Herbicidally Active Arylcarboxylic Acid Amides

Abstract

Benzamides of the general formula (I) are described as herbicides.

##STR00001##

In this formula (I), X, Z and R are radicals such as alkyl and cycloalkyl. Q is a 5-membered heterocycle.

Claims

1. A benzamide of formula (I) or salt thereof ##STR00061## where the symbols and indices are each defined as follows: Q is a Q1, Q2, Q3 or Q4 radical, ##STR00062## X is (C.sub.1-C.sub.6)-alkyl or (C.sub.3-C.sub.6)-cycloalkyl, Z is (C.sub.3-C.sub.6)-cycloalkyl, R is (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkyl-O(C.sub.1-C.sub.6)-alkyl, R.sup.X is methyl, ethyl, n-propyl, prop-2-en-1-yl, methoxyethyl, ethoxyethyl or methoxyethoxyethyl, R.sup.Y is methyl, ethyl, n-propyl, chlorine or amino, R.sup.Z is methyl, ethyl, n-propyl or methoxymethyl, n is 0, 1 or 2.

2. A benzamide or salt as claimed in claim 1, wherein Q is a Q1, Q2, Q3 or Q4 radical, ##STR00063## X is methyl, ethyl or cyclopropyl, Z is cyclopropyl or cyclobutyl, R is methyl, ethyl, cyclopropyl, cyclopropylmethyl or methoxyethyl, R.sup.X is methyl, ethyl, n-propyl, prop-2-en-1-yl, methoxyethyl, ethoxyethyl or methoxyethoxyethyl, R.sup.Y is methyl, ethyl, n-propyl, chlorine or amino, R.sup.Z is methyl, ethyl, n-propyl or methoxymethyl, n is 0, 1 or 2.

3. A herbicidal composition comprising a herbicidally active content of at least one compound of the formula (I) or salt as claimed in claim 1.

4. The herbicidal composition as claimed in claim 3 in a mixture with one or more formulation auxiliaries.

5. A method of controlling unwanted plants, comprising applying an effective amount of at least one compound of formula (I) or salt as claimed in claim 1 or a herbicidal composition thereof to one or more plants or to a site of unwanted vegetation.

6. A product comprising a compound of formula (I) or salt as claimed in claim 1 or a herbicidal composition thereof for controlling one or more unwanted plants.

7. The product as claimed in claim 6, wherein the compound of formula (I) or salt is used for controlling one or more unwanted plants in one or more crops of useful plants.

8. The product as claimed in claim 7, wherein the useful plants are transgenic useful plants.

9. A benzoic acid of formula (II) ##STR00064## in which X, R, Z and n are X is (C.sub.1-C.sub.6)-alkyl or (C.sub.3-C.sub.6)-cycloalkyl, Z is (C.sub.3-C.sub.6)-cycloalkyl, R is (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkyl-O(C.sub.1-C.sub.6)-alkyl, n is 0, 1 or 2.

10. A benzoyl chloride of formula (III) ##STR00065## in which X, R, Z and n are X is (C.sub.1-C.sub.6)-alkyl or (C.sub.3-C.sub.6)-cycloalkyl, Z is (C.sub.3-C.sub.6)-cycloalkyl, R is (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkyl-O(C.sub.1-C.sub.6)-alkyl, n is 0, 1 or 2.

Description

A. CHEMICAL EXAMPLES

4-Cyclopropyl-2-methyl-3-(methylsulfinyl)-N-(1-methyl-1H-tetrazol-5-yl)benzamide (Example No. 1-2)

Step 1: Synthesis of 1-bromo-3-fluoro-2-(methylsulfanyl)benzene

[0074] 1028 mL of a 2.5 M (2.57 mol) solution of n-butyllithium in n-hexane were dissolved in 1600 mL of dry THF. At 0 C., 400 mL (2.83 mol) of diisopropylamine were added. The reaction mixture was stirred at this temperature for 15 min. The mixture was then cooled down to 78 C. At this temperature, 287 mL (2.57 mol) of 1-bromo-3-fluorobenzene were added dropwise. The mixture was stirred at this temperature for 1 h. Thereafter, 254 mL (2.82 mol) of dimethyl disulfide were added. Subsequently, the reaction mixture was thawed to room temperature (RT). After the aqueous workup, the residue of the organic phase was subjected to a fractional distillation at 0.5 mbar. At 87 C., 504 g of the desired product were obtained.

Step 2: Synthesis of 4-bromo-2-fluoro-3-(methylsulfanyl)benzoic acid

[0075] 452 mL of a 2.5 M (1.13 mol) solution of n-butyllithium in n-hexane were added dropwise at 78 C. to a solution of 176 mL (1.24 mol) of diisopropylamine in 550 mL of dry THF. The solution was stirred at this temperature for 5 min and then at 0 C. for 15 min. Thereafter, the solution was cooled back down to 78 C. Subsequently, a solution of 250 g (1.13 mol) of 1-bromo-3-fluoro-2-(methylsulfanyl)benzene in 150 mL of dry THF was added dropwise. The solution was stirred at 78 C. for 1.5 h. Thereafter, 298 g (6.78 mol) of carbon dioxide were added in the form of dry ice. The reaction mixture was thawed gradually to RT. For workup, the mixture was acidified to pH=1 with dilute hydrochloric acid. The product was then extracted six times with diethyl ether. The combined organic phases were washed with a saturated aqueous sodium chloride solution. Subsequently, the product was extracted three times with a saturated aqueous sodium hydrogencarbonate solution. The combined aqueous extracts were washed three times with diethyl ether at pH=9 and then acidified gradually to pH=1 with concentrated hydrochloric acid. The product was extracted three times with diethyl ether, and the combined organic phases were washed with a saturated aqueous sodium chloride solution. Finally, the combined organic phases were dried over magnesium sulfate, and the filtrate was freed of the solvent. For further purification, the product was recrystallized from water, and 275 g of the desired product were obtained.

Step 3: Synthesis of 4-bromo-2-fluoro-N-(1-hydroxy-2-methylpropan-2-yl)-3-(methylsulfanyl)benzamide

[0076] To 340 g (1.28 mol) of 4-bromo-2-fluoro-3-(methylsulfanyl)benzoic acid in 1000 mL of dry dichloromethane were added 2 mL of N,N-dimethylformamide, and then the mixture was heated to a temperature of 35 C. 271 mL (3.20 mol) of oxalyl chloride were slowly added dropwise at this temperature. On conclusion of the evolution of gas, the reaction mixture was heated under reflux until the monitoring of the reaction no longer indicated any starting material. Subsequently, the mixture was freed of the solvent. 600 mL of toluene were added to the residue and the mixture was freed of the solvent once again. The acid chloride was taken up in 600 mL of anhydrous dichloromethane. At 5 C.-25 C., this solution was added dropwise to a mixture of 305 mL (3.20 mol) of 2-amino-2-methylpropan-1-ol and 100 mL of anhydrous dichloromethane. The reaction mixture was stirred at 0 C. for 1.5 h and then at room temperature for 16 h. For workup, the mixture was filtered and the filtrate was freed of the solvent. The residue obtained was 330 g of product, which was used without further purification in the next step.

Step 4: Synthesis of 2-[4-bromo-2-fluoro-3-(methylsulfanyl)phenyl]-4,4-dimethyl-4,5-dihydro-1,3-oxazole

[0077] To 330 g (0.98 mol) of 4-bromo-2-fluoro-N-(1-hydroxy-2-methylpropan-2-yl)-3-(methylsulfanyl)benzamide were added, at RT, 384 mL (5.3 mol) of thionyl chloride. On conclusion of the evolution of gas, the reaction mixture was stirred at RT for another 1 h. For workup, the mixture was poured cautiously into water. Subsequently, the mixture was extracted with diethyl ether. The aqueous phase was cooled down to 00 C. and alkalized with 20 percent sodium hydroxide solution. The mixture was then immediately and rapidly extracted with dichloromethane. The organic phase was dried and the filtrate was freed of the solvent. The crude product was recrystallized from diisopropyl ether, and 165 g of the desired product were isolated.

Step 5: Synthesis of 2-[4-bromo-2-methyl-3-(methylsulfanyl)phenyl]-4,4-dimethyl-4,5-dihydro-1,3-oxazole

[0078] To 45 g (141 mmol) of 2-[4-bromo-2-fluoro-3-(methylsulfanyl)phenyl]-4,4-dimethyl-4,5-dihydro-1,3-oxazole at RT in 440 mL of dry diethyl ether was slowly added dropwise, under protective gas, methylmagnesium iodide (freshly prepared from 12.37 g (507 mmol) of magnesium and 71.24 g (501 mmol) of iodomethane). It was ensured that the temperature did not rise above 30 C. Thereafter, the mixture was stirred at RT until the monitoring of the reaction no longer indicated any starting material. For workup, the mixture was poured gradually into a mixture of ice and dilute hydrochloric acid. Subsequently, sodium hydroxide solution was added until the pH was between 7 and 8. The aqueous phase was extracted twice with diethyl ether. The combined organic phases were dried and the filtrate was freed of the solvent. The residue was recrystallized from diisopropyl ether, and 38 g of the desired product were obtained.

Step 6: Synthesis of 4-bromo-2-methyl-3-(methylsulfanyl)benzoic acid

[0079] To 250 g (0.8 mol) of 2-[4-bromo-2-methyl-3-(methylsulfanyl)phenyl]-4,4-dimethyl-4,5-dihydro-1,3-oxazole were added 1300 mL of 6 M hydrochloric acid. The reaction mixture was heated under reflux for 24 h. For workup, the mixture was alkalized and washed twice with diethyl ether. The aqueous phase was acidified with hydrochloric acid. The product crystallized out and the mixture was filtered. 167 g of the desired product were obtained as residue.

Step 7: Synthesis of methyl 4-bromo-2-methyl-3-(methylsulfanyl)benzoate

[0080] To 10.1 g (38.7 mmol) of 4-bromo-2-methyl-3-(methylsulfanyl)benzoic acid in 100 mL of methanol were added 5 mL of concentrated sulfuric acid. The mixture was then heated under reflux for 8 h. The mixture was cooled to RT and freed of the solvent. The residue was taken up in water and cooled down in an ice bath. The mixture was filtered and the residue was washed with saturated aqueous sodium hydrogencarbonate solution. The residue was dried, and 9.82 g of the desired product were obtained.

