Triazole derivatives
09822099 · 2017-11-21
Assignee
Inventors
- Alexander Sudau (Langenfeld, DE)
- Sebastian Hoffmann (Neuss, DE)
- Peter Dahmen (Neuss, DE)
- Ulrike Wachendorff-Neumann (Neuwied, DE)
- David Bernier (Lyons, FR)
- Helene Lachaise (Lyons, FR)
- Stephane Brunet (St Andre de Corcy, FR)
- Jacky Vidal (Lozanne, FR)
- Pierre Genix (Lyons, FR)
- Pierre-Yves Coqueron (Lyons, FR)
- Julie Geist (Lyons, FR)
- Jean-Pierre Vors (Saint Foy les Lyons, FR)
- Philippe Kennel (Biot, FR)
- Ricarda Miller (Lyons, FR)
Cpc classification
C07D403/06
CHEMISTRY; METALLURGY
C07D405/06
CHEMISTRY; METALLURGY
International classification
C07D403/06
CHEMISTRY; METALLURGY
C07D401/06
CHEMISTRY; METALLURGY
C07D405/06
CHEMISTRY; METALLURGY
Abstract
The present invention relates to novel triazole derivatives, to processes for preparing these compounds, to compositions comprising these compounds, and to the use thereof as biologically active compounds, especially for control of harmful microorganisms in crop protection and in the protection of materials and as plant growth regulators.
Claims
1. Triazole derivative of formula (I) ##STR00026## wherein R.sup.1 represents C.sub.1-C.sub.8-haloalkyl; C.sub.2-C.sub.8-halooalkenyl; C.sub.2-C.sub.8-haloalkynyl; C.sub.3-C.sub.7-halocycloalkyl-C.sub.1-C.sub.4-alkyl; C.sub.3-C.sub.7-halocycloalkyl-C.sub.1-C.sub.4-haloalkyl; C.sub.3-C.sub.7-cycloalkyl-C.sub.1-C.sub.4-haloalkyl; substituted or non-substituted C.sub.3-C.sub.7-cycloalkyl; substituted or non-substituted C.sub.3-C.sub.7-cycloalkenyl; substituted or non-substituted arylalkyl; substituted or non-substituted arylalkenyl; substituted or non-substituted arylalkynyl; substituted or non-substituted phenoxyalkyl; substituted or non-substituted phenylcycloalkyl; substituted or non-substituted hetaryl; substituted hetarylalkyl; substituted or non-substituted heterocycloalkyl; or substituted or non-substituted heterocycloalkyl-C.sub.1-C.sub.8-alkyl; R.sup.2 represents H, C.sub.1-C.sub.8-alkyl, —Si(R.sup.3a)(R.sup.3b)(R.sup.3c), —P(O)(OH).sub.2, —CH.sub.2—O—P(O)(OH).sub.2, substituted or non-substituted —C(O)—C.sub.1-C.sub.8-alkyl or substituted, non-substituted —C(O)—C.sub.3-C.sub.7-cycloalkyl, substituted or non-substituted —C(O)NH—C.sub.1-C.sub.8-alkyl; substituted or non-substituted —C(O)N-di-C.sub.1-C.sub.8-alkyl; or substituted or non-substituted —C(O)O—C.sub.1-C.sub.8-alkyl; R.sup.3a, R.sup.3b, R.sup.3c independent from each other represent a substituted or non-substituted C.sub.1-C.sub.8-alkyl; and X represents a substituted or non-substituted unsaturated 6-membered heterocycle containing 1 or 2 nitrogen atom(s) as heteroatom(s) or a benzannulated derivative thereof; and/or a salt and/or N-oxide thereof.
2. Triazole derivative of formula (I) and/or salt and/or N-oxide according to claim 1, wherein R.sup.1 represents C.sub.1-C.sub.8-haloalkyl; C.sub.2-C.sub.5-halooalkenyl; C.sub.2-C.sub.8-haloalkynyl; C.sub.3-C.sub.7-halocycloalkyl-C.sub.1-C.sub.4-alkyl; C.sub.3-C.sub.7-halocycloalkyl-C.sub.1-C.sub.4-haloalkyl; C.sub.3-C.sub.7-cycloalkyl-C.sub.1-C.sub.4-haloalkyl; substituted or non-substituted C.sub.3-C.sub.7-cycloalkyl; substituted or non-substituted C.sub.3-C.sub.7-cycloalkenyl; substituted or non-substituted arylalkyl; substituted or non-substituted arylalkenyl; substituted or non-substituted arylalkynyl; substituted or non-substituted phenoxyalkyl; substituted or non-substituted phenylcycloalkyl; substituted or non-substituted hetaryl; substituted hetarylalkyl; substituted or non-substituted heterocycloalkyl; or substituted or non-substituted heterocycloalkyl-C.sub.1-C.sub.8-alkyl; R.sup.2 represents H, C.sub.1-C.sub.8-alkyl, —Si(R.sup.3a)(R.sup.3b)(R.sup.3c), —P(O)(OH).sub.2, —CH.sub.2—O—P(O)(OH).sub.2, substituted or non-substituted —C(O)—C.sub.1-C.sub.8-alkyl or substituted, non-substituted —C(O)—C.sub.3-C.sub.7-cycloalkyl, substituted or non-substituted —C(O)NH—C.sub.1-C.sub.5-alkyl; substituted or non-substituted —C(O)N-di-C.sub.1-C.sub.8-alkyl; or substituted or non-substituted —C(O)O—C.sub.1-C.sub.8-alkyl; R.sup.3a, R.sup.3b, R.sup.3c independent from each other represent a substituted or non-substituted C.sub.1-C.sub.8-alkyl; and X represents a substituted or non-substituted unsaturated 6 membered heterocycle containing 1 or 2 nitrogen atom(s) as heteroatom(s) or a benzannulated derivative thereof, with the provisio that X does not represent 2-pyridinyl.
3. Triazole derivative of formula (I) and/or salt and/or N-oxide according to claim 1, wherein R.sup.1 represents C.sub.1-C.sub.5-haloalkyl or substituted or non-substituted C.sub.3-C.sub.7-cycloalkyl; R.sup.2 represents H, C.sub.1-C.sub.8-alkyl or substituted or non-substituted —C(O)—C.sub.1-C.sub.8-alkyl; and X represents a substituted or non-substituted 3-pyridinyl, 4-pyridinyl, 4-pyrimidinyl, 5-pyrimidinyl, pyrazin-2-yl, pyridazin-3-yl, pyridazin-4-yl, quinoline-2-yl or quinoline-3-yl.
4. Method for controlling one or more harmful microorganisms, comprising applying a compound of formula (I) and/or salt and/or N-oxide according to claim 1, to the harmful microorganisms and/or a habitat thereof.
5. Method for controlling phytopathogenic harmful fungi, comprising applying a compound of formula (I) and/or salt and/or N-oxide according to claim 1, to the phytopathogenic harmful fungi and/or a habitat thereof.
6. The method according to claim 5, comprising treatment of one or more transgenic plants.
7. Composition for controlling harmful microorganisms, comprising a content of at least one compound of formula (I) and/or salt and/or N-oxide according to claim 1, in addition to one or more extenders and/or surfactants.
8. Composition according to claim 7 comprising at least one further active ingredient selected from the group of the insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides, fertilizers, safeners and semiochemicals.
9. The composition according to claim 7, for control of phytopathogenic harmful fungi.
10. Process for producing a composition for controlling harmful microorganisms, optionally for controlling phytopathogenic harmful fungi, comprising mixing a compound of formula (I) and/or salt and/or N-oxide according to claim 1, with one or more extenders and/or surfactants.
11. Seed treated with a compound of formula (I) and/or salt and/or N-oxide according to claim 1.
12. Compound of formula (V) ##STR00027## wherein X represents a substituted or non-substituted unsaturated 6-membered heterocycle containing 1 or 2 nitrogen atom(s) as heteroatom(s) or a benzannulated derivative thereof; and R.sup.1 represents a substituted or non-substituted 1-halogencyclopropyl, 1-halogen-2-methylpropan-2-yl or 2-halogen-propan-2-yl; and/or salt and/or N-oxide thereof.
13. Epoxide of formula (XII) ##STR00028## wherein X represents a substituted or non-substituted unsaturated 6-membered heterocycle containing 1 or 2 nitrogen atom(s) as heteroatom(s) or a benzannulated derivative thereof; and R.sup.1 represents C.sub.1-C.sub.8-haloalkyl; C.sub.2-C.sub.5-halooalkenyl; C.sub.2-C.sub.8-haloalkynyl; C.sub.3-C.sub.7-halocycloalkyl-C.sub.1-C.sub.4-alkyl; C.sub.3-C.sub.7-halocycloalkyl-C.sub.1-C.sub.4-haloalkyl; C.sub.3-C.sub.7-cycloalkyl-C.sub.1-C.sub.4-haloalkyl; substituted or non-substituted C.sub.3-C.sub.7-cycloalkyl; substituted or non-substituted C.sub.3-C.sub.7-cycloalkenyl; substituted or non-substituted arylalkenyl; substituted or non-substituted arylalkynyl; substituted or non-substituted phenoxyalkyl; substituted or non-substituted phenylcycloalkyl; substituted or non-substituted hetaryl; substituted hetarylalkyl; or substituted or non-substituted heterocycloalkyl and/or salt and/or N-oxide of the epoxide of formula (XII).
14. Compound of formula (V) ##STR00029## wherein X represents a substituted or non-substituted 3-pyridinyl or 4-pyridinyl or a benzannulated derivative thereof; and R.sup.1 represents a substituted or non-substituted 1-C.sub.1-C.sub.8-alkylcyclopropyl, 2-C.sub.1-C.sub.8-alkylcyclopropyl, C.sub.1-C.sub.8-haloalkyl, 1-C.sub.1-C.sub.8-alkylcyclohexyl, 1-arylcyclopropyl or 2-arylcyclopropyl; and/or salt and/or N-oxide of the compound of formula (V).
15. Alcohol of formula (XV) ##STR00030## wherein X represents a substituted or non-substituted unsaturated 6-membered heterocycle containing 1 or 2 nitrogen atom(s) as heteroatom(s) or a benzannulated derivative thereof, and R.sup.1 represents C.sub.1-C.sub.8-haloalkyl; C.sub.2-C.sub.5-halooalkenyl; C.sub.2-C.sub.8-haloalkynyl; C.sub.3-C.sub.7-halocycloalkyl-C.sub.1-C.sub.4-alkyl; C.sub.3-C.sub.7-halocycloalkyl-C.sub.1-C.sub.4-haloalkyl; C.sub.3-C.sub.7-cycloalkyl-C.sub.1-C.sub.4-haloalkyl; substituted or non-substituted C.sub.3-C.sub.7-cycloalkyl; substituted or non-substituted C.sub.3-C.sub.7-cycloalkenyl; substituted or non-substituted arylalkyl; substituted or non-substituted arylalkenyl; substituted or non-substituted arylalkynyl; substituted or non-substituted phenoxyalkyl; substituted or non-substituted phenylcycloalkyl; substituted or non-substituted hetaryl; substituted hetarylalkyl; substituted or non-substituted heterocycloalkyl; or substituted or non-substituted heterocycloalkyl-C.sub.1-C.sub.8-alkyl; and A represents chloro, bromo, iodo, O—SO.sub.2—C.sub.1-C.sub.8-alkyl or O—SO.sub.2-aryl; and/or salt and/or N-oxide thereof.
Description
EXAMPLES
Preparation Examples
Preparation of Compounds of the Formula (I-5) According to Process H
Preparation of 2-(1-chlorocyclopropyl)-1-(3-chloropyridin-4-yl)-3-(1H-1,2,4-triazol-1-yl)propan-2-ol (I-5)
(1) ##STR00018##
(2) To a solution of 1H-1,2,4-triazole (162 mg, 3 eq, 2.35 mmol) in 2.5 mL dimethylformamide was added potassium carbonate (326 mg, 3 eq, 2.35 mmol) and a solution of 3-chloro-4-{[2-(1-chlorocyclopropyl)oxiran-2-yl]methyl}pyridine (300 mg, 0.78 mmol) in 0.5 mL dimethylformamide Thereafter 5 mg potassium tert-butylate was added and the mixture was stirred for 5 h at 40° C. Thereafter the reaction mixture was evaporated in vacuo and treated with ethyl acetate. After filtration and evaporation of the solvent the crude product was purified by chromatography over silica using a 1:1 mixture of ethyl acetate/cyclohexane as eluent. After evaporation of the solvent 100 mg (40%) of 2-(1-chlorocyclopropyl)-1-(3-chloropyridin-4-yl)-3-(1H-1,2,4-triazol-1-yl)propan-2-ol were obtained as solid.
(3) MS (ESI): 313.0 ([M+1].sup.+)
Preparation of Intermediates of the Formula (XII-3) According to Process D
Preparation of 3-chloro-4-{[2-(1-chlorocyclopropyl)oxiran-2-yl]methyl}pyridine (XII-3)
(4) ##STR00019##
(5) A mixture of trimethylsulfoxonium chloride (330 mg, 2 eq, 1.5 mmol), sodium hydroxide (793 mg, 12 eq, 45% weight in H.sub.2O) and hexadecyltrimethylammoniumbromide (3 mg, 0.01 eq) in 1.4 mL dichloromethane was stirred for 10 min at ambient temperature. Thereafter, 1-(1-chlorocyclopropyl)-2-(3-chloropyridin-4-yl)ethanone (180 mg, 1 eq, 0.74 mmol) was added and the mixture was stirred for 4 h at 45° C. The obtained suspension was diluted with dichloromethane and filtered. The filtrate was evaporated and purified by column chromatography over silica gel (eluent cyclohexane/ethyl acetate gradient). After evaporation of the solvent 70 mg (35%) of 3-chloro-4-{[2-(1-chlorocyclopropyl)oxiran-2-yl]methyl}pyridine were obtained as colourless oil.
(6) MS (ESI): 244.0 ([M+H].sup.+)
Preparation of Intermediates of the Formula (XII-3) According to Process F
Preparation of 3-chloro-4-{[2-(1-chlorocyclopropyl)oxiran-2-yl]methyl}pyridine (XII-3)
(7) ##STR00020##
(8) To a solution of lithium diisopropylamide (30 mL, 2M in THF) at −70° C. is added under argon a solution of 3-chloro-4-methylpyridine (6.38 g, 1 eq, 50 mmol) in 25 mL THF. The mixture is stirred for 5 min at −70° C. and then allowed to reach −30° C. Thereafter the mixture is cooled down to −70° C. and a solution of 2-chloro-1-(1-chlorocyclopropyl)ethanone (9.18 g, 1.2 eq, 60 mmol) in 25 mL THF is added. Then the mixture is allowed to reach ambient temperature and stirred for 1 h. Thereafter the mixture is cooled to 0° C. and saturated aqueous ammonium chloride solution is added. After extraction with ethyl acetate and evaporation of the solvent the crude material is purified via column chromatography over silica gel (eluent cyclohexane/ethyl acetate gradient). After evaporation of the solvent 10 g (73%) of 3-chloro-4-{[2-(1-chlorocyclopropyl)oxiran-2-yl]methyl}pyridine are obtained as colourless oil.
Preparation of Intermediates of the Formula (V-3) According to Process A
Preparation of 1-(1-chlorocyclopropyl)-2-(2-chloropyridin-3-yl)ethanone (V-3)
(9) ##STR00021##
(10) To a suspension of zinc (2.72 g, 1.5 eq) in THF (40 mL) was added dropwise under argon a solution of 2-chloro-3-chloromethylpyridine (2.25 g, 0.5 eq) in THF (15 mL). Dibromoethane (100 μL) was then added to the reaction mixture, followed by a solution of 2-chloro-3-chloromethylpyridine (2.25 g, 0.5 eq) in THF (15 mL). The mixture was stirred at room temperature for 1 h. A suspension of 1-chlorocyclopropyl carbonyl chloride (3.86 g, 1 eq) and dichlorobis(triphenylphosphine)palladium (II) (1.17 g, 0.06 eq) in THF (30 mL) was then added dropwise and the mixture was stirred at 65° C. for 4 h30. The mixture was then stirred at room temperature and heated again to 65° C. for 1 h30. The mixture was filtered and the filtrate was poured over water (300 mL) and ethyl acetate (100 mL) was then added. The suspension was filtered and the 2 layers were separated. The water layer was extracted with ethyl acetate (2*100 mL). The organic phase were combined, dried over magnesium sulfate, filtered and evaporated. The residue was purified by chromatography on silica gel to afford 1-(1-chlorocyclopropyl)-2-(2-chloropyridin-3-yl)ethanone as a yellow oil (3.79 g, 56%).
(11) MS (ESI): 230.0 ([M+H].sup.+)
Preparation of Intermediates of the Formula (V-3) According to Process B
Preparation of 1-(1-chlorocyclopropyl)-2-(2-chloropyridin-3-yl)ethanone (V-3)
(12) ##STR00022##
(13) To a solution of lithium diisopropylamide (32 mL, 1.3 eq, 65 mmol, 2M in THF) in 40 mL THF at −70° C. is added under argon a solution of 2-chloro-3-methylpyridine (6.38 g, 1 eq, 50 mmol) in 10 mL THF. The mixture is stirred for 15 min at −70° C. and then allowed to reach −30° C. In a separate flask a solution of ethyl 1-chlorocyclopropanecarboxylate (11 g, 1.5 eq, 75 mmol) in 25 mL THF is cooled to −30° C. To this solution the methylpyridine solution is slowly added at −30° C. Thereafter the mixture is allowed to reach ambient temperature and stirred for 1 h. Thereafter the mixture is cooled to 0° C. and saturated aqueous ammonium chloride solution is added. After extraction with ethyl acetate and evaporation of the solvent the crude material is purified via column chromatography over silica gel (eluent cyclohexane/ethyl acetate gradient). After evaporation of the solvent 3.1 g (26%) of 1-(1-chlorocyclopropyl)-2-(2-chloropyridin-3-yl)ethanone are obtained as colourless oil.
(14) The exemplary compounds according to the invention listed in Table 1, 2 and 3 have been synthesized analogous to the above mentioned processes.
(15) The following Table 1 illustrates in a non-limiting manner examples of compounds according to formula (I).
(16) ##STR00023##
(17) TABLE-US-00001 TABLE 1 Ex N.sup.o R.sup.1 R.sup.2 X LogP I-1 1-chlorocyclopropyl H quinolin-2-yl 1.64.sup.[a] I-2 1-chlorocyclopropyl H 3-chloropyridin-2-yl 2.28.sup.[a] I-3 1-chlorocyclopropyl H 2-chloropyridin-3-yl 1.78.sup.[a] I-4 1-chlorocyclopropyl H 6-chloropyridin-3-yl 1.84.sup.[a] I-5 1-chlorocyclopropyl H 3-chloropyridin-4-yl 1.75.sup.[b]; 1.67.sup.[a] I-6 1,3-difluoro-2-methylpropan- H 3-chloropyridin-4-yl 1.54.sup.[a] 2-yl I-7 1-fluorocyclopropyl H 3-chloropyridin-4-yl 1.29.sup.[a] I-8 1-methylcyclopropyl H 2-chloropyridin-3-yl 1.73.sup.[a] I-9 1-chlorocyclopropyl H 6-chloropyrazin-2-yl 1.72.sup.[a] I-10 1-chlorocyclopropyl H 3-chloro-5-methylpyrazin-2-yl 2.05.sup.[a] I-11 1-chlorocyclopropyl H pyrazin-2-yl 1.13.sup.[a] I-12 2-fluorobenzyl H 3-chloropyridin-4-yl 1.96.sup.[a] I-13 6-chloropyridin-3-yl H 3-chloropyridin-4-yl 1.26.sup.[a] I-14 2-chloropyridin-3-yl H 3-chloropyridin-4-yl 1.23.sup.[a] I-15 3-chlorobenzyl H 3-chloropyridin-4-yl 2.27.sup.[a] I-16 1-(4-chlorophenoxy)ethyl H 2-chloropyridin-3-yl I-17 1-chlorocyclopropyl H 4,6-dichloropyridin-2-yl 2.76.sup.[a] I-18 1-chlorocyclopropyl H 3-fluoropyridin-4-yl 1.29.sup.[a] I-19 1-fluorocyclopropyl H 3-fluoropyridin-4-yl 0.91.sup.[a] I-20 2-fluorobenzyl H 3-fluoropyridin-4-yl 1.63.sup.[a] I-21 1,3-difluoro-2-methylpropan- H 3-fluoropyridin-4-yl 1.27.sup.[a] 2-yl I-22 3-chlorobenzyl H 3-fluoropyridin-4-yl 2.00.sup.[a] I-23 2-chloropyridin-3-yl H 3-fluoropyridin-4-yl 0.91.sup.[a] I-24 6-chloropyridin-3-yl H 3-fluoropyridin-4-yl 0.99.sup.[a] I-25 1-fluorocyclopropyl H 2-chloropyridin-3-yl 1.42.sup.[a] I-26 1-chlorocyclopropyl H 2,6-dichloropyridin-4-yl 2.54.sup.[a] I-27 1-chlorocyclopropyl H quinolin-4-yl 1.00.sup.[a] I-28 1-chlorocyclopropyl Si(Me)3 pyrazin-2-yl 2.75.sup.[a] I-29 1-chlorocyclopropyl H 6-chloropyridin-2-yl 2.18.sup.[a] I-30 1-chlorocyclopropyl H 3-chloropyrazin-2-yl 1.86.sup.[a] I-31 1-chlorocyclopropyl H 5,6-dichloropyridin-2-yl 2.66.sup.[a] I-32 1-chlorocyclopropyl H 6-chloro-4-[(5,6-dichloropyridin-2- 3.58.sup.[a] yl)methyl]pyridin-2-yl I-33 1-fluorocyclopropyl H 2-chloropyridin-4-yl 1.44.sup.[a] I-34 2-chloropyridin-3-yl H 2-chloropyridin-4-yl 1.35.sup.[a] I-35 2-fluorobenzyl H 2-chloropyridin-4-yl 2.06.sup.[a] I-36 1,3-difluoro-2-methylpropan- H 2-chloropyridin-4-yl 1.66.sup.[a] 2-yl I-37 3-chlorobenzyl H 2-chloropyridin-4-yl 2.42.sup.[a] I-38 6-chloropyridin-3-yl H 2-chloropyridin-4-yl 1.38.sup.[a] I-39 1-chlorocyclopropyl H 2-chloropyridin-4-yl 1.76.sup.[a] I-40 1-chlorocyclopropyl H 2-chloro-5-fluoropyridin-4-yl 2.06.sup.[a] I-41 1-fluorocyclopropyl H 2-chloro-5-fluoropyridin-4-yl 1.66.sup.[a] I-42 6-chloropyridin-3-yl H 2-chloro-5-fluoropyridin-4-yl 1.60.sup.[a] I-43 2-chloropyridin-3-yl H 2-chloro-5-fluoropyridin-4-yl 1.57.sup.[a] I-44 1,3-difluoro-2-methylpropan- H 2-chloro-5-fluoropyridin-4-yl 1.89.sup.[a] 2-yl I-45 1-chlorocyclopropyl H 3-chloropyridazin-4-yl 1.31.sup.[a] I-46 1-chlorocyclopropyl H 3,6-dichloropyridazin-4-yl 1.92.sup.[a] I-47 1-chlorocyclopropyl H 4-chloropyridin-2-yl 2.02.sup.[a] I-48 1-chlorocyclopropyl H 6-methylpyridin-2-yl 0.52.sup.[a] I-49 1-methylcyclopropyl H 3-chloropyridin-4-yl 1.57.sup.[a] I-50 1-chlorocyclopropyl H pyrimidin-4-yl 1.10.sup.[a] I-51 1-chlorocyclopropyl H 2-fluoropyridin-3-yl 1.64.sup.[a] I-52 1-chlorocyclopropyl H 4-methylpyridin-2-yl 0.52.sup.[a] I-53 1-chlorocyclopropyl H 2,6-dichloropyridin-3-yl 2.55.sup.[a] I-54 1-chlorocyclopropyl H 3-iodopyrazin-2-yl 2.07.sup.[a] I-55 1-chlorocyclopropyl H 3-chloro-6-(4-chlorophenoxy)pyridazin-4- 3.08.sup.[a] yl I-56 1-chlorocyclopropyl H 6-(4-chlorophenoxy)pyrazin-2-yl 2.88.sup.[a] I-57 1-chlorocyclopropyl H 5,6-dichloropyrimidin-4-yl 2.28.sup.[a] I-58 1-chlorocyclopropyl H 2,5-dichloropyridin-4-yl 2.53.sup.[a] I-59 2-chloropyridin-3-yl H 2-chloro-3-fluoropyridin-4-yl 1.54.sup.[a] I-60 1-chlorocyclopropyl H 2-chloro-3-fluoropyridin-4-yl 2.02.sup.[a] I-61 1,3-difluoro-2-methylpropan- H 2-chloro-3-fluoropyridin-4-yl 1.87.sup.[a] 2-yl I-62 1-fluorocyclopropyl H 3,5-dichloropyridin-4-yl 1.86.sup.[a] I-63 6-chloropyridin-3-yl H 3,5-dichloropyridin-4-yl 1.89.sup.[a] I-64 2-fluorobenzyl H 5-chloro-2-fluoropyridin-4-yl 2.46.sup.[a] I-65 1-fluorocyclopropyl H 5-chloro-2-fluoropyridin-4-yl 1.77.sup.[a] I-66 1,5-dimethyl-1H-pyrazol-3-yl H 3-chloropyridin-4-yl 0.84.sup.[a] I-67 1-chlorocyclopropyl H 5-chloropyridin-2-yl 2.23.sup.[a] I-68 2-(2-chlorophenyl)ethyl H 3-chloropyridin-4-yl 2.29.sup.[a] I-69 2-(4-chlorophenyl)ethyl H 3-chloropyridin-4-yl 2.40.sup.[a] I-70 2-(4-chlorophenoxy)propan-2- H 3-chloropyridin-4-yl 2.84.sup.[a] yl I-71 1-chlorocyclopropyl H 3-bromopyrazin-2-yl 1.96.sup.[a] I-72 1-chlorocyclopropyl H 3-methoxypyrazin-2-yl 1.88.sup.[a] I-73 2-fluorobenzyl H 2-chloro-5-fluoropyridin-4-yl 2.34.sup.[a] I-74 3-chlorobenzyl H 2-chloro-5-fluoropyridin-4-yl 2.69.sup.[a] I-75 4-fluorobenzyl H 3-chloropyridin-4-yl 1.93.sup.[a] I-76 2-fluoropropan-2-yl H 3-chloropyridin-4-yl 1.20.sup.[a] I-77 Cyclobutyl H 3-chloropyridin-4-yl 1.46.sup.[a] I-78 1-phenylcyclopropyl H 3-chloropyridin-4-yl 2.23.sup.[a] I-79 (4-fluorophenoxy)methyl H 3-chloropyridin-4-yl 1.86.sup.[a] I-80 dibenzo[b,d]furan-2-yl H 3-chloropyridin-4-yl 2.40.sup.[a] I-81 1-chlorocyclopropyl H 3-(trifluoromethyl)pyridin-4-yl 2.08.sup.[a] I-82 1-chlorocyclopropyl H 2,3-dichloropyridin-4-yl 2.39.sup.[a] I-83 1-chlorocyclopropyl H 2,5-dichloropyridin-3-yl 2.53.sup.[a] I-84 1-chlorocyclopropyl H 2-chloro-8-methylquinolin-3-yl 3.53.sup.[a] I-85 2-fluorobenzyl H 2-chloro-3-fluoropyridin-4-yl 1.73.sup.[a] I-86 6-chloropyridin-3-yl H 2-chloro-3-fluoropyridin-4-yl 1.23.sup.[a] I-87 1-fluorocyclopropyl H 2-chloro-3-fluoropyridin-4-yl 1.23.sup.[a] I-88 3-chlorobenzyl H 2-chloro-3-fluoropyridin-4-yl 2.02.sup.[a] I-89 1-chlorocyclopropyl H 5-chloro-2-fluoropyridin-4-yl 2.30.sup.[a] I-90 1-chloro-2-methylpropan-2-yl H 3-chloropyridin-4-yl 1.96.sup.[b]; 1.76.sup.[a] I-91 2-(4-fluorophenoxy)propan-2- H 3-chloropyridin-4-yl 2.60.sup.[b]; yl 2.48.sup.[a] I-92 1-chlorocyclopropyl H 2-chloroquinolin-4-yl 2.69.sup.[a] I-93 1-methylcyclopropyl H 3-chloropyridazin-4-yl 1.28.sup.[a] I-94 (*) 1-chlorocyclopropyl H 2-chloropyridin-3-yl 1.79.sup.[b]; 1.81.sup.[a] I-95 (*) 1-chlorocyclopropyl H 2-chloropyridin-3-yl 1.79.sup.[b]; 1.81.sup.[a] I-96 1-chlorocyclopropyl H 3,6-dichloropyridin-2-yl 2.73.sup.[a] I-97 1-chlorocyclopropyl H 3,5-dichloropyridin-2-yl 2.88.sup.[a] (*) Ex I-94 and I-95 are the 2 enantiomers of Ex I-3 Optical rotation: I-94 is the (−) Isomer −8.1° (MeOH) I-95 is the (+) Isomer +9.6° (MeOH)
(18) The following Table 2 illustrates in a non-limiting manner examples of compounds according to formula (V).
