1-PYRAZINYLPYRAZOLYL-3-OXYALKYL ACIDS AND THEIR DERIVATIVES, AND THEIR USE FOR CONTROL OF UNDESIRED PLANT GROWTH

Abstract

The present invention relates to novel, herbicidally active, substituted 1-pyrazinylpyrazolyl-3-oxyalkyl acids and their derivatives of the general formula (I) and their agrochemically compatible salts, N-oxides, hydrates, and hydrates of the salts and N-oxides, to processes for preparation thereof and to the use thereof for control of broadleaved weeds and weed grasses in crops of useful plants, and for general control of broadleaved weeds and weed grasses in areas of the environment where plant growth is troublesome.

Claims

1. Substituted 1-pyrazinylpyrazolyl-3-oxyalkyl acids of the general formula (I) and their agrochemically acceptable salts, N-oxides, hydrates, and hydrates of the salts and N-oxides, ##STR00037## where A is A1-A28: ##STR00038## ##STR00039## R.sup.1a is OR.sup.1a or NR.sup.9R.sup.10; in which R.sup.1a is hydrogen; is (C.sub.1-C.sub.12)-alkyl which is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.1-C.sub.4)-trialkylsilyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.4)-alkoxy-(C.sub.1-C.sub.4)-alkoxy, cyano and nitro; is (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-haloalkenyl; is (C.sub.2-C.sub.6)-alkynyl; is (C.sub.3-C.sub.6)-cycloalkyl which is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl; is (C.sub.1-C.sub.4)-alkyl-SO—(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkyl-SO.sub.2—(C.sub.1-C.sub.4)-alkyl; is heterocyclyl, heteroaryl and aryl which is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl; is heterocyclyl-(C.sub.1-C.sub.4)-alkyl, heteroaryl-(C.sub.1-C.sub.4)-alkyl and aryl-(C.sub.1-C.sub.4)-alkyl, where the heterocyclyl, heteroaryl and aryl is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl; is (C.sub.1-C.sub.6)-alkylideneamino; R.sup.9 is hydrogen and (C.sub.1-C.sub.12)-alkyl; R.sup.10 is hydrogen; is aryl, heteroaryl, heterocyclyl, which is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl; is (C.sub.3-C.sub.7)-cycloalkyl-(C.sub.1-C.sub.4)-alkyl, heterocyclyl-(C.sub.1-C.sub.4)-alkyl, heteroaryl-(C.sub.1-C.sub.4)-alkyl, aryl-(C.sub.1-C.sub.4)-alkyl, aryl-(C.sub.1-C.sub.4)-alkoxy; where the cycloalkyl, heterocyclyl, heteroaryl and aryl is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl; (C.sub.1-C.sub.12)-alkyl; (C.sub.3-C.sub.8)-cycloalkyl, (C.sub.2-C.sub.12)-alkenyl, (C.sub.8-C.sub.8)-cycloalkenyl, (C.sub.2-C.sub.12)-alkynyl; where the abovementioned alkyl, cycloalkenyl, alkenyl, cycloalkenyl and alkynyl radicals are unsubstituted or each independently substituted by m radicals selected from the group consisting of cyano, nitro, OR.sup.5, S(O).sub.nRS, SO.sub.2NR.sup.6R.sup.7, C(O)OR.sup.8, CONR.sup.6R.sup.8, COR.sup.6, NR.sup.6R.sup.8, NR.sup.6COR.sup.8, NR.sup.6CONR.sup.8R.sup.8, NR.sup.6CO.sub.2R.sup.8, NR.sup.6SO.sub.2R.sup.8, NR.sup.6SO.sub.2NR.sup.6R.sup.8, C(R.sup.6)═NOR.sup.8; is (C.sub.1-C.sub.12)-haloalkyl; is S(O).sub.nR.sup.5, cyano, nitro, OR.sup.5, SO.sub.2NR.sup.6R.sup.7, CO.sub.2R.sup.8, COR.sup.8, NR.sup.6R.sup.8, NR.sup.6COR.sup.8, NR.sup.6CO.sub.2R.sup.8, NR.sup.6SO.sub.2R.sup.8; or R.sup.9 and R.sup.10 together with the nitrogen atom to which they are bonded form a saturated or partly or fully unsaturated five-, six- or seven-membered ring which is optionally mono- to hexasubstituted by radicals from the group consisting of halogen, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, OR.sup.5, S(O).sub.nR.sup.5, CO.sub.2R.sup.8, CONR.sup.6R.sup.8, COR.sup.6 and C(R.sup.6)═NOR.sup.8 and which, in addition to this nitrogen atom, contains r carbon atoms, o oxygen atoms, p sulfur atoms and q elements from the group consisting of NR.sup.7, CO and NCOR.sup.7 as ring atoms; R.sup.5 is (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.2-C.sub.4)-alkenyl or aryl; R.sup.6 is hydrogen or R.sup.5; R.sup.7 is hydrogen, (C.sub.1-C.sub.8)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.2-C.sub.4)-alkenyl or (C.sub.3-C.sub.4)-alkynyl; R.sup.8 is hydrogen, (C.sub.1-C.sub.8)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.4)-alkenyl or (C.sub.3-C.sub.4)-alkynyl; R.sup.2a is hydrogen, halogen, cyano; (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.4)-alkoxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-alkoxy; (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-haloalkenyl; (C.sub.2-C.sub.6)-alkynyl, (C.sub.2-C.sub.6)-haloalkynyl; (C.sub.3-C.sub.6)-cycloalkyl; R.sup.2b is hydrogen and (C.sub.1-C.sub.4)-alkyl; R.sup.3 is halogen, cyano, isocyano, NO.sub.2; (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-alkylcarbonyl, (C.sub.1-C.sub.6)-haloalkylcarbonyl, (C.sub.1-C.sub.4)-alkyloxycarbonyl; (C.sub.2-C.sub.3)-alkenyl, (C.sub.2-C.sub.3)-haloalkenyl; (C.sub.2-C.sub.3)-alkynyl, (C.sub.2-C.sub.3)-haloalkynyl; (C.sub.1-C.sub.2)-alkyl-S(O).sub.n and (C.sub.1-C.sub.2)-haloalkyl-S(O).sub.n; CHO, C(O)NH.sub.2; NH.sub.2; R.sup.4 is halogen, cyano, isocyano, nitro; (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.3)-haloalkoxy; (C.sub.2-C.sub.3)-alkenyl, (C.sub.2-C.sub.3)-haloalkenyl; (C.sub.2-C.sub.3)-alkynyl, (C.sub.2-C.sub.3)-haloalkynyl; (C.sub.1-C.sub.4)-alkyl-S(O).sub.n, (C.sub.1-C.sub.4)-haloalkyl-S(O).sub.n; CHO, (C.sub.1-C.sub.4)-alkylcarbonyl, (C.sub.1-C.sub.4)-haloalkylcarbonyl, (C.sub.1-C.sub.4)-alkyloxycarbonyl; NH.sub.2; R.sup.12 is halogen, cyano, isocyano, NO.sub.2; (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-alkylcarbonyl, (C.sub.1-C.sub.6)-haloalkylcarbonyl, (C.sub.1-C.sub.4)-alkyloxycarbonyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.3)-haloalkoxy, (C.sub.1-C.sub.4)-alkyl-S(O).sub.n; (C.sub.2-C.sub.3)-alkenyl, (C.sub.2-C.sub.3)-haloalkenyl; (C.sub.2-C.sub.3)-alkynyl, (C.sub.2-C.sub.3)-haloalkynyl; NH.sub.2; and where the indices are as follows: 1 is 0, 1, 2 or 3; m is 0, 1 or 2; n is 0, 1 or 2; o is 0, 1 or 2; p is 0 or 1; q is 0 or 1; r is 3, 4, 5 or 6; and s is 0, 1, 2, 3, 4 or 5.

2. Compounds of the formula (I) according to claim 1 and their agrochemically acceptable salts, N-oxides, hydrates, and hydrates of the salts and N-oxides, where A is A1-A16: ##STR00040## ##STR00041## R.sup.1 is OR.sup.1a or NR.sup.9R.sup.10; in which R.sup.1a is hydrogen; is (C.sub.1-C.sub.6)-alkyl which is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.2)-alkoxy-(C.sub.1-C.sub.4)-alkoxy, cyano and nitro; is (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-haloalkenyl; is aryl-(C.sub.1-C.sub.2)-alkyl, heteroaryl-(C.sub.1-C.sub.2)-alkyl, where the aryl and hetaryl is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl; is (C.sub.1-C.sub.4)-alkylideneamino; R.sup.9 is hydrogen and (C.sub.1-C.sub.6)-alkyl; R.sup.10 is hydrogen; is (C.sub.3-C.sub.7)-cycloalkyl-(C.sub.1-C.sub.4)-alkyl, aryl-(C.sub.1-C.sub.4)-alkyl, aryl-(C.sub.1-C.sub.4)-alkoxy, where the cycloalkyl and aryl is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl; is (C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl; (C.sub.3-C.sub.8)-cycloalkyl; where the abovementioned alkyl, cycloalkyl, alkenyl, cycloalkenyl and alkynyl radicals are unsubstituted or are each independently substituted by m radicals selected from the group consisting of cyano, C(O)OR.sup.8; is (C.sub.1-C.sub.6)-haloalkyl; is S(O).sub.2R.sup.5, SO.sub.2NR.sup.6R.sup.7, NR.sup.6SO.sub.2R.sup.8; R.sup.5 is (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.2-C.sub.4)-alkenyl or aryl; R.sup.6 is hydrogen, (C.sub.1-C.sub.4)-alkyl or (C.sub.3-C.sub.6)-cycloalkyl; R.sup.7 is hydrogen, (C.sub.1-C.sub.4)-alkyl or (C.sub.3-C.sub.6)-cycloalkyl; R.sup.8 is hydrogen, (C.sub.1-C.sub.8)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl; R.sup.2a is hydrogen, cyano; (C.sub.1-C.sub.6)-alkyl; (C.sub.3-C.sub.6)-cycloalkyl; R.sup.2b is hydrogen; R.sup.3 is fluorine, chlorine, bromine, iodine, cyano, isocyano, NO.sub.2; (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.1-C.sub.6)-haloalkyl; R.sup.4 is fluorine, chlorine, bromine, cyano; methyl, ethyl; methoxy, ethoxy; R.sup.12 is halogen, cyano, nitro; methyl, ethyl, (C.sub.1-C.sub.2)-haloalkyl; methoxy, ethoxy; and where the indices are as follows: 1 is 0, 1 or 2; m is 0, 1 or 2; s is 0, 1, 2, 3.

3. Compounds of the formula (I) according to claim 1 and their agrochemically acceptable salts, N-oxides, hydrates, and hydrates of the salts and N-oxides, where: A is A1-A10: ##STR00042## R.sup.1 is OR.sup.1a or NR.sup.9R.sup.10; in which R.sup.1a is hydrogen; is methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, cyanomethyl, 2-methoxyethyl, 2-(2-methoxyethoxy)ethyl; is 1-propenyl, 2-propenyl; is benzyl, pyridylmethyl, where the phenyl and pyridyl radical is in each case unsubstituted or substituted by halogen; is isopropylideneamino; R.sup.9 is hydrogen; R.sup.10 is hydrogen; is cyclopropylmethyl; is benzyl, 1-phenylethyl, 2-phenylethyl, benzyloxy, where the phenyl radical in each of the four groups mentioned is unsubstituted or substituted by halogen; is methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, where the abovementioned radicals are unsubstituted or are monosubstituted by a C(O)OR.sup.8 radical; is cyclopropyl, cyclobutyl, cyclopentyl, where the three radicals mentioned are unsubstituted or are monosubstituted by a C(O)OR.sup.8 radical; is 1-propenyl, 2-propenyl, 2-methyl-2-propenyl, prop-2-yn-1-yl, but-2-yn-1-yl; is S(O).sub.2R.sup.5, SO.sub.2NR.sup.6R.sup.7; R.sup.5 is methyl, ethyl, propyl, 1-methylethyl, trifluoromethyl, 1,1-difluoroethyl, 2,2,2-trifluoroethyl, cyclopropyl or vinyl; R.sup.6 is hydrogen, methyl, ethyl, propyl, 1-methylethyl or cyclopropyl; R.sup.7 is hydrogen or methyl; R.sup.8 is hydrogen, methyl, ethyl; R.sup.2a is hydrogen; methyl; R.sup.2b is hydrogen; R.sup.3 is fluorine, chlorine, bromine, iodine, cyano, NO.sub.2; cyclopropyl, trifluoromethyl; R.sup.4 is fluorine, chlorine, bromine; methyl; R.sup.12 is fluorine, chlorine, bromine; and where the indices are as follows: l is 0 or 1; s is 0, 1 or 2.

4. Compounds of the formula (I) according to claim 1 and their agrochemically acceptable salts, N-oxides, hydrates, and hydrates of the salts and N-oxides, where: A is A1, A3, A4, A5 or A6: ##STR00043## R.sup.1 is OR.sup.1a or NR.sup.9R.sup.10; in which R.sup.1a is hydrogen; is methyl, ethyl; is cyanomethyl, 2-methoxyethyl, 2-(2-methoxyethoxy)ethyl; is pyridin-2-ylmethyl; is isopropylideneamino; R.sup.9 is hydrogen; R.sup.10 is cyclopentyl monosubstituted by C(O)OR.sup.8; is cyclopropylmethyl; is CH.sub.2C(O)OR.sup.8, CH.sub.2CH.sub.2C(O)OR.sup.8; is 2-propenyl; is S(O).sub.2R.sup.5, SO.sub.2NR.sup.6R.sup.7; R.sup.5 is methyl, ethyl, trifluoromethyl, 1,1-difluoroethyl, cyclopropyl or vinyl; R.sup.6 is methyl, ethyl, propyl or 1-methylethyl; R.sup.7 is hydrogen or methyl; R.sup.8 is hydrogen, methyl, ethyl; R.sup.2a is hydrogen; methyl; R.sup.2b is hydrogen; R.sup.3 is selected from the group consisting of chlorine, bromine, iodine, cyano, NO.sub.2; trifluoromethyl, cyclopropyl; R.sup.4 is fluorine, chlorine; R.sup.12 is fluorine; and where the indices are as follows: l is 0 or 1; s is 0, 1 or 2.

5. Compounds of the formula (I) according to claim 1 and their agrochemically acceptable salts, N-oxides, hydrates, and hydrates of the salts and N-oxides, where A is A1-1, A1-2, A1-3, A3-1, A3-2, A3-3, A3-4, A4-1, A5-1 or A5-2: ##STR00044## ##STR00045## R.sup.1 is OR.sup.1a or NR.sup.9R.sup.10; in which R.sup.1a is hydrogen; is methyl, ethyl; is cyanomethyl, 2-methoxyethyl, 2-(2-methoxyethoxy)ethyl; is pyridin-2-ylmethyl; is isopropylideneamino; R.sup.9 is hydrogen; R.sup.10 is cyclopentyl monosubstituted by C(O)OR.sup.8; is cyclopropylmethyl; is CH.sub.2C(O)OR.sup.8, CH.sub.2CH.sub.2C(O)OR.sup.8; is 2-propenyl; is S(O).sub.2R.sup.5, SO.sub.2NR.sup.6R.sup.7; R.sup.5 is methyl, ethyl, trifluoromethyl, cyclopropyl or vinyl; R.sup.6 is methyl, ethyl or 1-methylethyl; R.sup.7 is methyl; R.sup.8 is hydrogen, methyl, ethyl; R.sup.2a is hydrogen; methyl; R.sup.2b is hydrogen; R.sup.3 is chlorine, bromine, cyano, cyclopropyl; R.sup.4 is 3-fluoro, 3-chloro; where the index l is 0 or 1.

6. Compounds of the formula (Iz) and their agrochemically acceptable salts, N-oxides, hydrates, and hydrates of the salts and N-oxides ##STR00046## where the R.sup.1, R.sup.2a, R.sup.2b, R.sup.3 and A radicals are as defined in claim 2.

7. Process for preparing the compounds of the general formulae (Ia) and (Ib) and their agrochemically acceptable salts, N-oxides, hydrates, and hydrates of the salts and N-oxides according to claim 1, by reacting compounds of the general formula (II) with compounds of the general formula (III) to give compounds of the general formula (IV), and then converting these further using compounds of general formulae (V) and (VI) ##STR00047## in which R.sup.2a, R.sup.2b, R.sup.1a, R.sup.3, R.sup.4, 1 and A have the definition given above and M is metal, where the conversion of (Ia) to (Ib) is accomplished in the presence of a transition metal catalyst.

8. Agrochemical composition comprising a) at least one compound of the general formula (I) or an agrochemically acceptable salt, N-oxide, hydrate, hydrate of the salt/N-oxide thereof as defined in claim 1, and b) auxiliaries and additives customary in crop protection.

9. Agrochemical composition comprising a) at least one compound of the general formula (I) or an agrochemically acceptable salt, N-oxide, hydrate, hydrate of the salt/N-oxide thereof as defined in claim 1, b) one or more active agrochemical ingredients other than component a), and optionally c) auxiliaries and additives customary in crop protection.

10. Method of controlling unwanted plants or of regulating the growth of plants, wherein an effective amount of at least one compound of the general formula (I) or an agrochemically acceptable salt, N-oxide, hydrate, hydrate of the salt/N-oxide thereof as defined in claim 1 is applied to the plants, the seed or the area in which the plants grow.

11. Use of compounds of the general formula (I) or an agrochemically acceptable salt, N-oxide, hydrate, hydrate of the salt/N-oxide thereof as defined in claim 1 as herbicides or plant growth regulators.

12. Use according to claim 11, wherein the compounds of the general formula (I) or an agrochemically acceptable salt, N-oxide, hydrate, hydrate of the salt/N-oxide thereof are used for controlling harmful plants or for regulating growth in plant crops.

13. Use according to claim 12, wherein the crop plants are transgenic or nontransgenic crop plants.

14. Seed, characterized in that it is coated with compounds of the general formula (I) or an agrochemically acceptable salt, N-oxide, hydrate, hydrate of the salt/N-oxide thereof as defined in claim 1.

15. Seed, characterized in that it is coated with an agrochemical composition as claimed in claim 8.

16. Seed, characterized in that it is coated with an agrochemical composition as claimed in claim 9.

Description

EXAMPLES

[0588] The present invention is illustrated in detail by the examples which follow, but these examples do not restrict the invention in any way.

A. Synthesis Examples

[0589] Methyl[[4-bromo-5-(3,4-difluorophenyl)-]-(pyrazin-2-yl)-]H-pyrazol-3-yl]oxy}acetate (1-15): To a solution of 0.20 g (0.54 mmol) of 4-bromo-5-(3,4-difluorophenyl)-1-(pyrazin-2-yl)-1H-pyrazole-3-ol in 8 ml of dimethylformamide was added 0.27 g (0.81 mmol) of caesium carbonate, the mixture was stirred at room temperature for 10 minutes, 0.10 g (0.65 mmol) of methyl bromoacetate was added, and the mixture was stirred at room temperature for one hour. The mixture was filtered, the filtrate was concentrated under reduced pressure, the residue was taken up in water and extracted repeatedly with dichloromethane, the dried organic phases were dried over sodium sulfate, and the solvent was removed under reduced pressure. After purification by column chromatography on silica gel with heptane/ethyl acetate, 0.23 g (93% of theory) of a product with m/z=427 (50) [M.sup.+], 425 (50) [M.sup.+] was obtained. .sup.1H-NMR (400 MHz, CDCl.sub.3, δ, ppm): 8.95 (m, 1H), 8.38 (m, 1H), 8.06 (m, 1H), 7.22-7.17 (m, 2H), 7.10-7.05 (m, 1H), 4.97 (s, 2H), 3.84 (s, 3H).

