HERBICIDALLY ACTIVE BICYCLIC BENZOYLPYRAZOLES

Abstract

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

##STR00001##

In this formula (I), A, X.sup.1 and X.sup.2 represent (CH.sub.2).sub.n, O or S(O).sub.n, R, R.sup.a, R.sup.b, R.sup.p1, R.sup.p2 and R.sup.p3 represent radicals such as hydrogen, halogen, alkyl, alkyloxy and cycloalkyl.

Claims

1. A compound of formula (I) ##STR00028## And/or an agrochemically acceptable salt thereof, in which the symbols and indices have the following meanings: A represents (CH.sub.2).sub.n, X.sup.1, X.sup.2 independently of one another each each represent O or S(O).sub.n, R represents halo-(C.sub.1-C.sub.6)-alkyl, R.sup.a, R.sup.b independently of one another each represent hydrogen, fluorine, (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.p1 represents hydrogen, (C.sub.1-C.sub.4)-alkylcarbonyloxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-alkoxycarbonyloxy-(C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.6)-alkylsulfonyl, (C.sub.1-C.sub.4)-alkoxy-(C.sub.1-C.sub.6)-alkylsulfonyl, or phenylsulfonyl, thiophenyl-2-sulfonyl, benzoyl, benzoyl-(C.sub.1-C.sub.6)-alkyl or benzyl substituted in each case by n identical or different radicals from the group consisting of halogen, (C.sub.1-C.sub.4)-alkyl and (C.sub.1-C.sub.4)-alkoxy, R.sup.p2 represents (C.sub.1-C.sub.4)-alkyl, R.sup.p3 represents hydrogen, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.3-C.sub.8)-cycloalkyl, (C.sub.1-C.sub.4)-alkyl-(C.sub.3-C.sub.8)-cycloalkyl or (C.sub.3-C.sub.6)-halocycloalkyl, n represents 0, 1 or 2.

2. The compound as claimed in claim 1, in which A represents (CH.sub.2).sub.n, X.sup.1, X.sup.2 independently of one another each represent O or S(O).sub.n, R represents halo-(C.sub.1-C.sub.3)-alkyl, R.sup.a, R.sup.b independently of one another each represent hydrogen, fluorine, (C.sub.1-C.sub.6)-alkyl, halo-(C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.6)-alkyloxy, 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.p1 represents hydrogen, R.sup.p2 represents (C.sub.1-C.sub.4)-alkyl, R.sup.p3 represents hydrogen, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl or cyclopropyl, n represents 0, 1 or 2.

3. The compound as claimed in claim 1, in which A represents (CH.sub.2).sub.n, X.sup.1, X.sup.2 independently of one another each represent O or S(O).sub.n, R represents trifluoromethyl, difluoromethyl or pentafluoroethyl, R.sup.a, R.sup.b independently of one another each represent hydrogen, fluorine, methyl, ethyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, 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.p1 represents hydrogen, R.sup.p2 represents (C.sub.1-C.sub.4)-alkyl, R.sup.p3 represents hydrogen, (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl or cyclopropyl, n represents 0, 1 or 2.

4. A herbicidal composition comprising a herbicidally effective amount of at least one compound as claimed in claim 1.

5. The herbicidal composition as claimed in claim 4, mixed with one or more formulation auxiliaries.

6. A method for controlling unwanted plants, wherein an effective amount of at least one compound of the formula (I) as claimed in claim 1 or of a herbicidal composition as applied to the plants or the site of the unwanted vegetation.

7. A product comprising one or more compounds 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 one or more compounds are used for controlling one or more unwanted plants in one or more crops of one or more useful plants.

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

Description

A. CHEMICAL EXAMPLES

Example 1-44: Synthesis of 7-(5-hydroxy-1-ethyl-pyrazole-3-carbonyl)-4-(trifluoromethyl)-1,3-benzoxathiolane

[0398] ##STR00027##

[0399] 97 mg (0.6 mmol) of carbonyldiimidazole are added to 125 mg (0.5 mmol) of 4-(trifluoromethyl)-1,3-benzoxathiolane-7-carboxylic acid and 73 mg (0.65 mmol) of 5-hydroxy-1-ethylpyrazole in 10 ml of acetonitrile. After stirring for 4 d at RT, 101 mg (1 mmol) of triethylamine, 20 mg (0.2 mmol) of acetone cyanohydrin and a spatula tip of KCN are added. After 5 d the solvent is concentrated, the residue is taken up in dichloromethane and washed with 10% strength sulfuric acid. The organic phase is dried, concentrated and the residue obtained is purified via RP-HPLC. Yield 114 mg (65%).

