SUBSTITUTED 2-DIFLUOROMETHYL-NICOTIN(THIO)CARBOXANILIDE DERIVATIVES AND THEIR USE AS FUNGICIDES
20190023658 ยท 2019-01-24
Inventors
- Christophe DUBOST (LA TOUR DE SALVAGNY, FR)
- Simon MAECHLING (LYON, FR)
- Joerg Greul (Leverkusen, DE)
- Ulrike Wachendorff-Neumann (Neuwied, DE)
- Lionel Carles (Tramoyes, FR)
- Stephane Brunet (Saint Andre de Corcy, FR)
Cpc classification
C07D213/78
CHEMISTRY; METALLURGY
International classification
Abstract
The present invention relates to novel substituted 2-difluoromethyl-nicotin(thio)carboxanilides derivatives, to processes for preparing these compounds, to compositions comprising these compounds, and to the use thereof as biologically active compounds, especially for control of harmful microorganisms in crop protection and in the protection of materials and as plant growth regulators.
Claims
1. A compound of formula (I) ##STR00008## wherein X.sub.1 represents hydrogen, halogen, CN, NO.sub.2, C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-haloalkyl, C.sub.1-C.sub.3-alkyloxy, C.sub.1-C.sub.3-haloalkyloxy, tri(C.sub.1-C.sub.3)alkylsilyl, C.sub.1-C.sub.3-alkylsulfanyl, C.sub.1-C.sub.3-haloalkylsulfanyl, C.sub.1-C.sub.3-alkylsulfonyl; C.sub.1-C.sub.3-haloalkylsulfonyl, C.sub.1-C.sub.3-alkylamino; di-C.sub.1-C.sub.3-alkylamino; X.sub.2 represents H, halogen, CN, NO.sub.2, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halocycloalkyl, C.sub.1-C.sub.6-alkyloxy, C.sub.1-C.sub.6-haloalkyloxy, tri(C.sub.1-C.sub.8)alkylsilyl, C.sub.1-C.sub.6-alkylsulfanyl, C.sub.1-C.sub.6-haloalkylsulfanyl, C.sub.1-C.sub.6-alkylsulfonyl; C.sub.1-C.sub.6-haloalkylsulfonyl, C.sub.1-C.sub.8-alkylamino; di-C.sub.1-C.sub.8-alkylamino; Q represents O, S, SO, SO.sub.2, NR.sup.1 or a bond; T is O, S; Ar represents a phenyl which can be substituted by up to 5 groups X.sub.3, or a saturated or unsaturated 5, 6 or 7 membered heterocycle which can be substituted by up to 5 groups X.sub.3 X.sub.3 which can be the same or different, independently represents halogen; cyano; C.sub.1-C.sub.16-alkyl; C.sub.1-C.sub.16-haloalkyl having 1 to 9 identical or different halogen atoms; C.sub.3-C.sub.8-cycloalkyl; (C.sub.3-C.sub.8-cycloalkyl)-C.sub.1-C.sub.8-alkyl; (C.sub.3-C.sub.8-cycloalkyl)-C.sub.3-C.sub.8-cycloalkyl; C.sub.2-C.sub.8-alkenyl; C.sub.2-C.sub.8-alkynyl; C.sub.1-C.sub.16-alkoxy; C.sub.3-C.sub.8-cycloalkyloxy; (C.sub.3-C.sub.8-cycloalkyl)-C.sub.1-C.sub.8-alkyloxy; C.sub.1-C.sub.8-alkylsulfanyl; C.sub.3-C.sub.8-cycloalkylsulfanyl; (C.sub.3-C.sub.8-cycloalkyl)-C.sub.1-C.sub.8-alkylsulfanyl; C.sub.2-C.sub.8-alkenyloxy; C.sub.3-C.sub.8-alkynyloxy; (C.sub.3-C.sub.8-cycloalkyl)-C.sub.2-C.sub.8-alkenyl; (C.sub.3-C.sub.8-cycloalkyl)-C.sub.2-C.sub.8-alkynyl; tri(C.sub.1-C.sub.8)alkylsilyl; tri(C.sub.1-C.sub.8)alkylsilyl-C.sub.1-C.sub.8-alkyl; C.sub.1-C.sub.8-alkylamino; di-C.sub.1-C.sub.8-alkylamino; C.sub.1-C.sub.8-alkylcarbonyl; C.sub.1-C.sub.8-alkylcarbonyloxy; C.sub.1-C.sub.8-alkylcarbonylamino; C.sub.1-C.sub.8-alkoxycarbonyl; C.sub.1-C.sub.8-alkylo.xycarbonyloxy; C.sub.1-C.sub.8-alkylcarbamoyl; di-C.sub.1-C.sub.8-alkylcarbamoyl; C.sub.1-C.sub.8-alkylaminocarbonyloxy; di-C.sub.1-C.sub.8-alkylaminocarbonyloxy; N(C.sub.1-C.sub.8-alkyl)hydroxycarbamoyl; C.sub.1-C.sub.8-alkoxycarbamoyl; N(C.sub.1-C.sub.8-alkyl)-C.sub.1-C.sub.8-alkoxycarbamoyl; (C.sub.1-C.sub.8-alkoxyimino)-C.sub.1-C.sub.8-alkyl; (C.sub.2-C.sub.8-cycloalkoxyimino)-C.sub.1-C.sub.8 alkyl; C.sub.1-C.sub.8-alkyliminoxy; C.sub.1-C.sub.8-alkyliminoxy-C.sub.1-C.sub.8-alkyl; each of which is optionally substituted; or two vicinal substituents X.sub.3 may be OCH.sub.2O, OCF.sub.2O, O(CH.sub.2).sub.2O, O(CF.sub.2).sub.2O or NCHS, And/or a salt, solvate, N-oxide, solvate of a salt and/or an N-oxide thereof.
2. The compound of formula (I) according to claim 1 wherein X.sub.1 in formula (I) represents hydrogen, halogen, CN, NO.sub.2, C.sub.1-C.sub.3-alkyl or C.sub.1-C.sub.3-haloalkyl.
3. The compound of formula (I) according to claim 1, wherein X.sub.2 in formula (I) represents H, halogen, CN, NO.sub.2, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkyloxy or C.sub.1-C.sub.6-haloalkyloxy.
4. The compound of formula (I) according to claim 1, wherein Ar represents phenyl optionally substituted by 1, 2, 3, 4 or 5 groups X.sub.3 wherein X.sub.3 is independently selected from halogen, CN, NO.sub.2, C.sub.1-C.sub.8-alkyl, C.sub.1-C.sub.8-alkoxy, C.sub.1-C.sub.8-alkylsulfanyl, C.sub.1-C.sub.8-halogenoalkyl, C.sub.1-C.sub.8-halogenoalkoxy, (C.sub.1-C.sub.8-alkoxyimino)-C.sub.1-C.sub.8-alkyl; (C.sub.2-C.sub.8-cycloalkoxyimino)-C.sub.1-C.sub.8 alkyl; C.sub.1-C.sub.8-alkyliminoxy; C.sub.1-C.sub.8-alkyliminoxy-C.sub.1-C.sub.8-alkyl; C.sub.2-C.sub.8-alkynyl.
5. The compound of formula (I) according to claim 1, wherein Q represents O, S, SO.sub.2 or a bond.
6. The compound of formula (I) according to claim 1, wherein Ar represents phenyl optionally substituted by 1, 2, 3, 4 or 5 groups X.sub.3 wherein X.sub.3 is independently selected from halogen, CN, NO.sub.2, C.sub.1-C.sub.8-alkyl, C.sub.1-C.sub.8-alkoxy, C.sub.1-C.sub.8-alkylsulfanyl, C.sub.1-C.sub.8-halogenoalkyl, C.sub.1-C.sub.8-halogenoalkoxy, (C.sub.1-C.sub.8-alkoxyimino)-C.sub.1-C.sub.8-alkyl; (C.sub.2-C.sub.8-cycloalkoxyimino)-C.sub.1-C.sub.8 alkyl; C.sub.1-C.sub.8-alkyliminoxy; C.sub.1-C.sub.8-alkyliminoxy-C.sub.1-C.sub.8-alkyl; C.sub.2-C.sub.8-alkynyl,
7. The compound of formula (I) according to claim 6, wherein Ar represents phenyl optionally substituted by 1 to 3 (1, 2 or 3) groups X.sub.3 wherein X.sub.3 is independently selected from Cl, F, Br, I, CN, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-alkylsulfanyl, C.sub.1-C.sub.4-halogenoalkyl, C.sub.1-C.sub.4-halogenoalkoxy, (C.sub.1-C.sub.4-alkoxyimino)-C.sub.1-C.sub.4-alkyl; (C.sub.2-C.sub.8-cycloalkoxyimino)-C.sub.1-C.sub.4 alkyl; C.sub.1-C.sub.4-alkyliminoxy; C.sub.1-C.sub.4-alkyliminoxy-C.sub.1-C.sub.4-alkyl; C.sub.2-C.sub.8-alkynyl.
8. The compound according to claim 1, wherein Q is a bond and the compound is a compound of formula (II) ##STR00009##
9. The compound of formula (II) according to claim 8, wherein X.sub.1 represents hydrogen, chlorine, fluorine, bromine, methyl, trifluoromethyl; X.sub.2 represents hydrogen, chlorine, fluorine, bromine, methyl, trifluoromethyl; X.sub.3 which can be the same or different, independently represents halogen; cyano; C.sub.1-C.sub.16-alkyl; C.sub.1-C.sub.16-haloalkyl having 1 to 9 identical or different halogen atoms; C.sub.3-C.sub.8-cycloalkyl; (C.sub.3-C.sub.8-cycloalkyl)-C.sub.1-C.sub.8-alkyl; (C.sub.3-C.sub.8-cycloalkyl)-C.sub.3-C.sub.8-cycloalkyl; C.sub.2-C.sub.8-alkenyl; C.sub.2-C.sub.8-alkynyl; C.sub.1-C.sub.16-alkoxy; C.sub.3-C.sub.8-cycloalkyloxy; (C.sub.3-C.sub.8-cycloalkyl)-C.sub.1-C.sub.8-alkyloxy; C.sub.1-C.sub.8-alkylsulfanyl; C.sub.3-C.sub.8-cycloalkylsulfanyl; (C.sub.3-C.sub.8-cycloalkyl)-C.sub.1-C.sub.8-alkylsulfanyl; C.sub.2-C.sub.8-alkenyloxy; C.sub.3-C.sub.8-alkynyloxy; (C.sub.3-C.sub.8-cycloalkyl)-C.sub.2-C.sub.8-alkenyl; (C.sub.3-C.sub.8-cycloalkyl)-C.sub.2-C.sub.8-alkynyl; tri(C.sub.1-C.sub.5)alkylsilyl; tri(C.sub.1-C.sub.5)alkylsilyl-C.sub.1-C.sub.8-alkyl; C.sub.1-C.sub.8-alkylamino; di-C.sub.1-C.sub.8-alkylamino; C.sub.1-C.sub.8-alkylcarbonyl; C.sub.1-C.sub.8-alkylcarbonyloxy; C.sub.1-C.sub.8-alkylcarbonylamino; C.sub.1-C.sub.8-alkoxycarbonyl; C.sub.1-C.sub.8-alkylo.xycarbonyloxy; C.sub.1-C.sub.8-alkylcarbamoyl; di-C.sub.1-C.sub.8-alkylcarbamoyl; C.sub.1-C.sub.8-alkylaminocarbonyloxy; di-C.sub.1-C.sub.8-alkylaminocarbonyloxy; N(C.sub.1-C.sub.8-alkyl)hydroxycarbamoyl; C.sub.1-C.sub.8-alkoxycarbamoyl; N(C.sub.1-C.sub.8-alkyl)-C.sub.1-C.sub.8-alkoxycarbamoyl; (C.sub.1-C.sub.8-alkoxyimino)-C.sub.1-C.sub.8-alkyl; (C.sub.2-C.sub.8-cycloalkoxyimino)-C.sub.1-C.sub.8 alkyl; C.sub.1-C.sub.8-alkyliminoxy; C.sub.1-C.sub.8-alkyliminoxy-C.sub.1-C.sub.8-alkyl; each of which is optionally substituted; or two vicinal substituents X.sub.3 may be OCH.sub.2O, OCF.sub.2O, O(CH.sub.2).sub.2O, O(CF.sub.2).sub.2O or NCHS; and n represents 0 to 5.
10. The compound of formula (II) according to claim 8, wherein X.sub.1 represents hydrogen, chlorine, fluorine, bromine, methyl, trifluoromethyl; X.sub.2 represents hydrogen, Chlorine, fluorine, bromine, methyl, trifluoromethyl; X.sub.3 which can be the same or different, independently represents halogen; cyano; C.sub.1-C.sub.16-alkyl; C.sub.1-C.sub.16-haloalkyl having 1 to 9 identical or different halogen atoms; C.sub.3-C.sub.8-cycloalkyl; (C.sub.3-C.sub.8-cycloalkyl)-C.sub.1-C.sub.8-alkyl; (C.sub.3-C.sub.8-cycloalkyl)-C.sub.3-C.sub.8-cycloalkyl; C.sub.2-C.sub.8-alkenyl; C.sub.2-C.sub.8-alkynyl; C.sub.1-C.sub.16-alkoxy; C.sub.3-C.sub.8-cycloalkyloxy; (C.sub.3-C.sub.8-cycloalkyl)-C.sub.1-C.sub.8-alkyloxy; C.sub.1-C.sub.8-alkylsulfanyl; C.sub.3-C.sub.8-cycloalkylsulfanyl; (C.sub.3-C.sub.8-cycloalkyl)-C.sub.1-C.sub.8-alkylsulfanyl; C.sub.2-C.sub.8-alkenyloxy; C.sub.3-C.sub.8-alkynyloxy; (C.sub.3-C.sub.8-cycloalkyl)-C.sub.2-C.sub.8-alkenyl; (C.sub.3-C.sub.8-cycloalkyl)-C.sub.2-C.sub.8-alkynyl; C.sub.1-C.sub.8-alkylamino; di-C.sub.1-C.sub.8-alkylamino; (C.sub.1-C.sub.8-alkoxyimino)-C.sub.1-C.sub.8-alkyl; (C.sub.2-C.sub.8-cycloalkoxyimino)-C.sub.1-C.sub.8 alkyl; C.sub.1-C.sub.8-alkyliminoxy; each of which is optionally substituted; and n represents 0 to 3.
Description
PREPARATION EXAMPLES
[0209] In analogy to the examples above and according to the general description of the processes of preparing the compounds according to the invention the compounds in the following Table 1 may be obtained.
