SUBSTITUTED (2-HETEROARYLOXYPHENYL)SULFONATES, SALTS THEREOF AND THEIR USE AS HERBICIDAL AGENTS

Abstract

Described are substituted (2-heteroaryloxyphenyl)sulfonates of the general formula (I)

##STR00001##

and their use as herbicides, in particular for controlling broad-leaved weeds and/or weed grasses in crops of useful plants and/or as plant growth regulators for influencing the growth of crops of useful plants.

The present invention further relates to herbicidal and/or plant growth-regulating compositions comprising one or more compounds of the general formula (I).

Claims

1. A substituted (2-heteroaryloxyphenyl)sulfonate compound of general formula (I) or salt thereof ##STR00020## in which R.sup.1 is (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-halocycloalkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-haloalkenyl, (C.sub.3-C.sub.6)-cycloalkenyl, (C.sub.3-C.sub.6)-halocycloalkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.2-C.sub.6)-haloalkynyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.4)-alkyl, (C.sub.3-C.sub.6)-halocycloalkyl-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkyl-(C.sub.3-C.sub.6)-cycloalkyl, (C.sub.1-C.sub.4)-haloalkyl-(C.sub.3-C.sub.6)-cycloalkyl, (C.sub.1-C.sub.4)-alkoxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkoxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.3-C.sub.6)-cycloalkoxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.2-C.sub.4)-alkenyloxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.2-C.sub.4)-haloalkenyloxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.3-C.sub.6)-cycloalkenyloxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.2-C.sub.6)-cyanoalkyl, (C.sub.1-C.sub.4)-alkylthio-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkylthio-(C.sub.1-C.sub.4)-alkyl or (C.sub.3-C.sub.6)-cycloalkylthio-(C.sub.1-C.sub.4)-alkyl, R.sup.2 and R.sup.3 are independently hydrogen, halogen, hydroxy, amino, cyano, nitro, formyl, formamide, (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, (C.sub.2-C.sub.4)-alkynyl, (C.sub.2-C.sub.4)-haloalkenyl, (C.sub.2-C.sub.4)-haloalkynyl, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-haloalkoxy, (C.sub.3-C.sub.6)-cycloalkoxy, (C.sub.2-C.sub.4)-alkenyloxy, (C.sub.1-C.sub.4)-alkynyloxy, (C.sub.1-C.sub.4)-alkylthio, (C.sub.1-C.sub.4)-haloalkylthio, (C.sub.3-C.sub.6)-cycloalkylthio, (C.sub.1-C.sub.4)-alkylsulfinyl, (C.sub.1-C.sub.4)-haloalkylsulfinyl, (C.sub.3-C.sub.6)-cycloalkylsulfinyl, (C.sub.1-C.sub.4)-alkylsulfonyl, (C.sub.1-C.sub.4)-haloalkylsulfonyl, (C.sub.3-C.sub.6)-cycloalkylsulfonyl, (C.sub.1-C.sub.4)-alkoxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkoxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkylthio-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkylsulfinyl-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkylsulfonyl-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkylcarbonyl, (C.sub.1-C.sub.4)-haloalkylcarbonyl, (C.sub.3-C.sub.6)-cycloalkylcarbonyl, (C.sub.1-C.sub.4)-alkylcarbonyloxy, (C.sub.1-C.sub.4)-haloalkylcarbonyloxy, carboxyl, (C.sub.1-C.sub.4)-alkoxycarbonyl, (C.sub.1-C.sub.4)-haloalkoxycarbonyl, (C.sub.3-C.sub.6)-cycloalkoxycarbonyl, (C.sub.1-C.sub.4)-alkylaminocarbonyl, (C.sub.2-C.sub.6)-dialkylaminocarbonyl, (C.sub.3-C.sub.6)-cycloalkylaminocarbonyl, (C.sub.1-C.sub.4)-alkylcarbonylamino, (C.sub.1-C.sub.4)-haloalkylcarbonylamino, (C.sub.2-C.sub.6)-cycloalkylcarbonylamino, (C.sub.1-C.sub.4)-alkoxycarbonylamino, (C.sub.1-C.sub.4)-alkylaminocarbonylamino, (C.sub.2-C.sub.6)-dialkylaminocarbonylamino, carboxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkoxycarbonyl-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkoxycarbonyl-(C.sub.1-C.sub.4)-alkyl, (C.sub.3-C.sub.6)-cycloalkoxycarbonyl-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkylaminosulfonyl, (C.sub.2-C.sub.6)-dialkylaminosulfonyl or (C.sub.3-C.sub.6)-trialkylsilyl, R.sup.4 is hydrogen, halogen, cyano, nitro, (C.sub.1-C.sub.4)-alkyl or (C.sub.1-C.sub.4)-haloalkyl, X is N or CR.sup.5, Y is N or CH, and R.sup.5 is hydrogen, halogen or cyano.

2. The compound of the general formula (I) as claimed in claim 1 or salt thereof, in which R.sup.1 is (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-halocycloalkyl, (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-(C.sub.1-C.sub.4)-alkyl, (C.sub.3-C.sub.6)-halocycloalkyl-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkyl-(C.sub.3-C.sub.6)-cycloalkyl, (C.sub.1-C.sub.4)-haloalkyl-(C.sub.3-C.sub.6)-cycloalkyl, (C.sub.1-C.sub.4)-alkoxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkoxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.3-C.sub.6)-cycloalkoxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.2-C.sub.4)-alkenyloxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.2-C.sub.6)-cyanoalkyl, (C.sub.1-C.sub.4)-alkylthio-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkylthio-(C.sub.1-C.sub.4)-alkyl or (C.sub.3-C.sub.6)-cycloalkylthio-(C.sub.1-C.sub.4)-alkyl, R.sup.2 and R.sup.3 are independently hydrogen, halogen, hydroxy, cyano, nitro, formyl, formamide, (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, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-haloalkoxy, (C.sub.2-C.sub.4)-alkenyloxy, (C.sub.1-C.sub.4)-alkylthio, (C.sub.1-C.sub.4)-haloalkylthio, (C.sub.1-C.sub.4)-alkoxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkoxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkylcarbonyl, (C.sub.1-C.sub.4)-haloalkylcarbonyl, (C.sub.3-C.sub.6)-cycloalkylcarbonyl, carboxyl, (C.sub.1-C.sub.4)-alkoxycarbonyl, (C.sub.1-C.sub.4)-haloalkoxycarbonyl, (C.sub.3-C.sub.6)-cycloalkoxycarbonyl, (C.sub.1-C.sub.4)-alkylcarbonylamino, (C.sub.1-C.sub.4)-haloalkylcarbonylamino, (C.sub.1-C.sub.4)-alkoxycarbonylamino or (C.sub.3-C.sub.6)-trialkylsilyl, R.sup.4 is hydrogen, halogen, cyano, nitro, (C.sub.1-C.sub.4)-alkyl or (C.sub.1-C.sub.4)-haloalkyl, X is N or CR.sup.5, Y is N or CH, and R.sup.5 is hydrogen, halogen or cyano.

3. The compound of the general formula (I) as claimed in claim 1 or a salt thereof, in which R.sup.1 is (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.3-C.sub.6)-cycloalkyl, (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-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkoxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkoxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.2-C.sub.6)-cyanoalkyl, (C.sub.1-C.sub.4)-alkylthio-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkylthio-(C.sub.1-C.sub.4)-alkyl, (C.sub.3-C.sub.6)-halocycloalkyl-(C.sub.1-C.sub.4)-alkyl, or (C.sub.3-C.sub.6)-cycloalkoxy-(C.sub.1-C.sub.4)-alkyl, R.sup.2 and R.sup.3 are independently hydrogen, halogen, cyano, (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, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-haloalkoxy, (C.sub.1-C.sub.4)-alkylthio or (C.sub.1-C.sub.4)-haloalkylthio, R.sup.4 is hydrogen, halogen, cyano, nitro, methyl or trifluoromethyl, X is N or CR.sup.5, Y is N or CH, and R.sup.5 is hydrogen, halogen or cyano.

4. The compound of the general formula (I) as claimed in claim 1 or a salt thereof, in which R.sup.1 is (C.sub.1-C.sub.5)-alkyl, (C.sub.1-C.sub.5)-haloalkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.2-C.sub.5)-alkenyl, (C.sub.2-C.sub.5)-haloalkenyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.4)-alkyl, (C.sub.3-C.sub.6)-halocycloalkyl-(C.sub.1-C.sub.4)-alkyl, (C.sub.3-C.sub.6)-cycloalkoxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkoxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkoxy-(C.sub.1-C.sub.4)-alkyl or (C.sub.2-C.sub.6)-cyanoalkyl, R.sup.2 and R.sup.3 are independently hydrogen, halogen, cyano, (C.sub.1-C.sub.2)-alkyl, (C.sub.1-C.sub.2)-haloalkyl, vinyl, (C.sub.1-C.sub.2)-alkoxy or (C.sub.1-C.sub.2)-haloalkoxy, R.sup.4 is hydrogen, halogen, nitro, cyano or trifluoromethyl, X is N or CR.sup.5, Y is N or CH, and R.sup.5 is hydrogen, halogen or cyano.

5. The compound of the general formula (I) as claimed in claim 1 or a salt thereof, in which R.sup.1 is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, n-pentyl, isopentyl, chloromethyl, 1-chloroprop-3-yl, 1-chlorobut-4-yl, 1,1,1-trifluoroeth-2-yl, 1,1,1-trifluoroprop-3-yl, 1,1,1-trifluorobut-4-yl, cyclopropyl, cyclopentyl, cyclopropylmethyl, 1-methoxyeth-2-yl, prop-2-en-1-yl, vinyl, but-3-en-1-yl, 4,4-difluorobutyl, trifluorobut-3-enyl, 4,4,5,5,5-pentafluoropentyl, 3,3-dichloroallyl or 2-(2,2-dichlorocyclopropyl)ethan-1-yl, (3,3-difluorocyclobutane)methan-1-yl, tetrahydrofuran-2-ylmethyl, (2,2-dichlorocyclopropyl)methyl, 3-(trifluoromethoxy)propyl or 3-cyanopropyl, R.sup.2 is hydrogen, fluorine, chlorine, bromine, cyano, methyl or methoxy, R.sup.3 is hydrogen, fluorine or methyl, R.sup.4 is fluorine, chlorine, bromine, nitro, cyano or trifluoromethyl, X is N, CH, CF or CCN, and Y is N or CH.

6. A herbicidal composition comprising at least one compound of the general formula (I) as claimed in claim 1.

7. The herbicidal composition as claimed in claim 6, further comprising at least one formulation auxiliary.

8. The herbicidal composition as claimed in claim 6, further comprising at least one of an insecticide, acaricide, herbicide, fungicide, safener, and growth regulator.

9. The herbicidal composition as claimed in claim 8, wherein the composition comprises a safener.

10. The herbicidal composition as claimed in claim 9, further comprising one of cyprosulfamide, cloquintocet-mexyl, mefenpyr-diethyl or isoxadifen-ethyl.

11. The herbicidal composition as claimed in claim 6, further comprising a further herbicide.

12. A method of controlling unwanted plants, the method comprising applying at least one compound of the general formula (I) as claimed in claim 1 to the unwanted plants or to a site of the unwanted plants.

13. (canceled)

14. The method as claimed in claim 12, characterized in that each of the at least one compounds of the general formula (I) are used for controlling unwanted plants in crops.

15. The method as claimed in claim 14, wherein the crops comprise transgenic plants.

16. A method of controlling unwanted plants, the method comprising applying an herbicidal composition as claimed in claim 6 to the unwanted plants or to a site of the unwanted plants.

Description

SYNTHESIS EXAMPLES

Synthesis Example No. I-7

Synthesis Stage 1: 2-(5-Chloropyrimidin-2-yl)oxyphenol (=Intermediate A-01)

[0094] ##STR00006##

[0095] A mixture of catechol (4.00 g, 36.3 mmol), 2,5-dichloropyrimidine (4.87 ml, 32.7 mmol) and N,N-diisopropylethylamine (6.96 ml, 40.0 mmol) in 15 ml of chlorobenzene was heated at 140? C. for 9 h. The resulting reaction mixture was cooled down to room temperature, diluted with water and extracted repeatedly with ethyl acetate. The combined organic phases were then washed with water, dried over magnesium sulfate, filtered and concentrated. By subsequent purification of the resulting crude product by column chromatography (ethyl acetate/heptane gradient), 2-(5-chloropyrimidin-2-yl)oxyphenol was isolated.

[0096] The yield was 4.33 g (53% of theory).

Synthesis Stage 2: [2-(5-Chloropyrimidin-2-yl)oxyphenyl] 2-methylpropane-1-sulfonate (=Synthesis Example No. I-7)

[0097] ##STR00007##

[0098] A mixture of 2-(5-chloropyrimidin-2-yl)oxyphenol (intermediate A-01, 150 mg, 0.67 mmol) and 1-methylimidazole (160 ?l, 2.02 mmol) in 8 ml of dichloroethane was cooled down to 0? C., and isobutanesulfonyl chloride (114 ?l, 0.88 mmol) was added. The mixture was stirred at room temperature for 18 hours. The resulting reaction mixture was concentrated, diluted with 30 ml of water and 4 equivalents of 6M HCl, and then extracted repeatedly with ethyl acetate. The combined organic phases were then dried over magnesium sulfate, filtered and concentrated. In this way, [2-(5-chloropyrimidin-2-yl)oxyphenyl] 2-methylpropane-1-sulfonate (synthesis example no. I-7) was isolated.

[0099] The yield was 200 mg (86% of theory).

Synthesis Example No. I-28

Synthesis Stage 1: 2-Methoxy-3-methylphenol (=Intermediate A-02)

[0100] ##STR00008##

[0101] A mixture of 2-methoxy-3-methylbenzaldehyde (4.00 g, 26.6 mmol) in 80 ml of dichloromethane was cooled down to 0? C., and m-CPBA 77% (8.95 g, 39.9 mmol) was added. The mixture was stirred at room temperature for 18 hours. The resulting reaction mixture was concentrated, diluted with 100 ml of dichloromethane and a mixture of saturated NaHCO.sub.3/saturated Na.sub.2S.sub.2O.sub.3 solution 1:1 (1?200 ml), and then extracted repeatedly with dichloromethane. The combined organic phases were washed with water and saturated NaCl solution, dried over magnesium sulfate, filtered and concentrated. The intermediate was dissolved in 60 ml of methanol, and triethylamine was added. The mixture was stirred at room temperature for 48 hours and then concentrated. By subsequent purification of the resulting crude product by column chromatography (acetone/heptane gradient), 2-methoxy-3-methylphenol was isolated.

[0102] The yield was 3.45 g (89% of theory).

Synthesis Stage 2: 5-Chloro-2-(2-methoxy-3-methylphenoxy)pyrimidine (=Intermediate A-03)

[0103] ##STR00009##

[0104] A mixture of intermediate A02 (1.10 g, 7.96 mmol), 2,5-dichloropyrimidine (1.30 ml, 8.75 mmol) and potassium carbonate (2.75 g, 19.9 mmol) in 10 ml of dimethylformamide was heated at 80? C. for 2 h. The resulting reaction mixture was cooled down to room temperature, diluted with water and extracted repeatedly with tert-butyl methyl ether. The combined organic phases were then washed with water, dried over magnesium sulfate, filtered and concentrated. By subsequent purification of the resulting crude product by column chromatography (acetone/heptane gradient), 5-chloro-2-(2-methoxy-3-methylphenoxy)pyrimidine was isolated.

[0105] The yield was 1.88 g (84% of theory).

Synthesis Stage 3: 2-[(5-Chloropyrimidin-2-yl)oxy]-6-methylphenol (=Intermediate A-04)

[0106] ##STR00010##

[0107] A mixture of 5-chloro-2-(2-methoxy-3-methylphenoxy)pyrimidine A03 (1.80 g, 7.18 mmol) in 20 ml of dichloromethane was cooled down to ?78? C. under nitrogen, and boron tribromide (1M in dichloromethane) (21.50 ml, 21.50 mmol) was cautiously added dropwise at ?78? C. The mixture was then allowed to come to room temperature, and stirring was continued at room temperature. The resulting reaction mixture was diluted with ice-water and subsequently extracted repeatedly with dichloromethane. The combined organic phases were then washed with water and saturated NaCl solution, dried over magnesium sulfate, filtered and concentrated. 2-[(5-Chloropyrimidin-2-yl)oxy]-6-methylphenol was isolated without further purification. The yield was 1.59 g (79% of theory).

Synthesis Stage 4: 2-[(5-Chloropyrimidin-2-yl)oxy]-6-methylphenyl 4,4,4-trifluorobutane-1-sulfonate (=Synthesis Example No. I-28)

[0108] ##STR00011##

[0109] A mixture of 2-[(5-chloropyrimidin-2-yl)oxy]-6-methylphenol (intermediate A-04, 150 mg, 0.63 mmol) and 1-methylimidazole (202 ?l, 2.53 mmol) in 5 ml of dichloroethane was cooled down to 0? C., and 4,4,4-trifluorobutane-1-sulfonyl chloride (182 ?l, 1.26 mmol) was added. The mixture was stirred at room temperature for 18 hours. The resulting reaction mixture was concentrated, diluted with 30 ml of water and 4 equivalents of 6M HCl, and then extracted repeatedly with ethyl acetate. The combined organic phases were then dried over magnesium sulfate, filtered and concentrated. Subsequent purification of the resulting crude product by column chromatography (acetone/heptane gradient) resulted in isolation of 2-[(5-chloropyrimidin-2-yl)oxy]-6-methylphenyl 4,4,4-trifluorobutane-1-sulfonate (synthesis example no. I-28).

[0110] The yield was 145 mg (54% of theory).

[0111] In analogy to the preparation examples cited above and recited at the appropriate point, the inventive compounds of the general formula (I) specified hereinafter and shown in table 1 are obtained.

##STR00012##

TABLE-US-00001 TABLE 1 Exam- ple number R.sup.1 R.sup.2 R.sup.3 R.sup.4 X Y I-1 methyl H H Cl N CH I-2 1-chloroprop-3-yl H H Cl N CH I-3 n-propyl H H Cl N CH I-4 1,1,1-trifluoroeth-2-yl H H Cl N CH I-5 1-chloroprop-3-yl H H F N CH I-6 n-butyl H H Cl N CH I-7 isobutyl H H Cl N CH I-8 1,1,1-trifluoroprop-3-yl H H Cl N CH I-9 chloromethyl H H Cl N CH I-10 1,1,1-trifluorobut-4-yl H H Cl N CH I-11 1-chloroprop-3-yl Me H Cl N CH I-12 1-chloroprop-3-yl H Me Cl N CH I-13 1-chloroprop-3-yl H F Cl N CH I-14 1-chloroprop-3-yl F H Cl N CH I-15 1-chlorobut-4-yl H H Cl N CH I-16 ethyl H H Cl N CH I-17 n-butyl OMe H Cl N CH I-18 isopropyl H H Cl N CH I-19 cyclopentyl H H Cl N CH I-20 1-methoxyeth-2-yl H H Cl N CH I-21 cyclopropyl H H Cl N CH I-22 sec-butyl H H Cl N CH I-23 cyclopropylmethyl H H Cl N CH I-24 n-pentyl H H Cl N CH I-25 isopentyl H H Cl N CH I-26 1,1,1-trifluorobut-4-yl H H Cl CH CH I-27 1-chloroprop-3-yl H H Cl CH CH I-28 1,1,1-trifluorobut-4-yl Me H Cl N CH I-29 1,1,1-trifluoroprop-3-yl Me H Cl N CH I-30 1,1,1-trifluorobut-4-yl Br H Cl N CH I-31 1,1,1-trifluoroprop-3-yl Br H Cl N CH I-32 1,1,1-trifluoroprop-3-yl Cl H Br N CH I-33 1,1,1-trifluoroprop-3-yl Me H Br N CH I-34 1,1,1-trifluorobut-4-yl Cl H Br N CH I-35 1,1,1-trifluorobut-4-yl Me H Br N CH I-36 prop-2-en-1-yl H H Cl N CH I-37 vinyl H H Cl N CH I-38 1,1,1-trifluoroprop-3-yl Cl H Cl N CH I-39 1,1,1-trifluorobut-4-yl Cl H Cl N CH I-40 1,1,1-trifluoroprop-3-yl F H Br N CH I-41 1,1,1-trifluorobut-4-yl F H Br N CH I-42 1,1,1-trifluorobut-4-yl F H F N CH I-43 1,1,1-trifluoroprop-3-yl Br H F N CH I-44 1,1,1-trifluorobut-4-yl Br H F N CH I-45 1,1,1-trifluoroprop-3-yl Me H F N CH I-46 1,1,1-trifluorobut-4-yl Me H F N CH I-47 1,1,1-trifluoroprop-3-yl F H F N CH I-48 1,1,1-trifluoroprop-3-yl F H Cl N CH I-49 1,1,1-trifluorobut-4-yl F H Cl N CH I-50 but-3-en-1-yl F H Cl N CH I-51 2-(2,2-dichlorocyclo- F H Cl N CH propyl)ethan-1-yl I-52 2-methoxyethan-1-yl F H Cl N CH I-53 (3,3-difluorocyclobutyl)methan- F H Cl N CH 1-yl I-54 tetrahydrofuran-2-ylmethyl F H Cl N CH I-55 2-cyclopropylethyl F H Cl N CH I-56 4,4-difluorobutyl F H Cl N CH I-57 (2,2-dichlorocyclopropyl)methyl F H Cl N CH I-58 1-chloroprop-3-yl H H CN CH CH I-59 1-chloroprop-3-yl H H Cl CCN CH I-60 1-chloroprop-3-yl H H F CF CH I-61 1-chloroprop-3-yl H H NO2 CF CH I-62 1-chloroprop-3-yl H H NO2 CH CH I-63 1-chloroprop-3-yl H H CF3 CH CH I-64 1-chloroprop-3-yl H H Cl CF CH I-65 1-chloroprop-3-yl H H Br CF CH I-66 1-chloroprop-3-yl H H Cl CH N I-67 4,4,5,5,5-pentafluoropentyl Br H Cl N CH I-68 4,4,5,5,5-pentafluoropentyl F H Cl N CH I-69 4,4,5,5,5-pentafluoropentyl Me H Cl N CH I-70 3,4,4-trifluorobut-3-enyl F H Cl N CH I-71 3,4,4-trifluorobut-3-enyl Me H Cl N CH I-72 3,4,4-trifluorobut-3-enyl Br H Cl N CH I-73 3,4,4-trifluorobut-3-enyl Cl H Cl N CH I-74 (3,3-difluorocyclobutyl)methan- Me H Cl N CH 1-yl I-75 (3,3-difluorocyclobutyl)methan- Br H Cl N CH 1-yl I-76 (2,2-dichlorocyclopropyl)methyl Me H Cl N CH I-77 (2,2-dichlorocyclopropyl)methyl Br H Cl N CH I-78 (2,2-dichlorocyclopropyl)methyl CN H Cl N CH I-79 (3,3-difluorocyclobutyl)methan- CN H Cl N CH 1-yl I-80 1-chloroprop-3-yl CN H Cl N CH I-81 1,1,1-trifluorobut-4-yl CN H Cl N CH I-82 1,1,1-trifluoroprop-3-yl CN H Cl N CH I-83 3,3-dichloroallyl Me H Cl N CH I-84 3,3-dichloroallyl Br H Cl N CH I-85 3,3-dichloroallyl F H Cl N CH I-86 3-(trifluoromethoxy)propyl F H F N CH I-87 3-(trifluoromethoxy)propyl Me H Cl N CH I-88 3-(trifluoromethoxy)propyl Cl H Cl N CH I-89 3-cyanopropyl F H Cl N CH I-90 3-(trifluoromethoxy)propyl F H Cl N CH NMR data of selected examples

[0112] Selected detailed synthesis examples for the inventive compounds of the general formula (I) are adduced below. The .sup.1H NMR spectroscopic data given for the chemical examples described in the following sections (400 MHz for .sup.1H NMR, solvent CDCl.sub.3 or d.sub.6-DMSO, internal standard: tetramethylsilane ?=0.00 ppm) were obtained on a Bruker instrument, and the signals listed have the meanings given below: br=broad; s=singlet, d=doublet, t=triplet, dd=doublet of doublets, ddd=doublet of a doublet of doublets, m=multiplet, q=quartet, quint=quintet, sext=sextet, sept=septet, dq=doublet of quartets, dt=doublet of triplets. In the case of diastereomer mixtures, what is reported is either the significant signals for each of the two diastereomers or the characteristic signal of the main diastereomer.

Example No. I-1

[0113] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.49 (s, 2H), 7.50-7.32 (m, 4H), 3.17 (s, 3H).

Example No. I-2

[0114] .sup.1H NMR (400 MHz, d6-DMSO ?, ppm) 8.79 (s, 2H), 7.52-7.37 (m, 4H), 3.70 (tr, 2H), 3.60 (tr, 2H), 2.14 (m, 2H).

Example No. I-3

[0115] .sup.1H NMR (400 MHz, d6-DMSO ?, ppm) 8.79 (s, 2H), 7.50-7.37 (m, 4H), 3.45 (tr, 2H), 1.70 (m, 2H), 0.94 (tr, 3H).

Example No. I-4

[0116] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.50 (s, 2H), 7.48-7.26 (m, 4H), 4.18 (qu, 2H).

Example No. I-5

[0117] .sup.1H NMR (400 MHz, d6-DMSO ?, ppm) 8.77 (s, 2H), 7.52-7.37 (m, 4H), 3.70 (tr, 2H), 3.60 (tr, 2H), 2.14 (m, 2H).

Example No. I-6

[0118] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.49 (s, 2H), 7.51-7.31 (m, 4H), 3.26 (tr, 2H), 1.83 (m, 2H), 1.46 (m, 2H), 0.94 (tr, 3H).

Example No. I-7

[0119] .sup.1H NMR (400 MHz, d6-DMSO ?, ppm) 8.79 (s, 2H), 7.51-7.37 (m, 4H), 3.39 (d, 2H), 2.10 (m, 1H), 0.98 (d, 6H).

Example No. I-8

[0120] .sup.1H NMR (400 MHz, d6-DMSO ?, ppm) 8.79 (s, 2H), 7.55-7.38 (m, 4H), 3.85 (m, 2H), 2.81 (m, 2H).

Example No. I-9

[0121] .sup.1H NMR (400 MHz, d6-DMSO ?, ppm) 8.79 (s, 2H), 7.56-7.39 (m, 4H), 5.57 (s, 2H).

Example No. I-10

[0122] .sup.1H NMR (400 MHz, d6-DMSO ?, ppm) 8.79 (s, 2H), 7.52-7.38 (m, 4H), 3.63 (tr, 2H), 2.41 (m, 2H), 1.88 (m, 2H).

Example No. I-11

[0123] .sup.1H NMR (400 MHz, d6-DMSO ?, ppm) 8.79 (s, 2H), 7.35-7.26 (m, 3H), 3.69 (m, 4H), 2.36 (s, 3H), 2.13 (m, 2H).

Example No. I-12

[0124] .sup.1H NMR (400 MHz, d6-DMSO ?, ppm) 8.78 (s, 2H), 7.36-7.29 (m, 3H), 3.70 tr, 2H), 3.59 (tr, 2H), 2.16 (s, 3H), 2.10 (m, 2H).