[0400] Intermediate 1-44A: Synthesis of ethyl 2-hydroxy-3-methylsulfinyl-4-(trifluoromethyl)benzoate 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))

[0401] Intermediate 1-44B: Synthesis of ethyl 2-hydroxy-3-chloromethylsulfanyl-4-(trifluoromethyl)benzoate 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))

[0402] Intermediate 1-44C: Synthesis of 4-(trifluoromethyl)-1,3-benzoxathiolane-7-carboxylic acid 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.

[0403] 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. (NMR, DMSO-d.sub.6: 6=13.37 (br s, 1H); 7.63 (d, 1H); 7.31 (d, 1H); 5.99 (s, 2H))

[0404] 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 6 value in ppm and then, separated by a space, the signal intensity are listed. The 6 value/signal intensity number pairs for different signal peaks are listed with separation from one another by semicolons.

[0405] The peak list for one example therefore takes the form of:

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

[0406] 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.

[0407] 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.

[0408] 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.

[0409] 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.

[0410] 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.

[0411] 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”.

[0412] 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.

[0413] Further details of .sup.1H NMR peak lists can be found in the Research Disclosure Database Number 564025.

[0414] Analytical Data

TABLE-US-00002 No. NMR 1-15  .sup.1H-NMR(400.0 MHz, CDCl.sub.3): δ = 7.41 (s, 1H); 7.33 (d, 1H); 7.20 (dd, 1H); 4.47 (m, 2H); 3.70 (s, 3H); 3.18 (m, 2H) 1-18 .sup.1H-NMR(400.0 MHz, CDCl.sub.3): δ = 7.58 (s, 1H); 7.40 (dd, 1H); 7.27 (d, 1H); 5.86 (s, 2H); 4.06 (q, 2H); 1.45 (t, 3H) 1-20 .sup.1H-NMR(400.0 MHz, CDCl.sub.3): δ = 7.42 (s, 1H); 7.33 (d, 1H); 7.20 (dd, 1H); 4.48 (m, 2H); 4.06 (q, 2H); 3.18 (m, 2H); 1.45 (t, 3H) 1-23 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): δ = 7.29 (d, 1H); 7.15 (d, 1H); 5.85 (s, 2H); 3.37 (s, 3H); 2.17 (s, 3H) 1-25 .sup.1H-NMR(400.0 MHz, CDCl.sub.3): δ = 7.33 (d, 1H); 7.02 (dd, 1H); 4.46 (m, 2H); 3.62 (s, 3H); 3.15 (m, 2H); 1.83 (s, 3H) 1-28 .sup.1H-NMR(400.0 MHz, CDCl.sub.3): δ = 8.01 (d, 1H); 7.60 (s, 1H); 7.59 (d, 1H); 5.72 (d, 1H); 5.10 (d, 1H); 3.75 (s, 3H) 1-30 .sup.1H-NMR(400.0 MHz, CDCl.sub.3): δ = 7.69 (d, 1H); 7.50 (d, 1H); 7.42 (s, 1H); 5.03 (ddd, 1H); 4.66 (ddd, 1H); 3.73 (s, 3H); 3.32 (ddd, 1H); 3.04 (ddd, 1H) 1-35 .sup.1H-NMR(400.0 MHz, CDCl.sub.3): δ = 7.70 (d, 1H); 7.50 (d, 1H); 7.44 (s, 1H); 5.03 (ddd, 1H); 4.68 (ddd, 1H); 4.09 (q, 2H); 3.33 (ddd, 1H); 3.05 (ddd, 1H); 1.46 (t, 3H) 1-40 .sup.1H-NMR(400.0 MHz, CDCl.sub.3): δ = 7.55 (d, 1H); 7.51 (d, 1H); 4.99 (ddd, 1H); 4.66 (ddd, 1H); 3.68 (s, 3H); 3.35 (ddd, 1H); 3.03 (ddd, 1H); 1.84 (s, 3H) 1-44 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): δ = 7.89 (d, 1H); 7.62 (s, 1H); 7.55 (dd, 1H); 7.33 (t, 1H); 5.48 (s, 2H); 3.53 (s, 3H) 1-45 .sup.1H-NMR(400.0 MHz, CDCl.sub.3): δ = 7.66 (d, 1H); 7.58 (d, 1H); 