 1H-NMR (300.2 MHz, CDCl3): =8.115 (2.5); 8.087 (2.6); 7.839 (2.5); 7.832 (0.8); 7.816 (0.8); 7.809 (2.8); 7.798 (0.4); 7.290 (1.5); 7.263 (3.6); 6.982 (2.7); 6.954 (2.5); 2.720 (1.2); 2.716 (0.4); 2.708 (16.0); 2.698 (0.5); 1.432 (0.5); 0.072 (0.5); 0.000 (2.9)

Example V.31

[0526] 1H-NMR (300.2 MHz, CDCl3): =7.931 (2.8); 7.902 (3.0); 7.355 (3.3); 7.327 (3.0); 7.300 (15.7); 7.142 (0.8); 7.131 (1.4); 7.125 (2.2); 7.121 (6.6); 7.097 (6.5); 7.093 (2.1); 7.086 (1.3); 7.076 (0.7); 2.620 (15.4); 2.618 (16.0); 1.585 (4.9); 0.109 (2.3); 0.050 (0.7); 0.039 (17.2); 0.028 (0.8)

Example V.32

[0527] 1H-NMR (300.2 MHz, CDCl.sub.3): =7.899 (2.8); 7.898 (2.8); 7.871 (3.0); 7.870 (3.0); 7.626 (3.3); 7.597 (4.1); 7.337 (4.6); 7.308 (3.7); 7.300 (3.0); 7.193 (3.2); 7.192 (3.2); 7.165 (3.0); 7.164 (3.0); 6.908 (1.7); 6.720 (3.5); 6.532 (1.8); 3.200 (0.8); 2.617 (15.6); 2.615 (16.0); 1.630 (0.3); 1.469 (0.9); 1.381 (0.4); 1.268 (0.5); 1.247 (0.5); 0.036 (2.4)

Example V.33

[0528] 1H-NMR (499.9 MHz, CDCl.sub.3): =8.094 (5.1); 7.263 (2.3); 7.251 (0.5); 7.245 (3.7); 7.241 (1.5); 7.231 (1.7); 7.227 (6.9); 7.222 (1.9); 7.212 (1.3); 7.208 (4.2); 7.202 (0.5); 6.940 (0.5); 6.934 (4.1); 6.930 (1.6); 6.920 (1.7); 6.916 (4.7); 6.914 (5.3); 6.910 (2.0); 6.900 (1.3); 6.896 (3.7); 6.890 (0.4); 2.729 (0.4); 2.716 (16.0); 1.594 (6.2); 0.000 (2.4)

Example V.34

[0529] 1H-NMR (300.2 MHz, CDCl.sub.3): =8.138 (1.9); 8.110 (2.0); 7.599 (0.5); 7.588 (4.5); 7.581 (1.5); 7.566 (1.8); 7.559 (5.0); 7.548 (0.7); 7.358 (0.3); 7.302 (11.2); 7.264 (1.6); 7.169 (0.7); 7.159 (5.1); 7.151 (1.6); 7.136 (1.7); 7.129 (4.4); 7.118 (0.6); 7.095 (2.2); 7.083 (3.4); 7.067 (2.0); 6.902 (1.6); 3.789 (0.4); 3.558 (0.4); 3.450 (0.4); 2.694 (0.5); 2.685 (0.6); 2.661 (16.0); 1.895 (0.5); 1.595 (1.1); 1.473 (0.4); 1.293 (0.6); 0.110 (1.0); 0.051 (0.6); 0.040 (11.7); 0.029 (0.6)

Example V.35

[0530] 1H-NMR (300.2 MHz, CDCl.sub.3): =7.895 (2.8); 7.893 (2.8); 7.866 (3.0); 7.865 (3.0); 7.328 (1.6); 7.321 (0.9); 7.318 (0.8); 7.299 (7.0); 7.297 (6.5); 7.284 (2.4); 7.276 (10.4); 7.267 (1.8); 7.255 (1.3); 7.245 (2.1); 7.238 (0.4); 7.180 (3.3); 7.179 (3.3); 7.152 (3.0); 7.151 (3.0); 2.615 (15.9); 2.612 (16.0); 1.627 (0.4); 1.468 (1.2); 0.111 (0.4); 0.036 (1.7)

Example V.36

[0531] 1H-NMR (300.2 MHz, CDCl.sub.3): =8.768 (2.5); 7.690 (1.0); 7.628 (0.4); 7.617 (3.5); 7.610 (1.1); 7.595 (1.2); 7.587 (3.8); 7.577 (0.4); 7.508 (2.0); 7.407 (2.6); 7.326 (1.0); 7.298 (4.7); 7.126 (0.4); 7.115 (4.0); 7.108 (1.1); 7.093 (1.1); 7.086 (3.4); 7.075 (0.3); 2.648 (16.0); 1.594 (3.9); 0.107 (0.3); 0.037 (4.5)

Example V.37

[0532] 1H-NMR (300.2 MHz, CDCl.sub.3): =8.769 (2.6); 7.692 (1.0); 7.510 (2.1); 7.479 (0.3); 7.469 (3.3); 7.462 (1.1); 7.446 (1.2); 7.439 (4.0); 7.428 (0.4); 7.407 (2.7); 7.328 (1.1); 7.298 (23.0); 7.179 (0.4); 7.168 (4.1); 7.161 (1.2); 7.146 (1.0); 7.139 (3.3); 2.648 (16.0); 1.581 (20.7); 0.107 (2.5); 0.048 (0.7); 0.037 (22.4); 0.027 (0.9)

Example V.38

[0533] 1H-NMR (300.2 MHz, CDCl.sub.3): =7.904 (2.8); 7.903 (2.8); 7.876 (3.1); 7.300 (2.5); 7.288 (1.7); 7.287 (1.7); 7.281 (2.1); 7.265 (1.1); 7.258 (3.8); 7.252 (2.6); 7.247 (2.2); 7.238 (3.6); 7.231 (3.7); 7.230 (3.7); 7.226 (3.7); 7.221 (7.3); 7.217 (4.6); 7.197 (0.6); 7.190 (0.5); 2.610 (16.0); 2.608 (15.9); 1.715 (0.7); 1.469 (1.2); 0.036 (2.4)

Example V.40

[0534] 1H-NMR (300.2 MHz, d6-DMSO): =9.719 (2.7); 8.342 (5.8); 8.314 (6.2); 7.712 (1.3); 7.701 (13.7); 7.694 (4.4); 7.678 (4.6); 7.671 (15.5); 7.660 (1.6); 7.492 (6.7); 7.463 (6.3); 7.350 (2.1); 7.342 (0.7); 7.327 (0.7); 7.320 (2.3); 7.309 (0.5); 7.302 (1.7); 7.291 (16.0); 7.284 (4.7); 7.269 (4.3); 7.261 (13.5); 7.250 (1.3); 6.762 (2.5); 6.754 (0.7); 6.739 (0.7); 6.732 (2.2); 3.356 (19.8); 2.541 (3.5); 2.535 (7.6); 2.529 (10.5); 2.523 (7.7); 2.516 (4.1); 2.499 (1.9); 2.489 (2.2); 2.485 (1.5); 2.474 (3.6); 2.467 (1.7); 2.458 (2.1); 2.449 (2.1); 2.433 (1.0); 1.361 (0.3); 1.240 (0.4); 1.233 (1.0); 1.216 (3.2); 1.205 (7.7); 1.198 (4.3); 1.190 (3.1); 1.179 (8.5); 1.172 (5.1); 1.169 (5.1); 1.161 (7.4); 1.146 (9.3); 1.135 (3.5); 1.117 (0.9); 0.035 (0.3); 0.025 (9.6); 0.014 (0.4)

Example V.41

[0535] 1H-NMR (300.2 MHz, CDCl.sub.3): =7.931 (5.8); 7.903 (6.2); 7.453 (1.2); 7.442 (12.6); 7.434 (4.2); 7.419 (4.6); 7.412 (16.0); 7.401 (1.7); 7.301 (28.1); 7.246 (1.1); 7.239 (0.4); 7.224 (0.5); 7.217 (1.5); 7.212 (1.9); 7.202 (16.3); 7.194 (4.7); 7.179 (4.2); 7.172 (12.8); 7.166 (7.5); 7.138 (6.2); 6.820 (1.3); 6.812 (0.4); 6.797 (0.3); 6.790 (1.1); 4.825 (1.3); 2.366 (0.8); 2.351 (1.8); 2.340 (2.0); 2.325 (3.7); 2.311 (2.1); 2.300 (2.0); 2.285 (1.0); 1.592 (13.5); 1.471 (0.5); 1.407 (1.7); 1.393 (5.8); 1.381 (9.6); 1.367 (7.2); 1.356 (2.4); 1.320 (0.5); 1.306 (0.6); 1.294 (0.5); 1.277 (0.5); 1.251 (0.4); 1.228 (2.5); 1.216 (7.5); 1.205 (5.4); 1.202 (5.7); 1.190 (8.3); 1.183 (3.7); 1.179 (4.6); 1.163 (3.2); 0.110 (3.1); 0.051 (1.0); 0.040 (30.8); 0.029 (1.1)

Example V.44

[0536] 1H-NMR (300.2 MHz, d6-DMSO): =8.362 (9.6); 8.333 (10.2); 7.726 (11.4); 7.698 (14.0); 7.525 (11.0); 7.497 (10.4); 7.444 (16.0); 7.415 (13.0); 7.298 (5.7); 7.111 (12.3); 6.925 (6.0); 5.785 (0.9); 3.360 (11.1); 3.146 (1.1); 2.541 (2.8); 2.535 (6.1); 2.529 (8.7); 2.523 (7.6); 2.517 (3.3); 2.507 (3.1); 2.498 (3.6); 2.493 (2.5); 2.482 (6.0); 2.475 (2.6); 2.466 (3.4); 2.457 (3.5); 2.441 (1.6); 1.246 (0.6); 1.238 (1.6); 1.220 (5.1); 1.210 (12.9); 1.202 (7.0); 1.194 (4.8); 1.184 (14.4); 1.176 (10.9); 1.168 (12.6); 1.158 (10.7); 1.152 (15.7); 1.141 (5.6); 1.124 (1.4); 1.109 (0.4); 0.023 (10.1); 0.012 (0.4)

Example V.45

[0537] 1H-NMR (300.2 MHz, CDCl.sub.3): =7.806 (3.4); 7.778 (3.7); 7.432 (0.9); 7.422 (7.3); 7.414 (2.4); 7.399 (2.7); 7.392 (9.2); 7.381 (1.0); 7.297 (1.4); 7.213 (0.6); 7.191 (1.3); 7.181 (9.6); 7.173 (2.8); 7.158 (2.5); 7.151 (7.3); 7.143 (4.5); 7.115 (3.7); 6.805 (0.7); 6.775 (0.6); 2.902 (1.7); 2.878 (5.3); 2.854 (5.5); 2.830 (1.9); 1.388 (0.5); 1.363 (0.8); 1.337 (0.4); 1.297 (0.4); 1.259 (8.1); 1.235 (16.0); 1.211 (7.6); 0.911 (0.4); 0.031 (1.3)

Example V.46

[0538] 1H-NMR (300.2 MHz, CDCl.sub.3): =7.814 (3.5); 7.785 (3.8); 7.433 (0.7); 7.423 (7.5); 7.415 (2.6); 7.400 (2.8); 7.393 (9.2); 7.382 (1.0); 7.302 (1.1); 7.210 (0.4); 7.194 (1.1); 7.184 (9.7); 7.176 (2.8); 7.161 (2.6); 7.154 (7.3); 7.144 (4.7); 7.116 (3.8); 6.806 (0.4); 6.776 (0.3); 2.855 (3.5); 2.831 (7.0); 2.807 (3.9); 1.827 (0.8); 1.802 (2.9); 1.778 (5.4); 1.753 (5.3); 1.729 (2.8); 1.705 (0.7); 1.689 (0.8); 1.044 (8.2); 1.019 (16.0); 0.994 (7.3); 0.034 (1.0)

Example V.47

[0539] 1H-NMR (300.2 MHz, CDCl.sub.3): =7.816 (1.8); 7.788 (2.0); 7.441 (0.4); 7.431 (3.7); 7.423 (1.2); 7.408 (1.4); 7.401 (4.6); 7.390 (0.5); 7.302 (1.0); 7.199 (0.6); 7.188 (4.7); 7.181 (1.4); 7.166 (1.3); 7.159 (3.6); 7.148 (2.4); 7.119 (1.9); 2.760 (3.6); 2.737 (3.9); 2.337 (0.4); 2.314 (0.9); 2.292 (1.1); 2.270 (0.9); 2.247 (0.5); 1.625 (1.5); 1.039 (16.0); 1.017 (15.5); 0.989 (0.5); 0.967 (0.4); 0.038 (0.9)

Example V.48

[0540] 1H-NMR (300.2 MHz, CDCl.sub.3): =7.812 (3.3); 7.784 (3.6); 7.678 (0.4); 7.652 (0.4); 7.449 (0.7); 7.438 (7.2); 7.431 (2.4); 7.416 (3.0); 7.408 (8.9); 7.398 (1.1); 7.391 (0.6); 7.301 (24.8); 7.248 (1.2); 7.240 (0.4); 7.225 (0.5); 7.218 (1.4); 7.203 (1.1); 7.192 (9.2); 7.184 (2.6); 7.169 (2.5); 7.162 (7.0); 7.152 (4.4); 7.124 (3.6); 6.821 (1.5); 6.814 (0.4); 6.799 (0.4); 6.791 (1.2); 4.802 (0.7); 2.948 (0.4); 2.922 (0.5); 2.895 (0.5); 2.878 (3.3); 2.854 (6.1); 2.829 (3.6); 1.771 (1.2); 1.747 (3.0); 1.722 (3.7); 1.697 (2.7); 1.672 (1.2); 1.592 (17.5); 1.488 (0.7); 1.464 (2.2); 1.439 (3.2); 1.413 (3.3); 1.389 (2.2); 1.365 (0.8); 1.307 (1.2); 1.013 (1.0); 1.001 (8.2); 0.989 (2.2); 0.976 (16.0); 0.965 (1.2); 0.952 (6.6); 0.922 (1.3); 0.899 (0.5); 0.110 (2.8); 0.051 (0.9); 0.040 (26.0); 0.029 (1.0)

Example VI.01

[0541] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =7.879 (3.4); 7.851 (3.7); 7.460 (0.8); 7.449 (7.5); 7.442 (2.6); 7.427 (2.9); 7.419 (9.5); 7.409 (1.2); 7.300 (21.9); 7.246 (0.6); 7.216 (1.1); 7.210 (5.0); 7.199 (9.8); 7.192 (3.2); 7.180 (4.3); 7.177 (3.8); 7.169 (7.6); 7.158 (0.8); 6.819 (0.7); 6.790 (0.6); 4.798 (0.8); 4.509 (16.0); 2.616 (0.5); 1.587 (40.4); 1.347 (0.5); 1.306 (2.2); 0.942 (0.8); 0.921 (2.5); 0.897 (0.9); 0.108 (1.6); 0.049 (0.8); 0.039 (26.1); 0.028 (1.1)

Example VI.03

[0542] .sup.1H-NMR (299.9 MHz, d.sub.6-DMSO): =8.367 (4.1); 8.338 (4.3); 7.511 (1.7); 7.505 (0.8); 7.486 (3.3); 7.465 (1.2); 7.459 (2.8); 7.451 (0.5); 7.336 (0.7); 7.332 (1.4); 7.328 (0.9); 7.307 (2.0); 7.302 (0.7); 7.286 (0.5); 7.283 (0.8); 7.279 (0.5); 7.244 (2.9); 7.240 (3.8); 7.233 (1.1); 7.218 (1.7); 7.215 (2.9); 7.212 (2.5); 7.171 (4.2); 7.142 (4.1); 5.077 (16.0); 3.318 (33.7); 2.513 (4.2); 2.507 (9.0); 2.501 (12.4); 2.495 (9.1); 2.489 (4.4); 0.000 (4.6)

Example VI.04

[0543] .sup.1H-NMR (399.8 MHz, CDCl.sub.3): =8.091 (3.3); 8.090 (3.9); 8.069 (4.0); 7.417 (0.7); 7.409 (5.3); 7.404 (1.9); 7.392 (2.8); 7.387 (5.6); 7.381 (0.9); 7.379 (0.9); 7.262 (6.3); 7.260 (7.5); 7.135 (0.9); 7.128 (6.2); 7.122 (2.2); 7.110 (2.6); 7.106 (4.9); 7.100 (0.8); 6.937 (4.0); 6.918 (3.4); 6.916 (3.9); 4.761 (13.8); 4.759 (16.0); 2.693 (0.7); 1.575 (1.1); 0.001 (6.9); 0.000 (7.6)

Example VI.05

[0544] .sup.1H-NMR (299.9 MHz, CDCl.sub.3): =8.504 (5.4); 7.484 (0.4); 7.476 (1.7); 7.470 (0.8); 7.451 (3.5); 7.430 (1.2); 7.424 (2.9); 7.416 (0.5); 7.313 (1.4); 7.309 (0.9); 7.288 (2.1); 7.259 (5.4); 7.162 (2.9); 7.158 (3.8); 7.152 (1.1); 7.133 (2.9); 7.003 (5.7); 4.662 (0.3); 4.650 (16.0); 1.546 (2.7); 0.000 (5.4)

Example VI.06

[0545] .sup.1H-NMR (299.9 MHz, CDCl.sub.3): =8.473 (6.4); 7.428 (0.6); 7.417 (4.5); 7.411 (1.7); 7.395 (1.8); 7.388 (5.9); 7.377 (0.6); 7.260 (12.9); 7.120 (0.7); 7.109 (5.6); 7.102 (1.9); 7.086 (1.6); 7.079 (4.9); 7.069 (0.5); 7.037 (6.7); 4.646 (16.0); 1.543 (12.4); 1.254 (0.4); 0.010 (0.7); 0.009 (0.7); 0.000 (12.0); 0.011 (0.4)

Example VI.07

[0546] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.111 (0.7); 8.092 (3.8); 8.083 (0.8); 8.064 (4.0); 7.512 (3.5); 7.483 (4.0); 7.323 (3.2); 7.315 (3.5); 7.265 (2.2); 7.084 (2.3); 7.075 (2.1); 7.054 (2.0); 7.045 (1.9); 6.983 (0.8); 6.976 (4.1); 6.955 (0.8); 6.948 (3.9); 4.760 (2.6); 4.569 (16.0); 4.559 (0.3); 4.542 (0.5); 2.045 (0.9); 1.259 (0.7); 0.074 (1.1); 0.000 (1.1)

Example VI.08

[0547] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.110 (3.7); 8.081 (3.9); 7.608 (0.5); 7.305 (1.9); 7.274 (4.5); 7.263 (78.5); 7.232 (1.2); 7.221 (6.8); 7.213 (1.8); 7.198 (1.4); 7.191 (3.1); 6.963 (4.0); 6.935 (3.9); 6.911 (0.4); 4.767 (16.0); 4.723 (0.6); 3.678 (0.3); 1.569 (243.3); 1.456 (0.4); 1.336 (0.4); 1.300 (0.5); 1.253 (1.6); 0.882 (0.6); 0.195 (0.4); 0.081 (0.9); 0.069 (26.9); 0.057 (1.4); 0.011 (2.6); 0.000 (76.2); 0.011 (3.7)

Example VI.09

[0548] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.409 (0.5); 8.381 (0.6); 8.094 (3.8); 8.065 (4.2); 8.039 (0.5); 7.263 (21.4); 7.139 (14.5); 7.133 (2.7); 7.120 (7.1); 7.117 (7.4); 7.087 (0.4); 6.975 (1.3); 6.954 (2.1); 6.921 (4.9); 6.897 (2.5); 6.893 (4.2); 6.864 (0.5); 6.836 (0.4); 6.665 (0.6); 6.638 (0.5); 4.852 (2.1); 4.767 (16.0); 2.694 (2.6); 1.571 (75.5); 1.306 (0.9); 1.266 (5.7); 0.904 (2.0); 0.882 (6.1); 0.859 (2.4); 0.070 (1.8); 0.011 (0.7); 0.000 (20.9); 0.011 (1.1)

Example VI.10

[0549] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.381 (7.3); 7.494 (0.5); 7.483 (4.7); 7.476 (1.5); 7.461 (1.7); 7.454 (5.8); 7.443 (0.6); 7.300 (15.7); 7.209 (0.7); 7.198 (5.8); 7.191 (1.8); 7.176 (1.5); 7.169 (4.6); 7.158 (0.4); 5.339 (0.6); 4.954 (16.0); 3.371 (0.4); 1.580 (7.4); 0.108 (5.5); 0.049 (0.6); 0.039 (16.3); 0.028 (0.6)

Example VI.11

[0550] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.035 (2.7); 8.007 (2.9); 7.420 (0.6); 7.409 (5.8); 7.402 (2.0); 7.387 (2.4); 7.379 (7.3); 7.369 (1.0); 7.262 (14.2); 7.173 (1.4); 7.162 (7.0); 7.155 (2.2); 7.140 (2.1); 7.132 (5.4); 7.121 (0.7); 7.093 (2.7); 7.065 (2.6); 7.049 (2.2); 6.903 (0.4); 6.868 (4.1); 6.687 (2.1); 4.569 (16.0); 4.322 (1.6); 3.500 (0.6); 1.558 (39.3); 1.260 (0.8); 0.882 (0.7); 0.070 (7.3); 0.058 (0.4); 0.011 (0.7); 0.000 (17.8); 0.011 (0.9)

Example VI.12

[0551] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.421 (3.7); 8.393 (3.8); 7.413 (0.5); 7.403 (4.8); 7.396 (1.9); 7.380 (2.0); 7.373 (6.4); 7.363 (0.9); 7.342 (0.5); 7.262 (9.5); 7.153 (0.5); 7.142 (0.9); 7.132 (6.0); 7.125 (2.2); 7.109 (1.9); 7.102 (4.9); 7.091 (0.6); 6.925 (3.5); 6.897 (3.3); 6.807 (0.4); 4.722 (0.3); 4.713 (0.3); 4.668 (16.0); 3.916 (0.5); 3.896 (0.9); 3.214 (2.9); 2.617 (0.8); 1.550 (6.0); 1.306 (0.5); 1.266 (3.1); 0.903 (1.1); 0.882 (3.4); 0.858 (1.3); 0.070 (2.1); 0.011 (0.4); 0.000 (10.9); 0.011 (0.5)

Example VI.13

[0552] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.100 (2.8); 8.072 (3.0); 7.262 (6.1); 7.149 (2.2); 7.120 (2.7); 7.023 (2.2); 7.013 (2.5); 6.936 (3.1); 6.908 (3.0); 6.886 (1.6); 6.876 (1.5); 6.856 (1.3); 6.847 (1.3); 4.775 (11.9); 3.835 (16.0); 2.690 (0.6); 1.563 (11.7); 1.266 (0.7); 1.260 (0.7); 0.882 (0.8); 0.000 (6.6)

