Tetrazolylpropyl derivatives and their use as fungicides

Abstract

The present invention relates to tetrazolylpropyl derivatives of formula (I) ##STR00001##
wherein one of V.sup.1 and V.sup.2 represents CR.sup.3 and the other one of V.sup.1 and V.sup.2 represents N, Q represents a 6-membered aromatic cycle as defined in the specification, and R.sup.1, R.sup.2, R.sup.3, R.sup.4, and R.sup.5 are defined as disclosed in the specification, to compositions comprising such compounds, to the use of said compounds as fungicides, as well as to particular intermediates useful in the synthesis of said tetrazolylpropyl derivatives.

Claims

1. Compound of formula (I) ##STR00048## wherein R.sup.1 represents hydrogen, C.sub.1-C.sub.8-alkyl, C.sub.1-C.sub.8-haloalkyl, C.sub.2-C.sub.8-alkenyl, C.sub.2-C.sub.8-haloalkenyl, C.sub.2-C.sub.8-alkynyl, C.sub.2-C.sub.8-haloalkynyl, phenyl-C.sub.2-C.sub.8-alkynyl, [tri(C.sub.1-C.sub.8-alkyl)silyl]phenyl-C.sub.2-C.sub.8-alkynyl, C.sub.3-C.sub.7-cycloalkyl, bicycloalkyl, C.sub.3-C.sub.7-cycloalkyl-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.7-cycloalkyl-C.sub.3-C.sub.7-cycloalkyl, C.sub.3-C.sub.7-cycloalkenyl, tri(C.sub.1-C.sub.8-alkyl)silyl-C.sub.1-C.sub.4-alkyl, or tri(C.sub.1-C.sub.8-alkyl)silyl-C.sub.3-C.sub.7-cycloalkyl, wherein the phenyl-C.sub.2-C.sub.8-alkynyl, [tri(C.sub.1-C.sub.8-alkyl)silyl]phenyl-C.sub.2-C.sub.8-alkynyl, C.sub.3-C.sub.7-cycloalkyl, bicycloalkyl, C.sub.3-C.sub.7-cycloalkyl-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.7-cycloalkyl-C.sub.3-C.sub.7-cycloalkyl, C.sub.3-C.sub.7-cycloalkenyl, tri(C.sub.1-C.sub.8-alkyl)silyl-C.sub.1-C.sub.4-alkyl, and tri(C.sub.1-C.sub.8-alkyl)silyl-C.sub.3-C.sub.7-cycloalkyl is non-substituted or substituted by one or more group(s) selected from halogen, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-alkylthio and C.sub.1-C.sub.4-haloalkylthio; R.sup.2 represents hydrogen, halogen, cyano or —OR.sup.2a, wherein R.sup.2a represents hydrogen, C.sub.1-C.sub.8-alkyl, —Si(R.sup.6a)(R.sup.6b)(R.sup.6c), —P(O)(OH).sub.2, —CH.sub.2—O—P(O)(OH).sub.2, —C(O)—C.sub.1-C.sub.8-alkyl, —C(O)—C.sub.3-C.sub.7-cycloalkyl, —C(O)NH—C.sub.1-C.sub.8-alkyl, —C(O)N-di-C.sub.1-C.sub.8-alkyl, or —C(O)O—C.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)NH—C.sub.1-C.sub.8-alkyl, —C(O)N-di-C.sub.1-C.sub.8-alkyl and —C(O)O—C.sub.1-C.sub.8-alkyl is non-substituted or substituted by one or more group(s) selected from halogen and C.sub.1-C.sub.8-alkoxy, wherein R.sup.6a, R.sup.6b, R.sup.6c represent independently from each other phenyl or C.sub.1-C.sub.8-alkyl; one of V.sup.1 and V.sup.2 represents CR.sup.3 and the other one of V.sup.1 and V.sup.2 represents N, R.sup.3 represents hydrogen, halogen, hydroxyl, cyano, sulfanyl, C.sub.1-C.sub.8-alkyl, or C.sub.1-C.sub.8-haloalkyl; R.sup.4 represents hydrogen, fluorine, C.sub.1-C.sub.8-alkyl, C.sub.1-C.sub.8-haloalkyl or C.sub.1-C.sub.8-alkyloxy; R.sup.5 represents hydrogen, fluorine, C.sub.1-C.sub.8-alkyl, C.sub.1-C.sub.8-haloalkyl or C.sub.1-C.sub.8-alkyloxy; or R.sup.4 and R.sup.5 form together with the carbon atom to which they are attached C.sub.3-C.sub.7-cycloalkyl, wherein the C.sub.3-C.sub.7-cycloalkyl ring is non-substituted or substituted by one or more substituent(s) selected from halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-alkylthio and C.sub.1-C.sub.4-haloalkylthio; or R.sup.4 and R.sup.5 form together with the carbon atom to which they are attached C.sub.2-alkenyl, wherein the C.sub.2-alkenyl is non-substituted or substituted by one or more substituent(s) selected from halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-alkylthio and C.sub.1-C.sub.4-haloalkylthio; and Q represents a 6-membered aromatic cycle of formula (Q-I) ##STR00049## wherein U.sup.1 represents CX.sup.1 or N; U.sup.2 represents CX.sup.2 or N; U.sup.3 represents CX.sup.3 or N; U.sup.4 represents CX.sup.4 or N; U.sup.5 represents CX.sup.5 or N; wherein X.sup.1, X.sup.2, X.sup.3, X.sup.4, and X.sup.5 independently from each other represent hydrogen, halogen, nitro, cyano, sulfanyl, pentafluoro-λ.sup.6-sulfanyl, C.sub.1-C.sub.8-alkyl, C.sub.1-C.sub.8-haloalkyl having 1 to 5 halogen atoms, C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halocycloalkyl having 1 to 5 halogen atoms, C.sub.1-C.sub.8-haloalkyl-C.sub.3-C.sub.7-cycloalkyl, C.sub.3-C.sub.7-cycloalkenyl, C.sub.2-C.sub.8-alkenyl, C.sub.2-C.sub.8-alkynyl, C.sub.6-C.sub.12-bicycloalkyl, C.sub.3-C.sub.8-cycloalkyl-C.sub.2-C.sub.8-alkenyl, C.sub.3-C.sub.8-cycloalkyl-C.sub.2-C.sub.8-alkynyl, C.sub.1-C.sub.8-alkoxy, C.sub.1-C.sub.8-haloalkoxy having 1 to 5 halogen atoms, C.sub.1-C.sub.8-alkoxycarbonyl, C.sub.1-C.sub.8-haloalkoxycarbonyl, C.sub.1-C.sub.8-alkylsulfenyl, C.sub.2-C.sub.8-alkenyloxy, C.sub.3-C.sub.8-alkynyloxy, C.sub.3-C.sub.6-cycloalkoxy, C.sub.1-C.sub.8-alkylsulfinyl, C.sub.1-C.sub.8-alkylsulfonyl, tri(C.sub.1-C.sub.8-alkyl)-silyloxy, tri(C.sub.1-C.sub.8-alkyl)-silyl, tri(C.sub.1-C.sub.8-alkyl)-silyl-C.sub.2-C.sub.8-alkynyl, tri(C.sub.1-C.sub.8-alkyl)-silyl-C.sub.2-C.sub.8-alkynyloxy, C.sub.6-C.sub.14-aryl, C.sub.6-C.sub.14-aryloxy, C.sub.6-C.sub.14-arylsulfenyl, 5- or 6-membered heteroaryl, 5- or 6-membered heteroaryloxy, wherein the C.sub.6-C.sub.14-aryl, C.sub.6-C.sub.14-aryloxy, C.sub.6-C.sub.14-arylsulfenyl, 5- or 6-membered heteroaryl, 5- or 6-membered heteroaryloxy is non-substituted or substituted by one or more group(s) selected from halogen, cyanosulfanyl, pentafluoro-λ.sup.6-sulfanyl, C.sub.1-C.sub.8-alkyl, C.sub.1-C.sub.8-haloalkyl, C.sub.1-C.sub.8-cyanoalkyl, C.sub.1-C.sub.8-alkyloxy, C.sub.1-C.sub.8-haloalkyloxy, tri(C.sub.1-C.sub.8-alkyl)silyl, tri(C.sub.1-C.sub.8-alkyl)silyl-C.sub.1-C.sub.8-alkyl, C.sub.3-C.sub.7-cycloalkyl, C.sub.3-C.sub.7-halocycloalkyl, C.sub.3-C.sub.7-cycloalkenyl, C.sub.3-C.sub.7-halocycloalkenyl, C.sub.4-C.sub.10-cycloalkylalkyl, C.sub.4-C.sub.10-halocycloalkylalkyl, C.sub.6-C.sub.12-cycloalkylcycloalkyl, C.sub.1-C.sub.8-alkyl-C.sub.3-C.sub.7-cycloalkyl, C.sub.1-C.sub.8-alkoxy-C.sub.3-C.sub.7-cycloalkyl, tri(C.sub.1-C.sub.8-alkyl)silyl-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.2-C.sub.8-haloalkenyloxy, C.sub.3-C.sub.8-alkynyloxy, C.sub.3-C.sub.8-haloalkynyloxy, C.sub.1-C.sub.8-cyanoalkoxy, C.sub.4-C.sub.8-cycloalkylalkoxy, C.sub.3-C.sub.6-cycloalkoxy, C.sub.1-C.sub.8-alkylsulfanyl, C.sub.1-C.sub.8-haloalkylsulfanyl, C.sub.1-C.sub.8-alkylsulfinyl, C.sub.1-C.sub.8-haloalkylsulfinyl, C.sub.1-C.sub.8-alkylsulfonyl, C.sub.1-C.sub.8-haloalkylsulfonyl, C.sub.1-C.sub.8-alkylsulfonyloxy, C.sub.1-C.sub.8-haloalkylsulfonyloxy, C.sub.1-C.sub.8-alkoxyalkyl, C.sub.1-C.sub.8-alkylthioalkyl, C.sub.1-C.sub.8-alkoxyalkoxyalkyl, C.sub.1-C.sub.8-haloalkoxyalkyl, benzyl, phenyl, 5-membered heteroaryl, 6-membered heteroaryl, 6-membered heteroaryloxy, benzyloxy, phenyloxy, benzylsulfanyl, and phenylsulfanyl, wherein the benzyl, phenyl, 5-membered heteroaryl, 6-membered heteroaryl, 6-membered heteroaryloxy, benzyloxy, phenyloxy, benzylsulfanyl and phenylsulfanyl is non-substituted or substituted by one or more group(s) selected from halogen, CN, nitro, C.sub.1-C.sub.8-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy and pentafluoro-λ.sup.6-sulfanyl; and wherein at most two of U.sup.1, U.sup.2, U.sup.3, U.sup.4 and U.sup.5 represent N; or U.sup.1 and U.sup.2 or U.sup.2 and U.sup.3 or U.sup.3 and U.sup.4 form together an additional saturated or unsaturated 4 to 6-membered halogen- or C.sub.1-C.sub.8-alkyl-substituted or non-substituted ring; and/or a salt and/or N-oxide thereof.

2. The compound according to claim 1, wherein R.sup.1 represents C.sub.1-C.sub.8-alkyl, C.sub.1-C.sub.8-haloalkyl, or optionally halogen-, cyano-, C.sub.1-C.sub.4-alkyl-, C.sub.1-C.sub.4-haloalkyl-, C.sub.1-C.sub.4-alkoxy-, C.sub.1-C.sub.4-haloalkoxy-, C.sub.1-C.sub.4-alkylthio- or C.sub.1-C.sub.4-haloalkylthio-substituted C.sub.3-C.sub.7-cycloalkyl.

3. The compound according to claim 1, wherein R.sup.2 represents —OR.sup.2a, and wherein R.sup.2a represents hydrogen or C.sub.1-C.sub.8-alkyl.

4. The compound according to claim 1, wherein R.sup.3 represents hydrogen, fluorine, chlorine, bromine, or iodine.

5. The compound according to claim 1, wherein R.sup.4 represents hydrogen, fluorine or methyl and R.sup.5 represents hydrogen or fluorine, or R.sup.4 and R.sup.5 form together with the carbon atom to which they are attached C.sub.2-alkenyl, wherein the C.sub.2-alkenyl is non-substituted or substituted by one or more substituent(s) selected from halogen, C.sub.1-C.sub.4-alkyl, and C.sub.1-C.sub.4-haloalkyl.

6. The compound according to claim 1, wherein Q represents a 6-membered aromatic cycle selected from the group consisting of formula (Q-I-1) to (Q-I-10) ##STR00050## ##STR00051##

7. The compound according to claim 1, wherein Q represents a 6-membered aromatic cycle of formula (Q-I-1) or (Q-I-2) ##STR00052##

8. The compound according to claim 1, wherein X.sup.1, X.sup.2, X.sup.3, X.sup.4 and X.sup.5 independently from each other represent hydrogen, halogen, cyano, C.sub.1-C.sub.8-alkyl, C.sub.1-C.sub.8-haloalkyl having 1 to 5 halogen atoms, C.sub.2-C.sub.8-alkenyl, C.sub.2-C.sub.8-alkynyl, C.sub.3-C.sub.8-cycloalkyl-C.sub.2-C.sub.8-alkenyl, C.sub.3-C.sub.8-cycloalkyl-C.sub.2-C.sub.8-alkynyl, C.sub.1-C.sub.8-alkoxy, C.sub.1-C.sub.8-haloalkoxy having 1 to 5 halogen atoms, C.sub.6-C.sub.14-aryl, or C.sub.6-C.sub.14-aryloxy, wherein the C.sub.6-C.sub.14-aryl and C.sub.6-C.sub.14-aryloxy is non-substituted or 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-alkyloxy, and C.sub.1-C.sub.8-haloalkyloxy.

9. The compound according to claim 1, wherein R.sup.1 represents C.sub.1-C.sub.8-alkyl, or optionally halogen-, or C.sub.1-C.sub.4-alkyl-substituted C.sub.3-C.sub.7-cycloalkyl; R.sup.2 represents —OH; one of V.sup.1 and V.sup.2 represents CH and the other one of V.sup.1 and V.sup.2 represents N; R.sup.4 represents hydrogen, fluorine or methyl; R.sup.5 represents hydrogen or fluorine; or R.sup.4 and R.sup.5 form together with the carbon atom to which they are attached C.sub.2-alkenyl, wherein the C.sub.2-alkenyl is substituted by methyl non-substituted; and Q represents a 6-membered aromatic cycle of formula (Q-I-1) or (Q-I-2) ##STR00053## wherein X.sup.1, X.sup.2, X.sup.3, X.sup.4, and X.sup.5 independently from each other represent hydrogen, halogen, cyano, C.sub.1-C.sub.8-alkyl, C.sub.1-C.sub.8-haloalkyl having 1 to 5 halogen atoms, C.sub.2-C.sub.8-alkenyl, C.sub.2-C.sub.8-alkynyl, C.sub.3-C.sub.8-cycloalkyl-C.sub.2-C.sub.8-alkenyl, C.sub.3-C.sub.8-cycloalkyl-C.sub.2-C.sub.8-alkynyl, C.sub.1-C.sub.8-alkoxy, C.sub.1-C.sub.8-haloalkoxy having 1 to 5 halogen atoms, C.sub.6-C.sub.14-aryl, or C.sub.6-C.sub.14-aryloxy, wherein the C.sub.6-C.sub.14-aryl and C.sub.6-C.sub.14-aryloxy is non-substituted or 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-alkyloxy, and C.sub.1-C.sub.8-haloalkyloxy; and/or a salt and/or N-oxide thereof.

10. A composition for controlling one or more harmful microorganisms, optionally for controlling phytopathogenic harmful fungi, comprising at least one compound according to claim 1, and at least one carrier and/or surfactant.

11. A method for controlling one or more harmful microorganisms, optionally phytopathogenic harmful fungi, in crop protection and/or in protection of materials, comprising applying at least one compound according to claim 1 to the harmful microorganisms and/or a habitat thereof.

12. A product comprising at least one compound according to claim 1 for control of one or more harmful microorganisms, optionally phytopathogenic harmful fungi, in crop protection and/or in protection of materials.

13. A product comprising at least one compound of formula (I) according to claim 1 for treatment of a transgenic plant or for treatment of seed, optionally seed of a transgenic plant.

14. Ketone of formula (XVI) ##STR00054## wherein R.sup.1′ represents C.sub.3-C.sub.7-cycloalkyl, wherein the C.sub.3-C.sub.7-cycloalkyl is non-substituted or substituted by one or more group(s) selected from halogen, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-alkylthio and C.sub.1-C.sub.4-haloalkylthio; and one of V.sup.1′ and V.sup.2′ represents CH and the other one of V.sup.1′ and V.sup.2′ represents N; and/or a salt and/or N-oxide thereof.

15. Epoxide of formula (XVII) ##STR00055## wherein R.sup.1′ represents C.sub.3-C.sub.7-cycloalkyl, wherein the C.sub.3-C.sub.7-cycloalkyl is non-substituted or substituted by one or more group(s) selected from halogen, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-alkylthio and C.sub.1-C.sub.4-haloalkylthio; and one of V.sup.1′ and V.sup.2′ represents CH and the other one of V.sup.1′ and V.sup.2′ represents N; and/or a salt and/or N-oxide thereof.

Description

PREPARATION EXAMPLES

Preparation of 2-(1-chlorocyclopropyl)-1-(2-chlorophenyl)-3-(tetrazol-1-yl)propan-2-ol (Ia-05) and 2-(1-chlorocyclopropyl)-1-(2-chlorophenyl)-3-(tetrazol-2-yl)propan-2-ol (Ib-04)

(1) ##STR00035##

(2) In a 50 mL 2-neck round bottom flask, equipped with a magnetic stirrer and condenser, tetrazole (761 mg, 10.8 mmol) was dissolved in 8 ml DMF (dimethylformamide). K.sub.2CO.sub.3 (1500 mg, 10.8 mmol) was added and the reaction mixture was then stirred for 15 minutes at room temperature (21° C.), before 2-(1-chlorocyclopropyl)-2-[(2-chlorophenyl)methyl]oxirane (2000 mg, 7.23 mmol) in DMF (2 ml) was added in one portion. The reaction mixture was heated to 70° C. and maintained for 22 hours during which time the reaction mixture became deep orange in colour.

(3) The reaction mixture was cooled, added to ice/water, stirred vigorously for 1 hour, at which point a precipitate had formed. The solid was filtered, washed with water and dried.

(4) Purification by flash chromatography, using a 40 g silica cartridge and 0-5% ethyl acetate/dichloromethane as eluent afforded 200 mg (8.3%) of 2-(1-chlorocyclopropyl)-1-(2-chlorophenyl)-3-(tetrazol-1-yl)propan-2-ol as a colourless solid {MS (ESI): 313.2 ([M+H].sup.+)} and 190 mg of 2-(1-chlorocyclopropyl)-1-(2-chlorophenyl)-3-(tetrazol-2-yl)propan-2-ol as a colourless solid {MS (ESI): 313.2 ([M+H].sup.+)}.

Preparation of 2-(1-chlorocyclopropyl)-1-(2-fluorophenyl)-3-(tetrazol-1-yl)propan-2-ol (Ia-04) and 2-(1-chlorocyclopropyl)-1-(2-fluorophenyl)-3-(tetrazol-2-yl)propan-2-ol (Ib-02)

(5) ##STR00036##

(6) In a 50 mL 2-neck round bottom flask, equipped with a magnetic stirrer and condenser, tetrazole (816 mg, 11.5 mmol) was dissolved in 8 ml DMF (dimethylformamide). K.sub.2CO.sub.3 (1609 mg, 11.6 mmol) was added and the reaction mixture was then stirred for 15 minutes at room temperature, before 2-(1-chlorocyclopropyl)-2-[(2-fluorophenyl)methyl]oxirane (2000 mg, 7.76 mmol) in DMF (2 ml) was added in one portion. The reaction mixture was stirred at room temperature for 15 hours, then heated to 70° C. and further stirred for 22 hours at that temperature during which time the reaction mixture became deep orange in colour.

(7) The reaction mixture was cooled, added to ice/water, stirred vigorously for 1 hour, at which point a precipitate had formed. The solid was filtered, washed with water and dried.

(8) Purification by reverse phase preparative HPLC, afforded 460 mg (19%) of 2-(1-chlorocyclopropyl)-1-(2-fluorophenyl)-3-(tetrazol-1-yl)propan-2-ol as a colourless solid {MS (ESI): 297.2 ([M+H].sup.+)} and 450 mg (18%) of 2-(1-chlorocyclopropyl)-1-(2-fluorophenyl)-3-(tetrazol-2-yl)propan-2-ol as a colourless solid {MS (ESI): 297.2 ([M+H].sup.+)}.

Preparation of 2-(1-chlorocyclopropyl)-1-(2-chloro-3-pyridyl)-3-(tetrazol-1-yl)propan-2-ol (Ia-03) and 2-(1-chlorocyclopropyl)-1-(2-chloro-3-pyridyl)-3-(tetrazol-2-yl)propan-2-ol (Ib-05)

(9) ##STR00037##

(10) A solution of tetrazole (0.45 M solution in acetonitrile, 5.56 mL, 2.5 mmol) was diluted further with acetonitrile (6.0 mL), then potassium carbonate (2.5 mmol, 345 mg) was added and the suspension was stirred for 10 minutes at room temperature before 2-chloro-3-[[2-(1-chlorocyclopropyl)oxiran-2-yl]methyl]pyridine (2.5 mmol, 642 mg) dissolved in acetonitrile (2.0 mL) was added. The reaction mixture was heated to 75° C. and stirred for 18 h. The reaction mixture was cooled to room temperature, then quenched with water, extracted with ethyl acetate, dried over Na.sub.2SO.sub.4, and concentrated. Flash column chromatography yielded 60 g of (Ia-03) (97% pure, 7% yield) {MS (ESI): 314.05 ([M].sup.+)} and 50 mg of (Ib-05) (94% pure, 6% yield) {MS (ESI): 314.05 ([M].sup.+)}.

Preparation of 2-(1-chlorocyclopropyl)-1-phenyl-3-(tetrazol-1-yl)propan-2-ol (Ia-01)

Step 1: Preparation of 1-(1-chlorocyclopropyl)-2-(tetrazol-1-yl)ethanone and 1-(1-chlorocyclopropyl)-2-(tetrazol-2-yl)ethanone

(11) ##STR00038##

(12) To a solution of tetrazole (360 mg, 5.13 mmol) in acetonitrile (10.3 ml) under argon, in a 20 ml micro-wave tube, equipped with a magnetic stirrer, DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) (861 mg, 5.65 mmol) was added. The reaction mixture was stirred at room temperature for 5 minutes, then 2-chloro-1-(1-chlorocyclopropyl)ethanone (786 mg, 5.13 mmol) in acetonitrile (1 ml) was added dropwise. The resulting reaction mixture was stirred at room temperature for 1 hour, then heated to 40° C. and stirred for a further 1 hour. The reaction mixture was cooled, concentrated to about 5 ml of solvent, diluted with ethyl acetate (15 ml), washed sequentially with 10% Na.sub.2CO.sub.3 solution, brine, and dried over MgSO.sub.4 and finally the solvent was evaporated.

(13) Purification by reverse phase preparative HPLC afforded 350 mg (34.7%) of 1-(1-chlorocyclopropyl)-2-(tetrazol-1-yl)ethanone as a colourless solid {MS (ESI): 187.2 ([M+H].sup.+)} and 100 mg (10.4%) of 1-(1-chlorocyclopropyl)-2-(tetrazol-2-yl)ethanone as a colourless solid {MS (ESI): 187.2 ([M+H].sup.+)}.

(14) Step 2: Preparation of 2-(1-chlorocyclopropyl)-1-phenyl-3-(tetrazol-1-yl)propan-2-ol (Ia-01)

(15) ##STR00039##

(16) A THF (tetrahydrofuran) solution of benzylmagnesium chloride (1.38 ml, 1.01 mmol) was furnished under argon in an oven-dried 20 ml microwave tube, equipped with a magnetic stirrer and fitted with a rubber septum, and cooled to 0° C. A THF solution of manganese chloride bis(lithium chloride) complex (2.46 ml, 1.23 mmol) was added dropwise slowly over a period of 10 minutes. The reaction mixture was stirred at 0° C. for 10 minutes, then 1-(1-chlorocyclopropyl)-2-(tetrazol-1-yl)ethanone (135 mg, 0.72 mmol) in dichloromethane (3 ml) was added and the reaction mixture stirred at 0° C. for 2 hours. The reaction mixture was quenched by dropwise addition of saturated NH.sub.4Cl solution, partitioned between water and dichloromethane, the organic layer was separated, washed with brine, dried over MgSO.sub.4 and the solvent was evaporated.

(17) Purification by reverse phase preparative HPLC, afforded 95 mg (44.8%) of compound (Ia-01) as a colourless solid {MS (ESI): 279.2 ([M+H].sup.+)}.

Preparation of 2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-1-(tetrazol-1-yl)but-3-en-2-ol (Ia-en-02)

(18) ##STR00040##

(19) Magnesium turnings (163.2 mg, 6.71 mmol, 1.5 equivalents) were first stirred 1 h at room temperature under argon, then covered with Et.sub.2O (2 mL) and 1,2-dibromoethane (2 drops) was added under continuous stirring. The resulting suspension was stirred at room temperature for 20 min. A few drops of 1-(1-bromovinyl)-2-fluoro-benzene were added, then the resulting mixture was cooled down to 0-5° C., and the remaining amount of 1-(1-bromovinyl)-4-chloro-benzene (total amount: 1.00 g, 4.47 mmol) [as a solution in Et.sub.2O (6 mL)] was added dropwise over a period of 30 min. After addition, the reaction mixture was stirred for 10 min at 0-5° C. Rapid titration of the resulting solution using iodine as an indicator gave a concentration of 0.44 M.

(20) The obtained Grignard solution (6.84 mL, 0.44 M, 3.00 mmol) was added dropwise at 5° C. to a solution of 1-(1-chlorocyclopropyl)-2-(tetrazol-1-yl)ethanone (XVIa-01) (461 mg, 2.38 mmol, 1.0 equivalent) in a mixture of THF and dichloromethane (50:50, 5 mL). The reaction mixture was further stirred at 0-5° C. for 50 min, and then quenched by addition of saturated aqueous NH.sub.4Cl at 0-5° C. The resulting mixture was diluted with water, and then extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with brine, dried (ChemElut), and then concentrated to dryness in vacuo. The oily residue was purified by preparative HPLC to afford 235 mg (36%) of 2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-1-(tetrazol-1-yl)but-3-en-2-ol as a colourless solid.

(21) MS (ESI): 309 ([M+H].sup.+)

Preparation of 2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-1-(tetrazol-1-yl)butan-2-ol, diastereoisomer 1 and diastereoisomer 2 (Ia-20 & Ia-22)

(22) ##STR00041##

(23) A solution of 2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-1-(tetrazol-1-yl)but-3-en-2-ol (160 mg, 0.51 mmol) in methanol (25 mL) was hydrogenated in an H-Cube apparatus (full H.sub.2) over a Pd/C cartridge (flow: 1 mL/min) at room temperature. The resulting solution was concentrated to dryness in vacuo. The oily residue was purified by preparative HPLC to afford respectively 125 mg (74%) and 14 mg (8%) of each diastereoisomer (as a racemate) as a colourless solid.

(24) MS (ESI): 311 ([M+H].sup.+)

(25) The following tables illustrate in a non-limiting manner examples of compounds according to the invention. The compounds have been prepared according to the preparation examples outlined above or in analogy thereto.

