FIVE-MEMBERED C-N-ATTACHED ARYL SULPHIDE AND ARYL SULPHOXIDE DERIVATIVES AS PESTICIDES

Abstract

Provided are compounds of the formula (I)

##STR00001##

which are suitable for controlling animal pests including arthropods and in particular insects and acarids and in which the structural elements have the meanings given in the description.

Claims

1. A compound of formula (I) ##STR00036## wherein W represents hydrogen or halogen; n represents the number 0, 1 or 2; Y represents hydrogen, halogen, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy, halo-(C.sub.1-C.sub.6)-alkoxy or amino; or represents NR′″R″″, where R′″ and R″″ independently of one another represent hydrogen, (C.sub.1-C.sub.6)-alkyl or halo-(C.sub.2-C.sub.6)-alkyl; X represents hydrogen, halogen, cyano, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl or (C.sub.1-C.sub.6)-alkoxy; V.sup.1 and V.sup.2 independently of one another represent oxygen or sulphur; R.sup.1 and R.sup.2 independently of one another represent hydrogen, halogen, hydroxy, cyano or nitro; or represent alkyl, alkenyl, alkynyl, alkoxy, alkylsulphanyl, alkylsulphinyl, alkylsulphonyl, haloalkylcarbonyl, alkylcarbonyl or alkoxycarbonyl, where the radicals mentioned above may optionally be substituted by halogen, alkyl, cycloalkyl, cyano, nitro, alkoxy, haloalkyl or haloalkoxy, in particular fluorine, chlorine, (C.sub.1-C.sub.3)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, cyclopropyl, cyano, (C.sub.1-C.sub.3)-alkoxy, (C.sub.1-C.sub.3)-haloalkyl or (C.sub.1-C.sub.3)-haloalkoxy; or R.sup.1 and R.sup.2 form a saturated or unsaturated three- to six-membered ring which is optionally substituted by halogen, alkyl, cycloalkyl, cyano, nitro, alkoxy, haloalkyl or haloalkoxy, in particular fluorine, chlorine, (C.sub.1-C.sub.3)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, cyclopropyl, cyano, (C.sub.1-C.sub.3)-alkoxy, (C.sub.1-C.sub.3)-haloalkyl or (C.sub.1-C.sub.3)-haloalkoxy, and optionally interrupted by one or more heteroatoms independently selected from the group consisting of O, S and N, with the proviso that two oxygen atoms are not directly adjacent to one another; R.sup.3 represents alkyl, haloalkyl, alkoxyalkyl, haloalkoxyalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkyl-S(O).sub.m-alkyl, haloalkyl-S(O).sub.m-alkyl, N-alkylaminocarbonylalkyl or N,N-dialkylaminocarbonylalkyl, or represents cycloalkyl, cycloalkylalkyl, cycloalkenyl or cycloalkenylalkyl which is optionally mono- or disubstituted by identical or different substituents from the group consisting of halogen, cyano, nitro, hydroxy, amino, (C.sub.1-C.sub.4)-alkyl, halo-(C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-alkoxy, halo-(C.sub.1-C.sub.3)-alkoxy and cyclopropyl, or represents heterocyclyl, heterocyclylalkyl, aryl, arylalkyl, hetaryl or hetarylalkyl which is optionally mono- or disubstituted by identical or different substituents from the group consisting of halogen, cyano, nitro, hydroxy, amino, (C.sub.1-C.sub.4)-alkyl, halo-(C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-alkoxy, halo-(C.sub.1-C.sub.3)-alkoxy and cyclopropyl; R.sup.4 represents hydrogen, alkyl, haloalkyl, alkoxyalkyl, haloalkoxyalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkyl-S(O).sub.m-alkyl, haloalkyl-S(O).sub.m-alkyl, N-alkylaminocarbonylalkyl or N,N-dialkylaminocarbonylalkyl, or represents cycloalkyl, cycloalkylalkyl, cycloalkenyl or cycloalkenylalkyl which is optionally mono- or disubstituted by identical or different substituents from the group consisting of halogen, cyano, nitro, hydroxy, amino, (C.sub.1-C.sub.4)-alkyl, halo-(C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-alkoxy, halo-(C.sub.1-C.sub.3)-alkoxy and cyclopropyl, or represents heterocyclyl, heterocyclylalkyl, aryl, arylalkyl, hetaryl or hetarylalkyl which is optionally mono- or disubstituted by identical or different substituents from the group consisting of halogen, cyano, nitro, hydroxy, amino, (C.sub.1-C.sub.4)-alkyl, halo-(C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-alkoxy, halo-(C.sub.1-C.sub.3)-alkoxy and cyclopropyl; or R.sup.3 and R.sup.4 together with the nitrogen atom to which they are attached form a saturated to triunsaturated 3- to 6-membered ring which is optionally substituted by halogen, cyano, (C.sub.1-C.sub.4)-alkyl, halo-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkoxy, halo-(C.sub.1-C.sub.4)-alkoxy or (C.sub.3-C.sub.6)-cycloalkyl; m represents the number 0, 1 or 2.

2. A compound according to claim 1 wherein the structural elements are defined as follows: W represents hydrogen or halogen; n represents the number 0 or 1; Y represents hydrogen, halogen, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.1-C.sub.3)-alkoxy, (C.sub.1-C.sub.3)-haloalkoxy or amino; or represents NR′″R″″, where R′″ and R″″ independently of one another represent hydrogen, (C.sub.1-C.sub.4)-alkyl or (C.sub.2-C.sub.4)-haloalkyl; X represents hydrogen, halogen, cyano, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl or (C.sub.1-C.sub.3)-alkoxy; V.sup.1 and V.sup.2 independently of one another represent oxygen or sulphur; R.sup.1 and R.sup.2 independently of one another represent hydrogen or (C.sub.1-C.sub.3)-alkyl; or R.sup.1 and R.sup.2 together with the carbon atom to which they are attached represent a (C.sub.3-C.sub.6)-cycloalkyl ring; R.sup.3 represents (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-alkoxy-(C.sub.1-C.sub.3)-alkyl, halo-(C.sub.1-C.sub.3)-alkoxy-(C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.6)-alkenyl, halo-(C.sub.1-C.sub.3)-alkenyl, (C.sub.1-C.sub.6)-alkynyl, halo-(C.sub.1-C.sub.3)-alkynyl, (C.sub.1-C.sub.3)-alkyl-S(O).sub.m—(C.sub.1-C.sub.3)-alkyl, halo-(C.sub.1-C.sub.3)-alkyl-S(O).sub.m—(C.sub.1-C.sub.3)-alkyl, N—(C.sub.1-C.sub.3)-alkylaminocarbonyl-(C.sub.1-C.sub.3)-alkyl or N,N-di-(C.sub.1-C.sub.3)-alkylaminocarbonyl-(C.sub.1-C.sub.3)-alkyl, or represents (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.3)-alkyl, (C.sub.3-C.sub.6)-cycloalkenyl or (C.sub.3-C.sub.6)-cycloalkenyl-(C.sub.1-C.sub.3)-alkyl which is optionally mono- or disubstituted by identical or different substituents from the group consisting of halogen, cyano, nitro, hydroxy, amino, (C.sub.1-C.sub.4)-alkyl, halo-(C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-alkoxy, halo-(C.sub.1-C.sub.3)-alkoxy and cyclopropyl, or represents heterocyclyl, heterocyclyl-(C.sub.1-C.sub.3)-alkyl, aryl, aryl-(C.sub.1-C.sub.3)-alkyl, hetaryl or hetaryl-(C.sub.1-C.sub.3)-alkyl which is optionally mono- or disubstituted by identical or different substituents from the group consisting of halogen, cyano, nitro, hydroxy, amino, (C.sub.1-C.sub.4)-alkyl, halo-(C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-alkoxy, halo-(C.sub.1-C.sub.3)-alkoxy and cyclopropyl; R.sup.4 represents hydrogen, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.3)-alkyl or (C.sub.1-C.sub.3)-alkoxy-(C.sub.1-C.sub.3)-alkyl, or represents (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.3)-alkyl, phenyl, phenyl-(C.sub.1-C.sub.3)-alkyl, pyridyl or pyridyl-(C.sub.1-C.sub.3)-alkyl which is optionally mono- or disubstituted by identical or different substituents from the group consisting of halogen, cyano, nitro, hydroxy, amino, (C.sub.1-C.sub.4)-alkyl, halo-(C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-alkoxy, halo-(C.sub.1-C.sub.3)-alkoxy and cyclopropyl; or R.sup.3 and R.sup.4 together with the nitrogen atom to which they are attached form a saturated to triunsaturated 3- to 6-membered ring selected from the group consisting of aziridinyl, azirenyl, diaziridinyl, diazirenyl, azetidinyl, dihydroazetyl, diazetidinyl, dihydrodiazetyl, oxazetidinyl, oxazetyl, thiazetidinyl, thiazetyl, pyrrolidinyl, dihydropyrrolyl, pyrazolidinyl, dihydropyrazolyl, imidazolidinyl, dihydroimidazolyl, oxazolidinyl, dihydrooxazolyl, thiazolidinyl, dihydrothyazolyl, piperidinyl, piperazinyl, hexahydropyridazinyl, hexahydropyrimidinyl, morpholine, dioxazinanyl, thiomorpholine, dithiazinane, dioxothiazinane, pyrrolyl, pyrazolyl, imidazolyl, triazolyl and tetrazolyl which is optionally substituted by halogen, cyano, (C.sub.1-C.sub.4)-alkyl, halo-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkoxy, halo-(C.sub.1-C.sub.4)-alkoxy, (C.sub.3-C.sub.6)-cycloalkyl; m represents the number 0, 1 or 2.

3. A compound according to claim 1 wherein the structural elements are defined as follows: W represents hydrogen or fluorine; n represents the number 0 or 1; Y represents fluorine, chlorine, bromine, methyl, trifluoromethyl or methoxy; X represents hydrogen, chlorine, fluorine or methyl; in particular where X and Y represent the following combinations (Y,X): (Me, F), (Me,H), (Me,Cl), (Me,Me), (Cl,Cl), (Cl,F), (MeO,F), (MeO,H), (Cl,H), (Br,H), (Br,F), (F,F), (CF.sub.3,H), (CF.sub.3,F), particularly preferably (Me, F), (Me,Cl), (Me,Me), (Cl,Cl); V.sup.1 and V.sup.2 independently of one another represent oxygen or sulphur; R.sup.1 and R.sup.2 independently of one another represent hydrogen, methyl or ethyl; or R.sup.1 and R.sup.2 form a cyclopropyl or cyclobutyl ring; R.sup.3 represents methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 1,1-dimethylpropyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, 2,2-difluoro-n-propyl, 2-methoxyethyl, 2-ethoxyethyl, 3-methoxypropyl, 3-ethoxypropyl, dimethylaminocarbonylmethyl, diethylaminocarbonylmethyl, N-ethyl-N-methylaminocarbonylmethyl, N-isopropyl-N-methylaminocarbonylmethyl, dimethylaminocarbonylethyl, diethylaminocarbonylethyl, N-ethyl-N-methylaminocarbonylethyl, N-isopropyl-N-methylaminocarbonylethyl, N-cyclopropyl-N-methylaminocarbonylmethyl or N-cyclopropyl-N-methylaminocarbonylethyl, or represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 2-tetrahydrofurylmethyl, 3-tetrahydrofurylmethyl, 2-tetrahydrofurylethyl or 3-tetrahydrofurylethyl, or represents phenyl which is optionally mono- or disubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, cyano, nitro, hydroxy, amino, methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, trifluoromethyl, difluoromethyl, methoxy, trifluoromethoxy or difluoromethoxy, or represents pyridyl which is optionally mono- or disubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, cyano, nitro, hydroxy, amino, methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, trifluoromethyl, difluoromethyl, methoxy, trifluoromethoxy or difluoromethoxy, or represents pyridylmethyl or benzyl which is optionally mono- or disubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, cyano, nitro, hydroxy, amino, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, difluoromethyl, methoxy, trifluoromethoxy or difluoromethoxy; R.sup.4 represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, 2-methoxyethyl, 2-ethoxyethyl, cyclopropyl, cyclobutyl, cyclopropylmethyl, phenyl or benzyl; or R.sup.3 and R.sup.4 together with the nitrogen atom to which they are attached form an azetidine, oxetane, thiethane, morpholine, thiomorpholine, dioxothiazinane, piperidine or an N-methyl-substituted piperazine ring.

4. A compound according to claim 1 wherein the structural elements are defined as follows: W represents fluorine; n represents the number 0 or 1; Y represents chlorine or methyl; X represents hydrogen, fluorine, chlorine or methyl; in particular where X and Y represent the following combinations (Y,X): (Me,Cl), (Me, F), (Me,Me), (Cl,Cl); V.sup.1 and V.sup.2 independently of one another represent oxygen or sulphur; R.sup.1 and R.sup.2 independently of one another represent hydrogen or methyl; R.sup.3 represents methyl, ethyl, isopropyl, isobutyl, sec-butyl, tert-butyl, 1,1-dimethylpropyl, 2,2,2-trifluoroethyl, 2-methoxyethyl, or represents cyclopropyl or 2-tetrahydrofurylmethyl, or represents phenyl, 3-fluorophenyl, 4-fluorophenyl, 3-chlorophenyl, 3-trifluoromethylphenyl, 2-pyridyl, 3-pyridyl or benzyl; R.sup.4 represents hydrogen or methyl; or R.sup.3 and R.sup.4 together form one of the following rings: 1-morpholine, 1-(4-methylpiperazine), 1-(1,1-dioxo-1,4-thiazinane) or 1-(4,4-difluoropiperidine).

5. A compound according to claim 1, comprising a structure according to formula (I-A) ##STR00037##

6. A compound of formula (II) ##STR00038##

7. A compound of formula (III) ##STR00039## wherein R represents hydrogen or an alkyl group, optionally methyl or ethyl.

8. A compound of formula (VI) ##STR00040##

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

10. A formulation according to claim 9, further comprising at least one extender and/or at least one surface-active substance.

11. A formulation according to claim 9, wherein the compound of formula (I) is in a mixture with at least one further active compound.

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

13. A method according to claim 12, wherein the pest is an animal pest and comprises an insect, an acarid or a nematode, or the pest is an insect, an acarid or a nematode.

14. A product comprising a compound of formula (I) according to claim 1 or a formulation thereof according to claim 9 for controlling animal pests.

15. Product according to claim 14, wherein the animal pest comprises an insect, an acarid, or a nematode, or the animal pest is an insect, an acarid or a nematode.

16. Product according to claim 14 in crop protection.

17. Product according to claim 14 in the field of animal health.

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

19. Seed obtained by a method according to claim 18.

Description

EXAMPLES

[0408] The preparation and use examples which follow illustrate the invention without limiting it. The products were characterized by 1H NMR spectroscopy and/or LC-MS (Liquid Chromatography Mass Spectrometry) and/or GC-MS (Gas Chromatography-Mass Spectrometry).

[0409] The log P values were determined analogously to OECD Guideline 117 (EC Directive 92/69/EEC) by HPLC (high-performance liquid chromatography) using reversed-phase columns (C 18), by the following methods:

[a] The LC-MS determination in the acidic range was effected at pH 2.7 with 0.1% aqueous formic acid and acetonitrile (contains 0.1% formic acid) as eluents; linear gradient from 10% acetonitrile to 95% acetonitrile. log P[a] is also referred to as log P(HCOOH).
[b] LC-MS determination in the neutral range was effected at pH 7.8 with 0.001 molar aqueous ammonium hydrogencarbonate solution and acetonitrile as eluents; linear gradient from 10% acetonitrile to 95% acetonitrile. log P[b] is also referred to as log P(neutral).

[0410] Calibration is effected with solutions of a homologous series of unbranched alkan-2-ones (having 3 to 16 carbon atoms) with known log P values (log P values determined on the basis of the retention times by linear interpolation between two successive alkanones).

[0411] The NMR spectra were measured using a Bruker II Avance 400 fitted with a 1.7 mm TCI sample head. In individual cases, the NMR spectra were determined with a Bruker Avance II 600.

[0412] The NMR data of selected examples are stated in classic form (δ values, multiplet splitting, number of hydrogen atoms). The splitting of the signals was described as follows: s (singlet), d (doublet), t (triplet), q (quartet), m (multiplet), broad (for broad signals). Solvents used were CD.sub.3CN, CDCl.sub.3 or D6-DMSO, and tetramethylsilane (0.00 ppm) was used as reference.

[0413] The GC-MS spectra are determined using an Agilent 6890 GC, HP 5973 MSD on a dimethylsilicone phase, using a temperature gradient from 50° C. to 320° C. GC-MS indices are determined as Kovats indices using solutions of a homologous series of n-alkanes (having an even number of 8 to 38 carbon atoms).

Preparation Example 1: N-Cyclopropyl-3-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulphinyl)phenyl]-2,4-dioxoimidazolidine-1-carboxamide (Ex. No. 3)

Step 1: N-Cyclopropyl-3-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulphanyl)phenyl]-2,4-dioxoimidazolidine-1-carboxamide (Ex. No. 1)

[0414] ##STR00015##

[0415] 100 mg (0.31 mmol) of 3-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulphanyl)phenyl]imidazolidine-2,4-dione (IIa-1) were initially charged in 5 ml of dichloromethane. 52 mg (0.62 mmol) of cyclopropyl isocyanate were added and the suspension was stirred at room temperature for 1 h. 130 μl (0.93 mmol) of triethylamine were then added dropwise and the reaction mixture was stirred for another 1 h. According to TLC (cyclohexane/acetone 3:1), the reaction was complete. The solvent was removed under reduced pressure on a rotary evaporator and the residue was chromatographed by MPLC on an RP-18 column using a gradient of water/acetonitrile/0.1% formic acid. This gave 95 mg (purity 98% according to LC/MS, 74% of theory) of the title compound.

[0416] log P(HCOOH): 3.07; log P(neutral): 2.98

[0417] .sup.1H NMR (400.0 MHz, D6-DMSO) δ ppm: 7.79-7.78 (m, 1H), 7.67 (d, 1H), 7.44 (d, 1H), 4.47 (broad, 2H), 3.86 (q, 2H), 2.70-2.66 (m, 1H), 2.45 (s, 3H), 0.73-0.68 (m, 2H), 0.56-0.53 (m, 2H)

Step 2: N-Cyclopropyl-3-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulphinyl)phenyl]-2,4-dioxoimidazolidine-1-carboxamide (Ex. No. 3)

[0418] ##STR00016##

[0419] 60 mg (0.15 mmol) of N-cyclopropyl-3-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulphanyl)phenyl]-2,4-dioxoimidazolidine-1-carboxamide were initially charged in 6 ml of dichloromethane, 37 mg (75%, 0.16 mmol) of meta-chloroperbenzoic acid were added and the reaction mixture was stirred at room temperature overnight and then washed with sodium thiosulphate and sodium bicarbonate solution. The organic phase was dried over dry sodium sulphate and filtered. After removal of the solvent under reduced pressure, the residue was chromatographed by MPLC on an RP-18 column using a gradient of water/acetonitrile/0.1% formic acid. This gave 49 mg (purity 100% according to LC/MS, 78% of theory) of the title compound.

[0420] log P(HCOOH): 2.15; log P(neutral): 2.12

[0421] .sup.1H NMR (400.0 MHz, D6-DMSO) δ ppm: 7.99 (d, 1H), 7.78-7.77 (m, 1H), 7.55 (d, 1H), 4.46 (broad, 2H), 4.37-4.25 (m, 1H), 3.88-3.82 (m, 1H), 2.71-2.66 (m, 1H), 2.43 (s, 3H), 0.73-0.69 (m, 2H), 0.56-0.52 (m, 2H)

Preparation Example 2: N-Cyclopropyl-3-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulphinyl)phenyl]-4-oxo-2-thioxoimidazolidine-1-carboxamide (Ex. No. 4)

Step 1: N-Cyclopropyl-3-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulphanyl)phenyl]-4-oxo-2-thioxoimidazolidine-1-carboxamide (Ex. No. 2)

[0422] ##STR00017##

[0423] 100 mg (0.30 mmol) of 3-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulphanyl)phenyl]-2-thioxoimidazolidin-4-one (IIa-2) were initially charged in 5 ml of dichloromethane. 49 mg (0.59 mmol) of cyclopropyl isocyanate were added and the suspension was stirred at room temperature for 1 h. 124 μl (0.89 mmol) of triethylamine were then added dropwise and the reaction mixture was stirred for another 1 h. The solvent was removed under reduced pressure on a rotary evaporator and the residue was chromatographed by MPLC on an RP-18 column using a gradient of water/acetonitrile/0.1% formic acid. This gave 57 mg (purity 93% according to LC/MS, 42% of theory) of the title compound.

[0424] log P(HCOOH): 3.66; log P(neutral): 3.56

[0425] .sup.1H NMR (400.0 MHz, D6-DMSO) δ ppm: 9.50-9.49 (m, 1H), 7.65 (d, 1H), 7.45 (d, 1H), 4.86-4.60 (m, 2H), 3.86 (q, 2H), 2.77-2.72 (m, 1H), 2.46 (s, 3H), 0.79-0.74 (m, 2H), 0.60-0.52 (m, 2H)

Step 2: N-Cyclopropyl-3-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulphinyl)phenyl]-4-oxo-2-thioxoimidazolidine-1-carboxamide (Ex. No. 4)

[0426] ##STR00018##

[0427] 40 mg (0.095 mmol) of N-cyclopropyl-3-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulphanyl)phenyl]-4-oxo-2-thioxoimidazolidine-1-carboxamide were initially charged in 4 ml of dichloromethane, 24 mg (75%, 0.10 mmol) of meta-chloroperbenzoic acid were added and the reaction mixture was stirred at room temperature overnight and then washed with sodium thiosulphate and sodium bicarbonate solution. The organic phase was dried over dry sodium sulphate and filtered. After removal of the solvent under reduced pressure, the residue was chromatographed by MPLC on an RP-18 column using a gradient of water/acetonitrile/0.1% formic acid. This gave 18 mg (purity 100% according to LC/MS, 44% of theory) of the title compound.

[0428] log P(HCOOH): 2.64; log P(neutral): 2.65

[0429] .sup.1H NMR (400.0 MHz, D6-DMSO) δ ppm: 9.50-9.46 (m, 1H), 7.99-7.97 (m, 1H), 7.56 (d, 1H), 4.84-4.78 (m, 1H), 4.63-4.58 (m, 1H), 4.39-4.29 (m, 1H), 3.88-3.77 (m, 1H), 2.78-2.73 (m, 1H), 2.44 (s, 3H), 0.80-0.74 (m, 2H), 0.57-0.55 (m, 2H)

Preparation Example 3: 3-[2-Fluoro-4-methyl-5-(2,2,2-trifluoroethylsulphinyl)phenyl]-N-isobutyl-2,4-dioxoimidazolidine-1-carboxamide (Ex. No. 15)

Step 1: 3-[2-Fluoro-4-methyl-5-(2,2,2-trifluoroethylsulphanyl)phenyl]-N-isobutyl-2,4-dioxoimidazolidine-1-carboxamide (Ex. No. 12)

[0430] ##STR00019##

[0431] 100 mg (0.31 mmol) of 3-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulphanyl)phenyl]imidazolidine-2,4-dione (IIa-1) were initially charged in 5 ml of dichloromethane. 62 mg (0.62 mmol) of isobutyl isocyanate were added and the suspension was stirred at room temperature for 1 h. 130 μl (0.93 mmol) of triethylamine were then added dropwise and the reaction mixture was stirred for another 1 h. The solvent was removed under reduced pressure on a rotary evaporator and the residue was chromatographed by MPLC on a silica gel column using a gradient of cyclohexane/acetone. This gave 80 mg (purity 97% according to LC/MS, 60% of theory) of the title compound.

[0432] log P(HCOOH): 3.67; log P(neutral): 3.58

[0433] .sup.1H NMR (400.0 MHz, D6-DMSO) δ ppm: 7.85 (t, 1H), 7.70 (d, 1H), 7.45 (d, 1H), 4.46 (broad, 2H), 3.87 (q, 2H), 3.09-3.05 (m, 2H), 2.46 (s, 3H), 1.80-1.77 (m, 1H), 0.87 (d, 6H)

Step 2: 3-[2-Fluoro-4-methyl-5-(2,2,2-trifluoroethylsulphinyl)phenyl]-N-isobutyl-2,4-dioxoimidazolidine-1-carboxamide (Ex. No. 15)

[0434] ##STR00020##

[0435] 45 mg (0.11 mmol) of 3-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulphanyl)phenyl]-N-isobutyl-2,4-dioxoimidazolidine-1-carboxamide were initially charged in 4.5 ml of dichloromethane, 27 mg (75%, 0.12 mmol) of meta-chloroperbenzoic acid were added and the reaction mixture was stirred at room temperature overnight and then washed with sodium thiosulphate and sodium bicarbonate solution. The organic phase was dried over sodium sulphate and filtered. After removal of the solvent under reduced pressure, the residue was chromatographed by MPLC on an RP-18 column using a gradient of water/acetonitrile/0.1% formic acid. This gave 32 mg (purity 100% according to LC/MS, 69% of theory) of the title compound.

[0436] log P(HCOOH): 2.72; log P(neutral): 2.66

[0437] .sup.1H NMR (400.0 MHz, D6-DMSO) δ ppm: 8.01 (d, 1H), 7.85 (t, 1H), 7.56 (d, 1H), 4.55 (broad, 2H), 4.35-4.28 (m, 1H), 3.90-3.83 (m, 1H), 3.07 (t, 2H), 2.43 (s, 3H), 1.82-1.75 (m, 1H), 0.88 (d, 6H)

Preparation Example 4: N-Ethyl-3-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulphinyl)phenyl]-5-methyl-2,4-dioxoimidazolidine-1-carboxamide (Ex. No. 27)

Step 1: N-Ethyl-3-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulphanyl)phenyl]-5-methyl-2,4-dioxoimidazolidine-1-carboxamide (Ex. No. 24)

[0438] ##STR00021##

[0439] 200 mg (0.59 mmol) of 3-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulphanyl)phenyl]-5-methylimidazolidine-2,4-dione (IIa-3) were initially charged in 10 ml of dichloromethane. 85 mg (1.18 mmol) of ethyl isocyanate and 249 μl (1.78 mmol) of triethylamine were added dropwise and the reaction mixture was stirred for another 1 h. The volatile components were removed under reduced pressure on a rotary evaporator. The residue was chromatographed by MPLC on an RP-18 column using a gradient of water/acetonitrile/0.1% formic acid. This gave 153 mg (purity 99% according to LC/MS, 63% of theory) of the title compound.

[0440] log P(HCOOH): 3.38; log P(neutral): 3.30

[0441] .sup.1H NMR (400.0 MHz, D6-DMSO) δ ppm: 7.91-7.88 (m, 1H), 7.74 (broad, 1H), 7.45 (d, 1H), 4.73 (broad, 1H), 3.88 (q, 2H), 3.28-3.21 (m, 2H), 2.46 (s, 3H), 1.56 (d, 3H), 1.10 (t, 3H)

Step 2: N-Ethyl-3-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulphinyl)phenyl]-5-methyl-2,4-dioxoimidazolidine-1-carboxamide (Ex. No. 27)

[0442] ##STR00022##

[0443] 100 mg (0.24 mmol) of N-ethyl-3-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulphanyl)phenyl]-5-methyl-2,4-dioxoimidazolidine-1-carboxamide were initially charged in 10 ml of dichloromethane, 62 mg (75%, 0.27 mmol) of meta-chloroperbenzoic acid were added and the reaction mixture was stirred at room temperature overnight and then washed with sodium thiosulphate and sodium bicarbonate solution. The organic phase was dried over dry sodium sulphate and filtered. After removal of the solvent under reduced pressure, the residue was chromatographed by MPLC on an RP-18 column using a gradient of water/acetonitrile/0.1% formic acid. This gave 110 mg (purity 93% according to LC/MS, 98% of theory) of the title compound.