7.52 (s, 1H); 4.88 (m, 2H); 3.71 (s, 3H); 3.62 (m, 2H) 1-50 .sup.1H-NMR(400.0 MHz, CDCl.sub.3): δ = 7.67 (dd, 1H); 7.58 (d, 1H); 7.34 (s, 1H); 4.89 (m, 2H); 4.07 (q, 2H); 3.61 (m, 2H); 1.46 (t, 3H) 1-55 .sup.1H-NMR(400.0 MHz, CDCl.sub.3): δ = 7.59 (d, 1H); 7.51 (dd, 1H); 4.87 (m, 2H); 3.64 (s, 3H); 3.59 (m, 2H); 1.80 (s, 3H) 1-58 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): δ = 7.67 (d, 1H); 7.62 (s, 1H); 7.56 (d, 1H); 4.66 (s, 2H); 3.55 (s, 3H) 1-60 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): δ = 7.63 (d, 1H); 7.34 (s, 1H); 7.29 (d, 1H); 3.54 (s, 3H); 3.31 (m, 2H); 3.20 (m, 2H) 1-61 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): δ = 7.81 (d, 1H); 7.39 (d, 1H); 7.33 (s, 1H); 3.53 (s, 3H); 2.90 (m, 2H); 2.73 (m, 2H); 2.17 (m, 2H) 1-63 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): δ = 7.68 (d, 1H); 7.63 (s, 1H); 7.56 (d, 1H); 4.66 (s, 2H); 3.95 (q, 2H); 1.28 (t, 3H) 1-65 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): δ = 7.63 (d, 1H); 7.36 (s, 1H); 7.31 (d, 1H); 3.92 (q, 2H); 3.32 (m, 2H); 3.20 (m, 2H); 1.27 (t, 3H) 1-66 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): δ = 7.74 (d, 1H); 7.34 (d, 1H); 7.27 (s, 1H); 3.84 (q, 2H); 2.84 (m, 2H); 2.67 (m, 2H); 2.10 (m, 2H); 1.19 (t, 3H) 1-68 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): δ = 7.49 (s, 2H); 4.64 (s, 2H); 3.41 (s, 3H); 2.20 (s, 3H) 1-70 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): δ = 7.60 (d, 1H); 7.18 (d, 1H); 3.39 (s, 3H); 3.28 (m, 2H); 3.22 (m, 2H); 2.04 (s, 3H); 1-71 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): δ = 7.71 (d, 1H); 7.24 (d, 1H); 3.40 (s, 3H); 2.78 (m, 2H); 2.67 (m, 2H); 2.10 (m, 5H) 1-85 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): δ = 8.26 (d, 1H); 7.90 (d, 1H); 7.70 (s, 3H); 4.91 (s, 2H); 3.56 (s, 3H) 1-89 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): δ = 8.27 (d, 1H); 7.90 (d, 1H); 7.72 (s, 1H); 4.92 (s, 2H); 3.95 (q, 2H); 1.28 (t, 3H) 1-93 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): δ = 8.11 (d, 1H); 7.85 (d, 1H); 4.90 (s, 2H); 3.39 (s, 3H); 2.29 (s, 3H)  1-112 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): δ = 7.30 (d, 1H); 7.19 (d, 1H); 5.86 (s, 2H); 3.38 (s, 3H); 2.52 (m, 1H); 0.79 (m, 4H)  1-116 .sup.1H-NMR(400.0 MHz, CDCl.sub.3): δ = 7.59 (dd, 1H); 7.48 (d, 1H); 5.02 (ddd, 1H); 4.65 (ddd, 1H); 3.61 (s, 3H); 3.28 (ddd, 1H); 3.02 (ddd, 1H); 1.02 (m, 1H); 0.83-0.75 (m, 2H); 0.72-0.62 (m, 1H); 0.56-0.48 (m, 1H)  1-119 .sup.1H-NMR(400.0 MHz, CDCl.sub.3): δ = 7.59 (d, 1H); 7.57 (d, 1H); 4.88 (m, 2H); 3.60 (s, 3H); 3.60-3.58 (m, 2H); 0.97 (m, 1H); 0.82-0.77 (m, 2H); 0.60 (m, 2H)  1-127 .sup.1H-NMR(400.0 MHz, DMSO-d.sub.6): δ = 7.31 (d, 1H); 7.19 (dd, 1H); 5.86 (s, 2H); 3.48 (s, 3H); 2.86-2.82 (m, 2H); 2.59-2.52 (m, 2H)  1-128 .sup.1H-NMR(400.0 MHz, CDCl.sub.3): δ = 7.60 (s, 1H); 7.41 (d, 1H); 7.19 (d, 1H); 5.83 (s, 2H); 3.71 (s, 3H)  1-130 .sup.1H-NMR(400.0 MHz, CDCl.sub.3): δ = 7.97 (dt, 1H); 7.52 (s, 1H); 7.52 (d, 1H); 5.16 (s, 2H); 3.73 (s, 3H)  1-131 .sup.1H-NMR(400.0 MHz, CDCl.sub.3): δ = 7.60 (s, 1H); 7.41 (dd, 1H); 7.19 (d, 1H); 5.83 (s, 2H); 4.07 (q, 2H); 1.45 (t, 3H)