##STR00005##
TABLE-US-00001 TABLE 1 Ex X.sub.1 T X.sub.2 Q Ar LogP I-01 H O H O 4-methylphenyl 3.27.sup.[a] I-02 H O H O 2-methylphenyl 3.27.sup.[a] I-03 H O H O 4-chlorophenyl 3.33.sup.[a] I-04 H O H O 3-fluoro-5-(trifluoromethyl)phenyl 3.57.sup.[a] I-05 H O H O 3-methoxyphenyl 2.92.sup.[a] I-06 H O H O 3-chlorophenyl 3.29.sup.[a] I-07 H O H O 4-(trifluoromethyl)phenyl 3.46.sup.[a] I-08 H O H O 2,3-difluorophenyl 2.98.sup.[a] I-09 H O 3-Cl S phenyl 3.59.sup.[a] I-10 H O 3-Cl O 4-chlorophenyl 3.59.sup.[a] I-11 H O H S phenyl 3.21.sup.[a] I-12 H O H O 3,5-difluorophenyl 3.11.sup.[a] I-13 H O H O 4-methoxyphenyl 2.90.sup.[a] I-14 H O H S 4-chlorophenyl 3.57.sup.[a] I-15 H O H O 2-fluorophenyl 2.88.sup.[a] I-16 H O H O 3,4-difluorophenyl 3.09.sup.[a] I-17 H O H O 2,4-dichlorophenyl 3.65.sup.[a] I-18 H O H O 3-(trifluoromethyl)phenyl 3.44.sup.[a] I-19 H O H O 3-methylphenyl 3.23.sup.[a] I-20 H O H O phenyl 2.90.sup.[a] I-21 H O H O 2-methoxyphenyl 2.88.sup.[a] I-22 H O 3-Cl O phenyl 3.15.sup.[a] I-23 H O H SO.sub.2 phenyl 2.56.sup.[a] I-24 H O 5-CF.sub.3 O phenyl 3.63.sup.[a] I-25 H O H O 3,5-dichlorophenyl 3.81.sup.[a] I-26 H O H O 2-chlorophenyl 3.11.sup.[a] I-27 H O H O 3-fluorophenyl 2.96.sup.[a] I-28 H O H O 4-fluorophenyl 2.96.sup.[a] I-29 H O H O 4-cyanophenyl 2.51.sup.[a] I-30 H O H O 4-bromophenyl 3.39.sup.[a] I-31 4-CHF.sub.2 O 4-F bond 3,4-dichlorophenyl 3.96.sup.[a] I-32 H O H bond 4-[(methoxyimino)methyl]phenyl 2.86.sup.[a] I-33 H O 6-F bond 3,5-difluoro-4-[(methoxyimino)methyl]phenyl 2.97.sup.[a] I-34 H O H bond 4-fluorophenyl 2.66.sup.[a] I-35 H O H bond 4-chloro-3-fluorophenyl 3.06.sup.[a] I-36 H O H bond 4-cyano-3,5-difluorophenyl 2.71.sup.[a] I-37 H O 4-F bond 3,4-dichlorophenyl 3.44.sup.[a] I-38 H O H bond 3,5-difluorophenyl 2.80.sup.[a] I-39 H O H bond 3-(trifluoromethyl)phenyl 3.15.sup.[a] I-40 H O H bond 4-chlorophenyl 2.92.sup.[a] I-41 H O H bond 4-[(ethoxyimino)methyl]phenyl 3.23.sup.[a] I-42 H O H bond 3,4-difluorophenyl 2.78.sup.[a] I-43 H O H bond 3-fluoro-4-(trifluoromethyl)phenyl 3.25.sup.[a] I-44 H O H bond 2-(trifluoromethyl)phenyl 2.99.sup.[a]; 2.93.sup.[b] I-45 H O H bond 2,4-difluorophenyl 2.66.sup.[a] I-46 H O H bond 4-[(ethoxyimino)methyl]-3-fluorophenyl 3.27 + 3.48.sup.[a] I-47 H O 4-F bond 4-fluorophenyl 2.73.sup.[a] I-48 H O H bond 3,4,5-trifluorophenyl 2.92.sup.[a] I-49 H O H bond 3,5-difluoro-4-[(methoxyimino)methyl]phenyl 3.17.sup.[a] I-50 H O H bond 4-[(ethoxyimino)methyl]-3,5-difluorophenyl 3.46.sup.[a] I-51 H O H bond 2-chlorophenyl 2.74.sup.[a]; 2.68.sup.[b] I-52 H O H bond 3-chlorophenyl 2.96.sup.[a] I-53 H O H bond 3,5-dichlorophenyl 3.48.sup.[a] I-54 H O H bond 3,4-dichlorophenyl 3.35.sup.[a] I-55 H O 4-F bond 3,5-difluoro-4-(methoxycarbonoimidoyl)phenyl 3.16.sup.[a] I-56 H O H bond 4-(methylsulfanyl)phenyl 2.94.sup.[a] I-57 H O H bond 4-ethoxy-3,5-difluorophenyl 3.29.sup.[a] I-58 H O H bond 3,5-difluoro-4-propoxyphenyl 3.61.sup.[a] I-59 H O H bond 4-butoxy-3,5-difluorophenyl 3.99.sup.[a] I-60 H O 6-F bond 4-[(ethoxyimino)methyl]-3,5-difluorophenyl 3.35.sup.[a] I-61 H O H bond phenyl 2.55.sup.[a] I-62 H O H bond 4-(3,3-dimethylbut-1-yn-1-yl)phenyl 4.29.sup.[a] I-63 H O H bond 3-chloro-4-(trifluoromethyl)phenyl 3.50.sup.[a] I-64 H O H bond 3-fluoro-4-[(methoxyimino)methyl]phenyl 2.92 + 3.11.sup.[a] I-65 H O 4-F bond 4-[(ethoxyimino)methyl]-3,5-difluorophenyl 3.55.sup.[a] I-66 H O H bond 3-chloro-4-fluorophenyl 3.04.sup.[a] I-67 H S H bond 4-[(ethoxyimino)methyl]phenyl 3.70.sup.[a] I-68 H S H bond 3-chloro-4-(trifluoromethyl)phenyl 3.94.sup.[a] I-69 H S 4-F bond 3,5-difluoro-4-(methoxycarbonoimidoyl)phenyl 3.73.sup.[a] I-70 H S 4-F bond 4-[(ethoxyimino)methyl]-3,5-difluorophenyl 4.11.sup.[a] I-71 H S H bond 4-cyano-3,5-difluorophenyl 3.19.sup.[a] I-72 H S 6-F bond 4-[(ethoxyimino)methyl]-3,5-difluorophenyl 3.99.sup.[a] I-73 H S H bond 3,4-difluorophenyl 3.27.sup.[a] I-74 H S 6-F bond 3,5-difluoro-4-(methoxycarbonoimidoyl)phenyl 3.60.sup.[a] I-75 H S H bond 4-[(ethoxyimino)methyl]-3,5-difluorophenyl 3.92.sup.[a] I-76 H S H bond 3,5-difluoro-4-[(methoxyimino)methyl]phenyl 3.55.sup.[a]
[0210] Measurement of Log P values was performed according to EEC directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on reversed phase columns with the following methods:
[0211] [a] Log P value is determined by measurement of LC-UV, in an acidic range, with 0.1% formic acid in water and acetonitrile as eluent (linear gradient from 10% acetonitrile to 95% acetonitrile).
[0212] [b] Log P value is determined by measurement of LC-UV, in a neutral range, with 0.001 molar ammonium acetate solution in water and acetonitrile as eluent (linear gradient from 10% acetonitrile to 95% acetonitrile).
[0213] Calibration was done with straight-chain alkan2-ones (with 3 to 16 carbon atoms) with known Log P values (measurement of Log P values using retention times with linear interpolation between successive alkanones). Lambda-max-values were determined using UV-spectra from 200 nm to 400 nm and the peak values of the chromatographic signals.
NMR-Peak Lists
[0214] 1H-NMR data of selected examples are written in form of 1H-NMR-peak lists. To each signal peak are listed the -value in ppm and the signal intensity in round brackets. Between the -value-signal intensity pairs are semicolons as delimiters.
[0215] The peak list of an example has therefore the form:
.sub.1 (intensity.sub.1); .sub.2 (intensity.sub.2); . . . ; .sub.i (intensity.sub.i); . . . ; .sub.n (intensity.sub.n)
[0216] Intensity of sharp signals correlates with the height of the signals in a printed example of a NMR spectrum in cm and shows the real relations of signal intensities. From broad signals several peaks or the middle of the signal and their relative intensity in comparison to the most intensive signal in the spectrum can be shown.
[0217] For calibrating chemical shift for 1H spectra, we use tetramethylsilane and/or the chemical shift of the solvent used, especially in the case of spectra measured in DMSO. Therefore in NMR peak lists, tetramethylsilane peak can occur but not necessarily.
[0218] The 1H-NMR peak lists are similar to classical 1H-NMR prints and contains therefore usually all peaks, which are listed at classical NMR-interpretation.
[0219] Additionally they can show like classical 1H-NMR prints signals of solvents, stereoisomers of the target compounds, which are also object of the invention, and/or peaks of impurities.
[0220] To show compound signals in the delta-range of solvents and/or water the usual peaks of solvents, for example peaks of DMSO in DMSO-D.sub.6 and the peak of water are shown in our 1H-NMR peak lists and have usually on average a high intensity.
[0221] The peaks of stereoisomers of the target compounds and/or peaks of impurities have usually on average a lower intensity than the peaks of target compounds (for example with a purity >90%).
[0222] Such stereoisomers and/or impurities can be typical for the specific preparation process. Therefore their peaks can help to recognize the reproduction of our preparation process via side-products-fingerprints.
[0223] An expert, who calculates the peaks of the target compounds with known methods (MestreC, ACD-simulation, but also with empirically evaluated expectation values) can isolate the peaks of the target compounds as needed optionally using additional intensity filters. This isolation would be similar to relevant peak picking at classical 1H-NMR interpretation.
[0224] Further details of NMR-data description with peak lists you find in the publication Citation of NMR Peaklist Data within Patent Applications of the Research Disclosure Database Number 564025.
TABLE-US-00002 Example I-01: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 10.311 (2.7); 8.775 (1.9); 8.766 (1.9); 8.763 (1.9); 7.835 (2.0); 7.816 (2.1); 7.646 (1.1); 7.635 (1.2); 7.627 (1.1); 7.615 (1.0); 7.248 (0.5); 7.245 (0.6); 7.230 (1.5); 7.225 (1.5); 7.206 (2.7); 7.199 (2.2); 7.185 (5.6); 7.163 (5.0); 7.063 (3.2); 6.953 (1.5); 6.929 (2.3); 6.887 (3.6); 6.866 (3.3); 3.318 (43.1); 2.890 (0.6); 2.731 (0.5); 2.669 (0.3); 2.505 (39.5); 2.501 (52.1); 2.496 (39.9); 2.289 (1.0); 2.274 (16.0); 0.000 (3.3) Example I-02: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 10.316 (3.7); 8.787 (2.4); 8.777 (2.4); 7.912 (1.9); 7.893 (2.2); 7.867 (1.5); 7.850 (1.6); 7.670 (1.5); 7.658 (1.6); 7.651 (1.5); 7.639 (1.2); 7.315 (2.2); 7.297 (2.5); 7.248 (1.8); 7.215 (1.7); 7.196 (4.1); 7.177 (3.6); 7.153 (1.9); 7.134 (0.9); 7.112 (4.1); 7.104 (2.2); 7.085 (3.0); 7.067 (1.3); 6.977 (1.9); 6.841 (2.4); 6.821 (2.2); 6.758 (1.9); 6.739 (1.7); 3.318 (54.3); 2.890 (1.8); 2.731 (1.6); 2.670 (0.5); 2.505 (59.1); 2.501 (74.4); 2.497 (55.3); 2.327 (0.5); 2.199 (16.0); 0.000 (5.2) Example I-03: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 10.359 (6.0); 8.783 (4.1); 8.779 (4.4); 8.771 (4.4); 8.768 (4.3); 7.857 (2.4); 7.851 (2.3); 7.839 (5.6); 7.820 (4.3); 7.654 (2.6); 7.642 (2.8); 7.635 (2.5); 7.623 (2.2); 7.434 (1.3); 7.425 (14.4); 7.419 (4.6); 7.408 (4.9); 7.403 (16.0); 7.394 (1.5); 7.302 (0.7); 7.297 (1.1); 7.284 (3.5); 7.278 (4.5); 7.267 (7.7); 7.259 (5.0); 7.251 (3.5); 7.238 (1.1); 7.233 (0.7); 7.184 (3.7); 7.068 (3.1); 7.062 (2.9); 7.049 (10.5); 6.986 (9.8); 6.964 (8.9); 6.914 (4.1); 3.321 (76.9); 3.318 (75.4); 2.890 (1.5); 2.731 (1.3); 2.674 (0.5); 2.670 (0.7); 2.666 (0.5); 2.523 (1.6); 2.510 (41.6); 2.506 (82.3); 2.501 (107.1); 2.497 (77.0); 2.492 (37.3); 2.332 (0.5); 2.328 (0.6); 2.323 (0.5); 0.000 (6.2) Example I-04: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 10.415 (10.4); 8.781 (7.3); 8.769 (7.3); 7.952 (0.6); 7.868 (3.6); 7.857 (4.5); 7.838 (7.5); 7.818 (7.2); 7.654 (4.5); 7.642 (4.9); 7.635 (4.4); 7.623 (3.7); 7.435 (5.7); 7.414 (5.8); 7.370 (10.1); 7.361 (9.4); 7.355 (9.9); 7.346 (11.7); 7.249 (5.4); 7.235 (4.8); 7.225 (3.9); 7.130 (5.2); 7.104 (5.3); 7.079 (16.0); 6.995 (10.9); 6.860 (5.5); 3.702 (0.5); 3.324 (264.8); 2.891 (3.3); 2.731 (3.0); 2.671 (1.2); 2.506 (147.1); 2.502 (194.0); 2.498 (155.5); 2.329 (1.2); 0.000 (3.9) Example I-05: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 10.323 (2.0); 8.774 (1.5); 8.762 (1.5); 7.833 (0.9); 7.815 (0.9); 7.789 (1.2); 7.770 (1.4); 7.636 (0.9); 7.624 (0.9); 7.618 (0.8); 7.606 (0.7); 7.279 (1.2); 7.274 (1.2); 7.269 (1.3); 7.259 (2.7); 7.256 (3.0); 7.251 (2.2); 7.238 (2.0); 7.219 (0.4); 7.181 (1.1); 7.056 (1.2); 7.046 (2.8); 6.911 (1.1); 6.707 (1.5); 6.703 (1.2); 6.688 (1.1); 6.683 (1.2); 6.519 (3.4); 6.501 (1.2); 3.704 (16.0); 3.322 (40.4); 2.890 (1.8); 2.731 (1.6); 2.505 (30.3); 2.501 (40.8); 2.497 (32.8); 0.000 (1.4) Example I-06: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 10.369 (12.9); 8.780 (9.2); 8.770 (9.1); 7.952 (2.9); 7.855 (5.0); 7.840 (5.3); 7.833 (5.2); 7.807 (7.5); 7.788 (9.0); 7.650 (5.8); 7.637 (6.2); 7.631 (5.4); 7.618 (4.4); 7.406 (7.1); 7.385 (15.4); 7.365 (9.0); 7.326 (2.3); 7.309 (12.5); 7.299 (15.0); 7.290 (12.9); 7.272 (1.9); 7.181 (9.7); 7.179 (10.0); 7.169 (7.9); 7.163 (8.0); 7.161 (8.1); 7.159 (8.1); 7.130 (6.5); 7.123 (5.7); 7.108 (5.3); 7.034 (13.7); 6.973 (12.2); 6.931 (7.6); 6.910 (7.1); 6.905 (6.8); 6.899 (7.9); 3.702 (0.8); 3.321 (256.4); 2.891 (16.0); 2.732 (15.1); 2.670 (1.5); 2.505 (203.2); 2.501 (243.5); 2.328 (1.5); 0.000 (9.5) Example I-07: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 10.390 (10.2); 8.768 (6.7); 8.765 (7.0); 8.757 (7.2); 8.754 (6.9); 7.862 (3.5); 7.850 (4.2); 7.839 (3.8); 7.734 (14.4); 7.712 (16.0); 7.704 (9.7); 7.612 (4.9); 7.600 (5.1); 7.593 (4.0); 7.581 (3.5); 7.359 (1.3); 7.347 (9.6); 7.334 (10.0); 7.323 (11.0); 7.311 (1.5); 7.208 (5.1); 7.197 (4.6); 7.184 (3.8); 7.118 (5.4); 7.096 (13.3); 7.075 (12.5); 6.983 (11.6); 6.848 (5.7); 3.321 (257.4); 2.890 (0.9); 2.731 (0.9); 2.670 (1.3); 2.506 (164.0); 2.501 (208.5); 2.497 (153.6); 2.328 (1.3); 0.000 (8.8) Example I-08: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 10.450 (10.5); 8.792 (7.7); 8.780 (7.6); 8.313 (0.3); 7.965 (5.8); 7.946 (7.1); 7.905 (3.7); 7.892 (4.4); 7.882 (3.9); 7.685 (4.4); 7.673 (4.8); 7.666 (4.5); 7.654 (3.8); 7.294 (2.1); 7.285 (10.9); 7.276 (10.9); 7.270 (11.4); 7.261 (11.9); 7.251 (3.4); 7.230 (3.5); 7.226 (3.8); 7.209 (10.2); 7.189 (9.4); 7.168 (4.5); 7.147 (1.3); 7.075 (15.9); 7.055 (3.9); 6.940 (6.1); 6.833 (3.4); 6.812 (5.5); 6.795 (2.6); 3.702 (0.5); 3.323 (154.2); 3.320 (165.8); 2.890 (16.0); 2.731 (14.7); 2.670 (1.2); 2.505 (152.0); 2.501 (200.8); 2.497 (155.5); 2.328 (1.2); 2.324 (1.0); 0.000 (6.6) Example I-09: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 10.632 (7.0); 8.812 (4.3); 8.809 (4.5); 8.800 (4.6); 8.797 (4.4); 7.952 (0.9); 7.905 (3.3); 7.885 (4.0); 7.796 (0.5); 7.786 (3.1); 7.775 (3.7); 7.772 (3.7); 7.762 (3.9); 7.752 (0.7); 7.685 (3.1); 7.673 (3.2); 7.666 (2.8); 7.654 (2.6); 7.617 (0.9); 7.597 (9.6); 7.593 (9.5); 7.584 (16.0); 7.573 (1.1); 7.293 (4.3); 7.275 (10.3); 7.255 (7.4); 7.228 (3.3); 7.189 (3.7); 7.171 (5.4); 7.152 (1.9); 7.093 (7.3); 7.036 (8.0); 7.033 (10.2); 7.015 (8.7); 6.958 (3.6); 3.745 (0.4); 3.713 (0.4); 3.702 (0.5); 3.328 (103.1); 3.322 (103.7); 2.890 (6.1); 2.731 (5.4); 2.675 (0.5); 2.670 (0.6); 2.666 (0.5); 2.506 (83.1); 2.501 (106.1); 2.497 (76.0); 2.493 (37.0); 2.333 (0.5); 2.328 (0.6); 2.323 (0.5); 0.000 (2.6) Example I-10: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 10.507 (8.8); 10.024 (0.4); 8.770 (4.5); 8.761 (6.2); 8.754 (4.9); 8.237 (0.6); 7.953 (1.2); 7.857 (4.3); 7.838 (4.7); 7.634 (1.4); 7.620 (16.0); 7.615 (11.4); 7.610 (9.4); 7.589 (1.0); 7.545 (4.5); 7.542 (5.0); 7.525 (6.3); 7.521 (6.4); 7.423 (5.2); 7.403 (8.9); 7.389 (14.1); 7.384 (9.3); 7.372 (5.7); 7.366 (14.5); 7.337 (0.9); 7.318 (0.5); 7.070 (3.5); 6.935 (7.7); 6.835 (2.1); 6.827 (14.7); 6.823 (7.2); 6.809 (5.9); 6.804 (14.2); 3.330 (105.0); 3.324 (145.1); 2.891 (7.1); 2.732 (6.7); 2.671 (0.6); 2.506 (82.0); 2.502 (105.3); 2.498 (84.6); 2.329 (0.6); 0.000 (2.4) Example I-11: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 10.444 (7.8); 8.815 (5.2); 8.804 (5.2); 7.942 (3.4); 7.923 (4.0); 7.693 (2.9); 7.681 (3.3); 7.674 (3.1); 7.662 (2.8); 7.646 (3.4); 7.627 (4.0); 7.444 (2.0); 7.427 (3.8); 7.408 (2.1); 7.379 (4.0); 7.362 (11.1); 7.342 (10.7); 7.316 (5.9); 7.307 (9.1); 7.289 (11.1); 7.272 (12.9); 7.269 (16.0); 7.251 (9.0); 7.156 (8.5); 7.021 (4.2); 3.702 (0.9); 3.319 (86.0); 2.890 (1.8); 2.731 (1.6); 2.670 (0.8); 2.505 (95.3); 2.501 (127.4); 2.498 (100.7); 2.328 (0.8); 0.000 (6.1) Example I-12: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 10.398 (12.9); 8.787 (9.6); 8.778 (9.4); 8.776 (9.2); 7.953 (2.3); 7.859 (8.2); 7.840 (13.1); 7.821 (5.2); 7.673 (5.9); 7.661 (6.3); 7.654 (5.6); 7.642 (4.8); 7.362 (2.5); 7.352 (14.6); 7.343 (13.4); 7.338 (13.7); 7.328 (16.0); 7.319 (2.6); 7.214 (7.3); 7.205 (6.6); 7.190 (5.4); 7.163 (7.3); 7.027 (15.7); 7.005 (2.6); 7.000 (4.3); 6.994 (2.7); 6.982 (5.0); 6.976 (8.4); 6.971 (4.8); 6.958 (2.6); 6.953 (4.2); 6.948 (2.3); 6.892 (7.8); 6.642 (11.7); 6.637 (12.1); 6.621 (12.5); 6.616 (10.8); 3.702 (0.8); 3.322 (193.8); 2.891 (14.2); 2.732 (13.0); 2.671 (1.3); 2.506 (169.0); 2.502 (212.9); 2.498 (157.6); 2.329 (1.3); 1.236 (0.4); 0.000 (5.7) Example I-13: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 10.319 (2.0); 8.788 (1.4); 8.779 (1.5); 7.945 (1.1); 7.925 (1.2); 7.854 (1.0); 7.836 (1.1); 7.671 (0.8); 7.658 (1.0); 7.641 (0.7); 7.246 (0.9); 7.213 (0.5); 7.197 (1.2); 7.194 (1.2); 7.178 (1.2); 7.174 (1.2); 7.167 (1.1); 7.147 (1.2); 7.129 (0.6); 7.110 (1.9); 6.974 (1.7); 6.958 (9.3); 6.936 (0.8); 6.869 (1.3); 6.850 (1.2); 3.748 (0.9); 3.735 (16.0); 3.716 (0.4); 3.319 (17.3); 2.889 (0.9); 2.731 (0.8); 2.505 (35.0); 2.501 (42.2); 2.497 (32.5); 0.000 (2.9) Example I-14: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 10.495 (8.6); 8.824 (5.4); 8.815 (5.5); 8.291 (0.4); 7.996 (3.8); 7.976 (4.2); 7.712 (3.2); 7.699 (3.7); 7.693 (3.5); 7.680 (2.9); 7.648 (3.8); 7.628 (4.7); 7.508 (0.4); 7.477 (2.7); 7.459 (5.0); 7.439 (3.2); 7.425 (12.6); 7.404 (16.0); 7.386 (3.5); 7.368 (5.8); 7.337 (4.6); 7.319 (5.3); 7.299 (2.1); 7.289 (3.9); 7.251 (15.9); 7.230 (12.6); 7.196 (0.4); 7.176 (0.3); 7.154 (8.0); 7.138 (0.7); 7.116 (0.5); 7.019 (4.1); 3.319 (67.2); 2.890 (0.5); 2.731 (0.5); 2.670 (0.8); 2.505 (102.4); 2.501 (127.4); 2.497 (101.9); 2.328 (0.8); 1.237 (0.4); 0.000 (7.8) Example I-15: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 10.423 (10.3); 8.792 (7.3); 8.790 (7.9); 8.781 (7.7); 8.778 (7.6); 7.973 (5.7); 7.953 (8.4); 7.900 (4.1); 7.884 (4.2); 7.878 (4.3); 7.678 (4.5); 7.666 (4.9); 7.659 (4.6); 7.647 (3.8); 7.407 (0.6); 7.399 (3.7); 7.392 (2.4); 7.388 (3.8); 7.381 (2.9); 7.375 (5.2); 7.371 (4.6); 7.364 (2.6); 7.358 (3.4); 7.355 (2.9); 7.347 (4.6); 7.338 (0.7); 7.255 (1.3); 7.249 (2.6); 7.242 (7.6); 7.237 (7.9); 7.231 (11.3); 7.222 (14.0); 7.212 (13.3); 7.207 (14.3); 7.203 (13.8); 7.196 (12.3); 7.189 (13.0); 7.183 (9.6); 7.179 (8.9); 7.171 (2.2); 7.107 (13.2); 7.082 (3.2); 7.076 (2.5); 7.070 (3.3); 7.061 (4.4); 7.051 (3.2); 7.037 (2.2); 6.971 (6.5); 6.923 (4.9); 6.917 (4.6); 6.900 (4.4); 3.702 (0.7); 3.322 (108.0); 3.319 (129.9); 2.890 (16.0); 2.731 (14.1); 2.675 (0.9); 2.670 (1.2); 2.666 (0.8); 2.509 (74.8); 2.505 (144.7); 2.501 (188.4); 2.497 (138.8); 2.332 (0.8); 2.328 (1.2); 2.323 (0.9); 0.008 (0.4); 0.000 (9.1) Example I-16: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 10.374 (10.4); 8.788 (7.7); 8.780 (7.6); 8.777 (7.6); 7.952 (2.2); 7.911 (5.6); 7.892 (6.8); 7.856 (4.1); 7.840 (4.2); 7.833 (4.3); 7.678 (4.5); 7.666 (4.9); 7.659 (4.5); 7.647 (3.9); 7.475 (3.3); 7.452 (7.3); 7.426 (7.5); 7.403 (3.4); 7.312 (0.9); 7.306 (1.8); 7.293 (6.3); 7.287 (10.8); 7.278 (13.3); 7.269 (11.5); 7.264 (6.7); 7.250 (1.9); 7.235 (0.8); 7.229 (0.5); 7.212 (0.9); 7.188 (6.2); 7.107 (2.7); 7.100 (3.3); 7.088 (7.7); 7.082 (7.6); 7.070 (6.5); 7.064 (6.5); 7.053 (16.0); 7.030 (0.4); 7.019 (0.4); 6.917 (6.6); 6.800 (3.9); 6.790 (3.0); 6.780 (3.6); 3.702 (0.8); 3.321 (194.4); 2.890 (14.0); 2.731 (12.7); 2.674 (0.8); 2.670 (1.1); 2.666 (0.8); 2.506 (131.6); 2.501 (173.3); 2.497 (127.8); 2.332 (0.8); 2.328 (1.1); 2.324 (0.8); 0.000 (5.8) Example I-17: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 10.416 (6.0); 8.802 (3.7); 8.799 (4.0); 8.790 (4.0); 8.787 (3.9); 8.003 (3.0); 7.984 (3.4); 7.952 (2.4); 7.864 (1.9); 7.851 (2.3); 7.841 (2.0); 7.749 (8.4); 7.743 (8.7); 7.699 (2.4); 7.687 (2.6); 7.680 (2.4); 7.667 (2.1); 7.429 (4.5); 7.422 (4.4); 7.406 (5.0); 7.400 (4.9); 7.284 (0.8); 7.272 (5.7); 7.265 (4.2); 7.259 (5.4); 7.248 (6.3); 7.237 (3.8); 7.102 (6.8); 7.009 (4.6); 6.987 (4.3); 6.967 (3.9); 6.956 (2.7); 6.945 (2.5); 6.932 (2.3); 3.324 (142.5); 2.890 (16.0); 2.731 (14.3); 2.675 (0.5); 2.671 (0.6); 2.666 (0.5); 2.510 (38.5); 2.506 (76.2); 2.501 (99.9); 2.497 (73.3); 2.493 (36.7); 2.332 (0.4); 2.328 (0.6); 2.324 (0.4); 0.000 (2.5) Example I-18: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 10.390 (9.6); 8.774 (6.4); 8.770 (7.1); 8.762 (7.1); 8.759 (6.8); 7.952 (2.2); 7.875 (3.2); 7.862 (3.9); 7.851 (3.4); 7.761 (5.3); 7.742 (6.9); 7.624 (5.4); 7.613 (5.7); 7.601 (7.5); 7.600 (7.5); 7.597 (7.0); 7.578 (4.5); 7.515 (0.4); 7.495 (0.3); 7.473 (7.3); 7.454 (5.4); 7.372 (0.4); 7.351 (0.6); 7.344 (1.5); 7.332 (9.2); 7.325 (6.6); 7.319 (10.1); 7.314 (6.3); 7.308 (10.5); 7.295 (1.6); 7.232 (16.0); 7.215 (5.6); 7.165 (4.7); 7.154 (4.4); 7.148 (3.5); 7.141 (4.2); 7.134 (6.7); 7.101 (0.4); 7.013 (0.4); 6.998 (12.8); 6.909 (0.5); 6.889 (0.6); 