N-(1,3,4-OXADIAZOL-2-YL)PHENYLCARBOXAMIDES AS HERBICIDES

Abstract

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

##STR00001##

In this formula (I), X, R and Z are radicals such as alkyl and halogen.

Claims

1. A benzamide of the formula (I) or salt thereof ##STR00021## in which the symbols and indices are defined as follows: X is halogen, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.1-C.sub.6)-alkoxy, halo-(C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.4)-alkoxy-(C.sub.1-C.sub.4)-alkyl or (C.sub.1-C.sub.6)-alkyl-(O).sub.nS, Z is halo-(C.sub.1-C.sub.6)-alkoxy, R is (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl or (C.sub.3-C.sub.6)-cycloalkyl, n is 0, 1 or 2.

2. A benzamide as claimed in claim 1, in which X is halogen, (C.sub.1-C.sub.6)-alkyl, CF.sub.3, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.4)-alkoxy-(C.sub.1-C.sub.4)-alkyl or (C.sub.1-C.sub.6)-alkylthio, Z is halo-(C.sub.1-C.sub.6)-alkoxy, R is (C.sub.1-C.sub.6)-alkyl or cyclopropyl, n is 0, 1 or 2.

3. A benzamide as claimed in claim 1, in which X is halogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.4)-alkoxy-(C.sub.1-C.sub.4)-alkyl or (C.sub.1-C.sub.6)-alkylthio, Z is halo-(C.sub.1-C.sub.2)-alkoxy, R is (C.sub.1-C.sub.6)-alkyl, n is 0, 1 or 2.

4. A benzamide as claimed in claim 1, in which X is F, Cl, Br, Me, Et, MeO, EtO, MeOCH.sub.2 or MeS, Z is HF.sub.2CO or F.sub.3CO, R is Me or Et, n is 0, 1 or 2.

5. A herbicidal composition or plant growth-regulating composition, characterized in that it comprises one or more benzamides of the general formula (I) or salts thereof as claimed in claim 1.

6. The herbicidal composition as claimed in claim 5, further comprising a formulation auxiliary.

7. The herbicidal composition as claimed in claim 5, comprising at least one further active ingredient from the group of insecticides, acaricides, herbicides, fungicides, safeners and/or growth regulators.

8. The herbicidal composition as claimed in claim 56, comprising a safener.

9. The herbicidal composition as claimed in claim 8, in which the safener is selected from the group consisting of mefenpyr-diethyl, cyprosulfamide, isoxadifen-ethyl, cloquintocet-mexyl, benoxacor and dichlormid.

10. A method of controlling unwanted plants, characterized in that an effective amount of at least one benzamide of the formula (I) as claimed in claim 1 is applied to the plants or to the site of the unwanted vegetation.

11. The use of benzamides of the formula (I) as claimed in claim 1 for controlling unwanted plants.

12. The use as claimed in claim 11, characterized in that the benzamides of the formula (I) are used for controlling unwanted plants in crops of useful plants.

13. The use as claimed in claim 12, characterized in that the useful plants are transgenic useful plants.

14. A method of controlling unwanted plants, characterized in that an effective amount of an herbicidal composition as claimed in claim 5 is applied to the plants or to the site of the unwanted vegetation.

15. The use of herbicidal compositions as claimed in claim 5 for controlling unwanted plants.

Description

A. CHEMICAL EXAMPLES

[0335] The examples which follow illustrate the present invention.

Synthesis of 2-chloro-3-(methylsulfanyl)-N-(1,3,4-oxadiazol-2-yl)-4-(trifluoromethoxy)benzamide (Example no. 1-31)

[0336] ##STR00016##

[0337] To 653 mg (7.68 mmol) of 1,3,4-oxadiazole-2-amine and 2.00 g (6.98 mmol) of 2-chloro-3-(methylsulfanyl)-4-(trifluoromethoxy)benzoic acid in 50 ml of acetonitrile was added 2.67 ml (33.49 mmol) of 1-methyl-1H-imidazole. The mixture was cooled down to a temperature of 0? C.-5? C. 0.91 ml (10.47 mmol) of oxalyl chloride was added in portions. Then the reaction mixture was warmed to room temperature and stirred at that temperature for 3.5 h. For workup, the reaction mixture was freed of the solvent on a rotary evaporator, and the residue was taken up in dichloromethane and water. After phase separation, the organic phase was concentrated, and the residue was taken up in water. 6 M sodium hydroxide solution was added, then the mixture was washed repeatedly with dichloromethane. Thereafter, the aqueous phase was acidified with 6 M hydrochloric acid. The resultant solids were filtered off and dried. Thereafter, the solids were taken up once again in dichloromethane and an aqueous solution of sodium hydrogencarbonate. After phase separation, the organic phase was freed of the solvent on a rotary evaporator. 910 mg of the desired product was isolated with a purity of 85% by weight.