[0590] Synthesis of the Starting Compounds: [0591] a) 4-Bromo-5-(3,4-difluorophenyl)-1-(pyrazin-2-yl)-]H-pyrazole-3-ol: To 0.50 g (1.07 mmol) of 2-[3-(benzyloxy)-4-bromo-5-(3,4-difluorophenyl)-1H-pyrazol-1-yl]pyrazine was added, under argon, 18.50 g (162.25 mmol) of trifluoroacetic acid, and the mixture was stirred under reflux for one hour. The excess trifluoroacetic acid was removed under reduced pressure, the residue was dissolved in dichloromethane, and the solvent was removed under reduced pressure. 0.45 g (95% of theory) of a colourless solid with m/z=355 (50) [M.sup.+], 353 (50) [M.sup.+] was obtained. [0592] b) 2-[3-(Benzyloxy)-4-bromo-5-(3,4-difluorophenyl)-]H-pyrazol-1-yl]pyrazine: To a solution of 0.56 g (1.50 mmol) of 2-[3-(benzyloxy)-5-(3,4-difluorophenyl)-1H-pyrazol-1-yl]pyrazine in 8 ml of DMF was added 0.27 g (1.50 mmol) of N-bromosuccinimide, and the mixture was stirred at room temperature for one hour. The solvent was removed under reduced pressure, the residue was taken up in water and extracted repeatedly with dichloromethane, the dried organic phases were dried over sodium sulfate, and the solvent was removed under reduced pressure. After purification by column chromatography on silica gel with heptane/ethyl acetate, 0.50 g (71% of theory) of a product with m/z (%)=445 (50) [M.sup.+], 443 (50) [M.sup.+] was obtained. .sup.1H-NMR (400 MHz, CDCl.sub.3, δ, ppm): 9.00 (m, 1H), 8.38 (m, 1H), 8.07 (m, 1H), 7.56-7.52 (m, 2H), 7.44-7.36 (m, 3H), 7.22-7.16 (m, 2H), 7.08-7.05 (m, 1H), 5.44 (s, 2H). [0593] c) 2-[3-(Benzyloxy)-5-(3,4-difluorophenyl)-]H-pyrazol-1-yl]pyrazine: Added successively under an argon atmosphere to a solution of 1.50 g (3.97 mmol) of 2-[3-(benzyloxy)-5-iodo-1H-pyrazol-1-yl]pyrazine in 45 ml of dioxane were 1.14 g (4.76 mmol) of 2-(3,4-difluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 0.038 g (0.20 mmol) of copper(I) iodide, 2.58 g (7.93 mmol) of caesium carbonate, 4.5 ml of water and 0.23 g (0.20 mmol) of tetrakis(triphenylphosphine)palladium, and the reaction mixture was stirred at 70° C. for 3 hours. The solvent was removed under reduced pressure, the residue was taken up in water/ethyl acetate, the aqueous phase was extracted repeatedly with ethyl acetate, the dried organic phases were dried over sodium sulfate, and the solvent was removed under reduced pressure. After purification by column chromatography on silica gel with heptane/ethyl acetate, 0.58 g (38%) of a yellowish solid with m/z (%)=365 [M.sup.+] was obtained. .sup.1H-NMR (400 MHz, CDCl.sub.3, δ, ppm): 9.03 (m, 1H), 8.39 (m, 1H), 8.12 (m, 1H), 7.52-7.49 (m, 2H), 7.43-7.34 (m, 3H), 7.18-7.11 (m, 2H), 7.06-7.02 (m, 1H), 6.03 (s, 1H), 5.36 (s, 2H). [0594] d) 2-[3-(Benzyloxy)-5-iodo-]H-pyrazol-1-yl]pyrazine: Added dropwise under argon atmosphere to a solution of 5.00 g (15.86 mmol) of 2-[3-(benzyloxy)-1H-pyrazol-1-yl]pyrazine in 150 ml of dry tetrahydrofuran at −78° C. was a solution of 2.21 g (20.61 mmol) of lithium diisopropylamide (2 molar solution in tetrahydrofuran) in 50 ml of tetrahydrofuran, and the mixture was stirred at −78° C. for 0.5 hour. A solution of 5.23 g (20.61 mmol) of iodine in 50 ml of tetrahydrofuran was added dropwise, and the mixture was stirred at −78° C. for a further hour. The mixture was allowed to warm up to room temperature, water was added, and extraction was effected repeatedly with ethyl acetate. The combined organic phases were dried over sodium sulfate, and the solvent was removed under reduced pressure. After purification by column chromatography on silica gel with heptane/ethyl acetate, 1.84 g (31%) of a colourless solid with m/z (%)=379 [M.sup.+] was obtained. .sup.1H-NMR (400 MHz, CDCl.sub.3, δ, ppm): 9.13 (m, 1H), 8.50 (m, 1H), 8.42 (m, 1H), 7.48-7.45 (m, 2H), 7.42-7.32 (m, 3H), 6.26 (s, 1H), 5.30 (s, 2H). [0595] e) 2-[3-(Benzyloxy)-]H-pyrazol-1-yl]pyrazine: Added successively under argon atmosphere to a solution of 6.87 g (59.99 mmol) of 2-chloropyrazine in 60 ml of DMF were 24.88 g (76.35 mmol) of caesium carbonate, 10.00 g (54.54 mmol) of 3-(benzyloxy)-1H-pyrazole dissolved in 40 ml of DMF, and 1.45 g (7.62 mmol) of copper(J) iodide, and the reaction mixture was stirred at 120° C. for 5 hours. The mixture was filtered and washed with dichloromethane, and the solvent was removed under reduced pressure. The residue was taken up in aqueous ammonium chloride solution and extracted repeatedly with dichloromethane, the combined organic phases were dried over sodium sulfate, and the solvent was removed under reduced pressure. 17.00 g (98%) of a greenish solid with m/z (%)=253 [M.sup.+] was obtained. .sup.1H-NMR (400 MHz, CDCl.sub.3, δ, ppm): 9.17 (m, 1H), 8.38 (m, 1H), 8.31 (d, 1H), 8.28 (m, 1H), 7.52-7.50 (m, 2H), 7.42-7.34 (m, 3H), 6.02 (d, 1H), 5.35 (s, 2H).

[0596] Pyridin-2-ylmethyl[[4-bromo-5-(6-fluoropyridin-3-yl)-]-(pyrazin-2-yl)-]H-pyrazol-3-yl]oxy}acetate (I-70): Added successively to 0.04 g (0.36 mmol) of pyridin-2-ylmethanol in 3.0 ml of dichloromethane were 0.10 g (0.25 mmol) of {[4-bromo-5-(6-fluoropyridin-3-yl)-1-(pyrazin-2-yl)-1H-pyrazol-3-yl]oxy}acetic acid (I-49), 0.05 g (0.33 mmol) of 1H-benzotriazole-1-ol, 0.06 g (0.33 mmol) of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride and one spatula-tip of N,N-dimethylpyridine-4-amine, and the mixture was stirred at room temperature for one hour. Water and dichloromethane were added to the reaction mixture, the aqueous phase was extracted repeatedly with dichloromethane, the combined organic phases were dried over sodium sulfate, and the solvent was removed under reduced pressure. By column chromatography purification of the crude product obtained on silica gel with a heptane/ethyl acetate gradient, 0.08 g (65% of theory) of a product with m/z (%)=487 (50) [M.sup.+], 485 (50) [M.sup.+] was obtained. .sup.1H-NMR (600 MHz, CDCl.sub.3, δ, ppm): 9.01 (m, 1H), 8.61 (m, 1H), 8.39 (m, 1H), 8.22 (m, 1H), 7.99 (m, 1H), 7.85-7.81 (m, 1H), 7.69-7.65 (m, 1H), 7.39 (m, 1H), 7.26-7.22 (m, 1H), 7.03-7.00 (m, 1H), 5.39 (s, 2H), 5.09 (s, 2H).

[0597] [[4-Bromo-5-(6-fluoropyridin-3-yl)-]-(pyrazin-2-yl)-]H-pyrazol-3-yl]oxy}acetic acid (I-49): To 0.77 g (1.82 mmol) of ethyl {[4-bromo-5-(6-fluoropyridin-3-yl)-1-(pyrazin-2-yl)-1H-pyrazol-3-yl]oxy}acetate (I-52) in 7 ml of tetrahydrofuran was added a solution of 0.13 g (5.47 mmol) of lithium hydroxide in 10 ml of water, and the mixture was stirred at 65° C. for 2 h. The solvent was removed under reduced pressure, the residue was taken up with water and extracted twice with dichloromethane, and the aqueous phase was adjusted to pH=2-3 with 2M hydrochloric acid and extracted twice with dichloromethane. The combined organic phases were dried over sodium sulfate, and the solvent was removed under reduced pressure. A colourless solid (0.58 g, 76% of theory) was obtained. .sup.1H-NMR (600 MHz, DMSO-d.sub.6, δ, ppm): 13.17 (bs, 1H), 9.00 (m, 1H), 8.52 (m, 1H), 8.34 (m, 1H), 8.20 (m, 1H), 8.11-8.08 (m, 1H), 7.33-7.31 (m, 1H), 4.97 (s, 2H).

[0598] Ethyl[[4-bromo-5-(6-fluoropyridin-3-yl)-]-(pyrazin-2-yl)-]H-pyrazol-3-yl]oxy}acetate (I-52): To a solution of 0.81 g (2.36 mmol) of ethyl {[5-(6-fluoropyridin-3-yl)-1-(pyrazin-2-yl)-1H-pyrazol-3-yl]oxy}acetate in 5 ml of DMF was added 0.50 g (2.83 mmol) of N-bromosuccinimide, and the mixture was stirred at room temperature for ten hours. The solvent was removed under reduced pressure, the residue was taken up in water and extracted repeatedly with dichloromethane, the dried organic phases were dried over sodium sulfate, and the solvent was removed under reduced pressure. After purification by column chromatography on silica gel with a heptane/ethyl acetate gradient, 0.92 g (87% of theory) of a product with m/z (%)=424 (50) [M.sup.+], 422 (50) [M.sup.+] was obtained. .sup.1H-NMR (600 MHz, CDCl.sub.3, δ, ppm): 9.05 (m, 1H), 8.37 (m, 1H), 8.23 (m, 1H), 7.99 (m, 1H), 7.86-7.82 (m, 1H), 7.03-7.00 (m, 1H), 4.96 (s, 2H), 4.31 (q

[0599] Synthesis of the Starting Compounds: [0600] a) Ethyl[[5-(6-fluoropyridin-3-yl)-]-(pyrazin-2-yl)-]H-pyrazol-3-yl]oxy}acetate: To a solution of 1.58 g (5.84 mmol) of 5-(6-fluoropyridin-3-yl)-1-(pyrazin-2-yl)-1H-pyrazole-3-ol in 10 ml of dimethylformamide was added 2.85 g (8.75 mmol) of caesium carbonate, the mixture was stirred at room temperature for 10 minutes, 1.17 g (7.00 mmol) of ethyl bromoacetate was added, and the mixture was stirred at 65° C. for two further hours. The mixture was filtered, the filtrate was concentrated under reduced pressure, the residue was taken up in water and extracted repeatedly with dichloromethane, the dried organic phases were dried over sodium sulfate, and the solvent was removed under reduced pressure. After purification by column chromatography on silica gel with heptane/ethyl acetate, 1.53 g (73% of theory) of a product with m/z=344 [M.sup.+] was obtained. .sup.1H-NMR (600 MHz, CDCl.sub.3, δ, ppm): 9.08 (m, 1H), 8.37 (m, 1H), 8.23 (m, 1H), 8.02 (m, 1H), 7.81-7.78 (m, 1H), 6.96-6.94 (m, 1H), 6.13 (s, 1H), 4.91 (s, 2H), 4.31 (q, 2H), 1.33 (t, 3H). [0601] b) 5-(6-Fluoropyridin-3-yl)-1-(pyrazin-2-yl)-]H-pyrazole-3-ol: To a solution of 3.55 g (8.28 mmol) of 3-(6-fluoropyridin-3-yl)-N′-(pyrazin-2-yl)prop-2-yne hydrazide in 7 ml of acetonitrile was added 0.08 g (0.66 mmol) of copper(J) iodide, and the mixture was stirred at 80° C. for two hours. After purification by column chromatography on silica gel with heptane/ethyl acetate, 1.59 g (75% of theory) of a product with m/z=258 [M.sup.+] was obtained. .sup.1H-NMR (400 MHz, DMSO-d.sub.6, δ, ppm): 10.82 (s, 1H), 9.00 (m, 1H), 8.46 (m, 1H), 8.29 (m, 1H), 8.17 (m, 1H), 8.02-7.97 (m, 1H), 7.32-7.28 (m, 1H), 6.18 (s, 1H). [0602] c) 3-(6-Fluoropyridin-3-yl)-N′-(pyrazin-2-yl)prop-2-yne hydrazide: To a solution of 3.00 g (16.35 mmol) of 3-(6-fluoropyridin-3-yl)prop-2-ynoic acid in 20 ml of tetrahydrofuran were successively added 2.07 g (18.80 mmol) of 2-hydrazinopyrazine and 8.27 g (81.76 mmol) of triethylamine. 15.61 g (24.53 mmol) of propanephosphonic anhydride (T3P, 50% solution in tetrahydrofuran) was added dropwise, and the mixture was stirred at room temperature for one hour. The reaction mixture was poured onto water and extracted repeatedly with ethyl acetate, the combined organic phases were dried over sodium sulfate, the solvent was removed under reduced pressure, and 3.55 g (51% of theory) of an oily product (HPLC/MS purity=60%, m/z=258 [M.sup.+]) was obtained, which was converted further without purification. [0603] d) 3-(6-Fluoropyridin-3-yl)prop-2-ynoic acid: Under an argon atmosphere, the following were added successively to 9.20 g (41.26 mmol) of 2-fluoro-5-iodopyridine in 105 ml of dry tetrahydrofuran: 2.89 g (41.26 mmol) of propiolic acid, 0.58 g (0.83 mmol) of bis(triphenylphosphine)palladium(11) dichloride, 0.31 g (1.65 mmol) of copper(I) iodide and 14.61 g (144.41 mmol) of diisopropylamine. The mixture was stirred at room temperature for 2 hours, the reaction mixture was added to water, 30 ml of 2 N hydrochloric acid was added and extraction was effected repeatedly with ethyl acetate. The combined organic phases were dried over magnesium sulfate and concentrated under reduced pressure. The residue was admixed with diethyl ether, the mixture was stirred at an ultrasound bath for 10 min and filtered, and the solvent was removed under reduced pressure. 6.25 g (78% of theory) of a product with m/z=166 [M.sup.+] was obtained. .sup.1H-NMR (600 MHz, DMSO-d.sub.6, δ, ppm): 14.00 (bs, 1H), 8.57 (m, 1H), 8.32-8.28 (m, 1H), 7.35-7.32 (m, 1H).

[0604] Methyl (2R)-2-[[4-bromo-]-(pyrazin-2-yl)-5-(pyridazin-4-yl)-]H-pyrazol-3-yl]oxy}propanoate (I-31): To a solution of 0.71 g (1.75 mmol) of methyl (2R)-2-{[1-(pyrazin-2-yl)-5-(pyridazin-4-yl)-1H-pyrazol-3-yl]oxy}propanoate in 8 ml of DMF was added 0.37 g (2.10 mmol) of N-bromosuccinimide, and the mixture was stirred at room temperature for three hours. The solvent was removed under reduced pressure, the residue was taken up in water and extracted repeatedly with dichloromethane, the dried organic phases were dried over sodium sulfate, and the solvent was removed under reduced pressure. After purification by column chromatography on silica gel with a heptane/ethyl acetate gradient, 0.14 g (20% of theory) of a product with m/z (%)=405 (50) [M.sup.+], 407 (50) [M.sup.+] and a specific angle of rotation [α]=+56° was obtained. .sup.1H-NMR (400 MHz, CDCl.sub.3, δ, ppm): 9.32 (m, 1H), 9.14 (m, 1H), 9.08 (m, 1H), 8.40 (m, 1H), 7.94 (m, 1H), 7.55 (m, 1H), 5.26 (q, 1H), 3.83 (s, 3H), 1.74 (d, 3H).

[0605] Methyl (2R)-2-[[4-cyano-]-(pyrazin-2-yl)-5-(pyridazin-4-yl)-]H-pyrazol-3-yl]oxy}propanoate (I-32): A mixture consisting of 0.40 g (0.79 mmol) of methyl (2R)-2-{[4-bromo-1-(pyrazin-2-yl)-5-(pyridazin-4-yl)-1H-pyrazol-3-yl]oxy}propanoate (I-31), 0.09 g (0.75 mmol) of zinc cyanide and 0.09 g (0.08 mmol) of tetrakis(triphenylphosphine)palladium in 10 ml of dimethylacetamide was heated to 180° C. in a microwave under an argon atmosphere for 40 minutes. The solvent was removed under reduced pressure, the residue was taken up in water/dichloromethane, the aqueous phase was extracted repeatedly with dichloromethane, the combined organic phases were dried over sodium sulfate, and the solvent was removed under reduced pressure. After purification by column chromatography on silica gel with a heptane/ethyl acetate gradient, 0.21 g (70% of theory) of a product with m/z=352 [M.sup.+] and a specific angle of rotation [α]=+54° was obtained. .sup.1H-NMR (400 MHz, CDCl.sub.3, δ, ppm): 9.39 (m, 1H), 9.15 (m, 1H), 9.12 (m, 1H), 8.54 (m, 1H), 8.05 (m, 1H), 7.64 (m, 1H), 5.29 (q, 1H), 3.83 (s, 3H), 1.74

[0606] N-Allyl-2-[[4-bromo-5-(3-fluorophenyl)-]-(pyrazin-2-yl)-]H-pyrazol-3-yl]oxy}acetamide (11-01): Added successively under argon to a solution of 0.09 g (0.23 mmol) of {[4-bromo-5-(3-fluorophenyl)-1-(pyrazin-2-yl)-1H-pyrazol-3-yl]oxy}acetic acid in 5 ml of tetrahydrofuran were 0.01 g (0.25 mmol) of prop-2-ene-1-amine and 0.05 g (0.28 mmol) of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride in 5 ml of dichloromethane, and the mixture was stirred at room temperature for four hours. The solvent was removed under reduced pressure, the residue was taken up in dichloromethane, 2N hydrochloric acid was added, the mixture was extracted repeatedly with dichloromethane, the combined organic phases were dried over sodium sulfate, and the solvent was removed under reduced pressure. After purification by column chromatography on silica gel with heptane/ethyl acetate, 0.03 g (27% of theory) of a colourless oil with m/z (%)=434 (50) [M.sup.+], 432 (50) [M.sup.+] was obtained. .sup.1H-NMR (400 MHz, CDCl.sub.3, δ, ppm): 8.94 (m, 1H), 8.41 (m, 1H), 8.10 (m, 1H), 7.41-7.36 (m, 1H), 7.16-7.05 (m, 2H), 6.62 (bs, 1H), 5.94-5.87 (m, 1H), 5.30-5.25 (m, 1H), 5.20-5.17 (m, 1H), 4.93 (s, 2H), 4.05-4.01 (m, 1H).

NMR Data of Selected Examples

[0607] The .sup.1H NMR data of selected examples of compounds of the general formula (I) are stated in two different ways, namely (a) conventional NMR evaluation and interpretation or (b) in the form of .sup.1H NMR peak lists according to the method described below.

[0608] a) Conventional NMR interpretation

Example I-08

[0609] .sup.1H-NMR (400 MHz, CDCl.sub.3, δ, ppm): 9.03 (m, 1H), 8.52 (m, 1H), 8.39-8.37 (m, 2H), 7.98 (m, 1H), 7.51-7.48 (m, 1H), 5.27 (q, 1H), 3.82 (s, 3H), 1.73 (d, 3H).

Example I-15

[0610] .sup.1H-NMR (400 MHz, CDCl.sub.3, δ, ppm): 8.95 (m, 1H), 8.38 (m, 1H), 8.06 (m, 1H), 7.22-7.17 (m, 2H), 7.10-7.05 (m, 1H), 4.97 (s, 2H), 3.84 (s, 3H).

Example I-27

[0611] .sup.1H-NMR (400 MHz, CDCl.sub.3, δ, ppm): 9.01 (m, 1H), 8.82 (d, 2H), 8.33 (m, 1H), 7.90 (m, 1H), 7.32 (t, 1H), 5.29 (q, 1H), 3.80 (s, 3H), 1.72 (d, 3H).

Example I-31

[0612] .sup.1H-NMR (400 MHz, CDCl.sub.3, δ, ppm): 9.32 (m, 1H), 9.14 (m, 1H), 9.08 (m, 1H), 8.40 (m, 1H), 7.94 (m, 1H), 7.55 (m, 1H), 5.26 (q, 1H), 3.83 (s, 3H), 1.74 (d, 3H).

Example I-32

[0613] .sup.1H-NMR (400 MHz, CDCl.sub.3, δ, ppm): 9.39 (m, 1H), 9.15 (m, 1H), 9.12 (m, 1H), 8.54 (m, 1H), 8.05 (m, 1H), 7.64 (m, 1H), 5.29 (q, 1H), 3.83 (s, 3H), 1.74 (d, 3H).

Example I-36

[0614] .sup.1H-NMR (400 MHz, CDCl.sub.3, δ, ppm): 9.03 (m, 1H), 8.37 (m, 1H), 8.24 (m, 1H), 7.99 (m, 1H), 7.86-7.82 (m, 1H), 7.03-7.00 (m, 1H), 5.27 (q, 1H), 3.82 (s, 3H), 1.73 (d, 3H).

Example I-49

[0615] .sup.1H-NMR (600 MHz, DMSO-d.sub.6, δ, ppm): 13.17 (bs, 1H), 9.00 (m, 1H), 8.52 (m, 1H), 8.34 (m, 1H), 8.20 (m, 1H), 8.11-8.08 (m, 1H), 7.33-7.31 (m, 1H), 4.97 (s, 2H).

Example I-52

[0616] .sup.1H-NMR (600 MHz, CDCl.sub.3, δ, ppm): 9.05 (m, 1H), 8.37 (m, 1H), 8.23 (m, 1H), 7.99 (m, 1H), 7.86-7.82 (m, 1H), 7.03-7.00 (m, 1H), 4.96 (s, 2H), 4.31 (q, 2H), 1.34 (t, 3H).

Example I-54

[0617] .sup.1H-NMR (400 MHz, CDCl.sub.3, δ, ppm): 9.1 (s, 1H), 8.9 (d, 2H), 8.4 (s, 1H), 7.9 (s, 1H), 7.4 (m, 1H), 5.2 (q, 1H), 1.7 (d, 3H).

Example I-55

[0618] .sup.1H-NMR (400 MHz, CDCl.sub.3, δ, ppm): 9.1 (s, 1H), 8.7 (d, 2H), 8.5 (s, 1H), 8.1 (s, 1H), 7.4 (m, 1H), 5.4 (q, 1H), 1.8 (d, 3H).

Example I-70

[0619] .sup.1H-NMR (600 MHz, CDCl.sub.3, δ, ppm): 9.01 (m, 1H), 8.61 (m, 1H), 8.39 (m, 1H), 8.22 (m, 1H), 7.99 (m, 1H), 7.85-7.81 (m, 1H), 7.69-7.65 (m, 1H), 7.39 (m, 1H), 7.26-7.22 (m, 1H), 7.03-7.00 (m, 1H), 5.39 (s, 2H), 5.09 (s, 2H).