(26) TABLE-US-00001 TABLE 1 Compounds according to formula (Ia) (Ia) Ex N° R.sup.1 R.sup.2 R.sup.3 R.sup.4 R.sup.5 Q LogP Ia-01 1-chlorocyclopropyl OH H H H phenyl 2.41.sup.[a] Ia-02 1-chlorocyclopropyl OH H H H 3-chloro-2-fluorophenyl 2.72.sup.[a] Ia-03 1-chlorocyclopropyl OH H H H 2-chloropyridin-3-yl 1.72.sup.[a];1.68.sup.[b] Ia-04 1-chlorocyclopropyl OH H H H 2-fluorophenyl 2.46.sup.[a] Ia-05 1-chlorocyclopropyl OH H H H 2-chlorophenyl 2.65.sup.[a] Ia-06 1-chlorocyclopropyl OH H H H 2,3-difluorophenyl 2.46.sup.[a] Ia-07 1-chlorocyclopropyl OH H H H 2-(trifluoromethyl)phenyl 3.02.sup.[a] Ia-08 1-methylcyclopropyl OH H H H 2-chlorophenyl 2.80.sup.[a] Ia-09 1-methylcyclopropyl OH H H H 2-bromophenyl 2.92.sup.[a] Ia-10 1-methylcyclopropyl OH H H H phenyl 2.35.sup.[a] Ia-11 1-methylcyclopropyl OH H H H 2-(trifluoromethyl)phenyl 2.94.sup.[a] Ia-12 1-methylcyclopropyl OH H H H 2-methylphenyl 2.75.sup.[a] Ia-13 1-chlorocyclopropyl OH H H H 2,6-difluorophenyl 2.52.sup.[a] Ia-14 1-chlorocyclopropyl OH H H H 2-methoxyphenyl 2.73.sup.[a] Ia-15 1-chlorocyclopropyl OH H H H 2,3-dichlorophenyl 3.19.sup.[a] Ia-16* 1-chlorocyclopropyl OH H CH.sub.3 H 2,5-difluorophenyl 2.66.sup.[a] Ia-17 1-fluorocyclopropyl OH H H H phenyl 2.08.sup.[a] Ia-18* 1-chlorocyclopropyl OH H CH.sub.3 H 2,5-difluorophenyl 2.92.sup.[a] Ia-19 1-fluorocyclopropyl OH H H H 2-chlorophenyl 2.40.sup.[a] Ia-20*.sup.1 1-chlorocyclopropyl OH H CH.sub.3 H 2-fluorophenyl 2.61.sup.[a] Ia-21 1-fluorocyclopropyl OH H H H 2-bromophenyl 2.49.sup.[a] Ia-22*.sup.1 1-chlorocyclopropyl OH H CH.sub.3 H 2-fluorophenyl 2.80.sup.[a] Ia-23 1-fluorocyclopropyl OH H H H 3-bromophenyl 2.59.sup.[a] Ia-24 1-chlorocyclopropyl OH H H H 2-bromophenyl 2.88.sup.[a] Ia-25 1-chlorocyclopropyl OH H CH.sub.3 H 2,3-difluorophenyl 2.96.sup.[a] Ia-26 1-fluorocyclopropyl OH H H H 3-methoxyphenyl 2.11.sup.[a] Ia-27 1-fluorocyclopropyl OH H H H 4-methoxyphenyl 2.08.sup.[a] Ia-28 1-fluorocyclopropyl OH H H H 3-methylphenyl 2.42.sup.[a] Ia-29 1-chlorocyclopropyl OH H H H 5-chloro-2-fluorophenyl 2.86.sup.[a] Ia-30 1-methylcyclopropyl OH H H H 4-methylphenyl 2.73.sup.[a] Ia-31 1-chlorocyclopropyl OH H H H 3,5-difluorophenyl 2.63.sup.[a] Ia-32 1-chlorocyclopropyl OH H H H 2-(trifluoromethoxy)phenyl 3.06.sup.[a] Ia-33 1-fluorocyclopropyl OH H H H 4-methylphenyl 2.44.sup.[a] Ia-34 1-methylcyclopropyl OH H H H 4-methoxyphenyl 2.35.sup.[a] Ia-35 1-chlorocyclopropyl OH H H H 2,4,6-trifluorophenyl 2.64.sup.[a] Ia-36 1-chlorocyclopropyl OH H H H 2,6-difluoro-3-methylphenyl 2.90.sup.[a] Ia-37 1-chlorocyclopropyl OCH.sub.3 H H H 2-chlorophenyl 3.19.sup.[a] Ia-38 1-chlorocyclopropyl OH H H H 3-chloro-2,4-difluorophenyl 2.94.sup.[a] Ia-39 1-chlorocyclopropyl OH H H H 2-chloro-4-fluorophenyl 2.90.sup.[a] Ia-40 1-chlorocyclopropyl OH H H H 4-chloro-2-fluorophenyl 2.90.sup.[a] Ia-41 1-chlorocyclopropyl OH H H H 3-bromo-2-fluorophenyl 2.92.sup.[a] Ia-42 1-chlorocyclopropyl OH H H H 2,5-difluorophenyl 2.52.sup.[a] Ia-43 1-chlorocyclopropyl OH H H H 2,3,5-trifluorophenyl 2.66.sup.[a] Ia-44 1-chlorocyclopropyl OH H H H 2,3,4-trifluorophenyl 2.71.sup.[a] Ia-45 1-chlorocyclopropyl OH H H H 2-chloro-6-fluoro -3- 3.23.sup.[a] methylphenyl Ia-46 1-chlorocyclopropyl OH H H H 2,6-difluoro-3- 2.51.sup.[a] methoxyphenyl Ia-47 1-chlorocyclopropyl OH H H H 3-chlorophenyl 2.82.sup.[a] Ia-48 1-chlorocyclopropyl OH H H H 2,3-difluoro-4- 2.59.sup.[a] methoxyphenyl Ia-49 1-chlorocyclopropyl OH H H H 2,6-difluoro-4- 2.69.sup.[a] methoxyphenyl Ia-50 1-chlorocyclopropyl OH H H H 2,4-difluoro-3- 2.62.sup.[a] methoxyphenyl Ia-51 1-chlorocyclopropyl OH H H H 2,4,5-trifluorophenyl 2.66.sup.[a] Ia-52 1-chlorocyclopropyl OH H H H 3-chloro-4-fluorophenyl 2.90.sup.[a] Ia-53 1-chlorocyclopropyl OH H H H 2,4-difluorophenyl 2.57.sup.[a] Ia-54 1-chlorocyclopropyl OH H H H 2,3,6-trifluorophenyl 2.60.sup.[a] Ia-55 1-chlorocyclopropyl OH H H H 2,3-difluoro-4-methylphenyl 2.92.sup.[a] Ia-56 1-chlorocyclopropyl OH H H H 3,4-difluorophenyl 2.64.sup.[a] Ia-57 1-chlorocyclopropyl OH H H H 4-methylphenyl 2.78.sup.[a] Ia-58 1-chlorocyclopropyl OH H H H 4-methoxyphenyl 2.40.sup.[a] Ia-59 1-chlorocyclopropyl OH H H H 5-fluoropyridin-3-yl 1.53.sup.[a] Ia-60 1-chlorocyclopropyl OH H H H 3-methoxyphenyl 2.42.sup.[a] Ia-61 1-methylcyclopropyl OH H H H 3-methoxyphenyl 2.37.sup.[a] Ia-62 1-chlorocyclopropyl OH H H H 3-bromophenyl 2.92.sup.[a] Ia-63 1-methylcyclopropyl OH H H H 3-bromophenyl 2.84.sup.[a] Ia-64 1-chlorocyclopropyl OH H H H 3-methylphenyl 2.78.sup.[a] Ia-65 1-methylcyclopropyl OH H H H 3-methylphenyl 2.73.sup.[a] Ia-66 1-chlorocyclopropyl OH H H H 2-methylphenyl 2.77.sup.[a] Ia-67 1-chlorocyclopropyl OH H H H 4-bromo-2-fluorophenyl 3.23.sup.[a] Ia-68 1-methylcyclopropyl OH H H H 2-fluorophenyl 2.45.sup.[a] Ia-69 1-chlorocyclopropyl OH H H H 3-fluorophenyl 2.54.sup.[a] Ia-70 1-chlorocyclopropyl OCH.sub.3 H H H 2-bromophenyl 3.23.sup.[a] Ia-71 1-chlorocyclopropyl OH H H H 2-fluoro-3- 3.04.sup.[a] (trifluoromethyl)phenyl Ia-72 1-chlorocyclopropyl OH H H H 2-chloro-6-fluorophenyl 2.90.sup.[a] Ia-73 1-chlorocyclopropyl OH H H H 3-chloropyridin-4-yl 1.65.sup.[a] Ia-74 1-chlorocyclopropyl OH H H H 5-chloropyridin-3-yl 1.86.sup.[a] Ia-75 1-chlorocyclopropyl OH H H H 4-chloro-2,6-difluorophenyl 2.98.sup.[a] Ia-76 1-fluorocyclopropyl OH H H H 2-(trifluoromethyl)phenyl 2.71.sup.[a] *: Compounds Ia-16 and Ia-18 are diastereoisomers *.sup.1: Compounds Ia-20 and Ia-22 are diastereoisomers

(27) TABLE-US-00002 TABLE 2 Compounds according to formula (Ib) (Ib) Ex N° R.sup.1 R.sup.2 R.sup.3 R.sup.4 R.sup.5 Q LogP Ib-01 1-chlorocyclopropyl OH H H H 5-chloropyridin-3-yl 2.13.sup.[a] Ib-02 1-chlorocyclopropyl OH H H H 2-fluorophenyl 2.86.sup.[a] Ib-03 1-chlorocyclopropyl OH H H H 2,3-difluorophenyl 2.82.sup.[a] Ib-04 1-chlorocyclopropyl OH H H H 2-chlorophenyl 3.20.sup.[a] Ib-05 1-chlorocyclopropyl OH H H H 2-chloropyridin-3-yl 2.03.sup.[a] Ib-06 1-chlorocyclopropyl OH H H H 3-chloro-2-fluorophenyl 3.19.sup.[a] Ib-07 1-chlorocyclopropyl OH H H H 2,4,6-trifluorophenyl 3.09.sup.[a] Ib-08 1-chlorocyclopropyl OH H H H 4-chloro-2-fluorophenyl 3.37.sup.[a] Ib-09 1-chlorocyclopropyl OH H H H 2,6-difluoro-3-methylphenyl 3.37.sup.[a] Ib-10 1-chlorocyclopropyl OH H H H 2,3,4-trifluorophenyl 3.11.sup.[a] Ib-11 1-chlorocyclopropyl OH H H H 2,3,5-trifluorophenyl 3.06.sup.[a] Ib-12 1-chlorocyclopropyl OH H H H 3-chloro-2,4-difluorophenyl 3.37.sup.[a] Ib-13 1-chlorocyclopropyl OH H H H 2,3-difluoro-4-methoxyphenyl 2.94.sup.[a] Ib-14 1-chlorocyclopropyl OH H H H 2,4-difluoro-3-methoxyphenyl 3.00.sup.[a] Ib-15 1-chlorocyclopropyl OH H H H 2,6-difluoro-4-methoxyphenyl 3.11.sup.[a] Ib-16 1-chlorocyclopropyl OH H H H 2,4,5-trifluorophenyl 3.09.sup.[a] Ib-17 1-chlorocyclopropyl OH H H H 2,4-difluorophenyl 2.96.sup.[a] Ib-18 1-chlorocyclopropyl OH H H H 3-chloro-4-fluorophenyl 3.33.sup.[a] Ib-19 1-chlorocyclopropyl OH H H H 2,3,6-trifluorophenyl 3.02.sup.[a] Ib-20 1-chlorocyclopropyl OH H H H 2,6-difluoro-3-methoxyphenyl 2.86.sup.[a] Ib-21 1-chlorocyclopropyl OH H H H 2,3-difluoro-4-methylphenyl 3.33.sup.[a] Ib-22 1-chlorocyclopropyl OH H H H 3-chloropyridin-4-yl 1.96.sup.[b] Ib-23 1-chlorocyclopropyl OH H H H 5-fluoropyridin-3-yl 1.76.sup.[a] Ib-24 1-chlorocyclopropyl OH H H H 3,4-difluorophenyl 3.04.sup.[a] Ib-25 1-chlorocyclopropyl OH H H H 2-fluoropyridin-3-yl 1.91.sup.[a]

(28) TABLE-US-00003 TABLE 3 Compounds according to formula (Ia-en), wherein R.sup.3 is hydrogen Ex N° R.sup.1 R.sup.2 R.sup.4′ R.sup.5′ Q LogP Ia-en-01 1-chlorocyclopropyl OH H H 2,5-difluorophenyl 2.54.sup.[a] Ia-en-02 1-chlorocyclopropyl OH H H 2-fluorophenyl 2.46.sup.[a] Ia-en-03 1-chlorocyclopropyl OH H H phenyl 2.46.sup.[a] Ia-en-04 1-chlorocyclopropyl OH CH.sub.3 H 2-fluorophenyl 2.66.sup.[a] Ia-en-05 1-chlorocyclopropyl OH CH.sub.3 H 3-chloro-2-fluorophenyl 3.00.sup.[a] Ia-en-06 1-chlorocyclopropyl OH CH.sub.3 H 2,3-difluorophenyl 2.82.sup.[a] Ia-en-07 1-chlorocyclopropyl OH H CH.sub.3 2,3-difluorophenyl 2.75.sup.[a] Ia-en-08 1-chlorocyclopropyl OH H H 2,3-difluorophenyl 2.57.sup.[a] Ia-en-09 1-chlorocyclopropyl OH H H 2-chlorophenyl 2.71.sup.[a] Ia-en-10 1-chlorocyclopropyl OH H H 3-chloro-2-fluorophenyl 2.82.sup.[a] Ia-en-11* 1-chlorocyclopropyl OH CH.sub.3 H phenyl 2.73 + 2.80.sup.[a] *: mixture of isomer E-Z 70-30

(29) TABLE-US-00004 TABLE 4 Compounds according to formula (Ib-en), wherein R.sup.3 is hydrogen Ex N° R.sup.1 R.sup.2 R.sup.4′ R.sup.5′ Q LogP Ib-en-01 1-chlorocyclopropyl OH H H 2-fluorophenyl 2.96.sup.[a]

(30) TABLE-US-00005 TABLE 5 Compounds according to formula (XVIa) (XVIa) Ex N° R.sup.1′ LogP XVIa-01 1-chlorocyclopropyl 0.99.sup.[a] XVIa-02 1-methylcyclopropyl 0.79.sup.[a] XVIa-03 1-fluorocyclopropyl 0.59.sup.[a]

(31) TABLE-US-00006 TABLE 6 Compounds according to formula (XVIb) (XVIb) Ex N° R.sup.1′ LogP XVIb-01 1-chlorocyclopropyl 1.30.sup.[a] XVIb-02 1-methylcyclopropyl 1.05.sup.[a] XVIb-03 1-fluorocyclopropyl 0.86.sup.[a]

(32) Log P Values:

(33) Measurement of Log P 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]Log P 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]Log P 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]Log P 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).

(34) If more than one Log P value is available within the same method, all the values are given and separated by “+”.

(35) 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.

(36) NMR-Peak Lists

(37) .sup.1H-NMR data of selected examples are written in form of .sup.1H-NMR-peak lists. To each signal peak are listed the δ-value in ppm and the signal intensity in round brackets. Between the δ-value signal intensity pairs are semicolons as delimiters.

(38) The peak list of an example has therefore the form:

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

(40) 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.

(41) For calibrating chemical shift for .sup.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.

(42) The .sup.1H-NMR peak lists are similar to classical .sup.1H-NMR prints and contains therefore usually all peaks, which are listed at classical NMR-interpretation.

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

(44) 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 .sup.1H-NMR peak lists and have usually on average a high intensity.

(45) 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%).

(46) 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”.

(47) One skilled in the art, 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 .sup.1H-NMR interpretation.

(48) 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.

(49) Ia-01: .sup.1H-NMR (300.2 MHz, CDCl.sub.3):

(50) δ=8.8124 (3.1); 7.4263 (0.4); 7.4142 (0.3); 7.4078 (1.4); 7.4019 (0.8); 7.3962 (0.6); 7.3899 (1.5); 7.3828 (3.5); 7.3757 (1.6); 7.3635 (1.0); 7.3445 (2.3); 7.3373 (1.8); 7.3189 (1.1); 7.3131 (0.9); 7.2988 (10.7); 5.0090 (1.8); 4.9612 (2.4); 4.6641 (1.9); 4.6163 (1.5); 3.4710 (1.5); 3.4247 (1.8); 2.9562 (1.7); 2.9099 (1.5); 2.3696 (3.5); 1.5931 (16.0); 0.8136 (0.5); 0.8083 (0.5); 0.7975 (0.6); 0.7900 (0.8); 0.7739 (0.6); 0.7561 (0.7); 0.6362 (0.5); 0.6198 (0.5); 0.6136 (0.7); 0.5971 (0.9); 0.5793 (0.7); 0.5739 (1.1); 0.5686 (1.1); 0.5614 (0.6); 0.5453 (0.9); 0.5267 (0.8); 0.5222 (0.6); 0.5041 (0.6); 0.4497 (0.8); 0.4437 (0.4); 0.4335 (0.6); 0.4151 (0.8); 0.4096 (0.6); 0.3989 (0.4); 0.3918 (0.4); 0.0485 (0.4); 0.0376 (10.8); 0.0267 (0.4)

(51) Ia-02: .sup.1H-NMR (300.2 MHz. CDCl.sub.3):

(52) δ=8.9425 (1.6); 8.8963 (16.0); 7.4294 (0.6); 7.3966 (1.9); 7.3914 (3.1); 7.3833 (3.0); 7.3655 (6.2); 7.3572 (5.7); 7.3473 (2.7); 7.3415 (4.6); 7.3353 (4.4); 7.3129 (0.6); 7.3070 (0.6); 7.2989 (2.4); 7.1309 (3.6); 7.1285 (3.6); 7.1047 (5.7); 7.1023 (5.6); 7.0901 (0.9); 7.0870 (0.9); 7.0786 (2.6); 7.0762 (2.5); 7.0636 (0.9); 7.0610 (0.8); 7.0368 (0.5); 5.3237 (2.0); 5.2297 (0.8); 5.1772 (6.8); 5.1293 (7.7); 4.8871 (0.8); 4.8395 (0.6); 4.5683 (7.2); 4.5204 (6.2); 3.4400 (3.4); 3.4370 (3.3); 3.3892 (6.2); 3.3428 (7.1); 3.3351 (7.1); 3.2726 (5.1); 3.2668 (5.0); 3.2252 (3.0); 3.2193 (3.0); 2.0353 (1.0); 1.9878 (0.7); 1.5532 (1.7); 1.5293 (1.6); 1.2733 (0.6); 0.8244 (4.5); 0.7934 (9.8); 0.7632 (8.0); 0.5824 (2.3); 0.5626 (3.0); 0.5567 (2.6); 0.5478 (1.9); 0 5333 (3.5); 0.5221 (1.6); 0.5022 (1.7); 0.4006 (2.4); 0.3808 (2.5); 0.3708 (3.7); 0.3492 (2.8); 0.3399 (2.3); 0.3202 (1.6); 0.1512 (0.5); 0.0171 (2.0)

(53) Ia-03: .sup.1H-NMR (601.6 MHz, CD.sub.3CN):

(54) δ=8.9133 (1.0); 8.8488 (10.2); 8.3200 (5.6); 8.3138 (5.2); 8.2702 (1.0); 7.9249 (5.9); 7.9129 (5.3); 7.6749 (0.8); 7.6629 (0.8); 7.5475 (0.4); 7.5357 (0.4); 7.3484 (4.6); 7.3406 (5.0); 7.3367 (4.7); 7.3288 (3.6); 7.2820 (0.8); 7.2740 (0.9); 7.2624 (0.6); 6.8752 (0.4); 5.1587 (6.1); 5.1345 (6.3); 5.1194 (1.2); 4.9922 (0.6); 4.9675 (0.5); 4.8816 (3.6); 4.4961 (6.4); 4.4719 (5.8); 3.6531 (0.5); 3.6246 (0.6); 3.5196 (6.4); 3.4961 (16.0); 3.4383 (1.0); 3.4097 (0.8); 3.3264 (6.5); 3.3202 (8.3); 3.2957 (8.9); 3.2822 (16.0); 3.2750 (14.8); 3.1644 (0.4); 2.2519 (35.2); 2.1248 (0.4); 2.0570 (0.3); 1.9489 (7.0); 1.9458 (7.7); 1.2840 (0.6); 1.2673 (0.6); 0.9540 (0.5); 0.9450 (0.4); 0.9150 (0.6); 0.9036 (0.6); 0.8884 (0.7); 0.8723 (0.8); 0.8619 (0.9); 0.8183 (6.0); 0.8116 (6.8); 0.8008 (8.6); 0.7888 (6.3); 0.7835 (5.6); 0.7467 (1.5); 0.7288 (1.0); 0.6228 (0.6); 0.6044 (1.1); 0.5948 (1.8); 0.5910 (2.0); 0.5765 (1.4); 0.5628 (3.0); 0.5523 (4.0); 0.5492 (4.1); 0.5399 (3.9); 0.5361 (3.8); 0.5234 (2.4); 0.3664 (2.7); 0.3556 (4.1); 0.3489 (3.8); 0.3440 (3.8); 0.3391 (3.7); 0.3272 (2.3); −0.0002 (1.0)

(55) Ia-04: .sup.1H-NMR (499.9 MHz, CDCl.sub.3):

(56) δ=8.7891 (16.0); 7.4087 (2.3); 7.4054 (2.5); 7.3935 (4.5); 7.3902 (4.7); 7.3783 (2.5); 7.3749 (2.6); 7.3397 (1.5); 7.3361 (1.5); 7.3288 (1.7); 7.3248 (3.1); 7.3212 (2.4); 7.3128 (2.5); 7.3087 (3.3); 7.3048 (1.8); 7.2974 (1.9); 7.2939 (1.6); 7.2628 (17.7); 7.1923 (0.4); 7.1804 (3.6); 7.1783 (3.9); 7.1654 (5.7); 7.1633 (6.0); 7.1504 (2.7); 7.1483 (2.7); 7.1421 (0.4); 7.1179 (3.1); 7.1163 (3.0); 7.1013 (3.0); 7.0980 (3.9); 7.0808 (2.6); 7.0791 (2.5); 5.0851 (8.6); 5.0563 (9.3); 4.5071 (8.3); 4.4783 (7.5); 3.3756 (4.5); 3.3469 (6.0); 3.2027 (5.1); 3.2000 (5.2); 3.1741 (3.8); 3.1712 (3.8); 2.7319 (8.9); 2.7220 (8.8); 1.5881 (24.9); 0.8046 (1.5); 0.7923 (3.5); 0.7899 (2.4); 0.7831 (2.0); 0.7774 (3.8); 0.7711 (5.3); 0.7683 (3.1); 0.7578 (5.2); 0.7561 (5.2); 0.7513 (4.0); 0.7458 (1.9); 0.7388 (2.5); 0.7365 (4.3); 0.7243 (2.1); 0.5739 (2.9); 0.5619 (3.5); 0.5592 (3.1); 0.5523 (2.7); 0.5470 (3.3); 0.5404 (3.0); 0.5376 (2.5); 0.5255 (2.4); 0.4039 (2.9); 0.3918 (2.9); 0.3889 (3.2); 0.3825 (3.0); 0.3770 (2.7); 0.3703 (2.7); 0.3675 (2.8); 0.3554 (2.1); 0.0063 (0.7); −0.0002 (16.0); −0.0067 (0.7)

(57) Ia-05: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

(58) δ=9.1370 (16.0); 7.6228 (3.2); 7.6167 (3.3); 7.6042 (2.6); 7.5993 (3.6); 7.4764 (3.3); 7.4721 (2.4); 7.4700 (2.0); 7.4586 (4.1); 7.4531 (4.4); 7.3562 (0.9); 7.3515 (1.4); 7.3378 (4.0); 7.3332 (3.9); 7.3268 (4.1); 7.3207 (6.4); 7.3148 (3.3); 7.3082 (3.6); 7.3028 (3.1); 7.2897 (1.1); 7.2845 (0.8); 5.4601 (10.3); 5.1144 (4.6); 5.0786 (4.9); 4.2995 (5.9); 4.2637 (5.5); 3.5789 (5.1); 3.5435 (5.9); 3.3255 (31.5); 3.1369 (5.4); 3.1015 (4.6); 2.6711 (0.3); 2.5416 (3.0); 2.5246 (0.7); 2.5111 (19.4); 2.5067 (39.1); 2.5022 (51.0); 2.4977 (36.1); 2.4932 (16.9); 2.3290 (0.3); 0.9531 (1.1); 0.9380 (1.7); 0.9348 (1.7); 0.9262 (1.7); 0.9197 (1.8); 0.9112 (1.9); 0.9078 (1.8); 0.8928 (1.5); 0.7414 (1.2); 0.7260 (1.6); 0.7232 (1.8); 0.7147 (2.0); 0.7082 (1.6); 0.6995 (1.9); 0.6965 (2.1); 0.6816 (1.4); 0.4594 (1.4); 0.4454 (1.9); 0.4410 (1.8); 0.4328 (1.7); 0.4270 (2.0); 0.4188 (1.7); 0.4144 (1.4); 0.4003 (1.3); 0.2570 (1.4); 0.2427 (1.6); 0.2388 (1.8); 0.2301 (1.8); 0.2247 (1.7); 0.2159 (1.6); 0.2119 (1.6); 0.1977 (1.1); 0.0079 (2.4); −0.0002 (70.1); −0.0086 (2.3)

(59) Ia-06: .sup.1H-NMR (300.2 MHz, CDCl.sub.3):

(60) δ=8.9198 (0.4); 8.8717 (16.0); 7.2987 (4.2); 7.2356 (1.0); 7.2298 (1.5); 7.2252 (1.3); 7.2036 (3.9); 7.1806 (4.5); 7.1697 (1.3); 7.1579 (3.0); 7.1483 (4.4); 7.1450 (5.4); 7.1264 (6.5); 7.1185 (3.7); 7.1041 (2.2); 7.0916 (0.9); 7.0747 (0.8); 5.1789 (0.4); 5.1636 (7.4); 5.1157 (8.6); 4.5609 (7.7); 4.5130 (6.6); 3.4456 (3.1); 3.4417 (3.2); 3.3981 (5.6); 3.3942 (5.7); 3.2857 (5.0); 3.2795 (5.0); 3.2383 (2.8); 3.2320 (2.9); 3.0673 (6.6); 3.0593 (6.7); 1.7784 (1.6); 1.5673 (0.4); 1.5433 (0.4); 1.2809 (0.8); 0.8655 (0.5); 0.8453 (3.3); 0.8366 (3.7); 0.8187 (4.0); 0.8105 (8.9); 0.8022 (4.9); 0.7827 (5.5); 0.7773 (5.1); 0.7571 (1.0); 0.5990 (2.6); 0.5791 (3.3); 0.5745 (2.8); 0.5632 (2.1); 0.5530 (3.1); 0.5448 (2.6); 0.5386 (1.8); 0.5186 (2.0); 0.4141 (2.7); 0.3942 (2.5); 0.3861 (2.7); 0.3813 (3.0); 0.3678 (2.2); 0.3599 (2.5); 0.3534 (2.4); 0.3334 (1.7); 0.0262 (3.3)

(61) Ia-07: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(62) δ=8.9930 (3.2); 7.7323 (0.5); 7.5146 (1.4); 7.4597 (0.7); 7.4407 (0.9); 7.4077 (0.6); 7.3880 (1.0); 7.3397 (0.8); 7.3206 (1.0); 7.3013 (0.4); 5.4561 (2.9); 4.8215 (1.1); 4.7855 (1.3); 4.3194 (1.3); 4.2833 (1.1); 3.1066 (16.0); 3.0769 (1.1); 3.0423 (1.3); 2.8498 (1.2); 2.8152 (0.9); 2.6700 (3.2); 2.5105 (3.0); 2.2855 (3.2); 2.2814 (4.2); 2.2772 (3.3); 0.1929 (0.4); 0.1839 (0.7); 0.1755 (1.0); 0.1666 (3.6); −0.0002 (0.7); −0.0180 (0.4); −0.0269 (0.3)