Step 8: Synthesis of 4-cyclopropyl-2-methyl-3-(methylsulfanyl)benzoic acid (Example No. 9-1)

[0081] To 1.94 g (80.0 mmol) of magnesium turnings under protective gas were added 5 mL of dry tetrahydrofuran. Subsequently, a small amount of the total of 9.67 g (80.0 mmol) of cyclopropyl bromide and a catalytic amount of iodine were added in order to initiate the Grignard reaction. After the Grignard reaction had started, the rest of the cyclopropyl bromide, which had been diluted beforehand with 145 mL of dry tetrahydrofuran, was slowly added dropwise. To complete the reaction, the mixture was then heated under reflux for 15 min. The contents were cooled to RT, then 800 mg (18.9 mmol) of lithium chloride were added. Once the lithium chloride had dissolved, the mixture was cooled down to 20 C. Subsequently, 114 mL (0.7 M; 79.8 mmol) of a solution of zinc chloride in dry tetrahydrofuran were slowly added dropwise. The mixture was stirred at this temperature for another 15 min. Subsequently, the contents were thawed to RT and, for removal of oxygen, there was repeated application of reduced pressure and venting with argon in the reaction flask. Added to this mixture was a solution of 10.0 g (36.3 mmol) of methyl 4-bromo-2-methyl-3-(methylsulfanyl)benzoate and 2.35 g (2.04 mmol) of tetrakis(triphenylphosphine)palladium(0) in 200 mL of dry tetrahydrofuran (made up by first dissolving the substituted benzoic ester, repeatedly applying reduced pressure and venting with argon in the vessel to remove oxygen, then adding the palladium catalyst and finally once again repeatedly applying reduced pressure and venting with argon to remove oxygen). The reaction mixture was heated under reflux for 3 h and then cooled down to RT. To complete the reaction, half the abovementioned amount of Grignard reagent was prepared once again and correspondingly reacted with the zinc chloride solution. After the oxygen removal as described above, this amount of coupling reagent was added to the cross-coupling mixture. In addition, half the abovementioned amount of palladium catalyst was also added. The reaction mixture was heated again under reflux until, after 2 h, no starting material was detectable any longer. For workup, the contents were cooled to RT and 500 mL of a saturated aqueous ammonium chloride solution were added. The mixture was extracted twice with diethyl ether. The combined organic phases were dried, filtered and finally freed of the solvent with sufficient caution that no product went over as well. The residue was dissolved in 100 mL of methanol, and 10 mL of 20 percent sodium hydroxide solution were added. The mixture was stirred at RT for 16 h and then at 60 C. for 3 h. Thereafter, the reaction mixture was heated under reflux until the monitoring of the reaction no longer indicated any starting material. The mixture was concentrated and the residue was taken up in water. The mixture was washed with dichloromethane and the aqueous phase was filtered through Celite. The filtrate was acidified with 6 M hydrochloric acid and extracted three times with dichloromethane. The combined organic phases were dried, and the filtrate was concentrated to about half the volume. The residue was extracted three times with percent sodium hydroxide solution. The combined aqueous phases were acidified with 6 M hydrochloric acid and stirred in an ice bath, and the product precipitated out. The mixture was filtered and dried. 7.31 g of the desired product were obtained.

Step 9: Synthesis of 4-cyclopropyl-2-methyl-3-(methylsulfanyl)-N-(1-methyl-1H-tetrazol-5-yl)benzamide (Example No. 1-1)

[0082] To 330 mg (1.48 mmol) of 4-cyclopropyl-2-methyl-3-(methylsulfanyl)benzoic acid and 191 mg (98% purity; 1.89 mmol) of 5-amino-1-methyl-1H-tetrazole in 10 mL of pyridine were added 264 mg (2.08 mmol) of oxalyl chloride. The mixture was stirred at RT for 15 min and then at 50 C. for 2 h. To complete the conversion, the mixture was cooled down to RT and another quarter of the above-specified amount of oxalyl chloride was added. The mixture was stirred at 50 C. for another 2 h. For workup, the mixture was freed of the solvent. The residue was taken up in dichloromethane and a saturated aqueous sodium hydrogencarbonate solution, and stirred. After phase separation, the organic phase was freed of the solvent. The residue was taken up in toluene and the mixture was concentrated once again. The residue was purified chromatographically, and 320 mg of the desired product were isolated.

Step 10: Synthesis of 4-cyclopropyl-2-methyl-3-(methylsulfinyl)-N-(1-methyl-1H-tetrazol-5-yl)benzamide (Example No. 1-2)

[0083] To 107 mg (0.35 mmol) of 4-cyclopropyl-2-methyl-3-(methylsulfanyl)-N-(1-methyl-1H-tetrazol-5-yl)benzamide at RT in 10 mL of glacial acetic acid were added 34.3 mg (35 percent; 0.35 mmol) of an aqueous hydrogen peroxide solution. The reaction mixture was stirred at RT until the monitoring of the reaction no longer indicated any starting material. For workup, solid sodium metabisulfite was added until no peroxides were detectable any longer. The mixture was freed of the solvent, and the residue was taken up in a little water. After addition of 1 M hydrochloric acid, the mixture was stirred for 10 min and then filtered. The residue was dried and 80.4 mg of the desired product were obtained.

[0084] The compounds listed in tables below are very particularly preferred.

[0085] The abbreviations used mean:

Me=methyl Et=ethyl Pr=propyl c-Pr=cyclopropyl

TABLE-US-00001 TABLE 1 Inventive compounds of the general formula (I) in which Q is Q1 and R.sup.x is a methyl group [00008] No. X n R Z 1-1 Me 0 Me c-Pr 1-2 Me 1 Me c-Pr 1-3 Me 2 Me c-Pr 1-4 Me 0 Et c-Pr 1-5 Me 1 Et c-Pr 1-6 Me 2 Et c-Pr 1-7 Me 0 c-Pr c-Pr 1-8 Me 1 c-Pr c-Pr 1-9 Me 2 c-Pr c-Pr 1-10 Me 0 CH.sub.2c-Pr c-Pr 1-11 Me 1 CH.sub.2c-Pr c-Pr 1-12 Me 2 CH.sub.2c-Pr c-Pr 1-13 Me 0 CH.sub.2CH.sub.2OMe c-Pr 1-14 Me 1 CH.sub.2CH.sub.2OMe c-Pr 1-15 Me 2 CH.sub.2CH.sub.2OMe c-Pr 1-16 Me 0 Me c-Bu 1-17 Me 1 Me c-Bu 1-18 Me 2 Me c-Bu 1-19 Me 0 Et c-Bu 1-20 Me 1 Et c-Bu 1-21 Me 2 Et c-Bu 1-22 Me 0 c-Pr c-Bu 1-23 Me 1 c-Pr c-Bu 1-24 Me 2 c-Pr c-Bu 1-25 Me 0 CH.sub.2c-Pr c-Bu 1-26 Me 1 CH.sub.2c-Pr c-Bu 1-27 Me 2 CH.sub.2c-Pr c-Bu 1-28 Me 0 CH.sub.2CH.sub.2OMe c-Bu 1-29 Me 1 CH.sub.2CH.sub.2OMe c-Bu 1-30 Me 2 CH.sub.2CH.sub.2OMe c-Bu 1-31 Et 0 Me c-Pr 1-32 Et 1 Me c-Pr 1-33 Et 2 Me c-Pr 1-34 Et 0 Et c-Pr 1-35 Et 1 Et c-Pr 1-36 Et 2 Et c-Pr 1-37 Et 0 c-Pr c-Pr 1-38 Et 1 c-Pr c-Pr 1-39 Et 2 c-Pr c-Pr 1-40 Et 0 CH.sub.2c-Pr c-Pr 1-41 Et 1 CH.sub.2c-Pr c-Pr 1-42 Et 2 CH.sub.2c-Pr c-Pr 1-43 Et 0 CH.sub.2CH.sub.2OMe c-Pr 1-44 Et 1 CH.sub.2CH.sub.2OMe c-Pr 1-45 Et 2 CH.sub.2CH.sub.2OMe c-Pr 1-46 Et 0 Me c-Bu 1-47 Et 1 Me c-Bu 1-48 Et 2 Me c-Bu 1-49 Et 0 Et c-Bu 1-50 Et 1 Et c-Bu 1-51 Et 2 Et c-Bu 1-52 Et 0 c-Pr c-Bu 1-53 Et 1 c-Pr c-Bu 1-54 Et 2 c-Pr c-Bu 1-55 Et 0 CH.sub.2c-Pr c-Bu 1-56 Et 1 CH.sub.2c-Pr c-Bu 1-57 Et 2 CH.sub.2c-Pr c-Bu 1-58 Et 0 CH.sub.2CH.sub.2OMe c-Bu 1-59 Et 1 CH.sub.2CH.sub.2OMe c-Bu 1-60 Et 2 CH.sub.2CH.sub.2OMe c-Bu 1-61 c-Pr 0 Me c-Pr 1-62 c-Pr 1 Me c-Pr 1-63 c-Pr 2 Me c-Pr 1-64 c-Pr 0 Et c-Pr 1-65 c-Pr 1 Et c-Pr 1-66 c-Pr 2 Et c-Pr 1-67 c-Pr 0 c-Pr c-Pr 1-68 c-Pr 1 c-Pr c-Pr 1-69 c-Pr 2 c-Pr c-Pr 1-70 c-Pr 0 CH.sub.2c-Pr c-Pr 1-71 c-Pr 1 CH.sub.2c-Pr c-Pr 1-72 c-Pr 2 CH.sub.2c-Pr c-Pr 1-73 c-Pr 0 CH.sub.2CH.sub.2OMe c-Pr 1-74 c-Pr 1 CH.sub.2CH.sub.2OMe c-Pr 1-75 c-Pr 2 CH.sub.2CH.sub.2OMe c-Pr 1-76 c-Pr 0 Me c-Bu 1-77 c-Pr 1 Me c-Bu 1-78 c-Pr 2 Me c-Bu 1-79 c-Pr 0 Et c-Bu 1-80 c-Pr 1 Et c-Bu 1-81 c-Pr 2 Et c-Bu 1-82 c-Pr 0 c-Pr c-Bu 1-83 c-Pr 1 c-Pr c-Bu 1-84 c-Pr 2 c-Pr c-Bu 1-85 c-Pr 0 CH.sub.2c-Pr c-Bu 1-86 c-Pr 1 CH.sub.2c-Pr c-Bu 1-87 c-Pr 2 CH.sub.2c-Pr c-Bu 1-88 c-Pr 0 CH.sub.2CH.sub.2OMe c-Bu 1-89 c-Pr 1 CH.sub.2CH.sub.2OMe c-Bu 1-90 c-Pr 2 CH.sub.2CH.sub.2OMe c-Bu