Example VI.14

[0553] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.540 (4.2); 8.518 (0.5); 7.489 (0.5); 7.478 (5.3); 7.470 (1.9); 7.455 (2.0); 7.448 (6.5); 7.438 (1.2); 7.376 (4.6); 7.329 (0.5); 7.300 (25.9); 7.186 (0.7); 7.176 (6.5); 7.168 (2.0); 7.161 (0.9); 7.153 (2.0); 7.146 (5.1); 7.135 (0.7); 7.131 (0.6); 5.504 (0.4); 4.365 (16.0); 2.636 (1.6); 1.584 (37.7); 1.294 (0.4); 0.109 (2.6); 0.050 (1.0); 0.039 (28.1); 0.028 (1.2)

Example VI.15

[0554] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.759 (0.6); 8.540 (4.4); 8.517 (0.7); 7.638 (0.7); 7.633 (1.2); 7.627 (5.8); 7.620 (2.1); 7.617 (1.4); 7.610 (0.9); 7.604 (2.5); 7.597 (6.3); 7.587 (1.6); 7.398 (0.7); 7.377 (4.8); 7.330 (0.7); 7.300 (7.5); 7.133 (0.9); 7.130 (1.2); 7.123 (6.5); 7.115 (2.0); 7.108 (1.5); 7.100 (2.6); 7.093 (5.6); 7.082 (0.8); 7.079 (1.0); 6.454 (1.2); 4.366 (16.0); 2.636 (2.7); 1.587 (4.6); 1.306 (1.6); 0.943 (0.6); 0.921 (1.8); 0.898 (0.7); 0.110 (0.7); 0.039 (6.9)

Example VI.16

[0555] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.150 (3.8); 8.122 (4.0); 7.646 (2.9); 7.618 (3.3); 7.320 (3.7); 7.300 (17.0); 7.292 (3.4); 7.014 (4.0); 6.986 (3.8); 6.916 (1.4); 6.728 (2.9); 6.540 (1.5); 4.803 (16.0); 4.197 (0.4); 4.173 (1.3); 4.149 (1.3); 4.126 (0.5); 2.739 (1.2); 2.085 (5.9); 1.581 (7.3); 1.322 (1.6); 1.299 (3.2); 1.275 (1.5); 0.108 (1.3); 0.049 (0.5); 0.039 (16.8); 0.028 (0.6)

Example VI.17

[0556] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.131 (1.1); 8.103 (1.2); 7.646 (1.0); 7.618 (1.2); 7.324 (1.3); 7.300 (8.7); 7.007 (1.2); 6.979 (1.1); 6.917 (0.5); 6.728 (0.9); 6.540 (0.5); 4.615 (4.6); 4.588 (0.4); 2.740 (0.8); 2.085 (0.9); 1.580 (3.7); 1.370 (1.2); 1.346 (2.7); 1.306 (15.9); 0.943 (5.6); 0.922 (16.0); 0.898 (6.3); 0.109 (0.6); 0.050 (0.4); 0.039 (8.0); 0.029 (0.4)

Example VI.18

[0557] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =7.599 (0.5); 7.570 (0.6); 7.300 (5.0); 7.151 (0.6); 7.121 (0.5); 4.337 (1.2); 2.086 (0.5); 1.579 (2.4); 1.370 (0.9); 1.347 (2.1); 1.307 (13.6); 0.944 (5.0); 0.922 (16.0); 0.899 (5.9); 0.040 (5.0)

Example VI.19

[0558] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =7.972 (0.4); 7.944 (0.4); 7.881 (3.4); 7.852 (3.7); 7.609 (0.9); 7.599 (8.7); 7.591 (2.7); 7.576 (3.1); 7.569 (9.6); 7.558 (1.2); 7.358 (0.3); 7.300 (29.3); 7.212 (3.9); 7.183 (4.1); 7.158 (1.4); 7.153 (2.2); 7.147 (9.3); 7.140 (2.8); 7.125 (3.3); 7.118 (7.6); 7.107 (0.8); 6.777 (0.3); 4.511 (16.0); 4.301 (2.0); 3.948 (0.4); 3.303 (1.5); 2.617 (0.4); 1.588 (24.4); 1.367 (0.4); 1.344 (0.9); 1.305 (5.0); 0.942 (1.8); 0.920 (5.8); 0.897 (2.1); 0.108 (2.5); 0.049 (1.0); 0.038 (29.1); 0.027 (1.1)

Example VI.20

[0559] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.521 (3.8); 8.493 (4.8); 8.490 (4.6); 8.462 (3.9); 8.453 (0.7); 8.425 (0.7); 7.477 (1.1); 7.466 (10.0); 7.458 (3.3); 7.443 (3.7); 7.436 (12.2); 7.425 (1.6); 7.300 (40.9); 7.284 (0.5); 7.276 (1.0); 7.251 (0.8); 7.229 (0.3); 7.221 (1.0); 7.178 (1.5); 7.167 (12.2); 7.160 (3.8); 7.144 (3.3); 7.137 (9.6); 7.126 (1.0); 6.984 (4.3); 6.978 (4.9); 6.956 (4.4); 6.950 (4.9); 6.950 (4.9); 6.922 (1.0); 6.914 (0.4); 6.892 (0.8); 6.729 (0.7); 6.700 (0.6); 4.876 (3.1); 4.729 (16.0); 4.719 (16.0); 4.416 (0.4); 4.410 (0.4); 2.665 (0.5); 2.649 (0.6); 1.581 (19.3); 1.369 (0.5); 1.347 (0.9); 1.306 (5.0); 0.943 (1.8); 0.921 (5.7); 0.898 (2.1); 0.120 (0.5); 0.108 (12.2); 0.096 (0.5); 0.050 (1.7); 0.039 (44.7); 0.028 (1.7)

Example VI.21

[0560] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.573 (0.5); 8.490 (4.7); 7.397 (5.0); 7.363 (2.3); 7.334 (4.1); 7.300 (5.5); 7.269 (1.0); 7.258 (7.4); 7.250 (1.9); 7.235 (1.5); 7.228 (3.9); 7.217 (0.4); 7.159 (0.6); 6.870 (0.5); 6.839 (0.4); 4.586 (1.8); 4.554 (16.0); 4.091 (2.8); 3.898 (0.7); 3.309 (2.1); 2.640 (0.6); 1.605 (3.4); 1.305 (0.9); 0.920 (1.0); 0.897 (0.4); 0.110 (0.9); 0.038 (5.4)

Example VI.22

[0561] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.484 (3.0); 7.785 (2.2); 7.756 (2.6); 7.427 (3.3); 7.354 (2.4); 7.326 (2.2); 7.300 (8.2); 5.339 (0.4); 4.586 (0.9); 4.556 (10.7); 4.090 (1.5); 3.314 (0.7); 2.646 (1.0); 1.600 (16.0); 1.346 (0.4); 1.305 (2.1); 0.942 (0.8); 0.920 (2.4); 0.897 (0.9); 0.108 (1.6); 0.038 (7.6)

Example VI.23

[0562] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.573 (0.4); 8.482 (3.4); 7.637 (0.4); 7.626 (4.2); 7.619 (1.4); 7.604 (1.4); 7.597 (4.6); 7.587 (0.6); 7.378 (3.8); 7.356 (0.5); 7.300 (8.1); 7.159 (0.4); 7.128 (0.5); 7.117 (4.7); 7.110 (1.4); 7.095 (1.3); 7.088 (4.0); 7.078 (0.5); 6.775 (0.5); 6.745 (0.5); 4.921 (0.4); 4.586 (1.4); 4.552 (12.1); 4.090 (2.1); 2.636 (0.6); 1.602 (16.0); 1.304 (0.9); 0.942 (0.3); 0.920 (1.0); 0.897 (0.4); 0.108 (1.5); 0.038 (7.5)

Example VI.24

[0563] .sup.1H-NMR (300.2 MHz, d.sub.6-DMSO): =8.911 (0.8); 8.894 (5.3); 8.866 (0.4); 8.833 (1.0); 7.913 (0.4); 7.898 (0.7); 7.834 (5.6); 7.813 (1.2); 7.758 (1.3); 7.746 (2.3); 7.738 (2.5); 7.729 (0.7); 7.719 (0.7); 7.712 (2.3); 7.704 (2.4); 7.695 (0.5); 7.564 (1.6); 7.555 (0.6); 7.548 (0.5); 7.535 (3.5); 7.526 (0.6); 7.519 (0.9); 7.507 (2.7); 7.491 (0.6); 7.454 (2.2); 7.450 (2.3); 7.446 (2.4); 7.442 (2.0); 7.434 (0.6); 7.425 (1.2); 7.421 (1.4); 7.417 (1.3); 7.413 (1.2); 5.815 (0.7); 5.777 (3.6); 4.986 (16.0); 2.641 (5.2); 2.537 (0.6); 2.531 (1.1); 2.525 (1.5); 2.519 (1.1); 2.513 (0.5); 1.265 (0.5); 0.876 (0.5); 0.019 (1.9)

Example VI.25

[0564] .sup.1H-NMR (300.2 MHz, d.sub.6-DMSO): =8.858 (5.1); 8.833 (2.8); 7.843 (5.4); 7.760 (3.0); 7.747 (2.1); 7.740 (3.1); 7.732 (1.3); 7.713 (2.0); 7.705 (3.0); 7.697 (1.2); 7.558 (1.5); 7.549 (0.9); 7.529 (3.4); 7.520 (2.0); 7.511 (0.4); 7.501 (2.6); 7.492 (1.5); 7.454 (2.0); 7.449 (2.2); 7.446 (2.7); 7.442 (2.5); 7.435 (1.0); 7.425 (1.1); 7.420 (1.3); 7.417 (1.5); 7.413 (1.5); 7.406 (0.6); 5.778 (3.2); 5.188 (0.5); 5.171 (16.0); 4.031 (0.4); 4.025 (0.4); 3.348 (3.6); 3.203 (1.5); 2.641 (13.6); 2.537 (0.8); 2.531 (1.6); 2.525 (2.2); 2.519 (1.6); 2.513 (0.8); 2.011 (0.4); 1.266 (1.1); 0.900 (0.3); 0.878 (1.1); 0.855 (0.4); 0.020 (2.5)

Example VI.26

[0565] .sup.1H-NMR (300.2 MHz, d.sub.6-DMSO): =9.951 (0.5); 8.972 (0.6); 8.870 (4.9); 7.732 (8.2); 7.704 (3.7); 7.445 (4.1); 7.416 (3.5); 7.388 (0.9); 7.298 (1.4); 7.111 (3.1); 6.926 (1.5); 5.190 (2.3); 5.166 (16.0); 4.031 (3.2); 3.351 (2.7); 3.213 (0.3); 2.641 (1.0); 2.537 (0.5); 2.531 (1.0); 2.525 (1.4); 2.519 (1.0); 2.513 (0.5); 0.021 (1.7)

Example VI.27

[0566] .sup.1H-NMR (300.2 MHz, d.sub.6-DMSO): =8.906 (5.4); 8.845 (1.1); 7.829 (0.8); 7.781 (0.5); 7.733 (3.8); 7.721 (7.0); 7.705 (4.4); 7.650 (1.2); 7.470 (0.5); 7.451 (4.6); 7.423 (3.8); 7.408 (0.9); 7.298 (1.6); 7.112 (3.5); 6.926 (1.7); 5.777 (0.8); 4.976 (16.0); 3.375 (0.8); 2.641 (5.2); 2.537 (0.4); 2.531 (0.9); 2.525 (1.2); 2.519 (0.9); 2.513 (0.4); 0.021 (1.4)

Example VI.28

[0567] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =7.917 (3.4); 7.889 (3.8); 7.810 (0.4); 7.757 (4.7); 7.728 (5.6); 7.688 (0.4); 7.661 (0.4); 7.386 (5.0); 7.358 (4.4); 7.300 (36.4); 7.276 (4.0); 7.248 (3.9); 7.233 (0.4); 7.219 (0.4); 4.516 (16.0); 4.506 (1.7); 4.308 (1.3); 3.312 (0.4); 2.628 (1.0); 1.585 (41.2); 1.345 (0.4); 1.307 (1.9); 0.943 (0.6); 0.921 (2.0); 0.898 (0.8); 0.108 (8.4); 0.096 (0.3); 0.049 (1.2); 0.039 (37.1); 0.028 (1.3)

Example VI.29

[0568] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =7.931 (3.5); 7.902 (4.0); 7.886 (7.3); 7.879 (2.3); 7.863 (2.4); 7.856 (8.1); 7.845 (1.3); 7.837 (0.9); 7.810 (1.0); 7.688 (1.1); 7.661 (0.9); 7.646 (0.3); 7.378 (4.5); 7.348 (4.0); 7.300 (41.0); 7.269 (3.9); 7.239 (0.4); 4.517 (16.0); 4.506 (4.3); 4.309 (1.2); 4.301 (0.4); 3.314 (0.5); 2.631 (1.4); 1.585 (43.2); 1.346 (1.3); 1.306 (7.3); 0.943 (2.6); 0.921 (8.6); 0.898 (3.1); 0.108 (8.3); 0.050 (1.3); 0.039 (39.4); 0.028 (1.4)

Example VI.30

[0569] 1H-NMR (300.2 MHz, CDCl3): =8.148 (0.4); 8.135 (3.7); 8.120 (0.4); 8.106 (4.0); 7.862 (0.4); 7.851 (3.8); 7.844 (1.2); 7.827 (1.5); 7.820 (4.1); 7.810 (0.6); 7.300 (2.3); 7.269 (2.2); 7.263 (5.6); 7.051 (0.5); 7.031 (3.9); 7.022 (0.4); 7.003 (3.7); 6.865 (0.7); 4.803 (0.9); 4.787 (0.4); 4.765 (16.0); 4.724 (0.7); 2.708 (0.6); 1.572 (8.0); 1.266 (0.9); 1.260 (0.9); 0.903 (0.3); 0.882 (1.1); 0.858 (0.4); 0.000 (4.8)

Example VI.31

[0570] 1H-NMR (300.2 MHz, CDCl3): =7.939 (3.3); 7.911 (3.6); 7.816 (0.3); 7.702 (0.8); 7.697 (0.9); 7.690 (0.8); 7.677 (1.1); 7.671 (1.1); 7.573 (0.4); 7.548 (1.6); 7.524 (1.1); 7.400 (3.9); 7.372 (3.7); 7.355 (0.5); 7.343 (0.3); 7.327 (0.5); 7.312 (0.5); 7.300 (44.0); 7.149 (0.8); 7.139 (1 (2.6); 7.129 (8.1); 7.120 (1.3); 7.105 (7.9); 7.100 (2.7); 7.095 (2.1); 7.084 (0.9); 5.340 (2.0); 5.028 (3.2); 4.517 (16.0); 4.302 (1.2); 3.772 (3.2); 3.433 (15.9); 3.300 (0.8); 2.619 (1.8); 2.617 (1.9); 1.594 (22.3); 1.293 (0.6); 0.108 (5.0); 0.049 (1.6); 0.038 (48.2); 0.027 (1.9)

Example VI.32

[0571] 1H-NMR (300.2 MHz, CDCl3): =7.982 (3.1); 7.954 (3.4); 7.406 (0.4); 7.394 (3.7); 7.379 (0.4); 7.365 (3.4); 7.300 (30.6); 7.149 (0.7); 7.139 (1.5); 7.133 (2.7); 7.129 (7.1); 7.121 (0.9); 7.105 (7.0); 7.100 (2.3); 7.096 (1.6); 7.085 (0.7); 6.379 (0.7); 6.368 (0.3); 4.341 (16.0); 2.619 (1.3); 1.583 (29.3); 1.296 (0.4); 0.108 (6.3); 0.049 (1.1); 0.039 (32.1); 0.027 (1.2)

Example VI.33

[0572] 1H-NMR (300.2 MHz, CDCl3): =7.893 (3.3); 7.865 (3.6); 7.342 (1.9); 7.311 (7.1); 7.300 (23.1); 7.288 (12.0); 7.279 (2.3); 7.266 (1.5); 7.257 (2.8); 7.230 (3.9); 7.202 (3.6); 4.513 (16.0); 4.305 (0.5); 3.306 (0.7); 2.619 (0.3); 1.580 (9.3); 1.479 (0.7); 1.306 (0.8); 0.921 (0.7); 0.109 (1.1); 0.050 (0.7); 0.039 (24.0); 0.028 (0.9)

Example VI.34

[0573] 1H-NMR (300.2 MHz, CDCl3): =7.925 (3.2); 7.924 (3.1); 7.897 (3.4); 7.895 (3.4); 7.460 (0.8); 7.450 (7.2); 7.442 (2.5); 7.427 (2.8); 7.420 (9.1); 7.409 (1.1); 7.300 (24.4); 7.213 (1.4); 7.202 (12.8); 7.194 (3.0); 7.179 (3.3); 7.172 (9.2); 7.161 (0.8); 4.338 (16.0); 1.582 (18.1); 0.050 (1.2); 0.039 (26.1); 0.028 (1.0)

Example VI.35

[0574] 1H-NMR (300.2 MHz, CDCl.sub.3): =7.906 (3.3); 7.905 (3.4); 7.878 (3.6); 7.877 (3.7); 7.309 (4.4); 7.300 (16.0); 7.294 (3.2); 7.293 (3.2); 7.282 (4.1); 7.281 (4.1); 7.269 (1.6); 7.264 (3.3); 7.259 (2.8); 7.247 (4.1); 7.245 (3.9); 7.238 (4.0); 7.232 (8.9); 7.227 (5.7); 7.210 (0.7); 7.203 (0.7); 7.187 (0.4); 4.512 (16.0); 4.299 (1.0); 3.300 (0.6); 2.615 (0.4); 1.720 (1.1); 1.583 (3.9); 1.479 (0.8); 1.322 (0.3); 1.294 (0.5); 0.109 (3.4); 0.050 (0.7); 0.039 (15.4); 0.028 (0.4)

Example VI.36

[0575] 1H-NMR (300.2 MHz, CDCl.sub.3): =7.903 (3.4); 7.902 (3.4); 7.875 (3.7); 7.873 (3.6); 7.638 (4.0); 7.609 (4.9); 7.348 (5.5); 7.319 (4.4); 7.302 (2.5); 7.240 (3.9); 7.239 (3.9); 7.212 (3.6); 6.915 (2.1); 6.727 (4.2); 6.539 (2.1); 4.520 (16.0); 3.271 (0.5); 3.220 (0.3); 2.621 (0.5); 2.619 (0.5); 0.039 (2.5)

Example VII.01

[0576] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.222 (4.3); 8.019 (4.5); 7.927 (2.0); 7.898 (2.1); 7.462 (0.4); 7.452 (4.1); 7.444 (1.5); 7.429 (1.5); 7.422 (5.4); 7.411 (0.6); 7.300 (12.6); 7.206 (2.3); 7.196 (0.7); 7.185 (5.3); 7.178 (3.7); 7.163 (1.5); 7.155 (4.3); 7.145 (0.5); 5.424 (8.1); 1.608 (16.0); 0.108 (1.3); 0.049 (0.5); 0.038 (14.8); 0.028 (0.6)

Example VII.02

[0577] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.578 (5.9); 8.245 (6.7); 8.032 (6.7); 7.496 (0.8); 7.485 (6.2); 7.478 (2.3); 7.463 (2.4); 7.455 (7.7); 7.445 (1.0); 7.397 (6.3); 7.300 (39.6); 7.178 (0.9); 7.168 (7.5); 7.160 (2.6); 7.145 (2.1); 7.138 (6.2); 7.127 (0.7); 5.499 (16.0); 5.340 (7.4); 1.587 (19.7); 0.109 (1.6); 0.050 (2.3); 0.039 (51.8); 0.029 (2.6)

Example VII.03

[0578] .sup.1H-NMR (400.1 MHz, CDCl.sub.3): =8.235 (2.1); 8.195 (5.7); 8.174 (5.8); 8.004 (3.3); 7.927 (0.5); 7.906 (0.6); 7.523 (5.1); 7.518 (0.6); 7.501 (5.6); 7.374 (0.6); 7.354 (0.6); 7.328 (5.1); 7.321 (5.4); 7.309 (0.4); 7.297 (0.8); 7.259 (70.7); 7.209 (0.4); 7.078 (3.3); 7.072 (3.1); 7.057 (3.0); 7.050 (2.9); 6.999 (6.0); 6.978 (5.9); 5.704 (16.0); 5.686 (0.5); 5.298 (0.3); 4.555 (0.4); 2.804 (1.2); 2.704 (3.5); 2.003 (2.4); 1.640 (0.3); 1.561 (0.7); 1.505 (0.4); 1.333 (0.4); 1.314 (0.5); 1.284 (0.8); 1.256 (1.7); 0.881 (0.6); 0.069 (1.9); 0.008 (1.6); 0.000 (46.8); 0.008 (1.6)

Example VII.04

[0579] .sup.1H-NMR (499.9 MHz, d.sub.6-DMSO): =8.534 (8.6); 8.494 (5.1); 8.477 (5.3); 8.033 (8.1); 7.758 (4.7); 7.752 (4.9); 7.712 (2.1); 7.710 (2.2); 7.694 (2.4); 7.692 (2.5); 7.425 (2.9); 7.419 (2.9); 7.407 (2.6); 7.401 (2.6); 7.327 (5.4); 7.311 (5.3); 5.883 (16.0); 3.319 (14.6); 2.892 (0.5); 2.742 (0.8); 2.733 (0.5); 2.511 (1.1); 2.507 (2.4); 2.504 (3.3); 2.500 (2.5); 2.497 (1.3); 1.989 (0.5); 0.000 (1.3)

Example VII.05

[0580] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.615 (8.1); 8.232 (6.5); 8.005 (6.6); 7.497 (0.4); 7.489 (2.0); 7.483 (1.0); 7.464 (4.1); 7.463 (3.8); 7.443 (1.5); 7.437 (3.6); 7.429 (0.8); 7.333 (1.0); 7.329 (2.0); 7.326 (1.3); 7.310 (0.9); 7.305 (2.6); 7.299 (0.9); 7.284 (0.8); 7.280 (1.3); 7.276 (0.9); 7.273 (0.5); 7.271 (0.6); 7.270 (0.7); 7.262 (34.2); 7.252 (0.7); 7.247 (0.5); 7.244 (0.4); 7.171 (1.0); 7.167 (3.8); 7.162 (5.1); 7.155 (1.4); 7.141 (2.2); 7.138 (3.8); 7.134 (3.5); 7.125 (0.6); 7.039 (8.7); 5.629 (16.0); 5.302 (5.5); 1.583 (4.9); 1.253 (0.5); 0.011 (0.8); 0.008 (0.4); 0.000 (25.6); 0.009 (0.7); 0.011 (1.1)

Example VII.06

[0581] .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO): =8.530 (8.6); 8.461 (5.5); 8.440 (5.8); 8.032 (8.3); 7.526 (0.5); 7.520 (2.8); 7.515 (1.3); 7.501 (5.0); 7.499 (5.0); 7.485 (1.7); 7.480 (4.2); 7.475 (0.6); 7.344 (1.1); 7.341 (2.0); 7.339 (1.4); 7.323 (3.2); 7.307 (0.8); 7.304 (1.4); 7.302 (0.9); 7.259 (4.6); 7.256 (5.8); 7.251 (1.7); 7.239 (2.8); 7.237 (4.7); 7.235 (4.1); 7.228 (0.6); 7.200 (5.9); 7.179 (5.9); 5.878 (16.0); 3.314 (5.3); 2.897 (0.5); 2.738 (0.4); 2.517 (6.1); 2.512 (12.3); 2.508 (16.5); 2.503 (11.7); 2.499 (5.6)

