NOVEL-ALKYNYL-SUBSTITUTED 3-PHENYLPYRROLIDINE-2,4-DIONES AND USE THEREOF AS HERBICIDES

Abstract

Novel alkynyl-substituted 3-phenylpyrrolidine-2,4-diones and use thereof as herbicides

The present invention relates to novel effective alkynyl-substituted 3-phenylpyrrolidine-2,4-diones according to the general formula (I) or agrochemically acceptable salts thereof,

##STR00001##

where

XC.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl or C.sub.3-C.sub.6-cycloalkyl; YC.sub.1-C.sub.4-alkyl or C.sub.3-C.sub.6-cycloalkyl; n=1, 2 or 3; m=1 or 2; R.sup.1=C.sub.1-C.sub.6-alkyl, or C.sub.3-C.sub.6-cycloalkyl; R.sup.2=hydrogen or methyl; R.sup.3C.sub.1-C.sub.3-alkoxy-C.sub.1-C.sub.3-alkyl, or a saturated five- or six-membered heterocycle with an oxygen or sulphur atom; G=hydrogen, a cleavable group L or a cation E.

The invention also relates to the use of the compounds according to the invention for controlling weeds and weed grasses in crops of useful plants.

Claims

1. An alkynyl-substituted N-phenylpyrrolidine-2,4-dione of formula (I), ##STR00027## or an agrochemically acceptable salt thereof, wherein XC.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl or C.sub.3-C.sub.6-cycloalkyl, YC.sub.1-C.sub.4-alkyl or C.sub.3-C.sub.6-cycloalkyl, n=1,2 or 3, m=1 or 2, R.sup.1C.sub.1-C.sub.6-alkyl or C.sub.3-C.sub.6-cycloalkyl, R.sup.2=hydrogen or methyl, R.sup.3C.sub.1-C.sub.3-alkoxy-C.sub.1-C.sub.3-alkyl, or a saturated five- or six-membered heterocycle with an oxygen or sulphur atom, G=hydrogen, a cleavable group L or a cation E; where L=one of the following radicals ##STR00028## in which R.sup.4C.sub.1-C.sub.4-alkyl or C.sub.1-C.sub.3-alkoxy-C.sub.1-C.sub.4-alkyl; R.sup.5C.sub.1-C.sub.4-alkyl, R.sup.6C.sub.1-C.sub.4-alkyl or an unsubstituted phenyl or a phenyl substituted one or more times with halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, nitro or cyano, R.sup.7, R.sup.7=in each case independently of one another methoxy or ethoxy, R.sup.8 and R.sup.9=in each case independently of one another methyl, ethyl, phenyl or together form a saturated 5-, 6- or 7-membered ring, or together form a saturated 5-, 6- or 7-membered heterocycle with an oxygen or sulphur atom, E=an alkali metal ion, an ion equivalent of an alkaline earth metal, an ion equivalent of aluminium or an ion equivalent of a transition metal, a magnesium halogen cation, or an ammonium ion, in which optionally one, two, three or all four hydrogen atoms by identical or different radicals from the groups hydrogen, C.sub.1-C.sub.5-alkyl, C.sub.1-C.sub.5-alkoxy or C.sub.3-C.sub.7-cycloalkyl, which can in each case be substituted one or more times with fluorine, chlorine, bromine, cyano, hydroxy or be interrupted by one or more oxygen or sulphur atoms, or a cyclic secondary or tertiary aliphatic or heteroaliphatic amino ion, for example morpholinium, thiomorpholinium, piperidinium, pyrrolidinium, or in each case protonated 1,4-diazabicyclo[2.2.2]octane (DABCO) or 1,5-diazabicyclo[4.3.0]undec-7-ene (DBU), or a heterocyclic ammonium cation, for example in each case protonated pyridine, 2-methylpyridine, 3-methylpyridine, 4-methylpyridine, 2,4-dimethylpyridine, 2,5-di-methylpyridine, 2,6-dimethylpyridine, 5-ethyl-2-methylpyridine, pyrrole, imidazole, quinoline, quinoxaline, 1,2-dimethylimidazole, 1,3-dimethylimidazolium methyl sulphate, or a sulphonium ion.

2. A compound of formula (I) according to claim 1 or an agrochemically acceptable salt thereof, where X and Y, independently of one another, are in each case=C.sub.1-C.sub.4-alkyl or C.sub.3-C.sub.6-alkyl.

3. A compound of formula (I) according to claim 2 or an agrochemically acceptable salt thereof, where X and Y, independently of one another, are in each case defined as methyl, ethyl or cyclopropyl.

4. A compound of formula (I) according to claim 1 or an agrochemically acceptable salt thereof, where R.sup.1=methyl, ethyl, isopropyl or cyclopropyl.

5. A compound of formula (I) according to claim 1 or an agrochemically acceptable salt thereof, where n and m are in each case independently of one another defined as 1 or 2.

6. A compound of formula (I) according to claim 1 or an agrochemically acceptable salt thereof, where R.sup.3C.sub.1-C.sub.3-alkoxy-C.sub.1-C.sub.3-alkyl.

7. A compound of formula (I) according to claim 1, or an agrochemically acceptable salt thereof, where G=hydrogen, or a cleavable group L selected from ##STR00029## where R.sup.4C.sub.1-C.sub.4-alkyl, and R.sup.5C.sub.1-C.sub.4-alkyl, or an alkali metal ion or ion equivalent of an alkaline earth metal ion selected from Na, K, Ca or Mg.

8. A compound of formula (I) according to claim 7, or an agrochemically acceptable salt thereof, where G=hydrogen, or a cleavable group L selected from ##STR00030## where R.sup.4=methyl, ethyl, or isopropyl, and R.sup.5=methyl or ethyl, or a sodium, potassium, trimethylammonium, pyridinium, quinolinium or trimethylsulphonium cation or an ion equivalent of calcium or magnesium.

9. A compound of formula (I) according to claim 1 or an agrochemically acceptable salt thereof, where X=methyl, ethyl or cyclopropyl, Y=methyl or ethyl, R.sup.1=methyl, ethyl, isopropyl or cyclopropyl, and R.sup.3CH.sub.3CH.sub.2OCH.sub.2 or CH.sub.3OCH.sub.2.

10. A compound of formula (I) according to claim 1 or an agrochemically acceptable salt thereof, where X=methyl and Y=ethyl.

11. A compound of formula (I) according to claim 1 or an agrochemically acceptable salt thereof, where X=methyl, ethyl or cyclopropyl, Y=methyl, ethyl, R.sup.1=methyl, ethyl, isopropyl or cyclopropyl, and R.sup.2=hydrogen, R.sup.3CH.sub.3CH.sub.2OCH.sub.2or CH.sub.3OCH.sub.2 n and m are in each case independently of one another 1 or 2, G=hydrogen, or a cleavable group L selected from ##STR00031## where R.sup.4=methyl, ethyl, or isopropyl, and R.sup.5=methyl or ethyl, or a cation E selected from sodium, potassium or an ion equivalent of calcium or magnesium.

12. A alkynyl-substituted phenyl acetic acid of formula (VII), ##STR00032## where XC.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl or C.sub.3-C.sub.6-cycloalkyl, YC.sub.1-C.sub.4-alkyl or C.sub.3-C.sub.6-cycloalkyl, and R.sup.1C.sub.1-C.sub.6-alkyl or C.sub.3-C.sub.6-cycloalkyl, with the proviso that the compound 2,6-dimethyl-4-propargylphenyl acetic acid is excluded.

13. A compound of formula (VII) according to claim 12, where X=methyl, ethyl or cyclopropyl; Y=methyl or ethyl, and R.sup.1=methyl, ethyl, isopropyl or cyclopropyl, where the compound 2,6-dimethyl-4-propargylphenyl acetic acid is excluded.

14. An herbicidal composition comprising a compound of formula (I) according to claim 1 or an agrochemically acceptable salt thereof, and optionally an agrochemically acceptable carrier, diluent and/or solvent.

15. An herbicidal composition according to claim 14, comprising at least one further pesticidally active substance from the group of insecticides, acaricides, herbicides, fungicides, safeners and growth regulators.

16. An herbicidal composition according to claim 15, comprising a safener.

17. An herbicidal composition according to claim 14, comprising a further herbicide.

18. A method of controlling undesired plant growth, comprising applying the compound according to claim 1 or an agrochemically acceptable salt thereof, to the plant to be controlled, plant parts, plant seeds and/or an area on which undesired plant growth takes place.

19. A method according to claim 18, where the undesired plant growth is selected from grasslike monocotyledonous weeds.

20. A method according to claim 18, where plant growth of resistant grasses in useful plants is controlled, and where an herbicidal composition comprising said compound and/or salt is applied to the weed to be controlled.

21. A method according to claim 20, where the useful plant is selected from wheat, barley, rye, oats, rice, sugar cane, soybean, rapeseed, sunflower and corn.

22. A compound of formula (I) and/or an agrochemically acceptable salt thereof according to claim 1 for controlling harmful plants.

23. Compound and/or salt according to claim 22, wherein the compound of formula (I) or an agrochemically acceptable salt thereof is used for controlling harmful plants in crops of useful plants.

24. Compound and/or salt according to claim 23, wherein the useful plants are transgenic useful plants.

Description

A. CHEMICAL EXAMPLES

Example I-1

[0151] ##STR00016##

[0152] 1.14 g (2.67 mmol) of the precursor were added dropwise in a solution of 10 ml of DMF to a solution of 8 ml of DMF and 748 mg (2.5 eq) of potassium t-butylate over the course of 30 min at room temperature and stirred at this temperature for 18 h. Then, the mixture was heated for 4 h at 40 C., the solvent was removed under reduced pressure and the residue was taken up in 100 ml of water. The mixture was adjusted to pH=1 with 1 n hydrochloric acid and the resulting residue was filtered off, giving 1.00 g (95%) of the target compound A1 as colourless oil.