Synthesis of 2-chloro-3-(methylsulfinyl)-N-(1,3,4-oxadiazol-2-yl)-4-(trifluoromethoxy)benzamide (Example no. 1-32) and 2-chloro-3-(methylsulfonyl)-N-(1,3,4-oxadiazol-2-yl)-4-(trifluoromethoxy)benzamide (Example no. 1-35)

[0338] ##STR00017##

[0339] To 750 mg (85% by weight; 1.80 mmol) of 2-chloro-3-(methylsulfanyl)-N-(1,3,4-oxadiazol-2-yl)-4-(trifluoromethoxy)benzamide in 25 ml of dichloromethane at room temperature was added 713 mg (77% by weight; 3.18 mmol) of 3-chloroperoxybenzoic acid. The mixture was stirred at room temperature for 6 d. Subsequently, a further 119 mg (77% by weight; 0.53 mmol) of 3-chloroperoxybenzoic acid was added, and the mixture was stirred at room temperature until the monitoring of the reaction indicated a significant amount of sulfone as well as the sulfoxide. For workup, an aqueous solution of sodium metabisulfite was added. The mixture was stirred for a few minutes and, after phase separation, the organic phase was freed of the solvent on a rotary evaporator. The residue was purified by chromatography, giving 112 mg of 2-chloro-3-(methylsulfinyl)-N-(1,3,4-oxadiazol-2-yl)-4-(trifluoromethoxy)benzamide with a purity of 90% by weight and 68 mg of 2-chloro-3-(methylsulfonyl)-N-(1,3,4-oxadiazol-2-yl)-4-(trifluoromethoxy)benzamide with a purity of 90% by weight.

Synthesis of 2-chloro-4-(difluoromethoxy)-3-(methylsulfanyl)-N-(1,3,4-oxadiazol-2-yl)benzamide (Example no. 1-21)

[0340] ##STR00018##

[0341] To 697 mg (8.19 mmol) of 1,3,4-oxadiazole-2-amine and 2.00 g (7.44 mmol) of 2-chloro-4-(difluoromethoxy)-3-(methylsulfanyl)benzoic acid in 50 ml of acetonitrile was added 2.85 ml (35.73 mmol) of 1-methyl-1H-imidazole. The mixture was cooled down to a temperature of 0? C.-5? C. 0.97 ml (11.17 mmol) of oxalyl chloride was added in portions. Then the reaction mixture was warmed to room temperature and stirred at that temperature for 16 h. For workup, the reaction mixture was freed of the solvent on a rotary evaporator, and the residue was taken up in dichloromethane and water. After phase separation, the organic phase was concentrated, and the residue was taken up in water. 6 M sodium hydroxide solution was added, then the mixture was washed repeatedly with dichloromethane. Thereafter, the aqueous phase was acidified with 6 M hydrochloric acid. The mixture was filtered, and the resultant solids were dried. Thereafter, the solids were taken up once again in dichloromethane and an aqueous solution of sodium hydrogencarbonate. After phase separation, the organic phase was freed of the solvent on a rotary evaporator. The residue was stirred with a little dichloromethane, then the mixture was filtered. The solids were dried, and 605 mg of the desired product with a purity of 80% by weight was isolated.

Synthesis of 2-chloro-4-(difluoromethoxy)-3-(methylsulfonyl)-N-(1,3,4-oxadiazol-2-yl)benzamide (Example no. 1-25)

[0342] ##STR00019##

[0343] To 600 mg (80% by weight; 1.43 mmol) of 2-chloro-4-(difluoromethoxy)-3-(methylsulfanyl)-N-(1,3,4-oxadiazol-2-yl)benzamide in 36 ml of dichloromethane at room temperature was added 1001 mg (77% by weight; 4.47 mmol) of 3-chloroperoxybenzoic acid. The mixture was stirred at room temperature for 7 d. Subsequently, to complete the reaction, there were two additions each of 123 mg (77% by weight; 0.55 mmol) of 3-chloroperoxybenzoic acid and 5 ml of acetonitrile. The mixture was stirred at room temperature until the monitoring of the reaction indicated complete conversion to the sulfone. For workup, an aqueous solution of sodium metabisulfite was added. The mixture was stirred for a few minutes and, after phase separation, the organic phase was freed of the solvent on a rotary evaporator. The residue was taken up in tert-butyl methyl ether, then the mixture was filtered, and the isolated solids were dried. The solids isolated were 427 mg of the desired product with a purity of 90% by weight.

[0344] The examples listed in the tables below were prepared analogously to the methods mentioned above or can be obtained analogously to the methods mentioned above. These compounds are very particularly preferred.

[0345] The abbreviations used here mean:

TABLE-US-00001 Me = methyl Et = ethyl MeO = methoxy EtO = ethoxy MeOCH.sub.2 = methoxymethyl MeS = methylthio HF.sub.2CO = F.sub.3CO = trifluoromethoxy difluoromethoxy