Example VII.07

[0582] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.352 (5.4); 8.344 (5.5); 8.219 (6.7); 8.016 (6.8); 7.608 (0.5); 7.518 (2.0); 7.511 (1.0); 7.493 (4.2); 7.471 (1.5); 7.465 (3.5); 7.457 (0.7); 7.357 (1.0); 7.353 (2.0); 7.350 (1.2); 7.334 (1.0); 7.329 (2.6); 7.323 (0.8); 7.308 (0.7); 7.304 (1.2); 7.300 (0.7); 7.285 (5.7); 7.277 (5.8); 7.271 (1.1); 7.262 (77.9); 7.147 (3.9); 7.143 (5.1); 7.136 (1.4); 7.122 (2.3); 7.118 (3.9); 7.115 (3.5); 7.106 (0.6); 6.911 (0.4); 5.845 (16.0); 1.562 (52.8); 1.253 (0.5); 0.011 (1.9); 0.000 (56.2); 0.011 (2.2)

Example VII.08

[0583] .sup.1H-NMR (499.9 MHz, d.sub.6-DMSO): =8.527 (8.3); 8.478 (4.7); 8.461 (4.8); 8.029 (7.7); 7.506 (4.1); 7.488 (5.8); 7.414 (1.0); 7.407 (8.4); 7.402 (2.8); 7.393 (2.2); 7.389 (6.0); 7.382 (0.7); 7.277 (4.9); 7.260 (4.8); 5.877 (16.0); 3.315 (10.4); 2.505 (3.5); 2.502 (4.8); 2.499 (3.8); 0.000 (1.7)

Example VII.09

[0584] .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO): =8.530 (8.8); 8.472 (5.7); 8.451 (5.9); 8.032 (8.6); 7.569 (0.7); 7.561 (7.5); 7.555 (2.5); 7.544 (2.7); 7.538 (9.0); 7.530 (0.9); 7.322 (1.0); 7.314 (9.1); 7.308 (2.8); 7.297 (2.4); 7.291 (7.5); 7.283 (0.7); 7.260 (6.1); 7.239 (6.1); 5.878 (16.0); 5.859 (0.3); 3.312 (7.1); 2.897 (1.1); 2.739 (0.9); 2.517 (7.1); 2.512 (14.4); 2.508 (19.4); 2.503 (13.6); 2.499 (6.3)

Example VII.10

[0585] .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO): =8.522 (7.4); 8.470 (4.9); 8.449 (5.2); 8.028 (7.2); 7.489 (2.5); 7.488 (2.5); 7.483 (2.8); 7.482 (2.8); 7.379 (1.4); 7.378 (1.4); 7.372 (1.3); 7.371 (1.3); 7.357 (1.9); 7.356 (1.9); 7.351 (1.8); 7.350 (1.8); 7.242 (5.4); 7.230 (4.5); 7.221 (5.5); 7.209 (3.4); 5.877 (13.2); 5.859 (0.5); 3.312 (6.2); 2.897 (0.4); 2.739 (0.4); 2.738 (0.4); 2.530 (0.4); 2.517 (6.2); 2.513 (12.6); 2.508 (17.3); 2.504 (12.5); 2.499 (6.3); 2.108 (16.0)

Example VII.11

[0586] .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO): =8.530 (7.2); 8.463 (4.5); 8.442 (4.7); 8.032 (7.0); 7.474 (2.4); 7.452 (2.8); 7.406 (3.4); 7.400 (3.6); 7.240 (4.9); 7.219 (4.9); 7.172 (2.1); 7.166 (2.1); 7.151 (1.9); 7.145 (1.8); 5.877 (12.9); 3.313 (5.3); 2.897 (0.4); 2.738 (0.3); 2.517 (5.5); 2.512 (11.1); 2.508 (14.9); 2.503 (10.6); 2.499 (5.0); 2.366 (16.0)

Example VII.12

[0587] .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO): =8.529 (8.8); 8.461 (5.7); 8.440 (5.9); 8.031 (8.6); 7.352 (0.8); 7.345 (0.6); 7.337 (1.0); 7.329 (6.9); 7.325 (3.2); 7.320 (7.1); 7.309 (11.1); 7.307 (11.1); 7.297 (1.1); 7.285 (0.4); 7.222 (6.1); 7.201 (6.0); 5.876 (16.0); 5.856 (0.4); 3.313 (5.9); 2.517 (6.5); 2.512 (13.1); 2.508 (17.7); 2.503 (12.4); 2.499 (5.8)

Example VII.13

[0588] .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO): =8.524 (8.8); 8.506 (5.6); 8.485 (5.8); 8.030 (8.5); 7.562 (1.2); 7.555 (1.3); 7.550 (1.2); 7.540 (1.5); 7.535 (2.5); 7.527 (3.4); 7.513 (3.4); 7.505 (2.3); 7.491 (1.2); 7.379 (6.0); 7.358 (5.8); 7.242 (0.8); 7.238 (0.9); 7.235 (0.8); 7.231 (0.8); 7.218 (1.4); 7.215 (1.4); 7.212 (1.3); 7.199 (0.7); 7.195 (0.8); 7.192 (0.7); 7.188 (0.6); 5.887 (16.0); 3.313 (9.6); 2.530 (0.3); 2.517 (7.3); 2.512 (14.7); 2.508 (19.7); 2.503 (13.9); 2.499 (6.5)

Example VII.14

[0589] .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO): =8.525 (8.8); 8.505 (6.2); 8.484 (6.4); 8.031 (8.5); 7.472 (1.0); 7.468 (1.1); 7.460 (1.2); 7.456 (1.4); 7.452 (1.9); 7.448 (2.1); 7.441 (3.4); 7.436 (2.9); 7.425 (1.9); 7.421 (3.2); 7.416 (2.1); 7.409 (1.0); 7.404 (1.0); 7.396 (1.0); 7.390 (1.8); 7.385 (1.4); 7.378 (1.8); 7.373 (1.4); 7.370 (1.3); 7.362 (7.0); 7.358 (1.3); 7.353 (1.0); 7.341 (7.3); 7.335 (2.2); 7.320 (2.1); 7.316 (2.1); 7.301 (0.8); 7.300 (0.8); 7.297 (0.8); 5.889 (16.0); 5.872 (0.4); 3.315 (6.3); 2.897 (0.5); 2.739 (0.4); 2.738 (0.4); 2.530 (0.4); 2.526 (0.6); 2.517 (6.0); 2.513 (12.1); 2.508 (16.7); 2.504 (12.0); 2.499 (6.0); 2.463 (0.3)

Example VII.15

[0590] .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO): =8.537 (8.8); 8.494 (6.0); 8.472 (6.3); 8.035 (8.7); 7.500 (0.6); 7.491 (2.9); 7.485 (1.0); 7.475 (3.0); 7.469 (3.0); 7.460 (1.1); 7.454 (2.8); 7.445 (0.8); 7.436 (0.4); 7.317 (6.5); 7.295 (6.5); 5.882 (16.0); 5.862 (0.5); 3.311 (8.5); 2.531 (0.3); 2.517 (7.6); 2.513 (16.0); 2.508 (22.1); 2.504 (16.3); 2.499 (8.3); 2.463 (0.5); 2.459 (0.4)

Example VII.16

[0591] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.222 (8.9); 8.194 (4.8); 8.020 (2.0); 8.004 (5.5); 7.608 (0.4); 7.520 (3.5); 7.512 (3.9); 7.358 (2.0); 7.350 (1.8); 7.329 (2.9); 7.321 (2.8); 7.279 (0.4); 7.277 (0.4); 7.276 (0.4); 7.273 (0.7); 7.262 (62.1); 7.250 (1.2); 7.247 (0.9); 7.246 (0.8); 7.244 (0.8); 7.240 (0.6); 7.234 (0.5); 7.228 (0.4); 7.200 (4.7); 7.171 (3.2); 7.054 (4.8); 7.025 (4.7); 6.911 (0.4); 5.710 (12.5); 2.959 (16.0); 2.886 (13.8); 2.885 (13.5); 1.570 (15.1); 1.252 (0.4); 0.011 (1.8); 0.009 (1.1); 0.000 (49.7); 0.010 (1.4); 0.011 (1.9); 0.018 (0.4)

Example VII.17

[0592] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.231 (3.3); 8.222 (2.9); 8.194 (2.8); 8.091 (0.4); 8.082 (3.2); 8.075 (1.2); 8.059 (1.1); 8.053 (3.4); 8.044 (0.6); 8.019 (0.4); 8.008 (3.3); 7.299 (0.5); 7.290 (3.4); 7.283 (1.2); 7.278 (0.4); 7.276 (0.4); 7.275 (0.5); 7.273 (0.6); 7.263 (33.8); 7.252 (1.0); 7.031 (2.8); 7.002 (2.8); 5.719 (7.4); 2.959 (1.3); 2.887 (1.1); 2.885 (1.1); 2.641 (16.0); 2.562 (0.3); 2.048 (0.9); 1.567 (8.5); 1.261 (0.6); 0.011 (0.8); 0.007 (0.5); 0.000 (25.4); 0.009 (0.8); 0.011 (1.1)

Example VII.18

[0593] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.450 (5.1); 8.422 (5.4); 8.193 (7.8); 8.019 (7.8); 7.608 (0.5); 7.429 (0.8); 7.418 (6.5); 7.411 (2.4); 7.396 (2.6); 7.389 (8.3); 7.378 (1.2); 7.330 (0.4); 7.300 (0.5); 7.262 (77.9); 7.230 (0.3); 7.152 (1.1); 7.141 (7.6); 7.134 (2.5); 7.119 (2.3); 7.112 (6.4); 7.101 (0.6); 6.955 (4.7); 6.927 (4.6); 6.911 (0.6); 5.568 (16.0); 5.302 (0.9); 1.554 (49.9); 1.340 (0.4); 1.252 (1.1); 0.881 (0.3); 0.195 (0.5); 0.081 (0.9); 0.069 (25.4); 0.057 (1.3); 0.026 (0.3); 0.011 (2.9); 0.000 (87.8); 0.011 (4.3); 0.031 (0.6); 0.200 (0.4)

Example VII.19

[0594] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.221 (3.0); 8.196 (2.4); 8.167 (2.5); 8.001 (3.0); 7.264 (6.6); 7.157 (1.8); 7.127 (2.3); 7.031 (1.8); 7.022 (2.1); 6.965 (2.6); 6.937 (2.4); 6.897 (1.4); 6.887 (1.2); 6.867 (1.1); 6.857 (1.0); 5.716 (6.8); 5.301 (16.0); 3.841 (13.1); 3.827 (0.7); 3.818 (0.5); 3.808 (1.2); 1.610 (5.6); 0.070 (0.4); 0.000 (6.8)

Example VII.20

[0595] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.233 (10.0); 8.205 (3.0); 8.201 (5.1); 8.005 (7.2); 7.865 (6.9); 7.857 (3.0); 7.841 (5.6); 7.834 (6.7); 7.309 (5.6); 7.278 (5.7); 7.266 (5.9); 7.053 (5.2); 7.025 (4.9); 5.718 (16.0); 5.305 (6.6); 5.301 (12.5); 1.662 (6.4); 1.258 (0.5); 0.003 (3.1); 0.000 (5.5)

Example VII.21

[0596] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.572 (6.1); 8.248 (6.8); 8.034 (7.0); 7.931 (0.6); 7.920 (5.9); 7.914 (2.2); 7.897 (2.0); 7.890 (6.7); 7.452 (6.4); 7.332 (4.0); 7.300 (30.7); 5.503 (16.0); 5.340 (5.5); 1.593 (10.7); 1.308 (0.5); 1.295 (0.6); 0.109 (7.2); 0.050 (1.3); 0.039 (35.7); 0.029 (1.7)

Example VII.22

[0597] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.266 (6.8); 8.246 (4.8); 8.217 (4.9); 8.044 (6.7); 7.660 (3.3); 7.631 (4.0); 7.327 (4.6); 7.300 (44.3); 7.039 (5.0); 7.010 (4.7); 6.923 (1.7); 6.735 (3.4); 6.547 (1.7); 5.753 (16.0); 5.339 (0.4); 1.591 (21.4); 1.352 (0.4); 1.293 (1.1); 0.108 (3.0); 0.050 (1.5); 0.039 (42.6); 0.028 (1.5)

Example VII.23

[0598] .sup.1H-NMR (499.9 MHz, d.sub.6-DMSO): =8.946 (1.3); 8.897 (1.3); 8.756 (9.9); 8.532 (8.7); 8.416 (1.2); 8.027 (8.2); 8.015 (0.3); 7.597 (0.7); 7.590 (7.0); 7.586 (2.5); 7.577 (2.7); 7.572 (8.6); 7.566 (1.2); 7.555 (0.6); 7.545 (1.1); 7.541 (0.5); 7.538 (0.4); 7.532 (0.5); 7.528 (1.2); 7.402 (1.0); 7.395 (8.5); 7.391 (2.8); 7.381 (2.5); 7.377 (7.2); 7.370 (1.9); 7.356 (0.6); 7.351 (1.1); 5.929 (16.0); 3.300 (185.7); 2.681 (3.9); 2.591 (0.4); 2.560 (0.4); 2.507 (8.9); 2.503 (18.2); 2.500 (25.1); 2.496 (18.7); 2.493 (9.8); 2.070 (0.8); 0.006 (0.3); 0.000 (7.5); 0.007 (0.5)

Example VII.24

[0599] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.223 (8.6); 8.022 (8.8); 7.930 (3.9); 7.902 (4.2); 7.646 (0.6); 7.613 (0.8); 7.602 (8.5); 7.595 (2.8); 7.579 (2.8); 7.572 (9.5); 7.562 (1.1); 7.366 (0.6); 7.300 (100.9); 7.233 (0.5); 7.209 (4.3); 7.181 (4.0); 7.145 (1.0); 7.134 (9.5); 7.127 (3.0); 7.112 (2.6); 7.104 (8.2); 7.094 (0.9); 6.949 (0.5); 5.425 (16.0); 1.657 (0.6); 1.597 (38.8); 1.593 (86.1); 1.524 (0.5); 1.326 (0.4); 1.292 (0.9); 0.919 (0.3); 0.233 (0.4); 0.120 (0.7); 0.108 (20.9); 0.095 (0.7); 0.049 (3.4); 0.038 (102.6); 0.027 (3.3); 0.028 (0.4); 0.161 (0.4)

Example VII.25

[0600] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.518 (4.9); 8.490 (6.7); 8.487 (5.9); 8.459 (5.1); 8.265 (0.4); 8.237 (14.7); 8.057 (15.0); 7.646 (0.3); 7.492 (1.4); 7.481 (13.5); 7.473 (4.4); 7.458 (5.0); 7.451 (16.0); 7.440 (2.0); 7.412 (0.5); 7.300 (55.9); 7.191 (1.9); 7.180 (16.7); 7.173 (5.0); 7.158 (4.6); 7.150 (13.0); 7.140 (1.6); 7.016 (5.7); 7.010 (5.5); 6.988 (5.5); 6.982 (5.2); 6.949 (0.3); 5.619 (15.7); 5.607 (15.6); 5.571 (0.9); 2.692 (1.1); 2.046 (0.5); 1.610 (13.9); 1.306 (0.4); 1.292 (0.5); 0.119 (0.5); 0.107 (10.3); 0.095 (0.5); 0.048 (2.4); 0.047 (1.7); 0.038 (60.4); 0.030 (1.9); 0.028 (1.8); 0.027 (2.3); 0.018 (0.4)

Example VII.26

[0601] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.584 (5.9); 8.245 (6.9); 8.030 (6.9); 7.414 (6.1); 7.368 (2.9); 7.340 (4.7); 7.338 (4.5); 7.300 (12.6); 7.264 (1.1); 7.253 (9.0); 7.245 (2.4); 7.231 (1.9); 7.223 (5.0); 7.212 (0.5); 5.502 (16.0); 5.337 (9.8); 4.170 (0.7); 4.146 (0.7); 2.082 (3.1); 1.639 (5.4); 1.320 (0.9); 1.296 (1.8); 1.273 (0.8); 0.107 (1.4); 0.048 (0.4); 0.037 (12.6); 0.026 (0.5)

Example VII.27

[0602] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.578 (5.8); 8.244 (6.8); 8.031 (6.9); 7.645 (0.8); 7.634 (6.9); 7.627 (2.2); 7.612 (2.3); 7.605 (7.7); 7.594 (0.8); 7.398 (6.0); 7.300 (24.3); 7.124 (0.8); 7.113 (7.8); 7.106 (2.3); 7.091 (2.2); 7.084 (6.9); 7.073 (0.7); 5.500 (16.0); 5.339 (3.1); 1.609 (14.4); 0.108 (1.0); 0.049 (0.9); 0.038 (25.7); 0.027 (1.0)

Example VII.28

[0603] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.576 (4.9); 8.247 (5.7); 8.033 (5.9); 7.793 (3.5); 7.765 (4.0); 7.445 (5.3); 7.350 (3.8); 7.322 (3.6); 7.310 (1.1); 7.300 (32.4); 5.504 (13.7); 5.339 (13.6); 1.600 (16.0); 1.293 (0.4); 0.108 (1.3); 0.049 (1.6); 0.038 (34.7); 0.027 (1.3)

Example VII.29

[0604] .sup.1H-NMR (300.2 MHz, d.sub.6-DMSO): =9.008 (6.8); 8.549 (9.5); 8.059 (9.2); 7.752 (8.8); 7.717 (5.0); 7.462 (5.7); 7.434 (4.6); 7.307 (1.8); 7.121 (4.2); 6.935 (2.0); 5.945 (15.0); 5.781 (0.8); 4.088 (1.2); 4.064 (3.6); 4.057 (0.6); 4.041 (3.6); 4.017 (1.2); 3.347 (22.1); 2.537 (1.9); 2.531 (4.0); 2.525 (5.5); 2.519 (4.0); 2.513 (1.9); 2.012 (16.0); 1.221 (4.4); 1.198 (8.8); 1.174 (4.3); 0.023 (3.8)

Example VII.30

[0605] .sup.1H-NMR (300.2 MHz, d.sub.6-DMSO): =8.999 (7.1); 8.539 (10.0); 8.057 (10.0); 7.866 (7.7); 7.770 (2.8); 7.762 (2.9); 7.735 (2.7); 7.727 (2.8); 7.579 (2.1); 7.550 (4.6); 7.522 (3.5); 7.471 (2.7); 7.467 (2.7); 7.463 (2.5); 7.459 (2.2); 7.441 (1.4); 7.438 (1.6); 7.433 (1.4); 7.430 (1.3); 5.950 (16.0); 5.781 (15.8); 3.352 (4.1); 2.537 (2.1); 2.531 (4.4); 2.525 (6.0); 2.519 (4.4); 2.513 (2.1); 0.022 (7.5); 0.011 (0.4)

Example VII.31

[0606] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.225 (8.9); 8.021 (9.1); 7.974 (4.0); 7.946 (4.2); 7.899 (1.0); 7.888 (7.9); 7.881 (2.8); 7.865 (2.9); 7.858 (8.7); 7.847 (1.1); 7.362 (5.1); 7.332 (4.6); 7.300 (30.4); 7.288 (5.0); 7.260 (4.3); 5.433 (16.0); 5.338 (10.9); 1.606 (6.4); 1.293 (0.6); 0.108 (0.7); 0.049 (1.4); 0.038 (32.7); 0.027 (1.3)

Example VII.32

[0607] .sup.1H-NMR (499.9 MHz, CDCl.sub.3): =8.182 (8.2); 7.976 (8.1); 7.915 (3.9); 7.898 (4.1); 7.711 (5.5); 7.694 (6.0); 7.327 (5.7); 7.310 (5.3); 7.263 (5.1); 7.221 (4.3); 7.204 (4.1); 5.390 (16.0); 5.296 (0.4); 1.634 (0.7); 0.000 (5.5); 0.007 (0.4)

Example VII.33

[0608] 1H-NMR (300.2 MHz, CDCl.sub.3): =8.225 (8.1); 8.030 (8.4); 7.994 (3.9); 7.966 (4.1); 7.646 (0.5); 7.408 (4.5); 7.380 (4.1); 7.319 (0.6); 7.300 (86.9); 7.153 (0.9); 7.142 (1.8); 7.132 (8.7); 7.108 (8.5); 7.104 (2.6); 7.099 (1.7); 7.088 (0.8); 6.949 (0.4); 5.431 (16.0); 1.589 (31.8); 1.354 (0.5); 1.292 (1.3); 0.920 (0.4); 0.234 (0.4); 0.108 (12.4); 0.049 (3.3); 0.039 (93.5); 0.028 (3.2); 0.015 (0.4); 0.160 (0.3)

Example VII.34

[0609] 1H-NMR (499.9 MHz, CDCl.sub.3): =8.186 (4.0); 7.970 (4.1); 7.847 (1.8); 7.830 (1.9); 7.288 (3.1); 7.271 (3.8); 7.267 (1.9); 7.106 (0.6); 7.101 (4.1); 7.097 (1.4); 7.087 (1.3); 7.084 (3.4); 7.078 (0.4); 7.061 (2.0); 7.044 (2.0); 5.393 (7.4); 2.966 (0.8); 2.952 (1.1); 2.938 (0.8); 2.924 (0.4); 1.286 (15.9); 1.272 (16.0); 1.259 (0.5); 0.000 (1.2)

Example VII.35

[0610] 1H-NMR (300.2 MHz, CDCl.sub.3): =8.250 (6.6); 8.098 (3.8); 8.070 (4.2); 8.040 (7.3); 7.647 (0.5); 7.615 (1.0); 7.604 (8.3); 7.597 (2.6); 7.582 (3.1); 7.574 (9.1); 7.564 (1.3); 7.302 (68.9); 7.158 (3.9); 7.147 (1.4); 7.136 (10.1); 7.129 (6.3); 7.113 (3.0); 7.106 (8.0); 7.096 (1.0); 7.018 (2.7); 6.950 (0.5); 6.836 (5.1); 6.655 (2.6); 5.561 (16.0); 5.341 (1.5); 1.613 (15.8); 1.293 (1.5); 0.122 (0.4); 0.109 (8.8); 0.098 (0.4); 0.051 (1.4); 0.040 (42.7); 0.029 (1.6)

Example VII.36

[0611] 1H-NMR (300.2 MHz, CDCl.sub.3): =8.819 (4.9); 8.252 (7.2); 8.056 (7.3); 7.644 (0.5); 7.586 (1.8); 7.502 (0.7); 7.491 (6.8); 7.483 (6.1); 7.468 (2.4); 7.461 (8.0); 7.450 (0.9); 7.405 (3.7); 7.298 (87.1); 7.223 (1.9); 7.193 (0.8); 7.182 (8.1); 7.174 (2.3); 7.159 (2.1); 7.152 (6.5); 7.141 (0.6); 6.947 (0.5); 5.624 (16.0); 5.338 (6.7); 1.583 (53.8); 1.291 (2.3); 0.107 (1.7); 0.048 (2.8); 0.038 (89.7); 0.027 (3.3); 0.161 (0.4)