[0153] .sup.1H-NMR (400 MHz, d.sub.6-DMSO): 3.33 (s, 1H, CH.sub.2OCH.sub.3), 2.04 (s, 3H, CH.sub.3CC) Analogously to Example I-1 and also according to the general details relating to the production, the following compounds according to the invention were obtained.

##STR00017##

TABLE-US-00001 TABLE 1 Ex. No. n m R.sup.3 X Y R.sup.1 Note I-1 2 2 CH.sub.2CH.sub.2OCH.sub.3 Et Et Me nd I-2 2 2 CH.sub.2CH.sub.2OCH.sub.3 Me Et Me nd I-3 2 2 CH.sub.2CH.sub.2OCH.sub.3 Me Me Me nd I-4 2 2 CH.sub.2CH.sub.2OCH.sub.3 Me Me Cyclopropyl nd I-5 2 2 CH.sub.2OCH.sub.3 Me Et Me nd I-6 2 2 CH.sub.2OCH.sub.3 Et Et Me nd I-7 2 2 CH.sub.2OCH.sub.3 Me Et Cyclopropyl nd I-8 2 2 CH.sub.2OCH.sub.3 Me Me Cyclopropyl nd I-9 1 2 CH.sub.2OCH.sub.3 Me Et Me cis I-10 1 2 CH.sub.2OCH.sub.3 Me Et Me trans I-11 1 2 CH.sub.2OCH.sub.3 Me Et Cyclopropyl trans I-12 1 2 CH.sub.2OCH.sub.3 Me Et Cyclopropyl cis I-13 1 2 CH.sub.2OCH.sub.3 Me Me Cyclopropyl trans I-14 1 2 CH.sub.2OCH.sub.3 Me Me Cyclopropyl cis/trans mixture nd = not determined

Example Ia-1

[0154] ##STR00018##

[0155] 1.00 g (2.6 mmol) of the compound (I-11) according to the invention was introduced with 0.5 ml of triethylamine and 1.5 mg of DMAP in 8 ml of dichloromethane and stirred for 10 min at 40 C. Then 0.315 g (2.9 mmol) of ethyl chloroformate in 2 ml of dichloromethane was slowly added dropwise and the mixture was then stirred for 6 h at 40 C. and then overnight at RT. 10 ml of sodium hydrogencarbonate solution were added and the organic phase was separated off. The residue remaining after concentration was purified by column chromatography (silica gel, gradient EtOAc/n-heptane), giving 0.920 g (77%) of the compound B1 according to the invention as isomer mixture. This gave, by column chromatography over silica gel (ethyl acetate/hexane v/v=20:80), in total 0.43 g (47%) of the transisomer in the form of colourless crystals with m.p. 183-184 C.

[0156] Analogously to Example Ia-1 and according to the general details relating to the production, the following compounds of the formula (I-1-b) are obtained:

##STR00019##

TABLE-US-00002 TABLE 2 Ex. No. n m R.sup.3 X Y R.sup.1 L Note Ia-1 1 2 CH.sub.2OCH.sub.3 Me Et Cyclopropyl COOEt trans Ia-2 1 2 CH.sub.2OCH.sub.3 Me Me Cyclopropyl COOEt nd Ia-3 2 2 CH.sub.2OCH.sub.3 Me Et Me COCH(CH.sub.3).sub.2 trans Ia-4 2 2 CH.sub.2CH.sub.2OCH.sub.3 Me Et Me COCH(CH.sub.3).sub.2 nd Ia-5 2 2 CH.sub.2CH.sub.2OCH.sub.3 Et Et Me COCH(CH.sub.3).sub.2 nd Ia-6 1 2 CH.sub.2OCH.sub.3 Me Et Me COCH(CH.sub.3).sub.2 trans Ia-7 1 2 CH.sub.2OCH.sub.3 Me Et Me COCH(CH.sub.3).sub.2 cis Ia-8 1 2 CH.sub.2OCH.sub.3 Me Et Me COCH(CH.sub.3).sub.2 trans Ia-9 1 2 CH.sub.2OCH.sub.3 Me Et Me COCH(CH.sub.3).sub.2 cis Ia-10 1 2 CH.sub.2OCH.sub.3 Me Et Cyclopropyl COCH(CH.sub.3).sub.2 cis/trans mixture Ia-11 1 2 CH.sub.2OCH.sub.3 Me Et Cyclopropyl COCH(CH.sub.3).sub.2 trans Ia-12 1 2 CH.sub.2OCH.sub.3 Me Et Cyclopropyl COCH(CH.sub.3).sub.2 cis Ia-13 2 2 OCH.sub.2CH.sub.2OCH.sub.3 Et Et Me COCH(CH.sub.3).sub.2 nd Ia-14 2 2 OCH.sub.2CH.sub.2OCH.sub.3 Me Et Me COOEt nd Ia-15 1 2 OCH.sub.2CH.sub.2OCH.sub.3 Et Me Me COOEt nd Ia-16 1 2 CH.sub.2OCH.sub.3 Me Et Me SO.sub.2Me nd Ia-17 2 2 CH.sub.2OCH.sub.3 Me Et Me COOEt m.p. 197 C.

B. PREPARATION EXAMPLES (STARTING MATERIALS)

Example II-1

[0157] ##STR00020##

[0158] 1.10 g (4.5 mmol) of 4-cyclopropylethinyl-2-ethyl-6-methylphenyl acetic acid were dissolved in 20 ml of dichloromethane and admixed with one drop of DMF. 0.75 g (1.3 eq) of oxalyl chloride were added and the mixture was heated under reflux to boiling until gas stopped evolving. Then, the reaction solution was concentrated, admixed twice more with in each case 20 ml of dichloromethane and concentrated again in order finally to take up the residue in 4 ml of dichloromethane (solution 1). 1.015 (4.5 mmol) of 3-methoxymethylcyclopentane amino acid methyl ester-hydrochloride and 1 g of triethylamine were dissolved in 20 ml of dichloromethane and solution 1 was added dropwise over the course of 90 min. After stirring for 18 h, the mixture was admixed with 50 ml of water, and the organic phase was separated off, concentrated and purified by column chromatography (silica gel gradient EtOAc/n-heptane). This gave 1.16 g (62%) of the desired target compound.

[0159] Analogously to Example II-1 and according to the general details relating to the production, the following compounds of the formula (II) are obtained:

##STR00021##

TABLE-US-00003 TABLE 3 Ex. No. n m R.sup.3 X Y R.sup.1 Physical data II-2 2 1 CH.sub.2CH.sub.2OMe Me Et Me .sup.1H-NMR (400 MHz, CDCl.sub.3): 3.70 (s, 3H, OCH.sub.3), 3.44 (pseudo t, 2H, CH.sub.2OCH.sub.3), 2.05 (s, 3H, CH.sub.3CC) II-3 2 1 CH.sub.2OMe Me Et Me .sup.1H-NMR (400 MHz, CDCl.sub.3): 3.70 (s, 3H, OCH.sub.3), 3.07 (d, 2H, CH.sub.2OCH.sub.3), 2.05 (s, 3H, CH.sub.3CC) II-4 2 1 CH.sub.2CH.sub.2OMe Et Et Me .sup.1H-NMR (400 MHz, CDCl.sub.3): 3.67 (s, 3H, OCH.sub.3), 3.34 (pseudo t, 2H, CH.sub.2OCH.sub.3), 2.07 (s, 3H, CH.sub.3CC)

Example (VII-1)

[0160] ##STR00022##

[0161] 8.41 g (32.7 mmol) of literature-known methyl 4-bromo-2,6 dimethylphenyl acetate were initially introduced with 0.1 mol % of dichlorobistriphenylpalladium dichloride in a mixture of 45 ml of triethylamine and 18 ml of pyridine and 4.11 g (1.9 eq) of cyclopropylacetylene were added. The mixture was heated under reflux to boiling for 7.5 h and then stirred overnight at room temperature. The resulting salts were filtered off and in each case washed twice with triethylamine and diethyl ether. The mother liquor was concentrated under reduced pressure, and admixed firstly with water and then with 32 ml of a 3% strength hydrochloric acid solution. Then, extraction was carried out with ethyl acetate and this organic phase was washed twice with water. After drying the organic phase, concentration was performed and the resulting residue was purified by column chromatography (silica gel, gradient n-heptane/ethyl acetate). This thus gave 6.83 g (86%) of the desired compound.

[0162] .sup.1H-NMR (400 MHz, CDCl.sub.3): 7.07 (s, 2H, ArH), 3.67 (s, 5H, OCH.sub.3 and CH.sub.2Ar), 2.26 (s, 3H, ArCH.sub.3), 1.42 (s, 1 H, CH-c-Pr)

Example (VII-2)

[0163] ##STR00023##

[0164] 7.5 g (24.8 mmol) of methyl 2,6-diethyl-4-trimethylsilylpropynylphenyl acetate were dissolved in 200 ml of ethanol and admixed with a solution of 4 eq of potassium hydroxide in 200 ml of ethanol. The mixture was heated under reflux to boiling for 7 h, the solvent was removed and 500 ml of water were added. Then, hydrochloric acid was used to establish a pH of 1 and the mixture was extracted three times with 100 ml of ethyl acetate in each case. The combined organic phases were dried with sodium sulphate, concentrated and purified by column chromatography (silica gel, gradient EtOAc/n-heptane). This thus gave 4.3 g of compound (VII-2) according to the invention.