TABLE-US-00002 TABLE 2 Inventive compounds of the general formula (I) in which Q is Q1 and R.sup.x is a ethyl group [00009] No. X n R Z 2-1 Me 0 Me c-Pr 2-2 Me 1 Me c-Pr 2-3 Me 2 Me c-Pr 2-4 Me 0 Et c-Pr 2-5 Me 1 Et c-Pr 2-6 Me 2 Et c-Pr 2-7 Me 0 c-Pr c-Pr 2-8 Me 1 c-Pr c-Pr 2-9 Me 2 c-Pr c-Pr 2-10 Me 0 CH.sub.2c-Pr c-Pr 2-11 Me 1 CH.sub.2c-Pr c-Pr 2-12 Me 2 CH.sub.2c-Pr c-Pr 2-13 Me 0 CH.sub.2CH.sub.2OMe c-Pr 2-14 Me 1 CH.sub.2CH.sub.2OMe c-Pr 2-15 Me 2 CH.sub.2CH.sub.2OMe c-Pr 2-16 Me 0 Me c-Bu 2-17 Me 1 Me c-Bu 2-18 Me 2 Me c-Bu 2-19 Me 0 Et c-Bu 2-20 Me 1 Et c-Bu 2-21 Me 2 Et c-Bu 2-22 Me 0 c-Pr c-Bu 2-23 Me 1 c-Pr c-Bu 2-24 Me 2 c-Pr c-Bu 2-25 Me 0 CH.sub.2c-Pr c-Bu 2-26 Me 1 CH.sub.2c-Pr c-Bu 2-27 Me 2 CH.sub.2c-Pr c-Bu 2-28 Me 0 CH.sub.2CH.sub.2OMe c-Bu 2-29 Me 1 CH.sub.2CH.sub.2OMe c-Bu 2-30 Me 2 CH.sub.2CH.sub.2OMe c-Bu 2-31 Et 0 Me c-Pr 2-32 Et 1 Me c-Pr 2-33 Et 2 Me c-Pr 2-34 Et 0 Et c-Pr 2-35 Et 1 Et c-Pr 2-36 Et 2 Et c-Pr 2-37 Et 0 c-Pr c-Pr 2-38 Et 1 c-Pr c-Pr 2-39 Et 2 c-Pr c-Pr 2-40 Et 0 CH.sub.2c-Pr c-Pr 2-41 Et 1 CH.sub.2c-Pr c-Pr 2-42 Et 2 CH.sub.2c-Pr c-Pr 2-43 Et 0 CH.sub.2CH.sub.2OMe c-Pr 2-44 Et 1 CH.sub.2CH.sub.2OMe c-Pr 2-45 Et 2 CH.sub.2CH.sub.2OMe c-Pr 2-46 Et 0 Me c-Bu 2-47 Et 1 Me c-Bu 2-48 Et 2 Me c-Bu 2-49 Et 0 Et c-Bu 2-50 Et 1 Et c-Bu 2-51 Et 2 Et c-Bu 2-52 Et 0 c-Pr c-Bu 2-53 Et 1 c-Pr c-Bu 2-54 Et 2 c-Pr c-Bu 2-55 Et 0 CH.sub.2c-Pr c-Bu 2-56 Et 1 CH.sub.2c-Pr c-Bu 2-57 Et 2 CH.sub.2c-Pr c-Bu 2-58 Et 0 CH.sub.2CH.sub.2OMe c-Bu 2-59 Et 1 CH.sub.2CH.sub.2OMe c-Bu 2-60 Et 2 CH.sub.2CH.sub.2OMe c-Bu 2-61 c-Pr 0 Me c-Pr 2-62 c-Pr 1 Me c-Pr 2-63 c-Pr 2 Me c-Pr 2-64 c-Pr 0 Et c-Pr 2-65 c-Pr 1 Et c-Pr 2-66 c-Pr 2 Et c-Pr 2-67 c-Pr 0 c-Pr c-Pr 2-68 c-Pr 1 c-Pr c-Pr 2-69 c-Pr 2 c-Pr c-Pr 2-70 c-Pr 0 CH.sub.2c-Pr c-Pr 2-71 c-Pr 1 CH.sub.2c-Pr c-Pr 2-72 c-Pr 2 CH.sub.2c-Pr c-Pr 2-73 c-Pr 0 CH.sub.2CH.sub.2OMe c-Pr 2-74 c-Pr 1 CH.sub.2CH.sub.2OMe c-Pr 2-75 c-Pr 2 CH.sub.2CH.sub.2OMe c-Pr 2-76 c-Pr 0 Me c-Bu 2-77 c-Pr 1 Me c-Bu 2-78 c-Pr 2 Me c-Bu 2-79 c-Pr 0 Et c-Bu 2-80 c-Pr 1 Et c-Bu 2-81 c-Pr 2 Et c-Bu 2-82 c-Pr 0 c-Pr c-Bu 2-83 c-Pr 1 c-Pr c-Bu 2-84 c-Pr 2 c-Pr c-Bu 2-85 c-Pr 0 CH.sub.2c-Pr c-Bu 2-86 c-Pr 1 CH.sub.2c-Pr c-Bu 2-87 c-Pr 2 CH.sub.2c-Pr c-Bu 2-88 c-Pr 0 CH.sub.2CH.sub.2OMe c-Bu 2-89 c-Pr 1 CH.sub.2CH.sub.2OMe c-Bu

TABLE-US-00003 TABLE 3 Inventive compounds of the general formula (I) in which Q is Q1 and R.sup.x is a n-propyl group [00010] No. X n R Z 3-1 Me 0 Me c-Pr 3-2 Me 1 Me c-Pr 3-3 Me 2 Me c-Pr 3-4 Me 0 Et c-Pr 3-5 Me 1 Et c-Pr 3-6 Me 2 Et c-Pr 3-7 Me 0 c-Pr c-Pr 3-8 Me 1 c-Pr c-Pr 3-9 Me 2 c-Pr c-Pr 3-10 Me 0 CH.sub.2c-Pr c-Pr 3-11 Me 1 CH.sub.2c-Pr c-Pr 3-12 Me 2 CH.sub.2c-Pr c-Pr 3-13 Me 0 CH.sub.2CH.sub.2OMe c-Pr 3-14 Me 1 CH.sub.2CH.sub.2OMe c-Pr 3-15 Me 2 CH.sub.2CH.sub.2OMe c-Pr 3-16 Me 0 Me c-Bu 3-17 Me 1 Me c-Bu 3-18 Me 2 Me c-Bu 3-19 Me 0 Et c-Bu 3-20 Me 1 Et c-Bu 3-21 Me 2 Et c-Bu 3-22 Me 0 c-Pr c-Bu 3-23 Me 1 c-Pr c-Bu 3-24 Me 2 c-Pr c-Bu 3-25 Me 0 CH.sub.2c-Pr c-Bu 3-26 Me 1 CH.sub.2c-Pr c-Bu 3-27 Me 2 CH.sub.2c-Pr c-Bu 3-28 Me 0 CH.sub.2CH.sub.2OMe c-Bu 3-29 Me 1 CH.sub.2CH.sub.2OMe c-Bu 3-30 Me 2 CH.sub.2CH.sub.2OMe c-Bu 3-31 Et 0 Me c-Pr 3-32 Et 1 Me c-Pr 3-33 Et 2 Me c-Pr 3-34 Et 0 Et c-Pr 3-35 Et 1 Et c-Pr 3-36 Et 2 Et c-Pr 3-37 Et 0 c-Pr c-Pr 3-38 Et 1 c-Pr c-Pr 3-39 Et 2 c-Pr c-Pr 3-40 Et 0 CH.sub.2c-Pr c-Pr 3-41 Et 1 CH.sub.2c-Pr c-Pr 3-42 Et 2 CH.sub.2c-Pr c-Pr 3-43 Et 0 CH.sub.2CH.sub.2OMe c-Pr 3-44 Et 1 CH.sub.2CH.sub.2OMe c-Pr 3-45 Et 2 CH.sub.2CH.sub.2OMe c-Pr 3-46 Et 0 Me c-Bu 3-47 Et 1 Me c-Bu 3-48 Et 2 Me c-Bu 3-49 Et 0 Et c-Bu 3-50 Et 1 Et c-Bu 3-51 Et 2 Et c-Bu 3-52 Et 0 c-Pr c-Bu 3-53 Et 1 c-Pr c-Bu 3-54 Et 2 c-Pr c-Bu 3-55 Et 0 CH.sub.2c-Pr c-Bu 3-56 Et 1 CH.sub.2c-Pr c-Bu 3-57 Et 2 CH.sub.2c-Pr c-Bu 3-58 Et 0 CH.sub.2CH.sub.2OMe c-Bu 3-59 Et 1 CH.sub.2CH.sub.2OMe c-Bu 3-60 Et 2 CH.sub.2CH.sub.2OMe c-Bu 3-61 c-Pr 0 Me c-Pr 3-62 c-Pr 1 Me c-Pr 3-63 c-Pr 2 Me c-Pr 3-64 c-Pr 0 Et c-Pr 3-65 c-Pr 1 Et c-Pr 3-66 c-Pr 2 Et c-Pr 3-67 c-Pr 0 c-Pr c-Pr 3-68 c-Pr 1 c-Pr c-Pr 3-69 c-Pr 2 c-Pr c-Pr 3-70 c-Pr 0 CH.sub.2c-Pr c-Pr 3-71 c-Pr 1 CH.sub.2c-Pr c-Pr 3-72 c-Pr 2 CH.sub.2c-Pr c-Pr 3-73 c-Pr 0 CH.sub.2CH.sub.2OMe c-Pr 3-74 c-Pr 1 CH.sub.2CH.sub.2OMe c-Pr 3-75 c-Pr 2 CH.sub.2CH.sub.2OMe c-Pr 3-76 c-Pr 0 Me c-Bu 3-77 c-Pr 1 Me c-Bu 3-78 c-Pr 2 Me c-Bu 3-79 c-Pr 0 Et c-Bu 3-80 c-Pr 1 Et c-Bu 3-81 c-Pr 2 Et c-Bu 3-82 c-Pr 0 c-Pr c-Bu c-Pr 1 c-Pr c-Bu 3-83 c-Pr 2 c-Pr c-Bu 3-84 c-Pr 0 CH.sub.2c-Pr c-Bu 3-85 c-Pr 1 CH.sub.2c-Pr c-Bu 3-86 c-Pr 2 CH.sub.2c-Pr c-Bu 3-87 c-Pr 0 CH.sub.2CH.sub.2OMe c-Bu 3-88 c-Pr 1 CH.sub.2CH.sub.2OMe c-Bu 3-89 c-Pr 2 CH.sub.2CH.sub.2OMe c-Bu