TABLE-US-00002 TABLE 1 Inventive compounds of the general formula (I) in which the substituents have the definitions given below. In the case that n = 1, the compounds are chiral sulfoxides. In this case, the Sulfoxide configuration column states whether the sulfoxide is in the (R) configuration, in the (S) configuration, or in racemic form in both configurations. [00020] No. X Z n Sulfoxide configuration R 1-1 F HF.sub.2CO 0 Me 1-2 F HF.sub.2CO 1 racemic Me 1-3 F HF.sub.2CO 1 (R) Me 1-4 F HF.sub.2CO 1 (S) Me 1-5 F HF.sub.2CO 2 Me 1-6 F HF.sub.2CO 0 Et 1-7 F HF.sub.2CO 1 racemic Et 1-8 F HF.sub.2CO 1 (R) Et 1-9 F HF.sub.2CO 1 (S) Et 1-10 F HF.sub.2CO 2 Et 1-11 F F.sub.3CO 0 Me 1-12 F F.sub.3CO 1 racemic Me 1-13 F F.sub.3CO 1 (R) Me 1-14 F F.sub.3CO 1 (S) Me 1-15 F F.sub.3CO 2 Me 1-16 F F.sub.3CO 0 Et 1-17 F F.sub.3CO 1 racemic Et 1-18 F F.sub.3CO 1 (R) Et 1-19 F F.sub.3CO 1 (S) Et 1-20 F F.sub.3CO 2 Et 1-21 Cl HF.sub.2CO 0 Me 1-22 Cl HF.sub.2CO 1 racemic Me 1-23 Cl HF.sub.2CO 1 (R) Me 1-24 Cl HF.sub.2CO 1 (S) Me 1-25 Cl HF.sub.2CO 2 Me 1-26 Cl HF.sub.2CO 0 Et 1-27 Cl HF.sub.2CO 1 racemic Et 1-28 Cl HF.sub.2CO 1 (R) Et 1-29 Cl HF.sub.2CO 1 (S) Et 1-30 Cl HF.sub.2CO 2 Et 1-31 Cl F.sub.3CO 0 Me 1-32 Cl F.sub.3CO 1 racemic Me 1-33 Cl F.sub.3CO 1 (R) Me 1-34 Cl F.sub.3CO 1 (S) Me 1-35 Cl F.sub.3CO 2 Me 1-36 Cl F.sub.3CO 0 Et 1-37 Cl F.sub.3CO 1 racemic Et 1-38 Cl F.sub.3CO 1 (R) Et 1-39 Cl F.sub.3CO 1 (S) Et 1-40 Cl F.sub.3CO 2 Et 1-41 Br HF.sub.2CO 0 Me 1-42 Br HF.sub.2CO 1 racemic Me 1-43 Br HF.sub.2CO 1 (R) Me 1-44 Br HF.sub.2CO 1 (S) Me 1-45 Br HF.sub.2CO 2 Me 1-46 Br HF.sub.2CO 0 Et 1-47 Br HF.sub.2CO 1 racemic Et 1-48 Br HF.sub.2CO 1 (R) Et 1-49 Br HF.sub.2CO 1 (S) Et 1-50 Br HF.sub.2CO 2 Et 1-51 Br F.sub.3CO 0 Me 1-52 Br F.sub.3CO 1 racemic Me 1-53 Br F.sub.3CO 1 (R) Me 1-54 Br F.sub.3CO 1 (S) Me 1-55 Br F.sub.3CO 2 Me 1-56 Br F.sub.3CO 0 Et 1-57 Br F.sub.3CO 1 racemic Et 1-58 Br F.sub.3CO 1 (R) Et 1-59 Br F.sub.3CO 1 (S) Et 1-60 Br F.sub.3CO 2 Et 1-61 Me HF.sub.2CO 0 Me 1-62 Me HF.sub.2CO 1 racemic Me 1-63 Me HF.sub.2CO 1 (R) Me 1-64 Me HF.sub.2CO 1 (S) Me 1-65 Me HF.sub.2CO 2 Me 1-66 Me HF.sub.2CO 0 Et 1-67 Me HF.sub.2CO 1 racemic Et 1-68 Me HF.sub.2CO 1 (R) Et 1-69 Me HF.sub.2CO 1 (S) Et 1-70 Me HF.sub.2CO 2 Et 1-71 Me F.sub.3CO 0 Me 1-72 Me F.sub.3CO 1 racemic Me 1-73 Me F.sub.3CO 1 (R) Me 1-74 Me F.sub.3CO 1 (S) Me 1-75 Me F.sub.3CO 2 Me 1-76 Me F.sub.3CO 0 Et 1-77 Me F.sub.3CO 1 racemic Et 1-78 Me F.sub.3CO 1 (R) Et 1-79 Me F.sub.3CO 1 (S) Et 1-80 Me F.sub.3CO 2 Et 1-81 Et HF.sub.2CO 0 Me 1-82 Et HF.sub.2CO 1 racemic Me 1-83 Et HF.sub.2CO 1 (R) Me 1-84 Et HF.sub.2CO 1 (S) Me 1-85 Et HF.sub.2CO 2 Me 1-86 Et HF.sub.2CO 0 Et 1-87 Et HF.sub.2CO 1 racemic Et 1-88 Et HF.sub.2CO 1 (R) Et 1-89 Et HF.sub.2CO 