[0444] log P(HCOOH): 2.42; log P(neutral): 2.39

[0445] .sup.1H NMR (400.0 MHz, D6-DMSO) δ ppm: 8.06 (d, 1H), 7.90-7.87 (m, 1H), 7.56 (d, 1H), 4.71 (broad, 1H), 4.35-4.28 (m, 1H), 3.89-3.82 (m, 1H), 3.29-3.21 (m, 2H), 2.43 (s, 3H), 1.57 (d, 3H), 1.10 (t, 3H).

Preparation Example 5: 3-[2-Fluoro-4-methyl-5-(2,2,2-trifluoroethylsulphinyl)phenyl]-2,4-dioxo-N-(2,2,2-trifluoroethyl)imidazolidine-1-carboxamide (Ex. No. 36)

Step 1: 3-[2-Fluoro-4-methyl-5-(2,2,2-trifluoroethylsulphanyl)phenyl]-2,4-dioxo-N-(2,2,2-trifluoroethyl)imidazolidine-1-carboxamide (Ex. No. 30)

[0446] ##STR00023##

[0447] 300 mg (0.93 mmol) of 3-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulphanyl)phenyl]imidazolidine-2,4-dione (IIa-1) were initially charged in 15 ml of dichloromethane. 175 mg (1.40 mmol) of trifluoroethyl isocyanate and 259 μl (1.86 mmol) of triethylamine were added dropwise and the reaction mixture was stirred for another 1.5 h. The reaction mixture was then extracted twice with saturated sodium bicarbonate solution. The aqueous phase was extracted once with dichloromethane. The organic phases were combined, dried over dry sodium sulphate and filtered. The solvent was removed under reduced pressure on a rotary evaporator. The residue consisted of 376 mg (purity 100% according to LC/MS, 90% of theory) of the title compound.

[0448] log P(HCOOH): 3.28; log P(neutral): 3.21

[0449] .sup.1H NMR (400.0 MHz, D6-DMSO) δ ppm: 8.32 (t, 1H), 7.71 (d, 1H), 7.46 (d, 1H), 4.58-4.40 (broad, 2H), 4.10-4.05 (m, 2H), 3.91-3.83 (m, 2H), 2.46 (s, 3H)

Step 2: 3-[2-Fluoro-4-methyl-5-(2,2,2-trifluoroethylsulphinyl)phenyl]-2,4-dioxo-N-(2,2,2-trifluoroethyl)imidazolidine-1-carboxamide (Ex. No. 36)

[0450] ##STR00024##

[0451] 234 mg (0.50 mmol) of 3-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulphanyl)phenyl]-2,4-dioxo-N-(2,2,2-trifluoroethyl)imidazolidine-1-carboxamide were initially charged in 10 ml of dichloromethane, 126 mg (75%, 0.55 mmol) of meta-chloroperbenzoic acid were added and the reaction mixture was stirred at room temperature overnight and then washed with sodium thiosulphate and sodium bicarbonate solution. The organic phase was dried over dry sodium sulphate and filtered. After removal of the solvent under reduced pressure, the residue was chromatographed by MPLC on an RP-18 column using a gradient of water/acetonitrile/0.1% formic acid. This gave 93 mg (purity 100% according to LC/MS, 40% of theory) of the title compound.

[0452] log P(HCOOH): 2.46; log P(neutral): 2.42

[0453] .sup.1H NMR (400.0 MHz, D6-DMSO) δ ppm: 8.32 (t, 1H), 8.03 (d, 1H), 7.57 (d, 1H), 4.54-4.40 (broad, 2H), 4.39-4.27 (m, 1H), 4.13-4.04 (m, 2H), 3.88-3.82 (m, 1H), 2.43 (s, 3H)

[0454] The enantiomers were obtained from the racemate by separating them preparatively by HPLC on a chiral column (ChiralCel OJ-H, e.g. 5 nm 250×4.6 mm) using the mobile phase heptane/methanol/ethanol.

[0455] The optical rotations were determined on a Perkin Elmer 341, serial number 9123, at a wavelength of 589 nm and a temperature of 20° C.

[0456] The specific optical rotations below should be understood as an average from 5 different measurements:

Enantiomer 1 (Ex. No. 135): −35.6 in acetonitrile (c=0.010)
Enantiomer 2 (Ex. No. 136): 36.4 in acetonitrile (c=0.010)

Preparation Example 6: N-Cyclopropyl-3-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulphinyl)phenyl]-5,5-dimethyl-2,4-dioxoimidazolidine-1-carboxamide (Ex. No. 84)

Step 1: N-Cyclopropyl-3-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulphanyl)phenyl]-5,5-dimethyl-2,4-dioxoimidazolidine-1-carboxamide (Ex. No. 74)

[0457] ##STR00025##

[0458] 100 mg (0.28 mmol) of 3-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulphanyl)phenyl]-5,5-dimethylimidazolidine-2,4-dione (IIa-5) were initially charged in 5 ml of dichloromethane. 47 mg (0.57 mmol) of cyclopropyl isocyanate and 119 μl (0.85 mmol) of triethylamine were added dropwise and the reaction mixture was stirred for another 1 h. The volatile components were removed under reduced pressure on a rotary evaporator. The residue was chromatographed by MPLC on an RP-18 column using a gradient of water/acetonitrile/0.1% formic acid. This gave 102 mg (purity 100% according to LC/MS, 82% of theory) of the title compound.

[0459] log P(HCOOH): 3.76; log P(neutral): 3.72

[0460] .sup.1H NMR (400.0 MHz, D6-DMSO) δ ppm: 8.01-8.00 (m, 1H), 7.81 (d, 1H), 7.45 (d, 1H), 3.90 (q, 2H), 2.71-2.67 (m, 1H), 2.45 (s, 3H), 1.70 (s, 6H), 0.71-0.69 (m, 2H), 0.53 (broad, 2H)

Step 2: N-Cyclopropyl-3-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulphinyl)phenyl]-5,5-dimethyl-2,4-dioxoimidazolidine-1-carboxamide (Ex. No. 84)

[0461] ##STR00026##

[0462] 70 mg (0.16 mmol) of N-cyclopropyl-3-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethyl sulphanyl)phenyl]-5,5-dimethyl-2,4-dioxoimidazolidine-1-carboxamide were initially charged in 7 ml of dichloromethane, 41 mg (75%, 0.17 mmol) of meta-chloroperbenzoic acid were added and the reaction mixture was stirred at room temperature overnight and then washed with sodium thiosulphate and sodium bicarbonate solution. The organic phase was dried over dry sodium sulphate, filtered and concentrated. This gave 74 mg (purity 94% according to LC/MS, 96% of theory) of the title compound.

[0463] log P(HCOOH): 2.73; log P(neutral): 2.73

[0464] .sup.1H NMR (400.0 MHz, D6-DMSO) δ ppm: 8.14 (d, 1H), 8.00-7.99 (m, 1H), 7.56 (d, 1H), 4.43-4.18 (m, 1H), 4.04-3.72 (m, 1H), 2.72-2.67 (m, 1H), 2.44 (s, 3H), 1.71 (s, 6H), 0.71-0.70 (m, 2H), 0.53 (broad, 2H).

Preparation Example 7: 3-[2-Fluoro-4-methyl-5-(2,2,2-trifluoroethylsulphinyl)phenyl]-1-(morpholine-4-carbonyl)imidazolidine-2,4-dione (Ex. No. 125)

Step 1: 3-[2-Fluoro-4-methyl-5-(2,2,2-trifluoroethylsulphanyl)phenyl]-1-(morpholine-4-carbonyl)imidazolidine-2,4-dione (Ex. No. 122)

[0465] ##STR00027##

[0466] 300 mg (0.93 mmol) of 3-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulphanyl)phenyl]imidazolidine-2,4-dione (IIa-1) were initially charged in 10 ml of toluene. 0.26 ml (1.86 mm of of triethylamine and 0.12 ml (0.93 mmol) of trichloromethyl chloroformate were added. The reaction mixture was stirred at reflux temperature for 1 h and then cooled to 0° C. After the addition of 0.25 ml (2.78 mmol) of morpholine, the reaction mixture was stirred at room temperature overnight. The resulting suspension was filtered and the filtrate was freed of the solvent under reduced pressure on a rotary evaporator. The residue was dissolved in dichloromethane and washed twice with a saturated sodium bicarbonate solution and twice with a 10% strength hydrochloric acid solution. The organic phase was dried over dry sodium sulphate, filtered and concentrated. The residue was chromatographed by MPLC on an RP-18 column using a gradient of water/acetonitrile. This gave 178 mg (purity 100% according to LC/MS, 44% of theory) of the title compound.

[0467] log P(HCOOH): 2.61; log P(neutral): 2.58

[0468] .sup.1H NMR (400.0 MHz, D6-DMSO) δ ppm: 7.72 (d, 1H), 7.42 (d, 1H), 4.53 (s, 2H), 3.87 (q, 2H), 3.64-3.62 (m, 4H), 3.48-3.46 (m, 4H), 2.45 (s, 3H).

Step 2: 3-[2-Fluoro-4-methyl-5-(2,2,2-trifluoroethylsulphinyl)phenyl]-1-(morpholine-4-carbonyl)imidazolidine-2,4-dione (Ex. No. 125)

[0469] ##STR00028##

[0470] 128 mg (0.29 mmol) of 3-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulphanyl)phenyl]-1-(morpholine-4-carbonyl)imidazolidine-2,4-dione were initially charged in 5 ml of dichloromethane, and 71 mg (75%, 0.31 mmol) of meta-chloroperbenzoic acid were added. The reaction mixture was stirred at room temperature overnight and then washed with sodium thiosulphate and sodium bicarbonate solution. The organic phase was dried over dry sodium sulphate, filtered and concentrated. This gave 137 mg (purity 98% according to LC/MS, quantitative) of the title compound.

[0471] log P(HCOOH): 1.79; log P(neutral): 1.75

[0472] .sup.1H NMR (400.0 MHz, D6-DMSO) δ ppm: 8.04 (d, 1H), 7.53 (d, 1H), 4.53 (s, 2H), 4.33-4.24 (m, 1H), 3.88-3.79 (m, 1H), 3.64-3.62 (m, 4H), 3.49-3.47 (m, 4H), 2.43 (s, 3H).

Synthesis Intermediates

3-[2-Fluoro-4-methyl-5-(2,2,2)-trifluoroethylsulphanyl)phenyl]imidazolidine-2,4-dione (IIa-1)

[0473] ##STR00029##

[0474] 9.72 g (75.2 mmol) of ethyl isocyanatoacetate were initially charged in 270 ml of chloroform. 18.00 g (75.2 mmol) of 2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulphanyl)aniline were initially charged in 270 ml of chloroform and slowly added dropwise. The solution was stirred at room temperature overnight and then the solvent was removed under reduced pressure. The residue was taken up in 540 ml of a mixture of ethanol/35% strength hydrochloric acid 1:1 and the mixture was heated under reflux for 3 h and allowed to stand over the weekend. The white solid formed was filtered off using a nutsch filter and washed with a little ice-cold water to pH 5. This gave 18.55 g (purity 100% according to LC/MS, 77% of theory) of the title compound.

[0475] log P(HCOOH): 2.11; log P(neutral): 2.08

[0476] .sup.1H NMR (400.0 MHz, D6-DMSO) δ ppm: 8.42 (bs, 1H), 7.62 (d, 1H), 7.39 (d, 1H), 4.15 (broad, 2H), 3.91 (q, 2H), 2.43 (s, 3H)

3-[2-Fluoro-4-methyl-5-(2,2,2-trifluoroethylsulphanyl)phenyl]-2-thioxoimidazolidin-4-one (IIa-2)

[0477] ##STR00030##

[0478] 303 mg (2.09 mmol) of ethyl isothiocyanatoacetate were initially charged in 7.5 ml of chloroform. 500 mg (2.09 mmol) of 2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulphanyl)aniline were initially charged in 7.5 ml of chloroform and slowly added dropwise. The solution was stirred at room temperature overnight and then the solvent was removed under reduced pressure. The residue was taken up in 15 ml of a mixture of ethanol/35% strength hydrochloric acid 1:1 and the mixture was heated under reflux for 3 h. After cooling, the solvent was removed under reduced pressure. The residue was chromatographed by MPLC on an RP-18 column using a gradient of water/acetonitrile/0.1% formic acid. This gave 576 mg (purity 99% according to LC/MS, 81% of theory) of the title compound.

[0479] log P(HCOOH): 2.53; log P(neutral): 2.50

[0480] .sup.1H NMR (400.0 MHz, D6-DMSO) δ ppm: 10.56 (s, 1H), 7.61 (d, 1H), 7.39 (d, 1H), 4.48-4.30 (m, 2H), 3.93-3.85 (m, 2H), 2.44 (s, 3H)

3-[2-Fluoro-4-methyl-5-(2,2,2)-trifluoroethylsulphinyl)phenyl]imidazolidine-2,4-dione (IIb-1)

[0481] ##STR00031##

[0482] 50 mg (0.15 mmol) of 3-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulphanyl)phenyl]imidazolidine-2,4-dione (IIa-1) were initially charged in 5 ml of dichloromethane, 38 mg (75%, 0.16 mmol) of meta-chloroperbenzoic acid were added and the reaction mixture was stirred at room temperature for 2 h and then washed with sodium thiosulphate and sodium bicarbonate solution. The organic phase was dried over dry sodium sulphate and filtered. After removal of the solvent under reduced pressure, the residue was chromatographed by MPLC on an RP-18 column using a gradient of water/acetonitrile/0.1% formic acid. This gave 25 mg (purity 100% according to LC/MS, 49% of theory) of the title compound.

[0483] log P(HCOOH): 1.33; log P(neutral): 1.31

[0484] .sup.1H NMR (400.0 MHz, D6-DMSO) δ ppm: 8.47 (bs, 1H), 7.89 (d, 1H), 7.50 (d, 1H), 4.31-4.21 (m, 1H), 4.16 (broad, 2H), 3.96-3.87 (m, 1H), 2.42 (s, 3H).

3-[2-Fluoro-4-methyl-5-(2,2,2-trifluoroethylsulphanyl)phenyl]-5-methylimidazolidine-2,4-dione (IIa-3)

[0485] ##STR00032##

[0486] 598 mg (4.18 mmol) of ethyl 2-isocyanatopropionate were initially charged in 15 ml of chloroform. 1.00 g (4.18 mmol) of 2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulphanyl)aniline were initially charged in 15 ml of chloroform and slowly added dropwise. The solution was stirred at room temperature overnight and then the solvent was removed under reduced pressure. The residue was taken up in 30 ml of a mixture of ethanol/35% strength hydrochloric acid 1:1 and the mixture was heated under reflux for 3 h. After cooling, the solvent was removed under reduced pressure. The residue was chromatographed by MPLC on an RP-18 column using a gradient of water/acetonitrile/0.1% formic acid. This gave 395 mg (purity 99% according to LC/MS, 28% of theory) of the title compound.

[0487] log P(HCOOH): 2.34; log P(neutral): 2.31

[0488] .sup.1H NMR (400.0 MHz, D6-DMSO) δ ppm: 8.56 (s, 1H), 7.64 (d, 1H), 7.39 (d, 1H), 4.35-4.33 (m, 1H), 3.96-3.88 (m, 2H), 2.43 (s, 3H), 1.36 (d, 3H).

3-[2-Fluoro-4-methyl-5-(2,2,2-trifluoroethylsulphanyl)phenyl]-5,5-dimethylimidazolidine-2,4-dione (IIa-5)

[0489] ##STR00033##

[0490] 657 mg (4.18 mmol) of ethyl 2-isocyanato-2-methylpropionate were initially charged in 15 ml of chloroform. 1.00 g (4.18 mmol) of 2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulphanyl)aniline were initially charged in 15 ml of chloroform and slowly added dropwise. The solution was stirred at room temperature overnight and then the solvent was removed under reduced pressure. The residue was taken up in 30 ml of a mixture of ethanol/35% strength hydrochloric acid 1:1 and the mixture was heated under reflux for 3 h. After cooling, the solvent was removed under reduced pressure. The residue was chromatographed by MPLC on an RP-18 column using a gradient of water/acetonitrile/0.1% formic acid. This gave 402 mg (purity 100% according to LC/MS, 27% of theory) of the title compound.

[0491] log P(HCOOH): 2.61; log P(neutral): 2.53

[0492] .sup.1H NMR (400.0 MHz, D6-DMSO) δ ppm: 8.66 (s, 1H), 7.67 (d, 1H), 7.38 (d, 1H), 3.96-3.91 (m, 2H), 2.43 (s, 3H), 1.41 (s, 6H).

[0493] The following compounds of the formula (I) (cf. Table 1) were prepared by the processes described above.

TABLE-US-00001 TABLE 1 Compounds of the formula (I) (I) [00034] Ex. No. n Y X V.sup.1 V.sup.2 R.sup.1 R.sup.2 R.sup.3 R.sup.4 1 0 CH.sub.3 F O O H H cyclopropyl H 2 0 CH.sub.3 F S O H H cyclopropyl H 3 1 CH.sub.3 F O O H H cyclopropyl H 4 1 CH.sub.3 F S O H H cyclopropyl H 5 0 CH.sub.3 F S O H H isopropyl H 6 0 CH.sub.3 F O O H H ethyl H 7 0 CH.sub.3 F O O H H isopropyl H 8 0 CH.sub.3 F S O H H ethyl H 9 1 CH.sub.3 F O O H H ethyl H 10 1 CH.sub.3 F O O H H isopropyl H 11 0 CH.sub.3 F S O H H isobutyl H 12 0 CH.sub.3 F O O H H isobutyl H 13 1 CH.sub.3 F S O H H isobutyl H 14 1 CH.sub.3 F S O H H isopropyl H 15 1 CH.sub.3 F O O H H isobutyl H 16 0 CH.sub.3 F O O H H phenyl H 17 0 CH.sub.3 F O O H H 3-pyridyl H 18 0 CH.sub.3 F O O H H benzyl H 19 1 CH.sub.3 F O O H H phenyl H 20 1 CH.sub.3 F O O H H 3-pyridyl H 21 1 CH.sub.3 F O O H H benzyl H 22 0 CH.sub.3 CH.sub.3 O O H H isopropyl H 23 1 CH.sub.3 CH.sub.3 O O H H isopropyl H 24 0 CH.sub.3 F O O CH.sub.3 H ethyl H 25 0 CH.sub.3 F O O CH.sub.3 H cyclopropyl H 26 0 CH.sub.3 F O O CH.sub.3 H isopropyl H 27 1 CH.sub.3 F O O CH.sub.3 H ethyl H 28 1 CH.sub.3 F O O CH.sub.3 H cyclopropyl H 29 1 CH.sub.3 F O O CH.sub.3 H isopropyl H 30 0 CH.sub.3 F O O H H 2,2,2- H trifluoroethyl 31 0 CH.sub.3 CH.sub.3 O O H H ethyl H 32 1 CH.sub.3 CH.sub.3 O O H H ethyl H 33 0 CH.sub.3 CH.sub.3 O O H H tert-butyl H 34 0 CH.sub.3 CH.sub.3 O O H H isobutyl H 35 1 CH.sub.3 CH.sub.3 O O H H isobutyl H 36 1 CH.sub.3 F O O H H 2,2,2- H trifluoroethyl 37 0 CH.sub.3 F O O H H 3- H trifluoroethyl- phenyl 38 0 CH.sub.3 CH.sub.3 O O H H 2,2,2- H trifluoroethyl 39 0 CH.sub.3 F O O H H 4-fluorophenyl H 40 1 CH.sub.3 CH.sub.3 O O H H tert-butyl H 41 1 CH.sub.3 F O O H H 4-fluorophenyl H 42 0 CH.sub.3 F O O H H 3-fluorophenyl H 43 1 CH.sub.3 F O O H H 3- H trifluoroethyl- phenyl 44 0 CH.sub.3 F O O H H sec-butyl H 45 0 CH.sub.3 F O O H H 3- H chlorophenyl 46 1 CH.sub.3 F O O H H 3-fluorophenyl H 47 1 CH.sub.3 F O O H H sec-butyl H 48 1 CH.sub.3 F O O H H 3- H chlorophenyl 49 0 CH.sub.3 CH.sub.3 O O H H cyclopropyl H 50 0 CH.sub.3 Cl O O H H cyclopropyl H 51 0 CH.sub.3 Cl O O H H ethyl H 52 0 CH.sub.3 Cl O O H H isobutyl H 53 0 CH.sub.3 Cl O O H H 2,2,2- H trifluoroethyl 54 0 CH.sub.3 F O O H H tert-butyl H 55 0 CH.sub.3 CH.sub.3 O O H H 3- H trifluoroethyl- phenyl 56 0 CH.sub.3 CH.sub.3 O O H H 3- H chlorophenyl 57 0 CH.sub.3 Cl O O H H benzyl H 58 0 CH.sub.3 Cl O O H H 3- H trifluoroethyl- phenyl 59 0 CH.sub.3 Cl O O H H 3- H chlorophenyl 60 1 CH.sub.3 CH.sub.3 O O H H cyclopropyl H 61 1 CH.sub.3 CH.sub.3 O O H H 2,2,2- H trifluoroethyl 62 1 CH.sub.3 Cl O O H H cyclopropyl H 63 1 CH.sub.3 Cl O O H H 2,2,2- H trifluoroethyl 64 1 CH.sub.3 Cl O O H H ethyl H 65 1 CH.sub.3 Cl O O H H isobutyl H 66 0 CH.sub.3 F O O H H 2- H methoxyethyl 67 0 CH.sub.3 F O O H H 2- H tetrahydrofuryl- methyl 68 1 CH.sub.3 F O O H H tert-butyl H 69 1 CH.sub.3 CH.sub.3 O O H H 3- H chlorophenyl 70 1 CH.sub.3 Cl O O H H benzyl H 71 1 CH.sub.3 Cl O O H H 3- H trifluoroethyl- phenyl 72 1 CH.sub.3 Cl O O H H 3- H chlorophenyl 73 0 CH.sub.3 F O O CH.sub.3 CH.sub.3 ethyl H 74 0 CH.sub.3 F O O CH.sub.3 CH.sub.3 cyclopropyl H 75 0 CH.sub.3 F O O CH.sub.3 CH.sub.3 2,2,2- H trifluoroethyl 76 0 CH.sub.3 F O O CH.sub.3 CH.sub.3 isobutyl H 77 0 CH.sub.3 F O O CH.sub.3 CH.sub.3 benzyl H 78 0 CH.sub.3 F O O H H 2-pyridyl H 79 0 CH.sub.3 F O O CH.sub.3 H 2,2,2- H trifluoroethyl 80 0 CH.sub.3 F O O CH.sub.3 H isobutyl H 81 0 CH.sub.3 F O O CH.sub.3 H benzyl H 82 1 CH.sub.3 F O O H H 2- H methoxyethyl 83 1 CH.sub.3 F O O CH.sub.3 CH.sub.3 ethyl H 84 1 CH.sub.3 F O O CH.sub.3 CH.sub.3 cyclopropyl H 85 1 CH.sub.3 F O O CH.sub.3 CH.sub.3 2,2,2- H trifluoroethyl 86 1 CH.sub.3 F O O CH.sub.3 CH.sub.3 isobutyl H 87 1 CH.sub.3 F O O CH.sub.3 CH.sub.3 benzyl H 88 1 CH.sub.3 F O O CH.sub.3 H 2,2,2- H trifluoroethyl 89 1 CH.sub.3 F O O CH.sub.3 H isobutyl H 90 1 CH.sub.3 F O O CH.sub.3 H benzyl H 91 1 CH.sub.3 F O O H H 2- H tetrahydrofuryl- methyl 92 0 CH.sub.3 CH.sub.3 O O H H benzyl H 93 0 CH.sub.3 CH.sub.3 O O H H 4-fluorophenyl H 94 0 CH.sub.3 Cl O O H H 4-fluorophenyl H 95 0 CH.sub.3 CH.sub.3 O O H H 2-pyridyl H 96 0 CH.sub.3 Cl O O H H 2-pyridyl H 97 1 CH.sub.3 CH.sub.3 O O H H 3- H trifluoroethyl- phenyl 98 1 CH.sub.3 CH.sub.3 O O H H benzyl H 99 1 CH.sub.3 CH.sub.3 O O H H 4-fluorophenyl H 100 1 CH.sub.3 Cl O O H H 4-fluorophenyl H 101 0 CH.sub.3 F O O H H 1,1- H dimethylpropyl 102 0 CH.sub.3 F O S H H 2,2,2- H trifluoroethyl 103 0 Cl Cl O O H H ethyl H 104 0 Cl Cl O O H H cyclopropyl H 105 0 Cl Cl O O H H isobutyl H 106 0 Cl Cl O O H H 2,2,2- H trifluoroethyl 107 0 Cl Cl O O H H benzyl H 108 0 Cl Cl O O H H 4-fluorophenyl H 109 0 Cl Cl O O H H 3-chlorophenyl H 110 0 Cl Cl O O H H 3- H trifluoromethyl- phenyl 111 1 Cl Cl O O H H ethyl H 112 1 Cl Cl O O H H cyclopropyl H 113 1 Cl Cl O O H H isobutyl H 114 1 Cl Cl O O H H 2,2,2- H trifluoroethyl 115 1 Cl Cl O O H H benzyl H 116 1 Cl Cl O O H H 4-fluorophenyl H 117 1 Cl Cl O O H H 3-chlorophenyl H 118 1 CH.sub.3 CH.sub.3 O O H H 2-pyridyl H 119 1 CH.sub.3 Cl O O H H 2-pyridyl H 120 1 Cl Cl O O H H 3- H trifluoromethyl- phenyl 121 0 CH.sub.3 F O O H H cyclopropyl CH.sub.3 122 0 CH.sub.3 F O O H H 1-morpholine 123 0 CH.sub.3 F O O H H 1-(4-methylpiperazine) 124 0 CH.sub.3 F O O H H isobutyl CH.sub.3 125 1 CH.sub.3 F O O H H 1-morpholine 126 1 CH.sub.3 F O O H H isobutyl CH.sub.3 127 1 CH.sub.3 F O O H H 1-(4-methylpiperazine) 128 0 CH.sub.3 F O O H H 1-(1,1-dioxo-1,4- thiazinane) 129 0 CH.sub.3 F O O H H 1-(4,4- difluoropiperidine) 130 0 CH.sub.3 F O O H H CH.sub.3 CH.sub.3 131 1 CH.sub.3 F O O H H cyclopropyl CH.sub.3 132 1 CH.sub.3 F O O H H 1-(4,4- difluoropiperidine) 133 1 CH.sub.3 F O O H H CH.sub.3 CH.sub.3 134 1 CH.sub.3 F O O H H 1-(1,1-dioxo- 1,4-thiazinane) 135 1 CH.sub.3 F O O H H 2,2,2- H trifluoroethyl 136 1 CH.sub.3 F O O H H 2,2,2- H trifluoroethyl

NMR Peak List Method

[0494] The .sup.1H NMR data of selected examples are stated in the form of .sup.1H NMR peak lists. For each signal peak, first the δ value in ppm and then the signal intensity in round brackets are listed. The pairs of δ value-signal intensity numbers for different signal peaks are listed with separation from one another by semicolons.