Example I-78

[0620] .sup.1H-NMR (400 MHz, CDCl.sub.3, δ, ppm): 8.18-8.14 (m, 3H), 7.86-7.82 (m, 1H), 7.00-6.97 (m, 1H), 5.23 (q, 1H), 3.79 (s, 3H), 1.70 (d, 3H).

Example I-80

[0621] .sup.1H-NMR (400 MHz, CDCl.sub.3, δ, ppm): 8.18-8.14 (m, 3H), 7.86-7.82 (m, 1H), 7.00-6.97 (m, 1H), 5.23 (q, 1H), 3.79 (s, 3H), 1.70 (d, 3H).

Example I-83

[0622] .sup.1H-NMR (400 MHz, DMSO-d.sub.6, δ, ppm): 13.01 (bs, 1H), 8.94 (s, 1H), 8.42 (m, 1H), 8.30 (m, 1H), 8.12 (m, 1H), 8.06-8.02 (m, 1H), 7.28-7.25 (m, 1H), 4.88 (s, 2H), 1.56-1.49 (m, 1H), 0.73-0.63 (m, 4H).

Example I-84

[0623] .sup.1H-NMR (400 MHz, CDCl.sub.3, δ, ppm): 9.00 (s, 1H), 8.27 (m, 1H), 8.23 (m, 1H), 7.93 (m, 1H), 7.83-7.78 (m, 1H), 7.00-6.97 (m, 1H), 4.92 (s, 2H), 3.83 (s, 3H), 1.49-1.43 (m, 1H), 0.83-0.79 (m, 2H), 0.76-0.71 (m, 2H).

Example I-85

[0624] .sup.1H-NMR (400 MHz, CDCl.sub.3, δ, ppm): 9.00 (s, 1H), 8.27 (m, 1H), 8.23 (m, 1H), 7.93 (m, 1H), 7.83-7.78 (m, 1H), 7.00-6.97 (m, 1H), 4.90 (s, 2H), 4.29 (q, 2H), 1.48-1.43 (m, 1H), 1.33 (t, 3H), 0.84-0.80 (m, 2H), 0.76-0.71 (m, 2H).

Example I-86

[0625] .sup.1H-NMR (400 MHz, CDCl.sub.3, δ, ppm): 9.04 (s, 1H), 8.22 (m, 2H), 7.95 (s, 1H), 7.81-7.76 (m, 1H), 7.00-6.96 (m, 1H), 5.20 (q, 1H), 1.72 (d, 3H), 1.47-1.40 (m, 1H), 0.90-0.80 (m, 2H), 0.77-0.72 (m, 2H).

Example I-87

[0626] .sup.1H-NMR (400 MHz, CDCl.sub.3, δ, ppm): 8.98 (s, 1H), 8.26 (m, 1H), 8.23 (m, 1H), 7.91 (m, 1H), 7.82-7.78 (m, 1H), 6.99-6.96 (m, 1H), 5.23 (q, 1H), 3.80 (s, 3H), 1.66 (d, 3H), 1.48-1.43 (m, 1H), 0.87-0.82 (m, 2H), 0.74-0.72 (m, 2H).

Example I-88

[0627] .sup.1H-NMR (400 MHz, CDCl.sub.3, δ, ppm): 8.99 (s, 1H), 8.25 (m, 1H), 8.23 (m, 1H), 7.91 (m, 1H), 7.82-7.78 (m, 1H), 6.99-6.96 (m, 1H), 5.20 (q, 1H), 4.30-4.22 (m, 2H), 1.66 (d, 3H), 1.48-1.41 (m, 1H), 1.31 (t, 3H), 0.87-0.84 (m, 2H), 0.75-0.71 (m, 2H).

Example I-89

[0628] .sup.1H-NMR (400 MHz, CDCl.sub.3, δ, ppm): 9.03 (m, 1H), 8.34 (m, 1H), 8.20 (m, 1H), 7.96 (m, 1H), 7.83-7.78 (m, 1H), 7.03-7.00 (m, 1H), 5.25 (q, 1H), 3.82 (s, 3H), 1.72 (d, 3H).

Example II-01

[0629] .sup.1H-NMR (400 MHz, CDCl.sub.3, δ, ppm): 8.94 (m, 1H), 8.41 (m, 1H), 8.10 (m, 1H), 7.41-7.36 (m, 1H), 7.16-7.05 (m, 2H), 6.62 (bs, 1H), 5.94-5.87 (m, 1H), 5.30-5.25 (m, 1H), 5.20-5.17 (m, 1H), 4.93 (s, 2H), 4.05-4.01 (m, 1H).

Example II-02

[0630] .sup.1H-NMR (400 MHz, CDCl.sub.3, δ, ppm): 9.09 (m, 1H), 8.40 (m, 1H), 8.24 (m, 1H), 8.00 (m, 1H), 7.86-7.81 (m, 1H), 7.04-7.01 (m, 2H), 5.31 (q, 1H), 3.68-3.55 (m, 2H), 3.66 (s, 3H), 2.60-2.57 (m, 2H), 1.72 (d, 3H).

Example II-03

[0631] .sup.1H-NMR (400 MHz, CDCl.sub.3, δ, ppm): 9.10 (m, 1H), 8.41 (m, 1H), 8.24 (m, 1H), 8.01 (m, 1H), 7.86-7.81 (m, 1H), 7.04-7.01 (m, 2H), 5.40 (q, 1H), 4.17-4.10 (m, 2H), 3.78 (s, 3H), 1.75 (d, 3H).

Example II-04

[0632] .sup.1H-NMR (400 MHz, CDCl.sub.3, δ, ppm): 9.09 (m, 1H), 8.40 (m, 1H), 8.24 (m, 1H), 8.00 (m, 1H), 7.86-7.81 (m, 1H), 7.04-7.01 (m, 2H), 5.32 (q, 1H), 4.16-4.08 (m, 2H), 3.67-3.58 (m, 2H), 2.58-2.55 (m, 2H), 1.72 (d, 3H), 1.23 (t, 3H).

Example II-05

[0633] .sup.1H-NMR (400 MHz, CDCl.sub.3, δ, ppm): 9.09 (m, 1H), 8.39 (m, 1H), 8.24-8.21 (m, 1H), 8.00 (m, 1H), 7.86-7.81 (m, 1H), 7.10-7.00 (m, 2H), 5.33-5.24 (m, 1H), 4.47-4.38 (m, 1H), 3.68/3.66 (2s, 3H), 2.93-2.85 (m, 1H), 2.28-2.19 (m, 1H), 2.04-1.93 (m, 3H), 1.90-1.68 (m, 5H).

Example II-06

[0634] .sup.1H-NMR (400 MHz, CDCl.sub.3, δ, ppm): 9.10 (m, 1H), 8.41 (m, 1H), 8.24 (m, 1H), 8.01 (m, 1H), 7.86-7.81 (m, 1H), 7.04-7.00 (m, 1H), 6.62 (bm, 1H), 5.34 (q, 1H), 3.25-3.18 (m, 2H), 1.74 (d, 3H), 1.05-0.95 (m, 1H), 0.54-0.50 (m, 2H), 0.25-0.22 (m, 2H).

Example II-07

[0635] .sup.1H-NMR (400 MHz, CDCl.sub.3, δ, ppm): 9.10 (m, 1H), 8.42 (m, 1H), 8.24 (m, 1H), 8.01 (m, 1H), 7.86-7.81 (m, 1H), 7.08 (bt, 1H), 7.04-7.01 (m, 1H), 4.90 (s, 2H), 3.69 (s, 3H), 3.67 (q, 2H), 2.62 (t, 2H).

Example II-08

[0636] .sup.1H-NMR (400 MHz, CDCl.sub.3, δ, ppm): 9.11 (m, 1H), 8.42 (m, 1H), 8.24 (m, 1H), 8.02 (m, 1H), 7.86-7.82 (m, 1H), 7.04-7.00 (m, 2H), 4.96 (s, 2H), 4.18 (d, 2H), 3.80 (s, 3H).

Example II-09

[0637] .sup.1H-NMR (400 MHz, CDCl.sub.3, δ, ppm): 9.10 (m, 1H), 8.41 (m, 1H), 8.23 (m, 1H), 8.01 (m, 1H), 7.86-7.81 (m, 1H), 7.09 (bt, 1H), 7.04-7.01 (m, 1H), 4.90 (s, 2H), 4.17 (q, 2H), 3.67 (q, 2H), 2.61 (t, 2H), 1.26 (t, 3H).

Example II-10

[0638] .sup.1H-NMR (400 MHz, CDCl.sub.3, δ, ppm): 9.11 (m, 1H), 8.41 (m, 1H), 8.24 (m, 1H), 8.02 (m, 1H), 7.86-7.81 (m, 1H), 7.04-7.01 (m, 1H), 6.62 (bs, 1H), 4.91 (s, 2H), 3.27 (m, 2H), 1.06-1.02 (m, 1H), 0.58-0.53 (m, 2H), 0.29-0.26 (m, 2H).

Example II-11

[0639] .sup.1H-NMR (400 MHz, CDCl.sub.3, δ, ppm): 9.10 (m, 1H), 8.40 (m, 1H), 8.23 (m, 1H), 8.01 (m, 1H), 7.86-7.82 (m, 1H), 7.17 (bd, 1H), 7.04-7.01 (m, 1H), 4.89 (s, 2H), 4.55-4.48 (m, 1H), 3.68 (s, 3H), 2.98-2.95 (m, 1H), 2.28-2.20 (m, 1H), 2.08-1.82 (m, 4H), 1.81-1.73 (m, 1H).

Example II-12

[0640] .sup.1H-NMR (400 MHz, CDCl.sub.3, δ, ppm): 9.08 (s, 1H), 8.58 (bs, 1H), 8.44 (m, 1H), 8.24 (m, 1H), 8.04 (m, 1H), 7.88-7.83 (m, 1H), 7.07-7.03 (m, 1H), 4.96 (s, 2H), 3.02 (s, 6H).

Example II-13

[0641] .sup.1H-NMR (400 MHz, CDCl.sub.3, δ, ppm): 9.07 (s, 1H), 8.75 (bs, 1H), 8.44 (m, 1H), 8.24 (m, 1H), 8.04 (m, 1H), 7.87-7.82 (m, 1H), 7.05-7.02 (m, 1H), 4.93 (s, 2H), 4.25 (q, 1H), 2.93 (s, 3H), 1.17 (d, 6H).

Example II-14

[0642] .sup.1H-NMR (400 MHz, CDCl.sub.3, δ, ppm): 9.07 (s, 1H), 8.71 (bs, 1H), 8.44 (m, 1H), 8.24 (m, 1H), 8.05 (m, 1H), 7.87-7.82 (m, 1H), 7.06-7.03 (m, 1H), 5.01 (s, 2H), 3.40 (s, 3H).

[0643] b) NMR peak list method

[0644] 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 δ value-signal intensity number pairs for different signal peaks are listed with separation from one another by semicolons.

[0645] The peak list for one example therefore takes the form of:

[0646] δ.sub.1 (intensity.sub.1); δ.sub.2 (intensity.sub.2); . . . ; δ.sub.i (intensity.sub.i; . . . ; δ.sub.n(intensity.sub.n)

[0647] 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.

[0648] For calibration of the chemical shift of .sup.1H NMR spectra, we use 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.

[0649] 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.

[0650] In addition, like conventional .sup.1H NMR printouts, they may show solvent signals, signals of stereoisomers of the target compounds which are likewise provided by the invention, and/or peaks of impurities.

[0651] 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 DMSO-D.sub.6 and the peak of water, which usually have a high intensity on average.

[0652] 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%).

[0653] Such stereoisomers and/or impurities may be typical of the particular preparation process. Their peaks can thus help in identifying reproduction of our preparation process with reference to “by-product fingerprints”.

[0654] 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.

[0655] Further details of .sup.1H NMR peak lists can be found in the Research Disclosure Database Number 564025.