Example No. I-13

[0125] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.50 (s, 2H), 7.33-7.18 (m, 3H), 3.70 (m, 2H), 3.50 (m, 2H), 2.40 (m, 2H).

Example No. I-14

[0126] .sup.1H NMR (400 MHz, d6-DMSO ?, ppm) 8.82 (s, 2H), 7.52-7.34 (m, 3H), 3.71 (m, 4H), 2.18 (m, 2H).

Example No. I-15

[0127] .sup.1H NMR (400 MHz, d6-DMSO ?, ppm) 8.79 (s, 2H), 7.51-7.37 (m, 4H), 3.65 (m, 2H), 3.56 (m, 2H), 1.81 (m, 4H).

Example No. I-16

[0128] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.49 (s, 2H), 7.52-7.30 (m, 4H), 3.30 (qu, 2H), 1.45 (tr, 3H).

Example No. I-17

[0129] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.47 (s, 2H), 7.27 (m, 1H), 7.11 (m, 1H), 6.96 (m, 1H), 3.79 (s, 3H), 3.28 (m, 2H), 1.84 (m, 2H), 1.45 (m, 2H), 0.93 tr, 3H).

Example No. I-18

[0130] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.48 (s, 2H), 7.52-7.29 (m, 4H), 3.48 (m, 1H), 1.43 (d, 6H).

Example No. I-19

[0131] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.50 (s, 2H), 7.54-7.28 (m, 4H), 3.72 (m, 1H), 2.08 (m, 4H), 1.76 (m, 2H), 1.63 (m, 2H).

Example No. I-20

[0132] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.49 (s, 2H), 7.52-7.30 (m, 4H), 3.83 (tr, 2H), 3.56 (tr, 2H), 3.36 (s, 3H).

Example No. I-21

[0133] .sup.1H NMR (400 MHz, CDCl.sub.3, ppm) 8.48 (s, 2H), 7.50-7.30 (m, 4H), 2.69 (m, 1H), 1.13 (m, 4H).

Example No. I-22

[0134] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.49 (s, 2H), 7.53-7.28 (m, 4H), 3.24 (m, 1H), 2.06 (m, 1H), 1.64 (m, 1H), 1.42 (d, 3H), 1.02 (tr, 3H).

Example No. I-23

[0135] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.48 (s, 2H), 7.53-7.30 (m, 4H), 3.20 (d, 2H), 1.22 (m, 1H), 0.72 (m, 2H), 0.41 (m, 2H).

Example No. I-24

[0136] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.48 (s, 2H), 7.51-7.29 (m, 4H), 3.25 (m, 2H), 1.85 (m, 2H), 1.38 (m, 4H), 0.92 (m, 3H).

Example No. I-25

[0137] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.48 (s, 2H), 7.51-7.30 (m, 4H), 3.25 (m, 2H), 1.73 (m, 3H), 0.95 (m, 6H).

Example No. I-26

[0138] .sup.1H NMR (400 MHz, d6-DMSO, ?, ppm): 8.18 (s, 1H), 8.02-7.99 (m, 1H), 7.49-7.38 (m, 4H), 7.34-7.16 (m, 1H), 3.63-3.59 (m, 2H), 2.47-2.35 (m, 2H), 1.92-1.84 (m, 2H).

Example No. I-27

[0139] .sup.1H NMR (400 MHz, d6-DMSO, ?, ppm): 8.18 (s, 1H), 8.02-7.90 (m, 1H), 7.48-7.36 (m, 4H), 7.34-7.18 (m, 1H), 3.71-3.68 (m, 2H), 3.59-3.57 (m, 2H), 2.17-2.10 (m, 2H).

Example No. I-28

[0140] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.48 (s, 2H), 7.29-7.25 (m, 1H), 7.22-7.20 (m, 1H), 7.16-7.13 (m, 1H), 3.55-3.53 (m, 2H), 2.46 (s, 3H), 2.40-2.29 (m, 2H), 2.22-2.12 (m, 2H).

Example No. I-29

[0141] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.49 (s, 2H), 7.30-7.28 (m, 1H), 7.21-7.16 (m, 2H), 3.70-3.66 (m, 2H), 2.80-2.73 (m, 2H), 2.45 (s, 3H).

Example No. I-30

[0142] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.49 (s, 2H), 7.59-7.56 (m, 1H), 7.32-7.24 (m, 2H), 3.63-3.59 (m, 2H), 2.39-2.29 (m, 2H), 2.25-2.17 (m, 2H).

Example No. I-31

[0143] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.50 (s, 2H), 7.58-7.56 (m, 1H), 7.35-7.25 (m, 2H), 3.77-3.73 (m, 2H), 2.87-2.78 (m, 2H).

Example No. I-32

[0144] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.59 (s, 2H), 7.43-7.41 (m, 1H), 7.35-7.28 (m, 2H), 3.73-3.69 (m, 2H), 2.84-2.78 (m, 2H).

Example No. I-33

[0145] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.58 (s, 2H), 7.30-7.28 (m, 1H), 7.21-7.16 (m, 2H), 3.70-3.66 (m, 2H), 2.80-2.73 (m, 2H), 2.45 (s, 3H).

Example No. I-34

[0146] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.58 (s, 2H), 7.43-7.41 (m, 1H), 7.34-7.25 (m, 2H), 3.60-3.56 (m, 2H), 2.38-2.31 (m, 2H), 2.25-2.19 (m, 2H).

Example No. I-35

[0147] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.56 (s, 2H), 7.30-7.27 (m, 1H), 7.23-7.21 (m, 1H), 7.17-7.14 (m, 1H), 3.56 (tr, 2H), 2.47 (s, 3H), 2.41-2.30 (m, 2H), 2.21-2.13 (m, 2H).

Example No. I-36

[0148] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.49 (s, 2H), 7.51-7.48 (m, 1H), 7.39-7.30 (m, 3H), 5.91-5.83 (m, 1H), 5.49-5.44 (m, 2H), 4.01-3.99 (m, 2H).

Example No. I-37

[0149] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.48 (s, 2H), 7.49-7.41 (m, 1H), 7.41-7.27 (m, 3H), 6.73 (dd, 1H), 6.30 (dd, 1H), 6.13 (dd, 1H).

Example No. I-38

[0150] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.50 (s, 2H), 7.43-7.41 (m, 1H), 7.35-7.28 (m, 2H), 3.73-3.69 (m, 2H), 2.84-2.78 (m, 2H).

Example No. I-39

[0151] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.50 (s, 2H), 7.43-7.41 (m, 1H), 7.34-7.28 (m, 2H), 3.60-3.56 (m, 2H), 2.38-2.31 (m, 2H), 2.25-2.19 (m, 2H).

Example No. I-40

[0152] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.59 (s, 2H), 7.39-7.33 (m, 1H), 7.20-7.15 (m, 2H), 3.63-3.59 (m, 2H), 2.83-2.77 (m, 2H).

Example No. I-41

[0153] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.58 (s, 2H), 7.37-7.32 (m, 1H), 7.20-7.13 (m, 2H), 3.50-3.47 (m, 2H), 2.38-2.31 (m, 2H), 2.25-2.19 (m, 2H).

Example No. I-42

[0154] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.42 (s, 2H), 7.37-7.32 (m, 1H), 7.19-7.13 (m, 2H), 3.51-3.47 (m, 2H), 2.38-2.31 (m, 2H), 2.24-2.19 (m, 2H).

Example No. I-43

[0155] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.43 (s, 2H), 7.58-7.55 (m, 1H), 7.35-7.33 (m, 1H), 7.29-7.25 (m, 1H), 3.77-3.73 (m, 2H), 2.84-2.78 (m, 2H).

Example No. I-44

[0156] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.42 (s, 2H), 7.58-7.56 (m, 1H), 7.33-7.30 (m, 1H), 7.28-7.24 (m, 1H), 3.63-3.60 (m, 2H), 2.38-2.31 (m, 2H), 2.24-2.18 (m, 2H).

Example No. I-45

[0157] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.43 (s, 2H), 7.30-7.28 (m, 1H), 7.21-7.17 (m, 2H), 3.71-3.67 (m, 2H), 2.80-2.73 (m, 2H), 2.45 (s, 3H).

Example No. I-46

[0158] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.41 (s, 2H), 7.29-7.25 (m, 1H), 7.22-7.19 (m, 1H), 7.16-7.14 (m, 1H), 3.58-3.54 (m, 2H), 2.46 (s, 3H), 2.38-2.31 (m, 2H), 2.19-2.13 (m, 2H).

Example No. I-47

[0159] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.43 (s, 2H), 7.38-7.33 (m, 1H), 7.18-7.15 (m, 2H), 3.63-3.59 (m, 2H), 2.83-2.77 (m, 2H).

Example No. I-48

[0160] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.51 (s, 2H), 7.38-7.34 (m, 1H), 7.19-7.16 (m, 2H), 3.62-3.59 (m, 2H), 2.84-2.76 (m, 2H).

Example No. I-49

[0161] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.50 (s, 2H), 7.37-7.33 (m, 1H), 7.19-7.14 (m, 2H), 3.50-3.47 (m, 2H), 2.38-2.30 (m, 2H), 2.24-2.19 (m, 2H).

Example No. I-50

[0162] .sup.1H NMR (600 MHz, CDCl.sub.3 ?, ppm) 8.50 (s, 2H), 7.35-7.31 (m, 1H), 7.18-7.12 (m, 2H), 5.85-5.78 (m, 1H), 5.18-5.11 (m, 2H), 3.47-3.44 (m, 2H), 2.68-2.64 (m, 2H).

Example No. I-51

[0163] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.51 (s, 2H), 7.37-7.32 (m, 1H), 7.19-7.13 (m, 2H), 3.63-3.55 (m, 2H), 2.21-2.14 (m, 2H), 1.81-1.76 (m, 1H), 1.71-1.66 (m, 1H), 1.25-1.20 (m, 1H).

Example No. I-52

[0164] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.50 (s, 2H), 7.34-7.30 (m, 1H), 7.18-7.12 (m, 2H), 3.88-3.85 (m, 2H), 3.69-3.66 (m, 2H), 3.36 (s, 3H).

Example No. I-53

[0165] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.51 (s, 2H), 7.37-7.32 (m, 1H), 7.19-7.13 (m, 2H), 3.59 (d, 2H), 2.95-2.73 (m, 3H), 2.54-2.42 (m, 2H).

Example No. I-54

[0166] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.49 (s, 2H), 7.36-7.30 (m, 1H), 7.18-7.11 (m, 2H), 4.41-4.37 (m, 1H), 3.90-3.85 (m, 1H), 3.80-3.75 (m, 1H), 3.72-3.67 (m, 1H), 3.53-3.48 (m, 1H), 2.25-2.17 (m, 1H), 1.98-1.90 (m, 2H), 1.80-1.71 (m, 1H).

Example No. I-55

[0167] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.50 (s, 2H), 7.36-7.30 (m, 1H), 7.19-7.12 (m, 2H), 3.50-3.46 (m, 2H), 1.84-1.78 (m, 2H), 0.86-0.78 (m, 1H), 0.55-0.50 (m, 2H), 0.17-0.13 (m, 2H).

Example No. I-56

[0168] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.50 (s, 2H), 7.37-7.31 (m, 1H), 7.19-7.12 (m, 2H), 6.02-5.74 (m, 1H), 3.49-3.45 (m, 2H), 2.15-2.02 (m, 4H).

Example No. I-57

[0169] .sup.1H NMR (400 MHz, d6-DMSO ?, ppm) 8.81 (s, 2H), 7.52-7.41 (m, 2H), 7.38-7.35 (m, 1H), 4.11-4.05 (m, 1H), 3.74-3.69 (m, 1H), 2.10-1.93 (m, 2H), 1.62-1.58 (m, 1H).

Example No. I-58

[0170] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.46 (s, 1H), 8.45 (d, 1H), 8.15 (d, 1H), 7.46-7.20 (m, 4H), 3.64 (tr, 2H), 3.43 (tr, 2H), 2.24-2.18 (m, 2H).

Example No. I-59

[0171] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.23 (s, 1H), 8.01 (s, 1H), 7.39-7.31 (m, 4H), 3.69 (tr, 2H), 3.48 (tr, 2H), 2.42-2.35 (m, 2H).

Example No. I-60

[0172] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 7.81 (s, 1H), 7.51 (d, 1H), 7.37-7.25 (m, 4H), 3.68 (tr, 2H), 3.44 (tr, 2H), 2.42-2.32 (m, 2H).

Example No. I-61

[0173] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.80 (s, 1H), 8.33 (d, 1H), 7.51-7.26 (m, 4H), 3.66 (tr, 2H), 3.44 (tr, 2H), 2.38-2.33 (m, 2H).

Example No. I-62

[0174] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 9.00 (s, 1H), 8.51 (d, 1H), 7.35 (d, 1H), 7.33-7.25 (m, 3H), 7.12 (d, 1H), 3.61 (tr, 2H), 3.37 (tr, 2H), 2.31-2.27 (m, 2H).

Example No. I-63

[0175] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.44 (d, 1H), 7.96 (d, 1H), 7.55 (d, 1H), 7.38-7.27 (m, 3H), 7.12 (d, 1H), 3.62 (tr, 2H), 3.41 (tr, 2H), 2.34-2.29 (m, 2H).

Example No. I-64

[0176] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 7.86 (d, 1H), 7.53 (d, 1H), 7.37-7.25 (m, 4H), 3.63 (tr, 2H), 3.43 (tr, 2H), 2.35-2.31 (m, 2H).

Example No. I-65

[0177] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 7.96 (d, 1H), 7.69 (d, 1H), 7.38-7.26 (m, 4H), 3.67 (tr, 2H), 3.44 (tr, 2H), 2.37-2.34 (m, 2H).

Example No. I-66

[0178] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.12 (s, 1H), 7.99 (s, 1H), 7.51-6.99 (m, 4H), 3.66 (tr, 2H), 3.48 (tr, 2H), 2.37-2.32 (m, 2H).

Example No. I-67

[0179] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.49 (s, 2H), 7.60-7.58 (m, 1H), 7.34-7.25 (m, 2H), 3.64 (tr, 2H), 2.35-2.24 (m, 4H).

Example No. I-68

[0180] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.51 (s, 2H), 7.39-7.33 (m, 1H), 7.21-7.14 (m, 2H), 3.51 (tr, 2H), 2.35-2.28 (m, 4H).

Example No. I-69

[0181] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.47 (s, 2H), 7.29-7.27 (m, 1H), 7.25-7.13 (m, 2H), 3.56 (tr, 2H), 2.46 (s, 3H), 2.31-2.19 (m, 4H).

Example No. I-70

[0182] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.50 (s, 2H), 7.38-7.33 (m, 1H), 7.19-7.13 (m, 2H), 3.62-3.58 (m, 2H), 3.01-2.92 (m, 2H).

Example No. I-71

[0183] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.48 (s, 2H), 7.29-7.25 (m, 1H), 7.21-7.14 (m, 2H), 3.70-3.66 (m, 2H), 2.97-2.80 (m, 2H), 2.46 (s, 3H).

Example No. I-72

[0184] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.50 (s, 2H), 7.58-7.56 (m, 1H), 7.33-7.24 (m, 2H), 3.76-3.72 (m, 2H), 3.02-2.93 (m, 2H).

Example No. I-73

[0185] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.50 (s, 2H), 7.43-7.41 (m, 1H), 7.35-7.27 (m, 2H), 3.72-3.69 (m, 2H), 3.02-2.94 (m, 2H).

Example No. I-74

[0186] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.50 (s, 2H), 7.29-7.27 (m, 1H), 7.22-7.14 (m, 2H), 3.66 (d, 2H), 2.90-2.83 (m, 3H), 2.48-2.42 (m, 5H).

Example No. I-75

[0187] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.50 (s, 2H), 7.58-7.56 (m, 1H), 7.33-7.23 (m, 2H), 3.72 (d, 2H), 2.90-2.82 (m, 3H), 2.51-2.46 (m, 2H).

Example No. I-76

[0188] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.49 (s, 2H), 7.30-7.28 (m, 1H), 7.22-7.15 (m, 2H), 4.11-4.06 (m, 1H), 3.37-3.31 (m, 1H), 2.47 (s, 3H), 2.09-2.02 (m, 1H), 1.90-1.85 (m, 1H), 1.58-1.54 (m, 1H).

Example No. I-77

[0189] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.50 (s, 2H), 7.58-7.56 (m, 1H), 7.33-7.24 (m, 2H), 4.17-4.12 (m, 1H), 3.44-3.38 (m, 1H), 2.16-2.08 (m, 1H), 1.90-1.85 (m, 1H), 1.61-1.59 (m, 1H).

Example No. I-78

[0190] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.51 (s, 2H), 7.65-7.62 (m, 1H), 7.52-7.48 (m, 2H), 4.14-4.09 (m, 1H), 3.50-3.44 (m, 1H), 2.21-2.16 (m, 1H), 1.93-1.89 (m, 1H), 1.63-1.59 (m, 1H).

Example No. I-79

[0191] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.51 (s, 2H), 7.64-7.62 (m, 2H), 7.51-7.47 (m, 1H), 3.59 (d, 2H), 2.95-2.84 (m, 3H), 2.56-2.44 (m, 2H).

Example No. I-80

[0192] .sup.1H NMR (400 MHz, d6-DMSO ?, ppm): 8.51 (s, 2H), 7.65-7.61 (m, 2H), 7.51-7.47 (m, 1H), 3.73-3.69 (m, 4H), 2.50-2.43 (m, 2H).

Example No. I-81

[0193] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.50 (s, 2H), 7.65-7.62 (m, 2H), 7.52-7.48 (m, 1H), 3.62 (tr, 2H), 2.42-2.23 (m, 4H).

Example No. I-82

[0194] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.51 (s, 2H), 7.66-7.63 (m, 2H), 7.53-7.49 (m, 1H), 3.77-3.73 (m, 2H), 2.89-2.82 (m, 2H).

Example No. I-83

[0195] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.51 (s, 2H), 7.31-7.28 (m, 1H), 7.23-7.16 (m, 2H), 6.08 (tr, 1H), 4.34 (d, 2H), 2.46 (s, 3H).

Example No. I-84

[0196] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.50 (s, 2H), 7.58-7.56 (m, 1H), 7.33-7.24 (m, 2H), 6.11 (tr, 1H), 4.40 (d, 2H).

Example No. I-85

[0197] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.51 (s, 2H), 7.38-7.32 (m, 1H), 7.20-7.14 (m, 2H), 6.10 (tr, 1H), 4.27 (d, 2H).

Example No. I-86

[0198] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.42 (s, 2H), 7.37-7.31 (m, 1H), 7.19-7.13 (m, 2H), 4.14 (tr, 2H), 3.53 (tr, 2H), 2.37-2.31 (m, 2H).

Example No. I-87

[0199] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.48 (s, 2H), 7.29-7.14 (m, 3H), 4.15 (tr, 2H), 3.59 (tr, 2H), 2.47 (s, 3H), 2.33-2.30 (m, 2H).

Example No. I-88

[0200] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.50 (s, 2H), 7.43-7.40 (m, 1H), 7.34-7.28 (m, 2H), 4.14 (tr, 2H), 3.62 (tr, 2H), 2.36-2.33 (m, 2H).

Example No. I-89

[0201] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.51 (s, 2H), 7.39-7.33 (m, 1H), 7.20-7.15 (m, 2H), 3.56 (tr, 2H), 2.66 (tr, 2H), 2.37-2.30 (m, 2H).

Example No. I-90

[0202] .sup.1H NMR (400 MHz, CDCl.sub.3 ?, ppm) 8.51 (s, 2H), 7.36-7.32 (m, 1H), 7.19-7.14 (m, 2H), 4.14 (tr, 2H), 3.53 (tr, 2H), 2.36-2.33 (m, 2H).

[0203] The present invention further provides for the use of one or more compounds of the general formula (I) and/or salts thereof, as defined above, preferably in one of the embodiments identified as preferred or particularly preferred, in particular one or more compounds of the formulae (1-1) to (1-90) and/or salts thereof, in each case as defined above, as herbicide and/or plant growth regulator, preferably in crops of useful plants and/or ornamentals.

[0204] The present invention further provides a method of controlling harmful plants and/or for regulating the growth of plants, characterized in that an effective amount [0205] of one or more compounds of the general formula (I) and/or salts thereof, as defined above, preferably in one of the embodiments identified as preferred or particularly preferred, in particular one or more compounds of the formulae (1-1) to (1-90) and/or salts thereof, in each case as defined above, or [0206] of a composition of the invention, as defined below, [0207] is applied to the (harmful) plants, seeds of (harmful) plants, the soil in which or on which the (harmful) plants grow or the area under cultivation.

[0208] The present invention also provides a method for controlling unwanted plants, preferably in crops of useful plants, characterized in that an effective amount [0209] of one or more compounds of the general formula (I) and/or salts thereof, as defined above, preferably in one of the embodiments identified as preferred or particularly preferred, in particular one or more compounds of the formulae (1-1) to (1-90) and/or salts thereof, in each case as defined above, or [0210] of a composition of the invention, as defined below, [0211] is applied to unwanted plants (for example harmful plants such as mono- or dicotyledonous weeds or unwanted crop plants), the seed of the unwanted plants (i.e. plant seeds, for example grains, seeds or vegetative propagation organs such as tubers or shoot parts with buds), the soil in which or on which the unwanted plants grow (for example the soil of crop-growing land or non-crop-growing land) or the area under cultivation (i.e. the area on which the unwanted plants will grow).

[0212] The present invention also further provides a method for controlling for regulating the growth of plants, preferably of useful plants, characterized in that an effective amount [0213] of one or more compounds of the general formula (I) and/or salts thereof, as defined above, preferably in one of the embodiments identified as preferred or particularly preferred, in particular one or more compounds of the formulae (1-1) to (1-90) and/or salts thereof, in each case as defined above, or [0214] of a composition of the invention, as defined below, [0215] is applied to the plant, the seed of the plant (i.e. plant seed, for example grains, seeds or vegetative propagation organs such as tubers or shoot parts with buds), the soil in which or on which the plants grow (for example the soil of crop land or non-crop land) or the area under cultivation (i.e. the area on which the plants will grow).

[0216] In this context, the inventive compounds or the inventive compositions can be applied for example by pre-sowing (if appropriate also by incorporation into the soil), pre-emergence and/or post-emergence processes. Specific examples of some representatives of the monocotyledonous and dicotyledonous weed flora which can be controlled by the compounds of the invention are as follows, though there is no intention to restrict the enumeration to particular species.

[0217] In a method of the invention for controlling harmful plants or for regulating the growth of plants, preference is given to using one or more compounds of the general formula (I) and/or salts thereof for control of harmful plants or for regulation of growth in crops of useful plants or ornamental plants, where the useful plants or ornamental plants in a preferred configuration are transgenic plants.

[0218] The inventive compounds of the general formula (I) and/or salts thereof are suitable for controlling the following genera of monocotyledonous and dicotyledonous harmful plants: [0219] Monocotyledonous harmful plants of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum. [0220] Dicotyledonous harmful plants of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.

[0221] When the inventive compounds of the general formula (I) are applied to the soil surface before germination of the harmful plants (weed grasses and/or broad-leaved weeds) (pre-emergence method), either the seedlings of the weed grasses or broad-leaved weeds are prevented completely from emerging or they grow until they have reached the cotyledon stage, but then stop growing and eventually, after three to four weeks have elapsed, die completely.

[0222] If the active ingredients of the general formula (I) are applied post-emergence to the green parts of the plants, growth stops after the treatment, and the harmful plants remain at the growth stage at the time of application, or they die completely after a certain time, so that in this manner competition by the weeds, which is harmful to the crop plants, is eliminated very early and in a sustained manner.

[0223] Although the inventive compounds of the general formula (I) display outstanding herbicidal activity against monocotyledonous and dicotyledonous weeds, crop plants of economically important crops, for example dicotyledonous crops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Miscanthus, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous crops of the genera Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea, are damaged only to an insignificant extent, or not at all, depending on the structure of the respective inventive compound and its application rate. For these reasons, the present compounds are very suitable for selective control of unwanted plant growth in plant crops such as agriculturally useful plants or ornamental plants.

[0224] In addition, the inventive compounds of the general formula (I) (depending on their particular structure and the application rate deployed) have outstanding growth-regulating properties in crop plants. They intervene in the plants' own metabolism with regulatory effect, and can thus be used for the controlled influencing of plant constituents and to facilitate harvesting, for example by triggering desiccation and stunted growth. Furthermore, they are also suitable for the general control and inhibition of unwanted vegetative growth without killing the plants in the process. Inhibition of vegetative growth plays a major role for many mono- and dicotyledonous crops since, for example, this can reduce or completely prevent lodging.

[0225] By virtue of their herbicidal and plant growth regulatory properties, the active ingredients of the general formula (I) can also be used to control harmful plants in crops of genetically modified plants or plants modified by conventional mutagenesis. In general, the transgenic plants are characterized by particular advantageous properties, for example by resistances to certain pesticides, in particular certain herbicides, resistances to plant diseases or pathogens of plant diseases, such as certain insects or microorganisms such as fungi, bacteria or viruses. Other specific characteristics relate, for example, to the harvested material with regard to quantity, quality, storability, composition and specific constituents. For instance, there are known transgenic plants with an elevated starch content or altered starch quality, or those with a different fatty acid composition in the harvested material.

[0226] It is preferred with a view to transgenic crops to use the inventive compounds of the general formula (I) and/or salts thereof in economically important transgenic crops of useful plants and ornamentals, for example of cereals such as wheat, barley, rye, oats, millet, rice and corn or else crops of sugar beet, cotton, soybean, oilseed rape, potato, tomato, peas and other vegetables.

[0227] It is preferable to employ the inventive compounds of the general formula (I) also as herbicides in crops of useful plants which are resistant, or have been made resistant by recombinant means, to the phytotoxic effects of the herbicides.

[0228] By virtue of their herbicidal and plant growth regulatory properties, the inventive compounds of the general formula (I) can also be used to control harmful plants in crops of genetically modified plants which are known or are yet to be developed. In general, the transgenic plants are characterized by particular advantageous properties, for example by resistances to certain pesticides, in particular certain herbicides, resistances to plant diseases or pathogens of plant diseases, such as certain insects or microorganisms such as fungi, bacteria or viruses. Other specific characteristics relate, for example, to the harvested material with regard to quantity, quality, storability, composition and specific constituents. For instance, there are known transgenic plants with an elevated starch content or altered starch quality, or those with a different fatty acid composition in the harvested material. Further special properties may be tolerance or resistance to abiotic stressors, for example heat, cold, drought, salinity and ultraviolet radiation.

[0229] Preference is given to the use of the inventive compounds of the general formula (I) or salts thereof in economically important transgenic crops of useful plants and ornamentals, for example of cereals such as wheat, barley, rye, oats, triticale, millet, rice, cassava and corn, or else crops of sugar beet, cotton, soybean, oilseed rape, potatoes, tomatoes, peas and other vegetables.

[0230] It is preferable to employ the compounds of the general formula (I) as herbicides in crops of useful plants which are resistant, or have been made resistant by recombinant means, to the phytotoxic effects of the herbicides.