(63) Ia-08: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(64) δ=9.1781 (7.4); 7.6898 (1.6); 7.6839 (1.7); 7.6714 (1.6); 7.6665 (2.0); 7.5719 (1.7); 7.5675 (1.5); 7.5541 (2.1); 7.5489 (2.3); 7.4418 (0.5); 7.4375 (0.7); 7.4235 (2.0); 7.4192 (2.0); 7.4122 (2.2); 7.4064 (3.4); 7.4011 (1.9); 7.3936 (1.9); 7.3885 (1.7); 7.3752 (0.6); 7.3702 (0.5); 5.0967 (2.6); 5.0610 (2.8); 4.7673 (6.1); 4.3159 (2.9); 4.2802 (2.7); 3.4396 (31.0); 3.4115 (3.2); 3.1453 (2.9); 3.1101 (2.4); 3.0028 (1.0); 2.8433 (0.9); 2.6181 (5.8); 2.6141 (7.6); 2.6100 (5.9); 1.3648 (16.0); 0.5424 (0.5); 0.5288 (0.9); 0.5183 (1.4); 0.5078 (1.0); 0.4942 (0.7); 0.0230 (0.6); 0.0092 (1.0); −0.0002 (1.5); −0.0135 (1.1); −0.0234 (0.9); −0.0993 (0.7); −0.1093 (0.9); −0.1228 (1.4); −0.1329 (0.9); −0.1462 (0.6); −0.2979 (0.8); −0.3074 (0.9); −0.3122 (1.0); −0.3211 (1.5); −0.3300 (0.9); −0.3349 (0.9); −0.3444 (0.7)

(65) Ia-09: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(66) δ=9.1390 (7.5); 7.7165 (2.3); 7.6966 (2.7); 7.6792 (1.9); 7.6757 (1.9); 7.6600 (2.2); 7.6564 (2.2); 7.4587 (1.2); 7.4398 (2.4); 7.4214 (1.4); 7.3038 (1.3); 7.3000 (1.3); 7.2841 (2.0); 7.2812 (2.0); 7.2655 (1.0); 7.2617 (0.9); 5.0872 (2.5); 5.0516 (2.7); 4.7390 (5.8); 4.2521 (2.9); 4.2165 (2.7); 3.4727 (2.4); 3.4374 (2.9); 3.4083 (34.5); 3.1255 (2.8); 3.0902 (2.3); 2.9716 (1.5); 2.8122 (1.3); 2.5870 (7.0); 2.5830 (9.2); 2.5789 (7.1); 1.3418 (16.0); 1.2891 (0.5); 0.5755 (0.5); 0.5620 (0.9); 0.5515 (1.4); 0.5402 (1.0); 0.5278 (0.7); 0.0232 (0.6); 0.0094 (1.0); −0.0002 (1.4); −0.0135 (1.1); −0.0235 (0.8); −0.1160 (0.6); −0.1262 (0.9); −0.1396 (1.4); −0.1497 (0.9); −0.1631 (0.6); −0.3111 (0.7); −0.3208 (0.9); −0.3254 (1.0); −0.3344 (1.5); −0.3433 (0.9); −0.3483 (0.9); −0.3576 (0.7)

(67) Ia-10: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(68) δ=8.8636 (4.8); 7.1477 (1.9); 7.1300 (3.3); 7.0877 (1.5); 7.0699 (3.1); 7.0511 (1.8); 7.0222 (1.2); 7.0044 (1.4); 6.9864 (0.5); 4.7262 (1.7); 4.6905 (1.9); 4.4121 (4.1); 4.0267 (1.9); 3.9910 (1.8); 3.1141 (16.0); 2.7907 (1.0); 2.7563 (2.2); 2.7078 (2.2); 2.6754 (1.6); 2.5168 (0.9); 2.2916 (3.2); 2.2877 (4.2); 2.2835 (3.2); 0.9939 (10.7); 0.0148 (0.6); −0.0002 (1.0); −0.4875 (0.8); −0.4969 (1.9); −0.5090 (2.0); −0.5195 (0.9); −0.5336 (0.4); −0.7077 (0.7); −0.7148 (0.8); −0.7208 (1.1); −0.7354 (0.7); −0.7419 (0.4)

(69) Ia-11: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(70) δ=9.0018 (7.6); 7.8580 (1.1); 7.6330 (3.3); 7.5654 (1.6); 7.5465 (2.1); 7.4949 (1.3); 7.4754 (2.4); 7.4393 (1.9); 7.4202 (2.4); 7.4011 (0.9); 4.8719 (2.6); 4.8362 (2.8); 4.7197 (6.5); 4.1919 (2.9); 4.1561 (2.6); 3.2321 (37.1); 2.9602 (8.7); 2.7956 (6.7); 2.6361 (6.0); 2.4111 (6.9); 2.4070 (9.2); 2.4028 (7.0); 1.1316 (16.0); 0.0223 (0.5); 0.0100 (0.8); −0.0002 (1.4); −0.0084 (0.9); −0.0140 (0.9); −0.0239 (0.7); −0.3467 (0.5); −0.3602 (0.9); −0.3692 (1.3); −0.3843 (0.9); −0.3911 (1.0); −0.4024 (1.1); −0.4106 (0.9); −0.4239 (1.5); −0.4333 (1.1); −0.4471 (0.7); −0.5619 (0.8); −0.5704 (0.9); −0.5776 (1.0); −0.5845 (1.5); −0.5925 (0.9); −0.5985 (0.8); −0.6057 (0.6)

(71) Ia-12: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(72) δ=9.1510 (7.5); 8.0396 (0.4); 7.4486 (1.4); 7.4394 (1.7); 7.4264 (1.8); 7.2757 (0.7); 7.2625 (1.5); 7.2526 (2.7); 7.2455 (1.8); 7.2369 (5.0); 7.2281 (3.7); 7.2232 (3.1); 7.2142 (2.6); 5.0925 (2.7); 5.0568 (3.0); 4.4902 (6.9); 4.3394 (2.9); 4.3036 (2.7); 3.4145 (27.7); 3.2055 (2.2); 3.1704 (3.1); 3.0258 (3.1); 2.9907 (2.2); 2.9778 (2.7); 2.8184 (2.3); 2.5930 (5.5); 2.5891 (7.3); 2.5850 (5.7); 2.4088 (17.8); 2.3772 (0.5); 1.3293 (16.0); 1.2920 (0.5); 0.5385 (0.6); 0.5251 (0.9); 0.5148 (1.4); 0.5044 (0.9); 0.4913 (0.7); 0.0228 (0.6); 0.0090 (1.0); −0.0002 (1.5); −0.0134 (1.1); −0.0233 (0.8); −0.1395 (0.7); −0.1502 (1.0); −0.1629 (1.4); −0.1731 (1.0); −0.1860 (0.7); −0.3276 (0.8); −0.3372 (0.9); −0.3419 (1.0); −0.3507 (1.5); −0.3597 (0.9); −0.3645 (0.9); −0.3739 (0.7)

(73) Ia-13: .sup.1H-NMR (300.2 MHz, CDCl.sub.3):

(74) δ=8.8147 (16.0); 7.3931 (1.0); 7.3711 (2.2); 7.3652 (2.2); 7.3432 (4.6); 7.3375 (1.9); 7.3209 (2.2); 7.3153 (3.0); 7.2984 (9.8); 7.0492 (0.7); 7.0438 (1.1); 7.0314 (7.1); 7.0211 (1.2); 7.0052 (10.4); 6.9882 (1.2); 6.9783 (5.8); 6.9656 (0.9); 5.2615 (7.5); 5.2135 (8.4); 4.4717 (7.0); 4.4238 (6.2); 3.5303 (3.8); 3.4818 (6.3); 3.3387 (5.8); 3.2902 (3.6); 2.7543 (3.9); 2.0765 (0.4); 2.0422 (0.6); 1.2909 (0.4); 1.0026 (1.1); 0.9824 (3.4); 0.9769 (2.0); 0.9663 (1.5); 0.9601 (4.0); 0.9567 (4.5); 0.9465 (4.5); 0.9400 (3.7); 0.9357 (4.6); 0.9258 (4.4); 0.9201 (4.6); 0.9017 (4.5); 0.8815 (1.6); 0.6358 (2.7); 0.6158 (3.4); 0.6094 (2.6); 0.6019 (2.6); 0.5899 (3.0); 0.5813 (3.0); 0.5755 (2.2); 0.5553 (2.3); 0.4248 (2.8); 0.4045 (3.0); 0.4007 (3.3); 0.3884 (2.8); 0.3799 (2.6); 0.3687 (2.5); 0.3641 (2.8); 0.3439 (2.0); 0.0429 (0.4); 0.0321 (9.7); 0.0215 (0.4)

(75) Ia-14: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(76) δ=8.9811 (5.9); 7.8289 (0.6); 7.2702 (1.4); 7.2671 (1.6); 7.2517 (1.6); 7.2484 (1.7); 7.1687 (0.7); 7.1649 (0.7); 7.1482 (1.6); 7.1297 (1.0); 7.1259 (1.0); 6.9041 (2.2); 6.8838 (1.9); 6.8292 (1.2); 6.8108 (2.1); 6.7924 (1.0); 5.0384 (4.2); 4.9483 (1.9); 4.9122 (2.0); 4.0527 (2.4); 4.0167 (2.2); 3.6979 (16.0); 3.6653 (0.3); 3.4290 (2.0); 3.3944 (2.2); 3.2037 (25.6); 2.7668 (3.6); 2.7108 (2.1); 2.6761 (1.9); 2.6073 (3.4); 2.3820 (5.0); 2.3781 (6.7); 2.3741 (5.2); 0.8333 (0.4); 0.8158 (0.8); 0.8065 (0.7); 0.8001 (0.8); 0.7907 (0.9); 0.7734 (0.6); 0.5683 (0.5); 0.5507 (0.8); 0.5417 (0.8); 0.5354 (0.7); 0.5241 (1.0); 0.5087 (0.6); 0.2777 (0.6); 0.2637 (0.8); 0.2598 (0.8); 0.2510 (0.8); 0.2458 (0.8); 0.2373 (0.8); 0.2333 (0.7); 0.2192 (0.6); 0.0268 (0.6); 0.0122 (0.7); 0.0088 (0.8); −0.0002 (0.8); −0.0050 (0.8); −0.0141 (0.8); −0.0179 (0.8); −0.0321 (0.5)

(77) Ia-15: .sup.1H-NMR (300.2 MHz, CDCl.sub.3):

(78) δ=8.8413 (13.9); 7.4846 (11.9); 7.4584 (16.0); 7.2986 (5.3); 7.2790 (5.5); 7.2542 (5.3); 7.2515 (5.0); 7.2267 (3.5); 5.2157 (8.1); 5.1678 (9.2); 4.4632 (7.5); 4.4153 (6.7); 3.7664 (6.7); 3.7186 (8.2); 3.3348 (7.1); 3.2870 (5.8); 3.0126 (2.2); 2.0722 (1.1); 2.0401 (4.9); 1.3115 (0.3); 1.2878 (0.7); 0.9231 (3.7); 0.9193 (3.8); 0.8944 (5.1); 0.8908 (8.1); 0.8875 (5.5); 0.8606 (8.3); 0.6246 (2.2); 0.6146 (0.4); 0.6047 (2.7); 0.5951 (2.8); 0.5760 (2.6); 0.5726 (2.9); 0.5640 (1.6); 0.5440 (1.8); 0.4424 (2.3); 0.4224 (2.2); 0.4164 (2.7); 0.4077 (2.1); 0.3933 (2.4); 0.3912 (2.2); 0.3817 (2.0); 0.3617 (1.5); 0.0293 (5.4)

(79) Ia-16: .sup.1H-NMR (499.9 MHz, CDCl.sub.3):

(80) δ=8.7162 (10.7); 7.0953 (2.0); 7.0544 (1.9); 7.0480 (2.4); 7.0436 (2.4); 7.0366 (3.3); 7.0294 (2.4); 7.0251 (2.3); 7.0187 (1.9); 6.8545 (1.4); 6.8451 (1.6); 6.8361 (3.2); 6.8268 (3.2); 6.8173 (2.4); 6.8080 (2.2); 6.7809 (1.4); 6.7740 (2.2); 6.7665 (2.7); 6.7588 (2.9); 6.7417 (1.4); 6.7350 (0.8); 4.9992 (6.2); 4.9706 (7.3); 4.6638 (6.3); 4.6353 (5.4); 3.8060 (1.4); 3.0425 (4.3); 1.8675 (0.4); 1.3364 (16.0); 1.3221 (15.9); 1.0787 (0.8); 0.1952 (1.4); 0.1886 (1.8); 0.1790 (3.0); 0.1734 (3.0); 0.1652 (2.4); 0.1453 (0.8); 0.0224 (1.5); −0.0002 (5.7); −0.0100 (5.5); −0.0297 (1.6); −0.1050 (0.6); −0.1789 (2.6); −0.2830 (2.6); −0.2953 (1.6)

(81) Ia-17: .sup.1H-NMR (300.2 MHz, CDCl.sub.3):

(82) δ=8.7337 (16.0); 7.4468 (0.4); 7.4346 (1.4); 7.4243 (2.0); 7.4187 (1.5); 7.4055 (7.9); 7.3999 (4.8); 7.3940 (3.5); 7.3877 (8.3); 7.3807 (18.7); 7.3739 (7.2); 7.3616 (3.9); 7.3415 (1.3); 7.3355 (1.3); 7.3282 (0.9); 7.3101 (10.4); 7.2984 (36.3); 7.2844 (6.9); 7.2790 (5.3); 7.2319 (0.3); 5.3373 (2.0); 4.8846 (4.6); 4.8790 (4.7); 4.8369 (6.8); 4.8314 (6.9); 4.6474 (6.2); 4.6426 (6.3); 4.5998 (4.2); 4.5950 (4.2); 3.3368 (4.1); 3.3311 (4.2); 3.2905 (5.0); 3.2847 (5.2); 2.9134 (5.3); 2.9085 (5.4); 2.8670 (4.3); 2.8622 (4.4); 2.2992 (7.9); 1.5990 (1.2); 1.2904 (0.6); 0.8935 (1.0); 0.8711 (1.4); 0.8681 (1.4); 0.8527 (1.6); 0.8463 (1.3); 0.8312 (2.0); 0.8276 (2.3); 0.8066 (2.1); 0.8002 (1.5); 0.7848 (1.6); 0.7784 (1.3); 0.7634 (1.9); 0.7600 (2.0); 0.7389 (1.7); 0.7046 (1.4); 0.6848 (1.8); 0.6808 (1.9); 0.6606 (1.9); 0.6397 (2.4); 0.6194 (2.9); 0.6152 (2.1); 0.5992 (1.1); 0.5949 (1.9); 0.5792 (1.1); 0.5749 (1.3); 0.5542 (1.3); 0.4170 (1.2); 0.3922 (1.3); 0.3788 (2.2); 0.3707 (0.9); 0.3570 (3.2); 0.3441 (2.1); 0.3329 (2.0); 0.3221 (2.4); 0.2984 (1.7); 0.2803 (1.9); 0.2605 (1.9); 0.2557 (2.0); 0.2453 (2.3); 0.2353 (1.8); 0.2255 (2.2); 0.2209 (2.8); 0.2076 (1.1); 0.2003 (1.9); 0.1875 (1.2); 0.1828 (1.2); 0.1621 (1.0); 0.1034 (0.5); 0.0479 (1.6); 0.0371 (43.3); 0.0262 (1.9); −0.0291 (0.4)

(83) Ia-18: .sup.1H-NMR (499.9 MHz, CDCl.sub.3):

(84) δ=8.7699 (16.0); 7.2697 (6.3); 7.0708 (1.9); 7.0616 (2.1); 7.0526 (4.6); 7.0434 (4.7); 7.0343 (3.2); 7.0251 (3.0); 6.9897 (1.7); 6.9825 (2.7); 6.9751 (3.5); 6.9671 (3.6); 6.9606 (2.6); 6.9574 (2.6); 6.9499 (1.9); 6.9427 (1.2); 5.0710 (7.7); 5.0419 (8.3); 4.0819 (9.7); 4.0528 (8.3); 2.9483 (9.3); 2.0108 (0.5); 1.4709 (20.2); 1.4566 (20.7); 1.2609 (2.3); 1.2481 (3.3); 1.2460 (3.3); 1.2386 (3.0); 1.2333 (3.2); 1.2260 (3.6); 1.2239 (3.4); 1.2111 (2.7); 1.0129 (2.5); 0.9990 (3.8); 0.9910 (3.4); 0.9860 (3.1); 0.9775 (4.1); 0.9642 (2.7); 0.3433 (2.0); 0.3298 (3.2); 0.3215 (2.7); 0.3156 (2.8); 0.3084 (3.2); 0.2938 (2.1); −0.0002 (4.8); −0.1048 (1.6); −0.1185 (3.0); −0.1273 (2.5); −0.1314 (2.5); −0.1403 (3.0); −0.1539 (1.6)

(85) Ia-19: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(86) δ=9.1792 (16.0); 7.5901 (3.6); 7.5823 (3.6); 7.5669 (4.7); 7.4813 (3.7); 7.4644 (3.9); 7.4582 (5.1); 7.3477 (1.4); 7.3298 (8.6); 7.3206 (9.1); 7.3118 (7.4); 7.2935 (1.3); 5.5194 (10.8); 4.9831 (4.5); 4.9474 (5.2); 4.4727 (5.8); 4.4369 (5.1); 3.3378 (249.1); 3.2925 (8.2); 3.2473 (8.4); 3.2122 (3.6); 2.9111 (1.5); 2.7519 (1.4); 2.5220 (20.2); 0.7199 (0.6); 0.7041 (0.9); 0.6900 (1.1); 0.6851 (1.1); 0.6708 (1.8); 0.6560 (1.4); 0.6345 (1.3); 0.6211 (1.5); 0.6043 (1.0); 0.5515 (0.6); 0.5320 (1.4); 0.5250 (1.6); 0.5156 (1.4); 0.5051 (2.5); 0.4895 (3.6); 0.4771 (2.6); 0.4620 (2.2); 0.4416 (2.1); 0.4266 (1.9); 0.4085 (1.3); 0.3961 (1.1); 0.3770 (0.6); 0.0375 (0.8); 0.0208 (1.4); 0.0132 (1.9); −0.0002 (2.2); −0.0209 (1.8); −0.0475 (0.8)

(87) Ia-20: .sup.1H-NMR (499.9 MHz, CDCl.sub.3):

(88) δ=8.8645 (8.0); 7.4856 (2.3); 7.4826 (2.4); 7.4703 (4.4); 7.4675 (4.3); 7.4553 (2.4); 7.4523 (2.2); 7.2836 (1.3); 7.2807 (1.5); 7.2672 (9.6); 7.2540 (2.8); 7.2422 (1.4); 7.2393 (1.3); 7.1275 (3.2); 7.1131 (5.1); 7.0984 (2.4); 7.0719 (3.1); 7.0553 (3.0); 7.0540 (3.0); 7.0499 (3.3); 7.0333 (2.5); 5.1838 (6.8); 5.1554 (7.8); 4.8265 (5.8); 4.7981 (4.9); 4.1286 (0.5); 4.1143 (0.5); 3.9795 (0.9); 3.2614 (2.7); 3.2495 (3.7); 3.2375 (2.6); 3.0482 (1.7); 2.9224 (16.0); 2.0446 (2.0); 1.9994 (0.4); 1.9874 (1.0); 1.9755 (1.4); 1.9636 (0.9); 1.9517 (0.4); 1.5317 (15.8); 1.5172 (15.2); 1.2733 (0.8); 1.2589 (1.8); 1.2448 (0.7); 0.3270 (0.9); 0.3138 (1.7); 0.3065 (1.7); 0.2943 (2.0); 0.2806 (1.2); 0.1922 (1.8); 0.1805 (1.7); 0.1605 (1.0); 0.1185 (1.3); 0.1050 (1.7); 0.0975 (1.8); 0.0847 (1.9); 0.0715 (0.9); −0.0002 (6.1); −0.0636 (1.2); −0.0759 (1.9); −0.0835 (1.7); −0.0950 (1.5)

(89) Ia-21: .sup.1H-NMR (300.2 MHz, CDCl.sub.3):

(90) δ=8.7403 (16.0); 7.6467 (5.2); 7.6432 (5.2); 7.6202 (5.9); 7.6164 (5.8); 7.5123 (3.8); 7.5068 (4.1); 7.4868 (5.6); 7.4813 (5.8); 7.3885 (3.0); 7.3845 (3.0); 7.3637 (5.8); 7.3598 (5.5); 7.3385 (3.1); 7.3345 (2.8); 7.2985 (18.9); 7.2511 (3.4); 7.2453 (3.4); 7.2253 (4.5); 7.2200 (4.4); 7.1999 (2.4); 7.1941 (2.2); 5.3360 (0.7); 5.0391 (4.9); 5.0327 (4.9); 4.9914 (6.0); 4.9850 (6.0); 4.5810 (5.6); 4.5758 (5.6); 4.5333 (4.6); 4.5281 (4.6); 3.4960 (3.2); 3.4914 (3.2); 3.4480 (7.0); 3.4435 (6.9); 3.3665 (7.9); 3.3183 (3.7); 2.9938 (1.3); 2.9169 (1.2); 2.8843 (0.7); 2.7854 (9.2); 1.6239 (6.1); 0.9493 (0.8); 0.9339 (1.2); 0.9291 (1.2); 0.9159 (1.4); 0.9082 (1.4); 0.9010 (1.7); 0.8899 (1.5); 0.8684 (2.8); 0.8605 (1.3); 0.8485 (2.0); 0.8409 (1.3); 0.8224 (1.4); 0.8145 (0.9); 0.8031 (1.5); 0.7091 (1.1); 0.6884 (1.3); 0.6831 (1.7); 0.6700 (0.7); 0.6625 (2.0); 0.6439 (2.5); 0.6291 (2.6); 0.6232 (3.3); 0.6178 (2.2); 0.6075 (2.0); 0.5980 (2.5); 0.5912 (2.3); 0.5800 (4.6); 0.5716 (5.4); 0.5552 (2.3); 0.5451 (1.7); 0.5357 (1.8); 0.5294 (1.0); 0.5097 (1.1); 0.3056 (1.7); 0.2850 (1.4); 0.2696 (2.6); 0.2591 (2.2); 0.2500 (2.0); 0.2426 (1.4); 0.2338 (1.5); 0.2250 (2.3); 0.2142 (1.3); 0.2081 (1.8); 0.1741 (0.4); 0.0460 (0.8); 0.0354 (22.6); 0.0244 (0.8)

(91) Ia-22: .sup.1H-NMR (499.9 MHz, CDCl.sub.3):

(92) δ=8.8447 (16.0); 7.7614 (0.3); 7.7432 (0.3); 7.6133 (3.1); 7.3974 (1.6); 7.3946 (1.7); 7.3825 (4.6); 7.3682 (8.4); 7.3557 (2.8); 7.3529 (2.5); 7.2972 (6.0); 7.2826 (9.5); 7.2679 (4.1); 7.1931 (4.9); 7.1735 (6.6); 7.1560 (4.2); 5.5773 (1.2); 5.1868 (9.1); 5.1576 (9.7); 4.2271 (1.2); 4.2129 (3.0); 4.1987 (3.6); 4.1845 (2.3); 4.1602 (11.4); 4.1309 (10.6); 2.9888 (1.3); 2.1318 (6.3); 2.1006 (1.7); 1.9156 (0.5); 1.9085 (0.5); 1.6526 (0.6); 1.6455 (0.6); 1.5866 (22.1); 1.5722 (22.2); 1.3631 (1.7); 1.3491 (5.4); 1.3350 (5.5); 1.3283 (3.8); 1.3230 (4.0); 1.3157 (4.7); 1.3138 (4.4); 1.3009 (3.4); 1.0954 (3.5); 1.0812 (5.1); 1.0736 (4.5); 1.0685 (4.0); 1.0595 (5.4); 1.0467 (3.6); 0.4461 (2.4); 0.4326 (4.0); 0.4243 (3.2); 0.4186 (3.3); 0.4114 (3.8); 0.3969 (2.4); 0.0926 (3.0); 0.0134 (1.9); −0.0002 (3.4); −0.0094 (3.0); −0.0217 (3.3); −0.0352 (1.7)

(93) Ia-23: .sup.1H-NMR (300.2 MHz, CDCl.sub.3):

(94) δ=8.7375 (13.6); 8.0412 (1.4); 7.5255 (0.4); 7.5170 (1.4); 7.5105 (3.2); 7.4965 (11.2); 7.4853 (4.4); 7.4787 (1.5); 7.2987 (39.5); 7.2716 (8.2); 7.2658 (6.0); 7.2606 (6.8); 7.2505 (11.5); 7.2411 (1.1); 4.8678 (3.7); 4.8620 (3.8); 4.8201 (5.4); 4.8143 (5.5); 4.6224 (5.0); 4.6176 (5.2); 4.5747 (3.5); 4.5699 (3.5); 3.2828 (3.4); 3.2773 (3.5); 3.2363 (4.3); 3.2308 (4.4); 2.9962 (11.9); 2.9188 (10.2); 2.9025 (4.5); 2.8975 (4.6); 2.8559 (3.5); 2.8511 (3.6); 2.5205 (4.6); 1.6161 (16.0); 0.9021 (0.8); 0.8770 (1.1); 0.8622 (1.2); 0.8546 (1.0); 0.8359 (1.8); 0.8141 (1.8); 0.7941 (1.2); 0.7865 (1.0); 0.7721 (1.5); 0.7685 (1.5); 0.7466 (1.3); 0.6946 (1.1); 0.6734 (1.4); 0.6696 (1.5); 0.6545 (0.8); 0.6481 (1.5); 0.6291 (2.1); 0.6079 (2.4); 0.6041 (1.8); 0.5888 (0.7); 0.5824 (1.5); 0.5682 (0.8); 0.5638 (1.1); 0.5427 (1.1); 0.4635 (1.0); 0.4413 (1.1); 0.4254 (1.9); 0.4158 (0.8); 0.4029 (2.6); 0.3902 (1.6); 0.3783 (1.4); 0.3679 (1.6); 0.3431 (1.1); 0.2702 (1.3); 0.2491 (1.3); 0.2446 (1.5); 0.2349 (1.7); 0.2236 (1.3); 0.2100 (2.3); 0.1975 (1.1); 0.1885 (1.4); 0.1760 (1.1); 0.1718 (1.0); 0.1509 (0.8); 0.0472 (1.3); 0.0364 (45.7); 0.0255 (1.8)

(95) Ia-24: .sup.1H-NMR (300.2 MHz, CDCl.sub.3):

(96) δ=8.8251 (14.9); 7.6460 (4.7); 7.6424 (5.0); 7.6195 (5.3); 7.6157 (5.6); 7.5759 (3.7); 7.5705 (4.1); 7.5505 (5.0); 7.5451 (5.2); 7.3991 (2.6); 7.3951 (2.7); 7.3741 (5.2); 7.3703 (5.2); 7.3491 (2.9); 7.3451 (2.8); 7.2990 (38.6); 7.2548 (3.0); 7.2491 (3.2); 7.2286 (4.2); 7.2232 (4.1); 7.2035 (2.0); 7.1979 (1.9); 5.2076 (9.3); 5.1598 (10.6); 4.5091 (9.1); 4.4613 (8.0); 3.6882 (6.1); 3.6402 (8.1); 3.3676 (8.5); 3.3195 (6.4); 2.8204 (15.4); 2.0454 (1.1); 1.5862 (16.0); 1.2910 (1.2); 0.9459 (0.5); 0.9256 (3.5); 0.9167 (4.0); 0.8992 (4.0); 0.8908 (9.2); 0.8824 (5.0); 0.8634 (5.5); 0.8575 (5.3); 0.8373 (1.0); 0.6570 (2.6); 0.6372 (3.3); 0.6324 (2.9); 0.6214 (2.1); 0.6112 (3.0); 0.6030 (2.7); 0.5968 (2.0); 0.5769 (2.1); 0.4912 (2.8); 0.4715 (2.5); 0.4635 (2.7); 0.4584 (3.2); 0.4452 (2.2); 0.4372 (2.5); 0.4307 (2.5); 0.4107 (1.8); 0.0488 (1.6); 0.0380 (50.9); 0.0273 (2.1)

(97) Ia-25: .sup.1H-NMR (300.2 MHz, CDCl.sub.3):