(19) ##STR00024##
(20) TABLE-US-00002 TABLE 2 Ex N.sup.o R.sup.1 X LogP V-1 1-chlorocyclopropyl quinolin-2-yl 3.39.sup.[a] V-2 1-chlorocyclopropyl 3-chloropyridin-2-yl 2.40.sup.[a] V-3 1-chlorocyclopropyl 2-chloropyridin-3-yl 2.21.sup.[b]; 2.20.sup.[a] V-4 1-chlorocyclopropyl 3-chloropyridin-4-yl 2.13.sup.[a] V-5 1-chlorocyclopropyl 2,6-dichloropyridin-4-yl 3.25.sup.[a] V-6 1-chlorocyclopropyl 6-chloropyridin-3-yl 2.30.sup.[b]; 2.34.sup.[a] V-7 1-fluorocyclopropyl 3-chloropyridin-4-yl 1.76.sup.[a] V-8 2-fluoropropan-2-yl 3-chloropyridin-4-yl 1.97.sup.[a] V-9 1-methylcyclopropyl 2-chloropyridin-3-yl 1.96.sup.[a] V-10 1-phenylcyclopropyl 2-chloropyridin-3-yl 3.00.sup.[a] V-11 1-methylcyclopropyl 3-chloropyridin-4-yl 1.85.sup.[a] V-12 1-methylcyclohexyl 3-chloropyridin-4-yl 3.23.sup.[a] V-13 1-chlorocyclopropyl quinolin-3-yl 1.60.sup.[a] V-14 1-fluorocyclopropyl 2-chloropyridin-3-yl V-15 1,3-difluoro-2- 2-chloropyridin-3-yl 1.98.sup.[a] (fluoromethyl)propan-2-yl V-16 1-chlorocyclopropyl 2-fluoropyridin-3-yl 2.07.sup.[a] V-17 1-chlorocyclopropyl 2,6-dichloropyridin-3-yl 3.19.sup.[a] V-18 1-chlorocyclopropyl 2-chloro-8- 4.14.sup.[a] methylquinolin-3-yl V-19 1-chlorocyclopropyl pyridin-3-yl 0.23.sup.[a] V-20 1-chlorocyclopropyl 2,4-dichloropyridin-3-yl 2.96.sup.[a] V-21 1-chlorocyclopropyl 2,5-dichloropyridin-3-yl 3.12.sup.[a]
(21) The following Table 3 illustrates in a non-limiting manner examples of compounds according to formula (XII).
(22) ##STR00025##
(23) TABLE-US-00003 TABLE 3 Ex N.sup.o R.sup.1 X LogP XII-1 1-chlorocyclopropyl quinolin-2-yl 1.74.sup.[a] XII-2 1-chlorocyclopropyl 6-chloropyridin-3-yl 2.83.sup.[b]; 2.84.sup.[a] XII-3 1-chlorocyclopropyl 3-chloropyridin-4-yl 2.71.sup.[b]; 2.60.sup.[a] XII-4 1-chlorocyclopropyl 3-chloropyridin-2-yl 2.69.sup.[a] XII-5 1-chlorocyclopropyl 2-chloropyridin-3-yl 2.69.sup.[a] XII-6 1-chlorocyclopropyl 3-fluoropyridin-4-yl 2.13.sup.[a] XII-7 1-fluorocyclopropyl 3-fluoropyridin-4-yl 1.63.sup.[a] XII-8 1,3-difluoro-2-methylpropan-2-yl 3-fluoropyridin-4-yl 1.79.sup.[a] XII-9 1-fluorocyclopropyl 2-chloropyridin-4-yl 2.27.sup.[a] XII-10 1,3-difluoro-2-methylpropan-2-yl 2-chloropyridin-4-yl 2.38.sup.[a] XII-11 1-chlorocyclopropyl 2-chloropyridin-4-yl 2.80.sup.[a] XII-12 1,3-difluoro-2-methylpropan-2-yl 2-chloro-5-fluoropyridin-4-yl 2.69.sup.[a] XII-13 1-fluorocyclopropyl 2-chloro-5-fluoropyridin-4-yl 2.57.sup.[a] XII-14 1-chlorocyclopropyl 2-chloro-5-fluoropyridin-4-yl 3.15.sup.[a] XII-15 2-chloropropan-2-yl 3-chloropyridin-4-yl 2.57.sup.[a] XII-16 1-chlorocyclopentyl 3-chloropyridin-4-yl 3.42.sup.[a] XII-17 1-chlorocyclohexyl 3-chloropyridin-4-yl 3.80.sup.[a] XII-18 1,3-difluoro-2-methylpropan-2-yl 3-chloropyridin-4-yl 2.16.sup.[a] XII-19 1-fluorocyclopropyl 3-chloropyridin-4-yl 2.06.sup.[a] XII-20 1-chlorocyclopropyl 5-chloro-2-fluoropyridin-4-yl 3.41.sup.[a] XII-21 1-fluorocyclopropyl 5-chloro-2-fluoropyridin-4-yl 2.80.sup.[a] XII-22 1,3-difluoro-2-methylpropan-2-yl 5-chloro-2-fluoropyridin-4-yl 2.84.sup.[a] XII-23 1-fluorocyclopropyl 2-chloropyridin-3-yl 2.18.sup.[a] XII-24 1-chlorocyclopropyl 2,6-dichloropyridin-4-yl 3.80.sup.[a] XII-25 1-chlorocyclopropyl pyrimidin-4-yl 1.44.sup.[a] XII-26 1-chlorocyclopropyl 2-chloro-3-fluoropyridin-4-yl 3.11.sup.[a] XII-27 1,3-difluoro-2-methylpropan-2-yl 2-chloro-3-fluoropyridin-4-yl 2.65.sup.[a] XII-28 1-fluorocyclopropyl 2-chloro-3-fluoropyridin-4-yl 2.53.sup.[a] XII-29 1-chlorocyclopropyl 5,6-dichloropyrimidin-4-yl XII-30 1-chlorocyclopropyl 2,6-dichloropyridin-3-yl 3.71.sup.[a] XII-31 1-chlorocyclopropyl 2-fluoropyridin-3-yl 2.47.sup.[a] XII-32 1-chlorocyclopropyl 3,5-dichloropyridin-4-yl 3.68.sup.[a] XII-33 1,3-difluoro-2-methylpropan-2-yl 3,5-dichloropyridin-4-yl 2.89.sup.[a] XII-34 1-fluorocyclopropyl 3,5-dichloropyridin-4-yl 2.93.sup.[a] XII-35 1-phenylcyclopropyl 3-chloropyridin-4-yl XII-36 2-phenylpropan-2-yl 3-chloropyridin-4-yl XII-37 2-fluoropropan-2-yl 3-chloropyridin-4-yl XII-38 1-chlorocyclopropyl 3-(trifluoromethyl)pyridin-4-yl 3.04.sup.[a] XII-39 1-chlorocyclopropyl 2-chloro-8-methylquinolin-3-yl 4.90.sup.[a] XII-40 1-chlorocyclopropyl 2,4-dichloropyridin-3-yl 3.53.sup.[a] XII-41 1-chlorocyclopropyl 2,5-dichloropyridin-3-yl 3.87.sup.[a] XII-42 1-chlorocyclopropyl 2,5-dichloropyridin-4-yl 3.70.sup.[a]
(24) Measurement of Log P values for Tables 1, 2 and 3 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:
(25) .sup.[a] Measurement of LC-MS was done at pH 2.7 with 0.1% formic acid in water and with acetonitrile (contains 0.1% formic acid) as eluent with a linear gradient from 10% acetonitrile to 95% acetonitrile.
(26) .sup.[b] Measurement with LC-MS was done at pH 7.8 with 0.001 molar ammonium hydrogen carbonate solution in water as eluent with a linear gradient from 10% acetonitrile to 95% acetonitrile.
(27) Calibration was done with straight-chain alkan2-ones (with 3 to 16 carbon atoms) with known Log P values (measurement of Log P 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.
(28) 1H-NMR data and 1H-NMR-peak list 1H-NMR data of selected examples from Tables 1, 2 and 3 are either written in classical form (d-value in ppm, number of H-atoms, multiplet splitting) or as 1H-NMR-peak list.
(29) In the 1H-NMR-peak list to each signal peak are listed the δ-value in ppm and the signal intensity in round brackets. Between the δ-value—signal intensity pairs are semicolons as delimiters.
(30) The peak list of an example has therefore the form:
(31) δ.sub.1 (intensity.sub.1); δ.sub.2 (intensity.sub.2); . . . ; δ.sub.i(intensity.sub.i); . . . ; δ.sub.n(intensity.sub.n)
(32) 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.
(33) 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.
(34) 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.
(35) 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.
(36) 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-D.sub.6 and the peak of water are shown in our 1H-NMR peak lists and have usually on average a high intensity.
(37) 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%).
(38) 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”.
(39) 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.
(40) 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.
(41) 1H-NMR Data for Compounds in Table 1 Written in Classical Form
(42) TABLE-US-00004 Ex-no NMR I-2 1H-NMR (400 MHz, d3-CD3CN): δ = 8.47-8.46 (dd, 1H), 8.43 (s, 1H), 7.99-7.97 (dd, 1H), 7.93 (s, 1H), 7.39-7.37 (dd, 1H), 4.64 (d, 1H), 4.51 (d, 1H), 4.26 (s, 1H), 3.61 (d, 1H), 3.11 (d, 1H), 0.60-0.45 (m, 4H) ppm I-3 1H-NMR (400 MHz, d3-CD3CN): δ = 8.32 (s, 1H), 8.31-8.27 (dd, 1H), 7.93-7.90 (m, 2H), 7.32-7.29 (dd, 1H), 4.92 (d, 1H), 4.18 (s, 1H), 4.12 (d, 1H), 3.46 (d, 1H), 3.22 (d, 1H), 0.84-0.74 (m, 2H), 0.51-0.39 (m, 2H) ppm I-4 1H-NMR (400 MHz, d3-CD3CN): δ = 8.32-8.31 (m, 2H), 7.94 (s, 1H), 7.76-7.73 (dd, 1H), 7.34-7.32 (dd, 1H), 4.76 (d, 1H), 4.28 (d, 1H), 4.08 (s, 1H), 3.24 (d, 1H), 2.94 (d, 1H), 0.60-0.35 (m, 4H) ppm I-5 1H-NMR (400 MHz, d3-CD3CN): δ = 8.55 (s, 1H), 8.40 (d, 1H), 8.32 (s, 1H), 7.93 (s, 1H), 7.50 (d, 1H), 4.89 (d, 1H), 4.23 (s, 1H), 4.14 (d, 1H), 3.45 (d, 1H), 3.22 (d, 111), 0.86-0.74 (m, 2H), 0.51-0.39 (m, 2H) ppm I-6 1H-NMR (400 MHz, DMSO-d6): δ = 8.52 (s, 1H), 8.35-8.31 (m, 2H), 7.86 (s, 1H), 7.57 (d, 1H), 5.48 (s, 1H), 4.60-4.30 (m, 5H), 4.15 (d, 1H), 3.26 (d, 1H), 3.10 (d, 1H), 0.87 (t, 3H) ppm I-7 1H-NMR (400 MHz, DMSO-d6): δ = 8.57 (s, 1H), 8.44-8.41 (m, 2H), 7.98 (s, 1H), 7.55 (d, 1H), 5.44 (s, 1H), 4.59 (d, 1H), 4.35 (d, 1H), 3.25 (d, 1H), 3.09 (d, 1H), 0.70-0.50 (m, 2H), 0.45-0.35 (m, 1H), 0.30-0.25 (m, 1H) ppm
NMR-Peak Lists for Compounds in Table 1
(43) TABLE-US-00005 Example I-1: .sup.1H-NMR(300.2 MHz, CDCl3): δ = 8.337(15.7); 8.184(6.3); 8.156(6.8); 7.931(4.7); 7.921(16.0); 7.904(5.8); 7.845(3.9); 7.842(4.1); 7.818(4.8); 7.815(5.0); 7.743(3.0); 7.738(2.9); 7.720(4.2); 7.715(5.4); 7.710(2.5); 7.692(3.2); 7.687(2.8); 7.573(3.7); 7.569(3.6); 7.550(3.4); 7.546(5.6); 7.542(3.4); 7.523(2.5); 7.519(2.3); 7.448(9.5); 7.420(8.9); 7.271(9.7); 7.265(16.4); 4.723(5.3); 4.676(9.2); 4.554(10.2); 4.507(6.0); 3.658(8.5); 3.609(9.8); 3.021(8.0); 2.972(7.0); 2.045(0.8); 1.706(1.7); 1.259(0.6); 0.880(1.8); 0.862(2.5); 0.855(2.4); 0.845(2.6); 0.837(3.0); 0.826(3.1); 0.820(2.8); 0.801(2.9); 0.720(2.0); 0.702(1.9); 0.697(2.8); 0.685(3.1); 0.678(2.4); 0.666(2.6); 0.661(3.4); 0.643(2.6); 0.505(2.3); 0.485(3.5); 0.482(2.6); 0.469(2.3); 0.462(3.2); 0.450(3.2); 0.446(2.1); 0.426(2.3); 0.406(3.2); 0.386(2.7); 0.381(3.4); 0.370(3.1); 0.361(2.4); 0.351(2.3); 0.345(2.7); 0.326(1.6); 0.072(0.4); 0.011(0.4); 0.000(12.2); −0.011(0.5) Example I-8: .sup.1H-NMR(400.0 MHz, CD3CN): δ = 8.261(1.6); 8.256(1.8); 8.249(1.8); 8.244(1.7); 8.230(4.8); 7.926(0.6); 7.886(0.5); 7.869(5.7); 7.851(1.8); 7.846(1.7); 7.290(1.8); 7.278(1.8); 7.271(1.7); 7.259(1.6); 5.447(3.2); 4.664(3.0); 4.628(3.4); 4.094(3.3); 4.058(2.9); 3.571(5.5); 3.249(2.0); 3.214(3.1); 3.090(3.5); 3.054(2.3); 2.889(6.7); 2.772(5.9); 2.144(9.5); 1.972(0.4); 1.964(1.2); 1.958(1.9); 1.952(8.3); 1.946(14.6); 1.940(18.9); 1.934(12.9); 1.928(6.5); 1.276(1.5); 1.249(16.0); 0.392(0.5); 0.388(0.7); 0.382(0.7); 0.373(1.3); 0.368(0.8); 0.359(0.7); 0.350(0.8); 0.062(0.5); 0.048(0.9); 0.038(1.3); 0.023(1.0); 0.016(2.5); 0.009(1.4); 0.000(4.8); −0.004(2.1); −0.013(1.3); −0.018(0.9); −0.027 (0.8); −0.210(1.1); −0.219(1.0); −0.228(1.0); −0.232(1.3); −0.234(1.3); −0.242(0.9); −0.247(0.9); −0.253 (0.6) Example I-9: .sup.1H-NMR(400.1 MHz, CDCl3): δ = 8.551(15.8); 8.527(14.6); 8.269(15.0); 7.945(15.0); 7.261(50.6); 5.299(1.6); 4.760(16.0); 4.694(6.7); 4.658(9.8); 4.513(8.9); 4.477(6.1); 4.149(1.1); 4.131(3.3); 4.113(3.3); 4.095(1.1); 3.445(8.1); 3.409(9.7); 3.082(7.7); 3.047(6.4); 2.170(1.5); 2.044(14.6); 2.005(0.4); 1.566(23.6); 1.277(3.9); 1.259(8.3); 1.241(3.9); 0.731(0.6); 0.726(1.1); 0.720(0.4); 0.713(1.5); 0.708(1.6); 0.696(5.6); 0.692(4.9); 0.681(4.0); 0.673(9.4); 0.661(15.9); 0.649(8.2); 0.645(13.9); 0.639(5.0); 0.626(2.7); 0.613(0.8); 0.000(0.8) Example I-10: .sup.1H-NMR(499.9 MHz, CDCl3): δ = 8.279(5.2); 8.206(5.3); 7.901(5.5); 7.281(2.2); 5.731(3.6); 4.651(0.4); 4.622(7.2); 4.620(6.9); 4.591(0.5); 3.715(2.6); 3.685(3.0); 3.194(2.5); 3.163(2.2); 2.561(16.0); 2.051(0.6); 1.276(0.5); 1.262(1.3); 1.253(3.0); 0.880(0.5); 0.867(0.4); 0.846(0.7); 0.843(0.7); 0.830(1.9); 0.827(2.2); 0.822(2.0); 0.813(3.2); 0.805(1.8); 0.801(0.9); 0.794(0.7); 0.791(0.7); 0.783(0.4); 0.774(0.4); 0.768(0.6); 0.759(0.3); 0.741(0.7); 0.729(2.5); 0.721(4.2); 0.714(2.5); 0.713(2.5); 0.699(0.6); 0.000(0.4) Example I-11: .sup.1H-NMR(300.2 MHz, CDCl3): δ = 8.652(3.4); 8.649(3.5); 8.541(2.8); 8.532(3.1); 8.417(2.3); 8.412(2.6); 8.404(1.9); 8.277(2.1); 7.925(2.2); 7.263(30.2); 5.537(3.9); 5.302(6.8); 4.662(0.6); 4.613(1.9); 4.570(2.4); 4.522(0.8); 3.521(2.8); 3.472(3.3); 2.951(2.6); 2.902(2.2); 1.596(16.0); 1.254(0.7); 0.826(0.5); 0.807(0.8); 0.799(0.7); 0.791(0.7); 0.779(1.1); 0.774(1.0); 0.764(0.9); 0.745(1.4); 0.719(1.0); 0.708(1.2); 0.702(0.7); 0.685(1.4); 0.666(0.9); 0.586(0.6); 0.567(1.7); 0.557(1.8); 0.545(1.6); 0.534(2.0); 0.529(2.1); 0.521(1.5); 0.510(1.3); 0.503(0.7); 0.495(1.1); 0.069(3.5); 0.011(0.5); 0.000(16.4); −0.011(0.7) Example I-12: .sup.1H-NMR(400.0 MHz, DMSO): δ = 8.558(13.6); 8.433(8.5); 8.420(8.9); 8.397(16.0); 8.022(16.0); 7.639(6.6); 7.627(6.4); 7.565(1.3); 7.560(1.9); 7.545(3.1); 7.541(3.4); 7.526(1.8); 7.522(1.8); 7.334(0.8); 7.329(0.9); 7.320(1.1); 7.314(2.1); 7.311(1.6); 7.301(1.8); 7.295(2.4); 7.290(1.4); 7.281(1.4); 7.277(1.2); 7.178(6.6); 7.159(7.2); 7.153(3.4); 7.143(2.3); 7.140(2.2); 7.132(2.1); 7.130(1.7); 5.296(11.1); 4.251(2.6); 4.215(7.1); 4.184(7.0); 4.148(2.6); 3.342(22.6); 2.941(2.3); 2.907(6.5); 2.878(6.8); 2.848(1.5); 2.844(2.6); 2.815(5.7); 2.801(5.4); 2.765(1.1); 2.548(51.6); 2.531(0.3); 2.526(0.5); 2.518(6.8); 2.513(13.7); 2.509(18.0); 2.504(12.7); 2.500(5.9); 0.000(0.8) Example I-13: .sup.1H-NMR(400.0 MHz, DMSO): δ = 8.432(11.5); 8.351(0.6); 8.338(16.0); 8.327(8.4); 8.323(6.2); 8.317(5.6); 8.128(0.3); 7.856(12.8); 7.737(3.5); 7.730(3.4); 7.716(3.9); 7.709(3.8); 7.364(6.1); 7.348(6.1); 7.343(6.1); 7.335(5.6); 6.139(12.0); 4.854(3.1); 4.818(5.5); 4.744(5.4); 4.708(3.1); 3.519(3.8); 3.484(4.7); 3.333(38.9); 3.241(4.5); 3.205(3.6); 2.544(61.9); 2.527(0.5); 2.513(12.0); 2.509(24.2); 2.504(31.5); 2.500(22.7); 2.495(10.8); 0.000(1.7) Example I-14: .sup.1H-NMR(400.0 MHz, DMSO): δ = 9.752(0.8); 8.813(1.2); 8.764(0.5); 8.756(0.5); 8.601(0.6); 8.581(0.6); 8.515(1.9); 8.508(0.6); 8.480(13.9); 8.465(0.4); 8.420(0.4); 8.361(0.4); 8.345(1.1); 8.326(16.0); 8.315(9.4); 8.302(8.3); 8.258(5.1); 8.253(5.2); 8.246(5.3); 8.241(4.5); 8.179(0.6); 8.160(0.4); 8.156(0.4); 8.031(1.3); 7.999(1.3); 7.870(0.4); 7.859(0.5); 7.850(0.5); 7.839(0.5); 7.764(0.4); 7.740(0.5); 7.715(14.5); 7.696(4.6); 7.691(4.4); 7.676(5.2); 7.672(4.3); 7.598(0.5); 7.585(0.4); 7.579(0.5); 7.568(0.4); 7.438(0.4); 7.427(0.4); 7.407(0.3); 7.276(7.3); 7.264(7.0); 7.235(5.0); 7.224(5.1); 7.216(4.9); 7.204(4.8); 6.257(14.6); 5.313(5.7); 5.277(6.2); 5.164(1.1); 4.674(6.0); 4.638(5.4); 4.576(0.4); 4.548(0.6); 4.312(0.7); 4.286(0.5); 3.798(5.2); 3.762(6.3); 3.652(0.4); 3.616(0.4); 3.505(6.3); 3.469(5.0); 3.426(0.5); 3.409(0.7); 3.392(0.8); 3.363(2.3); 3.325(764.5); 3.283(0.4); 3.271(0.3); 3.264(0.5); 2.995(1.6); 2.711(0.6); 2.675(2.8); 2.671(3.4); 2.579(0.5); 2.541(119.6); 2.506(467.9); 2.502(564.3); 2.497(386.2); 2.368(0.6); 2.333(2.8); 2.329(3.6); 1.297(0.3); 1.259(0.4); 1.235(0.9); 1.210(1.0); 1.194(1.1); 0.000(13.6); −0.009(0.5) Example I-15: .sup.1H-NMR(400.0 MHz, DMSO): δ = 8.555(13.4); 8.435(8.1); 8.422(8.5); 8.391(15.7); 8.036(16.0); 7.601(6.5); 7.589(6.3); 7.429(6.7); 7.324(4.6); 7.311(13.7); 7.301(5.4); 7.296(4.6); 7.291(1.9); 7.289(2.2); 7.284(2.3); 7.276(0.7); 7.272(0.8); 5.297(10.4); 4.199(0.7); 4.163(11.4); 4.161(11.1); 4.124(0.7); 3.332(44.9); 2.932(0.5); 2.885(1.7); 2.850(7.9); 2.837(8.2); 2.832(4.5); 2.810(0.7); 2.797(6.7); 2.752(6.4); 2.718(3.1); 2.544(64.2); 2.527(0.7); 2.514(14.5); 2.510(29.4); 2.505(38.7); 2.500(27.5); 2.496(12.9); 0.000(2.0) Example I-16: .sup.1H-NMR(400.0 MHz, CD3CN): δ = 8.297(0.9); 8.292(0.9); 8.285(0.9); 8.280(0.9); 8.261(1.7); 8.256(1.8); 8.249(1.8); 8.244(1.7); 8.136(5.6); 7.952(1.0); 7.947(1.1); 7.938(3.2); 7.933(1.7); 7.928(2.1); 7.901(5.4); 7.846(2.0); 7.841(3.9); 7.827(1.9); 7.823(1.8); 7.336(0.9); 7.325(0.9); 7.317(0.9); 7.306(0.9); 7.286(2.0); 7.274(5.5); 7.272(6.4); 7.267(3.3); 7.255(4.0); 7.252(4.6); 7.249(6.1); 7.240(0.6); 6.842(0.4); 6.834(3.3); 6.827(6.5); 6.822(1.9); 6.817(1.2); 6.811(4.1); 6.805(5.3); 6.796(0.5); 4.712(1.5); 4.676(1.6); 4.519(2.1); 4.482(3.2); 4.349(3.8); 4.313(2.5); 4.216(0.7); 4.200(2.4); 4.185(2.4); 4.169(0.8); 4.086(1.1); 4.068(3.3); 4.050(5.6); 4.032(1.4); 4.028(1.3); 4.013(1.2); 3.997(0.4); 3.980(1.6); 3.945(1.5); 3.899(5.5); 3.351(0.9); 3.314(1.4); 3.292(2.5); 3.256(3.3); 3.175(1.6); 3.139(1.1); 3.024(3.4); 2.988(2.6); 2.888(16.0); 2.771(13.7); 2.140(9.2); 1.972(14.2); 1.964(2.5); 1.958(4.0); 1.952(16.6); 1.946(28.7); 1.940(37.0); 1.934(25.1); 1.927(12.8); 1.348(11.0); 1.332(11.0); 1.323(5.9); 1.307(5.7); 1.221(3.8); 1.204(7.6); 1.186(3.8); 0.008(0.5); 0.000(11.1); −0.009(0.4) Example I-17: .sup.1H-NMR(300.2 MHz, CDCl3): δ = 8.723(0.9); 8.271(16.0); 8.173(0.9); 7.937(15.6); 7.916(0.5); 7.627(1.2); 7.293(17.1); 7.290(17.7); 7.265(26.7); 7.247(0.6); 7.237(1.0); 7.229(0.6); 7.217(0.4); 7.178(0.7); 7.169(0.5); 7.149(0.4); 6.778(0.8); 5.380(11.7); 5.367(1.6); 5.301(2.2); 4.947(0.3); 4.611(1.2); 4.562(11.1); 4.552(14.9); 4.524(0.4); 4.504(1.7); 4.399(0.7); 4.373(0.7); 3.375(6.8); 3.327(8.8); 2.922(6.8); 2.874(6.0); 2.637(0.4); 1.681(1.6); 1.633(1.8); 1.395(0.7); 1.386(0.9); 1.381(0.7); 1.372(0.8); 1.367(0.9); 1.358(0.7); 1.342(1.3); 1.300(0.6); 1.254(6.7); 1.234(0.9); 1.224(0.6); 1.135(1.1); 1.065(1.9); 0.880(0.8); 0.855(0.5); 0.826(1.3); 0.809(2.4); 0.791(2.1); 0.786(2.5); 0.782(1.8); 0.775(3.6); 0.770(2.2); 0.766(3.4); 0.744(4.8); 0.722(3.2); 0.712(2.6); 0.707(3.8); 0.689(10.0); 0.674(2.2); 0.669(3.7); 0.655(3.1); 0.636(3.9); 0.614(3.1); 0.611(2.4); 0.606(3.5); 0.597(2.4); 0.591(2.3); 0.572(2.4); 0.555(1.1); 0.011(0.6); 0.000(17.1); −0.011(0.7) Example