1 (S) Et 1-90 Et HF.sub.2CO 2 Et 1-91 Et F.sub.3CO 0 Me 1-92 Et F.sub.3CO 1 racemic Me 1-93 Et F.sub.3CO 1 (R) Me 1-94 Et F.sub.3CO 1 (S) Me 1-95 Et F.sub.3CO 2 Me 1-96 Et F.sub.3CO 0 Et 1-97 Et F.sub.3CO 1 racemic Et 1-98 Et F.sub.3CO 1 (R) Et 1-99 Et F.sub.3CO 1 (S) Et 1-100 Et F.sub.3CO 2 Et 1-101 MeO HF.sub.2CO 0 Me 1-102 MeO HF.sub.2CO 1 racemic Me 1-103 MeO HF.sub.2CO 1 (R) Me 1-104 MeO HF.sub.2CO 1 (S) Me 1-105 MeO HF.sub.2CO 2 Me 1-106 MeO HF.sub.2CO 0 Et 1-107 MeO HF.sub.2CO 1 racemic Et 1-108 MeO HF.sub.2CO 1 (R) Et 1-109 MeO HF.sub.2CO 1 (S) Et 1-110 MeO HF.sub.2CO 2 Et 1-111 MeO F.sub.3CO 0 Me 1-112 MeO F.sub.3CO 1 racemic Me 1-113 MeO F.sub.3CO 1 (R) Me 1-114 MeO F.sub.3CO 1 (S) Me 1-115 MeO F.sub.3CO 2 Me 1-116 MeO F.sub.3CO 0 Et 1-117 MeO F.sub.3CO 1 racemic Et 1-118 MeO F.sub.3CO 1 (R) Et 1-119 MeO F.sub.3CO 1 (S) Et 1-120 MeO F.sub.3CO 2 Et 1-121 EtO HF.sub.2CO 0 Me 1-122 EtO HF.sub.2CO 1 racemic Me 1-123 EtO HF.sub.2CO 1 (R) Me 1-124 EtO HF.sub.2CO 1 (S) Me 1-125 EtO HF.sub.2CO 2 Me 1-126 EtO HF.sub.2CO 0 Et 1-127 EtO HF.sub.2CO 1 racemic Et 1-128 EtO HF.sub.2CO 1 (R) Et 1-129 EtO HF.sub.2CO 1 (S) Et 1-130 EtO HF.sub.2CO 2 Et 1-131 EtO F.sub.3CO 0 Me 1-132 EtO F.sub.3CO 1 racemic Me 1-133 EtO F.sub.3CO 1 (R) Me 1-134 EtO F.sub.3CO 1 (S) Me 1-135 EtO F.sub.3CO 2 Me 1-136 EtO F.sub.3CO 0 Et 1-137 EtO F.sub.3CO 1 racemic Et 1-138 EtO F.sub.3CO 1 (R) Et 1-139 EtO F.sub.3CO 1 (S) Et 1-140 EtC F.sub.3CO 2 Et 1-141 MeOCH.sub.2 HF.sub.2CO 0 Me 1-142 MeOCH.sub.2 HF.sub.2CO 1 racemic Me 1-143 MeOCH.sub.2 HF.sub.2CO 1 (R) Me 1-144 MeOCH.sub.2 HF.sub.2CO 1 (S) Me 1-145 MeOCH.sub.2 HF.sub.2CO 2 Me 1-146 MeOCH.sub.2 HF.sub.2CO 0 Et 1-147 MeOCH.sub.2 HF.sub.2CO 1 racemic Et 1-148 MeOCH.sub.2 HF.sub.2CO 1 (R) Et 1-149 MeOCH.sub.2 HF.sub.2CO 1 (S) Et 1-150 MeOCH.sub.2 HF.sub.2CO 2 Et 1-151 MeOCH.sub.2 F.sub.3CO 0 Me 1-152 MeOCH.sub.2 F.sub.3CO 1 racemic Me 1-153 MeOCH.sub.2 F.sub.3CO 1 (R) Me 1-154 MeOCH.sub.2 F.sub.3CO 1 (S) Me 1-155 MeOCH.sub.2 F.sub.3CO 2 Me 1-156 MeOCH.sub.2 F.sub.3CO 0 Et 1-157 MeOCH.sub.2 F.sub.3CO 1 racemic Et 1-158 MeOCH.sub.2 F.sub.3CO 1 (R) Et 1-159 MeOCH.sub.2 F.sub.3CO 1 (S) Et 1-160 MeOCH.sub.2 F.sub.3CO 2 Et 1-161 MeS HF.sub.2CO 0 Me 1-162 MeS HF.sub.2CO 1 racemic Me 1-163 MeS HF.sub.2CO 1 (R) Me 1-164 MeS HF.sub.2CO 1 (S) Me 1-165 MeS HF.sub.2CO 2 Me 1-166 MeS HF.sub.2CO 0 Et 1-167 MeS HF.sub.2CO 1 racemic Et 1-168 MeS HF.sub.2CO 1 (R) Et 1-169 MeS HF.sub.2CO 1 (S) Et 1-170 MeS HF.sub.2CO 2 Et 1-171 MeS F.sub.3CO 0 Me 1-172 MeS F.sub.3CO 1 racemic Me 1-173 MeS F.sub.3CO 1 (R) Me 1-174 MeS F.sub.3CO 1 (S) Me 1-175 MeS F.sub.3CO 2 Me 1-176 MeS F.sub.3CO 0 Et 1-177 MeS F.sub.3CO 1 racemic Et 1-178 MeS F.sub.3CO 1 (R) Et 1-179 MeS F.sub.3CO 1 (S) Et 1-180 MeS F.sub.3CO 2 Et