(98) δ=8.8260 (0.7); 8.7932 (12.7); 7.3574 (1.8); 7.3322 (1.4); 7.3103 (0.5); 7.3088 (0.5); 7.2983 (22.0); 7.2216 (0.6); 7.2030 (1.2); 7.1949 (6.6); 7.1807 (3.1); 7.1760 (6.6); 7.1670 (4.4); 7.1539 (4.6); 7.1440 (2.1); 7.1371 (2.0); 7.1165 (0.7); 7.1095 (0.5); 7.0355 (0.4); 5.1070 (5.5); 5.1039 (5.5); 5.0585 (6.2); 5.0554 (5.9); 4.9303 (0.5); 4.7467 (0.4); 4.1617 (1.6); 4.1382 (1.6); 4.1137 (6.0); 4.0654 (4.9); 2.8821 (0.4); 2.8422 (0.4); 2.8038 (0.3); 2.7762 (0.7); 2.0803 (0.7); 2.0440 (1.8); 1.6194 (0.7); 1.5731 (0.5); 1.5313 (16.0); 1.5075 (15.9); 1.3184 (0.4); 1.3104 (2.0); 1.2902 (3.0); 1.2849 (2.6); 1.2734 (2.4); 1.2646 (2.7); 1.2531 (2.7); 1.2479 (2.5); 1.2276 (2.5); 1.0719 (2.2); 1.0514 (2.4); 1.0476 (2.8); 1.0357 (2.9); 1.0273 (2.4); 1.0152 (2.8); 1.0114 (3.1); 0.9910 (2.3); 0.4010 (1.9); 0.3803 (2.4); 0.3756 (2.2); 0.3648 (2.0); 0.3548 (2.2); 0.3441 (2.3); 0.3394 (2.0); 0.3186 (1.8); 0.1063 (0.5); 0.0462 (0.6); 0.0354 (20.7); 0.0245 (0.8); −0.0483 (1.6); −0.0718 (2.2); −0.0853 (1.8); −0.0931 (1.7); −0.1086 (2.1); −0.1301 (1.3)

(99) Ia-26: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(100) δ=9.1840 (5.3); 7.9739 (0.7); 7.2541 (1.1); 7.2349 (2.0); 7.2152 (1.2); 6.9614 (4.1); 6.9423 (1.6); 6.8521 (1.2); 6.8490 (1.2); 6.8328 (1.2); 6.8275 (1.1); 5.4451 (2.9); 4.9197 (1.3); 4.8840 (1.5); 4.4374 (1.7); 4.4015 (1.5); 3.7625 (16.0); 3.3404 (87.2); 3.0066 (4.3); 2.9122 (4.2); 2.7532 (3.9); 2.5269 (4.8); 2.5228 (6.4); 2.5188 (4.9); 0.6057 (0.4); 0.6009 (0.4); 0.5941 (0.4); 0.5866 (0.5); 0.5544 (0.4); 0.5354 (0.4); 0.4848 (0.4); 0.4727 (1.2); 0.4572 (1.2); 0.4443 (0.8); 0.4278 (1.4); 0.4094 (0.5); 0.3959 (0.3); 0.0318 (0.4); 0.0190 (0.5); 0.0122 (0.5); 0.0069 (0.5); −0.0002 (0.6); −0.0060 (0.6); −0.0112 (0.6); −0.0265 (0.4)

(101) Ia-27: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(102) δ=9.1780 (5.5); 7.9749 (0.8); 7.2905 (3.6); 7.2694 (4.0); 6.8965 (4.2); 6.8754 (3.8); 5.3904 (3.4); 4.8853 (1.6); 4.8495 (1.8); 4.4299 (1.9); 4.3941 (1.7); 3.7574 (16.0); 3.3389 (97.6); 3.0063 (0.5); 2.9713 (2.7); 2.9566 (2.6); 2.9132 (4.6); 2.7542 (4.3); 2.5235 (6.7); 0.5851 (0.4); 0.5614 (0.5); 0.5544 (0.5); 0.5315 (0.5); 0.5137 (0.4); 0.4631 (0.5); 0.4481 (0.9); 0.4318 (1.1); 0.4091 (1.4); 0.3950 (1.2); 0.0252 (0.4); −0.0002 (0.8); −0.0110 (0.7); −0.0186 (0.5); −0.0323 (0.4)

(103) Ia-28: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(104) δ=9.1898 (7.0); 7.9830 (1.0); 7.2342 (0.8); 7.2156 (2.7); 7.1965 (5.0); 7.1806 (3.1); 7.1619 (1.2); 7.0966 (2.1); 7.0787 (1.6); 5.4282 (4.2); 4.9160 (1.9); 4.8802 (2.2); 4.4492 (2.4); 4.4135 (2.1); 3.3483 (108.4); 3.0413 (0.6); 3.0070 (3.4); 2.9932 (3.2); 2.9587 (0.6); 2.9215 (5.6); 2.7623 (5.2); 2.5321 (7.8); 2.3224 (16.0); 0.6140 (0.4); 0.5950 (0.6); 0.5748 (0.7); 0.5626 (0.4); 0.5476 (0.6); 0.5426 (0.5); 0.5341 (0.7); 0.5052 (0.3); 0.4913 (0.3); 0.4719 (0.6); 0.4611 (1.6); 0.4464 (1.5); 0.4234 (1.8); 0.4134 (1.2); 0.3933 (0.6); 0.0436 (0.4); 0.0330 (0.5); 0.0188 (0.6); 0.0084 (0.8); −0.0002 (1.0); −0.0111 (0.6); −0.0256 (0.6)

(105) Ia-29: .sup.1H-NMR (300.2 MHz, CDCl.sub.3):

(106) δ=8.8582 (16.0); 7.4632 (4.8); 7.4544 (5.5); 7.4419 (4.9); 7.4331 (5.3); 7.3212 (1.8); 7.3146 (2.1); 7.3072 (2.7); 7.2982 (8.0); 7.2854 (2.7); 7.2784 (3.2); 7.2704 (2.4); 7.0974 (4.3); 7.0671 (7.2); 7.0369 (3.4); 5.1457 (8.8); 5.0978 (10.2); 4.5378 (8.5); 4.4899 (7.3); 3.4102 (5.2); 3.3626 (7.8); 3.1847 (6.5); 3.1793 (6.6); 3.1372 (4.6); 3.1317 (4.7); 3.0483 (1.8); 2.0408 (0.4); 0.8811 (0.4); 0.8600 (3.4); 0.8546 (4.6); 0.8269 (9.2); 0.7958 (7.4); 0.7743 (0.9); 0.6037 (2.6); 0.5811 (3.7); 0.5682 (2.2); 0.5570 (3.0); 0.5501 (2.9); 0.5445 (2.1); 0.5233 (2.1); 0.4183 (3.1); 0.3983 (3.0); 0.3867 (4.1); 0.3715 (2.6); 0.3644 (3.1); 0.3577 (2.8); 0.3375 (2.1); 0.0286 (4.3)

(107) Ia-30: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(108) δ=9.0667 (6.8); 7.9605 (1.0); 7.2486 (4.0); 7.2290 (5.4); 7.1099 (5.0); 7.0904 (3.9); 4.9231 (2.6); 4.8874 (2.8); 4.5366 (6.0); 4.2227 (2.7); 4.1869 (2.5); 3.3278 (109.4); 2.9765 (1.6); 2.9420 (3.0); 2.8986 (5.7); 2.8689 (3.1); 2.8344 (1.7); 2.7396 (5.4); 2.5091 (8.2); 2.2865 (15.2); 1.2020 (16.0); 0.2794 (0.8); 0.2650 (1.5); 0.2507 (1.1); −0.2287 (0.4); −0.2430 (0.9); −0.2515 (1.5); −0.2691 (3.5); −0.2869 (1.4); −0.2954 (1.0); −0.3087 (0.6); −0.4797 (1.0); −0.4864 (1.0); −0.4946 (1.7); −0.5088 (0.9): −0.5168 (0.7)

(109) Ia-31: .sup.1H-NMR (300.2 MHz, CDCl.sub.3):

(110) δ=8.8515 (16.0); 7.2983 (7.3); 7.2933 (2.8); 6.9631 (8.3); 6.9562 (10.1); 6.9362 (9.9); 6.8371 (2.2); 6.8296 (3.0); 6.8224 (2.1); 6.8073 (4.3); 6.7998 (5.8); 6.7938 (3.6); 6.7775 (2.3); 6.7700 (2.9); 6.7641 (1.8); 5.0232 (8.6); 5.0186 (4.2); 4.9753 (10.8); 4.9708 (5.2); 4.6349 (9.6); 4.5871 (7.6); 4.1862 (0.4); 4.1624 (1.2); 4.1574 (0.6); 4.1385 (1.2); 4.1334 (0.6); 4.1146 (0.4); 3.3962 (7.2); 3.3500 (9.0); 3.0204 (9.6); 2.9741 (7.8); 2.9099 (0.6); 2.8057 (0.4); 2.0766 (5.4); 2.0715 (2.3); 2.0433 (1.2); 2.0384 (0.6); 1.3147 (1.6); 1.3097 (0.8); 1.2909 (3.2); 1.2859 (1.6); 1.2670 (1.7); 1.2620 (0.8); 0.8243 (1.7); 0.8040 (3.1); 0.7980 (3.3); 0.7884 (3.5); 0.7797 (3.7); 0.7683 (4.5); 0.7640 (4.3); 0.7460 (3.2); 0.7154 (0.4); 0.6862 (2.1); 0.6618 (3.9); 0.6569 (2.8); 0.6500 (3.6); 0.6419 (3.5); 0.6365 (2.5); 0.6316 (2.8); 0.6259 (4.5); 0.6209 (2.7); 0.6077 (6.0); 0.6018 (6.2); 0.5841 (4.4); 0.5784 (3.0); 0.5676 (3.6); 0.5599 (3.6); 0.5547 (2.7); 0.5484 (3.5); 0.5436 (2.7); 0.5241 (1.9); 0.4151 (3.0); 0.4101 (2.0); 0.3975 (4.0); 0.3927 (4.5); 0.3810 (3.8); 0.3734 (3.7); 0.3679 (2.6); 0.3636 (3.1); 0.3569 (3.0); 0.3372 (1.8); 0.0311 (7.4); 0.0261 (2.9)

(111) Ia-32: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(112) δ=8.9258 (0.8); 7.1126 (0.6); 5.2743 (0.6); 4.7317 (0.4); 4.1829 (0.4); 4.1470 (0.3); 3.0785 (16.0); 2.9966 (0.4); 2.9290 (0.4); 2.6507 (0.5); 2.4914 (0.5); 2.2615 (1.5); 2.2578 (1.4)

(113) Ia-33: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(114) δ=9.1899 (6.9); 7.9873 (0.8); 7.2763 (4.1); 7.2570 (5.8); 7.1505 (5.3); 7.1312 (4.2); 5.4164 (4.8); 4.9026 (2.1); 4.8669 (2.5); 4.4428 (2.6); 4.4070 (2.3); 3.3539 (105.0); 3.0361 (0.7); 3.0016 (3.7); 2.9873 (3.6); 2.9523 (0.7); 2.9260 (4.4); 2.7667 (4.0); 2.5370 (8.8); 2.5334 (8.1); 2.3189 (16.0); 0.6157 (0.4); 0.5976 (0.7); 0.5774 (0.7); 0.5650 (0.5); 0.5458 (0.6); 0.5359 (0.7); 0.5070 (0.3); 0.4936 (0.4); 0.4861 (0.3); 0.4746 (0.6); 0.4634 (1.7); 0.4461 (1.7); 0.4249 (2.0); 0.4128 (1.3); 0.3956 (0.6); 0.0431 (0.4); 0.0328 (0.5); 0.0099 (1.0); −0.0002 (1.1); −0.0242 (0.6); −0.0344 (0.4)

(115) Ia-34: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(116) δ=8.8291 (1.0); 7.0373 (0.6); 7.0159 (0.7); 6.6302 (0.7); 6.6088 (0.7); 4.6774 (0.4); 4.6417 (0.4); 4.2890 (0.8); 3.9810 (0.4); 3.9453 (0.4); 3.4996 (3.0); 3.0891 (16.0); 2.6826 (0.4); 2.6594 (1.0); 2.6132 (0.4); 2.5004 (0.9); 2.2701 (1.3); 2.2662 (1.0); 0.9597 (2.2); −0.5092 (0.5)

(117) Ia-35: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(118) δ=8.9567 (2.2); 6.9765 (0.7); 6.9544 (1.1); 6.9336 (0.7); 5.2074 (1.8); 4.8455 (0.8); 4.8095 (0.9); 4.3293 (0.8); 4.2932 (0.8); 3.1013 (16.0); 2.9949 (0.4); 2.9593 (0.7); 2.8834 (0.7); 2.8479 (0.4); 2.6742 (0.3); 2.2849 (2.4); 2.2810 (1.9); 0.5560 (0.3); 0.5529 (0.3); 0.4633 (0.3); 0.4456 (0.4); 0.1730 (0.3); 0.0267 (0.3)

(119) Ia-36: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(120) δ=8.9404 (1.1); 6.7651 (0.3); 5.1418 (0.9); 4.8611 (0.4); 4.8251 (0.4); 4.2631 (0.4); 4.2271 (0.4); 3.0983 (16.0); 2.9619 (1.0); 2.6701 (1.3); 2.5108 (1.2); 2.2848 (1.0); 2.2806 (1.3); 2.2764 (1.0); 1.9941 (1.4)

(121) Ia-37: .sup.1H-NMR (499.9 MHz, CDCl.sub.3):

(122) δ=8.7792 (4.2); 7.4743 (1.0); 7.4671 (1.0); 7.4627 (1.0); 7.4554 (1.2); 7.4101 (1.1); 7.4030 (1.0); 7.3986 (1.1); 7.3913 (1.3); 7.2619 (4.8); 7.2414 (0.6); 7.2340 (2.9); 7.2270 (2.4); 7.2222 (2.4); 7.2151 (2.5); 7.2076 (0.4); 5.2994 (1.4); 4.9454 (2.0); 4.9155 (2.9); 4.7902 (2.5); 4.7602 (1.8); 3.6313 (16.0); 3.5279 (0.5); 3.3315 (1.6); 3.3223 (1.4); 3.3016 (2.4); 3.2116 (0.3); 3.1822 (2.3); 3.1522 (2.2); 3.0866 (0.6); 3.0227 (1.3); 1.5695 (2.3); 0.8168 (0.8); 0.8128 (0.5); 0.8070 (0.9); 0.7997 (1.2); 0.7962 (1.4); 0.7920 (1.5); 0.7864 (1.1); 0.7789 (1.3); 0.7720 (1.3); 0.7595 (0.4); 0.6764 (0.4); 0.6645 (0.9); 0.6552 (0.5); 0.6499 (0.9): 0.6453 (1.4); 0.6344 (0.6); 0.6288 (1.4); 0.6176 (0.4); 0.6138 (0.4); 0.6087 (0.6); −0.0002 (5.6)

(123) Ia-38: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(124) δ=8.9360 (2.2); 7.7118 (0.5); 7.2690 (0.4); 7.2527 (0.4); 7.0732 (0.4); 7.0547 (0.6); 7.0513 (0.6); 5.3300 (1.8); 4.7934 (0.8); 4.7573 (0.9); 4.3086 (0.9); 4.2725 (0.8); 3.0767 (16.0); 2.9798 (0.4); 2.9440 (0.8); 2.8935 (0.8); 2.8581 (0.4); 2.6505 (3.0); 2.4909 (2.8); 2.2653 (2.1); 2.2611 (2.9); 2.2570 (2.3); 0.4004 (0.3); 0.3922 (0.4); 0.3738 (0.4); 0.3607 (0.4); 0.3527 (0.4); 0.3347 (0.4); 0.1862 (0.3); −0.0002 (0.3)

(125) Ia-39: .sup.1H-NMR (300.2 MHz, CDCl.sub.3):

(126) δ=8.8402 (16.0); 7.5669 (4.1); 7.5463 (4.7); 7.5382 (5.0); 7.5177 (4.6); 7.2984 (6.1); 7.2149 (4.5); 7.2062 (5.0); 7.1870 (4.6); 7.1782 (4.9); 7.0838 (2.9); 7.0750 (2.7); 7.0564 (4.4); 7.0481 (4.0); 7.0289 (2.6); 7.0201 (2.3); 5.1826 (9.1); 5.1348 (10.4); 4.4749 (9.2); 4.4271 (8.1); 3.6360 (7.0); 3.5876 (8.9); 3.2639 (8.2); 3.2155 (6.4); 2.9348 (5.7); 2.0411 (2.2); 0.9208 (0.5); 0.9008 (4.6); 0.8954 (5.1); 0.8737 (6.0); 0.8679 (11.0); 0.8619 (6.3); 0.8378 (8.4); 0.8165 (1.0); 0.6234 (2.7); 0.6034 (3.8); 0.5985 (3.3); 0.5882 (2.5); 0.5762 (3.5); 0.5704 (3.2); 0.5631 (2.2); 0.5430 (2.2); 0.4442 (2.9); 0.4353 (0.9); 0.4242 (2.9); 0.4134 (4.2); 0.3972 (2.7); 0.3907 (3.0); 0.3837 (2.8); 0.3637 (2.0); 0.0309 (6.4)

(127) Ia-40: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(128) δ=8.9562 (2.6); 7.7373 (0.6); 7.3142 (0.5); 7.2936 (1.0); 7.2730 (0.6); 7.1940 (0.6); 7.1890 (0.7); 7.1694 (0.6); 7.1644 (0.7); 7.0645 (0.7); 7.0599 (0.7); 7.0438 (0.6); 7.0392 (0.6); 5.3308 (2.0); 4.8135 (0.9); 4.7775 (1.0); 4.2748 (1.0); 4.2388 (0.9); 3.1054 (16.0); 2.9114 (2.4); 2.6756 (3.3); 2.5162 (3.1); 2.2905 (2.3); 2.2865 (3.1); 2.2825 (2.4); 0.4499 (0.4); 0.4415 (0.4); 0.3868 (0.4); 0.3785 (0.4); 0.3607 (0.4); 0.1930 (0.4); 0.1749 (0.4); 0.1668 (0.3); −0.0002 (0.4); −0.0104 (0.3); −0.0146 (0.3); −0.0262 (0.3)

(129) Ia-41: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(130) δ=8.9558 (1.1); 6.9037 (0.4); 5.3412 (0.8); 4.8319 (0.4); 4.7959 (0.4); 4.2936 (0.4); 4.2575 (0.4); 3.1025 (16.0); 2.9693 (0.5); 2.9625 (0.6); 2.6717 (1.6); 2.5123 (1.5); 2.2865 (1.0); 2.2824 (1.4); 2.2783 (1.1)

(131) Ia-42: .sup.1H-NMR (300.2 MHz, CDCl.sub.3):

(132) δ=8.8681 (16.0); 7.2983 (3.0); 7.2160 (1.8); 7.2059 (2.2); 7.1966 (2.1); 7.1871 (3.8); 7.1770 (2.3); 7.1680 (2.0); 7.1579 (2.0); 7.1138 (1.3); 7.0985 (1.5); 7.0839 (3.8); 7.0684 (4.0); 7.0541 (3.2); 7.0458 (2.3); 7.0380 (3.8); 7.0317 (2.6); 7.0212 (3.4); 7.0158 (1.6); 7.0102 (2.3); 7.0068 (2.8); 7.0015 (1.4); 6.9968 (1.9); 6.9912 (1.6); 6.9803 (1.0); 6.9772 (0.9); 6.9667 (0.7); 5.1444 (7.2); 5.0965 (8.4); 4.5628 (7.7); 4.5149 (6.6); 3.4093 (3.7); 3.3614 (5.6); 3.1988 (5.6); 3.1933 (5.8); 3.1672 (2.5); 3.1515 (4.5); 3.1459 (4.2); 2.0379 (0.7); 0.8447 (3.9); 0.8392 (4.2); 0.8173 (5.0); 0.8118 (9.8); 0.8059 (5.2); 0.7814 (8.4); 0.7607 (0.7); 0.6022 (2.6); 0.5824 (3.3); 0.5773 (2.8); 0.5669 (2.1); 0.5551 (3.2); 0.5494 (2.7); 0.5419 (1.8); 0.5220 (2.0); 0.4269 (2.7); 0.4175 (0.6); 0.4071 (2.5); 0.3963 (4.1); 0.3798 (2.3); 0.3738 (2.5); 0.3662 (2.4); 0.3464 (1.7); 0.0235 (2.8)

(133) Ia-43: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(134) δ=8.9510 (3.0); 7.2207 (0.4); 7.2154 (0.4); 7.2074 (0.4); 7.1991 (0.4); 7.1947 (0.4); 6.9408 (0.4); 6.9295 (0.4); 6.9178 (0.4); 5.4033 (2.6); 4.7982 (1.1); 4.7621 (1.3); 4.3148 (1.2); 4.2787 (1.0); 3.0769 (16.0); 2.9976 (0.4); 2.9621 (1.2); 2.9368 (1.3); 2.9015 (0.4); 2.6523 (0.6); 2.4930 (0.5); 2.2627 (3.6); 0.4704 (0.4); 0.4589 (0.3); 0.4530 (0.4); 0.4442 (0.5); 0.4262 (0.4); 0.3923 (0.4); 0.3840 (0.5); 0.3777 (0.3); 0.3663 (0.5); 0.3513 (0.3); 0.2208 (0.3); 0.2061 (0.4); 0.1942 (0.4); 0.1882 (0.4); 0.1802 (0.4); 0.0261 (0.4); 0.0153 (0.4); −0.0002 (0.4)

(135) Ia-44: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(136) δ=8.9397 (1.1); 7.0692 (0.5); 7.0525 (0.3); 5.3392 (0.8); 4.7874 (0.4); 4.7513 (0.5); 4.3202 (0.5); 4.2840 (0.4); 3.0804 (16.0); 2.9403 (0.4); 2.8785 (0.4); 2.6495 (1.2); 2.4899 (1.2); 2.2603 (1.5)

(137) Ia-45: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(138) δ=8.9002 (2.1); 7.7161 (0.4); 7.1316 (0.3); 7.1108 (0.5); 7.0951 (0.4); 6.9436 (0.5); 6.9210 (0.7); 6.8990 (0.4); 5.0078 (1.6); 4.8967 (0.7); 4.8608 (0.8); 4.2072 (0.7); 4.1714 (0.7); 3.2342 (0.3); 3.2043 (0.5); 3.1988 (0.6); 3.1160 (0.6); 3.1102 (0.6); 3.0812 (16.0); 2.6547 (2.3); 2.4952 (2.1); 2.2694 (1.7); 2.2653 (2.4); 2.2612 (1.9); 2.0974 (4.0); 0.5329 (0.3)

(139) Ia-46: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(140) δ=8.9466 (1.2); 7.7408 (0.3); 5.1863 (0.7); 4.8661 (0.4); 4.8301 (0.5); 4.2677 (0.4); 4.2317 (0.4); 3.6127 (3.4); 3.1102 (16.0); 2.9780 (1.1); 2.6794 (1.9); 2.5200 (1.8); 2.2942 (1.1); 2.2901 (1.5); 2.2859 (1.2)

(141) Ia-47: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(142) δ=8.9799 (2.1); 7.2264 (1.1); 7.1369 (0.6); 7.1218 (1.9); 7.1107 (0.8); 7.1062 (0.6); 5.3680 (1.8); 4.8108 (0.8); 4.7748 (0.9); 4.2737 (0.8); 4.2377 (0.8); 3.1034 (16.0); 2.9604 (0.6); 2.9258 (0.9); 2.8040 (0.9); 2.7695 (0.6); 2.6785 (1.8); 2.5195 (1.6); 2.2929 (1.7); 2.2890 (2.2); 0.2546 (0.3); 0.2374 (0.4); 0.1867 (0.4); −0.0002 (0.3)

(143) Ia-48: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(144) δ=8.9515 (1.1); 5.2688 (0.9); 4.8160 (0.4); 4.7801 (0.4); 4.2769 (0.4); 4.2409 (0.4); 3.6579 (3.1); 3.1130 (16.0); 2.8967 (1.1); 2.6827 (1.8); 2.5232 (1.7); 2.2935 (1.3); 2.2896 (1.1)

(145) Ia-49: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(146) δ=8.9527 (1.9); 7.7474 (0.4); 6.5422 (1.1); 6.5180 (1.1); 5.1221 (1.3); 4.8529 (0.6); 4.8170 (0.7); 4.2729 (0.7); 4.2369 (0.6); 3.5764 (5.5); 3.1107 (16.0); 2.8914 (1.1); 2.6859 (2.1); 2.5267 (1.9); 2.3006 (1.7); 2.2964 (2.3); 2.2922 (1.8)

(147) Ia-50: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(148) δ=8.9430 (1.1); 5.2744 (0.8); 4.8012 (0.4); 4.7653 (0.4); 4.2713 (0.4); 4.2353 (0.4); 3.6803 (2.5); 3.0966 (16.0); 2.8893 (1.0); 2.6672 (1.0); 2.5079 (0.9); 2.2820 (1.0); 2.2778 (1.4); 2.2737 (1.1)

(149) Ia-51: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(150) δ=8.9420 (2.3); 7.7154 (0.4); 7.2945 (0.6); 7.2882 (0.4); 7.2808 (0.6); 7.2705 (0.6); 7.2594 (0.4); 5.3449 (1.8); 4.7826 (0.8); 4.7466 (0.9); 4.2614 (0.9); 4.2254 (0.8); 3.0802 (16.0); 2.8787 (2.1); 2.6540 (2.1); 2.4947 (1.9); 2.2686 (2.0); 2.2645 (2.7); 2.2605 (2.1); 0.4528 (0.3); 0.4442 (0.4); 0.3898 (0.3); 0.3815 (0.4); 0.3636 (0.4); 0.1958 (0.3); 0.1920 (0.3); 0.1776 (0.3); 0.0094 (0.3)

(151) Ia-52: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(152) δ=8.9672 (1.0); 7.1424 (0.5); 7.1201 (0.4); 5.3604 (0.8); 4.7870 (0.4); 4.7509 (0.4); 4.2742 (0.4); 4.2382 (0.4); 3.0961 (16.0); 2.9084 (0.4); 2.7732 (0.4); 2.6660 (1.2); 2.5067 (1.1); 2.2809 (1.1); 2.2768 (1.4); 2.2726 (1.1)

(153) Ia-53: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(154) δ=8.9710 (2.1); 7.3273 (0.4); 7.3098 (0.5); 7.0036 (0.4); 6.9979 (0.4); 6.8648 (0.5); 6.8591 (0.4); 5.3259 (1.7); 4.8292 (0.7); 4.7932 (0.8); 4.2744 (0.8); 4.2384 (0.7); 3.1280 (16.0); 2.9166 (2.1); 2.6888 (1.5); 2.5292 (1.4); 2.3003 (2.1); 0.3636 (0.4)

(155) Ia-54: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(156) δ=8.9445 (2.1); 7.1978 (0.3); 6.8932 (0.4); 5.2688 (1.6); 4.8448 (0.8); 4.8087 (0.9); 4.3351 (0.8); 4.2990 (0.8); 3.0872 (16.0); 3.0577 (0.6); 3.0221 (0.8); 2.9462 (0.7); 2.9110 (0.4); 2.6551 (0.5); 2.4955 (0.5); 2.2659 (1.4); 0.5401 (0.4); 0.4656 (0.3); 0.4566 (0.3); 0.4395 (0.4); 0.1867 (0.3); 0.0262 (0.3)

(157) Ia-55: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(158) δ=8.9523 (1.1); 5.2942 (0.9); 4.8183 (0.4); 4.7823 (0.4); 4.2863 (0.4); 4.2503 (0.4); 3.1063 (16.0); 2.9234 (1.1); 2.6767 (1.3); 2.5173 (1.2); 2.2912 (1.1); 2.2874 (1.4); 2.2833 (1.1); 2.0546 (1.5); 2.0514 (1.5)