Example VII.37

[0612] 1H-NMR (300.2 MHz, CDCl.sub.3): =8.222 (7.7); 8.024 (8.6); 7.993 (0.4); 7.957 (3.9); 7.930 (4.2); 7.646 (0.4); 7.337 (0.3); 7.311 (5.7); 7.300 (83.2); 7.283 (5.0); 7.267 (2.9); 7.265 (3.4); 7.261 (3.9); 7.239 (7.6); 7.233 (7.7); 7.226 (6.4); 7.222 (3.9); 7.198 (0.6); 6.949 (0.4); 5.426 (16.0); 5.340 (1.1); 1.591 (25.1); 1.368 (0.4); 1.350 (0.5); 1.293 (1.0); 0.920 (0.4); 0.234 (0.4); 0.108 (10.6); 0.067 (0.4); 0.049 (3.6); 0.039 (88.4); 0.028 (3.1); 0.018 (0.4)

Example VII.38

[0613] 1H-NMR (300.2 MHz, d6-DMSO): =8.833 (10.2); 8.551 (9.6); 8.057 (9.4); 7.585 (0.8); 7.573 (7.8); 7.566 (2.5); 7.551 (3.0); 7.544 (9.5); 7.533 (1.1); 7.496 (10.9); 7.334 (1.1); 7.323 (9.8); 7.315 (2.8); 7.300 (2.7); 7.293 (7.4); 7.282 (0.8); 5.912 (16.0); 5.786 (1.3); 3.355 (11.4); 2.540 (3.3); 2.534 (6.8); 2.528 (9.2); 2.522 (6.6); 2.516 (3.1); 0.026 (8.5); 0.015 (0.3)

Example VII.39

[0614] 1H-NMR (300.2 MHz, CDCl.sub.3): =8.225 (7.9); 8.021 (8.6); 7.940 (3.9); 7.912 (4.3); 7.342 (3.0); 7.312 (7.6); 7.300 (34.5); 7.284 (2.2); 7.275 (13.6); 7.266 (3.0); 7.252 (2.2); 7.244 (4.8); 7.227 (4.8); 7.198 (4.4); 5.428 (16.0); 5.339 (3.2); 2.084 (0.4); 1.608 (5.6); 1.298 (0.5); 1.292 (0.5); 0.108 (4.4); 0.049 (1.2); 0.038 (37.2); 0.027 (1.4)

Example VII.40

[0615] 1H-NMR (300.2 MHz, CDCl.sub.3): =8.606 (8.2); 8.265 (6.7); 8.026 (7.0); 7.762 (4.0); 7.733 (4.6); 7.321 (4.4); 7.298 (5.9); 7.294 (4.1); 7.159 (8.6); 5.663 (16.0); 5.329 (10.2); 0.031 (3.8)

Example VII.41

[0616] 1H-NMR (300.2 MHz, CDCl.sub.3): =8.817 (5.5); 8.251 (7.2); 8.055 (7.1); 7.651 (0.8); 7.640 (6.4); 7.634 (2.7); 7.618 (2.3); 7.611 (7.3); 7.585 (1.8); 7.481 (5.6); 7.404 (3.9); 7.298 (49.1); 7.223 (1.9); 7.139 (0.9); 7.128 (7.1); 7.122 (2.9); 7.106 (2.2); 7.099 (6.5); 5.624 (16.0); 5.338 (4.5); 1.586 (30.9); 1.342 (0.5); 1.291 (2.2); 0.918 (0.4); 0.107 (2.0); 0.048 (2.4); 0.038 (51.2)

Example VII.42

[0617] 1H-NMR (300.2 MHz, CDCl.sub.3): =8.223 (8.7); 8.017 (9.0); 7.947 (3.9); 7.918 (4.2); 7.637 (4.5); 7.609 (5.4); 7.332 (6.2); 7.301 (8.5); 7.234 (4.5); 7.206 (4.2); 6.915 (2.3); 6.727 (4.6); 6.539 (2.3); 5.432 (16.0); 5.334 (1.5); 3.292 (0.4); 1.741 (0.6); 0.034 (4.6)

Example IX.01

[0618] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.496 (5.1); 7.450 (0.6); 7.439 (6.3); 7.432 (2.1); 7.417 (2.3); 7.409 (7.9); 7.399 (0.9); 7.300 (31.2); 7.183 (5.8); 7.151 (1.0); 7.140 (7.8); 7.133 (2.4); 7.118 (2.1); 7.110 (6.4); 7.099 (0.7); 5.340 (0.9); 3.053 (3.8); 3.037 (4.9); 2.917 (2.6); 2.901 (2.0); 1.682 (16.0); 1.582 (18.0); 1.304 (0.7); 0.921 (0.7); 0.109 (1.3); 0.050 (1.0); 0.049 (0.7); 0.047 (0.7); 0.039 (33.9); 0.029 (1.4)

Example IX.02

[0619] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): =8.630 (0.5); 8.170 (6.5); 7.467 (0.5); 7.462 (0.5); 7.450 (2.9); 7.445 (1.8); 7.431 (4.1); 7.429 (4.1); 7.415 (1.5); 7.410 (3.3); 7.404 (0.7); 7.281 (0.3); 7.263 (1.4); 7.260 (1.8); 7.258 (1.2); 7.242 (2.9); 7.236 (6.9); 7.226 (0.9); 7.223 (1.2); 7.220 (0.8); 7.191 (0.4); 7.188 (0.4); 7.173 (1.1); 7.170 (1.1); 7.155 (4.0); 7.152 (4.9); 7.147 (1.5); 7.135 (2.3); 7.133 (3.5); 7.131 (3.0); 7.124 (0.6); 7.105 (0.3); 6.428 (0.5); 3.327 (40.6); 3.251 (0.7); 3.077 (4.0); 3.022 (3.1); 3.009 (3.5); 2.996 (0.5); 2.825 (2.4); 2.812 (2.2); 2.711 (0.6); 2.622 (0.5); 2.592 (3.5); 2.562 (0.5); 2.542 (136.6); 2.525 (1.3); 2.511 (17.8); 2.507 (35.0); 2.502 (45.6); 2.498 (33.1); 2.493 (16.0); 2.472 (0.5); 2.432 (0.5); 2.429 (0.5); 2.368 (0.6); 2.329 (0.4); 1.989 (0.7); 1.642 (0.6); 1.582 (16.0); 1.258 (0.4); 1.235 (1.4); 1.135 (0.4); 1.119 (0.5); 1.106 (12.4); 0.853 (0.5); 0.836 (0.4); 0.000 (4.3)

Example IX.03

[0620] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): =9.657 (0.4); 8.172 (5.6); 7.502 (0.6); 7.496 (0.7); 7.487 (4.7); 7.481 (2.0); 7.470 (1.9); 7.465 (5.5); 7.456 (0.9); 7.447 (0.4); 7.430 (0.5); 7.421 (0.3); 7.408 (0.3); 7.303 (5.5); 7.218 (0.8); 7.213 (0.9); 7.204 (5.5); 7.199 (2.2); 7.188 (1.8); 7.182 (4.7); 7.176 (1.0); 7.149 (0.4); 6.772 (0.5); 6.750 (0.5); 3.748 (0.4); 3.660 (0.6); 3.602 (0.4); 3.327 (26.5); 3.251 (0.7); 3.077 (5.1); 3.025 (2.6); 3.013 (2.9); 2.996 (0.6); 2.821 (2.2); 2.808 (1.9); 2.712 (0.5); 2.594 (1.8); 2.564 (0.3); 2.542 (118.0); 2.511 (17.7); 2.507 (35.6); 2.502 (47.3); 2.498 (35.2); 2.494 (17.7); 2.368 (0.6); 2.329 (0.4); 1.989 (0.7); 1.760 (0.5); 1.622 (0.4); 1.581 (14.0); 1.298 (0.5); 1.259 (0.9); 1.235 (2.8); 1.193 (0.4); 1.183 (1.1); 1.169 (0.5); 1.135 (0.5); 1.119 (0.6); 1.106 (16.0); 1.082 (0.4); 1.046 (0.6); 0.867 (0.4); 0.854 (0.9); 0.836 (0.7); 0.813 (0.3); 0.000 (3.9)

Example IX.04

[0621] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): =9.319 (0.3); 7.931 (3.5); 7.910 (3.6); 7.489 (0.4); 7.473 (2.5); 7.453 (4.3); 7.434 (3.4); 7.421 (0.9); 7.401 (0.6); 7.285 (1.6); 7.266 (2.5); 7.248 (1.3); 7.234 (0.6); 7.216 (0.8); 7.197 (0.7); 7.179 (4.3); 7.160 (3.8); 7.134 (0.8); 7.120 (0.4); 7.013 (3.7); 6.993 (3.6); 6.389 (0.3); 3.744 (0.4); 3.628 (1.6); 3.601 (0.5); 3.329 (35.2); 3.251 (0.6); 3.077 (1.6); 3.040 (2.9); 3.027 (3.3); 2.996 (0.4); 2.818 (2.6); 2.805 (2.4); 2.712 (1.2); 2.569 (1.9); 2.542 (199.7); 2.521 (2.1); 2.507 (30.0); 2.503 (40.3); 2.498 (31.6); 2.459 (1.8); 2.368 (1.3); 2.330 (0.4); 1.989 (0.6); 1.769 (0.3); 1.760 (0.7); 1.751 (0.3); 1.630 (0.3); 1.585 (0.3); 1.565 (16.0); 1.259 (0.4); 1.235 (1.1); 1.183 (0.3); 1.135 (0.4); 1.119 (0.4); 1.106 (5.1); 0.854 (0.4); 0.000 (3.4)

Example IX.05

[0622] 1H-NMR (300.2 MHz, d6-DMSO): =8.216 (1.9); 8.188 (3.6); 8.163 (2.2); 8.115 (6.9); 8.086 (7.4); 7.721 (6.3); 7.707 (14.0); 7.678 (16.0); 7.450 (4.5); 7.417 (10.0); 7.403 (13.1); 7.389 (14.5); 7.374 (10.6); 7.362 (6.3); 7.289 (6.2); 7.103 (13.2); 6.917 (6.4); 3.358 (15.3); 3.070 (8.3); 3.054 (10.1); 2.921 (7.8); 2.905 (6.5); 2.540 (5.5); 2.534 (10.8); 2.528 (14.3); 2.522 (10.3); 1.616 (4.3); 1.592 (0.3); 1.556 (0.6); 1.399 (0.8); 1.381 (1.7); 1.371 (1.9); 1.354 (3.0); 1.337 (1.9); 1.329 (1.8); 1.311 (0.9); 1.269 (0.3); 1.218 (0.5); 1.165 (0.3); 1.140 (0.4); 1.133 (0.3); 1.125 (0.4); 1.110 (0.4); 0.519 (0.8); 0.512 (0.7); 0.500 (2.0); 0.482 (7.8); 0.468 (3.4); 0.455 (8.7); 0.449 (6.0); 0.441 (5.0); 0.427 (3.2); 0.422 (3.2); 0.410 (3.6); 0.404 (2.9); 0.392 (3.1); 0.361 (1.0); 0.356 (1.4); 0.348 (3.1); 0.331 (3.9); 0.322 (1.9); 0.309 (2.6); 0.301 (1.5); 0.293 (1.0); 0.034 (0.8); 0.024 (15.2); 0.013 (0.7)

Example IX.06

[0623] 1H-NMR (300.2 MHz, CDCl.sub.3): =7.441 (0.4); 7.418 (0.4); 7.411 (0.7); 7.389 (0.3); 7.371 (0.5); 7.360 (4.9); 7.353 (1.8); 7.343 (0.9); 7.338 (2.0); 7.330 (6.3); 7.320 (0.9); 7.313 (0.9); 7.300 (5.3); 7.202 (0.3); 7.193 (0.6); 7.181 (0.4); 7.172 (0.4); 7.163 (0.7); 7.143 (0.4); 7.135 (0.3); 7.124 (0.7); 7.114 (6.5); 7.106 (2.0); 7.091 (1.9); 7.084 (6.9); 7.071 (1.1); 7.064 (0.5); 7.054 (3.0); 7.042 (0.6); 5.883 (2.6); 5.851 (2.5); 4.844 (2.7); 4.809 (3.0); 4.633 (0.4); 4.198 (0.5); 4.192 (1.5); 4.186 (1.6); 4.181 (0.6); 4.162 (0.5); 4.157 (1.3); 4.151 (1.4); 4.145 (0.6); 3.827 (0.7); 3.536 (1.9); 3.171 (0.4); 2.892 (0.4); 2.654 (0.6); 2.616 (0.9); 2.614 (0.9); 2.533 (0.5); 2.081 (16.0); 1.985 (2.4); 1.725 (1.1); 1.676 (0.6); 1.596 (4.3); 1.550 (0.7); 1.263 (0.3); 0.041 (5.3)

Example IX.07

[0624] 1H-NMR (300.2 MHz, d6-DMSO): =8.092 (6.0); 8.064 (6.4); 7.891 (0.4); 7.864 (0.4); 7.565 (1.5); 7.554 (12.8); 7.546 (5.0); 7.531 (5.1); 7.524 (16.0); 7.515 (2.3); 7.380 (6.8); 7.352 (6.4); 7.322 (2.3); 7.311 (16.0); 7.304 (4.8); 7.289 (5.7); 7.282 (12.3); 7.270 (1.4); 7.258 (1.0); 4.810 (0.5); 4.651 (0.6); 4.252 (0.7); 4.234 (0.6); 3.480 (0.5); 3.462 (0.5); 3.354 (13.8); 3.065 (7.0); 3.049 (8.4); 2.910 (6.7); 2.894 (5.6); 2.534 (9.4); 2.528 (12.6); 2.522 (9.1); 2.387 (0.4); 2.364 (0.5); 1.389 (0.6); 1.372 (1.3); 1.362 (1.5); 1.345 (2.5); 1.328 (1.5); 1.320 (1.6); 1.302 (0.8); 1.262 (0.4); 0.515 (0.6); 0.495 (1.8); 0.477 (6.5); 0.465 (3.0); 0.449 (7.1); 0.436 (3.0); 0.433 (3.1); 0.420 (2.6); 0.415 (2.4); 0.408 (1.7); 0.401 (3.0); 0.383 (2.6); 0.350 (1.0); 0.341 (2.6); 0.324 (3.3); 0.303 (2.4); 0.294 (1.1); 0.036 (0.6); 0.025 (12.4); 0.014 (0.5)

Example IX.08

[0625] 1H-NMR (300.2 MHz, d6-DMSO): =8.193 (1.0); 8.165 (1.8); 8.140 (1.1); 8.092 (4.6); 8.064 (5.0); 7.696 (2.7); 7.689 (1.5); 7.678 (14.8); 7.671 (6.6); 7.656 (5.0); 7.648 (16.0); 7.637 (1.6); 7.414 (2.1); 7.383 (5.9); 7.354 (4.9); 7.262 (1.2); 7.251 (12.5); 7.243 (5.4); 7.241 (6.4); 7.233 (2.4); 7.228 (3.6); 7.221 (10.6); 7.211 (5.4); 7.200 (0.5); 3.357 (7.1); 3.064 (5.3); 3.048 (6.5); 2.910 (5.0); 2.894 (4.4); 2.540 (2.4); 2.534 (5.1); 2.528 (6.8); 2.522 (4.9); 2.516 (2.3); 2.014 (0.5); 1.604 (0.3); 1.591 (3.0); 1.391 (0.4); 1.372 (1.0); 1.361 (1.3); 1.344 (2.0); 1.328 (1.4); 1.320 (1.3); 1.302 (0.9); 1.268 (2.7); 0.902 (0.8); 0.880 (2.5); 0.857 (0.9); 0.513 (0.4); 0.493 (1.1); 0.475 (4.9); 0.462 (2.2); 0.448 (5.5); 0.434 (2.8); 0.420 (2.0); 0.415 (2.0); 0.401 (2.3); 0.384 (2.0); 0.349 (0.8); 0.341 (2.0); 0.324 (2.6); 0.311 (1.0); 0.302 (1.8); 0.294 (1.0); 0.286 (0.7); 0.022 (7.4)

Example IX.10

[0626] 1H-NMR (300.2 MHz, CDCl.sub.3): =8.255 (6.0); 7.429 (0.6); 7.418 (5.2); 7.410 (1.8); 7.395 (2.0); 7.388 (6.2); 7.377 (0.8); 7.300 (3.4); 7.128 (0.8); 7.117 (6.4); 7.109 (2.1); 7.094 (1.8); 7.087 (5.1); 7.076 (0.6); 6.970 (6.5); 5.337 (1.2); 3.029 (3.3); 3.012 (3.9); 2.841 (2.6); 2.839 (2.5); 2.824 (2.2); 2.822 (2.1); 1.696 (16.0); 1.612 (2.2); 0.039 (3.5)

Example IX.11

[0627] 1H-NMR (300.2 MHz, d6-DMSO): =9.802 (0.3); 8.242 (1.1); 8.215 (2.0); 8.189 (1.2); 8.140 (7.8); 8.111 (8.5); 7.960 (0.3); 7.875 (13.8); 7.847 (16.0); 7.813 (0.5); 7.754 (2.7); 7.729 (2.5); 7.502 (3.6); 7.489 (12.2); 7.472 (14.1); 7.461 (11.1); 7.444 (10.1); 7.015 (0.5); 6.986 (0.4); 3.355 (20.6); 3.075 (9.2); 3.059 (11.3); 3.035 (0.5); 3.027 (0.8); 3.010 (0.7); 2.925 (8.6); 2.908 (7.3); 2.879 (0.5); 2.540 (6.0); 2.534 (12.8); 2.528 (17.5); 2.522 (12.6); 2.516 (5.9); 1.898 (0.3); 1.605 (1.2); 1.591 (10.7); 1.543 (1.0); 1.474 (0.3); 1.405 (0.7); 1.378 (2.1); 1.358 (3.4); 1.342 (2.2); 1.333 (2.1); 1.315 (1.2); 1.269 (2.5); 0.903 (0.7); 0.881 (2.3); 0.858 (0.9); 0.503 (1.7); 0.485 (9.0); 0.472 (3.7); 0.458 (10.9); 0.448 (5.1); 0.430 (4.0); 0.417 (4.5); 0.397 (3.3); 0.385 (1.2); 0.354 (3.6); 0.345 (2.1); 0.336 (4.0); 0.324 (1.9); 0.315 (2.5); 0.307 (2.2); 0.298 (1.4); 0.277 (0.6); 0.034 (0.5); 0.023 (18.0); 0.012 (0.8)

Biological Examples

[0628] The advanced fungicidal activity of the active compound combinations according to the invention is evident from the examples below. While the individual active compounds exhibit weaknesses with regard to the fungicidal activity, the combinations have an activity which exceeds a simple addition of activities.

[0629] A synergistic effect of fungicides is always present when the fungicidal activity of the active compound combinations exceeds the total of the activities of the active compounds when applied individually. The expected activity for a given combination of two active compounds can be calculated as follows (cf. Colby, S. R., Calculating Synergistic and Antagonistic Responses of Herbicide Combinations, Weeds 1967, 15, 20-22):

[0630] If

[0631] X is the efficacy when active compound A is applied at an application rate of m ppm (or g/ha),

[0632] Y is the efficacy when active compound B is applied at an application rate of n ppm (or g/ha),

[0633] E is the efficacy when the active compounds A and B are applied at application rates of m and n ppm (or g/ha), respectively, and

[0634] then

[00001] $E = X + Y - \frac{X .Math. Y}{100}$

[0635] The degree of efficacy, expressed in % is denoted. 0% means an efficacy which corresponds to that of the control while an efficacy of 100% means that no disease is observed.

[0636] If the actual fungicidal activity exceeds the calculated value, then the activity of the combination is superadditive, i.e. a synergistic effect exists. In this case, the efficacy which was actually observed must be greater than the value for the expected efficacy (E) calculated from the abovementioned formula.

[0637] A further way of demonstrating a synergistic effect is the method of Tammes (cf. Isoboles, a graphic representation of synergism in pesticides in Neth. J. Plant Path., 1964, 70, 73-80).

[0638] The invention is illustrated by the following examples. However the invention is not limited to the examples.

Example A: In Vivo Preventive Test on Alternaria (Tomatoes)

[0639] Solvent: 24.5 parts by weight of acetone [0640] 24.5 parts by weight of dimethylacetamide [0641] Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0642] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

[0643] To test for preventive activity, young plants are sprayed with the preparation of active compound at the stated rate of application. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Alternaria solani. The plants are then placed in an incubation cabinet at approximately 20 C. and a relative atmospheric humidity of 100%.

[0644] The test is evaluated 3 days after the inoculation. 0% means an efficacy which corresponds to that of the untreated control while an efficacy of 100% means that no disease is observed.

[0645] The table below clearly shows that the observed activity of the active compound combination according to the invention is greater than the calculated activity, i.e. a synergistic effect is present.