TABLE-US-00004 TABLE 4 Inventive compounds of the general formula (I) in which Q is Q2 and R.sup.x is a methyl group [00011] No. X n R Z 4-1 Me 0 Me c-Pr 4-2 Me 1 Me c-Pr 4-3 Me 2 Me c-Pr 4-4 Me 0 Et c-Pr 4-5 Me 1 Et c-Pr 4-6 Me 2 Et c-Pr 4-7 Me 0 c-Pr c-Pr 4-8 Me 1 c-Pr c-Pr 4-9 Me 2 c-Pr c-Pr 4-10 Me 0 CH.sub.2c-Pr c-Pr 4-11 Me 1 CH.sub.2c-Pr c-Pr 4-12 Me 2 CH.sub.2c-Pr c-Pr 4-13 Me 0 CH.sub.2CH.sub.2OMe c-Pr 4-14 Me 1 CH.sub.2CH.sub.2OMe c-Pr 4-15 Me 2 CH.sub.2CH.sub.2OMe c-Pr 4-16 Me 0 Me c-Bu 4-17 Me 1 Me c-Bu 4-18 Me 2 Me c-Bu 4-19 Me 0 Et c-Bu 4-20 Me 1 Et c-Bu 4-21 Me 2 Et c-Bu 4-22 Me 0 c-Pr c-Bu 4-23 Me 1 c-Pr c-Bu 4-24 Me 2 c-Pr c-Bu 4-25 Me 0 CH.sub.2c-Pr c-Bu 4-26 Me 1 CH.sub.2c-Pr c-Bu 4-27 Me 2 CH.sub.2c-Pr c-Bu 4-28 Me 0 CH.sub.2CH.sub.2OMe c-Bu 4-29 Me 1 CH.sub.2CH.sub.2OMe c-Bu 4-30 Me 2 CH.sub.2CH.sub.2OMe c-Bu 4-31 Et 0 Me c-Pr 4-32 Et 1 Me c-Pr 4-33 Et 2 Me c-Pr 4-34 Et 0 Et c-Pr 4-35 Et 1 Et c-Pr 4-36 Et 2 Et c-Pr 4-37 Et 0 c-Pr c-Pr 4-38 Et 1 c-Pr c-Pr 4-39 Et 2 c-Pr c-Pr 4-40 Et 0 CH.sub.2c-Pr c-Pr 4-41 Et 1 CH.sub.2c-Pr c-Pr 4-42 Et 2 CH.sub.2c-Pr c-Pr 4-43 Et 0 CH.sub.2CH.sub.2OMe c-Pr 4-44 Et 1 CH.sub.2CH.sub.2OMe c-Pr 4-45 Et 2 CH.sub.2CH.sub.2OMe c-Pr 4-46 Et 0 Me c-Bu 4-47 Et 1 Me c-Bu 4-48 Et 2 Me c-Bu 4-49 Et 0 Et c-Bu 4-50 Et 1 Et c-Bu 4-51 Et 2 Et c-Bu 4-52 Et 0 c-Pr c-Bu 4-53 Et 1 c-Pr c-Bu 4-54 Et 2 c-Pr c-Bu 4-55 Et 0 CH.sub.2c-Pr c-Bu 4-56 Et 1 CH.sub.2c-Pr c-Bu 4-57 Et 2 CH.sub.2c-Pr c-Bu 4-58 Et 0 CH.sub.2CH.sub.2OMe c-Bu 4-59 Et 1 CH.sub.2CH.sub.2OMe c-Bu 4-60 Et 2 CH.sub.2CH.sub.2OMe c-Bu 4-61 c-Pr 0 Me c-Pr 4-62 c-Pr 1 Me c-Pr 4-63 c-Pr 2 Me c-Pr 4-64 c-Pr 0 Et c-Pr 4-65 c-Pr 1 Et c-Pr 4-66 c-Pr 2 Et c-Pr 4-67 c-Pr 0 c-Pr c-Pr 4-68 c-Pr 1 c-Pr c-Pr 4-69 c-Pr 2 c-Pr c-Pr 4-70 c-Pr 0 CH.sub.2c-Pr c-Pr 4-71 c-Pr 1 CH.sub.2c-Pr c-Pr 4-72 c-Pr 2 CH.sub.2c-Pr c-Pr 4-73 c-Pr 0 CH.sub.2CH.sub.2OMe c-Pr 4-74 c-Pr 1 CH.sub.2CH.sub.2OMe c-Pr 4-75 c-Pr 2 CH.sub.2CH.sub.2OMe c-Pr 4-76 c-Pr 0 Me c-Bu 4-77 c-Pr 1 Me c-Bu 4-78 c-Pr 2 Me c-Bu 4-79 c-Pr 0 Et c-Bu 4-80 c-Pr 1 Et c-Bu 4-81 c-Pr 2 Et c-Bu 4-82 c-Pr 0 c-Pr c-Bu 4-83 c-Pr 1 c-Pr c-Bu 4-84 c-Pr 2 c-Pr c-Bu 4-85 c-Pr 0 CH.sub.2c-Pr c-Bu 4-86 c-Pr 1 CH.sub.2c-Pr c-Bu 4-87 c-Pr 2 CH.sub.2c-Pr c-Bu 4-88 c-Pr 0 CH.sub.2CH.sub.2OMe c-Bu 4-89 c-Pr 1 CH.sub.2CH.sub.2OMe c-Bu 4-90 c-Pr 2 CH.sub.2CH.sub.2OMe c-Bu

TABLE-US-00005 TABLE 5 Inventive compounds of the general formula (I) in which Q is Q3 and R.sup.y is a methyl group [00012] No. X n R Z 5-1 Me 0 Me c-Pr 5-2 Me 1 Me c-Pr 5-3 Me 2 Me c-Pr 5-4 Me 0 Et c-Pr 5-5 Me 1 Et c-Pr 5-6 Me 2 Et c-Pr 5-7 Me 0 c-Pr c-Pr 5-8 Me 1 c-Pr c-Pr 5-9 Me 2 c-Pr c-Pr 5-10 Me 0 CH.sub.2c-Pr c-Pr 5-11 Me 1 CH.sub.2c-Pr c-Pr 5-12 Me 2 CH.sub.2c-Pr c-Pr 5-13 Me 0 CH.sub.2CH.sub.2OMe c-Pr 5-14 Me 1 CH.sub.2CH.sub.2OMe c-Pr 5-15 Me 2 CH.sub.2CH.sub.2OMe c-Pr 5-16 Me 0 Me c-Bu 5-17 Me 1 Me c-Bu 5-18 Me 2 Me c-Bu 5-19 Me 0 Et c-Bu 5-20 Me 1 Et c-Bu 5-21 Me 2 Et c-Bu 5-22 Me 0 c-Pr c-Bu 5-23 Me 1 c-Pr c-Bu 5-24 Me 2 c-Pr c-Bu 5-25 Me 0 CH.sub.2c-Pr c-Bu 5-26 Me 1 CH.sub.2c-Pr c-Bu 5-27 Me 2 CH.sub.2c-Pr c-Bu 5-28 Me 0 CH.sub.2CH.sub.2OMe c-Bu 5-29 Me 1 CH.sub.2CH.sub.2OMe c-Bu 5-30 Me 2 CH.sub.2CH.sub.2OMe c-Bu 5-31 Et 0 Me c-Pr 5-32 Et 1 Me c-Pr 5-33 Et 2 Me c-Pr 5-34 Et 0 Et c-Pr 5-35 Et 1 Et c-Pr 5-36 Et 2 Et c-Pr 5-37 Et 0 c-Pr c-Pr 5-38 Et 1 c-Pr c-Pr 5-39 Et 2 c-Pr c-Pr 5-40 Et 0 CH.sub.2c-Pr c-Pr 5-41 Et 1 CH.sub.2c-Pr c-Pr 5-42 Et 2 CH.sub.2c-Pr c-Pr 5-43 Et 0 CH.sub.2CH.sub.2OMe c-Pr 5-44 Et 1 CH.sub.2CH.sub.2OMe c-Pr 5-45 Et 2 CH.sub.2CH.sub.2OMe c-Pr 5-46 Et 0 Me c-Bu 5-47 Et 1 Me c-Bu 5-48 Et 2 Me c-Bu 5-49 Et 0 Et c-Bu 5-50 Et 1 Et c-Bu 5-51 Et 2 Et c-Bu 5-52 Et 0 c-Pr c-Bu 5-53 Et 1 c-Pr c-Bu 5-54 Et 2 c-Pr c-Bu 5-55 Et 0 CH.sub.2c-Pr c-Bu 5-56 Et 1 CH.sub.2c-Pr c-Bu 5-57 Et 2 CH.sub.2c-Pr c-Bu 5-58 Et 0 CH.sub.2CH.sub.2OMe c-Bu 5-59 Et 1 CH.sub.2CH.sub.2OMe c-Bu 5-60 Et 2 CH.sub.2CH.sub.2OMe c-Bu 5-61 c-Pr 0 Me c-Pr 5-62 c-Pr 1 Me c-Pr 5-63 c-Pr 2 Me c-Pr 5-64 c-Pr 0 Et c-Pr 5-65 c-Pr 1 Et c-Pr 5-66 c-Pr 2 Et c-Pr 5-67 c-Pr 0 c-Pr c-Pr 5-68 c-Pr 1 c-Pr c-Pr 5-69 c-Pr 2 c-Pr c-Pr 5-70 c-Pr 0 CH.sub.2c-Pr c-Pr 5-71 c-Pr 1 CH.sub.2c-Pr c-Pr 5-72 c-Pr 2 CH.sub.2c-Pr c-Pr 5-73 c-Pr 0 CH.sub.2CH.sub.2OMe c-Pr 5-74 c-Pr 1 CH.sub.2CH.sub.2OMe c-Pr 5-75 c-Pr 2 CH.sub.2CH.sub.2OMe c-Pr 5-76 c-Pr 0 Me c-Bu 5-77 c-Pr 1 Me c-Bu 5-78 c-Pr 2 Me c-Bu 5-79 c-Pr 0 Et c-Bu 5-80 c-Pr 1 Et c-Bu 5-81 c-Pr 2 Et c-Bu 5-82 c-Pr 0 c-Pr c-Bu 5-83 c-Pr 1 c-Pr c-Bu 5-84 c-Pr 2 c-Pr c-Bu 5-85 c-Pr 0 CH.sub.2c-Pr c-Bu 5-86 c-Pr 1 CH.sub.2c-Pr c-Bu 5-87 c-Pr 2 CH.sub.2c-Pr c-Bu 5-88 c-Pr 0 CH.sub.2CH.sub.2OMe c-Bu 5-89 c-Pr 1 CH.sub.2CH.sub.2OMe c-Bu 5-90 c-Pr 2 CH.sub.2CH.sub.2OMe c-Bu

TABLE-US-00006 TABLE 6 Inventive compounds of the general formula (I) in which Q is Q3 and R.sup.y is a chlorine atom [00013] No. X n R Z 6-1 Me 0 Me c-Pr 6-2 Me 1 Me c-Pr 6-3 Me 2 Me c-Pr 6-4 Me 0 Et c-Pr 6-5 Me 1 Et c-Pr 6-6 Me 2 Et c-Pr 6-7 Me 0 c-Pr c-Pr 6-8 Me 1 c-Pr c-Pr 6-9 Me 2 c-Pr c-Pr 6-10 Me 0 CH.sub.2c-Pr c-Pr 6-11 Me 1 CH.sub.2c-Pr c-Pr 6-12 Me 2 CH.sub.2c-Pr c-Pr 6-13 Me 0 CH.sub.2CH.sub.2OMe c-Pr 6-14 Me 1 CH.sub.2CH.sub.2OMe c-Pr 6-15 Me 2 CH.sub.2CH.sub.2OMe c-Pr 6-16 Me 0 Me c-Bu 6-17 Me 1 Me c-Bu 6-18 Me 2 Me c-Bu 6-19 Me 0 Et c-Bu 6-20 Me 1 Et c-Bu 6-21 Me 2 Et c-Bu 6-22 Me 0 c-Pr c-Bu 6-23 Me 1 c-Pr c-Bu 6-24 Me 2 c-Pr c-Bu 6-25 Me 0 CH.sub.2c-Pr c-Bu 6-26 Me 1 CH.sub.2c-Pr c-Bu 6-27 Me 2 CH.sub.2c-Pr c-Bu 6-28 Me 0 CH.sub.2CH.sub.2OMe c-Bu 6-29 Me 1 CH.sub.2CH.sub.2OMe c-Bu 6-30 Me 2 CH.sub.2CH.sub.2OMe c-Bu 6-31 Et 0 Me c-Pr 6-32 Et 1 Me c-Pr 6-33 Et 2 Me c-Pr 6-34 Et 0 Et c-Pr 6-35 Et 1 Et c-Pr 6-36 Et 2 Et c-Pr 6-37 Et 0 c-Pr c-Pr 6-38 Et 1 c-Pr c-Pr 6-39 Et 2 c-Pr c-Pr 6-40 Et 0 CH.sub.2c-Pr c-Pr 6-41 Et 1 CH.sub.2c-Pr c-Pr 6-42 Et 2 CH.sub.2c-Pr c-Pr 6-43 Et 0 CH.sub.2CH.sub.2OMe c-Pr 6-44 Et 1 CH.sub.2CH.sub.2OMe c-Pr 6-45 Et 2 CH.sub.2CH.sub.2OMe c-Pr 6-46 Et 0 Me c-Bu 6-47 Et 1 Me c-Bu 6-48 Et 2 Me c-Bu 6-49 Et 0 Et c-Bu 6-50 Et 1 Et c-Bu 6-51 Et 2 Et c-Bu 6-52 Et 0 c-Pr c-Bu 6-53 Et 1 c-Pr c-Bu 6-54 Et 2 c-Pr c-Bu 6-55 Et 0 CH.sub.2c-Pr c-Bu 6-56 Et 1 CH.sub.2c-Pr c-Bu 6-57 Et 2 CH.sub.2c-Pr c-Bu 6-58 Et 0 CH.sub.2CH.sub.2OMe c-Bu 6-59 Et 1 CH.sub.2CH.sub.2OMe c-Bu 6-60 Et 2 CH.sub.2CH.sub.2OMe c-Bu 6-61 c-Pr 0 Me c-Pr 6-62 c-Pr 1 Me c-Pr 6-63 c-Pr 2 Me c-Pr 6-64 c-Pr 0 Et c-Pr 6-65 c-Pr 1 Et c-Pr 6-66 c-Pr 2 Et c-Pr 6-67 c-Pr 0 c-Pr c-Pr 6-68 c-Pr 1 c-Pr c-Pr 6-69 c-Pr 2 c-Pr c-Pr 6-70 c-Pr 0 CH.sub.2c-Pr c-Pr 6-71 c-Pr 1 CH.sub.2c-Pr c-Pr 6-72 c-Pr 2 CH.sub.2c-Pr c-Pr 6-73 c-Pr 0 CH.sub.2CH.sub.2OMe c-Pr 6-74 c-Pr 1 CH.sub.2CH.sub.2OMe c-Pr 6-75 c-Pr 2 CH.sub.2CH.sub.2OMe c-Pr 6-76 c-Pr 0 Me c-Bu 6-77 c-Pr 1 Me c-Bu 6-78 c-Pr 2 Me c-Bu 6-79 c-Pr 0 Et c-Bu 6-80 c-Pr 1 Et c-Bu 6-81 c-Pr 2 Et c-Bu 6-82 c-Pr 0 c-Pr c-Bu 6-83 c-Pr 1 c-Pr c-Bu 6-84 c-Pr 2 c-Pr c-Bu 6-85 c-Pr 0 CH.sub.2c-Pr c-Bu 6-86 c-Pr 1 CH.sub.2c-Pr c-Bu 6-87 c-Pr 2 CH.sub.2c-Pr c-Bu 6-88 c-Pr 0 CH.sub.2CH.sub.2OMe c-Bu 6-89 c-Pr 1 CH.sub.2CH.sub.2OMe c-Bu 6-90 c-Pr 2 CH.sub.2CH.sub.2OMe c-Bu