NMR Data of Selected Examples

NMR Peak List Method

[0346] The 1H NMR data of selected examples are noted in the form of 1H NMR peak lists. For each signal peak, first the 6 value in ppm and then the signal intensity in round brackets are listed. The 6 value/signal intensity number pairs for different signal peaks are listed with separation from one another by semicolons.

[0347] 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)

[0348] 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.

[0349] For calibration of the chemical shift of 1H NMR spectra we use tetramethylsilane and/or the chemical shift of the solvent, particularly in the case of spectra measured in DMSO. Therefore, the tetramethylsilane peak may but need not occur in NMR peak lists.

[0350] The lists of the 1H NMR peaks are similar to the conventional 1H NMR printouts and thus usually contain all peaks listed in a conventional NMR interpretation.

[0351] In addition, like conventional 1H NMR printouts, they may show solvent signals, signals of stereoisomers of the target compounds, which likewise form part of the subject matter of the invention, and/or peaks of impurities.

[0352] In the reporting of compound signals in the delta range of solvents and/or water, our lists of 1H NMR peaks show the usual 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.

[0353] The peaks of stereoisomers of the target compounds and/or peaks of impurities usually have a lower intensity on average than the peaks of the target compounds (for example with a purity of >90%).

[0354] Such stereoisomers and/or impurities may be typical of the particular preparation process. Their peaks can thus help in this case to identify reproduction of our preparation process with reference to by product fingerprints.

[0355] 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.

[0356] Further details of 1H NMR peak lists can be found in the Research Disclosure Database Number 564025.

TABLE-US-00003 1-31: .sup.1H-NMR(400.6 MHz, CDCl3): ? = 8.1731 (2.7); 7.6629 (1.7); 7.6414 (2.0); 7.3533 (1.0); 7.3498 (1.1); 7.3319 (0.9); 7.3283 (0.9); 7.2619 (14.1); 2.4906 (0.6); 2.4651 (16.0); 0.0080 (0.6); ?0.0002 (18.8); ?0.0085 (0.5) 1-21: .sup.1H-NMR(400.6 MHz, CDCl3): ? = 8.2180 (0.5); 7.7136 (0.9); 7.6922 (0.9); 7.2606 (42.9); 7.2510 (2.0); 7.2293 (1.2); 6.8380 (1.1); 6.6559 (2.3); 6.4739 (1.2); 2.4937 (1.9); 2.4744 (16.0); 1.5691 (1.0); 0.0079 (1.9); ?0.0002 (60.1); ?0.0085 (3.0); ?0.0284 (0.5); ?0.0410 (0.7) 1-32: .sup.1H-NMR(400.6 MHz, CDCl3): ? = 7.5186 (1.1); 7.4207 (0.7); 7.3963 (0.7); 7.2602 (212.2); 6.9966 (1.1); 3.1170 (1.4); 3.1079 (16.0); 1.5462 (4.8); 1.2551 (1.3); 0.1458 (1.0); 0.0080 (8.1); ?0.0002 (311.2); ?0.0085 (10.1); ?0.1495 (0.9) 1-35: .sup.1H-NMR(400.6 MHz, CDCl3): ? = 7.8896 (0.6); 7.8679 (0.7); 7.5011 (0.5); 7.2605 (40.1); 3.3588 (16.0); 0.0079 (1.5); ?0.0002 (60.1); ?0.0060 (0.6); ?0.0085 (1.8) 1-22: .sup.1H-NMR(400.0 MHz, CD3CN): ? = 8.4638 (2.4); 7.7968 (1.5); 7.7754 (1.7); 7.4144 (1.4); 7.3930 (1.3); 7.0952 (1.3); 6.9171 (1.1); 6.9050 (1.2); 6.7270 (1.3); 3.0905 (16.0); 2.1649 (4.1); 2.1355 (1.1); 2.1292 (0.8); 1.9923 (2.2); 1.9861 (1.6); 1.9804 (20.1); 1.9742 (40.6); 1.9680 (57.6); 1.9619 (41.1); 1.9557 (20.8) 1-25: .sup.1H-NMR(400.0 MHz, CD3CN): ? = 8.4656 (1.7); 7.8657 (1.2); 7.8442 (1.4); 7.4762 (0.7); 7.4738 (1.3); 7.4714 (0.8); 7.4548 (0.7); 7.4524 (1.2); 7.4500 (0.7); 7.0819 (1.3); 6.8997 (2.7); 6.7174 (1.3); 3.3750 (16.0); 3.1600 (0.8); 1.9922 (1.2); 1.9862 (0.7); 1.9803 (10.5); 1.9742 (20.5); 1.9679 (30.1); 1.9618 (20.0); 1.9556 (10.3); 1.1635 (2.4)

B. FORMULATION EXAMPLES

[0357] a) A dusting product is obtained by mixing 10 parts by weight of a compound of the formula (I) and/or salts thereof and 90 parts by weight of talc as an inert substance and comminuting the mixture in a hammer mill. [0358] b) A readily water-dispersible, wettable powder is obtained by mixing 25 parts by weight of a compound of the formula (I) and/or salts thereof, 64 parts by weight of kaolin-containing quartz as inert substance, 10 parts by weight of potassium lignosulfonate and 1 part by weight of sodium oleoylmethyltaurate as wetting agent and dispersant and grinding in a pinned-disk mill. [0359] c) A readily water-dispersible dispersion concentrate is obtained by mixing 20 parts by weight of a compound of the formula (I) and/or salts thereof with 6 parts by weight of alkylphenol polyglycol ether (?Triton X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling range e.g. about 255? C. to more than 277? C.) and grinding to a fineness of below 5 microns in an attrition ball mill. [0360] d) An emulsifiable concentrate is obtained from 15 parts by weight of a compound of the formula (I) and/or salts thereof, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of oxethylated nonylphenol as emulsifier. [0361] e) Water-dispersible granules are obtained by mixing [0362] 75 parts by weight of a compound of the formula (I) and/or salts thereof, [0363] 10 parts by weight of calcium lignosulfonate, [0364] 5 parts by weight of sodium lauryl sulfate, [0365] 3 parts by weight of polyvinyl alcohol and [0366] 7 parts by weight of kaolin, [0367] 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. [0368] f) Water-dispersible granules are also obtained by homogenizing and precomminuting, in a colloid mill, [0369] 25 parts by weight of a compound of the formula (I) and/or salts thereof, [0370] 5 parts by weight of sodium 2,2-dinaphthylmethane-6,6-disulfonate, [0371] 2 parts by weight of sodium oleoylmethyltaurate, [0372] 1 part by weight of polyvinyl alcohol, [0373] 17 parts by weight of calcium carbonate and [0374] 50 parts by weight of water,
then grinding the mixture in a bead mill and atomizing and drying the resulting suspension in a spray tower by means of a one-phase nozzle.