[0495] The peak list for one example therefore has the form of:

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

[0496] The intensity of sharp signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the true ratios of the signal intensities. In the case of broad signals, several peaks or the middle of the signal and the relative intensity thereof may be shown in comparison to the most intense signal in the spectrum.

[0497] Calibration of the chemical shift of .sup.1H NMR spectra is accomplished using tetramethylsilane and/or the chemical shift of the solvent, particularly in the case of spectra which are measured in DMSO. Therefore, the tetramethylsilane peak may but need not occur in NMR peak lists.

[0498] The lists of the .sup.1H NMR peaks are similar to the conventional .sup.1H NMR printouts and thus usually contain all peaks listed in a conventional NMR interpretation.

[0499] In addition, like conventional .sup.1H NMR printouts, they may show solvent signals, signals of stereoisomers of the target compounds which likewise form part of the subject matter of the invention, and/or peaks of impurities.

[0500] In the reporting of compound signals within the delta range of solvents and/or water, our lists of .sup.1H NMR peaks show the standard solvent peaks, for example peaks of DMSO in D.sub.6-DMSO and the peak of water, which usually have a high intensity on average.

[0501] The peaks of stereoisomers of the target compounds and/or peaks of impurities usually have a lower intensity on average than the peaks of the target compounds (for example with a purity of >90%).

[0502] Such stereoisomers and/or impurities may be typical of the particular preparation process. Their peaks can thus help in this case to identify reproduction of our preparation process with reference to “by-product fingerprints”.

[0503] An expert calculating the peaks of the target compounds by known methods (MestreC, ACD simulation, but also with empirically evaluated expected values) can, if required, isolate the peaks of the target compounds, optionally using additional intensity filters. This isolation would be similar to the peak picking in question in conventional .sup.1H NMR interpretation.

[0504] Further details of .sup.1H NMR peak lists can be found in the Research Disclosure Database Number 564025.