(159) Ia-56: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(160) δ=8.9482 (3.6); 7.1654 (0.4); 7.1608 (0.4); 7.1523 (0.4); 7.1456 (0.5); 7.1405 (0.6); 7.1309 (1.2); 7.1098 (0.9); 7.1038 (0.8); 7.0822 (0.4); 6.9817 (0.5); 6.9710 (0.5); 6.9612 (0.4); 6.9504 (0.4); 5.5086 (1.3); 5.3303 (3.1); 4.7631 (1.3); 4.7270 (1.5); 4.2629 (1.5); 4.2268 (1.3); 3.0674 (16.0); 2.9251 (1.0); 2.8902 (1.4); 2.7526 (1.4); 2.7177 (0.9); 2.2641 (1.9); 2.2599 (2.5); 2.2558 (1.9); 0.3105 (0.4); 0.3065 (0.4); 0.2978 (0.3); 0.2920 (0.5); 0.2842 (0.5); 0.2795 (0.5); 0.2724 (0.4); 0.2658 (0.6); 0.2544 (0.5); 0.2467 (0.6); 0.2290 (0.7); 0.2151 (0.4); 0.1842 (0.5); 0.1711 (0.6); 0.1658 (0.5); 0.1586 (0.4); 0.1524 (0.5); 0.1454 (0.4); 0.0169 (0.4); 0.0035 (0.5); −0.0002 (0.5); −0.0097 (0.5); −0.0135 (0.5); −0.0228 (0.4); −0.0271 (0.4)

(161) Ia-57: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(162) δ=8.9997 (8.0); 7.7879 (1.4); 7.1011 (4.3); 7.0814 (5.7); 6.9512 (5.1); 6.9318 (4.1); 5.2562 (6.7); 4.8382 (2.8); 4.8024 (3.2); 4.2549 (3.1); 4.2189 (2.9); 3.1591 (14.0); 2.9275 (1.8); 2.8927 (3.3); 2.8243 (3.2); 2.7896 (1.8); 2.7256 (8.4); 2.5663 (7.8); 2.3409 (6.9); 2.3368 (9.3); 2.3326 (7.0); 2.1185 (16.0); 0.4520 (0.5); 0.4353 (0.9); 0.4253 (0.9); 0.4192 (1.1); 0.4077 (1.1); 0.3925 (0.9); 0.3400 (0.6); 0.3221 (1.0); 0.3137 (1.2); 0.3076 (0.8); 0.2% 1 (1.4); 0.2813 (0.9); 0.2141 (0.9); 0.2003 (1.2); 0.1961 (1.1); 0.1878 (0.9); 0.1821 (1.1); 0.1743 (0.9); 0.1557 (0.6); 0.0264 (0.8); 0.0087 (1.1); −0.0002 (1.1); −0.0047 (1.0); −0.0139 (0.9); −0.0179 (0.9); −0.0318 (0.6)

(163) Ia-58: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(164) δ=8.9996 (5.4); 7.7859 (0.9); 7.1259 (3.3); 7.1045 (3.7); 6.7085 (3.8); 6.6870 (3.6); 5.2435 (4.7); 4.8298 (1.9); 4.7939 (2.1); 4.2548 (2.1); 4.2190 (1.9); 3.5668 (16.0); 3.1574 (9.6); 2.9091 (1.3); 2.8739 (2.3); 2.7990 (2.2); 2.7640 (1.2); 2.7236 (5.0); 2.5643 (4.7); 2.3389 (4.6); 2.3349 (6.1); 2.3308 (4.6); 0.4386 (0.3); 0.4211 (0.6); 0.4121 (0.6); 0.4058 (0.7); 0.3973 (0.8); 0.3795 (0.6); 0.3364 (0.4); 0.3179 (0.7); 0.3098 (0.8); 0.3034 (0.5); 0.2919 (0.9); 0.2771 (0.6); 0.2121 (0.6); 0.1985 (0.8); 0.1855 (0.6); 0.1802 (0.8); 0.1723 (0.6); 0.1538 (0.4); 0.0266 (0.6); 0.0091 (0.7); −0.0002 (0.7); −0.0047 (0.7); −0.0142 (0.6); −0.0176 (0.6); −0.0318 (0.4)

(165) Ia-59: .sup.1H-NMR (300.2 MHz, CDCl.sub.3):

(166) δ=8.8560 (16.0); 8.4551 (8.3); 8.4456 (12.3); 8.4396 (9.0); 7.5781 (2.4); 7.5704 (3.1); 7.5635 (2.4); 7.5472 (2.4); 7.5402 (3.1); 7.5326 (2.3); 7.2988 (19.1); 5.0719 (8.3); 5.0241 (10.1); 4.6298 (9.0); 4.5820 (7.4); 3.4329 (5.6); 3.3861 (7.4); 3.3457 (12.0); 3.1140 (7.0); 3.0672 (5.3); 2.0445 (0.7); 1.6677 (7.5); 1.2899 (0.6); 0.7894 (1.5); 0.7697 (2.1); 0.7614 (1.7); 0.7537 (2.5); 0.7455 (2.5); 0.7338 (3.2); 0.7297 (3.0); 0.7137 (2.6); 0.6898 (0.6); 0.6494 (1.7); 0.6251 (3.0); 0.6134 (2.4); 0.6053 (2.6); 0.5891 (3.7); 0.5736 (9.0); 0.5583 (3.7); 0.5419 (2.6); 0.5339 (2.4); 0.5224 (2.7); 0.4980 (1.6); 0.3788 (0.5); 0.3552 (2.4); 0.3394 (2.8); 0.3351 (3.1); 0.3232 (2.6); 0.3155 (2.5); 0.3075 (1.9); 0.2990 (2.2); 0.2794 (1.7); 0.0454 (0.8); 0.0346 (24.8); 0.0238 (1.1)

(167) Ia-60: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(168) δ=8.9956 (5.5); 7.7750 (0.8); 7.0546 (1.0); 7.0355 (2.0); 7.0151 (1.2); 6.7876 (4.2); 6.7703 (1.6); 6.6526 (1.2); 6.6351 (1.1); 6.6294 (1.1); 5.2813 (4.7); 4.8482 (1.9); 4.8123 (2.1); 4.2499 (2.1); 4.2139 (1.9); 3.5619 (16.0); 3.1463 (11.4); 2.9265 (1.1); 2.8920 (2.5); 2.8479 (2.4); 2.8133 (1.1); 2.7126 (4.9); 2.5532 (4.5); 2.3279 (5.4); 2.3238 (7.2); 2.3197 (5.5); 0.4707 (0.4); 0.4529 (0.7); 0.4439 (0.6); 0.4376 (0.7); 0.4288 (0.8); 0.4112 (0.6); 0.3496 (0.4); 0.3316 (0.7); 0.3232 (0.8); 0.3170 (0.6); 0.3052 (0.9); 0.2907 (0.6); 0.2142 (0.6); 0.2005 (0.8); 0.1961 (0.7); 0.1879 (0.6); 0.1821 (0.8); 0.1742 (0.7); 0.1558 (0.4); 0.0267 (0.6); 0.0091 (0.7); −0.0002 (0.7); −0.0048 (0.7); −0.0138 (0.6); −0.0177 (0.6); −0.0317 (0.4)

(169) Ia-61: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(170) δ=9.3091 (5.4); 8.1908 (0.8); 7.4557 (1.1); 7.4362 (2.1); 7.4166 (1.4); 7.1921 (2.1); 7.1873 (2.0); 7.1778 (1.8); 7.1588 (1.5); 7.0454 (1.2); 7.0399 (1.2); 7.0252 (1.1); 7.0194 (1.1); 5.1863 (1.8); 5.1504 (2.0); 4.8257 (4.5); 4.4532 (2.0); 4.4174 (1.9); 3.9779 (16.0); 3.5628 (7.7); 3.2472 (1.3); 3.2129 (2.1); 3.1285 (4.8); 3.1061 (2.2); 3.0719 (1.4); 2.9693 (4.4); 2.7438 (3.7); 2.7397 (4.9); 2.7356 (3.7); 1.4440 (11.5); 0.5482 (0.4); 0.5383 (0.5); 0.5247 (1.0); 0.5145 (0.7); 0.5030 (0.5); 0.0228 (0.3); 0.0087 (0.6); −0.0002 (1.0); −0.0140 (0.8); −0.0225 (1.2); −0.0330 (0.8); −0.0482 (1.0); −0.0574 (0.7); −0.0712 (0.4); −0.2350 (0.5); −0.2424 (0.6); −0.2478 (0.7); −0.2562 (1.1); −0.2625 (0.6); −0.2700 (0.6); −0.2787 (0.5)

(171) Ia-62: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(172) δ=8.9922 (7.6); 7.7488 (1.8); 7.3830 (3.6); 7.2611 (1.6); 7.2412 (2.0); 7.1926 (1.7); 7.1735 (2.5); 7.0893 (2.3); 7.0698 (3.4); 7.0504 (1.4); 5.3806 (6.8); 4.8207 (2.7); 4.7846 (3.0); 4.2743 (3.0); 4.2382 (2.7); 3.1198 (16.0); 2.9569 (2.0); 2.9224 (3.0); 2.8065 (2.9); 2.7718 (2.0); 2.6866 (10.9); 2.5271 (10.1); 2.3018 (8.1); 2.2978 (10.8); 2.2937 (8.2); 0.3570 (0.4); 0.3427 (0.8); 0.3391 (0.8); 0.3298 (0.8); 0.3249 (1.1); 0.3163 (1.0); 0.3126 (1.0); 0.2985 (1.0); 0.2879 (0.7); 0.2699 (0.9); 0.2618 (1.2); 0.2442 (1.4); 0.2305 (1.0); 0.2057 (1.1); 0.1927 (1.2); 0.1883 (1.0); 0.1795 (0.8); 0.1745 (1.1); 0.1670 (0.8); 0.1485 (0.5); 0.0262 (0.8); 0.0128 (1.0); 0.0095 (1.0); −0.0002 (1.1); −0.0135 (0.9); −0.0175 (0.9); −0.0311 (0.6)

(173) Ia-63: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(174) δ=8.8860 (7.3); 7.7532 (1.6); 7.3848 (3.5); 7.2319 (1.5); 7.2120 (2.0); 7.1734 (1.7); 7.1541 (2.4); 7.0724 (2.3); 7.0529 (3.3); 7.0335 (1.4); 4.7482 (2.4); 4.7124 (2.7); 4.5231 (6.2); 4.0387 (2.8); 4.0029 (2.6); 3.1238 (16.0); 2.8083 (1.4); 2.7740 (3.2); 2.7311 (3.3); 2.6910 (9.7); 2.5316 (8.7); 2.3062 (8.1); 2.3022 (10.8); 2.2981 (8.2); 1.0101 (15.9); 0.0150 (0.9); −0.0002 (1.6); −0.0144 (1.1); −0.0302 (0.4); −0.4544 (0.5); −0.4700 (3.6); −0.4844 (3.7); −0.4992 (0.8); −0.6564 (0.3); −0.6721 (1.1); −0.6862 (1.8); −0.7006 (1.0)

(175) Ia-64: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(176) δ=8.9924 (7.3); 7.7781 (1.0); 7.0322 (0.5); 7.0136 (6.0); 6.9983 (6.1); 6.8916 (1.7); 6.8771 (1.3); 5.2575 (6.4); 4.8421 (2.6); 4.8062 (2.9); 4.2468 (2.9); 4.2109 (2.6); 3.1501 (10.2); 2.9196 (1.6); 2.8851 (3.4); 2.8343 (3.4); 2.7998 (1.6); 2.7156 (6.0); 2.5564 (5.5); 2.3310 (5.0); 2.3269 (6.6); 2.3228 (5.0); 2.1162 (16.0); 0.4570 (0.5); 0.4391 (0.9); 0.4303 (0.8); 0.4238 (1.0); 0.4152 (1.0); 0.3974 (0.8); 0.3406 (0.6); 0.3225 (0.9); 0.3141 (1.0); 0.3079 (0.7); 0.2964 (1.2); 0.2815 (0.8); 0.2091 (0.8); 0.1954 (1.1); 0.1910 (1.0); 0.1826 (0.8); 0.1771 (1.0); 0.1692 (0.9); 0.1507 (0.6); 0.0265 (0.8); 0.0124 (0.9); 0.0088 (1.0); −0.0002 (1.0); −0.0049 (0.9); −0.0140 (0.9); −0.0177 (0.9); −0.0318 (0.6)

(177) Ia-65: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(178) δ=9.3170 (7.3); 8.2029 (1.1); 7.4429 (0.7); 7.4231 (3.6); 7.4174 (3.7); 7.4065 (4.4); 7.4001 (3.4); 7.3820 (0.9); 7.2933 (2.0); 7.2758 (1.5); 5.1871 (2.5); 5.1514 (2.8); 4.8058 (6.3); 4.4644 (2.8); 4.4286 (2.6); 3.5740 (11.9); 3.2404 (1.8); 3.2062 (3.0); 3.1406 (6.3); 3.1099 (3.1); 3.0756 (1.9); 2.9813 (5.8); 2.7557 (6.4); 2.7518 (8.5); 2.7478 (6.6); 2.5399 (16.0); 1.4543 (16.0); 0.5451 (0.6); 0.5361 (0.7); 0.5217 (1.4); 0.5081 (1.0); 0.0226 (0.5); 0.0085 (1.0); −0.0002 (1.4); −0.0143 (1.3); −0.0210 (2.7); −0.0423 (1.4); −0.0507 (1.0); −0.0649 (0.6); −0.2312 (0.7); −0.2371 (0.9); −0.2428 (1.0); −0.2510 (1.6); −0.2652 (0.8); −0.2735 (0.7)

(179) Ia-66: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(180) δ=9.1775 (6.7); 7.9607 (1.3); 7.4355 (1.2); 7.4233 (1.6); 7.4138 (1.5); 7.1945 (0.4); 7.1824 (1.0); 7.1701 (3.5); 7.1631 (5.6); 7.1558 (2.9); 7.1488 (2.4); 7.1399 (1.9); 7.1316 (0.5); 5.2956 (5.8); 5.0457 (2.4); 5.0099 (2.7); 4.4154 (2.7); 4.3795 (2.4); 3.3321 (15.7); 3.2260 (1.8); 3.1903 (3.0); 3.1007 (3.0); 3.0651 (1.8); 2.8985 (7.8); 2.7391 (7.2); 2.5136 (6.4); 2.5096 (8.5); 2.5056 (6.6); 2.3174 (16.0); 0.8448 (0.5); 0.8266 (0.8); 0.8178 (0.8); 0.8113 (0.9); 0.8027 (1.0); 0.7846 (0.8); 0.7084 (0.6); 0.6906 (0.9); 0.6819 (0.9); 0.6754 (0.8); 0.6641 (1.1); 0.6490 (0.7); 0.4657 (0.7); 0.4515 (1.0); 0.4475 (0.9); 0.4392 (0.8); 0.4331 (0.9); 0.4251 (0.9); 0.4067 (0.6); 0.3092 (0.7); 0.2913 (0.9); 0.2824 (0.9); 0.2771 (0.8); 0.2679 (0.8); 0.2647 (0.9); 0.2503 (0.6)

(181) Ia-67: .sup.1H-NMR (300.2 MHz, CDCl.sub.3):

(182) δ=8.8395 (16.0); 7.3752 (0.9); 7.3646 (1.2); 7.3597 (1.1); 7.3463 (17.5); 7.3323 (21.4); 7.3048 (7.9); 7.2984 (21.9); 7.2741 (0.5); 7.2388 (0.4); 5.1197 (9.6); 5.0718 (11.2); 4.5284 (8.4); 4.4806 (7.2); 3.9167 (0.3); 3.3706 (5.3); 3.3670 (5.9); 3.3230 (9.2); 3.3193 (10.2); 3.1972 (8.3); 3.1923 (7.6); 3.1496 (4.9); 3.1444 (4.5); 2.9015 (1.2); 0.8616 (0.6); 0.8408 (3.7); 0.8297 (4.7); 0.8146 (4.2); 0.8049 (10.6); 0.7953 (6.3); 0.7787 (5.6); 0.7706 (7.1); 0.7505 (1.9); 0.6007 (3.8); 0.5807 (4.8); 0.5765 (4.5); 0.5648 (3.1); 0.5552 (4.5); 0.5459 (4.0); 0.5405 (3.1); 0.5202 (3.1); 0.4134 (4.2); 0.3935 (3.8); 0.3864 (4.1); 0.3798 (4.7); 0.3675 (3.5); 0.3587 (3.9); 0.3527 (4.0); 0.3327 (2.8); 0.0450 (0.4); 0.0340 (18.0); 0.0232 (0.9)

(183) Ia-68: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(184) δ=9.3417 (7.5); 7.7171 (0.8); 7.7135 (0.9); 7.6981 (1.6); 7.6943 (1.9); 7.6751 (1.0); 7.5635 (0.4); 7.5594 (0.4); 7.5451 (1.1); 7.5303 (1.0); 7.5253 (1.3); 7.5113 (0.7); 7.5074 (0.6); 7.4210 (1.4); 7.3971 (3.5); 7.3775 (3.2); 7.3614 (1.2); 5.1816 (2.5); 5.1459 (2.8); 4.9439 (6.8); 4.5716 (2.8); 4.5358 (2.5); 3.5714 (9.7); 3.2479 (6.0); 3.1384 (0.5); 2.9791 (0.5); 2.7538 (5.5); 2.74% (7.3); 2.7454 (5.5); 1.4694 (16.0); 0.4444 (0.6); 0.4349 (0.7); 0.4277 (0.8); 0.4208 (1.4); 0.4110 (0.9); 0.4068 (0.9); 0.3994 (0.7); 0.0228 (0.5); 0.0087 (0.9); −0.0002 (1.5); −0.0140 (1.2); −0.0222 (2.0); −0.0311 (1.1); −0.0462 (1.4); −0.0553 (0.9); −0.0693 (0.5); −0.2310 (0.8); −0.2380 (0.9); −0.2436 (1.0); −0.2519 (1.6); −0.2581 (0.8); −0.2660 (0.8); −0.2748 (0.7)

(185) Ia-69: .sup.1H-NMR (300.2 MHz, CDCl.sub.3):

(186) δ=8.8257 (9.8); 7.3963 (1.2); 7.3712 (2.6); 7.3485 (2.6); 7.3242 (1.8); 7.2992 (19.7); 7.1279 (6.8); 7.1035 (5.4); 7.0987 (6.0); 7.0674 (2.7); 7.0611 (2.1); 7.0418 (1.1); 7.0358 (1.1); 7.0303 (0.9); 5.3384 (4.5); 5.0096 (5.6); 4.9617 (7.2); 4.6334 (6.2); 4.5855 (4.8); 3.4356 (4.6); 3.3892 (5.5); 2.9866 (5.3); 2.9402 (4.3); 2.5564 (11.1); 1.5998 (16.0); 1.2889 (1.1); 0.8293 (1.0); 0.8232 (0.8); 0.8154 (1.5); 0.7995 (2.1); 0.7912 (2.0); 0.7861 (1.9); 0.7757 (2.0); 0.7696 (1.4); 0.7608 (0.6); 0.7438 (1.1); 0.6287 (1.0); 0.6202 (1.3); 0.6046 (2.4); 0.5964 (3.2); 0.5897 (6.2); 0.5734 (6.0); 0.5665 (3.6); 0.5599 (2.7); 0.5426 (1.3); 0.5357 (1.2); 0.4335 (1.1); 0.4166 (0.6); 0.4078 (1.3); 0.4025 (2.1); 0.3915 (1.8); 0.3856 (2.0); 0.3785 (2.6); 0.3612 (1.5); 0.3544 (0.8); 0.3479 (1.1); 0.0476 (1.2); 0.0369 (25.8); 0.0262 (1.7)

(187) Ia-70: .sup.1H-NMR (300.2 MHz, CDCl.sub.3):

(188) δ=8.7821 (4.1); 7.6375 (1.2); 7.6337 (1.4); 7.6109 (1.4); 7.6071 (1.6); 7.4840 (1.0); 7.4790 (1.2); 7.4582 (1.4); 7.4531 (1.5); 7.3263 (0.7); 7.3222 (0.8); 7.2996 (2.6); 7.2761 (0.8); 7.2720 (0.8); 7.1970 (0.8); 7.1915 (0.9); 7.1705 (1.2); 7.1656 (1.2); 7.1459 (0.5); 7.1405 (0.6); 5.0026 (1.8); 4.9529 (2.9); 4.7822 (2.7); 4.7325 (1.7); 3.6505 (16.0); 3.3884 (1.5); 3.3381 (2.4); 3.1839 (2.4); 3.1337 (1.5); 1.6923 (0.8); 0.9510 (0.6); 0.9437 (0.5); 0.9364 (0.4); 0.9229 (0.9); 0.9167 (1.6); 0.9087 (0.8); 0.8927 (1.2); 0.8889 (1.5); 0.8815 (1.1); 0.8739 (0.4); 0.8587 (1.4); 0.8387 (0.7); 0.7928 (0.6); 0.7740 (1.1); 0.7523 (1.8); 0.7398 (1.0); 0.7354 (1.0); 0.7252 (1.0); 0.7178 (1.3); 0.7069 (0.4); 0.6995 (0.4); 0.6907 (0.6); 0.0302 (1-5)

(189) Ia-71: .sup.1H-NMR (300.2 MHz, CDCl.sub.3):

(190) δ=8.8877 (6.1); 7.9951 (2.0); 7.7140 (0.8); 7.6910 (1.6); 7.6658 (0.9); 7.6197 (0.8); 7.5945 (1.6); 7.5711 (0.9); 7.2987 (4.0); 7.2725 (2.0); 7.2467 (0.9); 5.1869 (3.0); 5.1392 (3.5); 4.5522 (2.5); 4.5044 (2.2); 3.5584 (0.4); 3.4698 (1.4); 3.4225 (2.3); 3.2984 (2.0); 3.2919 (2.1); 3.2511 (1.2); 3.2445 (1.2); 2.9913 (16.0); 2.8944 (12.0); 0.8177 (1.2); 0.8113 (1.4); 0.7842 (3.1); 0.7774 (1.8); 0.7549 (2.3); 0.5807 (1.0); 0.5607 (1.3); 0.5561 (1.1); 0.5450 (0.8); 0.5340 (1.1); 0.5271 (1.0); 0.5204 (0.7); 0.5003 (0.7); 0.3906 (1.1); 0.3708 (1.0); 0.3588 (1.4); 0.3439 (0.9); 0.3369 (1.0); 0.3300 (1.0); 0.3099 (0.7); 0.0242 (2.7)

(191) Ia-72: .sup.1H-NMR (300.2 MHz, CDCl.sub.3):

(192) δ=8.7836 (16.0); 7.3657 (0.5); 7.3386 (4.6); 7.3317 (5.3); 7.3268 (11.5); 7.3192 (13.8); 7.3050 (5.8); 7.2983 (12.2); 7.2779 (1.1); 7.1709 (0.5); 7.1561 (2.6); 7.1433 (2.6); 7.1371 (1.8); 7.1245 (4.4); 7.1145 (2.0); 7.1029 (2.2); 7.0928 (1.9); 5.3527 (6.5); 5.3049 (7.2); 4.4365 (5.9); 4.3889 (5.3); 3.7761 (3.9); 3.7692 (4.0); 3.7272 (5.3); 3.7202 (5.5); 3.4713 (5.1); 3.4626 (5.1); 3.4224 (3.7); 3.4137 (3.8); 2.7707 (7.4); 2.7600 (7.4); 2.0416 (0.4); 1.6411 (2.7); 1.2878 (1.7); 1.0521 (1.1); 1.0319 (3.5); 1.0263 (2.0); 1.0160 (1.5); 1.0109 (3.6); 1.0060 (4.2); 0.9961 (4.5); 0.9899 (3.4); 0.9859 (4.5); 0.9764 (4.1); 0.9696 (4.4); 0.9557 (2.4); 0.9520 (4.3); 0.9318 (1.6); 0.6725 (2.8); 0.6525 (3.3); 0.6460 (2.6); 0.6385 (2.7); 0.6266 (3.0); 0.6179 (3.0); 0.6120 (2.2); 0.5920 (2.3); 0.4277 (2.8); 0.4075 (2.8); 0.4033 (3.2); 0.3913 (2.8); 0.3826 (2.7); 0.3718 (2.4); 0.3669 (2.7); 0.3468 (2.0); 0.0435 (0.4); 0.0327 (11.2); 0.0218 (0.4)

(193) Ia-73: .sup.1H-NMR (400.0 MHz, CD.sub.3CN):

(194) δ=8.8434 (9.3); 8.5811 (16.0); 8.4363 (9.2); 8.4239 (9.4); 7.5201 (7.4); 7.5077 (7.2); 5.4476 (1.0); 5.1436 (10.9); 5.1072 (12.2); 4.4898 (9.7); 4.4534 (8.7); 3.5309 (8.6); 3.4957 (11.2); 3.3315 (10.4); 3.2963 (7.4); 2.1487 (15.2); 2.1204 (0.9); 2.1142 (0.8); 2.1080 (0.8); 2.1018 (0.6); 2.0956 (0.4); 2.0866 (0.5); 1.9648 (2.6); 1.9587 (6.3); 1.9529 (32.1); 1.9467 (57.6); 1.9406 (76.1); 1.9344 (52.4); 1.9282 (26.9); 1.7751 (0.3); 1.7690 (0.5); 0.8591 (1.4); 0.8437 (4.2); 0.8397 (2.4); 0.8322 (1.7); 0.8243 (7.3); 0.8168 (5.2); 0.8124 (2.8); 0.8057 (4.2); 0.7973 (7.6); 0.7903 (1.4); 0.7799 (4.5); 0.7643 (1.6); 0.5756 (2.8); 0.5609 (3.3); 0.5559 (2.8); 0.5499 (2.6); 0.5415 (3.0); 0.5348 (2.9); 0.5302 (2.3); 0.5153 (2.3); 0.3820 (3.2); 0.3672 (3.7); 0.3634 (3.5); 0.3548 (3.3); 0.3483 (3.0); 0.3403 (3.2); 0.3362 (3.0); 0.3215 (2.3); 0.0081 (2.1); −0.0002 (61.8); −0.0086 (2.2)

(195) Ia-74: .sup.1H-NMR (300.2 MHz, CDCl.sub.3):

(196) δ=8.8556 (12.3); 8.5503 (6.3); 8.5426 (6.5); 8.5059 (6.2); 8.5000 (6.3); 7.8026 (3.6); 7.7958 (6.0); 7.7888 (3.5); 7.2984 (17.2); 5.0733 (6.3); 5.0256 (7.6); 4.6177 (6.4); 4.5699 (5.3); 3.5240 (16.0); 3.3990 (4.5); 3.3523 (6.1); 3.3251 (2.4); 3.0788 (5.8); 3.0320 (4.4); 1.6646 (1.8); 1.3018 (0.4); 1.2890 (0.8); 1.2786 (0.6); 1.2552 (0.3); 1.0800 (0.6); 0.7941 (1.2); 0.7741 (1.7); 0.7675 (1.4); 0.7581 (1.9); 0.7499 (1.9); 0.7381 (2.5); 0.7340 (2.2); 0.7165 (2.1); 0.6516 (1.4); 0.6271 (2.2); 0.6154 (1.8); 0.6072 (2.0); 0.5910 (2.8); 0.5733 (3.7); 0.5695 (3.7); 0.5520 (2.6); 0.5451 (0.8); 0.5358 (1.9); 0.5275 (1.8); 0.5161 (2.0); 0.4917 (1.2); 0.3427 (1.8); 0.3251 (2.1); 0.3213 (2.1); 0.3092 (1.8); 0.3013 (1.8); 0.2916 (1.4); 0.2849 (1.5); 0.2650 (1.2); 0.0450 (0.7); 0.0342 (19.8); 0.0233 (0.7)

(197) Ia-75: .sup.1H-NMR (300.2 MHz, CDCl.sub.3):

(198) δ=8.8447 (16.0); 7.2984 (3.2); 7.0606 (0.9); 7.0509 (1.7); 7.0394 (11.6); 7.0151 (11.5); 7.0038 (1.8); 6.9941 (1.0); 5.3287 (0.5); 5.2434 (6.7); 5.1955 (7.6); 4.4937 (6.3); 4.4458 (5.6); 3.4322 (2.5); 3.3838 (6.2); 3.3214 (6.0); 3.2730 (2.5); 3.0113 (5.3); 2.0368 (1.4); 0.9924 (1.1); 0.9722 (2.8); 0.9669 (1.9); 0.9561 (1.4); 0.9461 (4.0); 0.9435 (3.6); 0.9360 (3.8); 0.9302 (2.2); 0.9183 (3.6); 0.9090 (5.6); 0.8982 (1.3); 0.8838 (3.7); 0.8636 (1.5); 0.6038 (2.3); 0.5836 (3.0); 0.5779 (2.4); 0.5693 (2.3); 0.5579 (2.7); 0.5487 (2.7); 0.5433 (2.0); 0.5230 (2.0); 0.3928 (2.4); 0.3722 (2.7); 0.3687 (3.0); 0.3561 (2.5); 0.3480 (2.4); 0.3359 (2.3); 0.3320 (2.5); 0.3117 (1.7); 0.0244 (2.6

