HERBICIDALLY ACTIVE BICYCLIC BENZAMIDES

Abstract

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

##STR00001##

In this formula (I), B, X.sup.1 and X.sup.2 represent N, O or S(O).sub.n.

R, R.sup.a, R.sup.b and R.sup.x represent radicals such as hydrogen, halogen, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkyloxy and cyano.

Claims

1. A compound of formula (I) ##STR00041## and/or an agrochemically acceptable salt thereof, in which the symbols and indices have the following meanings: B represents N or CH, X.sup.1, X.sup.2 independently of one another each represent O or S(O).sub.n, R represents hydrogen, halogen, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, R.sup.1O or R.sup.2(O).sub.nS, R.sup.a, R.sup.b independently of one another each represent hydrogen, fluorine, chlorine, hydroxy, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkyloxy, (C.sub.1-C.sub.6)-alkylthio, cyano, or R.sup.a and R.sup.b together with the carbon atom to which they are attached form a carbonyl or a thiocarbonyl group, R.sup.x represents (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkyl-O(C.sub.1-C.sub.6)-alkyl or phenyl, R.sup.1 represents (C.sub.1-C.sub.6)-alkyl or halo-(C.sub.1-C.sub.6)-alkyl, R.sup.2 represents (C.sub.1-C.sub.6)-alkyl, n represents 0, 1 or 2.

2. The compound as claimed in claim 1, in which B represents N or CH, X.sup.1, X.sup.2 independently of one another each represent O or S(O).sub.n, R represents hydrogen, chlorine, bromine, iodine, (C.sub.1-C.sub.3)-alkyl, halo-(C.sub.1-C.sub.3)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, R.sup.1O or R.sup.2(O).sub.nS, R.sup.a, R.sup.b independently of one another each represent hydrogen, fluorine, chlorine, hydroxy, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkyloxy, (C.sub.1-C.sub.6)-alkylthio, cyano, or R.sup.a and R.sup.b together with the carbon atom to which they are attached form a carbonyl or a thiocarbonyl group, R.sup.x represents (C.sub.1-C.sub.3)-alkyl or (C.sub.1-C.sub.3)-alkyl-O(C.sub.1-C.sub.3)-alkyl, R.sup.1 represents (C.sub.1-C.sub.3)-alkyl or halo-(C.sub.1-C.sub.3)-alkyl, R.sup.2 represents (C.sub.1-C.sub.3)-alkyl, n represents 0, 1 or 2.

3. The compound as claimed in claim 1, in which B represents N or CH, X.sup.1, X.sup.2 independently of one another each represent O or S(O).sub.n, R represents hydrogen, chlorine, bromine, iodine, methyl, ethyl, cyclopropyl, trifluoromethyl, difluoromethyl, pentafluoroethyl, methylsulfanyl, methylsulfinyl, methylsulfonyl, ethylsulfonyl or methoxy, R.sup.a, R.sup.b independently of one another each represent hydrogen, fluorine, chlorine, methyl, ethyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, methylthio, ethylthio, cyano, or R.sup.a and R.sup.b together with the carbon atom to which they are attached form a carbonyl or a thiocarbonyl group, R.sup.x represents methyl, ethyl, propyl, methoxymethyl, methoxyethyl or 2-methoxy-2-methyl-1-propyl, n represents 0, 1 or 2.

4. A herbicidal composition comprising at least one compound as claimed in claim 1 mixed with one or more formulation auxiliaries.

5. The herbicidal composition as claimed in claim 1, comprising at least one further pesticidally active substance selected from the group consisting of insecticides, acaricides, herbicides, fungicides, safeners, and growth regulators.

6. A method for controlling one or more unwanted plants, comprising applying an effective amount of at least one compound as claimed in claim 1 or a herbicidal composition thereof to the plants and/or a site of unwanted vegetation.

7. A product comprising a compound as claimed in claim 1 or a herbicidal composition thereof for controlling one or more unwanted plants.

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

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

10. A compound of formula (II) ##STR00042## in which the symbols and indices are defined as follows: L represents chlorine, methoxy, ethoxy or hydroxy, X.sup.1, X.sup.2 independently of one another each represent O or S(O).sub.n, where X.sup.1 and X.sup.2 are not simultaneously O or S(O).sub.n, R represents SO.sub.2Me, SO.sub.2Et, trifluoromethyl, difluoromethyl or pentafluoroethyl, R.sup.a, R.sup.b independently of one another each represent hydrogen, fluorine, chlorine, methyl, ethyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, methylthio, ethylthio, cyano, or R.sup.a and R.sup.b together with the carbon atom to which they are attached form a carbonyl or a thiocarbonyl group, n represents 0, 1 or 2.

11. A compound of the formula (III) ##STR00043## in which the symbols and indices have the following meanings: L represents chlorine, methoxy, ethoxy or hydroxy, X represents hydroxy, SH, methylsulfanyl or halogen, Y represents chlorine or bromine, R represents hydrogen, methyl, ethyl, cyclopropyl, trifluoromethyl, difluoromethyl, pentafluoroethyl, methylsulfanyl, methylsulfinyl, methylsulfonyl, ethylsulfonyl or methoxy, R.sup.a, R.sup.b independently of one another each represent hydrogen or methyl.

12. A compound of formula (IV) ##STR00044## in which the symbols and indices have the following meanings: B represents N or CH, X represents hydroxy, SH or halogen, Y represents chlorine or bromine, R represents hydrogen, chlorine, bromine, iodine, methyl, ethyl, cyclopropyl, trifluoromethyl, difluoromethyl, pentafluoroethyl, methylsulfanyl, methylsulfinyl, methylsulfonyl, ethylsulfonyl, methoxy, R.sup.a, R.sup.b independently of one another each represent hydrogen or methyl, R.sup.x represents methyl, ethyl, propyl, methoxymethyl, methoxyethyl, 2-methoxy-2-methyl-1-propyl.