[0231] Conventional ways of producing novel plants which have modified properties in comparison to existing plants consist, for example, in traditional cultivation methods and the generation of mutants. Alternatively, novel plants with altered properties can be generated with the aid of recombinant methods.

[0232] A large number of molecular-biological techniques by means of which novel transgenic plants with modified properties can be generated are known to the person skilled in the art. For such genetic manipulations, nucleic acid molecules which allow mutagenesis or sequence alteration by recombination of DNA sequences can be introduced into plasmids. With the aid of standard methods, it is possible, for example, to undertake base exchanges, remove part sequences or add natural or synthetic sequences. To connect the DNA fragments to each other, adapters or linkers may be added to the fragments.

[0233] For example, the generation of plant cells with a reduced activity of a gene product can be achieved by expressing at least one corresponding antisense RNA, a sense RNA for achieving a cosuppression effect, or by expressing at least one suitably constructed ribozyme which specifically cleaves transcripts of the abovementioned gene product.

[0234] To this end, it is firstly possible to use DNA molecules which encompass the entire coding sequence of a gene product inclusive of any flanking sequences which may be present, and also DNA molecules which only encompass portions of the coding sequence, in which case it is necessary for these portions to be long enough to have an antisense effect in the cells. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but are not completely identical to them.

[0235] When expressing nucleic acid molecules in plants, the protein synthesized may be localized in any desired compartment of the plant cell. However, to achieve localization in a particular compartment, it is possible, for example, to join the coding region to DNA sequences which ensure localization in a particular compartment. Sequences of this kind are known to the person skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227). The nucleic acid molecules can also be expressed in the organelles of the plant cells.

[0236] The transgenic plant cells can be regenerated by known techniques to give rise to entire plants. In principle, the transgenic plants may be plants of any desired plant species, i.e. not only monocotyledonous but also dicotyledonous plants.

[0237] Obtainable in this way are transgenic plants having properties altered by overexpression, suppression or inhibition of homologous (=natural) genes or gene sequences or expression of heterologous (=foreign) genes or gene sequences.

[0238] The inventive compounds of the general formula (I) can preferably also be used in transgenic crops which are resistant to growth regulators, for example dicamba, or to herbicides which inhibit essential plant enzymes, for example acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS), hydroxyphenylpyruvate dioxygenases (HPPD), or protoporphyrinogen oxidase (PPO), or to herbicides from the group of the sulfonylureas, the glyphosates, glufosinates or benzoylisoxazoles and analogous active ingredients.

[0239] When the inventive compounds of the general formula (I) are employed in transgenic crops, not only do the effects toward harmful plants observed in other crops occur, but frequently also effects which are specific to application in the particular transgenic crop, for example an altered or specifically widened spectrum of weeds which can be controlled, altered application rates which can be used for the application, preferably good combinability with the herbicides to which the transgenic crop is resistant, and influencing of growth and yield of the transgenic crop plants.

[0240] The invention therefore also relates to the use of the inventive compounds of the general formula (I) and/or salts thereof as herbicides for controlling harmful plants in crops of useful plants or ornamentals, optionally in transgenic crop plants.

[0241] Preference is given to the use of compounds of the general formula (I) in cereals, here preferably corn, wheat, barley, rye, oats, millet or rice, by the pre- or post-emergence method.

[0242] Preference is also given to the use of compounds of the general formula (I) in soybean by the pre-emergence or post-emergence method.

[0243] The use of inventive compounds of the formula (I) for the control of harmful plants or for growth regulation of plants also includes the case in which a compound of the general formula (I) or its salt is not formed from a precursor substance (prodrug) until after application on the plant, in the plant or in the soil.

[0244] The invention also provides the use of one or more compounds of the general formula (I) or salts thereof or of a composition according to the invention (as defined below) (in a method) for controlling harmful plants or for regulating the growth of plants which comprises applying an effective amount of one or more compounds of the general formula (I) or salts thereof onto the plants (harmful plants, if appropriate together with the useful plants), plant seeds, the soil in which or on which the plants grow or the area under cultivation.

[0245] The invention also provides a herbicidal and/or plant growth-regulating composition, characterized in that the composition comprises [0246] (a) one or more compounds of the general formula (I) and/or salts thereof, as defined above, preferably in one of the embodiments identified as preferred or particularly preferred, in particular one or more compounds of the formulae (I-1) to (1-90) and/or salts thereof, in each case as defined above, [0247] and [0248] (b) one or more further substances selected from groups (i) and/or (ii): [0249] (i) one or more further agrochemically active substances, preferably selected from the group consisting of insecticides, acaricides, nematicides, further herbicides (i.e. those not conforming to the general formula (I) defined above), fungicides, safeners, fertilizers and/or further growth regulators, [0250] (ii) one or more formulation auxiliaries customary in crop protection.

[0251] The further agrochemically active substances of component (i) of a composition of the invention are preferably selected from the group of substances mentioned in The Pesticide Manual, 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012.

[0252] A herbicidal or plant growth-regulating composition of the invention comprises preferably one, two, three or more formulation auxiliaries (ii) customary in crop protection selected from the group consisting of surfactants, emulsifiers, dispersants, film formers, thickeners, inorganic salts, dusting agents, carriers that are solid at 25? C. and 1013 mbar, preferably adsorptive granulated inert materials, wetting agents, antioxidants, stabilizers, buffer substances, antifoam agents, water, organic solvents, preferably organic solvents miscible with water in any ratio at 25? C. and 1013 mbar.

[0253] The inventive compounds of the general formula (I) can be used in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusting products or granules in the customary formulations. The invention therefore also provides herbicidal and plant growth-regulating compositions which comprise compounds of the general formula (I) and/or salts thereof.

[0254] The inventive compounds of the general formula (I) and/or salts thereof can be formulated in various ways according to which biological and/or physicochemical parameters are specified. Possible formulations include, for example: wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), dispersions based on oil or water, oil-miscible solutions, capsule suspensions (CS), dusting products (DP), dressings, granules for scattering and soil application, granules (GR) in the form of microgranules, spray granules, absorption and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.

[0255] These individual formulation types and the formulation auxiliaries, such as inert materials, surfactants, solvents and further additives, are known to the person skilled in the art and are described, for example, in: Watkins, Handbook of Insecticide Dust Diluents and Carriers, 2nd ed., Darland Books, Caldwell N.J., H. v. Olphen, Introduction to Clay Colloid Chemistry, 2nd ed., J. Wiley & Sons, N.Y., C. Marsden, Solvents Guide, 2nd ed., Interscience, N.Y. 1963, McCutcheon's Detergents and Emulsifiers Annual, MC Publ. Corp., Ridgewood N.J., Sisley and Wood, Encyclopedia of Surface Active Agents, Chem. Publ. Co. Inc., N.Y. 1964, Sch?nfeldt, Grenzfl?chenaktive Athylenoxidaddukte [Interface-active Ethylene Oxide Adducts], Wiss. Verlagsgesellschaft, Stuttgart 1976, Winnacker-K?chler, Chemische Technologie, Volume 7, C. Hanser Verlag Munich, 4th ed. 1986.

[0256] Wettable powders are preparations which can be dispersed uniformly in water and, in addition to the active ingredient, apart from a diluent or inert substance, also comprise surfactants of the ionic and/or nonionic type (wetting agents, dispersants), for example polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonate, sodium 2,2-dinaphthylmethane-6,6-disulfonate, sodium dibutylnaphthalenesulfonate or else sodium oleoylmethyltaurate. To produce the wettable powders, the active herbicidal ingredients are finely ground, for example in customary apparatuses such as hammer mills, blower mills and air-jet mills, and simultaneously or subsequently mixed with the formulation auxiliaries.

[0257] Emulsifiable concentrates are produced by dissolving the active ingredient in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene, or else relatively high-boiling aromatics or hydrocarbons or mixtures of the organic solvents, with addition of one or more ionic and/or nonionic surfactants (emulsifiers). Examples of emulsifiers which may be used are: calcium alkylarylsulfonate salts, for example calcium dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters, for example sorbitan fatty acid esters, or polyoxyethylene sorbitan esters, for example polyoxyethylene sorbitan fatty acid esters.

[0258] Dusting products are obtained by grinding the active ingredient with finely distributed solids, for example talc, natural clays, such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.

[0259] Suspension concentrates may be water- or oil-based. They may be produced, for example, by wet-grinding by means of commercial bead mills and optional addition of surfactants as already listed above, for example, for the other formulation types.

[0260] Emulsions, for example oil-in-water emulsions (EW), can be produced, for example, by means of stirrers, colloid mills and/or static mixers using aqueous organic solvents and optionally surfactants as already listed above, for example, for the other formulation types.

[0261] Granules can be produced either by spraying the active ingredient onto granular inert material capable of adsorption or by applying active ingredient concentrates to the surface of carrier substances, such as sand, kaolinites or granular inert material, by means of adhesives, for example polyvinyl alcohol, sodium polyacrylate or else mineral oils. Suitable active ingredients can also be granulated in the manner customary for the production of fertilizer granulesif desired as a mixture with fertilizers.

[0262] Water-dispersible granules are produced generally by the customary processes such as spray-drying, fluidized-bed granulation, pan granulation, mixing with high-speed mixers and extrusion without solid inert material.

[0263] For the production of pan granules, fluidized bed granules, extruder granules and spray granules, see, for example, processes in Spray-Drying Handbook 3rd ed. 1979, G. Goodwin Ltd., London; J. E. Browning, Agglomeration, Chemical and Engineering 1967, pages 147 ff.; Perry's Chemical Engineer's Handbook, 5th Ed., McGraw-Hill, New York 1973, pp. 8-57.

[0264] For further details regarding the formulation of crop protection compositions, see, for example, G. C. Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, pages 81-96 and J. D. Freyer, S. A. Evans, Weed Control Handbook, 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.

[0265] The agrochemical preparations, preferably herbicidal or plant growth-regulating compositions, of the present invention preferably comprise a total amount of 0.1 to 99% by weight, preferably 0.5 to 95% by weight, more preferably 1 to 90% by weight, especially preferably 2 to 80% by weight, of active ingredients of the general formula (I) and salts thereof.

[0266] In wettable powders, the active ingredient concentration is, for example, about 10% to 90% by weight, the remainder to 100% by weight consisting of customary formulation constituents. In emulsifiable concentrates, the active ingredient concentration may be about 1% to 90% and preferably 5% to 80% by weight. Formulations in the form of dusts comprise 1% to 30% by weight of active ingredient, preferably usually 5% to 20% by weight of active ingredient; sprayable solutions contain about 0.05% to 80% by weight, preferably 2% to 50% by weight of active ingredient. In the case of water-dispersible granules, the active ingredient content depends partly on whether the active ingredient is in liquid or solid form and on which granulation auxiliaries, fillers, and so forth are used. In the water-dispersible granules, the content of active ingredient is, for example, between 1% and 95% by weight, preferably between 10% and 80% by weight.

[0267] In addition, the active ingredient formulations mentioned optionally comprise the respective customary stickers, wetters, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents and solvents, fillers, carriers and dyes, defoamers, evaporation inhibitors and agents which influence the pH and the viscosity. Examples of formulation auxiliaries are described, inter alia, in Chemistry and Technology of Agrochemical Formulations, ed. D. A. Knowles, Kluwer Academic Publishers (1998).

[0268] The inventive compounds of the general formula (I) or salts thereof can be used as such or in the form of their preparations (formulations) in a combination with other pesticidally active substances, for example insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and/or growth regulators, for example in the form of a finished formulation or of a tankmix. The combination formulations can be produced on the basis of the abovementioned formulations, taking account of the physical properties and stabilities of the active ingredients to be combined.

[0269] Combination partners usable for the inventive compounds of the general formula (I) in mixed formulations or in a tankmix are, for example, known active ingredients based on inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II, protoporphyrinogen oxidase, as described, for example, in Weed Research 26 (1986) 441-445 or The Pesticide Manual, 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012, and the literature cited therein.

[0270] Of particular interest is the selective control of harmful plants in crops of useful plants and ornamentals. Although the inventive compounds of the general formula (I) have already demonstrated very good to adequate selectivity in a large number of crops, in principle, in some crops and in particular also in the case of mixtures with other, less selective herbicides, phytotoxicities on the crop plants may occur. In this connection, combinations of inventive compounds (I) that are of particular interest are those which comprise the compounds of the general formula (I) or their combinations with other herbicides or pesticides and safeners. The safeners, which are used in an antidotically effective amount, reduce the phytotoxic side effects of the herbicides/pesticides employed, for example in economically important crops, such as cereals (wheat, barley, rye, corn, rice, millet), sugarbeet, sugarcane, oilseed rape, cotton and soybeans, preferably cereals.

[0271] The weight ratios of herbicide (mixture) to safener depend generally on the herbicide application rate and the efficacy of the safener in question and may vary within wide limits, for example in the range from 200:1 to 1:200, preferably 100:1 to 1:100, in particular 20:1 to 1:20. Analogously to the compounds of the general formula (I) or mixtures thereof, the safeners can be formulated with further herbicides/pesticides and be provided and employed as a finished formulation or tank mix with the herbicides.

[0272] For application, the herbicide formulations or herbicide-safener formulations in the commercial form are diluted if appropriate in a customary manner, for example with water in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules. Preparations in dust form, granules for soil application or granules for scattering and sprayable solutions are not normally diluted further with other inert substances prior to application.

[0273] The application rate of the compounds of the general formula (I) and/or their salts is affected to a certain extent by external conditions such as temperature, humidity, etc. The application rate may vary within wide limits. For the application as a herbicide for controlling harmful plants, the total amount of compounds of the general formula (I) and their salts is preferably in the range from 0.001 to 10.0 kg/ha, with preference in the range from 0.005 to 5 kg/ha, more preferably in the range from 0.01 to 1.5 kg/ha, particularly preferably in the range from 0.05 to 1 kg/ha. This applies both to pre-emergence and to post-emergence application.

[0274] When the inventive compounds of the general formula (I) and/or salts thereof are used as plant growth regulator, for example as culm stabilizer for crop plants like those mentioned above, preferably cereal plants, such as wheat, barley, rye, triticale, millet, rice or corn, the total application rate is preferably in the range of from 0.001 to 2 kg/ha, preferably in the range of from 0.005 to 1 kg/ha, in particular in the range of from 10 to 500 g/ha, very particularly preferably in the range from 20 to 250 g/ha. This applies both to pre-emergence and to post-emergence application.

[0275] The application as culm stabilizer may take place at various stages of the growth of the plants. Preferred is, for example, the application after the tillering phase, at the beginning of the longitudinal growth.

[0276] As an alternative, application as plant growth regulator is also possible by treating the seed, which includes various techniques for dressing and coating seed. The application rate depends on the particular techniques and can be determined in preliminary tests.

[0277] Combination partners usable for the inventive compounds of the general formula (I) in compositions of the invention (e.g. mixed formulations or in a tankmix) are, for example, known active ingredients based on inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II or protoporphyrinogen oxidase, as described, for example, from Weed Research 26 (1986) 441-445 or The Pesticide Manual, 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012, and literature cited therein. Known herbicides or plant growth regulators which can be combined with the compounds of the invention are, for example, the following, where said active ingredients are referred to either by their common name in accordance with the International Organization for Standardization (ISO) or by the chemical name or by the code number. They always encompass all the use forms, for example acids, salts, esters and also all isomeric forms such as stereoisomers and optical isomers, even if they are not mentioned explicitly.

[0278] Examples of such herbicidal mixing partners are: [0279] acetochlor, acifluorfen, acifluorfen-methyl, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryn, amicarbazone, amidochlor, amidosulfuron, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methylphenyl)-5-fluoropyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlor-potassium, aminocyclopyrachlor-methyl, aminopyralid, aminopyralid-dimethylammonium, aminopyralid-tripromine, amitrole, ammonium sulfamate, anilofos, asulam, asulam-potassium, asulam sodium, atrazine, azafenidin, azimsulfuron, beflubutamid, (S)-(?)-beflubutamid, beflubutamid-M, benazolin, benazolin-ethyl, benazolin-dimethylammonium, benazolin-potassium, benfluralin, benfuresate, bensulfuron, bensulfuron-methyl, bensulide, bentazone, bentazone-sodium, benzobicyclon, benzofenap, bicyclopyrone, bifenox, bilanafos, bilanafos-sodium, bipyrazone, bispyribac, bispyribac-sodium, bixlozone, bromacil, bromacil-lithium, bromacil-sodium, bromobutide, bromofenoxim, bromoxynil, bromoxynil-butyrate, -potassium, -heptanoate and -octanoate, busoxinone, butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim, butylate, cafenstrole, cambendichlor, carbetamide, carfentrazone, carfentrazone-ethyl, chloramben, chloramben-ammonium, chloramben-diolamine, chlroamben-methyl, chloramben-methylammonium, chloramben-sodium, chlorbromuron, chlorfenac, chlorfenac-ammonium, chlorfenac-sodium, chlorfenprop, chlorfenprop-methyl, chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorophthalim, chlorotoluron, chlorsulfuron, chlorthal, chlorthal-dimethyl, chlorthal-monomethyl, cinidon, cinidon-ethyl, cinmethylin, exo-(+)-cinmethylin, i.e. (1R,2S,4S)-4-isopropyl-1-methyl-2-[(2-methylbenzyl)oxy]-7-oxabicyclo[2.2.1]heptane, exo-(?)-cinmethylin, i.e. (1R,2S,4S)-4-isopropyl-1-methyl-2-[(2-methylbenzyl)oxy]-7-oxabicyclo[2.2.1]heptane, cinosulfuron, clacyfos, clethodim, clodinafop, clodinafop-ethyl, clodinafop-propargyl, clomazone, clomeprop, clopyralid, clopyralid-methyl, clopyralid-olamine, clopyralid-potassium, clopyralid-tripomine, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cycloate, cyclopyranil, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop, cyhalofop-butyl, cyprazine, 2,4-D (including the ammonium, butotyl, -butyl, choline, diethylammonium, -dimethylammonium, -diolamine, -doboxyl, -dodecylammonium, etexyl, ethyl, 2-ethylhexyl, heptylammonium, isobutyl, isooctyl, isopropyl, isopropylammonium, lithium, meptyl, methyl, potassium, tetradecylammonium, triethylammonium, triisopropanolammonium, tripromine and trolamine salt thereof), 2,4-DB, 2,4-DB-butyl, -dimethylammonium, isooctyl, -potassium and -sodium, daimuron (dymron), dalapon, dalapon-calcium, dalapon-magnesium, dalapon-sodium, dazomet, dazomet-sodium, n-decanol, 7-deoxy-D-sedoheptulose, desmedipham, detosyl-pyrazolate (DTP), dicamba and its salts, e. g. dicamba-biproamine, dicamba-N,N-bis(3-aminopropyl)methylamine, dicamba-butotyl, dicamba-choline, dicamba-diglycolamine, dicamba-dimethylammonium, dicamba-diethanolaminemmonium, dicamba-diethylammonium, dicamba-isopropylammonium, dicamba-methyl, dicamba-monoethanolaminedicamba-olamine, dicamba-potassium, dicamba-sodium, dicamba-triethanolamine, dichlobenil, 2-(2,4-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, 2-(2,5-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, dichlorprop, dichlorprop-butotyl, dichlroprop-dimethylammonium, dichhlorprop-etexyl, dichlorprop-ethylammonium, dichlorprop-isoctyl, dichlorprop-methyl, dichlorprop-potassium, dichlorprop-sodium, dichlorprop-P, dichlorprop-P-dimethylammonium, dichlorprop-P-etexyl, dichlorprop-P-potassium, dichlorprop-sodium, diclofop, diclofop-methyl, diclofop-P, diclofop-P-methyl, diclosulam, difenzoquat, difenzoquat-metilsulfate, diflufenican, diflufenzopyr, diflufenzopyr-sodium, dimefuron, dimepiperate, dimesulfazet, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimetrasulfuron, dinitramine, dinoterb, dinoterb-acetate, diphenamid, diquat, diquat-dibromid, diquat-dichloride, dithiopyr, diuron, DNOC, DNOC-ammonium, DNOC-potassium, DNOC-sodium, endothal, endothal-diammonium, endothal-dipotassium, endothal-disodium, epyrifenacil (S-3100), EPTC, esprocarb, ethalfluralin, ethametsulfuron, ethametsulfuron-methyl, ethiozin, ethofumesate, ethoxyfen, ethoxyfen-ethyl, ethoxysulfuron, etobenzanid, F-5231, i.e. N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]-phenyl]ethanesulfonamide, F-7967, i.e. 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenpyrazone, fenquinotrione, fentrazamide, flamprop, flamprop-isoproyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, florpyrauxifen, florpyrauxifen-benzyl, fluazifop, fluazifop-butyl, fluazifop-methyl, fluazifop-P, fluazifop-P-butyl, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, fluometuron, flurenol, flurenol-butyl, -dimethylammonium and -methyl, fluoroglycofen, fluoroglycofen-ethyl, flupropanate, flupropanate-sodium, flupyrsulfuron, flupyrsulfuron-methyl, flupyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium, foramsulfuron, foramsulfuron sodium salt, fosamine, fosamine-ammonium, glufosinate, glufosinate-ammonium, glufosinate-sodium, L-glufosinate-ammonium, L-glufosinate-sodium, glufosinate-P-sodium, glufosinate-P-ammonium, glyphosate, glyphosate-ammonium, -isopropylammonium, -diammonium, -dimethylammonium, -potassium, -sodium, sesquisodium and -trimesium, H-9201, i.e. O-(2,4-dimethyl-6-nitrophenyl)-O-ethyl isopropylphosphoramidothioate, halauxifen, halauxifen-methyl, halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, haloxifop-sodium, hexazinone, HNPC-A8169, i.e. prop-2-yn-1-yl (2S)-2-{3-[(5-tert-butylpyridin-2-yl)oxy]phenoxy}propanoate, HW-02, i.e. 1-(dimethoxyphosphoryl)ethyl (2,4-dichlorophenoxy)acetate, hydantocidin, imazamethabenz, imazamethabenz-methyl, imazamox, imazamox-ammonium, imazapic, imazapic-ammonium, imazapyr, imazapyr-isopropylammonium, imazaquin, imazaquin-ammonium, imazaquin-methyl, imazethapyr, imazethapyr-immonium, imazosulfuron, indanofan, indaziflam, iodosulfuron, iodosulfuron-methyl, iodosulfuron-methyl-sodium, ioxynil, ioxynil-lithium, -octanoate, -potassium and sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, karbutilate, KUH-043, i.e. 3-({[5-(difluoromethyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole, ketospiradox, ketospiradox-potassium, lactofen, lancotrione, lenacil, linuron, MCPA, MCPA-butotyl, -butyl, -dimethylammonium, -diolamine, -2-ethylhexyl, -ethyl, -isobutyl, isoctyl, -isopropyl, -isopropylammonium, -methyl, olamine, -potassium, -sodium and -trolamine, MCPB, MCPB-methyl, -ethyl and -sodium, mecoprop, mecoprop-butotyl, mecoprop-demethylammonium, mecoprop-diolamine, mecoprop-etexyl, mecoprop-ethadyl, mecoprop-isoctyl, mecoprop-methyl, mecoprop-potassium, mecoprop-sodium, and mecoprop-trolamine, mecoprop-P, mecoprop-P-butotyl, -dimethylammonium, -2-ethylhexyl and -potassium, mefenacet, mefluidide, mefluidide-diolamine, mefluidide-potassium, mesosulfuron, mesosulfuron-methyl, mesosulfuron sodium salt, mesotrione, methabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron, methiopyrsulfuron, methiozolin, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinate, monolinuron, monosulfuron, monosulfuron-methyl, MT-5950, i.e. N-[3-chloro-4-(1-methylethyl)phenyl]-2-methylpentanamide, NGGC-011, napropamide, NC-310, i.e. 4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole, NC-656, i.e. 3-[(isopropylsulfonyl)methyl]-N-(5-methyl-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)[1,2,4]triazolo[4,3-a]pyridine-8-carboxamide, neburon, nicosulfuron, nonanoic acid (pelargonic acid), norflurazon, oleic acid (fatty acids), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat, paraquat-dichloride, paraquat-dimethylsulfate, pebulate, pendimethalin, penoxsulam, pentachlorphenol, pentoxazone, pethoxamid, petroleum oils, phenmedipham, phenmedipham-ethyl, picloram, picloram-dimethylammonium, picloram-etexyl, picloram-isoctyl, picloram-methyl, picloram-olamine, picloram-potassium, picloram-triethylammonium, picloram-tripromine, picloram-trolamine, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propoxycarbazone-sodium, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen, pyraflufen-ethyl, pyrasulfotole, pyrazolynate (pyrazolate), pyrazosulfuron, pyrazosulfuron-ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinclorac-dimethylammonium, quinclorac-methyl, quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, QYM201, i.e. 1-{2-chloro-3-[(3-cyclopropyl-5-hydroxy-1-methyl-1H-pyrazol-4-yl)carbonyl]-6-(trifluoromethyl)phenyl}piperidin-2-one, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, SL-261, sulcotrione, sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosulfuron, SYP-249, i.e. 1-ethoxy-3-methyl-1-oxobut-3-en-2-yl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate, SYP-300, i.e. 1-[7-fluoro-3-oxo-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-3-propyl-2-thioxoimidazolidine-4,5-dione, 2,3,6-TBA, TCA (trichloroacetic acid) and its salts, e.g. TCA-ammonium, TCA-calcium, TCA-ethyl, TCA-magnesium, TCA-sodium, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbumeton, terbuthylazine, terbutryn, tetflupyrolimet, thaxtomin, thenylchlor, thiazopyr, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, tiafenacil, tolpyralate, topramezone, tralkoxydim, triafamone, tri-allate, triasulfuron, triaziflam, tribenuron, tribenuron-methyl, triclopyr, triclopyr-butotyl, triclopyr-choline, triclopyr-ethyl, triclopyr-triethylammonium, trietazine, trifloxysulfuron, trifloxysulfuron-sodium, trifludimoxazin, trifluralin, triflusulfuron, triflusulfuron-methyl, tritosulfuron, urea sulfate, vernolate, XDE-848, ZJ-0862, i.e. 3,4-dichloro-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}aniline, 3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydropyrimidin-1 (2H)-yl)phenyl)-5-methyl-4,5-dihydroisoxazole-5-carboxylic acid ethyl ester, ethyl-[(3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}pyridin-2-yl)oxy]acetate, 3-chloro-2-[3-(difluoromethyl)isoxazolyl-5-yl]phenyl 5-chloropyrimidin-2-yl ether, 2-(3,4-dimethoxyphenyl)-4-[(2-hydroxy-6-oxocyclohex-1-en-1-yl)carbonyl]-6-methylpyridazine-3(2H)-one, 2-({2-[(2-methoxyethoxy)methyl]-6-methylpyridin-3-yl}carbonyl)cyclohexane-1,3-dione, (5-hydroxy-1-methyl-1H-pyrazol-4-yl)(3,3,4-trimethyl-1,1-dioxido-2,3-dihydro-1-benzothiophen-5-yl)methanone, 1-methyl-4-[(3,3,4-trimethyl-1,1-dioxido-2,3-dihydro-1-benzothiophen-5-yl)carbonyl]-1H-pyrazol-5-yl propane-1-sulfonate, 4-{2-chloro-3-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]-4-(methylsulfonyl)benzoyl}-1-methyl-1H-pyrazol-5-yl 1,3-dimethyl-1H-pyrazole-4-carboxylate; cyanomethyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate, prop-2-yn-1-yl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate, methyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid, benzyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate, ethyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate, methyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1-isobutyryl-1H-indol-6-yl)pyridine-2-carboxylate, methyl 6-(1-acetyl-7-fluoro-1H-indol-6-yl)-4-amino-3-chloro-5-fluoropyridine-2-carboxylate, methyl 4-amino-3-chloro-6-[1-(2,2-dimethylpropanoyl)-7-fluoro-1H-indol-6-yl]-5-fluoropyridine-2-carboxylate, methyl 4-amino-3-chloro-5-fluoro-6-[7-fluoro-1-(methoxyacetyl)-1H-indol-6-yl]pyridine-2-carboxylate, potassium 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate, sodium 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate, butyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate, 4-hydroxy-1-methyl-3-[4-(trifluoromethyl)pyridin-2-yl]imidazolidin-2-one, 3-(5-tert-butyl-1,2-oxazol-3-yl)-4-hydroxy-1-methylimidazolidin-2-one, 3-[5-chloro-4-(trifluoromethyl)pyridin-2-yl]-4-hydroxy-1-methylimidazolidin-2-one, 4-hydroxy-1-methoxy-5-methyl-3-[4-(trifluoromethyl)pyridin-2-yl]imidazolidin-2-one, 6-[(2-hydroxy-6-oxocyclohex-1-en-1-yl)carbonyl]-1,5-dimethyl-3-(2-methylphenyl)quinazoline-2,4(1H,3H)-dione, 3-(2,6-dimethylphenyl)-6-[(2-hydroxy-6-oxocyclohex-1-en-1-yl)carbonyl]-1-methylquinazoline-2,4(1H,3H)-dione, 2-[2-chloro-4-(methylsulfonyl)-3-(morpholin-4-ylmethyl)benzoyl]-3-hydroxycyclohex-2-en-1-one, 1-(2-carboxyethyl)-4-(pyrimidin-2-yl)pyridazin-1-ium salt (with anions such as chloride, acetate or trifluoroacetate), 1-(2-carboxyethyl)-4-(pyridazin-3-yl)pyridazin-1-ium salt (with anions such as chloride, acetate or trifluoroacetate), 4-(pyrimidin-2-yl)-1-(2-sulfoethyl)pyridazin-1-ium salt (with anions such as chloride, acetate or trifluoroacetate), 4-(pyridazin-3-yl)-1-(2-sulfoethyl)pyridazin-1-ium salt (with anions such as chloride, acetate or trifluoroacetate).