TABLE-US-00007 TABLE 7 Inventive compounds of the general formula (I) in which Q is Q4 and R.sup.z is a methyl group [00014] No. X n R Z 7-1 Me 0 Me c-Pr 7-2 Me 1 Me c-Pr 7-3 Me 2 Me c-Pr 7-4 Me 0 Et c-Pr 7-5 Me 1 Et c-Pr 7-6 Me 2 Et c-Pr 7-7 Me 0 c-Pr c-Pr 7-8 Me 1 c-Pr c-Pr 7-9 Me 2 c-Pr c-Pr 7-10 Me 0 CH.sub.2c-Pr c-Pr 7-11 Me 1 CH.sub.2c-Pr c-Pr 7-12 Me 2 CH.sub.2c-Pr c-Pr 7-13 Me 0 CH.sub.2CH.sub.2OMe c-Pr 7-14 Me 1 CH.sub.2CH.sub.2OMe c-Pr 7-15 Me 2 CH.sub.2CH.sub.2OMe c-Pr 7-16 Me 0 Me c-Bu 7-17 Me 1 Me c-Bu 7-18 Me 2 Me c-Bu 7-19 Me 0 Et c-Bu 7-20 Me 1 Et c-Bu 7-21 Me 2 Et c-Bu 7-22 Me 0 c-Pr c-Bu 7-23 Me 1 c-Pr c-Bu 7-24 Me 2 c-Pr c-Bu 7-25 Me 0 CH.sub.2c-Pr c-Bu 7-26 Me 1 CH.sub.2c-Pr c-Bu 7-27 Me 2 CH.sub.2c-Pr c-Bu 7-28 Me 0 CH.sub.2CH.sub.2OMe c-Bu 7-29 Me 1 CH.sub.2CH.sub.2OMe c-Bu 7-30 Me 2 CH.sub.2CH.sub.2OMe c-Bu 7-31 Et 0 Me c-Pr 7-32 Et 1 Me c-Pr 7-33 Et 2 Me c-Pr 7-34 Et 0 Et c-Pr 7-35 Et 1 Et c-Pr 7-36 Et 2 Et c-Pr 7-37 Et 0 c-Pr c-Pr 7-38 Et 1 c-Pr c-Pr 7-39 Et 2 c-Pr c-Pr 7-40 Et 0 CH.sub.2c-Pr c-Pr 7-41 Et 1 CH.sub.2c-Pr c-Pr 7-42 Et 2 CH.sub.2c-Pr c-Pr 7-43 Et 0 CH.sub.2CH.sub.2OMe c-Pr 7-44 Et 1 CH.sub.2CH.sub.2OMe c-Pr 7-45 Et 2 CH.sub.2CH.sub.2OMe c-Pr 7-46 Et 0 Me c-Bu 7-47 Et 1 Me c-Bu 7-48 Et 2 Me c-Bu 7-49 Et 0 Et c-Bu 7-50 Et 1 Et c-Bu 7-51 Et 2 Et c-Bu 7-52 Et 0 c-Pr c-Bu 7-53 Et 1 c-Pr c-Bu 7-54 Et 2 c-Pr c-Bu 7-55 Et 0 CH.sub.2c-Pr c-Bu 7-56 Et 1 CH.sub.2c-Pr c-Bu 7-57 Et 2 CH.sub.2c-Pr c-Bu 7-58 Et 0 CH.sub.2CH.sub.2OMe c-Bu 7-59 Et 1 CH.sub.2CH.sub.2OMe c-Bu 7-60 Et 2 CH.sub.2CH.sub.2OMe c-Bu 7-61 c-Pr 0 Me c-Pr 7-62 c-Pr 1 Me c-Pr 7-63 c-Pr 2 Me c-Pr 7-64 c-Pr 0 Et c-Pr 7-65 c-Pr 1 Et c-Pr 7-66 c-Pr 2 Et c-Pr 7-67 c-Pr 0 c-Pr c-Pr 7-68 c-Pr 1 c-Pr c-Pr 7-69 c-Pr 2 c-Pr c-Pr 7-70 c-Pr 0 CH.sub.2c-Pr c-Pr 7-71 c-Pr 1 CH.sub.2c-Pr c-Pr 7-72 c-Pr 2 CH.sub.2c-Pr c-Pr 7-73 c-Pr 0 CH.sub.2CH.sub.2OMe c-Pr 7-74 c-Pr 1 CH.sub.2CH.sub.2OMe c-Pr 7-75 c-Pr 2 CH.sub.2CH.sub.2OMe c-Pr 7-76 c-Pr 0 Me c-Bu 7-77 c-Pr 1 Me c-Bu 7-78 c-Pr 2 Me c-Bu 7-79 c-Pr 0 Et c-Bu 7-80 c-Pr 1 Et c-Bu 7-81 c-Pr 2 Et c-Bu 7-82 c-Pr 0 c-Pr c-Bu 7-83 c-Pr 1 c-Pr c-Bu 7-84 c-Pr 2 c-Pr c-Bu 7-85 c-Pr 0 CH.sub.2c-Pr c-Bu 7-86 c-Pr 1 CH.sub.2c-Pr c-Bu 7-87 c-Pr 2 CH.sub.2c-Pr c-Bu 7-88 c-Pr 0 CH.sub.2CH.sub.2OMe c-Bu 7-89 c-Pr 1 CH.sub.2CH.sub.2OMe c-Bu 7-90 c-Pr 2 CH.sub.2CH.sub.2OMe c-Bu

TABLE-US-00008 TABLE 8 Inventive compounds of the general formula (I) in the form of the sodium salts, in which Q is Q1 and R.sup.x is a methyl group [00015] No. X n R Z 8-1 Me 0 Me c-Pr 8-2 Me 1 Me c-Pr 8-3 Me 2 Me c-Pr 8-4 Me 0 Et c-Pr 8-5 Me 1 Et c-Pr 8-6 Me 2 Et c-Pr 8-7 Me 0 c-Pr c-Pr 8-8 Me 1 c-Pr c-Pr 8-9 Me 2 c-Pr c-Pr 8-10 Me 0 CH.sub.2c-Pr c-Pr 8-11 Me 1 CH.sub.2c-Pr c-Pr 8-12 Me 2 CH.sub.2c-Pr c-Pr 8-13 Me 0 CH.sub.2CH.sub.2OMe c-Pr 8-14 Me 1 CH.sub.2CH.sub.2OMe c-Pr 8-15 Me 2 CH.sub.2CH.sub.2OMe c-Pr 8-16 Me 0 Me c-Bu 8-17 Me 1 Me c-Bu 8-18 Me 2 Me c-Bu 8-19 Me 0 Et c-Bu 8-20 Me 1 Et c-Bu 8-21 Me 2 Et c-Bu 8-22 Me 0 c-Pr c-Bu 8-23 Me 1 c-Pr c-Bu 8-24 Me 2 c-Pr c-Bu 8-25 Me 0 CH.sub.2c-Pr c-Bu 8-26 Me 1 CH.sub.2c-Pr c-Bu 8-27 Me 2 CH.sub.2c-Pr c-Bu 8-28 Me 0 CH.sub.2CH.sub.2OMe c-Bu 8-29 Me 1 CH.sub.2CH.sub.2OMe c-Bu 8-30 Me 2 CH.sub.2CH.sub.2OMe c-Bu 8-31 Et 0 Me c-Pr 8-32 Et 1 Me c-Pr 8-33 Et 2 Me c-Pr 8-34 Et 0 Et c-Pr 8-35 Et 1 Et c-Pr 8-36 Et 2 Et c-Pr 8-37 Et 0 c-Pr c-Pr 8-38 Et 1 c-Pr c-Pr 8-39 Et 2 c-Pr c-Pr 8-40 Et 0 CH.sub.2c-Pr c-Pr 8-41 Et 1 CH.sub.2c-Pr c-Pr 8-42 Et 2 CH.sub.2c-Pr c-Pr 8-43 Et 0 CH.sub.2CH.sub.2OMe c-Pr 8-44 Et 1 CH.sub.2CH.sub.2OMe c-Pr 8-45 Et 2 CH.sub.2CH.sub.2OMe c-Pr 8-46 Et 0 Me c-Bu 8-47 Et 1 Me c-Bu 8-48 Et 2 Me c-Bu 8-49 Et 0 Et c-Bu 8-50 Et 1 Et c-Bu 8-51 Et 2 Et c-Bu 8-52 Et 0 c-Pr c-Bu 8-53 Et 1 c-Pr c-Bu 8-54 Et 2 c-Pr c-Bu 8-55 Et 0 CH.sub.2c-Pr c-Bu 8-56 Et 1 CH.sub.2c-Pr c-Bu 8-57 Et 2 CH.sub.2c-Pr c-Bu 8-58 Et 0 CH.sub.2CH.sub.2OMe c-Bu 8-59 Et 1 CH.sub.2CH.sub.2OMe c-Bu 8-60 Et 2 CH.sub.2CH.sub.2OMe c-Bu 8-61 c-Pr 0 Me c-Pr 8-62 c-Pr 1 Me c-Pr 8-63 c-Pr 2 Me c-Pr 8-64 c-Pr 0 Et c-Pr 8-65 c-Pr 1 Et c-Pr 8-66 c-Pr 2 Et c-Pr 8-67 c-Pr 0 c-Pr c-Pr 8-68 c-Pr 1 c-Pr c-Pr 8-69 c-Pr 2 c-Pr c-Pr 8-70 c-Pr 0 CH.sub.2c-Pr c-Pr 8-71 c-Pr 1 CH.sub.2c-Pr c-Pr 8-72 c-Pr 2 CH.sub.2c-Pr c-Pr 8-73 c-Pr 0 CH.sub.2CH.sub.2OMe c-Pr 8-74 c-Pr 1 CH.sub.2CH.sub.2OMe c-Pr 8-75 c-Pr 2 CH.sub.2CH.sub.2OMe c-Pr 8-76 c-Pr 0 Me c-Bu 8-77 c-Pr 1 Me c-Bu 8-78 c-Pr 2 Me c-Bu 8-79 c-Pr 0 Et c-Bu 8-80 c-Pr 1 Et c-Bu 8-81 c-Pr 2 Et c-Bu 8-82 c-Pr 0 c-Pr c-Bu 8-83 c-Pr 1 c-Pr c-Bu 8-84 c-Pr 2 c-Pr c-Bu 8-85 c-Pr 0 CH.sub.2c-Pr c-Bu 8-86 c-Pr 1 CH.sub.2c-Pr c-Bu 8-87 c-Pr 2 CH.sub.2c-Pr c-Bu 8-88 c-Pr 0 CH.sub.2CH.sub.2OMe c-Bu 8-89 c-Pr 1 CH.sub.2CH.sub.2OMe c-Bu 8-90 c-Pr 2 CH.sub.2CH.sub.2OMe c-Bu

