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NOVEL TRIAZOLE DERIVATIVES

20180057467 ยท 2018-03-01

    Inventors

    Cpc classification

    International classification

    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) ##STR00030## wherein X represents fluorine or chlorine; R.sup.1 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.2OP(O)(OH).sub.2, C(O)C.sub.1-C.sub.8-alkyl, C(O)C.sub.3-C.sub.7-cycloalkyl, C(O)NHC.sub.1-C.sub.8-alkyl; C(O)N-di-C.sub.1-C.sub.8-alkyl or C(O)OC.sub.1-C.sub.8-alkyl; wherein the C(O)C.sub.1-C.sub.8-alkyl, C(O)C.sub.3-C.sub.7-cycloalkyl, C(O)NHC.sub.1-C.sub.8-alkyl; C(O)N-di-C.sub.1-C.sub.8-alkyl or C(O)OC.sub.1-C.sub.8-alkyl may be non-substituted or substituted by one or more group(s) selected from halogen or C.sub.1-C.sub.8-alkoxy; wherein R.sup.3a, R.sup.3b, R.sup.3c represent independent from each other a phenyl or C.sub.1-C.sub.8-alkyl; X.sup.1 represents halogen; C.sub.1-C.sub.8-alkyl; C.sub.1-C.sub.8-haloalkyl; C.sub.1-C.sub.8-halogenalkoxy; C.sub.3-C.sub.7-cycloalkyl; C.sub.2-C.sub.8-alkenyl; C.sub.2-C.sub.8-alkynyl; C.sub.2-C.sub.8-alkenyloxy; C.sub.3-C.sub.8-alkynyloxy; C.sub.3-C.sub.8-halogenoalkynyloxy; C.sub.1-C.sub.8-alkoxy; C.sub.1-C.sub.8-haloalkylsulfanyl; phenyl; 5-membered heteroaryl; 6-membered heteroaryl; benzyloxy; phenyloxy; benzylsulfanyl; benzylamino; phenylsulfanyl; or phenylamino; wherein the C.sub.2-C.sub.8-alkenyl, C.sub.2-C.sub.8-alkynyl, C.sub.3-C.sub.7-cycloalkyl, benzyl, phenyl, 5-membered heteroaryl, 6-membered heteroaryl, benzyloxy or phenyloxy may be optionally substituted by one or more group(s) selected from halogen; C.sub.1-C.sub.8-alkyl; C.sub.1-C.sub.8-haloalkyl; C.sub.1-C.sub.8-halogenalkoxy; C.sub.3-C.sub.7-cycloalkyl; C.sub.2-C.sub.8-alkenyl; C.sub.2-C.sub.8-alkynyl; C.sub.2-C.sub.8-alkenyloxy; C.sub.3-C.sub.8-alkynyloxy; C.sub.3-C.sub.8-halogenoalkynyloxy; C.sub.1-C.sub.8-alkoxy; C.sub.1-C.sub.8-haloalkylsulfanyl; X.sup.2 represents halogen; C.sub.1-C.sub.8-alkyl; C.sub.1-C.sub.8-haloalkyl; C.sub.1-C.sub.8-halogenalkoxy; C.sub.3-C.sub.7-cycloalkyl; C.sub.2-C.sub.8-alkenyl; C.sub.2-C.sub.8-alkynyl; C.sub.2-C.sub.8-alkenyloxy; C.sub.3-C.sub.8-alkynyloxy; C.sub.3-C.sub.8-halogenoalkynyloxy; C.sub.1-C.sub.8-alkoxy; or C.sub.1-C.sub.8-haloalkylsulfanyl; wherein the C.sub.2-C.sub.8-alkenyl, C.sub.2-C.sub.8-alkynyl, C.sub.3-C.sub.7-cycloalkyl, may be optionally substituted by one or more group(s) selected from halogen; C.sub.1-C.sub.8-alkyl; C.sub.1-C.sub.8-haloalkyl; C.sub.1-C.sub.8-halogenalkoxy; C.sub.3-C.sub.7-cycloalkyl; C.sub.2-C.sub.8-alkenyl; C.sub.2-C.sub.8-alkynyl; C.sub.2-C.sub.8-alkenyloxy; C.sub.3-C.sub.8-alkynyloxy; C.sub.3-C.sub.8-halogenoalkynyloxy; C.sub.1-C.sub.8-alkoxy; C.sub.1-C.sub.8-haloalkylsulfanyl; X.sup.3 represents halogen; C.sub.1-C.sub.8-alkyl; C.sub.1-C.sub.8-haloalkyl; C.sub.1-C.sub.8-halogenalkoxy; C.sub.3-C.sub.7-cycloalkyl; C.sub.2-C.sub.8-alkenyl; C.sub.2-C.sub.8-alkynyl; C.sub.2-C.sub.8-alkenyloxy; C.sub.3-C.sub.8-alkynyloxy; C.sub.3-C.sub.8-halogenoalkynyloxy; C.sub.1-C.sub.8-alkoxy or C.sub.1-C.sub.8-haloalkylsulfanyl; X.sup.4 represents halogen; X.sup.5 represents halogen; n represents 0 or 1; m represents 0 or 1; and/or a salt and/or N-oxide thereof.

    2. Triazole derivative of the formula (I) according to claim 1, wherein X represents fluorine or chlorine; R.sup.1 represents H, C.sub.1-C.sub.8-alkyl, halogen- or C.sub.1-C.sub.8-alkoxy-substituted or non-substituted C(O)C.sub.1-C.sub.8-alkyl; X.sup.1 represents halogen; C.sub.1-C.sub.8-alkyl; C.sub.1-C.sub.8-haloalkyl; C.sub.1-C.sub.8-halogenalkoxy; C.sub.3-C.sub.7-cycloalkyl; C.sub.2-C.sub.8-alkenyl; C.sub.2-C.sub.8-alkynyl; C.sub.2-C.sub.8-alkenyloxy; C.sub.3-C.sub.8-alkynyloxy; C.sub.3-C.sub.8-halogenoalkynyloxy; C.sub.1-C.sub.8-alkoxy; C.sub.1-C.sub.8-haloalkylsulfanyl; phenyl; 5-membered heteroaryl; 6-membered heteroaryl; benzyloxy; phenyloxy; benzylsulfanyl; benzylamino; phenylsulfanyl; or phenylamino; wherein the C.sub.2-C.sub.8-alkenyl, C.sub.2-C.sub.8-alkynyl, C.sub.3-C.sub.7-cycloalkyl, benzyl, phenyl, 5-membered heteroaryl, 6-membered heteroaryl, benzyloxy or phenyloxy may be optionally substituted by one or more group(s) selected from halogen; C.sub.1-C.sub.8-alkyl; C.sub.1-C.sub.8-haloalkyl; C.sub.1-C.sub.8-halogenalkoxy; C.sub.3-C.sub.7-cycloalkyl; C.sub.2-C.sub.8-alkenyl; C.sub.2-C.sub.8-alkynyl; C.sub.2-C.sub.8-alkenyloxy; C.sub.3-C.sub.8-alkynyloxy; C.sub.3-C.sub.8-halogenoalkynyloxy; C.sub.1-C.sub.8-alkoxy; C.sub.1-C.sub.8-haloalkylsulfanyl; X.sup.2 represents fluorine, chlorine, bromine, iodine, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-haloalkylthio or C.sub.2-C.sub.4-alkynyl; X.sup.3 represents fluorine, chlorine, bromine, iodine, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-haloalkylthio or C.sub.2-C.sub.4-alkynyl; X.sup.4 represents halogen; X.sup.5 represents halogen; n represents 0 or 1; m represents 0 or 1; and/or a salt and/or N-oxide thereof.

    3. Triazole derivative of the formula (I) according to claim 1, wherein X represents fluorine or chlorine; R.sup.1 represents H, C.sub.1-C.sub.8-alkyl, halogen- or C.sub.1-C.sub.8-alkoxy-substituted or non-substituted C(O)C.sub.1-C.sub.8-alkyl; X.sup.1 represents fluorine, chlorine, bromine, iodine, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-haloalkylthio; C.sub.2-C.sub.4-alkynyl; phenyl or phenyloxy; wherein the phenyl or phenyloxy may be optionally substituted by one or more group(s) selected from halogen or C.sub.1-C.sub.8-haloalkyl; X.sup.2 represents fluorine, chlorine, bromine, iodine, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-haloalkylthio or C.sub.2-C.sub.4-alkynyl; X.sup.3 represents fluorine, chlorine, bromine, iodine, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-haloalkylthio or C.sub.2-C.sub.4-alkynyl; X.sup.4 represents halogen; X.sup.5 represents halogen; n represents 0 or 1; m represents 0 or 1; and/or a salt and/or N-oxide thereof.

    4. Triazole derivative according to claim 1 of formula (I-a) ##STR00031## and/or a salt and/or N-oxide thereof.

    5. Method for controlling harmful microorganisms in crop protection and in the protection of one or more materials, comprising applying a compound of the formula (I) and/or a salt and/or an N-oxide thereof according to claim 1 to the harmful microorganisms and/or a habitat thereof.

    6. Method for controlling phytopathogenic harmful fungi, comprising applying a compound of the formula (I) and/or a salt and/or an N-oxide thereof according to claim 1 to the phytopathogenic harmful fungi and/or a habitat thereof.

    7. Composition for controlling harmful microorganisms in crop protection and in the protection of materials, optionally for controlling phytopathogenic harmful fungi, comprising a content of at least one compound of the formula (I) and/or a salt and/or an N-oxide thereof 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 consisting of insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides, fertilizers, safeners and semiochemicals.

    9. A product comprising a compound of the formula (I) and/or a salt and/or an N-oxide thereof according to claim 1 for control of harmful microorganisms, optionally phytopathogenic harmful fungi, for crop protection and/or for protection of one or more materials.

    10. Process for producing a composition for controlling harmful microorganisms, optionally for controlling phytopathogenic harmful fungi, comprising mixing a compound of the formula (I) and/or a salt and/or an N-oxide thereof according to claim 1 with one or more extenders and/or surfactants.

    11. A product comprising a compound of the formula (I) and/or a salt and/or an N-oxide thereof according to claim 1 for treatment of one or more transgenic plants.

    12. A product comprising a compound of the formula (I) and/or a salt and/or an N-oxide thereof according to claim 1 for treatment of seed and/or seed of one or more transgenic plants.

    13. Ketone of formula (IV) ##STR00032## wherein X represents fluorine or chlorine; X.sup.1 represents halogen; C.sub.1-C.sub.8-alkyl; C.sub.1-C.sub.8-haloalkyl; C.sub.1-C.sub.8-halogenalkoxy; C.sub.3-C.sub.7-cycloalkyl; C.sub.2-C.sub.8-alkenyl; C.sub.2-C.sub.8-alkynyl; C.sub.2-C.sub.8-alkenyloxy; C.sub.3-C.sub.8-alkynyloxy; C.sub.3-C.sub.8-halogenoalkynyloxy; C.sub.1-C.sub.8-alkoxy; C.sub.1-C.sub.8-haloalkylsulfanyl; phenyl; 5-membered heteroaryl; 6-membered heteroaryl; benzyloxy; phenyloxy; benzylsulfanyl; benzylamino; phenylsulfanyl; or phenylamino; wherein the C.sub.2-C.sub.8-alkenyl, C.sub.2-C.sub.8-alkynyl, C.sub.3-C.sub.7-cycloalkyl, benzyl, phenyl, 5-membered heteroaryl, 6-membered heteroaryl, benzyloxy or phenyloxy may be optionally substituted by one or more group(s) selected from halogen; C.sub.1-C.sub.8-alkyl; C.sub.1-C.sub.8-haloalkyl; C.sub.1-C.sub.8-halogenalkoxy; C.sub.3-C.sub.7-cycloalkyl; C.sub.2-C.sub.8-alkenyl; C.sub.2-C.sub.8-alkynyl; C.sub.2-C.sub.8-alkenyloxy; C.sub.3-C.sub.8-alkynyloxy; C.sub.3-C.sub.8-halogenoalkynyloxy; C.sub.1-C.sub.8-alkoxy; C.sub.1-C.sub.8-haloalkylsulfanyl; X.sup.2 represents halogen; C.sub.1-C.sub.8-alkyl; C.sub.1-C.sub.8-haloalkyl; C.sub.1-C.sub.8-halogenalkoxy; C.sub.3-C.sub.7-cycloalkyl; C.sub.2-C.sub.8-alkenyl; C.sub.2-C.sub.8-alkynyl; C.sub.2-C.sub.8-alkenyloxy; C.sub.3-C.sub.8-alkynyloxy; C.sub.3-C.sub.8-halogenoalkynyloxy; C.sub.1-C.sub.8-alkoxy or C.sub.1-C.sub.8-haloalkylsulfanyl; wherein the C.sub.2-C.sub.8-alkenyl, C.sub.2-C.sub.8-alkynyl, C.sub.3-C.sub.7-cycloalkyl, may be optionally substituted by one or more group(s) selected from halogen; C.sub.1-C.sub.8-alkyl; C.sub.1-C.sub.8-haloalkyl; C.sub.1-C.sub.8-halogenalkoxy; C.sub.3-C.sub.7-cycloalkyl; C.sub.2-C.sub.8-alkenyl; C.sub.2-C.sub.8-alkynyl; C.sub.2-C.sub.8-alkenyloxy; C.sub.3-C.sub.8-alkynyloxy; C.sub.3-C.sub.8-halogenoalkynyloxy; C.sub.1-C.sub.8-alkoxy; C.sub.1-C.sub.8-haloalkylsulfanyl; X.sup.3 represents halogen; C.sub.1-C.sub.8-alkyl; C.sub.1-C.sub.8-haloalkyl; C.sub.1-C.sub.8-halogenalkoxy; C.sub.3-C.sub.7-cycloalkyl; C.sub.2-C.sub.8-alkenyl; C.sub.2-C.sub.8-alkynyl; C.sub.2-C.sub.8-alkenyloxy; C.sub.3-C.sub.8-alkynyloxy; C.sub.3-C.sub.8-halogenoalkynyloxy; C.sub.1-C.sub.8-alkoxy or C.sub.1-C.sub.8-haloalkylsulfanyl; X.sup.4 represents halogen; X.sup.5 represents halogen; n represents 0 or 1; m represents 0 or 1; and/or a salt and/or N-oxide thereof.

    14. Epoxide of formula (V) ##STR00033## wherein X represents fluorine or chlorine; X.sup.1 represents halogen; C.sub.1-C.sub.8-alkyl; C.sub.1-C.sub.8-haloalkyl; C.sub.1-C.sub.8-halogenalkoxy; C.sub.3-C.sub.7-cycloalkyl; C.sub.2-C.sub.8-alkenyl; C.sub.2-C.sub.8-alkynyl; C.sub.2-C.sub.8-alkenyloxy; C.sub.3-C.sub.8-alkynyloxy; C.sub.3-C.sub.8-halogenoalkynyloxy; C.sub.1-C.sub.8-alkoxy; C.sub.1-C.sub.8-haloalkylsulfanyl; phenyl; 5-membered heteroaryl; 6-membered heteroaryl; benzyloxy; phenyloxy; benzylsulfanyl; benzylamino; phenylsulfanyl; or phenylamino; wherein the C.sub.2-C.sub.8-alkenyl, C.sub.2-C.sub.8-alkynyl, C.sub.3-C.sub.7-cycloalkyl, benzyl, phenyl, 5-membered heteroaryl, 6-membered heteroaryl, benzyloxy or phenyloxy may be optionally substituted by one or more group(s) selected from halogen; C.sub.1-C.sub.8-alkyl; C.sub.1-C.sub.8-haloalkyl; C.sub.1-C.sub.8-halogenalkoxy; C.sub.3-C.sub.7-cycloalkyl; C.sub.2-C.sub.8-alkenyl; C.sub.2-C.sub.8-alkynyl; C.sub.2-C.sub.8-alkenyloxy; C.sub.3-C.sub.8-alkynyloxy; C.sub.3-C.sub.8-halogenoalkynyloxy; C.sub.1-C.sub.8-alkoxy; C.sub.1-C.sub.8-haloalkylsulfanyl; X.sup.2 represents halogen; C.sub.1-C.sub.8-alkyl; C.sub.1-C.sub.8-haloalkyl; C.sub.1-C.sub.8-halogenalkoxy; C.sub.3-C.sub.7-cycloalkyl; C.sub.2-C.sub.8-alkenyl; C.sub.2-C.sub.8-alkynyl; C.sub.2-C.sub.8-alkenyloxy; C.sub.3-C.sub.8-alkynyloxy; C.sub.3-C.sub.8-halogenoalkynyloxy; C.sub.1-C.sub.8-alkoxy; C.sub.1-C.sub.8-haloalkylsulfanyl; wherein the C.sub.2-C.sub.8-alkenyl, C.sub.2-C.sub.8-alkynyl, C.sub.3-C.sub.7-cycloalkyl, may be optionally substituted by one or more group(s) selected from halogen; C.sub.1-C.sub.8-alkyl; C.sub.1-C.sub.8-haloalkyl; C.sub.1-C.sub.8-halogenalkoxy; C.sub.3-C.sub.7-cycloalkyl; C.sub.2-C.sub.8-alkenyl; C.sub.2-C.sub.8-alkynyl; C.sub.2-C.sub.8-alkenyloxy; C.sub.3-C.sub.8-alkynyloxy; C.sub.3-C.sub.8-halogenoalkynyloxy; C.sub.1-C.sub.8-alkoxy; C.sub.1-C.sub.8-haloalkylsulfanyl; X.sup.3 represents halogen; C.sub.1-C.sub.8-alkyl; C.sub.1-C.sub.8-haloalkyl; C.sub.1-C.sub.8-halogenalkoxy; C.sub.3-C.sub.7-cycloalkyl; C.sub.2-C.sub.8-alkenyl; C.sub.2-C.sub.8-alkynyl; C.sub.2-C.sub.8-alkenyloxy; C.sub.3-C.sub.8-alkynyloxy; C.sub.3-C.sub.8-halogenoalkynyloxy; C.sub.1-C.sub.8-alkoxy; C.sub.1-C.sub.8-haloalkylsulfanyl; X.sup.4 represents halogen; X.sup.5 represents halogen; n represents 0 or 1; m represents 0 or 1; and/or a salt and/or N-oxide thereof.

    Description

    EXAMPLES

    Preparation Examples

    Preparation of Compounds of the Formula (I-02) According to Process D:

    Example 1: Preparation of 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-[1-(2,4,6-trifluorophenoxy)cyclopropyl]ethanol (I-02)

    [0296] ##STR00015##

    [0297] Under argon, in a round-bottom flask equipped with a magnetic stirrer, was dissolved 1H-1,2,4-Triazole (1606 mg, 3.0 eq, 23.25 mmol) in 6 mL of N,N-dimethylformamide. Under stirring was added potassium tert-butoxide (174 mg, 0.2 eq, 1.55 mmol). The reaction mixture was warmed at 80 C., thereafter was added a solution of 2-(2,4-difluorophenyl)-2-[1-(2,4,6-trifluorophenoxy)cyclopropyl]oxirane in 4 ml of N,N-dimethylformamide. The reaction mixture was stirred overnight at 100 C. After cooling to room temperature (rt=21 C.), the reaction mixture was quenched by addition of water, and extracted with ethyl acetate. The combined organic phases were washed, dried over magnesium sulphate, diluted with 10 mL of di-isopropyl ether, filtered and concentrated in vacuo. The crude product was purified by column chromatography over silica gel (eluent cyclohexane/ethyl acetate gradient). After evaporation of the solvent, the collected fractions were concentrated to provide 494 mg (15%) of 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-[1-(2,4,6-trifluorophenoxy)cyclopropyl]ethanol (I-02) as a colourless solid

    [0298] MS (ESI): 412.09 ([M+H].sup.+)

    Preparation of Intermediates of the Formula (IV-1) According to Process A:

    Example 2: Preparation of (2,4-difluorophenyl)[1-(2,4,6-trifluorophenoxy)cyclopropyl]methanone (IV-1)

    [0299] ##STR00016##

    [0300] Under argon, a mixture of 2-bromo-4-chloro-1-(2,4-difluorophenyl)butan-1-one (50 g, 1 eq, 159.65 mmol), 2,4,6-trifluorophenol (23.64 g, 1.0 eq, 159.65 mmol) and potassium carbonate (44.12 g, 2.0 eq, 319.30 mmol) in 800 mL of acetonitrile was stirred for 1 hour at 50 C. and then for 2.5 additional hours at reflux temperature.