I-18: .sup.1H-NMR(400.0 MHz, DMSO): δ = 8.493(8.3); 8.490(8.1); 8.438(16.0); 8.348(5.3); 8.346(5.2); 8.336(5.4); 8.334(5.3); 7.998(15.4); 7.530(3.5); 7.517(4.3); 7.514(4.3); 7.501(3.4); 5.450(14.6); 4.693(5.8); 4.657(7.2); 4.402(7.1); 4.365(5.8); 3.353(54.7); 3.242(4.5); 3.207(5.8); 3.020(5.6); 2.986(4.2); 2.547(24.2); 2.516(5.4); 2.512(10.9); 2.507(14.2); 2.503(10.2); 2.498(4.8); 0.634(0.8); 0.620(1.6); 0.614(1.3); 0.607(2.0); 0.602(2.2); 0.593(2.8); 0.587(3.4); 0.575(3.2); 0.566(3.0); 0.564(3.0); 0.552(1.9); 0.544(3.2); 0.532(2.7); 0.512(1.8); 0.499(3.9); 0.493(4.4); 0.480(4.7); 0.472(3.5); 0.465(3.0); 0.458(2.2); 0.452(1.3); 0.446(1.9); 0.432(0.4); 0.000(2.1) Example I-19: .sup.1H-NMR(400.0 MHz, DMSO): δ = 8.480(8.2); 8.476(8.0); 8.420(16.0); 8.348(0.4); 8.337(5.1); 8.335(5.0); 8.324(5.2); 8.322(5.0); 7.987(15.8); 7.495(3.4); 7.482(3.9); 7.479(3.9); 7.467(3.2); 5.479(7.8); 5.474(7.5); 4.581(3.5); 4.545(5.2); 4.408(4.8); 4.372(3.3); 3.331(85.2); 3.177(3.2); 3.143(4.2); 2.933(4.0); 2.899(3.1); 2.542(25.5); 2.525(0.8); 2.512(18.7); 2.508(38.0); 2.503(49.7); 2.498(34.9); 2.494(16.2); 0.586(0.3); 0.564(1.0); 0.556(1.7); 0.548(3.9); 0.534(1.5); 0.513(1.5); 0.499(4.1); 0.484(1.2); 0.462(0.5); 0.451(0.5); 0.337(0.6); 0.332(0.4); 0.326(0.6); 0.323(0.6); 0.312(0.8); 0.294(2.7); 0.278(1.3); 0.273(1.8); 0.268(3.0); 0.265(2.8); 0.259(1.6); 0.253(1.1); 0.238(2.5); 0.233(1.8); 0.228(1.3); 0.219(0.7); 0.210(0.6); 0.205(0.5); 0.194(0.5); 0.008(0.7); 0.000(21.2); −0.009(0.7) Example I-20: .sup.1H-NMR(400.0 MHz, DMSO): δ = 8.470(8.0); 8.466(8.0); 8.392(15.7); 8.346(5.1); 8.334(5.2); 8.023(15.8); 7.586(3.2); 7.573(3.9); 7.570(3.9); 7.557(4.4); 7.537(3.4); 7.534(3.6); 7.519(1.9); 7.515(1.9); 7.331(0.8); 7.326(0.9); 7.317(1.1); 7.311(2.3); 7.298(1.9); 7.293(2.6); 7.287(1.4); 7.278(1.4); 7.274(1.2); 7.175(6.1); 7.157(6.1); 7.149(3.7); 7.141(2.5); 7.138(2.2); 7.128(2.2); 5.285(13.6); 4.218(0.3); 4.182(16.0); 3.352(34.8); 2.827(1.7); 2.784(12.8); 2.774(7.4); 2.739(1.7); 2.720(0.4); 2.550(72.9); 2.533(0.4); 2.519(5.2); 2.515(10.6); 2.510(13.9); 2.506(10.0); 2.502(4.8); 2.376(0.4); 0.000(4.1) Example I-21: .sup.1H-NMR(400.0 MHz, CD3CN): δ = 8.300(0.4); 8.273(0.3); 8.245(4.9); 8.240(4.7); 8.180(3.3); 8.178(3.2); 8.168(3.4); 8.166(3.3); 8.136(6.2); 8.010(0.4); 7.651(7.2); 7.255(2.0); 7.241(2.6); 7.226(1.9); 5.352(0.4); 4.675(6.3); 4.653(2.4); 4.650(4.0); 4.646(2.6); 4.627(2.2); 4.623(2.1); 4.603(0.8); 4.598(1.0); 4.559(1.6); 4.556(2.1); 4.533(4.1); 4.531(4.6); 4.528(2.8); 4.509(3.4); 4.505(2.3); 4.484(0.9); 4.480(1.0); 4.419(2.2); 4.415(1.9); 4.394(1.7); 4.386(6.6); 4.373(6.8); 4.336(1.1); 4.086(1.0); 4.068(2.9); 4.050(3.0); 4.033(1.0); 3.119(0.9); 3.083(4.3); 3.065(5.8); 3.030(1.2); 2.891(2.3); 2.775(1.9); 2.206(8.0); 1.973(12.8); 1.967(0.8); 1.960(1.4); 1.954(6.3); 1.948(11.3); 1.942(14.9); 1.936(10.2); 1.930(5.2); 1.285(0.5); 1.222(3.5); 1.204(6.8); 1.186(3.4); 1.093(0.6); 1.089(1.1); 1.085(0.6); 1.012(9.0); 1.006(16.0); 0.999(8.6); 0.008(1.0); 0.000(20.8); −0.009(0.8) Example I-22: .sup.1H-NMR(400.0 MHz, DMSO): δ = 8.468(7.8); 8.464(7.7); 8.380(15.8); 8.346(4.8); 8.345(4.7); 8.334(4.9); 8.332(4.8); 8.031(16.0); 7.539(3.0); 7.526(3.6); 7.523(3.7); 7.510(2.9); 7.430(6.8); 7.321(3.3); 7.316(3.0); 7.307(15.5); 7.301(6.5); 7.296(4.7); 7.289(1.9); 7.286(2.1); 7.281(1.0); 7.275(0.6); 7.271(0.7); 5.276(14.7); 4.181(2.4); 4.146(7.3); 4.120(7.2); 4.084(2.4); 3.330(93.6); 2.997(0.7); 2.794(2.0); 2.760(7.0); 2.733(14.2); 2.713(0.9); 2.704(2.1); 2.677(0.4); 2.673(0.5); 2.668(0.3); 2.543(117.5); 2.526(1.1); 2.512(23.7); 2.508(47.0); 2.503(61.0); 2.499(43.0); 2.494(19.8); 2.369(0.4); 2.330(0.4); 0.008(0.7); 0.000(18.7); −0.009(0.6) Example I-23: .sup.1H-NMR(400.0 MHz, DMSO): δ = 8.332(7.0); 8.326(16.0); 8.232(4.1); 8.227(4.3); 8.220(4.5); 8.216(4.4); 8.208(4.2); 8.206(4.0); 8.196(4.2); 8.194(4.1); 7.711(12.6); 7.589(3.7); 7.584(3.8); 7.569(4.3); 7.565(4.0); 7.189(2.7); 7.176(3.4); 7.173(3.5); 7.168(4.8); 7.160(3.0); 7.156(4.7); 7.148(4.1); 7.137(4.0); 6.256(10.7); 5.323(4.7); 5.287(5.1); 4.728(4.8); 4.692(4.3); 3.862(3.8); 3.827(4.1); 3.328(86.5); 3.260(4.0); 3.225(3.5); 2.996(4.4); 2.712(0.4); 2.671(0.4); 2.542(107.0); 2.525(1.0); 2.511(21.3); 2.507(43.5); 2.502(57.2); 2.498(40.5); 2.493(19.0); 2.368(0.4); 2.329(0.4); 0.008(0.7); 0.000(20.3); −0.009(0.6) Example I-24: .sup.1H-NMR(400.0 MHz, DMSO): δ = 8.333(8.1); 8.329(8.3); 8.320(16.0); 8.307(6.4); 8.301(6.3); 8.242(4.9); 8.240(4.8); 8.230(5.0); 8.228(4.9); 7.829(15.7); 7.758(3.7); 7.752(3.6); 7.737(4.1); 7.731(4.0); 7.370(7.0); 7.349(6.3); 7.249(3.1); 7.236(3.8); 7.233(3.8); 7.221(3.0); 6.117(14.5); 4.851(4.1); 4.815(6.0); 4.704(6.0); 4.668(4.0); 3.447(4.0); 3.413(4.8); 3.343(32.2); 3.155(4.4); 3.120(3.6); 3.001(0.5); 2.715(0.6); 2.545(121.5); 2.529(0.6); 2.515(6.8); 2.510(14.0); 2.506(18.6); 2.501(13.4); 2.497(6.4); 2.371(0.6); 0.000(7.5) Example I-25: .sup.1H-NMR(400.0 MHz, CD3CN): δ = 8.286(1.2); 8.281(1.2); 8.274(1.3); 8.269(1.3); 8.254(3.3); 7.920(4.2); 7.882(1.3); 7.877(1.2); 7.863(1.3); 7.858(1.2); 7.308(1.3); 7.296(1.3); 7.289(1.3); 7.277(1.2); 4.737(1.2); 4.732(1.2); 4.701(1.4); 4.696(1.4); 4.285(1.5); 4.282(1.4); 4.249(1.3); 4.246(1.2); 4.063(2.2); 3.231(4.6); 2.889(16.0); 2.772(14.1); 2.169(8.4); 1.965(0.6); 1.959(1.1); 1.953(5.2); 1.947(9.2); 1.941(12.0); 1.934(8.1); 1.928(4.1); 0.764(0.3); 0.749(0.4); 0.745(0.4); 0.736(0.4); 0.730(0.4); 0.715(0.6); 0.708(0.3); 0.699(0.4); 0.693(0.4); 0.689(0.3); 0.679(0.4); 0.665(0.5); 0.549(0.4); 0.545(0.4); 0.529(0.5); 0.515(0.6); 0.501(0.7); 0.495(0.5); 0.482(0.7); 0.480(0.6); 0.468(0.5); 0.466(0.5); 0.456(1.2); 0.452(0.8); 0.441(0.7); 0.436(0.4); 0.429(0.6); 0.421(0.5); 0.415(0.5); 0.259(0.4); 0.243(0.4); 0.238(0.4); 0.232(0.7); 0.224(0.4); 0.218(0.5); 0.211(0.4); 0.208(0.5); 0.206(0.4); 0.198(0.6); 0.190(0.3); 0.186(0.3); 0.008(0.4); 0.000(10.4); −0.009(0.4) Example I-26: .sup.1H-NMR(400.1 MHz, CDCl3): δ = 8.331(0.3); 8.257(16.0); 8.131(1.1); 8.057(0.3); 8.025(14.0); 7.987(1.1); 7.330(37.8); 7.295(0.7); 7.272(8.6); 5.611(3.2); 4.811(6.9); 4.776(7.7); 4.514(12.5); 4.155(8.1); 4.129(0.4); 4.120(7.4); 4.112(0.4); 3.200(5.3); 3.166(7.1); 2.978(7.0); 2.944(5.2); 2.043(0.9); 1.807(0.4); 1.794(1.2); 1.785(1.2); 1.773(0.5); 1.725(1.4); 1.538(0.5); 1.526(1.2); 1.517(1.2); 1.503(0.4); 1.276(0.6); 1.263(1.0); 1.259(1.4); 1.241(0.4); 0.898(0.5); 0.881(1.5); 0.864(0.6); 0.677(5.5); 0.670(1.2); 0.655(10.8); 0.653(10.8); 0.637(1.5); 0.631(8.7); 0.460(2.7); 0.452(0.4); 0.445(3.2); 0.439(3.1); 0.436(2.4); 0.422(4.6); 0.414(2.0); 0.405(0.4); 0.399(2.1); 0.256(2.7); 0.249(0.4); 0.241(2.7); 0.235(3.2); 0.231(2.6); 0.218(4.5); 0.210(2.5); 0.201(0.4); 0.195(2.0); 0.000(5.9) Example I-27: .sup.1H-NMR(300.2 MHz, CDCl3): δ = 8.882(7.3); 8.867(7.5); 8.249(16.0); 8.224(4.1); 8.221(4.0); 8.154(3.5); 8.151(3.6); 8.125(4.1); 8.123(4.1); 7.961(10.6); 7.760(2.1); 7.755(2.2); 7.737(3.2); 7.732(4.3); 7.727(2.1); 7.709(2.8); 7.704(2.6); 7.637(2.9); 7.632(2.9); 7.614(2.4); 7.609(4.3); 7.604(2.8); 7.586(2.0); 7.581(1.8); 7.532(6.5); 7.517(6.4); 7.265(16.7); 4.917(5.3); 4.870(5.8); 4.299(8.3); 4.109(0.3); 3.963(6.2); 3.915(5.7); 3.860(3.3); 3.857(3.3); 3.813(4.3); 3.810(4.3); 3.523(5.8); 3.476(4.5); 2.045(1.5); 2.006(5.3); 1.738(1.5); 1.283(0.4); 1.259(0.9); 1.235(0.4); 0.853(1.0); 0.833(2.3); 0.827(1.6); 0.817(1.4); 0.807(2.8); 0.797(4.9); 0.791(2.0); 0.772(4.0); 0.763(3.1); 0.754(1.4); 0.743(2.1); 0.739(3.2); 0.720(1.5); 0.491(2.0); 0.471(2.6); 0.465(2.1); 0.457(2.0); 0.445(2.4); 0.436(2.4); 0.431(1.7); 0.410(1.7); 0.301(2.1); 0.280(2.4); 0.277(2.7); 0.264(2.2); 0.257(2.1); 0.244(2.1); 0.241(2.3); 0.220(1.5); 0.011(0.3); 0.000(10.8); −0.011(0.5) Example I-28: .sup.1H-NMR(300.2 MHz, CDCl3): δ = 8.709(3.2); 8.705(3.3); 8.557(1.8); 8.549(2.7); 8.544(2.2); 8.491(3.3); 8.483(2.6); 8.388(3.5); 7.954(3.7); 7.262(38.2); 5.301(3.0); 4.767(0.9); 4.718(3.4); 4.688(3.4); 4.640(0.9); 3.331(10.0); 2.439(0.4); 1.569(16.0); 1.254(0.5); 0.792(0.5); 0.771(1.3); 0.760(1.8); 0.744(2.7); 0.729(3.7); 0.721(3.3); 0.713(2.1); 0.707(1.9); 0.693(1.0); 0.674(0.5); 0.662(0.3); 0.100(2.9); 0.089(76.3); 0.078(3.8); 0.011(1.0); 0.000(27.6); −0.011(1.2) Example I-29: .sup.1H-NMR(400.1 MHz, DMSO): δ = 8.410(14.0); 7.970(13.4); 7.842(4.0); 7.822(7.6); 7.803(4.9); 7.452(5.8); 7.434(5.2); 7.433(5.4); 7.428(5.9); 7.408(5.2); 5.759(4.9); 5.472(16.0); 4.673(4.8); 4.637(6.1); 4.401(6.1); 4.365(4.9); 3.319(47.5); 3.309(5.4); 3.275(6.3); 3.060(5.8); 3.026(4.5); 2.530(0.6); 2.525(1.0); 2.517(14.2); 2.512(29.2); 2.508(39.4); 2.503(27.7); 2.499(12.8); 0.635(1.0); 0.627(1.1); 0.622(0.7); 0.614(1.5); 0.611(1.2); 0.607(1.2); 0.600(2.8); 0.595(2.1); 0.586(0.9); 0.561(1.3); 0.540(2.0); 0.535(0.9); 0.520(11.5); 0.511(7.4); 0.490(2.9); 0.481(1.0); 0.472(0.9) Example I-30: .sup.1H-NMR(300.2 MHz, CDCl3): δ = 8.339(3.5); 8.331(16.0); 8.328(12.6); 8.319(3.0); 8.269(12.1); 7.884(11.9); 7.268(11.2); 5.647(13.3); 5.302(0.4); 4.694(0.7); 4.645(12.8); 4.640(13.4); 4.592(0.8); 3.773(6.3); 3.722(7.5); 3.283(7.0); 3.232(5.5); 1.680(3.2); 1.254(0.4); 0.894(0.5); 0.889(0.7); 0.884(0.7); 0.864(4.3); 0.850(3.9); 0.843(4.5); 0.839(5.0); 0.836(4.6); 0.830(4.4); 0.823(1.6); 0.818(1.5); 0.810(0.9); 0.804(0.9); 0.797(1.1); 0.769(2.4); 0.753(3.0); 0.746(5.3); 0.738(8.1); 0.726(4.1); 0.722(4.3); 0.713(1.5); 0.700(0.4); 0.000(7.3); −0.011(0.4) Example I-31: .sup.1H-NMR(300.2 MHz, CDCl3): δ = 8.282(9.4); 7.939(8.9); 7.772(5.9); 7.745(6.5); 7.274(9.0); 7.246(5.1); 5.254(8.7); 4.558(16.0); 3.412(4.8); 3.364(5.7); 2.908(4.8); 2.860(4.0); 1.819(0.8); 0.802(0.6); 0.784(1.5); 0.766(1.7); 0.759(1.5); 0.749(2.0); 0.741(1.9); 0.735(1.3); 0.725(1.2); 0.717(1.6); 0.703(1.9); 0.690(1.9); 0.677(0.5); 0.669(3.5); 0.664(5.1); 0.659(3.4); 0.638(2.0); 0.624(1.8); 0.601(2.3); 0.583(1.2); 0.577(1.9); 0.569(2.0); 0.559(1.6); 0.552(1.8); 0.534(1.6); 0.517(0.7); 0.000(2.8) Example I-32: .sup.1H-NMR(499.9 MHz, CDCl3): δ = 8.262(9.8); 7.905(9.3); 7.730(5.8); 7.722(0.5); 7.714(6.1); 7.271(4.0); 7.143(6.3); 7.121(6.0); 7.054(5.6); 7.037(5.4); 5.595(7.5); 4.600(2.4); 4.572(4.6); 4.510(6.0); 4.482(3.3); 4.070(16.0); 3.359(4.5); 3.330(5.0); 2.846(4.3); 2.817(3.9); 1.760(1.8); 0.815(1.0); 0.804(1.4); 0.800(1.4); 0.793(1.6); 0.789(1.7); 0.782(1.8); 0.779(1.7); 0.768(1.7); 0.705(1.1); 0.691(1.7); 0.683(1.7); 0.679(1.6); 0.672(1.5); 0.669(2.1); 0.658(1.6); 0.620(1.6); 0.608(2.0); 0.606(1.6); 0.598(1.6); 0.594(1.7); 0.586(1.7); 0.572(1.1); 0.500(1.6); 0.489(1.7); 0.486(1.9); 0.479(1.7); 0.474(1.6); 0.468(1.4); 0.464(1.5); 0.453(1.0); 0.000(3.2) Example I-33: .sup.1H-NMR(400.0 MHz, DMSO): δ = 8.407(15.4); 8.314(7.1); 8.302(7.3); 7.994(16.0); 7.443(9.0); 7.379(4.8); 7.376(4.6); 7.366(4.7); 7.363(4.4); 5.497(8.1); 5.493(8.3); 4.519(3.9); 4.483(5.6); 4.335(5.1); 4.299(3.6); 3.334(81.5); 3.065(2.7); 3.062(2.6); 3.032(4.1); 3.029(4.1); 2.997(0.4); 2.918(4.3); 2.886(2.8); 2.713(0.3); 2.543(82.0); 2.526(0.6); 2.521(1.0); 2.512(14.4); 2.508(29.6); 2.504(39.3); 2.499(28.0); 2.494(13.2); 0.605(0.5); 0.600(0.6); 0.586(1.1); 0.575(1.4); 0.571(1.5); 0.566(1.5); 0.555(1.8); 0.548(2.3); 0.533(1.7); 0.525(1.6); 0.520(2.1); 0.516(1.9); 0.504(1.6); 0.495(1.7); 0.482(1.3); 0.473(0.5); 0.468(0.5); 0.465(0.5); 0.360(0.5); 0.354(0.5); 0.339(1.4); 0.323(3.1); 0.313(3.7); 0.298(3.7); 0.287(2.8); 0.272(1.1); 0.260(0.4); 0.255(0.4); 0.251(0.4) Example I-34: .sup.1H-NMR(400.0 MHz, DMSO): δ = 8.413(0.8); 8.336(16.0); 8.235(5.2); 8.230(5.4); 8.224(5.5); 8.219(5.1); 8.155(7.4); 8.142(7.5); 7.965(0.7); 7.741(15.7); 7.632(4.8); 7.628(4.6); 7.613(5.4); 7.608(4.8); 7.198(5.6); 7.186(12.8); 7.179(6.4); 7.167(4.7); 7.055(5.4); 7.052(4.7); 7.042(5.1); 7.039(4.3); 6.327(15.9); 5.429(1.7); 5.189(5.7); 5.153(6.4); 4.707(6.2); 4.671(5.4); 3.837(5.3); 3.802(5.7); 3.336(124.8); 3.208(5.3); 3.174(4.8); 3.003(1.3); 2.719(0.6); 2.683(0.5); 2.679(0.6); 2.674(0.4); 2.549(138.9); 2.519(41.1); 2.514(73.2); 2.510(89.1); 2.505(61.0); 2.501(27.7); 2.376(0.5); 2.341(0.4); 2.337(0.5); 2.332(0.4); 1.631(0.6); 1.612(0.6); 1.149(5.8); 0.812(0.7); 0.793(1.5); 0.774(0.6) Example I-35: .sup.1H-NMR(400.0 MHz, DMSO): δ = 8.389(15.2); 8.294(6.9); 8.282(7.1); 8.032(16.0); 7.510(1.6); 7.505(1.9); 7.489(3.6); 7.486(3.7); 7.465(10.3); 7.389(5.0); 7.386(4.6); 7.376(4.8); 7.373(4.4); 7.331(0.9); 7.327(0.9); 7.317(1.1); 7.312(2.4); 7.298(2.0); 7.293(2.6); 7.288(1.5); 7.279(1.4); 7.274(1.3); 7.177(4.2); 7.173(3.4); 7.161(5.0); 7.158(5.3); 7.152(2.8); 7.147(3.8); 7.143(3.7); 7.140(2.4); 7.127(2.2); 5.276(15.4); 4.184(2.6); 4.148(7.7); 4.121(7.7); 4.085(2.6); 3.340(126.7); 3.004(1.4); 2.787(0.8); 2.768(1.6); 2.753(10.9); 2.734(6.9); 2.721(6.9); 2.686(1.2); 2.679(0.6); 2.674(0.4); 2.549(115.5); 2.532(1.0); 2.519(22.0); 2.514(44.3); 2.510(57.5); 2.505(41.0); 2.501(19.4); 2.376(0.4); 2.337(0.4) Example I-36: .sup.1H-NMR(400.0 MHz, DMSO): δ = 8.357(14.2); 8.216(6.4); 8.203(6.6); 7.918(16.0); 7.393(7.6); 7.341(4.5); 7.338(4.0); 7.328(4.3); 7.325(3.9); 5.428(14.8); 4.580(1.3); 4.557(2.9); 4.537(2.1); 4.496(1.8); 4.492(1.8); 4.472(1.2); 4.468(1.3); 4.462(1.4); 4.438(2.9); 4.418(2.1); 4.400(1.7); 4.396(1.7); 4.375(2.9); 4.354(1.1); 4.350(1.1); 4.312(0.6); 4.274(11.8); 4.257(1.5); 4.253(1.5); 4.234(0.5); 3.340(58.9); 3.326(0.3); 3.043(0.3); 3.007(12.9); 2.971(0.3); 2.549(82.4); 2.535(0.4); 2.533(0.5); 2.528(0.7); 2.519(10.7); 2.515(22.4); 2.510(29.6); 2.505(20.8); 2.501(9.6); 1.629(0.4); 0.904(9.1); 0.898(15.8); 0.892(8.8) Example I-37: .sup.1H-NMR(400.0 MHz, DMSO): δ = 8.486(0.7); 8.376(13.5); 8.302(6.4); 8.289(6.4); 8.046(14.8); 7.438(8.0); 7.413(4.1); 7.409(6.5); 7.362(4.8); 7.358(4.4); 7.349(4.6); 7.346(5.2); 7.326(3.2); 7.310(9.2); 7.305(7.8); 7.300(5.6); 7.290(5.3); 7.286(4.0); 7.277(1.5); 7.271(2.0); 7.267(1.4); 5.288(10.3); 4.095(16.0); 3.343(18.0); 3.005(2.9); 2.754(2.4); 2.748(1.2); 2.720(8.5); 2.714(9.0); 2.707(8.2); 2.693(6.7); 2.679(0.6); 2.674(1.2); 2.659(2.3); 2.550(133.0); 2.535(0.6); 2.533(0.6); 2.528(0.6); 2.519(9.0); 2.515(19.0); 2.510(25.4); 2.505(18.1); 2.501(8.6); 2.375(0.6); 2.083(0.6) Example I-38: .sup.1H-NMR(400.0 MHz, DMSO): δ = 8.323(6.8); 8.317(6.7); 8.285(15.5); 8.200(6.9); 8.188(7.1); 7.835(16.0); 7.770(4.0); 7.764(3.9); 7.749(4.5); 7.743(4.5); 7.405(7.4); 7.384(6.6); 7.230(8.9); 7.084(4.8); 7.081(4.7); 7.071(4.7); 7.068(4.5); 6.157(14.6); 4.741(4.5); 4.706(6.1); 4.560(6.0); 4.524(4.3); 3.350(14.5); 3.337(3.6); 3.303(6.1); 3.239(5.9); 3.205(3.2); 3.005(0.6); 2.719(0.6); 2.550(116.7); 2.528(0.5); 2.519(5.9); 2.514(12.3); 2.510(16.3); 2.505(11.9); 2.501(5.7); 2.375(0.6); 2.082(0.5) Example I-39: .sup.1H-NMR(400.0 MHz, DMSO): δ = 8.430(15.7); 8.328(6.9); 8.315(7.1); 8.009(15.3); 7.459(9.0); 7.411(4.9); 7.408(4.6); 7.399(4.7); 7.396(4.5); 5.530(10.1); 4.640(5.3); 4.604(6.9); 4.394(6.9); 4.358(5.3); 3.340(167.6); 3.203(5.1); 3.169(6.2); 2.911(5.9); 2.877(4.8); 2.719(0.4); 2.679(0.4); 2.550(107.1); 2.533(1.3); 2.519(26.5); 2.515(54.8); 2.510(72.9); 2.506(53.1); 2.501(26.1); 2.376(0.4); 2.341(0.4); 2.337(0.5); 2.332(0.4); 0.533(0.8); 0.527(0.8); 0.517(3.6); 0.500(16.0); 0.488(6.0); 0.477(5.2); 0.463(1.7); 0.460(1.5); 0.449(0.5); 0.440(0.8) Example I-40: .sup.1H-NMR(400.0 MHz, DMSO): δ = 8.429(16.0); 8.414(0.5); 8.398(9.9); 8.396(9.9); 7.994(15.3); 7.583(6.9); 7.570(6.8); 5.522(14.2); 4.676(5.5); 4.640(7.0); 4.402(6.9); 4.366(5.5); 3.412(0.4); 3.378(1.5); 3.341(496.9); 3.311(2.0); 3.280(0.6); 3.262(0.5); 3.244(4.5); 3.210(5.9); 3.028(5.5); 2.993(4.2); 2.713(0.3); 2.677(0.6); 2.672(0.8); 2.542(84.4); 2.507(91.6); 2.503(116.3); 2.499(84.9); 2.369(0.4); 2.334(0.6); 2.330(0.7); 0.679(0.8); 0.666(1.6); 0.660(1.5); 0.653(2.1); 0.648(2.2); 0.638(2.6); 0.634(2.5); 0.622(3.6); 0.602(2.8); 0.599(2.8); 0.588(2.1); 0.579(3.1); 0.567(2.8); 0.548(1.8); 0.535(4.0); 0.529(4.5); 0.517(4.9); 0.508(3.6); 0.502(3.1); 0.494(2.3); 0.489(1.5); 0.482(1.9); 0.468(0.4); 0.000(2.8) Example I-41: .sup.1H-NMR(400.0 MHz, DMSO): δ = 8.422(16.0); 8.384(10.5); 8.382(10.6); 7.992(15.6); 7.572(7.1); 7.560(7.0); 5.553(8.8); 5.549(8.6); 4.575(4.1); 4.539(6.3); 4.417(5.8); 4.380(3.8); 3.330(142.1); 3.190(4.0); 3.156(5.0); 2.996(0.4); 2.930(4.7); 2.896(3.7); 2.676(0.4); 2.672(0.5); 2.667(0.4); 2.542(72.7); 2.507(64.3); 2.503(80.6); 2.498(59.6); 2.368(0.3); 2.334(0.4); 2.329(0.5); 2.325(0.4); 