[0165] .sup.1H-NMR (400 MHz, CDCl.sub.3): 7.09 and 7.07 each s, 1H, ArH), 3.70 (s, 2H, CH.sub.2Ar), 2.62 (q, 2H, ArCH.sub.2), 2.29 (s, 3H, ArCH.sub.3), 2.03 (s, 3H, CH.sub.3CC), 1.18 (t, 3H, CH.sub.3CH.sub.2Ar)

[0166] The following compounds are obtained analogously

##STR00024##

TABLE-US-00004 TABLE 4 Ex. No. R X Y R.sup.3 Physical data VII-3 Me Et Et CH.sub.2SiMe.sub.3 .sup.1H-NMR (300 MHz, CDCl.sub.3): 7.07 (s, 2H, ArH), 3.70 (s, 2H, CH.sub.2Ar), 3.64 (s, 3H, OCH.sub.3), 2.59 (q, 2H, CH.sub.2Ar), 0.16 (s, 9H, Si(CH.sub.3).sub.3) VII-4 Me Me Et CH.sub.2SiMe.sub.3 .sup.1H-NMR (400 MHz, CDCl.sub.3): 3.68 (s, 2H, CH.sub.2Ar), 3.66 (s, 3H, OCH.sub.3), 2.62 (q, 2H, CH.sub.2Ar), 0.16 (s, 9H, Si(CH.sub.3).sub.3) VII-5 Me Me Me CH.sub.2SiMe.sub.3 Oil VII-6 Me Me Et Me .sup.1H-NMR (300 MHz, CDCl.sub.3): 3.66 (s, 2H, CH.sub.2Ar), 3.64 (s, 3H, OCH.sub.3), 2.01 (s, 3H, CH.sub.3CC) VII-7 Me Et Et Me Oil VII-8 Me Me Me Me .sup.1H-NMR (400 MHz, CDCl.sub.3): 3.68(s, 3H, OCH.sub.3), 3.67 (s, 2H, CH.sub.2Ar), 2.03 (s, 3H, CH.sub.3CC) VII-9 Me Me Cl Me .sup.1H-NMR (400 MHz, CDCl.sub.3): 3.81(s, 2H, CH.sub.2Ar), 3.67 (s, 3H, OCH.sub.3), 2.03 (s, 3H, CH.sub.3CC) VII-10 Me Me Et CH.sub.2C(OH)(CH.sub.3).sub.2 .sup.1H-NMR (400 MHz, CDCl.sub.3): 3.78(s, 2H, CH.sub.2Ar), 3.75 (s, 3H, OCH.sub.3), 1.63 (s, 6H, (CH.sub.3).sub.2) VII-11 Me Me Cl CH.sub.2C(OH)(CH.sub.3).sub.2 .sup.1H-NMR (400 MHz, CDCl.sub.3): 3.85(s, 2H, CH.sub.2Ar), 3.68 (s, 3H, OCH.sub.3), 1.60 (s, 6H, (CH.sub.3).sub.2) VII-12 Me Me Me CH.sub.2C(OH)(CH.sub.3).sub.2 .sup.1H-NMR (400 MHz, CDCl.sub.3): 3.67 (s, 5H, OCH.sub.3 and CH.sub.2Ar), 1.60 (s, 6H, (CH.sub.3).sub.2) VII-13 H Et Et Me .sup.1H-NMR (400 MHz, CDCl.sub.3): 7.12 (s, 2H, ArH), 3.72 (s, 2H CH.sub.2Ar), 2.62 (q, 2H, CH.sub.2Ar), 2.03 (s, 3H, ArCCCH.sub.3) VII-14 H Me Me Me .sup.1H-NMR (400 MHz, CDCl.sub.3): 7.05 (s, 2H, ArH), 3.70 (s, 2H, CH.sub.2Ar), 3.66 (s, 3H, OCH.sub.3), 2.01 (s, 3H, ArCCCH.sub.3), VII-15 H Me Et Cyclopropyl .sup.1H-NMR (400 MHz, d6-DMSO): 7.03 (s, 2H, ArH), 3.60 (s, 2H, CH.sub.2Ar), 1.51 (s, 1H, CHc-Pr) VII-16 H Me Me Cyclopropyl .sup.1H-NMR (400 MHz, d6-DMSO): 7.03 (s, 2H, ArH), 3.57 (s, 2H, CH.sub.2Ar), 1.51 (s, 1H, CHc-Pr)

[0167] NMR Data of Selected Examples

[0168] NMR Peak List Method

[0169] The .sup.1H NMR data of selected examples are stated in the form of .sup.1H NMR peak lists. For each signal peak, first the value in ppm and then the signal intensity in round brackets are listed. The pairs of value-signal intensity numbers for different signal peaks are listed with separation from one another by semicolons.

[0170] The peak list for one example therefore has the form of:

[0171] .sub.1 (intensity.sub.1); .sub.2 (intensity.sub.2); . . . ; .sub.i (intensity.sub.i); . . . ; .sub.n (intensity.sub.n)

[0172] 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.

[0173] 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.

[0174] To calibrate the chemical shift of .sup.1H-NMR spectra, we used 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.

[0175] 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.

[0176] In addition, like conventional .sup.1H NMR printouts, they may show solvent signals, signals of stereoisomers of the target compounds which likewise form part of the subject-matter of the invention, and/or peaks of impurities.

[0177] When stating compound signals in the delta range of solvents and/or water, in our lists of 1H NMR peaks, the usual solvent peaks, for example peaks of DMSO in DMSO-D.sub.6 and the peak of water are shown, which usually have on average a high intensity.

[0178] 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%).

[0179] 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.

[0180] 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 customary 1H-NMR interpretation.

[0181] Further details of .sup.1H NMR peak lists can be found in the Research Disclosure Database Number 564025.

[0182] Example Ia-7: .sup.1H-NMR(MHz, CDCl.sub.3): =7.261(50.0); 7.101(5.5); 7.084(5.2); 6.877(1.5); 6.851(1.5); 3.644(1.0); 3.456(1.0); 3.447(1. 8); 3.438(1.1); 3.434(1.7); 3.425(3.2); 3.416(1.9); 3.406(25.1); 3.403(24.7); 3.375(2.7); 3.36 6(2.6); 3.352(1.8); 3.348(2.8); 3.343(1.7); 3.338(2.3); 3.324(0.4); 3.146(1.8); 2.981(1.5); 2.5 73(0.3); 2.565(0.3); 2.554(1.0); 2.548(1.6); 2.535(1.8); 2.530(3.7); 2.517(2.9); 2.513(4.8); 2. 496(4.6); 2.478(2.9); 2.471(2.1); 2.465(2.3); 2.452(2.0); 2.446(2.1); 2.434(1.2); 2.428(1.2); 2.415(0.6); 2.409(0.6); 2.371(1.3); 2.344(1.0); 2.337(1.5); 2.314(1.3); 2.310(1.1); 2.287(1.0); 2.280(1.4); 2.253(1.0); 2.210(0.4); 2.199(2.1); 2.190(26.5); 2.178(1.5); 2.053(0.7); 2.046(0.8); 2.034(38.2); 2.017(1.0); 2.011(1.5); 2.004(2.0); 1.987(2.9); 1.969(1.2); 1.962(1.3); 1.9 53(0.5); 1.935(0.5); 1.887(0.4); 1.860(1.6); 1.843(3.0); 1.833(1.4); 1.825(2.1); 1.780(0.3); 1. 705(1.3); 1.701(1.3); 1.696(1.4); 1.692(1.3); 1.667(1.2); 1.662(1.2); 1.658(1.2); 1.571(4.1); 1.256(0.9); 1.193(0.8); 1.185(0.3); 1.174(1.5); 1.155(9.0); 1.148(1.1); 1.136(17.5); 1.129(1. 6); 1.118(8.0); 1.110(0.7); 1.014(1.2); 1.012(1.2); 0.996(12.7); 0.992(12.1); 0.984(1.7); 0.97 8(11.7); 0.975(11.7); 0.967(13.4); 0.966(15.7); 0.950(12.3); 0.948(14.3); 0.008(0.9); 0.000(32.2); 0.009(0.9)

[0183] Example I-1: .sup.1H-NMR(MHz, CDCl.sub.3): =7.758(0.9); 7.350(0.6); 7.265(50.0); 7.146(15.1); 7.127(0.4); 7.070(0.3); 6.407(1.1); 4.727(1.0); 3.444(2.5); 3.428(6.1); 3.413(3.5); 3.395(1.5); 3.379(0.7); 3.323(0.9); 3.310(36.6); 3.2 87(6.8); 2.879(7.4); 2.785(6.2); 2.516(0.6); 2.496(1.1); 2.478(1.8); 2.460(4.1); 2.445(4.4); 2. 442(4.4); 2.436(1.6); 2.427(4.3); 2.417(1.3); 2.409(2.0); 2.399(0.6); 2.391(0.9); 2.381(0.4); 2.372(0.4); 2.269(0.3); 2.217(0.4); 2.212(0.4); 2.063(0.7); 2.049(28.3); 2.039(1.9); 2.023(0. 7); 1.999(0.7); 1.985(1.3); 1.975(1.3); 1.951(1.9); 1.941(2.2); 1.918(1.1); 1.908(1.7); 1.883(1.7); 1.855(1.8); 1.699(1.3); 1.646(0.4); 1.630(0.6); 1.615(0.5); 1.580(2.3); 1.543(4.0); 1.52 7(4.1); 1.512(2.0); 1.479(0.7); 1.199(0.4); 1.182(0.6); 1.170(0.7); 1.164(0.8); 1.134(2.0); 1.1 31(1.9); 1.116(2.4); 1.113(2.3); 1.103(15.7); 1.092(2.1); 1.084(32.7); 1.065(14.5); 0.008(0. 6); 0.000(28.3); 0.008(0.9)