[0280] Examples of plant growth regulators as possible mixing partners are: [0281] abscisic acid, acibenzolar, acibenzolar-S-methyl, 1-aminocyclopro-1-yl carboxylic acid and derivatives thereof, 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine, bikinin, brassinolide, brassinolide-ethyl, catechin, chitooligosaccharides, chitinous compounds, chlormequat chloride, cloprop, cyclanilide, 3-(cycloprop-1-enyl)propionic acid, daminozide, dazomet, dazomet-sodium, n-decanol, dikegulac, dikegulac-sodium, endothal, endothal-dipotassium, -disodium, and mono(N,N-dimethylalkylammonium), ethephon, flumetralin, flurenol, flurenol-butyl, flurenol-methyl, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indol-3-acetic acid (IAA), 4-indol-3-ylbutyric acid, isoprothiolane, probenazole, jasmonic acid, jasmonic acid or derivatives thereof (such as jasmonic acid methyl ester), lipo-chitooligosaccharides, linoleic acid or derivatives thereof, linolenic acid or derivatives thereof, maleic hydrazide, mepiquat chloride, mepiquat pentaborate, 1-methylcyclopropene, 3-methyl abscisic acid, 2-(1-naphthyl)acetamide, 1-naphthylacetic acid, 2-naphthyloxyacetic acid, nitrophenolate-mixture, 4-oxo-4[(2-phenylethyl)amino]butyric acid, paclobutrazol, 4-phenylbutyric acid, N-phenylphthalamic acid, prohexadione, prohexadione-calcium, prohydrojasmon, salicylic acid, salicylic acid methyl ester, strigolactone, tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tsitodef, uniconazole, uniconazole-P, 2-fluoro-N-(3-methoxyphenyl)-9H-purin-6-amine.

[0282] Useful combination partners for the inventive compounds of the general formula (I) also include, for example, the following safeners: [0283] S1) Compounds from the group of heterocyclic carboxylic acid derivatives: [0284] S1.sup.a) Compounds of the dichlorophenylpyrazoline-3-carboxylic acid type (S1.sup.a), preferably compounds such as 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylic acid, ethyl 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylate (S1-1) (mefenpyr-diethyl), and related compounds as described in WO-A-91/07874; [0285] S1.sup.b) Derivatives of dichlorophenylpyrazolecarboxylic acid (S1.sup.b), preferably compounds such as ethyl 1-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylate (S1-2), ethyl 1-(2,4-dichlorophenyl)-5-isopropylpyrazole-3-carboxylate (S1-3), ethyl 1-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)pyrazole-3-carboxylate (S1-4) and related compounds as described in EP-A-333131 and EP-A-269806; [0286] S1.sup.c) Derivatives of 1,5-diphenylpyrazole-3-carboxylic acid (S1.sup.c), preferably compounds such as ethyl 1-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylate (S1-5), methyl 1-(2-chlorophenyl)-5-phenylpyrazole-3-carboxylate (S1-6) and related compounds as described, for example, in EP-A-268554; [0287] S1.sup.d) Compounds of the triazolecarboxylic acid type (S1.sup.d), preferably compounds such as fenchlorazole(-ethyl ester), i.e. ethyl 1-(2,4-dichlorophenyl)-5-trichloromethyl-1H-1,2,4-triazole-3-carboxylate (S1-7), and related compounds, as described in EP-A-174562 and EP-A-346620; [0288] S1.sup.e) Compounds of the 5-benzyl- or 5-phenyl-2-isoxazoline-3-carboxylic acid or of the 5,5-diphenyl-2-isoxazoline-3-carboxylic acid type (S1.sup.e), preferably compounds such as ethyl 5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate (S1-8) or ethyl 5-phenyl-2-isoxazoline-3-carboxylate (S1-9) and related compounds as described in WO-A-91/08202, or 5,5-diphenyl-2-isoxazolinecarboxylic acid (S1-10) or ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (S1-11) (isoxadifen-ethyl) or n-propyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (S1-12) or ethyl 5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate (S1-13) as described in patent application WO-A-95/07897. [0289] S2) Compounds from the group of the 8-quinolinoxy derivatives (S2): [0290] S2.sup.a) Compounds of the 8-quinolinoxyacetic acid type (S2.sup.a), preferably 1-methylhexyl (5-chloro-8-quinolinoxy)acetate (cloquintocet-mexyl) (52-1), 1,3-dimethylbut-1-yl (5-chloro-8-quinolinoxy)acetate (52-2), 4-allyloxybutyl (5-chloro-8-quinolinoxy)acetate (S2-3), 1-allyloxyprop-2-yl (5-chloro-8-quinolinoxy)acetate (S2-4), ethyl (5-chloro-8-quinolinoxy)acetate (S2-5), [0291] methyl (5-chloro-8-quinolinoxy)acetate (S2-6), [0292] allyl (5-chloro-8-quinolinoxy)acetate (52-7), 2-(2-propylideneiminoxy)-1-ethyl (5-chloro-8-quinolinoxy)acetate (52-8), 2-oxoprop-1-yl (5-chloro-8-quinolinoxy)acetate (S2-9) and related compounds, as described in EP-A-86750, EP-A-94349 and EP-A-191736 or EP-A-0 492 366, and also (5-chloro-8-quinolinoxy)acetic acid (S2-10), hydrates and salts thereof, for example the lithium, sodium, potassium, calcium, magnesium, aluminium, iron, ammonium, quaternary ammonium, sulfonium or phosphonium salts thereof, as described in WO-A-2002/34048; [0293] S2.sup.b) Compounds of the (5-chloro-8-quinolinoxy)malonic acid type (S2.sup.b), preferably compounds such as diethyl (5-chloro-8-quinolinoxy)malonate, diallyl (5-chloro-8-quinolinoxy)malonate, methyl ethyl (5-chloro-8-quinolinoxy)malonate and related compounds, as described in EP-A-0 582 198. [0294] S3) Active ingredients of the dichloroacetamide type (S3), which are frequently used as pre-emergence safeners (soil-acting safeners), for example [0295] dichlormid (N,N-diallyl-2,2-dichloroacetamide) (53-1), [0296] R-29148 (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) from Stauffer (S3-2), [0297] R-28725 (3-dichloroacetyl-2,2-dimethyl-1,3-oxazolidine) from Stauffer (S3-3), [0298] benoxacor (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine) (S3-4), [0299] PPG-1292 (N-allyl-N-[(1,3-dioxolan-2-yl)methyl]dichloroacetamide) from PPG Industries (S3-5), [0300] DKA-24 (N-allyl-N-[(allylaminocarbonyl)methyl]dichloroacetamide) from Sagro-Chem (S3-6), [0301] AD-67 or MON 4660 (3-dichloroacetyl-1-oxa-3-azaspiro[4.5]decane) from Nitrokemia or Monsanto (53-7), [0302] TI-34 (1-dichloroacetylazepane) from TRI-Chemical RT (S3-8), [0303] diclonon (dicyclonon) or BAS145138 or LAB145138 (S3-9) [0304] ((RS)-1-dichloroacetyl-3,3,8a-trimethylperhydropyrrolo[1,2-a]pyrimidin-6-one) from BASF, [0305] furilazole or MON 13900 ((RS)-3-dichloroacetyl-5-(2-furyl)-2,2-dimethyloxazolidine) (53-10), and the (R) isomer thereof (S3-11). [0306] S4) Compounds from the class of the acylsulfonamides (S4): [0307] S4.sup.a) N-Acylsulfonamides of the formula (S4.sup.a) and salts thereof, as described in WO-A-97/45016,

##STR00013## [0308] in which [0309] R.sub.A.sup.1 is (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, where the 2 latter radicals are substituted by v.sub.A substituents from the group of halogen, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.6)-haloalkoxy and (C.sub.1-C.sub.4)-alkylthio and, in the case of cyclic radicals, also by (C.sub.1-C.sub.4)-alkyl and (C.sub.1-C.sub.4)-haloalkyl; [0310] R.sub.A.sup.2 is halogen, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkoxy, CF.sub.3; [0311] m.sub.A is 1 or 2; [0312] v.sub.A is 0, 1, 2 or 3; [0313] S4.sup.b) Compounds of the 4-(benzoylsulfamoyl)benzamide type of the formula (S4.sup.b) and salts thereof, as described in WO-A-99/16744,

##STR00014## [0314] in which [0315] R.sub.B.sup.1, R.sub.B.sup.2 are independently hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-alkenyl, (C.sub.3-C.sub.6)-alkynyl, [0316] R.sub.B.sup.3 is halogen, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl or (C.sub.1-C.sub.4)-alkoxy and [0317] m.sub.B is 1 or 2, [0318] e.g. those in which [0319] R.sub.B.sup.1=cyclopropyl, R.sub.B.sup.2=hydrogen and (R.sub.B.sup.3)=2-OMe (cyprosulfamide, S4-1), [0320] R.sub.B.sup.1=cyclopropyl, R.sub.B.sup.2=hydrogen and (R.sub.B.sup.3)=5-Cl-2-OMe (S4-2), [0321] R.sub.B.sup.1=ethyl, R.sub.B.sup.2=hydrogen and (R.sub.B.sup.3)=2-OMe (S4-3), [0322] R.sub.B.sup.1=isopropyl, R.sub.B.sup.2=hydrogen and (R.sub.B.sup.3)=5-Cl-2-OMe (S4-4) and [0323] R.sub.B.sup.1=isopropyl, R.sub.B.sup.2=hydrogen and (R.sub.B.sup.3)=2-OMe (S4-5); [0324] S4.sup.c) Compounds from the class of the benzoylsulfamoylphenylureas of the formula (S4.sup.c), as described in EP-A-365484,

##STR00015## [0325] in which [0326] R.sub.C.sup.1, R.sub.C.sup.2 are independently hydrogen, (C.sub.1-C.sub.8)-alkyl, (C.sub.3-C.sub.8)-cycloalkyl, (C.sub.3-C.sub.6)-alkenyl, (C.sub.3-C.sub.6)-alkynyl, [0327] R.sub.C.sup.3 is halogen, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkoxy, CF.sub.3 and [0328] m.sub.C is 1 or 2; [0329] for example [0330] 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea, [0331] 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea, [0332] 1-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea; [0333] S4.sup.d) Compounds of the N-phenylsulfonylterephthalamide type of the formula (S4.sup.d) and salts thereof, which are known, for example, from CN 101838227,

##STR00016## [0334] in which [0335] R.sub.D.sup.4 is halogen, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkoxy, CF.sub.3; [0336] m.sub.D is 1 or 2; [0337] R.sub.D.sup.5 is hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.5-C.sub.6)-cycloalkenyl. [0338] S5) Active ingredients from the class of the hydroxyaromatics and the aromatic-aliphatic carboxylic acid derivatives (S5), for example [0339] ethyl 3,4,5-triacetoxybenzoate, 3,5-dimethoxy-4-hydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4-fluorosalicylic acid, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid, as described in WO-A-2004/084631, WO-A-2005/015994, WO-A-2005/016001. [0340] S6) Active ingredients from the class of the 1,2-dihydroquinoxalin-2-ones (S6), for example [0341] 1-methyl-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one, 1-methyl-3-(2-thienyl)-1,2-dihydroquinoxaline-2-thione, 1-(2-aminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one hydrochloride, 1-(2-methylsulfonylaminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one, as described in WO-A-2005/112630. [0342] S7) Compounds from the class of the diphenylmethoxyacetic acid derivatives (S7), e.g. methyl diphenylmethoxyacetate (CAS Reg. No. 41858-19-9) (S7-1), ethyl diphenylmethoxyacetate or diphenylmethoxyacetic acid, as described in WO-A-98/38856. [0343] S8) Compounds of the formula (S8), as described in WO-A-98/27049,

##STR00017## [0344] in which the symbols and indices are defined as follows: [0345] R.sub.D.sup.1 is halogen, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-haloalkoxy, [0346] R.sub.D.sup.2 is hydrogen or (C.sub.1-C.sub.4)-alkyl, [0347] R.sub.D.sup.3 is hydrogen, (C.sub.1-C.sub.8)-alkyl, (C.sub.2-C.sub.4)-alkenyl, (C.sub.2-C.sub.4)-alkynyl or aryl, where each of the aforementioned carbon-containing radicals is unsubstituted or substituted by one or more, preferably up to three, identical or different radicals from the group consisting of halogen and alkoxy; or salts thereof, [0348] n.sub.D is an integer from 0 to 2. [0349] S9) Active ingredients from the class of the 3-(5-tetrazolylcarbonyl)-2-quinolones (S9), for example [0350] 1,2-dihydro-4-hydroxy-1-ethyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No.: 219479-18-2), 1,2-dihydro-4-hydroxy-1-methyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No. 95855-00-8), as described in WO-A-1999/000020. [0351] S10) Compounds of the formulae (S10.sup.a) or (S10.sup.b) [0352] as described in WO-A-2007/023719 and WO-A-2007/023764,

##STR00018## [0353] in which [0354] R.sub.E.sup.1 is halogen, (C.sub.1-C.sub.4)-alkyl, methoxy, nitro, cyano, CF.sub.3, OCF.sub.3, [0355] Y.sub.E, Z.sub.E are independently O or S, [0356] n.sub.E is an integer from 0 to 4, [0357] R.sub.E.sup.2 is (C.sub.1-C.sub.16)-alkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.3-C.sub.6)-cycloalkyl, aryl; benzyl, halobenzyl, [0358] R.sub.E.sup.3 is hydrogen or (C.sub.1-C.sub.6)-alkyl. [0359] S11) Active ingredients of the oxyimino compounds type (S11), which are known as seed-dressing agents, for example [0360] oxabetrinil ((Z)-1,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile) (S11-1), which is known as a seed-dressing safener for millet/sorghum against metolachlor damage, [0361] fluxofenim (1-(4-chlorophenyl)-2,2,2-trifluoro-1-ethanone O-(1,3-dioxolan-2-ylmethyl)oxime) (S11-2), which is known as a seed-dressing safener for millet/sorghum against metolachlor damage, and [0362] cyometrinil or CGA-43089 ((Z)-cyanomethoxyimino(phenyl)acetonitrile) (S11-3), which is known as a seed-dressing safener for millet/sorghum against metolachlor damage. [0363] S12) Active ingredients from the class of the isothiochromanones (S12), for example methyl [(3-oxo-1H-2-benzothiopyran-4(3H)-ylidene)methoxy]acetate (CAS Reg. No. 205121-04-6) (S12-1) and related compounds from WO-A-1998/13361. [0364] S13) One or more compounds from group (S13): [0365] naphthalic anhydride (1,8-naphthalenedicarboxylic anhydride) (S13-1), which is known as a seed-dressing safener for maize against thiocarbamate herbicide damage, [0366] fenclorim (4,6-dichloro-2-phenylpyrimidine) (S13-2), which is known as a safener for pretilachlor in sown rice, [0367] flurazole (benzyl 2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate) (S13-3), which is known as a seed-dressing safener for millet/sorghum against alachlor and metolachlor damage, CL 304415 (CAS Reg. No. 31541-57-8) [0368] (4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid) (S13-4) from American Cyanamid, which is known as a safener for corn against damage by imidazolinones, [0369] MG 191 (CAS Reg. No. 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5) from Nitrokemia, which is known as a safener for maize, [0370] MG 838 (CAS Reg. No. 133993-74-5) [0371] (2-propenyl 1-oxa-4-azaspiro[4.5]decane-4-carbodithioate) (S13-6) from Nitrokemia [0372] disulfoton (0,0-diethyl S-2-ethylthioethyl phosphorodithioate) (S13-7), [0373] dietholate (0,0-diethyl O-phenyl phosphorothioate) (S13-8), [0374] mephenate (4-chlorophenyl methylcarbamate) (S13-9). [0375] S14) Active ingredients which, in addition to herbicidal action against harmful plants, also have safener action on crop plants such as rice, for example [0376] dimepiperate or MY-93 (S-1-methyl 1-phenylethylpiperidine-1-carbothioate), which is known as a safener for rice against damage by the herbicide molinate, [0377] daimuron or SK 23 (1-(1-methyl-1-phenylethyl)-3-p-tolylurea), which is known as a safener for rice against damage by the herbicide imazosulfuron, [0378] cumyluron=JC-940 (3-(2-chlorophenylmethyl)-1-(1-methyl-1-phenylethyl)urea, see JP-A-60087270), which is known as a safener for rice against damage by some herbicides, [0379] methoxyphenone or NK 049 (3,3-dimethyl-4-methoxybenzophenone), which is known as a safener for rice against damage by some herbicides, [0380] CSB (1-bromo-4-(chloromethylsulfonyl)benzene) from Kumiai, (CAS Reg. No. 54091-06-4), which is known as a safener against damage by some herbicides in rice. [0381] S15) Compounds of the formula (S15) or tautomers thereof

##STR00019## [0382] as described in WO-A-2008/131861 and WO-A-2008/131860 [0383] in which [0384] R.sub.H.sup.1 is a (C.sub.1-C.sub.6)-haloalkyl radical and [0385] R.sub.H.sup.2 is hydrogen or halogen and [0386] R.sub.H.sup.3, R.sub.H.sup.4 are independently hydrogen, (C.sub.1-C.sub.16)-alkyl, (C.sub.2-C.sub.16)-alkenyl or (C.sub.2-C.sub.16)-alkynyl, where each of the 3 latter radicals is unsubstituted or substituted by one or more radicals from the group of halogen, hydroxyl, cyano, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-haloalkoxy, (C.sub.1-C.sub.4)-alkylthio, (C.sub.1-C.sub.4)-alkylamino, di[(C.sub.1-C.sub.4)-alkyl]amino, [(C.sub.1-C.sub.4)-alkoxy]carbonyl, [(C.sub.1-C.sub.4)-haloalkoxy]carbonyl, (C.sub.3-C.sub.6)-cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted, and heterocyclyl which is unsubstituted or substituted, [0387] or (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.4-C.sub.6)-cycloalkenyl, (C.sub.3-C.sub.6)-cycloalkyl fused on one side of the ring to a 4 to 6-membered saturated or unsaturated carbocyclic ring, or (C.sub.4-C.sub.6)-cycloalkenyl fused on one side of the ring to a 4 to 6-membered saturated or unsaturated carbocyclic ring, [0388] where each of the 4 latter radicals is unsubstituted or substituted by one or more radicals from the group of halogen, hydroxyl, cyano, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-haloalkoxy, (C.sub.1-C.sub.4)-alkylthio, (C.sub.1-C.sub.4)-alkylamino, di[(C.sub.1-C.sub.4)-alkyl]amino, [(C.sub.1-C.sub.4)-alkoxy]carbonyl, [(C.sub.1-C.sub.4)-haloalkoxy]carbonyl, (C.sub.3-C.sub.6)-cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted, and heterocyclyl which is unsubstituted or substituted, [0389] or [0390] R.sub.H.sup.3 is (C.sub.1-C.sub.4)-alkoxy, (C.sub.2-C.sub.4)-alkenyloxy, (C.sub.2-C.sub.6)-alkynyloxy or (C.sub.2-C.sub.4)-haloalkoxy and [0391] R.sub.H.sup.4 is hydrogen or (C.sub.1-C.sub.4)-alkyl or [0392] R.sub.H.sup.3 and R.sub.H.sup.4 together with the directly bonded nitrogen atom are a four- to eight-membered heterocyclic ring which, as well as the nitrogen atom, may also contain further ring heteroatoms, preferably up to two further ring heteroatoms from the group of N, O and S, and which is unsubstituted or substituted by one or more radicals from the group of halogen, cyano, nitro, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.1-C.sub.4)-alkoxy, (C.sub.1-C.sub.4)-haloalkoxy and (C.sub.1-C.sub.4)-alkylthio. [0393] S16) Active ingredients which are used primarily as herbicides but also have safener action on crop plants, for example [0394] (2,4-dichlorophenoxy)acetic acid (2,4-D), [0395] (4-chlorophenoxy)acetic acid, [0396] (R,S)-2-(4-chloro-o-tolyloxy)propionic acid (mecoprop), [0397] 4-(2,4-dichlorophenoxy)butyric acid (2,4-DB), [0398] (4-chloro-o-tolyloxy)acetic acid (MCPA), [0399] 4-(4-chloro-o-tolyloxy)butyric acid, [0400] 4-(4-chlorophenoxy)butyric acid, [0401] 3,6-dichloro-2-methoxybenzoic acid (dicamba), [0402] 1-(ethoxycarbonyl)ethyl 3,6-dichloro-2-methoxybenzoate (lactidichloro-ethyl).

[0403] Preferred safeners in combination with the inventive compounds of the general formula (I) and/or salts thereof, especially with the compounds of the formulae (I-1) to (I-90) and/or salts thereof, are: cloquintocet-mexyl, cyprosulfamide, fenchlorazole ethyl ester, isoxadifen-ethyl, mefenpyr-diethyl, fenclorim, cumyluron, 54-1 and S4-5, and particularly preferred safeners are: cloquintocet-mexyl, cyprosulfamide, isoxadifen-ethyl and mefenpyr-diethyl.

Biological Examples

[0404] The following abbreviations are used in the examples below and the tables:

[0405] Harmful Plants Tested: [0406] ABUTH: Abutilon theophrasti [0407] ALOMY: Alopecurus myosuroides [0408] AMARE Amaranthus retroflexus [0409] AVEFA: Avena fatua [0410] DIGSA: Digitaria sanguinalis [0411] ECHCG: Echinochloa crus-galli [0412] KCHSC: Kochia scoparia [0413] LOLRI: Lolium rigidum [0414] MATIN: Matricaria inodora [0415] PHBPU: Pharbitis purpurea [0416] POAAN: Poa annua [0417] POLCO: Polygonum convolvulus [0418] SETVI: Setaria viridis [0419] STEME: Stellaria media [0420] VERPE: Veronica persica [0421] VIOTR: Viola tricolor

[0422] Useful Plants Tested [0423] BRSNW: Brassica napus [0424] GLXMA: Glycine max [0425] ORYSA: Oryza sativa [0426] TRZAS: Triticum aestivum [0427] ZEAMX: Zea mays

[0428] A. Herbicidal Pre-Emergence Efficacy

[0429] Seeds of mono- and dicotyledonous weed plants were 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), were 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 liters per hectare (converted). After the treatment, the pots were placed in a greenhouse and kept under good growth conditions for the test plants. After about 3 weeks, the efficacy of the preparations was scored visually in comparison with untreated controls as percentages.

[0430] For example, [0431] 100% efficacy=plants have died, [0432] 0% efficacy=like untreated control plants.

[0433] Tables A1a to A12c below show the effects of selected compounds of the general formula (I) according to table 1 on various harmful plants at an application rate corresponding to 1280 g/ha or less, which were obtained by the experimental procedure mentioned above.