0.617(0.4); 0.585(5.8); 0.556(0.8); 0.534(5.9); 0.506(0.6); 0.495(0.5); 0.375(0.7); 0.366(0.8); 0.338(4.2); 0.313(4.1); 0.309(4.1); 0.304(3.6); 0.277(3.7); 0.253(0.7); 0.241(0.5); 0.000(10.9) Example I-42: .sup.1H-NMR(400.0 MHz, DMSO): δ = 8.628(1.9); 8.470(0.4); 8.384(0.4); 8.371(0.5); 8.336(6.7); 8.331(7.0); 8.318(16.0); 8.234(9.8); 8.139(0.8); 8.135(0.8); 8.109(1.9); 8.070(0.3); 7.839(14.4); 7.774(3.6); 7.767(3.6); 7.753(4.0); 7.746(3.9); 7.714(0.3); 7.679(0.4); 7.491(1.6); 7.483(0.9); 7.396(7.2); 7.375(6.7); 7.359(6.3); 7.346(6.2); 7.016(0.7); 7.004(0.8); 6.166(14.2); 5.601(0.5); 5.589(0.8); 5.577(0.4); 4.828(3.9); 4.792(6.4); 4.702(6.3); 4.666(3.8); 4.611(0.4); 4.103(0.7); 4.096(0.7); 3.899(0.5); 3.866(0.7); 3.727(0.6); 3.693(0.4); 3.439(4.3); 3.405(5.3); 3.337(290.2); 3.294(0.7); 3.278(0.4); 3.155(4.8); 3.121(3.8); 2.996(1.3); 2.731(0.5); 2.712(0.8); 2.676(0.5); 2.672(0.6); 2.543(167.4); 2.507(72.9); 2.503(93.3); 2.499(69.8); 2.369(0.8); 2.330(0.6); 1.109(1.6); 0.000(9.9) Example I-43: .sup.1H-NMR(400.0 MHz, DMSO): δ = 17.301(0.6); 15.999(0.6); 15.266(0.5); 15.247(0.5); 9.719(1.6); 8.983(1.0); 8.916(0.6); 8.595(0.7); 8.530(0.8); 8.494(0.6); 8.464(0.6); 8.443(0.9); 8.428(0.6); 8.365(0.9); 8.355(0.8); 8.351(0.9); 8.329(16.0); 8.300(1.2); 8.259(5.8); 8.254(6.3); 8.247(6.1); 8.243(6.1); 8.235(10.5); 8.212(0.6); 8.200(0.6); 8.186(0.6); 8.053(0.7); 8.039(0.6); 8.023(0.5); 7.830(0.6); 7.777(0.7); 7.774(0.7); 7.755(0.8); 7.724(15.1); 7.629(4.7); 7.624(4.6); 7.609(5.8); 7.605(5.0); 7.544(0.7); 7.493(1.1); 7.480(0.8); 7.469(0.7); 7.459(0.9); 7.438(0.6); 7.428(0.6); 7.360(0.6); 7.305(6.9); 7.292(6.7); 7.236(0.6); 7.213(4.8); 7.202(5.2); 7.194(4.7); 7.182(4.2); 6.719(0.5); 6.319(15.2); 5.295(5.7); 5.259(6.1); 4.729(6.2); 4.693(5.4); 4.609(0.8); 4.490(0.5); 4.476(0.6); 4.467(0.7); 4.455(0.5); 4.109(0.6); 4.087(0.6); 3.968(0.5); 3.928(0.6); 3.866(0.6); 3.839(5.1); 3.804(5.5); 3.771(0.5); 3.759(0.5); 3.743(0.5); 3.719(0.5); 3.681(0.5); 3.672(0.6); 3.659(0.6); 3.634(0.8); 3.616(0.8); 3.602(0.8); 3.595(0.7); 3.591(0.7); 3.556(1.0); 3.549(0.9); 3.534(0.9); 3.520(1.3); 3.516(1.3); 3.499(1.2); 3.483(1.6); 3.462(1.8); 3.448(1.8); 3.438(2.0); 3.430(2.1); 3.406(3.4); 3.333(4113.1); 3.280(8.7); 3.244(6.5); 3.208(1.0); 3.193(0.8); 3.173(0.7); 3.161(0.9); 3.149(0.8); 3.135(0.6); 3.129(0.7); 3.082(0.5); 2.995(1.9); 2.729(1.0); 2.675(6.4); 2.671(7.8); 2.667(5.9); 2.603(0.8); 2.574(1.2); 2.541(45.0); 2.506(1030.8); 2.502(1286.1); 2.498(932.7); 2.392(1.4); 2.369(1.1); 2.357(0.9); 2.333(6.5); 2.329(8.4); 2.324(6.3); 2.298(0.9); 2.290(1.0); 2.262(0.5); 2.255(0.6); 2.230(0.6); 2.091(0.6); 2.074(1.2); 1.953(0.6); 1.299(0.8); 1.258(1.1); 1.235(2.2); 1.108(2.7); 0.000(47.8); −2.805(0.6); −3.081(0.5); −3.161(0.5); −3.344(0.7); −3.572(0.5) Example I-44: .sup.1H-NMR(400.0 MHz, DMSO): δ = 8.366(11.1); 8.261(7.8); 7.841(11.3); 7.456(5.3); 7.443(5.0); 5.499(11.6); 4.626(1.7); 4.613(1.7); 4.602(2.5); 4.589(2.5); 4.538(2.2); 4.509(2.5); 4.495(1.8); 4.483(3.0); 4.472(4.1); 4.450(1.5); 4.419(2.1); 4.394(1.4); 4.381(2.0); 4.344(6.7); 4.329(2.4); 4.319(6.5); 4.300(0.4); 4.282(1.9); 3.403(0.6); 3.330(575.1); 3.274(0.5); 3.248(0.4); 3.046(13.3); 2.995(0.6); 2.710(0.4); 2.671(1.5); 2.541(64.2); 2.506(198.9); 2.502(235.3); 2.368(0.4); 2.328(1.5); 1.243(0.4); 1.236(0.5); 0.912(16.0); 0.000(9.1) Example I-45: .sup.1H-NMR(300.2 MHz, CDCl3): δ = 9.080(5.4); 9.064(5.6); 8.283(8.8); 8.003(7.7); 7.696(4.8); 7.679(4.7); 7.264(28.6); 5.302(16.0); 5.007(4.1); 4.960(4.5); 4.568(5.5); 4.565(5.8); 4.110(0.3); 3.969(4.7); 3.922(4.3); 3.618(2.5); 3.613(2.6); 3.571(3.1); 3.567(3.2); 3.173(4.5); 3.127(3.7); 2.047(1.5); 1.594(17.0); 1.284(0.4); 1.260(1.0); 1.246(0.4); 1.236(0.5); 0.913(0.8); 0.894(1.7); 0.887(1.2); 0.876(1.0); 0.868(2.1); 0.858(3.5); 0.850(1.5); 0.832(3.0); 0.823(2.3); 0.815(1.1); 0.804(1.5); 0.800(2.4); 0.781(1.2); 0.547(1.6); 0.527(2.0); 0.521(1.6); 0.513(1.5); 0.501(1.8); 0.492(1.8); 0.487(1.3); 0.466(1.3); 0.361(1.6); 0.338(2.1); 0.325(1.7); 0.317(1.5); 0.304(1.6); 0.301(1.7); 0.280(1.1); 0.069(0.6); 0.011(0.8); 0.000(21.5); −0.011(1.0) Example I-46: .sup.1H-NMR(300.2 MHz, CDCl3): δ = 8.282(4.3); 8.128(0.4); 8.020(3.8); 7.993(0.4); 7.730(4.5); 7.262(27.3); 5.610(1.2); 5.301(7.0); 4.991(1.9); 4.944(2.1); 4.676(2.6); 4.673(2.8); 4.158(0.4); 4.134(1.3); 4.110(1.3); 4.087(0.5); 3.992(2.2); 3.945(2.1); 3.552(1.2); 3.548(1.3); 3.506(1.6); 3.501(1.7); 3.177(2.2); 3.131(1.7); 2.046(5.9); 1.800(0.4); 1.788(0.4); 1.564(16.0); 1.546(0.4); 1.530(0.5); 1.518(0.4); 1.284(1.6); 1.260(3.3); 1.236(1.6); 0.891(0.9); 0.884(0.6); 0.870(1.0); 0.865(1.2); 0.855(1.3); 0.846(1.5); 0.836(1.2); 0.828(1.4); 0.812(1.3); 0.793(0.5); 0.562(0.7); 0.541(0.9); 0.535(0.7); 0.528(0.7); 0.515(0.9); 0.507(0.9); 0.501(0.6); 0.481(0.6); 0.371(0.8); 0.351(0.8); 0.348(1.0); 0.335(0.8); 0.326(0.7); 0.315(0.7); 0.311(0.8); 0.290(0.5); 0.011(0.6); 0.000(20.1); −0.011(1.0) Example I-47: .sup.1H-NMR(400.1 MHz, DMSO): δ = 8.493(7.6); 8.479(7.8); 8.402(16.0); 7.959(15.1); 7.582(7.4); 7.577(8.2); 7.483(5.0); 7.478(4.7); 7.469(5.0); 7.464(4.6); 5.871(15.9); 4.641(5.4); 4.605(7.2); 4.417(7.1); 4.381(5.4); 3.334(6.0); 3.321(28.8); 3.299(7.7); 3.070(6.6); 3.035(5.3); 2.530(0.6); 2.517(11.5); 2.513(23.6); 2.508(32.5); 2.504(24.0); 2.499(12.4); 0.654(0.5); 0.643(1.1); 0.632(2.4); 0.615(2.7); 0.611(3.4); 0.607(2.8); 0.595(1.7); 0.585(4.0); 0.581(4.8); 0.564(7.2); 0.552(4.0); 0.544(4.9); 0.534(3.4); 0.523(4.0); 0.520(3.5); 0.502(2.7); 0.490(1.1); 0.487(1.0); 0.475(0.4) Example I-48: .sup.1H-NMR(400.1 MHz, DMSO): δ = 8.439(0.7); 8.418(16.0); 7.994(0.7); 7.944(15.1); 7.720(4.0); 7.700(8.4); 7.681(4.7); 7.237(5.1); 7.218(4.8); 7.202(5.3); 7.182(4.8); 6.745(12.5); 5.647(1.4); 4.580(4.7); 4.544(8.2); 4.456(7.0); 4.420(4.1); 3.376(1.7); 3.325(239.0); 3.314(8.2); 3.278(7.1); 2.878(5.7); 2.842(4.9); 2.677(0.4); 2.563(0.4); 2.558(0.5); 2.530(1.3); 2.517(23.4); 2.512(47.9); 2.508(64.9); 2.503(45.8); 2.499(21.4); 2.461(0.4); 2.439(40.2); 2.339(0.3); 2.335(0.4); 1.779(0.4); 1.771(0.4); 1.593(0.4); 1.585(0.4); 0.674(0.9); 0.661(1.8); 0.655(1.4); 0.648(1.7); 0.642(2.3); 0.634(2.8); 0.628(2.8); 0.616(3.2); 0.609(2.8); 0.600(2.7); 0.596(1.7); 0.583(3.1); 0.570(2.1); 0.543(2.5); 0.530(2.9); 0.527(2.1); 0.517(1.8); 0.513(2.6); 0.503(2.2); 0.486(1.4); 0.458(2.4); 0.444(2.2); 0.439(2.4); 0.432(2.4); 0.425(2.0); 0.418(1.7); 0.413(1.8); 0.399(1.1) Example I-49: .sup.1H-NMR(400.0 MHz, CD3CN): δ = 8.524(4.3); 8.369(2.6); 8.357(2.6); 8.228(4.5); 7.871(4.6); 7.460(2.6); 7.448(2.5); 4.635(2.9); 4.599(3.3); 4.115(3.2); 4.079(2.8); 4.068(0.6); 4.050(0.6); 3.595(3.7); 3.239(1.9); 3.205(3.3); 3.110(3.6); 3.075(2.1); 2.161(28.2); 2.155(30.3); 1.972(2.7); 1.965(1.9); 1.959(3.9); 1.953(17.9); 1.947(32.0); 1.940(42.2); 1.934(28.9); 1.928(14.8); 1.247(16.0); 1.222(0.7); 1.204(1.4); 1.186(0.7); 0.426(0.5); 0.418(0.7); 0.413(0.7); 0.403(1.3); 0.396(0.8); 0.389(0.7); 0.380(0.7); 0.080(0.6); 0.067(0.9); 0.056(1.2); 0.042(0.8); 0.033(1.1); 0.024(1.5); 0.016(1.2); 0.008(2.3); 0.000(51.6); −0.009(2.8); −0.020(0.9); −0.196(1.0); −0.206(1.0); −0.212 (1.1); −0.219(1.3); −0.221(1.3); −0.229(0.9); −0.233(0.9); −0.242(0.7) Example I-50: .sup.1H-NMR(600.1 MHz, DMSO): δ = 9.185(3.3); 9.183(3.1); 9.104(9.2); 9.102(8.8); 9.096(0.4); 8.865(3.0); 8.856(3.1); 8.727(8.4); 8.718(8.6); 8.413(15.9); 7.967(15.1); 7.781(1.9); 7.779(1.9); 7.772(1.9); 7.770(1.8); 7.558(5.4); 7.556(5.2); 7.549(5.3); 7.547(5.1); 6.689(1.6); 6.686(3.1); 6.682(1.6); 5.678(16.0); 5.529(0.4); 5.417(0.8); 5.408(1.7); 5.399(0.9); 4.657(6.1); 4.633(7.6); 4.452(7.5); 4.428(6.1); 4.313(2.5); 4.310(2.8); 4.304(2.7); 4.301(2.4); 3.327(85.6); 3.314(7.5); 3.291(7.6); 3.052(7.3); 3.029(6.2); 2.615(0.4); 2.542(0.8); 2.524(0.6); 2.521(0.8); 2.518(0.8); 2.506(52.7); 2.503(72.1); 2.500(52.9); 2.390(0.3); 2.387(0.5); 2.384(0.3); 1.261(1.5); 1.250(4.1); 1.249(4.2); 1.238(1.8); 0.886(1.8); 0.875(4.1); 0.873(4.2); 0.863(1.6); 0.651(2.0); 0.647(1.7); 0.643(2.7); 0.637(1.0); 0.633(2.3); 0.630(2.7); 0.626(2.3); 0.603(0.4); 0.560(1.8); 0.554(2.8); 0.543(8.0); 0.537(3.4); 0.532(15.9); 0.521(2.1); 0.514(0.9); 0.503(0.6); 0.000(6.5) Example I-51: .sup.1H-NMR(400.0 MHz, DMSO): δ = 8.427(15.7); 8.127(3.6); 8.115(3.6); 7.988(15.7); 7.968(2.3); 7.963(3.4); 7.957(2.0); 7.944(2.0); 7.939(1.8); 7.315(2.3); 7.310(2.4); 7.303(2.4); 7.297(3.6); 7.292(2.3); 7.284(2.2); 7.280(2.1); 5.358(16.0); 4.687(5.7); 4.651(7.1); 4.375(6.9); 4.339(5.7); 3.327(53.0); 3.192(5.0); 3.157(6.5); 2.973(6.1); 2.938(4.6); 2.676(0.4); 2.672(0.5); 2.667(0.4); 2.525(1.4); 2.511(29.2); 2.507(57.6); 2.503(74.4); 2.498(53.1); 2.494(25.3); 2.334(0.4); 2.329(0.5); 2.325(0.4); 0.581(1.7); 0.571(2.2); 0.562(2.7); 0.552(5.4); 0.534(5.2); 0.531(5.2); 0.518(1.7); 0.496(1.9); 0.484(3.6); 0.476(4.2); 0.464(6.1); 0.456(3.2); 0.448(2.6); 0.443(2.7); 0.435(0.9); 0.430(1.7); 0.416(0.4); 0.000(2.9) Example I-52: .sup.1H-NMR(499.9 MHz, CDCl3): δ = 8.278(5.4); 8.246(2.8); 8.236(2.8); 7.900(5.3); 7.108(3.8); 7.018(2.1); 7.008(2.1); 4.617(2.5); 4.589(3.8); 4.484(3.7); 4.456(2.5); 3.361(2.9); 3.331(3.3); 2.810(2.8); 2.781(2.5); 2.358(16.0); 0.846(0.7); 0.835(1.0); 0.832(1.0); 0.825(1.1); 0.820(1.2); 0.814(1.3); 0.810(1.2); 0.799(1.1); 0.697(0.8); 0.683(1.2); 0.675(1.2); 0.672(1.1); 0.664(1.2); 0.661(1.4); 0.650(1.1); 0.579(1.0); 0.567(1.4); 0.557(1.1); 0.553(1.2); 0.546(1.3); 0.532(0.9); 0.475(1.1); 0.463(1.2); 0.460(1.3); 0.454(1.2); 0.449(1.1); 0.442(1.1); 0.439(1.1); 0.427(0.8); 0.000(2.3) Example I-53: .sup.1H-NMR(300.2 MHz, CDCl3): δ = 8.276(16.0); 7.988(14.0); 7.871(8.8); 7.844(9.6); 7.284(10.7); 7.266(20.5); 7.258(10.5); 5.010(7.1); 4.963(7.8); 4.392(9.6); 4.387(9.7); 4.134(0.4); 4.110(0.5); 3.950(8.1); 3.903(7.5); 3.661(4.7); 3.656(4.6); 3.614(5.5); 3.608(5.4); 3.071(8.2); 3.023(7.1); 2.046(2.0); 2.011(0.7); 1.630(2.2); 1.284(0.8); 1.260(2.2); 1.255(2.1); 1.236(0.7); 0.947(1.7); 0.927(2.8); 0.921(2.4); 0.910(2.4); 0.902(3.4); 0.891(3.5); 0.885(2.8); 0.866(3.4); 0.854(2.8); 0.834(2.3); 0.830(3.4); 0.818(3.5); 0.811(2.3); 0.799(3.0); 0.795(3.8); 0.776(2.4); 0.521(2.6); 0.501(3.5); 0.496(2.8); 0.486(2.6); 0.476(3.3); 0.466(3.2); 0.461(2.4); 0.440(2.4); 0.338(2.8); 0.317(3.3); 0.315(3.5); 0.302(3.0); 0.294(2.7); 0.281(3.0); 0.278(3.1); 0.258(2.0); 0.070(0.7); 0.011(0.4); 0.000(10.8); −0.011(0.6) Example I-54: .sup.1H-NMR(300.2 MHz, CDCl3): δ = 8.292(2.3); 8.283(9.6); 8.279(7.8); 8.265(7.4); 7.886(7.6); 7.264(19.9); 5.816(8.7); 4.633(14.8); 3.747(3.8); 3.695(4.8); 3.362(4.4); 3.311(3.3); 2.047(0.6); 2.010(2.5); 1.604(16.0); 1.260(0.4); 1.254(0.4); 0.942(1.3); 0.933(0.9); 0.926(0.7); 0.914(1.1); 0.907(1.4); 0.899(2.7); 0.880(0.8); 0.859(0.8); 0.849(1.5); 0.845(1.9); 0.839(2.0); 0.834(1.7); 0.814(0.4); 0.805(1.5); 0.784(1.9); 0.766(1.6); 0.756(4.6); 0.750(5.2); 0.740(2.4); 0.736(2.3); 0.708(0.5); 0.011(0.4); 0.000(12.6); −0.011(0.6) Example I-55: .sup.1H-NMR(300.2 MHz, CDCl3): δ = 8.289(3.9); 8.280(3.5); 8.020(3.6); 8.015(3.5); 7.630(3.4); 7.414(0.6); 7.403(6.2); 7.396(2.7); 7.391(4.1); 7.381(2.4); 7.373(8.2); 7.363(1.0); 7.263(16.2); 7.198(0.5); 7.187(4.4); 7.179(1.4); 7.165(4.8); 7.157(4.5); 7.146(0.6); 7.142(1.1); 7.135(3.0); 7.124(0.4); 5.301(2.3); 5.020(1.5); 4.973(1.6); 4.947(1.3); 4.900(1.5); 4.590(2.1); 4.585(2.2); 4.546(2.3); 4.203(1.5); 4.156(1.4); 3.996(1.7); 3.949(1.6); 3.613(1.0); 3.608(1.0); 3.566(1.2); 3.561(1.2); 3.385(0.7); 3.340(1.3); 3.230(1.6); 3.184(1.0); 3.142(1.6); 3.096(1.3); 1.597(16.0); 1.255(0.3); 0.978(0.3); 0.959(0.6); 0.953(0.5); 0.941(0.5); 0.933(0.7); 0.922(0.7); 0.916(0.6); 0.897(0.7); 0.890(0.6); 0.882(0.3); 0.866(0.9); 0.855(1.0); 0.847(0.7); 0.834(1.2); 0.831(1.2); 0.820(0.6); 0.810(1.0); 0.800(1.1); 0.791(0.4); 0.780(0.5); 0.775(0.8); 0.756(0.4); 0.564(0.6); 0.557(0.5); 0.544(0.8); 0.538(0.9); 0.530(0.9); 0.522(0.7); 0.519(0.8); 0.509(1.0); 0.503(0.9); 0.497(0.5); 0.483(0.5); 0.476(0.5); 0.389(0.5); 0.377(0.6); 0.365(0.7); 0.353(1.2); 0.344(0.7); 0.341(0.8); 0.333(1.0); 0.317(0.7); 0.308(0.4); 0.296(0.4); 0.000(10.4); −0.011(0.5) Example I-56: .sup.1H-NMR(300.2 MHz, CDCl3): δ = 8.345(5.5); 8.311(5.8); 8.148(6.5); 7.904(6.3); 7.415(0.6); 7.404(5.9); 7.397(2.0); 7.382(2.1); 7.374(7.1); 7.364(0.8); 7.263(27.1); 7.068(0.7); 7.057(7.1); 7.050(2.1); 7.035(1.9); 7.027(5.9); 7.016(0.6); 5.301(1.7); 4.635(5.0); 4.633(5.1); 4.571(1.4); 4.523(3.3); 4.459(4.2); 4.411(1.8); 4.158(0.4); 4.134(1.2); 4.110(1.2); 4.087(0.4); 3.360(2.8); 3.311(3.3); 2.767(2.7); 2.719(2.3); 2.046(5.6); 1.588(16.0); 1.284(1.6); 1.260(3.2); 1.236(1.5); 0.723(0.9); 0.714(0.5); 0.705(1.2); 0.698(1.4); 0.686(1.7); 0.680(2.0); 0.674(1.7); 0.660(2.1); 0.650(1.9); 0.632(0.9); 0.594(1.1); 0.577(1.6); 0.569(0.7); 0.555(2.0); 0.552(1.9); 0.548(1.7); 0.539(1.3); 0.531(1.5); 0.519(1.6); 0.513(0.8); 0.502(0.6); 0.494(1.0); 0.477(0.3); 0.011(0.6); 0.000(17.7); −0.011(0.7) Example I-57: .sup.1H-NMR(400.0 MHz, DMSO): δ = 8.936(14.6); 8.409(13.9); 7.964(13.2); 5.523(16.0); 4.752(4.5); 4.716(6.8); 4.591(6.6); 4.555(4.4); 3.551(4.6); 3.517(7.5); 3.426(7.5); 3.391(4.6); 3.324(50.7); 2.676(0.4); 2.671(0.6); 2.667(0.4); 2.622(0.4); 2.542(2.3); 2.511(35.9); 2.507(68.9); 2.502(87.6); 2.498(61.7); 2.493(29.0); 2.333(0.4); 2.329(0.6); 2.324(0.4); 0.981(1.1); 0.967(1.5); 0.961(1.6); 0.956(2.0); 0.948(1.7); 0.940(2.0); 0.936(1.8); 0.922(1.6); 0.780(1.1); 0.765(1.2); 0.759(2.1); 0.755(1.9); 0.744(2.4); 0.735(2.1); 0.721(1.8); 0.635(0.8); 0.621(3.6); 0.617(4.0); 0.602(4.0); 0.597(4.3); 0.591(3.3); 0.577(2.6); 0.571(2.1); 0.556(0.4); 0.000(36.7); −0.009(1.3) Example I-58: .sup.1H-NMR(300.2 MHz, CDCl3): δ = 8.377(16.0); 8.269(15.1); 7.998(13.1); 7.543(15.6); 7.265(21.6); 4.963(6.7); 4.916(7.3); 4.465(9.5); 4.461(9.1); 3.962(7.7); 3.915(7.1); 3.645(5.0); 3.639(4.7); 3.599(5.8); 3.594(5.5); 3.073(7.4); 3.027(6.4); 1.620(12.6); 0.976(1.6); 0.957(2.7); 0.950(2.3); 0.939(2.5); 0.931(3.1); 0.920(3.3); 0.914(2.6); 0.895(3.0); 0.871(2.3); 0.852(2.2); 0.847(3.0); 0.835(3.3); 0.828(2.2); 0.816(2.8); 0.812(3.4); 0.793(2.3); 0.538(2.4); 0.517(3.4); 0.512(2.7); 0.502(2.4); 0.492(3.1); 0.482(3.1); 0.477(2.2); 0.456(2.3); 0.370(2.7); 0.349(3.1); 0.346(3.3); 0.333(2.9); 0.326(2.5); 0.312(2.8); 0.310(2.9); 0.289(1.8); 0.010(0.6); 0.000(16.2); −0.011(0.8) Example I-59: .sup.1H-NMR(400.0 MHz, DMSO): δ = 9.725(0.4); 8.923(0.5); 8.423(0.4); 8.414(1.4); 8.409(1.7); 8.402(1.5); 8.398(1.6); 8.360(0.3); 8.326(15.1); 8.316(1.5); 8.258(4.6); 8.254(5.3); 8.247(5.0); 8.242(5.1); 8.222(1.4); 8.218(1.4); 8.203(1.5); 8.198(1.6); 8.186(0.4); 8.058(8.5); 8.045(8.7); 8.024(0.5); 7.901(2.4); 7.890(2.5); 7.718(15.2); 7.600(4.2); 7.596(4.6); 7.581(4.7); 7.576(4.8); 7.550(1.4); 7.538(1.5); 7.530(1.4); 7.519(1.4); 7.243(2.0); 7.231(1.9); 7.196(4.8); 7.183(6.5); 7.177(5.8); 7.169(8.0); 7.157(3.9); 6.312(16.0); 6.170(0.3); 6.142(3.8); 5.304(6.1); 5.268(6.5); 4.843(1.6); 4.815(1.7); 4.754(6.3); 4.717(5.6); 4.287(1.1); 4.280(1.1); 4.259(1.0); 4.252(1.1); 3.881(5.2); 3.846(5.5); 3.813(1.4); 3.329(723.3); 3.293(5.5); 2.995(1.2); 2.960(1.0); 2.916(0.8); 2.711(0.9); 2.671(2.5); 2.542(218.0); 2.506(311.5); 2.502(415.4); 2.498(329.3); 2.367(1.2); 2.329(2.7); 2.293(0.3); 1.258(0.4); 1.235(1.8); 0.146(0.5); 0.000(109.5); −0.150(0.6) Example I-60: .sup.1H-NMR(400.0 MHz, DMSO): δ = 8.441(16.0); 8.191(8.0); 8.179(8.3); 8.001(15.1); 7.552(3.8); 7.540(7.1); 7.527(3.6); 5.517(12.9); 4.688(5.6); 4.652(7.3); 4.452(7.2); 4.416(5.5); 3.360(41.0); 3.303(4.5); 3.268(5.7); 3.052(5.5); 3.017(4.2); 3.005(0.3); 2.720(0.4); 2.550(72.9); 2.529(0.6); 2.515(8.8); 2.511(11.8); 2.506(9.1); 2.376(0.4); 0.652(0.6); 0.639(1.6); 0.632(1.2); 0.621(2.4); 0.612(3.3); 0.606(2.6); 0.594(7.1); 0.580(1.6); 0.574(3.4); 0.562(2.7); 0.547(1.6); 0.535(7.6); 0.516(6.2); 0.507(3.2); 0.495(2.3); 0.487(1.9); 0.000(2.7) Example I-61: .sup.1H-NMR(400.0 MHz, DMSO): δ = 8.823(0.9); 8.355(12.0); 8.157(0.5); 8.145(0.5); 8.051(6.4); 8.039(6.7); 7.941(0.8); 7.837(12.1); 7.463(1.3); 7.457(3.0); 7.445(5.6); 7.432(2.9); 6.737(0.8); 5.490(11.0); 4.626(1.7); 4.609(1.7); 4.602(2.5); 4.586(2.6); 4.534(2.1); 4.508(2.7); 4.490(1.8); 4.482(3.0); 4.467(2.9); 4.451(1.6); 4.415(2.2); 4.391(1.3); 4.369(1.3); 4.357(2.2); 4.332(9.3); 4.323(8.1); 4.286(1.2); 3.344(62.3); 3.154(1.4); 3.118(6.3); 3.102(5.5); 3.066(1.2); 2.545(58.9); 2.510(17.9); 