6.863 (6.3); 3.702 (0.8); 3.424 (0.4); 3.409 (0.5); 3.394 (0.4); 3.333 (118.7); 3.324 (160.1); 2.890 (16.0); 2.749 (0.3); 2.731 (13.9); 2.675 (0.8); 2.671 (1.1); 2.666 (0.8); 2.556 (0.3); 2.551 (0.3); 2.524 (2.6); 2.511 (64.1); 2.506 (131.0); 2.502 (173.4); 2.497 (125.2); 2.493 (60.6); 2.333 (0.8); 2.329 (1.1); 2.324 (0.8); 0.000 (5.0) Example I-19: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 10.311 (2.8); 8.771 (2.0); 8.760 (2.0); 7.845 (1.2); 7.827 (1.3); 7.785 (1.6); 7.766 (2.0); 7.638 (1.2); 7.626 (1.3); 7.619 (1.2); 7.607 (1.0); 7.270 (0.6); 7.260 (1.9); 7.257 (1.8); 7.251 (1.8); 7.240 (4.1); 7.232 (3.0); 7.221 (2.6); 7.195 (0.7); 7.187 (1.6); 7.051 (3.1); 7.010 (1.6); 6.991 (1.4); 6.944 (2.2); 6.924 (2.0); 6.916 (1.8); 6.793 (2.5); 6.762 (1.6); 6.741 (1.4); 3.320 (33.1); 2.889 (0.4); 2.730 (0.4); 2.669 (0.3); 2.504 (41.4); 2.501 (54.7); 2.496 (43.6); 2.328 (0.4); 2.290 (1.0); 2.265 (16.0); 0.000 (3.5) Example I-20: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 10.335 (9.7); 8.770 (6.9); 8.767 (7.3); 8.759 (7.3); 8.755 (7.1); 8.313 (0.4); 7.952 (1.3); 7.854 (4.1); 7.838 (4.4); 7.770 (5.8); 7.750 (7.4); 7.629 (4.6); 7.617 (4.9); 7.610 (4.0); 7.598 (3.5); 7.396 (1.6); 7.391 (9.9); 7.386 (3.7); 7.372 (16.0); 7.370 (15.5); 7.351 (12.5); 7.345 (1.6); 7.283 (1.6); 7.279 (2.1); 7.265 (5.6); 7.260 (6.0); 7.247 (10.1); 7.242 (9.3); 7.230 (5.7); 7.225 (5.4); 7.211 (2.0); 7.186 (6.0); 7.134 (5.7); 7.116 (10.0); 7.097 (4.4); 7.051 (13.3); 7.027 (5.4); 7.024 (5.3); 7.005 (4.6); 6.974 (13.1); 6.954 (11.9); 6.916 (6.7); 3.702 (0.9); 3.322 (252.3); 2.890 (8.7); 2.731 (7.7); 2.675 (0.9); 2.670 (1.2); 2.666 (0.9); 2.523 (3.0); 2.510 (74.8); 2.506 (147.5); 2.501 (191.0); 2.497 (137.3); 2.492 (66.7); 2.332 (0.9); 2.328 (1.2); 2.323 (0.9); 0.000 (7.8) Example I-21: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 10.289 (2.1); 8.795 (1.6); 8.785 (1.6); 8.051 (1.1); 8.032 (1.2); 7.951 (0.6); 7.891 (1.0); 7.874 (1.1); 7.690 (0.9); 7.678 (1.0); 7.659 (0.8); 7.293 (0.9); 7.206 (0.3); 7.203 (0.4); 7.186 (1.4); 7.182 (1.5); 7.170 (4.2); 7.166 (4.5); 7.158 (2.9); 7.150 (1.3); 7.144 (1.6); 7.120 (2.1); 7.102 (1.2); 7.085 (0.5); 7.022 (1.1); 7.012 (0.9); 6.992 (1.9); 6.973 (1.4); 6.968 (1.3); 6.957 (1.3); 6.953 (1.5); 6.938 (0.5); 6.932 (0.6); 6.707 (1.2); 6.688 (1.1); 3.739 (16.0); 3.320 (36.9); 2.890 (3.6); 2.731 (3.3); 2.504 (31.5); 2.501 (39.4); 2.497 (30.4); 0.000 (1.3) Example I-22: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 10.470 (8.8); 8.746 (5.5); 8.743 (5.8); 8.735 (5.7); 8.731 (5.6); 8.313 (0.5); 7.952 (2.6); 7.824 (4.4); 7.804 (4.8); 7.573 (3.2); 7.561 (3.4); 7.554 (4.6); 7.541 (8.9); 7.520 (6.9); 7.517 (6.7); 7.444 (6.1); 7.424 (4.5); 7.406 (5.9); 7.386 (9.6); 7.366 (4.2); 7.346 (6.4); 7.325 (11.2); 7.306 (8.1); 7.080 (4.0); 7.062 (6.9); 7.041 (5.5); 6.905 (8.6); 6.804 (12.3); 6.784 (11.1); 6.770 (4.5); 3.701 (0.4); 3.324 (179.8); 3.322 (185.9); 3.317 (186.0); 2.890 (16.0); 2.731 (14.6); 2.670 (2.0); 2.666 (1.5); 2.505 (259.0); 2.501 (333.8); 2.497 (250.1); 2.328 (2.1); 2.324 (1.6); 0.000 (18.2) Example I-23: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 10.383 (7.4); 8.887 (4.8); 8.884 (5.1); 8.876 (5.1); 8.872 (5.0); 8.229 (2.9); 8.210 (3.2); 8.128 (5.1); 8.125 (5.3); 8.108 (5.7); 8.105 (5.5); 7.953 (1.2); 7.881 (3.7); 7.861 (6.4); 7.843 (9.8); 7.824 (15.3); 7.821 (15.3); 7.809 (4.1); 7.802 (7.8); 7.790 (3.3); 7.784 (2.7); 7.780 (2.4); 7.710 (2.2); 7.692 (5.9); 7.673 (4.1); 7.595 (10.7); 7.575 (16.0); 7.556 (7.3); 7.261 (3.6); 7.126 (8.0); 6.991 (4.0); 3.702 (0.5); 3.320 (44.7); 3.318 (43.4); 2.890 (7.7); 2.731 (6.7); 2.675 (0.5); 2.670 (0.6); 2.666 (0.5); 2.523 (1.8); 2.506 (79.0); 2.501 (102.0); 2.497 (75.2); 2.332 (0.5); 2.328 (0.6); 2.323 (0.5); 0.000 (11.5) Example I-24: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 10.636 (11.1); 8.802 (7.4); 8.791 (7.6); 8.388 (8.0); 7.973 (6.2); 7.953 (9.1); 7.736 (1.9); 7.732 (1.9); 7.682 (4.8); 7.670 (5.1); 7.663 (4.6); 7.651 (4.2); 7.582 (5.3); 7.578 (5.3); 7.560 (6.0); 7.556 (6.3); 7.533 (1.0); 7.498 (1.4); 7.476 (3.6); 7.470 (8.4); 7.450 (16.0); 7.430 (10.1); 7.278 (4.8); 7.268 (1.7); 7.247 (5.8); 7.229 (8.8); 7.210 (3.8); 7.181 (2.5); 7.161 (2.5); 7.143 (9.9); 7.115 (13.7); 7.094 (12.5); 7.073 (7.7); 7.052 (7.1); 7.008 (4.9); 6.924 (1.6); 6.902 (1.5); 5.066 (3.2); 3.702 (0.8); 3.447 (0.5); 3.338 (122.3); 3.327 (108.4); 2.890 (12.7); 2.836 (0.4); 2.731 (11.7); 2.671 (1.1); 2.548 (0.6); 2.506 (142.4); 2.502 (176.8); 2.329 (1.0); 1.389 (0.5); 1.375 (0.7); 1.360 (0.5); 1.290 (0.4); 1.237 (0.6); 0.000 (14.8) Example I-25: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 10.393 (7.2); 8.793 (4.7); 8.782 (4.9); 7.953 (2.6); 7.874 (4.0); 7.855 (6.8); 7.834 (2.7); 7.675 (2.9); 7.663 (3.2); 7.656 (2.9); 7.644 (2.4); 7.362 (1.4); 7.353 (7.4); 7.341 (15.5); 7.338 (12.6); 7.329 (7.9); 7.320 (1.5); 7.213 (3.5); 7.204 (3.3); 7.199 (3.1); 7.189 (2.7); 7.167 (3.6); 7.032 (7.4); 6.960 (16.0); 6.896 (3.7); 3.326 (124.7); 3.324 (153.6); 2.891 (14.9); 2.732 (14.0); 2.671 (0.7); 2.506 (90.3); 2.502 (107.5); 2.329 (0.7); 0.000 (2.4) Example I-26: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 10.408 (12.2); 10.339 (0.4); 8.793 (8.6); 8.785 (8.4); 8.782 (8.3); 8.328 (0.5); 8.288 (0.4); 8.272 (0.4); 7.978 (6.6); 7.959 (7.6); 7.873 (4.5); 7.858 (4.9); 7.852 (4.9); 7.749 (0.3); 7.687 (5.0); 7.675 (5.7); 7.669 (5.4); 7.656 (4.6); 7.629 (0.6); 7.591 (8.4); 7.587 (9.2); 7.571 (9.5); 7.567 (10.0); 7.392 (0.5); 7.365 (4.1); 7.362 (4.4); 7.344 (8.8); 7.342 (8.8); 7.326 (5.8); 7.323 (5.8); 7.262 (2.4); 7.245 (16.0); 7.235 (14.0); 7.226 (12.5); 7.208 (7.3); 7.206 (7.5); 7.186 (9.6); 7.170 (4.3); 7.167 (4.4); 7.135 (0.5); 7.111 (12.9); 7.066 (0.7); 7.051 (0.9); 7.047 (0.9); 7.022 (7.6); 7.002 (6.8); 6.976 (6.8); 6.955 (0.5); 6.916 (0.3); 6.878 (5.4); 6.872 (5.2); 6.855 (5.1); 6.820 (0.4); 6.700 (0.4); 6.680 (0.4); 3.701 (0.7); 3.320 (153.2); 3.015 (0.5); 2.890 (3.5); 2.762 (0.5); 2.731 (3.2); 2.674 (1.3); 2.670 (1.7); 2.505 (199.2); 2.501 (253.8); 2.497 (201.0); 2.328 (1.5); 1.256 (0.5); 1.237 (0.9); 0.000 (15.7) Example I-27: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 10.370 (12.7); 8.776 (9.4); 8.767 (9.4); 8.764 (9.1); 8.314 (0.3); 7.952 (1.7); 7.849 (4.9); 7.834 (5.2); 7.828 (5.3); 7.799 (7.6); 7.779 (9.4); 7.647 (5.9); 7.636 (6.4); 7.629 (5.5); 7.616 (4.6); 7.422 (2.8); 7.402 (7.7); 7.383 (8.8); 7.363 (4.4); 7.325 (2.2); 7.312 (8.0); 7.306 (13.0); 7.297 (16.0); 7.288 (13.9); 7.283 (8.3); 7.269 (2.2); 7.164 (7.0); 7.132 (6.7); 7.125 (5.9); 7.109 (5.6); 7.029 (15.2); 6.966 (4.4); 6.948 (7.6); 6.942 (7.6); 6.926 (3.7); 6.921 (3.6); 6.893 (7.6); 6.841 (0.4); 6.820 (0.3); 6.784 (14.6); 6.762 (11.0); 6.756 (7.5); 3.702 (1.0); 3.318 (169.4); 2.890 (10.7); 2.731 (9.8); 2.674 (1.1); 2.670 (1.5); 2.505 (188.4); 2.501 (237.2); 2.497 (177.4); 2.328 (1.4); 0.000 (10.1) Example I-28: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 10.352 (6.2); 8.784 (4.5); 8.775 (4.6); 7.952 (1.1); 7.895 (3.4); 7.875 (4.2); 7.859 (2.9); 7.841 (2.9); 7.667 (2.7); 7.655 (2.9); 7.648 (2.7); 7.636 (2.2); 7.271 (1.0); 7.266 (1.3); 7.252 (3.6); 7.247 (4.0); 7.235 (12.3); 7.229 (8.3); 7.213 (16.0); 7.197 (3.8); 7.191 (7.9); 7.181 (0.9); 7.074 (7.3); 7.030 (5.2); 7.019 (5.7); 7.007 (4.8); 6.996 (4.5); 6.985 (3.9); 6.964 (3.0); 6.939 (3.7); 3.702 (0.4); 3.321 (97.9); 2.890 (6.8); 2.732 (6.2); 2.674 (0.5); 2.670 (0.7); 2.666 (0.5); 2.506 (84.5); 2.501 (105.9); 2.497 (77.5); 2.333 (0.5); 2.328 (0.7); 0.000 (3.7) Example I-29: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 10.404 (7.7); 8.773 (5.1); 8.762 (5.1); 7.953 (2.6); 7.864 (2.8); 7.849 (4.8); 7.842 (16.0); 7.820 (13.6); 7.799 (0.4); 7.777 (0.4); 7.757 (4.1); 7.738 (5.6); 7.644 (3.5); 7.632 (3.7); 7.625 (2.9); 7.613 (2.5); 7.372 (1.4); 7.363 (7.5); 7.354 (6.9); 7.348 (7.2); 7.339 (8.1); 7.330 (1.5); 7.224 (3.9); 7.210 (3.3); 7.200 (2.8); 7.125 (3.9); 7.073 (0.7); 7.056 (12.3); 7.034 (11.3); 6.989 (8.2); 6.854 (4.0); 3.320 (80.8); 2.890 (15.7); 2.731 (14.8); 2.670 (0.9); 2.557 (0.4); 2.501 (137.0); 2.328 (0.9); 1.237 (0.5); 0.000 (8.3) Example I-30: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 10.357 (7.5); 8.783 (4.9); 8.780 (5.1); 8.771 (5.2); 8.768 (5.0); 8.267 (0.9); 8.245 (0.3); 7.953 (0.7); 7.855 (2.8); 7.827 (5.1); 7.806 (5.0); 7.652 (3.1); 7.640 (3.4); 7.633 (3.1); 7.621 (2.6); 7.566 (0.9); 7.557 (1.7); 7.549 (15.6); 7.544 (6.5); 7.531 (5.9); 7.526 (16.0); 7.518 (1.9); 7.491 (0.3); 7.468 (0.3); 7.305 (0.8); 7.300 (1.3); 7.286 (4.1); 7.280 (6.1); 7.271 (8.8); 7.262 (6.7); 7.255 (4.3); 7.242 (1.3); 7.183 (4.0); 7.111 (0.5); 7.078 (3.7); 7.072 (3.5); 7.048 (9.6); 6.977 (0.5); 6.953 (1.3); 6.929 (11.5); 6.913 (9.1); 6.907 (10.8); 6.842 (0.4); 6.820 (0.5); 3.702 (0.4); 3.317 (68.0); 2.890 (4.2); 2.731 (3.8); 2.674 (0.6); 2.670 (0.8); 2.666 (0.6); 2.523 (2.1); 2.505 (99.0); 2.501 (126.3); 2.497 (95.4); 2.332 (0.6); 2.328 (0.8); 2.323 (0.6); 1.259 (0.4); 1.236 (0.8); 0.000 (9.3) Example I-31: .sup.1H-NMR (300.2 MHz, CDCl.sub.3): = 7.512 (0.4); 7.485 (0.5); 7.468 (0.4); 7.461 (0.5); 7.260 (2.3); 7.223 (0.4); 7.196 (0.3); 7.189 (0.3); 6.895 (0.4); 6.737 (0.5); 4.129 (0.5); 4.105 (0.6); 2.041 (2.5); 1.550 (1.8); 1.330 (0.9); 1.307 (2.1); 1.281 (4.5); 1.267 (13.4); 1.234 (1.8); 0.904 (4.9); 0.882 (16.0); 0.859 (5.8); 0.000 (1.7) Example I-32: .sup.1H-NMR (300.2 MHz, CDCl.sub.3): = 8.732 (0.9); 8.727 (1.0); 8.716 (1.0); 8.711 (1.0); 8.330 (0.6); 8.303 (0.7); 8.068 (3.4); 7.796 (0.6); 7.771 (0.7); 7.662 (2.5); 7.657 (1.0); 7.640 (1.1); 7.635 (3.2); 7.600 (0.8); 7.491 (0.3); 7.480 (0.4); 7.471 (0.5); 7.462 (1.2); 7.445 (1.0); 7.435 (0.9); 7.418 (1.2); 7.412 (3.1); 7.407 (1.2); 7.385 (2.5); 7.322 (0.4); 7.308 (3.1); 7.298 (1.6); 7.289 (1.2); 7.285 (1.1); 7.261 (4.1); 7.140 (0.8); 6.958 (1.6); 6.776 (0.8); 3.979 (16.0); 2.040 (0.7); 1.594 (2.7); 1.280 (0.3); 1.267 (0.5); 1.256 (0.8); 0.881 (0.6); 0.000 (2.4) Example I-33: .sup.1H-NMR (300.2 MHz, d.sub.6-DMSO): = 10.471 (2.5); 8.841 (1.2); 8.837 (1.3); 8.825 (1.4); 8.821 (1.3); 8.254 (4.4); 7.976 (1.0); 7.951 (1.3); 7.765 (0.9); 7.749 (1.0); 7.739 (0.9); 7.724 (0.8); 7.578 (0.3); 7.551 (0.8); 7.532 (0.9); 7.526 (1.0); 7.505 (1.3); 7.498 (1.1); 7.471 (1.1); 7.443 (0.5); 7.388 (1.4); 7.364 (1.1); 7.306 (0.5); 7.291 (3.2); 7.259 (3.2); 7.244 (0.7); 7.151 (0.9); 6.970 (1.9); 6.790 (0.9); 3.941 (16.0); 3.881 (0.7); 3.329 (22.2); 2.508 (4.2); 2.502 (5.7); 2.496 (4.2); 1.990 (0.5); 1.356 (1.3); 1.238 (0.4); 1.175 (0.5); 1.150 (0.4); 0.000 (2.8) Example I-34: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 10.290 (10.5); 8.783 (6.7); 8.771 (6.7); 7.965 (5.5); 7.945 (6.4); 7.695 (4.2); 7.683 (4.5); 7.676 (4.3); 7.663 (3.7); 7.550 (5.5); 7.530 (8.5); 7.479 (7.4); 7.464 (11.2); 7.458 (12.7); 7.444 (11.1); 7.435 (4.5); 7.405 (14.0); 7.395 (12.9); 7.281 (9.0); 7.259 (16.0); 7.237 (7.5); 6.962 (3.7); 6.827 (8.0); 6.692 (4.0); 3.326 (116.9); 3.320 (112.5); 2.890 (0.5); 2.731 (0.5); 2.670 (0.9); 2.501 (155.5); 2.328 (0.9); 0.000 (7.4) Example I-35: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 10.337 (11.6); 8.795 (6.8); 8.784 (7.2); 8.011 (5.7); 7.992 (6.5); 7.952 (0.6); 7.718 (4.2); 7.706 (4.8); 7.700 (4.6); 7.687 (3.8); 7.658 (4.7); 7.638 (9.5); 7.617 (5.3); 7.595 (5.6); 7.576 (8.4); 7.513 (2.7); 7.508 (3.1); 7.490 (10.0); 7.473 (4.3); 7.462 (6.5); 7.459 (6.5); 7.450 (3.7); 7.432 (16.0); 7.416 (5.9); 7.397 (1.6); 7.311 (6.4); 7.290 (5.8); 7.012 (3.6); 6.877 (7.5); 6.741 (3.8); 3.320 (265.1); 2.890 (2.9); 2.731 (2.7); 2.669 (1.4); 2.501 (234.9); 2.327 (1.5); 0.001 (7.2) Example I-36: .sup.1H-NMR (300.2 MHz, d.sub.6-DMSO): = 7.579 (0.5); 7.548 (0.5); 3.323 (16.0); 2.513 (1.1); 2.507 (2.5); 2.501 (3.5); 2.495 (2.6); 2.489 (1.3); 0.000 (2.3) Example I-37: .sup.1H-NMR (300.2 MHz, CDCl.sub.3): = 8.653 (4.3); 8.648 (4.4); 8.637 (4.6); 8.632 (4.4); 8.053 (2.4); 8.036 (2.6); 8.023 (2.8); 8.006 (2.6); 7.818 (3.1); 7.793 (3.6); 7.632 (3.9); 7.523 (0.4); 7.519 (0.4); 7.505 (9.4); 7.490 (0.7); 7.477 (12.2); 7.471 (9.7); 7.464 (11.0); 7.444 (3.4); 7.434 (3.0); 7.418 (2.7); 7.268 (5.3); 7.226 (6.2); 7.219 (5.9); 7.198 (5.3); 7.191 (5.4); 7.186 (2.4); 7.176 (2.2); 7.159 (2.5); 7.157 (2.5); 7.150 (2.8); 7.130 (1.8); 7.120 (1.9); 7.075 (3.7); 7.032 (5.0); 7.022 (4.4); 7.003 (5.1); 6.993 (4.3); 6.892 (7.7); 6.710 (3.8); 4.119 (1.1); 4.095 (3.4); 4.071 (3.5); 4.048 (1.2); 2.128 (0.4); 2.012 (16.0); 1.990 (0.4); 1.686 (4.8); 1.305 (0.5); 1.268 (7.3); 1.244 (9.2); 1.232 (0.5); 1.220 (4.4); 0.902 (1.1); 0.880 (3.8); 0.856 (1.4); 0.000 (2.8) Example I-38: .sup.1H-NMR (400.1 MHz, d.sub.6-DMSO): = 10.360 (16.0); 8.809 (8.6); 8.805 (9.6); 8.797 (9.6); 8.794 (9.6); 8.004 (7.6); 7.984 (8.9); 7.731 (6.1); 7.719 (6.7); 7.711 (6.3); 7.699 (5.6); 7.654 (0.4); 7.602 (7.6); 7.583 (12.0); 7.533 (4.8); 7.528 (5.6); 7.516 (7.1); 7.511 (8.9); 7.496 (4.6); 7.491 (5.8); 7.477 (3.9); 7.472 (5.8); 7.458 (15.8); 7.453 (13.1); 7.448 (13.2); 7.445 (12.6); 7.431 (8.5); 7.428 (9.5); 7.412 (3.3); 7.409 (3.3); 7.271 (2.5); 7.265 (4.9); 7.259 (3.2); 7.247 (5.2); 7.241 (9.7); 7.235 (6.3); 7.223 (3.1); 7.218 (5.2); 7.212 (3.4); 7.191 (1.5); 7.185 (2.6); 7.174 (11.7); 7.169 (13.8); 7.152 (15.1); 7.147 (11.2); 7.136 (3.2); 7.038 (5.8); 6.903 (12.5); 6.768 (6.2); 3.371 (0.5); 3.320 (193.8); 3.272 (1.0); 3.254 (0.4); 2.686 (0.4); 2.682 (0.8); 2.677 (1.2); 2.673 (0.9); 2.559 (0.6); 2.531 (3.8); 2.517 (67.3); 2.513 (139.4); 2.508 (192.5); 2.504 (142.5); 2.499 (73.2); 2.413 (0.6); 2.408 (0.6); 2.340 (1.0); 2.335 (1.3); 2.331 (1.0); 1.996 (0.8); 1.183 (0.5) Example I-39: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 10.392 (8.2); 8.784 (4.4); 8.780 (4.8); 8.772 (4.7); 8.769 (4.7); 7.952 (2.4); 7.929 (4.0); 7.909 (4.6); 7.752 (3.0); 7.734 (16.0); 7.717 (6.1); 7.698 (5.2); 7.679 (6.8); 7.667 (3.8); 7.660 (4.3); 7.648 (2.8); 7.581 (3.5); 7.562 (6.3); 7.531 (2.2); 7.525 (2.6); 7.515 (3.2); 7.509 (4.1); 7.495 (1.8); 7.489 (3.1); 7.481 (2.4); 7.467 (8.5); 7.462 (10.2); 7.443 (3.6); 7.426 (1.0); 7.424 (0.9); 6.935 (3.0); 6.800 (6.6); 6.665 (3.3); 3.321 (197.2); 2.890 (15.9); 2.731 (14.0); 2.675 (0.7); 2.670 (0.9); 2.666 (0.7); 2.524 (2.3); 2.510 (58.4); 2.506 (116.2); 2.501 (152.0); 2.497 (111.0); 2.493 (55.3); 2.332 (0.7); 2.328 (0.9); 2.323 (0.7); 0.000 (4.7) Example I-40: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 10.314 (5.6); 8.790 (2.9); 8.787 (3.2); 8.779 (3.1); 8.776 (3.0); 7.989 (2.6); 7.970 (3.0); 7.952 (0.4); 7.706 (2.1); 7.694 (2.2); 7.687 (2.1); 7.675 (1.8); 7.560 (2.6); 7.541 (4.2); 7.502 (4.5); 7.497 (2.3); 7.486 (4.3); 7.481 (16.0); 7.461 (12.9); 7.446 (2.9); 7.439 (4.3); 7.412 (6.3); 7.402 (6.4); 6.980 (1.9); 6.845 (4.1); 6.710 (2.1); 3.318 (80.1); 2.890 (2.2); 2.731 (2.0); 2.674 (0.8); 2.670 (1.1); 2.666 (0.8); 2.505 (136.3); 2.501 (174.4); 2.496 (130.3); 2.332 (0.8); 2.328 (1.1); 2.323 (0.8); 0.000 (19.7) Example I-41: .sup.1H-NMR (300.2 MHz, d.sub.6-DMSO): = 10.336 (1.3); 8.787 (0.6); 8.783 (0.6); 8.771 (0.7); 8.767 (0.6); 8.252 (2.1); 8.002 (0.5); 7.977 (0.6); 7.702 (0.4); 7.676 (1.8); 7.648 (2.0); 7.569 (0.5); 7.544 (0.8); 7.500 (1.7); 7.473 (1.4); 7.466 (0.8); 7.452 (0.4); 7.440 (0.7); 7.426 (1.9); 7.415 (0.8); 7.032 (0.4); 6.852 (0.9); 6.672 (0.4); 5.757 (4.5); 4.194 (0.6); 4.171 (1.9); 4.147 (2.0); 4.124 (0.6); 3.326 (16.0); 2.513 (0.9); 2.507 (1.9); 2.501 (2.7); 2.495 (2.0); 2.489 (1.0); 1.989 (1.3); 1.356 (0.7); 1.274 (2.3); 1.262 (0.4); 1.250 (4.5); 1.227 (2.1); 1.198 (0.4); 1.174 (0.8); 1.150 (0.4); 0.000 (2.2) Example I-42: .sup.1H-NMR (300.2 MHz, d.sub.6-DMSO): = 10.328 (4.6); 8.800 (2.4); 8.796 (2.6); 8.785 (2.7); 8.780 (2.6); 8.003 (2.1); 7.977 (2.5); 7.721 (1.8); 7.705 (1.9); 7.695 (1.7); 7.679 (1.5); 7.591 (2.3); 7.565 (3.5); 7.544 (1.4); 7.530 (1.4); 7.523 (1.6); 7.515 (3.2); 7.508 (2.5); 7.498 (2.8); 7.492 (3.2); 7.480 (5.1); 7.465 (2.4); 7.455 (2.9); 7.451 (2.4); 7.439 (1.6); 7.426 (8.1); 7.415 (3.6); 7.408 (2.8); 7.404 (2.2); 7.383 (0.5); 7.379 (0.5); 7.300 (1.0); 7.296 (1.3); 7.286 (1.4); 7.281 (1.5); 7.274 (1.4); 7.267 (1.2); 7.260 (1.1); 7.253 (1.1); 7.056 (1.8); 6.876 (3.9); 6.696 (2.0); 3.332 (16.0); 2.513 (1.4); 2.508 (3.0); 2.501 (4.1); 2.495 (3.0); 2.489 (1.5); 0.000 (2.2) Example I-43: .sup.1H-NMR (300.2 MHz, CDCl.sub.3): = 8.729 (4.8); 8.724 (4.9); 8.713 (5.2); 8.708 (4.8); 8.211 (3.0); 8.184 (3.2); 7.863 (3.3); 7.837 (3.9); 7.687 (2.7); 7.661 (5.8); 7.635 (3.6); 7.607 (0.3); 7.538 (5.5); 7.532 (5.0); 7.508 (5.1); 7.504 (5.5); 7.485 (5.7); 7.482 (5.2); 7.475 (4.0); 7.459 (3.1); 7.369 (2.3); 7.365 (2.3); 7.343 (6.3); 7.340 (5.9); 7.320 (6.2); 7.316 (7.2); 7.312 (9.2); 7.306 (9.8); 7.299 (5.9); 7.287 (4.0); 7.271 (11.0); 7.261 (18.9); 7.236 (4.9); 7.060 (5.0); 6.878 (10.4); 6.695 (5.2); 1.582 (16.0); 1.255 (0.4); 0.010 (0.5); 0.000 (11.7); 0.011 (0.5) Example I-44: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 10.004 (10.2); 8.737 (6.2); 8.734 (5.9); 8.725 (6.5); 8.722 (5.7); 8.316 (0.3); 7.828 (6.0); 7.808 (7.3); 7.698 (5.2); 7.688 (7.4); 7.680 (7.9); 7.670 (5.3); 7.628 (8.9); 7.616 (7.2); 7.607 (16.0); 7.587 (5.2); 7.514 (3.4); 7.511 (3.1); 7.495 (6.0); 7.475 (3.3); 7.472 (2.9); 7.413 (6.7); 7.395 (6.0); 7.379 (3.8); 7.360 (7.3); 7.341 (4.1); 7.273 (7.0); 7.255 (4.8); 6.890 (4.0); 6.755 (8.8); 6.620 (4.4); 3.323 (129.4); 2.671 (0.9); 2.506 (106.5); 2.501 (132.9); 2.497 (98.3); 2.328 (0.9); 1.989 (0.5); 1.398 (0.4); 0.146 (0.7); 0.008 (8.9); 0.000 (153.7); 0.008 (8.2); 0.149 (0.7) Example I-45: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 10.301 (11.4); 8.779 (7.0); 8.768 (7.0); 7.953 (0.5); 7.943 (0.3); 7.899 (5.4); 7.879 (6.5); 7.689 (4.4); 7.677 (4.8); 7.670 (4.5); 7.657 (3.9); 7.600 (5.6); 7.581 (8.7); 7.523 (3.0); 7.517 (3.5); 7.506 (4.4); 7.501 (5.4); 7.487 (2.9); 7.481 (3.1); 7.456 (2.3); 7.434 (5.2); 7.418 (5.9); 7.403 (8.8); 7.387 (16.0); 7.374 (2.6); 7.353 (3.2); 7.347 (3.3); 7.328 (5.2); 7.322 (5.4); 7.304 (3.0); 7.298 (3.1); 7.276 (0.5); 7.248 (0.4); 7.193 (0.4); 7.179 (3.1); 7.173 (3.1); 7.157 (5.6); 7.152 (5.4); 7.136 (2.8); 7.130 (2.6); 6.965 (4.0); 6.830 (8.4); 6.695 (4.3); 3.319 (122.9); 3.015 (0.8); 2.890 (1.9); 2.761 (0.8); 2.731 (1.7); 2.670 (1.3); 2.505 (164.8); 2.501 (214.3); 2.497 (172.6); 2.328 (1.4); 1.257 (0.7); 1.237 (1.5); 0.854 (0.4); 0.000 (11.5) Example I-46: .sup.1H-NMR (300.2 MHz, CDCl.sub.3): = 8.749 (2.1); 8.745 (2.2); 8.734 (2.3); 8.729 (2.2); 8.429 (0.3); 8.308 (7.4); 8.286 (1.6); 7.912 (1.7); 7.886 (3.2); 7.860 (2.7); 7.828 (1.8); 7.610 (0.7); 7.569 (1.8); 7.509 (0.9); 7.496 (2.4); 7.481 (2.8); 7.469 (2.2); 7.456 (1.9); 7.307 (6.6); 7.293 (6.1); 7.272 (0.5); 7.262 (17.5); 7.194 (2.2); 7.190 (2.4); 7.164 (2.3); 7.149 (2.6); 7.145 (2.1); 7.115 (3.2); 7.109 (2.2); 6.934 (4.0); 6.752 (2.0); 4.299 (0.7); 4.283 (2.2); 4.275 (0.9); 4.259 (6.9); 4.236 (7.0); 4.212 (2.4); 4.154 (0.4); 4.131 (1.2); 4.107 (1.2); 4.083 (0.4); 2.043 (5.2); 1.575 (25.6); 1.378 (0.7); 1.353 (8.1); 1.329 (16.0); 1.306 (9.4); 1.282 (5.6); 1.266 (14.9); 1.259 (14.2); 1.234 (2.7); 0.903 (5.1); 0.882 (15.8); 0.859 (6.0); 0.071 (0.3); 0.011 (0.5); 0.000 (12.1); 0.011 (0.5) Example I-47: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 10.287 (9.1); 8.789 (5.5); 8.786 (5.9); 8.777 (5.8); 8.774 (5.6); 7.959 (4.9); 7.940 (5.6); 7.698 (4.0); 7.686 (4.2); 7.678 (3.7); 7.667 (3.4); 7.585 (3.8); 7.571 (4.3); 7.563 (4.6); 7.549 (4.4); 7.508 (6.5); 7.503 (3.4); 7.494 (8.0); 7.487 (8.9); 7.478 (4.1); 7.473 (7.8); 7.336 (2.4); 7.329 (3.1); 7.315 (4.2); 7.307 (6.9); 7.300 (9.7); 7.291 (8.2); 