[0184] Example Ia-13: .sup.1H-NMR(MHz, CDCl.sub.3): =7.264(22.2); 7.141(18.0); 5.298(18.0); 4.031(3.7); 4.013(12.5); 3.995(12.6); 3.977(3.8); 3.4 24(2.9); 3.409(6.7); 3.394(3.1); 3.306(50.0); 2.589(0.5); 2.570(1.6); 2.551(3.2); 2.532(5.5); 2.521(1.9); 2.513(5.3); 2.502(5.2); 2.495(2.0); 2.484(5.6); 2.465(3.1); 2.446(1.6); 2.427(0.5); 2.049(34.9); 2.036(0.4); 1.931(0.9); 1.921(1.6); 1.894(4.7); 1.863(3.3); 1.682(2.7); 1.651(4.7); 1.521(2.8); 1.509(4.8); 1.499(2.9); 1.197(0.7); 1.190(0.9); 1.177(20.5); 1.165(2.9); 1.1 58(44.3); 1.146(2.1); 1.139(20.3); 1.133(15.1); 1.124(1.3); 1.115(27.9); 1.106(1.1); 1.097(1 3.0); 1.083(0.4); 1.038(0.6); 0.901(1.1); 0.882(0.5); 0.008(0.4); 0.000(13.6); 0.009(0.4)

[0185] Example Ia-5: .sup.1H-NMR(MHz, CDCl.sub.3): =7.266(0.4); 7.265(0.6); 7.262(45.3); 7.258(0.9); 7.256(0.5); 7.255(0.4); 7.126(13.8); 6.711(1.4); 5.299(2.1); 3.444(2.8); 3.429(6.6); 3.414(3.2); 3.326(50.0); 2.587(0.4); 2.568(1.4); 2.5 49(2.7); 2.534(1.6); 2.531(4.7); 2.517(4.3); 2.512(4.6); 2.500(7.0); 2.493(1.9); 2.482(4.3); 2. 480(4.9); 2.465(1.5); 2.461(2.7); 2.447(0.3); 2.442(1.4); 2.424(0.5); 2.046(29.5); 1.919(1.6); 1.887(1.7); 1.838(0.9); 1.828(0.7); 1.804(2.3); 1.795(1.9); 1.771(1.6); 1.761(1.3); 1.691(2. 5); 1.659(1.5); 1.594(16.1); 1.592(14.8); 1.554(0.6); 1.539(2.6); 1.524(3.9); 1.510(2.4); 1.49 8(0.9); 1.486(0.8); 1.460(0.4); 1.181(0.5); 1.169(17.2); 1.163(2.1); 1.150(38.2); 1.137(2.4); 1.131(17.5); 1.120(0.8); 1.110(1.1); 1.103(1.2); 1.077(0.5); 1.038(0.9); 1.025(0.4); 1.010(0. 4); 0.999(0.6); 0.993(0.5); 0.978(45.5); 0.961(45.0); 0.901(0.5); 0.008(0.7); 0.000(24.5); 0.009(0.7)

[0186] Example I-9: .sup.1H-NMR(MHz, d.sub.6-DMSO): =10.713(0.9); 7.069(0.5); 7.057(0.6); 3.339(0.4); 3.315(50.0); 3.251(4.2); 3.246(0.7); 2.510(6.2); 2.505(13.7); 2.500(19.3); 2.496(13.6); 2.491(6.2); 2.385(0.5); 2.367(0.5); 2.029(3.6); 1.025(0.5); 1.022(0.5); 1.007(1.0); 1.003(1.0); 0.988(0.5); 0.984(0.5)

[0187] Example Ia-8: .sup.1H-NMR(MHz, CDCl.sub.3): =7.270(0.3); 7.2696(0.4); 7.269(0.4); 7.268(0.5); 7.267(0.7); 7.266(1.0); 7.263(50.0); 7.258(0.5); 7.127(4.7); 7.103(4.7); 6.999(0.3); 6.583(2.2); 4.131(0.5); 4.113(0.5); 4.037(2.6); 4.02 8(0.3); 4.019(8.7); 4.001(9.3); 3.983(3.1); 3.403(0.7); 3.401(1.0); 3.393(0.7); 3.385(0.7); 3.3 77(0.9); 3.370(2.3); 3.362(2.3); 3.354(2.7); 3.348(29.4); 3.342(30.6); 3.334(2.5); 3.328(2.9); 3.322(0.9); 3.311(0.7); 3.306(0.7); 2.548(0.5); 2.537(0.8); 2.529(1.0); 2.518(1.6); 2.511(1. 8); 2.499(2.4); 2.492(2.1); 2.481(2.2); 2.475(2.2); 2.465(1.6); 2.456(1.8); 2.446(1.4); 2.438(0.9); 2.428(0.8); 2.419(0.5); 2.409(0.4); 2.303(0.5); 2.284(0.6); 2.279(0.7); 2.270(0.6); 2.26 0(0.7); 2.251(0.8); 2.245(1.0); 2.239(0.6); 2.227(0.9); 2.220(0.7); 2.211(0.8); 2.205(0.9); 2.1 91(12.4); 2.182(13.6); 2.054(0.9); 2.046(3.5); 2.041(35.7); 2.021(0.9); 2.013(1.3); 2.008(0. 5); 2.001(1.4); 1.993(0.7); 1.980(1.3); 1.956(2.3); 1.933(3.4); 1.926(2.4); 1.917(1.2); 1.901(1.8); 1.893(0.5); 1.867(0.6); 1.862(0.9); 1.849(1.1); 1.829(1.5); 1.816(0.9); 1.796(0.6); 1.67 7(0.4); 1.663(0.7); 1.658(0.5); 1.652(0.5); 1.644(0.9); 1.639(0.8); 1.631(1.0); 1.625(0.8); 1.6 20(1.2); 1.608(13.3); 1.588(0.6); 1.278(0.7); 1.260(1.5); 1.242(0.7); 1.163(5.8); 1.157(5.3); 1.144(13.0); 1.139(11.5); 1.126(13.3); 1.120(5.4); 1.109(22.0); 1.091(10.3); 0.008(0.8); 0.0 00(27.5); 0.009(0.7)

[0188] Example Ia-9: .sup.1H-NMR(MHz, CDCl.sub.3): =7.270(0.3); 7.269(0.4); 7.2684(0.4); 7.2676(0.5); 7.267(0.7); 7.266(1.0); 7.263(50.0); 7.259 (1.5); 7.258(0.5); 7.257(0.3); 7.125(3.8); 7.101(3.8); 6.999(0.3); 6.920(1.3); 6.909(1.3); 4.13 1(0.5); 4.113(0.5); 4.035(1.7); 4.021(1.1); 4.017(5.5); 4.015(3.5); 4.003(1.2); 3.999(5.6); 3.9 85(0.5); 3.982(1.8); 3.461(0.8); 3.458(0.9); 3.453(0.9); 3.449(0.8); 3.438(1.4); 3.435(1.5); 3. 430(1.5); 3.427(1.4); 3.410(23.2); 3.408(23.1); 3.381(2.1); 3.373(2.2); 3.355(3.8); 3.349(3. 7); 2.555(0.7); 2.537(1.3); 2.518(2.3); 2.499(2.5); 2.479(1.9); 2.474(1.4); 2.460(1.2); 2.455(1.3); 2.449(1.2); 2.442(0.7); 2.436(0.8); 2.422(0.9); 2.416(1.4); 2.406(1.1); 2.388(0.7); 2.37 8(0.7); 2.372(1.1); 2.344(0.7); 2.218(0.3); 2.196(19.0); 2.182(1.3); 2.139(0.6); 2.118(0.9); 2. 103(0.4); 2.094(0.8); 2.073(1.0); 2.058(0.7); 2.046(3.6); 2.039(29.0); 2.016(0.6); 2.008(1.0); 2.002(0.8); 1.987(0.4); 1.981(0.5); 1.963(0.3); 1.940(0.4); 1.877(1.0); 1.859(1.0); 1.847(1. 9); 1.829(1.8); 1.812(0.7); 1.713(0.5); 1.706(0.9); 1.701(1.0); 1.679(0.6); 1.673(0.9); 1.666(0.9); 1.585(12.2); 1.321(0.6); 1.303(1.3); 1.290(1.5); 1.286(1.6); 1.278(2.4); 1.264(5.9); 1.2 60(6.0); 1.242(1.5); 1.174(0.3); 1.164(7.9); 1.158(1.0); 1.145(17.2); 1.139(2.0); 1.132(6.1); 1.130(6.7); 1.126(8.2); 1.120(1.2); 1.1 14(12.2); 1.112(12.7); 1.096(5.7); 1.094(5.8); 0.899(3.4); 0.882(12.6); 0.864(4.7); 0.008(0.8); 0.000(28.7); 0.008(0.8)

[0189] Example I-10: .sup.1H-NMR(MHz, d.sub.6-DMSO): =10.693(0.5); 7.068(0.5); 7.057(0.5); 3.326(50.0); 3.295(0.4); 3.283(0.4); 3.278(0.4); 3.246(4.0); 2.510(4.1); 2.505(9.0); 2.501(12.7); 2.496(9.0); 2.491(4.1); 2.370(0.3); 2.035(1.3); 2.0 29(3.5); 1.024(0.4); 1.020(0.4); 1.005(1.0); 1.001(0.9); 0.986(0.4); 0.983(0.4)