TABLE-US-00002 TABLE 2 Spectroscopic data of the compounds of Table 1: Ex. No. logP[b] logP[a] .sup.1H NMR 1 2.98 3.07 (400.0 MHz, d.sub.6-DMSO): δ = 7.789(2.2); 7.781(2.3); 7.683(2.9); 7.665(3.0); 7.458(2.6); 7.431(2.6); 5.756(5.5); 4.467(0.6); 3.902(1.3); 3.876(3.9); 3.850(4.0); 3.825(1.4); 3.323(23.3); 2.700(0.6); 2.691(1.0); 2.682(1.5); 2.673(1.6); 2.664(1.3); 2.656(0.7); 2.524(0.8); 2.510(18.6); 2.506(38.1); 2.502(51.1); 2.497(38.6); 2.453(16.0); 2.328(0.3); 0.730(0.7); 0.716(2.4); 0.712(3.2); 0.699(3.0); 0.694(2.7); 0.683(1.0); 0.564(1.0); 0.553(2.9); 0.546(3.2); 0.538(2.6); 0.525(0.8); 0.008(0.6); 0.000(17.2); −0.008(0.8) 2 3.56 3.66 (400.0 MHz, d.sub.6-DMSO): δ = 9.503(2.1); 9.495(2.2); 7.659(2.8); 7.641(2.9); 7.462(2.6); 7.435(2.5); 5.756(3.9); 4.845(2.8); 4.796(4.2); 4.652(4.2); 4.603(2.7); 4.414(0.6); 3.898(1.2); 3.872(3.8); 3.846(3.9); 3.820(1.4); 3.323(57.0); 2.770(0.6); 2.761(1.0); 2.752(1.4); 2.743(1.5); 2.734(1.1); 2.726(0.7); 2.717(0.3); 2.675(0.5); 2.671(0.8); 2.666(0.6); 2.523(1.9); 2.510(41.4); 2.506(84.0); 2.502(112.6); 2.497(85.2); 2.459(16.0); 2.407(0.8); 2.333(0.5); 2.328(0.7); 2.324(0.6); 0.789(0.3); 0.770(2.9); 0.757(2.5); 0.753(2.8); 0.739(0.6); 0.597(0.4); 0.588(0.4); 0.571(2.0); 0.568(2.1); 0.559(2.2); 0.554(1.9); 0.550(2.0); 0.545(1.7); 0.525(0.4); 0.519(0.4); 0.008(1.2); 0.000(36.9); −0.008(1.9) 3 2.12 2.15 (600.1 MHz, d.sub.6-DMSO): δ = 7.993(2.6); 7.981(2.6); 7.782(2.2); 7.777(2.2); 7.562(2.2); 7.545(2.2); 4.484(0.3); 4.449(0.4); 4.331(0.8); 4.324(0.4); 4.313(1.0); 4.306(1.0); 4.294(0.4); 4.288(1.0); 4.270(0.3); 3.903(12.1); 3.870(0.5); 3.852(0.6); 3.846(0.5); 3.828(0.5); 3.321(142.8); 2.698(0.6); 2.692(1.0); 2.686(1.4); 2.681(1.4); 2.675(1.0); 2.669(0.6); 2.616(0.4); 2.613(0.6); 2.610(0.4); 2.522(1.1); 2.519(1.3); 2.516(1.5); 2.507(34.0); 2.504(71.6); 2.501(98.2); 2.498(71.7); 2.495(34.3); 2.425(16.0); 2.388(0.5); 2.385(0.6); 2.382(0.5); 0.724(0.6); 0.715(2.4); 0.713(2.9); 0.704(2.7); 0.701(2.5); 0.693(0.8); 0.556(0.9); 0.549(2.7); 0.545(2.9); 0.539(2.4); 0.531(0.7); 0.000(5.6) 4 2.65 2.64 (400.0 MHz, d.sub.6-DMSO): δ = 9.495(1.6); 9.487(1.7); 9.463(1.8); 9.455(1.9); 8.315(0.6); 7.991(2.4); 7.983(2.7); 7.973(2.5); 7.965(2.6); 7.576(3.2); 7.550(3.2); 5.755(7.9); 4.841(2.5); 4.830(2.3); 4.792(3.5); 4.782(3.3); 4.632(5.1); 4.584(3.3); 4.389(0.8); 4.379(0.5); 4.362(0.9); 4.352(1.6); 4.342(0.4); 4.335(0.4); 4.325(1.8); 4.315(1.0); 4.298(0.6); 4.288(1.0); 3.878(0.9); 3.867(0.4); 3.862(0.3); 3.851(1.1); 3.841(1.0); 3.836(1.0); 3.824(0.7); 3.814(1.0); 3.809(1.1); 3.798(0.8); 3.787(0.4); 3.782(0.4); 3.772(0.8); 3.321(105.4); 2.780(0.6); 2.771(1.3); 2.762(1.9); 2.753(2.3); 2.744(2.0); 2.735(1.4); 2.727(0.8); 2.675(1.1); 2.670(1.5); 2.666(1.1); 2.541(0.8); 2.524(3.9); 2.519(6.0); 2.510(80.6); 2.506(166.8); 2.501(222.8); 2.497(164.9); 2.492(82.4); 2.435(16.0); 2.337(0.5); 2.333(1.1); 2.328(1.5); 2.324(1.1); 0.796(0.4); 0.781(2.1); 0.778(3.2); 0.771(3.5); 0.765(3.1); 0.760(3.3); 0.757(3.1); 0.754(2.7); 0.749(1.7); 0.740(0.7); 0.594(0.4); 0.572(2.1); 0.563(4.0); 0.553(3.9); 0.528(0.4); 0.521(0.3); 0.146(1.0); 0.008(8.0); 0.000(238.8); −0.009(10.0); −0.150(1.0) 5 3.87 3.98 (600.1 MHz, d.sub.6-DMSO): δ = 9.419(1.8); 9.407(1.9); 7.671(2.5); 7.659(2.5); 7.461(2.3); 7.444(2.2); 4.832(3.2); 4.800(4.0); 4.638(4.2); 4.605(3.1); 3.937(0.9); 3.926(1.4); 3.914(1.5); 3.903(3.1); 3.891(1.2); 3.873(3.2); 3.856(3.3); 3.839(1.2); 3.318(38.7); 2.616(0.4); 2.613(0.5); 2.610(0.4); 2.522(1.0); 2.519(1.2); 2.516(1.3); 2.507(30.2); 2.504(62.2); 2.501(84.2); 2.498(61.2); 2.495(29.4); 2.461(16.0); 2.388(0.4); 2.385(0.5); 2.382(0.4); 1.908(0.4); 1.238(0.7); 1.227(0.7); 1.212(9.9); 1.206(10.4); 1.201(10.5); 1.195(9.9); 0.000(5.7) 6 2.93 2.98 (400.0 MHz, d.sub.6-DMSO): δ = 7.874(0.9); 7.860(1.9); 7.846(1.0); 7.701(2.9); 7.683(2.9); 7.462(2.6); 7.435(2.5); 4.466(0.6); 4.418(0.7); 3.908(1.2); 3.882(3.7); 3.856(3.9); 3.831(1.3); 3.324(26.4); 3.283(0.7); 3.265(2.2); 3.248(2.9); 3.232(2.3); 3.215(0.7); 2.671(0.4); 2.506(45.6); 2.502(60.0); 2.498(45.4); 2.457(16.0); 2.375(0.8); 2.329(0.4); 1.113(5.1); 1.095(10.7); 1.077(4.9); 1.066(0.7); 0.008(1.3); 0.000(35.5) 7 3.29 3.34 (400.0 MHz, d.sub.6-DMSO): δ = 7.700(1.9); 7.682(1.9); 7.616(1.2); 7.597(1.2); 7.460(1.6); 7.433(1.6); 5.488(0.7); 5.469(0.7); 4.466(0.3); 3.925(0.6); 3.907(1.5); 3.890(1.0); 3.880(2.6); 3.855(2.7); 3.829(0.9); 3.659(0.6); 3.643(0.9); 3.624(0.9); 3.608(0.6); 3.324(7.9); 2.525(0.3); 2.511(8.7); 2.507(17.7); 2.502(23.4); 2.498(17.1); 2.493(8.4); 2.458(10.3); 2.437(0.6); 2.086(0.6); 1.176(12.8); 1.160(12.7); 1.010(16.0); 0.993(15.7); 0.008(0.5); 0.000(15.5); −0.008(0.6) 8 3.86 3.91 (400.0 MHz, d.sub.6-DMSO): δ = 11.476(2.2); 8.315(0.9); 7.975(2.7); 7.956(2.7); 7.332(2.5); 7.303(2.5); 4.524(12.8); 3.905(1.3); 3.879(4.1); 3.853(4.2); 3.827(1.5); 3.523(1.2); 3.505(4.1); 3.487(4.1); 3.469(1.3); 3.323(71.4); 2.675(0.9); 2.671(1.3); 2.666(0.9); 2.524(2.8); 2.511(70.8); 2.506(145.7); 2.502(193.9); 2.497(140.0); 2.493(67.1); 2.408(16.0); 2.338(0.4); 2.333(0.9); 2.329(1.3); 2.324(0.9); 2.086(0.8); 1.181(4.6); 1.163(10.5); 1.145(4.5); 0.146(0.6); 0.008(4.5); 0.000(146.5); −0.008(4.9); −0.150(0.7) 9 2.05 2.05 (400.0 MHz, d.sub.6-DMSO): δ = 8.317(0.5); 8.016(3.0); 7.998(3.0); 7.867(1.1); 7.854(2.1); 7.839(1.0); 7.574(2.5); 7.547(2.6); 4.450(0.9); 4.379(0.4); 4.352(1.0); 4.341(0.5); 4.325(1.1); 4.315(1.1); 4.297(0.5); 4.287(1.1); 4.260(0.4); 3.884(0.8); 3.857(0.9); 3.847(0.8); 3.831(0.4); 3.820(0.7); 3.326(158.4); 3.324(144.6); 3.284(0.8); 3.267(2.5); 3.249(3.1); 3.234(2.5); 3.216(0.7); 2.719(0.8); 2.675(1.5); 2.671(2.0); 2.666(1.5); 2.506(247.6); 2.502(316.7); 2.498(233.6); 2.431(16.0); 2.333(1.5); 2.329(2.0); 2.324(1.5); 2.086(3.9); 1.115(5.3); 1.097(11.3); 1.079(5.2); 0.008(1.5); 0.000(32.5); −0.007(1.4) 10 2.38 2.40 (400.0 MHz, d.sub.6-DMSO): δ = 8.317(0.5); 8.012(2.4); 7.994(2.4); 7.614(1.6); 7.596(1.7); 7.572(2.1); 7.546(2.0); 5.487(0.3); 5.469(0.3); 4.445(0.7); 4.372(0.4); 4.345(0.8); 4.335(0.4); 4.318(0.9); 4.308(1.0); 4.290(0.4); 4.281(1.0); 3.923(0.8); 3.907(1.2); 3.891(1.5); 3.872(0.9); 3.867(1.0); 3.856(1.0); 3.840(0.4); 3.830(0.7); 3.640(0.4); 3.622(0.3); 3.325(183.3); 2.719(0.7); 2.675(1.2); 2.671(1.7); 2.666(1.3); 2.524(4.0); 2.506(206.5); 2.502(274.3); 2.497(205.2); 2.430(13.0); 2.333(1.3); 2.328(1.8); 2.324(1.3); 2.086(1.8); 1.237(0.3); 1.176(16.0); 1.160(15.9); 1.140(0.4); 1.008(6.4); 0.992(6.4); 0.008(0.9); 0.000(26.0); −0.008(1.2) 11 4.18 4.27 (400.0 MHz, d.sub.6-DMSO): δ = 9.451(0.7); 9.437(1.4); 9.422(0.7); 7.685(2.1); 7.667(2.1); 7.470(1.9); 7.443(1.8); 4.853(2.2); 4.804(3.2); 4.654(3.3); 4.606(2.1); 3.906(0.9); 3.881(2.7); 3.855(2.8); 3.829(1.0); 3.324(27.8); 3.198(0.4); 3.181(1.1); 3.165(1.6); 3.160(1.2); 3.149(1.3); 3.146(1.6); 3.129(1.1); 3.111(0.4); 2.675(0.3); 2.671(0.5); 2.666(0.3); 2.524(1.1); 2.511(25.5); 2.506(52.7); 2.502(70.3); 2.497(51.3); 2.493(25.1); 2.464(11.8); 2.442(0.4); 2.333(0.3); 2.328(0.4); 2.324(0.3); 1.844(0.4); 1.827(0.9); 1.811(1.1); 1.794(0.9); 1.778(0.5); 0.935(0.5); 0.923(16.0); 0.906(15.5); 0.000(4.7) 12 3.58 3.67 (400.0 MHz, d.sub.6-DMSO): δ = 7.868(0.4); 7.853(0.8); 7.838(0.4); 7.707(1.2); 7.688(1.2); 7.466(1.1); 7.439(1.1); 5.757(16.0); 3.911(0.5); 3.885(1.6); 3.860(1.7); 3.834(0.6); 3.086(0.8); 3.070(1.5); 3.055(0.9); 2.809(0.6); 2.792(0.6); 2.511(5.1); 2.506(10.7); 2.502(14.3); 2.497(10.5); 2.493(5.2); 2.459(6.5); 2.086(5.0); 1.802(0.5); 1.786(0.6); 1.769(0.5); 1.590(0.3); 1.398(0.8); 1.352(0.5); 1.229(0.5); 0.883(8.9); 0.866(8.7); 0.824(4.8); 0.807(4.6); 0.000(1.8) 13 3.24 3.33 (400.0 MHz, d.sub.6-DMSO): δ = 9.446(0.6); 9.432(1.2); 9.417(1.2); 9.403(1.3); 9.388(0.6); 8.316(0.8); 8.011(3.4); 7.993(3.4); 7.585(2.6); 7.559(2.6); 5.757(0.6); 4.848(1.9); 4.837(1.8); 4.800(2.6); 4.789(2.5); 4.633(5.1); 4.584(3.3); 4.392(0.6); 4.365(0.7); 4.356(0.9); 4.332(0.9); 4.328(0.9); 4.322(0.8); 4.301(0.4); 4.295(0.8); 3.884(0.8); 3.858(1.1); 3.847(0.8); 3.833(0.9); 3.821(1.0); 3.807(0.3); 3.796(0.7); 3.328(347.3); 3.326(339.5); 3.208(0.6); 3.192(1.0); 3.181(1.2); 3.176(1.4); 3.163(2.4); 3.148(2.6); 3.132(1.5); 3.115(0.6); 3.100(0.4); 2.675(2.4); 2.671(3.3); 2.666(2.4); 2.662(1.2); 2.524(8.5); 2.519(12.7); 2.511(186.9); 2.506(383.3); 2.502(508.7); 2.497(370.2); 2.493(180.3); 2.442(16.0); 2.378(0.5); 2.337(1.1); 2.333(2.4); 2.329(3.3); 2.324(2.4); 1.850(0.4); 1.844(0.4); 1.833(0.8); 1.827(0.9); 1.817(1.0); 1.811(1.1); 1.801(0.9); 1.794(0.9); 1.784(0.5); 1.777(0.5); 1.148(0.4); 0.930(13.3); 0.922(14.1); 0.913(13.4); 0.905(13.3); 0.893(0.6); 0.886(0.5); 0.866(0.6); 0.849(0.5); 0.146(2.4); 0.008(16.6); 0.000(509.8); −0.009(17.5); −0.150(2.4) 14 2.93 3.01 (400.0 MHz, d.sub.6-DMSO): δ = 9.420(1.4); 9.402(1.5); 9.383(1.5); 9.365(1.6); 8.316(0.7); 8.004(2.4); 7.996(2.6); 7.986(2.5); 7.978(2.6); 7.581(2.8); 7.555(2.8); 5.757(2.1); 4.838(2.4); 4.828(2.3); 4.790(3.4); 4.779(3.2); 4.623(6.5); 4.574(4.4); 4.397(0.7); 4.386(0.4); 4.370(0.8); 4.360(1.0); 4.356(0.9); 4.343(0.5); 4.333(1.0); 4.329(1.0); 4.319(0.9); 4.305(0.4); 4.301(0.4); 4.291(0.9); 3.945(0.9); 3.929(1.5); 3.912(1.5); 3.898(1.0); 3.895(0.9); 3.881(1.2); 3.870(0.4); 3.854(1.0); 3.841(1.1); 3.828(0.6); 3.817(1.1); 3.814(1.2); 3.803(0.8); 3.788(0.5); 3.777(0.8); 3.336(208.6); 3.335(210.7); 3.327(183.7); 2.680(0.9); 2.675(2.0); 2.671(2.7); 2.666(2.0); 2.662(1.0); 2.524(6.7); 2.519(10.4); 2.511(154.0); 2.506(315.8); 2.502(418.7); 2.497(305.0); 2.493(148.5); 2.439(15.6); 2.378(0.6); 2.333(2.0); 2.329(2.7); 2.324(2.0); 2.320(0.9); 1.215(15.8); 1.207(10.0); 1.198(16.0); 1.191(8.9); 1.175(0.5); 1.147(0.4); 1.140(0.5); 1.119(0.4); 0.146(2.2); 0.008(16.6); 0.000(503.2); −0.009(17.8); −0.150(2.2) 15 2.66 2.72 (400.0 MHz, d.sub.6-DMSO): □ δ = 8.021(2.3); 8.003(2.3); 7.861(0.7); 7.847(1.5); 7.832(0.8); 7.575(1.9); 7.548(1.9); 5.757(0.9); 4.455(0.5); 4.348(0.8); 4.338(0.4); 4.320(0.9); 4.311(0.9); 4.293(0.4); 4.283(0.9); 3.897(0.7); 3.870(0.8); 3.860(0.7); 3.833(0.7); 3.328(42.9); 3.325(42.8); 3.089(1.5); 3.073(2.7); 3.057(1.6); 2.675(0.5); 2.671(0.6); 2.666(0.5); 2.524(1.8); 2.510(37.6); 2.506(76.1); 2.502(100.7); 2.497(75.4); 2.493(38.4); 2.431(11.9); 2.333(0.5); 2.328(0.6); 2.324(0.5); 1.820(0.4); 1.803(0.9); 1.786(1.1); 1.770(0.9); 1.753(0.5); 0.885(16.0); 0.868(15.5); 0.146(0.4); 0.008(3.1); 0.000(92.2); −0.008(3.9); −0.150(0.4) 16 3.71 3.82 (400.0 MHz, d.sub.6-DMSO): δ = 9.824(4.1); 7.739(3.1); 7.721(3.1); 7.556(3.9); 7.537(4.6); 7.499(2.6); 7.472(2.6); 7.457(0.4); 7.438(0.4); 7.385(3.0); 7.380(1.1); 7.366(4.4); 7.345(2.9); 7.276(0.3); 7.149(1.5); 7.130(2.6); 7.112(1.1); 5.757(6.0); 4.587(0.6); 3.921(1.2); 3.896(3.9); 3.870(4.0); 3.844(1.4); 3.327(20.3); 2.524(0.7); 2.511(14.1); 2.506(28.8); 2.502(38.4); 2.497(28.3); 2.493(14.0); 2.477(16.0); 2.086(1.8); 1.398(1.1); 0.000(0.7) 17 2.75 2.37 (400.0 MHz, d.sub.6-DMSO): δ = 9.901(4.1); 8.747(3.1); 8.741(3.1); 8.345(2.1); 8.342(2.3); 8.334(2.3); 8.330(2.4); 8.027(1.2); 8.023(1.4); 8.021(1.4); 8.017(1.3); 8.006(1.3); 8.002(1.5); 8.000(1.5); 7.996(1.3); 7.743(2.9); 7.725(2.9); 7.504(2.5); 7.477(2.5); 7.421(1.7); 7.409(1.7); 7.400(1.7); 7.388(1.6); 4.591(0.7); 3.921(1.2); 3.895(3.7); 3.870(3.9); 3.844(1.3); 3.326(24.0); 2.671(0.4); 2.666(0.3); 2.524(0.9); 2.519(1.5); 2.511(24.9); 2.506(51.5); 2.502(68.7); 2.497(50.6); 2.493(25.2); 2.479(16.0); 2.389(0.4); 2.333(0.3); 2.328(0.5); 2.324(0.4); 2.086(4.9); 0.008(1.5); 0.000(47.9); −0.009(1.8) 18 3.53 3.64 (600.1 MHz, d.sub.6-DMSO): δ = 8.346(1.0); 8.336(2.1); 8.326(1.0); 7.701(2.6); 7.689(2.6); 7.460(2.3); 7.442(2.3); 7.336(14.4); 7.329(11.6); 7.319(0.4); 7.316(0.4); 7.314(0.5); 7.267(0.8); 7.260(1.4); 7.253(1.6); 7.246(1.0); 7.239(0.4); 4.435(3.3); 4.425(3.3); 3.891(1.0); 3.874(3.2); 3.857(3.4); 3.840(1.2); 3.319(13.8); 2.522(0.4); 2.519(0.5); 2.515(0.6); 2.504(25.5); 2.501(34.5); 2.498(25.1); 2.456(16.0); 0.000(2.5) 19 2.83 2.89 (400.0 MHz, d.sub.6-DMSO): δ = 9.825(4.2); 8.057(3.0); 8.039(3.0); 7.607(2.5); 7.580(2.5); 7.557(4.1); 7.537(4.9); 7.386(2.8); 7.367(4.5); 7.347(2.7); 7.149(1.5); 7.131(2.6); 7.112(1.1); 5.756(1.7); 4.569(0.8); 4.366(0.9); 4.356(0.4); 4.339(1.0); 4.329(1.1); 4.312(0.5); 4.302(1.1); 4.275(0.4); 4.163(0.3); 3.913(0.8); 3.902(0.4); 3.886(0.9); 3.875(0.8); 3.859(0.4); 3.849(0.7); 3.327(129.4); 2.675(0.8); 2.671(1.0); 2.666(0.8); 2.524(2.5); 2.506(126.0); 2.502(163.2); 2.497(122.9); 2.445(16.0); 2.424(1.5); 2.333(0.9); 2.328(1.1); 2.324(0.9); 2.086(5.5); 0.146(0.5); 0.008(4.9); 0.000(112.1); −0.008(5.6); −0.149(0.5) 20 1.98 1.51 (400.0 MHz, d.sub.6-DMSO): δ = 9.904(4.2); 8.746(3.1); 8.740(3.1); 8.343(2.4); 8.331(2.4); 8.060(2.9); 8.042(3.1); 8.029(1.6); 8.007(1.7); 7.611(2.6); 7.584(2.6); 7.423(1.6); 7.411(1.6); 7.402(1.6); 7.391(1.5); 4.589(0.9); 4.371(0.9); 4.362(0.4); 4.343(1.0); 4.334(1.1); 4.316(0.5); 4.306(1.1); 4.279(0.4); 3.902(0.6); 3.876(0.7); 3.868(0.7); 3.840(0.5); 3.326(35.7); 2.671(0.8); 2.506(103.9); 2.502(133.3); 2.447(16.0); 2.423(1.1); 2.328(0.9); 2.086(11.0); 1.140(0.6); 0.146(0.4); 0.000(82.7); −0.149(0.4) 21 2.71 2.77 (400.0 MHz, d.sub.6-DMSO): δ = 8.347(1.2); 8.333(2.2); 8.317(1.3); 8.021(2.8); 8.003(2.6); 7.575(2.5); 7.548(2.4); 7.338(12.4); 7.328(13.5); 7.273(1.3); 7.263(1.9); 7.252(1.8); 7.242(1.0); 7.230(0.4); 5.757(1.7); 4.442(5.1); 4.427(4.5); 4.375(0.5); 4.348(1.1); 4.339(0.6); 4.320(1.2); 4.311(1.2); 4.284(1.1); 4.256(0.4); 3.884(0.8); 3.857(1.0); 3.847(0.8); 3.821(0.7); 3.330(199.9); 2.717(0.3); 2.675(1.9); 2.671(2.0); 2.506(272.3); 2.502(287.5); 2.429(16.0); 2.333(2.1); 2.328(2.2); 2.267(0.3); 1.234(0.4); 0.146(0.7); 0.000(138.7); −0.008(7.4); −0.150(0.8) 22 3.38 3.48 (400.0 MHz, d.sub.6-DMSO): δ = 8.317(0.7); 8.076(1.3); 7.657(1.8); 7.638(1.9); 7.500(5.9); 7.289(4.5); 7.021(1.1); 6.441(0.4); 6.423(0.4); 4.505(2.7); 4.461(4.3); 4.351(4.4); 4.307(2.6); 3.924(0.8); 3.907(1.3); 3.889(1.5); 3.885(1.4); 3.873(1.0); 3.858(3.6); 3.833(3.6); 3.807(1.3); 3.748(0.4); 3.728(1.1); 3.702(1.1); 3.676(0.4); 3.326(209.4); 2.675(1.5); 2.671(2.1); 2.666(1.6); 2.524(5.6); 2.519(8.7); 2.511(114.0); 2.506(231.6); 2.502(307.3); 2.497(229.0); 2.493(115.7); 2.450(0.5); 2.389(15.1); 2.345(0.3); 2.333(1.7); 2.329(2.3); 2.324(1.8); 2.288(3.8); 2.169(0.4); 2.118(4.5); 2.110(16.0); 2.075(0.8); 1.175(14.5); 1.159(14.5); 1.123(0.5); 1.104(5.5); 1.088(5.2); 1.074(0.3); 0.146(1.7); 0.008(13.4); 0.000(380.9); −0.009(15.4); −0.150(1.8) 23 2.45 2.52 (400.0 MHz, d.sub.6-DMSO): δ = 8.438(0.3); 8.317(0.5); 7.835(3.2); 7.827(3.3); 7.676(0.3); 7.651(2.2); 7.632(2.3); 7.392(5.0); 5.757(0.6); 4.499(1.4); 4.493(1.4); 4.455(2.3); 4.450(2.5); 4.355(2.1); 4.344(2.2); 4.312(1.3); 4.301(1.5); 4.275(1.0); 4.248(1.1); 4.238(1.2); 4.211(1.1); 4.185(0.4); 3.921(0.7); 3.904(1.1); 3.892(1.1); 3.875(0.8); 3.842(0.3); 3.832(0.3); 3.816(0.7); 3.805(0.9); 3.789(0.8); 3.778(1.3); 3.769(0.8); 3.752(0.8); 3.742(0.7); 3.328(256.1); 2.671(2.1); 2.502(313.7); 2.379(16.0); 2.329(2.3); 2.281(0.4); 2.252(1.4); 2.209(16.0); 1.334(0.4); 1.318(0.3); 1.235(0.6); 1.173(13.2); 1.160(12.5); 1.156(12.9); 1.120(1.6); 1.104(1.6); 1.082(0.4); 0.146(1.8); 0.000(342.6); −0.150(1.9) 24 3.30 3.38 (400.0 MHz, d.sub.6-DMSO): δ = 7.905(1.0); 7.891(1.9); 7.877(1.0); 7.739(0.6); 7.464(2.2); 7.437(2.2); 4.731(0.4); 4.722(0.4); 3.923(0.7); 3.898(1.9); 3.872(1.9); 3.846(0.7); 3.325(25.0); 3.283(0.5); 3.265(1.8); 3.247(2.6); 3.230(1.9); 3.214(0.6); 2.506(32.8); 2.502(42.1); 2.497(31.5); 2.456(16.0); 1.572(3.8); 1.555(3.8); 1.114(5.4); 1.096(11.3); 1.078(5.2); 0.007(1.4); 0.000(28.0); −0.008(1.3) 25 3.35 3.43 (400.0 MHz, d.sub.6-DMSO): □ 7.831(2.3); 7.824(2.3); 7.720(0.6); 7.459(2.2); 7.432(2.2); 5.757(0.8); 4.732(0.4); 3.915(0.7); 3.890(2.0); 3.864(2.0); 3.839(0.7); 3.326(26.0); 2.709(0.7); 2.701(1.1); 2.692(1.6); 2.683(1.6); 2.674(1.3); 2.666(0.9); 2.506(30.7); 2.502(40.0); 2.498(30.5); 2.452(16.0); 1.572(3.7); 1.555(3.7); 0.726(0.7); 0.710(3.2); 0.699(2.7); 0.693(2.8); 0.682(1.1); 0.563(1.0); 0.552(3.0); 0.547(3.2); 0.527(0.8); 0.000(26.8); −0.008(1.4) 26 3.68 3.78 (400.0 MHz, d.sub.6-DMSO): δ = 7.740(0.6); 7.664(1.6); 7.645(1.7); 7.463(2.1); 7.436(2.1); 4.739(0.3); 4.730(0.3); 3.944(0.4); 3.927(1.3); 3.911(1.8); 3.895(2.9); 3.876(2.1); 3.872(2.1); 3.846(0.7); 3.325(46.1); 2.671(0.4); 2.524(1.0); 2.511(24.1); 2.506(47.7); 2.502(62.6); 2.497(46.3); 2.493(23.1); 2.456(16.0); 2.328(0.4); 1.575(3.5); 1.558(3.5); 1.178(10.3); 1.167(11.9); 1.162(11.6); 1.150(10.6); 1.009(0.7); 0.992(0.7); 0.008(2.0); 0.000(48.8); −0.009(1.9) 27 2.39 2.42 (400.0 MHz, d.sub.6-DMSO): δ = 8.318(0.3); 8.066(0.8); 8.051(0.8); 7.896(1.0); 7.882(1.9); 7.868(1.0); 7.575(2.5); 7.548(2.5); 4.725(0.4); 4.711(0.4); 4.353(0.6); 4.343(0.5); 4.325(0.8); 4.316(1.0); 4.298(0.4); 4.288(0.9); 4.281(0.4); 3.887(0.6); 3.877(0.4); 3.861(0.7); 3.851(0.6); 3.834(0.4); 3.824(0.5); 3.327(104.9); 3.287(0.6); 3.279(0.6); 3.269(1.6); 3.262(1.6); 3.249(2.2); 3.237(1.6); 3.230(1.7); 3.218(0.6); 3.212(0.6); 2.719(0.9); 2.675(0.9); 2.671(1.2); 2.666(0.9); 2.524(3.4); 2.511(68.9); 2.506(140.0); 2.502(185.5); 2.497(136.9); 2.493(68.9); 2.433(16.0); 2.337(0.4); 2.333(0.9); 2.328(1.2); 2.324(0.9); 1.581(4.1); 1.565(4.2); 1.116(6.5); 1.099(14.1); 1.081(6.4); 0.146(0.9); 0.008(7.5); 0.000(203.6); −0.009(9.2); −0.150(0.9) 28 2.42 2.46 (400.0 MHz, d.sub.6-DMSO): δ = 8.046(0.8); 7.831(1.5); 7.824(2.3); 7.569(2.4); 7.543(2.4); 5.758(3.8); 4.727(0.4); 4.718(0.4); 4.346(0.6); 4.336(0.5); 4.319(0.7); 4.309(1.0); 4.299(0.5); 4.292(0.4); 4.282(0.8); 4.272(0.4); 3.885(0.5); 3.876(0.4); 3.859(0.6); 3.848(0.5); 3.833(0.4); 3.821(0.4); 3.335(44.8); 3.330(105.2); 2.714(1.1); 2.705(1.0); 2.697(1.4); 2.688(1.4); 2.679(1.3); 2.671(1.4); 2.662(0.5); 2.524(1.8); 2.510(42.6); 2.506(86.4); 2.502(114.5); 2.497(84.0); 2.493(41.5); 2.428(16.0); 2.333(0.6); 2.329(0.8); 2.324(0.5); 1.582(3.9); 1.566(3.9); 0.730(0.7); 0.714(3.1); 0.697(2.8); 0.686(1.0); 0.560(0.9); 0.543(3.4); 0.524(0.8); 0.146(0.5); 0.008(3.1); 0.000(104.8); −0.008(4.0); −0.150(0.5) 29 2.73 2.77 (400.0 MHz, d.sub.6-DMSO): δ = 8.064(0.8); 8.049(0.8); 7.664(1.4); 7.645(1.5); 7.574(2.6); 7.547(2.6); 5.758(1.8); 4.714(0.4); 4.349(0.6); 4.336(0.5); 4.322(0.8); 4.311(0.9); 4.298(0.6); 4.284(0.8); 4.271(0.5); 3.943(0.4); 3.926(1.0); 3.910(1.6); 3.894(2.1); 3.877(1.2); 3.867(0.8); 3.858(0.9); 3.842(0.4); 3.831(0.5); 3.335(97.8); 3.333(109.6); 3.329(141.7); 2.680(0.4); 2.675(0.9); 2.671(1.2); 2.666(0.9); 2.524(3.0); 2.519(4.7); 2.511(68.5); 2.506(140.3); 2.502(186.0); 2.497(136.0); 2.493(67.3); 2.433(16.0); 2.333(0.9); 2.329(1.3); 2.324(0.9); 1.585(4.2); 1.568(4.2); 1.179(11.3); 1.168(13.4); 1.163(12.9); 1.152(12.0); 1.008(0.8); 0.992(0.8); 0.146(0.8); 0.008(5.8); 0.000(179.7); −0.009(6.9); −0.150(0.8) 30 3.21 3.28 (400.0 MHz, d.sub.6-DMSO): δ = 8.336(1.1); 8.320(2.2); 8.304(1.1); 7.714(2.8); 7.696(2.9); 7.478(2.6); 7.451(2.6); 5.757(3.8); 4.505(0.6); 4.491(0.6); 4.100(1.2); 4.079(1.5); 4.061(1.2); 3.909(1.2); 3.883(3.8); 3.857(4.0); 3.842(0.6); 3.832(1.4); 3.330(65.9); 2.671(0.5); 2.506(56.6); 2.502(76.4); 2.498(63.3); 2.463(16.0); 2.329(0.5); 2.086(4.9); 2.075(0.6); 0.000(4.4) 31 3.04 3.14 (400.0 MHz, d.sub.6-DMSO): δ = 7.894(0.9); 7.880(1.8); 7.866(1.0); 7.500(5.7); 7.291(4.6); 4.507(2.7); 4.463(4.2); 4.351(4.4); 4.307(2.6); 4.190(0.9); 3.885(1.2); 3.860(3.6); 3.834(3.8); 3.808(1.3); 3.434(0.4); 3.416(0.4); 3.328(123.2); 3.288(0.6); 3.282(0.5); 3.269(1.7); 3.264(1.4); 3.251(2.3); 3.237(1.6); 3.232(1.8); 3.220(0.7); 3.214(0.6); 2.676(0.8); 2.671(1.1); 2.667(0.9); 2.524(2.8); 2.510(65.2); 2.506(130.5); 2.502(171.3); 2.497(126.9); 2.389(15.3); 2.338(0.5); 2.333(0.9); 2.329(1.2); 2.324(0.9); 2.111(16.0); 1.398(7.6); 1.236(0.3); 1.125(0.5); 1.115(5.3); 1.108(1.3); 1.097(11.3); 1.079(5.2); 1.065(0.5); 0.146(0.9); 0.008(6.9); 0.000(185.7); −0.008(8.4); −0.150(0.9) 32 2.12 2.14 (400.0 MHz, d.sub.6-DMSO): δ = 7.881(1.0); 7.867(2.0); 7.853(1.1); 7.833(4.6); 7.394(5.0); 5.757(1.8); 4.501(1.5); 4.495(1.5); 4.457(2.4); 4.451(2.5); 4.359(2.3); 4.346(2.4); 4.315(1.4); 4.303(1.5); 4.289(0.5); 4.279(0.7); 4.262(0.6); 4.252(1.1); 4.242(0.7); 4.235(0.3); 4.225(0.8); 4.215(0.6); 4.190(1.3); 3.814(0.7); 3.787(1.2); 3.778(0.7); 3.760(0.9); 3.750(1.0); 3.723(0.7); 3.434(0.4); 3.416(0.5); 3.329(89.8); 3.292(0.4); 3.274(1.1); 3.265(1.5); 3.262(1.5); 3.256(1.9); 3.251(1.8); 3.248(2.0); 3.238(1.6); 3.231(1.4); 3.224(0.8); 3.206(0.3); 2.675(0.5); 2.671(0.7); 2.666(0.5); 2.524(1.6); 2.506(78.4); 2.502(103.4); 2.498(78.6); 2.381(14.6); 2.333(0.5); 2.329(0.7); 2.324(0.6); 2.211(16.0); 1.183(0.4); 1.119(3.1); 1.114(3.3); 1.107(1.8); 1.102(6.9); 1.096(6.9); 1.084(4.0); 1.078(3.3); 1.065(0.6); 0.000(7.1) 33 3.89 3.86 (400.0 MHz, d.sub.6-DMSO): δ = 7.754(1.3); 7.500(1.9); 7.285(1.5); 4.493(0.9); 4.449(1.4); 4.337(1.4); 4.293(0.9); 3.887(0.4); 3.861(1.1); 3.835(1.2); 3.809(0.4); 3.331(14.8); 2.511(4.9); 2.506(9.9); 2.502(13.1); 2.497(9.6); 2.493(4.8); 2.386(4.9); 2.107(5.2); 2.074(0.6); 1.340(16.0); 0.000(0.5) 34 3.69 3.80 (400.0 MHz, d.sub.6-DMSO): □ 7.902(0.8); 7.887(1.6); 7.873(0.8); 7.507(4.4); 7.293(3.6); 4.515(2.0); 4.471(3.1); 4.358(3.2); 4.314(1.9); 4.239(0.6); 3.887(0.9); 3.861(2.8); 3.835(2.9); 3.810(1.0); 3.334(230.1); 3.114(0.4); 3.097(1.2); 3.080(2.0); 3.064(2.2); 3.046(1.4); 3.029(0.5); 2.936(0.3); 2.676(0.6); 2.671(0.8); 2.667(0.6); 2.507(93.3); 2.502(119.7); 2.498(89.3); 2.451(0.4); 2.390(11.7); 2.333(0.7); 2.329(0.9); 2.325(0.7); 2.289(0.5); 2.131(0.5); 2.115(12.3); 1.989(0.4); 1.816(0.4); 1.799(0.9); 1.782(1.2); 1.766(1.0); 1.749(0.6); 1.398(2.0); 0.885(15.6); 0.869(16.0); 0.852(1.5); 0.846(2.0); 0.829(1.6); 0.818(0.8); 0.802(0.7); 0.008(0.8); 0.000(19.0); −0.008(0.9) 35 2.76 2.77 (400.0 MHz, d.sub.6-DMSO): δ = 7.878(1.3); 7.847(2.0); 7.836(1.7); 7.821(0.5); 7.806(0.5); 7.397(2.2); 7.376(0.3); 7.364(0.3); 4.508(0.8); 4.464(1.5); 4.434(0.4); 4.363(1.2); 4.351(1.1); 4.319(0.9); 4.308(0.9); 4.282(0.8); 4.254(0.9); 4.245(0.8); 4.220(0.7); 4.192(0.4); 3.819(0.6); 3.813(0.5); 3.792(0.7); 3.757(0.6); 3.730(0.4); 3.388(0.5); 3.328(19.8); 3.305(2.7); 3.286(3.0); 3.258(2.2); 3.086(1.4); 3.070(1.5); 3.060(1.2); 3.043(1.0); 2.674(1.0); 2.652(0.7); 2.506(89.1); 2.502(88.1); 2.468(16.0); 2.382(8.4); 2.335(1.8); 2.314(1.1); 2.216(7.0); 2.180(1.0); 2.144(0.7); 1.800(0.7); 1.787(0.8); 1.784(0.8); 1.768(0.8); 1.753(0.5); 0.891(7.1); 0.884(7.0); 0.874(7.0); 0.867(5.8); 0.000(1.8) 36 2.41 2.46 (400.0 MHz, d.sub.6-DMSO): δ = 8.333(1.0); 8.317(2.5); 8.300(1.1); 8.037(3.1); 8.019(3.1); 7.586(2.6); 7.559(2.5); 4.481(0.7); 4.388(0.4); 4.361(1.0); 4.351(0.5); 4.333(1.1); 4.323(1.1); 4.306(0.5); 4.296(1.1); 4.269(0.4); 4.127(0.4); 4.105(1.3); 4.083(1.5); 4.066(1.3); 4.041(0.5); 3.884(0.8); 3.875(0.3); 3.858(0.9); 3.847(0.8); 3.831(0.4); 3.821(0.7); 3.331(105.1); 2.675(0.4); 2.671(0.6); 2.667(0.4); 2.524(1.4); 2.511(32.5); 2.506(65.6); 2.502(86.5); 2.497(64.0); 2.493(32.3); 2.434(16.0); 2.333(0.4); 2.329(0.6); 2.324(0.5); 2.075(3.5); 0.000(6.8) 37 4.24 4.32 (400.0 MHz, d.sub.6-DMSO): δ = 10.047(3.7); 8.240(0.3); 8.061(2.8); 7.877(0.4); 7.818(2.0); 7.797(1.8); 7.763(0.4); 7.742(2.4); 7.724(2.2); 7.618(1.0); 7.598(2.0); 7.578(1.1); 7.505(2.1); 7.492(2.2); 7.477(2.9); 7.351(0.3); 4.598(0.8); 4.502(1.4); 3.919(0.9); 3.894(2.8); 3.868(2.9); 3.854(0.8); 3.843(1.1); 3.828(0.6); 3.332(99.3); 2.671(0.7); 2.502(101.7); 2.479(16.0); 2.434(0.5); 2.391(2.0); 2.329(0.7); 2.075(1.7); 0.000(10.9) 38 3.33 3.46 (400.0 MHz, d.sub.6-DMSO): δ = 8.346(1.0); 8.330(2.2); 8.313(1.0); 7.521(6.0); 7.301(4.7); 4.551(3.0); 4.508(4.5); 4.391(4.6); 4.348(2.9); 4.141(0.4); 4.119(1.0); 4.100(1.3); 4.096(1.2); 4.083(1.1); 4.078(1.3); 4.059(1.0); 4.036(0.4); 3.881(1.2); 3.856(3.9); 3.830(4.0); 3.804(1.4); 3.329(29.2); 2.524(0.5); 2.519(0.7); 2.511(9.5); 2.506(19.8); 2.502(26.4); 2.497(19.6); 2.493(9.7); 2.395(15.1); 2.127(16.0); 2.073(3.5); 0.008(0.6); 0.000(19.0); −0.009(0.7) 39 3.75 3.85 (400.0 MHz, d.sub.6-DMSO): δ = 9.811(4.2); 7.736(2.9); 7.718(2.9); 7.594(2.8); 7.589(1.1); 7.582(3.0); 7.577(1.8); 7.572(3.2); 7.565(1.2); 7.559(3.0); 7.498(2.5); 7.471(2.6); 7.227(3.1); 7.221(1.0); 7.205(5.3); 7.188(0.9); 7.183(2.8); 4.570(0.6); 4.566(0.6); 3.920(1.1); 3.894(3.7); 3.868(3.8); 3.842(1.3); 3.329(39.5); 2.676(0.4); 2.671(0.6); 2.667(0.4); 2.524(1.3); 2.511(33.5); 2.507(67.5); 2.502(88.0); 2.498(63.4); 2.493(30.7); 2.475(16.0); 2.333(0.4); 2.329(0.6); 2.324(0.5); 2.075(1.9); 0.008(0.9); 0.000(29.4); −0.009(1.1) 40 2.83 2.90 (400.0 MHz, d.sub.6-DMSO): δ = 7.835(1.8); 7.823(1.7); 7.754(1.4); 7.749(1.4); 7.389(2.5); 4.485(0.7); 4.479(0.7); 4.441(1.2); 4.435(1.2); 4.341(1.2); 4.331(1.2); 4.298(0.7); 4.287(0.7); 4.266(0.3); 4.249(0.3); 4.239(0.6); 4.229(0.3); 4.212(0.4); 3.819(0.6); 3.792(0.6); 3.782(0.5); 3.755(0.5); 3.329(53.1); 2.671(0.5); 2.506(57.1); 2.502(72.7); 2.498(53.9); 2.379(8.2); 2.329(0.5); 2.206(8.5); 2.075(1.4); 1.344(15.7); 1.338(16.0); 1.304(0.4); 0.008(0.5); 0.000(10.4) 41 2.86 2.92 (400.0 MHz, d.sub.6-DMSO): δ = 9.813(4.7); 8.054(3.2); 8.036(3.3); 7.606(2.8); 7.597(3.1); 7.591(1.4); 7.584(3.7); 7.579(4.4); 7.574(3.9); 7.567(1.4); 7.562(3.3); 7.553(0.4); 7.468(0.4); 7.464(0.3); 7.455(0.6); 7.445(0.5); 7.433(0.4); 7.229(3.2); 7.223(1.1); 7.207(5.3); 7.190(1.0); 7.184(2.8); 7.166(0.4); 7.144(0.6); 5.758(6.2); 4.561(0.7); 4.368(0.9); 4.358(0.4); 4.341(1.1); 4.331(1.1); 4.314(0.4); 4.304(1.1); 4.276(0.3); 3.904(0.6); 3.878(0.7); 3.868(0.6); 3.842(0.5); 3.344(0.6); 3.329(63.1); 2.676(0.5); 2.671(0.7); 2.667(0.6); 2.524(2.0); 2.520(3.0); 2.511(40.1); 2.507(82.9); 2.502(110.2); 2.498(81.4); 2.493(40.6); 2.473(0.5); 2.444(16.0); 2.333(0.6); 2.329(0.8); 2.324(0.6); 0.014(0.3); 0.008(1.5); 0.000(47.3); −0.009(1.9); −0.013(0.4) 42 3.94 3.90 (400.0 MHz, d.sub.6-DMSO): δ = 9.951(3.8); 8.975(0.4); 8.318(1.4); 7.736(3.0); 7.718(3.0); 7.628(0.3); 7.610(0.3); 7.573(1.1); 7.568(1.7); 7.562(1.1); 7.544(1.1); 7.539(1.7); 7.534(1.1); 7.502(2.6); 7.474(2.6); 7.463(0.3); 7.423(0.7); 7.403(2.1); 7.387(1.9); 7.383(1.7); 7.374(0.5); 7.367(1.5); 7.354(2.1); 7.351(2.8); 7.347(2.1); 7.334(1.0); 7.329(1.2); 7.326(0.9); 7.319(0.4); 7.301(0.3); 6.997(0.4); 6.987(0.8); 6.985(0.8); 6.979(1.1); 6.965(1.3); 6.959(1.5); 6.946(0.7); 6.943(0.8); 6.939(0.7); 6.936(0.6); 5.758(1.3); 5.372(0.4); 4.582(0.6); 4.487(0.7); 3.919(1.3); 3.893(3.9); 3.868(4.0); 3.850(0.4); 3.842(1.4); 3.332(49.8); 3.308(0.6); 2.671(0.4); 2.525(1.0); 2.511(23.0); 2.507(46.6); 2.502(60.9); 2.498(44.4); 2.494(21.9); 2.477(16.0); 2.433(1.8); 2.392(0.9); 2.329(0.4); 2.075(10.9); 0.008(0.6); 0.000(19.1); −0.009(0.7) 43 3.41 3.45 (400.0 MHz, d.sub.6-DMSO): δ = 10.229(0.4); 10.223(0.4); 10.051(4.3); 8.594(0.5); 8.574(0.5); 8.472(0.8); 8.317(1.1); 8.061(5.6); 8.042(3.2); 7.903(1.2); 7.884(1.5); 7.824(1.9); 7.802(1.7); 7.775(0.7); 7.752(0.5); 7.732(0.3); 7.716(0.3); 7.620(1.4); 7.614(2.7); 7.601(2.5); 7.587(2.6); 7.520(0.8); 7.494(2.8); 7.474(1.5); 7.451(0.4); 7.421(0.4); 7.196(0.6); 7.176(0.3); 6.829(0.8); 6.798(0.4); 6.778(0.4); 6.764(0.4); 6.744(0.4); 5.552(0.9); 5.453(0.4); 4.590(0.7); 4.518(1.8); 4.505(0.5); 4.373(0.8); 4.363(0.4); 4.346(1.0); 4.336(1.1); 4.319(0.4); 4.309(1.2); 4.280(0.6); 4.270(0.4); 4.243(0.4); 4.177(0.4); 4.164(1.5); 4.078(0.8); 4.076(0.8); 3.966(0.4); 3.954(0.4); 3.939(0.5); 3.928(0.5); 3.902(0.8); 3.874(0.7); 3.849(0.4); 3.839(0.4); 3.330(177.4); 2.680(0.5); 2.676(1.1); 2.671(1.5); 2.667(1.1); 2.662(0.5); 2.525(3.6); 2.520(5.7); 2.511(84.5); 2.507(174.6); 2.502(231.0); 2.498(167.9); 2.493(81.3); 2.447(16.0); 2.424(5.6); 2.350(2.7); 2.338(0.7); 2.334(1.3); 2.329(1.8); 2.324(1.6); 2.188(1.3); 2.075(1.2); 0.008(2.1); 0.000(73.0); −0.009(2.7) 44 3.58 3.64 (400.0 MHz, d.sub.6-DMSO): δ = 7.705(3.0); 7.687(3.0); 7.597(1.9); 7.577(1.9); 7.462(2.6); 7.435(2.5); 5.755(1.5); 5.465(0.4); 5.445(0.4); 4.470(0.5); 4.465(0.5); 3.909(1.2); 3.883(3.9); 3.857(4.1); 3.832(1.4); 3.765(0.4); 3.749(1.0); 3.732(1.1); 3.729(1.2); 3.712(1.0); 3.696(0.5); 3.471(0.3); 3.329(107.8); 2.671(0.4); 2.525(1.1); 2.520(1.7); 2.511(23.7); 2.507(49.0); 2.502(66.1); 2.498(49.6); 2.493(24.6); 2.458(16.0); 2.333(0.3); 2.329(0.5); 2.324(0.3); 2.086(1.6); 1.536(0.6); 1.518(2.3); 1.500(3.5); 1.482(2.8); 1.464(0.9); 1.342(1.0); 1.324(1.3); 1.307(1.1); 1.289(0.4); 