TABLE-US-00003 I-01: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ = 8.8165 (3.5); 8.8132 (3.6); 8.3518 (3.6); 8.3454 (3.6); 8.0976 (2.7); 8.0940 (2.9); 8.0913 (2.8); 8.0876 (2.5); 7.4276 (0.6); 7.4236 (0.9); 7.4219 (1.0); 7.4159 (5.6); 7.4115 (5.4); 7.4046 (2.4); 7.4026 (2.1); 7.3981 (3.5); 7.3963 (3.0); 7.3895 (1.0); 7.3858 (1.2); 7.3745 (0.6); 7.3465 (0.6); 7.3392 (3.8); 7.3348 (4.2); 7.3307 (1.2); 7.3274 (1.5); 7.3258 (1.4); 7.3232 (1.6); 7.3207 (1.7); 7.3147 (2.3); 7.2594 (15.4); 4.9613 (15.0); 4.9109 (0.8); 4.3231 (2.0); 4.3053 (6.3); 4.2874 (6.4); 4.2696 (2.1); 2.0424 (0.7); 1.5454 (3.1); 1.3379 (7.8); 1.3200 (16.0); 1.3097 (0.7); 1.3022 (7.9); 1.2918 (0.8); 1.2741 (1.0); 1.2649 (1.7); 1.2581 (1.3); 0.8986 (0.8); 0.8817 (2.9); 0.8640 (1.1); 0.0080 (0.5); −0.0002 (17.4); −0.0085 (0.6) I-02: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ = 8.9079 (3.9); 8.9044 (3.8); 8.3699 (3.7); 8.3635 (3.8); 8.0703 (2.9); 8.0667 (3.0); 8.0639 (2.9); 8.0603 (2.7); 7.3994 (0.8); 7.3847 (0.9); 7.3791 (1.4); 7.3647 (1.4); 7.3594 (1.2); 7.3447 (1.1); 7.2589 (40.6); 7.1506 (0.7); 7.1481 (0.9); 7.1442 (0.8); 7.1417 (0.9); 7.1294 (1.1); 7.1269 (1.5); 7.1230 (1.4); 7.1205 (1.8); 7.1165 (1.9); 7.1127 (2.4); 7.1102 (1.7); 7.1057 (0.9); 7.0975 (1.6); 7.0937 (2.2); 7.0911 (1.5); 7.0831 (1.5); 7.0773 (1.2); 7.0734 (0.8); 7.0599 (1.3); 7.0559 (1.2); 7.0500 (0.9); 4.9545 (15.9); 4.3261 (2.0); 4.3083 (6.4); 4.2904 (6.4); 4.2726 (2.1); 1.5303 (9.2); 1.3414 (7.8); 1.3236 (16.0); 1.3057 (7.7); 1.2640 (0.7); 0.8818 (0.7); 0.0079 (1.8); −0.0002 (50.7); −0.0085 (1.8) I-03: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ = 8.7968 (3.8); 8.3727 (3.4); 8.3668 (3.8); 8.1438 (2.7); 8.1402 (2.8); 7.5175 (4.6); 7.4221 (5.4); 7.4071 (3.5); 7.3400 (3.7); 7.3362 (4.3); 7.3160 (2.6); 7.2587 (846.2); 6.9947 (4.5); 5.0488 (16.0); 3.7462 (4.0); 1.8524 (5.2); 1.8356 (2.2); 1.5445 (2.0); 0.1460 (3.2); 0.0079 (30.5); −0.0002 (1013.4); −0.0085 (36.3); −0.1496 (3.3) I-05: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ = 9.0264 (2.8); 8.3995 (2.5); 8.3933 (2.5); 8.2805 (2.1); 8.2677 (2.2); 8.0068 (1.8); 8.0023 (2.2); 7.9984 (1.7); 7.2645 (9.4); 7.2638 (9.3); 7.1427 (1.6); 7.1298 (1.6); 6.9534 (2.5); 5.3007 (2.1); 5.2930 (0.7); 5.2754 (1.9); 5.2580 (1.9); 5.2406 (0.6); 3.8197 (16.0); 1.7355 (7.5); 1.7180 (7.5); 1.2562 (0.7); 0.0007 (5.9); −0.0002 (5.9) I-06: .sup.1H-NMR (599.7 MHz, CDCl.sub.3): δ = 9.0495 (3.8); 9.0474 (3.7); 8.4133 (3.5); 8.4091 (3.5); 8.2827 (2.8); 8.2741 (2.8); 8.0208 (2.4); 8.0184 (2.7); 8.0166 (2.6); 8.0142 (2.3); 7.2810 (0.3); 7.2736 (0.3); 7.2602 (47.8); 7.1444 (1.2); 7.1419 (2.0); 7.1395 (1.2); 7.1358 (1.2); 7.1333 (1.9); 7.1309 (1.1); 6.9568 (3.0); 5.2994 (0.4); 4.9827 (14.0); 3.8456 (24.2); 1.5402 (29.1); 1.2550 (0.6); 0.0692 (0.9); 0.0208 (0.3); 0.0133 (0.3); 0.0053 (1.8); −0.0001 (50.0); −0.0056(1.6) I-07: .sup.1H-NMR (599.6 MHz, CDCl.sub.3): δ = 9.0599 (8.9); 9.0580 (9.6); 8.5326 (8.0); 8.5280 (8.1); 8.3901 (9.0); 8.3874 (12.7); 8.3830 (8.8); 7.9956 (5.3); 7.9932 (6.4); 7.9916 (6.3); 7.9892 (5.4); 7.5126 (2.5); 7.5095 (3.1); 7.5083 (3.1); 7.5052 (2.6); 7.4979 (2.5); 7.4948 (3.1); 7.4936 (3.1); 7.4905 (2.4); 7.2671 (6.2); 4.9879 (30.4); 3.8473 (50.0); 3.8078 (0.3); 3.7215 (0.3); 2.7677 (9.5); 1.6668 (1.6); 1.3346 (0.5); 1.2853 (0.7); 1.2553 (2.0); 0.8795 (0.4); 0.0052 (0.3); −0.0001 (7.9); −0.0054 (0.3) I-09: .sup.1H-NMR (400.2 MHz, d.sub.6-DMSO): δ = 9.0108 (2.9); 9.0075 (2.9); 8.5511 (2.7); 8.5447 (2.8); 8.3492 (2.0); 8.3363 (2.0); 8.2088 (1.8); 8.2052 (1.9); 8.2024 (1.9); 8.1989 (1.7); 7.4259 (1.3); 7.4224 (0.9); 7.4169 (0.8); 7.4132 (1.2); 7.4095 (0.8); 7.3636 (2.3); 5.7550 (1.1); 5.0950 (7.8); 3.7455 (16.0); 3.3345 (139.7); 3.1755 (0.6); 3.1624 (0.5); 2.6718 (0.3); 2.5252 (1.0); 2.5118 (21.7); 2.5074 (43.2); 2.5029 (55.8); 2.4983 (39.9); 2.4939 (19.2); 2.3297 (0.3); −0.0002 (0.9) I-10: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ = 9.0305 (1.9); 9.0270 (2.0); 8.3930 (1.9); 8.3866 (1.9); 8.2798 (1.5); 8.2669 (1.5); 7.9922 (1.5); 7.9886 (1.6); 7.9859 (1.5); 7.9822 (1.4); 7.2621 (7.8); 7.1422 (0.7); 7.1385 (1.1); 7.1344 (0.8); 7.1293 (0.8); 7.1257 (1.0); 7.1215 (0.7); 6.9518 (1.1); 6.9485 (1.6); 6.9467 (1.2); 6.9451 (1.1); 5.2692 (1.6); 5.2517 (1.6); 3.8182 (16.0); 1.7341 (6.3); 1.7167 (6.2); 1.5654 (3.6); −0.0002 (10.1) I-11: .sup.1H-NMR (599.7 MHz, d.sub.6-DMSO): δ = 8.9948 (1.8); 8.9926 (1.8); 8.5268 (1.7); 8.5226 (1.8); 8.3421 (1.1); 8.3380 (1.1); 8.1967 (1.2); 8.1944 (1.3); 8.1925 (1.2); 8.1901 (1.1); 8.1081 (0.4); 8.1039 (0.4); 8.0942 (0.6); 8.0903 (0.6); 8.0810 (0.4); 8.0768 (0.4); 7.3247 (0.6); 7.3207 (0.6); 7.3105 (0.6); 7.3065 (0.6); 5.0913 (5.1); 3.7477 (10.0); 3.3265 (50.0); 2.5174 (0.3); 2.5087 (5.4); 2.5057 (11.1); 2.5026 (15.2); 2.4996 (11.2); 2.4966 (5.4); −0.0001 (0.3) I-12: .sup.1H-NMR (400.2 MHz, d.sub.6-DMSO): δ = 8.9454 (2.9); 8.9421 (3.0); 8.5221 (2.8); 8.5157 (2.9); 8.3370 (1.8); 8.3310 (1.8); 8.1907 (1.8); 8.1871 (1.9); 8.1844 (1.9); 8.1808 (1.7); 8.1107 (0.6); 8.1047 (0.6); 8.0901 (1.1); 8.0840 (1.0); 8.0701 (0.7); 8.0639 (0.7); 7.3270 (1.2); 7.3204 (1.1); 7.3057 (1.1); 7.2990 (1.1); 5.7551 (1.7); 5.3303 (0.5); 5.3131 (1.9); 5.2958 (2.0); 5.2785 (0.5); 3.7434 (16.0); 3.3280 (73.8); 2.6715 (0.4); 2.5247 (1.2); 2.5113 (23.3); 2.5070 (46.6); 2.5025 (60.7); 2.4980 (43.6); 2.4936 (21.2); 2.3291 (0.4); 1.6266 (6.4); 1.6093 (6.4); −0.0002 (5.5) I-16: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ = 8.9473 (1.6); 8.9440 (1.6); 8.3675 (1.6); 8.3611 (1.6); 8.0366 (1.2); 8.0330 (1.3); 8.0303 (1.3); 8.0266 (1.2); 7.2627 (6.6); 7.2166 (0.5); 7.2088 (0.9); 7.2044 (0.5); 7.1979 (0.5); 7.1925 (0.6); 7.1888 (0.9); 7.1842 (1.2); 7.1655 (0.6); 7.1632 (0.7); 5.2998 (2.7); 5.2681 (1.6); 5.2506 (1.6); 3.8109 (16.0); 1.7242 (6.3); 1.7067 (6.2); −0.0002 (4.6) I-17: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ = 9.0282 (1.9); 9.0249 (1.9); 8.3644 (1.8); 8.3580 (1.9); 8.2297 (1.2); 8.2236 (1.2); 7.9842 (1.4); 7.9806 (1.4); 7.9779 (1.4); 7.9742 (1.3); 7.8549 (0.6); 7.8487 (0.6); 7.8361 (0.7); 7.8338 (0.8); 7.8299 (0.7); 7.8276 (0.7); 7.8150 (0.6); 7.8088 (0.6); 7.2629 (13.1); 7.0246 (0.8); 7.0184 (0.8); 7.0173 (0.8); 7.0034 (0.8); 6.9973 (0.8); 6.9961 (0.8); 5.2732 (1.6); 5.2557 (1.6); 3.8205 (16.0); 1.7354 (6.3); 1.7179 (6.3); −0.0002 (8.0) I-18: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ = 9.0287 (1.7); 9.0257 (1.6); 9.0252 (1.6); 8.3659 (1.7); 8.3654 (1.7); 8.3591 (1.7); 8.2325 (0.7); 8.2306 (1.0); 8.2285 (0.8); 8.2265 (0.8); 8.2243 (1.0); 8.2224 (0.7); 7.9865 (1.5); 7.9829 (1.5); 7.9801 (1.5); 7.9764 (1.4); 7.8576 (0.6); 7.8514 (0.6); 7.8388 (0.7); 7.8365 (0.8); 7.8326 (0.7); 7.8303 (0.7); 7.8177 (0.7); 7.8115 (0.7); 7.2709 (3.9); 7.0281 (0.8); 7.0266 (0.8); 7.0207 (0.8); 7.0191 (0.8); 7.0070 (0.8); 7.0054 (0.8); 6.9995 (0.8); 6.9980 (0.8); 5.3019 (4.9); 5.2751 (1.6); 5.2577 (1.6); 3.8209 (16.0); 1.7355 (6.3); 1.7180 (6.3); −0.0002 (2.4) I-19: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ = 8.8278 (1.8); 8.8244 (1.8); 8.3398 (1.7); 8.3335 (1.7); 8.0695 (1.2); 8.0658 (1.2); 8.0631 (1.2); 8.0595 (1.1); 7.4127 (3.0); 7.4082 (2.8); 7.4012 (1.2); 7.3995 (1.0); 7.3949 (1.7); 7.3932 (1.5); 7.3828 (0.6); 7.3352 (2.0); 7.3308 (2.2); 7.3267 (0.5); 7.3232 (0.7); 7.3219 (0.7); 7.3193 (0.8); 7.3169 (0.8); 7.3126 (0.5); 7.3107 (1.2); 7.2613 (10.9); 5.2985 (2.2); 5.2813 (1.6); 3.8066 (16.0); 3.8036 (1.6); 1.7237 (6.3); 1.7062 (6.3); −0.0002 (6.6) I-20: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ = 8.9047 (2.2); 8.9012 (2.2); 8.3583 (2.2); 8.3519 (2.2); 8.0484 (1.4); 8.0447 (1.5); 8.0420 (1.5); 8.0384 (1.3); 7.3818 (0.5); 7.3763 (0.8); 7.3618 (0.8); 7.3565 (0.6); 7.3417 (0.6); 7.2611 (14.9); 7.1259 (0.6); 7.1237 (0.7); 7.1196 (0.7); 7.1173 (0.9); 7.1125 (0.9); 7.1090 (1.2); 7.1063 (0.9); 7.0936 (0.7); 7.0899 (1.1); 7.0874 (0.7); 7.0786 (0.8); 7.0726 (0.6); 7.0552 (0.7); 7.0511 (0.7); 5.2811 (1.6); 5.2636 (1.6); 3.8099 (16.0); 1.7252 (6.6); 1.7078 (6.5); 1.5687 (0.8); 1.2643 (0.6); 0.8818 (1.1); −0.0002 (8.7) I-22: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ = 8.9710 (0.8); 8.9676 (0.8); 8.5137 (0.7); 8.5077 (0.7); 8.1490 (0.5); 8.1453 (0.6); 8.1427 (0.5); 7.5191 (0.5); 7.2602 (91.5); 5.2646 (0.7); 5.2471 (0.7); 3.8093 (7.5); 1.7244 (2.9); 1.7069 (2.9); 1.5376 (16.0); 0.0080 (1.9); −0.0002 (55.0); −0.0085 (1.5) I-23: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ = 8.9863 (1.3); 8.9829 (1.3); 8.5294 (1.2); 8.5232 (1.3); 8.1691 (0.9); 8.1655 (1.0); 8.1628 (0.9); 8.1593 (0.8); 7.2604 (71.0); 7.2509 (0.5); 7.2420 (0.6); 7.2378 (0.8); 7.2325 (0.5); 4.9751 (5.5); 3.8384 (10.1); 1.5396 (16.0); 0.0080 (1.4); −0.0002 (42.7); −0.0085 (1.1) I-24: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ = 9.0984 (5.6); 8.3399 (4.8); 8.2296 (5.4); 8.0132 (5.0); 7.8235 (3.1); 7.2618 (102.0); 7.0201 (3.2); 6.9999 (3.2); 5.3011 (2.9); 5.2837 (3.2); 5.2672 (3.0); 2.0404 (1.2); 1.8015 (11.5); 1.7843 (11.9); 1.6790 (1.9); 1.2563 (16.0); 0.8808 (3.2); −0.0002 (60.1) I-25: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ = 9.0521 (1.6); 9.0489 (1.6); 8.5094 (1.6); 8.5032 (1.6); 8.2920 (1.1); 8.2901 (0.9); 8.2878 (0.9); 8.2857 (1.1); 8.0970 (1.4); 8.0934 (1.4); 8.0907 (1.4); 8.0871 (1.3); 7.9551 (0.7); 7.9487 (0.6); 7.9368 (0.7); 7.9339 (0.8); 7.9305 (0.7); 7.9275 (0.7); 7.9156 (0.7); 7.9092 (0.7); 7.2631 (13.5); 7.0763 (0.8); 7.0748 (0.9); 7.0688 (0.8); 7.0673 (0.9); 7.0551 (0.8); 7.0536 (0.8); 7.0476 (0.8); 7.0461 (0.8); 5.3007 (0.8); 5.2788 (1.6); 5.2613 (1.6); 3.8202 (16.0); 1.7377 (6.4); 1.7203 (6.4); −0.0002 (9.2) I-26: .sup.1H-NMR (400.6 MHz, CDCl.sub.3): δ = 9.0528 (1.9); 9.0523 (1.9); 9.0494 (2.0); 8.5115 (1.9); 8.5111 (1.9); 8.5052 (2.0); 8.2937 (1.1); 8.2917 (0.9); 8.2894 (0.9); 8.2874 (1.2); 8.1002 (1.5); 8.0966 (1.6); 8.0939 (1.6); 8.0903 (1.5); 7.9572 (0.6); 7.9509 (0.6); 7.9389 (0.7); 7.9360 (0.8); 7.9326 (0.7); 7.9297 (0.7); 7.9177 (0.7); 7.9114 (0.6); 7.2702 (2.1); 7.0787 (0.8); 7.0773 (0.8); 7.0713 (0.8); 7.0698 (0.8); 7.0575 (0.8); 7.0560 (0.8); 7.0500 (0.8); 7.0486 (0.8); 5.3029 (9.0); 5.2992 (0.7); 5.2813 (1.6); 5.2639 (1.6); 3.8211 (16.0); 1.7381 (6.2); 1.7207 (6.1); −0.0002(1.9) I-28: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ = 9.3202 (3.7); 9.1070 (1.9); 9.1038 (1.8); 8.8734 (5.9); 8.5225 (1.8); 8.5163 (1.8); 8.0755 (1.4); 8.0718 (1.5); 8.0692 (1.5); 8.0656 (1.4); 7.2655 (12.6); 5.3037 (0.8); 5.2927 (1.6); 5.2753 (1.6); 3.8311 (16.0); 3.8267 (0.9); 1.7521 (6.2); 1.7346 (6.1); −0.0002 (8.9) I-29: .sup.1H-NMR (400.6 MHz, CDCl.sub.3): δ = 8.9456 (1.7); 8.9425 (1.7); 8.7689 (5.3); 8.7566 (5.4); 8.5367 (1.7); 8.5304 (1.8); 8.1457 (1.4); 8.1421 (1.4); 8.1393 (1.4); 8.1358 (1.3); 7.3396 (1.5); 7.3274 (2.9); 7.3151 (1.5); 7.2615 (20.6); 5.3006 (0.6); 5.2933 (1.5); 5.2758 (1.5); 3.7919 (16.0); 1.7272 (6.2); 1.7098 (6.1); 1.5602 (2.3); 0.0080 (0.6); −0.0002 (18.6); −0.0085 (0.5) I-30: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ = 9.2600 (2.3); 9.0794 (1.4); 9.0763 (1.4); 8.7975 (2.4); 8.3821 (1.4); 8.3757 (1.4); 7.9706 (1.2); 7.9669 (1.3); 7.9642 (1.3); 7.9606 (1.1); 7.2669 (9.9); 5.2811 (1.5); 5.2636 (1.6); 3.8297 (16.0); 2.7777 (1.6); 2.0484 (2.0); 1.7470 (6.0); 1.7296 (6.0); 1.2789 (0.6); 1.2610 (1.2); 1.2431 (0.5); −0.0002 (7.1) I-33: .sup.1H-NMR (400.0 MHz, de-DMSO): δ = 13.2459 (0.5); 9.2662 (2.1); 9.2631 (2.7); 9.2530 (2.2); 9.2499 (2.8); 9.2346 (2.4); 9.2315 (2.5); 9.2289 (3.0); 9.2258 (2.2); 9.0122 (3.5); 9.0094 (3.8); 8.5536 (3.4); 8.5476 (3.5); 8.1475 (2.5); 8.1439 (2.7); 8.1411 (2.7); 8.1375 (2.5); 7.7303 (2.3); 7.7245 (2.3); 7.7171 (2.3); 7.7113 (2.3); 7.5943 (1.4); 6.9956 (1.4); 5.3275 (0.6); 5.3103 (2.5); 5.2930 (2.6); 5.2756 (0.6); 3.3408 (1.0); 3.3229 (16.0); 3.2967 (0.5); 2.6707 (0.6); 2.5240 (1.8); 2.5194 (2.7); 2.5105 (30.2); 2.5061 (64.8); 2.5015 (90.0); 2.4970 (65.9); 2.4926 (31.1); 2.3283 (0.6); 2.1169 (0.9); 2.0854 (2.0); 1.6767 (7.5); 1.6594 (7.4); 1.5463 (1.9); 1.1404 (2.0); 0.0080 (1.5); −0.0002 (45.8); −0.0085 (1.5) I-34: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ = 9.0305 (2.6); 8.3936 (2.2); 8.3874 (2.2); 8.2808 (2.0); 8.2679 (2.1); 7.9930 (1.7); 7.9893 (2.0); 7.2638 (9.8); 7.1393 (1.5); 7.1264 (1.5); 6.9500 (2.3); 5.2874 (0.6); 5.2699 (1.8); 5.2525 (1.8); 5.2352 (0.6); 3.8187 (16.0); 2.0454 (0.8); 1.7346 (7.2); 1.7172 (7.2); 1.2771 (0.6); 1.2606 (1.2); 0.8986 (0.5); 0.8819 (1.3); 0.8645 (0.6); −0.0002 (6.0) I-35: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ = 9.0560 (3.3); 8.5389 (2.8); 8.5328 (2.7); 8.3425 (2.2); 8.3298 (2.2); 8.1037 (2.1); 8.1000 (2.4); 7.2624 (13.2); 7.2025 (1.7); 7.1897 (1.7); 6.9756 (2.5); 5.2967 (0.6); 5.2791 (1.8); 5.2616 (1.8); 5.2444 (0.6); 3.8196 (16.0); 2.0453 (1.4); 1.7393 (7.3); 1.7218 (7.3); 1.2775 (0.7); 1.2606 (1.4); 0.8823 (0.9); −0.0002 (8.8) I-37: .sup.1H-NMR (400.0 MHz, de-DMSO): δ = 13.1410 (1.4); 8.9751 (5.9); 8.9718 (6.0); 8.6937 (5.1); 8.6866 (5.3); 8.5212 (5.6); 8.5148 (6.3); 8.5071 (5.5); 8.1800 (3.7); 8.1764 (4.0); 8.1737 (3.9); 8.1700 (3.6); 7.9732 (1.6); 7.9688 (1.9); 7.9620 (1.5); 7.9491 (1.7); 7.9447 (2.0); 7.9380 (1.6); 5.7563 (2.7); 5.2248 (0.9); 5.2074 (3.8); 5.1901 (3.9); 5.1728 (0.9); 3.6009 (0.6); 3.3191 (16.0); 2.6707 (0.8); 2.5236 (3.8); 2.5101 (48.7); 2.5057 (100.0); 2.5012 (135.1); 2.4967 (96.6); 2.4924 (44.6); 2.3285 (0.8); 1.7598 (0.7); 1.6165 (11.8); 1.5991 (11.7); 1.2346 (0.5); 0.0079 (2.9); −0.0002 (72.3); −0.0085 (2.3) I-38: .sup.1H-NMR (400.2 MHz, de-DMSO): δ = 8.9331 (2.8); 8.9297 (2.9); 8.6481 (1.2); 8.6441 (1.4); 8.6359 (1.3); 8.6320 (1.3); 8.5953 (1.8); 8.5912 (1.8); 8.5250 (2.6); 8.5186 (2.7); 8.1787 (1.7); 8.1752 (1.9); 8.1724 (1.9); 8.1688 (1.7); 7.8643 (0.8); 7.8594 (1.1); 7.8547 (0.8); 7.8446 (0.9); 7.8396 (1.2); 7.8349 (0.8); 7.5043 (1.0); 7.4921 (1.0); 7.4860 (0.9); 7.4845 (0.9); 7.4739 (0.8); 7.4723 (0.9); 5.7558 (2.3); 5.3261 (0.5); 5.3090 (1.9); 5.2917 (1.9); 5.2744 (0.5); 3.7424 (16.0); 3.3265 (40.5); 2.6712 (0.4); 2.5247 (1.0); 2.5112 (22.9); 2.5068 (46.8); 2.5022 (61.5); 2.4977 (44.4); 2.4932 (21.8); 2.3291 (0.4); 1.6255 (6.3); 1.6082 (6.2); −0.0002 (6.4) I-39: .sup.1H-NMR (400.2 MHz, de-DMSO): δ = 8.9575 (2.9); 8.9542 (2.9); 8.6949 (2.4); 8.6880 (2.4); 8.5270 (2.7); 8.5205 (2.9); 8.5088 (1.5); 8.5048 (2.6); 8.5011 (1.4); 8.1775 (1.7); 8.1740 (1.9); 8.1712 (1.9); 8.1676 (1.7); 7.9709 (0.8); 7.9665 (0.9); 7.9642 (0.9); 7.9598 (0.8); 7.9468 (0.8); 7.9425 (0.9); 7.9402 (0.9); 7.9357 (0.7); 5.7560 (2.0); 5.3378 (0.5); 5.3206 (1.9); 5.3033 (1.9); 5.2859 (0.5); 3.7458 (16.0); 3.3259 (46.9); 2.6712 (0.4); 2.5244 (1.3); 2.5111 (25.9); 2.5068 (51.0); 2.5023 (65.6); 2.4977 (46.8); 2.4933 (22.4); 2.3291 (0.4); 1.6295 (6.4); 1.6122 (6.3); −0.0002 (6.1) I-40: .sup.1H-NMR (400.2 MHz, d.sub.6-DMSO): δ = 9.0179 (3.0); 9.0150 (2.9); 8.7754 (2.5); 8.7685 (2.5); 8.6651 (2.7); 8.6588 (2.8); 8.6453 (1.6); 8.6416 (2.7); 8.2938 (1.9); 8.2902 (2.1); 8.2875 (2.0); 8.2840 (1.8); 8.1133 (0.8); 8.1089 (0.9); 8.1067 (0.9); 8.1023 (0.8); 8.0895 (0.8); 8.0851 (1.0); 8.0830 (0.9); 8.0785 (0.7); 5.7555 (1.7); 5.4233 (0.5); 5.4060 (1.9); 5.3887 (1.9); 5.3714 (0.5); 3.7568 (16.0); 3.3268 (51.2); 2.6714 (0.4); 2.5111 (24.4); 2.5069 (47.0); 2.5024 (59.7); 2.4979 (43.0); 2.4936 (21.1); 2.3292 (0.4); 1.6551 (6.5); 1.6378 (6.4); −0.0002 (6.1) I-41: .sup.1H-NMR (599.6 MHz, CDCl.sub.3): δ = 8.9739 (2.7); 8.3799 (1.9); 8.3761 (2.2); 8.0840 (1.9); 7.2597 (34.2); 7.2253 (0.4); 7.2097 (1.4); 7.1954 (1.7); 7.1802 (0.9); 7.0816 (0.8); 5.2993 (0.4); 5.0238 (6.8); 2.1085 (0.5); 1.4321 (0.7); 1.2555 (2.0); 0.8802 (0.4); 0.8677 (0.3); 0.8395 (0.3); −0.0001 (50.0) I-42: .sup.1H-NMR (400.6 MHz, CDCl.sub.3): δ = 9.0754 (1.6); 9.0723 (1.6); 8.4034 (1.5); 8.3971 (1.6); 8.0143 (1.2); 8.0107 (1.3); 8.0080 (1.3); 8.0043 (1.2); 7.9829 (1.2); 7.9783 (1.9); 7.9739 (1.3); 7.6793 (0.6); 7.6742 (0.6); 7.6563 (0.9); 7.6514 (0.9); 7.6341 (0.6); 7.6291 (0.6); 7.2608 (30.1); 4.9835 (8.5); 3.8467 (16.0); 1.5443 (7.4); 0.0080 (0.9); −0.0002 (32.3);−0.0085 (1.0) I-43: .sup.1H-NMR (400.6 MHz, CDCl.sub.3): δ = 9.0489 (1.8); 9.0482 (1.7); 9.0453 (1.9); 9.0447 (1.7); 8.3875 (1.8); 8.3868 (1.7); 8.3811 (1.9); 7.9988 (1.4); 7.9952 (1.5); 7.9924 (1.5); 7.9888 (1.4); 7.9777 (1.1); 7.9732 (1.6); 7.9686 (1.1); 7.6718 (0.6); 7.6668 (0.5); 7.6497 (0.8); 7.6487 (0.7); 7.6447 (0.8); 7.6437 (0.7); 7.6266 (0.6); 7.6215 (0.5); 7.2619 (11.2); 5.2695 (1.5); 5.2520 (1.5); 3.8209 (16.0); 1.7366 (6.1); 1.7192 (6.0); 1.5580 (2.4); 1.2646 (0.5); 1.2599 (0.5); 0.8819 (1.0); −0.0002 (11.3) I-44: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ = 9.0859 (1.9); 9.0828 (1.9); 8.7086 (4.8); 8.7046 (4.8); 8.3984 (1.9); 8.3921 (1.9); 7.9921 (1.4); 7.9884 (1.5); 7.9857 (1.5); 7.9821 (1.4); 7.2613 (13.6); 5.2786 (1.6); 5.2612 (1.6); 3.8262 (16.0); 1.7451 (6.2); 1.7276 (6.2); 1.5497 (4.2); −0.0002 (17.3) I-45: .sup.1H-NMR (599.6 MHz, CDCl.sub.3): δ = 8.9460 (8.2); 8.9439 (8.3); 8.3656 (7.6); 8.3614 (7.7); 8.0338 (5.0); 8.0313 (5.8); 8.0296 (5.5); 8.0272 (4.7); 7.2611 (17.1); 7.2171 (1.5); 7.2075 (2.0); 7.2036 (4.7); 7.1950 (2.2); 7.1896 (4.4); 7.1864 (5.0); 7.1772 (1.9); 7.1732 (3.2); 7.0810 (1.4); 7.0784 (1.9); 7.0745 (2.0); 7.0716 (2.0); 7.0681 (1.8); 7.0641 (1.6); 7.0609 (1.6); 7.0574 (1.5); 5.2769 (1.7); 5.2652 (5.5); 5.2536 (5.5); 5.2420 (1.6); 3.8105 (50.0); 3.7971 (0.4); 3.7884 (0.4); 3.6849 (0.3); 2.9568 (1.2); 2.8846 (1.1); 2.0444 (0.5); 1.7210 (21.6); 1.7094 (21.4); 1.5598 (10.0); 1.2897 (0.3); 1.2800 (0.4); 1.2710 (0.5); 1.2650 (0.8); 1.2591 (1.0); 1.2561 (0.9); 1.2473 (0.4); 0.8935 (0.7); 0.8820 (1.6); 0.8700 (0.8); 0.0053 (1.0); −0.0001 (23.6); −0.0056 (0.8) I-46: .sup.1H-NMR (599.6 MHz, CDCl.sub.3): δ = 8.9713 (8.7); 8.9692 (8.9); 8.5138 (8.0); 8.5097 (8.2); 8.1487 (5.4); 8.1462 (6.2); 8.1446 (6.0); 8.1422 (5.1); 7.2656 (7.1); 7.2525 (3.2); 7.2478 (2.4); 7.2441 (2.3); 7.2389 (3.0); 7.2359 (4.6); 7.2315 (3.0); 7.2267 (2.3); 7.2229 (2.4); 7.2181 (1.8); 7.2146 (2.0); 7.1842 (1.7); 7.1819 (2.1); 7.1779 (2.4); 7.1752 (2.2); 7.1715 (1.8); 7.1677 (1.5); 7.1639 (1.6); 7.1610 (1.4); 5.2763 (1.8); 5.2646 (5.8); 5.2530 (5.8); 5.2414 (1.8); 4.1343 (0.4); 3.8458 (0.5); 3.8096 (50.0); 3.7944 (0.4); 3.0148 (4.0); 2.9410 (3.1); 2.4778 (0.3); 2.4288 (0.4); 2.1029 (0.3); 2.0824 (3.3); 1.7216 (22.2); 1.7100 (22.1); 1.2565 (0.3); 0.0053 (0.4); −0.0001 (8.8) I-47: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ = 9.0078 (7.0); 9.0043 (7.0); 8.3413 (6.7); 8.3348 (7.0); 8.0668 (4.5); 8.0632 (4.7); 8.0603 (4.6); 8.0567 (4.2); 7.2604 (69.1); 7.2303 (1.4); 7.2091 (3.1); 7.1936 (1.9); 7.1886 (3.6); 7.1851 (3.9); 7.1805 (2.0); 7.1667 (1.8); 7.1636 (2.3); 7.0846 (1.2); 7.0808 (1.5); 7.0742 (1.6); 7.0703 (1.6); 7.0652 (1.3); 7.0597 (1.1); 7.0532 (1.2); 7.0488 (1.1); 7.0440 (0.8); 5.2976 (1.3); 5.2800 (5.0); 5.2625 (5.1); 5.2450 (1.2); 1.7868 (16.0); 1.7692 (15.8); 1.2626 (0.6); 0.8818 (0.8); 0.0079 (1.3); −0.0002 (41.9); −0.0085 (I-2) I-48: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ = 8.9693 (7.2); 8.9658 (7.1); 8.3291 (6.9); 8.3225 (7.1); 8.0811 (4.5); 8.0776 (4.7); 8.0747 (4.5); 8.0711 (4.1); 7.4001 (1.3); 7.3857 (1.5); 7.3800 (2.4); 7.3657 (2.4); 7.3602 (1.8); 7.3457 (1.8); 7.2599 (47.9); 7.1521 (1.3); 7.1455 (1.3); 7.1307 (2.2); 7.1244 (2.4); 7.1120 (3.4); 7.1089 (4.4); 7.1059 (3.4); 7.0895 (3.3); 7.0771 (2.2); 7.0729 (2.0); 7.0672 (1.4); 7.0539 (2.1); 7.0496 (2.1); 7.0437 (1.5); 5.3085 (1.2); 5.2910 (4.8); 5.2735 (5.0); 5.2561 (1.2); 1.7940 (16.0); 1.7765 (16.0); 1.2635 (1.6); 1.2428 (0.7); 0.8986 (0.8); 0.8820 (2.5); 0.8643 (1.0); 0.0079 (1.8); −0.0002 (61.9); −0.0084 (2.0) I-50: .sup.1H-NMR (400.2 MHz, d.sub.6-DMSO): δ = 9.0200 (5.6); 9.0173 (5.5); 8.6671 (4.9); 8.6609 (5.0); 8.4392 (3.6); 8.4334 (3.7); 8.3099 (3.4); 8.3064 (3.9); 8.3038 (3.7); 8.3004 (3.1); 8.2622 (1.2); 8.2562 (1.2); 8.2420 (2.0); 8.2363 (1.9); 8.2216 (1.3); 8.2156 (1.2); 7.3436 (2.1); 7.3375 (2.2); 7.3223 (2.1); 7.3162 (2.0); 5.7556 (2.5); 5.1833 (14.3); 4.2540 (2.2); 4.2363 (7.0); 4.2185 (7.0); 4.2008 (2.3); 3.3271 (79.8); 3.1753 (1.0); 3.1621 (1.0); 2.6759 (0.5); 2.6716 (0.6); 2.6671 (0.5); 2.5069 (81.6); 2.5025 (102.6); 2.4981 (74.4); 2.3337 (0.5); 2.3292 (0.6); 2.3248 (0.4); 1.2512 (7.8); 1.2334 (16.0); 1.2157 (7.5); −0.0002 (8.7); −0.0084 (0.4) I-51: .sup.1H-NMR (599.6 MHz, CDCl.sub.3): δ = 9.0519 (17.3); 8.3595 (13.2); 8.3555 (14.2); 8.2077 (10.4); 8.2044 (11.3); 7.9803 (8.5); 7.9780 (11.4); 7.9767 (11.8); 7.9743 (10.0); 7.8265 (3.4); 7.8225 (3.7); 7.8127 (5.9); 7.8091 (6.0); 7.8000 (3.6); 7.7960 (3.6); 7.2627 (22.1); 7.0247 (6.3); 7.0202 (6.6); 7.0106 (6.1); 7.0061 (6.2); 4.9533 (50.0); 4.9107 (0.4); 4.3238 (6.6); 4.3119 (19.6); 4.3000 (19.7); 4.2881 (6.6); 2.0444 (0.7); 1.5766 (31.7); 1.3464 (21.4); 1.3345 (42.2); 1.3227 (20.8); 1.2709 (0.3); 1.2592 (0.7); 1.2474 (0.3); 0.8818 (0.6); −0.0001 (32.6) I-53: .sup.1H-NMR (599.6 MHz, CDCl.sub.3): δ = 9.0493 (16.4); 8.3767 (13.1); 8.3727 (13.8); 8.2389 (11.1); 8.0000 (11.7); 7.8597 (3.4); 7.8558 (3.6); 7.8459 (6.0); 7.8430 (6.1); 7.8332 (3.7); 7.8292 (3.6); 7.2616 (33.4); 7.0261 (6.3); 7.0216 (6.6); 7.0121 (6.2); 7.0075 (6.3); 4.9628 (49.3); 4.3291 (6.4); 4.3172 (19.1); 4.3053 (19.3); 4.2935 (6.6); 1.5612 (47.3); 1.3481 (20.5); 1.3362 (40.5); 1.3244 (20.4); 1.2561 (0.6); −0.0001 (50.0) I-56: .sup.1H-NMR (400.2 MHz, d.sub.6-DMSO): δ = 9.3944 (7.0); 9.3920 (6.9); 9.3812 (7.2); 9.3788 (6.9); 9.3221 (7.8); 9.3192 (9.0); 9.3172 (9.0); 9.0142 (9.8); 8.5329 (10.3); 8.5266 (10.6); 8.3148 (0.5); 8.1442 (8.1); 8.1408 (8.1); 7.8633 (5.8); 7.8576 (6.0); 7.8501 (5.9); 7.8444 (5.6); 5.7554 (8.3); 5.2382 (1.4); 5.2210 (4.3); 5.2038 (4.3); 5.1867 (1.4); 4.0967 (0.8); 3.7493 (0.4); 3.3336 (65.0); 3.1691 (9.4); 2.6761 (1.4); 2.6716 (1.8); 2.6672 (1.4); 2.5731 (0.4); 2.5071 (247.0); 2.5027 (307.8); 2.4983 (222.9); 2.3339 (1.3); 2.3295 (1.7); 2.3250 (1.3); 1.6203 (16.0); 1.6031 (15.5); 0.0078 (0.8); −0.0002 (18.2) I-57: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ = 9.3511 (1.0); 8.8337 (4.8); 8.3295 (3.9); 8.3234 (4.0); 8.1274 (3.6); 7.5190 (0.9); 7.4320 (2.2); 7.4227 (9.6); 7.4193 (10.6); 7.4046 (7.1); 7.3954 (1.7); 7.3912 (2.0); 7.3815 (1.3); 7.3349 (8.0); 7.3308 (8.4); 7.3259 (3.4); 7.3162 (4.0); 7.3108 (5.0); 7.2601 (153.5); 6.9960 (0.8); 5.3488 (1.4); 5.3320 (3.7); 5.3143 (3.8); 5.2972 (1.0); 2.0080 (1.1); 1.7927 (16.0); 1.7752 (16.0); 0.0080 (5.3); −0.0002 (205.9); −0.0085 (6.0) I-58: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ = 9.3517 (0.5); 8.9574 (4.6); 8.9303 (0.8); 8.3520 (0.8); 8.3351 (3.9); 8.3287 (3.9); 8.0812 (4.0); 7.4009 (1.4); 7.3861 (1.8); 7.3808 (2.8); 7.3660 (2.9); 7.3606 (2.2); 7.3461 (2.0); 7.2606 (82.4); 7.1528 (1.5); 7.1464 (1.6); 7.1315 (2.7); 7.1251 (2.8); 7.1078 (4.7); 7.0887 (3.8); 7.0863 (3.0); 7.0773 (2.5); 7.0716 (2.3); 7.0540 (2.4); 7.0497 (2.4); 5.3110 (1.2); 5.2937 (4.2); 5.2762 (4.2); 5.2588 (1.2); 2.0082 (0.8); 1.7907 (16.0); 1.7825 (3.7); 1.7732 (15.9); 1.7650 (3.0); 0.0080 (3.5); −0.0002 (110.9); −0.0085 (3.3) I-59: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ = 9.1037 (4.0); 8.4860 (3.3); 8.4799 (3.3); 8.3072 (4.4); 8.3007 (4.6); 8.1276 (3.5); 7.9562 (1.9); 7.9498 (1.8); 7.9379 (2.3); 7.9349 (2.4); 7.9317 (2.2); 7.9286 (2.0); 7.9168 (2.0); 7.9104 (1.8); 7.2610 (70.3); 7.0829 (2.9); 7.0757 (3.0); 7.0607 (2.7); 7.0543 (2.8); 5.3203 (1.2); 5.3027 (4.6); 5.2852 (4.7); 5.2676 (1.2); 3.9928 (1.3); 2.0094 (10.0); 1.8014 (16.0); 1.7839 (15.9); 0.0080 (2.5); −0.0002 (92.1); −0.0085 (2.8) I-60: .sup.1H-NMR (400.0 MHz, de-DMSO): δ = 9.0269 (2.6); 9.0235 (2.5); 8.9748 (0.7); 8.7064 (0.6); 8.7000 (0.7); 8.6793 (2.4); 8.6729 (2.5); 8.4117 (1.8); 8.3989 (1.8); 8.3206 (1.6); 8.3171 (1.6); 8.3143 (1.6); 8.3107 (1.4); 7.5469 (1.2); 7.5341 (1.1); 7.5091 (1.9); 6.5316 (0.5); 5.2814 (1.8); 5.2641 (1.8); 5.2474 (0.5); 4.2028 (0.8); 2.6708 (1.0); 2.6664 (0.7); 2.5245 (2.5); 2.5198 (3.4); 2.5109 (54.9); 2.5064 (121.0); 2.5018 (170.4); 2.4973 (120.9); 2.4928 (54.7); 2.3286 (1.1); 1.9088 (16.0); 1.6388 (5.1); 1.6213 (5.7); 1.6022 (1.4); 1.2350 (0.7); 0.0081 (2.6); −0.0002 (102.0); −0.0085 (3.2) I-61: .sup.11H-NMR(400.0 MHz, CDCl.sub.3): δ = 9.1013 (3.9); 8.4901 (3.5); 8.2990 (5.5); 8.1226 (4.8); 7.9563 (1.7); 7.9498 (1.8); 7.9347 (3.0); 7.9167 (1.9); 7.9104 (1.6); 7.2613 (65.4); 7.0816 (3.6); 7.0743 (3.7); 7.0604 (3.5); 7.0531 (3.2); 5.3207 (1.9); 5.3045 (4.8); 5.2870 (4.5); 5.2693 (1.4); 3.9909 (0.7); 2.8309 (1.3); 2.0091 (8.4); 1.7981 (15.9); 1.7806 (16.0); −0.0002 (85.8) I-62: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ = 9.0841 (4.3); 9.0809 (4.4); 8.3653 (4.2); 8.3589 (4.5); 8.2889 (4.1); 8.2759 (4.2); 8.0389 (3.1); 8.0352 (3.3); 8.0324 (3.3); 8.0289 (3.1); 7.2615 (58.9); 7.1526 (1.6); 7.1487 (2.8); 7.1451 (1.8); 7.1397 (1.8); 7.1359 (2.8); 7.1321 (1.7); 6.9566 (4.4); 5.2990 (1.0); 5.2816 (4.1); 5.2641 (4.2); 5.2465 (1.0); 2.6568 (0.6); 2.0088 (16.0); 1.8008 (13.3); 1.7832 (13.3); 0.0079 (2.0); −0.0002 (77.1); −0.0085 (2.3) I-63: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ = 9.3518 (0.6); 9.0961 (2.1); 8.3374 (2.0); 8.2310 (4.1); 8.2250 (4.2); 8.0144 (2.7); 7.8452 (1.9); 7.8391 (1.7); 7.8242 (2.3); 7.8180 (2.2); 7.8054 (1.8); 7.7992 (1.9); 7.5198 (0.6); 7.2607 (118.4); 7.0280 (2.6); 7.0208 (2.6); 7.0059 (2.4); 6.9998 (2.6); 5.3036 (1.0); 5.2861 (4.6); 5.2686 (4.6); 5.2512 (1.2); 2.0086 (12.1); 1.8012 (16.0); 1.7837 (15.8); 0.1460 (0.6); 0.0080 (3.8); −0.0002 (156.2); −0.0085 (5.1); −0.1496 (0.7) I-64: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ = 9.0087 (2.9); 8.5297 (2.2); 8.1886 (2.7); 7.5191 (1.4); 7.2861 (1.3); 7.2602 (233.6); 7.2423 (3.2); 7.2214 (2.2); 7.1818 (1.7); 6.9962 (1.2); 5.0352 (16.0); 2.0083 (3.6); 0.0079 (7.9); −0.0002 (309.2); −0.0085 (9.2) I-65: .sup.1H-NMR (400.2 MHz, de-DMSO): δ = 9.0325 (4.8); 9.0291 (4.7); 8.5273 (4.5); 8.5209 (4.6); 8.3477 (2.8); 8.3416 (2.9); 8.1891 (2.9); 8.1855 (3.2); 8.1827 (3.0); 8.1792 (2.7); 8.1199 (1.0); 8.1137 (1.0); 8.0993 (1.7); 8.0936 (1.6); 8.0792 (1.1); 8.0730 (1.0); 7.3300 (1.8); 7.3235 (1.8); 7.3088 (1.7); 7.3023 (1.7); 5.7550 (6.2); 5.2077 (12.1); 5.1549 (16.0); 3.3246 (50.5); 2.6757 (0.4); 2.6711 (0.6); 2.6665 (0.4); 2.5245 (1.6); 2.5111 (38.4); 2.5067 (76.0); 2.5022 (97.5); 2.4976 (69.2); 2.4932 (33.3); 2.3334 (0.4); 2.3289 (0.6); 2.3243 (0.4); 0.0078 (0.4); −0.0002 (10.8); −0.0084 (0.4) I-66: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ = 9.0388 (2.2); 8.4295 (1.9); 8.4236 (1.9); 8.1949 (2.2); 8.1889 (2.3); 8.0107 (1.7); 8.0071 (2.0); 8.0013 (1.7); 7.8460 (0.9); 7.8397 (0.8); 7.8253 (1.2); 7.8209 (1.1); 7.8062 (0.9); 7.8001 (0.9); 7.2622 (25.3); 7.0195 (1.6); 7.0121 (1.6); 6.9983 (1.7); 6.9919 (1.5); 4.9721 (16.0); 4.3310 (2.1); 4.3131 (6.5); 4.2953 (6.6); 4.2774 (2.2); 1.5961 (0.9); 1.3488 (7.7); 1.3309 (15.7); 1.3131 (7.5); 0.0080 (0.6); −0.0002 (20.9); −0.0085 (0.6) I-67: .sup.1H-NMR (400.2 MHz, de-DMSO): δ = 9.0040 (2.6); 9.0008 (2.6); 8.5251 (2.4); 8.5186 (2.4); 8.3390 (1.6); 8.3333 (1.7); 8.1928 (1.5); 8.1893 (1.8); 8.1865 (1.7); 8.1830 (1.5); 8.1125 (0.5); 8.1061 (0.5); 8.0916 (1.0); 8.0855 (0.9); 8.0717 (0.6); 8.0655 (0.6); 7.3321 (1.0); 7.3260 (1.0); 7.3108 (1.0); 7.3043 (0.9); 5.7559 (1.5); 5.0966 (6.4); 4.2977 (1.6); 4.2864 (2.0); 4.2822 (1.5); 4.2748 (1.8); 3.6530 (1.8); 3.6456 (1.5); 3.6414 (2.0); 3.6300 (1.7); 3.5365 (1.7); 3.5256 (2.6); 3.5208 (1.7); 3.5129 (2.7); 3.4216 (2.7); 3.4138 (1.7); 3.4089 (2.5); 3.3979 (1.7); 3.3258 (55.4); 3.2167 (16.0); 2.6710 (0.4); 2.5065 (51.6); 2.5020 (66.2); 2.4976 (48.0); 2.3288 (0.4); −0.0002 (5.9) I-68: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ = 9.0637 (1.9); 9.0603 (2.0); 8.3755 (1.9); 8.3691 (1.9); 8.2318 (1.2); 8.2257 (1.2); 7.9927 (1.3); 7.9891 (1.4); 7.9864 (1.4); 7.9827 (1.3); 7.8577 (0.5); 7.8516 (0.5); 7.8389 (0.6); 7.8367 (0.7); 7.8328 (0.6); 7.8305 (0.7); 7.8178 (0.6); 7.8116 (0.6); 7.2618 (8.8); 7.0278 (0.8); 7.0205 (0.8); 7.0067 (0.8); 6.9993 (0.8); 5.0170 (7.5); 4.4140 (1.8); 4.4061 (1.0); 4.4024 (1.9); 4.3985 (1.0); 4.3907 (2.0); 3.6668 (2.1); 3.6591 (1.0); 3.6552 (2.0); 3.6516 (1.1); 3.6436 (2.0); 3.4034 (16.0); 1.5613 (2.4); 1.2559 (0.6); −0.0002 (11.4) I-69: .sup.1H-NMR (400.0 MHz, CDCl.sub.3): δ = 9.0639 (1.9); 9.0608 (1.9); 8.3795 (1.8); 8.3733 (1.9); 8.2312 (1.1); 8.2250 (1.1); 7.9998 (1.4); 7.9961 (1.5); 7.9934 (1.4); 7.9897 (1.3); 7.8588 (0.6); 7.8526 (0.6); 7.8400 (0.7); 7.8377 (0.7); 7.8338 (0.6); 7.8315 (0.7); 7.8190 (0.6); 7.8127 (0.6); 7.2616 (12.2); 7.0311 (0.8); 7.0249 (0.8); 7.0099 (0.7); 7.0039 (0.7); 5.1471 (8.4); 2.0748 (14.5); 2.0452 (1.1); 2.0393 (16.0); 1.5555 (4.0); 1.2596 (0.5); −0.0002 (16.3) I-71: .sup.1H-NMR (400.2 MHz, d.sub.6-DMSO): δ = 8.6595 (5.5); 8.6534 (6.3); 8.5824 (6.4); 8.5763 (5.5); 8.2516 (3.1); 8.2454 (3.2); 7.9742 (1.1); 7.9678 (1.1); 7.9531 (1.7); 7.9484 (1.6); 7.9337 (1.2); 7.9273 (1.2); 7.2903 (2.0); 7.2840 (2.0); 7.2688 (1.9); 7.2625 (1.8); 5.7558 (3.2); 4.9664 (13.3); 4.1944 (2.1); 4.1766 (6.8); 4.1589 (6.8); 4.1411 (2.2); 3.3251 (63.1); 2.6762 (0.5); 2.6716 (0.6); 2.6670 (0.5); 2.5248 (2.2); 2.5113 (41.9); 2.5071 (81.8); 2.5026 (104.7); 2.4981 (74.2); 2.4937 (35.5); 2.3338 (0.5); 2.3294 (0.6); 2.3249 (0.5); 1.2113 (7.6); 1.1936 (16.0); 1.1758 (7.4); 0.0079 (0.4); −0.0002 (9.6); −0.0085 (0.3) I-72: .sup.1H-NMR (400.2 MHz, de-DMSO): δ = 8.6533 (3.1); 8.6472 (3.5); 8.5633 (3.5); 8.5573 (3.1); 8.2491 (1.8); 8.2428 (1.9); 7.9691 (0.7); 7.9627 (0.6); 7.9481 (1.0); 7.9427 (1.0); 7.9286 (0.7); 7.9223 (0.7); 7.2860 (1.2); 7.2795 (1.2); 7.2647 (1.1); 7.2581 (1.1); 5.7557 (4.6); 5.1845 (0.5); 5.1674 (1.9); 5.1500 (1.9); 5.1328 (0.5); 3.6893 (16.0); 3.3245 (36.3); 2.6715 (0.4); 2.5246 (1.4); 2.5112 (26.3); 2.5070 (52.4); 2.5025 (68.1); 2.4980 (49.4); 2.4937 (24.4); 2.3295 (0.4); 1.5992 (6.4); 1.5819 (6.4); −0.0002 (7.1) I-74: .sup.1H-NMR (400.2 MHz, de-DMSO): δ = 8.3972 (2.0); 8.3910 (12.7); 8.3865 (4.9); 8.3798 (1.4); 7.6420 (1.0); 7.6369 (1.0); 7.6229 (1.1); 7.6173 (1.2); 7.6141 (1.3); 7.6084 (1.1); 7.5945 (1.0); 7.5894 (1.0); 7.5434 (0.9); 7.5219 (1.9); 7.5170 (1.1); 7.5005 (1.3); 7.4955 (1.8); 7.4742 (1.0); 7.2781 (1.2); 7.2724 (1.2); 7.2681 (1.2); 7.2625 (1.1); 7.2567 (1.0); 7.2517 (1.0); 7.2467 (0.9); 5.7560 (5.3); 4.9646 (13.9); 4.2064 (2.2); 4.1886 (7.0); 4.1708 (7.1); 4.1531 (2.3); 3.3250 (65.2); 2.6756 (0.6); 2.6713 (0.7); 2.6670 (0.5); 2.5069 (94.5); 2.5024 (119.5); 2.4980(85.2); 2.3337 (0.5); 2.3292 (0.7); 2.3249 (0.5); 1.2209 (7.7); 1.2032 (16.0); 1.1854 (7.5); 0.0079 (0.6); −0.0001 (13.2); −0.0083 (0.5) I-75: .sup.1H-NMR (400.2 MHz, de-DMSO): δ = 13.0565 (0.6); 8.6612 (0.4); 8.6540 (7.9); 8.6480 (9.3); 8.5767 (8.6); 8.5707 (7.7); 8.5631 (1.1); 8.5571 (0.9); 8.3149 (0.5); 8.2392 (4.2); 8.2329 (4.2); 7.9645 (1.5); 7.9582 (1.5); 7.9434 (2.5); 7.9388 (2.2); 7.9372 (2.2); 7.9241 (1.7); 7.9177 (1.6); 7.2870 (2.7); 7.2806 (2.8); 7.2655 (2.6); 7.2592 (2.5); 5.7551 (16.0); 5.1672 (0.4); 5.1498 (0.4); 5.0748 (1.0); 5.0574 (4.1); 5.0400 (4.3); 5.0224 (1.2); 4.1009 (0.9); 4.0885 (0.9); 3.8523 (0.7); 3.6893 (3.7); 3.3269 (54.0); 3.1746 (5.6); 3.1633 (5.4); 2.6804 (0.4); 2.6761 (0.8); 2.6715 (1.2); 2.6670 (0.9); 2.5249 (3.4); 2.5200 (5.6); 2.5115 (73.7); 2.5071 (148.8); 2.5025 (194.0); 2.4980 (138.2); 2.4935 (66.3); 2.3382 (0.4); 2.3339 (0.8); 2.3293 (1.2); 2.3248 (0.8); 1.5992 (1.8); 1.5869 (12.8); 1.5695 (12.7); 1.5465 (0.8); 1.5341 (0.4); 1.5164 (0.3); 1.3554 (1.0); 1.2360 (0.4); 0.0080 (0.8); −0.0001 (24.4); −0.0084 (0.8) I-76: .sup.1H-NMR (400.2 MHz, de-DMSO): δ = 8.3797 (2.6); 8.3737 (4.1); 8.3695 (3.7); 8.3628 (3.7); 8.3569 (3.6); 8.3463 (3.2); 8.3382 (3.7); 8.3315 (2.2); 8.1247 (1.2); 8.1186 (1.1); 8.1040 (1.9); 8.0986 (1.8); 8.0841 (1.2); 8.0779 (1.1); 7.3030 (2.1); 7.2966 (2.1); 7.2817 (2.0); 7.2753 (2.0); 5.7548 (1.7); 4.9789 (14.1); 4.2136 (2.2); 4.1958 (7.1); 4.1781 (7.1); 4.1603 (2.3); 3.3394 (320.5); 3.1756 (0.6); 3.1625 (0.6); 2.6764 (0.6); 2.6721 (0.7); 2.6677 (0.6); 2.5253 (2.2); 2.5076 (99.1); 2.5032 (124.0); 2.4987 (89.3); 2.3344 (0.6); 2.3300 (0.8); 2.3254 (0.6); 1.2289 (7.7); 1.2111 (16.0); 1.1934 (7.5); −0.0002 (1.5) I-77: .sup.1H-NMR (400.2 MHz, de-DMSO): δ = 8.3851 (1.4); 8.3790 (2.1); 8.3749 (1.9); 8.3628 (2.0); 8.3541 (2.5); 8.3457 (2.1); 8.3385 (1.2); 8.1251 (0.7); 8.1189 (0.6); 8.1048 (1.1); 8.0989 (1.0); 8.0846 (0.7); 8.0782 (0.7); 7.3040 (1.2); 7.2974 (1.2); 7.2828 (1.2); 7.2760 (1.1); 5.7559 (3.7); 5.0030 (8.0); 3.7172 (16.0); 3.3252 (37.1); 2.6714 (0.4); 2.5112 (27.7); 2.5069 (52.1); 2.5025 (66.1); 2.4981 (47.3); 2.4940 (23.2); 2.3293 (0.4); 0.0078 (0.4); −0.0002 (7.0) I-90: .sup.1H-NMR (400.6 MHz, CDCl.sub.3): δ = 9.0636 (3.8); 9.0601 (3.8); 8.5326 (2.8); 8.5257 (2.8); 8.3920 (1.8); 8.3883 (3.1); 8.3838 (4.7); 8.3767 (3.8); 7.9931 (2.6); 7.9895 (2.8); 7.9867 (2.8); 7.9831 (2.6); 7.5159 (1.2); 7.5115 (1.3); 7.5090 (1.4); 7.5047 (1.2); 7.4938 (1.3); 7.4895 (1.4); 7.4869 (1.4); 7.4826 (1.2); 7.2613 (38.7); 4.9648 (15.4); 4.9574 (1.2); 4.3381 (2.0); 4.3202 (6.2); 4.3024 (6.2); 4.2846 (2.0); 1.5635 (9.6); 1.3544 (7.8); 1.3366 (16.0); 1.3188 (7.5); 0.0080 (1.2); 0.0048 (0.6); −0.0002 (37.1); −0.0057 (0.5); −0.0084 (1.0) I-91: .sup.1H-NMR (400.6 MHz, CDCl.sub.3): δ = 9.0643 (3.3); 9.0612 (3.4); 8.5340 (2.2); 8.5272 (2.3); 8.3965 (2.6); 8.3915 (4.3); 8.3848 (3.4); 8.0073 (2.6); 8.0037 (2.8); 8.0009 (2.8); 7.9973 (2.6); 7.5254 (1.2); 7.5211 (1.4); 7.5185 (1.4); 7.5142 (1.2); 7.5033 (1.3); 7.4990 (1.4); 7.4964 (1.3); 7.4921 (1.2); 7.2634 (27.2); 4.9693 (15.1); 4.3412 (1.9); 4.3233 (6.1); 4.3055 (6.2); 4.2877 (2.0); 2.9283 (1.3); 1.5761 (2.8); 1.3571 (7.7); 1.3393 (16.0); 1.3215 (7.5); 0.0080 (1.0); −0.0002 (39.8); −0.0085 (1.1) I-92: .sup.1H-NMR (400.6 MHz, d.sub.6-DMSO): δ = 13.1958 (1.1); 9.0176 (5.7); 9.0167 (5.8); 9.0140 (5.7); 9.0131 (5.8); 8.7010 (5.2); 8.6940 (5.2); 8.5368 (6.0); 8.5359 (6.3); 8.5304 (10.8); 8.5295 (11.1); 8.5261 (2.6); 8.1973 (4.9); 8.1938 (5.0); 8.1909 (4.9); 8.1873 (4.7); 7.9956 (2.0); 7.9914 (2.0); 7.9886 (2.0); 7.9844 (1.8); 7.9715 (2.1); 7.9673 (2.2); 7.9646 (1.9); 7.9603 (1.8); 5.7569 (3.5); 4.9917 (16.0); 3.3214 (15.8); 2.6704 (0.7); 2.5649 (0.6); 2.5242 (1.6); 2.5195 (2.3); 2.5107 (35.7); 2.5061 (78.2); 2.5015 (109.9); 2.4969 (75.2); 2.4924 (32.7); 2.4797 (0.5); 2.3286 (0.6); 1.3552 (1.0); 0.0080 (1.0); −0.0002 (32.0); −0.0085 (0.9) I-93: .sup.1H-NMR (400.6 MHz, de-DMSO): δ = 9.0142 (6.0); 9.0133 (6.1); 9.0107 (6.0); 9.0097 (6.2); 8.6961 (5.5); 8.6891 (5.5); 8.5291 (6.0); 8.5282 (6.2); 8.5226 (6.5); 8.5217 (6.4); 8.5162 (3.0); 8.5127 (5.1); 8.5121 (5.4); 8.5085 (2.6); 8.1868 (5.2); 8.1832 (5.3); 8.1803 (5.2); 8.1767 (5.0); 7.9775 (2.0); 7.9733 (2.1); 7.9705 (2.1); 7.9663 (1.8); 7.9535 (2.2); 7.9492 (2.3); 7.9465 (2.0); 7.9422 (1.9); 5.7567 (0.6); 4.9803 (16.0); 3.6011 (0.7); 3.3269 (11.1); 2.5249 (1.0); 2.5203 (1.3); 2.5115 (19.2); 2.5069 (42.5); 2.5023 (59.7); 2.4977 (40.6); 2.4931 (17.7); 1.7595 (0.9); 0.0080 (1.9); −0.0002 (72.2); −0.0085 (1.9) I-94: .sup.1H-NMR (400.6 MHz, CDCl.sub.3): δ = 9.0685 (2.5); 9.0652 (2.5); 8.5224 (1.2); 8.5159 (1.3); 8.4348 (1.5); 8.3895 (2.5); 8.3832 (2.6); 8.0302 (2.1); 8.0265 (2.2); 8.0237 (2.2); 8.0201 (2.0); 7.5281 (0.7); 7.5233 (0.8); 7.5187 (1.0); 7.5059 (0.6); 7.5009 (0.9); 7.4958 (0.6); 7.2604 (96.5); 7.2570 (1.4); 7.2554 (0.8); 7.2546 (0.7); 4.9556 (14.2); 4.3417 (1.8); 4.3239 (5.6); 4.3061 (5.7); 4.2883 (1.8); 1.7764 (0.6); 1.3557 (7.6); 1.3379 (16.0); 1.3200 (7.4); 0.0080 (3.9); 0.0064 (0.6); 0.0055 (0.7); 0.0047 (1.0); 0.0039 (1.4); 0.0022 (5.6); −0.0002 (142.5); −0.0051 (1.5); −0.0059 (1.3); −0.0067 (1.1); −0.0084 (4.0) I-95: .sup.1H-NMR (400.6 MHz, CDCl.sub.3): δ = 9.0353 (1.8); 9.0318 (1.8); 8.5270 (1.3); 8.5201 (1.3); 8.3972 (0.8); 8.3936 (1.4); 8.3901 (0.9); 8.3757 (1.8); 8.3693 (1.8); 7.9903 (1.4); 7.9866 (1.5); 7.9839 (1.4); 7.9803 (1.4); 7.5160 (0.6); 7.5117 (0.7); 7.5091 (0.7); 7.5047 (0.6); 7.4938 (0.7); 7.4895 (0.7); 7.4869 (0.7); 7.4826 (0.6); 7.2634 (5.2); 5.2817 (1.5); 5.2642 (1.5); 3.8234 (16.0); 1.7391 (6.1); 1.7217 (6.1); 1.5994 (2.1); 0.8817 (0.6); −0.0002 (7.5) I-96: .sup.1H-NMR (400.6 MHz, CDCl.sub.3): δ = 9.0967 (3.3); 8.5409 (1.8); 8.3984 (1.9); 8.3369 (2.9); 8.3308 (3.0); 8.0012 (2.8); 7.9978 (3.3); 7.9951 (3.4); 7.9916 (2.9); 7.5184 (0.6); 7.5130 (1.5); 7.5089 (1.9); 7.5065 (2.0); 7.5023 (1.7); 7.4912 (1.7); 7.4870 (2.0); 7.4845 (1.9); 7.4804 (1.6); 7.2600 (74.5); 5.3000 (12.8); 5.2827 (5.1); 5.2652 (5.2); 5.2477 (1.2); 1.8013 (16.0); 1.7928 (1.7); 1.7838 (15.9); 1.2546 (0.9); 0.0080 (3.3); −0.0002 (112.6); −0.0084 (3.6) I-97: .sup.1H-NMR (400.6 MHz, CDCl.sub.3): δ = 9.0941 (5.0); 9.0913 (5.1); 8.5472 (3.3); 8.5407 (3.4); 8.4130 (4.0); 8.3333 (4.9); 8.3268 (5.2); 8.0103 (3.9); 8.0068 (4.3); 8.0039 (4.2); 8.0003 (3.8); 7.5276 (2.0); 7.5233 (2.2); 7.5208 (2.3); 7.5165 (2.0); 7.5057 (2.1); 7.5014 (2.4); 7.4989 (2.2); 7.4946 (1.9); 7.2608 (30.7); 5.3000 (4.9); 5.2804 (5.2); 5.2630 (5.3); 5.2455 (1.2); 1.7998 (16.0); 1.7823 (15.9); 1.7714 (0.9); 0.0080 (1.5); −0.0002 (46.9); −0.0084 (1.3) I-98: .sup.1H-NMR (400.6 MHz, CDCl.sub.3): δ = 9.0415 (2.1); 9.0389 (2.1); 8.5255 (0.7); 8.3960 (0.8); 8.3709 (2.1); 8.3646 (2.1); 7.9860 (1.8); 7.9824 (2.0); 7.9797 (2.0); 7.9761 (1.8); 7.5156 (0.8); 7.5114 (1.0); 7.5089 (1.0); 7.5047 (0.8); 7.4935 (0.9); 7.4892 (1.0); 7.4867 (1.0); 7.4825 (0.8); 7.2613 (28.0); 5.2665 (0.8); 5.2490 (3.0); 5.2316 (3.0); 5.2142 (0.8); 4.3139 (0.9); 4.3058 (1.1); 4.2961 (3.0); 4.2883 (3.0); 4.2783 (3.1); 4.2705 (3.0); 4.2607 (1.2); 4.2528 (1.0); 1.7348 (11.3); 1.7174 (11.2); 1.5681 (3.4); 1.3353 (7.6); 1.3175 (16.0); 1.2997 (7.3); 0.0080 (1.2); −0.0002 (43.5); −0.0085 (1.3) I-99: .sup.1H-NMR (400.6 MHz, CDCl.sub.3): δ = 9.0441 (2.8); 9.0409 (2.8); 8.5278 (1.1); 8.5228 (1.1); 8.3858 (1.4); 8.3663 (2.8); 8.3600 (2.9); 7.9750 (2.3); 7.9714 (2.5); 7.9686 (2.4); 7.9650 (2.2); 7.5090 (1.1); 7.5047 (1.2); 7.5021 (1.2); 7.4978 (1.0); 7.4868 (1.1); 7.4825 (1.2); 7.4800 (1.1); 7.4757 (1.0); 7.2619 (19.0); 5.2625 (0.8); 5.2451 (3.0); 5.2277 (3.0); 5.2103 (0.8); 4.3127 (0.9); 4.3048 (1.1); 4.2948 (3.0); 4.2872 (3.1); 4.2770 (3.2); 4.2695 (3.0); 4.2593 (1.2); 4.2518 (0.9); 1.7340 (11.4); 1.7166 (11.2); 1.5813 (2.0); 1.3350 (7.7); 1.3172 (16.0); 1.2994 (7.3); 0.8819 (0.6); 0.0079 (0.7); −0.0002 (29.1); −0.0028 (1.2); −0.0085 (0.9) I-100: .sup.1H-NMR (400.6 MHz, CDCl.sub.3): δ = 8.1032 (1.3); 8.0989 (1.0); 8.0969 (1.3); 7.7843 (0.6); 7.7780 (0.6); 7.7657 (0.7); 7.7632 (0.7); 7.7594 (0.7); 7.7569 (0.7); 7.7446 (0.6); 7.7383 (0.6); 7.2614 (7.7); 7.1845 (0.5); 7.1803 (0.6); 7.1674 (0.8); 7.1614 (0.9); 7.1489 (1.5); 7.1447 (1.7); 7.1419 (1.5); 7.1380 (1.2); 7.1344 (1.6); 7.1284 (1.0); 6.9809 (0.9); 6.9795 (0.9); 6.9734 (0.9); 6.9721 (0.9); 6.9598 (0.8); 6.9584 (0.9); 6.9523 (0.8); 6.9509 (0.8); 4.9150 (0.5); 4.9076 (8.6); 3.8047 (16.0); 2.0448 (0.9); 1.5524 (4.3); 1.2592 (0.6); −0.0002 (11.4)