13. A compound of the formula (V) ##STR00045## in which the symbols and indices have the following meanings: B represents N or CH, Z represents OH, SH, R represents hydrogen, chlorine, bromine, iodine, methyl, ethyl, cyclopropyl, trifluoromethyl, difluoromethyl, pentafluoroethyl, methylsulfanyl, methylsulfinyl, methylsulfonyl, ethylsulfonyl, methoxy, R.sup.x represents methyl, ethyl, propyl, methoxymethyl, methoxyethyl, 2-methoxy-2-methyl-1-propyl.

Description

CHEMICAL EXAMPLES

Example 2-21: Synthesis of 7-(trifluoromethyl)-1,3-benzodithiolane-N-(1-methyltetrazol-5-yl)-4-carboxamide

[0292] ##STR00035##

[0293] 0.12 ml (1.7 mmol) of thionyl chloride is added dropwise to 350 mg (1.3 mmol) of 7-(trifluoromethyl)-1,3-benzodithiolane-4-carboxylic acid, 0.52 ml (6.5 mmol) of N-methylimidazole and 195 mg (1.95 mmol) of 5-amino-1-methyltetrazole in 5 ml of acetonitrile. After 2 days (d) of stirring at room temperature (RT), 5 ml of water and 3 ml of 2N hydrochloric acid are added. The crystals obtained are filtered off, washed with water and dried. Yield 175 mg.

Intermediate 2-21A: Synthesis of methyl 2-fluoro-3-methylthio-4-(trifluoromethyl)benzoate

[0294] At 0 C., 3.2 ml (33 mmol) of dimethyl sulfate are added to 7.62 g (30 mmol) of 2-fluoro-3-methylthio-4-(trifluoromethyl)benzoic acid (synthesis according to US2011/45980) and 4.9 g (35 mmol) of potassium carbonate in 30 ml of DMF, and the mixture is stirred at RT for 3 h. The mixture is then poured onto water and extracted with ethyl acetate, and the organic phase is washed with 2N hydrochloric acid, water, sat. sodium bicarbonate solution and sat. sodium chloride solution. The organic phase is dried and concentrated and the crude product obtained is reacted further without purification. (NMR, CDCl.sub.3: 7.94 (t, 1H), 7.55 (dd, 1H), 3.97 (s, 3H), 2.48 (s, 3H))

Intermediate 2-21B: Synthesis of methyl 2-fluoro-3-methylsulfinyl-4-(trifluoromethyl)benzoate

[0295] At 0 C., 6.90 g (30 mmol) of m-chloroperbenzoic acid (about 77% strength) are added to 8.02 g (30 mmol) of methyl 2-fluoro-3-methylthio-4-(trifluoromethyl)benzoate in 200 ml of dichloromethane. After 30 min, the reaction is quenched with sodium bisulfite solution. The organic phase is washed with sat. sodium bicarbonate solution, dried and concentrated. The crude product obtained is reacted further without purification. (NMR, CDC.sub.3: 8.18 (t, 1H), 7.63 (dd, 1H), 4.00 (s, 3H), 3.13 (s, 3H))

Intermediate 2-21 C: Synthesis of methyl 2-fluoro-3-chloromethylsulfanyl-4-(trifluoromethyl)benzoate

[0296] 597 mg (2.1 mmol) of methyl 2-fluoro-3-methylsulfinyl-4-(trifluoromethyl)benzoate in 6 ml of thionyl chloride are heated at reflux for 3 h. The solution is then concentrated and the resulting crude product is reacted further without purification. (NMR, CDC.sub.3: 8.08 (t, 1H), 7.64 (dd, 1H), 4.93 (s, 2H), 3.99 (s, 3H))

Intermediate 2-21D: Synthesis of methyl 7-(trifluoromethyl)-1,3-benzodithiolane-4-carboxylate

[0297] At 0 C., 195 mg (2.5 mmol) of sodium sulfide (anhydrous) are added to obtained Intermediate 2-21C (about 2.1 mmol) methyl 2-fluoro-3-chloromethylsulfanyl-4-(trifluoromethyl)benzoate in 5 ml of dimethylformamide, and the mixture is then stirred at 80 C. for 5 h. The mixture is then poured onto 2N hydrochloric acid and extracted with ethyl acetate, and the organic phase is washed with water, sat. sodium bicarbonate solution and sat. sodium chloride solution. The organic phase is dried and concentrated and the crude product obtained is purified by column chromatography (heptene/ethyl acetate). Yield 385 mg (65% of theory). (NMR, CDCl.sub.3: 7.78 (dd, 1H), 7.35 (d, 1H), 4.50 (s, 2H) 3.96 (s, 3H))

Intermediate 2-21E: Synthesis of 7-(trifluoromethyl)-1,3-benzodithiolane-4-carboxylic acid

[0298] A mixture of 385 mg (1.3 mmol) of methyl 7-(trifluoromethyl)-1,3-benzodithiolane-4-carboxylate in 3 ml of methanol and 3 ml of 2N aqueous sodium hydroxide solution is stirred at 50 C. for 2 h. The mixture is then acidified with 2N hydrochloric acid and extracted with dichloromethane, the organic phase is dried and concentrated and the crude product obtained is reacted further without purification. (NMR, CDCl.sub.3: 7.84 (dd, 1H), 7.38 (d, 1H), 4.52 (s, 2H))

Example 2-53: Synthesis of 4-(trifluoromethyl)-1,3-benzoxathiolane-N-(1-methyltetrazol-5-yl)-7-carboxamide

[0299] ##STR00036##

[0300] 0.76 ml (8.7 mmol) of oxalyl chloride are added dropwise to 1.5 g (6 mmol) of 4-(trifluoromethyl)-1,3-benzoxathiolane-7-carboxylic acid and 788 mg (7.8 mmol) of 5-amino-1-methyltetrazole in a mixture of 7.5 ml of acetonitrile and 5 ml of pyridine. After 3 d at RT, water and 2N hydrochloric acid are added and the mixture is diluted with ethyl acetate. The organic phase is dried and concentrated and the residue obtained is washed with isopropanol. The crystals are dissolved in methanol and reprecipitated with water, washed with water and dried. Yield 1.15 g.