TABLE-US-00006 TABLE A1 in vivo preventive test on Alternaria (tomatoes) Application rate of active Efficacy in % Active compounds compound in ppm a.i. found* calc.** (I.01) 2-[6-(4-chlorophenoxy)-2- 5 49 (trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4- 1 13 triazol-1-yl)propan-2-ol (I.59) 2-[6-(4-bromophenoxy)-2- 5 54 (trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4- 1 13 triazol-1-yl)propan-2-ol 1.012 ipconazole 10 88 5 67 2.5 28 1.020 spiroxamine 100 49 50 38 25 13 1.021 tebuconazole 10 74 5 21 2.5 5 4.005 pencycuron 100 33 50 21 25 5 13.001 fludioxonil 20 95 10 85 5 77 (I.01) + 1.012 1:2 5 + 10 94 94 (I.01) + 1.012 1:1 5 + 5 85 83 (I.01) + 1.012 2:1 5 + 2.5 77 63 (I.01) + 1.012 1:10 1 + 10 90 90 (I.01) + 1.012 1:5 1 + 5 79 71 (I.01) + 1.012 1:2.5 1 + 2.5 44 37 (I.01) + 1.020 1:20 5 + 100 85 74 (I.01) + 1.020 1:10 5 + 50 67 68 (I.01) + 1.020 1:5 5 + 25 72 55 (I.01) + 1.020 1:100 1 + 100 64 55 (I.01) + 1.020 1:50 1 + 50 13 46 (I.01) + 1.020 1:25 1 + 25 0 24 (I.59) + 1.020 1:20 5 + 100 79 76 (I.59) + 1.020 1:10 5 + 50 77 72 (I.59) + 1.020 1:5 5 + 25 67 60 (I.59) + 1.020 1:100 1 + 100 85 55 (I.59) + 1.020 1:50 1 + 50 49 46 (I.59) + 1.020 1:25 1 + 25 33 24 (I.59) + 1.021 1:2 5 + 10 92 88 (I.59) + 1.021 1:1 5 + 5 87 63 (I.59) + 1.021 2:1 5 + 2.5 69 56 (I.59) + 1.021 1:10 1 + 10 69 78 (I.59) + 1.021 1:5 1 + 5 44 31 (I.59) + 1.021 1:2.5 1 + 2.5 33 17 (I.59) + 4.005 1:20 5 + 100 64 69 (I.59) + 4.005 1:10 5 + 50 79 63 (I.59) + 4.005 2:5 5 + 25 67 56 (I.59) + 4.005 1:100 1 + 100 64 42 (I.59) + 4.005 1:50 1 + 50 54 31 (I.59) + 4.005 1:25 1 + 25 5 17 (I.59) + 13.001 1:4 5 + 20 97 98 (I.59) + 13.001 1:2 5 + 10 95 93 (I.59) + 13.001 1:1 5 + 5 91 89 (I.59) + 13.001 1:20 1 + 20 95 96 (I.59) + 13.001 1:10 1 + 10 94 87 (I.59) + 13.001 1:5 1 + 5 87 80 *found = activity found **calc. = activity calculated using Colby's formula

TABLE-US-00007 TABLE A2 in vivo preventive test on Alternaria (tomatoes) Application rate of active Efficacy in % Active compounds compound in ppm a.i. found* calc.** (I.01) 2-[6-(4-chlorophenoxy)-2- 5 32 (trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4 - 1 3 triazol-1-yl)propan-2-ol (I.59) 2-[6-(4-bromophenoxy)-2- 5 18 (trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4 - 1 11 triazol-1-yl)propan-2-ol 2.005 fluopyram 20 84 10 61 5 53 2.017 penflufen 20 47 10 26 5 11 2.027 3-(difluoromethyl)-1-methyl-N-(1,1,3- 4 11 trimethyl-2,3-dihydro-1H-inden-4-yl)-1H- 2 3 pyrazole-4-carboxamide 1 0 3.020 trifloxystrobin 4 53 2 42 1 24 3.025 (3S,6S,7R,8R)-8-benzyl-3-[({3- 20 58 [(isobutyryloxy)methoxy]-4-methoxypyridin-2- 10 18 yl}carbonyl)amino]-6-methyl-4,9-dioxo-1,5- 5 18 dioxonan-7-yl 2-methylpropanoate (I.01) + 3.020 1:0.8 5 + 4 76 68 (I.01) + 3.020 1:0.4 5 + 2 63 60 (I.01) + 3.020 1:0.2 5 + 1 47 48 (I.01) + 3.020 1:4 1 + 4 66 54 (I.01) + 3.020 1:2 1 + 2 42 44 (I.01) + 3.020 1:1 1 + 1 11 26 (I.59) + 2.005 1:4 5 + 20 92 87 (I.59) + 2.005 1:2 5 + 10 82 68 (I.59) + 2.005 1:1 5 + 5 71 61 (I.59) + 2.005 1:20 1 + 20 86 86 (I.59) + 2.005 1:10 1 + 10 87 65 (I.59) + 2.005 1:5 1 + 5 53 58 (I.59) + 2.017 1:4 5 + 20 82 57 (I.59) + 2.017 1:2 5 + 10 37 40 (I.59) + 2.017 1:1 5 + 5 47 27 (I.59) + 2.017 1:20 1 + 20 63 53 (I.59) + 2.017 1:10 1 + 10 47 34 (I.59) + 2.017 1:5 1 + 5 32 20 (I.59) + 2.027 1:0.8 5 + 4 76 27 (I.59) + 2.027 1:0.4 5 + 2 37 21 (I.59) + 2.027 1:0.2 5 + 1 47 18 (I.59) + 2.027 1:4 1 + 4 37 20 (I.59) + 2.027 1:2 1 + 2 26 13 (I.59) + 2.027 1:1 1 + 1 11 11 (I.59) + 3.025 1:4 5 + 20 79 66 (I.59) + 3.025 1:2 5 + 10 71 33 (I.59) + 3.025 1:1 5 + 5 63 33 (I.59) + 3.025 1:20 1 + 20 76 62 (I.59) + 3.025 1:10 1 + 10 58 27 (I.59) + 3.025 1:5 1 + 5 53 27 *found = activity found **calc. = activity calculated using Colby's formula

TABLE-US-00008 TABLE A3 in vivo preventive test on Alternaria (tomatoes) Application rate of active compound Efficacy in % Active compounds in ppm a.i. found* calc.** (I.59) 2-[6-(4-bromophenoxy)-2- 5 21 (trifluoromethyl)pyridin-3-yl]-1- 1 13 (1H-1,2,4-triazol-1-yl)propan-2-ol 5.004 chlorothalonil 50 33 25 13 12.5 0 5.013 mancozeb 50 77 25 33 12.5 28 (I.59) + 5.004 1:10 5 + 50 59 47 (I.59) + 5.004 1:5 5 + 25 59 31 (I.59) + 5.004 1:2.5 5 + 12.5 49 21 (I.59) + 5.004 1:50 1 + 50 38 42 (I.59) + 5.004 1:25 1 + 25 33 24 (I.59) + 5.004 1:12.5 1 + 12.5 13 13 (I.59) + 5.013 1:10 5 + 50 88 82 (I.59) + 5.013 1:5 5 + 25 74 47 (I.59) + 5.013 1:2.5 5 + 12.5 38 43 (I.59) + 5.013 1:50 1 + 50 87 80 (I.59) + 5.013 1:25 1 + 25 33 42 (I.59) + 5.013 1:12.5 1 + 12.5 5 37 *found = activity found **calc. = activity calculated using Colby's formula

Example B: In Vivo Preventive Test on Colletotrichum (Tomatoes)

[0646] Solvent: 24.5 parts by weight of acetone [0647] 24.5 parts by weight of dimethylacetamide [0648] Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0649] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

[0650] To test for preventive activity, young plants are sprayed with the preparation of active compound at the stated rate of application. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Colletotrichum coccodes. The plants are then placed in an incubation cabinet at approximately 24 C. and a relative atmospheric humidity of 100%.

[0651] The test is evaluated 3 days after the inoculation. 0% means an efficacy which corresponds to that of the untreated control while an efficacy of 100% means that no disease is observed.

[0652] The table below clearly shows that the observed activity of the active compound combination according to the invention is greater than the calculated activity, i.e. a synergistic effect is present.

TABLE-US-00009 TABLE B1 in vivo preventive test on Colletotrichum (tomatoes) Application rate of active compound Efficacy in % Active compounds in ppm a.i. found* calc.** (I.59) 2-[6-(4-bromophenoxy)-2- 5 67 (trifluoromethyl)pyridin-3-yl]-1- 1 44 (1H-1,2,4-triazol-1-yl)propan-2-ol 1.018 prothioconazole 10 79 5 59 2.5 38 1.020 spiroxamine 100 49 50 44 25 33 1.021 tebuconazole 10 64 5 44 2.5 44 4.005 pencycuron 100 33 50 33 25 33 (I.59) + 1.018 1:2 5 + 10 92 93 (I.59) + 1.018 1:1 5 + 5 92 86 (I.59) + 1.018 2:1 5 + 2.5 92 79 (I.59) + 1.018 1:10 1 + 10 85 88 (I.59) + 1.018 1:5 1 + 5 87 77 (I.59) + 1.018 1:2.5 1 + 2.5 74 65 (I.59) + 1.020 1:20 5 + 100 87 83 (I.59) + 1.020 1:10 5 + 50 91 81 (I.59) + 1.020 1:5 5 + 25 87 78 (I.59) + 1.020 1:100 1 + 100 79 71 (I.59) + 1.020 1:50 1 + 50 87 68 (I.59) + 1.020 1:25 1 + 25 67 62 (I.59) + 1.021 1:2 5 + 10 94 88 (I.59) + 1.021 1:1 5 + 5 91 81 (I.59) + 1.021 2:1 5 + 2.5 92 81 (I.59) + 1.021 1:10 1 + 10 92 80 (I.59) + 1.021 1:5 1 + 5 64 68 (I.59) + 1.021 1:2.5 1 + 2.5 44 68 (I.59) + 4.005 1:20 5 + 100 90 78 (I.59) + 4.005 1:10 5 + 50 85 78 (I.59) + 4.005 2:5 5 + 25 87 78 (I.59) + 4.005 1:100 1 + 100 74 62 (I.59) + 4.005 1:50 1 + 50 64 62 (I.59) + 4.005 1:25 1 + 25 64 62 *found = activity found **calc. = activity calculated using Colby's formula

TABLE-US-00010 TABLE B2 in vivo preventive test on Colletotrichum (tomatoes) Application rate of active Efficacy in % Active compounds compound in ppm a.i. found* calc.** (I.59) 2-[6-(4-bromophenoxy)-2- 5 0 (trifluoromethyl)pyridin-3-yl]-1-(1H- 1 0 1,2,4-triazol-1-yl)propan-2-ol 5.004 chlorothalonil 50 8 25 8 12.5 0 5.013 mancozeb 50 0 25 0 12.5 0 (I.59) + 5.004 1:10 5 + 50 60 8 (I.59) + 5.004 1:5 5 + 25 60 8 (I.59) + 5.004 1:2.5 5 + 12.5 55 0 (I.59) + 5.004 1:50 1 + 50 8 8 (I.59) + 5.004 1:25 1 + 25 0 8 (I.59) + 5.004 1:12.5 1 + 12.5 0 0 (I.59) + 5.013 1:10 5 + 50 58 0 (I.59) + 5.013 1:5 5 + 25 65 0 (I.59) + 5.013 1:2.5 5 + 12.5 50 0 (I.59) + 5.013 1:50 1 + 50 35 0 (I.59) + 5.013 1:25 1 + 25 23 0 (I.59) + 5.013 1:12.5 1 + 12.5 0 0 *found = activity found **calc. = activity calculated using Colby's formula

Example C: In Vivo Preventive Test on Phakopsora (Soybeans)

[0653] Solvent: 24.5 parts by weight of acetone [0654] 24.5 parts by weight of dimethylacetamide [0655] Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0656] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

[0657] To test for preventive activity, young plants are sprayed with the preparation of active compound at the stated rate of application. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of the causal agent of soybean rust (Phakopsora pachyrhizi) and stay for 24 h without light in an incubation cabinet at approximately 24 C. and a relative atmospheric humidity of 95%. The plants remain in the incubation cabinet at approximately 24 C. and a relative atmospheric humidity of approximately 80% and a day/night interval of 12 h.

[0658] The test is evaluated 7 days after the inoculation. 0% means an efficacy which corresponds to that of the untreated control, while an efficacy of 100% means that no disease is observed.

[0659] The table below clearly shows that the observed activity of the active compound combination according to the invention is greater than the calculated activity, i.e. a synergistic effect is present.

TABLE-US-00011 TABLE C1 in vivo preventive test on Phakopsora test (soybeans) Application rate of active Efficacy in % Active compounds compound in ppm a.i. found* calc.** (I.01) 2-[6-(4-chlorophenoxy)-2- 5 50 (trifluoromethyl)pyridin-3-yl]-1-(1H- 1 0 1,2,4-triazol-1-yl)propan-2-ol (I.59) 2-[6-(4-bromophenoxy)-2- 5 50 (trifluoromethyl)pyridin-3-yl]-1-(1H- 1 8 1,2,4-triazol-1-yl)propan-2-ol 1.020 spiroxamine 100 75 50 50 25 23 (I.01) + 1.020 1:20 5 + 100 96 88 (I.01) + 1.020 1:10 5 + 50 95 75 (I.01) + 1.020 1:5 5 + 25 85 61 (I.01) + 1.020 1:100 1 + 100 93 75 (I.01) + 1.020 1:50 1 + 50 83 50 (I.01) + 1.020 1:25 1 + 25 35 23 (I.59) + 1.020 1:20 5 + 100 98 88 (I.59) + 1.020 1:10 5 + 50 90 75 (I.59) + 1.020 1:5 5 + 25 90 61 (I.59) + 1.020 1:100 1 + 100 88 77 (I.59) + 1.020 1:50 1 + 50 78 54 (I.59) + 1.020 1:25 1 + 25 35 28 *found = activity found **calc. = activity calculated using Colby's formula

TABLE-US-00012 TABLE C2 in vivo preventive test on Phakopsora (soybeans) Application rate of active Efficacy in % Active compounds compound in ppm a.i. found* calc.** (I.01) 2-[6-(4-chlorophenoxy)-2- 5 68 (trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4- 1 0 triazol-1-yl)propan-2-ol (I.59) 2-[6-(4-bromophenoxy)-2- 5 50 (trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4- 1 0 triazol-1-yl)propan-2-ol 2.002 bixafen 10 15 5 0 2.5 0 2.017 penflufen 20 83 10 43 5 8 2.027 3-(difluoromethyl)-1-methyl-N-(1,1,3- 4 100 trimethyl-2,3-dihydro-1H-inden-4-yl)-1H- 2 95 pyrazole-4-carboxamide 1 50 3.025 (3S,6S,7R,8R)-8-benzyl-3-[({3- 20 63 [(isobutyryloxy)methoxy]-4-methoxypyridin-2- 10 40 yl}carbonyl)amino]-6-methyl-4,9-dioxo-1,5- 5 23 dioxonan-7-yl 2-methylpropanoate (I.01) + 2.002 1:2 5 + 10 80 72 (I.01) + 2.002 1:1 5 + 5 65 68 (I.01) + 2.002 2:1 5 + 2.5 73 68 (I.01) + 2.002 1:10 1 + 10 0 15 (I.01) + 2.002 1:5 1 + 5 0 0 (I.01) + 2.002 1:2.5 1 + 2.5 0 0 (I.01) + 2.017 1:4 5 + 20 100 94 (I.01) + 2.017 1:2 5 + 10 90 81 (I.01) + 2.017 1:1 5 + 5 96 70 (I.01) + 2.017 1:20 1 + 20 85 83 (I.01) + 2.017 1:10 1 + 10 75 43 (I.01) + 2.017 1:5 1 + 5 50 8 (I.01) + 1.027 1:0.8 5 + 4 100 100 (I.01) + 1.027 1:0.4 5 + 2 94 98 (I.01) + 1.027 1:0.2 5 + 1 90 84 (I.01) + 1.027 1:4 1 + 4 100 100 (I.01) + 1.027 1:2 1 + 2 99 95 (I.01) + 1.027 1:1 1 + 1 84 50 (I.01) + 3.025 1:4 5 + 20 91 88 (I.01) + 3.025 1:2 5 + 10 91 88 (I.01) + 3.025 1:1 5 + 5 90 75 (I.01) + 3.025 1:20 1 + 20 80 63 (I.01) + 3.025 1:10 1 + 10 65 40 (I.01) + 3.025 1:5 1 + 5 30 23 (I.59) + 2.002 1:2 5 + 10 65 58 (I.59) + 2.002 1:1 5 + 5 58 50 (I.59) + 2.002 2:1 5 + 2.5 58 50 (I.59) + 2.002 1:10 1 + 10 8 15 (I.59) + 2.002 1:5 1 + 5 0 0 (I.59) + 2.002 1:2.5 1 + 2.5 0 0 (I.59) + 2.017 1:4 5 + 20 98 91 (I.59) + 2.017 1:2 5 + 10 69 71 (I.59) + 2.017 1:1 5 + 5 65 54 (I.59) + 2.017 1:20 1 + 20 81 83 (I.59) + 2.017 1:10 1 + 10 80 43 (I.59) + 2.017 1:5 1 + 5 23 8 (I.59) + 2.027 1:0.8 5 + 4 100 100 (I.59) + 2.027 1:0.4 5 + 2 96 98 (I.59) + 2.027 1:0.2 5 + 1 88 75 (I.59) + 2.027 1:4 1 + 4 100 100 (I.59) + 2.027 1:2 1 + 2 98 95 (I.59) + 2.027 1:1 1 + 1 65 50 (I.59) + 3.025 1:4 5 + 20 90 81 (I.59) + 3.025 1:2 5 + 10 70 70 (I.59) + 3.025 1:1 5 + 5 70 61 (I.59) + 3.025 1:20 1 + 20 78 63 (I.59) + 3.025 1:10 1 + 10 40 40 (I.59) + 3.025 1:5 1 + 5 28 23 *found = activity found **calc. = activity calculated using Colby's formula

TABLE-US-00013 TABLE C3 in vivo preventive test on Phakopsora (soybeans) Application rate of active Efficacy in % Active compounds compound in ppm a.i. found* calc.** (I.01) 2-[6-(4-chlorophenoxy)-2- 5 50 (trifluoromethyl)pyridin-3-yl]-1-(1H- 1 0 1,2,4-triazol-1-yl)propan-2-ol (I.59) 2-[6-(4-bromophenoxy)-2- 5 40 (trifluoromethyl)pyridin-3-yl]-1-(1H- 1 0 1,2,4-triazol-1-yl)propan-2-ol 5.004 chlorothalonil 50 0 25 8 12.5 0 5.013 mancozeb 50 90 25 45 12.5 23 5.018 propineb 20 83 10 23 5 0 12.003 metalaxyl 200 23 100 0 50 0 12.004 metalaxyl-M (mefenoxam) 200 15 100 0 50 0 (I.01) + 5.004 1:10 5 + 50 90 50 (I.01) + 5.004 1:5 5 + 25 48 54 (I.01) + 5.004 1:2.5 5 + 12.5 55 50 (I.01) + 5.004 1:50 1 + 50 40 0 (I.01) + 5.004 1:25 1 + 25 8 8 (I.01) + 5.004 1:12.5 1 + 12.5 0 0 (I.01) + 5.018 1:10 5 + 50 100 91 (I.01) + 5.018 1:5 5 + 25 73 61 (I.01) + 5.018 1:2.5 5 + 12.5 78 50 (I.01) + 5.018 1:50 1 + 50 94 83 (I.01) + 5.018 1:25 1 + 25 25 23 (I.01) + 5.018 1:12.5 1 + 12.5 8 0 (I.01) + 12.003 1:40 5 + 200 96 61 (I.01) + 12.003 1:20 5 + 100 85 50 (I.01) + 12.003 1:10 5 + 50 80 50 (I.01) + 12.003 1:200 1 + 200 53 23 (I.01) + 12.003 1:100 1 + 100 8 0 (I.01) + 12.003 1:50 1 + 50 0 0 (I.01) + 12.004 1:40 5 + 200 89 58 (I.01) + 12.004 1:20 5 + 100 86 50 (I.01) + 12.004 1:10 5 + 50 63 50 (I.01) + 12.004 1:200 1 + 200 50 15 (I.01) + 12.004 1:100 1 + 100 8 0 (I.01) + 12.004 1:50 1 + 50 0 0 (I.59) + 5.004 1:10 5 + 50 90 40 (I.59) + 5.004 1:5 5 + 25 53 45 (I.59) + 5.004 1:2.5 5 + 12.5 55 40 (I.59) + 5.004 1:50 1 + 50 38 0 (I.59) + 5.004 1:25 1 + 25 13 8 (I.59) + 5.004 1:12.5 1 + 12.5 0 0 (I.59) + 5.013 1:10 5 + 50 96 94 (I.59) + 5.013 1:5 5 + 25 81 67 (I.59) + 5.013 1:2.5 5 + 12.5 63 54 (I.59) + 5.013 1:50 1 + 50 89 90 (I.59) + 5.013 1:25 1 + 25 55 45 (I.59) + 5.013 1:12.5 1 + 12.5 8 23 (I.59) + 5.018 1:10 5 + 50 98 90 (I.59) + 5.018 1:5 5 + 25 80 54 (I.59) + 5.018 1:2.5 5 + 12.5 60 40 (I.59) + 5.018 1:50 1 + 50 89 83 (I.59) + 5.018 1:25 1 + 25 30 23 (I.59) + 5.018 1:12.5 1 + 12.5 0 0 (I.59) + 12.003 1:40 5 + 200 91 54 (I.59) + 12.003 1:20 5 + 100 89 40 (I.59) + 12.003 1:10 5 + 50 75 40 (I.59) + 12.003 1:200 1 + 200 65 23 (I.59) + 12.003 1:100 1 + 100 8 0 (I.59) + 12.003 1:50 1 + 50 0 0 (I.59) + 12.004 1:40 5 + 200 93 49 (I.59) + 12.004 1:20 5 + 100 88 40 (I.59) + 12.004 1:10 5 + 50 65 40 (I.59) + 12.004 1:200 1 + 200 60 15 (I.59) + 12.004 1:100 1 + 100 40 0 (I.59) + 12.004 1:50 1 + 50 0 0 *found = activity found **calc. = activity calculated using Colby's formula

Example D: In Vivo Preventive Test on Sphaerotheca (Cucumbers)

[0660] Solvent: 24.5 parts by weight of acetone [0661] 24.5 parts by weight of dimethylacetamide [0662] Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0663] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

[0664] To test for preventive activity, young plants are sprayed with the preparation of active compound at the stated rate of application. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Sphaerotheca fuliginea. The plants are then placed in a greenhouse at approximately 23 C. and a relative atmospheric humidity of approximately 70%.

[0665] The test is evaluated 7 days after the inoculation. 0% means an efficacy which corresponds to that of the untreated control, while an efficacy of 100% means that no disease is observed.

[0666] The table below clearly shows that the observed activity of the active compound combination according to the invention is greater than the calculated activity, i.e. a synergistic effect is present.