    [0301] The mixture was allowed to reach ambient temperature and concentrated in vacuo. The residue was partitioned between ethyl acetate and water. After separation of the phases, the aqueous layer was extracted with 100 mL of ethyl acetate. The combined organic phases were washed with brine, dried over magnesium sulphate to which was added activated charcoal and silica (50 g), the mixture was filtered through a pad of celite. The solvent was evaporated in vacuo, affording a pale brown oil, 45.0 g (81%) of (2,4-difluorophenyl)[1-(2,4,6-trifluorophenoxy)cyclopropyl]methanone (IV-1).

    [0302] MS (ESI): 329.05 ([M+H].sup.+)

    Preparation of Intermediates of the Formula (V-1) According to Process B:

    Example 3: Preparation of 2-(2,4-difluorophenyl)-2-[1-(2,4,6-trifluorophenoxy)cyclopropyl]oxirane (V-1)

    [0303] ##STR00017##

    [0304] Under argon, in a 500 ml 3-necked flask equipped with a magnetic stirrer, sodium hydride (1.15 g, 1.00 eq, 60% in oil suspension) was suspended in 90 mL of tetrahydrofuran. 45 ml of dimethylsulfoxide were then added. The reaction mixture was cooled down to 10 C. and trimethylsulfoxonium iodide (6.37 g, 1.00 eq, 28.94 mmol) was added portion wise. The reaction mixture was stirred for 30 min at room temperature. Thereafter, a solution of (2,4-difluorophenyl)[1-(2,4,6-trifluorophenoxy)cyclopropyl]methanone (IV-1) (10.0 g, 1.0 eq, 28.94 mmol) in 45 ml of dimethylsulfoxide was added dropwise to the reaction mixture. The reaction mixture was stirred for 18 hours at room temperature until no further evolution was observed. The reaction mixture was quenched with a saturated aqueous solution of ammonium chloride. The aqueous phase was extracted by 210 ml of methyltert-butylether. Combined organic layers were washed twice with water and then brine, dried over MgSO4 and concentrated to give 9.00 g of 2-(2,4-difluorophenyl)-2-[1-(2,4,6-trifluorophenoxy)cyclopropyl]oxirane (V-1), 85% pure (77%) as a pale brown oil which was used without further purification.

    [0305] MS (ESI): 343.07 ([M+H].sup.+)

    Preparation of Compounds of the Formula (I-04) According to Process E:

    Example 4: Preparation of 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-[1-(2,4,6-trifluorophenoxy)cyclopropyl]ethyl acetate (I-04)

    [0306] ##STR00018##

    [0307] To a solution of 85% pure 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-[1-(2,4,6-trifluorophenoxy)cyclopropyl]ethanol (I-02) (110 mg, 1 eq, 0.23 mmol) in 5 mL of dioxane, was added under stirring sodium hydride (11 mg, 1.20 eq, 60% in oil suspension). The reaction mixture was stirred for one hour before acetyl chloride (215 mg, 10.0 eq, 2.27 mmol) was added. The reaction mixture was stirred at 70 C. for 20 hours. After being allowed to room temperature, the reaction mixture was quenched by addition of an aqueous saturated solution of sodium hydrogenocarbonate. After separation of the phases, the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over magnesium sulphate, filtered and concentrated in vacuo. The crude product was purified by liquid chromatography (eluent acetonitrile/water gradient). After evaporation of the solvent, the collected fractions were concentrated to provide 10 mg (11%) of 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-[1-(2,4,6-trifluorophenoxy)cyclopropyl]ethyl acetate (I-04).

    [0308] MS (ESI): 454.1 ([M+H].sup.+)

    [0309] The following Table 1 illustrates in a non-limiting manner examples of compounds according to formula (I).

    ##STR00019##

    TABLE-US-00001 TABLE 1 Ex N R.sup.1 X X.sup.1 X.sup.2 X.sup.3 n X.sup.4 m X.sup.5 LogP I-01(*) H F 4-Cl 2-F 6-F 0 0 3.57.sup.[a] I-02 H F 4-F 2-F 6-F 0 0 3.11.sup.[a]; 3.10.sup.[b] I-03(*) H F 4-Br 2-F 6-F 0 0 3.70.sup.[a] I-04 acetyl F 4-F 2-F 6-F 0 0 3.32.sup.[a]; 3.29.sup.[b] I-05 H F 4-F 3-F 5-F 0 0 3.44.sup.[a] I-06 H F 5-Cl 2-Cl 6-Cl 0 0 4.19.sup.[a] I-07 H F 4-Cl 2-Cl 6-Cl 0 0 4.49.sup.[a] I-08 H F 5-Cl 2-F 6-F 0 0 3.39.sup.[a] I-09 H F 4-OCF.sub.3 2-Cl 6-Cl 0 0 4.62.sup.[a] I-10 H F 4-CF.sub.3 2-Cl 6-Cl 0 0 4.46.sup.[a] I-11 H F 4-SCF.sub.3 2-Cl 6-Cl 0 0 4.97.sup.[a] I-12 H F 4-Br 2-Cl 6-Cl 0 0 4.62.sup.[a] I-13 H F 5-F 2-F 6-F 0 0 3.14.sup.[a] I-14 Me F 5-F 2-F 6-F 0 0 3.50.sup.[a] I-15 Me F 5-Cl 2-Cl 6-Cl 0 0 4.46.sup.[a] I-16 H F 4-F 2-Cl 6-Cl 0 0 3.94.sup.[a] I-17 Me F 3-Cl 2-F 6-F 0 0 3.85.sup.[a] I-18 Me F 4-OCF.sub.3 2-Cl 6-Cl 0 0 4.87.sup.[a] I-19(*) H F 4-Cl 2-F 6-F 0 0 3.55.sup.[a] I-20(*) H F 4-Cl 2-F 6-F 0 0 3.55.sup.[a] I-21(*) H F 4-Br 2-F 6-F 0 0 3.63.sup.[a] I-22(*) H F 4-Br 2-F 6-F 0 0 3.63.sup.[a] I-23 H Cl 4-Cl 2-F 6-F 0 0 4.01.sup.[a] I-24 H Cl 4-F 2-F 6-F 0 0 3.51.sup.[a] I-25 Me Cl 4-Cl 2-F 6-F 0 0 4.41.sup.[a] I-26 Me Cl 4-F 2-F 6-F 0 0 3.97.sup.[a] I-27 H F 4-F 5-F 6-F 0 0 3.30.sup.[a] I-28 H F 4-F 3-F 6-F 0 0 3.17.sup.[a] I-29 H F 5-F 2-F 6-Cl 0 0 3.42.sup.[a] I-30 H F 4-Br 3-F 5-F 0 0 3.85.sup.[a] I-31 H Cl 4-Br 2-F 6-F 0 0

    Optical Rotation

    [0310] Concentration c is expressed in g/100 mL

    (*) Ex I-19 and I-20 are the 2 Enantiomers of Ex I-01

    [0311] Ex I-19: Optical rotation: +6.0 (c=1.00, DCM, 20 C.)
    Ex I-20: Optical rotation: 6.0 (c=1.00, DCM, 20 C.)
    (*) Ex I-21 and I-22 are the 2 enantiomers of Ex I-03
    Ex I-21: Optical rotation: +6.2 (c=0.97, DCM, 20 C.)
    Ex I-22: Optical rotation: 5.7 (c=1.05, DCM, 20 C.)

    [0312] The following Table 2 illustrates in a non-limiting manner examples of compounds according to formula (IV).

    ##STR00020##

    TABLE-US-00002 TABLE 2 Ex N X X.sup.1 X.sup.2 X.sup.3 n X.sup.4 m X.sup.5 LogP IV-1 F 4-F 2-F 6-F 0 0 3.96.sup.[a] IV-2 F 4-Cl 2-F 6-F 0 0 4.44.sup.[a] IV-3 F 4-Br 2-F 6-F 0 0 4.54.sup.[a] IV-4 F 4-Cl 2-Cl 6-Cl 0 0 5.34.sup.[a] IV-5 F 4-F 2-Cl 6-Cl 0 0 4.76.sup.[a] IV-6 F 3-F 2-F 6-F 0 0 3.99.sup.[a] IV-7 F 4-Br 2-Cl 6-Cl 0 0 5.01.sup.[a] IV-8 F 3-Cl 2-Cl 6-Cl 0 0 5.03.sup.[a] IV-9 F 3-Cl 2-F 6-F 0 0 4.27.sup.[a] IV-10 F 4-F 3-F 5-F 0 0 4.20.sup.[a] IV-11 F 4-CF.sub.3 2-Cl 6-Cl 0 0 5.25.sup.[a] IV-12 F 4-OCF.sub.3 2-Cl 6-Cl 0 0 5.39.sup.[a] IV-13 F 4-SCF.sub.3 2-Cl 6-Cl 0 0 5.85.sup.[a] IV-14 F 4-cyano 2-Cl 6-Cl 0 0 4.15.sup.[a] IV-15 Cl 4-F 2-F 6-F 0 0 4.49.sup.[a] IV-16 Cl 4-Cl 2-F 6-F 0 0 5.03.sup.[a] IV-17 F 4-F 2-F 3-F 0 0 4.01.sup.[a] IV-18 F 4-F 2-F 5-F 0 0 3.94.sup.[a] IV-19 F 4-Br 3-F 5-F 0 0 4.54.sup.[a] IV-20 F 3-F 2-Cl 6-F 0 0 4.25.sup.[a] IV-21 Cl 4-Br 2-F 6-F 0 0 5.05.sup.[a]

    [0313] The following Table 3 illustrates in a non-limiting manner examples of compounds according to formula (V).

    ##STR00021##

    TABLE-US-00003 TABLE 3 Ex N X X.sup.1 X.sup.2 X.sup.3 n X.sup.4 m X.sup.5 LogP V-01 F 4-F 2-F 6-F 0 0 4.26.sup.[a]; 4.26.sup.[b] V-02 F 4-Cl 2-F 6-F 0 0 4.59.sup.[a] V-03 F 4-Br 2-F 6-F 0 0 4.86.sup.[a]; 4.87.sup.[b] V-04 F 4-F 3-F 5-F 0 0 4.64.sup.[a] V-05 F 4-OCF3 2-Cl 6-Cl 0 0 5.62.sup.[a] V-06 F 5-Cl 2-F 6-F 0 0 4.65.sup.[a] V-07 F 4-Cl 2-Cl 6-Cl 0 0 5.56.sup.[a] V-08 F 4-Br 2-Cl 6-Cl 0 0 5.72.sup.[a] V-09 F 3-Cl 2-Cl 6-Cl 0 0 5.27.sup.[a] V-10 F 3-F 2-F 6-F 0 0 4.20.sup.[a] V-11 F 4-CF3 2-Cl 6-Cl 0 0 5.51.sup.[a] V-12 F 4-F 2-Cl 6-Cl 0 0 4.98.sup.[a] V-13 F 4-SCF3 2-Cl 6-Cl 0 0 6.07.sup.[a] V-14 Cl 4-Cl 2-F 6-F 0 0 5.23.sup.[a] V-15 Cl 4-F 2-F 6-F 0 0 4.72.sup.[a] V-16 F 4-F 5-F 6-F 0 0 4.28.sup.[a] V-17 F 4-F 3-F 6-F 0 0 4.10.sup.[a] V-18 F 4-Br 3-F 5-F 0 0 4.86.sup.[a] V-19 F 5-F 2-F 6-Cl 0 0 4.35.sup.[a] Measurement of LogP values was performed according to EEC directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on reversed phase columns with the following methods: .sup.[a]LogP value is determined by measurement of LC-UV, in an acidic range, with 0.1% formic acid in water and acetonitrile as eluent (linear gradient from 10% acetonitrile to 95% acetonitrile). .sup.[b]LogP value is determined by measurement of LC-UV, in a neutral range, with 0.001 molar ammonium acetate solution in water and acetonitrile as eluent (linear gradient from 10% acetonitrile to 95% acetonitrile). .sup.[c]LogP value is determined by measurement of LC-UV, in an acidic range, with 0.1% phosphoric acid and acetonitrile as eluent (linear gradient from 10% acetonitrile to 95% acetonitrile).

    [0314] If more than one Log P value is available within the same method, all the values are given and separated by +.

    [0315] 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.

    NMR-Peak Lists

    [0316] 1H-NMR data of selected examples are written in form of 1H-NMR-peak lists. To each signal peak are listed the -value in ppm and the signal intensity in round brackets. Between the -valuesignal intensity pairs are semicolons as delimiters.

    [0317] The peak list of an example has therefore the form:

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

    [0318] 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.

    [0319] 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.

    [0320] 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.

    [0321] 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.

    [0322] 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.

    [0323] 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%).

    [0324] 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.

    [0325] 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.

    [0326] Further details of NMR-data description with peak lists you find in the publication Citation of NMR Peaklist Data within Patent Applications of the Research Disclosure Database Number 564025.

    Example I-01

    [0327] .sup.1H-NMR (499.9 MHz, d.sub.6-DMSO): =8.375 (15.3); 7.795 (16.0); 7.534 (1.5); 7.516 (3.3); 7.502 (3.2); 7.485 (1.5); 7.361 (0.8); 7.354 (1.6); 7.346 (10.5); 7.330 (10.3); 7.322 (1.6); 7.314 (0.7); 7.142 (1.7); 7.137 (1.8); 7.123 (1.9); 7.118 (3.3); 7.112 (2.0); 7.099 (1.7); 7.094 (1.7); 6.989 (1.8); 6.984 (1.8); 6.972 (3.3); 6.968 (3.1); 6.955 (1.8); 6.950 (1.6); 6.112 (15.7); 5.117 (4.9); 5.088 (6.0); 4.884 (5.0); 4.855 (4.0); 3.302 (21.4); 2.505 (7.9); 2.501 (10.7); 2.498 (7.9); 0.993 (0.9); 0.978 (1.9); 0.970 (1.8); 0.965 (1.4); 0.956 (2.8); 0.942 (1.7); 0.894 (1.5); 0.881 (2.8); 0.867 (1.9); 0.858 (1.9); 0.844 (1.1); 0.684 (1.1); 0.670 (1.8); 0.661 (1.9); 0.647 (2.5); 0.633 (1.3); 0.562 (1.3); 0.548 (2.3); 0.536 (1.6); 0.525 (1.6); 0.512 (0.7); 0.000 (6.3)

    Example I-02

    [0328] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): =8.381 (14.1); 7.804 (13.7); 7.568 (1.5); 7.551 (2.0); 7.546 (3.2); 7.529 (3.1); 7.524 (2.0); 7.506 (1.5); 7.219 (0.5); 7.208 (1.2); 7.199 (4.5); 7.178 (7.2); 7.156 (4.4); 7.146 (2.6); 7.140 (2.0); 7.123 (1.9); 7.116 (3.1); 7.109 (1.9); 7.092 (1.7); 7.086 (1.6); 7.004 (1.7); 6.997 (1.6); 6.982 (3.0); 6.976 (2.6); 6.961 (1.6); 6.955 (1.4); 6.100 (16.0); 5.143 (4.1); 5.107 (5.3); 4.911 (4.2); 4.875 (3.0); 3.461 (0.3); 3.318 (733.6); 2.675 (0.5); 2.671 (0.7); 2.666 (0.5); 2.541 (1.6); 2.510 (37.6); 2.506 (67.0); 2.502 (85.1); 2.497 (58.7); 2.493 (28.1); 2.333 (0.4); 2.328 (0.6); 2.324 (0.4); 1.987 (0.3); 1.398 (0.6); 1.387 (0.4); 0.970 (0.8); 0.952 (1.6); 0.942 (1.7); 0.935 (1.3); 0.924 (2.4); 0.907 (1.6); 0.870 (1.5); 0.854 (2.6); 0.837 (1.8); 0.826 (1.5); 0.809 (0.9); 0.650 (1.0); 0.633 (1.5); 0.622 (1.7); 0.604 (2.1); 0.587 (1.1); 0.509 (1.2); 0.492 (2.0); 0.477 (1.5); 0.464 (1.4); 0.447 (0.6); 0.000 (0.7)

    Example I-03

    [0329] .sup.1H-NMR (499.9 MHz, d.sub.6-DMSO): =8.373 (15.3); 7.793 (16.0); 7.531 (1.4); 7.516 (2.0); 7.513 (3.1); 7.499 (3.1); 7.495 (2.0); 7.481 (1.5); 7.466 (0.8); 7.459 (1.6); 7.450 (10.1); 7.435 (9.9); 7.427 (1.5); 7.420 (0.6); 7.140 (1.6); 7.135 (1.6); 7.121 (1.9); 7.116 (3.1); 7.110 (1.8); 7.097 (1.7); 7.092 (1.6); 6.988 (1.8); 6.982 (1.7); 6.971 (3.1); 6.966 (2.8); 6.954 (1.7); 6.949 (1.5); 6.110 (15.1); 5.114 (4.7); 5.085 (5.8); 4.881 (4.7); 4.852 (3.6); 3.300 (24.0); 2.504 (10.8); 2.501 (14.4); 2.497 (10.2); 0.991 (0.9); 0.976 (1.7); 0.969 (1.7); 0.963 (1.3); 0.954 (2.6); 0.940 (1.6); 0.892 (1.4); 0.878 (2.6); 0.864 (1.8); 0.856 (1.7); 0.842 (1.0); 0.682 (1.0); 0.668 (1.6); 0.659 (1.7); 0.645 (2.3); 0.631 (1.2); 0.562 (1.2); 0.549 (2.1); 0.536 (1.5); 0.526 (1.5); 0.512 (0.7); 0.006 (0.6); 0.000 (13.8); 0.007 (0.5)

    Example I-04

    [0330] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): =8.480 (2.9); 8.064 (2.6); 7.641 (0.4); 7.635 (0.6); 7.618 (0.6); 7.612 (0.4); 7.286 (0.3); 7.280 (0.4); 7.263 (0.4); 7.256 (0.5); 7.247 (0.4); 7.231 (0.5); 7.224 (0.5); 7.212 (0.9); 7.190 (1.4); 7.169 (0.9); 7.151 (0.4); 7.144 (0.3); 7.130 (0.6); 7.123 (0.5); 5.887 (0.7); 5.851 (0.8); 5.747 (16.0); 5.307 (1.0); 5.271 (0.9); 3.306 (137.1); 3.282 (1.9); 2.540 (0.4); 2.509 (12.5); 2.505 (22.2); 2.501 (28.1); 2.496 (19.6); 2.070 (1.2); 2.026 (8.5); 1.009 (0.4); 0.997 (0.4); 0.980 (0.4); 0.354 (0.3); 0.337 (0.5); 0.324 (0.5); 0.306 (0.5); 0.050 (0.4); 0.034 (0.5); 0.021 (0.4); 0.000 (0.9)