TABLE-US-00009 TABLE 9 Inventive benzoic acids of the formula (II) [00016] No. X n R Z 9-1 Me 0 Me c-Pr 9-2 Me 1 Me c-Pr 9-3 Me 2 Me c-Pr 9-4 Me 0 Et c-Pr 9-5 Me 1 Et c-Pr 9-6 Me 2 Et c-Pr 9-7 Me 0 c-Pr c-Pr 9-8 Me 1 c-Pr c-Pr 9-9 Me 2 c-Pr c-Pr 9-10 Me 0 CH.sub.2c-Pr c-Pr 9-11 Me 1 CH.sub.2c-Pr c-Pr 9-12 Me 2 CH.sub.2c-Pr c-Pr 9-13 Me 0 CH.sub.2CH.sub.2OMe c-Pr 9-14 Me 1 CH.sub.2CH.sub.2OMe c-Pr 9-15 Me 2 CH.sub.2CH.sub.2OMe c-Pr 9-16 Me 0 Me c-Bu 9-17 Me 1 Me c-Bu 9-18 Me 2 Me c-Bu 9-19 Me 0 Et c-Bu 9-20 Me 1 Et c-Bu 9-21 Me 2 Et c-Bu 9-22 Me 0 c-Pr c-Bu 9-23 Me 1 c-Pr c-Bu 9-24 Me 2 c-Pr c-Bu 9-25 Me 0 CH.sub.2c-Pr c-Bu 9-26 Me 1 CH.sub.2c-Pr c-Bu 9-27 Me 2 CH.sub.2c-Pr c-Bu 9-28 Me 0 CH.sub.2CH.sub.2OMe c-Bu 9-29 Me 1 CH.sub.2CH.sub.2OMe c-Bu 9-30 Me 2 CH.sub.2CH.sub.2OMe c-Bu 9-31 Et 0 Me c-Pr 9-32 Et 1 Me c-Pr 9-33 Et 2 Me c-Pr 9-34 Et 0 Et c-Pr 9-35 Et 1 Et c-Pr 9-36 Et 2 Et c-Pr 9-37 Et 0 c-Pr c-Pr 9-38 Et 1 c-Pr c-Pr 9-39 Et 2 c-Pr c-Pr 9-40 Et 0 CH.sub.2c-Pr c-Pr 9-41 Et 1 CH.sub.2c-Pr c-Pr 9-42 Et 2 CH.sub.2c-Pr c-Pr 9-43 Et 0 CH.sub.2CH.sub.2OMe c-Pr 9-44 Et 1 CH.sub.2CH.sub.2OMe c-Pr 9-45 Et 2 CH.sub.2CH.sub.2OMe c-Pr 9-46 Et 0 Me c-Bu 9-47 Et 1 Me c-Bu 9-48 Et 2 Me c-Bu 9-49 Et 0 Et c-Bu 9-50 Et 1 Et c-Bu 9-51 Et 2 Et c-Bu 9-52 Et 0 c-Pr c-Bu 9-53 Et 1 c-Pr c-Bu 9-54 Et 2 c-Pr c-Bu 9-55 Et 0 CH.sub.2c-Pr c-Bu 9-56 Et 1 CH.sub.2c-Pr c-Bu 9-57 Et 2 CH.sub.2c-Pr c-Bu 9-58 Et 0 CH.sub.2CH.sub.2OMe c-Bu 9-59 Et 1 CH.sub.2CH.sub.2OMe c-Bu 9-60 Et 2 CH.sub.2CH.sub.2OMe c-Bu 9-61 c-Pr 0 Me c-Pr 9-62 c-Pr 1 Me c-Pr 9-63 c-Pr 2 Me c-Pr 9-64 c-Pr 0 Et c-Pr 9-65 c-Pr 1 Et c-Pr 9-66 c-Pr 2 Et c-Pr 9-67 c-Pr 0 c-Pr c-Pr 9-68 c-Pr 1 c-Pr c-Pr 9-69 c-Pr 2 c-Pr c-Pr 9-70 c-Pr 0 CH.sub.2c-Pr c-Pr 9-71 c-Pr 1 CH.sub.2c-Pr c-Pr 9-72 c-Pr 2 CH.sub.2c-Pr c-Pr 9-73 c-Pr 0 CH.sub.2CH.sub.2OMe c-Pr 9-74 c-Pr 1 CH.sub.2CH.sub.2OMe c-Pr 9-75 c-Pr 2 CH.sub.2CH.sub.2OMe c-Pr 9-76 c-Pr 0 Me c-Bu 9-77 c-Pr 1 Me c-Bu 9-78 c-Pr 2 Me c-Bu 9-79 c-Pr 0 Et c-Bu 9-80 c-Pr 1 Et c-Bu 9-81 c-Pr 2 Et c-Bu 9-82 c-Pr 0 c-Pr c-Bu 9-83 c-Pr 1 c-Pr c-Bu 9-84 c-Pr 2 c-Pr c-Bu 9-85 c-Pr 0 CH.sub.2c-Pr c-Bu 9-86 c-Pr 1 CH.sub.2c-Pr c-Bu 9-87 c-Pr 2 CH.sub.2c-Pr c-Bu 9-88 c-Pr 0 CH.sub.2CH.sub.2OMe c-Bu 9-89 c-Pr 1 CH.sub.2CH.sub.2OMe c-Bu 9-90 c-Pr 2 CH.sub.2CH.sub.2OMe c-Bu

TABLE-US-00010 TABLE 10 Inventive benzoyl chlorides of the formula (III) [00017] No. X n R Z 10-1 Me 0 Me c-Pr 10-2 Me 2 Me c-Pr 10-3 Me 0 Et c-Pr 10-4 Me 2 Et c-Pr 10-5 Me 0 c-Pr c-Pr 10-6 Me 2 c-Pr c-Pr 10-7 Me 0 CH.sub.2c-Pr c-Pr 10-8 Me 2 CH.sub.2c-Pr c-Pr 10-9 Me 0 CH.sub.2CH.sub.2OMe c-Pr 10-10 Me 2 CH.sub.2CH.sub.2OMe c-Pr 10-11 Me 0 Me c-Bu 10-12 Me 2 Me c-Bu 10-13 Me 0 Et c-Bu 10-14 Me 2 Et c-Bu 10-15 Me 0 c-Pr c-Bu 10-16 Me 2 c-Pr c-Bu 10-17 Me 0 CH.sub.2c-Pr c-Bu 10-18 Me 2 CH.sub.2c-Pr c-Bu 10-19 Me 0 CH.sub.2CH.sub.2OMe c-Bu 10-20 Me 2 CH.sub.2CH.sub.2OMe c-Bu 10-21 Et 0 Me c-Pr 10-22 Et 2 Me c-Pr 10-23 Et 0 Et c-Pr 10-24 Et 2 Et c-Pr 10-25 Et 0 c-Pr c-Pr 10-26 Et 2 c-Pr c-Pr 10-27 Et 0 CH.sub.2c-Pr c-Pr 10-28 Et 2 CH.sub.2c-Pr c-Pr 10-29 Et 0 CH.sub.2CH.sub.2OMe c-Pr 10-30 Et 2 CH.sub.2CH.sub.2OMe c-Pr 10-31 Et 0 Me c-Bu 10-32 Et 2 Me c-Bu 10-33 Et 0 Et c-Bu 10-34 Et 2 Et c-Bu 10-35 Et 0 c-Pr c-Bu 10-36 Et 2 c-Pr c-Bu 10-37 Et 0 CH.sub.2c-Pr c-Bu 10-38 Et 2 CH.sub.2c-Pr c-Bu 10-39 Et 0 CH.sub.2CH.sub.2OMe c-Bu 10-40 Et 2 CH.sub.2CH.sub.2OMe c-Bu 10-41 c-Pr 0 Me c-Pr 10-42 c-Pr 2 Me c-Pr 10-43 c-Pr 0 Et c-Pr 10-44 c-Pr 2 Et c-Pr 10-45 c-Pr 0 c-Pr c-Pr 10-46 c-Pr 2 c-Pr c-Pr 10-47 c-Pr 0 CH.sub.2c-Pr c-Pr 10-48 c-Pr 2 CH.sub.2c-Pr c-Pr 10-49 c-Pr 0 CH.sub.2CH.sub.2OMe c-Pr 10-50 c-Pr 2 CH.sub.2CH.sub.2OMe c-Pr 10-51 c-Pr 0 Me c-Bu 10-52 c-Pr 2 Me c-Bu 10-53 c-Pr 0 Et c-Bu 10-54 c-Pr 2 Et c-Bu 10-55 c-Pr 0 c-Pr c-Bu 10-56 c-Pr 2 c-Pr c-Bu 10-57 c-Pr 0 CH.sub.2c-Pr c-Bu 10-58 c-Pr 2 CH.sub.2c-Pr c-Bu 10-59 c-Pr 0 CH.sub.2CH.sub.2OMe c-Bu 10-60 c-Pr 2 CH.sub.2CH.sub.2OMe c-Bu

[0086] NMR data for numerous inventive compounds of the formulae (I) and (II) cited in the tables above are disclosed below using the NMR peak list method. The .sup.1H NMR data of selected examples are stated here in the form of .sup.1H NMR peak lists. For each signal peak, first the value in ppm and then the signal intensity in round brackets are listed. The pairs of value-signal intensity numbers for different signal peaks are listed with separation from one another by semicolons. The peak list for one example therefore has the form of:

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

[0087] 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. 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. In addition, like conventional .sup.1H NMR printouts, they may show solvent signals, signals of stereoisomers of the target compounds which likewise form part of the subject matter of the invention, and/or peaks of impurities.