(199) Ia-76: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(200) δ=8.9687 (3.2); 7.4527 (1.4); 7.4064 (0.7); 7.3861 (1.4); 7.3636 (1.0); 7.3163 (0.8); 7.2972 (1.0); 7.2780 (0.4); 5.3877 (1.5); 5.3836 (1.6); 4.6878 (0.8); 4.6521 (1.0); 4.2636 (1.0); 4.2277 (0.9); 3.0866 (16.0); 2.9401 (0.5); 2.9056 (1.0); 2.8309 (1.0); 2.7965 (0.6); 2.6498 (1.2); 2.4903 (1.1); 2.2653 (2.9); 2.2613 (3.9); 2.2571 (3.0); 0.2323 (0.9); 0.2206 (0.4); 0.1817 (1.0); 0.1709 (0.3); −0.0002 (0.5); −0.0255 (0.4); −0.2131 (0.4); −0.2395 (0.5)

(201) Ib-01: .sup.1H-NMR (300.2 MHz, CDCl.sub.3):

(202) δ=8.6492 (16.0); 8.5475 (0.4); 8.5293 (8.7); 8.5214 (9.2); 8.5124 (8.6); 8.5064 (8.3); 7.7704 (4.9); 7.7638 (8.0); 7.7564 (4.7); 7.2985 (12.7); 5.3745 (8.5); 5.3278 (10.0); 4.8517 (10.7); 4.8049 (9.1); 3.7676 (0.4); 3.7442 (0.6); 3.7065 (1.1); 3.5228 (3.0); 3.3920 (6.7); 3.3453 (8.3); 2.9531 (7.9); 2.9065 (6.5); 2.7212 (0.4); 2.7174 (0.4); 1.3004 (0.3); 1.2771 (0.7); 1.2537 (0.3); 0.7413 (0.6); 0.7220 (2.8); 0.7158 (1.4); 0.7046 (3.6); 0.6968 (3.4); 0.6861 (5.5); 0.6799 (6.7); 0.6693 (4.0); 0.6606 (5.6); 0.6459 (5.0); 0.6271 (2.1); 0.5797 (3.6); 0.5607 (3.9); 0.5567 (2.8); 0.5434 (2.1); 0.5365 (3.2); 0.5249 (2.6); 0.5203 (1.7); 0.5006 (1.9); 0.3933 (3.1); 0.3743 (2.8); 0.3677 (2.9); 0.3596 (3.0); 0.3491 (2.5); 0.3397 (2.5); 0.3336 (2.6); 0.3140 (1.8); 0.0435 (0.4); 0.0328 (15.8); 0.0219 (0.7)

(203) Ib-02: .sup.1H-NMR (300.2 MHz, CDCl.sub.3):

(204) δ=8.6050 (16.0); 7.4814 (2.2); 7.4757 (2.3); 7.4562 (4.6); 7.4504 (4.8); 7.4310 (2.6); 7.4252 (2.7); 7.3507 (1.2); 7.3447 (1.2); 7.3328 (1.3); 7.3259 (3.0); 7.3191 (2.4); 7.3070 (2.6); 7.2988 (9.4); 7.2929 (2.2); 7.2810 (2.1); 7.2749 (1.8); 7.1868 (3.8); 7.1829 (4.2); 7.1619 (5.8); 7.1580 (6.3); 7.1366 (3.0); 7.1322 (5.3); 7.1037 (3.0); 7.0985 (4.5); 7.0943 (3.3); 7.0702 (2.6); 7.0668 (2.4); 5.4574 (8.2); 5.4106 (9.3); 5.3334 (0.5); 4.7282 (9.2); 4.6814 (8.1); 3.4287 (4.4); 3.3814 (6.8); 3.2993 (7.4); 3.2928 (7.6); 3.2178 (5.9); 3.2128 (5.7); 3.1706 (3.8); 3.1654 (3.8); 1.6758 (2.0); 1.5284 (0.4); 1.5046 (0.4); 1.2889 (0.6); 0.9275 (1.8); 0.9081 (3.2); 0.9023 (2.6); 0.8911 (2.5); 0.8829 (3.7); 0.8717 (3.9); 0.8658 (3.0); 0.8463 (6.5); 0.8262 (2.3); 0.8220 (3.6); 0.8112 (3.8); 0.8027 (2.1); 0.7915 (3.1); 0.7873 (4.2); 0.7680 (2.6); 0.6057 (3.0); 0.5862 (4.0); 0.5804 (3.0); 0.5710 (2.6); 0.5610 (3.5); 0.5514 (3.3); 0.5457 (2.2); 0.5261 (2.5); 0.4565 (3.4); 0.4369 (3.4); 0.4328 (3.7); 0.4201 (3.4); 0.4131 (2.9); 0.4005 (2.9); 0.3963 (3.1); 0.3767 (2.1); 0.0337 (5.3)

(205) Ib-03: .sup.1H-NMR (300.2 MHz, CDCl.sub.3):

(206) δ=8.6538 (0.3); 8.6261 (16.0); 7.2987 (8.1); 7.2425 (2.0); 7.2229 (2.9); 7.2176 (4.2); 7.2060 (1.8); 7.1976 (2.5); 7.1924 (2.1); 7.1841 (1.1); 7.1776 (1.2); 7.1561 (2.6); 7.1510 (2.6); 7.1448 (1.4); 7.1331 (2.8); 7.1242 (3.7); 7.1164 (5.1); 7.1023 (3.5); 7.0966 (5.9); 7.0885 (3.3); 7.0744 (2.5); 7.0712 (2.6); 7.0607 (1.1); 7.0439 (0.9); 5.4444 (8.2); 5.3977 (9.4); 4.7669 (9.2); 4.7202 (8.1); 3.4183 (11.7); 3.3683 (2.8); 3.3210 (7.3); 3.2700 (6.6); 3.2639 (6.6); 3.2229 (2.5); 3.2166 (2.5); 1.6516 (3.0); 1.5305 (0.5); 1.5069 (0.5); 1.2878 (1.6); 0.9252 (1.7); 0.9058 (3.2); 0.8999 (2.5); 0.8887 (2.4); 0.8804 (3.7); 0.8694 (3.9); 0.8633 (3.0); 0.8516 (3.2); 0.8440 (4.1); 0.8317 (2.3); 0.8276 (3.8); 0.8168 (3.8); 0.8083 (2.0); 0.7971 (3.0); 0.7930 (4.3); 0.7736 (2.5); 0.6108 (2.9); 0.5912 (3.9); 0.5854 (3.0); 0.5762 (2.5); 0.5658 (3.4); 0.5564 (3.3); 0.5508 (2.2); 0.5310 (2.4); 0.4606 (3.3); 0.4408 (3.3); 0.4369 (3.7); 0.4240 (3.2); 04170 (2.8); 0.4043 (2.9); 0.4003 (3.1); 0.3805 (2.0); 0.0331 (6.9)

(207) Ib-04: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO):

(208) δ=8.9539 (16.0); 8.3162 (0.4); 7.6642 (0.3); 7.6544 (3.5); 7.6462 (2.8); 7.6404 (2.1); 7.6361 (2.6); 7.6308 (4.1); 7.6225 (0.4); 7.4588 (3.6); 7.4539 (2.4); 7.4497 (2.0); 7.4433 (2.9); 7.4416 (3.2); 7.4355 (5.0); 7.4253 (0.5); 7.3365 (0.6); 7.3310 (1.4); 7.3180 (5.0); 7.3127 (8.8); 7.3036 (10.1); 7.2947 (7.4); 7.2889 (3.9); 7.2763 (1.1); 7.2705 (0.6); 5.3482 (13.6); 5.2297 (5.9); 5.1947 (6.6); 4.5963 (6.7); 4.5614 (6.1); 3.5174 (5.7); 3.4819 (7.1); 3.3239 (63.3); 3.2275 (6.5); 3.1921 (5.2); 2.6755 (0.5); 2.6709 (0.7); 2.6666 (0.5); 2.5414 (4.3); 2.5244 (1.6); 2.5109 (39.6); 2.5065 (81.7); 2.5020 (109.0); 2.4974 (79.3); 2.4930 (38.5); 2.3333 (0.5); 2.3287 (0.7); 2.3242 (0.5); 0.9165 (1.2); 0.9017 (1.8); 0.8980 (2.0); 0.8897 (2.0); 0.8833 (2.1); 0.8750 (2.1); 0.8712 (2.1); 0.8565 (1.8); 0.7233 (1.3); 0.7085 (1.5); 0.7048 (2.1); 0.6971 (2.2); 0.6902 (1.9); 0.6823 (2.0); 0.6786 (2.5); 0.6639 (1.8); 0.5263 (1.6); 0.5120 (2.4); 0.5080 (2.0); 0.5001 (1.6); 0.4935 (2.4); 0.4859 (2.1); 0.4818 (1.5); 0.4672 (1.5); 0.4527 (1.8); 0.4343 (2.2); 0.4260 (2.1); 0.4201 (1.6); 0.4112 (1.6); 0.4076 (1.9); 0.3931 (1.0); 0.1460 (0.6); 0.0079 (5.5); −0.0002 (153.3); −0.0085 (5.7); −0.1497 (0.7)

(209) Ib-05: .sup.1H-NMR (601.6 MHz, CD.sub.3CN):

(210) δ=8.6518 (16.0); 8.6276 (1.4); 8.5220 (7.2); 8.3069 (5.6); 8.3037 (5.9); 8.2991 (5.8); 8.2959 (5.8); 8.2521 (0.6); 8.2490 (0.6); 8.2443 (0.6); 8.2412 (0.6); 7.9456 (5.8); 7.9424 (5.8); 7.9329 (6.1); 7.9297 (5.9); 7.8957 (2.1); 7.8947 (2.1); 7.8873 (2.1); 7.6440 (0.5); 7.6409 (0.6); 7.6315 (0.6); 7.6283 (0.6); 7.5107 (1.0); 7.5085 (2.4); 7.5061 (2.4); 7.5039 (1.1); 7.4987 (1.1); 7.4965 (2.4); 7.4940 (2.4); 7.4918 (1.1); 7.3304 (6.4); 7.3227 (6.4); 7.3178 (6.3); 7.3100 (6.1); 7.2578 (0.8); 7.2501 (0.7); 7.2454 (0.6); 7.2375 (0.6); 6.8458 (3.1); 6.8373 (3.1); 6.8338 (3.1); 6.8253 (2.9); 5.3811 (12.1); 5.3574 (13.0); 5.3187 (4.8); 5.2946 (8.1); 5.2264 (8.0); 5.2023 (4.8); 5.0782 (0.9); 5.0540 (1.8); 5.0183 (1.9); 4.9941 (0.8); 4.7277 (13.2); 4.7039 (12.4); 3.6345 (2.4); 3.6060 (4.4); 3.5390 (4.7); 3.5171 (13.6); 3.5127 (11.2); 3.4887 (12.0); 3.3644 (11.9); 3.3405 (8.8); 3.3025 (3.6); 3.2759 (0.7); 3.0856 (0.4); 2.7714 (0.4); 2.7431 (0.3); 2.6879 (0.4); 2.6317 (0.4); 2.5284 (0.7); 2.2392 (0.4); 2.1954 (1.1); 2.1664 (26.4); 2.1413 (1.4); 2.1270 (0.4); 1.9876 (1.1); 1.9661 (1.0); 1.9580 (2.4); 1.9539 (2.8); 1.9500 (15.7); 1.9459 (27.4); 1.9418 (40.5); 1.9377 (27.9); 1.9336 (14.2); 1.9250 (1.0); 1.9226 (0.9); 1.6708 (1.9); 1.6210 (0.3); 1.6088 (0.3); 1.4350 (0.6); 1.4245 (1.0); 1.3404 (1.2); 1.3090 (1.0); 1.2969 (0.3); 1.2848 (1.7); 1.2682 (2.9); 1.0314 (0.9); 1.0216 (1.4); 1.0177 (1.4); 1.0144 (1.5); 1.0075 (2.3); 1.0060 (2.3); 1.0015 (2.0); 0.9929 (2.7); 0.9837 (1.4); 0.9780 (0.4); 0.9722 (1.9); 0.9687 (0.4); 0.9656 (2.4); 0.9623 (0.8); 0.9544 (3.8); 0.9506 (0.6); 0.9456 (3.7); 0.9436 (2.8); 0.9395 (0.7); 0.9348 (4.1); 0.9302 (4.4); 0.9248 (2.8); 0.9215 (2.0); 0.9191 (4.0); 0.9173 (4.4); 0.9121 (2.0); 0.9077 (2.4); 0.9033 (0.8); 0.8993 (1.8); 0.8897 (0.5); 0.8809 (0.6); 0.8692 (0.4); 0.8656 (0.4); 0.8546 (0.7); 0.8440 (0.7); 0.8374 (1.2); 0.8333 (2.9); 0.8236 (4.3); 0.8208 (3.2); 0.8154 (3.0); 0.8109 (4.6); 0.8056 (5.0); 0.8027 (3.6); 0.8004 (4.3); 0.7928 (5.0); 0.7905 (3.1); 0.7881 (4.9); 0.7827 (4.6); 0.7782 (2.4); 0.7727 (3.1); 0.7706 (5.1); 0.7606 (2.7); 0.6725 (0.4); 0.6622 (0.4); 0.6551 (0.4); 0.6508 (0.5); 0.6437 (0.6); 0.5527 (3.4); 0.5427 (4.1); 0.5400 (3.6); 0.5352 (3.4); 0.5300 (3.9); 0.5251 (3.9); 0.5225 (3.2); 0.5124 (3.2); 0.4189 (3.8); 0.4088 (3.8); 0.4068 (4.3); 0.4008 (3.8); 0.3966 (3.6); 0.3907 (3.6); 0.3887 (3.9); 0.3786 (2.9); −0.0002 (9.2); −0.0057 (0.4)

(211) Ib-06: .sup.1H-NMR (300.2 MHz, CDCl.sub.3):

(212) δ=8.6552 (1.0); 8.6261 (16.0); 7.4803 (0.4); 7.4006 (1.6); 7.3947 (4.9); 7.3867 (1.9); 7.3700 (9.8); 7.3455 (7.2); 7.3121 (0.4); 7.2990 (19.4); 7.1242 (3.8); 7.1209 (3.8); 7.0980 (5.5); 7.0948 (6.0); 7.0719 (2.6); 7.0685 (2.7); 7.0551 (0.5); 7.0514 (0.5); 5.6332 (0.4); 5.5867 (0.4); 5.4441 (7.6); 5.3974 (8.6); 5.3373 (0.4); 4.9682 (0.6); 4.9219 (0.5); 4.7579 (8.6); 4.7112 (7.6); 3.5877 (0.4); 3.4269 (11.2); 3.3743 (3.0); 3.3273 (6.4); 3.2509 (6.0); 3.2444 (6.1); 3.2037 (2.9); 3.1972 (3.0); 1.6196 (12.1); 1.5277 (1.2); 1.5037 (1.2); 1.2896 (0.7); 0.9321 (1.6); 0.9127 (3.0); 0.9067 (2.4); 0.8955 (2.2); 0.8873 (3.6); 0.8762 (3.8); 0.8701 (2.9); 0.8579 (3.0); 0.8508 (4.0); 0.8384 (2.0); 0.8339 (3.7); 0.8231 (3.8); 0.8147 (2.0); 0.8036 (2.8); 0.7992 (4.2); 0.7800 (2.5); 0.6153 (2.9); 0.5958 (3.7); 0.5899 (2.8); 0.5807 (2.5); 0.5704 (3.4); 0.5610 (3.2); 0.5553 (2.2); 0.5355 (2.4); 0.4666 (3.2); 0.4469 (3.1); 0.4428 (3.6); 0.4301 (3.2); 0.4231 (2.9); 0.4105 (2.7); 0.4062 (3.1): 0.3865 (2.1); 0.0463 (0.6); 0.0354 (20.3); 0.0245 (0.8)

(213) Ib-07: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(214) δ=8.9873 (16.0); 7.9603 (0.4); 7.1788 (0.5); 7.1610 (5.0); 7.1394 (7.8); 7.1181 (5.1); 5.3429 (13.1); 5.2065 (5.8); 5.1712 (7.0); 4.8454 (6.6); 4.8102 (5.6); 3.3248 (120.1); 3.2514 (2.9); 3.2159 (5.5); 3.1505 (5.2); 3.1151 (2.7); 2.8986 (2.2); 2.7392 (2.0); 2.5132 (13.6); 2.5092 (18 0); 2.5051 (13.8); 0 8217 (1.1); 0.8075 (1.6); 0.7994 (2.3); 0.7849 (3.4); 0.7763 (1.9); 0.7621 (1.9); 0.7244 (1.4); 0.7100 (1.4); 0.7015 (2.8); 0.6914 (1.7); 0.6844 (2.3); 0.6803 (2.5); 0.6660 (1.7); 0.4801 (6.0); 0.4571 (8.0); 0.4348 (3.8)

(215) Ib-08: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(216) δ=8.9825 (16.0); 7.5560 (3.0); 7.5355 (6.4); 7.5149 (3.7); 7.3865 (4.0); 7.3818 (4.4); 7.3620 (4.2); 7.3572 (4.6); 7.2598 (4.4); 7.2553 (4.4); 7.2391 (4.1); 7.2345 (3.9); 5.5342 (13.1); 5.1837 (5.9); 5.1485 (7.1); 4.8139 (6.6); 4.7787 (5.7); 3.3241 (124.8); 3.2704 (4.8); 3.2352 (6.0); 3.0699 (5.4); 3.0348 (3.9); 2.8982 (0.8); 2.7390 (0.7); 2.5090 (18.2); 0.6367 (0.7); 0.6215 (1.8); 0.6034 (2.3); 0.5946 (2.8); 0.5898 (2.8); 0.5764 (2.8); 0.5683 (2.8); 0.5616 (2.8); 0.5544 (1.7); 0.5433 (3.0); 0.5292 (1.8); 0.4611 (1.7); 0.4470 (2.7); 0.4362 (1.6); 0.4282 (2.6); 0.4223 (2.5); 0.4057 (3.0); 0.3906 (2.7); 0.3797 (2.4); 0.3645 (2.1); 0.3479 (1.0)

(217) Ib-09: .sup.1H-NMR (400.1 MHz, CDCl.sub.3):

(218) δ=8.5910 (7.9); 7.2863 (9.9); 7.1503 (0.9); 7.1299 (2.4); 7.1126 (3.0); 7.0927 (2.0); 6.8750 (1.7); 6.8533 (3.6); 6.8332 (2.5); 5.5539 (3.7); 5.5189 (4.6); 4.6816 (3.6); 4.6466 (3.9); 3.4246 (1.5); 3.3888 (4.5); 3.3503 (4.8); 3.3150 (2.5); 3.2669 (6.5); 2.2821 (16.0); 1.5748 (8.6); 1.0649 (0.9); 1.0504 (1.7); 1.0464 (1.8); 1.0372 (2.2); 1.0316 (2.3); 1.0232 (2.7); 1.0043 (2.3); 0.9287 (1.1); 0.9108 (2.0); 0.9021 (2.4); 0.8963 (2.2); 0.8850 (2.9); 0.8701 (2.2); 0.5976 (1.0); 0.5791 (2.1); 0.5708 (2.2); 0.5641 (2.4); 0.5562 (2.6); 0.5375 (2.0): 0.4125 (1.1); 0.3951 (2.1); 0.3849 (2.4); 0.3800 (2.3); 0.3683 (2.7); 0.3529 (1.9)

(219) Ib-10: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(220) δ=8.9897 (16.0); 7.3764 (0.7); 7.3715 (0.8); 7.3548 (2.2); 7.3356 (2.7); 7.3202 (1.4); 7.3156 (1.4); 7.2964 (1.6); 7.2758 (2.8); 7.2531 (2.5); 7.2302 (0.9); 5.5829 (13.7); 5.1917 (6.0); 5.1564 (7.4); 4.8661 (7.1); 4.8307 (5.9); 3.3271 (196.4); 3.2826 (6.3); 3.0815 (4.7); 3.0460 (3.5); 2.8984 (0.5); 2.7390 (0.5); 2.5090 (15.8); 2.5050 (12.4); 0.6145 (0.4); 0.6006 (2.0); 0.5922 (2.5); 0.5801 (3.3); 0.5726 (5.2); 0.5683 (4.9); 0.5533 (4.8); 0.5354 (1.4); 0.4693 (1.8); 0.4557 (2.7); 0.4475 (2.4); 0.4327 (3.0); 0.4168 (2.7); 0.3991 (2.8); 0.3902 (2.3); 0.3842 (2.0); 0.3770 (1.7); 0.3721 (2.0); 0.3580 (1.0)

(221) Ib-11: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(222) δ=8.9945 (16.0); 7.4713 (0.8); 7.4634 (1.0); 7.4560 (1.1); 7.4486 (1.8); 7.4433 (1.8); 7.4356 (1.9); 7.4272 (1.8); 7.4230 (1.9); 7.4154 (1.2); 7.4076 (1.1); 7.3999 (1.0); 7.1951 (2.1); 7.1833 (2.2); 7.1783 (2.0); 7.1716 (2.2); 5.6560 (14.0); 5.2038 (5.8); 5.1684 (7.1); 4.8643 (6.9); 4.8289 (5.8); 3.3544 (4.0); 3.3243 (151.4); 3.1121 (4.5); 3.0763 (3.4); 2.8990 (0.6); 2.7391 (0.5); 2.5137 (15.2); 2.5095 (20.7); 2.5054 (16.2); 0.6562 (0.7); 0.6423 (1.8); 0.6378 (1.5); 0.6292 (1.5); 0.6234 (2.5); 0.6158 (4.0); 0.5970 (4.7); 0.5914 (3.3); 0.5839 (1.6); 0.5726 (3.0); 0.5589 (1.7); 0.4902 (1.7); 0.4763 (2.6); 0.4655 (1.6); 0.4574 (2.5); 0.4515 (2.4); 0.4339 (3.1); 0.4169 (2.6); 0.4080 (2.3); 0.4029 (1.9); 0.3899 (2.0); 0.3757 (1.0)

(223) Ib-12: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(224) δ=8.9912 (16.0); 7.5573 (1.5); 7.5366 (3.3); 7.5199 (3.4); 7.4992 (1.9); 7.2978 (2.6); 7.2791 (4.5); 7.2760 (4.7); 7.2570 (2.2); 7.2540 (2.2); 5.5833 (13.8); 5.1964 (6.0); 5.1611 (7.3); 4.8596 (7.1); 4.8243 (6.0); 3.3258 (150.7); 3.2907 (6.4); 3.0911 (4.8); 3.0553 (3.6); 2.8986 (0.3); 2.5136 (15.7); 2.5095 (20.8); 2.5057 (16.3); 0.6081 (0.4); 0.5945 (2.0); 0.5839 (2.5); 0.5743 (3.2); 0.5643 (4.9); 0.5611 (4.8); 0.5472 (4.5); 0.5418 (4.1); 0.5280 (1.4); 0.4707 (2.0); 0.4572 (2.7); 0.4490 (2.3); 0.4340 (3.0); 0.4180 (2.9); 0.4006 (2.9); 0.3915 (2.4); 0.3858 (2.0); 0.3779 (1.8); 0.3734 (2.0); 0.3593 (1.1)

(225) Ib-13: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(226) δ=8.7509 (1.2); 6.7528 (0.3); 5.2319 (0.9); 4.9482 (0.4); 4.9130 (0.5); 4.5737 (0.5); 4.5385 (0.5); 3.6415 (3.5); 3.1023 (16.0); 3.0040 (0.3); 2.9685 (0.5); 2.8390 (0.4); 2.2822 (1.4)

(227) Ib-14: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(228) δ=8.9778 (6.6); 7.2464 (0.6); 7.2254 (1.2); 7.2091 (1.3); 7.1895 (0.8); 7.1022 (1.0); 7.0991 (1.1); 7.0762 (1.8); 7.0536 (0.8); 7.0506 (0.8); 5.4744 (5.6); 5.1834 (2.4); 5.1482 (2.9); 4.8056 (2.8); 4.7704 (2.4); 3.9010 (16.0); 3.3263 (97.1); 3.2411 (1.6); 3.2058 (2.2); 3.0758 (2.0); 3.0403 (1.4); 2.5089 (8.1); 0.6602 (0.3); 0.6451 (0.8); 0.6324 (0.7); 0.6269 (1.0); 0.6186 (1.0); 0.6011 (1.2); 0.5859 (1.0); 0.5787 (1.1); 0.5720 (0.7); 0.5604 (1.2); 0.5465 (0.8); 0.4606 (0.7); 0.4463 (1.1); 0.4353 (0.7); 0.4279 (1.0); 0.4213 (1.0); 0.4016 (1.4); 0.3830 (1.1); 0.3738 (1.0); 0.3576 (0.9); 0.3419 (0.4)

(229) Ib-15: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(230) δ=8.9724 (5.6); 6.7210 (3.6); 6.6970 (3.6); 6.6802 (0.4); 5.2015 (5.6); 5.1622 (2.4); 4.7769 (2.2); 4.7418 (2.0); 3.7846 (16.0); 3.3225 (46.1); 3.1759 (0.3); 3.1353 (3.5); 3.0967 (0.4); 2.5090 (6.2); 0.8848 (0.4); 0.8703 (0.6); 0.8597 (0.7); 0.8513 (0.7); 0.8438 (0.8); 0.8252 (0.7); 0.7263 (0.5); 0.7061 (0.8); 0.6905 (0.9); 0.6820 (0.8); 0.6678 (0.6); 0.4593 (1.5); 0.4371 (2.2); 0.4168 (1.2); 0.4119 (1.1)

(231) Ib-16: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(232) δ=8.9867 (16.0); 7.5541 (1.5); 7.5320 (3.4); 7.5255 (2.4); 7.5144 (3.8); 7.5080 (4.6); 7.4874 (3.5); 7.4642 (1.8); 5.5938 (14.3); 5.1881 (6.0); 5.1528 (7.2); 4.8189 (6.8); 4.7836 (5.8); 3.3228 (121.0); 3.2727 (4.7); 3.2373 (5.7); 3.0433 (4.8); 3.0078 (3.7); 2.8987 (1.1); 2.7395 (1.0); 2.5092 (17.1); 0.6486 (0.7); 0.6341 (1.8); 0.6155 (2.4); 0.6070 (4.0); 0.5883 (4.7); 0.5813 (3.1); 0.5740 (1.7); 0.5628 (3.1); 0.5489 (1.8); 0.4778 (1.8); 0.4638 (2.6); 0.4529 (1.7); 0.4449 (2.5); 0.4390 (2.4); 0.4181 (3.0); 0.3990 (2.6); 0.3894 (2.4); 0.3724 (2.1); 0.3576 (1.1)

(233) Ib-17: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(234) δ=8.9824 (16.0); 7.5766 (1.6); 7.5554 (3.6); 7.5377 (3.7); 7.5164 (1.8); 7.2055 (1.8); 7.1992 (2.0); 7.1805 (3.3); 7.1747 (3.6); 7.1563 (2.0); 7.1499 (2.1); 7.0676 (1.8); 7.0623 (1.8); 7.0465 (3.6); 7.0406 (3.4); 7.0253 (1.9); 7.0193 (1.7); 5.5064 (13.4); 5.1843 (5.9); 5.1491 (7.0); 4.7979 (6.7); 4.7627 (5.8); 3.3316 (128.6); 3.2537 (4.2); 3.2184 (5.7); 3.0667 (5.2); 3.0312 (3.7); 2.8981 (0.4); 2.7389 (0.4); 2.5131 (13.8); 2.5092 (18.2); 2.5054 (14.3); 0.6254 (0.8); 0.6107 (1.8); 0.5980 (1.7); 0.5924 (2.4); 0.5839 (2.7); 0.5785 (2.9); 0.5651 (3.0); 0.5578 (2.8); 0.5509 (2.8); 0.5440 (1.7); 0.5326 (3.1); 0.5187 (1.8); 0.4520 (1.8); 0.4379 (2.7); 0.4268 (1.7); 0.4192 (2.6); 0.4129 (2.4); 0.3922 (3.0); 0.3737 (2.6); 0.3641 (2.4); 0.3464 (2.1); 0.3324 (1.1)