C. BIOLOGICAL DATA

[0375] The abbreviations utilized hereinafter have the following meanings:

Unwanted plants:

TABLE-US-00004 ALOMY: Alopecurus myosuroides SETVI: Setaria viridis AMARE: Amaranthus retroflexus AVEFA: Avena fatua LOLRI: Lolium rigidum ECHCG: Echinochloa crus-galli VERPE: Veronica persica VIOTR: Viola tricolor POLCO: Polygonum convolvulus ABUTH: Abutylon threophrasti PHBPU: Pharbitis purpurea MATIN: Matricaria inodora DIGSA Digitaria sanguinalis KCHSC: Kochia scoparia

1. Post-Emergence Herbicidal Action Against Harmful Plants

[0376] Seeds of monocotyledonous and dicotyledonous weed and crop plants are laid out in sandy loam soil in wood-fiber pots, covered with soil and cultivated in a greenhouse under good growth conditions. 2 to 3 weeks after sowing, the trial 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 at a water application rate equating to 600 to 800 l/ha with addition of 0.2% wetting agent. After the test plants have been left to stand in the greenhouse under optimal growth conditions for about 3 weeks, the action of the preparations is assessed visually in comparison to untreated controls (herbicidal action in percent (%): 100% activity=the plants have died, 0% activity=like control plants).

TABLE-US-00005 TABLE 1a Post-emergence effect at 20 g/ha against ABUTH in % Example number Dosage [g/ha] ABUTH 1-32 20 90 1-35 20 80 1-22 20 100 1-25 20 100

TABLE-US-00006 TABLE 1b Post-emergence effect at 80 g/ha against ABUTH in % Example number Dosage [g/ha] ABUTH 1-31 80 90 1-21 80 80 1-32 80 100 1-35 80 90 1-22 80 100 1-25 80 100

TABLE-US-00007 TABLE 2a Post-emergence effect at 20 g/ha against ALOMY in % Example number Dosage [g/ha] ALOMY 1-32 20 80

TABLE-US-00008 TABLE 2b Post-emergence effect at 80 g/ha against ALOMY in % Example number Dosage [g/ha] ALOMY 1-32 80 90

TABLE-US-00009 TABLE 3a Post-emergence effect at 20 g/ha against AMARE in % Example number Dosage [g/ha] AMARE 1-31 20 100 1-21 20 100 1-32 20 100 1-35 20 90 1-22 20 100 1-25 20 100

TABLE-US-00010 TABLE 3b Post-emergence effect at 80 g/ha against AMARE in % Example number Dosage [g/ha] AMARE 1-31 80 100 1-21 80 100 1-32 80 100 1-35 80 90 1-22 80 100 1-25 80 100

TABLE-US-00011 TABLE 4a Post-emergence effect at 20 g/ha against DIGSA in % Example number Dosage [g/ha] DIGSA 1-31 20 90 1-21 20 90 1-32 20 90 1-35 20 90 1-22 20 100 1-25 20 100

TABLE-US-00012 TABLE 4b Post-emergence effect at 80 g/ha against DIGSA in % Example number Dosage [g/ha] DIGSA 1-31 80 90 1-21 80 90 1-32 80 90 1-35 80 100 1-22 80 100 1-25 80 100

TABLE-US-00013 TABLE 5 Post-emergence effect at 80 g/ha against LOLRI in % Example number Dosage [g/ha] LOLRI 1-32 80 90 1-35 80 80 1-22 80 90

TABLE-US-00014 TABLE 6a Post-emergence effect at 20 g/ha against MATIN in % Example number Dosage [g/ha] MATIN 1-31 20 80 1-32 20 100 1-35 20 90 1-22 20 100 1-25 20 100

TABLE-US-00015 TABLE 6b Post-emergence effect at 80 g/ha against MATIN in % Example number Dosage [g/ha] MATIN 1-31 80 90 1-32 80 100 1-35 80 100 1-22 80 100 1-25 80 100

TABLE-US-00016 TABLE 7a Post-emergence effect at 20 g/ha against PHBPU in % Example number Dosage [g/ha] PHBPU 1-31 20 90 1-32 20 90 1-35 20 90 1-25 20 100

TABLE-US-00017 TABLE 7b Post-emergence effect at 80 g/ha against PHBPU in % Example number Dosage [g/ha] PHBPU 1-31 80 90 1-32 80 100 1-35 80 100 1-22 80 100 1-25 80 100

TABLE-US-00018 TABLE 8a Post-emergence effect at 20 g/ha against POLCO in % Example number Dosage [g/ha] POLCO 1-32 20 90 1-35 20 80

TABLE-US-00019 TABLE 8b Post-emergence effect at 80 g/ha against POLCO in % Example number Dosage [g/ha] POLCO 1-32 80 100 1-35 80 100 1-22 80 90

TABLE-US-00020 TABLE 9a Post-emergence effect at 20 g/ha against SETVI in % Example number Dosage [g/ha] SETVI 1-31 20 80 1-21 20 80 1-32 20 100 1-35 20 100 1-22 20 100 1-25 20 100

TABLE-US-00021 TABLE 9b Post-emergence effect at 80 g/ha against SETVI in % Example number Dosage [g/ha] SETVI 1-31 80 90 1-21 80 100 1-32 80 100 1-35 80 100 1-22 80 100 1-25 80 100