[0190] Example I-12: .sup.1H-NMR(MHz, d.sub.6-DMSO): =10.728(1.0); 8.135(1.3); 7.736(0.9); 7.41 1(1.5); 7.046(6.0); 7.029(6.0); 4.175(0.4); 4.157(1. 1); 4.140(1.1); 4.122(0.4); 3.465(15.7); 3.422(0.7); 3.359(1.0); 3.342(1.4); 3.336(3.5); 3.320 (4.2); 3.305(3.4); 3.293(0.7); 3.282(1.3); 3.263(0.9); 3.249(39.5); 3.244(7.7); 3.125(0.5); 2.8 35(0.5); 2.523(0.7); 2.510(16.7); 2.505(36.2); 2.501(50.0); 2.496(35.7); 2.492(16.2); 2.395(1.9); 2.375(11.0); 2.358(5.9); 2.339(2.6); 2.323(0.7); 2.224(1.0); 2.212(1.0); 2.201(0.9); 2.1 90(1.6); 2.178(1.2); 2.167(0.8); 2.155(0.8); 2.090(0.6); 2.074(0.5); 2.064(0.6); 2.054(0.7); 2. 046(0.8); 2.023(21.6); 2.006(1.6); 1.995(0.7); 1.987(0.7); 1.978(0.6); 1.910(0.7); 1.897(0.9); 1.892(1.0); 1.880(1.1); 1.867(1.1); 1.862(1.1); 1.849(0.5); 1.801(0.3); 1.654(1.0); 1.637(1. 1); 1.623(0.9); 1.588(0.8); 1.558(1.7); 1.545(2.3); 1.537(2.7); 1.533(1.8); 1.524(3.6); 1.516(1.7); 1.512(2.3); 1.504(2.1); 1.491(1.9); 1.470(1.1); 1.455(1.0); 1.437(0.9); 1.262(1.2); 1.24 5(2.4); 1.227(1.1); 1.059(0.4); 1.016(4.9); 1.013(5.1); 0.998(10.3); 0.994(10.5); 0.979(4.8); 0.975(4.7); 0.896(1.8); 0.885(4.7); 0.879(6.0); 0.870(2.7); 0.865(4.8); 0.858(5.5); 0.849(2.2); 0.833(0.3); 0.725(2.2); 0.716(6.0); 0.713(3.5); 0.710(5.3); 0.704(5.8); 0.697(5.5); 0.687(1. 6); 0.008(0.4); 0.000(15.1); 0.009(0.5)

[0191] Example Ia-12: .sup.1H-NMR(MHz, CDCl.sub.3): =7.263(50.0); 7.112(6.7); 7.090(6.5); 6.981(0.3); 6.518(2.7); 4.033(3.0); 4.015(9.5); 3.998(9. 8); 3.980(3.2); 3.420(0.3); 3.400(5.5); 3.392(0.8); 3.383(0.8); 3.375(1.4); 3.368(2.9); 3.360(2.6); 3.347(25.6); 3.341(26.0); 3.333(2.8); 3.327(3.1); 3.321(0.9); 3.310(0.8); 3.304(0.7); 2. 537(0.9); 2.526(1.1); 2.518(1.7); 2.508(2.1); 2.500(2.5); 2.489(3.0); 2.482(2.7); 2.470(2.8); 2.464(2.3); 2.454(2.1); 2.445(1.9); 2.436(1.8); 2.427(1.2); 2.417(1.0); 2.408(0.8); 2.398(0.7); 2.380(0.3); 2.299(0.5); 2.279(0.7); 2.275(0.7); 2.265(0.7); 2.256(0.9); 2.246(0.9); 2.240(1. 2); 2.223(1.1); 2.215(0.9); 2.206(0.9); 2.201(0.9); 2.180(15.1); 2.170(14.7); 2.156(0.7); 2.11 1(0.3); 2.066(0.3); 2.050(0.7); 2.030(1.6); 2.017(1.0); 2.009(1.6); 1.997(1.8); 1.976(1.6); 1.9 51(2.7); 1.928(4.3); 1.921(2.8); 1.912(1.5); 1.896(2.0); 1.888(0.5); 1.857(1.2); 1.844(1.6); 1. 823(2.0); 1.810(1.1); 1.790(0.8); 1.675(0.5); 1.661(0.9); 1.643(1.1); 1.638(0.9); 1.629(1.1); 1.618(1.2); 1.605(1.2); 1.591(7.3); 1.471(0.8); 1.458(1.7); 1.451(1.8); 1.446(1.1); 1.438(2.9); 1.425(1.9); 1.417(1.9); 1.405(1.0); 1.254(0.6); 1.156(6.3); 1.150(5.4); 1.137(14.3); 1.132(20.5); 1.115(24.6); 1.097(10.8); 0.881(1.7); 0.875(1.4); 0.868(3.6); 0.861(6.1); 0.854(3.7); 0.847(3.7); 0.841(6.0); 0.833(3.1); 0.827(1.5); 0.821(1.2); 0.809(3.1); 0.800(6.1); 0.795(5.9); 0.787(6.0); 0.782(5.1); 0.773(1.1); 0.769(1.3); 0.008(0.7); 0.000(25.7); 0.008(0.8)

[0192] Example I-11: .sup.1H-NMR(MHz, d.sub.6-DMSO): =10.699(2.1); 7.918(1.5); 7.046(6.7); 7.029(7.0); 3.398(23.7); 3.336(0.8); 3.316(1.0); 3.305(0.8); 3.292(3.2); 3.280(4.1); 3.276(3.7); 3.263(3.9); 3.258(1.8); 3.248(9.0); 3.244(42.4); 2.5 33(0.4); 2.523(0.7); 2.509(16.9); 2.505(36.1); 2.501(50.0); 2.496(36.3); 2.492(17.2); 2.452(0.6); 2.397(1.4); 2.379(3.9); 2.361(4.1); 2.339(1.6); 2.327(0.5); 2.188(0.3); 2.146(0.4); 2.13 6(0.5); 2.122(0.7); 2.114(1.1); 2.103(1.1); 2.093(1.2); 2.084(1.0); 2.073(0.8); 2.061(0.8); 2.0 26(15.4); 2.022(16.9); 1.980(0.5); 1.960(1.1); 1.949(0.7); 1.940(1.2); 1.929(1.3); 1.909(1.2); 1.890(0.5); 1.831(1.0); 1.825(0.9); 1.799(2.1); 1.793(1.3); 1.773(1.3); 1.767(1.1); 1.653(1. 0); 1.636(1.6); 1.620(1.5); 1.602(1.7); 1.588(1.3); 1.569(1.3); 1.558(1.7); 1.545(2.4); 1.537(2.3); 1.533(1.6); 1.524(3.7); 1.516(1.2); 1.512(2.1); 1.504(2.2); 1.491(1.4); 1.482(0.9); 1.47 6(0.9); 1.469(1.2); 1.457(1.2); 1.446(1.1); 1.438(0.8); 1.415(0.4); 1.016(5.6); 1.012(5.3); 0.9 97(11.8); 0.993(11.0); 0.978(5.5); 0.974(4.9); 0.896(2.0); 0.886(5.2); 0.879(6.6); 0.870(2.9); 0.865(5.2); 0.858(5.9); 0.849(2.3); 0.833(0.4); 0.813(0.3); 0.726(2.4); 0.717(6.5); 0.710(5. 8); 0.704(6.2); 0.698(5.9); 0.687(1.8); 0.008(0.6); 0.000(19.1); 0.008(0.6)

[0193] Example Ia-11: .sup.1H-NMR(MHz, CDCl.sub.3): =7.969(1.5); 7.283(2.0); 7.272(0.3); 7.271(0.4); 7.270(0.5); 7.269(0.7); 7.267(5.3); 7.266(4.9); 7.264(48.0); 7.263(50.0); 7.2585(1.0); 7.2576(0.7); 7.257(0.6); 7.256(0.4); 7.254(0.3); 7.1 11(8.0); 7.089(8.2); 6.920(2.7); 6.907(2.7); 6.231(0.7); 4.246(0.4); 4.229(1.3); 4.211(1.3); 4. 193(0.5); 4.031(3.1); 4.014(9.8); 3.996(10.1); 3.978(3.4); 3.639(0.4); 3.454(1.5); 3.450(1.7); 3.432(2.8); 3.427(2.7); 3.407(43.9); 3.379(4.0); 3.370(4.2); 3.354(5.4); 3.353(5.4); 3.348(5.7); 3.142(0.7); 2.980(0.6); 2.565(0.4); 2.546(1.4); 2.527(2.8); 2.509(4.8); 2.490(5.2); 2.470(3.6); 2.464(2.6); 2.451(2.5); 2.445(4.0); 2.433(1.7); 2.423(8.3); 2.422(8.5); 2.411(2.6); 2.40 1(2.0); 2.383(1.3); 2.373(1.2); 2.367(1.9); 2.340(1.3); 2.232(0.4); 2.212(0.5); 2.185(34.6); 2. 171(2.9); 2.134(1.2); 2.113(1.6); 2.097(0.7); 2.089(1.4); 2.068(1.9); 2.052(1.0); 2.027(2.1); 2.005(1.5); 1.999(1.5); 1.985(0.9); 1.979(0.9); 1.957(0.7); 1.934(0.8); 1.901(0.5); 1.891(0.5); 1.873(1.7); 1.855(1.9); 1.843(3.9); 1.825(3.6); 1.808(1.4); 1.696(2.0); 1.665(1.9); 1.586(1 5.8); 1.471(0.9); 1.458(1.9); 1.450(2.0); 1.445(1.2); 1.437(3.4); 1.425(2.2); 1.417(2.2); 1.40 4(1.2); 1.341(1.4); 1.323(2.7); 1.305(1.3); 1.259(0.3); 1.186(0.4); 1.158(11.7); 1.139(30.8); 1.119(33.8); 1.101(11.5); 1.083(0.4); 0.878(1.5); 0.872(1.4); 0.865(4.1); 0.859(7.3); 0.852(3.6); 0.844(4.6); 0.839(6.5); 0.830(3.2); 0.826(1.7); 0.818(1.3); 0.807(3.3); 0.799(8.3); 0.79 4(6.8); 0.787(7.5); 0.781(5.3); 0.771(1.4); 0.768(1.5); 0.008(0.7); 0.001(25.5); 0.000(27.0); 0.007(0.8)