B. Formulation Examples

[0656] a) A dusting product is obtained by mixing 10 parts by weight of a compound of the formula (I) and/or salts thereof and 90 parts by weight of talc as inert substance and comminuting the mixture in an impact mill.

[0657] b) A readily water-dispersible, wettable powder is obtained by mixing 25 parts by weight of a compound of the formula (I) and/or salts thereof, 64 parts by weight of kaolin-containing quartz as inert substance, 10 parts by weight of potassium lignosulfonate and 1 part by weight of sodium oleoylmethyltaurate as wetting agent and dispersant and grinding in a pinned-disc mill.

[0658] c) A readily water-dispersible dispersion concentrate is obtained by mixing 20 parts by weight of a compound of the formula (I) and/or salts thereof with 6 parts by weight of alkylphenol polyglycol ether (® Triton X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling range e.g. about 255 to more than 277° C.) and grinding to a fineness of below 5 microns in an attrition ball mill.

[0659] d) An emulsifiable concentrate is obtained from 15 parts by weight of a compound of the formula (I) and/or salts thereof, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of oxethylated nonylphenol as emulsifier.

[0660] e) Water-dispersible granules are obtained by mixing

[0661] 75 parts by weight of a compound of the formula (I) and/or salts thereof,

[0662] 10 parts by weight of calcium lignosulfonate,

[0663] 5 parts by weight of sodium lauryl sulfate,

[0664] 3 parts by weight of polyvinyl alcohol and

[0665] 7 parts by weight of kaolin,

[0666] grinding the mixture in a pinned-disk mill, and granulating the powder in a fluidized bed by spray application of water as a granulating liquid.

[0667] f) Water-dispersible granules are also obtained by homogenizing and precomminuting, in a colloid mill,

[0668] 25 parts by weight of a compound of the formula (I) and/or salts thereof,

[0669] 5 parts by weight of sodium 2,2′-dinaphthylmethane-6,6′-disulfonate,

[0670] 2 parts by weight of sodium oleoylmethyltaurate,

[0671] 1 part by weight of polyvinyl alcohol,

[0672] 17 parts by weight of calcium carbonate and

[0673] 50 parts by weight of water,

[0674] then grinding the mixture in a bead mill and atomizing and drying the resulting suspension in a spray tower by means of a one-phase nozzle.

C. Biological Examples

[0675] In Tables A1 to A21 and B1 to B21 below, the following abbreviations are used:

TABLE-US-00004 ABUTH: Abutilon theophrasti ALOMY: Alopecurus myosuroides AMARE: Amaranthus retroflexus AVEFA: Avena fatua DIGSA: Digitaria sanguinalis ECHCG: Echinochloa crus-galli HORMU: Hordeum murinum LOLRI: Lolium rigidum MATIN: Matricaria inodora PHBPU: Pharbitis purpurea POAAN: Poa annua POLCO: Polygonum convolvulus SETVI: Setaria viridis STEME: Stellaria media VERPE: Veronica persica VIOTR: Viola tricolor

[0676] 1. Herbicidal Post-Emergence Action

[0677] a) Seeds of monocotyledonous and dicotyledonous weeds and crop plants are placed in sandy loam in plastic or organic plant pots, covered with soil and cultivated in a greenhouse under controlled growth conditions. 2 to 3 weeks after sowing, the test plants are treated at the one-leaf stage. The compounds of the invention, formulated in the form of wettable powders (WP) or as emulsion concentrates (EC), are then sprayed onto the green parts of the plants as aqueous suspension or emulsion with addition of 0.5% additive at a water application rate of 600 1/ha (converted). After the test plants have been kept in the greenhouse under optimum growth conditions for about 3 weeks, the activity of the preparations is rated visually in comparison to untreated controls. For example, 100% activity=the plants have died, 0% activity=like control plants.

[0678] Tables A1 to A15 below show the effects of selected compounds of the general formula (I) according to Tables 1 and 2 on various harmful plants and an application rate corresponding to 320 g/ha and/or 80 g/ha, which were obtained by the experimental procedure mentioned above.