TABLE-US-00002 TABLE A1a Pre-emergence efficacy at 80 g/ha against ABUTH in % Example number Dosage [g/ha] ABUTH I-2 80 100 I-3 80 100 I-5 80 100 I-6 80 100 I-8 80 90 I-10 80 100 I-12 80 90 I-14 80 100 I-15 80 100 I-20 80 100 I-23 80 90 I-29 80 90 I-28 80 100 I-38 80 100 I-39 80 90 I-40 80 100 I-45 80 100 I-46 80 90 I-47 80 100 I-42 80 100 I-48 80 90 I-49 80 100 I-50 80 90 I-53 80 100 I-56 80 100

TABLE-US-00003 TABLE A1b Pre-emergence efficacy at 320 g/ha against ABUTH in % Example number Dosage [g/ha] ABUTH I-2 320 100 I-3 320 100 I-5 320 100 I-6 320 100 I-7 320 90 I-8 320 90 I-10 320 100 I-12 320 90 I-13 320 90 I-14 320 100 I-15 320 100 I-16 320 100 I-18 320 90 I-19 320 90 I-20 320 100 I-22 320 100 I-23 320 90 I-36 320 100 I-31 320 90 I-30 320 90 I-29 320 100 I-28 320 100 I-33 320 100 I-32 320 90 I-38 320 100 I-39 320 100 I-40 320 100 I-41 320 100 I-43 320 100 I-45 320 100 I-46 320 100 I-47 320 100 I-42 320 100 I-48 320 100 I-49 320 100 I-50 320 100 I-52 320 100 I-53 320 100 I-54 320 90 I-56 320 100 I-57 320 90

TABLE-US-00004 TABLE A1c Pre-emergence efficacy at 1280 g/ha against ABUTH in % Example number Dosage [g/ha] ABUTH I-1 1280 100 I-2 1280 100 I-3 1280 100 I-5 1280 100 I-6 1280 100 I-7 1280 100 I-8 1280 100 I-9 1280 90 I-10 1280 100 I-12 1280 100 I-13 1280 100 I-14 1280 100 I-15 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-25 1280 100 I-27 1280 90 I-36 1280 100 I-31 1280 90 I-30 1280 100 I-29 1280 100 I-28 1280 100 I-33 1280 100 I-35 1280 100 I-32 1280 100 I-34 1280 90 I-38 1280 100 I-39 1280 100 I-40 1280 100 I-41 1280 100 I-43 1280 100 I-44 1280 100 I-45 1280 100 I-46 1280 100 I-47 1280 100 I-42 1280 100 I-48 1280 100 I-49 1280 100 I-50 1280 100 I-52 1280 100 I-53 1280 100 I-54 1280 100 I-55 1280 100 I-56 1280 100 I-57 1280 100 I-58 1280 90 I-59 1280 90 I-68 1280 100 I-69 1280 90 I-72 1280 90 I-73 1280 90 I-74 1280 90 I-75 1280 100 I-80 1280 90 I-79 1280 90

TABLE-US-00005 TABLE A2a Pre-emergence efficacy at 320 g/ha against ALOMY in % Example number Dosage [g/ha] ALOMY I-2 320 100 I-3 320 90 I-10 320 90 I-14 320 90 I-39 320 90 I-40 320 90 I-45 320 90 I-47 320 100 I-42 320 100 I-48 320 90 I-56 320 90

TABLE-US-00006 TABLE A2b Pre-emergence efficacy at 1280 g/ha against ALOMY in % Example number Dosage [g/ha] ALOMY I-2 1280 100 I-3 1280 100 I-5 1280 90 I-6 1280 90 I-8 1280 90 I-10 1280 90 I-14 1280 100 I-23 1280 90 I-31 1280 90 I-29 1280 90 I-28 1280 100 I-35 1280 90 I-32 1280 90 I-38 1280 100 I-39 1280 100 I-40 1280 100 I-41 1280 100 I-43 1280 90 I-44 1280 100 I-45 1280 100 I-46 1280 100 I-47 1280 100 I-42 1280 100 I-48 1280 90 I-49 1280 90 I-53 1280 100 I-56 1280 100 I-57 1280 100 I-68 1280 90 I-74 1280 90

TABLE-US-00007 TABLE A3a Pre-emergence efficacy at 80 g/ha against DIGSA in % Example number Dosage [g/ha] DIGSA I-14 80 100 I-19 80 100 I-23 80 90 I-25 80 90 I-29 80 90 I-28 80 90 I-39 80 100 I-40 80 100 I-41 80 100 I-45 80 90 I-46 80 90 I-47 80 100 I-42 80 100 I-48 80 100 I-49 80 90 I-50 80 90 I-53 80 100 I-55 80 100 I-56 80 100 I-57 80 90

TABLE-US-00008 TABLE A3b Pre-emergence efficacy at 320 g/ha against DIGSA in % Example number Dosage [g/ha] DIGSA I-14 320 100 I-16 320 100 I-19 320 100 I-20 320 100 I-21 320 100 I-22 320 100 I-23 320 100 I-24 320 100 I-25 320 100 I-27 320 90 I-36 320 90 I-31 320 90 I-30 320 100 I-29 320 100 I-28 320 100 I-33 320 100 I-35 320 90 I-32 320 90 I-38 320 100 I-39 320 100 I-40 320 100 I-41 320 100 I-43 320 100 I-44 320 100 I-45 320 100 I-46 320 100 I-47 320 100 I-42 320 100 I-48 320 100 I-49 320 90 I-50 320 90 I-51 320 90 I-52 320 90 I-53 320 100 I-54 320 90 I-55 320 100 I-56 320 100 I-57 320 100 I-59 320 100 I-64 320 90 I-68 320 90 I-72 320 90 I-73 320 90 I-74 320 100 I-75 320 90 I-76 320 90 I-77 320 90 I-80 320 90 I-79 320 100

TABLE-US-00009 TABLE A3c Pre-emergence efficacy at 1280 g/ha against DIGSA in % Example number Dosage [g/ha] DIGSA I-13 1280 100 I-14 1280 100 I-16 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 100 I-25 1280 100 I-27 1280 100 I-26 1280 100 I-36 1280 100 I-31 1280 100 I-30 1280 100 I-29 1280 100 I-28 1280 100 I-33 1280 100 I-35 1280 100 I-32 1280 90 I-34 1280 90 I-38 1280 100 I-39 1280 100 I-40 1280 100 I-41 1280 100 I-43 1280 100 I-44 1280 100 I-45 1280 100 I-46 1280 100 I-47 1280 100 I-42 1280 100 I-48 1280 100 I-49 1280 90 I-50 1280 100 I-51 1280 100 I-52 1280 100 I-53 1280 100 I-54 1280 100 I-55 1280 100 I-56 1280 100 I-57 1280 100 I-58 1280 90 I-59 1280 100 I-64 1280 100 I-65 1280 90 I-67 1280 90 I-68 1280 100 I-69 1280 90 I-72 1280 100 I-73 1280 100 I-74 1280 100 I-75 1280 100 I-76 1280 90 I-77 1280 100 I-80 1280 100 I-79 1280 100

TABLE-US-00010 TABLE A4a Pre-emergence efficacy at 80 g/ha against ECHCG in % Example number Dosage [g/ha] ECHCG I-2 80 90 I-6 80 100 I-8 80 90 I-10 80 100 I-14 80 100 I-15 80 100 I-23 80 90 I-28 80 90 I-40 80 100 I-45 80 90 I-46 80 100 I-47 80 100 I-42 80 100 I-48 80 90 I-49 80 90 I-53 80 100 I-56 80 100

TABLE-US-00011 TABLE A4b Pre-emergence efficacy at 320 g/ha against ECHCG in % Example number Dosage [g/ha] ECHCG I-2 320 100 I-3 320 100 I-5 320 100 I-6 320 100 I-7 320 100 I-8 320 90 I-10 320 100 I-12 320 90 I-14 320 100 I-15 320 100 I-16 320 90 I-18 320 90 I-22 320 90 I-23 320 90 I-24 320 100 I-25 320 100 I-30 320 100 I-29 320 100 I-28 320 100 I-33 320 100 I-38 320 90 I-39 320 90 I-40 320 100 I-41 320 100 I-43 320 100 I-44 320 100 I-45 320 100 I-46 320 100 I-47 320 100 I-42 320 100 I-48 320 90 I-49 320 90 I-50 320 90 I-52 320 90 I-53 320 100 I-54 320 100 I-55 320 100 I-56 320 100 I-68 320 90 I-74 320 90

TABLE-US-00012 TABLE A4c Pre-emergence efficacy at 1280 g/ha against ECHCG in % Example number Dosage [g/ha] ECHCG I-1 1280 100 I-2 1280 100 I-3 1280 100 I-5 1280 100 I-6 1280 100 I-7 1280 100 I-8 1280 100 I-9 1280 100 I-10 1280 100 I-12 1280 100 I-13 1280 100 I-14 1280 100 I-15 1280 100 I-16 1280 100 I-18 1280 100 I-19 1280 90 I-20 1280 100 I-21 1280 100 I-22 1280 90 I-23 1280 90 I-24 1280 100 I-25 1280 100 I-27 1280 90 I-26 1280 90 I-36 1280 100 I-31 1280 100 I-30 1280 100 I-29 1280 100 I-28 1280 100 I-33 1280 100 I-35 1280 100 I-32 1280 100 I-38 1280 100 I-39 1280 100 I-40 1280 100 I-41 1280 100 I-43 1280 100 I-44 1280 100 I-45 1280 100 I-46 1280 100 I-47 1280 100 I-42 1280 100 I-48 1280 90 I-49 1280 90 I-50 1280 100 I-51 1280 90 I-52 1280 90 I-53 1280 100 I-54 1280 100 I-55 1280 100 I-56 1280 100 I-57 1280 100 I-59 1280 100 I-61 1280 100 I-64 1280 100 I-68 1280 100 I-69 1280 90 I-73 1280 90 I-74 1280 100 I-75 1280 100 I-80 1280 90 I-79 1280 90

TABLE-US-00013 TABLE A5a Pre-emergence efficacy at 80 g/ha against KCHSC in % Example number Dosage [g/ha] KCHSC I-2 80 100 I-3 80 100 I-5 80 100 I-6 80 90 I-7 80 90 I-8 80 100 I-9 80 90 I-10 80 100 I-14 80 100 I-15 80 100 I-16 80 100 I-20 80 90 I-21 80 90 I-23 80 90 I-25 80 90 I-31 80 90 I-39 80 100 I-40 80 100 I-41 80 100 I-47 80 100 I-42 80 100 I-48 80 100 I-49 80 100 I-50 80 90 I-53 80 100 I-56 80 100 I-68 80 90

TABLE-US-00014 TABLE A5b Pre-emergence efficacy at 320 g/ha against KCHSC in % Example number Dosage [g/ha] KCHSC I-1 320 100 I-2 320 100 I-3 320 100 I-5 320 100 I-6 320 90 I-7 320 100 I-8 320 100 I-9 320 100 I-10 320 100 I-12 320 90 I-14 320 100 I-15 320 100 I-16 320 100 I-19 320 90 I-20 320 90 I-21 320 100 I-22 320 90 I-23 320 100 I-25 320 100 I-36 320 90 I-31 320 100 I-30 320 100 I-29 320 90 I-28 320 90 I-32 320 90 I-38 320 100 I-39 320 100 I-40 320 100 I-41 320 100 I-44 320 100 I-45 320 100 I-47 320 100 I-42 320 100 I-48 320 100 I-49 320 100 I-50 320 100 I-52 320 90 I-53 320 100 I-55 320 100 I-56 320 100 I-57 320 100 I-59 320 100 I-68 320 100 I-73 320 90 I-74 320 90 I-75 320 90 I-80 320 90 I-79 320 90

TABLE-US-00015 TABLE A5c Pre-emergence efficacy at 1280 g/ha against KCHSC in % Example number Dosage [g/ha] KCHSC I-1 1280 100 I-2 1280 100 I-3 1280 100 I-4 1280 100 I-5 1280 100 I-6 1280 100 I-7 1280 100 I-8 1280 100 I-9 1280 100 I-10 1280 100 I-12 1280 100 I-13 1280 100 I-14 1280 100 I-15 1280 100 I-16 1280 100 I-19 1280 90 I-20 1280 100 I-21 1280 100 I-22 1280 100 I-23 1280 100 I-24 1280 100 I-25 1280 100 I-27 1280 100 I-26 1280 90 I-36 1280 100 I-31 1280 100 I-30 1280 100 I-29 1280 100 I-28 1280 90 I-35 1280 90 I-32 1280 100 I-34 1280 90 I-38 1280 100 I-39 1280 100 I-40 1280 100 I-41 1280 100 I-43 1280 100 I-44 1280 100 I-45 1280 100 I-46 1280 90 I-47 1280 100 I-42 1280 100 I-48 1280 100 I-49 1280 100 I-50 1280 100 I-51 1280 100 I-52 1280 100 I-53 1280 100 I-54 1280 90 I-55 1280 100 I-56 1280 100 I-57 1280 100 I-58 1280 90 I-59 1280 100 I-64 1280 90 I-67 1280 100 I-68 1280 100 I-69 1280 90 I-72 1280 90 I-73 1280 90 I-74 1280 100 I-75 1280 100 I-80 1280 100 I-79 1280 100 I-84 1280 90

TABLE-US-00016 TABLE A6a Pre-emergence efficacy at 320 g/ha against LOLRI in % Example number Dosage [g/ha] LOLRI I-2 320 90 I-3 320 100 I-6 320 90 I-8 320 90 I-10 320 90 I-14 320 100 I-23 320 90 I-25 320 90 I-30 320 90 I-29 320 100 I-28 320 90 I-39 320 100 I-40 320 100 I-41 320 100 I-43 320 100 I-44 320 100 I-45 320 100 I-46 320 100 I-47 320 100 I-42 320 100 I-48 320 90 I-49 320 90 I-50 320 90 I-53 320 90 I-56 320 100

TABLE-US-00017 TABLE A6b Pre-emergence efficacy at 1280 g/ha against LOLRI in % Example number Dosage [g/ha] LOLRI I-2 1280 100 I-3 1280 100 I-6 1280 90 I-7 1280 90 I-8 1280 90 I-9 1280 90 I-10 1280 90 I-12 1280 90 I-13 1280 90 I-14 1280 100 I-15 1280 90 I-16 1280 90 I-18 1280 90 I-20 1280 90 I-22 1280 90 I-23 1280 90 I-24 1280 100 I-25 1280 100 I-36 1280 100 I-31 1280 100 I-30 1280 100 I-29 1280 100 I-28 1280 100 I-33 1280 100 I-35 1280 100 I-32 1280 90 I-38 1280 100 I-39 1280 100 I-40 1280 100 I-41 1280 100 I-43 1280 100 I-44 1280 100 I-45 1280 100 I-46 1280 100 I-47 1280 100 I-42 1280 100 I-48 1280 90 I-49 1280 90 I-50 1280 90 I-51 1280 90 I-52 1280 100 I-53 1280 100 I-54 1280 90 I-55 1280 100 I-56 1280 100 I-57 1280 100 I-59 1280 90 I-68 1280 100 I-72 1280 90 I-73 1280 90 I-74 1280 100

TABLE-US-00018 TABLE A7a Pre-emergence efficacy at 320 g/ha against MATIN in % Example number Dosage [g/ha] MATIN I-1 320 90 I-3 320 100 I-5 320 90 I-7 320 100 I-8 320 90 I-9 320 90 I-10 320 100 I-12 320 90 I-16 320 100 I-23 320 90 I-38 320 100 I-39 320 100 I-40 320 100 I-41 320 100 I-44 320 90 I-47 320 100 I-42 320 90 I-48 320 100 I-49 320 100 I-51 320 90 I-57 320 90 I-59 320 90 I-68 320 100

TABLE-US-00019 TABLE A7b Pre-emergence efficacy at 1280 g/ha against MATIN in % Example number Dosage [g/ha] MATIN I-1 1280 100 I-2 1280 100 I-3 1280 100 I-5 1280 100 I-6 1280 100 I-7 1280 100 I-8 1280 100 I-9 1280 100 I-10 1280 100 I-12 1280 100 I-14 1280 100 I-16 1280 100 I-18 1280 90 I-20 1280 100 I-23 1280 100 I-25 1280 100 I-31 1280 90 I-30 1280 100 I-29 1280 90 I-28 1280 100 I-33 1280 90 I-35 1280 100 I-32 1280 90 I-38 1280 100 I-39 1280 100 I-40 1280 100 I-41 1280 100 I-43 1280 90 I-44 1280 100 I-45 1280 90 I-46 1280 90 I-47 1280 100 I-42 1280 100 I-48 1280 100 I-49 1280 100 I-50 1280 90 I-51 1280 90 I-52 1280 90 I-53 1280 100 I-54 1280 90 I-56 1280 100 I-57 1280 100 I-59 1280 100 I-68 1280 100

TABLE-US-00020 TABLE A8a Pre-emergence efficacy at 80 g/ha against POAAN in % Example number Dosage [g/ha] POAAN I-2 80 100 I-3 80 90 I-5 80 90 I-7 80 100 I-8 80 90 I-10 80 100 I-14 80 100 I-15 80 100 I-23 80 90 I-31 80 90 I-30 80 90 I-29 80 90 I-28 80 90 I-40 80 100 I-41 80 100 I-45 80 90 I-46 80 90 I-47 80 100 I-42 80 100 I-48 80 90 I-49 80 90 I-50 80 90 I-53 80 100 I-56 80 90

TABLE-US-00021 TABLE A8b Pre-emergence efficacy at 320 g/ha against POAAN in % Example number Dosage [g/ha] POAAN I-2 320 100 I-3 320 100 I-5 320 100 I-6 320 90 I-7 320 100 I-8 320 100 I-9 320 90 I-10 320 100 I-12 320 100 I-13 320 90 I-14 320 100 I-15 320 100 I-16 320 100 I-21 320 100 I-23 320 90 I-24 320 100 I-25 320 100 I-27 320 90 I-26 320 90 I-31 320 100 I-30 320 100 I-29 320 100 I-28 320 100 I-33 320 100 I-35 320 100 I-32 320 90 I-34 320 90 I-38 320 100 I-39 320 100 I-40 320 100 I-41 320 100 I-43 320 100 I-44 320 100 I-45 320 100 I-46 320 100 I-47 320 100 I-42 320 100 I-48 320 100 I-49 320 100 I-50 320 90 I-52 320 90 I-53 320 100 I-54 320 90 I-55 320 90 I-56 320 100 I-57 320 100 I-59 320 100 I-68 320 90 I-73 320 90 I-74 320 100 I-75 320 100 I-76 320 90 I-77 320 100 I-80 320 90

TABLE-US-00022 TABLE A8c Pre-emergence efficacy at 1280 g/ha against POAAN in % Example number Dosage [g/ha] POAAN I-1 1280 90 I-2 1280 100 I-3 1280 100 I-5 1280 100 I-6 1280 90 I-7 1280 100 I-8 1280 100 I-9 1280 100 I-10 1280 100 I-12 1280 100 I-13 1280 100 I-14 1280 100 I-15 1280 100 I-16 1280 100 I-18 1280 90 I-19 1280 90 I-20 1280 90 I-21 1280 100 I-22 1280 90 I-23 1280 90 I-24 1280 100 I-25 1280 100 I-27 1280 90 I-26 1280 100 I-36 1280 90 I-31 1280 100 I-30 1280 100 I-29 1280 100 I-28 1280 100 I-33 1280 100 I-35 1280 100 I-32 1280 90 I-34 1280 90 I-38 1280 100 I-39 1280 100 I-40 1280 100 I-41 1280 100 I-43 1280 100 I-44 1280 100 I-45 1280 100 I-46 1280 100 I-47 1280 100 I-42 1280 100 I-48 1280 100 I-49 1280 100 I-50 1280 100 I-51 1280 100 I-52 1280 100 I-53 1280 100 I-54 1280 100 I-55 1280 100 I-56 1280 100 I-57 1280 100 I-59 1280 100 I-64 1280 100 I-65 1280 90 I-68 1280 100 I-72 1280 100 I-73 1280 100 I-74 1280 100 I-75 1280 100 I-76 1280 90 I-77 1280 100 I-80 1280 90 I-79 1280 90

TABLE-US-00023 TABLE A9a Pre-emergence efficacy at 80 g/ha against SETVI in % Example number Dosage [g/ha] SETVI I-2 80 100 I-3 80 100 I-5 80 100 I-6 80 90 I-7 80 100 I-8 80 100 I-10 80 90 I-14 80 100 I-15 80 100 I-30 80 90 I-28 80 100 I-34 80 90 I-38 80 90 I-39 80 90 I-40 80 100 I-41 80 100 I-45 80 90 I-46 80 90 I-47 80 100 I-42 80 100 I-48 80 90 I-49 80 90 I-50 80 90 I-53 80 100 I-55 80 100 I-56 80 100 I-57 80 90 I-68 80 90

TABLE-US-00024 TABLE A9b Pre-emergence efficacy at 320 g/ha against SETVI in % Example number Dosage [g/ha] SETVI I-1 320 90 I-2 320 100 I-3 320 100 I-5 320 100 I-6 320 90 I-7 320 100 I-8 320 100 I-9 320 100 I-10 320 90 I-12 320 100 I-14 320 100 I-15 320 100 I-16 320 100 I-19 320 90 I-20 320 90 I-22 320 90 I-24 320 100 I-25 320 100 I-27 320 100 I-26 320 90 I-31 320 100 I-30 320 100 I-29 320 100 I-28 320 100 I-33 320 100 I-35 320 100 I-32 320 90 I-34 320 90 I-38 320 100 I-39 320 100 I-40 320 100 I-41 320 100 I-43 320 100 I-44 320 100 I-45 320 100 I-46 320 100 I-47 320 100 I-42 320 100 I-48 320 90 I-49 320 100 I-50 320 90 I-51 320 90 I-52 320 100 I-53 320 100 I-54 320 100 I-55 320 100 I-56 320 100 I-57 320 100 I-59 320 100 I-68 320 100 I-72 320 90 I-73 320 90 I-74 320 90 I-75 320 90 I-76 320 100 I-77 320 90 I-80 320 90 I-79 320 90

TABLE-US-00025 TABLE A9c Pre-emergence efficacy at 1280 g/ha against SETVI in % Example number Dosage [g/ha] SETVI I-1 1280 100 I-2 1280 100 I-3 1280 100 I-5 1280 100 I-6 1280 100 I-7 1280 100 I-8 1280 100 I-9 1280 100 I-10 1280 100 I-12 1280 100 I-13 1280 100 I-14 1280 100 I-15 1280 100 I-16 1280 100 I-18 1280 90 I-19 1280 100 I-20 1280 100 I-21 1280 100 I-22 1280 100 I-23 1280 100 I-24 1280 100 I-25 1280 100 I-27 1280 100 I-26 1280 100 I-36 1280 100 I-31 1280 100 I-30 1280 100 I-29 1280 100 I-28 1280 100 I-33 1280 100 I-35 1280 100 I-32 1280 100 I-34 1280 100 I-38 1280 100 I-39 1280 100 I-40 1280 100 I-41 1280 100 I-43 1280 100 I-44 1280 100 I-45 1280 100 I-46 1280 100 I-47 1280 100 I-42 1280 100 I-48 1280 100 I-49 1280 100 I-50 1280 100 I-51 1280 90 I-52 1280 100 I-53 1280 100 I-54 1280 100 I-55 1280 100 I-56 1280 100 I-57 1280 100 I-59 1280 100 I-64 1280 100 I-67 1280 100 I-68 1280 100 I-69 1280 100 I-72 1280 100 I-73 1280 100 I-74 1280 100 I-75 1280 100 I-76 1280 100 I-77 1280 100 I-80 1280 100 I-79 1280 100 I-84 1280 100

TABLE-US-00026 TABLE A10a Pre-emergence efficacy at 80 g/ha against STEME in % Example number Dosage [g/ha] STEME I-2 80 100 I-3 80 100 I-5 80 90 I-6 80 100 I-7 80 90 I-8 80 100 I-10 80 100 I-13 80 100 I-14 80 100 I-15 80 100 I-22 80 100 I-23 80 100 I-31 80 90 I-30 80 100 I-29 80 90 I-28 80 90 I-33 80 100 I-38 80 100 I-41 80 100 I-44 80 100 I-45 80 90 I-46 80 90 I-47 80 100 I-42 80 100 I-48 80 90 I-49 80 100 I-52 80 90 I-53 80 100 I-56 80 100 I-59 80 90 I-76 80 90

TABLE-US-00027 TABLE A10b Pre-emergence efficacy at 320 g/ha against STEME in % Example number Dosage [g/ha] STEME I-2 320 100 I-3 320 100 I-5 320 100 I-6 320 100 I-7 320 90 I-8 320 100 I-9 320 100 I-10 320 100 I-12 320 100 I-13 320 100 I-14 320 100 I-15 320 100 I-16 320 100 I-19 320 100 I-20 320 100 I-21 320 100 I-22 320 100 I-23 320 100 I-24 320 100 I-25 320 90 I-31 320 100 I-30 320 100 I-29 320 100 I-28 320 100 I-33 320 100 I-32 320 90 I-34 320 90 I-38 320 100 I-39 320 100 I-40 320 100 I-41 320 100 I-43 320 100 I-44 320 100 I-45 320 100 I-46 320 100 I-47 320 100 I-42 320 100 I-48 320 100 I-49 320 100 I-50 320 100 I-51 320 90 I-52 320 90 I-53 320 100 I-54 320 90 I-55 320 100 I-56 320 100 I-57 320 100 I-59 320 100 I-68 320 100 I-72 320 90 I-73 320 100 I-74 320 90 I-75 320 100 I-76 320 90 I-80 320 100 I-79 320 90

TABLE-US-00028 TABLE A10c Pre-emergence efficacy at 1280 g/ha against STEME in % Example number Dosage [g/ha] STEME I-2 1280 100 I-3 1280 100 I-5 1280 100 I-6 1280 100 I-7 1280 100 I-8 1280 100 I-9 1280 100 I-10 1280 100 I-12 1280 100 I-13 1280 100 I-14 1280 100 I-15 1280 100 I-16 1280 100 I-17 1280 90 I-18 1280 90 I-19 1280 100 I-20 1280 100 I-21 1280 100 I-22 1280 100 I-23 1280 100 I-24 1280 100 I-25 1280 100 I-27 1280 90 I-26 1280 90 I-36 1280 90 I-31 1280 100 I-30 1280 100 I-29 1280 100 I-28 1280 100 I-33 1280 100 I-35 1280 100 I-32 1280 90 I-34 1280 90 I-38 1280 100 I-39 1280 100 I-40 1280 100 I-41 1280 100 I-43 1280 100 I-44 1280 100 I-45 1280 100 I-46 1280 100 I-47 1280 100 I-42 1280 100 I-48 1280 100 I-49 1280 100 I-50 1280 100 I-51 1280 100 I-52 1280 100 I-53 1280 100 I-54 1280 100 I-55 1280 100 I-56 1280 100 I-57 1280 100 I-59 1280 100 I-64 1280 90 I-68 1280 100 I-69 1280 90 I-72 1280 100 I-73 1280 100 I-74 1280 100 I-75 1280 100 I-76 1280 100 I-77 1280 90 I-80 1280 100 I-79 1280 100

TABLE-US-00029 TABLE A11a Pre-emergence efficacy at 80 g/ha against VERPE in % Example number Dosage [g/ha] VERPE I-2 80 100 I-3 80 100 I-5 80 90 I-8 80 100 I-10 80 90 I-14 80 100 I-23 80 90 I-29 80 100 I-33 80 90 I-32 80 90 I-38 80 90 I-39 80 90 I-40 80 100 I-41 80 90 I-46 80 90 I-47 80 90 I-42 80 100 I-48 80 90 I-49 80 90 I-50 80 90 I-53 80 100 I-74 80 90

TABLE-US-00030 TABLE A11b Pre-emergence efficacy at 320 g/ha against VERPE in % Example number Dosage [g/ha] VERPE I-1 320 100 I-2 320 100 I-3 320 100 I-5 320 100 I-8 320 100 I-10 320 100 I-12 320 90 I-14 320 100 I-15 320 90 I-16 320 90 I-18 320 90 I-23 320 100 I-31 320 100 I-30 320 100 I-29 320 100 I-28 320 100 I-33 320 100 I-35 320 90 I-32 320 90 I-34 320 90 I-38 320 90 I-39 320 100 I-40 320 100 I-41 320 100 I-43 320 100 I-44 320 100 I-45 320 100 I-46 320 90 I-47 320 100 I-42 320 100 I-48 320 100 I-49 320 100 I-50 320 100 I-52 320 100 I-53 320 100 I-55 320 100 I-56 320 100 I-57 320 90 I-59 320 90 I-68 320 100 I-72 320 90 I-74 320 100 I-75 320 90 I-80 320 90 I-79 320 100