[0194] Example Ia-1: .sup.1H-NMR(MHz, CDCl.sub.3): =7.269(0.3); 7.2684(0.3); 7.2676(0.4); 7.267(0.6); 7.266(0.8); 7.262(50.0); 7.109(4.9); 7.087 (4.8); 6.491(2.1); 4.025(2.8); 4.007(9.1); 3.989(9.2); 3.972(2.9); 3.381(0.6); 3.350(45.3); 3.3 32(9.5); 3.230(0.5); 3.214(0.5); 2.542(0.8); 2.523(1.4); 2.505(2.3); 2.485(2.7); 2.466(2.7); 2. 446(2.5); 2.428(1.5); 2.409(0.8); 2.186(22.5); 2.159(0.4); 2.060(0.8); 2.039(1.5); 2.019(2.1); 1.999(1.1); 1.904(1.1); 1.781(0.8); 1.770(0.7); 1.757(1.7); 1.747(2.0); 1.736(2.1); 1.725(2. 1); 1.719(1.9); 1.708(1.4); 1.692(1.0); 1.678(1.2); 1.660(3.4); 1.634(2.9); 1.616(1.2); 1.575( 9.9); 1.470(0.7); 1.458(1.4); 1.450(1.5); 1.445(0.9); 1.437(2.4); 1.431(0.8); 1.424(1.5); 1.41 7(1.6); 1.404(0.9); 1.254(1.4); 1.187(0.3); 1.158(8.1); 1.139(17.2); 1.119(13.9); 1.101(19.6); 1.083(9.2); 0.881(1.5); 0.875(1.2); 0.868(2.9); 0.861(4.9); 0.854(2.8); 0.847(3.1); 0.841(4. 8); 0.833(2.5); 0.827(1.2); 0.820(1.0); 0.808(2.6); 0.800(4.6); 0.795(4.5); 0.788(4.7); 0.782(4.1); 0.773(0.9); 0.769(1.1); 0.008(0.9); 0.004(0.3); 0.000(32.8); 0.005(0.8); 0.0056(0.6); 0.0065(0.5); 0.008(1.1)

[0195] Example I-7: .sup.1H-NMR(MHz, CDCl.sub.3): =8.015(0.6); 7.520(0.3); 7.372(2.6); 7.261(50.0); 7.190(0.5); 7.110(5.1); 7.095(5.2); 7.033(0. 3); 6.296(1.3); 3.887(0.9); 3.670(0.5); 3.623(0.4); 3.343(31.5); 3.331(7.2); 3.326(2.4); 3.309 (0.3); 3.249(6.3); 3.233(6.6); 3.192(0.5); 3.115(0.4); 2.931(0.3); 2.883(19.6); 2.845(1.6); 2.7 90(17.4); 2.758(0.6); 2.649(0.4); 2.630(0.4); 2.493(0.4); 2.475(1.0); 2.463(1.1); 2.457(2.4); 2.445(2.7); 2.438(2.6); 2.426(2.8); 2.419(1.1); 2.408(1.2); 2.397(0.3); 2.390(0.4); 2.301(0.4); 2.288(0.9); 2.226(0.4); 2.167(0.6); 2.157(0.4); 2.129(0.4); 2.107(21.4); 2.035(0.5); 1.982(1.4); 1.966(1.4); 1.938(2.6); 1.923(2.3); 1.896(2.0); 1.773(0.5); 1.735(0.8); 1.724(0.7); 1.65 2(0.8); 1.644(1.0); 1.636(0.9); 1.614(2.7); 1.587(1.9); 1.468(0.8); 1.455(1.6); 1.449(3.1); 1.4 43(1.2); 1.435(2.9); 1.428(1.1); 1.422(1.8); 1.414(1.8); 1.402(0.9); 1.255(0.9); 1.237(0.3); 1. 225(0.4); 1.210(0.5); 1.193(1.1); 1.182(2.3); 1.174(1.2); 1.153(2.0); 1.122(1.7); 1.109(1.0); 1.098(8.4); 1.090(1.8); 1.079(17.4); 1.060(7.8); 0.887(1.3); 0.874(3.1); 0.868(4.9); 0.859(3. 4); 0.854(3.4); 0.847(4.2); 0.839(2.5); 0.821(1.0); 0.805(1.1); 0.800(2.4); 0.791(4.7); 0.786(4.5); 0.779(4.9); 0.773(4.5); 0.768(1.7); 0.760(1.2); 0.008(0.7); 0.000(29.2); 0.008(1.0)

[0196] Example Ia-6: .sup.1H-NMR(MHz, CDCl.sub.3): =7.261(50.0); 7.104(7.2); 7.086(7.4); 6.630(2.5); 3.398(1.2); 3.395(1.3); 3.373(0.8); 3.357(1. 1); 3.350(3.2); 3.340(37.2); 3.330(38.8); 3.321(4.1); 3.315(5.2); 3.298(0.9); 3.291(0.4); 2.56 1(1.6); 2.548(0.9); 2.543(4.2); 2.537(1.3); 2.526(6.1); 2.518(2.3); 2.508(5.7); 2.500(3.2); 2.4 91(4.5); 2.481(3.1); 2.471(2.8); 2.460(2.6); 2.452(2.4); 2.441(2.2); 2.433(1.4); 2.423(1.3); 2. 415(0.8); 2.404(0.7); 2.227(0.7); 2.207(1.1); 2.204(1.1); 2.187(20.0); 2.179(19.1); 2.151(1. 8); 2.142(0.8); 2.132(1.0); 2.122(1.2); 2.099(1.1); 2.036(48.2); 2.020(1.9); 2.001(1.5); 1.987 (1.9); 1.967(1.7); 1.947(1.3); 1.930(2.4); 1.920(3.6); 1.914(2.5); 1.896(3.5); 1.887(0.7); 1.86 4(2.5); 1.847(1.1); 1.839(2.8); 1.830(2.4); 1.820(1.3); 1.815(1.6); 1.805(1.7); 1.797(1.1); 1.7 82(0.7); 1.651(0.5); 1.638(0.5); 1.628(1.1); 1.615(1.1); 1.610(1.1); 1.605(1.1); 1.590(5.4); 1. 577(1.1); 1.564(0.8); 1.554(0.5); 1.541(0.4); 1.258(0.8); 1.244(0.3); 1.154(7.0); 1.148(7.2); 1.135(15.4); 1.129(15.5); 1.1 16(6.9); 1.110(6.8); 1.012(17.4); 1.010(19.4); 0.995(17.9); 0.9 92(19.8); 0.987(16.8); 0.982(16.6); 0.970(15.6); 0.964(16.4); 0.948(0.8); 0.008(0.8); 0.000(33.3); 0.002(12.6); 0.008(0.9)

[0197] Example Ia-16: .sup.1H-NMR(MHz, CDCl.sub.3): =7.267(0.3); 7.2666(0.5); 7.262(37.0); 7.256(0.4); 7.212(2.5); 7.174(7.3); 7.149(7.2); 7.068(0.7); 7.016(0.4); 4.054(0.4); 4.037(0.7); 4.021(0.4); 3.615(0.6); 3.388(2.7); 3.370(2.8); 3.35 2(14.9); 3.327(1.9); 3.315(50.0); 3.220(9.3); 3.205(9.5); 2.859(1.1); 2.777(0.6); 2.598(0.3); 2.579(1.0); 2.561(2.1); 2.542(3.7); 2.530(1.3); 2.523(3.6); 2.511(3.6); 2.504(1.4); 2.493(3.8); 2.474(2.2); 2.462(0.4); 2.455(1.3); 2.440(43.2); 2.422(12.1); 2.378(0.3); 2.323(0.3); 2.263 (0.3); 2.241(0.6); 2.222(34.1); 2.115(0.4); 2.101(0.5); 2.088(0.7); 2.063(2.3); 2.044(48.1); 2. 022(1.2); 2.009(1.3); 1.999(1.9); 1.976(2.7); 1.965(5.5); 1.951(2.9); 1.940(4.0); 1.929(3.1); 1.915(3.0); 1.878(0.6); 1.867(0.5); 1.830(0.6); 1.818(0.6); 1.748(0.6); 1.737(0.8); 1.706(2.3); 1.700(2.3); 1.690(2.0); 1.673(3.6); 1.652(1.8); 1.644(2.1); 1.622(2.1); 1.588(0.7); 1.570(0. 6); 1.555(0.5); 1.448(0.3); 1.430(0.3); 1.252(1.0); 1.240(0.9); 1.207(2.2); 1.191(13.5); 1.172 (29.8); 1.153(12.9); 1.089(0.4); 1.076(0.4); 1.070(1.0); 1.051(1.0); 1.032(0.4); 0.983(0.8); 0. 965(1.5); 0.946(0.6); 0.008(0.6); 0.000(22.0); 0.008(0.6)