1.228(1.5); 1.212(1.5); 1.147(10.3); 1.130(10.2); 1.059(0.4); 1.042(0.4); 1.017(0.4); 1.001(0.4); 0.990(0.6); 0.980(4.3); 0.964(4.3); 0.924(0.7); 0.906(1.5); 0.890(5.2); 0.872(11.0); 0.853(4.6); 0.829(2.1); 0.810(3.6); 0.792(1.6); 0.000(8.0) 45 4.16 4.23 (400.0 MHz, d.sub.6-DMSO): δ = 9.926(4.2); 8.317(0.8); 7.773(2.2); 7.768(4.2); 7.763(2.4); 7.736(3.0); 7.718(3.0); 7.702(0.3); 7.501(2.6); 7.490(1.5); 7.488(1.4); 7.486(1.4); 7.473(3.8); 7.467(2.3); 7.403(2.4); 7.383(3.9); 7.363(1.9); 7.289(0.3); 7.203(1.7); 7.201(1.9); 7.198(1.8); 7.196(1.7); 7.183(1.4); 7.181(1.5); 7.178(1.6); 7.176(1.4); 4.580(0.6); 3.918(1.2); 3.893(3.7); 3.867(3.9); 3.841(1.3); 3.331(40.0); 3.307(0.4); 2.671(0.3); 2.525(0.9); 2.511(20.1); 2.507(40.7); 2.502(53.4); 2.498(39.0); 2.494(19.1); 2.477(16.0); 2.433(1.5); 2.329(0.4); 2.075(9.7); 0.000(6.6) 46 2.97 3.02 (400.0 MHz, d.sub.6-DMSO): δ = 9.951(4.1); 8.974(0.4); 8.467(0.4); 8.315(1.6); 8.054(3.1); 8.036(3.2); 7.902(0.5); 7.884(0.5); 7.607(2.6); 7.580(2.6); 7.572(1.3); 7.567(1.9); 7.561(1.3); 7.544(1.2); 7.538(1.9); 7.533(1.2); 7.518(0.4); 7.491(0.7); 7.461(0.4); 7.424(0.7); 7.404(1.9); 7.387(2.0); 7.384(1.8); 7.368(1.6); 7.351(2.7); 7.339(0.5); 7.334(1.0); 7.330(1.3); 7.318(0.6); 7.301(0.5); 7.138(0.3); 7.135(0.3); 6.996(0.6); 6.984(0.9); 6.978(1.3); 6.964(1.5); 6.959(1.7); 6.945(0.7); 6.942(0.8); 6.939(0.7); 6.936(0.7); 6.363(0.4); 6.360(0.4); 6.358(0.4); 6.342(0.3); 6.339(0.4); 6.337(0.4); 6.306(0.4); 6.276(0.4); 6.227(0.4); 5.756(2.1); 5.366(0.7); 4.576(0.8); 4.500(0.8); 4.367(0.9); 4.357(0.4); 4.340(1.1); 4.330(1.2); 4.312(0.5); 4.303(1.2); 4.277(0.5); 4.163(0.8); 3.927(0.3); 3.901(0.7); 3.875(0.7); 3.866(0.6); 3.839(0.5); 3.506(0.4); 3.328(181.6); 2.736(0.7); 2.676(0.8); 2.671(1.1); 2.667(0.9); 2.524(2.7); 2.520(4.1); 2.511(55.3); 2.507(114.3); 2.502(155.2); 2.497(119.3); 2.493(62.3); 2.445(16.0); 2.424(2.8); 2.349(0.8); 2.333(0.8); 2.329(1.1); 2.324(0.8); 2.086(14.3); 1.234(0.6); 0.008(0.6); 0.000(17.8); −0.008(0.8) 47 2.65 2.70 (400.0 MHz, d.sub.6-DMSO): δ = 8.018(2.5); 8.000(2.6); 7.595(2.0); 7.573(4.2); 7.545(2.6); 5.756(0.7); 5.465(0.6); 5.445(0.6); 5.004(0.3); 4.979(0.3); 4.450(0.9); 4.371(0.4); 4.343(0.9); 4.334(0.5); 4.315(1.0); 4.306(1.0); 4.287(0.5); 4.279(1.0); 4.252(0.3); 3.901(0.7); 3.893(0.6); 3.874(0.7); 3.865(0.9); 3.857(0.5); 3.848(0.3); 3.837(0.7); 3.831(0.5); 3.768(0.5); 3.751(1.1); 3.733(1.4); 3.716(1.2); 3.699(0.5); 3.486(0.4); 3.471(0.5); 3.455(0.4); 3.328(108.1); 2.720(1.5); 2.671(0.6); 2.506(71.2); 2.502(91.7); 2.498(70.0); 2.431(16.0); 2.333(0.5); 2.329(0.6); 2.324(0.5); 1.537(0.7); 1.518(2.6); 1.500(4.0); 1.483(2.9); 1.465(0.9); 1.360(0.4); 1.342(1.2); 1.324(1.8); 1.307(1.4); 1.288(0.5); 1.148(9.8); 1.132(9.7); 1.058(0.4); 1.042(0.4); 0.980(4.8); 0.963(4.8); 0.893(5.3); 0.874(10.8); 0.856(4.8); 0.828(2.7); 0.810(4.6); 0.792(2.1); 0.146(0.6); 0.008(5.8); 0.000(119.1); −0.150(0.6) 48 3.25 3.31 (400.0 MHz, d.sub.6-DMSO): δ = 9.927(4.5); 8.316(0.4); 8.054(3.2); 8.036(3.2); 7.772(2.4); 7.767(4.4); 7.762(2.4); 7.608(2.5); 7.581(2.5); 7.493(1.4); 7.490(1.3); 7.488(1.2); 7.474(1.9); 7.472(2.0); 7.470(2.0); 7.404(2.4); 7.384(4.1); 7.364(2.0); 7.203(1.8); 7.201(2.0); 7.198(1.9); 7.196(1.7); 7.183(1.5); 7.181(1.6); 7.178(1.6); 7.176(1.4); 5.756(2.3); 4.572(0.7); 4.369(0.9); 4.359(0.4); 4.342(1.0); 4.332(1.1); 4.315(0.4); 4.305(1.1); 4.278(0.3); 3.901(0.5); 3.874(0.6); 3.865(0.5); 3.838(0.5); 3.326(59.8); 2.737(1.0); 2.676(0.6); 2.671(0.8); 2.666(0.6); 2.524(2.0); 2.520(2.9); 2.511(42.5); 2.506(88.1); 2.502(117.6); 2.497(85.8); 2.493(41.6); 2.445(16.0); 2.333(0.6); 2.329(0.8); 2.324(0.6); 0.146(0.9); 0.008(6.7); 0.000(200.4); −0.009(7.5); −0.025(0.3); −0.063(0.3); −0.150(0.9) 49 2.81 1.36 (400.0 MHz, d.sub.6-DMSO): δ = 7.827(2.2); 7.820(2.3); 7.482(5.9); 7.285(4.7); 4.510(2.8); 4.466(4.4); 4.358(4.5); 4.314(2.7); 3.876(1.2); 3.850(3.6); 3.824(3.7); 3.799(1.3); 3.327(23.0); 2.699(0.6); 2.691(1.1); 2.681(1.5); 2.673(1.6); 2.664(1.2); 2.655(0.7); 2.524(0.7); 2.510(14.1); 2.506(28.5); 2.502(37.9); 2.497(29.0); 2.385(15.3); 2.099(16.0); 2.074(1.3); 0.731(0.6); 0.727(0.7); 0.718(2.1); 0.714(2.9); 0.710(2.1); 0.702(2.6); 0.697(2.6); 0.685(0.8); 0.552(1.4); 0.544(3.3); 0.535(2.9); 0.528(1.9); 0.522(1.0); 0.008(1.0); 0.000(26.3); −0.008(1.4) 50 3.19 3.29 (400.0 MHz, d.sub.6-DMSO): δ = 7.794(2.3); 7.786(2.3); 7.716(6.6); 7.637(5.5); 4.625(3.1); 4.580(4.5); 4.444(4.7); 4.399(3.0); 3.989(1.2); 3.963(3.7); 3.938(3.9); 3.912(1.4); 3.329(52.5); 2.702(0.6); 2.693(1.1); 2.684(1.5); 2.676(1.7); 2.667(1.3); 2.658(0.7); 2.525(0.6); 2.520(1.0); 2.511(14.2); 2.507(29.1); 2.502(38.7); 2.498(28.6); 2.493(14.3); 2.412(16.0); 2.075(2.4); 0.730(0.5); 0.723(0.6); 0.715(2.0); 0.712(2.9); 0.708(1.8); 0.699(2.6); 0.694(2.5); 0.681(0.7); 0.567(1.4); 0.557(3.1); 0.549(2.8); 0.541(1.7); 0.535(1.0); 0.008(1.0); 0.000(29.5); −0.008(1.1) 51 3.13 3.19 (400.0 MHz, d.sub.6-DMSO): δ = 8.317(0.3); 7.878(0.9); 7.863(1.9); 7.849(1.0); 7.734(6.5); 7.641(5.5); 4.618(3.0); 4.573(4.5); 4.435(4.6); 4.390(2.9); 3.996(1.2); 3.971(3.7); 3.945(3.9); 3.920(1.4); 3.326(34.9); 3.288(0.6); 3.281(0.5); 3.270(1.5); 3.263(1.4); 3.252(1.8); 3.249(1.9); 3.238(1.4); 3.231(1.6); 3.220(0.5); 3.213(0.6); 2.675(0.5); 2.671(0.7); 2.666(0.6); 2.524(1.7); 2.519(2.6); 2.511(39.3); 2.506(81.8); 2.502(110.1); 2.497(82.6); 2.493(41.9); 2.415(16.0); 2.333(0.7); 2.329(0.8); 2.324(0.6); 2.074(4.5); 1.114(5.4); 1.096(11.8); 1.078(5.3); 0.146(0.7); 0.008(5.3); 0.000(158.0); −0.009(6.4); −0.150(0.7) 52 3.78 3.93 (400.0 MHz, d.sub.6-DMSO): δ = 7.869(0.7); 7.855(1.5); 7.840(0.7); 7.739(4.8); 7.643(4.0); 4.629(2.3); 4.584(3.3); 4.444(3.4); 4.399(2.2); 3.999(0.9); 3.973(2.7); 3.948(2.9); 3.922(1.0); 3.328(33.5); 3.121(0.5); 3.104(1.2); 3.087(1.5); 3.072(1.4); 3.059(1.3); 3.042(1.2); 3.025(0.5); 2.524(0.6); 2.519(1.0); 2.511(13.0); 2.507(27.0); 2.502(36.2); 2.497(27.1); 2.493(13.7); 2.417(11.7); 2.075(1.2); 1.821(0.4); 1.804(0.9); 1.787(1.2); 1.770(0.9); 1.754(0.5); 0.882(16.0); 0.865(15.4); 0.846(1.5); 0.830(1.4); 0.819(0.6); 0.802(0.6); 0.008(0.8); 0.000(26.5); −0.009(1.1) 53 3.40 3.51 (400.0 MHz, d.sub.6-DMSO): δ = 8.336(1.0); 8.320(2.2); 8.304(1.1); 7.749(6.5); 7.655(5.6); 4.687(3.0); 4.643(4.2); 4.479(4.4); 4.434(2.9); 4.148(0.5); 4.141(0.4); 4.126(0.9); 4.110(0.8); 4.103(1.1); 4.086(1.0); 4.080(1.0); 4.063(1.0); 4.056(0.8); 4.040(1.0); 4.032(0.4); 4.026(0.4); 4.017(0.6); 3.994(1.3); 3.969(3.7); 3.943(3.9); 3.918(1.4); 3.327(23.5); 2.671(0.3); 2.524(1.0); 2.506(36.5); 2.502(48.4); 2.497(37.0); 2.422(16.0); 2.333(0.4); 2.329(0.4); 2.075(0.8); 0.008(1.2); 0.000(31.0); −0.008(1.6) 54 3.71 3.84 (400.0 MHz, d.sub.6-DMSO): δ = 7.697(2.1); 7.678(0.9); 7.459(0.8); 7.432(0.8); 3.909(0.4); 3.884(1.2); 3.858(1.2); 3.832(0.4); 3.330(37.9); 2.506(29.3); 2.502(38.3); 2.498(30.9); 2.455(5.1); 2.336(0.8); 1.339(16.0); 1.283(2.5); 0.000(11.9) 55 4.35 4.43 (400.0 MHz, d.sub.6-DMSO): δ = 10.107(4.3); 8.069(3.4); 7.811(1.7); 7.790(2.0); 7.617(1.2); 7.597(2.5); 7.577(1.4); 7.547(5.8); 7.488(2.2); 7.468(1.6); 7.329(4.9); 4.638(2.3); 4.594(3.8); 4.499(4.1); 4.455(2.2); 3.892(1.1); 3.866(3.4); 3.840(3.5); 3.815(1.2); 3.329(32.0); 2.671(0.5); 2.502(68.3); 2.412(15.3); 2.344(0.3); 2.329(0.5); 2.161(16.0); 0.000(6.0) 56 4.19 4.32 (400.0 MHz, d.sub.6-DMSO): δ = 9.992(4.3); 7.782(2.2); 7.777(4.2); 7.772(2.4); 7.540(6.0); 7.479(1.3); 7.476(1.2); 7.474(1.2); 7.460(1.8); 7.458(2.0); 7.456(2.1); 7.453(1.8); 7.401(2.4); 7.381(3.9); 7.361(1.9); 7.324(4.7); 7.198(1.6); 7.195(1.9); 7.193(1.8); 7.190(1.7); 7.178(1.4); 7.176(1.5); 7.173(1.5); 7.171(1.4); 4.622(2.7); 4.579(4.3); 4.484(4.5); 4.440(2.6); 3.890(1.1); 3.864(3.4); 3.838(3.4); 3.813(1.2); 3.330(33.7); 2.524(0.6); 2.511(14.7); 2.506(30.6); 2.502(40.8); 2.497(30.1); 2.493(15.1); 2.409(15.1); 2.155(16.0); 0.000(5.8) 57 3.61 3.81 (400.0 MHz, d.sub.6-DMSO): δ = 8.358(1.0); 8.343(2.2); 8.328(1.1); 8.317(0.4); 7.734(6.6); 7.643(5.6); 7.340(13.3); 7.329(15.0); 7.310(0.5); 7.308(0.5); 7.284(0.4); 7.275(1.1); 7.264(1.8); 7.254(1.8); 7.243(1.1); 7.232(0.4); 4.645(3.0); 4.600(4.3); 4.485(0.6); 4.470(0.7); 4.454(4.6); 4.448(2.6); 4.432(2.3); 4.425(2.3); 4.410(5.2); 4.387(0.7); 4.372(0.6); 3.991(1.2); 3.965(3.7); 3.940(3.9); 3.914(1.3); 3.329(75.1); 2.675(0.4); 2.671(0.6); 2.666(0.4); 2.524(1.5); 2.506(68.5); 2.502(90.4); 2.497(66.7); 2.414(16.0); 2.333(0.5); 2.329(0.6); 2.324(0.5); 2.075(0.4); 0.008(0.4); 0.000(11.5); −0.009(0.5) 58 4.38 4.51 (400.0 MHz, d.sub.6-DMSO): δ = 10.045(4.4); 8.400(0.4); 8.064(3.1); 7.822(1.6); 7.801(1.7); 7.771(6.6); 7.681(5.7); 7.619(1.2); 7.599(2.4); 7.579(1.4); 7.494(2.1); 7.474(1.5); 4.763(2.7); 4.719(4.0); 4.587(4.2); 4.542(2.7); 4.516(0.6); 4.003(1.2); 3.978(3.6); 3.952(3.8); 3.927(1.4); 3.329(47.8); 2.676(0.4); 2.672(0.5); 2.667(0.4); 2.525(1.3); 2.507(58.6); 2.502(77.5); 2.498(57.2); 2.438(16.0); 2.393(0.4); 2.356(0.9); 2.333(0.4); 2.329(0.5); 2.325(0.4); 2.075(1.3); 0.000(9.6); −0.008(0.4) 59 4.28 4.46 (400.0 MHz, d.sub.6-DMSO): δ = 9.923(4.6); 7.769(4.8); 7.764(8.6); 7.677(5.8); 7.491(1.6); 7.489(1.5); 7.470(2.3); 7.468(2.3); 7.403(2.1); 7.383(3.6); 7.363(1.8); 7.202(2.1); 7.199(2.1); 7.182(1.7); 7.180(1.7); 4.751(2.7); 4.706(4.0); 4.572(4.1); 4.528(2.6); 4.002(1.2); 3.976(3.7); 3.951(3.9); 3.925(1.4); 3.330(17.4); 2.506(30.8); 2.502(38.6); 2.499(29.1); 2.436(16.0); 2.075(2.0); 0.000(4.3) 60 2.17 2.24 (400.0 MHz, d.sub.6-DMSO): δ = 7.814(8.9); 7.388(4.9); 5.756(11.8); 4.506(1.5); 4.499(1.4); 4.463(2.4); 4.455(2.4); 4.363(2.3); 4.352(2.4); 4.319(1.3); 4.309(1.5); 4.278(0.6); 4.274(0.7); 4.251(0.7); 4.246(0.8); 4.242(0.9); 4.237(0.8); 4.224(0.3); 4.214(0.8); 4.210(0.8); 3.811(0.6); 3.784(0.7); 3.778(0.8); 3.775(0.8); 3.751(0.8); 3.748(0.8); 3.742(0.6); 3.715(0.6); 3.327(25.0); 2.707(0.4); 2.699(0.9); 2.690(1.3); 2.681(1.6); 2.672(1.6); 2.664(1.1); 2.655(0.5); 2.506(32.4); 2.501(42.5); 2.497(32.9); 2.375(14.8); 2.328(0.3); 2.199(16.0); 0.738(0.4); 0.722(2.0); 0.719(1.8); 0.711(3.1); 0.705(2.4); 0.701(1.9); 0.693(1.9); 0.682(0.5); 0.550(1.5); 0.541(3.3); 0.532(3.2); 0.525(2.2); 0.000(7.1) 61 2.47 2.54 (400.0 MHz, d.sub.6-DMSO): δ = 8.337(1.1); 8.321(2.3); 8.304(1.2); 7.867(3.4); 7.859(3.4); 7.402(5.1); 5.756(8.6); 4.544(1.5); 4.539(1.5); 4.501(2.3); 4.495(2.4); 4.391(2.1); 4.375(2.1); 4.347(1.2); 4.331(1.4); 4.298(0.5); 4.286(0.7); 4.271(0.7); 4.260(1.0); 4.248(0.7); 4.234(0.7); 4.222(0.6); 4.123(0.9); 4.106(1.5); 4.084(1.7); 4.066(1.2); 4.041(0.4); 3.808(0.7); 3.781(1.1); 3.771(0.8); 3.754(0.9); 3.744(1.0); 3.717(0.7); 3.328(31.1); 2.670(0.4); 2.502(44.7); 2.384(15.3); 2.328(0.3); 2.226(16.0); 0.000(5.4) 62 2.29 2.38 (400.0 MHz, d.sub.6-DMSO): δ = 8.035(7.3); 7.774(7.7); 5.757(7.5); 4.610(1.7); 4.606(1.6); 4.566(2.5); 4.561(2.5); 4.420(2.2); 4.407(2.4); 4.375(2.0); 4.363(1.9); 4.348(0.7); 4.340(1.1); 4.331(0.8); 4.321(0.3); 4.312(0.8); 4.304(0.7); 3.915(0.7); 3.904(0.4); 3.888(0.7); 3.877(1.1); 3.861(0.4); 3.851(1.1); 3.840(0.6); 3.824(0.4); 3.814(0.5); 3.328(31.6); 2.709(0.5); 2.701(0.8); 2.692(1.3); 2.682(1.5); 2.673(1.5); 2.665(1.1); 2.656(0.5); 2.506(34.8); 2.502(44.4); 2.498(35.0); 2.416(16.0); 1.214(0.4); 1.183(0.3); 1.175(0.4); 0.734(0.4); 0.721(2.1); 0.708(3.3); 0.696(2.2); 0.691(2.0); 0.679(0.5); 0.551(3.7); 0.544(3.6); 0.000(6.7) 63 2.58 2.66 (400.0 MHz, d.sub.6-DMSO): δ = 8.318(1.2); 8.303(2.3); 8.286(1.2); 8.084(3.9); 8.076(3.8); 7.790(5.6); 5.756(9.8); 4.672(1.8); 4.666(1.7); 4.628(2.4); 4.622(2.4); 4.449(2.1); 4.429(2.1); 4.405(1.6); 4.393(0.7); 4.385(1.9); 4.366(0.8); 4.355(1.0); 4.343(0.8); 4.329(0.8); 4.316(0.7); 4.153(0.5); 4.135(0.8); 4.115(1.1); 4.093(1.4); 4.070(1.3); 4.054(0.9); 4.047(0.9); 4.032(0.5); 4.023(0.4); 3.917(0.8); 3.891(1.2); 3.880(0.8); 3.864(0.9); 3.853(1.1); 3.827(0.7); 3.327(17.7); 2.506(35.4); 2.502(44.3); 2.497(34.6); 2.425(16.0); 2.329(0.5); 1.214(0.3); 0.000(6.6) 64 2.24 2.23 (400.0 MHz, d.sub.6-DMSO): δ = 8.317(0.4); 8.054(5.4); 8.053(5.4); 7.858(1.1); 7.844(2.3); 7.830(1.1); 7.779(5.9); 4.602(1.9); 4.597(1.8); 4.557(2.6); 4.553(2.7); 4.414(2.5); 4.399(2.5); 4.385(0.6); 4.369(1.8); 4.355(1.9); 4.347(1.2); 4.336(0.7); 4.321(0.8); 4.309(0.7); 3.915(0.7); 3.888(1.2); 3.878(0.7); 3.861(0.9); 3.851(1.0); 3.824(0.7); 3.331(266.7); 3.293(0.5); 3.275(1.1); 3.265(1.6); 3.261(1.7); 3.255(1.6); 3.247(2.1); 3.236(1.3); 3.232(1.3); 3.229(1.4); 2.676(0.8); 2.671(1.2); 2.667(0.9); 2.524(3.0); 2.507(133.5); 2.502(176.0); 2.498(131.1); 2.421(16.0); 2.333(0.9); 2.329(1.2); 2.324(0.9); 1.119(3.1); 1.112(3.4); 1.101(6.7); 1.094(7.0); 1.083(3.2); 1.076(3.2); 0.146(1.4); 0.008(10.6); 0.000(291.1); −0.009(13.3); −0.150(1.4) 65 2.88 2.95 (400.0 MHz, d.sub.6-DMSO): δ = 8.317(0.5); 8.066(4.1); 8.056(4.0); 7.850(0.8); 7.841(1.4); 7.836(1.5); 7.826(0.8); 7.782(5.6); 4.611(1.8); 4.607(1.7); 4.567(2.5); 4.563(2.6); 4.419(2.2); 4.405(2.4); 4.375(2.3); 4.360(1.7); 4.348(1.1); 4.339(1.1); 4.321(0.4); 4.311(1.1); 4.284(0.4); 3.920(0.6); 3.912(0.7); 3.893(0.7); 3.884(1.0); 3.875(0.6); 3.857(0.7); 3.848(0.6); 3.329(229.6); 3.129(0.4); 3.121(0.5); 3.113(0.9); 3.105(1.0); 3.096(1.1); 3.088(1.2); 3.080(1.2); 3.072(0.8); 3.065(1.3); 3.048(1.3); 3.035(0.9); 3.017(0.5); 2.676(1.1); 2.671(1.6); 2.667(1.2); 2.524(4.3); 2.511(89.8); 2.507(181.1); 2.502(237.5); 2.498(175.1); 2.494(88.4); 2.422(16.0); 2.333(1.1); 2.329(1.6); 2.324(1.2); 1.818(0.4); 1.804(0.8); 1.801(0.8); 1.788(1.0); 1.784(1.0); 1.771(0.8); 1.767(0.8); 1.754(0.5); 0.888(11.5); 0.880(12.5); 0.871(11.5); 0.864(11.7); 0.146(1.8); 0.008(14.1); 0.000(373.3); −0.008(16.8); −0.150(1.8) 66 2.76 2.77 (400.0 MHz, d.sub.6-DMSO): δ = 7.926(0.9); 7.913(1.8); 7.901(0.9); 7.701(2.9); 7.683(2.9); 7.467(2.5); 7.440(2.5); 5.756(0.6); 4.470(0.5); 3.912(1.2); 3.886(3.8); 3.860(4.0); 3.834(1.4); 3.445(0.5); 3.439(1.0); 3.427(3.7); 3.417(6.6); 3.405(3.1); 3.393(2.0); 3.329(58.9); 3.287(0.4); 3.269(0.5); 3.256(27.7); 3.236(1.1); 3.231(0.4); 2.675(0.4); 2.671(0.5); 2.667(0.4); 2.524(1.5); 2.511(31.0); 2.507(63.3); 2.502(83.7); 2.498(62.0); 2.459(16.0); 2.333(0.4); 2.329(0.6); 2.324(0.4); 0.146(0.6); 0.016(0.3); 0.015(0.3); 0.008(4.4); 0.000(124.7); −0.009(5.5); −0.150(0.6) 67 2.98 2.99 (400.0 MHz, d.sub.6-DMSO): δ = 7.923(1.0); 7.909(2.1); 7.895(1.1); 7.701(2.9); 7.683(3.0); 7.467(2.7); 7.440(2.7); 5.756(2.0); 4.470(0.5); 3.964(0.4); 3.948(1.2); 3.937(1.3); 3.931(1.4); 3.920(1.4); 3.913(1.8); 3.903(0.7); 3.887(4.0); 3.861(4.2); 3.835(1.5); 3.779(0.9); 3.762(1.7); 3.759(1.7); 3.742(2.2); 3.726(1.2); 3.649(1.0); 3.631(2.1); 3.612(1.7); 3.595(0.8); 3.408(0.5); 3.393(0.8); 3.382(0.6); 3.374(0.9); 3.362(1.1); 3.348(0.9); 3.329(12.4); 3.258(0.8); 3.243(1.2); 3.226(1.1); 3.208(0.8); 3.193(0.6); 2.506(18.6); 2.502(24.7); 2.498(18.8); 2.459(16.0); 2.436(0.4); 1.930(0.6); 1.918(0.8); 1.912(0.8); 1.907(0.7); 1.898(1.1); 1.886(1.0); 1.869(1.0); 1.856(0.7); 1.840(1.3); 1.830(1.8); 1.820(1.8); 1.813(2.0); 1.796(1.3); 1.776(0.7); 1.576(0.5); 1.559(1.0); 1.543(0.7); 1.537(0.9); 1.529(1.0); 1.521(0.6); 1.509(0.9); 1.492(0.4); 0.008(1.0); 0.000(25.8); −0.008(1.5) 68 2.75 2.84 (400.0 MHz, d.sub.6-DMSO): δ = 8.008(0.9); 7.990(0.9); 7.699(1.3); 7.569(0.8); 7.543(0.8); 4.312(0.3); 4.302(0.4); 4.275(0.4); 3.901(0.3); 3.874(0.4); 3.329(49.9); 2.506(34.0); 2.502(45.1); 2.498(34.1); 2.454(0.3); 2.429(4.8); 2.276(0.7); 1.341(16.0); 1.296(2.4); 0.000(5.1) 69 3.33 3.37 (400.0 MHz, d.sub.6-DMSO): δ = 9.994(2.5); 9.984(2.8); 7.878(6.9); 7.780(1.4); 7.775(3.3); 7.770(3.3); 7.765(1.3); 7.483(0.9); 7.478(1.1); 7.470(0.8); 7.463(1.3); 7.457(1.8); 7.424(5.1); 7.408(1.3); 7.397(1.3); 7.388(2.0); 7.377(2.2); 7.367(1.1); 7.357(1.1); 7.199(1.1); 7.193(1.5); 7.188(1.2); 7.182(1.0); 7.179(1.0); 7.174(1.2); 7.168(0.9); 5.757(1.2); 4.624(1.6); 4.616(1.4); 4.581(2.4); 4.572(2.3); 4.482(2.3); 4.472(2.5); 4.439(1.3); 4.428(1.5); 4.310(0.5); 4.297(0.6); 4.284(0.7); 4.273(0.8); 4.270(0.8); 4.259(0.8); 4.246(0.7); 4.232(0.7); 3.836(0.6); 3.810(0.7); 3.799(0.6); 3.790(0.6); 3.782(0.4); 3.773(0.6); 3.763(0.7); 3.753(0.6); 3.726(0.5); 3.329(21.8); 2.506(36.4); 2.502(46.8); 2.497(34.4); 2.393(14.2); 2.376(0.6); 2.328(0.3); 2.253(16.0); 1.215(0.4); 1.188(0.4); 1.183(0.5); 1.174(0.4); 0.008(1.8); 0.000(46.6); −0.008(2.1) 70 2.91 2.95 (400.0 MHz, d.sub.6-DMSO): δ = 8.342(0.7); 8.328(1.6); 8.316(1.6); 8.301(0.7); 8.064(3.9); 8.055(3.8); 7.780(5.3); 7.342(7.0); 7.336(9.5); 7.332(11.1); 7.325(9.1); 7.291(0.5); 7.279(0.9); 7.269(1.6); 7.258(2.3); 7.248(1.5); 7.239(1.0); 7.227(0.3); 7.219(0.4); 5.757(3.5); 4.629(2.0); 4.584(3.0); 4.498(0.4); 4.483(0.5); 4.470(0.5); 4.460(1.3); 4.447(2.0); 4.434(4.1); 4.417(3.8); 4.390(1.9); 4.373(2.4); 4.349(1.1); 4.339(1.1); 4.321(0.7); 4.311(1.2); 4.285(0.4); 4.238(0.3); 3.916(0.8); 3.889(1.2); 3.879(0.8); 3.863(0.9); 3.852(1.0); 3.826(0.7); 3.329(42.0); 2.675(0.4); 2.671(0.6); 2.666(0.4); 2.506(68.2); 2.502(85.0); 2.497(64.2); 2.419(16.0); 2.329(0.6); 2.324(0.5); 2.320(0.4); 0.146(0.4); 0.000(72.7); −0.150(0.3) 71 3.64 3.68 (400.0 MHz, d.sub.6-DMSO): δ = 10.049(2.7); 10.039(2.9); 8.772(0.4); 8.100(6.4); 8.064(2.6); 7.815(7.9); 7.798(2.1); 7.636(0.4); 7.625(0.7); 7.614(0.8); 7.605(1.5); 7.594(1.6); 7.585(0.9); 7.574(0.9); 7.491(1.5); 7.474(1.1); 5.757(1.5); 4.754(1.9); 4.747(1.7); 4.710(2.6); 4.703(2.4); 4.563(2.3); 4.552(2.5); 4.530(0.7); 4.519(1.6); 4.508(1.7); 4.410(0.5); 4.392(0.6); 4.382(0.8); 4.372(0.7); 4.365(0.7); 4.355(0.9); 4.345(0.7); 4.338(0.4); 4.327(0.7); 3.946(0.7); 3.919(0.8); 3.909(0.8); 3.892(0.4); 3.882(1.1); 3.856(0.8); 3.846(0.6); 3.820(0.6); 3.332(21.9); 2.525(0.6); 2.511(12.2); 2.507(24.5); 2.503(31.9); 2.498(23.7); 2.494(12.0); 2.438(16.0); 2.416(0.8); 2.333(1.1); 0.008(1.3); 0.000(37.8); −0.008(1.7) 72 3.50 3.55 (400.0 MHz, d.sub.6-DMSO): δ = 9.925(2.6); 9.914(2.8); 8.091(6.8); 7.812(6.0); 7.765(3.6); 7.487(1.4); 7.467(2.1); 7.410(1.2); 7.399(1.3); 7.390(2.1); 7.379(2.3); 7.369(1.0); 7.359(1.1); 7.206(1.1); 7.200(1.6); 7.195(1.3); 7.189(1.0); 7.187(1.0); 7.181(1.3); 7.175(1.0); 5.757(1.7); 4.741(1.8); 4.734(1.6); 4.696(2.4); 4.690(2.3); 4.545(2.2); 4.532(2.4); 4.500(1.5); 4.488(1.6); 4.405(0.5); 4.388(0.6); 4.378(0.8); 4.368(0.7); 4.362(0.7); 4.351(0.9); 4.341(0.7); 4.324(0.7); 3.944(0.6); 3.917(0.8); 3.907(0.6); 3.889(0.8); 3.880(0.7); 3.862(0.7); 3.852(0.7); 3.825(0.5); 3.329(66.7); 2.675(0.5); 2.671(0.7); 2.667(0.6); 2.506(80.3); 2.502(104.7); 2.498(78.6); 2.434(16.0); 2.329(0.9); 1.215(0.5); 1.188(0.4); 1.183(0.6); 1.174(0.5); 0.146(0.5); 0.008(3.8); 0.000(99.2); −0.008(4.9); −0.150(0.5) 73 3.70 3.72 (400.0 MHz, d.sub.6-DMSO): δ = 8.317(1.0); 8.067(0.8); 8.053(1.7); 8.039(0.9); 7.841(2.8); 7.823(2.8); 7.469(2.4); 7.442(2.4); 3.949(1.1); 3.924(3.6); 3.898(3.7); 3.872(1.3); 3.328(342.7); 3.257(1.4); 3.241(1.9); 3.224(1.4); 2.675(2.0); 2.671(2.8); 2.667(2.1); 2.524(6.9); 2.511(156.5); 2.506(322.1); 2.502(427.9); 2.498(318.4); 2.455(16.0); 2.333(2.1); 2.329(2.9); 2.324(2.2); 1.698(6.9); 1.351(0.4); 1.297(0.3); 1.235(0.8); 1.148(0.4); 1.110(5.1); 1.092(10.9); 1.074(5.0); 0.827(0.5); 0.146(3.3); 0.008(26.0); 0.000(717.9); −0.009(30.0); −0.031(0.6); −0.150(3.3) 74 3.72 3.76 (400.0 MHz, d.sub.6-DMSO): δ = 8.005(2.4); 7.998(2.5); 7.820(2.9); 7.802(2.9); 7.464(2.6); 7.437(2.6); 5.757(1.5); 3.941(1.2); 3.915(3.7); 3.889(3.8); 3.864(1.3); 3.330(61.4); 2.708(0.6); 2.700(1.1); 2.691(1.5); 2.682(1.6); 2.673(1.4); 2.665(0.9); 2.506(44.6); 2.502(56.1); 2.452(16.0); 2.329(0.4); 1.701(8.5); 0.709(3.1); 0.692(3.0); 0.528(3.0); 0.146(0.4); 0.000(73.5); −0.150(0.4) 75 3.95 4.02 (400.0 MHz, d.sub.6-DMSO): δ = 8.912(0.4); 8.522(1.0); 8.506(2.1); 8.489(1.0); 7.868(2.9); 7.850(2.9); 7.483(2.5); 7.456(2.5); 6.824(0.3); 6.808(0.6); 6.792(0.4); 5.756(0.9); 4.754(0.3); 4.731(0.4); 4.672(0.4); 4.649(1.3); 4.627(1.3); 4.605(0.5); 4.080(0.8); 4.065(0.8); 4.048(0.7); 4.040(0.8); 4.024(0.6); 4.016(0.6); 4.001(0.5); 3.942(1.2); 3.917(3.7); 3.891(4.2); 3.874(0.6); 3.866(2.4); 3.850(1.2); 3.842(1.3); 3.826(1.2); 3.817(0.5); 3.801(0.4); 3.328(55.1); 2.676(0.4); 2.671(0.6); 2.667(0.5); 2.525(1.5); 2.511(33.8); 2.507(67.4); 2.502(88.0); 2.498(64.3); 2.494(32.0); 2.463(16.0); 2.334(0.4); 2.329(0.6); 2.325(0.4); 1.708(8.2); 0.146(0.5); 0.008(4.0); 0.000(109.1); −0.009(4.5); −0.150(0.5) 76 4.42 4.51 (400.0 MHz, d.sub.6-DMSO): δ = 8.086(0.7); 8.071(1.5); 8.057(0.8); 7.846(2.2); 7.828(2.3); 7.472(2.0); 7.445(2.0); 3.950(0.9); 3.925(2.9); 3.899(3.0); 3.873(1.0); 3.331(113.4); 3.077(1.1); 3.063(1.9); 3.049(1.2); 2.676(0.4); 2.672(0.5); 2.667(0.4); 2.525(1.4); 2.507(65.6); 2.502(84.5); 2.498(62.4); 2.458(12.4); 2.334(0.4); 2.329(0.5); 2.325(0.4); 1.809(0.5); 1.792(0.9); 1.775(1.2); 1.759(1.1); 1.742(0.7); 1.697(5.6); 0.884(16.0); 0.867(15.5); 0.146(0.6); 0.008(4.7); 0.000(119.0); −0.008(5.4); −0.150(0.6) 77 4.33 4.37 (400.0 MHz, d.sub.6-DMSO): δ = 8.524(1.0); 8.509(2.0); 8.494(1.0); 7.846(2.9); 7.828(2.9); 7.470(2.5); 7.443(2.4); 7.362(0.7); 7.359(0.5); 7.349(1.1); 7.343(4.6); 7.335(5.1); 7.328(16.0); 7.319(1.2); 7.314(1.2); 7.278(0.9); 7.272(1.2); 7.263(1.2); 7.257(1.3); 7.253(0.8); 7.248(0.7); 7.242(0.6); 7.235(0.3); 5.757(4.8); 4.436(2.0); 4.425(2.0); 3.939(1.1); 3.914(3.5); 3.888(3.7); 3.862(1.3); 23.33(36.6); 2.541(0.4); 2.511(14.6); 2.507(28.4); 2.502(37.0); 2.498(27.4); 2.493(14.1); 2.455(15.1); 1.709(9.2); 0.008(3.0); 0.000(63.8); −0.009(3.4) 78 3.29 3.37 (400.0 MHz, d.sub.6-DMSO): δ = 10.275(4.2); 8.342(1.8); 8.339(1.9); 8.330(1.9); 8.327(1.8); 8.005(2.3); 7.984(3.3); 7.900(1.2); 7.895(1.3); 7.877(1.8); 7.861(0.9); 7.856(0.9); 7.729(2.9); 7.711(2.9); 7.507(2.8); 7.480(2.6); 7.198(1.4); 7.196(1.6); 7.184(1.7); 7.180(1.6); 7.178(1.5); 7.168(1.4); 7.166(1.4); 4.589(0.6); 4.547(1.1); 3.927(1.2); 3.901(3.9); 3.875(4.2); 3.849(1.6); 3.330(19.4); 2.525(0.7); 2.511(15.1); 2.507(30.7); 2.503(40.7); 2.498(30.5); 2.494(15.7); 2.480(16.0); 2.390(1.1); 2.075(0.4); 0.000(5.5) 79 3.56 3.55 (400.0 MHz, d.sub.6-DMSO): δ = 8.377(1.0); 8.361(2.2); 8.345(1.1); 7.756(0.5); 7.478(2.1); 7.451(2.1); 5.757(0.8); 4.773(0.4); 4.765(0.4); 4.119(0.6); 4.101(0.7); 4.080(0.8); 4.059(0.7); 3.922(0.8); 3.896(2.1); 3.871(2.1); 3.845(0.8); 3.329(17.9); 2.507(35.9); 2.502(47.3); 2.498(36.2); 2.462(16.0); 2.420(0.4); 1.587(4.5); 1.570(4.5); 0.008(2.1); 0.000(51.1); −0.008(2.8) 80 3.98 3.99 (400.0 MHz, d.sub.6-DMSO): δ = 7.906(0.7); 7.891(1.4); 7.877(0.7); 7.745(0.4); 7.466(1.6); 7.439(1.6); 5.757(0.9); 3.924(0.5); 3.899(1.4); 3.874(1.4); 3.848(0.5); 3.328(19.6); 3.112(0.4); 3.095(0.8); 3.079(1.2); 3.071(0.9); 3.063(1.0); 3.056(1.2); 3.039(0.8); 3.023(0.3); 2.524(0.8); 2.507(29.8); 2.502(38.8); 2.498(28.7); 2.458(12.2); 1.818(0.5); 1.801(1.0); 1.784(1.2); 1.768(1.0); 1.751(0.6); 1.570(2.8); 1.553(2.7); 0.884(16.0); 0.867(15.4); 0.846(1.4); 0.830(1.3); 0.819(0.6); 0.802(0.6); 0.008(1.7); 0.000(43.9); −0.008(2.0) 81 3.91 3.94 (400.0 MHz, d.sub.6-DMSO): δ = 8.388(1.0); 8.373(2.0); 8.358(1.0); 7.745(0.5); 7.465(2.0); 7.438(2.0); 7.360(0.3); 7.339(10.0); 7.328(16.0); 7.284(0.4); 7.275(1.1); 7.264(1.9); 7.253(1.8); 7.242(1.3); 7.232(0.4); 7.215(0.4); 7.147(0.5); 7.130(0.4); 5.757(5.1); 5.052(0.4); 4.746(0.3); 4.495(0.5); 4.480(0.5); 4.458(1.4); 4.443(1.4); 4.425(1.4); 4.410(1.5); 4.387(0.5); 4.373(0.5); 4.322(0.5); 4.307(0.5); 3.917(0.6); 3.891(1.7); 3.866(1.7); 3.840(0.7); 3.332(18.8); 2.506(22.0); 2.502(28.6); 2.497(21.7); 2.456(14.5); 2.074(0.4); 1.583(4.0); 1.566(4.0); 0.008(1.2); 0.000(32.3) 82 1.94 1.97 (400.0 MHz, d.sub.6-DMSO): δ = 8.158(0.6); 8.020(3.1); 8.001(3.1); 7.926(1.0); 7.913(2.0); 7.901(1.0); 7.576(2.5); 7.549(2.5); 4.452(0.7); 4.377(0.4); 4.349(1.0); 4.339(0.5); 4.322(1.1); 4.312(1.2); 4.295(0.5); 4.285(1.2); 4.258(0.4); 3.898(1.1); 3.888(0.4); 3.871(1.2); 3.861(1.0); 3.845(0.5); 3.834(1.0); 3.807(0.3); 3.441(1.1); 3.430(4.1); 3.420(7.0); 3.407(3.5); 3.395(2.3); 3.331(5.9); 3.258(27.9); 2.524(0.7); 2.506(34.2); 2.502(45.1); 2.497(33.4); 2.432(16.0); 0.008(0.9); 0.000(27.0); −0.008(1.2) 83 2.70 2.73 (400.0 MHz, d.sub.6-DMSO): δ = 20.011(0.4); 8.317(4.0); 8.171(2.8); 8.152(2.7); 8.059(1.1); 8.044(2.1); 8.030(1.0); 7.581(2.4); 7.554(2.5); 5.758(0.4); 4.345(0.6); 4.308(0.8); 4.282(0.7); 4.252(0.4); 3.872(0.5); 3.328(955.0); 3.260(2.0); 3.244(2.6); 3.228(2.0); 3.212(0.7); 2.676(7.3); 2.671(10.1); 2.667(7.6); 2.524(27.3); 2.507(1169.7); 2.502(1521.2); 2.498(1110.4); 2.442(16.0); 2.333(7.2); 2.329(9.8); 2.324(7.2); 1.710(11.7); 1.351(0.8); 1.297(0.6); 1.260(0.9); 1.234(3.2); 1.114(5.3); 1.096(11.0); 1.078(5.1); 0.854(0.7); 0.826(0.6); 0.146(2.3); 0.008(18.1); 0.000(502.1); −0.008(19.2); −0.150(2.2) 84 2.73 2.73 (400.0 MHz, d.sub.6-DMSO): δ = 8.317(0.7); 8.146(2.9); 8.128(2.9); 8.004(2.3); 7.996(2.4); 7.576(2.5); 7.549(2.5); 5.757(2.3); 4.337(0.5); 4.310(0.7); 4.300(0.7); 4.273(0.6); 3.903(0.3); 3.879(0.4); 3.857(0.3); 3.568(0.6); 3.328(178.0); 2.717(1.4); 2.707(1.2); 2.698(1.6); 2.689(1.6); 2.680(1.8); 2.676(1.9); 2.671(2.7); 2.667(1.8); 2.506(234.8); 2.502(310.2); 2.498(230.6); 2.435(16.0); 2.333(1.4); 2.329(2.0); 2.324(1.5); 1.712(12.2); 1.235(0.5); 0.713(3.0); 0.700(2.7); 0.696(2.8); 0.526(2.9); 0.146(0.4); 0.008(3.3); 0.000(101.0); −0.008(4.6); −0.150(0.5) 85 3.05 3.07 (400.0 MHz, d.sub.6-DMSO): δ = 8.911(0.4); 8.518(1.1); 8.502(2.4); 8.486(1.2); 8.317(0.8); 8.212(2.1); 8.194(2.2); 7.591(2.5); 7.565(2.5); 6.806(0.4); 5.757(1.1); 4.752(0.3); 4.730(0.4); 4.671(0.4); 4.649(1.2); 4.627(1.2); 4.605(0.4); 4.355(0.5); 4.320(0.6); 4.291(0.6); 4.088(1.4); 4.041(0.7); 4.025(0.6); 4.015(0.5); 4.000(0.4); 3.891(0.5); 3.866(1.0); 3.850(1.0); 3.842(1.0); 3.826(0.8); 3.800(0.4); 3.331(487.4); 2.727(1.1); 2.676(1.6); 2.671(2.3); 2.667(1.8); 2.524(5.5); 2.507(258.6); 2.502(344.8); 2.498(264.5); 2.444(16.0); 2.333(1.6); 2.329(2.2); 2.324(1.7); 1.718(13.8); 1.233(0.9); 0.146(0.5); 0.008(3.8); 0.000(103.2); −0.150(0.4) 86 3.39 3.41 (400.0 MHz, d.sub.6-DMSO): δ = 8.318(0.8); 8.180(1.6); 8.161(1.6); 8.080(0.8); 8.066(1.6); 8.051(0.8); 7.583(1.8); 7.557(1.8); 4.343(0.5); 4.315(0.6); 4.307(0.6); 4.278(0.6); 3.897(0.4); 3.328(183.7); 3.082(1.2); 3.067(1.9); 2.725(0.4); 2.675(2.0); 2.671(2.7); 2.667(2.1); 2.564(0.4); 2.506(328.5); 2.502(417.8); 2.498(309.0); 2.442(12.1); 2.333(2.1); 2.329(2.7); 2.324(2.0); 1.811(0.5); 1.794(0.9); 1.777(1.2); 1.761(1.1); 1.744(0.8); 1.708(9.1); 1.351(0.4); 1.235(1.0); 0.887(16.0); 0.871(15.7); 0.146(0.6); 0.000(126.5); −0.008(6.6); −0.150(0.6) 87 3.38 3.48 (400.0 MHz, d.sub.6-DMSO): δ = 8.516(0.9); 8.502(1.9); 8.486(0.9); 8.180(2.2); 8.162(2.2); 7.581(2.4); 7.555(2.4); 7.363(0.7); 7.343(4.4); 7.335(4.8); 7.328(16.0); 7.314(1.2); 7.278(0.9); 7.272(1.1); 7.263(1.1); 7.256(1.3); 7.248(0.7); 7.242(0.6); 4.444(2.4); 4.429(2.5); 4.342(0.6); 4.314(0.7); 4.304(0.7); 4.277(0.7); 3.872(0.4); 3.331(119.1); 2.676(0.5); 2.671(0.6); 2.666(0.5); 2.524(1.6); 2.511(35.7); 2.506(73.5); 2.502(97.4); 2.498(71.5); 2.493(35.3); 2.438(15.1); 2.333(0.5); 2.329(0.6); 2.324(0.5); 2.086(13.9); 1.929(0.9); 1.768(1.0); 1.720(13.2); 0.008(0.6); 0.000(18.1); −0.009(0.6) 88 2.71 2.75 (400.0 MHz, d.sub.6-DMSO): δ = 8.357(0.3); 8.139(2.4); 7.582(0.4); 7.555(0.4); 3.420(34.4); 3.170(0.3); 2.511(16.9); 2.507(21.9); 2.503(16.8); 2.438(2.7); 2.088(16.0); 1.598(0.8); 1.582(0.8); 0.000(3.9) 89 3.02 3.10 (400.0 MHz, d.sub.6-DMSO): δ = 8.317(0.6); 8.071(0.6); 8.059(0.6); 7.886(1.1); 7.872(0.6); 7.576(1.8); 7.550(1.8); 4.351(0.4); 4.340(0.4); 4.324(0.5); 4.314(0.7); 4.301(0.4); 4.287(0.6); 4.275(0.4); 3.895(0.5); 3.869(0.5); 3.859(0.5); 3.832(0.4); 3.328(165.7); 3.118(0.5); 3.102(0.9); 3.086(1.3); 3.070(1.2); 3.056(1.1); 3.041(0.8); 3.024(0.4); 2.676(1.0); 2.671(1.4); 2.667(1.1); 2.524(3.7); 2.511(80.2); 2.507(163.7); 2.502(215.7); 2.497(156.7); 2.493(76.7); 2.434(12.0); 2.333(1.0); 2.329(1.4); 2.324(1.0); 1.819(0.5); 1.802(1.0); 1.785(1.4); 1.768(1.1); 1.752(0.6); 1.580(3.1); 1.564(3.0); 0.886(16.0); 0.869(15.6); 0.846(1.5); 0.829(1.5); 0.818(0.7); 0.801(0.6); 0.008(2.0); 0.000(65.0); −0.009(2.4) 90 3.05 3.12 (400.0 MHz, d.sub.6-DMSO): δ = 8.377(0.6); 8.363(1.2); 8.347(0.6); 8.074(0.5); 8.060(0.5); 7.575(1.4); 7.548(1.4); 7.339(6.2); 7.328(11.2); 7.274(0.6); 7.264(1.0); 7.253(1.0); 7.241(0.5); 4.486(0.3); 4.464(0.9); 4.449(0.8); 4.425(1.0); 4.411(1.1); 4.388(0.4); 4.374(0.4); 4.351(0.3); 4.324(0.4); 