2.506(23.4); 2.502(18.0); 1.234(0.3); 1.001(1.5); 0.919(16.0); 0.751(0.4); 0.000(4.2) Example I-62: .sup.1H-NMR(400.0 MHz, DMSO): δ = 8.574(16.0); 8.430(7.7); 8.398(0.3); 7.989(7.6); 5.215(4.8); 4.686(2.0); 4.649(2.8); 4.474(2.7); 4.438(1.9); 3.487(3.0); 3.453(4.5); 3.349(389.1); 3.309(4.1); 2.996(0.4); 2.713(0.5); 2.673(0.7); 2.545(26.1); 2.543(41.4); 2.508(48.7); 2.504(63.9); 2.500(48.7); 2.369(0.4); 2.331(0.6); 1.235(0.5); 0.851(0.5); 0.836(0.6); 0.822(0.8); 0.803(1.1); 0.780(0.8); 0.772(0.7); 0.754(0.7); 0.740(0.6); 0.659(0.4); 0.639(0.8); 0.633(0.9); 0.625(0.9); 0.608(2.4); 0.586(1.2); 0.573(1.3); 0.556(0.9); 0.541(0.6); 0.526(0.5); 0.307(0.8); 0.299(1.1); 0.281(1.0); 0.275(0.8); 0.266(0.8); 0.239(0.4); 0.000(0.4) Example I-63: .sup.1H-NMR(400.0 MHz, DMSO): δ = 8.721(1.1); 8.597(1.0); 8.527(1.4); 8.503(16.0); 8.438(7.5); 8.413(0.9); 8.397(1.3); 8.332(1.8); 8.320(1.7); 8.285(1.6); 8.101(1.4); 7.970(11.4); 7.786(1.4); 7.761(0.8); 7.726(0.9); 7.643(1.3); 7.543(2.3); 7.522(3.1); 7.516(2.9); 7.448(4.8); 7.428(3.0); 6.626(0.9); 6.412(5.8); 5.165(0.9); 4.299(3.1); 4.283(5.0); 4.267(3.0); 3.355(4984.0); 3.310(5.4); 3.278(3.7); 3.263(5.2); 3.224(0.8); 3.002(2.1); 2.718(2.3); 2.680(6.8); 2.550(214.4); 2.510(791.2); 2.507(670.6); 2.376(2.0); 2.337(5.5); 1.242(4.8); 0.006(2.0) Example I-64: .sup.1H-NMR(400.0 MHz, DMSO): δ = 9.346(0.7); 8.534(0.6); 8.404(16.0); 8.354(1.6); 8.310(0.8); 8.301(1.3); 8.273(12.4); 8.114(1.6); 8.013(16.0); 7.752(0.6); 7.559(1.7); 7.554(2.3); 7.535(4.2); 7.520(2.1); 7.516(2.2); 7.408(8.4); 7.404(8.5); 7.333(1.0); 7.329(1.1); 7.314(2.8); 7.296(3.3); 7.281(1.9); 7.277(1.7); 7.262(0.3); 7.203(0.5); 7.177(6.8); 7.159(7.1); 7.151(4.5); 7.143(3.3); 7.130(2.5); 7.043(0.6); 6.864(0.4); 6.861(0.4); 6.847(0.4); 6.547(0.7); 6.543(0.8); 5.584(0.6); 5.365(14.9); 4.265(1.5); 4.229(9.9); 4.219(9.7); 4.184(1.5); 4.041(0.4); 4.028(0.4); 3.788(0.7); 3.780(0.7); 3.686(0.7); 3.506(0.8); 3.480(0.8); 3.383(0.8); 3.343(91.6); 3.001(0.5); 2.962(2.4); 2.927(8.1); 2.903(8.2); 2.868(3.4); 2.834(8.8); 2.828(8.6); 2.792(1.0); 2.716(0.5); 2.546(98.6); 2.511(31.5); 2.507(41.6); 2.502(31.3); 2.372(0.5); 1.233(0.4); 0.008(0.4); 0.000(9.9) Example I-65: .sup.1H-NMR(400.0 MHz, DMSO): δ = 8.448(0.6); 8.417(16.0); 8.400(0.3); 8.334(0.3); 8.313(11.8); 7.985(16.0); 7.329(8.2); 7.325(8.2); 5.525(8.8); 5.521(8.9); 4.614(4.1); 4.578(5.6); 4.393(5.1); 4.357(3.8); 3.336(107.5); 3.303(4.1); 3.269(5.8); 3.139(5.0); 3.105(3.4); 2.713(0.4); 2.543(83.0); 2.508(40.8); 2.504(53.1); 2.500(38.8); 2.369(0.4); 2.330(0.3); 1.235(0.5); 0.699(0.5); 0.686(0.6); 0.681(0.7); 0.670(1.3); 0.656(1.3); 0.651(1.5); 0.638(1.5); 0.631(0.9); 0.619(2.2); 0.601(2.7); 0.588(2.4); 0.568(1.4); 0.555(1.6); 0.551(1.6); 0.537(1.4); 0.521(0.7); 0.507(0.8); 0.483(0.9); 0.469(0.9); 0.465(0.9); 0.455(1.8); 0.442(1.9); 0.429(1.7); 0.416(1.4); 0.399(0.9); 0.347(1.0); 0.334(1.2); 0.330(1.3); 0.321(1.9); 0.304(1.9); 0.295(1.2); 0.290(1.4); 0.281(0.9); 0.263(0.6); 0.008(0.6); 0.000(13.0); −0.008(0.5) Example I-66: .sup.1H-NMR(400.0 MHz, DMSO): δ = 8.452(4.8); 8.293(2.8); 8.281(3.0); 8.236(5.3); 7.920(5.3); 7.315(2.3); 7.302(2.2); 5.777(3.9); 5.587(4.5); 4.477(5.9); 3.662(16.0); 3.652(0.8); 3.370(0.6); 3.338(185.7); 3.310(0.4); 3.234(1.3); 3.199(2.1); 3.118(2.3); 3.082(1.4); 2.671(0.3); 2.542(36.3); 2.525(1.1); 2.511(20.4); 2.507(41.2); 2.502(54.1); 2.498(39.3); 2.493(19.3); 2.329(0.4); 2.160(12.2); 2.126(0.3); 0.000(4.0) Example I-67: .sup.1H-NMR(400.0 MHz, DMSO): δ = 8.557(7.3); 8.551(7.4); 8.398(16.0); 7.961(15.2); 7.920(4.4); 7.913(4.4); 7.899(4.9); 7.892(4.8); 7.482(7.6); 7.461(7.0); 5.673(15.6); 4.637(5.6); 4.601(7.5); 4.405(7.3); 4.369(5.6); 4.039(0.4); 4.021(0.4); 3.330(63.7); 3.297(7.4); 3.033(7.1); 2.998(5.8); 2.673(0.4); 2.508(41.4); 2.503(54.0); 2.499(40.0); 2.330(0.3); 1.990(1.5); 1.910(0.6); 1.193(0.4); 1.175(0.8); 1.158(0.4); 0.616(0.6); 0.609(1.0); 0.598(1.6); 0.594(2.1); 0.576(3.8); 0.562(0.9); 0.552(3.1); 0.545(4.3); 0.531(8.6); 0.510(8.8); 0.504(5.9); 0.488(2.0); 0.480(1.2); 0.467(0.8); 0.008(1.1); 0.000(28.5); −0.008(1.4) Example I-68: .sup.1H-NMR(400.0 MHz, DMSO): δ = 8.581(15.4); 8.493(16.0); 8.452(8.1); 8.440(9.6); 8.426(1.7); 8.024(15.6); 7.997(0.7); 7.657(7.5); 7.645(7.2); 7.379(1.5); 7.367(6.5); 7.349(6.2); 7.284(0.7); 7.276(1.6); 7.265(10.6); 7.258(8.1); 7.251(6.9); 7.232(1.9); 7.230(1.9); 7.218(3.5); 7.211(2.8); 7.202(2.5); 7.199(3.3); 7.192(2.5); 7.183(1.6); 7.176(1.4); 5.327(1.3); 5.285(13.7); 4.462(4.7); 4.426(6.7); 4.293(6.7); 4.257(4.7); 3.356(59.0); 3.135(4.4); 3.100(6.9); 3.053(5.2); 3.001(6.8); 2.966(4.4); 2.926(0.4); 2.904(0.9); 2.891(1.1); 2.870(2.4); 2.858(2.6); 2.839(2.3); 2.826(3.4); 2.814(2.2); 2.795(2.5); 2.783(2.3); 2.762(1.1); 2.750(0.9); 2.718(0.6); 2.548(98.1); 2.513(17.2); 2.509(21.7); 2.504(16.0); 2.374(0.5); 1.641(1.0); 1.629(1.3); 1.608(2.3); 1.595(2.3); 1.577(1.7); 1.564(1.5); 1.507(1.6); 1.494(1.8); 1.475(2.3); 1.463(2.2); 1.441(1.3); 1.429(1.0); 0.000(3.0) Example I-69: .sup.1H-NMR(400.0 MHz, CD3CN): δ = 8.538(14.7); 8.394(8.8); 8.382(9.0); 8.203(14.9); 8.160(0.4); 7.907(14.8); 7.483(7.8); 7.471(7.5); 7.282(1.4); 7.276(11.1); 7.271(4.6); 7.260(5.0); 7.255(16.0); 7.161(14.1); 7.140(9.7); 4.440(7.0); 4.404(9.5); 4.221(9.2); 4.185(6.7); 4.085(0.4); 4.068(1.3); 4.050(1.4); 4.032(0.5); 3.565(8.6); 3.109(5.5); 3.075(10.4); 3.004(10.1); 2.970(5.3); 2.844(1.1); 2.831(1.3); 2.811(2.6); 2.798(2.8); 2.780(2.5); 2.767(2.3); 2.749(2.2); 2.736(2.4); 2.718(2.9); 2.705(2.8); 2.685(1.3); 2.672(1.2); 2.150(20.4); 2.107(0.4); 1.972(6.2); 1.964(2.0); 1.958(4.5); 1.952(23.0); 1.946(41.5); 1.940(55.3); 1.934(37.9); 1.928(19.4); 1.769(0.3); 1.701(1.3); 1.688(1.5); 1.666(3.1); 1.657(1.7); 1.653(3.0); 1.636(3.0); 1.622(2.9); 1.616(3.2); 1.603(3.2); 1.586(3.0); 1.582(1.9); 1.573(3.0); 1.551(1.5); 1.538(1.2); 1.221(1.6); 1.204(3.2); 1.186(1.6); 0.146(0.6); 0.022(0.3); 0.020(0.4); 0.0192(0.4); 0.0185(0.5); 0.018(0.5); 0.017(0.5); 0.008(5.6); 0.000(138.8); −0.009(5.5); −0.150 (0.6) Example I-70: .sup.1H-NMR(400.0 MHz, DMSO): δ = 20.014(0.6); 8.732(0.4); 8.627(0.5); 8.575(2.4); 8.519(7.2); 8.466(0.5); 8.443(7.7); 8.434(1.8); 8.422(1.7); 8.387(0.7); 8.345(4.0); 8.333(4.3); 7.863(7.8); 7.641(3.5); 7.629(3.4); 7.379(1.5); 7.367(1.7); 7.356(6.1); 7.334(7.5); 7.041(6.8); 7.019(6.2); 5.471(6.8); 5.325(0.8); 4.601(2.3); 4.564(3.1); 4.374(3.1); 4.338(2.5); 3.361(2793.1); 3.267(6.8); 3.255(6.0); 3.219(2.1); 3.163(1.6); 3.053(5.6); 2.996(1.2); 2.714(1.0); 2.673(2.9); 2.543(145.3); 2.509(300.0); 2.504(388.0); 2.500(283.9); 2.370(0.7); 2.331(2.5); 2.196(0.8); 2.029(0.9); 2.010(1.5); 1.991(1.6); 1.627(1.1); 1.501(2.2); 1.438(1.2); 1.417(1.3); 1.391(2.3); 1.360(2.3); 1.330(1.8); 1.236(7.5); 1.199(16.0); 1.171(1.1); 1.129(15.6); 1.067(1.0); 0.854(2.0); 0.837(1.0); 0.000(19.6) Example I-71: .sup.1H-NMR(300.2 MHz, CDCl3): δ = 8.349(4.5); 8.341(6.1); 8.303(5.1); 8.295(3.7); 8.268(8.6); 7.886(8.4); 7.266(12.8); 5.696(9.5); 5.612(0.9); 5.302(0.5); 4.642(15.5); 3.782(4.0); 3.730(5.0); 3.336(4.5); 3.285(3.6); 1.789(0.3); 1.634(16.0); 1.531(0.4); 1.254(0.8); 0.918(1.2); 0.909(1.0); 0.890(1.4); 0.884(2.0); 0.879(2.7); 0.875(2.4); 0.846(3.5); 0.840(3.1); 0.834(2.1); 0.808(1.6); 0.780(2.3); 0.768(1.6); 0.747(7.0); 0.737(3.8); 0.730(1.7); 0.708(0.6); 0.070(1.0); 0.011(0.3); 0.000(8.3) Example I-72: .sup.1H-NMR(300.2 MHz, CDCl3): δ = 8.261(3.1); 8.113(0.7); 8.027(2.0); 8.018(2.4); 7.986(0.8); 7.924(2.8); 7.915(2.4); 7.860(3.3); 7.268(4.6); 6.110(2.8); 5.302(0.9); 4.814(0.7); 4.784(1.1); 4.731(0.7); 4.680(0.3); 4.634(0.4); 4.586(3.6); 4.576(3.8); 4.528(0.4); 4.006(16.0); 3.932(0.4); 3.563(1.9); 3.511(2.3); 3.081(2.1); 3.029(1.7); 2.047(1.3); 1.697(1.9); 1.284(0.7); 1.254(2.7); 1.236(0.7); 1.224(0.5); 1.208(0.4); 1.147(0.4); 0.877(0.3); 0.849(2.7); 0.839(3.9); 0.811(0.5); 0.801(0.6); 0.786(0.4); 0.746(0.7); 0.708(1.7); 0.704(2.0); 0.670(1.7); 0.666(1.8); 0.641(0.7); 0.633(0.5); 0.628(0.5); 0.070(0.4); 0.000(2.9) Example I-73: .sup.1H-NMR(400.0 MHz, DMSO): δ = 8.699(1.3); 8.542(1.1); 8.508(0.8); 8.408(1.2); 8.404(1.2); 8.393(12.8); 8.353(1.2); 8.340(10.2); 8.303(1.3); 8.124(1.2); 8.084(1.5); 8.076(0.9); 8.009(12.7); 7.974(0.5); 7.632(5.5); 7.620(5.5); 7.537(2.3); 7.521(3.8); 7.502(2.0); 7.412(0.7); 7.399(0.7); 7.376(0.3); 7.357(0.6); 7.345(0.8); 7.322(1.8); 7.307(3.3); 7.288(3.6); 7.274(2.3); 7.270(2.3); 7.259(2.0); 7.245(2.2); 7.225(0.9); 7.220(1.0); 7.206(1.3); 7.187(1.6); 7.169(6.7); 7.150(7.5); 7.141(5.4); 7.119(3.7); 7.111(2.7); 7.092(1.6); 7.046(0.6); 7.027(0.8); 7.010(0.5); 6.970(0.8); 6.957(0.8); 6.851(0.4); 6.832(0.5); 6.726(0.9); 6.617(0.6); 6.353(0.5); 6.018(0.4); 5.903(0.7); 5.849(0.5); 5.814(1.0); 5.616(1.0); 5.568(0.5); 5.551(0.9); 5.340(11.8); 5.319(0.4); 5.306(0.5); 5.205(0.5); 5.191(0.8); 5.176(0.4); 5.064(0.4); 5.018(0.4); 4.761(0.4); 4.738(0.4); 4.408(0.3); 4.313(0.4); 4.198(16.0); 4.149(0.6); 4.126(0.5); 4.001(1.8); 3.986(1.7); 3.971(0.7); 3.749(0.4); 3.740(0.4); 3.721(0.4); 3.704(1.2); 3.683(0.6); 3.543(2.7); 3.415(0.3); 3.377(2.0); 3.338(374.1); 3.282(0.7); 3.256(0.3); 3.018(0.4); 2.997(2.6); 2.926(0.4); 2.820(1.7); 2.795(12.5); 2.768(6.6); 2.733(1.6); 2.713(0.9); 2.691(0.5); 2.673(0.8); 2.543(165.1); 2.508(94.1); 2.504(118.8); 2.500(90.6); 2.369(0.9); 2.331(0.8); 2.289(0.5); 2.255(0.4); 0.000(5.6) Example I-74: .sup.1H-NMR(400.0 MHz, DMSO): δ = 8.609(0.8); 8.474(0.8); 8.462(0.5); 8.417(0.4); 8.399(0.4); 8.383(12.7); 8.344(9.3); 8.309(0.9); 8.132(0.7); 8.115(1.0); 8.056(0.5); 8.027(12.9); 7.600(5.7); 7.588(5.4); 7.430(6.8); 7.394(0.7); 7.372(0.9); 7.360(0.7); 7.352(0.7); 7.333(0.8); 7.319(3.5); 7.306(16.0); 7.296(6.1); 7.288(3.7); 7.274(1.9); 7.243(1.1); 7.225(0.8); 7.207(0.8); 7.200(0.5); 7.177(0.7); 7.163(0.8); 7.140(0.6); 7.076(0.3); 6.971(0.7); 6.965(0.7); 6.950(0.6); 6.771(0.4); 5.871(0.5); 5.467(0.6); 5.414(0.5); 5.339(10.4); 4.210(2.8); 4.196(0.3); 4.175(6.0); 4.144(0.4); 4.122(5.9); 4.087(2.9); 3.979(0.5); 3.969(0.6); 3.665(0.4); 3.635(0.9); 3.544(0.5); 3.405(0.5); 3.337(383.2); 3.299(1.3); 3.258(0.6); 3.224(0.5); 2.996(3.2); 2.813(2.1); 2.779(6.1); 2.753(6.5); 2.736(12.2); 2.719(2.5); 2.701(0.5); 2.677(0.8); 2.672(0.9); 2.668(0.7); 2.646(0.3); 2.570(0.5); 2.543(177.7); 2.526(3.4); 2.508(92.8); 2.503(118.9); 2.499(87.7); 2.369(0.9); 2.334(0.7); 2.330(0.9); 2.326(0.7); 2.314(0.4); 1.235(0.3); 0.000(6.1) Example I-75: .sup.1H-NMR(400.0 MHz, DMSO): δ = 8.557(15.2); 8.439(8.3); 8.427(8.7); 8.387(15.2); 8.327(0.6); 8.314(0.6); 8.300(1.2); 8.102(1.2); 8.036(16.0); 7.608(6.9); 7.596(6.7); 7.412(4.8); 7.398(6.0); 7.391(6.5); 7.376(5.4); 7.135(6.0); 7.113(10.4); 7.091(5.2); 7.041(0.7); 7.018(0.9); 7.002(0.6); 6.995(0.3); 6.760(0.5); 6.747(0.5); 5.594(0.5); 5.251(14.4); 4.185(0.6); 4.148(14.5); 4.111(0.6); 3.485(0.5); 3.450(0.9); 3.422(0.6); 3.359(24.5); 3.257(0.4); 2.887(2.4); 2.853(7.9); 2.830(7.9); 2.809(2.8); 2.795(2.6); 2.775(6.9); 2.742(6.7); 2.721(0.5); 2.708(2.5); 2.551(50.7); 2.534(0.5); 2.516(12.2); 2.512(16.4); 2.508(12.5); 0.000(6.2) Example I-76: .sup.1H-NMR(400.0 MHz, DMSO): δ = 8.581(0.5); 8.575(0.6); 8.550(0.4); 8.539(11.4); 8.525(0.4); 8.384(12.5); 8.373(6.8); 8.360(6.9); 8.136(0.6); 7.896(12.6); 7.596(5.7); 7.583(5.5); 5.597(10.8); 4.447(3.9); 4.411(5.1); 4.197(3.5); 4.162(2.7); 4.160(2.7); 3.365(0.3); 3.337(118.7); 3.102(16.0); 2.997(0.4); 2.672(0.3); 2.543(71.1); 2.526(1.1); 2.512(21.2); 2.508(41.3); 2.503(53.2); 2.499(38.1); 2.495(18.4); 2.330(0.3); 1.570(0.6); 1.513(0.6); 1.454(0.9); 1.424(12.5); 1.397(1.1); 1.367(12.5); 1.223(0.6); 1.177(12.5); 1.120(12.4); 0.000(6.8) Example I-77: .sup.1H-NMR(400.0 MHz, DMSO): δ = 8.564(1.4); 8.531(14.7); 8.465(1.7); 8.430(15.8); 8.415(0.4); 8.401(8.6); 8.388(8.9); 8.295(0.9); 8.283(0.9); 8.060(1.7); 7.982(16.0); 7.613(7.2); 7.601(7.0); 6.675(0.7); 6.662(0.7); 5.290(0.7); 5.062(14.8); 4.172(3.9); 4.137(8.3); 4.085(8.3); 4.050(3.9); 3.947(0.4); 3.735(0.3); 3.723(0.3); 3.376(1.0); 3.368(0.6); 3.339(213.1); 3.305(0.6); 2.963(5.3); 2.929(7.0); 2.901(0.3); 2.729(6.6); 2.713(0.5); 2.695(5.1); 2.677(0.5); 2.673(0.6); 2.668(0.4); 2.543(97.3); 2.526(1.5); 2.512(35.7); 2.508(72.1); 2.504(94.2); 2.499(68.4); 2.495(33.4); 2.432(0.6); 2.410(1.8); 2.388(2.7); 2.368(2.3); 2.353(0.5); 2.345(0.6); 2.335(0.5); 2.330(0.7); 2.326(0.5); 1.956(0.3); 1.934(2.0); 1.911(3.0); 1.887(2.6); 1.863(1.1); 1.851(0.9); 1.828(1.9); 1.804(3.0); 1.779(2.6); 1.756(0.9); 1.694(0.5); 1.671(1.1); 1.647(2.1); 1.625(2.3); 1.605(2.4); 1.587(2.0); 1.577(2.0); 1.556(1.3); 1.540(0.7); 1.530(1.2); 1.525(1.3); 1.501(2.3); 1.476(1.9); 1.460(0.7); 1.438(0.6); 1.406(1.6); 1.401(1.6); 1.393(1.4); 1.386(1.4); 1.234(0.5); 0.008(0.7); 0.000(17.6); −0.009(0.7) Example I-78: .sup.1H-NMR(400.0 MHz, DMSO): δ = 17.141(0.9); 8.469(3.4); 8.397(3.8); 8.316(4.3); 8.167(2.2); 8.154(1.9); 8.077(4.1); 7.679(0.9); 7.193(16.0); 6.430(1.6); 6.418(1.7); 5.277(1.6); 3.708(1.1); 3.677(1.4); 3.670(1.3); 3.576(1.0); 3.542(1.6); 3.455(2.4); 3.413(2.3); 3.400(2.6); 3.385(2.6); 3.370(6.4); 3.334(3525.6); 3.294(4.3); 3.263(1.5); 3.249(1.1); 3.221(1.1); 3.206(1.3); 3.189(0.9); 2.711(1.2); 2.671(10.8); 2.591(1.9); 2.579(1.9); 2.573(1.6); 2.542(240.5); 2.507(1420.4); 2.502(1769.6); 2.498(1247.5); 2.400(1.2); 2.368(1.6); 2.334(8.7); 2.329(11.1); 2.325(8.1); 2.290(1.4); 2.278(0.9); 1.299(1.2); 1.259(1.5); 1.235(4.8); 1.112(1.2); 0.865(1.1); 0.854(1.4); 0.840(1.2); 0.146(1.2); 0.008(11.6); 0.000(290.5); −0.009(10.4); −0.150(1.5) Example I-79: .sup.1H-NMR(400.0 MHz, DMSO): δ = 19.997(0.4); 8.546(12.2); 8.538(1.1); 8.522(0.9); 8.417(15.0); 8.407(7.4); 8.380(0.6); 8.354(0.4); 8.317(1.5); 8.303(0.3); 8.291(0.3); 8.035(0.8); 7.969(12.8); 7.513(5.8); 7.501(5.9); 7.131(4.8); 7.109(9.0); 7.093(2.5); 7.087(5.7); 7.076(1.1); 7.062(0.5); 6.933(0.5); 6.911(0.5); 6.882(6.0); 6.871(6.2); 6.865(3.5); 6.859(5.2); 6.848(4.9); 6.816(0.4); 6.739(0.4); 5.581(10.8); 5.520(0.3); 4.908(0.6); 4.526(3.4); 4.490(5.5); 4.394(5.5); 4.358(3.5); 3.816(0.4); 3.800(0.5); 3.750(0.4); 3.593(16.0); 3.463(0.4); 3.456(0.4); 3.427(0.4); 3.384(0.5); 3.334(1146.6); 3.293(2.5); 3.271(1.3); 3.232(0.7); 3.195(3.8); 3.161(5.5); 3.124(0.5); 3.100(0.5); 3.071(0.6); 3.047(5.4); 3.013(3.5); 2.996(1.7); 2.968(0.4); 2.712(1.2); 2.676(2.6); 2.671(3.4); 2.542(299.5); 2.511(225.9); 2.507(450.3); 2.502(586.9); 2.498(425.5); 2.441(1.0); 2.368(1.6); 2.333(2.9); 2.329(3.8); 2.325(2.8); 2.291(0.8); 1.298(0.5); 1.258(0.7); 1.235(2.3); 0.855(0.3); 0.146(0.6); 0.008(4.4); 0.000(112.6); −0.008 (4.0); −0.149(0.6) Example I-80: .sup.1H-NMR(400.0 MHz, CD3CN): δ = 12.038(0.5); 12.028(0.5); 8.391(1.5); 8.381(8.9); 8.367(0.3); 8.357(0.3); 8.332(0.5); 8.325(0.5); 8.269(0.7); 8.258(0.7); 8.227(0.6); 8.203(0.6); 8.180(1.5); 8.173(5.9); 8.168(1.7); 8.160(6.0); 8.118(0.5); 8.062(11.6); 8.057(8.2); 8.054(4.7); 8.028(0.9); 8.005(3.8); 7.986(3.9); 7.985(3.8); 7.963(0.7); 7.950(1.2); 7.930(1.5); 7.792(9.0); 7.609(3.1); 7.598(1.2); 7.589(4.8); 7.581(0.8); 7.525(2.1); 7.522(2.3); 7.500(16.0); 7.497(14.3); 7.486(2.1); 7.483(2.0); 7.416(0.5); 7.412(0.5); 7.398(2.9); 7.396(3.1); 7.379(4.4); 7.361(2.0); 7.359(1.9); 7.148(0.7); 7.132(4.9); 7.119(4.6); 4.839(4.1); 4.803(6.5); 4.699(6.7); 4.685(1.2); 4.664(5.9); 4.650(0.9); 4.288(0.4); 4.086(0.9); 4.068(2.6); 4.051(2.7); 4.033(0.9); 3.509(3.5); 3.474(6.7); 3.400(6.4); 3.365(3.4); 2.952(0.7); 2.890(3.8); 2.775(3.3); 2.191(9.4); 1.973(11.9); 1.965(1.2); 1.959(2.8); 1.954(13.7); 1.947(24.4); 1.941(32.2); 1.935(21.9); 1.929(11.2); 1.221(3.1); 1.203(6.1); 1.186(3.0); 0.146(0.5); 0.008(5.1); 0.000(101.6); −0.009(4.2); −0.150(0.5) Example I-81: .sup.1H-NMR(300.2 MHz, CDCl3): δ = 8.902(11.3); 8.745(6.9); 8.728(7.4); 8.241(16.0); 7.989(15.0); 7.846(6.3); 7.829(6.2); 7.265(28.4); 4.843(7.1); 4.796(7.8); 4.591(8.2); 4.158(0.5); 4.134(1.7); 4.111(1.7); 4.087(0.6); 3.749(12.4); 3.702(12.7); 3.117(6.5); 3.068(5.7); 2.173(0.6); 2.047(7.5); 1.830(0.3); 1.705(1.5); 1.458(3.7); 1.284(2.0); 1.260(4.1); 1.236(2.0); 1.061(2.0); 1.042(2.8); 1.036(2.7); 1.025(2.8); 1.017(3.3); 1.006(3.3); 1.000(3.0); 0.980(3.1); 0.898(2.4); 0.878(2.5); 0.874(3.3); 0.862(3.4); 0.855(2.6); 0.843(3.1); 0.839(3.8); 0.820(2.7); 0.539(2.6); 0.519(3.6); 0.514(3.1); 0.504(2.6); 0.493(3.4); 0.483(3.3); 0.479(2.6); 0.458(2.6); 0.378(3.0); 0.355(3.8); 0.342(3.2); 0.334(2.8); 0.319(3.5); 