TABLE-US-00014 TABLE D1 in vivo preventive test on Sphaerotheca test (cucumbers) Application rate of active Efficacy in % Active compounds compound in ppm a.i. found* calc.** (I.01) 2-[6-(4-chlorophenoxy)-2- 5 93 (trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4- 1 20 triazol-1-yl)propan-2-ol (I.59) 2-[6-(4-bromophenoxy)-2- 5 89 (trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4- 1 20 triazol-1-yl)propan-2-ol 1.012 ipconazole 10 100 5 87 2.5 26 1.018 prothioconazole 10 100 5 96 2.5 71 1.020 spiroxamine 100 49 50 37 25 31 1.021 tebuconazole 10 83 5 69 2.5 37 (I.01) + 1.018 1:2 5 + 10 100 100 (I.01) + 1.018 1:1 5 + 5 100 100 (I.01) + 1.018 2:1 5 + 2.5 100 98 (I.01) + 1.018 1:10 1 + 10 100 100 (I.01) + 1.018 1:5 1 + 5 100 97 (I.01) + 1.018 1:2.5 1 + 2.5 96 77 (I.01) + 1.020 1:20 5 + 100 96 96 (I.01) + 1.020 1:10 5 + 50 96 96 (I.01) + 1.020 1:5 5 + 25 87 95 (I.01) + 1.020 1:100 1 + 100 91 59 (I.01) + 1.020 1:50 1 + 50 66 50 (I.01) + 1.020 1:25 1 + 25 20 45 (I.01) + 1.021 1:2 5 + 10 100 99 (I.01) + 1.021 1:1 5 + 5 99 98 (I.01) + 1.021 2:1 5 + 2.5 94 96 (I.01) + 1.021 1:10 1 + 10 93 86 (I.01) + 1.021 1:5 1 + 5 81 75 (I.01) + 1.021 1:2.5 1 + 2.5 63 50 (I.59) + 1.012 1:2 5 + 10 100 100 (I.59) + 1.012 1:1 5 + 5 100 99 (I.59) + 1.012 2:1 5 + 2.5 97 92 (I.59) + 1.012 1:10 1 + 10 97 100 (I.59) + 1.012 1:5 1 + 5 86 90 (I.59) + 1.012 1:2.5 1 + 2.5 63 41 *found = activity found **calc. = activity calculated using Colby's formula

TABLE-US-00015 TABLE D2 in vivo preventive test on Sphaerotheca (cucumbers) Application rate of active Efficacy in % Active compounds compound in ppm a.i. found* calc.** (I.01) 2-[6-(4-chlorophenoxy)-2- 5 65 (trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4- 1 15 triazol-1-yl)propan-2-ol (I.59) 2-[6-(4-bromophenoxy)-2- 5 55 (trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4- 1 8 triazol-1-yl)propan-2-ol 15.047 3-(4,4-difluoro-3,3-dimethyl-3,4- 10 8 dihydroisoquinolin-1-yl)quinoline 5 0 2.5 0 (I.01) + 15.047 1:2 5 + 10 93 68 (I.01) + 15.047 1:1 5 + 5 83 65 (I.01) + 15.047 2:1 5 + 2.5 88 65 (I.01) + 15.047 1:10 1 + 10 23 21 (I.01) + 15.047 1:5 1 + 5 0 15 (I.01) + 15.047 1:2.5 1 + 2.5 0 15 (I.59) + 15.047 1:2 5 + 10 93 58 (I.59) + 15.047 1:1 5 + 5 91 55 (I.59) + 15.047 2:1 5 + 2.5 70 55 (I.59) + 15.047 1:10 1 + 10 15 14 (I.59) + 15.047 1:5 1 + 5 0 8 (I.59) + 15.047 1:2.5 1 + 2.5 0 8 *found = activity found **calc. = activity calculated using Colby's formula

TABLE-US-00016 TABLE D3 in vivo preventive test on Sphaerotheca (cucumbers) Application rate of active Efficacy in % Active compounds compound in ppm a.i. found* calc.** (I.59) 2-[6-(4-bromophenoxy)-2- 5 88 (trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4- 1 0 triazol-1-yl)propan-2-ol 2.038 N-(5-chloro-2-isopropylbenzyl)-N- 4 98 cyclopropyl-3-(difluoromethyl)-5-fluoro-1- 2 93 methyl-1H-pyrazole-4-carboxamide 1 40 (I.59) + 2.038 1:0.8 5 + 4 100 100 (I.59) + 2.038 1:0.4 5 + 2 96 99 (I.59) + 2.038 1:0.2 5 + 1 86 93 (I.59) + 2.038 1:4 1 + 4 99 98 (I.59) + 2.038 1:2 1 + 2 98 93 (I.59) + 2.038 1:1 1 + 1 58 40 *found = activity found **calc. = activity calculated using Colby's formula

Example E: In Vivo Preventive Test on Venturia (Apples)

[0667] Solvent: 24.5 parts by weight of acetone [0668] 24.5 parts by weight of dimethylacetamide [0669] Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0670] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

[0671] To test for preventive activity, young plants are sprayed with the preparation of active compound at the stated rate of application. After the spray coating has dried on, the plants are inoculated with an aqueous conidia suspension of the causal agent of apple scab (Venturia inaequalis) and then remain for 1 day in an incubation cabinet at approximately 20 C. and a relative atmospheric humidity of 100%. The plants are then placed in a greenhouse at approximately 21 C. and a relative atmospheric humidity of approximately 90%.

[0672] The test is evaluated 10 days after the inoculation. 0% means an efficacy which corresponds to that of the untreated control, while an efficacy of 100% means that no disease is observed.

[0673] The table below clearly shows that the observed activity of the active compound combination according to the invention is greater than the calculated activity, i.e. a synergistic effect is present.

TABLE-US-00017 TABLE E1 in vivo preventive test on Venturia (apples) Application rate of active com- Efficacy in % Active compounds pound in ppm a.i. found* calc.** (I.01) 2-[6-(4-chlorophenoxy)-2- 5 74 (trifluoromethyl)pyridin-3-yl]-1- 1 78 (1H-1,2,4-triazol-1-yl)propan-2-ol (I.59) 2-[6-(4-bromophenoxy)-2- 5 74 (trifluoromethyl)pyridin-3-yl]-1- 1 58 (1H-1,2,4-triazol-1-yl)propan-2-ol 1.018 prothioconazole 10 61 5 30 2.5 0 1.020 spiroxamine 100 14 50 0 25 0 1.021 tebuconazole 10 44 5 34 2.5 4 4.005 pencycuron 100 4 50 0 25 0 13.001 fludioxonil 20 4 10 4 5 8 13.004 proquinazid 50 0 25 0 12.5 0 (I.01) + 1.020 1:20 5 + 100 95 77 (I.01) + 1.020 1:10 5 + 50 86 74 (I.01) + 1.020 1:5 5 + 25 86 74 (I.01) + 1.020 1:100 1 + 100 91 81 (I.01) + 1.020 1:50 1 + 50 94 78 (I.01) + 1.020 1:25 1 + 25 73 78 (I.01) + 1.021 1:2 5 + 10 86 85 (I.01) + 1.021 1:1 5 + 5 91 83 (I.01) + 1.021 2:1 5 + 2.5 83 75 (I.01) + 1.021 1:10 1 + 10 93 87 (I.01) + 1.021 1:5 1 + 5 93 85 (I.01) + 1.021 1:2.5 1 + 2.5 89 78 (I.01) + 4.005 1:20 5 + 100 86 75 (I.01) + 4.005 1:10 5 + 50 94 74 (I.01) + 4.005 1:5 5 + 25 94 74 (I.01) + 4.005 1:100 1 + 100 92 78 (I.01) + 4.005 1:50 1 + 50 81 78 (I.01) + 4.005 1:25 1 + 25 86 78 (I.01) + 13.001 1:4 5 + 20 96 75 (I.01) + 13.001 1:2 5 + 10 93 75 (I.01) + 13.001 1:1 5 + 5 94 76 (I.01) + 13.001 1:20 1 + 20 90 78 (I.01) + 13.001 1:10 1 + 10 94 78 (I.01) + 13.001 1:5 1 + 5 93 79 (I.01) + 13.004 1:10 5 + 50 90 74 (I.01) + 13.004 1:5 5 + 25 92 74 (I.01) + 13.004 1:2.5 5 + 12.5 79 74 (I.01) + 13.004 1:50 1 + 50 90 78 (I.01) + 13.004 1:25 1 + 25 92 78 (I.01) + 13.004 1:12.5 1 + 12.5 76 78 (I.59) + 1.018 1:2 5 + 10 88 90 (I.59) + 1.018 1:1 5 + 5 74 82 (I.59) + 1.018 2:1 5 + 2.5 87 74 (I.59) + 1.018 1:10 1 + 10 85 84 (I.59) + 1.018 1:5 1 + 5 91 70 (I.59) + 1.018 1:2.5 1 + 12.5 70 58 (I.59) + 1.020 1:20 5 + 100 85 77 (I.59) + 1.020 1:10 5 + 50 90 74 (I.59) + 1.020 1:5 5 + 25 86 74 (I.59) + 1.020 1:100 1 + 100 79 63 (I.59) + 1.020 1:50 1 + 50 79 58 (I.59) + 1.020 1:25 1 + 25 88 58 (I.59) + 1.021 1:2 5 + 10 87 85 (I.59) + 1.021 1:1 5 + 5 85 83 (I.59) + 1.021 2:1 5 + 2.5 89 75 (I.59) + 1.021 1:10 1 + 1090 90 76 (I.59) + 1.021 1:5 1 + 5 80 72 (I.59) + 1.021 1:2.5 1 + 2.5 74 59 (I.59) + 4.005 1:20 5 + 100 94 75 (I.59) + 4.005 1:10 5 + 50 94 74 (I.59) + 4.005 1:5 5 + 25 84 74 (I.59) + 4.005 1:100 1 + 100 81 59 (I.59) + 4.005 1:50 1 + 50 92 58 (I.59) + 4.005 1:25 1 + 25 81 58 (I.59) + 13.001 1:4 5 + 20 89 75 (I.59) + 13.001 1:2 5 + 10 94 75 (I.59) + 13.001 1:1 5 + 5 90 76 (I.59) + 13.001 1:20 1 + 20 92 59 (I.59) + 13.001 1:10 1 + 10 83 59 (I.59) + 13.001 1:5 1 + 5 88 61 (I.59) + 13.004 1:10 5 + 50 86 74 (I.59) + 13.004 1:5 5 + 25 84 74 (I.59) + 13.004 1:2.5 5 + 12.5 78 74 (I.59) + 13.004 1:50 1 + 50 83 58 (I.59) + 13.004 1:25 1 + 25 82 58 (I.59) + 13.004 1:12.5 1 + 12.5 91 58 *found = activity found **calc. = activity calculated using Colby's formula

TABLE-US-00018 TABLE E2 in vivo preventive test on Venturia (apples) Application rate of active Efficacy in % Active compounds compound in ppm a.i. found* calc.** (I.01) 2-[6-(4-chlorophenoxy)-2- 5 88 (trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4- 1 61 triazol-1-yl)propan-2-ol (I.59) 2-[6-(4-bromophenoxy)-2- 5 37 (trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4- 1 33 triazol-1-yl)propan-2-ol 5.004 chlorothalonil 50 93 25 14 12.5 24 5.013 mancozeb 50 95 25 18 12.5 0 5.018 propineb 20 100 10 94 5 54 12.003 metalaxyl 200 19 100 11 50 11 12.004 metalaxyl-M (mefenoxam) 200 30 100 11 50 0 15.008 cyflufenamid 20 4 10 0 5 0 (I.01) + 5.004 1:10 5 + 50 100 99 (I.01) + 5.004 1:5 5 + 25 99 89 (I.01) + 5.004 1:2.5 5 + 12.5 94 90 (I.01) + 5.004 1:50 1 + 50 100 97 (I.01) + 5.004 1:25 1 + 25 99 67 (I.01) + 5.004 1:12.5 1 + 12.5 88 70 (I.01) + 5.013 1:10 5 + 50 98 99 (I.01) + 5.013 1:5 5 + 25 98 90 (I.01) + 5.013 1:2.5 5 + 12.5 96 88 (I.01) + 5.013 1:50 1 + 50 99 98 (I.01) + 5.013 1:25 1 + 25 97 68 (I.01) + 5.013 1:12.5 1 + 12.5 95 61 (I.01) + 5.018 1:10 5 + 50 99 100 (I.01) + 5.018 1:5 5 + 25 99 99 (I.01) + 5.018 1:2.5 5 + 12.5 99 94 (I.01) + 5.018 1:50 1 + 50 100 100 (I.01) + 5.018 1:25 1 + 25 98 98 (I.01) + 5.018 1:12.5 1 + 12.5 96 82 (I.01) + 12.003 1:40 5 + 200 88 90 (I.01) + 12.003 1:20 5 + 100 82 89 (I.01) + 12.003 1:10 5 + 50 81 89 (I.01) + 12.003 1:200 1 + 200 78 69 (I.01) + 12.003 1:100 1 + 100 74 66 (I.01) + 12.003 1:50 1 + 50 70 66 (I.01) + 12.004 1:40 5 + 200 80 91 (I.01) + 12.004 1:20 5 + 100 84 89 (I.01) + 12.004 1:10 5 + 50 86 88 (I.01) + 12.004 1:200 1 + 200 93 73 (I.01) + 12.004 1:100 1 + 100 78 66 (I.01) + 12.004 1:50 1 + 50 60 61 (I.59) + 5.004 1:10 5 + 50 99 96 (I.59) + 5.004 1:5 5 + 25 99 45 (I.59) + 5.004 1:2.5 5 + 12.5 96 52 (I.59) + 5.004 1:50 1 + 50 98 95 (I.59) + 5.004 1:25 1 + 25 98 42 (I.59) + 5.004 1:12.5 1 + 12.5 93 49 (I.59) + 5.013 1:10 5 + 50 99 97 (I.59) + 5.013 1:5 5 + 25 98 48 (I.59) + 5.013 1:2.5 5 + 12.5 83 37 (I.59) + 5.013 1:50 1 + 50 100 97 (I.59) + 5.013 1:25 1 + 25 96 44 (I.59) + 5.013 1:12.5 1 + 12.5 90 33 (I.59) + 5.018 1:10 5 + 50 100 100 (I.59) + 5.018 1:5 5 + 25 100 96 (I.59) + 5.018 1:2.5 5 + 12.5 95 71 (I.59) + 5.018 1:50 1 + 50 99 100 (I.59) + 5.018 1:25 1 + 25 99 96 (I.59) + 5.018 1:12.5 1 + 12.5 96 69 (I.59) + 12.003 1:40 5 + 200 93 49 (I.59) + 12.003 1:20 5 + 100 86 44 (I.59) + 12.003 1:10 5 + 50 92 44 (I.59) + 12.003 1:200 1 + 200 91 45 (I.59) + 12.003 1:100 1 + 100 85 40 (I.59) + 12.003 1:50 1 + 50 84 40 (I.59) + 12.004 1:40 5 + 200 91 46 (I.59) + 12.004 1:20 5 + 100 94 44 (I.59) + 12.004 1:10 5 + 50 84 37 (I.59) + 12.004 1:200 1 + 200 80 53 (I.59) + 12.004 1:100 1 + 100 81 40 (I.59) + 12.004 1:50 1 + 50 81 33 (I.59) + 15.008 1:4 5 + 20 79 39 (I.59) + 15.008 1:2 5 + 10 81 37 (I.59) + 15.008 1:1 5 + 5 75 37 (I.59) + 15.008 1:20 1 + 20 79 35 (I.59) + 15.008 1:10 1 + 10 65 33 (I.59) + 15.008 1:5 1 + 5 69 33 *found = activity found **calc. = activity calculated using Colby's formula

Example F: In Vivo Preventive Blumeria Test (Barley)

[0674] Solvent: 49 parts by weight of N,N-dimethylacetamide [0675] Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0676] To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

[0677] To test for preventive activity, young plants are sprayed with the preparation of active compound or active compound combination at the stated rate of application. After the spray coating has been dried, the plants are dusted with spores of Blumeria graminis f.sp. hordei. The plants are placed in the greenhouse at a temperature of approximately 18 C. and a relative atmospheric humidity of approximately 80% to promote the development of mildew pustules.

[0678] The test is evaluated 7 days after the inoculation. 0% means an efficacy which corresponds to that of the untreated control, while an efficacy of 100% means that no disease is observed.

[0679] The table below clearly shows that the observed activity of the active compound combination according to the invention is greater than the calculated activity, i.e. a synergistic effect is present.

TABLE-US-00019 TABLE F1 in vivo preventive Blumeria test (barley) Application rate of active Efficacy in % Active compounds compound in ppm a.i. found* calc.** (I.59) 2-[6-(4-bromophenoxy)-2- 100 93 (trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4- 50 57 triazol-1-yl)propan-2-ol 25 57 2.005 fluopyram 60 29 30 0 15 0 (I.59) + 2.005 1.67:1 100 + 600 100 95 (I.59) + 2.005 1.67:1 50 + 30 100 57 (I.59) + 2.005 1.67:1 25 + 15 29 57 *found = activity found **calc. = activity calculated using Colby's formula

TABLE-US-00020 TABLE F2 in vivo preventive Blumeria test (barley) Application rate of active com- Efficacy in % Active compounds pound in ppm a.i. found* calc.** (I.59) 2-[6-(4-bromophenoxy)-2- 100 78 (trifluoromethyl)pyridin-3-yl]-1- 50 56 (1H-1,2,4-triazol-1-yl)propan-2-ol 25 22 1.020 spiroxamine 250 100 125 89 62.5 33 5.004 chlorothalonil 250 44 125 44 62.5 22 (I.59) + 1.020 1:2.5 100 + 250 100 100 (I.59) + 1.020 1:2.5 50 + 125 100 95 (I.59) + 1.020 1:2.5 25 + 62.5 67 48 (I.59) + 5.004 1:2.5 100 + 250 100 88 (I.59) + 5.004 1:2.5 50 + 125 100 75 (I.59) + 5.004 1:2.5 25 + 62.5 44 40 *found = activity found **calc. = activity calculated using Colby's formula

Example G: In Vivo Preventive Leptosphaeria nodorum Test (Wheat)

[0680] Solvent: 49 parts by weight of N,N-dimethylacetamide [0681] Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0682] To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

[0683] To test for preventive activity, young plants are sprayed with the preparation of active compound or active compound combination at the stated rate of application. After the spray coating has been dried, the plants are sprayed with a spore suspension of Leptosphaeria nodorum. The plants remain for 48 hours in an incubation cabinet at approximately 20 C. and a relative atmospheric humidity of approximately 100%. The plants are placed in the greenhouse at a temperature of approximately 25 C. and a relative atmospheric humidity of approximately 80%.

[0684] The test is evaluated 8 days after the inoculation. 0% means an efficacy which corresponds to that of the untreated control, while an efficacy of 100% means that no disease is observed.

[0685] The table below clearly shows that the observed activity of the active compound combination according to the invention is greater than the calculated activity, i.e. a synergistic effect is present.

TABLE-US-00021 TABLE G1 in vivo preventive Leptosphaeria nodorum test (wheat) Application rate of active Efficacy in % Active compounds compound in ppm a.i. found* calc.** (I.01) 2-[6-(4-chlorophenoxy)-2- 80 86 (trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4- 40 57 triazol-1-yl)propan-2-ol 20 43 4.005 pencycuron 250 29 125 14 62.5 14 5.013 mancozeb 1000 14 500 14 250 14 12.003 metalaxyl 1000 0 500 0 250 29 12.004 metalaxyl-M (mefenoxam) 1000 14 500 0 250 0 13.004 proquinazid 1000 14 500 14 250 0 15.008 cyflufenamid 1000 0 500 0 250 0 (I.01) + 4.005 1:3.125 80 + 250 93 90 (I.01) + 4.005 1:3.125 40 + 125 86 63 (I.01) + 4.005 1:3.125 20 + 62.5 57 51 (I.01) + 5.013 1:12.5 80 + 1000 100 88 (I.01) + 5.013 1:12.5 40 + 500 93 63 (I.01) + 5.013 1:12.5 20 + 250 43 51 (I.01) + 12.003 1:12.5 80 + 1000 93 86 (I.01) + 12.003 1:12.5 40 + 500 86 57 (I.01) + 12.003 1:12.5 20 + 250 57 59 (I.01) + 12.004 1:12.5 80 + 1000 100 88 (I.01) + 12.004 1:12.5 40 + 500 93 57 (I.01) + 12.004 1:12.5 20 + 250 71 43 (I.01) + 13.004 1:12.5 80 + 1000 100 88 (I.01) + 13.004 1:12.5 40 + 500 93 63 (I.01) + 13.004 1:12.5 20 + 250 86 43 (I.01) + 15.008 1:12.5 80 + 1000 93 86 (I.01) + 15.008 1:12.5 40 + 500 71 57 (I.01) + 15.008 1:12.5 20 + 250 29 43 *found = activity found **calc. = activity calculated using Colby's formula

Example H: In Vivo Preventive Puccinia triticina Test (Wheat)

[0686] Solvent: 49 parts by weight of N,N-dimethylacetamide [0687] Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0688] To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

[0689] To test for preventive activity, young plants are sprayed with the preparation of active compound or active compound combination at the stated rate of application. After the spray coating has been dried, the plants are sprayed with a spore suspension of Puccinia triticina. The plants remain for 48 hours in an incubation cabinet at approximately 20 C. and a relative atmospheric humidity of approximately 100%. The plants are placed in the greenhouse at a temperature of approximately 20 C. and a relative atmospheric humidity of approximately 80%.

[0690] The test is evaluated 8 days after the inoculation. 0% means an efficacy which corresponds to that of the untreated control, while an efficacy of 100% means that no disease is observed.

[0691] The table below clearly shows that the observed activity of the active compound combination according to the invention is greater than the calculated activity, i.e. a synergistic effect is present.