7.284 (8.8); 7.278 (16.0); 7.267 (7.1); 7.260 (6.6); 7.256 (7.7); 6.959 (3.7); 6.824 (8.3); 6.689 (4.1); 3.319 (113.1); 3.015 (0.6); 2.890 (4.2); 2.762 (0.6); 2.731 (3.6); 2.674 (0.6); 2.670 (0.8); 2.666 (0.6); 2.505 (104.6); 2.501 (132.5); 2.496 (97.5); 2.332 (0.7); 2.328 (0.9); 2.323 (0.7); 0.000 (11.9); 0.008 (0.5) Example I-48: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 10.313 (10.9); 8.802 (6.0); 8.799 (6.2); 8.790 (6.4); 8.787 (6.1); 8.033 (5.2); 8.014 (5.9); 7.729 (4.0); 7.717 (4.3); 7.710 (4.0); 7.698 (3.5); 7.627(5.7); 7.607 (7.7); 7.526 (2.7); 7.520 (3.0); 7.509 (4.1); 7.504 (5.1); 7.489 (2.8); 7.484 (3.3); 7.449 (3.0); 7.436 (12.0); 7.430 (16.0); 7.421 (8.6); 7.414 (7.8); 7.404 (8.5); 7.399 (8.4); 7.382 (6.8); 7.077 (3.8); 6.942 (8.2); 6.807 (4.1); 3.322 (62.2); 3.318 (63.8); 2.890 (0.8); 2.731 (0.7); 2.675 (0.7); 2.670 (0.9); 2.666 (0.7); 2.506 (109.9); 2.501 (138.9); 2.497 (100.7); 2.332 (0.6); 2.328 (0.8); 2.324 (0.6); 1.237 (0.7); 0.000 (14.7); 0.008 (0.6) Example I-49: .sup.1H-NMR (300.2 MHz, d.sub.6-DMSO): = 10.391 (1.0); 8.808 (0.5); 8.803 (0.5); 8.792 (0.6); 8.788 (0.5); 8.244 (2.0); 8.045 (0.4); 8.019 (0.5); 7.741 (0.3); 7.726 (0.4); 7.716 (0.3); 7.627 (0.4); 7.600 (0.7); 7.518 (0.5); 7.498 (0.5); 7.492 (0.5); 7.478 (0.9); 7.451 (0.6); 7.447 (0.6); 7.424 (0.5); 7.304 (1.2); 7.271 (1.2); 7.144 (0.3); 6.963 (0.7); 6.783 (0.4); 3.933 (8.7); 3.323 (16.0); 2.513 (1.9); 2.507 (4.1); 2.501 (5.6); 2.495 (4.1); 2.489 (2.0); 0.000 (3.7) Example I-50: .sup.1H-NMR (300.2 MHz, d.sub.6-DMSO): = 10.389 (0.7); 8.808 (0.6); 8.804 (0.7); 8.792 (0.7); 8.788 (0.6); 8.233 (2.5); 8.047 (0.5); 8.021 (0.6); 7.741 (0.4); 7.725 (0.5); 7.715 (0.4); 7.699 (0.4); 7.626 (0.5); 7.602 (0.8); 7.540 (0.4); 7.523 (0.5); 7.517 (0.6); 7.497 (0.6); 7.491 (0.6); 7.477 (1.0); 7.472 (0.7); 7.451 (0.7); 7.447(0.7); 7.425 (0.6); 7.298 (1.5); 7.265 (1.5); 7.141 (0.4); 6.961 (1.0); 6.781 (0.5); 4.229 (0.8); 4.205 (2.5); 4.182 (2.6); 4.159 (0.9); 3.325 (16.0); 2.514 (1.3); 2.508 (2.9); 2.501 (4.1); 2.495 (3.0); 2.489 (1.4); 1.276 (2.6); 1.253 (5.6); 1.229 (2.6); 0.000 (2.7) Example I-51: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 10.218 (8.0); 8.759 (4.9); 8.755 (5.3); 8.747 (5.3); 8.743 (5.1); 8.103 (0.8); 8.099 (0.6); 8.090 (0.6); 8.086 (0.9); 7.812 (3.7); 7.792 (4.6); 7.652 (3.4); 7.640 (3.5); 7.633 (3.0); 7.621 (2.8); 7.600 (4.1); 7.581 (5.9); 7.565 (0.5); 7.560 (0.7); 7.551 (4.2); 7.546 (3.2); 7.539 (4.8); 7.536 (3.6); 7.529 (6.0); 7.518 (1.3); 7.511 (2.8); 7.507 (3.0); 7.493 (4.8); 7.489 (4.9); 7.473 (2.8); 7.469 (2.8); 7.439 (0.3); 7.429 (0.4); 7.417 (1.3); 7.411 (3.6); 7.405 (9.1); 7.399 (4.2); 7.392 (16.0); 7.389 (10.1); 7.383 (10.3); 7.381 (10.6); 7.371 (12.2); 7.362 (4.3); 7.355 (2.2); 7.348 (2.2); 7.336 (6.7); 7.332 (6.6); 7.317 (4.0); 7.313 (3.6); 6.899 (2.9); 6.764 (6.3); 6.629 (3.2); 6.593 (0.9); 6.589 (0.7); 6.580 (0.7); 6.576 (0.9); 5.756 (8.0); 4.038 (0.8); 4.020 (0.8); 3.329 (54.1); 2.946 (11.0); 2.670 (0.4); 2.523 (1.0); 2.510 (21.1); 2.505 (42.2); 2.501 (55.5); 2.496 (40.2); 2.492 (19.3); 2.328 (0.4); 1.988 (3.5); 1.192 (1.0); 1.174 (1.9); 1.157 (0.9); 0.146 (0.4); 0.008 (3.5); 0.000 (88.5); 0.009 (3.4); 0.150 (0.4) Example I-52: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 10.347 (6.4); 8.790 (3.8); 8.781 (4.0); 8.778 (3.8); 7.953 (5.2); 7.934 (3.8); 7.703 (2.4); 7.691 (2.7); 7.684 (2.6); 7.672 (2.2); 7.564 (3.0); 7.545 (5.0); 7.505 (1.5); 7.497 (2.1); 7.487 (3.6); 7.483 (4.0); 7.469 (11.4); 7.450 (7.0); 7.434 (16.0); 7.419 (6.0); 7.415 (5.7); 7.410 (5.7); 7.406 (5.8); 7.392 (2.7); 7.388 (3.3); 6.994 (2.2); 6.859 (4.6); 6.724 (2.3); 3.317 (58.3); 3.015 (0.8); 2.890 (12.9); 2.761 (0.7); 2.731 (11.3); 2.669 (0.8); 2.666 (0.6); 2.505 (94.1); 2.500 (118.7); 2.496 (94.7); 2.327 (0.8); 2.323 (0.6); 1.236 (0.6); 0.000 (9.1) Example I-53: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 10.376 (6.6); 8.803 (3.8); 8.795 (3.7); 8.792 (3.7); 7.965 (3.1); 7.946(3.7); 7.725 (2.5); 7.713 (2.6); 7.706 (2.4); 7.694 (2.1); 7.611 (4.6); 7.606 (8.8); 7.601 (5.7); 7.596 (3.3); 7.576 (4.8); 7.531 (1.8); 7.526 (2.1); 7.509 (3.5); 7.493 (1.7); 7.489 (2.4); 7.474 (16.0); 7.469 (15.6); 7.463 (7.1); 7.440 (3.7); 7.423 (3.4); 7.404 (1.1); 7.059 (2.3); 6.924 (5.1); 6.789 (2.5); 3.322 (133.6); 2.890 (2.4); 2.731 (2.2); 2.675 (0.4); 2.671 (0.6); 2.666 (0.4); 2.506 (74.1); 2.501 (96.7); 2.497 (72.2); 2.332 (0.4); 2.328 (0.6); 0.000 (3.0) Example I-54: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 10.348 (7.4); 8.796 (4.4); 8.785 (4.3); 7.995 (3.7); 7.976 (4.1); 7.952 (0.4); 7.719 (2.9); 7.707 (3.5); 7.698 (10.4); 7.687 (3.6); 7.677 (16.0); 7.595 (3.7); 7.575 (5.4); 7.516 (1.8); 7.511 (2.2); 7.494 (3.7); 7.480 (1.8); 7.475 (2.4); 7.456 (2.4); 7.440 (10.0); 7.435 (11.5); 7.418 (6.4); 7.415 (7.0); 7.397 (1.1); 7.033 (2.6); 6.898 (5.6); 6.763 (2.8); 3.323 (124.7); 2.890 (1.9); 2.731 (1.7); 2.670 (0.6); 2.506 (77.2); 2.501 (98.5); 2.497 (74.4); 2.328 (0.6); 0.000 (2.7) Example I-55: .sup.1H-NMR (300.2 MHz, d.sub.6-DMSO): = 10.378 (2.4); 8.806 (1.3); 8.795 (1.3); 8.247 (4.2); 8.039 (1.0); 8.013 (1.2); 7.743 (0.9); 7.728 (0.9); 7.717 (1.1); 7.702 (0.8); 7.663 (0.6); 7.645 (0.7); 7.637 (0.9); 7.615 (0.7); 7.414 (2.4); 7.385 (2.7); 7.361 (1.1); 7.348 (3.0); 7.316 (2.8); 7.268 (0.3); 7.137 (0.8); 6.957 (1.8); 6.777 (0.9); 4.017 (0.4); 3.946 (1.2); 3.936 (16.0); 3.878 (1.1); 3.326 (73.3); 2.513 (6.2); 2.508 (13.2); 2.502 (18.5); 2.496 (13.9); 2.490 (7.0); 1.989 (1.2); 1.355 (0.8); 1.198 (0.4); 1.174 (0.7); 1.150 (0.4); 0.011 (0.5); 0.000 (12.8); 0.011 (0.6) Example I-56: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 10.275 (7.4); 8.788 (3.6); 8.785 (3.9); 8.776 (3.9); 8.773 (3.9); 7.986 (3.3); 7.967 (3.7); 7.699 (2.6); 7.688 (2.7); 7.680 (2.5); 7.668 (2.3); 7.617 (0.4); 7.596 (0.5); 7.547 (3.4); 7.529 (4.9); 7.457 (1.3); 7.448 (1.9); 7.443 (2.2); 7.434 (3.1); 7.425 (2.2); 7.415 (3.3); 7.395 (15.6); 7.386 (8.2); 7.373 (13.5); 7.351 (0.6); 7.329 (16.0); 7.307 (8.4); 6.988 (2.4); 6.853 (5.3); 6.718 (2.6); 3.318 (63.3); 3.014 (1.3); 2.889 (0.6); 2.761 (1.3); 2.730 (0.6); 2.674 (0.5); 2.669 (0.7); 2.664 (0.5); 2.661 (0.5); 2.522 (2.1); 2.509 (40.0); 2.505 (80.4); 2.500 (104.9); 2.496 (79.0); 2.488 (63.9); 2.331 (0.5); 2.327 (0.7); 2.322 (0.5); 0.008 (0.4); 0.000 (12.2); 0.009 (0.5) Example I-57: .sup.1H-NMR (300.2 MHz, CDCl.sub.3): = 8.700 (2.8); 8.695 (2.9); 8.684 (3.0); 8.679 (2.9); 8.198 (1.7); 8.171 (1.9); 7.854 (1.8); 7.829 (2.1); 7.691 (2.4); 7.473 (2.1); 7.458 (2.9); 7.448 (3.1); 7.439 (2.4); 7.432 (2.8); 7.422 (1.5); 7.411 (1.4); 7.312 (0.9); 7.309 (0.8); 7.287 (3.9); 7.283 (4.2); 7.273 (5.4); 7.266 (11.7); 7.263 (8.6); 7.249 (1.1); 7.240 (0.3); 7.073 (3.0); 6.968 (0.6); 6.957 (0.9); 6.936 (7.4); 6.906 (7.4); 6.891 (6.7); 6.885 (1.5); 6.874 (0.7); 6.709 (3.2); 4.262 (2.2); 4.239 (6.6); 4.215 (6.7); 4.192 (2.3); 2.021 (0.6); 1.681 (0.9); 1.416 (8.1); 1.392 (16.0); 1.369 (7.9); 1.271 (0.5); 1.258 (0.6); 1.247 (0.4); 0.880 (0.5); 0.000 (2.5) Example I-58: .sup.1H-NMR (400.1 MHz, CDCl.sub.3): = 8.770 (0.3); 8.683 (2.2); 8.680 (2.2); 8.671 (2.2); 8.668 (2.1); 8.160 (1.2); 8.140 (1.3); 7.839 (1.8); 7.822 (1.5); 7.819 (1.9); 7.740 (2.0); 7.451 (1.7); 7.441 (2.0); 7.433 (2.4); 7.422 (2.1); 7.413 (1.1); 7.406 (1.0); 7.300 (0.8); 7.297 (0.7); 7.281 (2.8); 7.278 (2.9); 7.267 (6.5); 7.264 (4.4); 7.262 (6.3); 7.248 (1.0); 7.242 (0.4); 7.198 (0.4); 7.061 (0.8); 7.025 (2.0); 6.946 (0.5); 6.943 (0.5); 6.938 (0.9); 6.922 (5.4); 6.900 (5.2); 6.889 (4.4); 6.875 (0.4); 6.752 (2.1); 4.129 (3.2); 4.113 (6.4); 4.097 (3.3); 2.013 (0.8); 1.823 (0.6); 1.805 (2.0); 1.787 (3.9); 1.769 (4.1); 1.752 (2.2); 1.735 (1.6); 1.260 (0.5); 1.242 (0.5); 1.049 (8.1); 1.031 (16.0); 1.012 (7.5); 0.000 (0.8) Example I-59: .sup.1H-NMR (400.1 MHz, CDCl.sub.3): = 8.779 (0.3); 8.683 (2.1); 8.680 (2.2); 8.671 (2.2); 8.668 (2.2); 8.162 (1.2); 8.142 (1.2); 7.842 (1.3); 7.839 (1.7); 7.822 (1.5); 7.819 (1.9); 7.737 (2.0); 7.450 (1.7); 7.440 (1.9); 7.432 (2.3); 7.421 (2.0); 7.413 (1.0); 7.406 (1.0); 7.299 (0.7); 7.296 (0.7); 7.280 (2.7); 7.277 (2.9); 7.266 (5.9); 7.263 (4.3); 7.261 (6.2); 7.248 (0.9); 7.197 (0.4); 7.061 (0.8); 7.024 (2.0); 6.943 (0.5); 6.937 (0.9); 6.921 (5.2); 6.899 (5.2); 6.888 (4.4); 6.874 (0.4); 6.751 (2.1); 4.169 (3.0); 4.153 (6.1); 4.136 (3.1); 2.013 (1.0); 1.775 (0.8); 1.758 (2.5); 1.751 (0.8); 1.741 (3.1); 1.736 (2.4); 1.721 (2.7); 1.705 (1.1); 1.541 (0.6); 1.522 (2.1); 1.508 (1.2); 1.503 (3.2); 1.490 (1.3); 1.484 (3.2); 1.471 (0.6); 1.466 (2.0); 1.448 (0.6); 1.260 (0.4); 1.242 (0.5); 0.986 (0.3); 0.978 (8.1); 0.959 (16.0); 0.941 (7.0); 0.000 (1.2) Example I-60: .sup.1H-NMR (300.2 MHz, d.sub.6-DMSO): = 10.470 (5.8); 8.837 (3.2); 8.821 (3.3); 8.243 (8.7); 7.979 (2.5); 7.953 (3.1); 7.764 (2.0); 7.748 (2.2); 7.738 (1.9); 7.722 (1.8); 7.705 (0.4); 7.577 (0.6); 7.550 (1.8); 7.526 (2.3); 7.503 (2.8); 7.498 (2.6); 7.466 (2.7); 7.439 (1.1); 7.386 (3.4); 7.361 (2.6); 7.284 (6.6); 7.253 (6.7); 7.214 (0.4); 7.149 (1.8); 6.968 (3.9); 6.787 (1.9); 4.236 (2.4); 4.213 (7.6); 4.189 (7.7); 4.166 (2.7); 4.137 (0.3); 3.328 (42.6); 3.287 (0.3); 2.508 (9.7); 2.502 (13.8); 2.498 (12.1); 2.183 (0.3); 1.990 (0.9); 1.356 (2.1); 1.279 (7.9); 1.256 (16.0); 1.233 (8.4); 1.195 (0.7); 1.171 (1.1); 1.150 (0.8); 0.000 (5.1) Example I-61: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 10.289 (3.5); 8.775 (2.1); 8.766 (2.1); 8.764 (2.1); 7.942 (1.8); 7.922 (2.1); 7.680 (1.4); 7.668 (1.6); 7.661 (1.4); 7.648 (1.3); 7.544 (1.8); 7.525 (2.8); 7.474 (1.0); 7.465 (1.2); 7.460 (1.6); 7.452 (2.2); 7.440 (11.7); 7.429 (16.0); 7.412 (5.5); 7.402 (4.2); 7.380 (1.6); 7.370 (2.0); 7.358 (2.2); 7.347 (1.2); 7.337 (0.6); 6.914 (1.3); 6.779 (2.8); 6.644 (1.4); 3.321 (43.8); 3.015 (0.7); 