4.314(0.5); 4.301(0.4); 4.287(0.4); 3.880(0.3); 3.854(0.3); 3.845(0.3); 3.330(19.7); 2.524(0.5); 2.510(11.2); 2.506(22.8); 2.502(30.2); 2.497(22.5); 2.493(11.5); 2.431(8.5); 2.086(16.0); 1.593(2.7); 1.576(2.7); 0.000(6.0) 91 2.13 2.19 (400.0 MHz, d.sub.6-DMSO): δ = 8.317(0.5); 8.147(1.0); 8.018(3.1); 8.000(3.1); 7.920(1.0); 7.906(1.9); 7.892(1.0); 7.577(2.5); 7.550(2.4); 4.455(0.6); 4.376(0.4); 4.349(1.0); 4.339(0.5); 4.321(1.1); 4.312(1.2); 4.294(0.5); 4.284(1.2); 4.257(0.4); 3.963(0.4); 3.946(1.2); 3.935(1.3); 3.929(1.6); 3.918(1.3); 3.912(0.6); 3.903(1.2); 3.894(0.4); 3.877(1.2); 3.866(1.0); 3.850(0.5); 3.840(1.0); 3.813(0.3); 3.779(0.8); 3.762(1.5); 3.759(1.4); 3.742(1.9); 3.726(1.0); 3.649(1.0); 3.631(2.0); 3.612(1.6); 3.594(0.7); 3.415(0.6); 3.400(0.8); 3.389(0.8); 3.381(1.0); 3.366(1.3); 3.355(1.4); 3.329(78.8); 3.257(0.8); 3.242(1.2); 3.225(1.1); 3.208(0.7); 3.192(0.5); 2.676(0.7); 2.671(1.0); 2.667(0.8); 2.524(2.7); 2.511(57.4); 2.507(117.9); 2.502(156.1); 2.498(114.7); 2.493(56.8); 2.432(16.0); 2.333(0.8); 2.329(1.0); 2.324(0.8); 1.932(0.6); 1.920(0.7); 1.916(0.7); 1.909(0.6); 1.900(1.0); 1.887(0.9); 1.871(0.9); 1.857(0.6); 1.841(1.1); 1.837(1.0); 1.831(1.5); 1.821(1.5); 1.814(1.6); 1.794(1.0); 1.777(0.4); 1.578(0.5); 1.561(0.9); 1.545(0.6); 1.539(0.9); 1.531(1.0); 1.523(0.5); 1.511(0.8); 0.008(0.9); 0.000(29.2); −0.009(1.1) 92 3.66 3.75 (400.0 MHz, d.sub.6-DMSO): δ = 8.365(1.0); 8.350(2.1); 8.334(1.0); 7.505(5.8); 7.342(12.5); 7.331(10.2); 7.316(0.5); 7.309(0.7); 7.291(4.8); 7.275(1.0); 7.263(1.5); 7.253(1.6); 7.242(1.0); 7.232(0.4); 4.529(2.5); 4.485(4.2); 4.468(0.5); 4.446(2.4); 4.432(3.7); 4.418(2.4); 4.396(0.4); 4.372(4.2); 4.328(2.5); 3.879(1.1); 3.853(3.5); 3.827(3.7); 3.802(1.3); 3.335(108.4); 2.671(0.4); 2.506(50.0); 2.502(65.5); 2.498(49.8); 2.388(15.1); 2.333(0.4); 2.329(0.4); 2.117(16.0); 2.074(1.2); 0.008(0.6); 0.000(16.5) 93 3.86 3.95 (400.0 MHz, d.sub.6-DMSO): δ = 9.875(4.3); 7.594(2.7); 7.589(1.1); 7.582(2.9); 7.577(1.8); 7.571(3.2); 7.565(1.2); 7.559(3.0); 7.550(0.4); 7.540(5.9); 7.321(4.7); 7.226(3.0); 7.220(1.0); 7.203(5.2); 7.187(0.9); 7.181(2.7); 4.615(2.5); 4.571(4.2); 4.474(4.3); 4.430(2.5); 3.891(1.1); 3.866(3.4); 3.840(3.5); 3.814(1.2); 3.330(35.0); 2.671(0.4); 2.524(1.0); 2.507(43.1); 2.502(56.4); 2.498(41.9); 2.408(15.1); 2.329(0.4); 2.154(16.0); 2.075(0.4); 0.008(2.1); 0.000(57.2); −0.008(2.6) 94 3.96 4.05 (400.0 MHz, d.sub.6-DMSO): δ = 9.807(4.5); 7.764(6.7); 7.674(5.7); 7.596(2.8); 7.591(1.2); 7.584(3.1); 7.578(1.9); 7.573(3.4); 7.566(1.3); 7.561(3.2); 7.552(0.4); 7.227(3.2); 7.222(1.1); 7.205(5.5); 7.188(1.0); 7.183(2.9); 4.741(3.0); 4.696(4.3); 4.561(4.4); 4.516(2.8); 4.003(1.2); 3.978(3.7); 3.952(3.9); 3.927(1.3); 3.329(47.9); 2.676(0.4); 2.671(0.5); 2.667(0.4); 2.524(1.4); 2.511(30.5); 2.507(61.0); 2.502(79.9); 2.498(59.1); 2.493(30.1); 2.434(16.0); 2.333(0.5); 2.329(0.6); 2.325(0.4); 0.146(0.4); 0.008(3.0); 0.000(80.2); −0.008(3.7); −0.150(0.4) 95 3.42 3.47 (400.0 MHz, d.sub.6-DMSO): δ = 10.346(4.1); 8.333(1.8); 8.323(1.8); 8.321(1.8); 8.319(1.8); 8.016(2.3); 7.995(3.1); 7.898(1.1); 7.893(1.2); 7.875(1.7); 7.858(0.9); 7.854(0.9); 7.532(5.8); 7.328(4.6); 7.189(1.5); 7.177(1.6); 7.173(1.5); 7.158(1.4); 4.632(2.5); 4.588(4.1); 4.495(4.3); 4.451(2.4); 3.895(1.2); 3.870(3.8); 3.844(3.9); 3.818(1.4); 3.330(245.6); 2.675(1.1); 2.671(1.5); 2.667(1.1); 2.524(3.5); 2.510(83.5); 2.506(171.1); 2.502(227.6); 2.498(168.6); 2.412(15.3); 2.374(0.6); 2.333(1.1); 2.329(1.5); 2.324(1.2); 2.156(16.0); 2.061(0.5); 0.146(1.2); 0.008(9.1); 0.000(268.8); −0.009(11.0); −0.150(1.3) 96 3.51 3.55 (400.0 MHz, d.sub.6-DMSO): δ = 10.405(0.8); 10.263(4.3); 8.415(1.1); 8.341(1.8); 8.339(1.9); 8.329(1.9); 8.327(1.8); 8.318(0.4); 8.084(0.4); 8.079(0.4); 8.007(2.3); 7.986(3.4); 7.904(1.2); 7.899(1.2); 7.881(1.8); 7.864(0.9); 7.860(0.9); 7.750(6.4); 7.681(5.5); 7.531(0.5); 7.513(1.2); 7.201(1.5); 7.199(1.5); 7.187(1.6); 7.183(1.6); 7.181(1.5); 7.170(1.4); 7.168(1.4); 4.774(2.9); 4.730(4.1); 4.580(4.3); 4.555(1.9); 4.535(2.9); 4.008(1.1); 3.982(3.6); 3.957(3.8); 3.931(1.4); 3.920(0.8); 3.895(0.7); 3.330(94.1); 2.676(0.6); 2.671(0.9); 2.667(0.6); 2.524(2.2); 2.511(49.3); 2.507(99.2); 2.502(129.9); 2.498(95.1); 2.493(47.2); 2.439(16.0); 2.365(0.6); 2.354(2.7); 2.333(1.1); 2.329(1.1); 2.325(0.7); 2.206(0.4); 0.146(0.7); 0.008(5.6); 0.000(152.0); −0.008(6.5); −0.150(0.7) 97 3.47 3.57 (400.0 MHz, d.sub.6-DMSO): δ = 10.110(2.6); 10.102(2.9); 8.073(1.8); 8.067(1.6); 8.061(1.7); 7.885(7.1); 7.809(1.5); 7.789(1.9); 7.623(0.6); 7.612(0.7); 7.604(1.3); 7.592(1.4); 7.584(0.8); 7.572(0.8); 7.483(1.3); 7.466(1.0); 7.428(5.1); 4.639(1.6); 4.631(1.4); 4.596(2.4); 4.587(2.2); 4.498(2.3); 4.488(2.5); 4.455(1.3); 4.445(1.5); 4.314(0.5); 4.299(0.6); 4.287(0.7); 4.277(0.7); 4.272(0.8); 4.262(0.8); 4.250(0.7); 4.235(0.7); 3.839(0.6); 3.812(0.8); 3.802(0.6); 3.785(0.8); 3.775(0.8); 3.758(0.6); 3.748(0.7); 3.721(0.5); 3.330(34.0); 2.524(0.6); 2.511(14.7); 2.506(30.5); 2.502(40.6); 2.497(30.0); 2.493(15.1); 2.396(13.5); 2.312(0.3); 2.295(0.4); 2.259(16.0); 2.075(8.8); 0.008(1.2); 0.000(35.4); −0.009(1.4) 98 2.77 2.85 (400.0 MHz, d.sub.6-DMSO): δ = 8.359(0.5); 8.344(1.7); 8.329(1.7); 8.314(0.6); 7.847(3.4); 7.838(3.4); 7.393(4.8); 7.344(7.0); 7.337(8.3); 7.333(8.4); 7.326(6.5); 7.312(0.5); 7.304(0.4); 7.278(0.7); 7.268(1.3); 7.257(1.7); 7.247(1.3); 7.236(0.7); 5.757(1.7); 4.522(1.6); 4.518(1.6); 4.478(2.8); 4.475(2.8); 4.455(1.3); 4.440(2.9); 4.425(2.1); 4.420(1.7); 4.402(0.3); 4.380(2.3); 4.365(2.3); 4.336(1.3); 4.322(1.6); 4.306(0.5); 4.280(0.9); 4.270(0.4); 4.252(1.0); 4.243(1.1); 4.225(0.4); 4.216(1.1); 4.188(0.3); 3.813(0.7); 3.786(1.1); 3.776(0.7); 3.759(0.8); 3.749(1.0); 3.722(0.7); 3.328(45.0); 2.675(0.4); 2.671(0.6); 2.666(0.5); 2.662(0.5); 2.524(1.2); 2.506(63.5); 2.501(84.5); 2.497(63.5); 2.378(15.3); 2.333(0.5); 2.328(0.6); 2.324(0.5); 2.249(0.4); 2.217(16.0); 0.000(0.9) 99 2.92 3.01 (400.0 MHz, d.sub.6-DMSO): δ = 9.875(2.6); 9.868(2.8); 7.877(7.1); 7.597(1.7); 7.591(2.0); 7.585(2.2); 7.579(2.5); 7.574(2.8); 7.568(2.4); 7.562(2.4); 7.556(1.8); 7.422(5.0); 7.232(1.7); 7.222(1.9); 7.216(1.1); 7.210(3.0); 7.205(1.4); 7.200(3.2); 7.188(1.7); 7.184(0.7); 7.178(1.7); 5.757(2.9); 4.617(1.6); 4.608(1.4); 4.573(2.4); 4.565(2.3); 4.473(2.3); 4.463(2.5); 4.430(1.3); 4.419(1.5); 4.306(0.5); 4.296(0.7); 4.279(0.6); 4.269(1.2); 4.259(0.7); 4.242(0.8); 4.232(0.7); 3.837(0.6); 3.826(0.3); 3.810(0.7); 3.799(1.0); 3.783(0.3); 3.772(1.1); 3.761(0.6); 3.745(0.4); 3.735(0.5); 3.329(37.6); 2.679(0.4); 2.671(0.4); 2.524(0.9); 2.510(21.5); 2.506(43.9); 2.502(58.1); 2.497(43.0); 2.393(13.9); 2.328(0.4); 2.285(0.3); 2.251(16.0); 0.000(0.6) 100 3.09 3.17 (400.0 MHz, d.sub.6-DMSO): δ = 9.808(2.6); 9.799(2.8); 8.317(0.3); 8.091(8.0); 7.810(6.2); 7.593(2.2); 7.583(2.2); 7.580(2.5); 7.573(2.7); 7.570(2.4); 7.560(2.4); 7.234(1.8); 7.224(2.0); 7.217(1.1); 7.212(3.2); 7.207(1.4); 7.202(3.4); 7.190(1.7); 7.179(1.7); 5.757(1.8); 4.731(1.8); 4.724(1.6); 4.686(2.5); 4.680(2.4); 4.534(2.2); 4.522(2.4); 4.490(1.5); 4.478(1.7); 4.400(0.5); 4.388(0.7); 4.373(0.7); 4.362(1.0); 4.351(0.7); 4.335(0.8); 4.323(0.7); 3.943(0.6); 3.916(0.7); 3.905(0.6); 3.896(0.6); 3.889(0.4); 3.879(0.6); 3.869(0.7); 3.859(0.6); 3.832(0.5); 3.329(73.0); 2.676(0.6); 2.671(0.9); 2.667(0.6); 2.524(2.2); 2.506(100.5); 2.502(132.5); 2.498(98.0); 2.434(16.0); 2.333(0.6); 2.329(0.9); 2.324(0.7); 2.320(0.5); 0.000(1.5) 101 3.96 4.09 (400.0 MHz, d.sub.6-DMSO): δ = 7.702(1.3); 7.684(1.4); 7.649(1.8); 7.460(1.2); 7.434(1.2); 3.912(0.6); 3.886(1.8); 3.860(1.8); 3.835(0.6); 3.328(23.5); 2.671(0.4); 2.506(47.9); 2.502(62.7); 2.498(47.1); 2.456(7.5); 2.335(0.5); 2.329(0.4); 1.692(0.5); 1.673(1.6); 1.655(1.7); 1.636(0.6); 1.292(16.0); 1.230(0.7); 0.861(2.0); 0.843(4.3); 0.824(1.9); 0.008(1.2); 0.000(34.6) 102 3.84 3.71 (400.0 MHz, d.sub.6-DMSO): δ = 10.263(0.9); 10.248(1.8); 10.232(0.9); 7.730(2.9); 7.712(2.9); 7.491(2.5); 7.464(2.5); 4.755(0.5); 4.714(0.6); 4.644(0.9); 3.897(1.2); 3.871(3.7); 3.845(3.9); 3.820(1.3); 3.328(46.7); 2.675(0.4); 2.671(0.5); 2.666(0.4); 2.524(1.5); 2.511(30.7); 2.506(62.1); 2.502(81.4); 2.497(59.1); 2.493(28.8); 2.468(16.0); 2.333(0.4); 2.329(0.5); 2.324(0.4); 2.075(5.8); 0.008(0.5); 0.000(14.2); −0.009(0.5) 103 3.26 3.25 (400.0 MHz, d.sub.6-DMSO): δ = 8.318(0.6); 8.030(12.2); 7.904(9.6); 7.878(1.4); 7.864(2.8); 7.850(1.4); 4.656(4.3); 4.611(6.1); 4.461(6.2); 4.416(4.1); 4.132(1.5); 4.107(4.8); 4.082(5.0); 4.056(1.8); 3.328(73.7); 3.307(0.4); 3.291(0.8); 3.282(0.7); 3.274(2.1); 3.265(1.9); 3.256(2.4); 3.250(2.4); 3.241(2.0); 3.232(2.1); 3.224(0.7); 3.215(0.8); 2.676(1.0); 2.671(1.4); 2.667(1.0); 2.524(3.3); 2.510(79.0); 2.506(160.6); 2.502(212.5); 2.498(156.1); 2.493(78.0); 2.333(1.0); 2.329(1.4); 2.324(1.0); 1.989(0.7); 1.398(8.4); 1.175(0.4); 1.114(7.4); 1.096(16.0); 1.078(7.3); 1.068(0.6); 0.146(0.4); 0.008(2.7); 0.000(85.3); −0.008(3.5); −0.150(0.4) 104 3.37 3.3 (400.0 MHz, d.sub.6-DMSO): δ = 8.313(0.4); 8.018(16.0); 7.882(15.1); 7.780(6.1); 7.773(6.6); 4.658(6.3); 4.613(9.5); 4.469(9.7); 4.424(6.3); 4.120(2.8); 4.095(8.5); 4.070(8.8); 4.044(3.1); 4.020(0.5); 3.318(112.5); 2.715(0.6); 2.706(1.5); 2.698(2.6); 2.688(3.6); 2.680(4.0); 2.671(3.7); 2.663(2.2); 2.501(154.6); 2.498(125.0); 2.328(1.0); 1.988(1.7); 1.398(9.9); 1.193(0.5); 1.175(0.9); 1.158(0.4); 0.732(1.1); 0.714(7.8); 0.701(7.3); 0.697(7.2); 0.684(1.9); 0.609(0.4); 0.591(0.7); 0.582(0.9); 0.570(4.4); 0.561(8.2); 0.553(8.1); 0.518(0.6); 0.146(0.5); 0.000(101.9); −0.150(0.5) 105 3.99 3.91 (400.0 MHz, d.sub.6-DMSO): δ = 8.025(5.8); 7.906(5.5); 7.857(1.0); 7.842(2.1); 7.828(1.2); 4.663(2.2); 4.618(3.4); 4.470(3.4); 4.425(2.2); 4.130(1.0); 4.105(3.2); 4.080(3.3); 4.055(1.2); 3.321(68.8); 3.143(0.3); 3.128(0.7); 3.111(1.3); 3.095(1.8); 3.078(1.7); 3.060(1.7); 3.044(1.3); 3.028(0.7); 3.012(0.4); 2.671(0.3); 2.502(48.4); 1.825(0.5); 1.808(1.0); 1.792(1.3); 1.775(1.1); 1.758(0.6); 1.398(9.9); 0.883(16.0); 0.867(15.7); 0.002(22.6); 0.000(26.7) 106 3.53 3.5 (400.0 MHz, d.sub.6-DMSO): δ = 10.398(0.4); 8.485(0.6); 8.330(2.4); 8.314(5.2); 8.298(2.5); 8.038(16.0); 8.024(0.8); 7.913(14.0); 7.876(0.7); 4.718(6.0); 4.674(8.5); 4.617(0.4); 4.509(8.6); 4.490(1.1); 4.464(5.9); 4.171(0.7); 4.154(1.2); 4.148(1.1); 4.125(3.5); 4.117(2.6); 4.100(8.8); 4.075(9.5); 4.062(2.9); 4.050(4.0); 4.038(3.1); 4.021(1.3); 4.015(1.4); 4.001(0.8); 3.347(0.7); 3.321(211.5); 3.292(0.5); 2.671(0.8); 2.502(123.2); 2.498(97.3); 2.329(0.8); 1.988(1.8); 1.398(8.1); 1.193(0.5); 1.175(1.0); 1.158(0.5); 0.883(1.7); 0.867(1.7); 0.146(0.4); 0.000(79.7); −0.150(0.4) 107 3.90 3.86 (400.0 MHz, d.sub.6-DMSO): δ = 8.353(1.5); 8.339(2.9); 8.324(1.5); 8.025(7.6); 8.016(1.2); 7.901(7.4); 7.340(16.0); 7.330(16.0); 7.275(1.6); 7.264(2.5); 7.254(2.3); 7.243(1.6); 7.150(0.3); 4.678(3.0); 4.633(4.4); 4.480(5.0); 4.452(2.9); 4.435(5.7); 4.427(3.4); 4.411(2.8); 4.388(0.8); 4.374(0.7); 4.322(0.3); 4.122(1.4); 4.097(4.2); 4.072(4.4); 4.046(1.5); 3.318(50.8); 3.309(7.3); 2.670(0.7); 2.505(91.2); 2.501(99.6); 2.328(0.7); 1.988(0.4); 1.398(2.7); 0.000(51.9); −0.008(8.6) 108 4.20 4.09 (400.0 MHz, d.sub.6-DMSO): δ = 9.783(7.7); 8.313(0.6); 8.056(16.0); 7.952(0.5); 7.929(12.4); 7.831(0.4); 7.605(0.5); 7.596(5.1); 7.591(2.0); 7.584(5.5); 7.579(3.3); 7.573(6.1); 7.567(2.1); 7.561(5.8); 7.552(0.6); 7.236(0.6); 7.227(5.9); 7.222(1.9); 7.215(0.9); 7.205(9.8); 7.189(1.7); 7.183(5.3); 7.174(0.5); 4.770(5.5); 4.725(7.8); 4.590(8.1); 4.545(5.3); 4.495(0.4); 4.136(1.9); 4.110(6.0); 4.085(6.2); 4.060(2.2); 3.343(0.5); 3.318(251.1); 2.675(1.0); 2.671(1.5); 2.666(1.1); 2.662(0.5); 2.524(3.5); 2.519(5.3); 2.510(79.0); 2.506(165.5); 2.501(222.7); 2.497(164.1); 2.492(81.0); 2.333(1.1); 2.328(1.5); 2.324(1.1); 2.319(0.6); 1.988(0.5); 1.398(7.4); 0.146(0.9); 0.008(6.3); 0.000(204.6); −0.009(8.0); −0.150(0.9) 109 4.56 4.49 (400.0 MHz, d.sub.6-DMSO): δ = 9.897(9.1); 8.520(0.4); 8.313(0.5); 8.059(16.0); 7.927(13.6); 7.871(0.6); 7.773(4.4); 7.768(8.3); 7.763(5.0); 7.593(0.5); 7.494(3.0); 7.492(2.9); 7.474(4.3); 7.471(4.5); 7.406(4.5); 7.385(7.6); 7.365(3.7); 7.206(4.1); 7.203(4.1); 7.186(3.3); 7.183(3.4); 4.780(5.6); 4.735(8.2); 4.601(8.5); 4.556(5.5); 4.507(0.6); 4.134(2.2); 4.109(6.9); 4.084(7.2); 4.059(2.5); 4.039(0.3); 4.021(0.3); 3.371(0.4); 3.365(0.4); 3.357(0.8); 3.321(307.7); 2.675(0.9); 2.671(1.2); 2.667(0.9); 2.506(147.4); 2.502(194.8); 2.497(148.1); 2.333(0.9); 2.329(1.2); 1.988(1.2); 1.398(9.4); 1.193(0.3); 1.175(0.7); 1.157(0.3); 0.146(0.7); 0.016(0.6); 0.008(5.7); 0.000(149.8); −0.008(6.5); −0.150(0.7) 110 4.61 4.56 (400.0 MHz, d.sub.6-DMSO): δ = 10.023(6.2); 8.313(0.4); 8.064(16.0); 7.951(0.7); 7.937(9.5); 7.827(2.0); 7.805(2.4); 7.621(1.6); 7.601(3.4); 7.581(1.9); 7.497(2.9); 7.478(2.1); 4.793(4.1); 4.748(5.8); 4.617(6.1); 4.572(3.9); 4.137(1.5); 4.112(4.7); 4.086(4.9); 4.061(1.7); 3.317(49.9); 2.675(0.5); 2.671(0.7); 2.666(0.5); 2.524(1.8); 2.511(40.2); 2.506(81.9); 2.502(109.0); 2.497(81.2); 2.493(41.2); 2.333(0.5); 2.329(0.7); 2.324(0.5); 2.073(0.5); 0.008(0.4); 0.000(11.8); −0.008(0.5) 111 2.59 2.56 (400.0 MHz, d.sub.6-DMSO): δ = 8.209(5.0); 8.207(4.7); 8.127(4.5); 8.123(4.6); 7.848(1.0); 7.834(2.1); 7.820(1.1); 4.617(1.8); 4.613(1.8); 4.572(2.5); 4.569(2.5); 4.494(0.5); 4.471(0.7); 4.467(0.7); 4.456(0.7); 4.444(0.6); 4.433(0.8); 4.430(0.8); 4.404(2.6); 4.396(2.4); 4.359(1.5); 4.352(1.6); 4.075(0.6); 4.064(0.3); 4.048(0.7); 4.037(1.0); 4.022(0.4); 4.010(1.1); 3.999(0.6); 3.983(0.4); 3.972(0.5); 3.316(21.1); 3.295(0.4); 3.277(1.0); 3.268(1.5); 3.264(1.5); 3.250(2.1); 3.237(1.4); 3.232(1.3); 3.220(0.5); 2.670(0.3); 2.506(40.8); 2.501(53.5); 2.497(41.0); 2.328(0.4); 1.398(16.0); 1.236(0.4); 1.120(2.9); 1.115(3.2); 1.102(6.3); 1.097(6.7); 1.085(3.0); 1.079(3.1); 0.008(0.5); 0.000(13.7) 112 2.65 2.61 (400.0 MHz, d.sub.6-DMSO): δ = 8.203(3.5); 8.202(3.3); 8.107(3.3); 8.105(3.2); 7.762(1.3); 7.756(0.9); 4.624(1.1); 4.620(1.1); 4.580(1.5); 4.576(1.5); 4.466(0.3); 4.455(0.4); 4.444(0.4); 4.440(0.4); 4.429(0.5); 4.417(0.5); 4.411(1.6); 4.406(1.6); 4.367(1.0); 4.361(1.0); 4.073(0.3); 4.046(0.4); 4.038(0.4); 4.035(0.4); 4.028(0.4); 4.020(0.4); 4.009(0.4); 4.002(0.5); 3.991(0.3); 3.316(10.5); 2.704(0.5); 2.695(0.8); 2.686(0.9); 2.677(0.8); 2.669(0.7); 2.660(0.3); 2.524(0.5); 2.519(0.8); 2.510(11.9); 2.506(24.4); 2.501(32.4); 2.497(23.8); 2.492(11.8); 1.988(0.8); 1.398(16.0); 1.175(0.4); 0.722(1.1); 0.718(1.1); 0.711(1.4); 0.704(1.1); 0.700(1.2); 0.694(0.9); 0.565(0.8); 0.555(1.9); 0.548(1.7); 0.539(1.1); 0.533(0.5); 0.000(10.0); −0.009(0.4) 113 3.28 3.21 (400.0 MHz, d.sub.6-DMSO): δ = 8.210(3.5); 8.137(2.6); 8.128(2.5); 7.836(0.4); 7.825(0.8); 7.822(0.8); 7.810(0.4); 4.625(1.1); 4.622(1.0); 4.581(1.5); 4.578(1.4); 4.477(0.3); 4.473(0.3); 4.450(0.4); 4.446(0.4); 4.439(0.4); 4.436(0.4); 4.410(1.6); 4.404(1.4); 4.365(0.9); 4.359(0.9); 4.078(0.3); 4.062(0.3); 4.052(0.5); 4.041(0.3); 4.035(0.4); 4.025(0.4); 4.014(0.3); 3.316(17.1); 3.116(0.5); 3.110(0.5); 3.100(0.6); 3.093(0.6); 3.084(0.4); 3.078(0.6); 3.068(0.4); 3.064(0.6); 3.053(0.5); 3.047(0.5); 3.037(0.5); 2.524(0.5); 2.510(13.7); 2.506(28.1); 2.501(37.5); 2.497(27.7); 2.492(13.7); 1.808(0.4); 1.805(0.4); 1.792(0.5); 1.788(0.5); 1.775(0.4); 1.771(0.4); 1.398(16.0); 0.888(6.3); 0.882(6.8); 0.872(6.2); 0.866(6.5); 0.000(10.8); −0.009(0.4) 114 2.91 2.88 (400.0 MHz, d.sub.6-DMSO): δ = 8.801(0.4); 8.310(1.0); 8.294(2.0); 8.278(1.0); 8.222(5.2); 8.219(5.1); 8.152(4.6); 8.144(4.6); 8.052(0.4); 4.686(1.8); 4.680(1.8); 4.641(2.3); 4.636(2.4); 4.500(0.9); 4.477(0.7); 4.474(0.8); 4.463(0.8); 4.450(0.8); 4.440(3.0); 4.431(2.4); 4.413(0.9); 4.396(1.6); 4.386(1.9); 4.156(0.4); 4.134(0.6); 4.117(1.0); 4.111(0.8); 4.101(0.8); 4.094(1.3); 4.079(1.4); 4.070(1.4); 4.053(1.5); 4.045(1.4); 4.034(0.7); 4.026(0.7); 4.018(1.2); 4.008(0.7); 3.991(0.4); 3.981(0.6); 3.318(61.4); 2.675(0.3); 2.670(0.4); 2.666(0.3); 2.523(1.1); 2.510(24.8); 2.506(49.8); 2.501(65.5); 2.115497(49.0); 2.492(25.0); 2.328(0.4); 1.988(0.9); 1.398(16.0); 1.175(0.5); 0.888(0.4); 0.882(0.4); 0.872(0.4); 0.865(0.4); 0.008(0.6); 0.000(17.7) 115 3.29 3.23 (400.0 MHz, d.sub.6-DMSO): δ = 8.335(1.0); 8.320(2.3); 8.310(2.3); 8.296(1.0); 8.209(7.9); 8.206(7.7); 8.135(7.5); 8.125(7.4); 7.342(11.9); 7.336(13.8); 7.331(16.0); 7.326(14.1); 7.304(0.4); 7.278(1.1); 7.268(1.9); 7.257(2.4); 7.248(1.9); 7.238(1.0); 7.236(0.9); 7.227(0.4); 4.642(3.9); 4.597(5.4); 4.499(0.8); 4.489(0.8); 4.482(1.4); 4.471(1.6); 4.462(2.5); 4.452(3.0); 4.445(3.8); 4.434(4.5); 4.429(3.7); 4.424(5.1); 4.416(7.3); 4.407(1.6); 4.396(0.9); 4.391(1.1); 4.380(3.5); 4.371(2.8); 4.075(1.0); 4.065(0.5); 4.055(0.4); 4.048(1.2); 4.038(2.1); 4.029(0.5); 4.020(1.1); 4.013(1.6); 4.002(1.2); 3.986(0.6); 3.976(0.9); 3.317(35.3); 2.674(0.4); 2.670(0.5); 2.666(0.4); 2.523(1.2); 2.509(28.8); 2.505(58.2); 2.501(77.1); 2.496(57.8); 2.332(0.4); 2.328(0.5); 2.323(0.4); 1.988(2.6); 1.398(4.1); 1.193(0.7); 1.175(1.4); 1.157(0.7); 0.008(0.8); 0.000(22.4); −0.008(0.9) 116 3.46 3.39 (400.0 MHz, d.sub.6-DMSO): δ = 9.782(2.5); 9.778(2.7); 8.239(7.3); 8.160(7.9); 7.598(1.6); 7.595(1.8); 7.585(1.8); 7.582(2.0); 7.575(2.2); 7.572(1.9); 7.563(2.0); 7.560(1.8); 7.232(1.6); 7.224(1.7); 7.219(0.7); 7.210(2.6); 7.202(2.8); 7.194(0.7); 7.188(1.5); 7.180(1.5); 4.743(1.6); 4.739(1.6); 4.699(2.2); 4.694(2.1); 4.531(2.1); 4.526(2.3); 4.504(0.5); 4.487(1.8); 4.481(1.8); 4.467(0.6); 4.458(0.6); 4.448(0.7); 4.440(0.6); 4.421(0.6); 4.099(0.5); 4.073(0.7); 4.062(0.5); 4.049(0.6); 4.035(0.6); 4.022(0.6); 4.011(0.5); 3.985(0.5); 3.317(29.7); 2.670(0.4); 2.524(0.9); 2.519(1.4); 2.510(21.4); 2.506(44.2); 2.501(58.9); 2.497(43.4); 2.492(21.4); 2.328(0.4); 1.398(16.0); 0.008(0.6); 0.000(17.9); −0.008(0.6) 117 3.89 3.81 (400.0 MHz, d.sub.6-DMSO): δ = 9.897(0.7); 9.892(0.7); 8.241(2.2); 8.159(2.2); 7.771(0.4); 7.767(0.8); 7.763(0.8); 7.758(0.4); 7.494(0.3); 7.492(0.4); 7.473(0.5); 7.471(0.5); 7.390(0.5); 7.381(0.5); 7.202(0.5); 7.183(0.4); 4.752(0.5); 4.748(0.4); 4.708(0.6); 4.704(0.6); 4.542(0.6); 4.537(0.6); 4.498(0.4); 4.492(0.5); 3.317(6.4); 2.524(0.4); 2.510(7.3); 2.506(14.1); 2.501(18.0); 2.497(13.2); 2.493(6.5); 1.398(16.0); 0.000(5.2) 118 2.50 2.46 (400.0 MHz, d.sub.6-DMSO): δ = 10.360(1.9); 10.326(1.8); 8.332(2.1); 8.330(2.0); 8.317(4.9); 8.021(1.5); 8.018(1.6); 8.016(1.6); 8.000(2.3); 7.997(2.3); 7.995(2.2); 7.901(0.9); 7.896(1.5); 7.892(1.0); 7.882(7.4); 7.862(0.6); 7.857(1.1); 7.852(0.6); 7.428(5.2); 7.193(1.0); 7.191(1.1); 7.186(1.0); 7.174(1.8); 7.162(1.0); 7.160(1.1); 4.634(1.6); 4.627(1.6); 4.591(2.5); 4.584(2.6); 4.492(2.6); 4.479(2.5); 4.448(1.5); 4.436(1.5); 4.317(0.6); 4.307(0.3); 4.301(0.6); 4.290(0.8); 4.281(0.7); 4.273(0.7); 4.264(0.8); 4.253(0.7); 4.247(0.4); 4.236(0.6); 3.850(0.6); 3.834(0.7); 3.823(0.9); 3.813(0.7); 3.807(0.8); 3.797(0.8); 3.786(0.6); 3.770(0.6); 3.328(328.0); 2.680(2.2); 2.676(4.1); 2.671(5.8); 2.667(4.3); 2.604(0.4); 2.573(0.6); 2.525(14.3); 2.520(21.6); 2.511(315.2); 2.507(659.0); 2.502(876.5); 2.498(638.1); 2.493(311.7); 2.394(16.0); 2.338(2.0); 2.333(4.1); 2.329(5.7); 2.324(4.2); 2.320(2.1); 2.288(0.6); 2.255(14.5); 2.075(0.8); 1.148(0.4); 0.146(1.4); 0.008(10.5); 0.000(355.8); −0.008(13.2); −0.150(1.4) 119 2.65 2.65 (400.0 MHz, d.sub.6-DMSO): δ = 10.276(2.4); 10.240(2.3); 8.336(2.0); 8.334(2.0); 8.324(2.0); 8.313(0.6); 8.092(4.9); 8.090(4.9); 8.011(1.4); 8.008(1.4); 8.005(1.4); 7.990(2.0); 7.987(2.0); 7.984(2.0); 7.904(0.8); 7.900(1.4); 7.895(0.8); 7.881(1.8); 7.865(0.6); 7.860(1.0); 7.856(0.6); 7.811(5.7); 7.196(1.1); 7.182(1.7); 7.166(1.0); 5.753(1.7); 4.768(1.6); 4.759(1.6); 4.723(2.2); 4.715(2.2); 4.550(2.3); 4.538(2.2); 4.506(1.5); 4.494(1.5); 4.403(0.5); 4.385(0.5); 4.376(0.8); 4.366(0.7); 4.359(0.7); 4.349(0.8); 4.339(0.7); 4.321(0.6); 3.944(0.7); 3.939(0.7); 3.917(0.8); 3.912(0.9); 3.907(0.8); 3.902(0.7); 3.890(0.3); 3.880(0.7); 3.875(0.6); 3.317(123.4); 2.675(0.8); 2.670(1.1); 2.666(0.8); 2.540(0.5); 2.523(3.1); 2.506(129.8); 2.501(168.4); 2.497(125.9); 2.436(16.0); 2.416(0.5); 2.332(0.8); 2.328(1.1); 2.324(0.8); 1.235(0.5); 0.007(2.8); 0.000(67.1); −0.008(3.2) 120 4.02 3.92 (400.0 MHz, d.sub.6-DMSO): δ = 10.021(2.1); 10.017(2.3); 8.313(0.5); 8.246(5.1); 8.165(7.1); 8.061(1.5); 7.822(1.1); 7.802(1.3); 7.625(0.5); 7.617(0.5); 7.605(0.9); 7.597(1.0); 7.585(0.5); 7.577(0.5); 7.495(1.1); 7.475(0.8); 4.764(1.3); 4.759(1.2); 4.719(1.8); 4.715(1.7); 4.557(1.7); 4.553(1.9); 4.513(1.6); 4.508(1.4); 4.487(0.7); 4.477(0.6); 4.461(0.6); 4.450(0.9); 4.424(0.6); 4.102(0.5); 4.075(0.5); 4.064(0.5); 4.038(0.7); 4.010(0.6); 3.999(0.4); 3.972(0.4); 3.317(86.6); 2.675(0.7); 2.671(0.9); 2.666(0.7); 2.661(0.3); 2.524(2.1); 2.510(50.2); 2.506(103.2); 2.501(137.0); 2.497(99.8); 2.492(48.4); 2.333(0.6); 2.328(0.9); 2.324(0.7); 1.398(16.0); 0.146(0.5); 0.008(3.9); 0.000(116.5); −0.008(4.1); −0.150(0.5) 121 3.03 2.99 (400.0 MHz, d.sub.6-DMSO): δ = 7.716(2.3); 7.697(2.3); 7.436(2.0); 7.409(2.0); 5.753(3.2); 4.554(8.3); 3.925(0.9); 3.899(2.9); 3.874(3.0); 3.848(1.0); 3.318(27.5); 2.945(16.0); 2.898(0.7); 2.885(1.0); 2.871(0.8); 2.524(0.8); 2.510(17.0); 2.506(34.5); 2.501(45.9); 2.497(34.3); 2.446(12.5); 2.073(4.3); 0.720(2.6); 0.703(2.1); 0.000(5.6) 122 2.62 2.58 (400.0 MHz, d.sub.6-DMSO): δ = 7.734(2.9); 7.715(3.0); 7.437(2.6); 7.410(2.6); 4.529(10.2); 3.911(1.2); 3.885(3.8); 3.8594.0); (3.833(1.4); 3.641(3.8); 3.630(6.3); 3.618(5.1); 3.484(4.5); 3.473(5.7); 3.463(3.5); 3.316(9.9); 2.506(34.5); 2.501(46.3); 2.497(35.3); 2.472(0.4); 2.467(0.4); 2.449(16.0); 2.073(0.4); 0.000(5.8) 123 1.51 2.5 (400.0 MHz, d.sub.6-DMSO): δ = 7.734(2.9); 7.716(3.0); 7.436(2.5); 7.409(2.5); 5.753(0.4); 4.517(9.4); 3.913(1.2); 3.888(3.7); 3.862(3.9); 3.836(1.3); 3.462(4.8); 3.317(23.0); 2.670(0.4); 2.524(1.1); 2.510(22.0); 2.506(44.8); 2.502(59.5); 2.497(44.7); 2.449(16.0); 2.361(3.7); 2.349(5.4); 2.337(3.7); 2.191(14.2); 2.073(0.4); 1.235(0.5); 0.000(3.2) 124 3.59 3.53 (400.0 MHz, d.sub.6-DMSO): δ = 7.740(2.9); 7.722(2.9); 7.438(2.6); 7.411(2.6); 4.496(10.4); 3.919(1.2); 3.893(3.8); 3.868(3.9); 3.842(1.4); 3.317(21.4); 3.208(1.0); 2.993(9.2); 2.671(0.3); 2.505(38.3); 2.502(50.4); 2.498(42.0); 2.450(16.0); 2.328(0.3); 2.073(0.8); 1.984(0.5); 1.967(0.9); 1.950(1.2); 1.933(1.0); 1.916(0.5); 0.869(14.8); 0.852(14.7); 0.000(1.7) 125 1.79 1.75 (400.0 MHz, d.sub.6-DMSO): δ = 8.052(3.0); 8.034(3.0); 7.545(2.6); 7.519(2.5); 5.753(15.6); 4.528(8.2); 4.327(0.9); 4.318(0.4); 4.300(1.1); 4.291(1.2); 4.273(0.4); 4.263(1.1); 4.236(0.4); 3.884(1.1); 3.874(0.4); 3.857(1.2); 3.847(1.0); 3.831(0.5); 3.820(1.0); 3.794(0.3); 3.642(4.0); 3.631(6.5); 3.619(5.3); 3.492(5.1); 3.481(6.4); 3.470(3.8); 3.317(46.0); 2.670(0.5); 2.506(60.3); 2.501(78.5); 2.497(58.6); 2.427(16.0); 2.328(0.5); 0.008(2.4); 0.000(62.8) 126 2.66 2.6 (400.0 MHz, d.sub.6-DMSO): δ = 8.059(2.9); 8.041(2.9); 7.548(2.6); 7.521(2.6); 5.753(12.4); 4.494(9.3); 4.324(0.9); 4.315(0.4); 4.297(1.0); 4.288(1.1); 4.270(0.4); 4.260(1.1); 4.233(0.3); 3.904(0.9); 3.894(0.4); 3.877(1.0); 3.867(0.9); 3.850(0.4); 3.840(0.9); 3.317(39.3); 3.216(1.4); 3.000(7.8); 2.670(0.4); 2.505(49.1); 2.501(63.0); 2.430(16.0); 2.328(0.4); 1.984(0.5); 1.967(0.9); 1.950(1.2); 1.934(1.0); 1.916(0.5); 1.235(0.5); 0.872(15.4); 0.855(15.0); 0.008(1.9); 0.000(46.9) 127 1.61 1.72 (400.0 MHz, d.sub.6-DMSO): δ = 13.321(0.7); 8.314(0.6); 7.902(16.0); 7.898(13.8); 7.893(9.5); 7.886(9.4); 7.740(1.3); 7.721(1.5); 7.716(4.8); 7.713(5.3); 7.711(4.8); 7.708(4.2); 7.696(5.9); 7.693(6.3); 7.691(6.3); 7.565(8.5); 7.558(1.4); 7.551(1.5); 7.544(14.1); 7.535(1.3); 7.524(6.1); 7.453(1.1); 7.440(0.4); 7.426(1.0); 7.413(0.4); 4.535(3.4); 4.519(1.2); 4.087(0.8); 4.051(1.0); 3.897(0.6); 3.885(0.6); 3.871(1.5); 3.859(0.7); 3.846(1.5); 3.820(0.6); 3.738(2.1); 3.648(0.5); 3.639(0.6); 3.614(0.7); 3.602(0.6); 3.586(0.5); 3.578(0.5); 3.538(4.7); 3.520(1.1); 3.507(1.7); 3.320(19.9); 2.676(1.1); 2.671(1.6); 2.667(1.2); 2.524(4.1); 2.507(186.3); 2.502(245.9); 2.498(184.1); 2.461(6.7); 2.451(2.6); 2.434(1.0); 2.333(1.7); 2.329(2.0); 2.325(1.4); 1.337(0.5); 1.298(1.2); 1.259(2.0); 1.235(5.5); 1.203(0.7); 1.187(1.0); 1.166(1.0); 1.149(0.5); 0.870(0.5); 0.862(0.5); 0.854(1.0); 0.845(0.7); 0.837(0.5); 0.826(0.6); 0.146(1.0); 0.008(7.5); 0.000(207.3); −0.150(1.0) 128 2.44 2.4 (400.0 MHz, d.sub.6-DMSO): δ = 7.742(3.0); 7.724(3.0); 7.447(2.6); 7.420(2.6); 4.543(5.8); 3.901(1.6); 3.875(8.5); 3.850(5.3); 3.824(1.5); 3.316(28.2); 3.280(5.3); 2.671(0.5); 2.505(56.3); 2.501(72.1); 2.497(54.9); 2.455(16.0); 2.328(0.5); 2.073(8.8); 1.235(0.7); 0.007(2.4); 0.000(52.2) 129 3.29 3.27 (400.0 MHz, d.sub.6-DMSO): δ = 7.743(2.9); 7.725(2.9); 7.442(2.5); 7.415(2.5); 5.753(3.9); 4.534(8.0); 3.909(1.2); 3.884(3.8); 3.858(3.9); 3.832(1.4); 3.584(3.2); 3.570(4.8); 3.556(3.4); 3.319(23.4); 2.524(0.8); 2.510(18.1); 2.506(37.1); 2.501(49.4); 2.497(36.7); 2.493(18.7); 2.452(15.7); 2.328(0.3); 2.105(1.2); 2.084(2.0); 2.073(16.0); 2.055(1.9); 2.034(1.3); 2.022(0.8); 0.008(2.4); 0.000(64.0); −0.009(3.0) 130 2.60 2.58 (400.0 MHz, d.sub.6-DMSO): δ = 7.734(1.9); 7.716(1.9); 7.438(1.6); 7.411(1.6); 5.753(0.9); 4.498(7.6); 3.918(0.8); 3.892(2.5); 3.867(2.6); 3.841(0.9); 3.317(25.5); 2.973(16.0); 2.506(36.5); 2.501(47.2); 2.497(35.0); 2.447(10.4); 0.008(0.4); 0.000(9.1); −0.008(0.5) 131 2.16 2.08 (400.0 MHz, d.sub.6-DMSO): δ = 8.033(2.6); 8.015(2.6); 7.547(2.2); 7.521(2.1); 5.753(0.7); 4.558(8.4); 4.326(0.8); 4.317(0.4); 4.299(0.9); 4.289(1.0); 4.272(0.4); 4.262(1.0); 3.909(0.9); 3.899(0.4); 3.882(1.0); 3.872(0.9); 3.855(0.4); 3.845(0.8); 3.317(17.0); 2.950(16.0); 2.912(0.3); 2.899(0.8); 2.886(1.1); 2.871(0.9); 2.505(29.9); 2.501(38.5); 2.497(29.5); 2.428(13.4); 2.085(7.2); 2.073(2.8); 1.235(0.5); 0.725(3.7); 0.709(2.9); 0.000(4.5) 132 2.46 2.41 (400.0 MHz, d.sub.6-DMSO): δ = 8.062(3.1); 8.044(3.1); 7.550(2.6); 7.523(2.5); 5.753(13.0); 4.533(6.9); 4.332(1.0); 4.322(0.4); 4.305(1.1); 4.295(1.2); 4.277(0.5); 4.268(1.2); 4.240(0.4); 3.881(1.1); 3.871(0.4); 3.854(1.3); 3.844(1.1); 3.827(0.5); 3.817(1.0); 3.791(0.3); 3.590(3.6); 3.577(5.4); 3.563(3.7); 3.316(34.0); 2.675(0.3); 2.670(0.4); 2.666(0.3); 2.506(53.2); 2.501(69.4); 2.497(52.2); 2.428(16.0); 2.332(0.4); 2.328(0.5); 2.323(0.4); 2.104(1.4); 2.086(4.0); 2.073(8.0); 2.056(2.1); 2.036(1.5); 1.234(0.5); 0.008(0.4); 0.000(9.6) 133 1.78 1.75 (400.0 MHz, d.sub.6-DMSO): δ = 8.052(2.1); 8.033(2.1); 7.548(1.7); 7.522(1.7); 5.753(0.7); 4.498(7.0); 4.330(0.7); 4.303(0.8); 4.294(0.8); 4.276(0.3); 4.266(0.8); 3.890(0.8); 3.863(0.9); 3.853(0.7); 3.836(0.3); 3.826(0.7); 3.317(22.7); 2.978(16.0); 2.505(35.6); 2.501(45.7); 2.497(34.4); 2.428(10.9); 2.086(1.6); 2.073(2.7); 0.000(3.4) 134 1.69 1.66 (400.0 MHz, d.sub.6-DMSO): δ = 8.063(3.0); 8.045(2.9); 7.553(2.7); 7.526(2.6); 5.753(3.8); 4.544(5.5); 4.363(0.3); 4.336(1.0); 4.327(0.6); 4.309(1.2); 4.299(1.3); 4.281(0.6); 4.272(1.2); 4.245(0.4); 3.872(7.0); 3.845(1.8); 3.835(1.3); 3.817(0.7); 3.808(1.1); 3.781(0.4); 3.506(0.4); 3.316(38.3); 3.282(6.9); 2.670(0.8); 2.501(112.4); 2.426(16.0); 2.328(0.8); 2.073(2.0); 1.235(0.9); 0.000(4.4) 135 2.44 2.4 (400.0 MHz, d.sub.6-DMSO): δ = 8.326(0.9); 8.310(1.9); 8.294(0.9); 8.037(2.7); 8.019(2.7); 7.582(2.1); 7.555(2.1); 4.494(0.7); 4.355(0.8); 4.345(0.4); 4.328(0.9); 4.318(1.0); 4.300(0.4); 4.291(1.0); 4.264(0.3); 4.129(0.4); 4.106(1.1); 4.089(1.3); 4.083(1.3); 4.066(1.1); 4.043(0.4); 3.880(0.7); 3.853(0.8); 3.843(0.7); 3.827(0.3); 3.817(0.6); 3.317(81.6); 2.674(0.4); 2.670(0.5); 2.666(0.4); 2.523(1.3); 2.510(34.3); 2.506(69.0); 2.501(90.5); 2.497(66.0); 2.435(13.5); 2.332(0.4); 2.328(0.6); 2.323(0.4); 2.073(16.0); 0.008(1.2); 0.000(32.8); −0.008(1.2) 136 2.43 2.4 (400.0 MHz, d.sub.6-DMSO): δ = 8.327(0.8); 8.311(1.7); 8.294(0.8); 8.037(2.5); 8.019(2.5); 7.582(2.0); 7.555(1.9); 4.495(0.6); 4.493(0.6); 4.355(0.8); 4.345(0.3); 4.328(0.9); 4.318(0.9); 4.301(0.4); 4.291(0.9); 4.129(0.3); 4.106(1.0); 4.089(1.1); 4.083(1.2); 4.065(1.0); 4.043(0.3); 3.880(0.6); 3.853(0.7); 3.843(0.6); 3.816(0.6); 3.318(40.5); 2.670(0.4); 2.523(1.0); 2.510(25.0); 2.506(50.7); 2.501(66.5); 2.496(47.9); 2.492(22.9); 2.435(12.5); 2.328(0.4); 2.073(16.0); 0.008(1.0); 0.000(26.4); 0.009(0.9)