    Example I-05

    [0331] .sup.1H-NMR (499.9 MHz, CDCl.sub.3): =8.072 (8.0); 8.069 (7.8); 7.781 (13.2); 7.700 (2.1); 7.687 (2.4); 7.682 (4.2); 7.669 (4.2); 7.664 (2.4); 7.651 (2.1); 7.260 (17.6); 6.864 (1.9); 6.859 (2.0); 6.847 (2.9); 6.845 (3.2); 6.831 (1.9); 6.826 (1.9); 6.568 (2.2); 6.563 (2.1); 6.551 (2.4); 6.546 (2.6); 6.544 (2.7); 6.539 (2.2); 6.527 (2.3); 6.522 (2.1); 6.473 (0.6); 6.465 (1.3); 6.458 (5.5); 6.446 (5.6); 6.439 (5.5); 6.427 (5.2); 6.420 (1.2); 6.412 (0.5); 5.452 (3.9); 5.449 (3.7); 5.424 (4.0); 5.420 (4.1); 5.398 (16.0); 4.660 (4.3); 4.657 (4.2); 4.632 (4.0); 4.629 (4.0); 1.578 (6.9); 1.422 (1.5); 1.415 (0.4); 1.334 (3.9); 1.293 (1.1); 1.285 (5.2); 1.256 (4.8); 1.218 (0.6); 1.215 (0.6); 1.202 (0.6); 1.184 (0.6); 1.171 (0.5); 1.159 (1.6); 1.144 (2.5); 1.135 (6.1); 1.123 (6.7); 1.120 (5.3); 1.112 (3.6); 1.098 (1.7); 1.093 (0.7); 1.087 (0.6); 1.072 (0.9); 1.043 (0.4); 1.024 (0.4); 1.010 (0.3); 0.960 (0.4); 0.943 (1.4); 0.928 (4.9); 0.918 (9.8); 0.914 (6.8); 0.907 (4.2); 0.892 (1.4); 0.880 (1.0); 0.875 (0.8); 0.866 (0.8); 0.846 (2.9); 0.840 (2.8); 0.811 (1.1); 0.006 (0.7); 0.000 (16.4); 0.007 (0.7)

    Example I-06

    [0332] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.309 (7.6); 8.303 (7.7); 7.891 (13.8); 7.789 (2.1); 7.767 (2.3); 7.760 (4.4); 7.737 (4.2); 7.730 (2.4); 7.708 (2.1); 7.646 (0.4); 7.366 (0.3); 7.300 (77.2); 7.268 (0.4); 7.255 (0.7); 7.225 (36.1); 7.195 (0.5); 6.949 (0.6); 6.921 (1.7); 6.914 (2.0); 6.894 (2.8); 6.886 (3.0); 6.867 (1.6); 6.859 (1.8); 6.764 (2.2); 6.756 (2.1); 6.735 (2.4); 6.723 (3.0); 6.714 (2.2); 6.694 (2.4); 6.686 (2.0); 5.826 (3.9); 5.774 (4.4); 5.444 (16.0); 5.339 (0.8); 4.893 (4.1); 4.888 (4.2); 4.846 (3.7); 4.840 (3.9); 1.658 (0.3); 1.592 (63.0); 1.293 (0.5); 1.126 (0.8); 1.108 (0.7); 1.087 (3.1); 1.070 (9.7); 1.064 (10.9); 1.047 (3.5); 1.024 (0.9); 1.009 (1.1); 0.793 (0.7); 0.767 (0.3); 0.746 (4.2); 0.727 (2.4); 0.708 (3.3); 0.690 (1.9); 0.468 (2.2); 0.451 (4.2); 0.434 (2.1); 0.412 (4.4); 0.367 (0.5); 0.234 (0.4); 0.105 (0.4); 0.050 (3.1); 0.039 (80.8); 0.028 (3.1); 0.160 (0.4)

    Example I-07

    [0333] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.302 (7.9); 8.295 (7.7); 7.888 (14.2); 7.778 (2.1); 7.756 (2.4); 7.748 (4.4); 7.726 (4.4); 7.719 (2.5); 7.696 (2.2); 7.320 (0.4); 7.299 (28.7); 7.285 (44.5); 7.274 (0.8); 7.273 (0.8); 6.914 (1.8); 6.906 (2.0); 6.886 (2.8); 6.881 (2.8); 6.878 (2.9); 6.859 (1.7); 6.851 (1.8); 6.762 (2.4); 6.753 (2.1); 6.733 (2.5); 6.724 (2.9); 6.721 (2.9); 6.712 (2.2); 6.692 (2.4); 6.683 (2.1); 5.784 (3.9); 5.737 (4.2); 5.733 (4.3); 5.429 (16.0); 5.338 (1.8); 4.893 (4.2); 4.888 (4.1); 4.846 (3.7); 4.841 (3.8); 1.612 (8.7); 1.294 (0.7); 1.105 (0.9); 1.084 (0.8); 1.067 (3.0); 1.046 (10.0); 1.040 (11.7); 1.021 (3.6); 1.001 (1.2); 0.983 (1.3); 0.775 (0.7); 0.730 (4.3); 0.709 (2.6); 0.691 (3.3); 0.671 (2.0); 0.463 (2.2); 0.445 (4.2); 0.426 (2.1); 0.405 (5.5); 0.361 (0.4); 0.049 (1.0); 0.038 (30.9); 0.027 (1.3)

    Example I-08

    [0334] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.271 (9.2); 8.267 (8.8); 8.046 (0.7); 7.899 (15.1); 7.778 (2.2); 7.755 (2.6); 7.748 (4.6); 7.726 (4.9); 7.718 (2.8); 7.696 (2.3); 7.300 (11.8); 7.175 (2.3); 7.158 (2.6); 7.150 (2.8); 7.145 (3.1); 7.132 (2.9); 7.127 (3.1); 7.119 (3.0); 7.102 (2.7); 6.992 (0.3); 6.975 (0.4); 6.929 (2.0); 6.922 (2.2); 6.903 (3.5); 6.897 (3.7); 6.894 (3.9); 6.889 (4.6); 6.881 (3.7); 6.876 (2.6); 6.874 (2.6); 6.865 (2.6); 6.857 (5.4); 6.850 (5.2); 6.826 (2.6); 6.819 (2.6); 6.779 (2.5); 6.771 (2.3); 6.750 (2.7); 6.741 (3.0); 6.739 (3.1); 6.730 (2.4); 6.709 (2.5); 6.701 (2.2); 5.562 (4.6); 5.514 (5.4); 5.340 (16.0); 5.028 (5.1); 5.024 (5.0); 4.981 (4.3); 4.977 (4.2); 1.666 (4.8); 1.293 (0.8); 1.059 (1.2); 1.037 (2.2); 1.022 (2.5); 1.017 (1.8); 1.000 (3.8); 0.977 (2.9); 0.941 (2.6); 0.919 (4.8); 0.896 (3.3); 0.881 (2.4); 0.860 (1.7); 0.747 (1.3); 0.724 (1.8); 0.709 (2.4); 0.687 (3.2); 0.665 (1.7); 0.616 (2.0); 0.595 (3.0); 0.576 (2.0); 0.573 (2.1); 0.557 (1.8); 0.534 (0.8); 0.047 (0.7); 0.037 (12.2); 0.026 (0.6)

    Example I-09

    [0335] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.304 (7.9); 8.298 (7.9); 7.892 (14.4); 7.786 (2.1); 7.764 (2.3); 7.756 (4.4); 7.734 (4.3); 7.727 (2.5); 7.705 (2.2); 7.300 (32.5); 7.186 (19.9); 7.183 (19.7); 6.921 (1.8); 6.913 (2.0); 6.894 (2.8); 6.889 (2.8); 6.886 (3.0); 6.867 (1.7); 6.858 (1.8); 6.764 (2.4); 6.755 (2.1); 6.734 (2.5); 6.723 (3.0); 6.714 (2.2); 6.694 (2.4); 6.685 (2.1); 5.799 (3.9); 5.748 (4.3); 5.456 (16.0); 4.891 (4.1); 4.886 (4.2); 4.844 (3.7); 4.839 (3.9); 1.605 (10.0); 1.293 (0.6); 1.133 (0.8); 1.115 (0.6); 1.095 (3.0); 1.077 (9.7); 1.071 (11.2); 1.053 (3.5); 1.032 (1.0); 1.015 (1.2); 0.793 (0.6); 0.747 (4.6); 0.726 (2.4); 0.709 (3.2); 0.690 (1.9); 0.470 (2.0); 0.453 (4.2); 0.436 (2.0); 0.414 (4.8); 0.369 (0.4); 0.049 (1.2); 0.039 (35.4); 0.028 (1.4)

    Example I-10

    [0336] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.310 (4.8); 8.305 (4.6); 7.892 (8.6); 7.792 (1.4); 7.769 (1.6); 7.762 (2.8); 7.740 (2.8); 7.732 (1.6); 7.710 (1.4); 7.547 (16.0); 7.300 (6.3); 6.927 (1.3); 6.918 (1.4); 6.898 (2.1); 6.894 (2.1); 6.890 (2.1); 6.871 (1.3); 6.863 (1.3); 6.766 (1.6); 6.757 (1.4); 6.737 (1.7); 6.725 (2.0); 6.716 (1.5); 6.696 (1.6); 6.687 (1.3); 5.812 (2.7); 5.764 (2.9); 5.761 (3.0); 5.490 (5.9); 5.335 (0.4); 4.900 (2.8); 4.895 (2.8); 4.853 (2.6); 4.848 (2.6); 1.291 (1.6); 1.255 (0.9); 1.234 (0.8); 1.156 (0.5); 1.138 (0.4); 1.118 (1.9); 1.100 (6.6); 1.094 (7.4); 1.077 (2.5); 1.055 (0.7); 1.039 (0.9); 0.793 (0.4); 0.747 (2.9); 0.726 (1.6); 0.708 (2.3); 0.690 (1.3); 0.471 (1.3); 0.453 (2.8); 0.436 (1.3); 0.414 (3.0); 0.108 (20.2); 0.036 (4.5)

    Example I-11

    [0337] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.307 (4.2); 8.301 (4.0); 7.888 (7.7); 7.786 (1.1); 7.764 (1.3); 7.756 (2.5); 7.734 (2.4); 7.727 (1.3); 7.705 (1.2); 7.620 (1.2); 7.579 (16.0); 7.300 (4.8); 7.107 (0.3); 6.923 (1.1); 6.914 (1.2); 6.895 (1.6); 6.890 (1.6); 6.886 (1.7); 6.868 (1.0); 6.859 (1.1); 6.765 (1.3); 6.757 (1.2); 6.736 (1.4); 6.725 (1.6); 6.716 (1.2); 6.695 (1.3); 6.687 (1.1); 5.802 (2.1); 5.751 (2.3); 5.477 (7.8); 5.334 (0.5); 4.896 (2.2); 4.890 (2.2); 4.848 (2.0); 4.843 (2.3); 3.059 (1.2); 2.543 (0.4); 2.471 (0.5); 1.291 (1.0); 1.149 (0.4); 1.110 (1.4); 1.091 (5.1); 1.085 (6.1); 1.067 (1.9); 1.047 (0.7); 1.029 (0.8); 0.916 (0.4); 0.753 (2.5); 0.733 (1.3); 0.714 (1.7); 0.695 (1.1); 0.477 (1.0); 0.459 (2.2); 0.441 (1.1); 0.420 (2.8); 0.107 (0.4); 0.035 (3.7)

    Example I-12

    [0338] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.301 (2.8); 8.294 (2.8); 7.886 (5.0); 7.776 (0.8); 7.754 (0.8); 7.746 (1.6); 7.724 (1.6); 7.717 (0.9); 7.695 (0.8); 7.425 (16.0); 7.300 (8.8); 6.911 (0.6); 6.903 (0.7); 6.885 (1.0); 6.880 (1.0); 6.877 (1.1); 6.856 (0.6); 6.849 (0.6); 6.760 (0.9); 6.752 (0.8); 6.731 (0.9); 6.720 (1.1); 6.711 (0.8); 6.691 (0.8); 6.682 (0.7); 5.781 (1.4); 5.777 (1.4); 5.734 (1.5); 5.730 (1.5); 5.428 (5.8); 4.891 (1.5); 4.886 (1.5); 4.844 (1.3); 4.839 (1.4); 1.625 (8.4); 1.305 (0.7); 1.298 (0.7); 1.104 (0.3); 1.066 (1.1); 1.045 (3.5); 1.039 (4.1); 1.020 (1.3); 1.001 (0.4); 0.982 (0.5); 0.920 (0.7); 0.729 (1.4); 0.727 (1.4); 0.708 (0.9); 0.690 (1.1); 0.688 (1.1); 0.670 (0.7); 0.463 (0.8); 0.445 (1.5); 0.426 (0.8); 0.405 (1.9); 0.038 (8.7); 0.027 (0.4)

    Example I-13

    [0339] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.269 (6.6); 8.264 (6.7); 7.899 (11.5); 7.778 (1.8); 7.756 (2.0); 7.748 (3.7); 7.726 (3.7); 7.718 (2.1); 7.696 (1.9); 7.300 (12.7); 6.978 (0.8); 6.962 (0.9); 6.951 (1.0); 6.946 (2.0); 6.935 (1.3); 6.930 (3.3); 6.920 (3.5); 6.915 (2.2); 6.904 (3.6); 6.900 (3.6); 6.892 (3.0); 6.889 (3.3); 6.873 (2.8); 6.868 (2.4); 6.864 (2.1); 6.861 (2.1); 6.852 (1.7); 6.845 (1.6); 6.837 (2.2); 6.829 (2.2); 6.821 (2.1); 6.814 (2.2); 6.805 (0.9); 6.798 (1.0); 6.789 (0.8); 6.779 (2.2); 6.770 (1.8); 6.750 (2.1); 6.741 (2.2); 6.738 (2.5); 6.729 (1.9); 6.709 (2.0); 6.700 (1.8); 5.567 (3.3); 5.520 (4.0); 5.338 (16.0); 5.025 (3.7); 5.021 (3.8); 4.978 (3.2); 4.973 (3.3); 2.083 (1.2); 1.649 (9.7); 1.320 (0.5); 1.297 (1.1); 1.273 (0.4); 1.067 (0.9); 1.045 (1.6); 1.030 (1.9); 1.024 (1.3); 1.007 (2.8); 0.986 (2.4); 0.952 (2.0); 0.931 (3.5); 0.919 (0.9); 0.908 (2.5); 0.893 (1.8); 0.872 (1.4); 0.773 (1.0); 0.752 (1.3); 0.749 (1.4); 0.735 (1.8); 0.713 (2.3); 0.711 (2.4); 0.690 (1.3); 0.639 (1.5); 0.617 (2.2); 0.600 (1.4); 0.596 (1.6); 0.580 (1.3); 0.558 (0.7); 0.048 (0.5); 0.037 (12.6); 0.026 (0.6)

    Example I-14

    [0340] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.419 (4.1); 7.970 (4.1); 7.535 (0.6); 7.514 (0.6); 7.506 (1.2); 7.484 (1.2); 7.477 (0.7); 7.455 (0.6); 7.300 (1.5); 6.989 (0.5); 6.982 (0.5); 6.962 (0.7); 6.958 (0.8); 6.952 (0.9); 6.936 (0.7); 6.925 (0.8); 6.920 (0.7); 6.907 (1.0); 6.899 (0.7); 6.893 (0.7); 6.889 (0.6); 6.878 (1.3); 6.873 (0.7); 6.870 (0.8); 6.866 (0.9); 6.858 (0.7); 6.847 (0.5); 6.837 (0.7); 6.829 (1.0); 6.822 (0.5); 6.814 (0.5); 6.807 (0.5); 6.798 (0.7); 6.791 (0.7); 6.783 (0.6); 6.775 (0.7); 5.691 (1.1); 5.644 (1.3); 5.641 (1.3); 5.023 (1.7); 4.973 (1.5); 3.570 (16.0); 2.038 (1.9); 1.818 (0.4); 1.453 (0.5); 1.283 (0.4); 0.956 (0.3); 0.936 (0.4); 0.920 (0.7); 0.912 (0.5); 0.896 (0.8); 0.885 (0.4); 0.598 (0.4); 0.574 (0.6); 0.553 (0.5); 0.546 (0.5); 0.537 (0.6); 0.495 (0.4); 0.473 (0.7); 0.450 (0.5); 0.435 (0.4); 0.425 (1.2); 0.417 (0.9); 0.395 (0.8); 0.378 (0.5); 0.029 (1.2)

    Example I-15

    [0341] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.522 (4.3); 7.930 (4.3); 7.585 (0.6); 7.563 (0.7); 7.556 (1.2); 7.534 (1.2); 7.527 (0.8); 7.505 (0.6); 7.300 (3.3); 7.228 (12.2); 6.959 (0.5); 6.950 (0.7); 6.932 (0.8); 6.924 (1.0); 6.909 (1.0); 6.897 (0.8); 6.880 (0.9); 6.869 (0.9); 6.860 (0.6); 6.840 (0.7); 6.831 (0.6); 5.741 (1.0); 5.734 (1.0); 5.691 (1.2); 5.684 (1.2); 5.335 (0.8); 5.188 (1.6); 5.137 (1.4); 3.691 (16.0); 1.690 (2.1); 1.289 (0.5); 0.924 (0.3); 0.904 (0.7); 0.892 (0.5); 0.889 (0.5); 0.881 (0.6); 0.877 (0.6); 0.867 (0.7); 0.843 (0.6); 0.796 (0.6); 0.774 (0.7); 0.768 (0.4); 0.758 (0.8); 0.749 (0.6); 0.735 (0.9); 0.712 (0.6); 0.539 (0.6); 0.514 (1.0); 0.503 (0.5); 0.492 (0.8); 0.477 (0.8); 0.457 (0.9); 0.446 (1.1); 0.425 (0.8); 0.409 (0.8); 0.399 (0.6); 0.385 (0.8); 0.361 (0.4); 0.106 (0.5); 0.035 (2.3)

    Example I-16

    [0342] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.303 (4.4); 8.297 (4.5); 7.886 (7.9); 7.780 (1.2); 7.757 (1.3); 7.750 (2.5); 7.728 (2.5); 7.720 (1.4); 7.698 (1.3); 7.300 (10.4); 7.058 (11.1); 7.045 (0.5); 7.032 (11.1); 6.914 (1.0); 6.906 (1.1); 6.886 (1.6); 6.878 (1.7); 6.859 (1.0); 6.850 (1.1); 6.764 (1.4); 6.755 (1.2); 6.734 (1.4); 6.723 (1.7); 6.714 (1.3); 6.694 (1.3); 6.685 (1.2); 5.792 (2.3); 5.745 (2.5); 5.741 (2.6); 5.418 (9.3); 5.337 (1.0); 4.893 (2.4); 4.888 (2.4); 4.846 (2.2); 4.840 (2.3); 2.083 (0.5); 1.638 (16.0); 1.320 (0.3); 1.297 (0.9); 1.098 (0.5); 1.078 (0.5); 1.060 (1.8); 1.040 (5.9); 1.034 (7.0); 1.016 (2.0); 0.996 (0.7); 0.978 (0.7); 0.919 (0.7); 0.772 (0.4); 0.727 (2.8); 0.706 (1.5); 0.688 (2.0); 0.668 (1.1); 0.456 (1.3); 0.438 (2.5); 0.420 (1.2); 0.399 (3.4); 0.048 (0.4); 0.037 (9.3); 0.026 (0.3)

    Example I-17

    [0343] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.425 (4.0); 7.976 (4.0); 7.539 (0.5); 7.517 (0.6); 7.509 (1.1); 7.487 (1.1); 7.480 (0.7); 7.458 (0.6); 7.300 (5.5); 7.153 (0.6); 7.135 (0.6); 7.128 (0.7); 7.123 (0.8); 7.110 (0.7); 7.105 (0.8); 7.097 (0.8); 7.079 (0.7); 6.996 (0.4); 6.988 (0.5); 6.970 (0.7); 6.965 (0.8); 6.962 (0.8); 6.942 (0.4); 6.933 (0.5); 6.913 (0.7); 6.904 (0.5); 6.884 (0.7); 6.872 (0.8); 6.863 (0.6); 6.854 (0.8); 6.847 (0.9); 6.843 (0.8); 6.834 (0.6); 6.823 (1.3); 6.816 (1.3); 6.792 (0.6); 6.785 (0.6); 5.687 (1.1); 5.641 (1.2); 5.637 (1.2); 5.337 (3.9); 5.025 (1.6); 4.975 (1.4); 3.575 (16.0); 2.209 (0.5); 1.656 (5.9); 0.958 (0.3); 0.938 (0.4); 0.922 (0.5); 0.915 (0.6); 0.899 (0.8); 0.591 (0.5); 0.572 (0.7); 0.542 (0.6); 0.530 (0.5); 0.484 (0.4); 0.462 (0.6); 0.444 (0.4); 0.439 (0.6); 0.434 (0.4); 0.419 (1.2); 0.414 (1.2); 0.392 (0.7); 0.376 (0.5); 0.036 (5.4)