Intermediate 2-53A: Synthesis of ethyl 2-hydroxy-3-methylsulfinyl-4-(trifluoromethyl)benzoate

[0301] 20 mg of sulfuric acid and 2.4 ml (27 mmol) of hydrogen peroxide (35% strength) are added to 6.45 g (22.5 mmol) of ethyl 2-hydroxy-3-methylthio-4-(trifluoromethyl)benzoate in 15 ml of acetonitrile, and the mixture is then heated at 60 C. for 20 h. After addition of sodium bisulfite solution, the mixture is concentrated and the residue is filtered off with suction and washed with water and a little ethyl acetate. The organic phase is washed with sat. sodium chloride solution, dried and concentrated and the crude product obtained is reacted further without purification. Yield 6.64 g. (NMR, DMSO-D.sub.6: 11.80 (brs, 1H), 8.05 (d, 1H), 7.45 (d, 1H), 4.39 (q, 2H), 3.15 (s, 3H), 1.34 (t, 3H))

Intermediate 2-53B: Synthesis of ethyl 2-hydroxy-3-chloromethylsulfanyl-4-(trifluoromethyl)benzoate

[0302] With cooling with water, 6 ml of thionyl chloride are added dropwise to 5.6 g (18.2 mmol) of ethyl 2-hydroxy-3-methylsulfinyl-4-(trifluoromethyl)benzoate (evolution of gas!), and stirring is then continued for 15 min. The mixture is concentrated and reacted further without purification. (NMR, DMSO-D.sub.6: 11.68 (brs, 1H), 8.07 (dd, 1H), 7.45 (d, 1H), 5.32 (s, 2H), 4.45 (q, 2H), 1.38 (t, 3H))

Intermediate 6-1: Synthesis of 4-(trifluoromethyl)-1,3-benzoxathiolane-7-carboxylic acid

[0303] With ice bath cooling, 5 g (18.2 mmol) of ethyl 2-hydroxy-3-chloromethylsulfanyl-4-(trifluoromethyl)benzoate, dissolved in 5 ml of acetonitrile, are added to 170 g of 20% strength aqueous sodium hydroxide solution. The mixture is allowed to stand overnight and then acidified to pH 1 with conc. hydrochloric acid, and the precipitate is filtered off with suction and washed with water. Subsequent dissolution in 5% strength aqueous sodium hydroxide solution, removal of undissolved byproducts by filtration with suction and precipitation by acidification with conc. hydrochloric acid gives, after drying, 3.9 g of product.

Example 2-68: Synthesis of 4-(trifluoromethyl)-1,3-benzoxathiolane-N-(1-methyltetrazol-5-yl)-7-carboxamide 3-oxide

[0304] ##STR00037##

[0305] 10 mg of sulfuric acid and 0.37 ml (3.6 mmol) of hydrogen peroxide (30% strength) are added to 400 mg (1.2 mmol) of 4-(trifluoromethyl)-1,3-benzoxathiolane-N-(1-methyltetrazol-5-yl)-7-carboxamide in 10 ml of acetonitrile, and the mixture is then heated at 50 C. for 13 h. After addition of sodium bisulfite solution, the mixture is concentrated and the residue is filtered off with suction and washed with water and a little ethyl acetate. Yield 190 mg.

Example 2-94: Synthesis of 2-methyl-4-(trifluoromethyl)-1,3-benzoxathiolane-N-(1-methyltetrazol-5-yl)-7-carboxamide

[0306] ##STR00038##

[0307] 0.08 ml (0.88 mmol) of oxalyl chloride are added dropwise to 200 mg (0.6 mmol) of 2-methyl-4-(trifluoromethyl)-1,3-benzoxathiolane-7-carboxylic acid and 83 mg (0.8 mmol) of 5-amino-1-methyltetrazole in a mixture of 1 ml of acetonitrile and 0.5 ml of pyridine. After standing overnight at RT, the mixture is diluted with water and ethyl acetate. The organic phase is washed with sat. sodium bicarbonate solution and sat. sodium chloride solution, dried and concentrated and the crude product obtained is purified by column chromatography (heptene/ethyl acetate). Yield 50 mg.

Intermediate 2-94A: Synthesis of ethyl 2-hydroxy-3-mercapto-4-(trifluoromethyl)benzoate

[0308] 5 g (15.9 mmol) of ethyl 2-hydroxy-3-chloromethylsulfanyl-4-(trifluoromethyl)benzoate (intermediate 2-53B) in 20 ml of ethanol and 20 ml of conc. hydrochloric acid are heated under reflux for 8 h. The ethanol is then evaporated under reduced pressure, the residue is diluted with ethyl acetate and the organic phase is dried and partially concentrated. Addition of heptane yields crystals. Yield 3.97 g. (NMR, DMSO-D.sub.6: 11.5 (brs), 7.73 (d, 1H), 7.31 (d, 1H), 4.43 (q, 2H), 1.37 (t, 3H))

Intermediate 6-10: Synthesis of 2-methyl-4-(trifluoromethyl)-1,3-benzoxathiolane-7-carboxylic acid

[0309] A mixture of 400 mg (1.05 mmol) of ethyl 2-hydroxy-3-mercapto-4-(trifluoromethyl)benzoate, 0.75 ml (3.15 mmol) of tributylamine and 296 mg (1.58 mmol) of 1,1-dibromoethane in 4 ml of acetonitrile are stirred at 65 C. Once no more starting material is detectable, the mixture is concentrated and dissolved in 5 ml of ethanol. After addition of 1 ml of aqueous sodium hydroxide solution (50% strength), the mixture is stirred at room temperature for 1 h. The mixture is then diluted with water, the ethanol is evaporated under reduced pressure and the residue is acidified. The precipitated solid is filtered off with suction, washed with water and dried. Yield 235 mg.