TABLE-US-00022 TABLE 10a Post-emergence effect at 20 g/ha against VERPE in % Example number Dosage [g/ha] VERPE 1-32 20 90 1-35 20 90 1-22 20 90 1-25 20 90

TABLE-US-00023 TABLE 10b Post-emergence effect at 80 g/ha against VERPE in % Example number Dosage [g/ha] VERPE 1-31 80 80 1-32 80 100 1-35 80 100 1-22 80 100 1-25 80 100

TABLE-US-00024 TABLE 11a Post-emergence effect at 20 g/ha against VIOTR in % Example number Dosage [g/ha] VIOTR 1-31 20 90 1-21 20 100 1-32 20 100 1-35 20 100 1-22 20 100 1-25 20 100

TABLE-US-00025 TABLE 11b Post-emergence effect at 80 g/ha against VIOTR in % Example number Dosage [g/ha] VIOTR 1-31 80 100 1-21 80 100 1-32 80 100 1-35 80 100 1-22 80 100 1-25 80 100

TABLE-US-00026 TABLE 12a Post-emergence effect at 20 g/ha against KCHSC in % Example number Dosage [g/ha] KCHSC 1-31 20 100 1-21 20 90 1-32 20 100 1-35 20 100 1-22 20 100 1-25 20 100

TABLE-US-00027 TABLE 12b Post-emergence effect at 80 g/ha against KCHSC in % Example number Dosage [g/ha] KCHSC 1-31 80 100 1-21 80 100 1-32 80 100 1-35 80 100 1-22 80 100 1-25 80 100

TABLE-US-00028 TABLE 13a Post-emergence effect at 20 g/ha against A VEFA in % Example number Dosage [g/ha] AVEFA 1-22 20 90

TABLE-US-00029 TABLE 13b Post-emergence effect at 80 g/ha against AVEFA in % Example number Dosage [g/ha] AVEFA 1-22 80 100 1-25 80 100

TABLE-US-00030 TABLE 14a Post-emergence effect at 20 g/ha against ECHCG in % Example number Dosage [g/ha] ECHCG 1-22 20 100 1-25 20 80

TABLE-US-00031 TABLE 14b Post-emergence effect at 80 g/ha against ECHCG in % Example number Dosage [g/ha] ECHCG 1-22 80 100 1-25 80 100

[0377] As shown by the results from tables 1a/b, 2a/b, 3a/b, 4a/b, 5, 6a/b, 7a/b, 8a/b, 9a/b, 10a/b, 11a/b, 12a/b, 13a/b and 14a/b, the compounds of the invention have good herbicidal post-emergence efficacy against a broad spectrum of weed grasses and broad-leaved weeds. For example, the examples listed, at an application rate of 80/20 g/ha, show 80-100% activity against Alopecurus myosuroides, Digitaria sanguinalis, Setaria viridis, Veronica persica and Viola tricolor, among other plants. The compounds of the invention are therefore suitable for control of unwanted plant growth by the post-emergence method.

2. Pre-Emergence Herbicidal Effect and Crop Plant Compatibility

[0378] Seeds of monocotyledonous and dicotyledonous weed plants and crop plants are laid out in sandy loam soil in wood-fiber 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 to the surface of the covering soil as aqueous suspension or emulsion at a water application rate equating to 600 to 800 l/ha with addition of 0.2% wetting agent.

[0379] After the treatment, the pots are placed in a greenhouse and kept under good growth conditions for the trial plants. The damage to the test plants is scored visually after a test period of 3 weeks by comparison with untreated controls (herbicidal activity in percent (%): 100% activity=the plants have died, 0% activity=like control plants).

TABLE-US-00032 TABLE 1a Pre-emergence effect at 20 g/ha against ABUTH in % Example number Dosage [g/ha] ABUTH 1-31 20 90 1-35 20 90 1-22 20 80 1-25 20 100

TABLE-US-00033 TABLE 1b Pre-emergence effect at 80 g/ha against ABUTH in % Example number Dosage [g/ha] ABUTH 1-31 80 100 1-21 80 100 1-32 80 100 1-35 80 100 1-22 80 100 1-25 80 100

TABLE-US-00034 TABLE 2a Pre-emergence effect at 20 g/ha against ALOMY in % Example number Dosage [g/ha] ALOMY 1-32 20 80

TABLE-US-00035 TABLE 2b Pre-emergence effect at 80 g/ha against ALOMY in % Example number Dosage [g/ha] ALOMY 1-32 80 100 1-35 80 80 1-22 80 80

TABLE-US-00036 TABLE 3a Pre-emergence effect at 20 g/ha against AMARE in % Example number Dosage [g/ha] AMARE 1-21 20 90 1-32 20 100 1-35 20 100 1-22 20 100 1-25 20 100

TABLE-US-00037 TABLE 3b Pre-emergence effect at 80 g/ha against AMARE in % Example number Dosage [g/ha] AMARE 1-31 80 100 1-21 80 100 1-32 80 100 1-35 80 100 1-22 80 100 1-25 80 100

TABLE-US-00038 TABLE 4a Pre-emergence effect at 20 g/ha against AVEFA in % Example number Dosage [g/ha] AVEFA 1-32 20 80 1-35 20 90

TABLE-US-00039 TABLE 4b Pre-emergence effect at 80 g/ha against A VEFA in % Example number Dosage [g/ha] AVEFA 1-32 80 100 1-35 80 100 1-22 80 80 1-25 80 90