(235) Ib-18: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(236) δ=8.9901 (16.0); 7.5619 (4.1); 7.5581 (4.4); 7.5436 (4.3); 7.5395 (4.4); 7.4078 (1.2); 7.4034 (1.2); 7.3950 (1.7); 7.3866 (3.7); 7.3821 (3.6); 7.3738 (3.6); 7.3690 (3.6); 7.3629 (6.2); 7.3400 (6.7); 7.3184 (2.5); 5.6206 (14.1); 5.1597 (6.1); 5.1244 (7.4); 4.8072 (7.0); 4.7720 (5.9); 3.3672 (0.4); 3.3263 (270.2); 3.2453 (5.7); 3.2106 (6.8); 2.9675 (6.0); 2.9326 (4.9); 2.8981 (1.4); 2.7390 (1.2); 2.5088 (22.2); 0.4627 (0.4); 0.4269 (12.1); 0.4213 (12.9); 0.3934 (1.4); 0.3617 (0.9); 0.3249 (4.1); 0.3050 (2.5); 0.2956 (1.8)

(237) Ib-19: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(238) δ=8.9923 (16.0); 7.9598 (0.4); 7.4656 (0.8); 7.4528 (0.9); 7.4421 (2.2); 7.4295 (2.3); 7.4180 (2.4); 7.4056 (2.3); 7.3947 (1.1); 7.3821 (0.9); 7.1325 (1.1); 7.1276 (1.4); 7.1233 (1.4); 7.1182 (1.4); 7.1099 (2.2); 7.1047 (2.6); 7.1009 (2.6); 7.0957 (2.4); 7.0874 (1.3); 7.0821 (1.4); 7.0782 (1.3); 7.0730 (1.1); 5.4275 (13.9); 5.2243 (6.1); 5.1890 (7.3); 4.8686 (6.9); 4.8334 (5.9); 3.3299 (150.1); 3.2965 (7.0); 3.2346 (5.6); 3.1995 (2.8); 2.8984 (2.2); 2.7392 (2.0); 2.5134 (9.2); 2.5093 (12.4); 2.5052 (9.6); 0.8238 (1.1); 0.8097 (1.8); 0.8019 (2.3); 0.7869 (3.7); 0.7781 (2.1); 0.7641 (2.2); 0.7374 (1.6); 0.7230 (1.5); 0.7139 (2.9); 0.7046 (1.8); 0.6931 (2.8); 0.6790 (1.8); 0.5101 (0.4); 0.4957 (6.4); 0.4727 (8.3); 0.4501 (3.9)

(239) Ib-20: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(240) δ=8.9753 (5.6); 7.1389 (0.5); 7.1259 (0.5); 7.1158 (1.1); 7.1028 (1.2); 7.0927 (0.8); 7.0797 (0.7); 7.0251 (0.9); 7.0217 (1.0); 7.0023 (1.4); 6.9988 (1.5); 6.9760 (0.7); 5.2620 (4.8); 5.2155 (2.0); 5.1804 (2.3); 4.7815 (2.2); 4.7464 (1.9); 3.8246 (16.0); 3.3253 (39.5); 3.2279 (5.1); 2.8992 (0.3); 2.5139 (4.4); 2.5099 (6.1); 2.5059 (4.9); 0.8954 (0.4); 0.8811 (0.6); 0.8752 (0.7); 0.8703 (0.8); 0.8621 (0.8); 0.8548 (0.9); 0.8505 (0.8); 0.8358 (0.7); 0.7380 (0.5); 0.7180 (0.8); 0.7136 (0.8); 0.7019 (0.9); 0.6934 (0.9); 0.6793 (0.6); 0.4699 (1.5); 0.4497 (2.2); 0.4298 (1.2); 0.4238 (1.1)

(241) Ib-21: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(242) δ=8.9788 (11.6); 7.2307 (1.4); 7.2132 (3.0); 7.1954 (1.8); 7.0431 (1.7); 7.0245 (3.0); 7.0055 (1.5); 5.4859 (9.7); 5.1791 (4.3); 5.1439 (5.2); 4.8193 (5.0); 4.7841 (4.2); 3.3277 (116.8); 3.2682 (3.0); 3.2329 (4.0); 3.0929 (3.7); 3.0575 (2.6); 2.8979 (0.4); 2.7388 (0.4); 2.5088 (9.1); 2.5049 (7.0); 2.2704 (15.9); 2.2673 (16.0); 0.6694 (0.7); 0.6548 (1.3); 0.6422 (1.4); 0.6370 (1.6); 0.6282 (1.8); 0.6103 (1.5); 0.5939 (1.0); 0.5752 (1.6); 0.5683 (1.8); 0.5613 (1.2); 0.5498 (2.0); 0.5359 (1.4); 0.4657 (1.2); 0.4516 (2.0); 0.4402 (1.1); 0.4332 (1.9); 0.4264 (1.8); 0.4159 (1.8); 0.4073 (1.6); 0.3979 (1.9); 0.3891 (1.8); 0.3711 (1.5); 0.3565 (0.7)

(243) Ib-22: .sup.1H-NMR (400.0 MHz, CD.sub.3CN):

(244) δ=8.6529 (15.1); 8.5685 (16.0); 8.4194 (9.6); 8.4069 (9.7); 7.5499 (9.0); 7.5374 (8.6); 5.3631 (10.8); 5.3274 (12.1); 4.7419 (12.1); 4.7063 (10.8); 3.6335 (7.8); 3.5160 (7.2); 3.4810 (12.3); 3.3867 (12.4); 3.3517 (7.3); 2.4745 (0.4); 2.4699 (0.7); 2.4652 (0.9); 2.4606 (0.6); 2.1797 (217.2); 2.1205 (0.8); 2.1143 (1.1); 2.1082 (1.2); 2.1021 (0.9); 2.0958 (0.5); 2.0869 (0.7); 1.9650 (8.6); 1.9586 (19.3); 1.9530 (76.1); 1.9470 (132.4); 1.9408 (168.8); 1.9346 (113.8); 1.9285 (56.5); 1.7815 (0.4); 1.7753 (0.8); 1.7693 (1.0); 1.7631 (0.7); 1.7569 (0.3); 1.2037 (0.4); 0.8658 (2.0); 0.8509 (4.1); 0.8467 (2.9); 0.8385 (2.7); 0.8318 (4.3); 0.8237 (4.8); 0.8194 (3.2); 0.8104 (4.0); 0.8045 (4.7); 0.7955 (3.0); 0.7921 (4.3); 0.7842 (4.3); 0.7773 (2.3); 0.7692 (3.8); 0.7659 (4.8); 0.7510 (2.7); 0.5685 (3.3); 0.5535 (4.7); 0.5494 (3.4); 0.5422 (3.0); 0.5343 (3.9); 0.5272 (4.0); 0.5231 (2.6); 0.5080 (2.9); 0.4412 (3.7); 0.4260 (4.2); 0.4229 (4.1); 0.4138 (3.8); 0.4077 (3.1); 0.3988 (3.7); 0.3956 (3.5); 0.3805 (2.4); 0.1459 (0.6); −0.0004 (132.8); −0.0087 (4.8); −0.1497 (0.6)

(245) Ib-23: .sup.1H-NMR (300.2 MHz, CDCl.sub.3):

(246) δ=8.6512 (16.0); 8.4527 (8.8); 8.4387 (8.7); 8.4295 (8.5); 7.5423 (2.6); 7.5342 (3.2); 7.5277 (2.5); 7.5110 (2.6); 7.5035 (3.2); 7.4963 (2.5); 7.2989 (14.8); 5.3808 (8.5); 5.3340 (10.0); 4.8482 (10.8); 4.8014 (9.2); 3.6834 (13.4); 3.4203 (6.2); 3.3736 (7.7); 2.9896 (7.6); 2.9429 (6.2); 2.0425 (13.7); 1.6764 (4.4); 1.2887 (0.6); 0.7345 (0.6); 0.7151 (3.1); 0.7087 (1.5); 0.7002 (3.7); 0.6897 (3.5); 0.6793 (6.7); 0.6761 (6.8); 0.6655 (4.3); 0.6534 (5.6); 0.6423 (5.5); 0.6234 (2.0); 0.5763 (3.8); 0.5573 (4.2); 0.5534 (3.2); 0.5399 (2.2); 0.5330 (3.4); 0.5217 (2.8); 0.5170 (1.8); 0.4972 (2.0); 0.3875 (3.3); 0.3685 (3.0); 0.3614 (3.0); 0.3544 (3.2); 0.3431 (2.6); 0.3341 (2.7); 0.3278 (2.7); 0.3082 (1.9); 0.0446 (0.6); 0.0337 (18.9); 0.0228 (0.8)

(247) Ib-24: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(248) δ=8.7578 (5.6); 7.1772 (0.6); 7.1726 (0.7); 7.1575 (1.2); 7.1525 (0.9); 7.1470 (0.8); 7.1416 (0.9); 7.1364 (1.4); 7.1299 (1.0); 7.1221 (0.8); 7.1149 (0.9); 7.1091 (1.3); 7.0877 (0.7); 7.0109 (0.8); 7.0003 (0.9); 6.9797 (0.6); 5.3780 (5.5); 4.9295 (2.1); 4.8942 (2.5); 4.5816 (2.5); 4.5464 (2.1); 3.0898 (16.0); 3.0144 (1.7); 2.9797 (2.1); 2.7373 (2.0); 2.7026 (1.6); 2.2854 (1.7); 2.2812 (2.3); 2.2770 (1.7); 0.2259 (0.7); 0.2154 (1.6); 0.2107 (1.8); 0.1989 (7.4); 0.1865 (0.8); 0.1760 (0.4); 0.1000 (1.4); 0.0829 (0.8); 0.0724 (0.5); 0.0649 (0.4)

(249) Ib-25: .sup.1H-NMR (300.2 MHz, CDCl.sub.3):

(250) δ=8.6392 (9.3); 8.4076 (0.4); 8.1985 (2.4); 8.1878 (2.0); 8.1829 (2.4); 7.9444 (1.4); 7.9380 (1.3); 7.9197 (1.6); 7.9129 (2.6); 7.9061 (1.4); 7.8878 (1.5); 7.8814 (1.4); 7.2988 (12.4); 7.2412 (1.7); 7.2350 (1.8); 7.2251 (1.7); 7.2179 (2.6); 7.2105 (1.7); 7.2005 (1.6); 7.1944 (1.5); 5.4464 (4.8); 5.39% (5.5); 5.3249 (0.4); 5.2655 (0.4); 4.7919 (5.7); 4.7451 (5.0); 3.5383 (6.7); 3.2430 (16.0); 2.0435 (0.7); 1.6264 (9.0); 1.3191 (0.3); 1.2897 (2.9); 1.2691 (0.4); 1.1386 (0.4); 0.8823 (0.9); 0.8632 (2.0); 0.8566 (1.4); 0.8460 (1.1); 0.8371 (2.8); 0.8342 (2.5); 0.8271 (2.6); 0.8199 (1.6); 0.8144 (1.2); 0.8095 (2.6); 0.8002 (4.4); 0.7905 (0.9); 0.7799 (1.6); 0.7757 (2.7); 0.7566 (1.3); 0.6218 (1.8); 0.6022 (2.2); 0.5956 (1.6); 0.5880 (1.5); 0.5764 (2.0); 0.5680 (1.9); 0.5619 (1.2); 0.5421 (1.4); 0.4705 (1.9); 0.4507 (1.9); 0.4469 (2.2); 0.4339 (1.8); 0.4267 (1.6); 0.4146 (1.6); 0.4102 (1.7); 0.3904 (1.1); 0.1048 (0.4); 0.0456 (0.4); 0.0348 (10.7); 0.0239 (0.4)

(251) Ia-en-01: .sup.1H-NMR (300.2 MHz, CDCl.sub.3):

(252) δ=8.8949 (11.8); 7.2983 (5.0); 7.1351 (0.9); 7.1313 (1.0); 7.1228 (2.1); 7.1166 (1.1); 7.1104 (2.6); 7.1034 (3.0); 7.0947 (6.2); 7.0855 (2.7); 7.0790 (5.2); 7.0743 (7.3); 7.0682 (4.3); 7.0540 (5.3); 7.0453 (1.5); 7.0329 (0.4); 5.9069 (15.5); 5.5023 (16.0); 5.3327 (2.7); 5.2811 (6.0); 5.2334 (7.8); 4.9165 (7.3); 4.8688 (5.7); 3.3473 (1.0); 2.0748 (0.9); 1.2891 (0.5); 0.9095 (2.8); 0.9027 (3.4); 0.8821 (3.7); 0.8757 (7.7); 0.8685 (4.0); 0.8463 (5.6); 0.8232 (0.7); 0.6798 (2.2); 0.6601 (2.8); 0.6549 (2.3); 0.6442 (1.6); 0.6332 (2.5); 0.6263 (2.2); 0.6193 (1.5); 0.5994 (1.7); 0.5206 (2.3); 0.5009 (2.0); 0.4889 (2.8); 0.4736 (1.8): 0.4670 (2.0): 0.4595 (1.9); 0.4396 (1.4): 0.0298 (6.2)

(253) Ia-en-02: .sup.1H-NMR (300.2 MHz, CDCl.sub.3):

(254) δ=8.8741 (10.4); 7.4257 (0.7); 7.41% (0.9); 7.4077 (0.9); 7.4012 (2.0); 7.3949 (1.7); 7.3925 (1.5); 7.3830 (1.4); 7.3800 (1.5); 7.3737 (2.9); 7.3677 (2.6); 7.3560 (1.4); 7.3461 (4.1); 7.3401 (3.2); 7.3210 (2.5); 7.3150 (1.9); 7.2984 (7.1); 7.2310 (2.9); 7.2272 (3.2); 7.2061 (4.0); 7.2025 (4.0); 7.1811 (1.7); 7.1774 (1.7); 7.1552 (2.3); 7.1519 (2.0); 7.1276 (2.1); 7.1225 (3.1); 7.1184 (2.2); 7.0941 (1.9); 7.0910 (1.7); 5.9075 (14.9); 5.4932 (16.0); 5.2678 (5.8); 5.2201 (7.5); 4.9133 (7.0); 4.8657 (5.4); 3.1080 (1.5); 2.0771 (0.4); 2.0418 (1.0); 1.6734 (0.3); 0.9083 (0.4); 0.8879 (2.4); 0.8817 (1.2); 0.8756 (2.5); 0.8613 (2.7); 0.8522 (5.0); 0.8411 (3.0); 0.8255 (3.6); 0.8166 (3.6); 0.7962 (1.0); 0.6804 (2.1); 0.6610 (2.7); 0.6562 (2.1); 0.6446 (1.6); 0.6355 (2.4); 0.6261 (2.0); 0.6202 (1.4); 0.6006 (1.6); 0.5278 (2.2); 0.5084 (1.9); 0.5004 (2.0); 0.4944 (2.2); 0.4819 (1.7); 0.4738 (1.8); 0.4669 (1.8); 0.4472 (1.3); 0.0329 (7.4

(255) Ia-en-03: .sup.1H-NMR (300.2 MHz, CDCl.sub.3):

(256) δ=8.8620 (10.7); 7.4051 (1.5); 7.3969 (6.2); 7.3845 (9.8); 7.3750 (14.2); 7.3640 (3.7); 7.3585 (2.9); 7.3501 (4.1); 7.3462 (7.6); 7.3362 (5.0); 7.3263 (2.7); 7.3230 (3.4); 7.3132 (2.5); 7.2983 (5.1); 5.7061 (15.0); 5.3896 (16.0); 5.3322 (2.4); 5.0613 (2.9); 5.0136 (10.2); 4.9806 (9.6); 4.9329 (2.7); 2.9895 (0.8); 2.9075 (0.4); 1.2882 (3.3); 1.2723 (0.6); 1.2490 (0.4); 1.0048 (0.9); 0.9835 (2.0); 0.9797 (1.6); 0.9688 (1.6); 0.9585 (2.2); 0.9476 (2.9); 0.9437 (2.3); 0.9304 (2.2); 0.9226 (3.0); 0.9061 (3.0); 0.8942 (2.7); 0.8850 (1.9); 0.8701 (3.4); 0.8491 (2.0); 0.7697 (2.3); 0.7498 (2.8); 0.7458 (2.2); 0.7338 (1.8); 0.7256 (2.4); 0.7139 (2.2); 0.7099 (1.6); 0.6896 (1.6); 0.5850 (2.2); 0.5651 (2.1); 0.5600 (2.3); 0.5492 (2.2); 0.5401 (1.9); 0.5291 (1.9); 0.5240 (2.0); 0.5039 (1.4); 0.1048 (7.7); 0.0324 (5.4); 0.0215 (0.3)

(257) Ia-en-04: .sup.1H-NMR (499.9 MHz, CDCl.sub.3):

(258) δ=8.8291 (6.8); 8.7802 (0.3); 7.3153 (1.0); 7.3117 (1.0); 7.3046 (1.1); 7.3006 (2.0); 7.2968 (1.6); 7.2893 (1.5); 7.2879 (1.6); 7.2844 (2.0); 7.2804 (1.3); 7.2734 (1.2); 7.2696 (1.5); 7.2651 (6.8); 7.2216 (0.6); 7.2086 (1.2); 7.2070 (1.2); 7.1990 (1.3); 7.1966 (1.3); 7.1883 (1.0); 7.1854 (1.0); 7.1726 (0.4); 7.1692 (0.4); 7.1236 (2.5); 7.1217 (2.4); 7.1086 (3.7); 7.1068 (3.6); 7.0985 (0.5); 7.0937 (1.6); 7.0917 (1.5); 7.0501 (2.1); 7.0484 (1.9); 7.0333 (2.2); 7.0308 (3.0); 7.0136 (1.8); 5.8214 (1.5); 5.8062 (4.7); 5.7910 (4.7); 5.7759 (1.5); 5.2219 (0.4); 5.1933 (1.1); 5.1623 (1.0); 5.0770 (0.3); 5.0480 (1.0); 5.0417 (1.0); 5.0139 (0.7); 4.8760 (0.4); 2.9792 (1.0); 2.0536 (16.0); 2.0430 (2.9); 2.0384 (15.7); 2.0075 (1.1); 1.9499 (0.8); 1.9356 (0.7); 1.6321 (0.9); 1.5054 (2.0); 1.4919 (2.0); 1.2729 (0.3); 1.2586 (0.7); 1.2443 (0.3); 0.9932 (0.4); 0.9867 (0.5); 0.9804 (0.4); 0.9745 (0.4); 0.9674 (0.5); 0.9533 (0.6); 0.9403 (0.6); 0.9334 (0.6); 0.9186 (1.0); 0.9041 (1.2); 0.8911 (1.1); 0.8844 (1.2); 0.8733 (0.7); 0.7032 (0.3); 0.6953 (0.8); 0.6826 (1.3); 0.6672 (1.2); 0.6623 (1.2); 0.6437 (1.9); 0.6310 (1.7); 0.6288 (1.7); 0.6215 (1.6); 0.6164 (1.1); 0.6065 (1.7); 0.5942 (0.8); 0.0062 (0.3); −0.0002 (5.8)

(259) Ia-en-05: .sup.1H-NMR (300.2 MHz, CDCl.sub.3):

(260) δ=8.8801 (6.3); 7.4117 (1.2); 7.4053 (1.0); 7.3880 (1.7); 7.3794 (2.0); 7.3636 (0.9); 7.3558 (1.4); 7.2983 (5.6); 7.1310 (0.8); 7.1002 (2.9); 7.0746 (2.7); 7.0483 (0.9); 5.8812 (1.1); 5.8558 (3.7); 5.8306 (3.8); 5.8054 (1.1); 5.2647 (0.9); 5.2168 (1.4); 5.0664 (1.0); 5.0183 (0.6); 3.1478 (0.5); 2.1035 (13.8); 2.0782 (13.7); 2.0517 (0.3); 2.0500 (0.4); 2.0427 (16.0); 2.0350 (0.4); 0.9891 (0.3); 0.9572 (0.7); 0.9290 (1.1); 0.9075 (0.9); 0.8981 (1.0); 0.8780 (0.6); 0.6970 (2.0); 0.6688 (2.1); 0.6611 (1.8); 0.6407 (1.0); 0.6336 (1.2); 0.0324 (6.9)

(261) Ia-en-06: .sup.1H-NMR (300.2 MHz, CDCl.sub.3):

(262) δ=8.8798 (8.0); 7.2983 (5.3); 7.1980 (0.6); 7.1918 (0.6); 7.1708 (1.1); 7.1649 (1.5); 7.1584 (0.6); 7.1459 (1.1); 7.1396 (1.7); 7.1317 (1.1); 7.1137 (0.9); 7.1070 (1.1); 7.1023 (0.9); 7.0985 (0.8); 7.0853 (0.9); 7.0822 (0.8); 7.0766 (1.4); 7.0725 (1.5); 7.0599 (1.5); 7.0566 (1.5); 7.0492 (0.8); 7.0454 (0.9); 7.0324 (0.9); 7.0299 (0.9); 7.0087 (1.0); 6.9886 (1.1); 6.9646 (0.5); 5.8930 (1.2); 5.8676 (4.2); 5.8424 (4.2); 5.8172 (1.3); 5.2593 (1.7); 5.2113 (2.9); 5.0790 (2.2); 5.0310 (1.3); 3.1565 (1.7); 2.1087 (16.0); 2.0835 (15.8); 2.0429 (0.6); 1.6642 (1.7); 1.2880 (0.4); 0.9692 (1.2); 0.9420 (1.5); 0.9194 (1.1); 0.9099 (1.5); 0.8891 (0.9); 0.7326 (0.4); 0.7118 (1.7); 0.7066 (2.7); 0.6859 (2.1); 0.6796 (2.8); 0.6699 (1.9); 0.6535 (1.2); 0.6432 (1.6); 0.0323 (6.7)

(263) Ia-en-07: .sup.1H-NMR (300.2 MHz, CDCl.sub.3):

(264) δ=8.8914 (7.9); 8.8455 (4.2); 8.6702 (0.3); 7.2981 (5.8); 7.2667 (0.4); 7.2618 (0.4); 7.2533 (0.5); 7.2363 (1.3); 7.2288 (1.3); 7.2121 (2.2); 7.2040 (2.7); 7.1952 (1.6); 7.1841 (2.8); 7.1792 (2.8); 7.1731 (2.6); 7.1629 (4.1); 7.1534 (3.2); 7.1432 (3.1); 7.1275 (1.8); 7.1187 (0.9); 7.1110 (0.6); 7.1034 (0.5); 6.9178 (0.8); 6.8976 (1.1); 6.8927 (1.1); 6.8789 (0.4); 6.8733 (0.6); 6.5314 (0.6); 6.5087 (1.7); 6.4860 (1.7); 6.4634 (0.6); 6.3933 (1.0); 6.3707 (2.9); 6.3482 (2.9); 6.3258 (0.9); 5.8609 (0.4); 5.8357 (0.4); 5.2712 (3.5); 5.2236 (4.4); 5.1648 (2.0); 5.1173 (2.5); 4.8870 (4.1); 4.8395 (3.3); 4.7728 (2.4); 4.7252 (1.9); 3.0857 (3.9); 3.0748 (3.9); 2.9721 (2.6); 2.9678 (2.7); 2.2117 (0.7); 2.2074 (0.7); 2.1026 (1.5); 2.0773 (1.5); 2.0402 (6.4); 1.5549 (15.8); 1.5325 (16.0); 1.4720 (0.4); 1.4497 (0.3); 1.3105 (0.5); 1.2849 (1.1); 1.1011 (0.4); 1.0286 (0.4); 1.0073 (0.9); 0.9927 (0.6); 0.9825 (0.9); 0.9703 (1.7); 0.9461 (1.8); 0.9337 (1.2); 0.9241 (0.7); 0.9091 (1.4); 0.8857 (1.0); 0.8639 (1.5); 0.8486 (0.9); 0.8384 (1.8); 0.8340 (1.8); 0.8282 (2.1); 0.8089 (2.1); 0.8026 (2.2); 0.7989 (2.0); 0.7887 (0.8); 0.7738 (1.9); 0.7533 (0.9); 0.6733 (0.9); 0.6642 (0.3); 0.6531 (1.1); 0.6370 (1.0); 0.6308 (1.9); 0.6119 (2.1); 0.5947 (1.5); 0.5870 (1.5); 0.5757 (1.3); 0.5712 (1.0); 0.5554 (1.0); 0.5514 (1.1); 0.5358 (0.8); 0.5309 (0.9); 0.5202 (0.8); 0.5110 (0.7); 0.4998 (0.7); 0.4950 (0.8); 0.4750 (0.4); 0.4233 (1.2); 0.4036 (1.3); 0.3982 (1.3); 0.3880 (1.3); 0.3786 (1.1); 0.3679 (1.2); 0.3627 (1.2); 0.3428 (0.8); 0.0284 (6.9)

(265) Ia-en-08: .sup.1H-NMR (499.9 MHz, CDCl.sub.3):

(266) δ=8.8950 (13.5); 7.2701 (3.2); 7.1954 (0.9); 7.1854 (1.5); 7.1803 (1.2); 7.1755 (2.7); 7.1688 (1.5); 7.1654 (1.6); 7.1608 (2.4); 7.1556 (1.5); 7.1525 (1.1); 7.1490 (1.0); 7.1406 (1.2); 7.1335 (0.4); 7.1165 (1.1); 7.1006 (5.2); 7.0963 (5.6); 7.0896 (8.0); 7.0820 (5.3); 7.0736 (0.7); 7.0672 (0.4); 5.8827 (15.2); 5.4694 (16.0); 5.3025 (0.7); 5.2582 (6.8); 5.22% (7.9); 4.9026 (7.6); 4.8740 (6.5); 3.4180 (2.5); 0.8768 (0.4); 0.8640 (4.2); 0.8627 (4.2); 0.8451 (8.3); 0.8267 (6.7); 0.8137 (0.4); 0.6333 (2.1); 0.6212 (2.7); 0.6176 (2.4); 0.6124 (2.0); 0.6041 (2.7); 0.6019 (2.4); 0.5967 (1.7); 0.5846 (1.7); 0.4882 (2.1); 0.4828 (0.6); 0.4761 (2.2); 0.4698 (3.4); 0.4595 (2.0); 0.4560 (2.2); 0.4515 (2.0); 0.4395 (1.5); −0.0002 (3.8)

(267) Ia-en-09: .sup.1H-NMR (300.2 MHz, CDCl.sub.3):

(268) δ=8.8523 (9.2); 7.4688 (2.2); 7.4596 (1.9); 7.4529 (2.4); 7.4446 (2.6); 7.4373 (4.6); 7.4250 (1.9); 7.4192 (2.0); 7.4038 (1.9); 7.3805 (0.7); 7.3706 (1.7); 7.3558 (5.9); 7.3514 (6.5); 7.3461 (4.4); 7.3385 (6.6); 7.3300 (3.4); 7.3225 (5.5); 7.2984 (28.0); 5.9813 (2.3); 5.4793 (16.0); 5.2571 (2.8); 5.2092 (3.8); 4.9221 (1.0); 4.8784 (0.8); 2.9630 (8.8); 2.0445 (2.0); 1.6030 (7.3); 1.2912 (1.2); 0.9791 (1.2); 0.9426 (2.0); 0.9193 (2.0); 0.7109 (2.0); 0.6914 (2.7); 0.6864 (2.0); 0.6751 (1.6); 0.6665 (2.1); 0.6560 (1.9); 0.6505 (1.6); 0.6310 (1.6); 0.5392 (2.1); 0.5198 (2.1); 0.5135 (1.9); 0.5042 (2.1); 0.4945 (1.6); 0.4844 (1.7); 0.4783 (2.0): 0.4587 (1.3); 0.0471 (0.9); 0.0364 (29.4): 0.0255 (1.2)