    Example I-18

    [0344] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.520 (3.9); 7.938 (4.5); 7.581 (0.6); 7.559 (0.7); 7.552 (1.2); 7.530 (1.2); 7.523 (0.7); 7.501 (0.6); 7.300 (8.2); 7.185 (6.1); 7.182 (5.8); 6.965 (0.5); 6.956 (0.6); 6.936 (0.8); 6.928 (1.0); 6.911 (1.2); 6.902 (1.0); 6.882 (0.8); 6.871 (0.9); 6.862 (0.6); 6.842 (0.7); 6.834 (0.6); 5.740 (1.0); 5.733 (1.0); 5.689 (1.2); 5.682 (1.2); 5.338 (2.2); 5.165 (1.7); 5.115 (1.4); 3.682 (16.0); 1.630 (2.7); 1.292 (2.2); 0.941 (0.4); 0.918 (0.9); 0.892 (1.1); 0.882 (1.2); 0.858 (0.8); 0.787 (0.6); 0.765 (0.7); 0.748 (0.8); 0.739 (0.5); 0.726 (0.9); 0.702 (0.5); 0.540 (0.5); 0.515 (0.9); 0.503 (0.5); 0.493 (0.8); 0.478 (0.7); 0.457 (0.8); 0.445 (1.0); 0.423 (0.8); 0.407 (0.8); 0.398 (0.5); 0.384 (0.8); 0.359 (0.4); 0.107 (1.2); 0.048 (0.4); 0.037 (7.9); 0.026 (0.4)

    Example I-19

    [0345] .sup.1H-NMR (499.9 MHz, CDCl.sub.3): =8.217 (9.6); 7.856 (14.6); 7.713 (2.1); 7.700 (2.7); 7.695 (4.4); 7.682 (4.5); 7.677 (2.5); 7.664 (2.1); 7.260 (17.9); 6.911 (1.1); 6.903 (2.2); 6.895 (13.1); 6.880 (12.8); 6.871 (3.8); 6.865 (3.0); 6.853 (3.5); 6.851 (3.5); 6.837 (2.1); 6.832 (2.0); 6.722 (2.5); 6.717 (2.2); 6.704 (2.7); 6.698 (3.3); 6.692 (2.3); 6.680 (2.5); 6.675 (2.1); 5.485 (5.3); 5.457 (5.8); 5.296 (7.1); 5.259 (16.0); 4.975 (5.6); 4.946 (5.0); 1.580 (4.2); 0.977 (1.5); 0.963 (2.9); 0.954 (2.5); 0.949 (2.0); 0.940 (4.1); 0.926 (2.6); 0.862 (2.3); 0.848 (4.2); 0.839 (1.8); 0.834 (2.9); 0.826 (2.9); 0.812 (1.9); 0.675 (1.5); 0.661 (2.3); 0.652 (2.3); 0.638 (3.3); 0.624 (1.7); 0.554 (1.8); 0.540 (3.2); 0.527 (2.0); 0.517 (2.2); 0.502 (1.1); 0.000 (16.7); 0.007 (0.6)

    Example I-20

    [0346] .sup.1H-NMR (499.9 MHz, CDCl.sub.3): =8.215 (9.1); 7.856 (14.4); 7.713 (2.0); 7.700 (2.4); 7.695 (4.4); 7.682 (4.3); 7.677 (2.6); 7.664 (2.1); 7.260 (18.2); 6.911 (1.0); 6.903 (1.9); 6.895 (12.7); 6.880 (12.5); 6.871 (3.7); 6.865 (3.0); 6.853 (3.2); 6.851 (3.3); 6.849 (3.4); 6.837 (1.9); 6.832 (2.0); 6.721 (2.3); 6.716 (2.2); 6.704 (2.5); 6.697 (3.2); 6.692 (2.4); 6.680 (2.3); 6.674 (2.2); 5.485 (5.1); 5.456 (5.6); 5.296 (6.8); 5.259 (16.0); 4.973 (5.3); 4.945 (4.7); 2.001 (0.5); 1.580 (2.8); 0.977 (1.4); 0.962 (2.7); 0.954 (2.4); 0.949 (2.0); 0.940 (4.0); 0.926 (2.5); 0.862 (2.2); 0.848 (4.0); 0.839 (1.7); 0.834 (2.8); 0.825 (2.8); 0.812 (1.8); 0.675 (1.4); 0.661 (2.2); 0.652 (2.2); 0.638 (3.1); 0.624 (1.6); 0.553 (1.7); 0.539 (3.0); 0.526 (1.9); 0.516 (2.1); 0.502 (1.0); 0.006 (0.7); 0.000 (17.1); 0.007 (1.1)

    Example I-21

    [0347] .sup.1H-NMR (499.9 MHz, CDCl.sub.3): =8.213 (9.4); 7.855 (13.1); 7.711 (1.8); 7.697 (2.2); 7.693 (3.9); 7.680 (3.8); 7.675 (2.4); 7.662 (1.9); 7.260 (14.1); 7.057 (0.9); 7.050 (1.8); 7.042 (11.7); 7.027 (11.6); 7.019 (1.8); 7.012 (0.9); 6.868 (2.0); 6.864 (2.1); 6.848 (3.5); 6.835 (1.9); 6.830 (1.9); 6.719 (2.0); 6.714 (2.0); 6.702 (2.2); 6.695 (3.3); 6.690 (2.1); 6.677 (2.1); 6.672 (1.9); 5.483 (5.2); 5.454 (5.8); 5.296 (4.0); 5.258 (16.0); 4.970 (5.5); 4.942 (4.9); 1.578 (10.9); 0.977 (1.3); 0.963 (2.6); 0.955 (2.2); 0.949 (1.9); 0.940 (3.8); 0.926 (2.2); 0.863 (2.0); 0.849 (3.9); 0.839 (1.6); 0.835 (2.6); 0.826 (2.7); 0.812 (1.6); 0.676 (1.4); 0.661 (2.2); 0.652 (2.2); 0.638 (3.1); 0.625 (1.6); 0.555 (1.7); 0.541 (3.0); 0.528 (2.0); 0.518 (2.1); 0.504 (1.0); 0.000 (12.4)

    Example I-22

    [0348] .sup.1H-NMR (499.9 MHz, CDCl.sub.3): =8.213 (9.7); 7.855 (14.2); 7.711 (2.0); 7.698 (2.4); 7.693 (4.3); 7.680 (4.2); 7.675 (2.7); 7.662 (2.1); 7.260 (19.4); 7.057 (0.9); 7.051 (1.9); 7.042 (12.5); 7.028 (12.6); 7.019 (2.4); 7.012 (1.2); 6.869 (2.0); 6.864 (2.2); 6.848 (3.6); 6.836 (2.1); 6.831 (2.1); 6.719 (2.2); 6.714 (2.2); 6.702 (2.4); 6.695 (3.3); 6.690 (2.4); 6.677 (2.3); 6.672 (2.2); 5.483 (5.3); 5.454 (5.9); 5.297 (9.2); 5.257 (16.0); 4.970 (5.6); 4.942 (5.0); 1.573 (9.2); 0.978 (1.4); 0.963 (2.7); 0.955 (2.4); 0.950 (2.1); 0.941 (4.0); 0.927 (2.5); 0.863 (2.1); 0.849 (4.0); 0.840 (1.8); 0.835 (2.9); 0.826 (2.9); 0.813 (1.8); 0.676 (1.4); 0.662 (2.3); 0.653 (2.4); 0.639 (3.3); 0.625 (1.7); 0.556 (1.7); 0.542 (3.1); 0.528 (2.1); 0.519 (2.3); 0.505 (1.1); 0.006 (0.8); 0.000 (17.4)

    Example I-23

    [0349] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.257 (8.6); 8.253 (8.3); 7.896 (14.4); 7.711 (4.2); 7.683 (8.6); 7.654 (4.6); 7.298 (14.2); 7.169 (4.4); 7.163 (4.7); 7.141 (4.0); 7.134 (4.3); 7.040 (5.0); 7.033 (4.4); 7.000 (5.0); 6.993 (4.6); 6.966 (1.2); 6.954 (2.2); 6.940 (12.4); 6.915 (12.1); 6.901 (2.0); 6.889 (1.0); 5.546 (4.3); 5.498 (5.1); 5.336 (16.0); 5.004 (4.8); 5.001 (4.8); 4.957 (4.0); 4.954 (4.0); 1.651 (14.9); 1.290 (0.7); 1.033 (1.1); 1.011 (1.9); 0.996 (2.4); 0.974 (3.6); 0.953 (2.9); 0.927 (2.6); 0.906 (4.3); 0.884 (3.0); 0.868 (2.2); 0.847 (1.7); 0.730 (1.2); 0.707 (1.8); 0.692 (2.3); 0.671 (3.0); 0.649 (1.7); 0.600 (1.9); 0.579 (2.8); 0.557 (2.0); 0.541 (1.6); 0.520 (0.8); 0.046 (0.7); 0.035 (12.1); 0.025 (0.6)

    Example I-24

    [0350] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.264 (3.6); 8.260 (3.6); 7.901 (6.2); 7.717 (1.8); 7.688 (3.8); 7.660 (2.0); 7.298 (10.9); 7.173 (1.9); 7.166 (2.1); 7.144 (1.7); 7.137 (1.9); 7.047 (2.1); 7.040 (1.9); 7.008 (2.1); 7.001 (1.9); 6.708 (0.5); 6.696 (2.6); 6.680 (0.7); 6.669 (4.0); 6.658 (0.7); 6.642 (2.5); 6.630 (0.5); 5.549 (1.9); 5.500 (2.2); 5.336 (0.5); 5.324 (6.7); 5.015 (2.0); 5.012 (2.0); 4.968 (1.7); 4.965 (1.7); 1.622 (16.0); 1.295 (0.4); 1.019 (0.5); 0.997 (0.8); 0.982 (1.0); 0.959 (1.5); 0.938 (1.4); 0.911 (1.2); 0.890 (1.9); 0.868 (1.3); 0.853 (0.9); 0.831 (0.7); 0.714 (0.5); 0.691 (0.7); 0.676 (1.0); 0.653 (1.2); 0.632 (0.7); 0.579 (0.8); 0.557 (1.2); 0.536 (0.8); 0.520 (0.7); 0.498 (0.3); 0.047 (0.4); 0.036 (9.7); 0.025 (0.4)

    Example I-25

    [0351] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.398 (4.1); 7.963 (4.2); 7.468 (1.0); 7.440 (2.2); 7.412 (1.4); 7.298 (2.0); 7.228 (1.2); 7.221 (1.4); 7.200 (0.9); 7.192 (1.3); 7.177 (1.5); 7.170 (1.0); 7.137 (1.4); 7.130 (1.2); 6.911 (0.5); 6.898 (3.5); 6.873 (3.4); 6.859 (0.5); 5.670 (1.1); 5.622 (1.2); 5.620 (1.2); 5.006 (1.6); 4.956 (1.4); 3.566 (16.0); 1.285 (0.5); 0.917 (0.3); 0.897 (0.4); 0.882 (0.6); 0.873 (0.6); 0.860 (0.9); 0.563 (0.4); 0.554 (0.5); 0.545 (0.5); 0.516 (0.7); 0.504 (0.5); 0.456 (0.4); 0.433 (0.6); 0.429 (0.6); 0.412 (0.6); 0.403 (1.2); 0.398 (1.3); 0.389 (0.6); 0.376 (0.8); 0.361 (0.5); 0.030 (1.6)

    Example I-26

    [0352] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.407 (4.3); 7.965 (4.2); 7.473 (1.0); 7.445 (2.2); 7.417 (1.4); 7.298 (2.0); 7.231 (1.2); 7.224 (1.5); 7.203 (0.9); 7.195 (1.5); 7.184 (1.6); 7.178 (1.0); 7.145 (1.4); 7.138 (1.2); 6.667 (0.3); 6.655 (1.7); 6.639 (0.5); 6.629 (2.6); 6.618 (0.5); 6.602 (1.6); 6.590 (0.3); 5.680 (1.1); 5.632 (1.3); 5.009 (1.8); 4.959 (1.5); 3.568 (16.0); 1.286 (0.7); 0.900 (0.4); 0.891 (0.4); 0.882 (0.6); 0.866 (0.7); 0.858 (0.9); 0.847 (0.6); 0.841 (0.8); 0.562 (0.4); 0.544 (0.7); 0.517 (0.6); 0.505 (0.5); 0.432 (0.4); 0.418 (0.5); 0.413 (0.5); 0.408 (0.6); 0.389 (1.6); 0.376 (0.7); 0.366 (1.1); 0.354 (0.6); 0.030 (1.7)

    Example I-27

    [0353] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.166 (7.1); 8.160 (7.2); 7.839 (12.6); 7.764 (2.1); 7.742 (2.0); 7.734 (4.3); 7.712 (4.5); 7.704 (2.5); 7.682 (2.3); 7.644 (1.2); 7.344 (0.5); 7.298 (212.6); 7.200 (0.4); 6.947 (0.9); 6.912 (1.6); 6.903 (1.9); 6.883 (2.6); 6.879 (2.8); 6.857 (1.6); 6.847 (1.6); 6.721 (1.0); 6.713 (1.2); 6.689 (2.5); 6.681 (2.4); 6.662 (2.5); 6.654 (2.7); 6.649 (1.7); 6.626 (2.9); 6.618 (2.5); 6.598 (2.3); 6.589 (2.5); 6.585 (2.6); 6.577 (2.2); 6.557 (2.6); 6.548 (2.1); 6.537 (1.5); 6.529 (1.6); 6.521 (1.5); 6.510 (1.7); 6.501 (1.8); 6.494 (1.9); 6.485 (1.8); 6.469 (1.1); 6.462 (0.9); 6.453 (1.1); 5.583 (3.4); 5.577 (3.2); 5.535 (3.5); 5.529 (3.9); 5.436 (16.0); 4.815 (3.9); 4.810 (4.1); 4.768 (3.4); 4.762 (3.6); 1.582 (186.8); 1.552 (0.7); 1.292 (2.4); 1.206 (0.6); 1.190 (1.4); 1.174 (1.9); 1.153 (4.0); 1.128 (4.4); 1.124 (4.2); 1.109 (3.3); 1.092 (1.2); 1.088 (1.3); 1.076 (0.6); 1.044 (0.7); 0.969 (1.1); 0.941 (3.7); 0.926 (7.4); 0.916 (4.9); 0.909 (5.1); 0.897 (3.1); 0.877 (0.9); 0.234 (0.9); 0.048 (6.8); 0.038 (218.6); 0.027 (8.4); 0.007 (0.6); 0.160 (0.6); 2.587 (0.5)

    Example I-28

    [0354] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.150 (7.4); 8.144 (7.4); 7.833 (12.4); 7.778 (2.2); 7.756 (2.4); 7.748 (4.4); 7.726 (4.4); 7.718 (2.5); 7.696 (2.3); 7.298 (29.2); 6.970 (2.1); 6.945 (2.3); 6.936 (3.9); 6.927 (2.1); 6.925 (2.1); 6.916 (2.5); 6.911 (4.2); 6.902 (4.1); 6.894 (3.2); 6.890 (2.9); 6.877 (2.5); 6.872 (3.8); 6.863 (2.0); 6.845 (4.0); 6.832 (2.2); 6.819 (2.2); 6.806 (3.9); 6.779 (2.0); 6.645 (2.4); 6.637 (2.3); 6.617 (2.5); 6.608 (2.6); 6.604 (2.7); 6.596 (2.3); 6.576 (2.4); 6.567 (2.2); 5.563 (3.4); 5.557 (3.2); 5.516 (3.7); 5.509 (3.8); 5.474 (16.0); 5.337 (2.7); 4.807 (4.0); 4.802 (3.9); 4.760 (3.5); 4.754 (3.5); 4.171 (0.7); 4.147 (0.7); 2.082 (3.0); 1.616 (3.3); 1.602 (4.0); 1.320 (0.9); 1.296 (1.7); 1.272 (0.8); 1.170 (1.0); 1.160 (1.1); 1.157 (1.1); 1.129 (5.8); 1.094 (5.6); 1.090 (5.6); 1.085 (4.4); 1.061 (0.9); 1.053 (1.6); 1.049 (2.3); 1.007 (1.2); 0.996 (1.7); 0.982 (1.3); 0.953 (11.4); 0.943 (7.5); 0.917 (0.7); 0.903 (0.5); 0.047 (1.2); 0.037 (32.1); 0.026 (1.1)

    Example I-29

    [0355] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.308 (8.3); 8.303 (8.1); 7.911 (14.6); 7.785 (2.1); 7.763 (2.3); 7.755 (4.4); 7.733 (4.4); 7.725 (2.4); 7.703 (2.2); 7.643 (0.4); 7.365 (0.4); 7.298 (83.9); 7.005 (1.0); 6.988 (1.3); 6.974 (4.1); 6.956 (5.4); 6.953 (5.0); 6.945 (5.1); 6.937 (6.5); 6.927 (9.1); 6.912 (6.4); 6.905 (3.6); 6.901 (3.3); 6.897 (3.2); 6.881 (2.3); 6.874 (1.9); 6.776 (2.3); 6.768 (2.1); 6.747 (2.5); 6.735 (2.8); 6.727 (2.2); 6.706 (2.4); 6.698 (2.1); 5.586 (4.2); 5.537 (5.0); 5.356 (16.0); 5.049 (4.7); 5.001 (3.9); 4.998 (3.9); 1.586 (42.4); 1.289 (0.6); 1.065 (1.2); 1.041 (2.0); 1.027 (2.4); 1.020 (1.4); 1.004 (3.7); 0.982 (3.1); 0.954 (2.7); 0.933 (4.4); 0.911 (3.0); 0.895 (2.2); 0.873 (1.7); 0.740 (1.2); 0.720 (1.9); 0.708 (1.8); 0.702 (2.2); 0.682 (2.6); 0.661 (1.3); 0.656 (1.2); 0.538 (1.4); 0.533 (1.6); 0.516 (2.4); 0.511 (2.4); 0.493 (2.3); 0.477 (1.8); 0.473 (1.7); 0.456 (0.8); 0.450 (0.8); 0.233 (0.4); 0.105 (0.4); 0.048 (3.6); 0.037 (95.7); 0.026 (3.4); 0.162 (0.4)

    Example I-30

    [0356] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =8.110 (7.3); 8.104 (7.0); 7.845 (0.4); 7.813 (12.3); 7.756 (2.0); 7.734 (2.2); 7.726 (4.0); 7.704 (4.0); 7.696 (2.3); 7.674 (2.0); 7.298 (7.9); 6.914 (1.6); 6.905 (1.9); 6.886 (2.5); 6.881 (2.8); 6.878 (2.7); 6.859 (1.6); 6.850 (1.7); 6.619 (2.2); 6.610 (2.0); 6.591 (2.3); 6.582 (2.4); 6.578 (2.6); 6.569 (2.1); 6.558 (0.5); 6.550 (2.4); 6.541 (3.5); 6.530 (4.2); 6.525 (12.0); 6.497 (11.9); 6.492 (4.2); 6.482 (1.5); 6.369 (0.7); 6.363 (0.5); 6.338 (0.7); 5.527 (0.4); 5.503 (3.1); 5.497 (3.0); 5.460 (16.0); 5.451 (3.8); 5.408 (1.1); 4.701 (3.7); 4.696 (3.7); 4.655 (3.3); 4.649 (3.3); 1.672 (6.5); 1.342 (0.3); 1.301 (2.0); 1.269 (0.3); 1.246 (0.4); 1.220 (0.8); 1.203 (3.3); 1.193 (3.8); 1.183 (7.1); 1.169 (5.7); 1.144 (0.4); 1.100 (0.6); 1.066 (0.6); 1.024 (0.5); 1.020 (0.5); 0.997 (6.0); 0.983 (8.1); 0.974 (4.1); 0.969 (3.8); 0.945 (0.6); 0.938 (1.0); 0.916 (2.2); 0.893 (0.8); 0.045 (0.4); 0.034 (8.7)