B. FORMULATION EXAMPLES

[0415] 1. Dusting Products

[0416] 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

[0417] 2. Dispersible Powder

[0418] 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

[0419] 3. Dispersion Concentrate

[0420] 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.

[0421] 4. Emulsifiable Concentrate

[0422] 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.

[0423] 5. Water-Dispersible Granules

[0424] Water-dispersible granules are obtained by mixing 75 parts by weight of a compound of the formula (I),

TABLE-US-00003 75 parts by weight of a compund of the formula (I), 10 parts by weight of calcium lignosulfonate, 5 parts by weight of sodium laurylsulfate, 3 parts by weight of polyvinyl alcohol and 7 parts by weight of kaolin,

[0425] 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.

[0426] 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),

TABLE-US-00004 25 parts by weight of a compound of the formula (I), 5 parts by weight of sodium 2,2′-dinaphthylmethane-6,6′-disulfonate, 2 parts by weight of sodium oleoylmethyltaurinate, 1 parts by weight of polyvinyl alcohol, 17 parts by weight of calcium carbonate and 50 parts by weight of water,

[0427] 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

[0428] Test Description

[0429] In the tables below, the following abbreviations are used:

[0430] Undesired Plants/Weeds:

[0431] ABUTH: Abutilon theophrasti

[0432] AMARE: Amaranthus retroflexus

[0433] CYPES: Cyperus esculentus

[0434] ECHCG: Echinochloa crus-galli

[0435] SETVI: Setaria viridis

[0436] STEME: Stellaria media

[0437] VERPE: Veronica persica

[0438] VIOTR: Viola tricolor

[0439] 1. Pre-Emergence Herbicidal Action and Crop Plant Compatibility

[0440] 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 6001/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-00005 TABLE 1 Pre-emergence action against CYPES Example Dosage number [g/ha] CYPES 1-28 320 90 1-43 320 100 1-44 320 80

TABLE-US-00006 TABLE 2 Pre-emergence action against ECHCG Example Dosage number [g/ha] ECHCG 1-13 320 100 1-28 320 100 1-43 320 100 1-44 320 80 1-15 80 80 1-20 80 100 1-25 80 90 1-30 80 100 1-35 80 100 1-40 80 80 1-45 80 100 1-50 80 100 1-55 80 100 1-65 80 80  1-116 80 80  1-119 80 80  1-128 80 90

TABLE-US-00007 TABLE 3 Pre-emergence action against SETVI Example Dosage number [g/ha] SETVI 1-13 320 100 1-28 320 100 1-43 320 100 1-44 320 100 1-15 80 100 1-20 80 100 1-23 80 100 1-25 80 100 1-30 80 100 1-35 80 100 1-40 80 100 1-45 80 100 1-50 80 100 1-65 80 90  1-116 80 100  1-128 80 100  1-131 80 100

TABLE-US-00008 TABLE 4 Pre-emergence action against ABUTH Example Dosage number [g/ha] ABUTH 1-13 320 100 1-28 320 100 1-43 320 90 1-20 80 100 1-23 80 100 1-25 80 100 1-30 80 100 1-35 80 100 1-40 80 100 1-45 80 100 1-50 80 100 1-55 80 100 1-89 80 90  1-116 80 80  1-119 80 100  1-128 80 90  1-131 80 100

TABLE-US-00009 TABLE 5 Pre-emergence action against AMARE Example Dosage number [g/ha] AMARE 1-13 320 100 1-18 320 100 1-43 320 100 1-44 320 100 1-15 80 100 1-20 80 100 1-23 80 80 1-25 80 100 1-30 80 100 1-35 80 100 1-40 80 100 1-45 80 100 1-50 80 100 1-55 80 100 1-58 80 80 1-60 80 100 1-63 80 100 1-65 80 100 1-68 80 100 1-70 80 100 1-85 80 100 1-89 80 100 1-93 80 100  1-112 80 100  1-116 80 100  1-119 80 100  1-128 80 100  1-130 80 100  1-131 80 100