[0088] When stating compound signals in the delta range of solvents and/or water, in our lists of 1H NMR peaks, the usual solvent peaks, for example peaks of DMSO in DMSO-D.sub.6 and the peak of water are shown, which usually have on average a high intensity.

[0089] The peaks of stereoisomers of the compounds of the invention and/or peaks of impurities usually have a lower intensity on average than the peaks of the compounds of the invention (for example with a purity of >90%).

[0090] 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.

[0091] 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 compounds of the invention, optionally using additional intensity filters. This isolation would be similar to the peak picking in question in conventional .sup.1H NMR interpretation.

[0092] Compounds of the formula (I):

Example 1-1

[0093] .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =7.556 (0.8); 7.535 (0.8); 7.519 (0.6); 7.2694 (0.6); 7.2685 (0.6); 7.268 (0.8); 7.267 (1.0); 7.266 (1.1); 7.260 (117.2); 6.996 (0.6); 6.809 (0.9); 6.789 (0.9); 4.101 (11.9); 2.840 (0.8); 2.789 (7.6); 2.307 (16.0); 2.267 (0.7); 1.547 (4.4); 1.143 (1.2); 1.139 (1.1); 1.134 (0.6); 1.127 (0.7); 1.122 (1.1); 1.117 (1.2); 1.106 (0.6); 0.786 (0.5); 0.775 (1.2); 0.770 (1.2); 0.762 (1.1); 0.757 (1.3); 0.008 (1.5); 0.000 (54.5); 0.009 (1.5)

Example 1-2

[0094] .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =9.854 (0.6); 7.605 (1.3); 7.584 (1.3); 7.519 (1.8); 7.260 (323.9); 6.996 (1.7); 6.933 (1.5); 6.912 (1.4); 4.103 (0.6); 4.088 (14.6); 3.022 (16.0); 2.831 (0.7); 2.708 (8.1); 2.307 (0.6); 2.096 (3.3); 1.545 (16.5); 1.254 (0.5); 1.195 (0.6); 1.177 (1.1); 1.156 (1.2); 0.881 (0.6); 0.867 (0.6); 0.858 (0.6); 0.805 (0.7); 0.796 (0.6); 0.008 (4.6); 0.000 (137.8); 0.009 (3.9); 0.150 (0.5)

Example 1-3

[0095] .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =7.704 (0.8); 7.683 (0.9); 7.262 (29.8); 7.093 (1.1); 7.073 (1.0); 4.115 (8.3); 3.264 (16.0); 3.034 (0.8); 3.028 (0.6); 2.823 (8.5); 1.285 (0.7); 1.256 (3.3); 1.215 (0.7); 1.203 (1.6); 1.199 (1.6); 1.194 (0.9); 1.187 (0.9); 1.182 (1.5); 1.178 (1.5); 1.166 (0.6); 0.880 (0.8); 0.874 (0.9); 0.862 (1.9); 0.859 (2.0); 0.849 (1.8); 0.845 (1.8); 0.833 (0.7); 0.000 (13.3)

Example 2-1

[0096] .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =7.542 (0.6); 7.519 (1.3); 7.260 (142.8); 6.996 (0.8); 6.800 (0.8); 6.780 (0.8); 4.486 (1.0); 4.468 (3.1); 4.450 (3.1); 4.432 (1.0); 2.850 (0.5); 2.836 (1.1); 2.829 (0.9); 2.823 (0.7); 2.815 (0.6); 2.785 (9.1); 2.310 (1.3); 2.304 (16.0); 2.264 (1.6); 2.044 (0.7); 1.637 (3.3); 1.619 (6.9); 1.600 (3.4); 1.591 (0.6); 1.573 (1.4); 1.555 (2.1); 1.259 (0.6); 1.151 (0.6); 1.140 (1.6); 1.135 (1.7); 1.130 (0.9); 1.124 (0.9); 1.119 (1.7); 1.114 (1.8); 1.103 (0.7); 0.882 (0.6); 0.782 (0.7); 0.770 (1.8); 0.766 (1.9); 0.757 (1.8); 0.753 (2.1); 0.741 (0.7); 0.008 (1.6); 0.000 (50.7); 0.009 (1.5)

Example 2-2

[0097] .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =7.605 (1.1); 7.585 (1.2); 7.519 (1.2); 7.374 (0.5); 7.260 (199.6); 7.248 (0.6); 6.996 (1.2); 6.921 (1.5); 6.900 (1.4); 4.454 (0.8); 4.437 (2.1); 4.435 (2.2); 4.419 (2.2); 4.417 (2.2); 4.401 (0.8); 3.014 (16.0); 2.782 (0.8); 2.690 (7.5); 2.306 (1.5); 2.090 (0.8); 1.637 (0.6); 1.631 (3.9); 1.618 (1.2); 1.612 (8.6); 1.594 (4.1); 1.551 (3.2); 1.177 (1.4); 1.171 (0.9); 1.161 (0.9); 1.156 (1.4); 1.140 (0.5); 0.878 (0.5); 0.864 (0.6); 0.855 (0.6); 0.794 (0.6); 0.786 (0.6); 0.771 (0.5); 0.008 (2.4); 0.000 (71.6); 0.009 (2.1)

Example 2-3

[0098] .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =7.687 (1.0); 7.666 (1.0); 7.271 (0.6); 7.270 (0.7); 7.269 (0.8); 7.268 (0.9); 7.261 (83.2); 7.095 (1.2); 7.074 (1.1); 4.501 (0.9); 4.482 (2.8); 4.464 (2.8); 4.446 (0.9); 3.264 (16.0); 3.043 (0.7); 2.834 (9.0); 2.006 (1.2); 1.642 (3.4); 1.624 (7.6); 1.606 (3.5); 1.574 (1.0); 1.219 (0.5); 1.207 (1.3); 1.202 (1.3); 1.198 (0.7); 1.191 (0.7); 1.185 (1.2); 1.181 (1.3); 1.170 (0.6); 0.873 (0.6); 0.862 (1.3); 0.858 (1.4); 0.848 (1.3); 0.844 (1.4); 0.008 (0.9); 0.000 (27.8); 0.009 (0.8)

Example 3-1

[0099] .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =7.519 (1.3); 7.495 (0.7); 7.2763 (0.5); 7.2755 (0.6); 7.275 (0.6); 7.273 (0.7); 7.2723 (0.8); 7.2715 (0.9); 7.271 (1.0); 7.270 (1.1); 7.2683 (1.5); 7.2675 (1.7); 7.267 (1.9); 7.260 (158.8); 6.996 (0.9); 6.800 (0.9); 6.780 (0.9); 5.300 (4.4); 4.412 (1.4); 4.394 (1.8); 4.375 (1.5); 2.837 (0.7); 2.781 (7.0); 2.314 (0.6); 2.305 (16.0); 2.049 (0.8); 2.031 (1.5); 2.012 (1.5); 1.994 (0.9); 1.551 (2.0); 1.153 (0.5); 1.142 (1.3); 1.137 (1.3); 1.132 (0.7); 1.126 (0.7); 1.121 (1.3); 1.116 (1.3); 1.105 (0.6); 1.003 (3.1); 0.984 (6.6); 0.966 (3.0); 0.780 (0.6); 0.769 (1.3); 0.764 (1.4); 0.755 (1.3); 0.751 (1.5); 0.739 (0.5); 0.008 (2.0); 0.006 (0.8); 0.000 (60.1); 0.006 (0.7); 0.007 (0.5); 0.009 (1.7)

Example 3-2

[0100] .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =7.584 (1.0); 7.564 (1.0); 7.519 (2.2); 7.292 (0.6); 7.276 (1.4); 7.273 (2.0); 7.260 (387.6); 7.252 (1.5); 7.250 (0.9); 7.249 (0.9); 7.210 (0.7); 6.996 (2.2); 6.927 (1.5); 6.907 (1.4); 4.384 (1.1); 4.381 (1.2); 4.366 (2.0); 4.361 (1.9); 4.347 (1.2); 4.344 (1.2); 3.247 (1.2); 3.016 (16.0); 2.834 (0.7); 2.702 (7.1); 2.093 (0.9); 2.044 (1.1); 2.025 (2.1); 2.007 (2.1); 1.988 (1.2); 1.548 (17.9); 1.189 (0.5); 1.174 (1.4); 1.168 (0.9); 1.153 (1.3); 1.007 (4.1); 0.995 (0.9); 0.989 (8.7); 0.970 (3.8); 0.860 (0.6); 0.851 (0.6); 0.799 (0.7); 0.791 (0.6); 0.008 (4.3); 0.000 (134.5); 0.009 (3.9)

Example 3-3

[0101] .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =7.664 (1.0); 7.644 (1.1); 7.519 (0.7); 7.311 (0.8); 7.273 (1.0); 7.272 (0.9); 7.261 (126.8); 7.237 (1.0); 7.211 (0.6); 7.183 (1.0); 7.176 (0.5); 7.167 (0.6); 7.165 (0.7); 7.163 (0.7); 7.162 (0.6); 7.092 (1.2); 7.071 (1.2); 6.997 (0.8); 4.427 (1.5); 4.409 (1.9); 4.391 (1.5); 3.356 (0.6); 3.270 (0.8); 3.261 (16.0); 3.235 (0.5); 3.043 (0.8); 2.836 (9.4); 2.356 (3.7); 2.088 (1.2); 2.050 (0.9); 2.032 (1.6); 2.013 (1.7); 1.995 (1.0); 1.567 (1.1); 1.219 (0.5); 1.207 (1.3); 1.203 (1.4); 1.198 (0.8); 1.191 (0.8); 1.186 (1.3); 1.182 (1.4); 1.170 (0.6); 1.010 (3.5); 0.991 (7.4); 0.973 (3.3); 0.869 (0.6); 0.857 (1.4); 0.854 (1.6); 0.844 (1.4); 0.840 (1.5); 0.828 (0.6); 0.008 (1.4); 0.000 (45.9); 0.009 (1.4)

Example 4-1

[0102] .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =7.519 (1.2); 7.494 (1.8); 7.456 (0.9); 7.436 (0.9); 7.260 (214.1); 6.996 (1.1); 6.777 (1.0); 6.756 (1.0); 3.880 (10.0); 2.830 (0.7); 2.757 (8.3); 2.297 (16.0); 2.045 (0.6); 1.542 (13.1); 1.146 (0.5); 1.134 (1.2); 1.130 (1.2); 1.125 (0.6); 1.118 (0.7); 1.113 (1.2); 1.108 (1.1); 1.097 (0.5); 0.768 (0.5); 0.757 (1.2); 0.752 (1.2); 0.743 (1.1); 0.739 (1.3); 0.008 (2.8); 0.000 (95.1); 0.009 (2.6)

Example 4-2

[0103] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): =10.987 (1.4); 7.877 (2.3); 7.562 (0.7); 7.543 (0.8); 7.048 (1.1); 7.028 (1.1); 3.743 (16.0); 3.420 (0.5); 3.390 (0.5); 3.359 (0.7); 3.354 (0.9); 3.350 (1.0); 3.320 (733.1); 3.297 (31.4); 3.270 (1.4); 3.174 (0.7); 3.161 (0.7); 3.018 (14.4); 2.863 (0.5); 2.844 (0.6); 2.675 (1.3); 2.670 (1.8); 2.665 (1.4); 2.661 (0.8); 2.646 (9.4); 2.540 (1.1); 2.523 (4.9); 2.519 (7.6); 2.510 (96.8); 2.506 (208.5); 2.501 (288.8); 2.496 (201.8); 2.492 (89.9); 2.474 (1.2); 2.469 (1.1); 2.460 (0.8); 2.456 (0.8); 2.451 (0.9); 2.447 (0.5); 2.337 (0.5); 2.332 (1.2); 2.328 (1.7); 2.323 (1.3); 2.299 (0.5); 1.094 (0.5); 1.085 (0.6); 0.999 (0.5); 0.926 (0.6); 0.913 (0.7); 0.735 (0.6); 0.720 (0.6); 0.000 (0.5)