[0505] Furthermore, the following compounds of the formula (II) (cf. Table 3) were prepared by the processes described above.

TABLE-US-00003 TABLE 3 Compounds of the formula (II) (II) [00035] Compound .sup.1H NMR(400.0 MHz, number n Y X V.sup.1 R.sup.1 R.sup.2 logP[a] logP[b] D6-DMSO) IIa-1 0 CH.sub.3 F O H H 2.11 2.08 8.42(bs, 1H), 7.62(d, 1H), 7.39(d, 1H), 4.15(broad, 2H), 3.91(q, 2H), 2.43(s, 3H) IIa-2 0 CH.sub.3 F S H H 2.53 2.50 10.56(s, 1H), 7.61(d, 1H), 7.39(d, 1H), 4.48- 4.30(m, 2H), 3.93- 3.85(m, 2H), 2.44(s, 3H) IIb-1 1 CH.sub.3 F O H H 1.33 1.31 8.47(bs, 1H), 7.89(d, 1H), 7.50(d, 1H), 4.31- 4.21(m, 1H), 4.16(broad, 2H), 3.96- 3.87(m, 1H), 2.42(s, 3H) IIa-3 0 CH.sub.3 F O CH.sub.3 H 2.34 2.31 8.56(s, 1H), 7.64(d, 1H), 7.39(d, 1H), 4.35- 4.33(m, 1H), 3.96- 3.88(m, 2H), 2.43(s, 3H), 1.36 (d, 3H) IIa-4 0 CH.sub.3 F S CH.sub.3 H 2.79 2.71 4.121(1.4); 4.108(4.2); 4.095(4.2); 4.081(1.5); 3.923(0.3); 3.898(0.4); 3.345(6.4); 3.178(16.0); 3.164(15.1); 2.512(1.6); 2.508(3.3); 2.504(4.4); 2.499(3.3); 2.443(2.4); 1.427(0.7); 1.410(0.7); 1.385(0.8); 1.367(0.8); 0.000(4.4) IIa-5 0 CH.sub.3 F O CH.sub.3 CH.sub.3 2.61 2.53 8.66(s, 1H), 7.67(d, 1H), 7.38(d, 1H), 3.96- 3.91(m, 2H), 2.43(s, 3H), 1.41(s, 6H) IIa-6 0 CH.sub.3 CH.sub.3 O H H 2.21 2.13 8.288(2.6); 7.383(5.6); 7.257(4.5); 4.181(1.3); 4.136(3.3); 4.084(3.1); 4.082(3.2); 4.039(1.2); 4.037(1.2); 3.923(1.2); 3.897(3.7); 3.871(3.8); 3.845(1.3); 3.331(51.4); 2.671(0.3); 2.524(0.8); 2.506(40.7); 2.502(52.9); 2.498(39.1); 2.375(15.4); 2.329(0.4); 2.062(16.0); 0.008(0.7); 0.000(19.9) −0.008(0.9) IIa-7 0 Cl Cl O H H 2.36 2.31 8.472(7.9); 7.951(16.0); 7.831(15.9); 4.255(4.1); 4.209(9.7); 4.196(2.9); 4.170(8.1); 4.147(13.7); 4.119(2.9); 4.103(4.0); 4.038(0.7); 4.021(0.8); 3.317(38.2); 2.671(0.7); 2.502(110.4); 2.498(87.7); 2.328(0.7); 1.988(3.0); 1.193(0.8); 1.175(1.6); 1.158(0.8); 0.146(0.4); 0.000(71.1); −0.150(0.4) IIa-8 0 CH.sub.3 Cl O H H 2.23 2.19 8.401(2.7); 7.643(6.4); 7.583(5.3); 4.222(1.3); 4.220(1.3); 4.175(3.6); 4.133(3.3); 4.131(3.5); 4.088(1.2); 4.085(1.2); 4.053(1.1); 4.027(3.3); 4.002(3.4); 3.976(1.2); 3.345(13.3); 2.524(0.7); 2.520(1.1); 2.511(16.2); 2.507(33.6); 2.502(44.7); 2.497(32.8); 2.493(16.2); 2.392(16.0); 2.333(0.3); 2.329(0.4); 1.056(0.5); 0.008(0.7); 0.000(22.8); −0.009(0.9)