TABLE-US-00022 TABLE H1 in vivo preventive Puccinia triticina test (wheat) Application rate of active Efficacy in % Active compounds compound in ppm a.i. found* calc.** (I.01) 2-[6-(4-chlorophenoxy)-2- 80 67 (trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4- 40 33 triazol-1-yl)propan-2-ol 20 22 1.012 ipconazole 80 89 40 67 20 0 1.018 prothioconazole 100 0 50 0 25 0 2.002 bixafen 100 67 50 33 25 22 2.005 fluopyram 60 33 30 0 15 0 2.038 N-(5-chloro-2-isopropylbenzyl)-N- 30 33 cyclopropyl-3-(difluoromethyl)-5-fluoro-1- 15 33 methyl-1H-pyrazole-4-carboxamide 7.5 33 3.020 trifloxystrobin 10 11 5 0 2.5 0 3.025 (3S,6S,7R,8R)-8-benzyl-3-[({3- 150 89 [(isobutyryloxy)methoxy]-4-methoxypyridin-2- 75 67 yl}carbonyl)amino]-6-methyl-4,9-dioxo-1,5- 37.5 22 dioxonan-7-yl 2-methylpropanoate 13.001 fludioxonil 80 22 40 0 20 0 (I.01) + 1.012 1:1 80 + 80 94 96 (I.01) + 1.012 1:1 40 + 40 94 78 (I.01) + 1.012 1:1 20 + 20 56 22 (I.01) + 1.018 1:1.25 80 + 100 89 67 (I.01) + 1.018 1:1.25 40 + 50 44 33 (I.01) + 1.018 1:1.25 20 + 25 0 22 (I.01) + 2.002 1:1.25 80 + 100 100 89 (I.01) + 2.002 1:1.25 40 + 50 67 56 (I.01) + 2.002 1:1.25 20 + 25 33 40 (I.01) + 2.005 1.33:1 80 + 60 94 78 (I.01) + 2.005 1.33:1 40 + 30 67 33 (I.01) + 2.005 1.33:1 20 + 15 33 22 (I.01) + 2.038 1.67:1 80 + 30 100 78 (I.01) + 2.038 1.67:1 40 + 15 94 56 (I.01) + 2.038 1.67:1 20 + 7.5 56 48 (I.01) + 3.020 8:1 80 + 10 89 70 (I.01) + 3.020 8:1 40 + 5 67 33 (I.01) + 3.020 8:1 20 + 2.5 0 22 (I.01) + 3.025 1:1.875 80 + 150 94 96 (I.01) + 3.025 1:1.875 40 + 75 94 78 (I.01) + 3.025 1:1.875 20 + 37.5 33 40 (I.01) + 13.001 1:1 80 + 80 89 74 (I.01) + 13.001 1:1 40 + 40 56 33 (I.01) + 13.001 1:1 20 + 20 22 22 *found = activity found **calc. = activity calculated using Colby's formula

TABLE-US-00023 TABLE H2 in vivo preventive Puccinia triticina test (wheat) Application rate of active Efficacy in % Active compounds compound in ppm a.i. found* calc.** (I.59) 2-[6-(4-bromophenoxy)-2- 100 78 (trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4- 50 44 triazol-1-yl)propan-2-ol 25 11 1.012 ipconazole 80 100 40 44 20 0 1.018 prothioconazole 100 0 50 0 25 0 1.021 tebuconazole 100 89 50 78 25 22 2.005 fluopyram 60 0 30 0 15 0 2.017 penflufen 80 100 40 89 20 56 2.038 N-(5-chloro-2-isopropylbenzyl)-N- 30 44 cyclopropyl-3-(difluoromethyl)-5-fluoro-1- 15 33 methyl-1H-pyrazole-4-carboxamide 7.5 22 13.001 fludioxonil 80 0 40 0 20 0 (I.59) + 1.012 1.25:1 100 + 80 100 100 (I.59) + 1.012 1.25:1 50 + 40 100 69 (I.59) + 1.012 1.25:1 25 + 20 22 11 (I.59) + 1.018 1:1 100 + 100 100 78 (I.59) + 1.018 1:1 50 + 50 44 44 (I.59) + 1.018 1:1 25 + 25 22 11 (I.59) + 1.021 1:1 100 + 100 100 98 (I.59) + 1.021 1:1 50 + 50 100 88 (I.59) + 1.021 1:1 25 + 25 22 31 (I.59) + 2.005 1.67:1 100 + 60 94 78 (I.59) + 2.005 1.67:1 50 + 30 67 44 (I.59) + 2.005 1.67:1 25 + 15 0 11 (I.59) + 2.017 1.25:1 100 + 80 100 100 (I.59) + 2.017 1.25:1 50 + 40 100 94 (I.59) + 2.017 1.25:1 25 + 20 89 60 (I.59) + 2.038 3.33:1 100 + 30 89 88 (I.59) + 2.038 3.33:1 50 + 15 89 63 (I.59) + 2.038 3.33:1 25 + 7.5 44 31 (I.59) + 13.001 1.25:1 100 + 80 100 78 (I.59) + 13.001 1.25:1 50 + 40 78 44 (I.59) + 13.001 1.25:1 25 + 20 22 11 *found = activity found **calc. = activity calculated using Colby's formula

TABLE-US-00024 TABLE H3 in vivo preventive Puccinia triticina test (wheat) Application rate of active Efficacy in % Active compounds compound in ppm a.i. found* calc.** (I.01) 2-[6-(4-chlorophenoxy)-2- 80 60 (trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4- 40 50 triazol-1-yl)propan-2-ol 20 30 4.005 pencycuron 250 0 125 0 62.5 0 5.004 chlorothalonil 250 40 125 0 62.5 0 12.003 metalaxyl 1000 30 500 0 250 0 12.004 metalaxyl-M (mefenoxam) 1000 0 500 0 250 0 13.004 proquinazid 1000 0 500 0 250 0 (I.01) + 4.005 1:3:125 80 + 250 80 60 (I.01) + 4.005 1:3:125 40 + 125 70 50 (I.01) + 4.005 1:3:125 20 + 62.5 20 30 (I.01) + 5.004 1:3:125 80 + 250 100 76 (I.01) + 5.004 1:3:125 40 + 125 80 50 (I.01) + 5.004 1:3:125 20 + 62.5 50 30 (I.01) + 12.003 1:12:5 80 + 1000 70 72 (I.01) + 12.003 1:12:5 40 + 500 70 50 (I.01) + 12.003 1:12:5 20 + 250 40 30 (I.01) + 12.004 1:12:5 80 + 1000 90 60 (I.01) + 12.004 1:12:5 40 + 500 80 50 (I.01) + 12.004 1:12:5 20 + 250 60 30 (I.01) + 13.004 1:12:5 80 + 1000 90 60 (I.01) + 13.004 1:12:5 40 + 500 90 50 (I.01) + 13.004 1:12:5 20 + 250 60 30 *found = activity found **calc. = activity calculated using Colby's formula

TABLE-US-00025 TABLE 114 in vivo preventive Puccinia triticina test (wheat) Application rate of active Efficacy in % Active compounds compound in ppm a.i. found* calc.** (I.59) 2-[6-(4-bromophenoxy)-2- 100 94 (trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4- 50 56 triazol-1-yl)propan-2-ol 25 11 1.020 spiroxamine 250 33 125 33 62.5 11 4.005 pencycuron 250 33 125 11 62.5 0 5.004 chlorothalonil 250 33 125 33 62.5 0 12.003 metalaxyl 1000 44 500 44 250 11 12.004 metalaxyl-M (mefenoxam) 1000 44 500 22 250 0 13.004 proquinazid 1000 33 500 33 250 11 15.008 cyflufenamid 1000 22 500 0 250 0 15.047 quinofumelin 500 22 250 11 125 11 (I.59) + 1.020 1:2.5 100 + 250 100 96 (I.59) + 1.020 1:2.5 50 + 125 89 70 (I.59) + 1.020 1:2.5 25 + 62.5 33 21 (I.59) + 4.005 1:2.5 100 + 250 100 96 (I.59) + 4.005 1:2.5 50 + 125 94 60 (I.59) + 4.005 1:2.5 25 + 62.5 56 11 (I.59) + 5.004 1:2.5 100 + 250 100 96 (I.59) + 5.004 1:2.5 50 + 125 100 70 (I.59) + 5.004 1:2.5 25 + 62.5 44 11 (I.59) + 12.003 1:10 100 + 1000 100 97 (I.59) + 12.003 1:10 50 + 500 94 75 (I.59) + 12.003 1:10 25 + 250 78 21 (I.59) + 12.004 1:10 100 + 1000 100 97 (I.59) + 12.004 1:10 50 + 500 94 65 (I.59) + 12.004 1:10 25 + 250 89 11 (I.59) + 13.004 1:10 100 + 1000 100 96 (I.59) + 13.004 1:10 50 + 500 100 70 (I.59) + 13.004 1:10 25 + 250 33 21 (I.59) + 15.008 1:10 100 + 1000 94 96 (I.59) + 15.008 1:10 50 + 500 94 56 (I.59) + 15.008 1:10 25 + 250 44 11 (I.59) + 15.047 1:5 100 + 500 94 96 (I.59) + 15.047 1:5 50 + 250 89 60 (I.59) + 15.047 1:5 25 + 125 22 21 *found = activity found **calc. = activity calculated using Colby's formula

Example I: In Vivo Preventive Septoria tritici Test (Wheat)

[0692] Solvent: 49 parts by weight of N,N-dimethylacetamide [0693] Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0694] To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

[0695] To test for preventive activity, young plants are sprayed with the preparation of active compound or active compound combination at the stated rate of application. After the spray coating has been dried, the plants are sprayed with a spore suspension of Septoria tritici. The plants remain for 48 hours in an incubation cabinet at approximately 20 C. and a relative atmospheric humidity of approximately 100% and afterwards for 60 hours at approximately 15 C. in a translucent incubation cabinet at a relative atmospheric humidity of approximately 100%. The plants are placed in the greenhouse at a temperature of approximately 15 C. and a relative atmospheric humidity of approximately 80%.

[0696] The test is evaluated 21 days after the inoculation. 0% means an efficacy which corresponds to that of the untreated control, while an efficacy of 100% means that no disease is observed.

[0697] The table below clearly shows that the observed activity of the active compound combination according to the invention is greater than the calculated activity, i.e. a synergistic effect is present.

TABLE-US-00026 TABLE I1 in vivo preventive Septoria tritici test (wheat) Application rate of active Efficacy in % Active compounds compound in ppm a.i. found* calc.** (I.01) 2-[6-(4-chlorophenoxy)-2- 80 100 (trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4-triazol-1-yl) 40 63 propan-2-ol 20 13 2.005 fluopyram 60 88 30 38 15 13 2.027 3-(difluoromethyl)-1-methyl-N-(1,1,3- 250 88 trimethyl-2,3-dihydro-1H-inden-4-yl)-1H- 125 63 pyrazole-4-carboxamide 62.5 25 3.025 (3S,6S,7R,8R)-8-benzyl-3-[({3- 150 63 [(isobutyryloxy)methoxy]-4-methoxypyridin-2- 75 13 yl}carbonyl)amino]-6-methyl-4,9-dioxo-1,5- 37.5 13 dioxonan-7-yl 2-methylpropanoate (I.01) + 2.005 1.33:1 80 + 60 100 100 (I.01) + 2.005 1.33:1 40 + 30 88 77 (I.01) + 2.005 1.33:1 20 + 15 38 23 (I.01) + 2.027 1:3.125 80 + 250 100 100 (I.01) + 2.027 1:3.125 40 + 125 100 86 (I.01) + 2.027 1:3.125 20 + 62.5 63 34 (I.01) + 3.025 1:1.875 80 + 150 100 100 (I.01) + 3.025 1:1.875 40 + 75 94 67 (I.01) + 3.025 1:1.875 20 + 37.5 13 23 *found = activity found **calc. = activity calculated using Colby's formula

TABLE-US-00027 TABLE I2 in vivo preventive Septoria tritici test (wheat) Application rate of active Efficacy in % Active compounds compound in ppm a.i. found* calc.** (I.59) 2-[6-(4-chlorophenoxy)-2- 100 86 (trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4-triazol-1-yl) 50 0 propan-2-ol 25 0 1.012 ipconazole 80 0 40 0 20 0 1.018 prothioconazole 100 43 50 14 25 0 1.021 tebuconazole 100 0 50 0 25 0 2.005 fluopyram 60 71 30 29 15 29 2.017 penflufen 80 0 40 0 20 29 2.027 3-(difluoromethyl)-1-methyl-N-(1,1,3- 250 43 trimethyl-2,3-dihydro-1H-inden-4-yl)-1H- 125 43 pyrazole-4-carboxamide 62.5 29 3.020 trifloxystrobin 10 29 5 29 2.5 29 3.025 (3S,6S,7R,8R)-8-benzyl-3-[({3- 150 71 [(isobutyryloxy)methoxy]-4-methoxypyridin-2- 75 71 yl]}carbonyl)amino]-6-methyl-4,9-dioxo-1,5- 37.5 14 dioxonan-7-yl 2-methylpropanoate 13.001 fludioxonil 80 29 40 29 20 29 (I.59) + 1.012 1.25:1 100 + 80 86 86 (I.59) + 1.012 1.25:1 50 + 40 57 0 (I.59) + 1.012 1.25:1 25 + 20 0 0 (I.59) + 1.018 1:1 100 + 100 86 92 (I.59) + 1.018 1:1 50 + 50 57 14 (I.59) + 1.018 1:1 25 + 25 43 0 (I.59) + 1.021 1:1 100 + 100 93 86 (I.59) + 1.021 1:1 50 + 50 71 0 (I.59) + 1.021 1:1 25 + 25 57 0 (I.59) + 2.005 1.67:1 100 + 60 100 96 (I.59) + 2.005 1.67:1 50 + 30 86 29 (I.59) + 2.005 1.67:1 25 + 15 43 29 (I.59) + 2.017 1.25:1 100 + 80 86 86 (I.59) + 2.017 1.25:1 50 + 40 86 0 (I.59) + 2.017 1.25:1 25 + 20 0 29 (I.59) + 2.027 1:2.5 100 + 250 100 92 (I.59) + 2.027 1:2.5 50 + 125 57 43 (I.59) + 2.027 1:2.5 25 + 62.5 43 29 (I.59) + 3.020 10:1 100 + 10 93 90 (I.59) + 3.020 10:1 50 + 5 57 29 (I.59) + 3.020 10:1 25 + 6.5 29 29 (I.59) + 3.025 1:1.5 100 + 150 100 96 (I.59) + 3.025 1:1.5 50 + 75 86 71 (I.59) + 3.025 1:1.5 25 + 37.5 71 14 (I.59) + 13.001 1.25:1 100 + 80 93 90 (I.59) + 13.001 1.25:1 50 + 40 93 29 (I.59) + 13.001 1.25:1 25 + 20 57 29 *found = activity found **calc. = activity calculated using Colby's formula

TABLE-US-00028 TABLE I3 in vivo preventive Septoria tritici test (wheat) Application rate of active Efficacy in % Active compounds compound in ppm a.i. found* calc.** (I.01) 2-[6-(4-chlorophenoxy)-2- 80 71 (trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4-triazol-1-yl) 40 43 propan-2-ol 20 29 1.020 spiroxamine 250 57 125 14 62.5 0 4.005 pencycuron 250 0 125 0 62.5 0 5.004 chlorothalonil 250 14 125 0 62.5 0 5.013 mancozeb 1000 29 500 29 250 29 12.003 metalaxyl 1000 0 500 0 250 0 12.004 metalaxyl-M (mefenoxam) 1000 0 500 0 250 0 13.004 proquinazid 1000 0 500 0 250 0 15.008 cyflufenamid 1000 29 500 29 250 14 15.047 quinofumelin 500 0 250 0 125 0 (I.01) + 1.020 1:3.125 80 + 250 93 88 (I.01) + 1.020 1:3.125 40 + 125 71 51 (I.01) + 1.020 1:3.125 20 + 62.5 43 29 (I.01) + 4.005 1:3.125 80 + 250 100 71 (I.01) + 4.005 1:3.125 40 + 125 93 43 (I.01) + 4.005 1:3.125 20 + 62.5 71 29 (I.01) + 5.004 1:3.125 80 + 250 100 76 (I.01) + 5.004 1:3.125 40 + 125 86 43 (I.01) + 5.004 1:3.125 20 + 62.5 43 29 (I.01) + 5.013 1:12.5 80 + 1000 100 80 (I.01) + 5.013 1:12.5 40 + 500 93 59 (I.01) + 5.013 1:12.5 20 + 250 29 49 (I.01) + 12.003 1:12.5 80 + 1000 100 71 (I.01) + 12.003 1:12.5 40 + 500 100 43 (I.01) + 12.003 1:12.5 20 + 250 71 29 (I.01) + 12.004 1:12.5 80 + 1000 100 71 (I.01) + 12.004 1:12.5 40 + 500 100 43 (I.01) + 12.004 1:12.5 20 + 250 71 29 (I.01) + 13.004 1:12.5 80 + 1000 100 71 (I.01) + 13.004 1:12.5 40 + 500 93 43 (I.01) + 13.004 1:12.5 20 + 250 71 29 (I.01) + 15.008 1:12.5 80 + 1000 100 80 (I.01) + 15.008 1:12.5 40 + 500 86 59 (I.01) + 15.008 1:12.5 20 + 250 29 39 (I.01) + 15.047 1:6.25 80 + 500 100 71 (I.01) + 15.047 1:6.25 40 + 250 71 43 (I.01) + 15.047 1:6.25 20 + 125 0 29 *found = activity found **calc. = activity calculated using Colby's formula

Example J: In Vitro-Test with Fungal Microorganisms

[0698] Wells of 96-well microtiter plates are filled with 10 l of a preparation of test compound or compound combination in methanol+emulsifier alkylaryl-polyglycol-ether. Thereafter, the solvent is evaporated in a hood. At the next step, into each well 100 l of liquid potato dextrose medium is given, that has been amended with an appropriate concentration of spores or mycelium suspension of the test fungus.

[0699] With the aid of a photometer the extinction in all wells is measured at the wavelength of 620 nm.

[0700] The microtiter plates are incubated at 20 C. and 85% relative humidity. The inhibition of growth is determined again photometrically 3-5 days after the application. Efficacy is calculated in relation to the untreated control, 0% efficacy means fungal growth as high as in untreated control while 100% efficacy means no fungal growth is measured.

TABLE-US-00029 TABLE J1 in vitro-Test with Alternaria alternata Ex. 1.018 Ex. I.01 prothioconazole Colby expected (ppm) (ppm) Ratio Efficacy % value % 0.04 0 0.2 91 0.04 0.2 1:5 99 91

TABLE-US-00030 TABLE J2 in vitro-Test with Alternaria alternata Ex. 1.021 Ex. I.01 tebuconazole Colby expected (ppm) (ppm) Ratio Efficacy % value % 0.2 10 0.04 0 0.008 12 1 36 0.2 24 0.04 19 0.2 1 1:5 100 42 0.04 0.2 1:5 44 24 0.008 0.04 1:5 43 29

TABLE-US-00031 TABLE J3 in vitro-Test with Alternaria alternata Ex. 2.002 Ex. I.01 bixafen Colby expected (ppm) (ppm) Ratio Efficacy % value % 0.2 0 0.04 0 1 88 0.2 84 0.2 1 1:5 90 88 0.04 0.2 1:5 91 84

TABLE-US-00032 TABLE J4 in vitro-Test with Alternaria alternata Ex. 1.015 Ex. I.59 paclobutrazol Colby expected (ppm) (ppm) Ratio Efficacy % value % 0.2 38 1 0 0.2 1 1:5 85 38

TABLE-US-00033 TABLE J5 in vitro-Test with Alternaria alternata Ex. 1.018 Ex. I.59 prothioconazole Colby expected (ppm) (ppm) Ratio Efficacy % value % 0.008 44 0.04 0 0.008 0.04 1:5 72 44

TABLE-US-00034 TABLE J6 in vitro-Test with Alternaria alternata Ex. 2.002 Ex. I.59 bixafin Colby expected (ppm) (ppm) Ratio Efficacy % value % 0.04 0 0.008 0 0.2 57 0.04 55 0.04 0.2 1:5 83 57 0.008 0.04 1:5 66 55

TABLE-US-00035 TABLE J7 in vitro-Test with Alternaria alternata Ex. 13.004 Ex. I.59 proquinazid Colby expected (ppm) (ppm) Ratio Efficacy % value % 0.04 50 0.008 44 4 0 0.8 0 0.04 4 1:100 53 50 0.008 0.8 1:100 55 44

TABLE-US-00036 TABLE J8 in vitro-Test with Botrytis cinerea Ex. 1.020 Ex. I.59 spiroxamine Colby expected (ppm) (ppm) Ratio Efficacy % value % 0.2 1 0.04 0 20 9 4 7 0.2 20 1:100 83 10 0.04 4 1:100 27 7

TABLE-US-00037 TABLE J9 in vitro-Test with Botrytis cinerea Ex. 2.002 Ex. I.59 bixafin Colby expected (ppm) (ppm) Ratio Efficacy % value % 1 100 0.2 0 5 91 1 63 1 5 1:5 99 100 0.2 1 1:5 70 63

TABLE-US-00038 TABLE J10 in vitro-Test with Botrytis cinerea Ex. I.59 Ex. 15.047 Colby expected (ppm) (ppm) Ratio Efficacy % value % 1 100 0.2 0 5 0 1 0 1 5 1:5 100 100 0.2 1 1:5 77 0

TABLE-US-00039 TABLE J11 in vitro-Test with Fusarium culmorum Ex. 1.012 Ex. I.01 ipconazole Colby expected (ppm) (ppm) Ratio Efficacy % value % 1 19 0.2 26 5 99 1 96 1 5 1:5 100 99 0.2 1 1:5 99 97

TABLE-US-00040 TABLE J12 in vitro-Test with Fusarium culmorum Ex. 1.018 Ex. I.01 prothioconazole Colby expected (ppm) (ppm) Ratio Efficacy % value % 0.04 44 0.2 99 0.04 0.2 1:5 100 99

TABLE-US-00041 TABLE J13 in vitro -Test with Fusarium culmorum Ex. 1.012 Ex. I.59 ipconazole Colby expected (ppm) (ppm) Ratio Efficacy % value % 0.04 0 0.008 0 0.2 13 0.04 7 0.04 0.2 1:5 85 13 0.008 0.04 1:5 31 7

TABLE-US-00042 TABLE J14 in vitro -Test with Fusarium culmorum Ex. I.59 Ex. 15.047 Colby expected (ppm) (ppm) Ratio Efficacy % value % 0.04 0 0.008 0 0.2 100 0.04 83 0.04 0.2 1:5 100 100 0.008 0.04 1:5 90 83

TABLE-US-00043 TABLE J15 in vitro -Test with Leptosphaeria nodorum Ex. 5.004 Ex. I.01 chlorothalonil Colby expected (ppm) (ppm) Ratio Efficacy % value % 0.008 91 0.04 0 0.008 0.04 1:5 99 91

TABLE-US-00044 TABLE J16 in vitro -Test with Pyrenophora teres Ex. 1.018 Ex. I.01 prothioconazole Colby expected (ppm) (ppm) Ratio Efficacy % value % 0.04 26 0.2 22 0.04 0.2 1:5 56 42

TABLE-US-00045 TABLE J17 in vitro -Test with Pyrenophora teres Ex. 2.002 Ex. I.01 bixafen Colby expected (ppm) (ppm) Ratio Efficacy % value % 1 5 0.2 0 0.04 0 5 72 1 60 0.2 46 1 5 1:5 91 73 0.2 1 1:5 68 60 0.04 0.2 1:5 51 46

TABLE-US-00046 TABLE J18 in vitro -Test with Pyrenophora teres Ex. I.01 Ex. 2.027 Colby expected (ppm) (ppm) Ratio Efficacy % value % 0.2 0 0.04 0 20 62 4 43 0.2 20 1:100 74 62 0.04 4 1:100 48 43

TABLE-US-00047 TABLE J19 in vitro -Test with Pyrenophora teres Ex. I.01 Ex. 2.038 Colby expected (ppm) (ppm) Ratio Efficacy % value % 0.2 0 0.04 0 0.008 0 20 55 4 82 0.8 57 0.2 20 1:100 92 55 0.04 4 1:100 88 82 0.008 0.8 1:100 68 57

TABLE-US-00048 TABLE J20 in vitro -Test with Pyrenophora teres Ex. 3.020 Ex. I.01 trifloxystrobin Colby expected (ppm) (ppm) Ratio Efficacy % value % 1 5 5 6 1 5 1:5 32 11

TABLE-US-00049 TABLE J21 in vitro -Test with Pyrenophora teres Ex. I.01 Ex. 3.025 Colby expected (ppm) (ppm) Ratio Efficacy % value % 1 5 100 10 1 100 1:100 53 15

TABLE-US-00050 TABLE J22 in vitro -Test with Pyrenophora teres Ex. 4.005 Ex. I.01 pencycuron Colby expected (ppm) (ppm) Ratio Efficacy % value % 1 21 0.2 19 100 5 20 17 1 100 1:100 51 25 0.2 20 1:100 35 33

TABLE-US-00051 TABLE J23 in vitro -Test with Pyrenophora teres Ex. 5.013 Ex. I.01 mancozeb Colby expected (ppm) (ppm) Ratio Efficacy % value % 0.2 14 0.04 1 20 81 4 25 0.2 20 1:100 91 84 0.04 4 1:100 32 26

TABLE-US-00052 TABLE J24 in vitro -Test with Pyrenophora teres Ex. 5.018 Ex. I.01 propineb Colby expected (ppm) (ppm) Ratio Efficacy % value % 0.04 1 4 22 0.04 4 1:100 45 23

TABLE-US-00053 TABLE J25 in vitro -Test with Pyrenophora teres Ex. I.01 Ex. 15.047 Colby expected (ppm) (ppm) Ratio Efficacy % value % 0.2 14 0.04 1 0.008 0 1 64 0.2 76 0.04 28 0.2 1 1:5 81 69 0.04 0.2 1:5 82 76 0.008 0.04 1:5 45 28

TABLE-US-00054 TABLE J26 in vitro -Test with Pyrenophora teres Ex. 5.013 Ex. I.59 mancozeb Colby expected (ppm) (ppm) Ratio Efficacy % value % 1 0 0.04 0 100 83 4 76 1 100 1:100 94 83 0.04 4 1:100 93 76