Example 2-112: Synthesis of 2-methoxy-4-(trifluoromethyl)-1,3-benzoxathiolane-N-(1-methyltetrazol-5-yl)-7-carboxamide

[0310] ##STR00039##

[0311] 0.2 ml (2.8 mmol) of thionyl chloride is added to 200 mg (0.56 mmol) of 4-(trifluoromethyl)-1,3-benzoxathiolan-3-one-N-(1-methyltetrazol-5-yl)-7-carboxamide in 2.5 ml of acetonitrile, and the mixture is stirred at RT for 1 h. The mixture is then diluted with 5 ml of methanol. After 10 min, the mixture is diluted with water and extracted with ethyl acetate, and the organic phase is washed with sat. sodium chloride solution. Concentration and washing of the residue with a little ethyl acetate gives 105 mg of a colorless solid.

Example 2-238: Synthesis of 7-(trifluoromethyl)-1,3-benzoxathiolane-N-(1-methyltetrazol-5-yl)-4-carboxamide

[0312] ##STR00040##

[0313] 95 mg (0.27 mmol) of 3-hydroxy-2-methylsulfinyl-4-(trifluoromethyl)-N-(1-methyltetrazol-5-yl)benzamide are stirred in 1 ml of thionyl chloride for 30 min. Excess thionyl chloride is then removed on a rotary evaporator, the residue is taken up in 1 ml of DMF and 60 mg (0.82 mmol) of sodium methanethiolate are added at 0 C. After 1 h, 0.04 ml (0.54 mmol) of dibromomethane are added and the mixture is stirred at RT for 2 h and at 80 C. for 1 h. After cooling, sat. ammonium chloride solution is added and the mixture is extracted with ethyl acetate. The organic phase is washed with sat. sodium chloride solution, dried and concentrated and the crude product obtained is purified by column chromatography (heptane/ethyl acetate). Yield 14 mg.

Intermediate 2-238A: Synthesis of 3-fluoro-2-methylthio-4-(trifluoromethyl)-N-(1-methyltetrazol-5-yl)benzamide

[0314] At 0 C., 0.15 ml (1.95 mmol) of thionyl chloride are added dropwise to 381 mg (1.5 mmol) of 3-fluoro-2-methylthio-4-(trifluoromethyl)benzoic acid (synthesis: EP2105437), 0.24 ml (3 mmol) of N-methylimidazole and 182 mg (1.8 mmol) of 5-amino-1-methyltetrazole in 5 ml of pyridine. After 2 d at RT, water and 2N hydrochloric acid are added. The crystals obtained are filtered off, washed with water and dried. Yield 430 mg. (NMR, DMSO-D.sub.6: 11.86 (brs, 1H), 7.94 (dd, 1H), 7.71 (d, 1H), 4.04 (s, 3H), 3.14 (s, 3H))

Intermediate 2-238B: Synthesis of 3-fluoro-2-methylsulfinyl-4-(trifluoromethyl)-N-(1-methyltetrazol-5-yl)benzamide

[0315] A mixture of 1.01 g (3 mmol) of 3-fluoro-2-methylthio-4-(trifluoromethyl)-N-(1-methyltetrazol-5-yl)benzamide and 0.17 ml of hydrogen peroxide (50%) in 10 ml of acetic acid is stirred at 40 C. for 13 h. The mixture is then diluted with 140 ml of water and the crystals obtained are filtered off with suction and dried. Yield 645 mg. (NMR, DMSO-D.sub.6: 12.02 (brs, 1H), 8.18 (dd, 1H), 7.87 (d, 1H), 4.04 (s, 3H), 2.52 (s, 3H))

Intermediate 2-238C: Synthesis of 3-(4-methoxybenzyloxy)-2-methylsulfinyl-4-(trifluoromethyl)-N-(1-methyltetrazol-5-yl)benzamide

[0316] At 0 C., 430 mg (3.75 mmol) of potassium tert-butoxide are added to a mixture of 600 mg (1.7 mmol) of 3-fluoro-2-methylsulfinyl-4-(trifluoromethyl)-N-(1-methyltetrazol-5-yl)benzamide and 0.32 ml (2.6 mmol) of anisyl alcohol in 10 ml of THF. After 16 h at room temperature, 2N hydrochloric acid is added, the mixture is extracted with dichloromethane and the organic phase is dried and concentrated. The crude product obtained is reacted further without purification. Yield 970 mg. (NMR, CDCl.sub.3: 11.42 (brs, 1H), 7.87 (d, 1H), 7.66 (d, 1H), 7.29 (m, 2H), 6.95 (m, 2H), 5.06 (d, 1H), 5.00 (d, 1H), 4.19 (s, 3H), 3.85 (s, 3H), 2.98 (s, 3H))

Intermediate 2-238D: Synthesis of 3-hydroxy-2-methylsulfinyl-4-(trifluoromethyl)-N-(1-methyltetrazol-5-yl)benzamide

[0317] 0.23 ml (3.03 mmol) of trifluoroacetic acid is added to a mixture of 475 mg (1.01 mmol) of 3-(4-methoxybenzyloxy)-2-methylsulfinyl-4-(trifluoromethyl)-N-(1-methyltetrazol-5-yl)benzamide and 0.33 ml (3.03 mmol) of anisole in 10 ml of dichloromethane, and the mixture is stirred at room temperature for 6 d. Water is then added, and the mixture is diluted with ethyl acetate. The organic phase is washed with sat. sodium bicarbonate solution, the aqueous phase obtained is acidified with 2N hydrochloric acid and the resulting crystals are filtered off with suction, washed with water and dried. Yield 115 mg. (NMR, DMSO-D.sub.6: 12.98 (brs, 1H), 12.07 (brs, 1H), 8.00 (d, 1H), 7.66 (d, 1H), 3.97 (s, 3H), 3.23 (s, 3H))

[0318] The NMR data of disclosed examples are listed either in conventional form (6 values, number of hydrogen atoms, multiplet splitting) or as so-called NMR peak lists. In the NMR peak list method, the NMR data of selected examples are recorded in the form of NMR peak lists, where for each signal peak first the value in ppm and then, separated by a space, the signal intensity are listed. The value/signal intensity number pairs for different signal peaks are listed with separation from one another by semicolons.