TABLE-US-00010 TABLE 6 Pre-emergence action against STEME Example Dosage number [g/ha] STEME 1-13 320 100 1-28 320 100 1-43 320 90 1-44 320 90 1-15 80 100 1-20 80 100 1-23 80 100 1-25 80 90 1-30 80 100 1-35 80 100 1-40 80 100 1-45 80 100 1-50 80 100 1-55 80 100 1-58 80 90 1-60 80 90 1-63 80 90 1-65 80 100 1-68 80 100 1-70 80 100 1-85 80 100 1-89 80 100 1-93 80 90  1-112 80 90  1-116 80 100  1-119 80 100  1-128 80 100  1-130 80 100  1-131 80 90

TABLE-US-00011 TABLE 7 Pre-emergence action against VIOTR Example Dosage number [g/ha] VIOTR 1-13 320 100 1-28 320 100 1-43 320 100 1-15 80 100 1-20 80 100 1-25 80 100 1-30 80 100 1-35 80 100 1-45 80 100 1-55 80 90 1-58 80 100 1-60 80 100 1-63 80 100 1-65 80 100 1-70 80 90  1-112 80 90  1-116 80 100  1-119 80 100  1-128 80 100  1-131 80 100

TABLE-US-00012 TABLE 8 Pre-emergence action against VERPE Example Dosage number [g/ha] VERPE 1-13 320 100 1-28 320 100 1-43 320 100 1-44 320 90 1-15 80 90 1-25 80 80 1-45 80 100 1-50 80 90 1-55 80 90 1-85 80 90  1-116 80 80  1-119 80 90

[0441] 2. Post-Emergence Herbicidal Action and Crop Plant Compatibility

[0442] 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-00013 TABLE 9 Post-emergence action against ECHCG Example Dosage number [g/ha] ECHCG 1-13 20 90 1-15 20 80 1-18 20 80 1-20 20 80 1-25 20 90 1-28 20 90 1-30 20 100 1-35 20 80 1-40 20 90 1-50 20 80 1-55 20 100 1-63 20 80 1-65 20 80 1-68 20 80 1-93 20 80  1-112 20 80  1-116 20 100  1-128 20 90  1-131 20 80

TABLE-US-00014 TABLE 10 Post-emergence action against SETVI Example Dosage number [g/ha] SETVI 1-13 20 100 1-15 20 80 1-18 20 80 1-20 20 80 1-28 20 90 1-30 20 90 1-35 20 100 1-40 20 80 1-44 20 80 1-50 20 80 1-58 20 80 1-65 20 100  1-116 20 90  1-128 20 90  1-131 20 80

TABLE-US-00015 TABLE 11 Post-emergence action against ABUTH Example Dosage number [g/ha] ABUTH 1-13 20 90 1-18 20 80 1-20 20 80 1-28 20 90 1-30 20 80 1-35 20 90 1-40 20 80 1-50 20 90 1-55 20 90 1-63 20 80  1-116 20 90  1-119 20 90

TABLE-US-00016 TABLE 12 Post-emergence action against AMARE Example Dosage number [g/ha] AMARE 1-13 20 90 1-15 20 80 1-23 20 100 1-28 20 100 1-30 20 100 1-35 20 100 1-40 20 80 1-45 20 100 1-50 20 100 1-55 20 100 1-58 20 90 1-60 20 90 1-63 20 100 1-65 20 80 1-68 20 90 1-70 20 90 1-85 20 90 1-89 20 90 1-93 20 90  1-112 20 100  1-116 20 90  1-119 20 100  1-128 20 80  1-130 20 100

TABLE-US-00017 TABLE 13 Post-emergence action against STEME Example Dosage number [g/ha] STEME 1-13 20 100 1-15 20 90 1-23 20 80 1-18 20 90 1-25 20 100 1-28 20 90 1-35 20 90 1-40 20 100 1-44 20 90 1-45 20 100 1-50 20 80 1-55 20 90 1-58 20 80 1-60 20 80 1-63 20 80 1-70 20 80 1-85 20 80 1-89 20 80  1-112 20 80  1-116 20 100  1-119 20 100  1-128 20 80  1-130 20 90

TABLE-US-00018 TABLE 14 Post-emergence action against VIOTR Example Dosage number [g/ha] VIOTR 1-18 20 100 1-15 20 80 1-28 20 90 1-30 20 90 1-35 20 100 1-40 20 80 1-45 20 90 1-55 20 80 1-68 20 80  1-127 20 80

TABLE-US-00019 TABLE 15 Post-emergence action against VERPE Example Dosage number [g/ha] VERPE 1-28 20 90 1-45 20 90 1-85 20 80