TABLE-US-00005 TABLE A1 Post-emergence action against ALOMY in % Example Dosage ALOMY number [g/ha] (%) I-01 320 90 I-02 320 80 I-04 320 90 I-05 320 100 I-07 320 100 I-08 320 100 I-09 320 90 I-10 320 90 I-11 320 100 I-12 320 90 I-15 320 80 I-16 320 100 I-17 320 100 I-20 320 90 I-21 320 90 I-22 320 100 I-25 320 80 I-34 320 100 I-36 320 100 I-37 320 100 I-39 320 100 I-40 320 90 I-45 320 90 I-46 320 90 I-52 320 90 I-05 80 100 I-07 80 90 I-08 80 100 I-09 80 80 I-10 80 90 I-12 80 90 I-13 80 90 I-15 80 80 I-16 80 90 I-17 80 100 I-20 80 80 I-22 80 90 I-34 80 80 I-37 80 90 I-39 80 90 I-40 80 80 I-45 80 90 I-46 80 90 I-47 80 90 I-48 80 90 I-52 80 80 I-65 80 80 I-67 80 90 I-68 80 80 I-72 80 90 I-89 320 100 I-88 320 100 I-83 320 80 II-03 320 90 I-92 320 80 I-90 320 100 I-93 320 100 I-94 320 80 I-97 320 90 I-96 320 100 I-95 320 100 I-99 320 100 I-98 320 80 I-89 80 80 I-87 80 100 I-88 80 80 I-86 80 90 I-83 80 80 II-03 80 80 I-90 80 80 I-95 80 100 I-99 80 80 I-98 80 80

TABLE-US-00006 TABLE A2 Post-emergence action against AVEFA in % Example Dosage AVEFA number [g/ha] (%) I-05 320 100 I-07 320 100 I-08 320 100 I-09 320 90 I-10 320 90 I-12 320 100 I-15 320 90 I-16 320 100 I-17 320 100 I-20 320 90 I-21 320 80 I-22 320 100 I-34 320 90 I-36 320 90 I-37 320 90 I-39 320 90 I-40 320 80 I-45 320 80 I-46 320 80 I-05 80 90 I-07 80 100 I-08 80 100 I-09 80 90 I-10 80 80 I-12 80 100 I-13 80 100 I-15 80 90 I-16 80 90 I-17 80 90 I-20 80 90 I-22 80 100 I-36 80 90 I-37 80 90 I-39 80 80 I-46 80 80 I-48 80 80 I-72 80 90 I-89 320 100 I-88 320 100 II-03 320 90 I-92 320 90 I-90 320 100 I-91 320 90 I-93 320 100 I-94 320 80 I-97 320 100 I-96 320 90 I-95 320 90 I-99 320 100 I-98 320 80 I-89 80 90 I-87 80 90 I-86 80 90 I-92 80 90 I-93 80 100 I-95 80 80 I-99 80 80 I-98 80 80

TABLE-US-00007 TABLE A3 Post-emergence action against DIGSA in % Example Dosage DIGSA number [g/ha] (%) I-01 320 80 I-05 320 90 I-07 320 90 I-08 320 80 I-10 320 80 I-12 320 80 I-13 320 90 I-15 320 90 I-16 320 90 I-17 320 90 I-20 320 90 I-22 320 80 I-34 320 80 I-36 320 90 I-37 320 90 I-39 320 90 I-40 320 80 I-05 80 80 I-07 80 80 I-13 80 80 I-17 80 80 I-20 80 80 I-36 80 80 I-39 80 80 I-47 80 80 I-53 80 90

TABLE-US-00008 TABLE A4 Post-emergence action against ECHCG in % Example Dosage ECHCG number [g/ha] (%) I-01 320 90 I-02 320 80 I-07 320 90 I-08 320 90 I-09 320 80 I-11 320 80 I-12 320 80 I-13 320 90 I-15 320 90 I-16 320 90 I-17 320 90 I-20 320 80 I-37 320 90 I-39 320 90 I-45 320 80 I-52 320 80 I-07 80 80 I-08 80 80 I-09 80 80 I-13 80 80 I-39 80 80 I-48 80 90 I-53 80 80 I-68 80 80 I-89 320 80 II-03 320 80 I-92 320 90 I-90 320 90 I-91 320 90 I-93 320 90 I-94 320 90 I-97 320 90 I-96 320 90 I-95 320 90 I-99 320 90 I-98 320 80 I-92 80 90 I-97 80 90 I-96 80 80 I-95 80 90 I-99 80 90 I-98 80 80

TABLE-US-00009 TABLE A5 Post-emergence action against LOLRI in % Example Dosage LOLRI number [g/ha] (%) I-01 320 90 I-04 320 80 I-05 320 90 I-07 320 90 I-08 320 90 I-09 320 90 I-10 320 90 I-12 320 90 I-15 320 90 I-16 320 90 I-17 320 90 I-20 320 100 I-21 320 90 I-22 320 100 I-34 320 80 I-36 320 90 I-37 320 90 I-39 320 90 I-40 320 80 I-45 320 90 I-46 320 90 I-07 80 80 I-13 80 80 I-15 80 90 I-17 80 90 I-20 80 90 I-22 80 80 I-39 80 90 I-45 80 90 I-46 80 90 I-89 320 100 I-88 320 100 I-92 320 90 I-90 320 80 I-91 320 90 I-93 320 90 I-94 320 90 I-97 320 100 I-96 320 100 I-95 320 90 I-99 320 100 I-98 320 90 I-97 80 90 I-96 80 100 I-95 80 90 I-99 80 100

TABLE-US-00010 TABLE A6 Post-emergence action against SETVI in % Example Dosage SETVI number [g/ha] (%) I-05 320 80 I-07 320 80 I-08 320 80 I-10 320 80 I-11 320 90 I-12 320 80 I-15 320 90 I-16 320 90 I-17 320 80 I-20 320 90 I-22 320 80 I-34 320 90 I-36 320 100 I-37 320 90 I-39 320 80 I-40 320 90 I-45 320 80 I-07 80 80 I-08 80 80 I-15 80 90 I-16 80 80 I-20 80 80 I-22 80 80 I-34 80 80 I-37 80 90 I-39 80 80 I-48 80 80 I-53 80 80 I-89 320 90 I-78 320 100 II-03 320 90 I-92 320 80 I-90 320 90 I-91 320 90 I-93 320 90 I-94 320 90 I-97 320 90 I-96 320 90 I-95 320 90 I-99 320 90 I-98 320 80 I-78 80 80 II-03 80 90 I-92 80 80 I-90 80 80 I-91 80 80 I-93 80 90 I-97 80 90 I-96 80 90 I-95 80 90 I-99 80 90 I-98 80 80

TABLE-US-00011 TABLE A7 Post-emergence action against ABUTH in % Example Dosage ABUTH number [g/ha] (%) I-01 320 80 I-05 320 80 I-07 320 90 I-08 320 90 I-11 320 80 I-12 320 80 I-13 320 80 I-15 320 80 I-16 320 80 I-17 320 80 I-20 320 90 I-36 320 80 I-37 320 80 I-39 320 80 I-40 320 80 I-45 320 80 I-52 320 80 I-07 80 80 I-08 80 80 I-15 80 80 I-17 80 80 I-20 80 80 I-37 80 80 I-39 80 80 I-40 80 80 I-53 80 80 I-89 320 90 I-92 320 90 I-90 320 90 I-91 320 80 I-93 320 80 I-94 320 90 I-97 320 90 I-95 320 90 I-98 320 80 I-89 80 90 II-09 80 90 I-90 80 90 I-91 80 80 I-93 80 80 I-97 80 90 I-95 80 90 I-98 80 80

TABLE-US-00012 TABLE A8 Post-emergence action against AMARE in % Example Dosage AMARE number [g/ha] (%) I-01 320 90 I-02 320 80 I-04 320 90 I-05 320 80 I-07 320 80 I-08 320 80 I-10 320 80 I-11 320 90 I-12 320 80 I-15 320 80 I-16 320 90 I-17 320 80 I-20 320 100 I-21 320 90 I-22 320 90 I-25 320 80 I-34 320 80 I-36 320 90 I-37 320 90 I-39 320 80 I-40 320 90 I-45 320 90 I-46 320 80 I-52 320 80 I-01 80 80 I-04 80 90 I-11 80 90 I-12 80 80 I-13 80 80 I-15 80 80 I-17 80 80 I-20 80 90 I-21 80 80 I-22 80 90 I-36 80 90 I-40 80 80 I-46 80 80 I-47 80 80 I-52 80 90 I-53 80 80 I-72 80 80 I-89 320 90 I-84 320 90 I-88 320 80 I-80 320 80 II-03 320 90 I-92 320 90 I-90 320 90 I-91 320 90 I-93 320 90 I-94 320 80 I-97 320 90 I-95 320 90 I-99 320 90 I-98 320 80 I-89 80 90 II-10 80 80 II-09 80 90 II-08 80 80 I-87 80 80 II-13 80 80 I-84 80 90 I-80 80 80 I-92 80 80 I-91 80 80 I-93 80 90 I-97 80 90 I-95 80 90 I-99 80 90

TABLE-US-00013 TABLE A9 Post-emergence action against MATIN in % Example Dosage MATIN number [g/ha] (%) I-01 320 90 I-02 320 80 I-04 320 90 I-07 320 90 I-08 320 90 I-11 320 80 I-12 320 80 I-13 320 80 I-15 320 80 I-16 320 80 I-22 320 80 I-34 320 90 I-36 320 80 I-37 320 80 I-39 320 90 I-45 320 80 I-46 320 80 I-01 80 80 I-04 80 80 I-07 80 90 I-08 80 80 I-39 80 80 I-53 80 80 I-89 320 80 I-83 320 80 I-94 320 80 I-97 320 90 I-96 320 90 I-95 320 90 I-99 320 90 I-97 80 90 I-96 80 80 I-95 80 80 I-99 80 80

TABLE-US-00014 TABLE A10 Post-emergence action against PHBPU in % Example Dosage PHBPU number [g/ha] (%) I-01 320 80 I-02 320 90 I-04 320 80 I-07 320 90 I-08 320 90 I-11 320 80 I-12 320 90 I-15 320 90 I-16 320 90 I-20 320 90 I-21 320 80 I-22 320 90 I-34 320 80 I-36 320 90 I-37 320 80 I-39 320 90 I-40 320 90 I-45 320 90 I-01 80 80 I-04 80 80 I-07 80 90 I-08 80 80 I-11 80 80 I-12 80 80 I-13 80 80 I-15 80 90 I-22 80 80 I-36 80 90 I-39 80 80 I-47 80 80 I-52 80 80 I-53 80 80 I-68 80 80 I-92 320 90 I-91 320 90 I-93 320 90 I-94 320 100 I-97 320 100 I-96 320 90 I-95 320 90 I-99 320 90 I-98 320 90 II-10 80 80 I-92 80 80 I-93 80 90 I-97 80 90 I-96 80 90 I-95 80 90 I-99 80 80 I-98 80 90

TABLE-US-00015 TABLE A11 Post-emergence action against POLCO in % Example Dosage POLCO number [g/ha] (%) I-01 320 80 I-04 320 90 I-07 320 90 I-08 320 100 I-09 320 100 I-11 320 90 I-12 320 90 I-16 320 90 I-17 320 90 I-20 320 80 I-22 320 80 I-34 320 100 I-36 320 100 I-37 320 100 I-39 320 90 I-40 320 80 I-45 320 100 I-46 320 100 I-48 320 100 I-52 320 80 I-53 320 90 I-01 80 80 I-04 80 80 I-05 80 80 I-07 80 80 I-13 80 80 I-36 80 90 I-40 80 80 I-53 80 90 I-89 320 90 I-84 320 80 I-88 320 80 I-80 320 80 II-03 320 80 I-90 320 80 I-91 320 80 I-94 320 80 I-97 320 90 I-96 320 80 I-95 320 90 I-99 320 80 I-98 320 80 I-89 80 90 II-09 80 80 I-90 80 80 I-91 80 80 I-97 80 90 I-96 80 80 I-95 80 90 I-99 80 80

TABLE-US-00016 TABLE A12 Post-emergence action against STEME in % Example Dosage STEME number [g/ha] (%) I-01 320 90 I-02 320 80 I-04 320 80 I-05 320 80 I-07 320 90 I-08 320 90 I-09 320 80 I-10 320 90 I-12 320 90 I-07 80 90 I-08 80 90 I-12 80 80 I-13 80 90

TABLE-US-00017 TABLE A13 Post-emergence action against VIOTR in % Example Dosage VIOTR number [g/ha] (%) I-01 320 90 I-02 320 80 I-04 320 80 I-05 320 90 I-07 320 90 I-08 320 90 I-09 320 90 I-10 320 100 I-11 320 100 I-12 320 100 I-15 320 90 I-16 320 90 I-17 320 90 1-20 320 90 I-21 320 90 I-22 320 90 I-25 320 90 I-34 320 90 I-36 320 90 I-37 320 90 I-39 320 90 I-40 320 80 I-45 320 90 I-52 320 80 I-01 80 90 I-05 80 90 I-07 80 80 I-08 80 90 I-09 80 90 I-10 80 90 I-11 80 90 I-12 80 90 I-13 80 90 I-15 80 90 I-16 80 80 I-17 80 90 I-20 80 80 I-21 80 80 I-22 80 80 I-34 80 90 I-36 80 90 I-37 80 80 I-39 80 80 I-45 80 80 I-53 80 90 I-65 80 80

TABLE-US-00018 TABLE A14 Post-emergence action against VERPE in % Example Dosage VERPE number [g/ha] (%) I-01 320 90 I-02 320 80 I-04 320 80 I-05 320 90 I-07 320 90 I-08 320 90 I-10 320 90 I-11 320 90 I-12 320 90 I-15 320 90 I-16 320 80 I-17 320 90 I-20 320 90 I-21 320 80 I-22 320 90 I-34 320 80 I-36 320 90 I-37 320 90 I-39 320 90 I-40 320 80 I-45 320 80 I-46 320 80 I-52 320 90 I-01 80 80 I-05 80 80 I-07 80 90 I-08 80 90 II-09 80 90 I-10 80 80 I-11 80 90 I-12 80 80 I-13 80 90 I-15 80 90 I-20 80 80 I-22 80 80 I-37 80 80 I-39 80 80 I-53 80 80 I-65 80 80 I-89 320 90 I-78 320 80 I-84 320 80 I-88 320 80 I-92 320 90 I-90 320 90 I-91 320 80 I-93 320 80 I-94 320 90 I-97 320 90 I-96 320 90 I-95 320 90 I-99 320 90 I-98 320 80 I-89 80 80 I-09 80 90 I-92 80 80 I-90 80 90 I-91 80 80 I-93 80 80 I-94 80 90 I-97 80 90 I-96 80 90 I-95 80 90 I-99 80 90 I-98 80 80

TABLE-US-00019 TABLE A15 Post-emergence action against HORMU in % Example Dosage HORMU number [g/ha] (%) I-05 320 90 I-07 320 90 I-08 320 90 I-09 320 90 I-10 320 80 I-12 320 90 I-13 320 90 I-07 80 80 I-08 80 80 I-09 80 80 I-10 80 80 I-12 80 90 I-13 80 90

[0679] As the results show, inventive compounds, for example compound nos. I-01, I-05, I-07, I-08, I-10, I-11, I-12, I-15, I-16, I-17, I-20, I-22, I-34, I-36, I-37, I-39, I-40, I-45 and I-53 and other compounds from Tables A1 to A15, show good herbicidal efficacy against harmful plants in the case of post-emergence treatment. For example, compound nos. I-05, I-07, I-08, I-10, I-12, I-16, I-17, I-22, I-36, I-37, I-39 and I-40 in the post-emergence method have very good action (80% to 100% herbicidal activity) against harmful plants such as Alopecurus myosuroides, Amaranthus retroflexus, Avena fatua, Lolium rigidum, Polygonum convolvulus, Setaria viridis, Veronica persica and Viola tricolor at an application rate of 0.32 kg of active substance per hectare.

[0680] b) Seeds of mono- and dicotyledonous weed plants are placed in plastic pots in sandy loam soil (twin sowing with one species each of mono- or dicotyledonous weed plants per pot), covered with soil and cultivated in a greenhouse under controlled growth conditions. 2 to 3 weeks after sowing, the test plants are treated at the one-leaf stage. The compounds of the invention, formulated in the form of wettable powders (WP) or as emulsion concentrates (EC), are applied to the green parts of the plants as aqueous suspension or emulsion with addition of 0.5% additive at a water application rate equivalent to 600 litres per hectare. After the test plants have been kept in the greenhouse under optimum growth conditions for about 3 weeks, the activity of the preparations is rated visually in comparison to untreated controls. For example, 100% activity=the plants have died, 0% activity=like control plants.

[0681] Tables A16 to A21 below show the effects of selected compounds of the general formula (I) according to Tables 1 and 2 on various harmful plants and at an application rate corresponding to 1280 g/ha, which were obtained by the experimental procedure mentioned above.

TABLE-US-00020 TABLE A16 Post-emergence action at 1280 g/ha against POAAN in % Example Dosage POAAN number [g/ha] (%) I-02 1280 90 I-04 1280 90 I-05 1280 100 I-10 1280 100 I-11 1280 100 I-12 1280 100 I-16 1280 100 I-18 1280 100 I-19 1280 100 I-20 1280 100 I-21 1280 100 I-22 1280 100 I-24 1280 100 I-25 1280 90 I-26 1280 100 I-30 1280 100 I-34 1280 100 I-35 1280 100 I-36 1280 100 I-37 1280 100 I-38 1280 100 I-39 1280 100 I-40 1280 100 I-41 1280 100 I-42 1280 100 I-43 1280 100 I-45 1280 100 I-46 1280 100 I-47 1280 100 I-48 1280 100 I-49 1280 100 I-50 1280 90 I-53 1280 100 I-65 1280 100 I-66 1280 90 I-67 1280 100 I-68 1280 100 I-69 1280 90 I-71 1280 100 I-72 1280 100 I-73 1280 100 I-74 1280 90

TABLE-US-00021 TABLE A17 Post-emergence action at 1280 g/ha against DIGSA in % Example Dosage DIGSA number [g/ha] (%) I-11 1280 100 I-18 1280 100 I-30 1280 100 I-34 1280 100 I-35 1280 90 I-36 1280 100 I-37 1280 100 I-38 1280 90 I-39 1280 100 I-40 1280 90 I-42 1280 90 I-45 1280 100 I-46 1280 100 I-47 1280 100 I-49 1280 90 I-53 1280 100 I-65 1280 100 I-67 1280 100 I-68 1280 100 I-69 1280 90 I-70 1280 100 I-71 1280 90 I-72 1280 100 I-74 1280 90

TABLE-US-00022 TABLE A18 Post-emergence action at 1280 g/ha against ECHCG in % Example Dosage ECHCG number [g/ha] (%) I-02 1280 90 I-06 1280 100 I-11 1280 90 I-12 1280 90 I-16 1280 100 I-20 1280 100 I-26 1280 100 I-30 1280 90 I-34 1280 100 I-36 1280 100 I-37 1280 100 I-38 1280 100 I-39 1280 100 I-45 1280 100 I-46 1280 100 I-47 1280 100 I-48 1280 100 I-49 1280 100 I-53 1280 100 I-65 1280 90 I-67 1280 90 I-68 1280 100 I-69 1280 90 I-70 1280 90 I-71 1280 100 I-72 1280 100 I-73 1280 100

TABLE-US-00023 TABLE A19 Post-emergence action at 1280 g/ha against ABUTH in % Example Dosage ABUTH number [g/ha] (%) I-05 1280 90 I-11 1280 90 I-16 1280 90 I-18 1280 90 I-20 1280 90 I-24 1280 90 I-30 1280 90 I-36 1280 90 I-37 1280 90 I-45 1280 90 I-46 1280 90 I-47 1280 90 I-48 1280 90 I-49 1280 100 I-53 1280 90 I-65 1280 90 I-66 1280 90 I-67 1280 90 I-68 1280 100 I-70 1280 100 I-73 1280 90

TABLE-US-00024 TABLE A20 Post-emergence action at 1280 g/ha against MATIN in % Example Dosage MATIN number [g/ha] (%) I-01 1280 90 I-02 1280 90 I-04 1280 90 I-06 1280 90 I-12 1280 90 I-16 1280 90 I-18 1280 90 I-20 1280 100 I-21 1280 90 I-22 1280 90 I-26 1280 100 I-34 1280 90 I-36 1280 90 I-37 1280 90 I-38 1280 90 I-39 1280 90 I-40 1280 100 I-41 1280 90 I-42 1280 100 I-43 1280 100 I-46 1280 90 I-47 1280 90 I-48 1280 100 I-49 1280 100 I-50 1280 90 I-52 1280 90 I-53 1280 100 I-65 1280 100 I-66 1280 90 I-67 1280 100 I-68 1280 90 I-69 1280 90 I-70 1280 100 I-71 1280 100 I-72 1280 100 I-73 1280 100 I-74 1280 90

TABLE-US-00025 TABLE A21 Post-emergence action at 1280 g/ha against STEME in % Example Dosage STEME number [g/ha] (%) I-01 1280 100 I-02 1280 90 I-04 1280 100 I-05 1280 90 I-10 1280 90 I-11 1280 90 I-12 1280 100 I-16 1280 100 I-18 1280 100 I-20 1280 100 I-21 1280 100 I-22 1280 100 I-25 1280 90 I-30 1280 90 I-34 1280 100 I-36 1280 100 I-37 1280 100 I-38 1280 100 I-39 1280 100 I-40 1280 100 I-43 1280 90 I-45 1280 100 I-46 1280 90 I-47 1280 100 I-48 1280 100 I-49 1280 90 I-50 1280 90 I-53 1280 100 I-65 1280 90 I-67 1280 90 I-68 1280 100 I-69 1280 90 I-70 1280 100 I-72 1280 90

[0682] As shown by the results, inventive compounds of the general formula (I), in post-emergence treatment, have very good herbicidal efficacy (90% to 100% herbicidal activity) against harmful plants such as Abutilon theophrasti, Digitaria sanguinalis, Echinochloa crus-galli, Matricaria inodora, Poa annua, Stellaria media at an application rate of 1.28 kg of active substance per hectare.