[0319] The peak list for one example therefore takes the form of:

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

[0320] The intensity of sharp signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the true ratios of the signal intensities. In the case of broad signals, several peaks or the middle of the signal and the relative intensity thereof may be shown in comparison to the most intense signal in the spectrum.

[0321] Calibration of the chemical shift of .sup.1H NMR spectra is accomplished using tetramethylsilane and/or the chemical shift of the solvent, particularly in the case of spectra which are measured in DMSO. Therefore, the tetramethylsilane peak may but need not occur in NMR peak lists.

[0322] The lists of the .sup.1H NMR peaks are similar to the conventional .sup.1H NMR printouts and thus usually contain all peaks listed in a conventional NMR interpretation.

[0323] In addition, like conventional .sup.1H NMR printouts, they may show solvent signals, signals of stereoisomers of the target compounds which are likewise provided by the invention, and/or peaks of impurities.

[0324] In the reporting of compound signals within the delta range of solvents and/or water, our lists of .sup.1H NMR peaks show the standard solvent peaks, for example peaks of DMSO in DMSO-D.sub.6 and the peak of water, which usually have a high intensity on average.

[0325] Such stereoisomers and/or impurities may be typical of the particular preparation process. Their peaks can thus help in identifying reproduction of our preparation process with reference to by-product fingerprints.

[0326] An expert calculating the peaks of the target compounds by known methods (MestreC, ACD simulation, but also with empirically evaluated expected values) can, if required, isolate the peaks of the target compounds, optionally using additional intensity filters. This isolation would be similar to the relevant peak picking in conventional 1H NMR interpretation.

[0327] Further details of .sup.1H NMR peak lists can be found in the Research Disclosure Database Number 564025.