    Example IV-1

    [0357] .sup.1H-NMR (499.9 MHz, CDCl.sub.3): =7.758 (2.4); 7.742 (3.8); 7.729 (3.8); 7.713 (2.5); 7.262 (4.0); 6.961 (2.1); 6.959 (2.1); 6.956 (2.4); 6.955 (2.4); 6.943 (4.1); 6.939 (4.5); 6.928 (2.1); 6.926 (2.1); 6.923 (2.3); 6.922 (2.2); 6.892 (3.2); 6.888 (2.8); 6.874 (3.9); 6.872 (4.2); 6.870 (3.8); 6.868 (3.5); 6.854 (3.2); 6.850 (2.9); 6.679 (0.3); 6.633 (0.7); 6.625 (1.4); 6.617 (8.0); 6.608 (1.9); 6.600 (14.5); 6.592 (2.0); 6.583 (7.9); 6.575 (1.5); 6.566 (0.6); 4.458 (0.5); 4.143 (1.2); 4.129 (3.7); 4.115 (3.7); 4.100 (1.3); 2.882 (0.3); 2.041 (16.0); 1.709 (0.3); 1.676 (5.6); 1.665 (15.7); 1.658 (15.5); 1.648 (7.0); 1.614 (0.7); 1.588 (2.8); 1.461 (0.6); 1.427 (5.7); 1.416 (13.2); 1.410 (13.8); 1.399 (4.7); 1.271 (4.3); 1.257 (8.5); 1.243 (4.2); 0.000 (4.2)

    Example IV-2

    [0358] .sup.1H-NMR (499.9 MHz, CDCl.sub.3): =7.735 (1.8); 7.719 (3.0); 7.706 (3.0); 7.690 (2.0); 7.260 (5.6); 6.952 (1.6); 6.951 (1.8); 6.946 (2.3); 6.935 (3.3); 6.930 (4.0); 6.919 (1.8); 6.918 (1.8); 6.915 (2.0); 6.913 (2.0); 6.886 (2.7); 6.881 (2.4); 6.877 (1.4); 6.868 (4.2); 6.866 (4.1); 6.863 (4.2); 6.860 (15.1); 6.848 (4.1); 6.843 (16.0); 6.834 (2.3); 6.827 (1.3); 5.296 (1.5); 4.467 (0.4); 2.890 (0.3); 1.696 (4.4); 1.685 (12.3); 1.678 (12.2); 1.668 (5.7); 1.634 (0.6); 1.558 (4.3); 1.472 (0.4); 1.438 (4.4); 1.428 (10.4); 1.421 (10.9); 1.410 (3.9); 0.000 (5.4)

    Example IV-3

    [0359] .sup.1H-NMR (499.9 MHz, d.sub.6-DMSO): =7.802 (0.4); 7.788 (0.5); 7.782 (2.3); 7.765 (4.2); 7.752 (4.3); 7.741 (0.7); 7.736 (2.3); 7.576 (0.5); 7.560 (0.5); 7.494 (1.2); 7.487 (2.2); 7.477 (16.0); 7.460 (15.7); 7.451 (2.3); 7.444 (1.5); 7.425 (2.7); 7.420 (2.7); 7.403 (3.9); 7.401 (3.9); 7.385 (2.6); 7.380 (2.5); 7.276 (0.4); 7.272 (0.4); 7.260 (0.7); 7.255 (0.7); 7.246 (2.6); 7.242 (2.7); 7.229 (4.7); 7.225 (4.5); 7.212 (2.4); 7.208 (2.2); 5.757 (3.3); 4.426 (0.4); 3.313 (6.5); 2.871 (0.4); 2.519 (1.8); 2.515 (3.8); 2.511 (5.2); 2.508 (3.8); 2.504 (1.8); 1.778 (1.0); 1.771 (0.9); 1.767 (1.0); 1.761 (1.1); 1.751 (0.4); 1.629 (4.4); 1.617 (10.5); 1.610 (12.8); 1.600 (6.7); 1.592 (0.7); 1.581 (1.3); 1.574 (1.2); 1.571 (1.2); 1.566 (1.9); 1.554 (0.5); 1.546 (0.9); 1.511 (6.0); 1.502 (11.6); 1.495 (10.0); 1.483 (3.8); 0.000 (3.6)

    Example IV-4

    [0360] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =7.879 (3.0); 7.857 (3.7); 7.853 (4.7); 7.829 (4.6); 7.825 (4.0); 7.803 (3.2); 7.360 (0.4); 7.340 (1.9); 7.325 (1.2); 7.320 (2.4); 7.300 (20.5); 7.293 (60.0); 7.280 (1.0); 7.040 (2.4); 7.037 (2.5); 7.032 (3.0); 7.011 (4.6); 7.008 (4.1); 7.003 (5.5); 6.985 (2.4); 6.982 (2.3); 6.973 (5.5); 6.965 (3.0); 6.942 (4.5); 6.939 (5.0); 6.935 (4.3); 6.931 (3.9); 6.909 (3.7); 6.901 (3.2); 5.339 (6.8); 4.511 (0.3); 4.479 (0.6); 4.448 (0.3); 4.173 (0.6); 4.150 (0.6); 2.819 (0.5); 2.085 (2.8); 2.043 (0.4); 2.019 (0.4); 1.691 (6.0); 1.672 (15.0); 1.661 (16.0); 1.644 (9.0); 1.609 (1.3); 1.586 (1.8); 1.501 (1.1); 1.444 (8.5); 1.427 (15.7); 1.416 (15.0); 1.397 (6.0); 1.343 (0.5); 1.323 (1.1); 1.299 (2.7); 1.275 (1.0); 0.919 (0.3); 0.110 (0.7); 0.050 (0.8); 0.039 (24.2); 0.028 (1.1)

    Example IV-5

    [0361] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =7.891 (1.5); 7.869 (1.8); 7.864 (2.4); 7.862 (2.4); 7.841 (2.4); 7.836 (2.2); 7.814 (1.6); 7.300 (8.0); 7.114 (0.5); 7.111 (0.4); 7.103 (0.5); 7.088 (0.6); 7.084 (0.5); 7.069 (15.2); 7.057 (0.8); 7.043 (16.0); 7.035 (2.1); 7.032 (2.0); 7.014 (2.3); 7.011 (2.1); 7.006 (2.9); 6.987 (1.1); 6.985 (1.2); 6.975 (2.7); 6.967 (1.5); 6.944 (2.2); 6.941 (2.6); 6.937 (2.3); 6.933 (2.1); 6.911 (1.9); 6.903 (1.6); 4.476 (0.3); 2.085 (1.3); 1.677 (3.0); 1.658 (7.1); 1.647 (8.0); 1.630 (4.5); 1.590 (6.5); 1.573 (0.7); 1.499 (0.6); 1.442 (4.3); 1.425 (7.9); 1.414 (7.5); 1.395 (3.0); 1.323 (0.5); 1.299 (1.0); 1.275 (0.4); 0.039 (10.6); 0.029 (0.5)

    Example IV-6

    [0362] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =7.797 (2.5); 7.771 (4.4); 7.748 (4.4); 7.721 (2.6); 7.300 (8.2); 7.008 (2.5); 7.006 (2.6); 7.001 (3.1); 6.980 (4.6); 6.972 (5.5); 6.951 (2.8); 6.944 (6.5); 6.936 (3.3); 6.913 (5.2); 6.910 (5.3); 6.906 (4.5); 6.881 (4.0); 6.873 (3.5); 6.852 (1.5); 6.837 (3.3); 6.820 (11.1); 6.809 (4.2); 6.802 (5.2); 6.798 (8.1); 6.791 (7.5); 6.771 (9.0); 6.756 (1.3); 6.740 (0.9); 4.557 (0.4); 4.526 (0.6); 4.494 (0.4); 4.197 (0.5); 4.173 (1.5); 4.149 (1.6); 4.125 (0.5); 2.962 (0.5); 2.084 (6.8); 1.830 (0.4); 1.777 (5.6); 1.759 (14.9); 1.747 (16.0); 1.731 (7.9); 1.673 (1.2); 1.599 (4.8); 1.576 (1.1); 1.555 (0.4); 1.518 (6.7); 1.502 (14.5); 1.491 (13.8); 1.472 (4.9); 1.418 (0.4); 1.322 (2.0); 1.298 (4.0); 1.274 (1.9); 0.111 (0.4); 0.049 (0.5); 0.038 (10.9)

    Example IV-7

    [0363] .sup.1H-NMR (499.9 MHz, CDCl.sub.3): =7.820 (0.9); 7.806 (1.1); 7.804 (1.3); 7.790 (1.3); 7.787 (1.2); 7.774 (0.9); 7.437 (0.4); 7.422 (0.4); 7.390 (16.0); 7.259 (2.6); 6.981 (0.7); 6.977 (0.8); 6.964 (1.4); 6.960 (1.5); 6.948 (0.8); 6.944 (0.8); 6.914 (1.0); 6.909 (0.9); 6.895 (1.3); 6.893 (1.4); 6.891 (1.3); 6.889 (1.1); 6.875 (1.1); 6.871 (0.9); 1.639 (1.9); 1.628 (5.1); 1.621 (5.1); 1.611 (2.5); 1.546 (1.2); 1.394 (2.3); 1.383 (4.8); 1.377 (5.2); 1.365 (2.0); 0.000 (2.4)

    Example IV-8

    [0364] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =7.889 (3.0); 7.867 (3.6); 7.862 (4.4); 7.841 (4.3); 7.839 (4.3); 7.834 (3.7); 7.812 (3.1); 7.300 (10.8); 7.268 (0.5); 7.264 (1.3); 7.243 (5.7); 7.213 (25.1); 7.197 (24.5); 7.183 (0.8); 7.168 (5.4); 7.063 (0.8); 7.039 (2.4); 7.036 (2.7); 7.032 (2.9); 7.029 (2.6); 7.010 (4.2); 7.003 (5.0); 6.984 (2.3); 6.982 (2.1); 6.976 (2.9); 6.973 (3.2); 6.970 (4.1); 6.962 (3.0); 6.940 (4.4); 6.936 (4.6); 6.932 (4.0); 6.928 (3.6); 6.906 (3.6); 6.898 (3.1); 6.472 (0.8); 6.443 (0.7); 4.480 (0.4); 2.825 (0.3); 2.048 (2.1); 2.042 (10.3); 2.024 (1.5); 1.696 (6.0); 1.678 (14.4); 1.667 (16.0); 1.649 (8.9); 1.592 (1.2); 1.517 (1.1); 1.459 (8.3); 1.442 (14.3); 1.431 (13.4); 1.412 (5.8); 1.359 (0.4); 1.292 (1.1); 0.049 (0.4); 0.038 (10.5); 0.027 (0.4)

    Example IV-9

    [0365] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =7.806 (2.5); 7.780 (4.3); 7.757 (4.2); 7.731 (2.7); 7.300 (16.3); 7.071 (3.2); 7.054 (3.5); 7.046 (3.7); 7.040 (4.6); 7.028 (3.7); 7.023 (4.7); 7.015 (6.4); 7.006 (3.3); 7.004 (3.4); 6.998 (4.7); 6.985 (4.6); 6.982 (3.8); 6.977 (5.5); 6.959 (2.3); 6.956 (2.4); 6.951 (3.1); 6.948 (3.9); 6.945 (4.7); 6.937 (3.1); 6.926 (0.7); 6.915 (4.7); 6.912 (5.1); 6.908 (4.4); 6.904 (4.2); 6.882 (3.8); 6.874 (3.3); 6.856 (4.5); 6.849 (4.6); 6.835 (0.6); 6.825 (4.1); 6.822 (5.5); 6.818 (4.9); 6.815 (5.2); 6.791 (3.3); 6.784 (3.3); 4.553 (0.4); 4.522 (0.7); 4.490 (0.4); 4.197 (0.8); 4.173 (2.5); 4.149 (2.6); 4.125 (0.9); 2.949 (0.5); 2.084 (11.5); 1.767 (5.8); 1.748 (15.2); 1.737 (16.0); 1.720 (8.1); 1.663 (1.1); 1.598 (9.2); 1.559 (0.9); 1.502 (6.7); 1.485 (14.4); 1.474 (13.8); 1.455 (4.8); 1.322 (3.2); 1.298 (6.6); 1.274 (3.1); 0.049 (0.6); 0.038 (15.1); 0.027 (0.6)

    Example IV-10

    [0366] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =7.625 (1.7); 7.620 (1.2); 7.599 (4.6); 7.577 (4.2); 7.574 (2.9); 7.570 (3.6); 7.549 (2.8); 7.300 (12.2); 6.926 (2.1); 6.924 (1.9); 6.918 (3.0); 6.897 (4.4); 6.891 (10.7); 6.872 (2.0); 6.863 (10.1); 6.854 (3.1); 6.832 (3.4); 6.825 (2.7); 6.745 (0.4); 6.725 (0.4); 6.716 (0.4); 6.697 (0.4); 6.532 (0.7); 6.517 (1.5); 6.513 (1.3); 6.504 (7.2); 6.485 (7.2); 6.474 (7.1); 6.455 (6.8); 6.442 (1.3); 6.427 (0.6); 4.646 (0.6); 4.615 (1.1); 4.583 (0.6); 2.986 (0.5); 2.954 (0.9); 2.922 (0.5); 1.886 (5.8); 1.869 (16.0); 1.857 (15.8); 1.841 (7.2); 1.784 (0.7); 1.584 (5.3); 1.566 (0.7); 1.549 (0.3); 1.509 (7.0); 1.493 (15.2); 1.482 (15.3); 1.463 (5.4); 0.109 (4.2); 0.049 (0.6); 0.038 (13.4); 0.027 (0.5)

    Example IV-11

    [0367] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =7.869 (1.5); 7.848 (1.8); 7.843 (2.2); 7.841 (2.2); 7.821 (2.1); 7.819 (2.2); 7.815 (1.9); 7.793 (1.5); 7.601 (0.4); 7.588 (1.8); 7.554 (16.0); 7.553 (15.2); 7.300 (6.4); 7.041 (1.2); 7.039 (1.2); 7.033 (1.5); 7.031 (1.4); 7.012 (2.2); 7.005 (2.7); 6.986 (1.2); 6.984 (1.2); 6.978 (1.7); 6.976 (1.8); 6.971 (2.3); 6.963 (1.5); 6.941 (2.3); 6.937 (2.5); 6.934 (2.1); 6.929 (2.0); 6.915 (0.6); 6.907 (2.0); 6.900 (1.6); 4.504 (0.4); 4.154 (0.8); 4.130 (0.8); 2.078 (1.5); 2.069 (3.7); 2.054 (1.5); 1.736 (2.8); 1.717 (7.2); 1.706 (7.3); 1.689 (4.1); 1.631 (0.7); 1.517 (0.5); 1.459 (3.9); 1.442 (7.2); 1.431 (7.4); 1.412 (3.0); 1.312 (1.1); 1.295 (0.7); 1.289 (2.2); 1.265 (1.0); 0.039 (6.7); 0.028 (0.4)

    Example IV-12

    [0368] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =7.878 (3.2); 7.856 (3.9); 7.852 (4.7); 7.828 (4.7); 7.824 (4.1); 7.802 (3.3); 7.300 (13.9); 7.262 (0.4); 7.230 (1.5); 7.223 (1.8); 7.198 (29.7); 7.195 (29.2); 7.041 (2.6); 7.038 (2.6); 7.033 (3.0); 7.031 (2.9); 7.012 (4.7); 7.004 (5.6); 6.986 (2.4); 6.983 (2.4); 6.972 (4.7); 6.964 (3.2); 6.942 (4.7); 6.938 (5.2); 6.935 (4.3); 6.930 (3.9); 6.908 (4.0); 6.901 (3.3); 4.524 (0.4); 4.493 (0.7); 4.461 (0.4); 2.899 (0.3); 2.868 (0.6); 2.080 (1.1); 2.058 (1.1); 2.034 (1.1); 1.710 (6.3); 1.691 (15.3); 1.680 (16.0); 1.663 (8.9); 1.605 (1.5); 1.513 (1.1); 1.455 (8.7); 1.438 (15.8); 1.427 (15.4); 1.408 (6.2); 1.355 (0.4); 1.319 (0.5); 1.296 (1.1); 1.272 (0.4); 0.112 (0.4); 0.049 (0.5); 0.039 (14.9); 0.028 (0.7)

    Example IV-13

    [0369] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =7.858 (1.2); 7.837 (1.4); 7.832 (1.7); 7.830 (1.8); 7.808 (1.7); 7.804 (1.6); 7.782 (1.2); 7.624 (0.8); 7.609 (0.8); 7.587 (16.0); 7.424 (0.5); 7.300 (9.3); 7.035 (0.9); 7.032 (1.0); 7.027 (1.1); 7.024 (1.2); 7.006 (1.8); 6.998 (2.2); 6.979 (0.9); 6.977 (1.0); 6.971 (1.2); 6.969 (1.3); 6.962 (1.6); 6.954 (1.2); 6.932 (1.7); 6.928 (1.9); 6.924 (1.7); 6.920 (1.6); 6.898 (1.5); 6.890 (1.3); 4.131 (0.3); 4.107 (0.3); 2.066 (0.7); 2.045 (1.6); 1.725 (2.3); 1.706 (5.5); 1.695 (5.8); 1.677 (3.2); 1.620 (0.7); 1.609 (0.5); 1.515 (0.4); 1.457 (3.2); 1.440 (5.7); 1.429 (5.8); 1.410 (2.3); 1.299 (0.5); 1.276 (0.8); 1.252 (0.4); 0.050 (0.4); 0.040 (9.9); 0.029 (0.5)

    Example IV-14

    [0370] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =7.849 (0.8); 7.827 (1.0); 7.823 (1.2); 7.821 (1.1); 7.801 (1.1); 7.799 (1.1); 7.794 (1.0); 7.773 (0.8); 7.626 (0.7); 7.622 (0.4); 7.603 (0.5); 7.600 (0.7); 7.591 (16.0); 7.300 (5.2); 7.045 (0.7); 7.042 (0.7); 7.037 (0.9); 7.035 (0.8); 7.016 (1.2); 7.008 (1.5); 6.990 (0.7); 6.987 (0.6); 6.982 (0.9); 6.979 (1.0); 6.975 (1.2); 6.968 (0.8); 6.946 (1.2); 6.942 (1.3); 6.938 (1.1); 6.934 (1.0); 6.926 (0.3); 6.912 (1.0); 6.904 (0.8); 4.172 (0.8); 4.148 (0.9); 2.083 (3.9); 1.847 (0.5); 1.839 (0.4); 1.766 (1.6); 1.747 (4.1); 1.736 (3.9); 1.718 (2.1); 1.619 (0.4); 1.557 (0.5); 1.548 (0.5); 1.451 (2.1); 1.433 (3.8); 1.422 (4.0); 1.403 (1.6); 1.321 (1.1); 1.297 (2.2); 1.273 (1.1); 0.037 (5.6)

    Example IV-15

    [0371] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =7.717 (4.4); 7.692 (7.4); 7.666 (5.3); 7.594 (0.3); 7.300 (16.9); 7.270 (5.6); 7.268 (5.3); 7.263 (6.8); 7.242 (4.6); 7.235 (8.7); 7.230 (8.5); 7.224 (4.7); 7.198 (7.5); 7.192 (6.0); 7.152 (0.6); 6.769 (0.5); 6.761 (0.4); 6.742 (0.8); 6.735 (0.6); 6.714 (0.6); 6.707 (0.5); 6.700 (0.8); 6.685 (1.6); 6.672 (8.8); 6.657 (1.9); 6.644 (16.0); 6.630 (1.8); 6.616 (8.5); 6.602 (1.5); 6.588 (0.7); 4.532 (0.4); 4.501 (0.7); 4.469 (0.4); 2.910 (0.5); 2.085 (1.4); 1.782 (0.6); 1.770 (0.6); 1.753 (0.4); 1.732 (5.6); 1.713 (14.3); 1.702 (15.3); 1.685 (8.0); 1.628 (1.1); 1.598 (2.5); 1.537 (0.9); 1.503 (0.6); 1.491 (0.6); 1.479 (6.4); 1.463 (13.7); 1.452 (12.8); 1.433 (4.6); 1.322 (0.7); 1.313 (0.4); 1.298 (1.0); 1.275 (0.4); 1.140 (0.3); 1.114 (0.4); 0.049 (0.6); 0.038 (18.1); 0.027 (0.7)