[0683] Thus, the compounds of the invention have good herbicidal action against a broad spectrum of weed grasses and broadleaved weeds and are therefore suitable for controlling unwanted vegetation by the post-emergence method.

[0684] 2. Herbicidal Pre-Emergence Action

[0685] a) Seeds of monocotyledonous and dicotyledonous weed plants and crop plants are placed in plastic or organic plant pots and covered with soil. The compounds of the invention, formulated in the form of wettable powders (WP) or as emulsion concentrates (EC), are then applied onto the surface of the covering soil as aqueous suspension or emulsion with addition of 0.5% additive at a water application rate of 600 1/ha (converted). After the treatment, the pots are placed in a greenhouse and kept under good growth conditions for the trial plants. After about 3 weeks, the effect of the preparations is scored visually in comparison with untreated controls as percentages. For example, 100% activity=the plants have died, 0% activity=like control plants.

[0686] Tables B1 to B15 below show the effects of selected compounds of the general formula (I) according to Tables 1 and 2 on various harmful plants and an application rate corresponding to 320 g/ha and/or 80 g/ha, which were obtained by the experimental procedure mentioned above.

TABLE-US-00026 TABLE B1 Pre-emergence action against ALOMY in % Example Dosage ALOMY number [g/ha] (%) I-01 320 80 I-04 320 80 I-05 320 100 I-07 320 100 I-08 320 100 I-09 320 90 I-10 320 100 I-11 320 100 I-12 320 100 I-13 320 100 I-15 320 90 I-16 320 90 I-17 320 100 I-20 320 90 I-21 320 80 I-22 320 100 I-25 320 80 I-34 320 100 I-36 320 100 I-37 320 100 I-39 320 100 I-40 320 100 I-45 320 100 I-46 320 100 I-48 320 100 I-52 320 90 I-53 320 100 I-65 320 90 I-67 320 100 I-68 320 100 I-72 320 90 I-75 320 100 I-89 320 100 I-87 320 100 I-88 320 100 I-86 320 100 I-80 320 100 II-03 320 100 II-02 320 80 I-92 320 90 I-90 320 90 I-91 320 80 I-93 320 90 I-97 320 100 I-96 320 100 I-95 320 100 I-99 320 100 I-98 320 90

TABLE-US-00027 TABLE B2 Pre-emergence action against AVEFA in % Example Dosage AVEFA number [g/ha] (%) I-05 320 80 I-07 320 90 I-08 320 90 I-09 320 90 I-10 320 90 I-12 320 90 I-13 320 90 I-15 320 80 I-16 320 90 I-17 320 100 I-20 320 80 I-22 320 90 I-34 320 90 I-36 320 100 I-37 320 90 I-39 320 90 I-45 320 80 I-46 320 90 I-48 320 90 I-53 320 90 I-67 320 80 I-68 320 90 I-72 320 80 I-75 320 90 I-87 320 90 I-88 320 90 II-03 320 100 I-92 320 100 I-90 320 100 I-91 320 90 I-93 320 100 I-97 320 90 I-96 320 90 I-95 320 90 I-99 320 90 I-98 320 80

TABLE-US-00028 TABLE B3 Pre-emergence action against DIGSA in % Example Dosage DIGSA number [g/ha] (%) I-01 320 90 I-02 320 90 I-04 320 90 I-05 320 100 I-07 320 100 I-08 320 100 I-09 320 100 I-10 320 100 I-11 320 100 I-12 320 100 I-13 320 100 I-15 320 100 I-16 320 100 I-17 320 100 I-20 320 100 I-21 320 90 I-22 320 100 I-34 320 100 I-36 320 100 I-37 320 100 I-39 320 100 I-40 320 100 I-45 320 100 I-46 320 100 I-47 80 100 I-48 320 100 I-52 320 100 I-53 320 100

TABLE-US-00029 TABLE B4 Pre-emergence action against ECHCG in % Example Dosage ECHCG number [g/ha] (%) I-01 320 80 I-05 320 90 I-07 320 100 I-08 320 100 I-09 320 100 I-13 320 100 I-15 320 100 I-17 320 100 I-20 320 90 I-34 320 80 I-36 320 100 I-37 320 90 I-39 320 100 I-46 320 100 I-48 320 100 I-53 320 100 I-67 320 90 I-68 320 90 I-92 320 90 I-90 320 100 I-91 320 100 I-93 320 100 I-94 320 100 1-97 320 100 I-96 320 100 I-95 320 100 I-99 320 100 I-98 320 100

TABLE-US-00030 TABLE B5 Pre-emergence action against LOLRI in % Example Dosage LOLRI number [g/ha] (%) I-01 320 80 I-04 320 90 I-05 320 100 I-07 320 100 I-08 320 100 I-09 320 90 I-10 320 100 I-11 320 100 I-12 320 100 I-15 320 100 I-16 320 100 I-17 320 100 1-20 320 100 I-21 320 90 I-22 320 100 I-34 320 100 I-36 320 100 I-37 320 100 I-39 320 100 I-40 320 90 I-45 320 90 I-46 320 100 I-48 320 100 I-52 320 100 I-53 320 80 I-65 320 80 I-68 320 80 I-72 320 100 I-75 320 100 I-89 320 100 I-87 320 100 I-88 320 100 I-86 320 100 I-80 320 80 II-03 320 100 I-92 320 100 I-90 320 100 I-91 320 100 I-93 320 100 I-94 320 90 I-97 320 100 I-96 320 100 I-95 320 100 I-99 320 100 I-98 320 90

TABLE-US-00031 TABLE B6 Pre-emergence action against SETVI in % Example Dosage SETVI number [g/ha] (%) I-05 320 90 I-07 320 100 I-08 320 100 I-09 320 90 I-10 320 100 I-11 320 100 I-12 320 100 I-13 320 100 I-15 320 100 I-16 320 100 I-17 320 100 I-20 320 100 I-21 320 90 I-22 320 100 I-34 320 100 I-36 320 100 I-37 320 100 I-39 320 100 I-40 320 100 I-45 320 100 I-46 320 100 I-48 320 100 I-52 320 90 I-53 320 100 I-65 320 100 I-67 320 90 I-68 320 100 I-89 320 100 I-78 320 90 II-12 320 100 I-87 320 100 I-88 320 80 II-03 320 100 I-92 320 100 I-90 320 100 I-91 320 100 I-93 320 100 I-97 320 100 I-96 320 100 I-95 320 100 I-99 320 100 I-98 320 100

TABLE-US-00032 TABLE B7 Pre-emergence action against ABUTH in % Example Dosage ABUTH number [g/ha] (%) I-08 320 80 I-39 320 90 I-46 320 80 I-48 320 100 I-92 320 90 I-91 320 90 I-97 320 90 I-96 320 90 I-95 320 90 I-99 320 90 I-98 320 90

TABLE-US-00033 TABLE B8 Pre-emergence action against AMARE in % Example Dosage AMARE number [g/ha] (%) I-01 320 100 I-02 320 100 I-04 320 100 I-05 320 100 I-07 320 100 I-08 320 100 I-09 320 100 I-10 320 90 I-11 320 90 I-12 320 100 I-13 320 100 I-15 320 100 I-16 320 100 I-17 320 100 I-20 320 100 I-21 320 100 I-22 320 90 I-34 320 90 I-36 320 100 I-37 320 90 I-39 320 100 I-40 320 90 I-45 320 100 I-46 320 100 I-47 80 90 I-48 320 100 I-52 320 100 I-53 320 100 I-65 320 100 I-67 320 100 I-68 320 100 I-72 320 100 I-75 320 90 I-76 320 90 I-77 320 80 I-89 320 100 I-78 320 80 II-08 320 90 II-12 320 80 II-14 320 80 II-13 320 90 I-84 320 90 I-86 320 80 I-80 320 100 II-03 320 100 I-92 320 100 I-90 320 100 I-91 320 100 I-93 320 100 I-97 320 100 I-96 320 100 I-95 320 100 I-99 320 100 I-98 320 100

TABLE-US-00034 TABLE B9 Pre-emergence action against MATIN in % Example Dosage MATIN number [g/ha] (%) I-01 320 90 I-02 320 90 I-04 320 90 I-07 320 90 I-08 320 90 I-11 320 90 I-15 320 100 I-16 320 90 I-20 320 90 I-21 320 80 I-36 320 80 I-37 320 90 I-39 320 90 I-45 320 100 I-46 320 100 I-48 320 100 I-52 320 90 I-53 320 100 I-65 320 90 I-67 320 80 I-68 320 90 I-76 320 90 I-77 320 80 I-92 320 100 I-90 320 100 I-91 320 100 I-93 320 100 I-94 320 90 I-97 320 100 I-96 320 100 I-95 320 100 I-99 320 100 I-98 320 90

TABLE-US-00035 TABLE B10 Pre-emergence action against PHBPU in % Example Dosage PHBPU number [g/ha] (%) I-05 320 80 I-07 320 90 I-08 320 90 I-11 320 90 I-15 320 90 I-48 320 90 I-52 320 100 I-67 320 80 I-68 320 80 I-92 320 90 I-91 320 90 I-93 320 100 I-97 320 100 I-96 320 90 I-95 320 90 I-99 320 90 I-98 320 80

TABLE-US-00036 TABLE B11 Pre-emergence action against POLCO in % Example Dosage POLCO number [g/ha] (%) I-01 320 80 I-04 320 90 I-07 320 90 I-08 320 100 I-09 320 100 I-11 320 90 I-12 320 90 I-13 320 90 I-16 320 90 I-17 320 90 I-20 320 80 I-22 320 80 I-34 320 100 I-36 320 100 I-37 320 100 I-39 320 90 I-40 320 80 I-45 320 100 I-46 320 100 I-48 320 100 I-52 320 80 I-53 320 90 I-67 320 90 I-72 320 90 I-75 320 80 I-88 320 80 I-86 320 80 II-03 320 90 I-92 320 90 I-90 320 100 I-91 320 90 I-93 320 100 I-97 320 90 I-96 320 100 I-95 320 100 I-99 320 90 I-98 320 90

TABLE-US-00037 TABLE B12 Pre-emergence action against STEME in % Example Dosage STEME number [g/ha] (%) I-01 320 80 I-04 320 90 I-05 320 100 I-07 320 100 I-08 320 100 I-12 320 90 I-13 320 90

TABLE-US-00038 TABLE B13 Pre-emergence action against VIOTR in % Example Dosage VIOTR number [g/ha] (%) I-05 320 100 I-07 320 100 I-08 320 100 I-09 320 90 I-10 320 80 I-11 320 100 I-12 320 100 I-13 320 100 I-15 320 100 I-16 320 100 I-17 320 100 I-20 320 90 I-21 320 100 I-22 320 90 I-25 320 90 I-34 320 100 I-36 320 100 I-37 320 100 I-39 320 100 I-40 320 90 I-45 320 100 I-46 320 100 I-48 320 100 I-52 320 90 I-53 320 100 I-65 320 90 I-67 320 90 I-68 320 90 I-72 320 90 I-75 320 80 I-77 320 80

TABLE-US-00039 TABLE B14 Pre-emergence action against VERPE in % Example Dosage VERPE number [g/ha] (%) I-01 320 90 I-02 320 100 I-04 320 90 I-05 320 100 I-07 320 100 I-08 320 100 I-11 320 90 I-12 320 80 I-13 320 100 I-15 320 100 I-16 320 100 I-17 320 100 I-20 320 100 I-21 320 90 I-25 320 90 I-32 320 90 I-36 320 100 I-37 320 100 I-39 320 100 I-45 320 80 I-46 320 100 I-48 320 100 I-52 320 90 I-53 320 90 I-65 320 90 I-67 320 90 I-68 320 90 I-72 320 80 I-89 320 100 I-87 320 80 I-88 320 90 I-80 320 80 II-03 320 100 II-06 320 100 I-92 320 100 I-90 320 100 I-91 320 90 I-93 320 100 I-97 320 100 I-96 320 100 I-95 320 100 I-99 320 100 I-98 320 100

TABLE-US-00040 TABLE B15 Pre-emergence action against HORMU in % Example Dosage HORMU number [g/ha] (%) I-05 320 90 I-07 320 90 I-08 320 100 I-10 320 80 I-12 320 90 I-13 320 100

[0687] As the results show, inventive compounds, for example compound nos. I-01, I-05, I-07, I-08, I-11, I-12, I-13, I-15, I-16, I-17, I-20, I-22, I-34, I-36, I-37, I-39, I-45, I-46, I-48, I-52 and I-53 and other compounds from Tables B1 to B15, show good herbicidal efficacy against harmful plants in the case of pre-emergence treatment. For example, compound nos. I-07, I-08, I-11, I-12, I-13, I-16, I-17, I-20, I-36, I-37, I-39, I-45, I-46, I-48, I-52 and I-53 in the pre-emergence method have very good action (80% to 100% herbicidal activity) against harmful plants such as Alopecurus myosuroides, Amaranthus retroflexus, Digitaria sanguinalis, Lolium rigidum, Polygonum convolvulus, Setaria viridis, Veronica persica and Viola tricolor at an application rate of 0.32 kg of active substance per hectare.

[0688] b) Seeds of mono- and dicotyledonous weed plants are placed in plastic pots in sandy loam soil (doubly sown with one species each of mono- or dicotyledonous weed plants per pot) and covered with soil. The compounds of the invention, formulated in the form of wettable powders (WP) or as emulsion concentrates (EC), are then applied onto the surface of the covering soil as aqueous suspension or emulsion with addition of 0.5% additive at a water application rate equivalent to 600 litres per hectare. After the treatment, the pots are placed in a greenhouse and kept under good growth conditions for the trial plants. After about 3 weeks, the effect of the preparations is scored visually in comparison with untreated controls as percentages. For example, 100% activity=the plants have died, 0% activity=like control plants.

[0689] Tables B16 to B21 below show the effects of selected compounds of the general formula (I) according to Tables 1 and 2 on various harmful plants and at an application rate corresponding to 1280 g/ha, which were obtained by the experimental procedure mentioned above.

TABLE-US-00041 TABLE B16 Pre-emergence action at 1280 g/ha against POAAN in % Example Dosage POAAN number [g/ha] (%) I-01 1280 100 I-02 1280 100 I-04 1280 100 I-05 1280 100 I-06 1280 100 I-09 1280 100 I-10 1280 100 I-11 1280 100 I-12 1280 100 I-16 1280 100 I-18 1280 100 I-19 1280 100 I-20 1280 100 I-21 1280 100 I-22 1280 100 I-24 1280 100 I-25 1280 100 I-26 1280 100 I-30 1280 100 I-34 1280 100 I-35 1280 100 I-36 1280 100 I-37 1280 100 I-38 1280 100 I-39 1280 100 I-40 1280 100 I-41 1280 100 I-42 1280 100 I-43 1280 100 I-45 1280 100 I-46 1280 100 I-47 1280 100 I-48 1280 100 I-49 1280 100 I-50 1280 100 I-52 1280 100 I-53 1280 100 I-65 1280 100 I-66 1280 100 I-67 1280 100 I-68 1280 100 I-69 1280 100 I-70 1280 100 I-71 1280 100 I-72 1280 100 I-73 1280 100 I-74 1280 100 II-01 1280 100

TABLE-US-00042 TABLE B17 Pre-emergence action at 1280 g/ha against DIGSA in % Example Dosage DIGSA number [g/ha] (%) I-11 1280 90 I-18 1280 100 I-24 1280 100 I-25 1280 100 I-26 1280 100 I-30 1280 100 I-34 1280 100 I-35 1280 90 I-36 1280 100 I-37 1280 100 I-38 1280 100 I-39 1280 100 I-40 1280 100 I-41 1280 100 I-42 1280 100 I-43 1280 100 I-45 1280 100 I-46 1280 100 I-47 1280 100 I-48 1280 100 I-49 1280 100 I-50 1280 100 I-52 1280 100 I-53 1280 100 I-65 1280 100 I-66 1280 100 I-67 1280 100 I-68 1280 100 I-69 1280 100 I-70 1280 100 I-71 1280 100 I-72 1280 100 I-74 1280 100

TABLE-US-00043 TABLE B18 Pre-emergence action at 1280 g/ha against ECHCG in % Example Dosage ECHCG number [g/ha] (%) I-01 1280 100 I-02 1280 100 I-04 1280 100 I-05 1280 100 I-06 1280 100 I-09 1280 100 I-11 1280 90 I-12 1280 100 I-16 1280 100 I-18 1280 100 I-20 1280 100 I-21 1280 100 I-22 1280 100 I-23 1280 100 I-25 1280 90 I-26 1280 100 I-30 1280 100 I-34 1280 90 I-36 1280 90 I-37 1280 100 I-38 1280 100 I-39 1280 100 I-40 1280 100 I-41 1280 100 I-45 1280 100 I-46 1280 100 I-47 1280 100 I-48 1280 100 I-49 1280 100 I-53 1280 100 I-65 1280 100 I-66 1280 90 I-67 1280 100 I-68 1280 100 I-69 1280 100 I-70 1280 100 I-71 1280 100 I-72 1280 100 I-73 1280 100 II-01 1280 90

TABLE-US-00044 TABLE B19 Pre-emergence action at 1280 g/ha against AMARE in % Example Dosage AMARE number [g/ha] (%) I-01 1280 100 I-02 1280 100 I-04 1280 100 I-05 1280 100 I-06 1280 90 I-09 1280 90 I-10 1280 100 I-11 1280 100 I-12 1280 100 I-16 1280 100 I-18 1280 100 I-19 1280 100 I-20 1280 100 I-21 1280 100 I-22 1280 100 I-23 1280 100 I-24 1280 90 I-25 1280 100 I-26 1280 90 I-30 1280 100 I-34 1280 100 I-35 1280 90 I-36 1280 100 I-37 1280 100 I-38 1280 100 I-39 1280 100 I-40 1280 100 I-41 1280 100 I-42 1280 90 I-43 1280 100 I-45 1280 100 I-46 1280 100 I-47 1280 100 I-48 1280 100 I-49 1280 100 I-50 1280 100 I-52 1280 90 I-53 1280 100 I-65 1280 100 I-66 1280 100 I-67 1280 100 I-68 1280 100 I-69 1280 100 I-70 1280 100 I-71 1280 100 I-72 1280 100 I-73 1280 100 I-74 1280 100 II-01 1280 100

TABLE-US-00045 TABLE B20 Pre-emergence action at 1280 g/ha against MATIN in % Example Dosage MATIN number [g/ha] (%) I-01 1280 100 I-02 1280 100 I-04 1280 100 I-05 1280 90 I-06 1280 90 I-09 1280 100 I-10 1280 90 I-11 1280 90 I-12 1280 90 I-16 1280 100 I-18 1280 90 I-20 1280 100 I-21 1280 100 I-22 1280 90 I-25 1280 90 I-30 1280 90 I-34 1280 100 I-36 1280 90 I-37 1280 100 I-38 1280 100 I-39 1280 100 I-40 1280 100 I-41 1280 100 I-42 1280 90 I-43 1280 90 I-45 1280 100 I-46 1280 100 I-47 1280 100 I-48 1280 100 I-49 1280 100 I-50 1280 90 I-52 1280 90 I-53 1280 100 I-65 1280 100 I-66 1280 100 I-67 1280 100 I-68 1280 100 I-69 1280 100 I-70 1280 100 I-71 1280 100 I-72 1280 100 I-73 1280 100 I-74 1280 100 II-01 1280 100

TABLE-US-00046 TABLE B21 Pre-emergence action at 1280 g/ha against STEME in % Example Dosage STEME number [g/ha] (%) I-01 1280 100 I-02 1280 100 I-04 1280 100 I-05 1280 100 I-06 1280 100 I-09 1280 100 I-10 1280 100 I-11 1280 100 I-12 1280 100 I-16 1280 100 I-18 1280 100 I-19 1280 100 I-20 1280 100 I-21 1280 100 I-22 1280 100 I-24 1280 90 I-26 1280 100 I-30 1280 100 I-34 1280 100 I-35 1280 100 I-36 1280 100 I-37 1280 100 I-38 1280 100 I-39 1280 100 I-40 1280 100 I-41 1280 100 I-42 1280 90 I-43 1280 100 I-45 1280 100 I-46 1280 100 I-47 1280 100 I-48 1280 100 I-49 1280 100 I-50 1280 90 I-52 1280 100 I-53 1280 100 I-65 1280 100 I-66 1280 100 I-67 1280 100 I-68 1280 100 I-69 1280 100 I-70 1280 100 I-71 1280 100 I-72 1280 100 I-73 1280 100 I-74 1280 100 II-01 1280 100

[0690] As shown by the results, inventive compounds of the general formula (I), in pre-emergence treatment, have very good herbicidal efficacy (90% to 100% herbicidal activity) against harmful plants such as Amaranthus retroflexus, Digitaria sanguinalis, Echinochloa crus-galli, Matricaria inodora, Poa annua, Stellaria media at an application rate of 1.28 kg of active substance per hectare.

[0691] Thus, the compounds of the invention have good herbicidal action against a broad spectrum of weed grasses and broad-leaved weeds and are therefore suitable for controlling unwanted vegetation by the pre-emergence method.