TABLE-US-00008 Analytical data No. NMR 1-35 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): = 10.73 (br s, 1H); 7.90 (s, 1H); 7.58 (d, 1H); 7.39 (d, 1H); 6.02 (s, 2H); 3.70 (s, 3H) 1-50 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): = 8.23 (d, 1H); 7.93 (s, 1H); 7.76 (d, 1H); 5.90 (d, 1H); 5.38 (d, 1H); 3.76 (s, 3H) 1-65 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): = 11.28 (br s, 1H); 8.25 (d, 1H); 7.92 (s, 1H); 7.82 (d, 1H); 5.63 (s, 2H); 3.75 (s, 3H) 2-4 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): = 7.46 (d, 1H); 7.28 (d, 1H); 6.37 (s, 2H); 3.94 (s, 3H) 2-7 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): = 11.68 (br s, 1H); 7.73 (m, 2H); 7.41 (t, 1H); 3.96 (s, 3H) 2-13 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): = 11.60 (br s, 1H); 7.76 (d, 1H); 7.33 (d, 1H); 3.95 (s, 3H); 2.67 (s, 3H) 2-15 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): = 11.91 (br s, 1H); 7.92 (d, 1H); 7.77 (d, 1H); 3.97 (s, 3H); 3.43 (s, 3H) 2-19 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): = 11.85 (br s, 1H); 7.79 (d, 1H); 7.40 (d, 1H); 4.64 (s, 2H); 3.92 (s, 3H) 2-20 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): = 11.56 (br s, 1H); 7.73 (d, 1H); 7.13 (d, 1H); 4.55 (s, 2H); 3.91 (s, 3H); 2.29 (s, 3H) 2-21 .sup.1H-NMR(400.0 MHz, CDCl.sub.3): = 11.82 (br s, 1H); 8.05 (d, 1H); 7.55 (d, 1H); 4.49 (s, 2H); 4.09 (s, 3H) 2-22 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): = 11.82 (br s, 1H); 7.49 (d, 1H); 7.51 (d, 1H); 7.08 (t, 1H); 4.65 (s, 2H); 3.94 (s, 3H) 2-41 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): = 12.31 (br s, 1H); 8.40 (d, 1H); 8.34 (d, 1H); 6.00 (s, 2H); 4.00 (s, 3H) 2-43 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): = 12.45 (br s, 1H); 8.65 (d, 1H); 8.58 (d, 1H); 6.10 (s, 2H); 4.02 (s, 3H) 2-50 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): = 10.71 (br s, 1H); 7.43 (d, 1H); 6.94 (d, 1H); 5.95 (s, 2H); 3.91 (s, 3H); 2.27 (s, 3H) 2-53 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): = 11.20 (br s, 1H); 7.62 (d, 1H); 7.42 (d, 1H); 6.04 (s, 2H); 3.94 (s, 3H) 2-54 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): = 11.08 (br s, 1H); 7.56 (d, 1H); 7.26 (d, 1H); 7.11 (t, 1H); 5.99 (s, 2H); 3.94 (s, 3H) 2-55 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): = 11.25 (br s, 1H); 7.64 (d, 1H); 7.35 (d, 1H); 6.01 (s, 2H); 3.95 (s, 3H) 2-58 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): = 11.23 (br s, 1H); 7.64 (d, 1H); 7.53 (d, 1H); 5.98 (s, 2H); 3.94 (s, 3H); 3.27 (s, 3H) 2-65 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): = 11.07 (br s, 1H); 8.01 (d, 1H); 7.25 (d, 1H); 5.79 (d, 1H); 5.29 (d, 1H); 3.96 (s, 3H); 2.68 (s, 3H) 2-68 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): = 11.58 (br s, 1H); 8.26 (d, 1H); 7.78 (d, 1H); 5.91 (d, 1H); 5.39 (d, 1H); 3.99 (s, 3H) 2-69 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): = 11.44 (br s, 1H); 8.20 (d, 1H); 7.58 (d, 1H); 7.46 (t, 1H); 5.86 (d, 1H); 5.33 (d, 1H); 3.98 (s, 3H) 2-70 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): = 11.62 (br s, 1H); 8.29 (d, 1H); 7.73 (d, 1H); 5.91 (d, 1H); 5.38 (d, 1H); 3.99 (s, 3H) 2-73 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): = 11.60 (br s, 1H); 8.29 (d, 1H); 7.86 (d, 1H); 5.85 (d, 1H); 5.38 (d, 1H); 3.99 (s, 3H); 3.39 (s, 3H) 2-80 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): = 11.19 (br s, 1H); 8.01 (d, 1H); 7.26 (d, 1H); 5.47 (s, 2H); 3.94 (s, 3H); 2.58 (s, 3H) 2-83 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): = 11.60 (br s, 1H); 8.29 (d, 1H); 7.85 (d, 1H); 5.63 (s, 2H); 3.98 (s, 3H) 2-84 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): = 11.50 (br s, 1H); 8.22 (d, 1H); 7.64 (d, 1H); 7.37 (t, 1H); 5.56 (s, 2H); 3.97 (s, 3H) 2-85 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): = 11.63 (br s, 1H); 8.31 (d, 1H); 7.79 (d, 1H); 5.63 (s, 2H); 3.98 (s, 3H) 2-88 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): = 11.62 (br s, 1H); 8.32 (d, 1H); 7.86 (d, 1H); 5.60 (s, 2H); 3.97 (s, 3H); 3.42 (s, 3H) 2-94 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): = 11.16 (br s, 1H); 7.63 (d, 1H); 7.41 (d, 1H); 6.57 (q, 1H); 3.95 (s, 3H); 1.80 (d, 3H) 2-106 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): = 8.24 (br d, 1H); 7.69 (d, 1H); 5.62 (br s, 1H); 3.81 (br s, 3H); 1.65 (br s, 3H) 2-112 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): = 11.42 (br s, 1H); 7.72 (d, 1H); 7.55 (d, 1H); 7.53 (s, 1H); 3.97 (s, 3H); 3.41 (s, 3H) 2-130 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): = 11.40 (br.s, 1H); 7.71 (d, 1H); 7.54 (d, 1H); 7.54 (s, 1H); 3.97 (s, 3H); 3.80 (m, 1H); 3.59 (m, 1H); 1.17 (t, 3H) 2-202 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): = 11.86 (br s, 1H); 8.04 (d, 1H); 7.94 (d, 1H); 4.00 (s, 3H) 2-238 .sup.1H-NMR(400.0 MHz, CDCl.sub.3): = 8.21 (dd, 1H); 7.65 (d, 1H); 5.23 (br s, 1H); 5.11 (br s, 1H); 3.97 (s, 3H) 2-253 .sup.1H-NMR(400.0 MHz, CDCl.sub.3): = 11.02 (br.s, 1H); 7.88 (d, 1H); 7.05 (d, 1H); 4.47 (s, 2H); 4.07 (s, 3H); 2.60 (s, 3H) 2-254 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): = 11.92 (br s, 1H); 7.96 (d, 1H); 7.92 (d, 1H); 4.62 (d, 1H); 4.48 (d, 1H); 3.97 (s, 3H) 2-255 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): = 12.09 (br s, 1H); 8.48 (d, 1H); 7.99 (d, 1H); 4.72 (d, 1H); 4.44 (d, 1H); 3.98 (s, 3H) 2-256 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): = 8.46 (d, 1H); 7.80 (d, 1H); 4.68 (s, 2H); 3.76 (s, 3H) 2-257 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): = 11.97 (br s, 1H); 8.08 (d, 1H); 7.83 (d, 1H); 7.05 (s, 1H); 3.97 (s, 3H); 3.15 (s, 3H) 3-7 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): = 11.55 (br s, 1H); 7.72 (m, 2H); 7.41 (t, 1H); 4.32 (q, 2H); 1.46 (t, 3H) 3-20 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): = 11.78 (br s, 1H); 7.90 (d, 1H); 7.66 (d, 1H); 4.69 (s, 2H); 4.28 (q, 2H); 1.44 (t, 3H) 3-52 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): = 11.12 (br s, 1H); 7.61 (d, 1H); 7.42 (d, 1H); 6.03 (s, 2H); 4.30 (q, 2H); 1.44 (t, 3H) 3-53 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): = 11.00 (br s, 1H); 7.56 (d, 1H); 7.26 (d, 1H); 7.11 (t, 1H); 5.98 (s, 2H); 4.29 (q, 2H); 1.44 (t, 3H) 3-67 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): = 11.50 (br s, 1H); 8.28 (d, 1H); 7.79 (d, 1H); 5.93 (d, 1H); 5.41 (d, 1H); 4.36 (q, 2H); 1.48 (t, 3H) 3-82 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): = 11.50 (br s, 1H); 8.29 (d, 1H); 7.85 (d, 1H); 5.63 (s, 2H); 4.34 (q, 2H); 1.45 (t, 3H) 4-16 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): = 11.77 (br s, 1H); 7.88 (d, 1H); 7.65 (d, 1H); 4.70 (s, 2H); 4.24 (t, 2H); 2.86 (tq, 2H); 0.86 (t, 3H) 5-64 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): = 7.67 (d, 1H); 7.45 (d, 1H); 5.96 (d, 1H); 3.84 (s, 3H), 3.24 (s, 3H) 6-1 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): = 13.37 (br s, 1H); 7.63 (d, 1H); 7.31 (d, 1H); 5.99 (s, 2H) 6-2 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): = 13.18 (br s, 1H); 7.58 (d, 1H); 7.16 (d, 1H); 7.06 (t, 1H); 5.93 (s, 2H) 6-3 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): = 13.43 (br s, 1H); 7.65 (d, 1H); 7.23 (d, 1H); 5.96 (s, 2H) 6-4 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): = 13.78 (br s, 1H); 8.28 (d, 1H); 7.68 (d, 1H); 5.87 (d, 1H); 5.36 (d, 1H) 6-5 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): = 13.56 (br s, 1H); 8.23 (d, 1H); 7.50 (d, 1H); 7.43 (t, 1H); 5.84 (d, 1H); 5.30 (d, 1H) 6-7 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): = 13.92 (br s, 1H); 8.30 (d, 1H); 7.74 (d, 1H); 5.63 (s, 2H) 6-8 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): = 8.23 (d, 1H); 7.54 (d, 1H); 7.33 (t, 1H); 5.55 (s, 2H) 6-10 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): = 13.31 (br s, 1H); 7.63(d, 1H); 7.30 (d, 1H); 6.53 (q, 1H); 1.75 (d, 3H) 6-64 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): = 7.65 (d, 1H); 7.43 (d, 1H); 5.94 (d, 1H); 3.23 (s, 3H)

B. Formulation Examples

1. Dusting Products

[0328] A dusting product is obtained by mixing 10 parts by weight of a compound of the formula (I) and 90% parts by weight of talc as an inert substance and comminuting the mixture in a hammer mill.