2.761 (0.7); 2.669 (0.4); 2.505 (43.4); 2.501 (56.2); 2.496 (43.4); 2.327 (0.3); 1.237 (0.5); 0.000 (3.5) Example I-62: .sup.1H-NMR (300.2 MHz, CDCl.sub.3): = 8.718 (0.4); 8.713 (0.4); 8.702 (0.4); 8.697 (0.4); 7.457 (1.2); 7.451 (0.6); 7.436 (0.8); 7.429 (1.7); 7.424 (0.5); 7.416 (0.4); 7.303 (1.4); 7.296 (0.5); 7.281 (1.6); 7.278 (1.7); 7.268 (0.8); 7.266 (0.8); 7.263 (0.8); 7.261 (1.0); 6.972 (0.6); 1.316 (16.0) Example I-63: .sup.1H-NMR (300.2 MHz, d.sub.6-DMSO): = 10.436 (8.1); 8.806 (3.8); 8.801 (4.2); 8.790 (4.2); 8.785 (4.2); 8.037 (3.2); 8.011 (3.8); 7.924 (5.9); 7.897 (7.1); 7.776 (7.0); 7.730 (2.9); 7.714 (2.9); 7.703 (2.7); 7.688 (2.5); 7.629 (6.5); 7.603 (8.2); 7.568 (2.3); 7.562 (2.7); 7.546 (3.3); 7.539 (4.1); 7.513 (4.4); 7.491 (6.7); 7.485 (4.6); 7.474 (5.0); 7.469 (4.8); 7.451 (3.3); 7.447 (3.6); 7.426 (1.3); 7.421 (1.2); 7.015 (2.8); 6.834 (6.4); 6.654 (3.2); 3.334 (16.0); 2.515 (1.7); 2.509 (3.6); 2.503 (5.0); 2.496 (3.5); 2.490 (1.6); 1.990 (0.4); 1.359 (2.0); 1.235 (0.6); 0.000 (4.0) Example I-64: .sup.1H-NMR (400.1 MHz, CDCl.sub.3): = 8.731 (1.0); 8.728 (1.0); 8.719 (1.0); 8.716 (1.0); 8.289 (3.4); 8.265 (0.5); 7.891 (0.8); 7.871 (1.5); 7.852 (1.0); 7.841 (0.6); 7.822 (0.7); 7.594 (0.8); 7.588 (0.7); 7.496 (0.4); 7.482 (1.0); 7.473 (0.8); 7.464 (1.0); 7.450 (0.7); 7.307 (1.7); 7.304 (3.0); 7.294 (3.0); 7.292 (2.7); 7.261 (4.4); 7.191 (0.9); 7.188 (1.1); 7.171 (0.9); 7.168 (1.0); 7.142 (1.1); 7.139 (0.9); 7.115 (1.0); 7.111 (0.9); 7.060 (0.9); 6.923 (1.9); 6.787 (0.9); 4.034 (1.8); 3.992 (16.0); 2.036 (0.8); 1.590 (4.4); 1.273 (0.4); 1.265 (0.3); 1.255 (0.6); 0.882 (0.5); 0.000 (2.7) Example I-65: .sup.1H-NMR (300.2 MHz, d.sub.6-DMSO): = 10.376 (6.1); 8.809 (3.8); 8.793 (4.0); 8.236 (9.5); 8.042 (3.2); 8.017 (3.7); 7.743 (2.4); 7.725 (2.7); 7.701 (2.3); 7.665 (1.7); 7.637 (2.5); 7.617 (2.0); 7.413 (6.0); 7.384 (7.0); 7.359 (3.0); 7.342 (7.3); 7.310 (7.2); 7.269 (0.8); 7.137 (2.0); 6.955 (4.2); 6.776 (2.1); 4.231 (2.5); 4.208 (7.7); 4.185 (7.9); 4.161 (3.1); 4.135 (0.5); 4.041 (0.4); 3.326 (68.2); 2.504 (34.2); 2.501 (34.7); 1.989 (1.2); 1.355 (1.4); 1.276 (8.0); 1.253 (16.0); 1.229 (8.2); 1.198 (0.9); 1.174 (1.2); 1.149 (0.7); 0.003 (10.9); 0.000 (12.7) Example I-66: .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): = 10.325 (10.5); 8.796 (5.6); 8.793 (6.1); 8.784 (6.0); 8.781 (5.9); 7.976 (4.9); 7.956 (6.1); 7.711 (3.9); 7.699 (4.2); 7.691 (3.8); 7.679 (3.5); 7.631 (5.1); 7.626 (5.5); 7.613 (5.3); 7.608 (5.3); 7.583 (5.2); 7.564 (7.6); 7.501 (5.3); 7.488 (4.1); 7.479 (13.2); 7.469 (3.0); 7.462 (4.2); 7.456 (9.8); 7.451 (5.5); 7.445 (5.9); 7.438 (6.1); 7.430 (15.0); 7.424 (16.0); 7.411 (6.0); 7.392 (1.3); 7.389 (1.2); 7.021 (3.7); 6.886 (8.2); 6.751 (4.1); 3.320 (185.4); 2.890 (7.5); 2.731 (6.6); 2.675 (0.6); 2.670 (0.8); 2.666 (0.6); 2.523 (2.0); 2.510 (51.2); 2.506 (102.7); 2.501 (134.7); 2.497 (98.3); 2.492 (48.5); 2.332 (0.6); 2.328 (0.8); 2.323 (0.6); 0.000 (5.2) Example I-67: .sup.1H-NMR (300.2 MHz, d.sub.6-DMSO): = 12.160 (0.4); 8.276 (0.7); 7.718 (0.5); 7.712 (0.4); 7.691 (0.7); 7.533 (0.3); 7.505 (1.0); 7.488 (0.4); 7.482 (0.5); 7.477 (0.6); 6.798 (0.4); 4.189 (0.7); 4.166 (0.7); 3.568 (16.0); 3.329 (4.2); 2.513 (0.3); 2.507 (0.7); 2.501 (0.9); 2.495 (0.7); 2.489 (0.3); 1.287 (0.8); 1.264 (1.6); 1.240 (0.7); 0.000 (0.6) Example I-68: .sup.1H-NMR (300.2 MHz, d.sub.6-DMSO): = 12.198 (0.8); 8.729 (0.6); 8.723 (0.7); 8.713 (0.7); 8.708 (0.6); 7.997 (0.8); 7.970 (0.9); 7.759 (1.2); 7.738 (0.7); 7.736 (0.7); 7.675 (0.6); 7.659 (0.5); 7.649 (0.4); 7.627 (1.2); 7.621 (1.6); 7.615 (1.6); 7.606 (0.9); 7.592 (0.6); 7.581 (0.6); 7.566 (1.6); 7.556 (0.8); 7.553 (0.9); 7.541 (0.4); 6.952 (0.4); 6.774 (0.9); 6.595 (0.4); 5.758 (0.7); 3.568 (10.5); 3.326 (16.0); 2.513 (0.8); 2.507 (1.8); 2.501 (2.5); 2.495 (1.8); 2.489 (0.9); 0.000 (1.7) Example I-69: .sup.1H-NMR (300.2 MHz, CDCl.sub.3): = 8.666 (1.2); 8.654 (1.2); 8.595 (1.0); 8.234 (3.7); 7.890 (1.0); 7.885 (1.0); 7.863 (1.3); 7.859 (1.3); 7.830 (1.0); 7.813 (0.9); 7.800 (1.0); 7.783 (1.0); 7.501 (0.9); 7.485 (1.0); 7.474 (0.8); 7.459 (0.9); 7.434 (0.3); 7.289 (0.7); 7.279 (0.9); 7.262 (21.8); 7.234 (0.7); 7.224 (0.8); 7.178 (1.4); 7.168 (1.1); 7.149 (1.4); 7.140 (1.1); 7.110 (0.4); 7.103 (0.6); 7.093 (3.1); 7.063 (3.3); 7.053 (0.6); 7.046 (0.4); 7.040 (0.5); 7.017 (1.1); 6.835 (2.2); 6.826 (0.4); 6.653 (1.1); 4.040 (16.0); 3.991 (1.8); 1.560 (33.3); 0.011 (0.6); 0.000 (14.6); 0.011 (0.6) Example I-70: .sup.1H-NMR (300.2 MHz, CDCl.sub.3): = 8.668 (0.9); 8.652 (1.1); 8.638 (0.8); 8.239 (2.3); 7.882 (0.7); 7.856 (0.9); 7.831 (0.6); 7.813 (0.6); 7.801 (0.7); 7.784 (0.6); 7.499 (0.6); 7.484 (0.6); 7.474 (0.6); 7.458 (0.5); 7.285 (0.4); 7.277 (0.6); 7.263 (15.5); 7.261 (13.3); 7.231 (0.5); 7.222 (0.5); 7.176 (0.8); 7.166 (0.7); 7.147 (0.8); 7.137 (0.7); 7.086 (2.0); 7.057 (2.0); 7.039 (0.4); 7.020 (0.7); 6.838 (1.3); 6.656 (0.6); 4.328 (0.7); 4.304 (2.1); 4.281 (2.2); 4.257 (0.8); 4.154 (0.4); 4.130 (1.3); 4.106 (1.4); 4.082 (0.5); 2.043 (5.8); 2.008 (3.9); 2.006 (3.4); 1.585 (12.9); 1.365 (2.3); 1.349 (1.0); 1.342 (4.7); 1.328 (1.5); 1.318 (3.1); 1.305 (2.6); 1.282 (5.6); 1.280 (5.8); 1.264 (15.3); 1.259 (16.0); 1.235 (3.2); 0.902 (4.9); 0.882 (13.3); 0.858 (5.8); 0.000 (9.3); 0.002 (7.9) Example I-71: .sup.1H-NMR (300.2 MHz, CDCl.sub.3): = 8.742 (0.6); 8.683 (0.8); 8.678 (0.8); 8.667 (0.8); 8.662 (0.8); 7.885 (0.7); 7.880 (0.7); 7.859 (0.9); 7.854 (0.8); 7.775 (0.7); 7.749 (1.0); 7.648 (0.4); 7.642 (0.5); 7.623 (0.9); 7.617 (0.9); 7.597 (0.6); 7.591 (0.6); 7.569 (0.5); 7.564 (0.5); 7.544 (0.9); 7.539 (0.9); 7.524 (0.8); 7.520 (0.7); 7.514 (0.6); 7.508 (0.7); 7.497 (0.6); 7.482 (0.6); 7.447 (1.1); 7.442 (1.0); 7.422 (0.8); 7.416 (0.7); 7.262 (9.4); 7.225 (2.5); 7.198 (2.5); 7.025 (0.8); 6.842 (1.7); 6.660 (0.9); 5.301 (1.0); 1.563 (16.0); 0.000 (2.0) Example I-72: .sup.1H-NMR (300.2 MHz, CDCl.sub.3): = 8.680 (2.9); 8.675 (3.0); 8.664 (3.1); 8.660 (3.0); 8.539 (3.2); 8.253 (8.2); 7.826 (2.4); 7.800 (2.8); 7.558 (1.1); 7.540 (1.2); 7.532 (2.4); 7.514 (2.4); 7.505 (1.8); 7.486 (2.4); 7.466 (2.2); 7.456 (2.1); 7.440 (2.7); 7.417 (0.3); 7.346 (2.1); 7.318 (3.2); 7.291 (1.6); 7.287 (1.6); 7.262 (34.4); 7.232 (3.0); 7.112 (0.9); 7.095 (7.3); 7.065 (7.0); 7.055 (1.5); 7.046 (1.7); 7.030 (0.3); 6.910 (4.6); 6.888 (0.7); 6.730 (2.2); 6.707 (0.3); 4.331 (2.5); 4.307 (7.7); 4.284 (7.9); 4.260 (2.8); 4.242 (1.2); 4.219 (0.4); 4.123 (0.4); 4.099 (0.4); 2.036 (1.6); 2.005 (0.5); 1.566 (51.8); 1.533 (0.4); 1.369 (8.0); 1.345 (16.0); 1.322 (8.0); 1.313 (1.9); 1.289 (2.7); 1.279 (1.4); 1.266 (3.4); 1.256 (2.4); 1.231 (0.7); 0.903 (0.8); 0.882 (2.3); 0.859 (0.9); 0.000 (20.9); 0.011 (1.2) Example I-73: .sup.1H-NMR (300.2 MHz, CDCl.sub.3): = 8.669 (1.5); 8.664 (1.6); 8.653 (1.8); 8.648 (1.7); 8.618 (1.0); 7.954 (1.5); 7.929 (1.7); 7.838 (1.4); 7.833 (1.4); 7.811 (1.6); 7.807 (1.6); 7.565 (0.7); 7.559 (0.8); 7.540 (1.6); 7.534 (1.6); 7.515 (1.2); 7.508 (1.3); 7.498 (1.0); 7.493 (1.1); 7.473 (2.9); 7.468 (2.2); 7.458 (1.5); 7.448 (2.3); 7.445 (1.6); 7.432 (1.4); 7.426 (2.6); 7.420 (2.2); 7.400 (1.3); 7.394 (1.0); 7.332 (0.9); 7.325 (1.0); 7.306 (0.9); 7.300 (1.1); 7.295 (1.0); 7.288 (1.0); 7.261 (24.5); 7.233 (1.5); 7.208 (1.4); 7.200 (1.4); 7.192 (1.3); 7.186 (1.2); 7.183 (1.2); 7.175 (2.7); 7.169 (1.7); 7.157 (0.5); 7.146 (0.4); 7.140 (0.4); 7.030 (1.7); 6.848 (3.5); 6.666 (1.7); 5.300 (1.7); 1.546 (16.0); 0.011 (0.7); 0.000 (22.2); 0.011 (0.9) Example I-74: .sup.1H-NMR (300.2 MHz, CDCl.sub.3): = 8.712 (1.2); 8.707 (1.2); 8.696 (1.3); 8.692 (1.2); 8.453 (1.1); 8.253 (3.6); 7.835 (1.0); 7.811 (1.2); 7.561 (0.5); 7.544 (0.6); 7.535 (1.0); 7.517 (1.1); 7.508 (0.8); 7.491 (1.4); 7.476 (1.0); 7.466 (0.9); 7.450 (1.2); 7.354 (0.8); 7.350 (0.9); 7.322 (1.4); 7.294 (0.8); 7.290 (0.8); 7.262 (35.4); 7.235 (1.5); 7.122 (0.4); 7.105 (3.1); 7.093 (1.2); 7.075 (3.4); 7.066 (0.7); 7.058 (0.6); 7.050 (0.6); 6.912 (2.2); 6.878 (0.3); 6.732 (1.0); 4.047 (16.0); 4.000 (2.4); 2.042 (0.5); 2.007 (1.0); 1.559 (52.5); 1.258 (0.5); 0.011 (0.9); 0.000 (22.8); 0.011 (1.0) Example I-75: .sup.1H-NMR (300.2 MHz, CDCl.sub.3): = 8.670 (1.0); 8.664 (0.9); 8.653 (0.7); 8.648 (0.7); 8.243 (2.1); 7.903 (0.6); 7.893 (0.6); 7.888 (0.6); 7.878 (0.8); 7.867 (0.7); 7.862 (0.7); 7.568 (0.6); 7.562 (0.6); 7.542 (0.5); 7.536 (0.5); 7.522 (0.4); 7.517 (0.4); 7.496 (1.2); 7.493 (1.1); 7.479 (0.6); 7.472 (0.8); 7.469 (0.9); 7.453 (1.4); 7.448 (1.0); 7.428 (0.5); 7.422 (0.4); 7.262 (10.1); 7.091 (1.8); 7.061 (1.8); 7.051 (0.3); 7.036 (0.7); 6.854 (1.3); 6.672 (0.7); 5.301 (1.8); 4.324 (0.7); 4.300 (2.3); 4.277 (2.3); 4.253 (0.8); 1.560 (16.0); 1.364 (2.4); 1.340 (4.9); 1.317 (2.3); 0.000 (4.4) Example I-76: .sup.1H-NMR (300.2 MHz, CDCl.sub.3): = 8.675 (1.2); 8.670 (1.2); 8.654 (1.6); 8.241 (3.3); 7.899 (1.4); 7.892 (1.1); 7.872 (1.7); 7.595 (0.5); 7.589 (0.6); 7.571 (1.1); 7.565 (1.2); 7.545 (0.9); 7.539 (0.9); 7.525 (0.7); 7.520 (0.7); 7.499 (2.1); 7.495 (1.8); 7.482 (1.1); 7.475 (1.4); 7.472 (1.5); 7.456 (2.6); 7.450 (1.8); 7.437 (0.6); 7.431 (0.9); 7.425 (0.7); 7.261 (28.1); 7.117 (0.3); 7.109 (0.5); 7.100 (2.8); 7.069 (3.0); 7.060 (0.6); 7.052 (0.4); 7.046 (0.6); 7.035 (1.1); 6.853 (2.1); 6.846 (0.5); 6.671 (1.0); 5.301 (0.7); 4.038 (16.0); 3.993 (2.7); 2.007 (0.6); 1.548 (15.3); 0.011 (0.8); 0.000 (25.5); 0.011 (1.1)
Example: In Vivo Preventive Test on Alternaria brassicae (Leaf Spot on Radish)
[0225]
TABLE-US-00003 Solvent: 5% by volume of Dimethyl sulfoxide 10% by volume of Acetone Emulsifier: 1 l of Tween 80 per mg of active ingredient
[0226] The active ingredients are made soluble and homogenized in a mixture of Dimethyl sulfoxide/Acetone/Tween 80 and then diluted in water to the desired concentration.