TABLE-US-00031 TABLE A11c Pre-emergence efficacy at 1280 g/ha against VERPE in % Example number Dosage [g/ha] VERPE I-1 1280 100 I-2 1280 100 I-3 1280 100 I-5 1280 100 I-6 1280 90 I-7 1280 100 I-8 1280 100 I-9 1280 100 I-10 1280 100 I-12 1280 100 I-13 1280 100 I-14 1280 100 I-15 1280 90 I-16 1280 100 I-18 1280 100 I-21 1280 90 I-22 1280 90 I-23 1280 100 I-25 1280 90 I-27 1280 90 I-26 1280 100 I-36 1280 100 I-31 1280 100 I-30 1280 100 I-29 1280 100 I-28 1280 100 I-33 1280 100 I-35 1280 100 I-32 1280 100 I-34 1280 100 I-38 1280 100 I-39 1280 100 I-40 1280 100 I-41 1280 100 I-43 1280 100 I-44 1280 100 I-45 1280 100 I-46 1280 100 I-47 1280 100 I-42 1280 100 I-48 1280 100 I-49 1280 100 I-50 1280 100 I-51 1280 100 I-52 1280 100 I-53 1280 100 I-54 1280 90 I-55 1280 100 I-56 1280 100 I-57 1280 100 I-59 1280 100 I-64 1280 100 I-67 1280 100 I-68 1280 100 I-69 1280 100 I-72 1280 90 I-73 1280 100 I-74 1280 100 I-75 1280 100 I-80 1280 100 I-79 1280 100

TABLE-US-00032 TABLE A12a Pre-emergence efficacy at 80 g/ha against AMARE in % Example number Dosage [g/ha] AMARE I-1 80 100 I-2 80 100 I-3 80 100 I-5 80 100 I-6 80 100 I-7 80 100 I-8 80 90 I-9 80 100 I-10 80 100 I-12 80 100 I-14 80 100 I-15 80 100 I-16 80 100 I-19 80 90 I-21 80 100 I-22 80 90 I-23 80 90 I-24 80 90 I-25 80 90 I-31 80 100 I-30 80 100 I-29 80 90 I-28 80 100 I-33 80 90 I-32 80 90 I-34 80 90 I-38 80 100 I-39 80 100 I-40 80 100 I-41 80 100 I-43 80 100 I-44 80 100 I-45 80 90 I-46 80 100 I-47 80 100 I-42 80 100 I-48 80 90 I-49 80 90 I-50 80 90 I-51 80 90 I-52 80 90 I-53 80 100 I-55 80 100 I-56 80 100 I-57 80 100 I-59 80 100 I-69 80 90 I-73 80 90 I-74 80 90 I-75 80 90 I-80 80 90 I-79 80 90

TABLE-US-00033 TABLE A12b Pre-emergence efficacy at 320 g/ha against AMARE in % Example number Dosage [g/ha] AMARE I-1 320 100 I-2 320 100 I-3 320 100 I-5 320 100 I-6 320 100 I-7 320 100 I-8 320 90 I-9 320 100 I-10 320 100 I-12 320 100 I-14 320 100 I-15 320 100 I-16 320 100 I-18 320 100 I-19 320 100 I-21 320 100 I-22 320 90 I-23 320 100 I-24 320 100 I-25 320 100 I-27 320 90 I-26 320 90 I-36 320 100 I-31 320 100 I-30 320 100 I-29 320 100 I-28 320 100 I-33 320 100 I-35 320 90 I-32 320 90 I-34 320 90 I-38 320 100 I-39 320 100 I-40 320 100 I-41 320 100 I-43 320 100 I-44 320 100 I-45 320 100 I-46 320 100 I-47 320 100 I-42 320 100 I-48 320 90 I-49 320 100 I-50 320 90 I-51 320 100 I-52 320 100 I-53 320 100 I-54 320 100 I-55 320 100 I-56 320 100 I-57 320 100 I-59 320 100 I-64 320 90 I-67 320 100 I-68 320 100 I-69 320 100 I-72 320 90 I-73 320 100 I-74 320 100 I-75 320 90 I-76 320 90 I-77 320 100 I-80 320 90 I-79 320 100 I-84 320 90

TABLE-US-00034 TABLE A12c Pre-emergence efficacy at 1280 g/ha against AMARE in % Example number Dosage [g/ha] AMARE I-1 1280 100 I-2 1280 100 I-3 1280 100 I-4 1280 100 I-5 1280 100 I-6 1280 100 I-7 1280 100 I-8 1280 100 I-9 1280 100 I-10 1280 100 I-12 1280 100 I-13 1280 100 I-14 1280 100 I-15 1280 100 I-16 1280 100 I-18 1280 100 I-19 1280 100 I-20 1280 90 I-21 1280 100 I-22 1280 100 I-23 1280 100 I-24 1280 100 I-25 1280 100 I-27 1280 90 I-26 1280 100 I-36 1280 100 I-31 1280 100 I-30 1280 100 I-29 1280 100 I-28 1280 100 I-33 1280 100 I-35 1280 100 I-32 1280 100 I-34 1280 100 I-38 1280 100 I-39 1280 100 I-40 1280 100 I-41 1280 100 I-43 1280 100 I-44 1280 100 I-45 1280 100 I-46 1280 100 I-47 1280 100 I-42 1280 100 I-48 1280 100 I-49 1280 100 I-50 1280 100 I-51 1280 100 I-52 1280 100 I-53 1280 100 I-54 1280 100 I-55 1280 100 I-56 1280 100 I-57 1280 100 I-59 1280 100 I-64 1280 100 I-65 1280 100 I-67 1280 100 I-68 1280 100 I-69 1280 100 I-72 1280 100 I-73 1280 100 I-74 1280 100 I-75 1280 100 I-76 1280 100 I-77 1280 100 I-80 1280 100 I-79 1280 100 I-84 1280 100

[0434] As shown by way of example by the results from tables A1a-A12c, the inventive compounds of the formula I in the case of pre-emergence treatment showed very good herbicidal efficacy against the harmful plants Abutilon theophrasti (ABUTH), Alopecurus myosuroides (ALOMY), Amaranthus retroflexus (AMARE), Echinochloa crus-galli (ECHCG), Bassia scoparia (KCHSC), Lolium rigidum (LOLRI), Poa annua (POAAN), Setaria viridis (SETVI), Stellaria media (STEME) and Veronica persica (VERPE) at an application rate of 1280 g or less of active substance per hectare.

[0435] B. Herbicidal Post-Emergence Efficacy

[0436] Seeds of mono- and dicotyledonous weed plants were placed in plastic pots in sandy loam soil (doubly sown with in each case one species 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 were treated at the one-leaf stage. The compounds of the invention, formulated in the form of wettable powders (WP) or as emulsion concentrates (EC), were applied 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 liters per hectare (converted). After the test plants had been kept in the greenhouse under optimum growth conditions for about 3 weeks, the activity of the preparations was rated visually in comparison to untreated controls.

[0437] For example, [0438] 100% efficacy=plants have died, [0439] 0% efficacy=like untreated control plants

[0440] Tables B1a to B12c below show the effects of selected inventive compounds of the general formula (I) according to table 1 on various harmful plants at an application rate corresponding to 1280 g/ha or less, which were obtained by the experimental procedure mentioned above.

TABLE-US-00035 TABLE B1a Post-emergence efficacy at 80 g/ha against ABUTH in % Example number Dosage [g/ha] ABUTH I-2 80 100 I-5 80 90 I-10 80 90 I-14 80 90 I-15 80 100 I-31 80 90 I-30 80 90 I-29 80 90 I-32 80 100 I-34 80 90 I-47 80 90 I-42 80 100 I-48 80 90 I-49 80 90 I-53 80 90 I-55 80 90 I-56 80 90 I-57 80 90 I-67 80 90 I-68 80 100 I-69 80 90 I-73 80 90 I-74 80 100 I-75 80 90 I-76 80 90 I-77 80 90 I-80 80 90

TABLE-US-00036 TABLE B1b Post-emergence efficacy at 320 g/ha against ABUTH in % Example number Dosage [g/ha] ABUTH I-2 320 100 I-3 320 90 I-5 320 100 I-6 320 90 I-7 320 90 I-9 320 90 I-10 320 90 I-14 320 100 I-15 320 100 I-16 320 90 I-19 320 90 I-22 320 90 I-23 320 90 I-24 320 90 I-25 320 90 I-31 320 100 I-30 320 90 I-29 320 100 I-28 320 100 I-33 320 90 I-35 320 100 I-32 320 100 I-34 320 100 I-43 320 90 I-44 320 90 I-45 320 100 I-46 320 100 I-47 320 100 I-42 320 100 I-48 320 90 I-49 320 90 I-50 320 90 I-51 320 90 I-53 320 90 I-55 320 90 I-56 320 90 I-57 320 90 I-59 320 90 I-64 320 90 I-67 320 90 I-68 320 100 I-69 320 90 I-72 320 90 I-73 320 100 I-74 320 100 I-75 320 90 I-76 320 90 I-77 320 90 I-80 320 90 I-79 320 90

TABLE-US-00037 TABLE B1c Post-emergence efficacy at 1280 g/ha against ABUTH in % Example number Dosage [g/ha] ABUTH I-2 1280 100 I-3 1280 100 I-4 1280 90 I-5 1280 100 I-6 1280 90 I-7 1280 90 I-8 1280 90 I-9 1280 90 I-10 1280 90 I-13 1280 90 I-14 1280 100 I-15 1280 100 I-16 1280 100 I-18 1280 90 I-19 1280 90 I-20 1280 90 I-22 1280 100 I-23 1280 100 I-24 1280 90 I-25 1280 100 I-26 1280 90 I-31 1280 100 I-30 1280 100 I-29 1280 100 I-28 1280 100 I-33 1280 100 I-35 1280 100 I-32 1280 100 I-34 1280 100 I-39 1280 90 I-43 1280 100 I-44 1280 100 I-45 1280 100 I-46 1280 100 I-47 1280 100 I-42 1280 100 I-48 1280 90 I-49 1280 90 I-50 1280 90 I-51 1280 90 I-52 1280 90 I-53 1280 90 I-54 1280 90 I-55 1280 90 I-56 1280 90 I-57 1280 90 I-58 1280 90 I-59 1280 90 I-64 1280 90 I-65 1280 90 I-67 1280 100 I-68 1280 100 I-69 1280 100 I-72 1280 100 I-73 1280 100 I-74 1280 100 I-75 1280 100 I-76 1280 100 I-77 1280 100 I-80 1280 100 I-79 1280 100 I-84 1280 90

TABLE-US-00038 TABLE B2a Post-emergence efficacy at 320 g/ha against ALOMY in % Example number Dosage [g/ha] ALOMY I-2 320 90 I-14 320 100 I-23 320 90 I-47 320 90 I-42 320 100 I-53 320 90

TABLE-US-00039 TABLE B2b Post-emergence efficacy at 1280 g/ha against ALOMY in % Example number Dosage [g/ha] ALOMY I-2 1280 90 I-3 1280 90 I-5 1280 100 I-14 1280 100 I-16 1280 90 I-23 1280 90 I-32 1280 90 I-41 1280 90 I-45 1280 90 I-46 1280 90 I-47 1280 100 I-42 1280 100 I-48 1280 90 I-49 1280 90 I-53 1280 90 I-55 1280 90 I-73 1280 90 I-74 1280 90

TABLE-US-00040 TABLE B3a Post-emergence efficacy at 320 g/ha against DIGSA in % Example number Dosage [g/ha] DIGSA I-14 320 100 I-23 320 90 I-24 320 90 I-25 320 90 I-32 320 90 I-40 320 90 I-41 320 90 I-48 320 90 I-49 320 90 I-53 320 90 I-55 320 90 I-56 320 90 I-57 320 90 I-59 320 90 I-68 320 90 I-73 320 90 I-74 320 90 I-79 320 90

TABLE-US-00041 TABLE B3b Post-emergence efficacy at 1280 g/ha against DIGSA in % Example number Dosage [g/ha] DIGSA I-13 1280 90 I-14 1280 100 I-16 1280 90 I-23 1280 100 I-24 1280 90 I-25 1280 100 I-26 1280 90 I-31 1280 90 I-30 1280 90 I-29 1280 100 I-28 1280 90 I-33 1280 90 I-32 1280 100 I-34 1280 100 I-38 1280 90 I-39 1280 90 I-40 1280 90 I-41 1280 90 I-48 1280 90 I-49 1280 90 I-50 1280 90 I-52 1280 90 I-53 1280 90 I-54 1280 90 I-55 1280 90 I-56 1280 90 I-57 1280 90 I-59 1280 90 I-68 1280 100 I-73 1280 100 I-74 1280 100 I-75 1280 90 I-80 1280 90 I-79 1280 100

TABLE-US-00042 TABLE B4a Post-emergence efficacy at 80 g/ha against ECHCG in % Example number Dosage [g/ha] ECHCG I-2 80 90 I-5 80 90 I-10 80 100 I-15 80 90 I-32 80 90 I-46 80 90 I-47 80 90 I-42 80 100 I-49 80 90 I-53 80 90

TABLE-US-00043 TABLE B4b Post-emergence efficacy at 320 g/ha against ECHCG in % Example number Dosage [g/ha] ECHCG I-2 320 100 I-5 320 100 I-6 320 90 I-7 320 90 I-8 320 90 I-10 320 100 I-14 320 100 I-15 320 100 I-23 320 90 I-25 320 90 I-30 320 90 I-29 320 90 I-28 320 90 I-32 320 90 I-34 320 90 I-43 320 90 I-45 320 100 I-46 320 90 I-47 320 100 I-42 320 100 I-48 320 90 I-49 320 90 I-53 320 90 I-55 320 90 I-56 320 90 I-57 320 90 I-68 320 90 I-73 320 90 I-74 320 100 I-76 320 90 I-77 320 90

TABLE-US-00044 TABLE B4c Post-emergence efficacy at 1280 g/ha against ECHCG in % Example number Dosage [g/ha] ECHCG I-2 1280 100 I-3 1280 90 I-5 1280 100 I-6 1280 90 I-7 1280 90 I-8 1280 100 I-9 1280 90 I-10 1280 100 I-13 1280 90 I-14 1280 100 I-15 1280 100 I-16 1280 90 I-18 1280 90 I-19 1280 90 I-23 1280 90 I-24 1280 100 I-25 1280 100 I-26 1280 90 I-31 1280 100 I-30 1280 90 I-29 1280 100 I-28 1280 100 I-33 1280 100 I-35 1280 90 I-32 1280 100 I-34 1280 90 I-43 1280 90 I-44 1280 100 I-45 1280 100 I-46 1280 100 I-47 1280 100 I-42 1280 100 I-48 1280 90 I-49 1280 90 I-50 1280 90 I-51 1280 90 I-52 1280 90 I-53 1280 90 I-54 1280 90 I-55 1280 90 I-56 1280 90 I-57 1280 90 I-64 1280 90 I-68 1280 100 I-69 1280 100 I-72 1280 100 I-73 1280 100 I-74 1280 100 I-75 1280 90 I-76 1280 100 I-77 1280 100 I-80 1280 100 I-79 1280 100

TABLE-US-00045 TABLE B5a Post-emergence efficacy at 80 g/ha against KCHSC in % Example number Dosage [g/ha] KCHSC I-1 80 90 I-2 80 100 I-3 80 90 I-5 80 100 I-6 80 90 I-8 80 90 I-10 80 90 I-14 80 100 I-15 80 100 I-16 80 90 I-21 80 90 I-22 80 90 I-23 80 100 I-24 80 90 I-25 80 90 I-31 80 90 I-30 80 100 I-32 80 100 I-34 80 100 I-39 80 90 I-40 80 90 I-41 80 90 I-43 80 90 I-44 80 100 I-47 80 100 I-42 80 90 I-48 80 90 I-49 80 90 I-53 80 90 I-56 80 90 I-57 80 90 I-64 80 90 I-67 80 90 I-68 80 100 I-69 80 90 I-72 80 90 I-73 80 90 I-74 80 90 I-75 80 90 I-77 80 90 I-79 80 90

TABLE-US-00046 TABLE B5b Post-emergence efficacy at 320 g/ha against KCHSC in % Example number Dosage [g/ha] KCHSC I-1 320 100 I-2 320 100 I-3 320 90 I-5 320 100 I-6 320 90 I-8 320 90 I-10 320 90 I-13 320 90 I-14 320 100 I-15 320 100 I-16 320 100 I-18 320 100 I-19 320 90 I-20 320 90 I-21 320 100 I-22 320 90 I-23 320 100 I-24 320 100 I-25 320 100 I-26 320 90 I-31 320 100 I-30 320 100 I-29 320 100 I-28 320 90 I-32 320 100 I-34 320 100 I-38 320 90 I-39 320 90 I-40 320 90 I-41 320 90 I-43 320 90 I-44 320 100 I-45 320 90 I-47 320 100 I-42 320 100 I-48 320 90 I-49 320 90 I-53 320 90 I-55 320 90 I-56 320 90 I-57 320 90 I-59 320 90 I-61 320 90 I-64 320 90 I-67 320 100 I-68 320 100 I-69 320 100 I-72 320 100 I-73 320 100 I-74 320 100 I-75 320 100 I-77 320 90 I-80 320 90 I-79 320 100 I-84 320 90

TABLE-US-00047 TABLE B5c Post-emergence efficacy at 1280 g/ha against KCHSC in % Example number Dosage [g/ha] KCHSC I-1 1280 100 I-2 1280 100 I-3 1280 90 I-4 1280 90 I-5 1280 100 I-6 1280 90 I-7 1280 90 I-8 1280 90 I-9 1280 90 I-10 1280 90 I-12 1280 90 I-13 1280 100 I-14 1280 100 I-15 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 100 I-25 1280 100 I-27 1280 90 I-26 1280 90 I-36 1280 90 I-31 1280 100 I-30 1280 100 I-29 1280 100 I-28 1280 100 I-33 1280 100 I-35 1280 100 I-32 1280 100 I-34 1280 100 I-38 1280 90 I-39 1280 90 I-40 1280 90 I-41 1280 90 I-43 1280 100 I-44 1280 100 I-45 1280 100 I-46 1280 100 I-47 1280 100 I-42 1280 100 I-48 1280 90 I-49 1280 100 I-50 1280 90 I-51 1280 90 I-53 1280 90 I-54 1280 90 I-55 1280 90 I-56 1280 90 I-57 1280 90 I-58 1280 90 I-59 1280 90 I-61 1280 90 I-64 1280 90 I-67 1280 100 I-68 1280 100 I-69 1280 100 I-72 1280 100 I-73 1280 100 I-74 1280 100 I-75 1280 100 I-76 1280 90 I-77 1280 100 I-80 1280 90 I-79 1280 100 I-84 1280 100

TABLE-US-00048 TABLE B6a Post-emergence efficacy at 320 g/ha against LOLRI in % Example number Dosage [g/ha] LOLRI I-10 320 90 I-12 320 90 I-15 320 90 I-48 320 90

TABLE-US-00049 TABLE B6b Post-emergence efficacy at 1280 g/ha against LOLRI in % Example number Dosage [g/ha] LOLRI I-2 1280 90 I-8 1280 90 I-10 1280 100 I-12 1280 90 I-14 1280 100 I-15 1280 90 I-24 1280 90 I-25 1280 90 I-29 1280 90 I-32 1280 90 I-38 1280 90 I-41 1280 90 I-48 1280 90 I-49 1280 90 I-52 1280 90 I-53 1280 90 I-73 1280 90 I-74 1280 100 I-76 1280 90

TABLE-US-00050 TABLE B7a Post-emergence efficacy at 320 g/ha against MATIN in % Example number Dosage [g/ha] MATIN I-56 320 90 I-57 320 90

TABLE-US-00051 TABLE B7b Post-emergence efficacy at 1280 g/ha against MATIN in % Example number Dosage [g/ha] MATIN I-5 1280 90 I-50 1280 90 I-56 1280 90 I-57 1280 90

TABLE-US-00052 TABLE B8a Post-emergence efficacy at 80 g/ha against POAAN in % Example number Dosage [g/ha] POAAN I-2 80 90 I-14 80 90 I-23 80 90 I-32 80 90 I-48 80 90 I-50 80 90 I-53 80 90 I-56 80 90 I-74 80 90

TABLE-US-00053 TABLE B8b Post-emergence efficacy at 320 g/ha against POAAN in % Example number Dosage [g/ha] POAAN I-2 320 100 I-5 320 90 I-14 320 100 I-15 320 90 I-23 320 90 I-24 320 90 I-25 320 90 I-31 320 90 I-30 320 90 I-29 320 90 I-28 320 90 I-33 320 90 I-32 320 100 I-34 320 100 I-39 320 90 I-40 320 90 I-41 320 90 I-48 320 90 I-50 320 90 I-52 320 90 I-53 320 90 I-55 320 90 I-56 320 90 I-57 320 90 I-68 320 90 I-74 320 100 I-75 320 90 I-76 320 90

TABLE-US-00054 TABLE B8c Post-emergence efficacy at 1280 g/ha against POAAN in % Example number Dosage [g/ha] POAAN I-2 1280 100 I-3 1280 90 I-4 1280 90 I-5 1280 100 I-6 1280 100 I-7 1280 90 I-8 1280 90 I-9 1280 90 I-10 1280 90 I-12 1280 90 I-13 1280 100 I-14 1280 100 I-15 1280 90 I-16 1280 100 I-18 1280 90 I-19 1280 90 I-20 1280 90 I-21 1280 100 I-22 1280 90 I-23 1280 100 I-24 1280 100 I-25 1280 100 I-36 1280 90 I-31 1280 100 I-30 1280 100 I-29 1280 100 I-28 1280 100 I-33 1280 100 I-35 1280 90 I-32 1280 100 I-34 1280 100 I-38 1280 90 I-39 1280 90 I-40 1280 90 I-41 1280 90 I-48 1280 90 I-49 1280 90 I-50 1280 90 I-51 1280 90 I-52 1280 90 I-53 1280 90 I-54 1280 90 I-55 1280 90 I-56 1280 90 I-57 1280 90 I-59 1280 90 I-64 1280 90 I-67 1280 100 I-68 1280 100 I-69 1280 90 I-72 1280 90 I-73 1280 100 I-74 1280 100 I-75 1280 90 I-76 1280 100 I-80 1280 90

TABLE-US-00055 TABLE B9a Post-emergence efficacy at 320 g/ha against SETVI in % Example number Dosage [g/ha] SETVI I-2 320 100 I-5 320 90 I-8 320 90 I-10 320 100 I-14 320 90 I-25 320 90 I-29 320 100 I-28 320 90 I-32 320 90 I-39 320 90 I-40 320 90 I-41 320 90 I-48 320 90 I-49 320 90 I-53 320 90 I-55 320 90 I-56 320 90 I-57 320 90 I-68 320 90

TABLE-US-00056 TABLE B9b Post-emergence efficacy at 1280 g/ha against SETVI in % Example number Dosage [g/ha] SETVI I-2 1280 100 I-3 1280 90 I-5 1280 100 I-6 1280 90 I-7 1280 90 I-8 1280 90 I-9 1280 90 I-10 1280 100 I-12 1280 90 I-14 1280 100 I-15 1280 100 I-16 1280 90 I-23 1280 100 I-24 1280 90 I-25 1280 90 I-36 1280 90 I-31 1280 90 I-29 1280 100 I-28 1280 90 I-33 1280 100 I-32 1280 100 I-34 1280 90 I-38 1280 90 I-39 1280 90 I-40 1280 90 I-41 1280 90 I-48 1280 90 I-49 1280 90 I-50 1280 90 I-52 1280 90 I-53 1280 90 I-54 1280 90 I-55 1280 90 I-56 1280 90 I-57 1280 90 I-59 1280 90 I-68 1280 90 I-73 1280 90 I-74 1280 100 I-80 1280 90 I-79 1280 90

TABLE-US-00057 TABLE B10a Post-emergence efficacy at 80 g/ha against STEME in % Example number Dosage [g/ha] STEME I-2 80 90 I-5 80 100 I-10 80 90 I-12 80 90 I-14 80 100 I-15 80 100 I-16 80 90 I-19 80 90 I-22 80 90 I-23 80 90 I-24 80 90 I-25 80 90 I-31 80 100 I-30 80 100 I-29 80 90 I-28 80 90 I-33 80 90 I-35 80 90 I-32 80 100 I-34 80 100 I-38 80 90 I-39 80 90 I-41 80 90 I-44 80 100 I-45 80 100 I-46 80 90 I-47 80 100 I-42 80 100 I-48 80 90 I-49 80 90 I-51 80 90 I-53 80 90 I-55 80 90 I-56 80 90 I-57 80 90 I-68 80 90 I-72 80 90 I-73 80 90 I-74 80 100 I-76 80 90 I-80 80 90 I-79 80 90

TABLE-US-00058 TABLE B10b Post-emergence efficacy at 320 g/ha against STEME in % Example number Dosage [g/ha] STEME I-2 320 100 I-3 320 90 I-5 320 100 I-6 320 90 I-7 320 90 I-8 320 90 I-10 320 90 I-12 320 90 I-13 320 90 I-14 320 100 I-15 320 100 I-16 320 100 I-19 320 100 I-21 320 90 I-22 320 90 I-23 320 100 I-24 320 90 I-25 320 100 I-31 320 100 I-30 320 100 I-29 320 100 I-28 320 100 I-33 320 100 I-35 320 100 I-32 320 100 I-34 320 100 I-38 320 90 I-39 320 90 I-41 320 90 I-43 320 100 I-44 320 100 I-45 320 100 I-46 320 100 I-47 320 100 I-42 320 100 I-48 320 90 I-49 320 90 I-51 320 90 I-53 320 90 I-55 320 90 I-56 320 90 I-57 320 90 I-59 320 90 I-67 320 100 I-68 320 100 I-69 320 90 I-72 320 100 I-73 320 100 I-74 320 100 I-75 320 100 I-76 320 100 I-80 320 100 I-79 320 100

TABLE-US-00059 TABLE B10c Post-emergence efficacy at 1280 g/ha against STEME in % Example number Dosage [g/ha] STEME I-2 1280 100 I-3 1280 100 I-4 1280 90 I-5 1280 100 I-6 1280 90 I-7 1280 90 I-8 1280 90 I-9 1280 90 I-10 1280 100 I-12 1280 100 I-13 1280 100 I-14 1280 100 I-15 1280 100 I-16 1280 100 I-18 1280 90 I-19 1280 100 I-20 1280 100 I-21 1280 100 I-22 1280 90 I-23 1280 100 I-24 1280 100 I-25 1280 100 I-27 1280 90 I-26 1280 90 I-36 1280 100 I-31 1280 100 I-30 1280 100 I-29 1280 100 I-28 1280 100 I-33 1280 100 I-35 1280 100 I-32 1280 100 I-34 1280 100 I-38 1280 90 I-39 1280 90 I-41 1280 90 I-43 1280 100 I-44 1280 100 I-45 1280 100 I-46 1280 100 I-47 1280 100 I-42 1280 100 I-48 1280 90 I-49 1280 90 I-51 1280 90 I-52 1280 90 I-53 1280 90 I-54 1280 90 I-55 1280 90 I-56 1280 90 I-57 1280 90 I-59 1280 90 I-61 1280 90 I-64 1280 90 I-65 1280 90 I-67 1280 100 I-68 1280 100 I-69 1280 100 I-72 1280 100 I-73 1280 100 I-74 1280 100 I-75 1280 100 I-76 1280 100 I-77 1280 90 I-80 1280 100 I-79 1280 100 I-84 1280 100