Example 4-3

[0104] .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =7.604 (0.8); 7.584 (0.9); 7.410 (1.1); 7.261 (52.3); 7.063 (1.1); 7.042 (1.1); 3.890 (9.3); 3.230 (16.0); 3.042 (0.7); 2.815 (9.1); 2.055 (0.9); 1.285 (0.6); 1.255 (1.8); 1.212 (0.6); 1.200 (1.4); 1.196 (1.4); 1.191 (0.8); 1.184 (0.8); 1.179 (1.4); 1.175 (1.4); 1.163 (0.7); 0.849 (0.7); 0.837 (1.5); 0.834 (1.6); 0.824 (1.4); 0.820 (1.5); 0.808 (0.5); 0.008 (0.7); 0.000 (23.5); 0.009 (0.7)

Example 7-1

[0105] .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =7.261 (70.3); 6.751 (1.2); 6.731 (1.2); 5.300 (1.6); 2.821 (0.9); 2.762 (11.2); 2.543 (10.9); 2.296 (16.0); 2.007 (7.2); 1.561 (2.5); 1.133 (0.6); 1.121 (1.4); 1.117 (1.4); 1.112 (0.8); 1.105 (0.8); 1.100 (1.4); 1.095 (1.4); 1.084 (0.6); 0.759 (0.7); 0.748 (1.6); 0.744 (1.6); 0.735 (1.5); 0.731 (1.6); 0.719 (0.5); 0.008 (0.9); 0.000 (28.7); 0.009 (0.7)

Example 7-2

[0106] .sup.1H-NMR (400.0 MHz, CDCl.sub.3): =7.532 (0.7); 7.520 (0.7); 7.511 (0.8); 7.261 (98.5); 7.228 (0.7); 6.997 (0.5); 6.871 (1.5); 6.851 (1.4); 3.001 (16.0); 2.655 (7.4); 2.547 (15.5); 1.333 (0.7); 1.285 (1.0); 1.255 (0.7); 1.119 (0.6); 1.110 (0.7); 1.106 (0.6); 1.097 (0.8); 1.087 (0.5); 1.076 (0.5); 0.834 (0.6); 0.768 (0.5); 0.758 (0.6); 0.74458 (0.5); 0.008 (1.0); 0.000 (34.6); 0.009 (1.0)

Example 7-3

[0107] .sup.1H-NMR (400.0 MHz, d.sub.6-DMSO): =12.049 (4.0); 7.606 (13.5); 7.586 (15.1); 7.145 (13.9); 7.124 (12.9); 5.755 (10.3); 3.352 (147.7); 3.314 (712.8); 3.290 (37.0); 2.894 (7.6); 2.880 (4.2); 2.674 (6.3); 2.670 (9.0); 2.665 (6.6); 2.638 (96.5); 2.539 (10.8); 2.534 (12.5); 2.530 (10.5); 2.523 (23.2); 2.518 (34.1); 2.510 (496.8); 2.505 (1075.7); 2.501 (1494.7); 2.496 (1040.4); 2.491 (467.1); 2.475 (130.1); 2.332 (5.6); 2.328 (8.5); 2.323 (6.0); 2.073 (13.1); 1.335 (2.9); 1.298 (3.0); 1.259 (4.6); 1.250 (4.7); 1.235 (4.9); 1.118 (4.6); 1.107 (12.3); 1.102 (13.3); 1.091 (7.4); 1.086 (13.0); 1.081 (13.4); 1.070 (5.8); 0.864 (5.7); 0.848 (16.0); 0.835 (14.5); 0.824 (4.3); 0.034 (2.6); 0.008 (15.2); 0.000 (516.1); 0.009 (15.7)

Compounds of the Formula (II):

Example 9-1

[0108] .sup.1H-NMR (400.0 MHz, de-DMSO):

[0109] =7.628 (1.5); 7.608 (1.6); 6.806 (1.3); 6.785 (1.2); 3.320 (3.2); 2.772 (0.6); 2.749 (9.5); 2.737 (0.9); 2.723 (0.5); 2.511 (4.4); 2.507 (9.5); 2.502 (13.3); 2.498 (9.6); 2.493 (4.7); 2.478 (0.6); 2.258 (16.0); 2.029 (0.7); 1.078 (1.2); 1.072 (1.3); 1.068 (0.7); 1.062 (0.7); 1.057 (1.3); 1.051 (1.3); 1.041 (0.6); 0.752 (0.5); 0.741 (1.3); 0.736 (1.4); 0.728 (1.3); 0.723 (1.4); 0.712 (0.5); 0.000 (5.4)

B. FORMULATION EXAMPLES

[0110] 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 an inert substance and comminuting the mixture in a hammer mill. [0111] 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 an inert substance, 10 parts by weight of potassium lignosulfonate and 1 part by weight of sodium oleoylmethyltaurate as a wetting agent and dispersant, and grinding the mixture in a pinned-disk mill. [0112] c) A readily water-dispersible dispersion concentrate is obtained by mixing 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 for example about 255 to above 277 C), and grinding the mixture in a friction ball mill to a fineness of below 5 microns. [0113] 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 a solvent and 10 parts by weight of ethoxylated nonylphenol as an emulsifier. [0114] e) Water-dispersible granules are obtained by mixing [0115] 75 parts by weight of a compound of the formula (I) and/or salts thereof, [0116] 10 parts by weight of calcium lignosulfonate, [0117] 5 parts by weight of sodium lauryl sulfate, [0118] 3 parts by weight of polyvinyl alcohol and [0119] 7 parts by weight of kaolin, [0120] grinding the mixture in a pinned-disk mill, and granulating the powder in a [0121] fluidized bed by spray application of water as a granulating liquid. [0122] f) Water-dispersible granules are also obtained by homogenizing and precomminuting, in a colloid mill, [0123] 25 parts by weight of a compound of the formula (I) and/or salts thereof, [0124] 5 parts by weight of sodium 2,2-dinaphthylmethane-6,6-disulfonate [0125] 2 parts by weight of sodium oleoylmethyltaurate, [0126] 1 part by weight of polyvinyl alcohol [0127] 17 parts by weight of calcium carbonate and [0128] 50 parts by weight of water, [0129] 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

[0130] The abbreviations used here are:

TABLE-US-00011 ABUTH Abutilon theophrasti ALOMY Alopecurus myosuroides AMARE Amaranthus retroflexus AVEFA Avena fatua CYPES Cyperus serotinus ECHCG Echinochloa crus galli LOLMU Lolium multiflorum MATIN Matricaria inodora PHBPU Pharbitis purpureum PHBPU Pharbitis purpureum POLCO Polygonum convolvulus STEME Stellaria media VERPE Veronica persica

1. Pre-Emergence Herbicidal Action Against Harmful Plants

[0131] Seeds of monocotyledonous and dicotyledonous weed plants and crop plants are laid out in wood-fiber pots in sandy loam and covered with soil. The compounds of the invention and, for comparative purposes, the compounds known from the prior art, formulated in the form of wettable powders (WP) or as emulsion concentrates (EC), are then applied to the surface of the covering soil as aqueous suspension or emulsion at a water application rate equating to 600 to 800 I/ha with addition of 0.2% of wetting agent. After the treatment, the pots are placed in a greenhouse and kept under good growth conditions for the trial plants. The damage to the test plants is scored visually after a test period of 3 weeks by comparison with untreated controls (herbicidal activity in percent (%): 100% activity=the plants have died, 0% activity=like control plants).

[0132] The experiments show that the compounds of the invention tested have higher herbicidal action against numerous harmful plants and have lower damage in crop plants than the structurally closest compounds known from the prior art. The data from these experiments are listed in the following tables:

TABLE-US-00012 TABLE A Dosage Activity against Compound [g/ha] CYPES POLCO [00018] 320 90% 90% [00019] 320 30% 0% [00020] 320 0% 70%

TABLE-US-00013 TABLE B Dosage Activity against Compound [g/ha] CYPES POLCO [00021] 320 90% 90% [00022] 320 0% 20% [00023] 320 30% 0% [00024] 320 0% 30% [00025] 320 0% 0%

TABLE-US-00014 TABLE C Dosage Activity against Compound [g/ha] ALOMY AMARE [00026] 320 90% 100% [00027] 320 20% 20% [00028] 320 0% 0% [00029] 320 0% 0%

TABLE-US-00015 TABLE D Dosage Activity against Compound [g/ha] ALOMY POLCO [00030] 320 100% 90% [00031] 320 70% 40% [00032] 320 20% 60% [00033] 320 0% 60%

TABLE-US-00016 TABLE E Dosage Activity against Compound [g/ha] AMARE VERPE [00034] 320 100% 90% [00035] 320 80% 70% [00036] 320 60% 0% [00037] 320 30% 0% [00038] 320 0% 0%

TABLE-US-00017 TABLE F Dosage Activity against Compound [g/ha] AMARE MATIN [00039] 320 90% 80% [00040] 320 70% 30% [00041] 320 60% 0% [00042] 320 40% 0% [00043] 320 20% 0%

TABLE-US-00018 TABLE G Dosage Activity against Compound [g/ha] ECHCG AMARE [00044] 320 90% 100% [00045] 320 30% 10% [00046] 320 0% 40% [00047] 320 20% 0% [00048] 320 40% 60%

TABLE-US-00019 TABLE H Dosage Activity against Compound [g/ha] AVEFA LOLMU [00049] 320 100% 90% [00050] 320 60% 30%

TABLE-US-00020 TABLE I Dosage Activity against Compound [g/ha] LOLMU PHBPU [00051] 320 100% 100% [00052] 320 30% 60%

TABLE-US-00021 TABLE J Dosage Activity against Compound [g/ha] CYPES ABUTH [00053] 80 80% 100% [00054] 80 40% 80%

2. Post-Emergence Herbicidal Action Against Harmful Plants

[0133] Seeds of monocotyledonous and dicotyledonous weed and crop plants are laid out in sandy loam in wood-fiber pots, covered with soil and cultivated in a greenhouse under good 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 in the form of an aqueous suspension or emulsion at a water application rate equating to 600 to 800 I/ha, with addition of 0.2% wetting agent. After the test plants have been left to stand in the greenhouse under optimal growth conditions for about 3 weeks, the action of the preparations is assessed visually in comparison to untreated controls (herbicidal action in percent (%): 100% activity=the plants have died, 0% activity=like control plants). The experiments show that the compounds of the invention tested have higher herbicidal action against numerous harmful plants and have lower damage in crop plants than the structurally closest compounds known from the prior art. The data from these experiments are listed in the following tables:

TABLE-US-00022 TABLE K Dosage Activity against Compound [g/ha] MATIN STEME [00055] 80 80% 90% [00056] 80 60% 70% [00057] 80 40% 60%

TABLE-US-00023 TABLE L Dosage Activity against Compound [g/ha] MATIN POLCO [00058] 80 80% 60% [00059] 80 60% 20% [00060] 80 60% 0%