    Example IV-16

    [0372] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =7.697 (3.6); 7.672 (6.0); 7.645 (4.5); 7.300 (9.1); 7.260 (4.4); 7.254 (5.7); 7.233 (3.7); 7.226 (8.2); 7.223 (7.6); 7.217 (4.0); 7.191 (6.4); 7.184 (5.3); 7.150 (0.5); 7.004 (0.5); 6.996 (0.9); 6.978 (0.7); 6.971 (0.9); 6.948 (0.4); 6.937 (1.3); 6.925 (2.1); 6.909 (16.0); 6.881 (15.8); 6.866 (2.0); 6.853 (1.1); 5.338 (1.8); 4.509 (0.6); 4.477 (0.4); 2.919 (0.4); 2.085 (0.6); 1.801 (0.6); 1.789 (0.6); 1.772 (0.3); 1.751 (4.8); 1.733 (12.0); 1.721 (12.8); 1.705 (6.8); 1.647 (1.0); 1.549 (0.8); 1.538 (0.3); 1.521 (0.5); 1.509 (0.5); 1.491 (5.5); 1.475 (11.4); 1.464 (10.9); 1.445 (3.9); 1.323 (0.5); 1.311 (0.3); 1.298 (0.7); 0.039 (7.1)

    Example IV-17

    [0373] .sup.1H-NMR (499.9 MHz, CDCl.sub.3): =7.632 (2.3); 7.619 (3.1); 7.617 (3.9); 7.604 (3.8); 7.600 (3.0); 7.587 (2.5); 7.262 (5.1); 6.878 (2.0); 6.877 (2.0); 6.873 (2.5); 6.872 (2.3); 6.861 (3.7); 6.856 (4.8); 6.848 (3.7); 6.844 (3.5); 6.841 (2.9); 6.831 (4.1); 6.828 (4.1); 6.827 (3.2); 6.824 (2.8); 6.811 (3.0); 6.806 (2.4); 6.793 (1.2); 6.788 (1.2); 6.777 (1.6); 6.774 (3.2); 6.769 (2.9); 6.758 (2.9); 6.753 (3.3); 6.750 (1.9); 6.739 (1.6); 6.734 (1.6); 6.683 (1.7); 6.679 (1.8); 6.674 (1.9); 6.669 (2.2); 6.667 (2.1); 6.664 (2.0); 6.662 (2.3); 6.659 (2.5); 6.655 (1.9); 6.653 (2.1); 6.650 (1.6); 6.648 (1.4); 6.643 (1.3); 6.639 (1.2); 6.634 (1.1); 1.867 (0.3); 1.833 (5.9); 1.823 (16.0); 1.816 (15.7); 1.806 (7.0); 1.772 (0.6); 1.562 (0.9); 1.551 (0.6); 1.517 (6.9); 1.507 (15.0); 1.500 (15.6); 1.489 (5.7); 1.456 (0.3); 0.000 (5.3)

    Example IV-18

    [0374] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =7.680 (2.0); 7.673 (0.8); 7.653 (4.0); 7.632 (3.7); 7.625 (3.8); 7.603 (2.8); 7.298 (80.7); 6.947 (0.7); 6.935 (2.1); 6.925 (3.0); 6.917 (3.2); 6.907 (5.8); 6.901 (12.1); 6.893 (4.1); 6.882 (6.0); 6.874 (16.0); 6.859 (5.5); 6.850 (6.8); 6.845 (4.5); 6.837 (7.2); 6.825 (2.8); 6.813 (2.6); 1.887 (5.9); 1.869 (15.1); 1.858 (15.2); 1.841 (7.8); 1.784 (0.8); 1.625 (0.8); 1.579 (49.6); 1.568 (8.5); 1.551 (15.1); 1.540 (14.9); 1.522 (5.6); 1.502 (0.4); 1.468 (0.4); 1.291 (1.1); 0.232 (0.3); 0.048 (3.2); 0.038 (83.1); 0.027 (3.0); 0.161 (0.3)

    Example IV-19

    [0375] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =7.628 (1.5); 7.624 (1.1); 7.607 (2.0); 7.602 (4.0); 7.598 (2.2); 7.580 (3.8); 7.577 (2.4); 7.573 (3.0); 7.552 (2.5); 7.298 (17.5); 6.926 (1.7); 6.924 (1.7); 6.918 (2.3); 6.916 (2.5); 6.898 (3.2); 6.890 (10.0); 6.872 (1.6); 6.863 (7.4); 6.853 (2.6); 6.831 (2.9); 6.823 (2.2); 6.746 (0.4); 6.693 (0.4); 6.670 (0.4); 6.539 (0.5); 6.533 (1.8); 6.522 (6.2); 6.515 (16.0); 6.490 (15.6); 6.483 (6.4); 6.472 (1.9); 5.337 (3.9); 4.625 (0.4); 2.974 (0.3); 1.898 (5.3); 1.880 (13.7); 1.869 (13.4); 1.852 (6.8); 1.837 (0.5); 1.795 (0.6); 1.585 (11.4); 1.557 (0.4); 1.548 (0.4); 1.521 (6.3); 1.505 (12.9); 1.494 (13.3); 1.476 (5.0); 1.422 (0.4); 0.048 (0.6); 0.037 (18.4); 0.026 (0.6)

    Example IV-20

    [0376] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =7.816 (2.1); 7.793 (3.7); 7.789 (4.2); 7.768 (4.2); 7.764 (3.9); 7.740 (2.2); 7.298 (29.1); 7.007 (2.4); 7.004 (2.5); 6.999 (2.9); 6.996 (3.0); 6.977 (7.2); 6.972 (4.4); 6.970 (5.7); 6.960 (3.8); 6.944 (9.0); 6.936 (3.9); 6.929 (5.7); 6.925 (4.0); 6.911 (10.1); 6.903 (4.3); 6.894 (5.4); 6.881 (4.1); 6.873 (3.4); 6.861 (5.1); 6.847 (5.4); 6.835 (5.2); 6.830 (3.5); 6.821 (5.4); 6.816 (3.3); 6.804 (3.1); 6.790 (2.8); 5.338 (3.3); 4.540 (0.5); 4.509 (0.6); 4.477 (0.3); 2.906 (0.4); 1.809 (0.3); 1.756 (6.1); 1.737 (15.0); 1.726 (16.0); 1.709 (8.5); 1.652 (1.1); 1.585 (19.9); 1.553 (1.0); 1.496 (6.8); 1.480 (14.6); 1.469 (13.9); 1.450 (4.8); 1.291 (0.5); 0.048 (1.0); 0.037 (30.1); 0.026 (1.2)

    Example IV-21

    [0377] .sup.1H-NMR (499.9 MHz, CDCl.sub.3): =7.641 (4.3); 7.625 (6.5); 7.610 (4.6); 7.529 (0.4); 7.260 (26.2); 7.211 (5.1); 7.207 (5.9); 7.194 (4.6); 7.191 (5.8); 7.174 (6.4); 7.170 (5.2); 7.154 (6.1); 7.151 (5.4); 7.133 (0.3); 7.116 (0.3); 7.106 (0.8); 7.101 (0.4); 7.097 (0.3); 7.091 (0.8); 7.081 (0.4); 7.076 (0.4); 7.025 (1.3); 7.018 (2.2); 7.009 (16.0); 6.993 (15.8); 6.983 (2.2); 6.976 (1.1); 4.487 (0.5); 4.468 (0.9); 4.449 (0.5); 4.143 (0.8); 4.129 (2.4); 4.115 (2.4); 4.100 (0.8); 3.214 (3.7); 2.955 (2.6); 2.899 (0.4); 2.883 (2.4); 2.861 (0.4); 2.817 (0.5); 2.044 (10.6); 1.701 (5.3); 1.690 (15.1); 1.683 (14.8); 1.673 (6.5); 1.638 (0.7); 1.543 (15.0); 1.477 (0.6); 1.443 (5.5); 1.433 (13.0); 1.426 (13.4); 1.415 (4.5); 1.273 (2.9); 1.259 (5.9); 1.244 (2.8); 1.190 (11.4); 0.882 (0.5); 0.006 (0.9); 0.000 (25.9); 0.007 (1.2)

    Example V-01

    [0378] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =7.813 (0.3); 7.785 (0.5); 7.763 (0.5); 7.737 (0.4); 7.609 (3.1); 7.586 (4.2); 7.582 (5.2); 7.560 (4.3); 7.556 (6.3); 7.532 (3.5); 7.300 (14.5); 7.017 (0.3); 7.014 (0.3); 7.009 (0.4); 7.006 (0.4); 6.988 (0.7); 6.980 (0.8); 6.970 (0.4); 6.962 (0.6); 6.949 (3.1); 6.941 (4.3); 6.926 (3.2); 6.918 (4.5); 6.912 (4.5); 6.897 (6.4); 6.889 (5.4); 6.878 (1.0); 6.865 (5.6); 6.856 (5.4); 6.832 (4.1); 6.824 (3.3); 6.738 (1.1); 6.723 (2.0); 6.710 (10.1); 6.695 (2.5); 6.683 (16.0); 6.670 (3.3); 6.655 (9.9); 6.642 (3.9); 6.628 (1.1); 6.614 (1.3); 6.600 (0.4); 4.502 (0.4); 3.809 (1.5); 3.800 (1.0); 3.795 (1.4); 3.787 (3.8); 3.779 (1.4); 3.773 (1.0); 3.765 (1.6); 3.255 (0.8); 3.165 (7.9); 3.148 (11.8); 3.083 (14.4); 3.066 (9.8); 2.921 (0.3); 1.915 (1.6); 1.904 (1.6); 1.893 (4.6); 1.886 (1.2); 1.881 (1.6); 1.871 (1.5); 1.728 (0.9); 1.709 (2.1); 1.698 (2.2); 1.681 (1.2); 1.591 (7.3); 1.475 (1.0); 1.459 (2.1); 1.447 (1.9); 1.428 (0.8); 1.296 (6.0); 1.262 (2.4); 1.230 (2.8); 1.200 (0.4); 1.183 (0.4); 1.157 (0.7); 1.136 (3.5); 1.126 (4.3); 1.108 (4.6); 1.098 (9.8); 1.068 (8.4); 1.046 (1.5); 0.962 (2.2); 0.942 (5.1); 0.933 (2.9); 0.925 (7.0); 0.913 (6.9); 0.905 (4.6); 0.897 (6.7); 0.887 (5.9); 0.867 (2.4); 0.861 (3.9); 0.840 (1.2); 0.050 (0.7); 0.039 (20.1); 0.028 (0.7)

    Example V-02

    [0379] .sup.1H-NMR (499.9 MHz, CDCl.sub.3): =7.527 (2.3); 7.514 (2.8); 7.510 (4.3); 7.497 (4.4); 7.493 (3.0); 7.480 (2.5); 7.257 (4.1); 6.944 (0.6); 6.929 (0.6); 6.921 (1.2); 6.914 (2.2); 6.905 (14.3); 6.889 (16.0); 6.880 (3.0); 6.873 (4.6); 6.868 (4.4); 6.858 (2.0); 6.856 (1.9); 6.853 (2.2); 6.851 (2.1); 6.833 (2.9); 6.828 (2.4); 6.815 (3.4); 6.812 (3.7); 6.810 (3.3); 6.808 (3.0); 6.795 (2.9); 6.790 (2.5); 4.465 (0.5); 4.142 (0.3); 4.128 (1.1); 4.114 (1.1); 4.100 (0.4); 3.129 (6.3); 3.119 (7.8); 3.024 (8.7); 3.014 (7.5); 2.888 (0.4); 2.040 (4.6); 1.554 (2.2); 1.271 (2.2); 1.257 (5.6); 1.242 (2.0); 1.223 (0.7); 1.101 (0.6); 1.088 (2.6); 1.081 (3.2); 1.071 (3.3); 1.065 (6.0); 1.061 (4.4); 1.049 (4.4); 1.044 (4.2); 1.032 (1.2); 0.931 (1.7); 0.918 (2.7); 0.913 (2.1); 0.901 (2.8); 0.897 (3.1); 0.887 (3.9); 0.881 (3.2); 0.874 (3.4); 0.872 (4.2); 0.865 (3.7); 0.858 (2.6); 0.853 (2.7); 0.850 (3.2); 0.837 (1.9); 0.000 (4.6)

    Example V-03

    [0380] .sup.1H-NMR (499.9 MHz, CDCl.sub.3): =7.522 (2.5); 7.509 (3.0); 7.505 (4.7); 7.492 (4.8); 7.488 (3.5); 7.475 (3.1); 7.471 (0.8); 7.464 (0.4); 7.458 (0.6); 7.454 (0.3); 7.257 (15.2); 7.093 (0.4); 7.078 (0.4); 7.068 (1.3); 7.061 (2.2); 7.052 (16.0); 7.037 (16.0); 7.028 (2.7); 7.021 (1.5); 6.909 (0.3); 6.907 (0.3); 6.891 (2.4); 6.889 (2.3); 6.886 (2.4); 6.884 (2.3); 6.881 (0.9); 6.874 (3.9); 6.869 (4.4); 6.858 (2.1); 6.856 (2.1); 6.853 (2.4); 6.851 (2.3); 6.847 (0.8); 6.841 (0.6); 6.833 (3.2); 6.828 (3.0); 6.815 (3.7); 6.812 (4.1); 6.810 (3.7); 6.807 (3.5); 6.794 (3.2); 6.789 (2.8); 5.295 (4.1); 4.466 (0.4); 3.130 (6.6); 3.120 (8.2); 3.108 (0.9); 3.097 (1.4); 3.086 (1.0); 3.029 (0.8); 3.022 (9.3); 3.012 (7.9); 2.998 (0.8); 2.988 (0.6); 1.851 (0.3); 1.528 (8.2); 1.332 (0.3); 1.326 (0.4); 1.321 (0.4); 1.320 (0.4); 1.310 (0.5); 1.306 (0.5); 1.300 (0.6); 1.258 (4.3); 1.235 (0.9); 1.223 (1.0); 1.213 (0.6); 1.210 (0.7); 1.200 (0.6); 1.190 (0.7); 1.185 (0.7); 1.177 (0.6); 1.172 (0.3); 1.166 (0.5); 1.163 (0.4); 1.159 (0.4); 1.153 (0.4); 1.149 (0.4); 1.145 (0.4); 1.135 (0.4); 1.123 (0.4); 1.120 (0.5); 1.117 (0.5); 1.113 (0.4); 1.101 (0.6); 1.088 (2.9); 1.081 (3.4); 1.070 (3.9); 1.065 (6.8); 1.060 (5.0); 1.048 (5.1); 1.044 (4.7); 1.032 (1.6); 1.023 (0.6); 1.012 (0.6); 1.008 (0.5); 1.002 (0.4); 0.997 (0.4); 0.994 (0.3); 0.933 (1.8); 0.920 (2.8); 0.915 (2.3); 0.901 (3.0); 0.899 (3.1); 0.888 (4.1); 0.882 (3.2); 0.875 (3.6); 0.872 (4.5); 0.866 (4.0); 0.859 (2.8); 0.854 (2.9); 0.850 (3.5); 0.837 (2.2); 0.006 (0.6); 0.000 (16.6); 0.007 (0.9)

    Example V-04

    [0381] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =7.732 (0.5); 7.710 (0.5); 7.312 (3.0); 7.300 (15.0); 7.290 (3.6); 7.285 (4.5); 7.264 (4.3); 7.255 (3.2); 7.247 (0.8); 7.234 (2.7); 6.964 (0.5); 6.961 (0.5); 6.956 (0.5); 6.948 (0.4); 6.935 (0.5); 6.926 (0.4); 6.910 (0.5); 6.894 (2.6); 6.886 (4.1); 6.876 (1.9); 6.868 (4.8); 6.859 (6.3); 6.852 (4.9); 6.844 (6.8); 6.836 (3.8); 6.831 (4.3); 6.823 (4.6); 6.818 (4.2); 6.808 (2.0); 6.803 (1.3); 6.789 (2.0); 6.777 (8.1); 6.757 (8.2); 6.745 (8.0); 6.726 (7.7); 6.714 (1.8); 6.700 (1.0); 6.585 (0.4); 6.574 (0.3); 6.567 (0.4); 6.558 (0.3); 6.551 (0.3); 6.534 (0.4); 6.524 (0.4); 6.505 (0.4); 6.494 (0.6); 6.476 (0.5); 6.464 (0.4); 4.647 (0.4); 4.616 (0.8); 4.584 (0.4); 3.027 (0.4); 2.991 (11.8); 2.976 (16.0); 2.955 (0.8); 2.923 (0.5); 2.901 (13.0); 2.886 (9.4); 2.661 (4.0); 2.629 (0.9); 2.048 (2.4); 1.593 (1.6); 1.294 (0.5); 1.274 (0.6); 1.263 (2.3); 1.252 (1.8); 1.244 (3.3); 1.238 (2.8); 1.225 (3.1); 1.220 (4.1); 1.206 (4.7); 1.201 (4.1); 1.195 (2.3); 1.190 (2.3); 1.182 (5.4); 1.175 (1.6); 1.167 (3.1); 1.162 (4.6); 1.158 (2.9); 1.144 (2.5); 1.135 (3.8); 1.131 (3.6); 1.117 (2.8); 1.113 (2.9); 1.081 (2.9); 1.060 (5.7); 1.042 (6.4); 1.037 (5.6); 1.030 (5.1); 1.022 (3.7); 1.015 (4.8); 1.004 (6.7); 0.995 (1.9); 0.984 (2.4); 0.978 (3.4); 0.957 (1.1); 0.417 (0.4); 0.195 (0.4); 0.050 (0.6); 0.039 (15.8); 0.028 (0.6)

    Example V-05

    [0382] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =7.645 (0.5); 7.635 (3.3); 7.613 (3.9); 7.608 (5.7); 7.586 (5.7); 7.580 (4.4); 7.558 (3.6); 7.300 (22.5); 7.245 (3.6); 7.242 (3.7); 7.224 (1.1); 7.221 (1.1); 7.189 (30.8); 7.186 (31.4); 7.014 (0.4); 7.006 (0.4); 6.974 (0.5); 6.959 (2.8); 6.957 (2.8); 6.951 (3.4); 6.949 (3.5); 6.931 (5.1); 6.922 (6.2); 6.904 (3.1); 6.902 (3.4); 6.898 (6.0); 6.891 (3.9); 6.868 (5.1); 6.865 (5.5); 6.860 (4.1); 6.857 (4.2); 6.835 (4.2); 6.827 (3.4); 4.493 (0.6); 4.461 (0.3); 3.353 (13.6); 3.335 (16.0); 3.137 (11.5); 3.120 (10.1); 2.868 (0.5); 2.656 (2.6); 2.138 (0.4); 2.047 (3.6); 1.713 (0.4); 1.694 (0.8); 1.683 (0.8); 1.665 (0.5); 1.456 (0.5); 1.439 (0.8); 1.428 (0.8); 1.409 (0.4); 1.295 (0.7); 1.262 (0.4); 1.048 (1.1); 1.027 (2.3); 1.014 (2.7); 1.002 (2.4); 0.999 (2.8); 0.994 (3.0); 0.991 (3.4); 0.988 (3.4); 0.985 (3.1); 0.977 (1.8); 0.973 (1.8); 0.961 (1.9); 0.958 (2.0); 0.939 (2.0); 0.916 (3.5); 0.899 (4.3); 0.877 (5.8); 0.871 (7.9); 0.867 (8.9); 0.860 (7.4); 0.851 (2.2); 0.845 (2.8); 0.838 (6.7); 0.824 (6.4); 0.810 (4.4); 0.803 (8.3); 0.791 (3.6); 0.783 (2.9); 0.765 (3.5); 0.744 (1.3); 0.050 (0.6); 0.039 (23.9); 0.028 (1.4)