0.298(2.0); 0.011(0.7); 0.000(21.2); −0.011(1.1) Example I-82: .sup.1H-NMR(400.1 MHz, DMSO): δ = 8.417(15.8); 8.307(8.8); 8.294(9.2); 7.989(15.5); 7.618(8.5); 7.606(8.2); 5.378(16.0); 4.714(5.6); 4.678(6.7); 4.364(6.6); 4.327(5.5); 4.046(0.5); 4.028(0.5); 3.383(1.9); 3.366(0.8); 3.349(10.0); 3.336(10.1); 3.316(113.0); 3.301(2.5); 3.265(0.6); 2.677(0.3); 2.530(1.0); 2.517(20.4); 2.512(40.9); 2.508(54.7); 2.503(38.7); 2.499(18.2); 2.458(0.4); 2.335(0.3); 2.079(0.6); 1.995(2.1); 1.200(0.6); 1.182(1.1); 1.164(0.6); 0.879(1.1); 0.865(1.6); 0.856(2.5); 0.845(1.8); 0.839(2.3); 0.834(1.9); 0.820(1.8); 0.750(1.2); 0.735(1.1); 0.728(3.2); 0.712(2.1); 0.705(2.4); 0.691(1.9); 0.591(5.9); 0.570(6.9); 0.547(2.8); 0.545(2.9) Example I-83: .sup.1H-NMR(499.9 MHz, CDCl3): δ = 8.289(4.4); 8.284(4.7); 8.269(7.7); 7.985(6.7); 7.895(4.4); 7.890(4.4); 7.265(5.9); 5.005(3.6); 4.977(3.9); 4.424(4.9); 4.421(4.8); 3.957(4.0); 3.929(3.9); 3.662(2.6); 3.659(2.5); 3.633(2.8); 3.630(2.7); 3.056(3.9); 3.027(3.6); 1.643(16.0); 0.948(1.0); 0.936(1.4); 0.933(1.3); 0.926(1.3); 0.921(1.6); 0.914(1.6); 0.911(1.4); 0.899(1.5); 0.850(1.2); 0.839(1.3); 0.836(1.5); 0.829(1.6); 0.825(1.3); 0.817(1.5); 0.815(1.7); 0.803(1.2); 0.522(1.2); 0.510(1.7); 0.507(1.5); 0.501(1.4); 0.495(1.6); 0.488(1.6); 0.486(1.3); 0.473(1.2); 0.353(1.3); 0.340(1.7); 0.339(1.7); 0.331(1.5); 0.326(1.4); 0.318(1.7); 0.317(1.6); 0.304(1.1); 0.000(0.8) Example I-84: .sup.1H-NMR(499.9 MHz, CDCl3): δ = 8.285(6.1); 8.272(6.5); 7.943(5.6); 7.662(1.9); 7.645(2.2); 7.565(1.7); 7.551(2.2); 7.462(2.2); 7.446(2.5); 7.431(1.5); 7.258(6.9); 5.087(2.9); 5.059(3.1); 4.308(3.9); 4.306(4.0); 3.965(3.3); 3.936(3.1); 3.896(2.0); 3.893(2.0); 3.867(2.1); 3.864(2.2); 3.226(3.0); 3.197(2.7); 2.767(16.0); 1.589(6.0); 1.000(0.8); 0.988(1.1); 0.985(1.1); 0.978(1.1); 0.973(1.2); 0.966(1.2); 0.963(1.1); 0.951(1.1); 0.882(0.4); 0.865(0.9); 0.853(1.0); 0.850(1.2); 0.843(1.2); 0.839(1.0); 0.831(1.2); 0.829(1.3); 0.817(0.9); 0.525(1.0); 0.513(1.3); 0.510(1.2); 0.504(1.1); 0.498(1.3); 0.491(1.2); 0.489(1.1); 0.476(0.9); 0.364(1.0); 0.350(1.4); 0.342(1.2); 0.337(1.1); 0.329(1.3); 0.328(1.3); 0.316(0.8); 0.000(5.2) Example I-85: .sup.1H-NMR(400.0 MHz, DMSO): δ = 8.428(16.0); 8.129(4.2); 8.116(4.2); 7.420(2.2); 7.408(3.8); 7.395(2.0); 7.344(1.5); 7.324(3.1); 7.304(2.8); 7.282(2.0); 7.268(1.1); 7.173(2.0); 7.146(3.2); 7.143(3.2); 7.124(4.4); 7.104(1.6); 5.370(2.3); 4.160(1.6); 4.125(4.3); 4.091(4.3); 4.056(1.6); 3.335(69.1); 2.997(0.5); 2.932(0.5); 2.878(2.3); 2.844(3.1); 2.825(2.1); 2.814(0.8); 2.790(3.3); 2.702(3.3); 2.666(5.2); 2.631(2.3); 2.543(76.4); 2.503(63.4); 2.368(0.4); 2.330(0.4); 1.234(0.4); 0.000(13.9) Example I-86: .sup.1H-NMR(400.0 MHz, DMSO): δ = 8.327(4.0); 8.322(3.8); 8.194(16.0); 8.089(4.2); 8.077(4.1); 7.775(2.1); 7.769(2.0); 7.754(2.3); 7.748(2.1); 7.425(3.8); 7.404(3.4); 7.175(2.0); 7.163(3.6); 7.150(1.8); 6.302(4.5); 4.727(2.3); 4.691(3.2); 4.531(3.2); 4.495(2.3); 3.435(2.3); 3.400(2.8); 3.338(60.3); 3.156(2.7); 3.122(2.2); 2.997(0.3); 2.713(0.3); 2.543(74.6); 2.507(36.6); 2.504(42.5); 2.369(0.4); 1.234(0.4); 0.000(10.4) Example I-87: .sup.1H-NMR(400.0 MHz, DMSO): δ = 8.379(16.0); 8.199(4.3); 8.187(4.4); 7.470(2.0); 7.458(3.7); 7.445(1.9); 5.654(3.8); 5.651(3.8); 4.493(1.8); 4.455(2.4); 4.235(2.7); 4.199(2.0); 3.334(112.6); 3.217(1.9); 3.183(2.5); 2.996(0.3); 2.979(2.4); 2.945(1.8); 2.672(0.4); 2.542(49.5); 2.507(43.6); 2.503(56.2); 2.499(42.7); 2.330(0.4); 1.235(0.3); 0.612(0.4); 0.597(0.6); 0.579(0.9); 0.565(0.8); 0.547(0.7); 0.533(0.9); 0.528(0.9); 0.519(1.0); 0.505(0.8); 0.488(0.8); 0.473(1.0); 0.454(0.7); 0.439(0.4); 0.425(0.4); 0.340(0.4); 0.322(0.5); 0.312(0.9); 0.297(1.1); 0.284(0.8); 0.280(0.8); 0.271(0.7); 0.254(0.4); 0.142(0.5); 0.124(0.7); 0.116(0.9); 0.099(1.1); 0.089(0.7); 0.084(0.7); 0.074(0.6); 0.008(0.6); 0.000(13.0) Example I-88: .sup.1H-NMR(400.0 MHz, DMSO): δ = 8.402(16.0); 8.132(3.9); 8.120(4.1); 7.390(1.8); 7.377(3.3); 7.365(1.7); 7.318(0.8); 7.294(4.9); 7.281(6.4); 7.267(0.8); 7.261(0.7); 7.224(0.3); 7.203(2.2); 7.192(1.2); 7.186(1.5); 5.390(2.0); 4.151(1.8); 4.115(3.1); 4.033(3.1); 3.998(1.9); 3.335(104.7); 2.996(0.5); 2.828(1.7); 2.793(2.4); 2.773(1.4); 2.739(3.3); 2.712(0.6); 2.701(3.2); 2.666(1.9); 2.658(2.5); 2.624(1.7); 2.567(0.4); 2.543(75.5); 2.507(49.2); 2.503(65.0); 2.499(48.8); 2.368(0.4); 2.330(0.4); 1.234(0.5); 0.000(16.7); −0.008(0.8) Example I-89: .sup.1H-NMR(300.2 MHz, CDCl3): δ = 8.273(16.0); 8.234(0.3); 8.213(12.0); 7.995(14.3); 7.270(13.1); 7.186(8.7); 7.178(8.9); 4.967(7.4); 4.920(8.1); 4.468(9.7); 4.463(10.1); 3.960(8.6); 3.913(7.9); 3.682(4.4); 3.636(5.2); 3.106(8.2); 3.060(7.1); 2.010(1.4); 1.704(6.8); 1.255(0.4); 0.986(1.9); 0.967(3.0); 0.961(2.6); 0.949(2.7); 0.941(3.5); 0.930(3.5); 0.924(3.0); 0.905(3.5); 0.873(2.6); 0.853(2.3); 0.849(3.4); 0.837(3.6); 0.830(2.5); 0.818(2.9); 0.813(4.0); 0.794(2.6); 0.542(2.8); 0.521(3.7); 0.516(3.1); 0.506(2.7); 0.496(3.5); 0.486(3.3); 0.481(2.5); 0.461(2.6); 0.378(3.1); 0.357(3.2); 0.354(3.7); 0.341(3.2); 0.334(2.8); 0.320(3.0); 0.317(3.3); 0.297(2.1); 0.071(1.4); 0.000(5.7) Example I-90: .sup.1H-NMR(400.0 MHz, CD3CN): δ = 8.442(4.5); 8.259(2.6); 8.246(2.6); 8.008(4.2); 7.672(4.3); 7.517(2.4); 7.504(2.3); 4.324(2.0); 4.287(3.4); 4.184(3.3); 4.147(2.0); 4.068(0.7); 4.050(0.7); 4.009(0.6); 3.992(0.8); 3.988(1.7); 3.971(1.8); 3.967(1.2); 3.950(1.0); 3.921(1.0); 3.906(1.1); 3.899(1.7); 3.885(1.7); 3.878(0.7); 3.864(0.6); 3.194(2.2); 3.158(3.4); 3.026(2.7); 2.989(1.8); 2.157(3.6); 1.972(3.2); 1.965(0.3); 1.959(0.7); 1.953(3.6); 1.947(6.4); 1.940(8.7); 1.934(6.0); 1.928(3.4); 1.915(0.8); 1.909(0.7); 1.898(1.0); 1.895(0.8); 1.884(0.9); 1.878(0.9); 1.863(0.8); 1.677(0.8); 1.660(0.9); 1.655(0.9); 1.645(0.7); 1.639(0.8); 1.628(0.7); 1.624(0.7); 1.607(0.6); 1.221(0.9); 1.203(16.0); 1.186(0.9); 1.047(14.5); 0.008(0.6); 0.000(17.2); −0.009(0.6) Example I-91: .sup.1H-NMR(400.0 MHz, CD3CN): δ = 8.483(5.5); 8.310(3.3); 8.297(3.4); 8.153(5.4); 7.739(5.4); 7.507(3.0); 7.494(2.9); 7.063(0.7); 7.055(0.5); 7.047(0.8); 7.039(4.7); 7.034(2.0); 7.028(5.1); 7.019(6.7); 7.015(6.3); 7.005(1.1); 7.000(0.5); 6.992(0.5); 4.697(2.8); 4.660(3.4); 4.366(5.4); 4.311(3.7); 4.274(3.1); 3.379(1.4); 3.343(4.0); 3.308(4.0); 3.273(1.4); 2.500(5.1); 2.138(66.4); 2.120(0.9); 2.113(0.9); 2.107(1.1); 2.101(0.8); 2.095(0.4); 1.964(4.9); 1.958(11.8); 1.952(64.0); 1.946(115.7); 1.940(154.7); 1.934(106.4); 1.927(55.2); 1.781(0.4); 1.774(0.7); 1.768(0.9); 1.762(0.6); 1.756(0.3); 1.422(1.7); 1.291(1.5); 1.233(15.5); 1.190(16.0); 0.146(1.3); 0.008(10.2); 0.000(285.3); −0.009(10.9); −0.150(1.3) Example I-92: .sup.1H-NMR(400.1 MHz, CDCl3): δ = 8.250(16.0); 8.205(4.4); 8.204(4.4); 8.184(4.7); 8.182(4.6); 8.050(4.4); 8.048(4.5); 8.029(5.1); 8.027(5.1); 7.964(13.7); 7.758(2.6); 7.755(2.7); 7.741(3.7); 7.737(5.2); 7.734(2.5); 7.719(3.0); 7.716(2.9); 7.626(3.4); 7.623(3.4); 7.609(3.0); 7.606(5.3); 7.602(3.3); 7.588(2.5); 7.585(2.4); 7.530(15.6); 7.275(5.4); 4.909(6.4); 4.873(6.9); 4.424(10.6); 4.125(0.4); 4.107(0.4); 3.990(7.4); 3.955(6.9); 3.777(4.1); 3.776(4.0); 3.742(5.1); 3.740(5.1); 3.489(6.8); 3.453(5.4); 2.038(1.8); 1.866(2.2); 1.302(0.3); 1.284(0.4); 1.272(1.1); 1.263(1.5); 1.255(1.6); 1.237(0.6); 0.897(0.7); 0.880(2.2); 0.862(0.9); 0.828(1.2); 0.813(2.7); 0.808(1.9); 0.801(1.6); 0.794(3.3); 0.786(5.5); 0.781(2.2); 0.768(4.5); 0.760(3.4); 0.754(1.5); 0.745(2.3); 0.742(3.5); 0.728(1.6); 0.486(2.3); 0.471(2.9); 0.467(2.4); 0.460(2.4); 0.451(2.7); 0.444(2.7); 0.440(2.1); 0.425(2.0); 0.292(2.4); 0.276(2.8); 0.274(3.1); 0.265(2.5); 0.259(2.5); 0.249(2.5); 0.247(2.7); 0.232(1.8); 0.077(0.4); 0.000(2.0) Example I-93: .sup.1H-NMR(300.2 MHz, CDCl3): δ = 9.040(3.3); 9.024(3.4); 8.160(5.2); 7.967(4.8); 7.705(2.9); 7.689(2.8); 7.266(9.8); 5.303(2.5); 4.647(2.4); 4.600(2.8); 4.189(3.4); 4.185(3.4); 3.971(2.8); 3.925(2.5); 3.317(1.4); 3.313(1.3); 3.270(1.9); 3.266(1.9); 3.058(2.8); 3.011(2.0); 2.047(0.4); 1.639(4.0); 1.233(16.0); 0.521(0.7); 0.516(0.7); 0.496(1.3); 0.475(0.8); 0.471(0.8); 0.452(0.3); 0.106(0.8); 0.087(2.0); 0.081(3.3); 0.070(1.6); 0.063(3.5); 0.058(2.1); 0.039(0.9); 0.000(6.9); −0.011(0.3); −0.111(0.4); −0.131(0.8); −0.137(1.0); −0.153(1.2); −0.157(1.3); −0.173(0.8); −0.181 (0.6) Example I-94: 1H-NMR(400.0 MHz, CD3CN): δ = 8.324(16.0); 8.293(5.0); 8.289(5.3); 8.282(5.3); 8.277(5.4); 7.929(15.1); 7.921(6.3); 7.907(5.8); 7.902(5.7); 7.323(6.0); 7.311(5.9); 7.304(5.8); 7.292(5.5); 4.935(9.1); 4.899(10.0); 4.193(14.4); 4.142(11.0); 4.106(10.1); 3.478(6.4); 3.442(8.5); 3.230(10.7); 3.194(8.1); 2.157(27.2); 2.108(0.4); 1.965(1.7); 1.959(4.1); 1.953(23.4); 1.947(42.8); 1.940(58.1); 1.934(40.9); 1.928(21.7); 1.769(0.4); 0.849(1.8); 0.834(3.5); 0.830(2.6); 0.822(2.4); 0.815(4.0); 0.807(4.3); 0.802(3.2); 0.798(3.6); 0.788(4.5); 0.783(2.6); 0.780(4.2); 0.772(4.0); 0.765(2.2); 0.757(2.8); 0.753(4.5); 0.739(2.5); 0.514(2.8); 0.499(4.6); 0.495(3.1); 0.488(2.5); 0.480(4.2); 0.473(4.4); 0.469(2.5); 0.456(5.2); 0.454(5.0); 0.441(3.3); 0.438(4.6); 0.429(4.0); 0.423(2.7); 0.414(2.9); 0.411(3.9); 0.396(2.0); 0.146(0.6); 0.008(4.2); 0.000(127.5); −0.009(7.0); −0.150(0.6) Example I-95: 1H-NMR(400.0 MHz, CD3CN): δ = 8.324(16.0); 8.294(5.1); 8.289(5.5); 8.282(5.5); 8.277(5.6); 7.929(15.8); 7.922(6.4); 7.907(5.8); 7.902(5.7); 7.323(6.0); 7.311(6.0); 7.304(5.9); 7.292(5.5); 4.936(9.5); 4.900(10.4); 4.189(13.1); 4.142(10.3); 4.106(9.5); 3.478(6.3); 3.443(8.4); 3.230(10.6); 3.194(8.0); 2.147(42.3); 2.120(0.5); 2.114(0.6); 2.108(0.7); 2.101(0.5); 1.964(3.1); 1.958(7.2); 1.952(41.8); 1.946(76.7); 1.940(104.5); 1.934(73.9); 1.928(39.5); 1.775(0.5); 1.769(0.6); 1.762(0.4); 0.849(1.9); 0.835(3.7); 0.830(2.7); 0.822(2.5); 0.815(4.2); 0.807(4.6); 0.803(3.4); 0.798(3.9); 0.788(4.7); 0.784(2.7); 0.780(4.5); 0.772(4.3); 0.766(2.3); 0.758(2.9); 0.754(4.8); 0.739(2.7); 0.514(2.8); 0.499(4.6); 0.495(3.1); 0.488(2.5); 0.480(4.2); 0.473(4.4); 0.468(2.5); 0.456(5.2); 0.454(4.7); 0.441(3.3); 0.438(4.6); 0.429(4.0); 0.423(2.7); 0.414(2.9); 0.411(3.9); 0.396(2.0); 0.146(1.2); 0.008(8.9); 0.000(263.7); −0.009(14.6); −0.150(1.2) Example I-96: 1H-NMR(400.1 MHz, CDCl3): δ = 8.286(16.0); 7.914(15.2); 7.696(10.2); 7.675(11.0); 7.262(27.6); 7.207(8.7); 7.186(7.9); 5.721(14.7); 4.662(2.2); 4.626(11.5); 4.610(13.7); 4.574(2.8); 3.751(8.4); 3.713(9.4); 3.060(7.9); 3.022(7.1); 1.595(11.7); 1.305(0.5); 1.287(0.7); 1.265(2.6); 0.909(0.6); 0.898(2.3); 0.893(2.5); 0.882(5.5); 0.872(4.6); 0.866(8.2); 0.852(6.5); 0.849(5.5); 0.838(4.1); 0.825(1.9); 0.822(1.5); 0.809(0.7); 0.788(0.7); 0.782(0.5); 0.761(0.5); 0.745(1.7); 0.740(1.0); 0.728(4.1); 0.717(9.0); 0.704(4.9); 0.699(5.6); 0.690(3.3); 0.678(1.2); 0.672(1.7); 0.657(0.4); 0.008(0.7); 0.000(20.3); −0.009(0.7) Example I-97: 1H-NMR(400.1 MHz, CDCl3): δ = 8.311(12.2); 8.306(12.2); 8.276(15.7); 7.905(16.0); 7.784(12.8); 7.779(12.4); 7.264(23.8); 6.141(9.0); 4.637(3.5); 4.601(13.4); 4.578(14.8); 4.542(3.9); 4.130(0.6); 4.112(0.6); 3.759(10.1); 3.720(11.2); 3.050(10.3); 3.012(9.3); 2.042(2.6); 2.003(11.3); 1.276(0.8); 1.258(1.9); 1.240(0.8); 0.871(1.5); 0.865(1.9); 0.859(2.0); 0.850(3.9); 0.845(2.7); 0.833(3.7); 0.823(4.9); 0.800(3.4); 0.791(3.6); 0.787(4.4); 0.775(4.7); 0.760(2.8); 0.755(4.6); 0.748(4.7); 0.742(2.8); 0.734(1.6); 0.726(4.2); 0.716(4.3); 0.712(3.8); 0.703(3.8); 0.686(5.4); 0.676(4.0); 0.664(3.1); 0.661(4.1); 0.650(2.3); 0.644(2.1); 0.639(1.7); 0.616(0.3); 0.070(2.2); 0.008(0.3); 0.000(10.4); −0.009(0.4)
1H-NMR Data for Compounds in Table 2 Written in Classical Form
(44) TABLE-US-00006 Ex-no NMR V-2 1H-NMR (400 MHz, d3-CD3CN): δ = 8.44-843 (dd, 1H), 7.79-7.77 (dd, 1H), 7.29-7.26 (dd, 1H), 4.41 (s, 2H), 1.72-1.68 (m, 2H), 1.49-1.46 (m, 2H) ppm V-3 1H-NMR (400 MHz, d3-CD3CN): δ = 8.30-8.28 (dd, 1H), 7.65-7.63 (dd, 1H), 7.33-7.30 (dd, 1H), 4.27 (s, 2H), 1.72-1.64 (m, 2H), 1.49-1.46 (m, 2H) ppm V-4 1H-NMR (400 MHz, d3-CD3CN): δ = 8.55 (s, 1H), 8.43 (d, 1H), 7.25 (d, 1H), 4.30 (s, 2H), 1.71-1.64 (m, 2H), 1.50-1.47 (m, 2H) ppm V-6 1H-NMR (400 MHz, d3-CD3CN): δ = 8.17 (d, 1H), 7.58-7.56 (dd, 1H), 7.35 (d, 1H), 4.17 (s, 2H), 1.69-1.61 (m, 2H), 1.47-1.43 (m, 2H) ppm V-7 1H-NMR (400 MHz, d3-CD3CN): δ = 8.56 (s, 1H), 8.44 (d, 1H), 7.28 (d, 1H), 4.27 (d, 2H), 1.54-1.36 (m, 4H) ppm V-8 1H-NMR (400 MHz, d3-CD3CN): δ = 8.56 (s, 1H), 8.44 (d, 1H), 7.26 (d, 1H), 4.20 (d, 2H), 1.53 (d, 6H, J = 22 Hz) ppm V-9 1H-NMR (400 MHz, d3-CD3CN): δ = 8.27-8.26 (dd, 1H), 7.60-7.58 (dd, 1H), 7.30-7.27 (m, 1H), 3.91 (s, 2H), 1.40 (s, 3H), 1.29 (m, 2H), 0.84-0.81 (m, 2H) ppm V-10 1H-NMR (400 MHz, d3-CD3CN): δ = 8.24-8.22 (dd, 1H), 7.52-7.50 (m, 3H), 7.43-7.40 (m, 3H), 7.26-7.23 (m, 1H), 3.72 (s, 2H), 1.60-1.58 (m, 2H), 1.27-1.24 (m, 2H) ppm V-11 1H-NMR (400 MHz, d3-CD3CN): δ = 8.52 (s, 1H), 8.39 (d, 1H), 7.19 (d, 1H), 3.94 (s, 2H), 1.40 (s, 3H), 1.30-1.27 (m, 2H), 0.85-0.82 (m, 2H) ppm V-12 1H-NMR (400 MHz, d3-CD3CN): δ = 8.53 (s, 1H), 8.40 (d, 1H), 7.20 (d, 1H), 4.05 (s, 2H), 2.04-1.99 (m, 2H), 1.60-1.50 (m, 2H), 1.50-1.36 (m, 6H), 1.21 (s, 3H) ppm
NMR-Peak Lists for Compounds in Table 2
(45) TABLE-US-00007 Example V-1: 1H-NMR(499.9 MHz, CDCl3): δ = 14.874(1.3); 8.194(0.7); 8.177(0.8); 8.072(0.6); 8.055(0.7); 7.820(0.6); 7.803(0.7); 7.739(0.4); 7.724(0.6); 7.722(0.6); 7.707(0.4); 7.705(0.4); 7.701(0.3); 7.608(1.4); 7.599(7.1); 7.591(1.5); 7.581(7.2); 7.563(0.5); 7.548(0.7); 7.533(0.4); 7.496(3.5); 7.486(6.1); 7.481(7.2); 7.471(6.2); 7.467(4.9); 7.325(6.6); 7.308(5.1); 7.262(2.7); 7.233(3.6); 7.217(6.0); 7.203(2.8); 6.775(6.1); 6.756(5.8); 6.138(16.0); 4.833(3.7); 4.568(0.5); 4.224(1.3); 4.212(2.3); 4.200(1.1); 4.182(0.7); 4.169(1.0); 4.156(0.5); 3.575(1.3); 3.563(2.3); 3.560(1.5); 3.551(1.3); 3.546(0.7); 3.441(1.2); 3.428(2.2); 3.415(1.1); 1.908(0.4); 1.905(0.4); 1.899(0.5); 1.891(0.8); 1.887(0.7); 1.879(1.1); 1.873(1.0); 1.866(1.4); 1.862(1.4); 1.853(1.4); 1.849(1.3); 1.841(0.9); 1.836(0.9); 1.823(0.4); 1.766(0.6); 1.759(0.6); 1.751(0.6); 1.739(1.0); 1.729(1.3); 1.719(3.2); 1.712(3.6); 1.706(6.1); 1.696(14.1); 1.690(14.0); 1.681(5.5); 1.662(0.6); 1.648(1.0); 1.640(1.2); 1.634(1.3); 1.624(0.5); 1.514(0.8); 1.505(2.1); 1.498(2.4); 1.490(1.0); 1.419(1.0); 1.410(2.4); 1.403(2.1); 1.393(1.0); 1.369(1.3); 1.361(3.2); 1.355(2.8); 1.345(1.3); 1.339(0.6); 1.305(5.5); 1.296(13.6); 1.290(13.3); 1.280(4.6); 1.247(0.4); 0.000(2.2) Example V-5: 1H-NMR(300.2 MHz, CDCl3): δ = 7.756(0.3); 7.733(0.4); 7.728(0.3); 7.712(0.4); 7.689(0.4); 7.684(0.3); 7.475(0.4); 7.465(0.4); 7.451(0.4); 7.441(0.4); 7.262(14.8); 7.163(0.5); 7.124(16.2); 4.204(16.0); 1.741(2.5); 1.724(6.3); 1.712(7.3); 1.697(3.4); 1.641(0.7); 1.553(11.7); 1.534(0.6); 1.479(3.4); 1.464(7.1); 1.452(6.2); 1.434(2.5); 0.069(0.5); 0.011(0.5); 0.000(12.5); −0.011(0.5) Example V-13: 1H-NMR(499.9 MHz, CDCl3): δ = 8.762(4.4); 8.758(4.2); 8.109(2.7); 8.092(2.9); 7.998(3.7); 7.995(3.6); 7.798(2.5); 7.782(2.8); 7.715(1.6); 7.712(1.5); 7.701(2.1); 7.698(2.9); 7.695(1.5); 7.684(1.8); 7.681(1.5); 7.558(2.0); 7.556(1.8); 7.542(3.1); 7.528(1.5); 7.526(1.3); 7.258(44.3); 4.394(16.0); 1.731(2.8); 1.720(8.3); 1.713(8.4); 1.704(3.4); 1.671(0.3); 1.561(23.3); 1.471(0.4); 1.437(3.3); 1.428(8.3); 1.421(8.3); 1.411(2.8); 1.256(0.8); 0.069(1.7); 0.006(1.2); 0.000(29.0); −0.007(1.1) Example V-15: 1H-NMR(400.0 MHz, CD3CN): δ = 8.320(2.0); 8.315(2.0); 8.308(2.0); 8.303(2.0); 7.641(2.0); 7.637(2.0); 7.623(2.3); 7.618(2.2); 7.338(2.4); 7.326(2.4); 7.319(2.2); 7.307(2.1); 5.447(1.9); 4.899(16.0); 4.783(16.0); 4.178(13.9); 2.143(19.3); 1.972(0.5); 1.964(0.8); 1.958(1.3); 1.952(5.6); 1.946(9.9); 1.940(12.9); 1.934(8.8); 1.927(4.6); 0.008(0.3); 0.000(8.7); −0.008(0.4) Example V-16: 1H-NMR(400.0 MHz, DMSO): δ = .148(2.0); 8.145(1.6); 8.137(2.0); 7.868(1.1); 7.863(1.2); 7.850(1.3); 7.844(2.0); 7.839(1.2); 7.825(1.3); 7.820(1.2); 7.340(1.5); 7.335(1.6); 7.328(1.5); 7.322(2.7); 7.317(1.5); 7.310(1.5); 7.304(1.4); 4.186(16.0); 3.319(14.7); 2.675(0.5); 2.671(0.7); 2.666(0.5); 2.524(1.5); 2.510(37.7); 2.506(77.7); 2.501(103.0); 2.497(73.5); 2.492(34.9); 2.333(0.5); 2.328(0.7); 2.324(0.5); 2.231(0.4); 1.764(2.8); 1.751(7.0); 1.742(6.9); 1.730(3.7); 1.688(0.4); 1.596(0.5); 1.554(3.8); 1.541(6.8); 1.533(6.9); 1.519(2.8); 0.146(0.3); 0.008(2.9); 0.000(81.4); −0.009(2.6); −0.150(0.4) Example V-17: 1H-NMR(400.1 MHz, DMSO): δ = 7.902(4.6); 7.882(5.1); 7.593(5.7); 7.573(5.0); 4.296(16.0); 3.308(3.3); 2.517(4.9); 2.512(9.7); 2.508(13.1); 2.503(9.2); 2.499(4.3); 1.774(2.4); 1.760(5.8); 1.752(5.9); 1.739(3.2); 1.698(0.4); 1.619(0.4); 1.577(3.2); 1.564(5.8); 1.556(5.8); 1.542(2.3) Example V-18: 1H-NMR(400.1 MHz, DMSO): δ = 8.345(0.5); 8.332(6.2); 7.818(1.8); 7.798(2.2); 7.681(1.6); 7.663(2.2); 7.573(2.4); 7.553(2.5); 7.535(1.5); 4.421(11.1); 4.156(1.7); 4.141(3.2); 4.126(1.4); 3.693(1.4); 3.677(3.3); 3.671(0.5); 3.661(1.7); 3.319(12.6); 3.290(0.6); 2.714(0.4); 2.667(16.0); 2.531(0.4); 2.517(8.3); 2.513(17.0); 2.508(23.1); 2.504(16.6); 2.499(7.9); 1.995(0.4); 1.817(1.8); 1.803(4.8); 1.795(4.8); 1.783(3.0); 1.775(1.0); 1.765(1.2); 1.763(1.2); 1.759(0.8); 1.752(1.1); 1.741(1.4); 1.729(0.9); 1.723(1.0); 1.720(0.7); 1.714(0.7); 1.707(0.6); 1.624(1.0); 1.610(2.3); 1.606(3.0); 1.603(2.9); 1.593(4.7); 1.585(4.6); 1.571(1.7); 1.456(1.4); 1.443(2.3); 1.435(2.1); 1.421(1.0) Example V-19: 1H-NMR(400.1 MHz, DMSO): δ = 8.462(2.4); 8.459(2.5); 8.450(2.5); 8.447(2.5); 8.403(3.6); 8.399(3.6); 7.627(1.3); 7.623(2.1); 7.618(1.3); 7.608(1.5); 7.603(2.4); 7.599(1.5); 7.360(2.1); 7.348(2.1); 7.340(1.9); 7.328(1.8); 4.141(16.0); 3.336(1.3); 2.512(9.7); 2.508(12.9); 2.504(9.4); 1.775(2.4); 1.761(6.7); 1.753(6.7); 1.741(3.2); 1.699(0.4); 1.572(0.4); 1.530(3.1); 1.517(6.4); 1.509(6.7); 1.495(2.4) Example V-20: 1H-NMR(400.1 MHz, DMSO): δ = 8.351(4.5); 8.337(4.6); 7.665(4.7); 7.652(4.5); 4.415(16.0); 3.318(11.9); 2.517(4.5); 2.513(8.8); 2.508(11.8); 2.504(8.4); 2.499(4.0); 1.808(2.1); 1.794(5.3); 1.786(5.5); 1.773(2.9); 1.732(0.4); 1.661(0.3); 1.619(2.9); 1.607(5.4); 1.599(5.3); 1.585(2.0) Example V-21: 1H-NMR(400.1 MHz, DMSO): δ = 8.449(4.4); 8.443(4.5); 8.034(4.9); 8.027(4.7); 5.221(0.5); 4.298(16.0); 3.317(21.6); 3.028(0.4); 2.531(0.3); 2.517(7.7); 2.513(15.5); 2.508(20.9); 2.504(15.1); 2.500(7.3); 1.774(2.2); 1.760(5.8); 1.752(6.1); 1.740(3.2); 1.698(0.6); 1.626(0.4); 1.585(3.1); 1.572(5.9); 1.564(5.8); 1.550(2.2)