[0227] The young plants of radish are treated by spraying the active ingredient prepared as described above. Control plants are treated only with an aqueous solution of Acetone/Dimethyl sulfoxide/Tween 80.
[0228] After 24 hours, the plants are contaminated by spraying the leaves with an aqueous suspension of Alternaria brassicae spores. The contaminated radish plants are incubated for 6 days at 20 C. and at 100% relative humidity.
[0229] The test is evaluated 6 days after the inoculation. 0% means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease is observed.
[0230] In this test, the following compounds according to the invention showed efficacy of at least 70% at a concentration of 100 ppm of active ingredient: I-07; I-17; I-32; I-34; I-35; I-36; I-37; I-38; I-39; I-41; I-42; I-43; I-46; I-49; I-50; I-53; I-54; I-55; I-57; I-58; I-59; I-60; I-62; I-63; I-64; I-65; I-66; I-67; I-68; I-69; I-70; I-72; I-74
Example: In Vivo Preventive Test on Botrytis cinerea (Grey Mould)
[0231]
TABLE-US-00004 Solvent: 5% by volume of Dimethyl sulfoxide 10% by volume of Acetone Emulsifier: 1 l of Tween 80 per mg of active ingredient
[0232] The active ingredients are made soluble and homogenized in a mixture of Dimethyl sulfoxide/Acetone/Tween 80 and then diluted in water to the desired concentration.
[0233] The young plants of gherkin are treated by spraying the active ingredient prepared as described above. Control plants are treated only with an aqueous solution of Acetone/Dimethyl sulfoxide/Tween 80.
[0234] After 24 hours, the plants are contaminated by spraying the leaves with an aqueous suspension of Botrytis cinerea spores. The contaminated gherkin plants are incubated for 4 to 5 days at 17 C. and at 90% relative humidity.
[0235] The test is evaluated 4 to 5 days after the inoculation. 0% means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease is observed.
[0236] In this test, the following compounds according to the invention showed efficacy of at least 70% at a concentration of 100 ppm of active ingredient: I-17; I-32; I-34; I-35; I-36; I-37; I-38; I-41; I-42; I-43; I-46; I-49; I-50; I-54; I-57; I-58; I-59; I-62; I-63; I-64; I-66; I-67; I-68; I-73; I-76
Example: In Vivo Preventive Test on Puccinia recondita (Brown Rust on Wheat)
[0237]
TABLE-US-00005 Solvent: 5% by volume of Dimethyl sulfoxide 10% by volume of Acetone Emulsifier: 1 l of Tween 80 per mg of active ingredient
[0238] The active ingredients are made soluble and homogenized in a mixture of Dimethyl sulfoxide/Acetone/Tween 80 and then diluted in water to the desired concentration.
[0239] The young plants of wheat are treated by spraying the active ingredient prepared as described above. Control plants are treated only with an aqueous solution of Acetone/Dimethyl sulfoxide/Tween 80.
[0240] After 24 hours, the plants are contaminated by spraying the leaves with an aqueous suspension of Puccinia recondita spores. The contaminated wheat plants are incubated for 24 hours at 20 C. and at 100% relative humidity and then for 10 days at 20 C. and at 70-80% relative humidity.
[0241] The test is evaluated 11 days after the inoculation. 0% means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease is observed.
[0242] In this test, the following compounds according to the invention showed efficacy of at least 70% at a concentration of 100 ppm of active ingredient: I-01; I-02; I-03; I-04; I-05; I-06; I-07; I-08; I-11; I-12; I-13; I-14; I-15; I-16; I-17; I-18; I-19; I-20; I-25; I-26; I-27; I-28; I-30; I-32; I-33; I-34; I-35; I-36; I-37; I-38; I-39; I-41; I-42; I-43; I-45; I-46; I-49; I-50; I-52; I-53; I-54; I-55; I-56; I-57; I-58; I-59; I-61; I-62; I-63; I-64; I-66; I-67; I-68; I-69; I-70; I-71; I-72; I-73; I-74; I-76
[0243] In this test, the following compounds according to the invention showed efficacy of at least 70% at a concentration of 10 ppm of active ingredient: I-6
Example: In Vivo Preventive Test on Pyrenophora teres (Net Blotch on Barley)
[0244]
TABLE-US-00006 Solvent: 5% by volume of Dimethyl sulfoxide 10% by volume of Acetone Emulsifier: 1 l of Tween 80 per mg of active ingredient
[0245] The active ingredients are made soluble and homogenized in a mixture of Dimethyl sulfoxide/Acetone/Tween 80 and then diluted in water to the desired concentration.
[0246] The young plants of barley are treated by spraying the active ingredient prepared as described above. Control plants are treated only with an aqueous solution of Acetone/Dimethyl sulfoxide/Tween 80.
[0247] After 24 hours, the plants are contaminated by spraying the leaves with an aqueous suspension of Pyrenophora teres spores. The contaminated barley plants are incubated for 48 hours at 20 C. and at 100% relative humidity and then for 12 days at 20 C. and at 70-80% relative humidity.
[0248] The test is evaluated 14 days after the inoculation. 0% means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease is observed.
[0249] In this test, the following compounds according to the invention showed efficacy of at least 70% at a concentration of 100 ppm of active ingredient: I-07; I-08; I-12; I-17; I-18; I-32; I-33; I-34; I-35; I-37; I-38; I-39; I-41; I-43; I-46; I-49; I-52; I-53; I-54; I-57; I-58; I-59; I-60; I-62; I-63; I-64; I-66; I-67; I-68; I-69; I-71; I-73; I-74; I-76
Example: In Vivo Preventive Test on Septoria tritici (Leaf Spot on Wheat)
[0250]
TABLE-US-00007 Solvent: 5% by volume of Dimethyl sulfoxide 10% by volume of Acetone Emulsifier: 1 l of Tween 80 per mg of active ingredient
[0251] The active ingredients are made soluble and homogenized in a mixture of Dimethyl sulfoxide/Acetone/Tween 80 and then diluted in water to the desired concentration.
[0252] The young plants of wheat are treated by spraying the active ingredient prepared as described above. Control plants are treated only with an aqueous solution of Acetone/Dimethyl sulfoxide/Tween 80.
[0253] After 24 hours, the plants are contaminated by spraying the leaves with an aqueous suspension of Septoria tritici spores. The contaminated wheat plants are incubated for 72 hours at 18 C. and at 100% relative humidity and then for 21 days at 20 C. and at 90% relative humidity.
[0254] The test is evaluated 24 days after the inoculation. 0% means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease is observed.
[0255] In this test, the following compounds according to the invention showed efficacy of at least 70% at a concentration of 100 ppm of active ingredient: I-03; I-04; I-06; I-07; I-08; I-12; I-15; I-16; I-17; I-18; I-20; I-22; I-25; I-27; I-28; I-31; I-33; I-34; I-35; I-38; I-39; I-41; I-45; I-46; I-47; I-49; I-52; I-53; I-54; I-55; I-57; I-58; I-59; I-60; I-61; I-63; I-64; I-66; I-68; I-69; I-70; I-74
[0256] In this test, the following compounds according to the invention showed efficacy of at least 70% at a concentration of 10 ppm of active ingredient: I-11; I-21
Example: In Vivo Preventive Test on Sphaerotheca fuliginea (Powdery Mildew on Cucurbits)
[0257]
TABLE-US-00008 Solvent: 5% by volume of Dimethyl sulfoxide 10% by volume of Acetone Emulsifier: 1 l of Tween 80 per mg of active ingredient
[0258] The active ingredients are made soluble and homogenized in a mixture of Dimethyl sulfoxide/Acetone/Tween 80 and then diluted in water to the desired concentration.
[0259] The young plants of gherkin are treated by spraying the active ingredient prepared as described above. Control plants are treated only with an aqueous solution of Acetone/Dimethyl sulfoxide/Tween 80.
[0260] After 24 hours, the plants are contaminated by spraying the leaves with an aqueous suspension of Sphaerotheca fuliginea spores. The contaminated gherkin plants are incubated for 72 hours at 18 C. and at 100% relative humidity and then for 12 days at 20 C. and at 70-80% relative humidity.
[0261] The test is evaluated 15 days after the inoculation. 0% means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease is observed.
[0262] In this test, the following compounds according to the invention showed efficacy of at least 70% at a concentration of 100 ppm of active ingredient: I-03; I-04; I-07; I-08; I-12; I-16; I-17; I-18; I-25; I-26; I-28; I-30; I-32; I-33; I-34; I-35; I-36; I-37; I-38; I-39; I-41; I-42; I-43; I-45; I-46; I-47; I-49; I-50; I-52; I-53; I-54; I-55; I-57; I-58; I-59; I-60; I-61; I-62; I-63; I-64; I-65; I-66; I-67; I-68; I-69; I-70; I-71; I-72; I-73; I-74; I-76
Example: In Vivo Preventive Test on Uromyces appendiculatus (Bean Rust)
[0263]
TABLE-US-00009 Solvent: 5% by volume of Dimethyl sulfoxide 10% by volume of Acetone Emulsifier: 1 l of Tween 80 per mg of active ingredient
[0264] The active ingredients are made soluble and homogenized in a mixture of Dimethyl sulfoxide/Acetone/Tween 80 and then diluted in water to the desired concentration.
[0265] The young plants of bean are treated by spraying the active ingredient prepared as described above. Control plants are treated only with an aqueous solution of Acetone/Dimethyl sulfoxide/Tween 80.
[0266] After 24 hours, the plants are contaminated by spraying the leaves with an aqueous suspension of Uromyces appendiculatus spores. The contaminated bean plants are incubated for 24 hours at 20 C. and at 100% relative humidity and then for 10 days at 20 C. and at 70-80% relative humidity.
[0267] The test is evaluated 11 days after the inoculation. 0% means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease is observed.
[0268] In this test, the following compounds according to the invention showed efficacy of at least 70% at a concentration of 500 ppm of active ingredient: I-31
[0269] In this test, the following compounds according to the invention showed efficacy of at least 70% at a concentration of 100 ppm of active ingredient: I-03; I-04; I-06; I-07; I-08; I-12; I-15; I-16; I-17; I-18; I-19; I-25; I-26; I-27; I-28; I-30; I-32; I-33; I-35; I-36; I-38; I-39; I-41; I-42; I-43; I-46; I-49; I-50; I-52; I-53; I-54; I-55; I-57; I-58; I-59; I-60; I-62; I-63; I-64; I-65; I-66; I-67; I-68; I-69; I-70; I-71; I-72; I-73; I-74; I-76
Example: In Vivo Preventive Test on Phakopsora Test (Soybeans)
[0270]
TABLE-US-00010 Solvent: 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide Emulsifier: 1 part by weight of alkylaryl polyglycol ether
[0271] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
[0272] To test for preventive activity, young plants are sprayed with the preparation of active compound at the stated rate of application. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of the causal agent of soybean rust (Phakopsora pachyrhizi) and stay for 24 h without light in an incubation cabinet at approximately 24 C. and a relative atmospheric humidity of 95%.
[0273] The plants remain in the incubation cabinet at approximately 24 C. and a relative atmospheric humidity of approximately 80% and a day/night interval of 12 h.
[0274] The test is evaluated 7 days after the inoculation. 0% means an efficacy which corresponds to that of the untreated control, while an efficacy of 100% means that no disease is observed.
[0275] In this test, the following compounds according to the invention showed efficacy of at least 70% at a concentration of 10 ppm of active ingredient: I-43; I-49
Experimental Examples
Process (a)
[0276] ##STR00006##
2-(difluoromethyl)-N-[2-(4-methylphenoxy)phenyl]nicotinamide (ex I-01)
[0277] In a microwave sealable tube, propanephosphonic anhydride (50% in AcOEt, 809 mg, 1.272 mmol, 2.2 eq) is added to a solution of 2-(difluoromethyl)-5-methylnicotinic acid (120 mg, 0.694 mmol, 1.2 eq) and 2-(4-methylphenoxy)aniline (115 mg, 0.578 mmol, 1 eq.) in 2 ml of DMF. The tube is sealed and the reaction is microwaved 20 min at 150 C. The resulting solution is evaporated to dryness and diluted with DCM, treated with 1N NaOH (1.5 ml) and filtered through a silica cartridge follow by washing with DCM. The solvent is evaporated to give pure material (71%)
Process (b)
[0278] ##STR00007##
N-[3-chloro-4-(trifluoromethyl)biphenyl-2-yl]-2-(difluoromethyl)pyridine-3-carbothioamide (ex. I-68)
[0279] In a microwave sealable tube, P.sub.2S.sub.5 (31 mg, 0.141 mmol, 0.5 eq) is added to a solution of N-[3-chloro-4-(trifluoromethyl)biphenyl-2-yl]-2-(difluoromethyl)nicotinamide (120 mg, 0.281 mmol, 1 eq) in 1.7 ml of dioxane. The tube is sealed and the reaction is microwaved 20 min at 130 C. The resulting solution is filtered through alumina and washed with dioxane. The solvent is evaporated and the residue purified by chromatography on silica gel to give pure material (86%)