TABLE-US-00060 TABLE B11a Post-emergence efficacy at 80 g/ha against VERPE in % Example number Dosage [g/ha] VERPE I-2 80 100 I-3 80 90 I-5 80 100 I-13 80 90 I-14 80 100 I-15 80 100 I-16 80 100 I-19 80 90 I-21 80 90 I-22 80 90 I-23 80 90 I-24 80 90 I-25 80 100 I-31 80 90 I-30 80 90 I-29 80 90 I-28 80 100 I-33 80 100 I-35 80 90 I-32 80 100 I-34 80 100 I-38 80 90 I-39 80 90 I-40 80 90 I-41 80 90 I-53 80 90 I-54 80 90 I-55 80 90 I-56 80 90 I-57 80 90 I-59 80 90 I-64 80 90 I-67 80 90 I-68 80 100 I-69 80 100 I-72 80 100 I-73 80 100 I-74 80 100 I-75 80 100 I-76 80 90 I-77 80 100 I-80 80 90 I-79 80 100 I-84 80 100

TABLE-US-00061 TABLE B11b Post-emergence efficacy at 320 g/ha against VERPE in % Example number Dosage [g/ha] VERPE I-1 320 90 I-2 320 100 I-3 320 100 I-4 320 90 I-5 320 100 I-6 320 90 I-13 320 100 I-14 320 100 I-15 320 100 I-16 320 100 I-18 320 90 I-19 320 90 I-20 320 90 I-21 320 100 I-22 320 100 I-23 320 100 I-24 320 100 I-25 320 100 I-27 320 90 I-26 320 90 I-36 320 90 I-31 320 90 I-30 320 100 I-29 320 90 I-28 320 100 I-33 320 100 I-35 320 90 I-32 320 100 I-34 320 100 I-38 320 90 I-39 320 90 I-40 320 90 I-41 320 90 I-48 320 90 I-50 320 90 I-53 320 90 I-54 320 90 I-55 320 90 I-56 320 90 I-59 320 90 I-64 320 90 I-67 320 100 I-68 320 100 I-69 320 100 I-72 320 100 I-73 320 100 I-74 320 100 I-75 320 100 I-76 320 100 I-77 320 100 I-80 320 90 I-79 320 100 I-84 320 100

TABLE-US-00062 TABLE B11c Post-emergence efficacy at 1280 g/ha against VERPE in % Example number Dosage [g/ha] VERPE I-1 1280 100 I-2 1280 100 I-3 1280 100 I-4 1280 100 I-5 1280 100 I-6 1280 90 I-8 1280 90 I-9 1280 100 I-12 1280 90 I-13 1280 100 I-14 1280 100 I-15 1280 100 I-16 1280 100 I-18 1280 90 I-19 1280 100 I-20 1280 100 I-21 1280 100 I-22 1280 100 I-23 1280 100 I-24 1280 100 I-25 1280 100 I-27 1280 90 I-26 1280 90 I-36 1280 100 I-31 1280 100 I-30 1280 100 I-29 1280 100 I-28 1280 100 I-33 1280 100 I-35 1280 100 I-32 1280 100 I-34 1280 100 I-38 1280 90 I-39 1280 90 I-40 1280 90 I-41 1280 90 I-48 1280 90 I-49 1280 90 I-50 1280 90 I-51 1280 90 I-53 1280 90 I-54 1280 90 I-55 1280 90 I-56 1280 90 I-57 1280 90 I-58 1280 90 I-59 1280 90 I-61 1280 90 I-62 1280 90 I-63 1280 90 I-64 1280 90 I-65 1280 90 I-67 1280 100 I-68 1280 100 I-69 1280 100 I-72 1280 100 I-73 1280 100 I-74 1280 100 I-75 1280 100 I-76 1280 100 I-77 1280 100 I-80 1280 100 I-79 1280 100 I-84 1280 100

TABLE-US-00063 TABLE B12a Post-emergence efficacy at 80 g/ha against AMARE in % Example number Dosage [g/ha] AMARE I-1 80 100 I-2 80 100 I-3 80 90 I-5 80 100 I-6 80 90 I-8 80 90 I-9 80 90 I-10 80 90 I-14 80 100 I-15 80 100 I-16 80 100 I-21 80 90 I-23 80 100 I-24 80 90 I-25 80 90 I-31 80 100 I-30 80 100 I-29 80 90 I-32 80 100 I-34 80 100 I-48 80 90 I-49 80 90 I-50 80 90 I-51 80 90 I-53 80 90 I-55 80 90 I-56 80 90 I-57 80 90 I-58 80 90 I-59 80 90 I-61 80 90 I-64 80 90 I-67 80 100 I-68 80 100 I-69 80 100 I-72 80 100 I-73 80 100 I-74 80 100 I-75 80 100 I-76 80 90 I-77 80 100 I-80 80 100 I-79 80 90 I-84 80 90

TABLE-US-00064 TABLE B12b Post-emergence efficacy at 320 g/ha against AMARE in % Example number Dosage [g/ha] AMARE I-1 320 100 I-2 320 100 I-3 320 100 I-5 320 100 I-6 320 100 I-7 320 90 I-8 320 100 I-9 320 100 I-10 320 90 I-12 320 90 I-13 320 90 I-14 320 100 I-15 320 100 I-16 320 100 I-18 320 100 I-19 320 90 I-20 320 90 I-21 320 100 I-22 320 90 I-23 320 100 I-24 320 100 I-25 320 100 I-27 320 90 I-26 320 90 I-36 320 90 I-31 320 100 I-30 320 100 I-29 320 100 I-28 320 90 I-33 320 90 I-35 320 90 I-32 320 100 I-34 320 100 I-39 320 90 I-40 320 90 I-41 320 90 I-48 320 90 I-49 320 90 I-50 320 90 I-51 320 90 I-52 320 90 I-53 320 90 I-55 320 90 I-56 320 90 I-57 320 90 I-58 320 90 I-59 320 90 I-61 320 90 I-64 320 90 I-65 320 90 I-67 320 100 I-68 320 100 I-69 320 100 I-72 320 100 I-73 320 100 I-74 320 100 I-75 320 100 I-76 320 100 I-77 320 100 I-80 320 100 I-79 320 100 I-84 320 100

TABLE-US-00065 TABLE B12c Post-emergence efficacy at 1280 g/ha against AMARE in % Example number Dosage [g/ha] AMARE I-1 1280 100 I-2 1280 100 I-3 1280 100 I-4 1280 90 I-5 1280 100 I-6 1280 100 I-7 1280 90 I-8 1280 100 I-9 1280 100 I-10 1280 100 I-12 1280 100 I-13 1280 100 I-14 1280 100 I-15 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 100 I-25 1280 100 I-27 1280 100 I-26 1280 90 I-36 1280 100 I-31 1280 100 I-30 1280 100 I-29 1280 100 I-28 1280 100 I-33 1280 100 I-35 1280 100 I-32 1280 100 I-34 1280 100 I-38 1280 90 I-39 1280 90 I-40 1280 90 I-41 1280 90 I-48 1280 90 I-49 1280 100 I-50 1280 100 I-51 1280 90 I-52 1280 90 I-53 1280 90 I-54 1280 90 I-55 1280 90 I-56 1280 90 I-57 1280 90 I-58 1280 90 I-59 1280 90 I-61 1280 90 I-62 1280 90 I-63 1280 90 I-64 1280 90 I-65 1280 90 I-67 1280 100 I-68 1280 100 I-69 1280 100 I-72 1280 100 I-73 1280 100 I-74 1280 100 I-75 1280 100 I-76 1280 100 I-77 1280 100 I-80 1280 100 I-79 1280 100 I-84 1280 100

[0441] As shown by the results from tables B1a-B12c by way of example, the inventive compounds of the formula I in the case of post-emergence treatment showed very good herbicidal efficacy against the harmful plants Abutilon theophrasti (ABUTH), Alopecurus myosuroides (ALOMY), Amaranthus retroflexus (AMARE), Echinochloa crus-galli (ECHCG), Bassia scoparia (KCHSC), Lolium rigidum (LOLRI), Poa annua (POAAN), Setaria viridis (SETVI), Stellaria media (STEME) and Veronica persica (VERPE) at an application rate of 1280 g or less of active substance per hectare.

[0442] C. Herbicidal Pre-Emergence Efficacy

[0443] Seeds of monocotyledonous and dicotyledonous weed plants and crop plants were placed in plastic or organic planting pots and covered with soil. The compounds of the invention, formulated in the form of wettable powders (WP) or as emulsion concentrates (EC), were then applied to 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 l/ha (converted). After the treatment, the pots were placed in a greenhouse and kept under good growth conditions for the test plants. After about 3 weeks, the efficacy of the preparations was scored visually in comparison with untreated controls as percentages. For example, [0444] 100% efficacy=plants have died, [0445] 0% efficacy=like untreated control plants.

[0446] Tables C1a to C14b below show the effects of selected compounds of the general formula (I) according to table 1 on various harmful plants at an application rate corresponding to 320 g/ha or less, which were obtained by the experimental procedure mentioned above.

TABLE-US-00066 TABLE C1a Pre-emergence efficacy at 80 g/ha against ABUTH in % Example number Application rate [g/ha] ABUTH I-2 80 100 I-3 80 100 I-6 80 90 I-8 80 100 I-10 80 100 I-11 80 90 I-12 80 80 I-14 80 90 I-23 80 100 I-32 80 90 I-34 80 80 I-38 80 100 I-39 80 100 I-40 80 100 I-41 80 100 I-43 80 80 I-45 80 100 I-46 80 100 I-47 80 100 I-42 80 100 I-48 80 100 I-49 80 100 I-52 80 80 I-53 80 100 I-56 80 100 I-68 80 100 I-70 80 80 I-71 80 80

TABLE-US-00067 TABLE C1b Pre-emergence efficacy at 320 g/ha against ABUTH in % Example number Application rate [g/ha] ABUTH I-2 320 100 I-3 320 100 I-5 320 100 I-6 320 100 I-7 320 100 I-8 320 100 I-10 320 100 I-11 320 90 I-12 320 90 I-13 320 90 I-14 320 100 I-15 320 100 I-23 320 100 I-25 320 100 I-36 320 90 I-32 320 100 I-34 320 90 I-38 320 100 I-39 320 100 I-40 320 100 I-41 320 100 I-43 320 100 I-45 320 100 I-46 320 100 I-47 320 100 I-42 320 100 I-48 320 100 I-49 320 100 I-50 320 100 I-52 320 100 I-53 320 100 I-56 320 100 I-68 320 100 I-70 320 100 I-71 320 100 I-73 320 90 I-74 320 90 I-81 320 100

TABLE-US-00068 TABLE C2a Pre-emergence efficacy at 80 g/ha against ALOMY in % Example number Application rate [g/ha] ALOMY I-2 80 90 I-5 80 90 I-6 80 80 I-7 80 90 I-8 80 90 I-10 80 100 I-14 80 90 I-23 80 80 I-47 80 100 I-42 80 100 I-48 80 100 I-49 80 100 I-53 80 90 I-56 80 100

TABLE-US-00069 TABLE C2b Pre-emergence efficacy at 320 g/ha against ALOMY in % Example number Application rate [g/ha] ALOMY I-2 320 100 I-3 320 100 I-5 320 100 I-6 320 90 I-7 320 100 I-8 320 100 I-9 320 80 I-10 320 100 I-11 320 90 I-14 320 100 I-15 320 90 I-23 320 100 I-25 320 80 I-32 320 100 I-34 320 80 I-38 320 100 I-39 320 100 I-40 320 100 I-41 320 100 I-45 320 100 I-46 320 100 I-47 320 100 I-42 320 100 I-48 320 100 I-49 320 100 I-50 320 90 I-52 320 100 I-53 320 100 I-56 320 100 I-68 320 90 I-70 320 100 I-71 320 80 I-81 320 90

TABLE-US-00070 TABLE C3a Pre-emergence efficacy at 80 g/ha against AMARE in % Example number Application rate [g/ha] AMARE I-2 80 100 I-3 80 100 I-5 80 100 I-6 80 100 I-7 80 100 I-8 80 100 I-9 80 100 I-10 80 100 I-11 80 100 I-12 80 100 I-14 80 100 I-15 80 90 I-23 80 100 I-24 80 100 I-25 80 100 I-32 80 100 I-34 80 100 I-38 80 100 I-39 80 100 I-40 80 100 I-41 80 100 I-43 80 100 I-45 80 80 I-46 80 80 I-47 80 100 I-42 80 100 I-48 80 100 I-49 80 100 I-50 80 100 I-52 80 100 I-53 80 100 I-55 80 100 I-56 80 100 I-68 80 100 I-70 80 100 I-71 80 100 I-73 80 90 I-74 80 90 I-81 80 100 I-78 80 100 I-85 80 100 I-83 80 80

TABLE-US-00071 TABLE C3b Pre-emergence efficacy at 320 g/ha against AMARE in % Example number Application rate [g/ha] AMARE I-2 320 100 I-3 320 100 I-5 320 100 I-6 320 100 I-7 320 100 I-8 320 100 I-9 320 100 I-10 320 100 I-11 320 100 I-12 320 100 I-13 320 100 I-14 320 100 I-15 320 100 I-23 320 100 I-24 320 100 I-25 320 100 I-36 320 100 I-32 320 100 I-34 320 100 I-38 320 100 I-39 320 100 I-40 320 100 I-41 320 100 I-43 320 100 I-45 320 100 I-46 320 100 I-47 320 100 I-42 320 100 I-48 320 100 I-49 320 100 I-50 320 100 I-52 320 100 I-53 320 100 I-55 320 100 I-56 320 100 I-68 320 100 I-70 320 100 I-71 320 100 I-73 320 100 I-74 320 100 I-81 320 100 I-82 320 80 I-78 320 100 I-85 320 100 I-83 320 100

TABLE-US-00072 TABLE C4 Pre-emergence efficacy at 320 g/ha against AVEFA in % Example number Application rate [g/ha] AVEFA I-2 320 100 I-5 320 80 I-6 320 80 I-7 320 90 I-8 320 90 I-10 320 90 I-11 320 90 I-14 320 80 I-23 320 90 I-40 320 100 I-47 320 100 I-42 320 100 I-48 320 100 I-53 320 80 I-56 320 80

TABLE-US-00073 TABLE C5a Pre-emergence efficacy at 80 g/ha against DIGSA in % Example number Application rate [g/ha] DIGSA I-6 80 100 I-7 80 100 I-8 80 100 I-10 80 100 I-12 80 90 I-15 80 100 I-23 80 100 I-24 80 90 I-25 80 100 I-34 80 90 I-38 80 100 I-39 80 100 I-40 80 100 I-41 80 100 I-45 80 100 I-46 80 100 I-47 80 100 I-42 80 100 I-48 80 100 I-49 80 100 I-50 80 100 I-52 80 80 I-53 80 100 I-55 80 100 I-56 80 100 I-68 80 100 I-70 80 100 I-74 80 100 I-81 80 100 I-83 80 80

TABLE-US-00074 TABLE C5b Pre-emergence efficacy at 320 g/ha against DIGSA in % Example number Application rate [g/ha] DIGSA I-6 320 100 I-7 320 100 I-8 320 100 I-9 320 100 I-10 320 100 I-12 320 100 I-15 320 100 I-23 320 100 I-24 320 100 I-25 320 100 I-36 320 100 I-32 320 100 I-34 320 100 I-38 320 100 I-39 320 100 I-40 320 100 I-41 320 100 I-43 320 100 I-45 320 100 I-46 320 100 I-47 320 100 I-42 320 100 I-48 320 100 I-49 320 100 I-50 320 100 I-52 320 100 I-53 320 100 I-55 320 100 I-56 320 100 I-68 320 100 I-70 320 100 I-71 320 100 I-73 320 100 I-74 320 100 I-81 320 100 I-85 320 100 I-83 320 100

TABLE-US-00075 TABLE C6a Pre-emergence efficacy at 80 g/ha against ECHCG in % Example number Application rate [g/ha] ECHCG I-2 80 90 I-3 80 90 I-5 80 100 I-6 80 100 I-7 80 100 I-8 80 100 I-10 80 100 I-11 80 90 I-12 80 90 I-14 80 100 I-23 80 100 I-25 80 100 I-38 80 100 I-39 80 90 I-40 80 100 I-41 80 100 I-45 80 100 I-46 80 90 I-47 80 100 I-42 80 100 I-48 80 100 I-49 80 100 I-50 80 80 I-52 80 100 I-53 80 100 I-55 80 90 I-56 80 100 I-70 80 90

TABLE-US-00076 TABLE C6b Pre-emergence efficacy at 320 g/ha against ECHCG in % Example number Application rate [g/ha] ECHCG I-2 320 100 I-3 320 100 I-5 320 100 I-6 320 100 I-7 320 100 I-8 320 100 I-9 320 90 I-10 320 100 I-11 320 100 I-12 320 90 I-13 320 80 I-14 320 100 I-15 320 90 I-23 320 100 I-24 320 100 I-25 320 100 I-36 320 80 I-32 320 90 I-34 320 90 I-38 320 100 I-39 320 100 I-40 320 100 I-41 320 100 I-43 320 90 I-45 320 100 I-46 320 100 I-47 320 100 I-42 320 100 I-48 320 100 I-49 320 100 I-50 320 100 I-52 320 100 I-53 320 100 I-55 320 100 I-56 320 100 I-68 320 90 I-70 320 100 I-71 320 100 I-73 320 90 I-74 320 100 I-81 320 100 I-83 320 90

TABLE-US-00077 TABLE C7a Pre-emergence efficacy at 80 g/ha against LOLRI in % Example number Application rate [g/ha] LOLRI I-6 80 80 I-10 80 90 I-47 80 90 I-42 80 100 I-48 80 90 I-49 80 80 I-56 80 100

TABLE-US-00078 TABLE C7b Pre-emergence efficacy at 320 g/ha against LOLRI in % Example number Application rate [g/ha] LOLRI I-2 320 100 I-3 320 90 I-5 320 80 I-6 320 100 I-7 320 90 I-8 320 100 I-10 320 100 I-11 320 80 I-14 320 100 I-15 320 80 I-23 320 100 I-38 320 100 I-39 320 100 I-40 320 100 I-41 320 100 I-45 320 90 I-46 320 100 I-47 320 100 I-42 320 100 I-48 320 100 I-49 320 90 I-50 320 100 I-52 320 90 I-53 320 100 I-55 320 90 I-56 320 100 I-70 320 100 I-71 320 80 I-73 320 80 I-81 320 90 I-83 320 80

TABLE-US-00079 TABLE C8a Pre-emergence efficacy at 80 g/ha against MATIN in % Example number Application rate [g/ha] MATIN I-8 80 80 I-10 80 90 I-38 80 80 I-47 80 90 I-42 80 90 I-48 80 100 I-49 80 80 I-68 80 90

TABLE-US-00080 TABLE C8b Pre-emergence efficacy at 320 g/ha against MATIN in % Example number Application rate [g/ha] MATIN I-2 320 100 I-3 320 90 I-5 320 90 I-8 320 80 I-9 320 80 I-10 320 100 I-11 320 80 I-23 320 100 I-32 320 80 I-38 320 80 I-39 320 80 I-40 320 80 I-43 320 80 I-47 320 100 I-42 320 100 I-48 320 100 I-49 320 100 I-53 320 90 I-68 320 100 I-85 320 80

TABLE-US-00081 TABLE C9a Pre-emergence efficacy at 80 g/ha against PHBPU in % Example number Application rate [g/ha] PHBPU I-10 80 100 I-41 80 80 I-47 80 90 I-42 80 100 I-48 80 100 I-49 80 90 I-53 80 100 I-56 80 100

TABLE-US-00082 TABLE C9b Pre-emergence efficacy at 320 g/ha against PHBPU in % Example number Application rate [g/ha] PHBPU I-2 320 90 I-3 320 80 I-5 320 80 I-6 320 80 I-8 320 80 I-10 320 100 I-15 320 90 I-23 320 80 I-39 320 90 I-40 320 100 I-41 320 100 I-47 320 100 I-42 320 100 I-48 320 100 I-49 320 100 I-53 320 100 I-56 320 100 I-81 320 100

TABLE-US-00083 TABLE C10a Pre-emergence efficacy at 80 g/ha against POLCO in % Example number Application rate [g/ha] POLCO I-2 80 90 I-5 80 90 I-6 80 90 I-7 80 90 I-8 80 90 I-10 80 90 I-11 80 80 I-14 80 90 I-15 80 80 I-23 80 100 I-25 80 80 I-38 80 100 I-39 80 100 I-40 80 100 I-41 80 100 I-43 80 90 I-45 80 100 I-46 80 90 I-47 80 100 I-42 80 100 I-48 80 100 I-49 80 100 I-50 80 80 I-52 80 90 I-53 80 100 I-55 80 90 I-56 80 100 I-68 80 90 I-70 80 100 I-81 80 80

TABLE-US-00084 TABLE C10b Pre-emergence efficacy at 320 g/ha against POLCO in % Example number Application rate [g/ha] POLCO I-2 320 100 I-3 320 100 I-5 320 100 I-6 320 90 I-7 320 100 I-8 320 90 I-9 320 90 I-10 320 100 I-11 320 80 I-14 320 100 I-15 320 100 I-23 320 100 I-24 320 80 I-25 320 90 I-36 320 90 I-32 320 100 I-34 320 100 I-38 320 100 I-39 320 100 I-40 320 100 I-41 320 100 I-43 320 90 I-45 320 100 I-46 320 100 I-47 320 100 I-42 320 100 I-48 320 100 I-49 320 100 I-50 320 90 I-52 320 100 I-53 320 100 I-55 320 90 I-56 320 100 I-68 320 90 I-70 320 100 I-71 320 100 I-73 320 90 I-74 320 90 I-81 320 90

TABLE-US-00085 TABLE C11a Pre-emergence efficacy at 80 g/ha against SETVI in % Example number Application rate [g/ha] SETVI I-2 80 100 I-3 80 100 I-5 80 90 I-6 80 90 I-7 80 100 I-8 80 100 I-10 80 100 I-11 80 90 I-14 80 100 I-15 80 80 I-23 80 100 I-25 80 80 I-32 80 90 I-34 80 80 I-38 80 100 I-39 80 100 I-40 80 100 I-41 80 100 I-43 80 100 I-45 80 100 I-46 80 100 I-47 80 100 I-42 80 100 I-48 80 100 I-49 80 100 I-50 80 100 I-53 80 100 I-55 80 80 I-56 80 100 I-70 80 90 I-74 80 100 I-81 80 100

TABLE-US-00086 TABLE C11b Pre-emergence efficacy at 320 g/ha against SETVI in % Example number Application rate [g/ha] SETVI I-2 320 100 I-3 320 100 I-5 320 100 I-6 320 100 I-7 320 100 I-8 320 100 I-9 320 90 I-10 320 100 I-11 320 100 I-14 320 100 I-15 320 100 I-23 320 100 I-24 320 80 I-25 320 100 I-32 320 100 I-34 320 100 I-38 320 100 I-39 320 100 I-40 320 100 I-41 320 100 I-43 320 100 I-45 320 100 I-46 320 100 I-47 320 100 I-42 320 100 I-48 320 100 I-49 320 100 I-50 320 100 I-52 320 100 I-53 320 100 I-55 320 90 I-56 320 100 I-68 320 100 I-70 320 100 I-71 320 100 I-73 320 100 I-74 320 100 I-81 320 100 I-85 320 90 I-83 320 100

TABLE-US-00087 TABLE C12a Pre-emergence efficacy at 80 g/ha against VERPE in % Example number Application rate [g/ha] VERPE I-2 80 90 I-5 80 100 I-6 80 80 I-7 80 90 I-8 80 100 I-10 80 100 I-11 80 100 I-14 80 100 I-23 80 100 I-25 80 80 I-32 80 80 I-34 80 80 I-38 80 100 I-39 80 100 I-40 80 100 I-41 80 100 I-42 80 100 I-53 80 100 I-68 80 90 I-70 80 80 I-74 80 80 I-81 80 100

TABLE-US-00088 TABLE C12b Pre-emergence efficacy at 320 g/ha against VERPE in % Example number Application rate [g/ha] VERPE I-2 320 100 I-3 320 100 I-5 320 100 I-6 320 90 I-7 320 100 I-8 320 100 I-9 320 100 I-10 320 100 I-11 320 100 I-12 320 90 I-13 320 90 I-14 320 100 I-15 320 80 I-23 320 100 I-24 320 90 I-25 320 100 I-32 320 100 I-34 320 100 I-38 320 100 I-39 320 100 I-40 320 100 I-41 320 100 I-42 320 100 I-53 320 100 I-55 320 100 I-68 320 90 I-70 320 100 I-71 320 90 I-73 320 80 I-74 320 100 I-81 320 100 I-83 320 90

TABLE-US-00089 TABLE C13a Pre-emergence efficacy at 80 g/ha against VIOTR in % Example number Application rate [g/ha] VIOTR I-2 80 100 I-3 80 90 I-5 80 100 I-6 80 80 I-7 80 80 I-8 80 90 I-9 80 90 I-10 80 90 I-11 80 100 I-14 80 100 I-15 80 100 I-23 80 100 I-24 80 80 I-25 80 90 I-32 80 100 I-34 80 100 I-38 80 100 I-39 80 100 I-40 80 100 I-41 80 100 I-43 80 90 I-45 80 100 I-46 80 100 I-47 80 100 I-42 80 100 I-48 80 100 I-49 80 100 I-52 80 100 I-53 80 100 I-56 80 100 I-68 80 100 I-70 80 100 I-71 80 100 I-74 80 100 I-81 80 100 I-83 80 90

TABLE-US-00090 TABLE C13b Pre-emergence efficacy at 320 g/ha against VIOTR in % Example number Application rate [g/ha] VIOTR I-2 320 100 I-3 320 100 I-5 320 100 I-6 320 90 I-7 320 100 I-8 320 90 I-9 320 100 I-10 320 100 I-11 320 100 I-12 320 90 I-14 320 100 I-15 320 100 I-23 320 100 I-24 320 80 I-25 320 100 I-32 320 100 I-34 320 100 I-38 320 100 I-39 320 100 I-40 320 100 I-41 320 100 I-43 320 100 I-45 320 100 I-46 320 100 I-47 320 100 I-42 320 100 I-48 320 100 I-49 320 100 I-50 320 90 I-52 320 100 I-53 320 100 I-55 320 100 I-56 320 100 I-68 320 100 I-70 320 100 I-71 320 100 I-73 320 100 I-74 320 100 I-81 320 100 I-78 320 100 I-85 320 80 I-83 320 100

TABLE-US-00091 TABLE C14a Pre-emergence efficacy at 80 g/ha against KCHSC in % Example number Application rate [g/ha] KCHSC I-32 80 100 I-34 80 90 I-38 80 100 I-39 80 100 I-40 80 100 I-41 80 100 I-43 80 100 I-45 80 90 I-47 80 100 I-42 80 100 I-48 80 100 I-49 80 100 I-50 80 90 I-52 80 100 I-53 80 100 I-55 80 80 I-56 80 100 I-68 80 100 I-70 80 100 I-81 80 100 I-78 80 100

TABLE-US-00092 TABLE C14b Pre-emergence efficacy at 320 g/ha against KCHSC in % Example number Application rate [g/ha] KCHSC I-36 320 100 I-32 320 100 I-34 320 100 I-38 320 100 I-39 320 100 I-40 320 100 I-41 320 100 I-43 320 100 I-45 320 100 I-46 320 100 I-47 320 100 I-42 320 100 I-48 320 100 I-49 320 100 I-50 320 100 I-52 320 100 I-53 320 100 I-55 320 100 I-56 320 100 I-68 320 100 I-70 320 100 I-71 320 100 I-73 320 100 I-74 320 90 I-81 320 100 I-78 320 100 I-85 320 100 I-83 320 80

[0447] As shown by way of example by the results from tables C1a-C14b, the inventive compounds of the formula I in the case of pre-emergence treatment showed very good herbicidal efficacy against the harmful plants Abutilon theophrasti (ABUTH), Alopecurus myosuroides (ALOMY), Amaranthus retroflexus (AMARE), Avena fatua (AVEFA), Digitaria sanguinalis (DIGSA), Echinochloa crus-galli (ECHCG), Kochia scoparia (KCHSC), Lolium rigidum (LOLRI), Matricaria inodora (MATIN), Pharbitis purpurea (PHBPU), Polygonum convolvulus (POLCO), Setaria viridis (SETVI), Veronica persica (VERPE) and Viola tricolor (VIOTR) at an application rate of 320 g or less of active substance per hectare.