1H-NMR Data for Compounds in Table 3 Written in Classical Form
(46) TABLE-US-00008 Ex-no NMR XII-2 1H-NMR (400 MHz, d3-CD3CN): δ = 8.26 (d, 1H), 7.67-7.64 (dd, 1H), 7.34-7.32 (d, 1H), 3.37 (d, 1H), 3.13 (d, 1H), 2.72 (d, 1H), 2.56 (d, 1H), 0.95-0.90 (m, 1H), 0.80-0.70 (m, 2H), 0.70- 0.60 (m, 1H) ppm XII-3 1H-NMR (400 MHz, d3-CD3CN): δ = 8.52 (s, 1H), 8.37 (d, 1H), 7.29 (d, 1H), 3.54 (d, 1H), 3.42 (d, 1H), 2.69 (d, 1H), 2.41 (d, 1H), 1.05-0.85 (m, 4H) ppm XII-5 1H-NMR (400 MHz, d3-CD3CN: δ = 8.32-8.30 (dd, 1H), 7.79-7.74 (dd, 1H), 7.38-7.36 (dd, 1H), 3.50 (d, 1H), 3.35 (d, 1H), 2.73 (d, 1H), 2.33 (d, 1H), 1.10-1.00 (m, 2H), 0.95-0.85 (m, 2H) ppm
NMR-Peak Lists for Compounds in Table 3
(47) TABLE-US-00009 Example XII-1: .sup.1H-NMR(400.1 MHz, DMSO): δ = 8.298(9.1); 8.277(9.6); 8.009(0.5); 7.996(6.5); 7.975(8.1); 7.966(6.6); 7.964(6.8); 7.946(6.9); 7.943(7.1); 7.764(4.0); 7.760(4.1); 7.746(5.3); 7.743(7.7); 7.739(4.1); 7.725(4.4); 7.722(4.2); 7.599(4.8); 7.596(4.9); 7.582(4.9); 7.579(7.9); 7.576(5.2); 7.561(3.8); 7.559(3.7); 7.542(0.7); 7.521(0.6); 7.493(13.5); 7.472(13.0); 7.140(0.3); 3.616(4.9); 3.581(15.5); 3.551(16.0); 3.516(5.2); 3.319(6.6); 3.210(0.4); 3.178(0.4); 2.799(9.1); 2.787(12.4); 2.725(13.1); 2.713(10.2); 2.686(0.4); 2.682(0.5); 2.677(0.6); 2.673(0.4); 2.663(0.7); 2.530(1.5); 2.517(19.4); 2.512(39.4); 2.508(53.8); 2.503(39.6); 2.499(20.3); 2.463(1.4); 2.339(0.3); 2.335(0.4); 2.330(0.3); 1.290(1.8); 0.968(1.2); 0.954(2.5); 0.947(1.9); 0.941(2.1); 0.934(3.1); 0.928(4.6); 0.923(6.2); 0.911(5.2); 0.906(5.3); 0.897(4.9); 0.880(6.7); 0.871(9.1); 0.869(9.2); 0.861(6.7); 0.846(4.5); 0.841(2.6); 0.835(4.9); 0.828(5.7); 0.818(6.3); 0.811(5.2); 0.804(3.6); 0.798(2.8); 0.794(2.5); 0.785(3.1); 0.772(1.6) Example XII-20: .sup.1H-NMR(400.1 MHz, DMSO): δ = 8.321(16.0); 7.256(12.5); 7.251(12.6); 3.584(8.9); 3.549(14.0); 3.435(12.5); 3.400(7.9); 3.315(43.4); 2.764(11.3); 2.754(12.3); 2.678(0.4); 2.673(0.3); 2.531(1.1); 2.517(24.9); 2.513(51.7); 2.509(71.0); 2.504(52.4); 2.491(14.7); 2.480(13.1); 2.463(0.5); 2.340(0.4); 2.335(0.5); 2.331(0.3); 1.106(0.6); 1.091(3.9); 1.081(5.0); 1.066(8.3); 1.063(8.4); 1.056(7.1); 1.043(7.6); 1.038(8.5); 1.024(2.3); 0.968(3.5); 0.955(6.5); 0.937(11.2); 0.930(5.8); 0.924(4.4); 0.913(8.6); 0.902(2.2); 0.898(2.7); 0.891(4.1); 0.877(1.5) Example XII-23: .sup.1H-NMR(400.0 MHz, CD3CN): δ = 8.284(7.1); 8.279(7.4); 8.272(7.3); 8.267(7.3); 7.729(7.4); 7.724(7.3); 7.710(8.1); 7.705(7.8); 7.293(9.2); 7.281(9.1); 7.274(8.5); 7.262(8.2); 3.467(7.7); 3.430(15.2); 3.359(16.0); 3.322(8.1); 2.686(13.0); 2.675(14.1); 2.470(9.0); 2.465(9.3); 2.459(8.3); 2.454(8.2); 2.152(6.8); 1.965(0.7); 1.959(1.8); 1.953(9.7); 1.947(17.4); 1.941(23.3); 1.935(15.9); 1.928(8.1); 1.207(0.3); 1.054(1.3); 1.039(1.4); 1.036(1.5); 1.030(0.9); 1.022(2.8); 1.010(3.3); 1.006(4.4); 0.994(4.0); 0.988(1.6); 0.980(1.5); 0.976(4.4); 0.973(3.0); 0.965(4.6); 0.962(7.2); 0.958(3.7); 0.950(3.8); 0.945(3.9); 0.935(1.8); 0.932(2.1); 0.927(4.1); 0.916(4.5); 0.912(4.3); 0.901(3.1); 0.895(1.4); 0.886(1.6); 0.883(2.0); 0.869(2.4); 0.753(2.4); 0.738(2.1); 0.735(2.0); 0.728(2.7); 0.725(3.5); 0.714(2.6); 0.710(5.0); 0.707(4.4); 0.701(3.2); 0.695(4.6); 0.686(4.2); 0.683(4.2); 0.671(7.8); 0.659(3.9); 0.655(4.0); 0.648(4.9); 0.641(3.2); 0.636(4.0); 0.631(5.1); 0.626(2.7); 0.617(2.6); 0.612(2.0); 0.608(2.0); 0.604(1.8); 0.590(1.8); 0.008(2.0); 0.000(49.3); −0.009(1.7) Example XII-24: .sup.1H-NMR(400.1 MHz, CDCl3): δ = 7.315(0.8); 7.296(49.5); 7.265(9.5); 7.250(0.8); 7.236(0.6); 7.232(0.6); 7.093(0.4); 5.581(0.4); 5.377(0.4); 4.037(12.0); 4.008(16.0); 3.849(16.0); 3.820(12.0); 3.740(0.4); 3.732(0.4); 3.723(0.4); 3.720(0.4); 3.708(0.3); 3.195(8.3); 3.161(13.7); 3.109(0.7); 3.064(12.4); 3.030(7.5); 2.924(0.4); 2.366(13.5); 2.349(1.0); 1.788(0.3); 1.697(0.5); 1.688(0.5); 1.607(2.1); 1.520(0.5); 1.518(0.6); 1.512(0.5); 1.431(0.5); 1.210(0.7); 1.208(0.7); 1.204(0.5); 1.147(2.7); 1.141(0.5); 1.131(3.4); 1.124(6.1); 1.111(3.6); 1.106(4.4); 1.101(3.8); 1.093(0.6); 1.086(4.0); 0.977(3.0); 0.962(2.6); 0.955(6.4); 0.941(3.2); 0.938(4.0); 0.932(4.5); 0.924(0.6); 0.917(3.7); 0.751(12.5); 0.745(1.9); 0.729(15.5); 0.727(14.8); 0.711(1.6); 0.705(7.8); 0.071(1.4); 0.000(5.6) Example XII-25: .sup.1H-NMR(400.0 MHz, DMSO): δ = 9.110(10.8); 9.106(10.5); 8.719(12.2); 8.706(12.4); 8.693(0.3); 7.481(7.8); 7.477(7.7); 7.468(7.6); 7.464(7.3); 3.411(5.8); 3.377(14.3); 3.332(15.9); 3.322(14.4); 3.297(6.3); 2.801(8.6); 2.789(13.5); 2.753(14.8); 2.741(9.4); 2.672(0.4); 2.525(0.8); 2.512(21.0); 2.507(42.5); 2.503(55.5); 2.498(39.1); 2.494(18.1); 2.330(0.4); 2.288(1.0); 1.909(0.5); 1.292(0.5); 1.235(0.4); 0.989(0.3); 0.984(0.3); 0.966(1.6); 0.953(3.3); 0.939(3.5); 0.934(3.3); 0.926(4.6); 0.921(4.0); 0.917(2.5); 0.906(3.2); 0.902(3.8); 0.889(5.2); 0.879(4.5); 0.875(4.4); 0.863(8.8); 0.859(16.0); 0.843(4.4); 0.840(4.5); 0.830(4.5); 0.827(1.2); 0.814(2.7); 0.803(3.7); 0.787(3.0); 0.784(4.9); 0.778(5.0); 0.771(4.1); 0.766(4.1); 0.752(4.3); 0.739(2.0); 0.000(1.1) Example XII-29: .sup.1H-NMR(400.0 MHz, DMSO): δ = 8.885(8.7); 8.851(1.1); 5.458(0.3); 4.910(16.0); 4.558(2.7); 3.943(1.2); 3.913(1.6); 3.742(1.4); 3.711(1.1); 3.321(18.2); 3.287(2.3); 3.286(2.2); 3.271(6.1); 3.255(5.0); 3.181(0.5); 3.174(4.8); 3.158(5.7); 3.142(2.2); 2.622(6.3); 2.525(0.4); 2.520(0.7); 2.512(12.6); 2.507(26.1); 2.503(34.7); 2.498(24.9); 2.494(11.8); 1.890(0.3); 1.884(0.4); 1.877(0.4); 1.873(0.4); 1.863(0.4); 1.851(0.4); 1.744(1.8); 1.730(4.0); 1.721(3.8); 1.709(2.4); 1.702(0.5); 1.689(0.6); 1.685(0.4); 1.678(3.0); 1.664(6.7); 1.656(6.8); 1.644(3.7); 1.638(0.6); 1.630(0.6); 1.617(0.4); 1.602(0.5); 1.578(0.5); 1.574(0.4); 1.566(0.5); 1.556(0.4); 1.554(0.4); 1.545(0.4); 1.541(0.4); 1.532(2.4); 1.525(0.7); 1.519(3.9); 1.511(4.0); 1.497(1.6); 1.484(3.7); 1.472(6.5); 1.463(6.4); 1.450(2.7); 1.322(0.3); 1.303(0.4); 1.294(0.5); 1.291(0.4); 1.275(0.4); 1.233(0.5); 1.229(0.6); 1.216(0.4); 1.208(0.5); 1.192(0.4); 1.113(0.7); 1.105(0.7); 1.094(0.6); 1.089(0.7); 1.084(0.7); 1.078(0.5); 1.069(0.5); 1.057(0.4); 0.008(0.6); 0.000(21.0); −0.009(0.7) Example XII-30: .sup.1H-NMR(300.2 MHz, CDCl3): δ = 7.746(0.5); 7.719(0.5); 7.588(9.2); 7.562(10.6); 7.288(0.4); 7.265(12.4); 7.226(11.3); 7.200(9.8); 3.576(7.0); 3.527(11.8); 3.387(9.7); 3.338(5.8); 3.013(0.3); 2.997(0.4); 2.713(8.5); 2.698(9.3); 2.383(9.5); 2.368(8.8); 1.575(12.9); 1.485(0.5); 1.462(0.6); 1.453(0.8); 1.430(0.7); 1.176(1.3); 1.152(1.3); 1.113(1.1); 1.105(3.5); 1.082(3.5); 1.070(4.5); 1.065(3.7); 1.038(1.6); 1.002(0.6); 0.993(0.9); 0.973(1.7); 0.961(2.0); 0.949(4.6); 0.941(4.8); 0.931(12.5); 0.926(16.0); 0.918(5.2); 0.914(6.7); 0.901(8.3); 0.897(10.1); 0.886(2.9); 0.880(2.1); 0.862(4.6); 0.851(2.8); 0.824(0.5); 0.816(0.4); 0.796(0.4); 0.070(2.8); 0.000(7.4) Example XII-31: .sup.1H-NMR(400.0 MHz, DMSO): δ = 8.316(0.3); 8.142(5.6); 8.139(4.7); 8.134(4.6); 8.130(5.5); 8.127(4.2); 7.881(3.4); 7.877(3.3); 7.863(3.9); 7.857(5.7); 7.852(3.4); 7.838(3.6); 7.833(3.3); 7.318(4.4); 7.313(4.5); 7.306(4.4); 7.301(7.0); 7.295(4.2); 7.288(3.9); 7.283(3.8); 3.485(0.5); 3.324(113.3); 3.281(19.8); 3.274(18.7); 3.237(1.8); 2.755(12.6); 2.744(13.6); 2.676(0.7); 2.671(0.9); 2.667(0.7); 2.558(1.0); 2.541(13.8); 2.530(13.0); 2.511(46.9); 2.507(91.6); 2.502(118.9); 2.498(84.8); 2.493(40.0); 2.333(0.6); 2.329(0.8); 2.324(0.6); 2.320(0.4); 1.260(0.3); 1.249(0.3); 1.234(0.7); 1.213(0.3); 1.206(0.3); 1.200(0.3); 1.189(0.3); 1.180(0.3); 1.169(0.4); 1.161(0.4); 1.152(0.4); 1.143(0.4); 1.025(0.5); 1.006(2.0); 0.997(3.0); 0.983(5.5); 0.979(4.3); 0.976(4.0); 0.966(4.7); 0.957(1.5); 0.946(2.8); 0.904(2.4); 0.896(3.5); 0.887(5.4); 0.880(10.3); 0.876(9.2); 0.863(16.0); 0.859(8.8); 0.854(6.8); 0.844(5.1); 0.837(7.5); 0.825(2.1); 0.817(6.9); 0.808(5.0); 0.799(5.9); 0.784(3.0); 0.775(1.7); 0.758(0.3); 0.008(2.0); 0.000(47.5); −0.009(1.6) Example XII-35: .sup.1H-NMR(400.0 MHz, DMSO): δ = 8.604(15.7); 8.562(3.1); 8.507(4.3); 8.422(2.1); 8.409(2.5); 8.355(2.0); 8.342(2.1); 8.321(4.7); 8.316(3.8); 8.296(8.5); 8.283(8.4); 7.961(4.3); 7.850(1.0); 7.813(0.8); 7.743(2.3); 7.725(2.7); 7.645(2.1); 7.633(2.0); 7.625(1.0); 7.540(0.7); 7.443(13.0); 7.421(0.8); 7.388(0.7); 7.376(1.5); 7.356(7.4); 7.337(12.7); 7.317(7.9); 7.304(1.3); 7.286(1.5); 7.266(1.0); 7.240(0.9); 7.225(4.5); 7.207(5.9); 7.188(2.2); 7.145(8.9); 7.133(16.0); 7.116(9.3); 7.092(1.8); 7.079(1.7); 7.059(8.7); 7.037(0.8); 7.015(0.7); 5.390(3.0); 5.376(6.7); 5.362(3.0); 5.051(3.4); 4.790(0.8); 4.475(1.2); 4.441(1.6); 4.188(7.9); 4.183(8.3); 4.174(8.1); 4.169(7.5); 3.932(1.7); 3.897(1.6); 3.717(4.1); 3.702(0.8); 3.597(0.7); 3.495(0.9); 3.466(1.1); 3.455(1.2); 3.418(1.4); 3.403(1.8); 3.385(2.9); 3.364(6.2); 3.334(3090.6); 3.311(10.1); 3.301(3.1); 3.293(2.9); 3.271(1.4); 3.261(1.3); 3.237(1.0); 3.193(0.8); 3.184(0.9); 3.076(1.6); 3.037(5.0); 2.711(2.0); 2.671(9.4); 2.667(7.0); 2.620(0.8); 2.581(2.2); 2.571(2.4); 2.559(3.8); 2.542(460.9); 2.511(584.8); 2.507(1170.5); 2.502(1524.3); 2.498(1095.2); 2.367(2.2); 2.350(0.8); 2.333(7.0); 2.329(9.6); 2.325(6.6); 2.291(0.9); 1.463(0.8); 1.298(1.2); 1.259(1.8); 1.235(5.5); 1.218(0.7); 1.143(4.1); 1.131(11.4); 1.127(11.5); 1.115(4.1); 0.848(4.4); 0.837(11.3); 0.831(11.4); 0.820(3.7); 0.517(0.9); 0.507(0.8); 0.391(0.9); 0.383(0.8); 0.358(0.7); 0.340(0.8); 0.334(0.9); 0.146(1.0); 0.008(6.7); 0.000(197.0); −0.008(6.9); −0.150(1.0); −3.238(0.8) Example XII-38: .sup.1H-NMR(499.9 MHz, CDCl3): δ = 8.859(14.7); 8.672(9.2); 8.662(9.3); 7.315(8.3); 7.305(8.3); 7.261(14.5); 6.564(0.5); 3.739(6.2); 3.709(7.3); 3.383(7.2); 3.353(6.1); 2.655(9.9); 2.646(10.4); 2.209(10.2); 2.200(10.1); 2.056(0.4); 2.049(0.5); 1.658(0.6); 1.650(1.2); 1.642(1.7); 1.624(4.7); 1.510(0.4); 1.498(0.6); 1.494(0.6); 1.483(0.4); 1.382(0.3); 1.353(0.5); 1.351(0.4); 1.349(0.4); 1.161(1.2); 1.146(0.5); 1.123(2.2); 1.117(3.4); 1.115(3.6); 1.109(3.0); 1.094(4.8); 1.069(1.2); 1.018(1.4); 1.015(1.7); 1.009(0.6); 0.997(6.2); 0.991(13.7); 0.988(16.0); 0.984(10.2); 0.970(0.8); 0.963(2.4); 0.961(2.2); 0.947(1.9); 0.923(5.1); 0.918(4.4); 0.917(4.0); 0.907(3.2); 0.901(3.4); 0.897(3.3); 0.892(2.4); 0.006(0.4); 0.000(10.0) Example XII-39: .sup.1H-NMR(400.1 MHz, DMSO): δ = 8.656(0.7); 8.342(0.5); 8.318(6.8); 8.205(0.5); 7.826(1.8); 7.807(2.0); 7.676(0.3); 7.674(0.3); 7.658(1.4); 7.655(1.7); 7.653(1.3); 7.641(1.8); 7.638(2.3); 7.548(2.7); 7.530(2.5); 7.528(2.6); 7.510(1.7); 7.360(0.5); 4.305(0.4); 4.151(2.9); 4.136(5.6); 4.120(2.5); 3.716(2.8); 3.696(0.4); 3.687(2.7); 3.679(4.1); 3.672(6.2); 3.656(3.1); 3.517(3.1); 3.481(2.2); 3.311(14.9); 3.286(0.5); 2.750(3.1); 2.740(3.2); 2.677(1.6); 2.654(16.0); 2.512(1.9); 2.507(4.0); 2.503(5.5); 2.498(3.9); 2.494(2.1); 2.373(3.7); 2.362(3.6); 1.798(0.7); 1.796(0.7); 1.792(0.9); 1.786(0.8); 1.779(1.1); 1.776(1.6); 1.770(1.4); 1.760(1.9); 1.758(1.8); 1.753(1.1); 1.747(1.7); 1.740(1.2); 1.736(1.8); 1.734(2.0); 1.724(1.7); 1.718(1.9); 1.715(1.5); 1.709(1.0); 1.702(1.4); 1.695(0.7); 1.685(0.4); 1.619(1.9); 1.605(3.6); 1.597(3.9); 1.585(2.7); 1.543(0.4); 1.539(0.5); 1.532(0.5); 1.519(0.4); 1.511(0.9); 1.494(1.0); 1.482(0.5); 1.475(0.4); 1.450(2.7); 1.438(4.0); 1.429(3.7); 1.419(0.5); 1.416(1.9); 1.402(0.3); 1.128(0.6); 1.121(1.8); 1.117(1.5); 1.107(0.5); 1.096(4.2); 1.089(0.9); 1.074(3.0); 0.982(0.6); 0.968(2.1); 0.964(2.5); 0.949(2.4); 0.946(2.1); 0.940(2.1); 0.938(1.8); 0.931(0.6); 0.925(1.5); 0.917(1.3); 0.000(4.3) Example XII-40: .sup.1H-NMR(400.1 MHz, DMSO): δ = 8.351(1.4); 8.338(1.5); 8.303(15.5); 8.290(15.9); 7.666(1.4); 7.653(1.4); 7.607(15.9); 7.594(15.0); 4.415(4.9); 3.814(11.7); 3.777(16.0); 3.590(11.5); 3.554(8.3); 3.368(0.6); 3.318(87.1); 3.267(0.3); 2.732(10.6); 2.723(11.0); 2.682(0.3); 2.677(0.4); 2.558(0.4); 2.554(0.3); 2.530(1.3); 2.517(24.5); 2.513(48.6); 2.508(64.9); 2.504(46.3); 2.500(21.9); 2.335(0.4); 2.199(13.7); 2.189(13.4); 1.809(0.6); 1.795(1.6); 1.786(1.7); 1.774(0.9); 1.620(0.9); 1.607(1.7); 1.599(1.6); 1.585(0.6); 1.209(0.7); 1.194(4.6); 1.185(5.7); 1.169(9.4); 1.166(9.3); 1.161(8.0); 1.146(8.2); 1.142(8.4); 1.127(2.0); 1.033(3.0); 1.019(6.8); 1.016(3.8); 1.007(7.4); 1.001(7.5); 0.994(7.2); 0.984(7.0); 0.982(7.4); 0.976(5.0); 0.971(2.4); 0.967(2.9); 0.960(4.5); 0.946(1.4) Example XII-41: .sup.1H-NMR(300.2 MHz, CDCl3): δ = 8.315(0.4); 8.306(0.9); 8.301(1.0); 8.295(1.3); 8.284(1.6); 8.272(9.5); 8.264(9.8); 7.859(0.4); 7.823(0.5); 7.814(0.5); 7.616(9.6); 7.608(9.6); 7.582(0.7); 7.574(0.7); 7.539(0.8); 7.530(0.8); 7.503(1.2); 7.494(1.2); 7.264(16.9); 5.077(0.7); 5.053(0.7); 4.329(2.9); 4.045(0.5); 3.590(7.3); 3.541(11.2); 3.376(9.1); 3.327(5.8); 3.265(0.3); 3.251(0.4); 3.247(0.4); 3.233(0.4); 3.058(0.4); 3.042(0.5); 2.836(0.4); 2.725(8.1); 2.710(9.0); 2.683(0.5); 2.675(0.5); 2.665(0.5); 2.656(0.4); 2.390(9.2); 2.375(8.6); 1.763(0.4); 1.745(1.2); 1.733(1.5); 1.718(1.3); 1.702(0.9); 1.691(0.7); 1.683(2.4); 1.655(0.4); 1.645(0.5); 1.576(15.3); 1.496(0.3); 1.483(3.7); 1.471(1.6); 1.459(4.7); 1.441(0.7); 1.429(0.9); 1.417(1.1); 1.410(1.2); 1.396(0.9); 1.389(0.4); 1.377(0.5); 1.199(0.7); 1.175(0.7); 1.127(0.8); 1.118(3.0); 1.112(1.9); 1.094(2.4); 1.078(4.8); 1.050(1.4); 1.014(0.5); 1.009(0.8); 0.987(1.4); 0.980(1.3); 0.969(1.3); 0.963(4.2); 0.957(4.4); 0.946(10.0); 0.941(16.0); 0.930(7.4); 0.912(7.2); 0.908(8.4); 0.901(2.9); 0.891(1.9); 0.873(4.2); 0.862(2.6); 0.827(0.4); 0.011(0.5); 0.000(12.9); −0.011(0.7) Example XII-42: .sup.1H-NMR(400.1 MHz, DMSO): δ = 8.486(15.6); 8.469(0.7); 7.617(0.4); 7.556(16.0); 3.554(6.0); 3.519(9.6); 3.413(8.0); 3.377(5.0); 3.315(28.9); 2.762(7.3); 2.752(7.9); 2.531(1.2); 2.526(1.6); 2.518(14.2); 2.513(29.0); 2.509(39.4); 2.504(28.5); 2.499(14.2); 2.470(9.6); 2.459(9.1); 2.336(0.3); 1.101(0.4); 1.087(2.7); 1.078(3.5); 1.062(5.8); 1.060(5.9); 1.053(5.7); 1.039(6.3); 1.036(6.3); 1.021(1.6); 0.964(2.3); 0.950(4.5); 0.947(2.6); 0.936(5.0); 0.932(5.1); 0.926(4.2); 0.922(3.4); 0.912(6.0); 0.907(3.3); 0.900(1.8); 0.897(2.2); 0.889(3.1); 0.875(2.0); 0.858(0.7)
Use Examples
Example A: In Vivo Preventive Test on Botrytis cinerea (Grey Mould)
(48) The tested active ingredients are prepared by homogenization in a mixture of acetone/Dimethyl sulfoxide/Tween®, and then diluted with water to obtain the desired active material concentration.