2. Dispersible Powder

[0329] A readily water-dispersible wettable powder is obtained by mixing 25 parts by weight of a compound of the formula (I), 64 parts by weight of kaolin-containing quartz as an inert substance, 10 parts by weight of potassium lignosulfonate and 1 part by weight of sodium oleoylmethyltaurate as a wetting agent and dispersant, and grinding the mixture in a pinned-disk mill.

3. Dispersion Concentrate

[0330] A readily water-dispersible dispersion concentrate is obtained by mixing 20 parts by weight of a compound of the formula (I), 6 parts by weight of alkylphenol polyglycol ether (@Triton X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling range for example about 255 to more than 277 C.) and grinding the mixture in a friction ball mill to a fineness of below 5 microns.

4. Emulsifiable Concentrate

[0331] An emulsifiable concentrate is obtained from 15 parts by weight of a compound of the formula (I), 75 parts by weight of cyclohexanone as a solvent and 10 parts by weight of ethoxylated nonylphenol as an emulsifier.

5. Water-Dispersible Granules

[0332] Water-dispersible granules are obtained by mixing

75 parts by weight of a compound of the formula (I),
10 of calcium lignosulfonate,
5 of sodium laurylsulfate,
3 of polyvinyl alcohol and
7 of kaolin,
grinding the mixture in a pinned-disk mill, and granulating the powder in a fluidized bed by spray application of water as a granulating liquid.

[0333] Water-dispersible granules are also obtained by homogenizing and precomminuting, in a colloid mill,

25 parts by weight of a compound of the formula (I),
5 of sodium 2,2-dinaphthylmethane-6,6-disulfonate,
2 of sodium oleoylmethyltaurinate,
1 of polyvinyl alcohol,
17 of calcium carbonate and
50 of water,
then grinding the mixture in a bead mill and atomizing and drying the suspension thus obtained in a spray tower by means of a one-phase nozzle.

C. Biological Examples

Test Description

[0334] In the tables below, the following abbreviations are used:

Undesired Plants/Weeds:

[0335]

TABLE-US-00009 ABUTH: Abutilon theophrasti ALOMY Alopecurus myosuroides AMARE: Amaranthus retroflexus AVEFA: Avena fatua CYPES: Cyperus esculentus ECHCG: Echinochloa crus-galli LOLMU: Lolium multiflorum MATIN: Matricaria inodora PHBPU: Ipomoea purpurea POLCO: Polygonum convolvulus SETVI: Setaria viridis STEME: Stellaria media VERPE: Veronica persica VIOTR: Viola tricolor

1. Pre-Emergence Herbicidal Action and Crop Plant Compatibility

[0336] Seeds of monocotyledonous and dicotyledonous weed plants and crop plants are 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), are then applied onto the surface of the covering soil as aqueous suspension or emulsion with addition of 0.5% additive at a water application rate of 600 l/ha (converted). After the treatment, the pots are placed in a greenhouse and kept under good growth conditions for the trial plants. After about 3 weeks, the effect of the preparations is scored visually in comparison with untreated controls as percentages. The tables below show the herbicidal activity of numerous compounds according to the invention against important harmful plants. For example, 100% activity=the plants have died, 0% activity=like control plants.

TABLE-US-00010 Example Dosage number [g/ha] CYPES 2-65 320 90% 2-68 320 90% 2-83 320 100% 2-106 320 90% 3-67 320 80% 3-82 320 90%

TABLE-US-00011 Example Dosage number [g/ha] ECHCG 2-68 320 90% 2-69 320 90% 2-83 320 100% 2-106 320 90% 3-52 320 90% 3-67 320 100% 3-82 320 100%

TABLE-US-00012 Example Dosage number [g/ha] SETVI 2-68 320 100% 2-69 320 90% 2-83 320 100% 2-84 320 90% 2-94 320 100% 2-106 320 90% 3-52 320 90% 3-67 320 80%

TABLE-US-00013 Example Dosage number [g/ha] ABUTH 2-68 320 90% 2-69 320 100% 2-83 320 100% 2-84 320 90% 2-94 320 90% 2-106 320 100% 3-52 320 90% 3-67 320 90% 3-82 320 90% 2-43 80 100% 2-112 80 100% 2-130 80 100%

TABLE-US-00014 Example Dosage number [g/ha] AMARE 2-54 320 80% 2-65 320 90% 2-68 320 100% 2-69 320 100% 2-80 320 90% 2-83 320 100% 2-84 320 100% 2-94 320 100% 2-106 320 100% 3-52 320 100% 3-53 320 90% 3-67 320 100% 3-82 320 100% 2-43 80 100% 2-112 80 90% 2-254 80 80%

TABLE-US-00015 Example Dosage number [g/ha] MATIN 2-68 320 90% 2-69 320 90% 2-80 320 80% 2-83 320 90% 2-84 320 100% 2-106 320 100% 3-52 320 90% 3-67 320 90% 3-82 320 100% 1-50 80 90% 2-43 80 80%

TABLE-US-00016 Example Dosage number [g/ha] STEME 2-68 320 90% 2-69 320 90% 2-83 320 100% 2-84 320 90% 2-94 320 100% 2-106 320 90% 3-52 320 100% 3-67 320 100% 3-82 320 100% 2-21 80 90% 2-43 80 90% 2-130 80 100%