TABLE-US-00055 TABLE J27 in vitro -Test with Pyricularia oryzae Ex. 1.021 Ex. I.01 tebuconazole Colby expected (ppm) (ppm) Ratio Efficacy % value % 0.2 7 0.04 0 1 87 0.2 87 0.2 1 1:5 96 88 0.04 0.2 1:5 100 87

TABLE-US-00056 TABLE J28 in vitro -Test with Pyricularia oryzae Ex. 2.017 Ex. I.01 penflufen Colby expected (ppm) (ppm) Ratio Efficacy % value % 1 61 0.2 0 5 91 1 44 1 5 1:5 100 96 0.2 1 1:5 72 44

TABLE-US-00057 TABLE J29 in vitro -Test with Pyricularia oryzae Ex. I.01 Ex. 2.038 Colby expected (ppm) (ppm) Ratio Efficacy % value % 0.2 0 0.04 1 0.008 4 20 75 4 51 0.8 0 0.2 20 1:100 96 75 0.04 4 1:100 63 51 0.008 0.8 1:100 23 4

TABLE-US-00058 TABLE J30 in vitro -Test with Pyricularia oryzae Ex. 3.020 Ex. I.01 trifloxystrobin Colby expected (ppm) (ppm) Ratio Efficacy % value % 1 61 5 98 1 5 1:5 100 99

TABLE-US-00059 TABLE J31 in vitro -Test with Pyricularia oryzae Ex. I.01 Ex. 3.025 Colby expected (ppm) (ppm) Ratio Efficacy % value % 0.2 0 0.04 1 0.008 4 20 100 4 84 0.8 91 0.2 20 1:100 100 100 0.04 4 1:100 97 84 0.008 0.8 1:100 100 91

TABLE-US-00060 TABLE J32 in vitro -Test with Pyricularia oryzae Ex. 13.001 Ex. I.01 fludioxonil Colby expected (ppm) (ppm) Ratio Efficacy % value % 1 95 0.2 7 5 89 1 87 1 5 1:5 100 99 0.2 1 1:5 97 88

TABLE-US-00061 TABLE J33 in vitro -Test with Pyricularia oryzae Ex. 1.021 Ex. I.59 tebuconazole Colby expected (ppm) (ppm) Ratio Efficacy % value % 0.2 0 1 89 0.2 1 1:5 91 89

TABLE-US-00062 TABLE J34 in vitro -Test with Pyricularia oryzae Ex. I.59 Ex. 3.025 Colby expected (ppm) (ppm) Ratio Efficacy % value % 0.2 0 0.04 13 0.008 11 20 72 4 85 0.8 67 0.2 20 1:100 85 72 0.04 4 1:100 96 87 0.008 0.8 1:100 82 71

TABLE-US-00063 TABLE J35 in vitro -Test with Pyricularia oryzae Ex. 13.001 Ex. I.59 fludioxonil Colby expected (ppm) (ppm) Ratio Efficacy % value % 1 49 0.2 0 0.04 0 5 79 1 88 0.2 82 1 5 1:5 97 89 0.2 1 1:5 89 88 0.04 0.2 1:5 95 82

TABLE-US-00064 TABLE J36 in vitro -Test with Pyricularia oryzae Ex. 15.008 Ex. I.59 cyflufenamid Colby expected (ppm) (ppm) Ratio Efficacy % value % 0.2 0 0.04 0 20 91 4 17 0.2 20 1:100 93 91 0.04 20 1:100 20 17

TABLE-US-00065 TABLE J37 in vitro -Test with Rhizoctonia solani Ex. 5.018 Ex. I.01 propineb Colby expected (ppm) (ppm) Ratio Efficacy % value % 0.04 0 4 34 0.04 4 1:100 58 34

TABLE-US-00066 TABLE J38 in vitro -Test with Rhizoctonia solani Ex. 1.012 Ex. I.59 ipconazole Colby expected (ppm) (ppm) Ratio Efficacy % value % 0.04 0 0.008 0 0.2 96 0.04 35 0.04 0.2 1:5 97 96 0.008 0.04 1:5 52 35

TABLE-US-00067 TABLE J39 in vitro -Test with Rhizoctonia solani Ex. 5.013 Ex. I.59 mancozeb Colby expected (ppm) (ppm) Ratio Efficacy % value % 0.2 97 0.04 23 20 99 4 57 0.2 20 1:100 99 100 0.04 4 1:100 91 67

TABLE-US-00068 TABLE J40 in vitro -Test with Rhizoctonia solani Ex. I.59 Ex. 15.047 Colby expected (ppm) (ppm) Ratio Efficacy % value % 1 100 0.2 97 5 0 1 0 1 5 1:5 100 100 0.2 1 1:5 100 97

TABLE-US-00069 TABLE J41 in vitro -Test with Septoria tritici Ex. 1.020 Ex. I.01 spiroxamine Colby expected (ppm) (ppm) Ratio Efficacy % value % 0.04 95 0.008 69 4 34 0.8 25 0.04 4 1:100 100 97 0.008 0.8 1:100 85 77

TABLE-US-00070 TABLE J42 in vitro -Test with Septoria tritici Ex. 2.005 Ex. I.01 fluopyram Colby expected (ppm) (ppm) Ratio Efficacy % value % 0.04 94 0.008 61 0.2 93 0.04 43 0.04 0.2 1:5 100 100 0.008 0.04 1:5 87 78

TABLE-US-00071 TABLE J43 in vitro -Test with Septoria tritici Ex. 12.003 Ex. I.01 metalaxyl Colby expected (ppm) (ppm) Ratio Efficacy % value % 1 86 0.2 85 100 35 20 51 1 100 1:100 100 91 0.2 20 1:100 100 93

TABLE-US-00072 TABLE J44 in vitro -Test with Septoria tritici Ex. 12.004 Ex. I.01 mefenxam Colby expected (ppm) (ppm) Ratio Efficacy % value % 1 86 0.2 85 100 28 20 45 1 100 1:100 100 90 0.2 20 1:100 100 92

TABLE-US-00073 TABLE J45 in vitro -Test with Septoria tritici Ex. 13.004 Ex. I.01 mefenxam Colby expected (ppm) (ppm) Ratio Efficacy % value % 1 86 0.2 85 100 28 20 55 1 100 1:100 100 90 0.2 20 1:100 100 93

TABLE-US-00074 TABLE J46 in vitro -Test with Septoria tritici Ex. 1.015 Ex. I.59 paclobutrazol Colby expected (ppm) (ppm) Ratio Efficacy % value % 0.2 53 1 13 0.2 1 1:5 96 59

TABLE-US-00075 TABLE J47 in vitro -Test with Septoria tritici Ex. 2.005 Ex. I.59 fluopyram Colby expected (ppm) (ppm) Ratio Efficacy % value % 0.04 86 0.008 49 0.2 67 0.04 22 0.04 0.2 1:5 100 95 0.008 0.04 1:5 76 60

TABLE-US-00076 TABLE J48 in vitro -Test with Septoria tritici Ex. 3.020 Ex. I.59 trifloxystrobin Colby expected (ppm) (ppm) Ratio Efficacy % value % 1 70 5 90 1 5 1:5 100 97

TABLE-US-00077 TABLE J49 in vitro -Test with Septoria tritici Ex. 4.005 Ex. I.59 pencycuron Colby expected (ppm) (ppm) Ratio Efficacy % value % 1 65 0.2 55 100 0 20 8 1 100 1:100 71 65 0.2 20 1:100 68 59

TABLE-US-00078 TABLE J50 in vitro -Test with Septoria tritici Ex. 5.018 Ex. I.59 propineb Colby expected (ppm) (ppm) Ratio Efficacy % value % 0.04 96 0.008 54 4 19 0.8 12 0.04 4 1:100 100 97 0.008 0.8 1:100 71 60

TABLE-US-00079 TABLE J51 in vitro -Test with Septoria tritici Ex. 12.003 Ex. I.59 metalaxyl Colby expected (ppm) (ppm) Ratio Efficacy % value % 1 65 0.2 55 100 5 20 15 1 100 1:100 100 67 0.2 20 1:100 94 62

TABLE-US-00080 TABLE J52 in vitro -Test with Septoria tritici Ex. 12.004 Ex. I.59 mefenxam Colby expected (ppm) (ppm) Ratio Efficacy % value % 1 65 0.2 55 100 28 20 40 1 100 1:100 96 75 0.2 20 1:100 96 73

TABLE-US-00081 TABLE J53 in vitro -Test with Ustilago avenae Ex. 1.018 Ex. I.59 prothioconazole Colby expected (ppm) (ppm) Ratio Efficacy % value % 1 100 0.2 0 5 100 1 85 1 5 1:5 100 100 0.2 1 1:5 97 85

TABLE-US-00082 TABLE J54 in vitro -Test with Ustilago avenae Ex. 1.020 Ex. I.59 spiroxamine Colby expected (ppm) (ppm) Ratio Efficacy % value % 1 100 0.2 0 100 100 20 12 1 100 1:100 100 100 0.2 20 1:100 93 12

TABLE-US-00083 TABLE J55 in vitro -Test with Ustilago avenae Ex. 2.005 Ex. I.59 fluopyram Colby expected (ppm) (ppm) Ratio Efficacy % value % 1 86 5 0 1 5 1:5 100 86

TABLE-US-00084 TABLE J56 in vitro -Test with Ustilago avenae Ex. I.59 Ex. 2.038 Colby expected (PPm) (ppm) Ratio Efficacy % value % 0.2 0 0.04 0 0.008 0 20 52 4 49 0.8 43 0.2 20 1:100 55 52 0.04 4 1:100 54 49 0.008 0.8 1:100 57 43

[0701] Effect on Non-Target Species

[0702] Some of the active compound combinations according to the invention have an improved compatibility with non-target species, thus potentially providing more environmental friendly solutions. This is evident from the example below. Experiments show that the combinations have the potential for reducing undesirable effects against these non-target species compared to the prediction based on the properties of the individual active compounds. Thereby, the invention will bring environmental benefit. The invention can also bring agronomic benefit through the possibility of e.g. higher registered application rates where/if needed to minimize pest resistance while preserving environmental quality or reducing the mitigation measures that are needed to ensure the safe use of the product towards the environment.

[0703] A more environmentally friendly fungicidal product is identified when the effect of the active compound combination is lower than expected under the hypothesis of concentration addition, which hypothesis is classically used for the regulatory environmental risk assessment of plant protection products. Under the hypothesis of concentration addition for a mixture of the several active compounds, the sum of the concentration of chemicals (c.sub.i) multiplied with their respective potency in a mixture provoking x % effect (1/EC.sub.xi) is equal to 1 (cf. Cedergreen, N., Quantifying Synergy: A Systematic Review of Mixture Toxicity Studies within Environmental Toxicology, PLOSone 2014, 9(5), e96580):

[00002] $\begin{matrix} {.Math.}_{i = 1}^{n} .Math. \frac{c_{i}}{{EC}_{xi}} = 1 & [1] \end{matrix}$

with EC.sub.xi the Effect Concentration (EC) of each chemical i (in ppm) causing x % effect on the ecotoxicity test endpoint.

[0704] Under this hypothesis, the expected effect of the combination of active compounds can be calculated as follows:

[00003] $\begin{matrix} {EC}_{x .Math. .Math. mix} = {({.Math.}_{i = 1}^{n} .Math. \frac{p_{i}}{{EC}_{xi}})}^{- 1} & [2] \end{matrix}$

[0705] With p.sub.i being the proportion of each active compound i in the combination.

[0706] For each compound combination, the predicted EC.sub.x value is calculated. It is then compared to an experimentally measured value. The ratio of predicted versus measured effect for the combination (thereafter called the Model Deviation Ratio or MDR) is then calculated. Results are interpreted as follows: [0707] if MDR <1, the compound combination shows less effects, i.e. is more environmentally favorable than expected; [0708] if MDR >1, the compound combination shows more effects, i.e. is less environmentally favorable than expected.

[0709] The environmental effect of the compound combinations was measured experimentally in laboratory ecotoxicity screening studies with fish (Danio rerio). Fish embryos were exposed at 28.5 C. for 96 hours to the active compounds alone and in combinations according to the invention. Mortality was recorded after 96 h for each tested concentration and a reference control. These data were then used in order to calculate the concentration causing the mortality of 50% of exposed fish i.e. lethal concentration 50%, LC.sub.50. The LC.sub.50 values (in ppm (=mg/L) a.i.) obtained for the active compounds alone were used to estimate the predicted toxicity of the compound combination, using Equation [2]. Then, the MDR values were calculated.

[0710] The invention is illustrated by the following examples. However the invention is not limited to the examples.

Example K: In Vivo Ecotoxicity Screening Test on Fish (Danio rerio)

[0711] Solvent: 0.5% by weight dimethyl sulfoxide

[0712] To produce a suitable preparation of active compound, the compound is first diluted in a pure solution of the vehicle solvent dimethyl sulfoxide. This concentrate is then diluted with water to the desired a.i. concentration, leading to a maximal solvent concentration of 0.5% by weight. The compounds alone and the combinations were tested for five increasing concentrations between 0.01 and 1000 ppm a.i., (e.g. 0.1, 1.0, 10 and 100 ppm a.i). For the combinations, compounds A and B were mixed in a weight ratio of 5:1 to 1:5 and five increasing concentrations were tested for each ratio.

[0713] The table below clearly shows that the observed effect of active compound combinations according to the invention is lower than the predicted effect, i.e. the combinations according to the invention have the potential for lowering undesirable environmental effects on non-target species.

TABLE-US-00085 TABLE K1 in vivo ecotoxicity screening test on fish (D. rerio): results after 96 h Ecotoxicity Tested concentration LC.sub.50-96 h (ppm a.i.) Active compounds range in ppm a.i. found* calc.** MDR (I-01) 2-[6-(4-chlorophenoxy)-2- 1-12 6.21 (trifluoromethyl)pyridin-3-yl]-1- (1H-1,2,4-triazol-1-yl)propan-2-ol (I-59) 2-[6-(4-bromophenoxy)-2- 1-16 6.00 (trifluoromethyl)pyridin-3-yl]-1- (1H-1,2,4-triazol-1-yl)propan-2-ol 1.012 ipconazole 0.01-40 6.57 1.018 prothioconazole 0.01-100.sup. 3.16 1.020 spiroxamine 0.01-40 14.81 1.021 tebuconazole 0.01-100.sup. 19.7 2.002 bixafen 0.01-100.sup. 0.154 2.005 fluopyram 10-200 >200 2.017 penflufen 0.01-100.sup. 0.62 2.038 N-(5-chloro-2-isopropylbenzyl)-N- 0.01-100.sup. 1.74 cyclopropyl-3-(difluoromethyl)-5- fluoro-1-methyl-1H-pyrazole-4- carboxamide 3.020 trifloxystrobin 0.01-30 0.24 3.025 (3S,6S,7R,8R)-8-benzyl-3-[({3- 0.01-30 1.87 [(isobutyryloxy)methoxy]-4- methoxypyridin-2-yl}carbonyl)amino]- 6-methyl-4,9-dioxo-1,5-dioxonan-7-yl 2-methylpropanoate 4.005 pencycuron 0.01-35 >200 5.018 propineb 0.01-100.sup. 25.18 12.003 metalaxyl 0.01-200.sup. >200 12.004 metalaxyl-M (mefenoxam) 0.01-200.sup. >200 13.001 fludioxonil 0.1-10.sup. 0.89 13.004 proquinazid 0.01-100.sup. 9.89 15.008 cyflufenamid 0.01-100.sup. 5.2 15.047 3-(4,4-difluoro-3,3-dimethyl-3,4- 1-40 7.82 dihydro isoquinolin-1-yl)quinoline (I-01) + 1.012 1:5 0.1 + 0.5-10 + 50 6.70 6.51 0.97 (I-01) + 1.012 5:1 1 + 0.2-12 + 2.4 7.28 6.27 0.86 (I-01) + 1.018 1:5 0.1 + 0.5-1.2 + 6 3.18 3.44 1.08 (I-01) + 1.018 5:1 1 + 0.2-12 + 2.4 6.58 5.35 0.81 (I-01) + 1.020 1:5 1 + 5-12 + 60 13.43 12.04 0.90 (I-01) + 1.020 5:1 1 + 0.2-12 + 2.4 11.06 6.88 0.62 (I-01) + 1.021 1:5 1 + 5-12 + 60 17.52 14.47 0.83 (I-01) + 1.021 5:1 1 + 0.2-12 + 2.4 7.58 7.01 0.93 (I-01) + 2.002 1:5 0.01 + 0.05-0.12 + 0.6 0.18 0.18 1.00 (I-01) + 2.002 5:1 0.1 + 0.02-10 + 2 1.21 0.82 0.68 (I-01) + 2.005 1:5 1 + 5-12 + 60 27.63 32.27 1.17 (I-01) + 2.005 5:1 1 + 0.2-12 + 2.4 11.06 7.41 0.67 (I-01) + 2.017 1:5 0.1 + 0.5-1.2 + 6 1.14 0.73 0.64 (I-01) + 2.017 5:1 1 + 0.2-12 + 2.4 2.75 2.48 0.90 (I-01) + 2.038 1:5 0.1 + 0.5-1.2 + 6 1.56 1.98 1.27 (I-01) + 2.038 5:1 1 + 0.2-12 + 2.4 7.28 4.35 0.60 (I-01) + 3.020 1:5 0.01 + 0.05-0.12 + 0.6 0.36 0.29 0.78 (I-01) + 3.020 5:1 1 + 0.2-12 + 2.4 1.29 1.21 0.94 (I-01) + 3.025 1:5 0.1 + 0.5-1.2 + 6 3.80 2.12 0.56 (I-01) + 3.025 5:1 1 + 0.2-12 + 2.4 38.60 4.48 0.12 (I-01) + 4.005 1:5 1 + 5-12 + 60 55.32 32.27 0.58 (I-01) + 4.005 5:1 1 + 0.2-12 + 2.4 7.60 7.41 0.97 (I-01) + 5.018 1:5 0.3 + 1.5-30 + 150 19.22 16.69 0.87 (I-01) + 5.018 5:1 1 + 0.2-12 + 2.4 7.72 7.11 0.92 (I-01) + 12.003 1:5 1 + 5-12 + 60 42.08 32.27 0.77 (I-01) + 12.003 5:1 1 + 0.2-12 + 2.4 10.17 7.41 0.73 (I-01) + 12.004 1:5 1 + 5-12 + 60 38.32 32.27 0.84 (I-01) + 12.004 5:1 0.1 + 0.02-10 + 2 7.55 7.41 0.98 (I-01) + 13.001 1:5 0.01 + 0.05-1 + 5 0.77 1.04 1.34 (I-01) + 13.001 5:1 1 + 0.2-12 + 2.4 3.52 6.21 0.89 (I-01) + 13.004 1:5 0.1 + 0.5-10 + 50 9.47 9.00 0.95 (I-01) + 13.004 5:1 1 + 0.2-12 + 2.4 7.34 6.62 0.90 (I-01) + 15.008 1:5 1 + 5-12 + 60 8.00 2.83 0.35 (I-01) + 15.008 5:1 1 + 0.2-12 + 2.4 7.12 6.02 0.85 (I-01) + 15.047 1:5 1 + 5-12 + 60 6.17 7.50 1.21 (I-01) + 15.047 5:1 1 + 0.2-12 + 2.4 7.72 6.43 0.83 (I-59) + 1.012 1:5 0.1 + 0.5-10 + 50 10.40 6.47 0.62 (I-59) + 1.012 5:1 1 + 0.2-12 + 2.4 7.41 6.09 0.82 (I-59) + 1.018 1:5 0.1 + 0.5-1.2 + 6 3.46 3.43 0.99 (I-59) + 1.018 5:1 1 + 0.2-12 + 2.4 6.93 5.22 0.75 (I-59) + 1.020 1:5 1 + 5-12 + 60 14.69 11.90 0.81 (I-59) + 1.020 5:1 1 + 0.2-12 + 2.4 7.49 6.66 0.89 (I-59) + 1.021 1:5 1 + 5-12 + 60 17.88 14.27 0.80 (I-59) + 1.021 5:1 1 + 0.2-12 + 2.4 7.12 6.79 0.95 (I-59) + 2.002 1:5 0.01 + 0.05-0.12 + 0.6 0.18 0.18 1.00 (I-59) + 2.002 5:1 0.1 + 0.02-10 + 2 1.30 0.82 0.63 (I-59) + 2.005 1:5 1 + 5-12 + 60 22.69 31.30 1.38 (I-59) + 2.005 5:1 1 + 0.2-12 + 2.4 7.34 7.16 0.97 (I-59) + 2.017 1:5 0.1 + 0.5-1.2 + 6 0.85 0.73 0.86 (I-59) + 2.017 5:1 1 + 0.2-12 + 2.4 1.90 2.45 1.29 (I-59) + 2.038 1:5 0.05 + 0.25-1.2 + 6 1.76 1.97 1.12 (I-59) + 2.038 5:1 1 + 0.2-12 + 2.4 6.46 4.26 0.66 (I-59) + 3.020 1:5 0.005 + 0.025-0.12 + 0.6 0.35 0.29 0.83 (I-59) + 3.020 5:1 0.1 + 0.02-10 + 2 2.36 1.20 0.51 (I-59) + 3.025 1:5 0.1 + 0.5-1.2 + 6 2.98 2.11 0.71 (I-59) + 3.025 5:1 1 + 0.2-12 + 2.4 7.28 4.39 0.60 (I-59) + 4.005 1:5 1 + 5-12 + 60 33.59 31.30 0.93 (I-59) + 4.005 5:1 1 + 0.2-12 + 2.4 6.25 7.16 1.15 (I-59) + 5.018 1:5 0.05 + 0.25-25 + 125 19.23 16.43 0.85 (I-59) + 5.018 5:1 1 + 0.2-12 + 2.4 7.03 6.87 0.98 (I-59) + 12.003 1:5 1 + 5-12 + 60 37.07 31.30 0.84 (I-59) + 12.003 5:1 1 + 0.2-12 + 2.4 7.96 7.16 0.90 (I-59) + 12.004 1:5 1 + 5-12 + 60 37.06 31.30 0.84 (I-59) + 12.004 5:1 1 + 0.2-12 + 2.4 7.28 7.16 0.98 (I-59) + 13.001 1:5 0.1 + 0.5-1.2 + 6 0.64 1.03 1.61 (I-59) + 13.001 5:1 0.1 + 0.2-12 + 2.4.sup. 3.59 3.06 0.85 (I-59) + 13.004 1:5 0.1 + 0.5-10 + 50 9.55 8.93 0.94 (I-59) + 13.004 5:1 1 + 0.2-12 + 2.4 6.84 6.42 0.94 (I-59) + 15.008 1:5 1 + 5-12 + 60 9.22 2.79 0.30 (I-59) + 15.008 5:1 1 + 0.2-12 + 2.4 7.28 5.85 0.80 (I-59) + 15.047 1:5 1 + 5-12 + 60 6.24 7.44 1.19 (I-59) + 15.047 5:1 1 + 0.2-12 + 2.4 7.12 6.24 0.88 *found = experimentally measured value **calc. = predicted value

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