(49) The young plants of gherkin are treated by spraying the active ingredient prepared as described above. Control plants are treated only with an aqueous solution of acetone/Dimethyl sulfoxide/Tween®.
(50) After 24 hours, the plants are contaminated by spraying the leaves with an aqueous suspension of Botrytis cinerea spores. The contaminated gherkin plants are incubated for 4 to 5 days at 17° C. and at 90% relative humidity.
(51) The test is evaluated 4 to 5 days after the inoculation. 0% means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease is observed.
(52) In this test the following compounds according to the invention showed efficacy of at least 70% at a concentration of 500 ppm of active ingredient.
(53) TABLE-US-00010 Ex_no. Eff. % I-2 94 I-3 100 I-4 100 I-5 100 I-29 94 I-39 99 I-40 97 I-49 99 I-50 100 I-51 100 I-53 100 I-54 100 I-58 98 I-60 100 I-61 99 I-62 100 I-65 100 I-67 99 I-71 100 I-76 100 I-77 100 I-79 99 I-81 99 I-82 100 I-83 100 I-89 100 I-90 100 I-91 95
(54) In this test the following compounds according to the invention showed efficacy of at least 70% at a concentration of 100 ppm of active ingredient.
(55) TABLE-US-00011 Ex_no. Eff. % I-6 76 I-7 100 I-8 87 I-16 87 I-18 100 I-19 100 I-25 99 I-27 98 I-33 94
Example B: In Vivo Preventive Test on Puccinia recondita (Brown Rust on Wheat)
(56) The tested active ingredients are prepared by homogenization in a mixture of acetone/Dimethyl sulfoxide/Tween®, and then diluted with water to obtain the desired active material concentration.
(57) The young plants of wheat are treated by spraying the active ingredient prepared as described above. Control plants are treated only with an aqueous solution of acetone/Dimethyl sulfoxide/Tween®.
(58) After 24 hours, the plants are contaminated by spraying the leaves with an aqueous suspension of Puccinia recondita spores. The contaminated wheat plants are incubated for 24 hours at 20° C. and at 100% relative humidity and then for 10 days at 20° C. and at 70-80% relative humidity.
(59) The test is evaluated 11 days after the inoculation. 0% means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease is observed.
(60) In this test the following compounds according to the invention showed efficacy of at least 70% at a concentration of 500 ppm of active ingredient.
(61) TABLE-US-00012 Ex_no. Eff. % I-2 94 I-3 98 I-4 100 I-5 100 I-29 97 I-33 93 I-36 97 I-39 97 I-40 97 I-49 100 I-50 94 I-51 98 I-53 94 I-54 97 I-55 79 I-56 86 I-57 86 I-58 97 I-59 98 I-60 98 I-61 98 I-62 98 I-64 83 I-65 98 I-67 98 I-68 94 I-69 98 I-70 94 I-71 94 I-75 81 I-76 100 I-77 98 I-79 98 I-80 88 I-81 100 I-82 98 I-83 100 I-84 88 I-87 89 I-88 89 I-89 100 I-91 89
(62) In this test the following compounds according to the invention showed efficacy of at least 70% at a concentration of 100 ppm of active ingredient.
(63) TABLE-US-00013 Ex_no. Eff. % I-6 81 I-7 94 I-8 94 I-16 75 I-18 94 I-19 88 I-21 98 I-25 100 I-31 83 I-32 75 I-45 97 I-46 88
Example C: In Vivo Preventive Test on Pyrenophora teres (Net Blotch on Barley)
(64) The tested active ingredients are prepared by homogenization in a mixture of acetone/Dimethyl sulfoxide/Tween®, and then diluted with water to obtain the desired active material concentration.
(65) The young plants of barley are treated by spraying the active ingredient prepared as described above. Control plants are treated only with an aqueous solution of acetone/Dimethyl sulfoxide/Tween®.
(66) After 24 hours, the plants are contaminated by spraying the leaves with an aqueous suspension of Pyrenophora teres spores. The contaminated barley plants are incubated for 48 hours at 20° C. and at 100% relative humidity and then for 12 days at 20° C. and at 70-80% relative humidity.
(67) The test is evaluated 14 days after the inoculation. 0% means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease is observed.
(68) In this test the following compounds according to the invention showed efficacy of at least 70% at a concentration of 500 ppm of active ingredient.
(69) TABLE-US-00014 Ex_no. Eff. % I-3 100 I-29 95 I-33 75 I-36 88 I-39 100 I-40 100 I-49 93 I-50 79 I-51 100 I-53 86 I-56 88 I-57 88 I-58 95 I-60 100 I-61 93 I-62 100 I-65 100 I-67 86 I-68 71 I-69 93 I-71 79 I-76 79 I-77 86 I-81 97 I-82 97 I-83 88 I-89 100
(70) In this test the following compounds according to the invention showed efficacy of at least 70% at a concentration of 100 ppm of active ingredient.
(71) TABLE-US-00015 Ex_no. Eff. % I-1 83 I-7 92 I-18 83 I-19 75 I-25 97
Example D: In Vivo Preventive Test on Septoria tritici (Leaf Spot on Wheat)
(72) The tested active ingredients are prepared by homogenization in a mixture of acetone/Dimethyl sulfoxide/Tween®, and then diluted with water to obtain the desired active material concentration.
(73) The young plants of wheat are treated by spraying the active ingredient prepared as described above. Control plants are treated only with an aqueous solution of acetone/Dimethyl sulfoxide/Tween®.
(74) After 24 hours, the plants are contaminated by spraying the leaves with an aqueous suspension of Septoria tritici spores. The contaminated wheat plants are incubated for 72 hours at 18° C. and at 100% relative humidity and then for 21 days at 20° C. and at 90% relative humidity.
(75) The test is evaluated 24 days after the inoculation. 0% means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease is observed.
(76) In this test the following compounds according to the invention showed efficacy of at least 70% at a concentration of 500 ppm of active ingredient.
(77) TABLE-US-00016 Ex_no. Eff. % I-2 100 I-3 100 I-4 96 I-5 100 I-29 100 I-33 100 I-36 100 I-39 100 I-40 100 I-49 100 I-50 100 I-51 100 I-53 100 I-54 100 I-55 100 I-56 92 I-57 92 I-58 100 I-59 100 I-60 97 I-61 100 I-62 100 I-64 97 I-65 100 I-66 92 I-67 100 I-68 100 I-69 100 I-70 100 I-71 100 I-72 80 I-73 100 I-74 100 I-75 100 I-76 100 I-77 100 I-79 100 I-80 100 I-81 100 I-82 100 I-83 100 I-85 78 I-86 72 I-87 83 I-88 100 I-89 100 I-90 78 I-91 100
(78) In this test the following compounds according to the invention showed efficacy of at least 70% at a concentration of 100 ppm of active ingredient.
(79) TABLE-US-00017 Ex_no. Eff. % I-6 100 I-7 98 I-8 94 I-12 88 I-15 94 I-16 98 I-17 97 I-18 98 I-19 75 I-21 100 I-22 88 I-25 100 I-26 97 I-31 100 I-45 100 I-46 100 I-84 81
Example E: In Vivo Preventive Test on Sphaerotheca fuliginea (Powdery Mildew on Cucurbits)
(80) The tested active ingredients are prepared by homogenization in a mixture of acetone/Dimethyl sulfoxide/Tween®, and then diluted with water to obtain the desired active material concentration.
(81) The young plants of gherkin are treated by spraying the active ingredient prepared as described above. Control plants are treated only with an aqueous solution of acetone/Dimethyl sulfoxide/Tween®.
(82) After 24 hours, the plants are contaminated by spraying the leaves with an aqueous suspension of Sphaerotheca fuliginea spores. The contaminated gherkin plants are incubated for 72 hours at 18° C. and at 100% relative humidity and then for 12 days at 20° C. and at 70-80% relative humidity.
(83) The test is evaluated 15 days after the inoculation. 0% means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease is observed.
(84) In this test the following compounds according to the invention showed efficacy of at least 70% at a concentration of 500 ppm of active ingredient.
(85) TABLE-US-00018 Ex_no. Eff. % I-2 95 I-4 100 I-5 100 I-29 100 I-33 100 I-36 100 I-39 100 I-40 100 I-48 83 I-49 100 I-50 100 I-51 100 I-53 100 I-54 100 I-55 100 I-56 100 I-57 95 I-58 100 I-59 100 I-60 100 I-61 100 I-62 100 I-64 100 I-65 100 I-66 80 I-67 98 I-68 100 I-69 100 I-70 100 I-71 100 I-72 98 I-73 100 I-74 100 I-75 100 I-76 100 I-77 100 I-79 100 I-80 100 I-81 100 I-82 100 I-83 100 I-85 89 I-87 72 I-88 98 I-89 100 I-90 100 I-91 98
(86) In this test the following compounds according to the invention showed efficacy of at least 70% at a concentration of 100 ppm of active ingredient.
(87) TABLE-US-00019 Ex_no. Eff. % I-3 100 I-6 100 I-7 100 I-8 100 I-9 94 I-10 75 I-11 79 I-12 100 I-13 94 I-14 100 I-15 98 I-16 100 I-17 100 I-18 100 I-19 100 I-21 100 I-23 88 I-24 94 I-25 100 I-26 100 I-27 100 I-30 94 I-31 90 I-34 100 I-35 78 I-38 100 I-41 100 I-42 98 I-43 100 I-44 100 I-45 100 I-46 100
Example F: In Vivo Preventive Test on Uromyces appendiculatus (Bean Rust)
(88) The tested active ingredients are prepared by homogenization in a mixture of acetone/Dimethyl sulfoxide/Tween®, and then diluted with water to obtain the desired active material concentration.
(89) The young plants of bean are treated by spraying the active ingredient prepared as described above. Control plants are treated only with an aqueous solution of acetone/Dimethyl sulfoxide/Tween®.
(90) After 24 hours, the plants are contaminated by spraying the leaves with an aqueous suspension of Uromyces appendiculatus spores. The contaminated bean plants are incubated for 24 hours at 20° C. and at 100% relative humidity and then for 10 days at 20° C. and at 70-80% relative humidity.
(91) The test is evaluated 11 days after the inoculation. 0% means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease is observed.
(92) In this test the following compounds according to the invention showed efficacy of at least 70% at a concentration of 500 ppm of active ingredient.
(93) TABLE-US-00020 Ex_no. Eff. % I-2 100 I-3 100 I-4 97 I-5 98 I-29 100 I-33 100 I-36 100 I-39 100 I-40 100 I-48 81 I-49 81 I-50 100 I-51 86 I-53 98 I-54 100 I-55 98 I-56 96 I-57 96 I-58 100 I-59 100 I-60 100 I-61 100 I-62 100 I-64 94 I-65 100 I-67 100 I-68 100 I-69 100 I-70 99 I-71 99 I-72 100 I-76 100 I-77 100 I-79 100 I-80 99 I-81 100 I-82 100 I-83 100 I-84 100 I-87 78 I-89 100 I-91 97
(94) In this test the following compounds according to the invention showed efficacy of at least 70% at a concentration of 100 ppm of active ingredient.
(95) TABLE-US-00021 Ex_no. Eff. % I-1 80 I-6 100 I-7 100 I-8 100 I-11 75 I-13 95 I-14 87 I-16 91 I-17 94 I-18 97 I-19 98 I-21 100 I-23 92 I-24 92 I-25 100 I-27 98 I-30 100 I-31 94 I-41 94 I-44 94 I-45 100
Example G: Blumeria Test (Barley)/Preventive
(96) Solvent: 49 parts by weight of N,N-dimethylacetamide
(97) Emulsifier: 1 part by weight of alkylaryl polyglycol ether
(98) 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.
(99) 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.
(100) After the spray coating has been dried, the plants are dusted with spores of Blumeria graminis f. sp. hordei.
(101) 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.
(102) 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.
(103) In this test the following compounds according to the invention showed an efficacy of 70% or even higher at a concentration of 500 ppm of active ingredient.
(104) TABLE-US-00022 Ex_no. Eff. % I-3 100 I-4 100 I-5 100 I-6 100 I-7 100 I-8 100 I-18 100 I-19 100 I-21 100 I-25 100 I-27 100 I-29 100 I-31 100 I-33 100 I-36 100 I-39 100 I-40 100 I-45 100 I-49 100 I-51 100 I-53 100 I-54 100 I-57 100 I-58 100 I-60 100 I-61 100 I-62 100 I-65 100 I-69 100 I-70 100 I-71 100 I-76 100 I-77 100 I-81 100 I-82 100 I-94 100 I-95 100
Example H: Fusarium culmorum-Test (Wheat)/Curative
(105) Solvent: 49 parts by weight of N,N-dimethylacetamide
(106) Emulsifier: 1 part by weight of alkylaryl polyglycol ether
(107) 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.
(108) To test for curative activity, young plants are slightly injured by using a sandblast and afterwards they are sprayed with a conidia suspension of Fusarium culmorum and placed for 24 hours in a greenhouse under a translucent incubation cabinet at a temperature of approximately 22° C. and a relative atmospheric humidity of approximately 100% and are subsequently sprayed with the preparation of active compound at the stated rate of application.
(109) After the spray coating has been dried, the plants remain in the greenhouse under translucent incubation cloches at a temperature of approximately 22° C. and a relative atmospheric humidity of approximately 100%.
(110) The test is evaluated 5 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.
(111) In this test the following compounds according to the invention showed an efficacy of 70% or even higher at a concentration of 500 ppm of active ingredient.
(112) TABLE-US-00023 Ex_no. Eff. % I-3 100 I-4 92 I-5 100 I-6 100 I-7 100 I-8 100 I-18 100 I-19 100 I-21 100 I-25 100 I-29 100 I-39 100 I-45 100 I-49 100 I-51 100 I-53 90 I-60 83 I-61 100 I-62 83 I-65 100
Example I: Fusarium graminearum-Test (Barley)/Preventive
(113) Solvent: 49 parts by weight of N,N-dimethylacetamide
(114) Emulsifier: 1 part by weight of alkylaryl polyglycol ether
(115) 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.
(116) 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.
(117) After the spray coating has been dried, the plants are slightly injured by using a sandblast and afterwards they are sprayed with a conidia suspension of Fusarium graminearum.
(118) The plants are placed in the greenhouse under a translucent incubation cabinet at a temperature of approximately 22° C. and a relative atmospheric humidity of approximately 100%.
(119) The test is evaluated 5 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.
(120) In this test the following compounds according to the invention showed an efficacy of 70% or even higher at a concentration of 500 ppm of active ingredient.
(121) TABLE-US-00024 Ex_no. Eff. % I-3 100 I-5 100 I-6 100 I-7 100 I-8 100 I-18 100 I-19 100 I-21 100 I-25 100 I-27 100 I-29 100 I-33 100 I-36 94 I-39 100 I-40 100 I-45 100 I-46 92 I-49 100 I-51 100 I-53 100 I-54 100 I-58 100 I-60 100 I-61 100 I-62 100 I-65 100 I-69 71 I-71 100 I-76 86 I-77 86 I-81 100 I-82 100 I-95 100
Example J: Fusarium nivale (var. majus)-Test (Wheat)/Preventive
(122) Solvent: 49 parts by weight of N,N-dimethylacetamide
(123) Emulsifier: 1 part by weight of alkylaryl polyglycol ether
(124) 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.
(125) 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.
(126) After the spray coating has been dried, the plants are slightly injured by using a sandblast and afterwards they are sprayed with a conidia suspension of Fusarium nivale (var. majus).
(127) The plants are placed in the greenhouse under a translucent incubation cabinet at a temperature of approximately 10° C. and a relative atmospheric humidity of approximately 100%.
(128) The test is evaluated 5 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.
(129) In this test the following compounds according to the invention showed an efficacy of 70% or even higher at a concentration of 500 ppm of active ingredient.
(130) TABLE-US-00025 Ex_no. Eff. % I-3 100 I-4 71 I-5 100 I-6 100 I-7 100 I-8 100 I-18 100 I-19 100 I-21 100 I-25 100 I-27 93 I-29 100 I-31 75 I-33 93 I-39 100 I-40 86 I-45 100 I-46 100 I-49 100 I-51 100 I-53 100 I-54 100 I-57 71 I-58 100 I-60 100 I-61 100 I-62 100 I-65 100 I-70 88 I-71 94 I-76 100 I-77 83 I-81 100 I-82 100 I-94 100 I-95 100
Example K: Leptosphaeria nodorum Test (Wheat)/Preventive
(131) Solvent: 49 parts by weight of N,N-dimethylacetamide
(132) Emulsifier: 1 part by weight of alkylaryl polyglycol ether
(133) 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.
(134) 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.
(135) 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%.
(136) The plants are placed in the greenhouse at a temperature of approximately 22° C. and a relative atmospheric humidity of approximately 80%.
(137) 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.
(138) In this test the following compounds according to the invention showed an efficacy of 70% or even higher at a concentration of 500 ppm of active ingredient.
(139) TABLE-US-00026 Ex_no. Eff. % I-3 100 I-4 80 I-5 90 I-6 100 I-7 100 I-8 92 I-18 100 I-19 100 I-21 94 I-25 100 I-29 100 I-31 88 I-33 86 I-39 100 I-40 100 I-45 88 I-46 83 I-49 100 I-51 100 I-53 100 I-58 93 I-60 100 I-61 75 I-62 100 I-65 100 I-69 89 I-70 89 I-81 100 I-82 100 I-94 71 I-95 100
Example L: Phakopsora Test (Soybeans)/Preventive
(140) Solvent: 24.5 parts by weight of acetone
(141) 24.5 parts by weight of dimethylacetamide
Emulsifier: 1 part by weight of alkylaryl polyglycol ether
(142) 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.
(143) 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%.
(144) 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.
(145) 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.
(146) In this test the following compounds according to the invention showed efficacy of 70% or even higher at a concentration of 100 ppm of active ingredient.
(147) TABLE-US-00027 Ex_no. Eff. % I-3 100 I-4 95 I-5 100 I-6 95 I-7 94 I-8 95 I-18 95 I-25 99 I-49 96 I-51 100 I-53 93 I-54 99 I-60 100 I-62 99 I-65 100 I-69 91 I-76 100 I-77 100 I-82 100
(148) In this test the following compounds according to the invention showed efficacy of 70% or even higher at a concentration of 10 ppm of active ingredient.
(149) TABLE-US-00028 Ex_no. Eff. % I-19 96 I-21 93 I-30 75 I-39 88 I-40 73 I-45 93 I-58 89 I-61 80 I-81 85
Example M: Podosphaera Test (Apples)/Preventive
(150) Solvent: 24.5 parts by weight of acetone
(151) 24.5 parts by weight of dimethylacetamide
Emulsifier: 1 part by weight of alkylaryl polyglycol ether
(152) 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.
(153) 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 apple mildew (Podosphaera leucotricha). The plants are then placed in a greenhouse at approximately 23° C. and a relative atmospheric humidity of approximately 70%.
(154) 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.
(155) In this test the following compounds according to the invention showed efficacy of 70% or even higher at a concentration of 100 ppm of active ingredient.
(156) TABLE-US-00029 Ex_no. Eff. % I-3 100 I-5 100 I-18 97
Example N: Pyricularia Oryzae-Test (Rice)/Preventive
(157) Solvent: 49 parts by weight of N,N-dimethylacetamide
(158) Emulsifier: 1 part by weight of alkylaryl polyglycol ether
(159) 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.
(160) 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.
(161) After the spray coating has been dried, the plants are sprayed with a spore suspension of Pyricularia oryzae. The plants remain for 25 hours in an incubation cabinet at approximately 25° C. and a relative atmospheric humidity of approximately 100%.
(162) The plants are placed in the greenhouse under a translucent incubations cabinet at a temperature of approximately 25° C. and a relative atmospheric humidity of approximately 100%.
(163) The test is evaluated 8 days after the inoculation. 0% means an efficacy which corresponds to that of the control, while an efficacy of 100% means that no disease is observed.
(164) In this test the following compounds according to the invention showed an efficacy of 70% or even higher at a concentration of 500 ppm of active ingredient.
(165) TABLE-US-00030 Ex_no. Eff. % I-3 100 I-5 75 I-6 83 I-7 100 I-8 100 I-19 100 I-27 89 I-29 70 I-39 80 I-46 78 I-51 80 I-53 80 I-54 78 I-58 100 I-65 86 I-71 80 I-76 71 I-77 86 I-81 100 I-82 100 I-94 70 I-95 100
Example O: Venturia Test (Apples)/Preventive
(166) Solvent: 24.5 parts by weight of acetone
(167) 24.5 parts by weight of dimethylacetamide
Emulsifier: 1 part by weight of alkylaryl polyglycol ether
(168) 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.
(169) 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%.
(170) The plants are then placed in a greenhouse at approximately 21° C. and a relative atmospheric humidity of approximately 90%.
(171) 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.
(172) In this test the following compounds according to the invention showed efficacy of 70% or even higher at a concentration of 100 ppm of active ingredient.
(173) TABLE-US-00031 Ex_no. Eff. % I-3 98 I-5 100 I-6 100 I-7 98 I-8 100 I-18 100 I-25 89 I-49 100 I-51 94 I-53 97 I-54 89 I-60 100 I-62 100 I-65 100 I-69 100 I-76 74 I-82 95