[0198] Example Ia-10: .sup.1H-NMR(MHz, CDCl.sub.3): =7.262(50.0); 7.205(1.0); 7.070(18.7); 6.916(3.0); 6.371(1.5); 4.055(0.6); 4.051(0.7); 4.037(0.6); 4.033(0.9); 4.029(2.2); 4.026(3.5); 4.011(6.9); 4.008(10.9); 3.994(7.0); 3.990(11.0); 3. 976(2.3); 3.972(3.6); 3.450(1.7); 3.442(1.8); 3.428(3.3); 3.419(3.1); 3.406(4.0); 3.402(43.0); 3.389(1.0); 3.378(3.4); 3.370(3.8); 3.367(3.0); 3.356(2.5); 3.345(28.5); 3.333(2.5); 3.327(0.9); 3.310(0.8); 2.529(0.6); 2.511(1.4); 2.501(1.1); 2.491(1.6); 2.485(1.1); 2.472(1.3); 2.455(0.4); 2.423(2.7); 2.395(1.7); 2.389(2.9); 2.362(1.8); 2.285(0.6); 2.266(0.8); 2.261(0.8); 2.25 2(0.7); 2.242(0.8); 2.233(1.1); 2.228(0.9); 2.209(0.9); 2.193(3.2); 2.184(1.7); 2.170(28.2); 2. 166(41.9); 2.157(16.1); 2.129(0.5); 2.112(1.9); 2.091(2.5); 2.070(0.6); 2.051(1.8); 2.029(1. 8); 2.018(1.4); 2.009(1.7); 2.001(2.0); 1.990(0.6); 1.979(1.3); 1.957(0.5); 1.939(4.2); 1.917( 3.7); 1.883(0.6); 1.866(1.5); 1.855(1.4); 1.842(3.2); 1.836(2.8); 1.830(1.5); 1.821(3.8); 1.80 1(1.5); 1.789(0.5); 1.702(1.3); 1.698(1.4); 1.694(1.4); 1.676(0.6); 1.669(1.3); 1.664(1.6); 1.6 44(0.7); 1.634(0.6); 1.625(0.5); 1.620(0.7); 1.611(0.5); 1.606(0.4); 1.601(0.5); 1.587(10.7); 1.460(1.0); 1.447(2.0); 1.439(2.1); 1.434(1.3); 1.426(3.7); 1.420(1.2); 1.414(2.2); 1.406(2.4); 1.393(1.2); 1.264(0.8); 1.154(0.8); 1.134(12.9); 1.116(24.5); 1.114(16.6); 1.098(11.4); 1.0 96(8.0); 0.899(0.4); 0.882(1.4); 0.874(1.0); 0.871(1.5); 0.862(2.4); 0.853(5.5); 0.847(2.6); 0. 844(3.5); 0.841(2.4); 0.837(4.0); 0.834(4.0); 0.831(5.0); 0.827(2.1); 0.823(2.7); 0.813(1.5); 0.810(1.0); 0.794(3.6); 0.786(6.2); 0.781(5.7); 0.774(7.1); 0.768(5.2); 0.760(1.2); 0.755(1.3); 0.008(0.7); 0.000(29.1); 0.008(0.9)

[0199] Example I-14: .sup.1H-NMR(MHz, d.sub.6-DMSO): =10.713(0.6); 7.898(0.3); 7.713(0.6); 7.267(0.6); 7.249(2.4); 7.230(1.7); 7.181(1.8); 7.163(1. 5); 7.142(0.8); 7.029(12.1); 3.423(8.7); 3.361(0.6); 3.338(2.1); 3.324(2.4); 3.321(2.3); 3.307 (2.1); 3.293(1.4); 3.282(1.5); 3.276(1.3); 3.265(1.3); 3.250(25.1); 3.245(15.9); 2.544(0.3); 2. 509(15.6); 2.504(35.2); 2.499(50.0); 2.495(35.5); 2.490(16.0); 2.377(0.5); 2.358(0.7); 2.33 5(0.6); 2.299(7.3); 2.226(1.0); 2.202(0.9); 2.192(1.4); 2.168(0.9); 2.123(0.5); 2.095(0.6); 2.0 71(2.4); 2.037(28.1); 2.016(1.1); 2.005(0.7); 1.988(0.8); 1.963(0.4); 1.911(0.7); 1.882(0.7); 1.833(0.6); 1.801(0.8); 1.775(0.6); 1.651(1.0); 1.635(0.7); 1.619(0.9); 1.593(0.5); 1.564(0.8); 1.552(1.1); 1.539(2.0); 1.531(1.6); 1.527(1.0); 1.519(3.1); 1.511(1.1); 1.506(1.7); 1.498(1. 8); 1.486(1.3); 1.472(1.1); 1.457(0.9); 1.439(0.8); 0.895(1.4); 0.884(3.7); 0.878(4.9); 0.868(2.0); 0.864(3.8); 0.857(4.3); 0.848(1.7); 0.718(1.7); 0.709(4.8); 0.702(4.2); 0.697(4.6); 0.69 0(4.3); 0.680(1.2); 0.008(0.7); 0.000(27.3); 0.009(0.8)

[0200] Example I-8: .sup.1H-NMR(MHz, d.sub.6-DMSO): =10.635(5.0); 10.594(1.4); 8.044(2.8); 7.948(0.7); 7.268(0.7); 7.249(2.0); 7.230(1.8); 7.181(2.0); 7.163(1.6); 7.142(0.9); 7.124(0.3); 7.026(13.8); 6.979(0.3); 3.362(1.3); 3.343(1.6); 3.3 20(49.2); 3.259(8.3); 3.235(28.7); 3.165(4.9); 3.149(5.1); 2.509(16.1); 2.504(35.7); 2.500(5 0.0); 2.495(35.5); 2.490(16.1); 2.299(7.7); 2.280(0.6); 2.210(0.7); 2.076(2.5); 2.044(42.1); 1.898(1.3); 1.874(2.0); 1.840(1.2); 1.716(1.5); 1.686(1.7); 1.551(1.4); 1.539(2.0); 1.530(2.1); 1.526(1.5); 1.518(3.4); 1.506(1.9); 1.498(1.8); 1.485(1.0); 1.396(2.0); 1.358(2.3); 1.324(1.8); 1.294(1.6); 1.261(0.5); 0.894(1.6); 0.883(4.0); 0.877(5.2); 0.868(2.4); 0.863(4.2); 0.856(4. 6); 0.847(1.9); 0.718(1.9); 0.709(5.2); 0.703(4.6); 0.697(5.0); 0.690(4.7); 0.680(1.5); 0.008(0.5); 0.000(14.6); 0.009(0.4)

[0201] Example Ia-2: .sup.1H-NMR(MHz, CDCl.sub.3): =7.261(37.4); 7.206(0.8); 7.070(14.2); 6.859(2.2); 4.131(0.6); 4.113(0.6); 4.050(0.6); 4.032(0.7); 4.024(3.2); 4.007(9.8); 3.989(10.0); 3.971(3.2); 3.693(0.6); 3.350(2.3); 3.333(38.7); 3. 303(0.4); 3.300(0.4); 3.232(8.1); 3.217(8.2); 2.358(0.3); 2.324(0.3); 2.298(0.4); 2.195(3.2); 2.167(50.0); 2.044(2.9); 2.005(0.4); 1.948(2.1); 1.926(3.3); 1.913(2.6); 1.901(4.1); 1.890(2. 1); 1.867(2.0); 1.857(1.5); 1.704(3.4); 1.667(2.8); 1.650(1.0); 1.642(0.9); 1.628(0.7); 1.587( 10.7); 1.460(0.7); 1.447(1.4); 1.439(1.5); 1.435(0.9); 1.426(2.6); 1.420(0.8); 1.414(1.5); 1.4 06(1.6); 1.393(0.9); 1.277(1.1); 1.259(2.0); 1.241(1.3); 1.237(1.0); 1.204(2.3); 1.195(1.7); 1. 173(2.0); 1.165(1.6); 1.152(0.9); 1.132(10.7); 1.114(21.5); 1.101(1.7); 1.096(9.9); 1.084(0. 6); 0.899(0.5); 0.882(1.5); 0.874(1.5); 0.867(1.6); 0.861(3.3); 0.855(5.1); 0.847(3.4); 0.841( 3.2); 0.834(4.1); 0.826(2.5); 0.814(1.1); 0.794(3.2); 0.786(5.0); 0.781(4.6); 0.774(5.4); 0.76 8(4.5); 0.761(1.1); 0.755(1.2); 0.008(0.7); 0.0004(19.8); 0.0002(22.6); 0.009(0.7)

[0202] Example I-13: .sup.1H-NMR(MHz, d.sub.6-DMSO): =10.689(0.9); 7.897(0.6); 7.030(3.7); 3.326(50.0); 3.293(0.8); 3.282(0.8); 3.276(1.0); 3.265(0.8); 3.250(2.5); 3.245(9.6); 2.509(12.0); 2.505(26.9); 2.500(38.0); 2.496(26.8); 2.491(12.0); 2.072(0.6); 2.041(5.9); 2.036(6.6); 1.831(0.3); 1.799(0.5); 1.774(0.4); 1.651(0.3); 1.635(0. 3); 1.601(0.3); 1.540(0.5); 1.532(0.4); 1.519(0.9); 1.507(0.5); 1.499(0.5); 1.486(0.4); 0.895(0.4); 0.885(1.1); 0.878(1.5); 0.869(0.6); 0.864(1.2); 0.858(1.3); 0.848(0.5); 0.719(0.6); 0.70 9(1.5); 0.703(1.3); 0.697(1.4); 0.690(1.3); 0.680(0.4); 0.000(5.2)

C. FORMULATION EXAMPLES

[0203] 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 inert substance and comminuting the mixture in an impact mill.