    Example V-06

    [0383] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =7.589 (4.0); 7.567 (4.6); 7.561 (7.5); 7.540 (7.3); 7.534 (5.2); 7.512 (4.3); 7.300 (38.5); 7.141 (4.2); 7.124 (4.5); 7.116 (4.8); 7.110 (5.8); 7.098 (4.8); 7.093 (5.8); 7.085 (5.6); 7.068 (5.2); 6.951 (3.2); 6.949 (3.5); 6.943 (4.0); 6.940 (4.1); 6.923 (5.9); 6.914 (7.9); 6.903 (6.9); 6.896 (12.5); 6.887 (7.6); 6.871 (8.7); 6.865 (13.6); 6.853 (5.4); 6.840 (5.0); 6.832 (7.6); 6.823 (4.2); 4.523 (0.4); 3.691 (0.6); 3.205 (10.5); 3.188 (13.8); 3.085 (16.0); 3.068 (12.3); 3.027 (0.8); 2.951 (0.4); 2.800 (0.4); 2.655 (11.4); 2.085 (0.6); 2.047 (12.5); 1.588 (10.7); 1.299 (0.7); 1.263 (0.5); 1.188 (0.5); 1.167 (4.0); 1.157 (5.3); 1.138 (5.5); 1.129 (12.3); 1.100 (11.8); 1.077 (1.8); 0.998 (2.8); 0.977 (5.4); 0.953 (9.2); 0.933 (4.3); 0.927 (6.6); 0.916 (8.4); 0.905 (2.6); 0.897 (2.6); 0.889 (4.4); 0.869 (1.5); 0.050 (1.4); 0.039 (41.3); 0.029 (1.8)

    Example V-07

    [0384] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =7.640 (3.5); 7.618 (4.0); 7.613 (6.2); 7.591 (6.1); 7.585 (4.5); 7.564 (3.7); 7.353 (0.5); 7.350 (0.5); 7.340 (1.3); 7.332 (0.4); 7.329 (0.4); 7.328 (0.4); 7.326 (0.4); 7.325 (0.4); 7.321 (0.5); 7.319 (0.5); 7.300 (18.3); 7.287 (66.6); 7.274 (1.2); 7.269 (0.4); 7.267 (0.4); 7.002 (0.4); 6.994 (0.3); 6.959 (2.7); 6.957 (2.8); 6.951 (3.4); 6.948 (3.3); 6.930 (5.0); 6.922 (6.2); 6.904 (2.9); 6.897 (6.4); 6.890 (4.0); 6.867 (5.3); 6.865 (5.8); 6.860 (4.5); 6.856 (4.4); 6.834 (4.3); 6.826 (3.5); 4.479 (0.4); 3.370 (0.4); 3.351 (13.6); 3.333 (16.0); 3.160 (0.4); 3.134 (12.4); 3.116 (10.9); 2.827 (0.5); 2.819 (0.5); 2.654 (0.9); 2.046 (1.0); 1.293 (0.8); 1.025 (1.1); 1.006 (2.1); 0.991 (2.5); 0.978 (2.5); 0.975 (3.0); 0.971 (3.3); 0.967 (3.7); 0.965 (3.6); 0.949 (2.4); 0.946 (2.6); 0.932 (1.6); 0.923 (2.3); 0.900 (3.8); 0.883 (4.3); 0.862 (5.8); 0.853 (7.5); 0.847 (8.9); 0.838 (7.3); 0.817 (5.7); 0.803 (7.6); 0.792 (4.4); 0.785 (7.1); 0.773 (4.2); 0.764 (2.7); 0.757 (1.7); 0.746 (3.3); 0.725 (1.3); 0.711 (0.5); 0.050 (0.3); 0.039 (17.5); 0.029 (1.0)

    Example V-08

    [0385] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =7.637 (0.8); 7.615 (1.0); 7.609 (1.5); 7.588 (1.4); 7.582 (1.1); 7.560 (0.9); 7.449 (0.3); 7.438 (0.4); 7.426 (16.0); 7.300 (4.6); 6.958 (0.6); 6.955 (0.6); 6.949 (0.8); 6.947 (0.8); 6.929 (1.2); 6.920 (1.5); 6.902 (0.7); 6.896 (1.5); 6.889 (0.9); 6.866 (1.3); 6.863 (1.3); 6.858 (1.0); 6.855 (1.0); 6.833 (1.0); 6.825 (0.8); 3.349 (3.3); 3.332 (3.8); 3.131 (2.9); 3.114 (2.6); 2.654 (0.5); 2.046 (8.1); 1.005 (0.5); 0.990 (0.6); 0.977 (0.6); 0.974 (0.7); 0.969 (0.8); 0.966 (0.9); 0.963 (0.8); 0.948 (0.6); 0.945 (0.6); 0.930 (0.4); 0.922 (0.5); 0.900 (0.9); 0.883 (1.0); 0.861 (1.4); 0.852 (1.8); 0.846 (2.0); 0.837 (1.7); 0.820 (1.0); 0.816 (1.3); 0.805 (1.5); 0.802 (1.7); 0.791 (1.0); 0.784 (1.6); 0.772 (0.9); 0.763 (0.6); 0.756 (0.4); 0.745 (0.8); 0.039 (4.7)

    Example V-09

    [0386] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =7.644 (2.0); 7.616 (3.7); 7.595 (3.6); 7.589 (2.6); 7.567 (2.1); 7.300 (13.5); 7.265 (0.7); 7.240 (1.7); 7.211 (19.4); 7.206 (19.3); 7.177 (1.7); 6.961 (1.7); 6.959 (1.6); 6.953 (2.1); 6.951 (2.0); 6.933 (3.1); 6.924 (3.9); 6.901 (3.8); 6.895 (3.2); 6.870 (3.5); 6.868 (3.6); 6.862 (3.0); 6.838 (2.5); 6.829 (2.1); 3.369 (8.1); 3.352 (9.3); 3.163 (0.4); 3.145 (7.4); 3.127 (6.6); 2.858 (0.4); 2.846 (0.4); 2.654 (2.0); 2.084 (0.6); 2.046 (16.0); 1.730 (0.4); 1.702 (0.4); 1.298 (0.6); 1.037 (0.7); 1.016 (1.5); 1.001 (1.7); 0.985 (1.9); 0.978 (2.4); 0.975 (2.3); 0.961 (1.3); 0.945 (1.1); 0.927 (1.3); 0.904 (2.2); 0.887 (2.8); 0.865 (3.6); 0.858 (4.7); 0.852 (5.4); 0.845 (4.5); 0.825 (4.4); 0.810 (5.2); 0.799 (2.7); 0.792 (4.3); 0.779 (2.5); 0.771 (1.7); 0.753 (2.1); 0.732 (0.8); 0.038 (13.8)

    Example V-10

    [0387] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =7.591 (3.8); 7.568 (4.9); 7.563 (7.5); 7.541 (7.6); 7.535 (5.2); 7.514 (4.3); 7.300 (26.4); 6.952 (3.3); 6.949 (3.6); 6.943 (4.6); 6.940 (5.1); 6.923 (7.1); 6.914 (8.7); 6.893 (12.2); 6.885 (11.8); 6.878 (6.7); 6.875 (7.3); 6.870 (7.8); 6.867 (8.8); 6.856 (15.2); 6.844 (6.4); 6.838 (9.3); 6.830 (7.6); 6.827 (7.7); 6.822 (9.1); 6.813 (2.0); 6.807 (2.1); 6.790 (1.7); 3.214 (11.0); 3.197 (14.3); 3.084 (16.0); 3.067 (12.7); 3.026 (0.4); 2.656 (5.4); 2.047 (10.9); 1.692 (0.5); 1.670 (0.4); 1.295 (0.9); 1.173 (4.8); 1.167 (5.8); 1.137 (15.2); 1.108 (15.5); 1.087 (1.5); 1.017 (3.3); 0.996 (5.6); 0.988 (3.5); 0.963 (10.8); 0.936 (9.3); 0.925 (5.2); 0.911 (3.2); 0.907 (3.0); 0.898 (4.3); 0.877 (1.8); 0.050 (0.9); 0.039 (26.8); 0.028 (1.1)

    Example V-11

    [0388] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =7.655 (0.4); 7.632 (0.7); 7.604 (1.2); 7.583 (0.9); 7.579 (1.3); 7.549 (5.6); 7.548 (5.4); 7.373 (0.4); 7.300 (10.9); 6.960 (0.5); 6.951 (0.8); 6.945 (0.7); 6.937 (0.8); 6.928 (0.8); 6.923 (0.9); 6.918 (0.8); 6.902 (1.2); 6.894 (0.9); 6.871 (1.3); 6.862 (1.4); 6.839 (1.1); 6.831 (0.9); 6.812 (0.4); 5.589 (0.4); 5.285 (0.4); 5.206 (0.4); 3.793 (0.4); 3.690 (0.4); 3.381 (0.6); 3.367 (2.3); 3.350 (2.9); 3.143 (2.1); 3.125 (1.9); 3.065 (0.3); 3.022 (0.6); 2.823 (0.3); 2.806 (0.5); 2.788 (0.3); 2.773 (0.7); 2.759 (0.3); 2.691 (2.4); 2.675 (0.5); 2.641 (16.0); 2.624 (0.8); 2.590 (0.7); 2.582 (0.4); 2.045 (8.9); 1.686 (0.4); 1.315 (1.0); 1.312 (0.9); 1.294 (0.4); 1.067 (0.4); 1.047 (0.6); 1.031 (0.5); 1.021 (0.6); 1.007 (0.7); 0.980 (0.5); 0.948 (0.4); 0.925 (0.6); 0.908 (0.9); 0.887 (2.1); 0.882 (2.2); 0.867 (0.7); 0.862 (1.1); 0.847 (1.8); 0.822 (1.1); 0.816 (1.0); 0.802 (0.6); 0.795 (0.6); 0.777 (0.6); 0.037 (11.4); 0.027 (0.6)

    Example V-12

    [0389] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =7.647 (1.6); 7.626 (1.8); 7.620 (2.8); 7.598 (2.8); 7.592 (2.0); 7.571 (1.7); 7.300 (8.0); 7.108 (0.5); 7.082 (0.5); 7.071 (0.5); 7.059 (16.0); 7.048 (0.7); 7.045 (0.7); 7.033 (15.9); 6.961 (1.2); 6.958 (1.3); 6.952 (1.5); 6.949 (1.5); 6.931 (2.2); 6.923 (2.8); 6.905 (1.3); 6.898 (3.0); 6.894 (2.0); 6.891 (1.7); 6.868 (2.4); 6.865 (2.6); 6.861 (2.0); 6.857 (2.0); 6.835 (2.1); 6.827 (1.8); 3.350 (6.4); 3.333 (7.6); 3.135 (5.6); 3.118 (4.9); 2.657 (0.4); 1.019 (0.5); 1.017 (0.6); 0.998 (1.1); 0.983 (1.3); 0.979 (1.0); 0.971 (1.2); 0.968 (1.3); 0.963 (1.5); 0.959 (1.7); 0.957 (1.6); 0.954 (1.4); 0.943 (1.0); 0.940 (1.0); 0.928 (0.8); 0.925 (0.8); 0.911 (1.0); 0.889 (1.8); 0.872 (2.1); 0.850 (2.9); 0.842 (3.8); 0.837 (4.1); 0.829 (3.5); 0.814 (1.2); 0.808 (3.8); 0.794 (4.5); 0.780 (2.1); 0.773 (3.6); 0.761 (1.7); 0.753 (1.2); 0.748 (0.7); 0.735 (1.6); 0.714 (0.6); 0.039 (8.3); 0.028 (0.4)

    Example V-13

    [0390] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =7.579 (1.4); 7.438 (0.8); 7.300 (1.8); 6.860 (0.4); 3.355 (0.4); 3.337 (0.5); 3.130 (0.4); 3.113 (0.4); 2.562 (16.0); 2.035 (1.7); 1.305 (0.4); 1.302 (0.4); 0.034 (1.9)

    Example V-14

    [0391] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =7.538 (2.1); 7.512 (4.7); 7.485 (3.2); 7.300 (11.7); 7.199 (2.5); 7.197 (2.3); 7.193 (3.2); 7.191 (3.0); 7.172 (2.0); 7.164 (7.4); 7.158 (2.3); 7.138 (0.7); 7.131 (3.7); 7.124 (3.0); 7.111 (0.3); 6.984 (0.8); 6.971 (1.3); 6.956 (8.6); 6.930 (8.8); 6.915 (1.3); 6.903 (0.8); 3.682 (0.3); 3.170 (3.4); 3.153 (4.7); 3.063 (5.7); 3.046 (4.4); 3.026 (0.6); 2.662 (11.0); 2.047 (16.0); 2.030 (0.4); 1.135 (1.2); 1.128 (1.6); 1.099 (5.0); 1.070 (4.9); 1.052 (0.5); 0.992 (1.1); 0.972 (2.3); 0.943 (4.5); 0.923 (1.4); 0.916 (2.4); 0.907 (2.2); 0.891 (1.2); 0.880 (1.5); 0.859 (0.7); 0.038 (11.9); 0.027 (0.7)

    Example V-15

    [0392] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =7.646 (0.5); 7.620 (0.4); 7.599 (0.5); 7.592 (0.6); 7.563 (4.2); 7.538 (9.1); 7.510 (6.0); 7.378 (0.4); 7.367 (0.5); 7.300 (58.7); 7.235 (0.5); 7.204 (5.0); 7.197 (6.3); 7.177 (4.1); 7.169 (15.0); 7.163 (3.9); 7.136 (7.0); 7.130 (5.1); 6.740 (0.9); 6.726 (1.6); 6.713 (8.2); 6.698 (2.0); 6.686 (13.2); 6.673 (1.7); 6.658 (7.5); 6.645 (1.2); 6.631 (0.4); 5.340 (1.6); 3.686 (0.6); 3.404 (0.4); 3.388 (0.4); 3.160 (6.7); 3.143 (9.7); 3.075 (11.5); 3.058 (7.8); 3.028 (0.5); 2.658 (16.0); 2.048 (0.5); 1.891 (0.3); 1.777 (0.5); 1.756 (0.5); 1.739 (0.5); 1.692 (0.5); 1.631 (0.5); 1.607 (0.4); 1.552 (0.3); 1.472 (0.4); 1.356 (0.4); 1.294 (1.0); 1.268 (0.4); 1.221 (0.3); 1.182 (0.7); 1.119 (3.6); 1.089 (10.8); 1.060 (9.8); 1.042 (0.7); 0.971 (2.5); 0.951 (4.5); 0.929 (5.1); 0.921 (5.9); 0.910 (3.0); 0.902 (4.1); 0.892 (5.2); 0.879 (1.7); 0.865 (2.6); 0.844 (0.8); 0.050 (2.4); 0.039 (62.2); 0.028 (2.1)

    Example V-16

    [0393] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =7.310 (3.0); 7.298 (51.9); 7.288 (3.5); 7.283 (4.2); 7.273 (1.1); 7.268 (2.2); 7.260 (4.9); 7.253 (4.6); 7.243 (2.3); 7.240 (2.5); 7.236 (2.8); 7.232 (4.3); 7.227 (2.8); 7.224 (2.4); 7.220 (2.4); 7.215 (2.1); 7.212 (2.4); 7.208 (2.2); 7.199 (2.0); 7.192 (1.8); 7.184 (1.8); 6.970 (1.9); 6.962 (2.0); 6.943 (2.2); 6.938 (3.8); 6.930 (3.5); 6.911 (3.5); 6.903 (3.8); 6.898 (2.2); 6.892 (2.6); 6.884 (4.1); 6.879 (3.1); 6.870 (4.9); 6.864 (3.6); 6.856 (5.2); 6.851 (5.9); 6.846 (7.0); 6.837 (3.0); 6.829 (3.1); 6.820 (5.7); 6.810 (1.7); 3.785 (0.8); 3.777 (0.3); 3.253 (0.8); 3.034 (12.1); 3.018 (16.0); 2.926 (11.4); 2.910 (8.6); 2.655 (0.9); 1.914 (0.3); 1.892 (0.9); 1.582 (16.3); 1.295 (8.2); 1.279 (4.5); 1.266 (6.0); 1.252 (3.9); 1.243 (4.6); 1.235 (4.2); 1.229 (3.8); 1.218 (4.8); 1.192 (1.7); 1.188 (1.7); 1.181 (0.9); 1.173 (1.1); 1.164 (2.4); 1.160 (4.1); 1.156 (2.8); 1.147 (1.4); 1.137 (2.5); 1.133 (4.9); 1.128 (3.6); 1.114 (3.3); 1.110 (3.3); 1.085 (0.9); 1.072 (9.6); 1.040 (9.6); 1.015 (3.7); 1.007 (3.4); 0.919 (1.8); 0.888 (2.0); 0.865 (1.3); 0.049 (1.5); 0.038 (53.0); 0.027 (2.1)

    Example V-17

    [0394] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =7.504 (0.4); 7.481 (2.8); 7.455 (5.2); 7.442 (2.8); 7.429 (2.8); 7.416 (5.1); 7.390 (2.5); 7.329 (2.6); 7.307 (3.7); 7.298 (25.0); 7.281 (4.2); 7.273 (3.3); 7.260 (1.0); 7.252 (2.3); 6.962 (2.9); 6.947 (0.8); 6.937 (3.3); 6.928 (5.3); 6.903 (5.7); 6.894 (5.4); 6.886 (4.7); 6.880 (2.7); 6.875 (4.4); 6.872 (5.0); 6.870 (4.9); 6.857 (5.9); 6.852 (6.5); 6.848 (7.9); 6.840 (3.3); 6.830 (3.5); 6.822 (6.8); 6.812 (1.9); 3.043 (12.5); 3.027 (16.0); 2.929 (11.4); 2.913 (8.7); 2.656 (0.8); 1.590 (2.7); 1.383 (0.4); 1.307 (4.1); 1.295 (7.7); 1.289 (6.7); 1.276 (6.0); 1.262 (4.5); 1.252 (5.1); 1.245 (4.5); 1.237 (1.5); 1.228 (5.4); 1.204 (1.9); 1.199 (2.0); 1.184 (1.4); 1.180 (2.0); 1.172 (4.0); 1.168 (3.2); 1.161 (1.8); 1.157 (1.7); 1.149 (2.6); 1.144 (4.9); 1.140 (3.8); 1.126 (3.6); 1.122 (3.5); 1.081 (9.9); 1.053 (9.4); 1.047 (9.6); 1.023 (4.0); 1.016 (3.7); 0.983 (0.7); 0.964 (0.8); 0.934 (1.1); 0.918 (2.0); 0.911 (1.8); 0.888 (2.1); 0.864 (1.4); 0.810 (0.3); 0.048 (0.9); 0.038 (24.4); 0.027 (1.0)