TABLE-US-00017 Example Dosage number [g/ha] VIOTR 2-68 320 100% 2-69 320 100% 2-83 320 100% 2-84 320 100% 2-94 320 100% 2-106 320 100% 3-52 320 90% 3-53 320 100% 3-67 320 100% 3-82 320 100% 2-43 80 100% 2-112 80 100% 2-130 80 100%

TABLE-US-00018 Example Dosage number [g/ha] VERPE 2-13 320 90% 2-15 320 90% 2-65 320 80% 2-68 320 100% 2-69 320 90% 2-83 320 100% 2-84 320 100% 3-52 320 80% 3-67 320 100% 3-82 320 100% 2-112 80 80%

[0337] In a comparative experiment, by way of example, the herbicidal activity of compound No. 2-53 according to the invention was compared to that of compound No. A-117 known from WO 2013/076315 A2. Here, the superiority of the compound according to the invention was demonstrated clearly on the basis of numerous harmful plants:

TABLE-US-00019 Dosage Herbicidal action against Example No. [g/ha] SETVI ALOMY AVEFA ABUTH MATIN 2-53, according to the invention 320 80% 30% 60% 90% 90% A-117, known from WO 2013/076315 320 0% 0% 0% 0% 30%

2. Post-Emergence Herbicidal Action and Crop Plant Compatibility

[0338] Seeds of monocotyledonous and dicotyledonous weeds and crop plants are 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 are treated at the one-leaf stage. The compounds of the invention, formulated in the form of wettable powders (WP) or as emulsion concentrates (EC), are then sprayed onto the green parts of the plants as aqueous suspension or emulsion with addition of 0.5% additive at a water application rate of 6001/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 is rated visually in comparison to untreated controls. The tables below show the herbicidal activity of numerous compounds according to the invention against important harmful plants. For example, 100% activity=the plants have died, 0% activity=like control plants.

TABLE-US-00020 Example Dosage number [g/ha] ECHCG 2-54 80 100% 2-68 80 100% 2-69 80 100% 2-83 80 90% 2-84 80 90% 2-94 80 80% 2-106 80 100% 3-52 80 100% 3-53 80 80% 3-67 80 100% 3-82 80 80% 2-112 20 80% 2-257 20 100%

TABLE-US-00021 Example Dosage number [g/ha] SETVI 2-54 80 90% 2-83 80 90% 2-68 80 90% 2-69 80 80% 2-84 80 100% 2-94 80 80% 2-106 80 100% 3-52 80 100% 3-53 80 80% 2-112 20 80%

TABLE-US-00022 Example Dosage number [g/ha] ABUTH 2-13 80 80% 2-54 80 80% 2-69 80 90% 2-83 80 90% 2-84 80 90% 2-94 80 90% 2-106 80 90% 3-52 80 80% 3-53 80 90% 3-67 80 80% 1-35 20 80% 1-50 20 80% 2-58 20 80% 2-112 20 90% 2-130 20 90% 2-253 20 90% 2-257 20 90%

TABLE-US-00023 Example Dosage number [g/ha] AMARE 2-13 80 80% 2-15 80 80% 2-54 80 90% 2-68 80 100% 2-69 80 90% 2-80 80 90% 2-83 80 100% 2-84 80 100% 2-94 80 90% 2-106 80 100% 3-52 80 100% 3-53 80 100% 3-67 80 100% 3-82 80 100% 1-50 20 80% 1-65 20 80% 2-43 20 80% 2-58 20 80% 2-112 20 80%

TABLE-US-00024 Example Dosage number [g/ha] MATIN 2-68 80 90% 2-69 80 90% 2-80 80 80% 2-83 80 100% 2-84 80 100% 2-106 80 90% 3-52 80 90% 3-53 80 80% 3-67 80 90% 3-82 80 100%

TABLE-US-00025 Example Dosage number [g/ha] PHBPU 2-50 80 80% 2-54 80 80% 2-68 80 90% 2-69 80 80% 2-83 80 90% 2-84 80 90% 2-106 80 80% 3-52 80 100% 3-67 80 100% 3-82 80 90% 1-65 20 80% 2-22 20 80%

TABLE-US-00026 Example Dosage number [g/ha] STEME 2-21 20 80% 2-255 20 80% 2-13 80 80% 2-68 80 100% 2-69 80 100% 2-80 80 90% 2-83 80 100% 2-84 80 100% 2-94 80 100% 2-106 80 100% 3-52 80 100% 3-53 80 90% 3-67 80 100% 3-82 80 100%

TABLE-US-00027 Example Dosage number [g/ha] VIOTR 2-54 80 100% 2-68 80 100% 2-69 80 100% 2-80 80 90% 2-83 80 100% 2-84 80 100% 2-94 80 80% 2-106 80 100% 3-52 80 100% 3-53 80 90% 3-67 80 100% 3-82 80 100% 1-35 20 80% 1-50 20 80% 2-21 20 80% 2-22 20 100% 2-43 20 90% 2-130 20 90% 2-255 20 80 2-257 20 80%

TABLE-US-00028 Example Dosage number [g/ha] VERPE 2-13 80 90% 2-54 80 90% 2-68 80 100% 2-69 80 90% 2-83 80 90% 2-84 80 100% 3-52 80 100% 3-53 80 80% 3-67 80 100% 3-82 80 100% 2-112 20 80%

[0339] In a comparative experiment, by way of example, the herbicidal activity of compound No. 2-53 according to the invention was compared to that of compound No. A-117 known from WO 2013/076315 A2. Here, the superiority of the compound according to the invention was demonstrated clearly on the basis of numerous harmful plants.

TABLE-US-00029 Dosage Herbicidal action against Example No. [g/ha] LOLMU ALOMY AVEFA ABUTH POLCO 2-53, according to the invention 80 70% 80% 100% 80% 80% A-117, WO 2013/076315 A2 known 80 0% 20% 0% 50% 10%