(269) Ia-en-10: .sup.1H-NMR (300.2 MHz, CDCl.sub.3):

(270) δ=8.9078 (4.9); 7.4593 (0.7); 7.4534 (0.8); 7.4328 (1.2); 7.4301 (1.2); 7.4275 (1.2); 7.4092 (0.8); 7.4033 (0.9); 7.2988 (1.8); 7.2821 (0.6); 7.2763 (0.7); 7.2608 (0.7); 7.2559 (1.4); 7.2507 (1.0); 7.2353 (1.0); 7.2294 (0.9); 7.1580 (1.3); 7.1558 (1.4); 7.1296 (2.0); 7.1058 (0.7); 7.1032 (0.8); 5.9069 (5.7); 5.4875 (5.9); 5.2872 (2.3); 5.2395 (3.0); 4.9157 (2.8); 4.8680 (2.2); 3.3541 (0.4); 2.0477 (0.4); 2.0405 (16.0); 0.9064 (1.1); 0.9001 (1.3); 0.8787 (1.4); 0.8730 (2.8); 0.8666 (1.5); 0.8422 (2.4); 0.6740 (0.8); 0.6543 (1.0); 0.6491 (0.8); 0.6386 (0.6); 0.6272 (0.9); 0.6208 (0.8); 0.6135 (0.5); 0.5936 (0.6); 0.5254 (0.8); 0.5057 (0.8); 0.4942 (1.2); 0.4782 (0.6); 0.4722 (0.7); 0.4643 (0.7); 0.4445 (0.5); 0.0284 (1.7)

(271) Ia-en-11: .sup.1H-NMR (499.9 MHz, CDCl.sub.3):

(272) δ=8.8522 (0.4); 8.8186 (16.0); 8.7289 (6.1); 8.7109 (1.3); 8.0178 (0.7); 8.0033 (0.8); 8.0007 (0.6); 7.6984 (0.5); 7.6835 (0.3); 7.5806 (0.7); 7.5651 (1.0); 7.5493 (0.6); 7.4706 (0.5); 7.4568 (0.5); 7.4532 (0.5); 7.4427 (0.7); 7.4259 (1.0); 7.4109 (4.2); 7.4078 (4.7); 7.3955 (11.5); 7.3794 (10.0); 7.3677 (4.5); 7.3649 (7.1); 7.3621 (4.5); 7.3553 (2.7); 7.3507 (6.8); 7.3444 (1.8); 7.3385 (2.0); 7.3358 (2.4); 7.3301 (1.3); 7.3217 (1.3); 7.3178 (1.4); 7.2923 (6.7); 7.2857 (7.4); 7.2796 (7.5); 7.2715 (1.7); 7.2640 (20.8); 7.2302 (0.5); 7.2127 (0.5); 7.1434 (4.3); 7.1053 (1.4); 7.0969 (3.9); 7.0938 (2.9); 7.0905 (3.8); 7.0864 (2.9); 7.0834 (3.2); 7.0780 (2.9); 7.0698 (0.5); 6.1672 (2.7); 6.1538 (8.1); 6.1403 (8.0); 6.1268 (2.5); 5.7372 (1.3); 5.7281 (1.2); 5.7129 (3.4); 5.6977 (3.4); 5.6825 (1.1); 5.1379 (2.7); 5.1221 (0.6); 5.1096 (3.3); 5.0152 (0.8); 4.9866 (0.9); 4.9718 (0.5); 4.9559 (2.6); 4.9388 (1.8); 4.9274 (14.8); 4.9177 (15.7); 4.8890 (2.9); 4.8836 (4.4); 4.8552 (3.4); 4.4802 (0.7); 4.4545 (0.7); 4.4518 (0.6); 4.3187 (0.4); 4.3042 (0.4); 2.9573 (0.3); 2.8808 (0.4); 2.7094 (3.9); 2.4860 (10.0); 2.0414 (14.0); 2.0262 (13.7); 1.9761 (0.4); 1.9741 (0.4); 1.6047 (0.7); 1.5642 (0.7); 1.5508 (0.6); 1.4928 (0.6); 1.4814 (0.9); 1.4672 (2.6); 1.4526 (3.1); 1.4387 (35.8); 1.4252 (35.1); 1.3515 (0.4); 1.3399 (0.4); 1.3363 (0.4); 1.3294 (0.4); 1.3250 (0.4); 1.3179 (0.5); 1.3144 (0.5); 1.3095 (0.5); 1.3029 (0.5); 1.2963 (0.5); 1.2886 (0.5); 1.2836 (0.4); 1.2729 (0.6); 1.2582 (1.5); 1.2559 (1.4); 1.2442 (0.5); 1.2394 (0.4); 1.2273 (0.3); 1.1065 (0.4); 1.0970 (1.0); 1.0921 (0.4); 1.0838 (1.6); 1.0754 (1.4); 1.0689 (1.6); 1.0623 (2.0); 1.0475 (1.7); 1.0319 (1.3); 1.0175 (1.9); 1.0098 (1.6); 1.0044 (1.3); 0.9956 (2.0); 0.9826 (1.5); 0.9710 (0.5); 0.9677 (0.5); 0.9609 (0.5); 0.9562 (0.5); 0.9494 (0.6); 0.9459 (0.6); 0.9321 (1.9); 0.9245 (2.8); 0.9194 (3.0); 0.9121 (3.8); 0.9049 (5.0); 0.8975 (4.9); 0.8911 (4.5); 0.8890 (4.2); 0.8808 (3.0); 0.8672 (1.4); 0.8548 (0.4); 0.8387 (0.3); 0.8090 (0.3); 0.8003 (0.3); 0.7940 (0.3); 0.7872 (0.4); 0.7587 (2.6); 0.7439 (4.8); 0.7373 (3.2); 0.7315 (4.9); 0.7274 (2.8); 0.7225 (5.6); 0.7152 (12.0); 0.7085 (6.1); 0.6990 (4.2); 0.6937 (3.6); 0.6876 (3.8); 06847 (2.1); 0.6729 (2.2); 0.6596 (0.3); 0.5780 (0.3); 0.5660 (0.4); 0.5630 (0.4); 0 5563 (0.4); 0.5510 (0.4); 0.5443 (0.4); 0.5413 (0.4); 0.5291 (0.5); 0.5225 (1.2); 0.5089 (2.6); 0.5016 (3.6); 0.4984 (3.7); 0.4918 (3.4); 0.4867 (3.7); 0.4770 (2.8); 0.4711 (1.0); 0.4656 (2.3); 0.0062 (1.2); −0.0002 (20.8); −0.0067 (0.9)

(273) Ib-en-01: .sup.1H-NMR (300.2 MHz, CDCl.sub.3):

(274) δ=8.6325 (11.0); 8.5864 (1.4); 7.4097 (0.4); 7.4044 (0.4); 7.3848 (0.3); 7.3788 (0.4); 7.3698 (0.9); 7.3636 (1.4); 7.3521 (1.0); 7.3454 (2.5); 7.3395 (4.4); 7.3276 (1.4); 7.3184 (5.5); 7.3146 (5.6); 7.2981 (19.1); 7.2918 (3.3); 7.2877 (1.6); 7.2800 (0.4); 7.2523 (0.3); 7.1771 (3.0); 7.1732 (3.2); 7.1520 (4.5); 7.1468 (2.8); 7.1272 (2.1); 7.1234 (2.2); 7.0939 (2.3); 7.0901 (2.0); 7.0651 (2.4); 7.0608 (3.3); 7.0324 (1.9); 6.9378 (0.6); 6.8844 (0.7); 6.5812 (0.9); 6.5278 (0.7); 5.9281 (0.7); 5.7171 (15.7); 5.4783 (5.1); 5.4311 (7.9); 5.3574 (16.0); 5.3365 (0.5); 5.2709 (8.8); 5.2238 (6.2); 4.0859 (6.9); 4.0746 (6.9); 3.6646 (1.4); 1.6370 (0.3); 1.6043 (7.6); 1.2912 (0.6); 1.0447 (0.4); 1.0324 (0.6); 1.0227 (0.4); 1.0127 (0.4); 1.0062 (0.8); 0.9869 (1.1); 0.9686 (1.6); 0.9591 (1.4); 0.9517 (1.5); 0.9413 (2.5); 0.9345 (2.5); 0.9252 (2.2); 0.9083 (4.0); 0.8849 (2.3); 0.8715 (2.7); 0.8500 (3.4); 0.8334 (3.5); 0.8270 (3.0); 0.8112 (3.6); 0.7898 (5.5); 0.7770 (3.5); 0.7733 (2.8); 0.7631 (3.3); 0.7548 (3.9); 0.7460 (1.2); 0.7385 (1.0); 0.7282 (1.8); 0.7105 (0.6); 0.0471 (0.5); 0.0363 (17.0); 0.0286 (0.6); 0.0271 (0.6); 0.0254 (0.6)

(275) XVIa-01: .sup.1H-NMR (499.9 MHz, d.sub.6-DMSO):

(276) δ=9.2718 (7.3); 6.0189 (16.0); 3.3267 (4.2); 2.5059 (2.4); 2.5026 (3.2); 2.4993 (2.4); 1.8135 (2.0); 1.8022 (5.5); 1.7953 (5.7); 1.7853 (2.7); 1.6384 (2.7); 1.6284 (5.6); 1.6216 (5.6); 1.6102 (2.0)

(277) XVIa-02: .sup.1H-NMR (499.9 MHz, CDCl.sub.3):

(278) δ=8.7454 (4.9); 7.2666 (4.0); 5.4668 (16.0); 1.6069 (2.5); 1.5219 (19.1); 1.4422 (1.4); 1.4337 (4.6) 1.4279 (4.7); 1.4198 (1.4); 0.9815 (1.6); 0.9738 (6.2); 0.9678 (6.1); 0.9598 (1.4); −0.0002 (3.7)

(279) XVIa-03: .sup.1H-NMR (499.9 MHz, CDCl.sub.3):

(280) δ=8.7514 (8.8); 7.2646 (10.1); 5.8175 (15.7); 5.8130 (16.0); 1.6993 (0.3); 1.6688 (1.7); 1.6592 (2.3); 1.6548 (3.4); 1.6484 (4.3); 1.6385 (3.1); 1.6336 (1.9); 1.6261 (2.0); 1.6189 (3.4); 1.6139 (3.7); 1.6125 (4.3); 1.6063 (1.8); 1.6034 (3.9); 1.5850 (10.3); 1.5711 (3.5); 1.5616 (4.4); 1.5606 (4.2); 1.5544 (5.9); 1.5508 (2.9); 1.5454 (4.4); 1.5440 (4.0); 1.5391 (3.5); 1.5318 (1.8); 1.5241 (1.5); 0.0063 (0.6); −0.0002 (9.8); −0.0068 (0.6)

(281) XVIb-01: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO):

(282) δ=9.0517 (73); 6.2906 (16.0); 3.3356 (8.4); 2.5136 (1.6); 2.5096 (2.2); 2.5054 (1.7); 1.8770 (1.8); 1.8626 (5.1); 1.8543 (5.4); 1.8414 (2.8); 1.7996 (0.4); 1.6608 (2.5); 1.6479 (5.1); 1.6395 (5.5); 1.6251 (2.0)

(283) XVIb-02: .sup.1H-NMR (300.2 MHz, CDCl.sub.3):

(284) δ=8.6112 (3.9); 7.2986 (14.9); 5.7117 (14.1); 1.5870 (1.8); 1.5545 (16.0); 1.4828 (1.2); 1.4688 (3.8); 1.4590 (3.9); 1.4457 (1.3); 0.9877 (1.4); 0.9753 (5.2); 0.9653 (5.0); 0.9521 (1.2); 0.0483 (0.8); 0.0375 (16.8); 0.0266 (0.7)

(285) XVIb-03: .sup.1H-NMR (300.2 MHz, CDCl.sub.3):

(286) δ=8.6414 (8.7); 7.2982 (4.4); 6.0367 (15.9); 6.0289 (16.0); 1.6948 (1.3); 1.6703 (2.6); 1.6688 (2.6); 1.6612 (3.2); 1.6580 (4.0); 1.6445 (4.1); 1.6347 (2.4); 1.6105 (2.5); 1.6090 (2.6); 1.5983 (8.2); 1.5876 (6.3); 1.5818 (3.5); 1.5742 (3.2); 1.5724 (3.0); 1.5678 (4.0); 1.5602 (5.2); 1.5535 (3.2); 1.5473 (3.6); 1.5172 (0.7); 0.0316 (4.7)

BIOLOGICAL EXAMPLES

Example A

In Vivo Preventive Test on Alternaria brassicae (Leaf Spot on Radish or Cabbage)

(287) Solvent: 5% by volume of Dimethyl sulfoxide 10% by volume of Acetone

(288) Emulsifier: 1 μl of Tween® 80 per mg of active ingredient

(289) The active ingredients were made soluble and homogenized in a mixture of Dimethyl sulfoxide/Acetone/Tween® 80 and then diluted in water to the desired concentration.

(290) The young plants of radish or cabbage were treated by spraying the active ingredient prepared as described above. Control plants were treated only with an aqueous solution of Acetone/Dimethyl sulfoxide/Tween® 80.

(291) After 24 hours, the plants were contaminated by spraying the leaves with an aqueous suspension of Alternaria brassicae spores. The contaminated radish or cabbage plants were incubated for 6 days at 20° C. and at 100% relative humidity.

(292) The test was 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 was observed.

(293) 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: Ia-06; Ia-36; Ia-46; Ia-48; Ia-52; Ia-55; Ia-57; Ia-58; Ia-61; Ia-en-05; Ia-en-11; Ib-09; lb-10; Ib-18.

(294) 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: Ia-44; Ia-50; Ia-63; Ia-en-06; Ib-25.

(295) 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: Ia-18; Ia-22; Ia-24; Ia-41; Ia-66; Ia-en-01; Ia-en-02; Ia-en-07; Ia-en-09.

Example B

In Vivo Preventive Test on Botrytis cinerea (Grey Mould)

(296) Solvent: 5% by volume of Dimethyl sulfoxide 10% by volume of Acetone

(297) Emulsifier: 1 μl of Tween®80 per mg of active ingredient

(298) The active ingredients were made soluble and homogenized in a mixture of Dimethyl sulfoxide/Acetone/Tween® 80 and then diluted in water to the desired concentration.

(299) The young plants of gherkin were treated by spraying the active ingredient prepared as described above. Control plants were treated only with an aqueous solution of Acetone/Dimethyl sulfoxide/Tween® 80.

(300) After 24 hours, the plants were contaminated by spraying the leaves with an aqueous suspension of Botrytis cinerea spores. The contaminated gherkin plants were incubated for 4 to 5 days at 17° C. and at 90% relative humidity.

(301) The test was evaluated 4 to 5 days after the inoculation. 0% means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease was observed.

(302) 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: Ia-37; Ia-en-01.

(303) 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: Ia-03; Ia-06; Ia-24; Ia-69; Ia-en-03.

(304) 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: Ia-01; Ia-15; Ia-18; Ia-22; Ia-66; Ia-en-02; Ia-en-09; Ib-03.

Example C

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

(305) Solvent: 5% by volume of Dimethyl sulfoxide 10% by volume of Acetone

(306) Emulsifier: 1 μl of Tween® 80 per mg of active ingredient

(307) The active ingredients were made soluble and homogenized in a mixture of Dimethyl sulfoxide/Acetone/Tween®80 and then diluted in water to the desired concentration.

(308) The young plants of wheat were treated by spraying the active ingredient prepared as described above. Control plants were treated only with an aqueous solution of Acetone/Dimethyl sulfoxide/Tween® 80.

(309) After 24 hours, the plants were contaminated by spraying the leaves with an aqueous suspension of Puccinia recondita spores. The contaminated wheat plants were 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.

(310) The test was 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 was observed.

(311) 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: Ia-17; Ia-29; Ia-55; Ia-62; Ia-69; Ib-02; Ib-03.

(312) 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: Ia-01; Ia-03; Ia-04; Ia-07; Ia-08; Ia-42; Ia-58; Ia-68; Ia-71; Ia-en-04; Ia-en-06; Ib-06.

(313) 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: Ia-02; Ia-05; Ia-06; Ia-09; Ia-15; Ia-16; Ia-18; Ia-20; Ia-21; Ia-22; Ia-24; Ia-25; Ia-32; Ia-37; Ia-39; Ia-41; Ia-44; Ia-53; Ia-66; Ia-67; Ia-72; Ia-73; Ia-en-01; Ia-en-02; Ia-en-03; Ia-en-05; Ia-en-07; Ia-en-08; Ia-en-09; Ia-en-10; Ia-en-11.

Example D

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

(314) Solvent: 5% by volume of Dimethyl sulfoxide 10% by volume of Acetone

(315) Emulsifier: 1 μl of Tween® 80 per mg of active ingredient

(316) The active ingredients were made soluble and homogenized in a mixture of Dimethyl sulfoxide/Acetone/Tween® 80 and then diluted in water to the desired concentration.

(317) The young plants of wheat were treated by spraying the active ingredient prepared as described above. Control plants were treated only with an aqueous solution of Acetone/Dimethyl sulfoxide/Tween® 80.

(318) After 24 hours, the plants were contaminated by spraying the leaves with an aqueous suspension of Septoria tritici spores. The contaminated wheat plants were incubated for 72 hours at 17° C. and at 100% relative humidity and then for 15 days at 20° C. and at 90% relative humidity.

(319) The test was evaluated 19 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 was observed.

(320) 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: Ia-01; Ia-07; Ia-18; lb-13.

(321) 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: Ia-08; Ia-13; Ia-14; Ia-31; Ia-42; Ia-48; Ia-55; Ia-en-04.

(322) 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: Ia-02; Ia-03; Ia-04; Ia-05; Ia-06; Ia-09; Ia-15; Ia-17; Ia-20; Ia-21; Ia-22; Ia-24; Ia-29; Ia-39; Ia-41; Ia-44; Ia-53; Ia-66; Ia-72; Ia-73; Ia-en-02; Ia-en-03; Ia-en-07; Ia-en-08; Ia-en-11; Ib-01; Ib-02; lb-05; Ib-06.

Example E

In Vivo Preventive Test on Sphaerotheca fulikinea (Powdery Mildew on Cucurbits)

(323) Solvent: 5% by volume of Dimethyl sulfoxide 10% by volume of Acetone

(324) Emulsifier: 1 μl of Tween® 80 per mg of active ingredient

(325) The active ingredients were made soluble and homogenized in a mixture of Dimethyl sulfoxide/Acetone/Tween® 80 and then diluted in water to the desired concentration.

(326) The young plants of gherkin were treated by spraying the active ingredient prepared as described above. Control plants were treated only with an aqueous solution of Acetone/Dimethyl sulfoxide/Tween® 80.

(327) After 24 hours, the plants were contaminated by spraying the leaves with an aqueous suspension of Sphaerotheca fuliginea spores. The contaminated gherkin plants were incubated for 8 days at 20° C. and at 70-80% relative humidity.

(328) The test was evaluated 8 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 was observed.

(329) 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: Ia-30; lb-19.

(330) 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: Ia-01; Ia-02; Ia-03; Ia-04; Ia-05; Ia-06; Ia-07; Ia-08; Ia-09; Ia-13; Ia-14; Ia-15; Ia-16; Ia-17; Ia-18; Ia-20; Ia-21; Ia-22; Ia-24; Ia-25; Ia-26; Ia-27; Ia-28; Ia-29; Ia-31; Ia-32; Ia-33; Ia-34; Ia-36; Ia-37; Ia-39; Ia-41; Ia-42; Ia-44; Ia-46; Ia-48; Ia-50; Ia-52; Ia-53; Ia-54; Ia-55; Ia-56; Ia-57; Ia-58; Ia-59; Ia-60; Ia-61; Ia-62; Ia-63; Ia-64; Ia-65; Ia-66; Ia-67; Ia-68; Ia-69; Ia-71; Ia-72; Ia-73; Ia-76; Ia-en-01; Ia-en-02; Ia-en-03; Ia-en-04; Ia-en-06; Ia-en-07; Ia-en-08; Ia-en-09; Ia-en-10; Ia-en-11; Ib-02; Ib-03; lb-05; Ib-06; Ib-09; lb-10; Ib-13; Ib-14; Ib-21; Ib-22.

Example F

In Vivo Preventive Test on Uromyces appendiculatus (Bean Rust)

(331) Solvent: 5% by volume of Dimethyl sulfoxide 10% by volume of Acetone

(332) Emulsifier: 1 μl of Tween® 80 per mg of active ingredient

(333) The active ingredients were made soluble and homogenized in a mixture of Dimethyl sulfoxide/Acetone/Tween® 80 and then diluted in water to the desired concentration.

(334) The young plants of bean were treated by spraying the active ingredient prepared as described above. Control plants were treated only with an aqueous solution of Acetone/Dimethyl sulfoxide/Tween® 80.

(335) After 24 hours, the plants were contaminated by spraying the leaves with an aqueous suspension of Uromyces appendiculatus spores. The contaminated bean plants were 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.

(336) The test was 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 was observed.

(337) 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: Ia-69; Ib-05

(338) 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: Ia-17; Ia-68; Ia-en-03.

(339) 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: Ia-01; Ia-02; Ia-03; Ia-04; Ia-05; Ia-06; Ia-08; Ia-09; Ia-15; Ia-18; Ia-20; Ia-21; Ia-22; Ia-24; Ia-25; Ia-32; Ia-37; Ia-39; Ia-41; Ia-42; Ia-44; Ia-53; Ia-67; Ia-73; Ia-en-01; Ia-en-02; Ia-en-04; Ia-en-05; Ia-en-06; Ia-en-07; Ia-en-08; Ia-en-09; Ia-en-10; Ia-en-11; Ib-02; Ib-06.

Example G

In Vivo Preventive Test on Colletotrichum lindemuthianum (leaf spot on bean)

(340) Solvent: 5% by volume of Dimethyl sulfoxide 10% by volume of Acetone

(341) Emulsifier: 1 μl of Tween® 80 per mg of active ingredient

(342) The active ingredients were made soluble and homogenized in a mixture of Dimethyl sulfoxide/Acetone/Tween®80 and then diluted in water to the desired concentration.

(343) The young plants of bean were treated by spraying the active ingredient prepared as described above. Control plants were treated only with an aqueous solution of Acetone/Dimethyl sulfoxide/Tween® 80.

(344) After 24 hours, the plants were contaminated by spraying the leaves with an aqueous suspension of Colletotrichum lindemuthianum spores. The contaminated bean plants were incubated for 24 hours at 20° C. and at 100% relative humidity and then for 6 days at 20° C. and at 90% relative humidity.

(345) The test was evaluated 7 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 was observed.

(346) 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: Ia-01; Ia-08; Ia-en-05.

(347) 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: Ia-02; Ia-03; Ia-04; Ia-05; Ia-06; Ia-09; Ia-15; Ia-18; Ia-21; Ia-22; Ia-24; Ia-25; Ia-27; Ia-32; Ia-39; Ia-42; Ia-44; Ia-53; Ia-62; Ia-64; Ia-en-01; Ia-en-02; Ia-en-03; Ia-en-07; Ia-en-08; Ia-en-09; Ia-en-10; Ia-en-11.

Example H

In Vivo Preventive Test on Phakospora pachyrhizi (Soybean Rust)

(348) Solvent: 5% by volume of Dimethyl sulfoxide 10% by volume of Acetone

(349) Emulsifier: 1 μl of Tween® 80 per mg of active ingredient

(350) The active ingredients were made soluble and homogenized in a mixture of Dimethyl sulfoxide/Acetone/Tween® 80 and then diluted in water to the desired concentration.

(351) The young plants of soybean were treated by spraying the active ingredient prepared as described above. Control plants were treated only with an aqueous solution of Acetone/Dimethyl sulfoxide/Tween® 80.

(352) After 24 hours, the plants were contaminated by spraying the leaves with an aqueous suspension of Phakospora pachyrhizi spores. The contaminated soybean plants were incubated for 24 hours at 24° C. and at 100% relative humidity and then for 11 days at 24° C. and at 70-80% relative humidity.

(353) The test was evaluated 12 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 was observed.

(354) hi this test the following compounds according to the invention showed efficacy between 70% and 79% at a concentration of 500 ppm of active ingredient: Ia-32.

(355) 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: Ia-69.

(356) hi this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 500 ppm of active ingredient: Ia-37.

Example I

In Vivo Preventive Test on Phakopsora Test (Soybeans)

(357) Solvent: 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide

(358) Emulsifier: 1 part by weight of alkylaryl polyglycol ether

(359) To produce a suitable preparation of active compound, 1 part by weight of active compound was mixed with the stated amounts of solvent and emulsifier, and the concentrate was diluted with water to the desired concentration.

(360) To test for preventive activity, young plants were sprayed with the preparation of active compound at the stated rate of application. After the spray coating had dried on, the plants were 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%.

(361) The plants remained in the incubation cabinet at approximately 24° C. and a relative atmospheric humidity of approximately 80% and a day/night interval of 12 h.

(362) The test was 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.

(363) In this test the following compounds according to the invention showed efficacy between 80% and 89% at a concentration of 50 ppm of active ingredient: Ia-22; Ia-en-07.

(364) In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 50 ppm of active ingredient: Ia-06; Ia-15; Ia-18; Ia-24; Ia-39; Ia-en-01; Ia-en-02; Ia-en-04; Ia-en-08; Ia-en-09; Ia-en-10; Ia-en-11.

Example J

In Vivo Preventive Blumeria Test (Barley)

(365) Solvent: 49 parts by weight of N,N-dimethylacetamide

(366) Emulsifier: 1 part by weight of alkylaryl polyglycol ether

(367) To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination was mixed with the stated amounts of solvent and emulsifier, and the concentrate was diluted with water to the desired concentration.

(368) To test for preventive activity, young plants were sprayed with the preparation of active compound or active compound combination at the stated rate of application.

(369) After the spray coating had been dried, the plants were dusted with spores of Blumeria graminis f. sp. hordei.

(370) The plants were 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.

(371) The test was 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.

(372) 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: Ia-03; Ia-04; Ia-05; Ia-06; Ia-24; Ia-53; Ia-73; Ia-en-02; Ia-en-08; Ib-04.

Example K

In Vivo Preventive Fusarium culmorum Test (Wheat)

(373) Solvent: 49 parts by weight of N,N-dimethylacetamide

(374) Emulsifier: 1 part by weight of alkylaryl polyglycol ether

(375) To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination was mixed with the stated amounts of solvent and emulsifier, and the concentrate was diluted with water to the desired concentration.

(376) To test for preventive activity, young plants were sprayed with the preparation of active compound or active compound combination at the stated rate of application. After the spray coating had been dried, the plants were slightly injured by using a sandblast and afterwards they were sprayed with a conidia suspension of Fusarium culmorum.

(377) The plants were placed in the greenhouse under a translucent incubation cabinet at a temperature of approximately 22° C. and a relative atmospheric humidity of approximately 100%.

(378) The test was evaluated 5 days after the inoculation. 0% means an efficacy which corresponds to that of the untreated control, while an efficacy of 100% means that no disease is observed.

(379) 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: Ia-05.

Example L

In Vivo Preventive Leptosphaeria nodorum Test (Wheat)

(380) Solvent: 49 parts by weight of N,N-dimethylacetamide

(381) Emulsifier: 1 part by weight of alkylaryl polyglycol ether

(382) To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination was mixed with the stated amounts of solvent and emulsifier, and the concentrate was diluted with water to the desired concentration.

(383) To test for preventive activity, young plants were sprayed with the preparation of active compound or active compound combination at the stated rate of application.

(384) After the spray coating had been dried, the plants were sprayed with a spore suspension of Leptosphaeria nodorum. The plants remained for 48 hours in an incubation cabinet at approximately 20° C. and a relative atmospheric humidity of approximately 100%.

(385) The plants were placed in the greenhouse at a temperature of approximately 25° C. and a relative atmospheric humidity of approximately 80%.

(386) The test was 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.

(387) 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: Ib-04.

(388) 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: Ia-05.