Use Examples

[0506] 1. Boophilus microplus—Injection Test
Solvent: dimethyl sulphoxide

[0507] To produce a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of solvent and the concentrate is diluted with solvent to the desired concentration.

[0508] 1 μl of the active compound solution is injected into the abdomen of 5 engorged adult female cattle ticks (Boophilus microplus). The animals are transferred into dishes and kept in a climate-controlled room.

[0509] Efficacy is assessed after 7 days by laying of fertile eggs. Eggs which are not visibly fertile are stored in a climate-controlled cabinet until the larvae hatch after about 42 days. An efficacy of 100% means that none of the ticks has laid any fertile eggs; 0% means that all the eggs are fertile.

[0510] In this test, for example, the following compounds of the Preparation Examples showed an efficacy of 100% at an application rate of 20 μg/animal: 1, 6, 7, 9, 10, 15, 21, 23, 27, 28, 29, 36, 41, 42, 43, 46, 47, 48, 54, 62, 63, 68, 72, 79, 88, 89, 91, 99

2. Meloidogyne incognita—Test
Solvent: 125.0 parts by weight of acetone

[0511] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and the concentrate is diluted with water to the desired concentration.

[0512] Vessels are filled with sand, active compound solution, an egg/larvae suspension of the southern root-knot nematode (Meloidogyne incognita) and lettuce seeds. The lettuce seeds germinate and the plants develop. The galls develop on the roots.

[0513] After 14 days, the nematicidal efficacy in % is determined by the formation of galls. 100% means that no galls were found; 0% means that the number of galls on the treated plants corresponds to the untreated control.

[0514] In this test, for example, the following compounds of the Preparation Examples showed an efficacy of 100% at an application rate of 20 ppm: 9, 10, 20, 23, 43, 47, 54, 78, 125, 126, 128, 129, 130, 131, 132

[0515] In this test, for example, the following compounds of the Preparation Examples showed an efficacy of 90% at an application rate of 20 ppm: 1, 6, 7, 21, 36, 42, 48, 50, 68, 71, 72, 99, 101, 103, 108, 121, 122

3. Myzus persicae—Spray Test
Solvent: 78 parts by weight of acetone [0516] 1.5 parts by weight of dimethylformamide
Emulsifier: alkylaryl polyglycol ether

[0517] To produce a suitable preparation of active compound, 1 part by weight of active compound is dissolved using the stated parts by weight of solvent and made up with water containing an emulsifier concentration of 1000 ppm until the desired concentration is attained. To produce further test concentrations, the preparation is diluted with emulsifier-containing water.

[0518] Discs of Chinese cabbage leaves (Brassica pekinensis) infested by all stages of the green peach aphid (Myzus persicae) are sprayed with an active compound preparation of the desired concentration.

[0519] After 6 days, the efficacy in % is determined. 100% means that all the aphids have been killed; 0% means that no aphids have been killed.

[0520] In this test, for example, the following compounds from the preparation examples showed an efficacy of 90% at an application rate of 500 g/ha: 46

4. Phaedon cochleariae—Spray Test
Solvent: 78.0 parts by weight of acetone [0521] 1.5 parts by weight of dimethylformamide
Emulsifier: alkylaryl polyglycol ether

[0522] To produce a suitable preparation of active compound, 1 part by weight of active compound is dissolved using the stated parts by weight of solvent and made up with water containing an emulsifier concentration of 1000 ppm until the desired concentration is attained. To produce further test concentrations, the preparation is diluted with emulsifier-containing water.

[0523] Discs of Chinese cabbage leaves (Brassica pekinensis) are sprayed with an active compound preparation of the desired concentration and, after drying, populated with larvae of the mustard beetle (Phaedon cochleariae).

[0524] After 7 days, the efficacy in % is determined. 100% means that all the beetle larvae have been killed; 0% means that no beetle larvae have been killed.

[0525] In this test, for example, the following compounds from the preparation examples showed an efficacy of 100% at an application rate of 500 g/ha: 38, 39, 44, 54, 71, 72, 79, 118

[0526] In this test, for example, the following compounds from the preparation examples showed an efficacy of 83% at an application rate of 500 g/ha: 30, 37, 43, 48, 53, 101, 106

5. Tetranychus urticae—Spray Test, OP-Resistant
Solvent: 78.0 parts by weight of acetone [0527] 1.5 parts by weight of dimethylformamide
Emulsifier: alkylaryl polyglycol ether

[0528] To produce a suitable preparation of active compound, 1 part by weight of active compound is dissolved using the stated parts by weight of solvent and made up with water containing an emulsifier concentration of 1000 ppm until the desired concentration is attained. To produce further test concentrations, the preparation is diluted with emulsifier-containing water.

[0529] Discs of bean leaves (Phaseolus vulgaris) infested with all stages of the greenhouse red spider mite (Tetranychus urticae) are sprayed with an active compound preparation of the desired concentration.

[0530] After 6 days, the efficacy in % is determined. 100% means that all the spider mites have been killed; 0% means that no spider mites have been killed.

[0531] In this test, for example, the following compounds from the preparation examples showed an efficacy of 100% at an application rate of 500 g/ha: 1, 3, 4, 6, 7, 9, 10, 12, 14, 15, 16, 20, 21, 22, 24, 25, 26, 27, 28, 29, 32, 33, 34, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 57, 58, 59, 60, 61, 62, 63, 64, 66, 67, 68, 70, 71, 72, 74, 76, 77, 78, 79, 80, 81, 82, 84, 85, 86, 87, 88, 89, 90, 91, 94, 100, 101, 102, 104, 105, 106, 108, 110, 111, 112, 113, 114, 115, 116, 117, 120, 121, 122, 123, 125, 126, 127, 129, 130, 131, 133, IIa-2, IIb-1

[0532] In this test, for example, the following compounds from the preparation examples showed an efficacy of 90% at an application rate of 500 g/ha: 13, 18, 19, 30, 31, 55, 59, 76, 83, 92, 97, 98, 103, 109, 130, 132, 134, IIa-1

[0533] In this test, for example, the following compounds from the preparation examples showed an efficacy of 90% at an application rate of 100 g/ha: 65, 69, 99

6. Tetranychus urticae—Spray Test, OP-Resistant
Solvent: 7 parts by weight of dimethylformamide
Emulsifier: alkylaryl polyglycol ether

[0534] To produce a suitable preparation of active compound, 1 part by weight of active compound is dissolved using the stated parts by weight of solvent and made up with water containing an emulsifier concentration of 1000 ppm until the desired concentration is attained. To produce further test concentrations, the preparation is diluted with emulsifier-containing water. If the addition of ammonium salts or/and penetrants is required, these are each added in a concentration of 1000 ppm to the formulation solution.

[0535] Bean plants (Phaseolus vulgaris) heavily infested by all stages of the greenhouse red spider mite (Tetranychus urticae) are treated by spraying with the active compound preparation of the desired concentration.

[0536] After 7 days, the efficacy in % is determined. 100% means that all the spider mites have been killed; 0% means that no spider mites have been killed.

[0537] In this test, for example, the following compounds from the preparation examples showed an efficacy of 100% at an application rate of 20 ppm: 136