    Example V-18

    [0395] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =7.322 (0.3); 7.310 (2.7); 7.298 (35.1); 7.289 (3.5); 7.283 (4.1); 7.261 (3.9); 7.253 (2.9); 7.245 (0.9); 7.232 (2.4); 6.947 (0.4); 6.895 (2.1); 6.887 (3.5); 6.876 (1.6); 6.867 (4.5); 6.859 (5.6); 6.852 (4.4); 6.844 (6.2); 6.836 (3.8); 6.831 (3.9); 6.823 (3.7); 6.818 (3.9); 6.807 (2.5); 6.803 (2.9); 6.794 (5.7); 6.787 (16.0); 6.760 (15.6); 6.754 (6.3); 6.744 (2.1); 6.722 (0.3); 6.675 (0.4); 6.665 (0.7); 6.658 (0.7); 6.635 (0.8); 6.628 (0.7); 6.543 (0.5); 6.518 (0.5); 6.502 (0.4); 6.495 (0.5); 6.487 (0.4); 6.474 (0.4); 6.466 (0.5); 6.458 (0.5); 6.450 (0.3); 3.254 (1.2); 3.126 (0.4); 3.022 (0.8); 3.006 (1.2); 2.994 (9.9); 2.978 (13.7); 2.940 (0.4); 2.902 (11.2); 2.887 (8.2); 1.585 (18.9); 1.459 (0.3); 1.294 (7.8); 1.280 (3.6); 1.261 (4.9); 1.254 (3.3); 1.242 (3.5); 1.236 (4.2); 1.229 (5.2); 1.223 (4.8); 1.217 (4.1); 1.199 (5.3); 1.180 (3.3); 1.175 (4.3); 1.148 (3.5); 1.144 (3.4); 1.129 (2.8); 1.125 (3.1); 1.094 (2.7); 1.072 (6.0); 1.057 (5.6); 1.049 (4.9); 1.043 (5.1); 1.030 (4.3); 1.019 (4.9); 0.999 (2.0); 0.993 (2.9); 0.972 (1.0); 0.918 (1.9); 0.888 (2.1); 0.863 (1.4); 0.048 (1.2); 0.037 (34.7); 0.027 (1.4)

    Example V-19

    [0396] .sup.1H-NMR (300.2 MHz, CDCl.sub.3): =7.644 (0.4); 7.574 (4.2); 7.552 (4.9); 7.546 (7.8); 7.525 (7.8); 7.518 (5.3); 7.497 (4.7); 7.298 (56.3); 7.072 (0.4); 7.055 (4.7); 7.038 (5.1); 7.024 (8.2); 7.021 (6.0); 7.007 (7.8); 7.004 (5.9); 6.990 (7.2); 6.973 (7.0); 6.943 (3.6); 6.940 (3.6); 6.934 (4.4); 6.932 (4.5); 6.917 (10.8); 6.903 (13.2); 6.891 (8.9); 6.886 (13.2); 6.877 (14.2); 6.872 (5.9); 6.860 (6.8); 6.857 (7.7); 6.853 (7.4); 6.846 (8.7); 6.823 (5.6); 6.815 (4.5); 6.771 (0.4); 6.757 (0.4); 6.741 (0.5); 6.730 (0.4); 6.713 (0.3); 6.699 (0.3); 4.540 (0.4); 4.509 (0.7); 4.477 (0.4); 3.253 (9.7); 3.248 (9.8); 3.236 (11.8); 3.231 (11.9); 3.087 (15.7); 3.070 (12.9); 2.937 (0.3); 2.907 (0.5); 2.656 (0.6); 1.586 (12.9); 1.491 (0.3); 1.468 (0.4); 1.460 (0.5); 1.451 (0.4); 1.294 (11.9); 1.261 (2.2); 1.229 (1.1); 1.180 (1.2); 1.154 (5.1); 1.146 (5.7); 1.120 (15.8); 1.087 (16.0); 1.068 (1.2); 1.032 (0.4); 0.989 (3.0); 0.985 (3.1); 0.965 (6.7); 0.949 (2.1); 0.942 (5.6); 0.933 (12.2); 0.919 (4.1); 0.912 (7.1); 0.901 (10.6); 0.889 (3.9); 0.880 (6.0); 0.869 (6.2); 0.848 (2.4); 0.048 (1.8); 0.038 (56.0); 0.027 (2.0)

    USE EXAMPLES

    Example A: In Vivo Preventive Test on Alternaria brassicae (Leaf Spot on Radish)

    [0397]

    TABLE-US-00004 Solvent: 5% by volume of Dimethyl sulfoxide 10% by volume of Acetone Emulsifier: 1 l of Tween 80 per mg of active ingredient

    [0398] The active ingredients are made soluble and homogenized in a mixture of Dimethyl sulfoxide/Acetone/Tween 80 and then diluted in water to the desired concentration.

    [0399] The young plants of radish 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 80.

    [0400] After 24 hours, the plants are contaminated by spraying the leaves with an aqueous suspension of Alternaria brassicae spores. The contaminated radish plants are incubated for 6 days at 20 C. and at 100% relative humidity.

    [0401] The test is evaluated 6 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.

    [0402] In this test the following compounds according to the invention showed efficacy between 70% and 79% at a concentration of 500 ppm of active ingredient: I-24.

    [0403] In this test the following compounds according to the invention showed efficacy between 80% and 89% at a concentration of 500 ppm of active ingredient: I-28.

    [0404] In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 500 ppm of active ingredient: I-29.

    Example B: In Vivo Preventive Test on Puccinia recondita (Brown Rust on Wheat)

    [0405]

    TABLE-US-00005 Solvent: 5% by volume of Dimethyl sulfoxide 10% by volume of Acetone Emulsifier: 1 l of Tween 80 per mg of active ingredient

    [0406] The active ingredients are made soluble and homogenized in a mixture of Dimethyl sulfoxide/Acetone/Tween 80 and then diluted in water to the desired concentration.

    [0407] 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 80.

    [0408] 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.

    [0409] 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.

    [0410] In this test the following compounds according to the invention showed efficacy between 80% and 89% at a concentration of 500 ppm of active ingredient: I-04; I-06; I-09; I-10.

    [0411] In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 500 ppm of active ingredient: I-01; I-05; I-07; I-08; I-11; I-12; I-13; I-14; I-15; I-16; I-17; I-18; I-19; I-20; I-21; I-22; I-23; I-24; I-25; I-26; I-27; I-28; I-29; I-30.

    Example C: In Vivo Preventive Test on Septoria tritici (Leaf Spot on Wheat)

    [0412]

    TABLE-US-00006 Solvent: 5% by volume of Dimethyl sulfoxide 10% by volume of Acetone Emulsifier: 1 l of Tween 80 per mg of active ingredient

    [0413] The active ingredients are made soluble and homogenized in a mixture of Dimethyl sulfoxide/Acetone/Tween 80 and then diluted in water to the desired concentration.

    [0414] 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 80.

    [0415] 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.

    [0416] 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.

    [0417] In this test the following compounds according to the invention showed efficacy between 70% and 79% at a concentration of 500 ppm of active ingredient: I-06.

    [0418] In this test the following compounds according to the invention showed efficacy between 80% and 89% at a concentration of 500 ppm of active ingredient: I-15; I-18.

    [0419] In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 500 ppm of active ingredient: I-01; I-04; I-05; I-07; I-08; I-10; I-11; I-12; I-13; I-14; I-16; I-17; I-19; I-20; I-21; I-22; I-23; I-24; I-25; I-26; I-27; I-28; I-29; I-30.

    Example D: In Vivo Preventive Test on Sphaerotheca Fuliginea (Powdery Mildew on Cucurbits)

    [0420]

    TABLE-US-00007 Solvent: 5% by volume of Dimethyl sulfoxide 10% by volume of Acetone Emulsifier: 1 l of Tween 80 per mg of active ingredient

    [0421] The active ingredients are made soluble and homogenized in a mixture of Dimethyl sulfoxide/Acetone/Tween 80 and then diluted in water to the desired concentration.

    [0422] 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 80.

    [0423] 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.

    [0424] 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.

    [0425] In this test the following compounds according to the invention showed efficacy between 80% and 89% at a concentration of 500 ppm of active ingredient: I-29.

    [0426] In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 500 ppm of active ingredient: I-01; I-04; I-05; I-06; I-07; I-08; I-09; I-10; I-11; I-12; I-13; I-14; I-15; I-16; I-17; I-18; I-20; I-22; I-23; I-24; I-25; I-26; I-27; I-28; I-30.

    Example E: In Vivo Preventive Test on Uromyces appendiculatus (Bean Rust)

    [0427]

    TABLE-US-00008 Solvent: 5% by volume of Dimethyl sulfoxide 10% by volume of Acetone Emulsifier: 1 l of Tween 80 per mg of active ingredient

    [0428] The active ingredients are made soluble and homogenized in a mixture of Dimethyl sulfoxide/Acetone/Tween 80 and then diluted in water to the desired concentration.

    [0429] 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 80.

    [0430] 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.

    [0431] 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.

    [0432] In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 500 ppm of active ingredient: I-01; I-05; I-06; I-07; I-08; I-09; I-10; I-11; I-12; I-13; I-14; I-15; I-16; I-17; I-18; I-19; I-20; I-21; I-22; I-23; I-24; I-25; I-26; I-27; I-28; I-29; I-30.

    Example F: In Vivo Preventive Test on Botrytis Test (Beans)

    [0433]

    TABLE-US-00009 Solvent: 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether

    [0434] 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.

    [0435] To test for preventive activity, young plants are sprayed with the preparation of active compound. After the spray coating has dried on, 2 small pieces of agar covered with growth of Botrytis cinerea are placed on each leaf. The inoculated plants are placed in a darkened chamber at 20 C. and a relative atmospheric humidity of 100%.

    [0436] 2 days after the inoculation, the size of the lesions on the leaves is evaluated. 0% means an efficacy which corresponds to that of the untreated control, while an efficacy of 100% means that no disease is observed.

    [0437] In this test the following compounds according to the invention showed efficacy between 70% and 79% at a concentration of 250 ppm of active ingredient: I-01; I-02; I-03.

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

    [0438]

    TABLE-US-00010 Solvent: 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether

    [0439] 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.

    [0440] 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%.

    [0441] 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.

    [0442] 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.

    [0443] In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 100 ppm of active ingredient: I-02; I-08; I-13; I-20; I-22; I-23.

    [0444] In this test the following compounds according to the invention showed efficacy between 70% and 79% at a concentration of 10 ppm of active ingredient: I-10; I-16.

    [0445] In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 10 ppm of active ingredient: I-01; I-03; I-05; I-24.

    Example H: In Vivo Preventive Test on Uromyces Test (Beans)

    [0446]

    TABLE-US-00011 Solvent: 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether

    [0447] 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.

    [0448] 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 bean rust (Uromyces appendiculatus) and then remain for 1 day in an incubation cabinet at approximately 20 C. and a relative atmospheric humidity of 100%.

    [0449] The plants are then placed in a greenhouse at approximately 21 C. and a relative atmospheric humidity of approximately 90%.

    [0450] 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.

    [0451] In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 100 ppm of active ingredient: I-01; I-02; I-03; I-08; I-13; I-20; I-22; I-23.

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

    [0452]

    TABLE-US-00012 Solvent: 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether

    [0453] 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.

    [0454] 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%.

    [0455] The plants are then placed in a greenhouse at approximately 21 C. and a relative atmospheric humidity of approximately 90%.

    [0456] 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.

    [0457] In this test the following compounds according to the invention showed efficacy between 80% and 89% at a concentration of 100 ppm of active ingredient: I-13; I-20.

    [0458] In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 100 ppm of active ingredient: I-01; I-02; I-03; I-08; I-22; I-23.

    Example J: In Vivo Preventive Blumeria Test (Barley)

    [0459]

    TABLE-US-00013 Solvent: 49 parts by weight of N,N-dimethylacetamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether

    [0460] 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.

    [0461] 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.

    [0462] After the spray coating has been dried, the plants are dusted with spores of Blumeria graminis f sp. hordei.

    [0463] 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.

    [0464] 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.

    [0465] In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 500 ppm of active ingredient: I-01; I-03; I-05; I-08; I-13; I-14; I-16; I-17; I-20; I-22.

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

    [0466]

    TABLE-US-00014 Solvent: 49 parts by weight of N,N-dimethylacetamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether

    [0467] 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.

    [0468] 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.

    [0469] 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%.

    [0470] The plants are placed in the greenhouse at a temperature of approximately 25 C. and a relative atmospheric humidity of approximately 80%.

    [0471] 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.

    [0472] In this test the following compounds according to the invention showed efficacy between 70% and 79% at a concentration of 500 ppm of active ingredient: I-08; I-22.

    [0473] In this test the following compounds according to the invention showed efficacy between 80% and 89% at a concentration of 500 ppm of active ingredient: I-13.

    [0474] In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 500 ppm of active ingredient: I-01; I-02; I-03; I-20.

    Example L: In Vivo Preventive Pyrenophora Teres Test (Barley)

    [0475]

    TABLE-US-00015 Solvent: 49 parts by weight of N,N-dimethylacetamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether

    [0476] 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.

    [0477] 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.

    [0478] After the spray coating has been dried, the plants are sprayed with a spore suspension of Pyrenophora teres. The plants remain for 48 hours in an incubation cabinet at approximately 20 C. and a relative atmospheric humidity of approximately 100%.

    [0479] The plants are placed in the greenhouse at a temperature of approximately 20 C. and a relative atmospheric humidity of approximately 80%.

    [0480] 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.

    [0481] In this test the following compounds according to the invention showed efficacy between 70% and 79% at a concentration of 500 ppm of active ingredient: I-13.

    [0482] In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 500 ppm of active ingredient: I-01; I-02; I-03; I-20; I-22.

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

    [0483]

    TABLE-US-00016 Solvent: 49 parts by weight of N,N-dimethylacetamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether

    [0484] 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.

    [0485] 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.

    [0486] After the spray coating has been dried, the plants are sprayed with a spore suspension of Septoria tritici. The plants remain for 48 hours in an incubation cabinet at approximately 20 C. and a relative atmospheric humidity of approximately 100% and afterwards for 60 hours at approximately 15 C. in a translucent incubation cabinet at a relative atmospheric humidity of approximately 100%.

    [0487] The plants are placed in the greenhouse at a temperature of approximately 15 C. and a relative atmospheric humidity of approximately 80%.

    [0488] The test is evaluated 21 days after the inoculation. 0% means an efficacy which corresponds to that of the untreated control, while an efficacy of 100% means that no disease is observed.

    [0489] In this test the following compounds according to the invention showed efficacy between 80% and 89% at a concentration of 500 ppm of active ingredient: I-05.

    [0490] In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 500 ppm of active ingredient: I-01; I-02; I-03; I-08; I-13; I-14; I-17; I-20; I-22.

    Example N: Alternaria Test (Tomato)/Preventive

    [0491]

    TABLE-US-00017 Solvent: 49 parts by weight of N,N-dimethylformamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether

    [0492] 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.

    [0493] To test for preventive activity, young plants are sprayed with the preparation of active compound at the stated rate of application. One day after this treatment, the plants are inoculated with an aqueous spore suspension of Alternaria solani. The plants remain for one day in an incubation cabinet at approximately 22 C. and a relative atmospheric humidity of 100%. Then the plants are placed in an incubation cabinet at approximately 20 C. and a relative atmospheric humidity of 96%.

    [0494] 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.

    [0495] In this test the following compounds according to the invention showed efficacy between 70% and 79% at a concentration of 100 ppm of active ingredient: I-02.

    Example O: Leptosphaeria Test (Wheat)/Preventive

    [0496]

    TABLE-US-00018 Solvent: 49 parts by weight of N,N-dimethylformamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether

    [0497] 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.

    [0498] To test for preventive activity, young plants are sprayed with a preparation of active compound at the stated rate of application. One day after this treatment, the plants are inoculated with an aqueous spore suspension of Leptosphaeria nodorum. The plants remain for 48 hours in an incubation cabinet at 22 C. and a relative atmospheric humidity of 100%. Then the plants are placed in a greenhouse at a temperature of approximately 22 C. and a relative atmospheric humidity of approximately 90%.

    [0499] The test is evaluated 7-9 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.

    [0500] In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 100 ppm of active ingredient: I-01.

    Example P: Puccinia Test (Wheat)/Preventive

    [0501]

    TABLE-US-00019 Solvent: 49 parts by weight of N,N-dimethylformamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether

    [0502] 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.

    [0503] To test for preventive activity, young plants are sprayed with the preparation of active compound at the stated rate of application. One day after this treatment, the plants are inoculated with an aqueous spore suspension of Puccinia recondita. The plants remain for 48 hours in an incubation cabinet at 22 C. and a relative atmospheric humidity of 100%. Then the plants are placed in a greenhouse at a temperature of approximately 20 C. and a relative atmospheric humidity of approximately 80%.

    [0504] The test is evaluated 7-9 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.

    [0505] In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 100 ppm of active ingredient: I-01; I-02; I-03.

    Example 0: Pyricularia Test (Rice)/Preventive

    [0506]

    TABLE-US-00020 Solvent: 49 parts by weight of N,N-dimethylformamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether

    [0507] 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.

    [0508] To test for preventive activity, young plants are sprayed with a preparation of active compound at the stated rate of application. One day after this treatment, the plants are inoculated with an aqueous spore suspension of Pyricularia oryzae. The plants remain for 48 hours in an incubation cabinet at 24 C. and a relative atmospheric humidity of 100%. Then the plants are placed in a greenhouse at a temperature of approximately 24 C. and a relative atmospheric humidity of approximately 80%.

    [0509] 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.

    [0510] In this test the following compounds according to the invention showed efficacy between 70% and 79% at a concentration of 100 ppm of active ingredient: I-01.

    [0511] In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 100 ppm of active ingredient: I-02; I-03.

    Example R: Pyrenophora Test (Barley)/Preventive

    [0512]

    TABLE-US-00021 Solvent: 49 parts by weight of N,N-dimethylformamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether

    [0513] 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.

    [0514] To test for preventive activity, young plants are sprayed with the preparation of active compound at the stated rate of application. One day after this treatment, the plants are inoculated with an aqueous spore suspension of Pyrenophora teres. The plants remain for 48 hours in an incubation cabinet at 22 C. and a relative atmospheric humidity of 100%. Then the plants are placed in a greenhouse at a temperature of approximately 20 C. and a relative atmospheric humidity of approximately 80%.

    [0515] The test is evaluated 7-9 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.

    [0516] In this test the following compounds according to the invention showed efficacy between 70% and 79% at a concentration of 100 ppm of active ingredient: I-01.

    [0517] In this test the following compounds according to the invention showed efficacy between 80% and 89% at a concentration of 100 ppm of active ingredient: I-03.

    Example S: Sphaerotheca Test (Cucumber)/Preventive

    [0518]

    TABLE-US-00022 Solvent: 49 parts by weight of N,N-dimethylformamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether

    [0519] 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.

    [0520] To test for preventive activity, young plants are sprayed with the preparation of active compound at the stated rate of application. One day after this treatment, the plants are inoculated with an aqueous spore suspension of Sphaerotheca fuliginea. Then the plants are placed in a greenhouse at approximately 23 C. and a relative atmospheric humidity of approximately 70%.

    [0521] 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.

    [0522] In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 100 ppm of active ingredient: I-01; I-02; I-03.

    Example T: In Vivo Preventive Test on Venturia Test (Apples) Comparison of Compounds According to the Invention Vs. Known Compounds

    [0523]

    TABLE-US-00023 Solvent: 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether

    [0524] 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.

    [0525] 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%.

    [0526] The plants are then placed in a greenhouse at approximately 21 C. and a relative atmospheric humidity of approximately 90%.

    [0527] 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.

    TABLE-US-00024 TABLE results of in vivo preventive test on Venturia test (apples) Rate of application of active compound in Efficacy Active compound ppm in % Comparison compound: Known from: DE-A 3522440 Ex. I-44 [00022]embedded image 10 0 Known from: DE-A 3522440 Ex. I-134 [00023]embedded image 10 76 According to the invention: Ex. I-01 [00024]embedded image 10 98 Ex. I-03 [00025]embedded image 10 93

    Example U: In Vivo Preventive Test on Phakopsora Test (Soybeans); Comparison of Compounds According to the Invention Vs. Known Compounds

    [0528]

    TABLE-US-00025 Solvent: 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether

    [0529] 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.

    [0530] 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%.

    [0531] 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.

    [0532] 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.

    TABLE-US-00026 TABLE result of in vivo preventive test on Phakopsora test (soybeans) Rate of application of active compound in Efficacy Active compound ppm in % Comparison compound: Known from: DE-A 3522440 Ex. I-44 [00026]embedded image 5 15 Known from: DE-A 3522440 Ex. I-134 [00027]embedded image 5 0 According to the invention: Ex. I-01 [00028]embedded image 5 95 Ex. I-03 [00029]embedded image 5 89