[0448] D. Pre-Emergence Effect on Useful Plants

[0449] Tables D1a to D5b below show the effects of selected compounds of the general formula (I) according to table 1 on various useful plants at an application rate corresponding to 320 g/ha or less, which were obtained by the experimental procedure mentioned above.

TABLE-US-00093 TABLE D1a Pre-emergence efficacy at 80 g/ha against ORYSA in % Example number Application rate [g/ha] ORYSA I-3 80 20 I-9 80 0 I-11 80 20 I-13 80 10 I-24 80 0 I-25 80 0

TABLE-US-00094 TABLE D1b Pre-emergence efficacy at 320 g/ha against ORYSA in % Example number Application rate [g/ha] ORYSA I-24 320 20

TABLE-US-00095 TABLE D2a Pre-emergence efficacy at 80 g/ha against ZEAMX in % Example number Application rate [g/ha] ZEAMX I-5 80 20 I-9 80 0 I-12 80 20 I-13 80 10 I-23 80 0 I-24 80 0 I-25 80 0 I-36 80 0 I-39 80 0 I-43 80 0 I-45 80 0 I-46 80 0 I-48 80 0 I-50 80 0 I-52 80 0 I-55 80 10 I-68 80 10 I-71 80 0 I-74 80 0 I-81 80 0 I-82 80 0 I-78 80 0 I-85 80 0 I-83 80 0

TABLE-US-00096 TABLE D2b Pre-emergence efficacy at 320 g/ha against ZEAMX in % Example number Application rate [g/ha] ZEAMX I-9 320 20 I-13 320 20 I-24 320 0 I-45 320 20 I-78 320 20 I-83 320 0

TABLE-US-00097 TABLE D3a Pre-emergence efficacy at 80 g/ha against TRZAS in % Example number Application rate [g/ha] TRZAS I-2 80 0 I-3 80 10 I-8 80 20 I-9 80 20 I-12 80 0 I-13 80 10 I-23 80 0 I-24 80 0 I-25 80 0 I-36 80 0 I-32 80 0 I-34 80 0 I-38 80 0 I-41 80 20 I-43 80 0 I-45 80 0 I-50 80 0 I-52 80 0 I-55 80 0 I-68 80 0 I-70 80 0 I-71 80 0 I-73 80 0 I-74 80 0 I-81 80 0 I-82 80 0 I-78 80 0 I-85 80 0

TABLE-US-00098 TABLE D3b Pre-emergence efficacy at 320 g/ha against TRZAS in % Example number Application rate [g/ha] TRZAS I-13 320 10 I-24 320 0 I-25 320 0 I-36 320 0 I-32 320 10 I-34 320 0 I-68 320 10 I-73 320 20 I-82 320 0 I-78 320 0 I-85 320 10

TABLE-US-00099 TABLE D4a Pre-emergence efficacy at 80 g/ha against GLXMA in % Example number Application rate [g/ha] GLXMA I-11 80 20 I-13 80 10 I-25 80 0 I-36 80 0 I-32 80 0 I-34 80 0 I-55 80 10 I-68 80 10 I-71 80 10 I-81 80 0 I-85 80 0

TABLE-US-00100 TABLE D4b Pre-emergence efficacy at 320 g/ha against GLXMA in % Example number Application rate [g/ha] GLXMA I-13 320 20 I-32 320 0 I-85 320 0

TABLE-US-00101 TABLE D5a Pre-emergence efficacy at 80 g/ha against BRSNW in % Example number Application rate [g/ha] BRSNW I-24 80 0 I-78 80 20 I-85 80 0

TABLE-US-00102 TABLE D5b Pre-emergence efficacy at 320 g/ha against BRSNW in % Example number Application rate [g/ha] BRSNW I-24 320 0 I-85 320 0

[0450] As shown by way of example by the results from tables D1a-D5b, the inventive compounds of the formula I in the case of pre-emergence treatment have only a small harmful effect, if any, on crop plants such as Triticum aestivum (TRZAS), Zea Mays (ZEAMX), Oryza sativa (ORYSA), Glycine max (GLXMA) and Brassica napus (BRSNW).

[0451] E. Herbicidal Post-Emergence Efficacy

[0452] Seeds of monocotyledonous and dicotyledonous weeds and crop plants were placed in sandy loam in plastic or organic planting pots, covered with soil and cultivated in a greenhouse under controlled growth conditions. 2 to 3 weeks after sowing, the test plants were treated at the one-leaf stage. The compounds of the invention, formulated in the form of wettable powders (WP) or as emulsion concentrates (EC), were 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 l/ha (converted). After the test plants had been kept in the greenhouse under optimum growth conditions for about 3 weeks, the activity of the preparations was rated visually in comparison to untreated controls.

[0453] For example, [0454] 100% efficacy=plants have died, [0455] 0% action=like untreated control plants.

[0456] Tables E1a to E12b below show the effects of selected compounds of the general formula (I) according to table 1 on various harmful plants at an application rate corresponding to 320 g/ha or less, which were obtained by the experimental procedure mentioned above.

TABLE-US-00103 TABLE E1a Post-emergence efficacy at 80 g/ha against ABUTH in % Example number Application rate [g/ha] ABUTH I-6 80 80 I-8 80 90 I-9 80 80 I-10 80 90 I-11 80 80 I-32 80 80 I-34 80 80 I-39 80 80 I-40 80 90 I-41 80 90 I-42 80 80 I-48 80 90 I-49 80 80 I-53 80 100 I-70 80 80 I-81 80 80

TABLE-US-00104 TABLE E1b Post-emergence efficacy at 320 g/ha against ABUTH in % Example number Application rate [g/ha] ABUTH I-2 320 100 I-5 320 90 I-6 320 90 I-7 320 100 I-8 320 100 I-9 320 80 I-10 320 100 I-11 320 90 I-12 320 90 I-14 320 90 I-15 320 80 I-23 320 90 I-24 320 90 I-25 320 80 I-32 320 80 I-34 320 80 I-38 320 100 I-39 320 100 I-40 320 100 I-41 320 100 I-46 320 90 I-47 320 100 I-42 320 100 I-48 320 100 I-49 320 80 I-53 320 100 I-55 320 100 I-56 320 100 I-68 320 90 I-70 320 90 I-71 320 100 I-73 320 80 I-74 320 90 I-81 320 90 I-85 320 80 I-83 320 80

TABLE-US-00105 TABLE E2a Post-emergence efficacy at 80 g/ha against ALOMY in % Example number Application rate [g/ha] ALOMY I-5 80 80 I-10 80 90 I-42 80 90 I-53 80 90

TABLE-US-00106 TABLE E2b Post-emergence efficacy at 320 g/ha against ALOMY in % Example number Application rate [g/ha] ALOMY I-2 320 90 I-3 320 80 I-5 320 90 I-6 320 90 I-7 320 90 I-8 320 90 I-10 320 100 I-11 320 90 I-14 320 90 I-23 320 80 I-38 320 80 I-40 320 90 I-41 320 100 I-47 320 100 I-42 320 100 I-48 320 100 I-49 320 80 I-53 320 100 I-56 320 80 I-81 320 90

TABLE-US-00107 TABLE E3a Post-emergence efficacy at 80 g/ha against AMARE in % Example number Application rate [g/ha] AMARE I-2 80 100 I-5 80 100 I-6 80 90 I-7 80 90 I-8 80 100 I-9 80 100 I-10 80 100 I-11 80 90 I-12 80 90 I-14 80 100 I-15 80 100 I-23 80 100 I-24 80 90 I-32 80 100 I-34 80 100 I-38 80 100 I-39 80 100 I-40 80 100 I-41 80 100 I-43 80 100 I-47 80 100 I-42 80 100 I-48 80 100 I-49 80 100 I-50 80 100 I-53 80 100 I-55 80 90 I-56 80 100 I-68 80 90 I-70 80 100 I-71 80 90 I-73 80 80 I-74 80 90 I-81 80 100 I-82 80 90 I-78 80 90 I-85 80 90 I-83 80 90

TABLE-US-00108 TABLE E3b Post-emergence efficacy at 320 g/ha against AMARE in % Example number Application rate [g/ha] AMARE I-2 320 100 I-3 320 100 I-5 320 100 I-6 320 100 I-7 320 100 I-8 320 100 I-9 320 100 I-10 320 100 I-11 320 100 I-12 320 90 I-13 320 80 I-14 320 100 I-15 320 100 I-23 320 100 I-24 320 100 I-25 320 90 I-32 320 100 I-34 320 100 I-38 320 100 I-39 320 100 I-40 320 100 I-41 320 100 I-43 320 100 I-45 320 80 I-46 320 90 I-47 320 100 I-42 320 100 I-48 320 100 I-49 320 100 I-50 320 100 I-52 320 100 I-53 320 100 I-55 320 100 I-56 320 100 I-68 320 100 I-70 320 100 I-71 320 100 I-73 320 100 I-74 320 100 I-81 320 100 I-82 320 100 I-78 320 100 I-85 320 100 I-83 320 100

TABLE-US-00109 TABLE E4a Post-emergence efficacy at 80 g/ha against DIGSA in % Example number Application rate [g/ha] DIGSA I-6 80 80 I-7 80 90 I-8 80 80 I-10 80 90 I-15 80 80 I-39 80 90 I-40 80 80 I-41 80 100 I-42 80 90 I-49 80 90 I-53 80 90 I-81 80 80

TABLE-US-00110 TABLE E4b Post-emergence efficacy at 320 g/ha against DIGSA in % Example number Application rate [g/ha] DIGSA I-6 320 100 I-7 320 100 I-8 320 90 I-9 320 80 I-10 320 90 I-15 320 90 I-23 320 100 I-32 320 90 I-34 320 90 I-38 320 90 I-39 320 100 I-40 320 100 I-41 320 100 I-42 320 90 I-48 320 100 I-49 320 100 I-53 320 90 I-55 320 90 I-56 320 100 I-68 320 90 I-70 320 90 I-81 320 90

TABLE-US-00111 TABLE E5a Post-emergence efficacy at 80 g/ha against ECHCG in % Example number Application rate [g/ha] ECHCG I-5 80 80 I-6 80 90 I-7 80 80 I-8 80 90 I-10 80 90 I-11 80 90 I-14 80 90 I-39 80 90 I-40 80 100 I-41 80 90 I-42 80 100 I-48 80 100 I-49 80 100 I-53 80 100 I-55 80 90 I-56 80 80 I-70 80 80 I-81 80 80

TABLE-US-00112 TABLE E5b Post-emergence efficacy at 320 g/ha against ECHCG in % Example number Application rate [g/ha] ECHCG I-2 320 100 I-3 320 90 I-5 320 100 I-6 320 100 I-7 320 100 I-8 320 90 I-10 320 90 I-11 320 90 I-12 320 90 I-14 320 100 I-15 320 80 I-23 320 100 I-24 320 80 I-25 320 100 I-32 320 90 I-34 320 90 I-38 320 100 I-39 320 100 I-40 320 100 I-41 320 100 I-46 320 100 I-47 320 100 I-42 320 100 I-48 320 100 I-49 320 100 I-50 320 100 I-52 320 100 I-53 320 100 I-55 320 100 I-56 320 100 I-68 320 90 I-70 320 100 I-71 320 90 I-74 320 100 I-81 320 80 I-83 320 80

TABLE-US-00113 TABLE E6a Post-emergence efficacy at 80 g/ha against LOLRI in % Example number Application rate [g/ha] LOLRI I-42 80 80 I-53 80 80

TABLE-US-00114 TABLE E6b Post-emergence efficacy at 320 g/ha against LOLRI in % Example number Application rate [g/ha] LOLRI I-5 320 90 I-8 320 80 I-10 320 90 I-11 320 90 I-47 320 100 I-42 320 100 I-48 320 90 I-49 320 80 I-53 320 100 I-55 320 80 I-81 320 80

TABLE-US-00115 TABLE E7a Post-emergence efficacy at 80 g/ha against PHBPU in % Example number Application rate [g/ha] PHBPU I-6 80 80 I-10 80 100 I-12 80 90 I-14 80 100 I-15 80 90 I-25 80 80 I-32 80 80 I-34 80 80 I-38 80 100 I-39 80 90 I-40 80 100 I-41 80 100 I-43 80 80 I-46 80 80 I-47 80 90 I-42 80 100 I-48 80 100 I-49 80 100 I-50 80 90 I-53 80 100 I-55 80 90 I-56 80 100 I-68 80 80 I-70 80 80 I-71 80 80 I-81 80 90 I-78 80 90

TABLE-US-00116 TABLE E7b Post-emergence efficacy at 320 g/ha against PHBPU in % Example number Application rate [g/ha] PHBPU I-2 320 100 I-3 320 90 I-5 320 80 I-6 320 100 I-7 320 90 I-8 320 100 I-10 320 100 I-12 320 90 I-14 320 100 I-15 320 100 I-23 320 100 I-24 320 80 I-25 320 90 I-32 320 80 I-34 320 100 I-38 320 100 I-39 320 100 I-40 320 100 I-41 320 100 I-43 320 90 I-46 320 90 I-47 320 100 I-42 320 100 I-48 320 100 I-49 320 100 I-50 320 90 I-53 320 100 I-55 320 100 I-56 320 100 I-68 320 90 I-70 320 100 I-71 320 90 I-74 320 90 I-81 320 100 I-78 320 100 I-85 320 90 I-83 320 100

TABLE-US-00117 TABLE E8a Post-emergence efficacy at 80 g/ha against POLCO in % Example number Application rate [g/ha] POLCO I-2 80 100 I-5 80 90 I-6 80 90 I-8 80 90 I-10 80 90 I-14 80 80 I-15 80 80 I-23 80 100 I-32 80 80 I-38 80 100 I-40 80 100 I-41 80 100 I-47 80 100 I-42 80 100 I-48 80 100 I-49 80 100 I-53 80 100 I-55 80 90 I-68 80 80 I-81 80 90

TABLE-US-00118 TABLE E8b Post-emergence efficacy at 320 g/ha against POLCO in % Example number Application rate [g/ha] POLCO I-2 320 100 I-3 320 90 I-5 320 100 I-6 320 100 I-7 320 100 I-8 320 90 I-9 320 90 I-10 320 100 I-11 320 100 I-12 320 100 I-13 320 80 I-14 320 90 I-15 320 100 I-23 320 100 I-32 320 100 I-34 320 100 I-38 320 100 I-39 320 100 I-40 320 100 I-41 320 100 I-43 320 90 I-45 320 100 I-46 320 100 I-47 320 100 I-42 320 100 I-48 320 100 I-49 320 100 I-50 320 100 I-52 320 80 I-53 320 100 I-55 320 100 I-56 320 100 I-68 320 90 I-70 320 100 I-71 320 100 I-81 320 100

TABLE-US-00119 TABLE E9a Post-emergence efficacy at 80 g/ha against SETVI in % Example number Application rate [g/ha] SETVI I-2 80 100 I-5 80 90 I-6 80 90 I-7 80 90 I-8 80 90 I-10 80 100 I-14 80 100 I-15 80 80 I-23 80 80 I-32 80 80 I-34 80 90 I-38 80 100 I-39 80 100 I-40 80 100 I-41 80 100 I-42 80 100 I-48 80 100 I-49 80 100 I-53 80 100 I-55 80 80 I-56 80 80 I-68 80 100 I-70 80 100

TABLE-US-00120 TABLE E9b Post-emergence efficacy at 320 g/ha against SETVI in % Example number Application rate [g/ha] SETVI I-2 320 100 I-3 320 90 I-5 320 100 I-6 320 100 I-7 320 100 I-8 320 90 I-9 320 100 I-10 320 100 I-11 320 100 I-12 320 90 I-14 320 100 I-15 320 100 I-23 320 100 I-24 320 100 I-25 320 100 I-32 320 100 I-34 320 90 I-38 320 100 I-39 320 100 I-40 320 100 I-41 320 100 I-45 320 80 I-46 320 80 I-47 320 100 I-42 320 100 I-48 320 100 I-49 320 100 I-50 320 90 I-52 320 80 I-53 320 100 I-55 320 90 I-56 320 100 I-68 320 100 I-70 320 100 I-71 320 100 I-74 320 90 I-81 320 100

TABLE-US-00121 TABLE E10a Post-emergence efficacy at 80 g/ha against VERPE in % Example number Application rate [g/ha] VERPE I-2 80 100 I-3 80 80 I-5 80 90 I-6 80 90 I-7 80 90 I-8 80 90 I-9 80 80 I-10 80 100 I-11 80 100 I-12 80 100 I-14 80 100 I-15 80 90 I-23 80 90 I-24 80 90 I-25 80 90 I-36 80 80 I-32 80 100 I-34 80 100 I-38 80 100 I-39 80 100 I-40 80 100 I-41 80 100 I-43 80 100 I-45 80 80 I-46 80 100 I-47 80 100 I-42 80 100 I-48 80 100 I-49 80 100 I-50 80 90 I-52 80 100 I-53 80 100 I-55 80 100 I-56 80 100 I-68 80 100 I-70 80 100 I-71 80 80 I-73 80 90 I-74 80 90 I-81 80 100 I-82 80 100 I-78 80 100 I-85 80 100 I-83 80 80

TABLE-US-00122 TABLE E10b Post-emergence efficacy at 320 g/ha against VERPE in % Example number Application rate [g/ha] VERPE I-2 320 100 I-3 320 90 I-5 320 100 I-6 320 90 I-7 320 100 I-8 320 100 I-9 320 90 I-10 320 100 I-11 320 100 I-12 320 100 I-13 320 90 I-14 320 100 I-15 320 100 I-23 320 100 I-24 320 100 I-25 320 100 I-36 320 100 I-32 320 100 I-34 320 100 I-38 320 100 I-39 320 100 I-40 320 100 I-41 320 100 I-43 320 100 I-45 320 100 I-46 320 100 I-47 320 100 I-42 320 100 I-48 320 100 I-49 320 100 I-50 320 100 I-52 320 100 I-53 320 100 I-55 320 100 I-56 320 100 I-68 320 100 I-70 320 100 I-71 320 100 I-73 320 100 I-74 320 100 I-81 320 100 I-82 320 100 I-78 320 100 I-85 320 100 I-83 320 100

TABLE-US-00123 TABLE E11a Post-emergence efficacy at 80 g/ha against VIOTR in % Example number Application rate [g/ha] VIOTR I-5 80 80 I-6 80 80 I-8 80 80 I-10 80 90 I-11 80 90 I-14 80 90 I-15 80 90 I-23 80 100 I-32 80 100 I-34 80 100 I-38 80 100 I-39 80 100 I-40 80 100 I-41 80 100 I-43 80 90 I-45 80 90 I-46 80 90 I-47 80 100 I-42 80 100 I-48 80 100 I-49 80 100 I-50 80 90 I-53 80 100 I-56 80 100 I-68 80 100 I-70 80 100 I-71 80 90 I-73 80 90 I-74 80 100 I-81 80 100 I-82 80 80 I-78 80 90

TABLE-US-00124 TABLE E11b Post-emergence efficacy at 320 g/ha against VIOTR in % Example number Application rate [g/ha] VIOTR I-2 320 100 I-5 320 90 I-6 320 90 I-7 320 90 I-8 320 100 I-9 320 80 I-10 320 100 I-11 320 100 I-12 320 80 I-14 320 90 I-15 320 100 I-23 320 100 I-24 320 80 I-32 320 100 I-34 320 100 I-38 320 100 I-39 320 100 I-40 320 100 I-41 320 100 I-43 320 100 I-45 320 100 I-46 320 100 I-47 320 100 I-42 320 100 I-48 320 100 I-49 320 100 I-50 320 100 I-52 320 80 I-53 320 100 I-55 320 80 I-56 320 100 I-68 320 100 I-70 320 100 I-71 320 100 I-73 320 100 I-74 320 100 I-81 320 100 I-82 320 80 I-78 320 100 I-83 320 100

TABLE-US-00125 TABLE E12a Post-emergence efficacy at 80 g/ha against KCHSC in % Example number Application rate [g/ha] KCHSC I-32 80 90 I-34 80 100 I-38 80 100 I-39 80 100 I-40 80 100 I-41 80 100 I-43 80 90 I-47 80 100 I-42 80 90 I-48 80 100 I-49 80 100 I-50 80 80 I-52 80 90 I-53 80 90 I-55 80 80 I-56 80 100 I-68 80 80 I-70 80 90 I-71 80 100 I-73 80 90 I-81 80 100 I-82 80 90 I-78 80 100 I-85 80 80

TABLE-US-00126 TABLE E12b Post-emergence efficacy at 320 g/ha against KCHSC in % Example number Application rate [g/ha] KCHSC I-36 320 90 I-32 320 100 I-34 320 100 I-38 320 100 I-39 320 100 I-40 320 100 I-41 320 100 I-43 320 100 I-45 320 90 I-46 320 100 I-47 320 100 I-42 320 90 I-48 320 100 I-49 320 100 I-50 320 100 I-52 320 100 I-53 320 90 I-55 320 90 I-56 320 100 I-68 320 90 I-70 320 100 I-71 320 100 I-73 320 90 I-74 320 80 I-81 320 100 I-82 320 90 I-78 320 100 I-85 320 100 I-83 320 80

[0457] As shown by way of example by the results from tables Ela-E12b, the inventive compounds of the formula I in the case of post-emergence treatment showed very good herbicidal efficacy against the harmful plants Abutilon theophrasti (ABUTH), Alopecurus myosuroides (ALOMY), Amaranthus retroflexus (AMARE), Digitaria sanguinalis (DIGSA), Echinochloa crus-galli (ECHCG), Kochia scoparia (KCHSC), Lolium rigidum (LOLRI), Pharbitis purpurea (PHBPU), Polygonum convolvulus (POLCO), Setaria viridis (SETVI), Veronica persica (VERPE) and Viola tricolor (VIOTR) at an application rate of 320 g or less of active substance per hectare.

[0458] F. Post-Emergence Effect on Useful Plants

[0459] Tables F1a to F4 below show the effects of selected compounds of the general formula (I) according to table 1 on various useful plants at an application rate corresponding to 320 g/ha or less, which were obtained by the experimental procedure mentioned above.

TABLE-US-00127 TABLE F1a Post-emergence efficacy at 80 g/ha against ORYSA in % Example number Application rate [g/ha] ORYSA I-2 80 0 I-3 80 10 I-5 80 20 I-8 80 20 I-9 80 10 I-13 80 10 I-15 80 0 I-23 80 0 I-24 80 0 I-25 80 0

TABLE-US-00128 TABLE F1b Post-emergence efficacy at 320 g/ha against ORYSA in % Example number Application rate [g/ha] ORYSA I-9 320 10 I-15 320 20 I-24 320 0

TABLE-US-00129 TABLE F2a Post-emergence efficacy at 80 g/ha against ZEAMX in % Example number Application rate [g/ha] ZEAMX I-2 80 20 I-3 80 10 I-9 80 20 I-11 80 20 I-13 80 20 I-23 80 20 I-24 80 20 I-36 80 0 I-32 80 20 I-39 80 20 I-41 80 0 I-43 80 0 I-48 80 0 I-52 80 0 I-56 80 20 I-70 80 20 I-71 80 0 I-73 80 20 I-74 80 0 I-82 80 0 I-83 80 10

TABLE-US-00130 TABLE F2b Post-emergence efficacy at 320 g/ha against ZEAMX in % Example number Application rate [g/ha] ZEAMX I-9 320 20 I-13 320 20 I-36 320 0 I-41 320 20 I-43 320 0 I-52 320 0 I-82 320 20 I-83 320 20

TABLE-US-00131 TABLE F3a Post-emergence efficacy at 80 g/ha against TRZAS in % Example number Application rate [g/ha] TRZAS I-2 80 0 I-3 80 0 I-5 80 20 I-7 80 20 I-8 80 20 I-9 80 20 I-11 80 20 I-12 80 0 I-13 80 10 I-14 80 20 I-23 80 0 I-24 80 0 I-25 80 0 I-36 80 0 I-32 80 0 I-34 80 0 I-38 80 10 I-39 80 0 I-40 80 10 I-41 80 0 I-43 80 0 I-45 80 0 I-46 80 0 I-47 80 0 I-48 80 10 I-49 80 20 I-50 80 0 I-52 80 0 I-55 80 20 I-56 80 10 I-68 80 20 I-70 80 20 I-71 80 0 I-73 80 0 I-74 80 0 I-81 80 0 I-82 80 0 I-78 80 0 I-85 80 0 I-83 80 0

TABLE-US-00132 TABLE F3b Post-emergence efficacy at 320 g/ha against TRZAS in % Example number Application rate [g/ha] TRZAS I-3 320 10 I-12 320 0 I-13 320 10 I-24 320 0 I-25 320 0 I-36 320 0 I-32 320 20 I-34 320 20 I-38 320 20 I-39 320 20 I-40 320 20 I-43 320 0 I-45 320 0 I-46 320 10 I-50 320 10 I-52 320 0 I-68 320 20 I-71 320 0 I-73 320 20 I-82 320 0 I-83 320 20

TABLE-US-00133 TABLE F4 Post-emergence efficacy at 80 g/ha against GLXMA in % Example number Application rate [g/ha] GLXMA I-13 80 10

[0460] As shown by way of example by the results from tables Fla-F4, the inventive compounds of the formula I in the case of post-emergence treatment have only a small harmful effect, if any, on useful plants such as Triticum aestivum (TRZAS), Zea Mays (ZEAMX), Oryza sativa (ORYSA) and Glycine max (GLXMA).