[0204] 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 ligninosulphonate and 1 part by weight of sodium oleoylmethyltaurate as wetting agent and dispersant and grinding in a pinned-disc mill.

[0205] 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 to more than 277 C.) and grinding to a fineness of below 5 microns in an attrition ball mill.

[0206] 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.

[0207] e) Water-dispersible granules are obtained by mixing

[0208] 75 parts by weight of a compound of the formula (I) and/or salts thereof,

[0209] 10 parts by weight of calcium ligninosulphonate,

[0210] 5 parts by weight of sodium laurylsulphate,

[0211] 3 parts by weight of polyvinyl alcohol and

[0212] 7 parts by weight of kaolin,

[0213] grinding the mixture in a pinned-disc mill, and granulating the powder in a fluidized bed by spray application of water as a granulating liquid.

[0214] f) Water-dispersible granules are also obtained by homogenizing and precomminuting

[0215] 25 parts by weight of a compound of the formula (I) and/or salts thereof,

[0216] 5 parts by weight of sodium 2,2 dinaphthylmethane-6,6 disulphonate,

[0217] 2 parts by weight of sodium oleoylmethyltaurate,

[0218] 1 part by weight of polyvinyl alcohol,

[0219] 17 parts by weight of calcium carbonate and

[0220] 50 parts by weight of water on a colloid mill,

[0221] 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.

D. BIOLOGICAL DATA

[0222] 1. Pre-Emergence Herbicidal Effect and Crop Plant Compatibility

[0223] Seeds of monocotyledonous and dicotyledonous weed plants and crop plants are laid out in wood-fibre pots in sandy loam and covered with soil. The compounds according to the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) are then applied as aqueous suspension or emulsion at a water application rate of 600 to 800 l/ha (converted) with the addition of 0.2% wetting agent to the surface of the covering soil.

[0224] 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).

[0225] Undesired Plants/Weeds:

TABLE-US-00005 ALOMY: Alopecurus myosuroides SETVI: Setaria viridis AMARE: Amaranthus retroflexus AVEFA: Avena fatua CYPES: Cyperus esculentus ECHCG: Echinochloa crus-galli LOLMU: Lolium multiflorum STEME: Stellaria media VERPE: Veronica persica VIOTR: Viola tricolor POLCO: Polygonum convolvulus

TABLE-US-00006 TABLE 5 Pre-emergence effectiveness Ex. Dosage No. [g/ha] ALOMY AVEFA CYPES ECHCG LOLMU SETVI AMARE VIOTR VERPE I-1 320 100 80 100 100 100 80 80 100 100 100 I-2 320 100 100 100 100 100 100 100 80 100 80 100 100 100 I-5 320 100 100 100 100 100 100 80 80 100 100 100 100 100 I-7 320 100 100 100 100 80 80 100 100 90 I-8 320 100 100 100 90 90 80 90 100 90 80 I-9 320 100 90 100 100 100 80 100 100 80 90 I-10 320 100 100 100 100 100 80 90 80 100 100 80 I-11 320 100 80 100 100 100 100 80 80 100 100 100 90 I-12 320 100 80 100 100 100 80 100 90 100 90 I-13 320 100 100 90 100 80 100 90 I-14 320 100 80 100 100 90 80 100 90

TABLE-US-00007 TABLE 6 Pre-emergence effectiveness Ex. Dosage No. [g/ha] ALOMY AVEFA CYPES ECHCG LOLMU SETVI AMARE VIOTR VERPE Ia-1 320 100 90 100 100 100 90 80 90 80 100 100 100 Ia-2 320 100 100 100 80 100 80 80 100 90 Ia-3 320 100 90 100 100 100 90 80 90 80 100 100 100 Ia-4 320 80 100 90 100 100 90 80 100 100 Ia-5 320 100 100 100 100 100 100 100 100 80 100 80 100 100 100 100 Ia-6 320 100 90 100 100 100 80 100 90 100 100 100 Ia-7 80 100 100 100 100 Ia-8 320 100 90 100 100 100 80 100 90 100 100 80 Ia-10 320 100 80 100 100 100 80 90 100 80 90 Ia-11 320 100 80 100 100 100 80 100 100 100 100 Ia-12 320 100 90 100 100 100 80 100 100 100 90 Ia-13 320 100 100 100 100 100 80 100 80 100 100 100 Ia-14 320 100 80 100 100 100 100 80 80 80 100 90 100 Ia-16 320 90 100 90 90 80 90 90 90

[0226] As the results from Tables 5 and 6 show, compounds according to the invention have a good herbicidal pre-emergence effectiveness against a broad spectrum of weed grasses and weeds. For example, the compounds No. I-1, I-2, I-5, I-9, I-10, I-11, I-12, I-14, Ia-1, Ia-2, Ia-3, Ia-5, Ia-6, Ia-8, Ia-9, Ia-10, Ia-11, Ia-12, Ia-13 and Ia-14, and at an application rate of 320 g/ha in each case exhibit an 80-100% effect against Alopecurus myosuroides, Avena fatua, Echinochloa crus-galli, Lolium multiflorum and Setaria viridis. The compounds I-7, I-8, I-13, Ia-4 and Ia-16, by contrast, at an application rate of 320 g/ha in each case exhibit an 80-100% effect against Alopecurus myosuroides, Echinochloa crus-galli, Lolium multiflorum and Setaria viridis. Accordingly, the compounds according to the invention are suitable for controlling unwanted plant growth by the pre-emergence method.

[0227] 2. Post-Emergence Herbicidal Effect and Crop Plant Compatibility

[0228] Seeds of monocotyledonous and dicotyledonous weed and crop plants are laid out in sandy loam in wood-fibre pots, covered with soil and cultivated in a greenhouse under good growth conditions. 2 to 3 weeks after sowing, the test plants are treated at the one-leaf stage. The compounds according to the invention, formulated in the form of wettable powders (WP) or as emulsion concentrates (EC), are then sprayed as aqueous suspension or emulsion at a water application rate of 600 to 800 l/ha (converted) with the addition of 0.2% of wetting agent onto the green parts of the plants. 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-00008 TABLE 7 Post-emergence effectiveness Dosage Ex. No. [g/ha] ALOMY AVEFA ECHCG LOLMU SETVI POLCO VERPE I-1 80 90 90 100 90 100 20 100 90 90 I-2 80 100 100 100 100 100 20 90 90 100 90 100 I-5 80 100 100 100 100 100 20 90 90 100 90 90 I-7 80 100 100 100 100 100 80 20 90 100 90 100 I-8 80 100 80 100 90 100 20 90 100 90 100 I-9 80 100 100 100 100 100 20 100 90 100 100 100 I-10 80 100 100 100 100 100 20 100 100 100 100 90 I-11 80 100 100 100 100 100 20 80 80 100 90 100 I-12 80 90 80 100 90 100 20 80 100 100 I-13 80 80 90 90 90 20 90 90 I-14 80 80 100 90 90 20 90 90 90

TABLE-US-00009 TABLE 8 Post-emergence action Dosage Ex. No. [g/ha] ALOMY AVEFA ECHCG LOLMU SETVI POLCO VERPE Ia-1 80 80 100 90 20 90 Ia-2 80 80 80 Ia-3 80 100 100 100 100 90 20 90 90 90 Ia-6 80 100 100 90 100 20 100 90 Ia-7 80 100 100 100 80 20 90 Ia-8 80 100 100 100 100 100 20 100 100 100 100 Ia-9 80 100 90 100 90 100 20 100 90 100 90 100 Ia-10 80 80 90 90 100 20 90 80 100 Ia-11 80 90 100 90 90 20 100 80 Ia-12 80 90 100 100 100 100 20 90 100 100 90 100 Ia-13 80 100 80 20 80

[0229] As the results from Tables 7 and 8 show, compounds according to the invention have a good herbicidal post-emergence effectiveness against a broad spectrum of weed grasses and weeds. For example, the compounds No. I-1, I-2, I-5, I-7, I-8, I-9, I-10, I-11, I-12, I-13, I-14, Ia-3, Ia-6, Ia-7, Ia-8, Ia-9, Ia-11 and Ia-12, and at an application rate of 80 g/ha in each case exhibit an 80-100% effect against Alopecurus myosuroides, Avena fatua, Echinochloa crus-galli, Lolium multiflorum and Setaria viridis. Accordingly, the compounds according to the invention are suitable for controlling unwanted plant growth by the post-emergence method.

[0230] Compared to the closest prior art (WO 2015/040114, compound 42.03), the compounds of the present invention have an improved herbicidal effect both pre-emergence and post-emergence, as the following table shows.

TABLE-US-00010 TABLE 9 Comparison data for pre-emergence effectiveness Dosage Ex. No. (g a.i./ha) AVEFA CYPES SETVI Ia-17 20 60 100 100 WO 2015/040114 20 50 0 80 [00025]

TABLE-US-00011 TABLE 10 Comparison data for post-emergence effect Dosage Ex. No. (g a.i./ha) ALOMY AVEFA PHBPU I-5 20 90 90 30 WO 2015/040114 20 80 70 0 [00026]