TABLE-US-00040 TABLE 5a Pre-emergence effect at 20 g/ha against DIGSA in % Example number Dosage [g/ha] DIGSA 1-31 20 90 1-21 20 90 1-32 20 100 1-35 20 100 1-22 20 100 1-25 20 100

TABLE-US-00041 TABLE 5b Pre-emergence effect at 80 g/ha against DIGSA in % Example number Dosage [g/ha] DIGSA 1-31 80 100 1-21 80 100 1-32 80 100 1-35 80 100 1-22 80 100 1-25 80 100

TABLE-US-00042 TABLE 6a Pre-emergence effect at 20 g/ha against ECHCG in % Example number Dosage [g/ha] ECHCG 1-32 20 100 1-35 20 100 1-22 20 90 1-25 20 100

TABLE-US-00043 TABLE 6b Pre-emergence effect at 80 g/ha against ECHCG in % Example number Dosage [g/ha] ECHCG 1-31 80 100 1-21 80 100 1-32 80 100 1-35 80 100 1-22 80 100 1-25 80 100

TABLE-US-00044 TABLE 7a Pre-emergence effect at 20 g/ha against LOLRI in % Example number Dosage [g/ha] LOLRI 1-32 20 90 1-35 20 80

TABLE-US-00045 TABLE 7b Pre-emergence effect at 80 g/ha against LOLRI in % Example number Dosage [g/ha] LOLRI 1-32 80 90 1-35 80 90 1-25 80 90

TABLE-US-00046 TABLE 8a Pre-emergence effect at 20 g/ha against MATIN in % Example number Dosage [g/ha] MATIN 1-32 20 100 1-35 20 100 1-22 20 100 1-25 20 100

TABLE-US-00047 TABLE 8b Pre-emergence effect at 80 g/ha against MATIN in % Example number Dosage [g/ha] MATIN 1-32 80 100 1-35 80 100 1-22 80 100 1-25 80 100

TABLE-US-00048 TABLE 9a Pre-emergence effect at 20 g/ha against PHBPU in % Example number Dosage [g/ha] PHBPU 1-35 20 80

TABLE-US-00049 TABLE 9b Pre-emergence effect at 80 g/ha against PHBPU in % Example number Dosage [g/ha] PHBPU 1-32 80 90 1-35 80 100 1-22 80 80 1-25 80 90

TABLE-US-00050 TABLE 10a Pre-emergence effect at 20 g/ha against POLCO in % Example number Dosage [g/ha] POLCO 1-32 20 90 1-35 20 90

TABLE-US-00051 TABLE 10b Pre-emergence effect at 80 g/ha against POLCO in % Example number Dosage [g/ha] POLCO 1-21 80 100 1-32 80 90 1-35 80 100 1-22 80 90

TABLE-US-00052 TABLE 11a Pre-emergence effect at 20 g/ha against SETVI in % Example number Dosage [g/ha] SETVI 1-32 20 90 1-35 20 100 1-22 20 90 1-25 20 100

TABLE-US-00053 TABLE 11b Pre-emergence effect at 80 g/ha against SETVI in % Example number Dosage [g/ha] SETVI 1-31 80 100 1-21 80 90 1-32 80 100 1-35 80 100 1-22 80 100 1-25 80 100

TABLE-US-00054 TABLE 12a Pre-emergence effect at 20 g/ha against VERPE in % Example number Dosage [g/ha] VERPE 1-32 20 80 1-22 20 80 1-25 20 90

TABLE-US-00055 TABLE 12b Pre-emergence effect at 80 g/ha against VERPE in % Example number Dosage [g/ha] VERPE 1-32 80 90 1-35 80 100 1-22 80 90 1-25 80 100

TABLE-US-00056 TABLE 13a Pre-emergence effect at 20 g/ha against VIOTR in % Example number Dosage [g/ha] VIOTR 1-31 20 90 1-21 20 100 1-32 20 100 1-35 20 100 1-22 20 100 1-25 20 100

TABLE-US-00057 TABLE 13b Pre-emergence effect at 80 g/ha against VIOTR in % Example number Dosage [g/ha] VIOTR 1-31 80 90 1-21 80 100 1-32 80 100 1-35 80 100 1-22 80 100 1-25 80 100

TABLE-US-00058 TABLE 14a Pre-emergence effect at 20 g/ha against KCHSC in % Example number Dosage [g/ha] KCHSC 1-31 20 90 1-21 20 90 1-32 20 100 1-35 20 100 1-22 20 100 1-25 20 100

TABLE-US-00059 TABLE 14b Pre-emergence effect at 80 g/ha against KCHSC in % Example number Dosage [g/ha] KCHSC 1-31 80 100 1-21 80 90 1-32 80 100 1-35 80 100 1-22 80 100 1-25 80 100

[0380] As shown by the results from tables 1a/b, 2a/b, 3a/b, 4a/b, 5a/b, 6a/b, 7a/b, 8a/b, 9a/b, 10a/b, 11a/b, 12a/b, 13a/b and 14a/b, the compounds of the invention have good herbicidal pre-emergence efficacy against a broad spectrum of weed grasses and broad-leaved weeds. For example, the compounds, at an application rate of 80/20 g/ha, show 80-100% activity against Alopecurus myosuroides, Avenafatua, Digitaria sanguinalis, Echinochloa crus-galli, Lolium rigidum, Setaria viridis, Amaranthus retroflexus, Viola tricolor and Veronica persica, among other plants. The compounds of the invention are therefore suitable for control of unwanted plant growth by the pre-emergence method.