2-BROMO-6-ALKOXYPHENYL-SUBSTITUTED PYRROLIN-2-ONES AND THEIR USE AS HERBICIDES

Abstract

The present invention relates to novel herbicidally active 2-bromo-6-alkoxyphenyl-substituted pyrrolidine-2,4-diones of the general formula (I) or agrochemically acceptable salts thereof and to their use for controlling broad-leaved weeds and weed grasses in crops of useful plants.

Claims

1: A compound of formula (I) ##STR00042## or an agrochemically acceptable salt thereof, wherein R.sup.1 is (C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.6)-haloalkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-halocycloalkyl or (C.sub.1-C.sub.3)-alkoxy-(C.sub.2-C.sub.4)-alkyl; R.sup.2 is (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.3-C.sub.6)-cycloalkyl or (C.sub.3-C.sub.6)-halocycloalkyl; R.sup.3 is methyl, halomethyl, dihalomethyl or trihalomethyl; G is hydrogen, a leaving group L or a cation E, where L is one of the radicals below ##STR00043## wherein R.sup.4 is (C.sub.1-C.sub.4)-alkyl or (C.sub.1-C.sub.3)-alkoxy-(C.sub.2-C.sub.4)-alkyl; R.sup.5 is (C.sub.1-C.sub.4)-alkyl; R.sup.6 is (C.sub.1-C.sub.4)-alkyl, unsubstituted phenyl or phenyl which is mono- or polysubstituted by 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 and R.sup.7′ are independently of one another methoxy or ethoxy; R.sup.8 and R.sup.9 are independently of one another methyl, ethyl, or phenyl, or R.sup.8 and R.sup.9 are taken together to form a saturated 5-, 6- or 7-membered ring, or R.sup.8 and R.sup.9 are taken together to form a saturated 5-, 6- or 7-membered heterocycle having an oxygen or sulfur atom, E is 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 or a magnesium halogen cation, or is an ammonium ion in which optionally one, two, three or all four hydrogen atoms can be replaced by identical or different radicals selected from the group consisting of (C.sub.1-C.sub.10)-alkyl and (C.sub.3-C.sub.7)-cycloalkyl, wherein the C.sub.1-C.sub.10)-alkyl and (C.sub.3-C.sub.7)-cycloalkyl independently of one another may each be mono- or polysubstituted by fluorine, chlorine, bromine, cyano, hydroxy or interrupted by one or more oxygen or sulfur atoms, or is a cyclic secondary or tertiary aliphatic or heteroaliphatic ammonium ion, is a heteroaromatic ammonium cation, or is a trimethylsulfonium ion.

2: The compound according to claim 1 or an agrochemically acceptable salt thereof, wherein R.sup.1 is (C.sub.1-C.sub.3)-alkyl, (C.sub.2-C.sub.3)-haloalkyl, cyclopropyl, halocyclopropyl or (C.sub.1-C.sub.6)-alkoxyethyl; R.sup.2 is (C.sub.1-C.sub.4)-alkyl, (C.sub.1-C.sub.4)-haloalkyl, (C.sub.3-C.sub.6)-cycloalkyl or (C.sub.3-C.sub.6)-halocycloalkyl; R.sup.3 is methyl, fluoromethyl, difluoromethyl or trifluoromethyl; G is hydrogen, a leaving group L or a cation E, where L is one of the radicals below ##STR00044## wherein R.sup.4 is (C.sub.1-C.sub.4)-alkyl or (C.sub.1-C.sub.2)-alkoxyethyl; R.sup.5 is (C.sub.1-C.sub.4)-alkyl; R.sup.6 is (C.sub.1-C.sub.4)-alkyl, unsubstituted phenyl or phenyl which is mono- or polysubstituted by halogen, methyl, methoxy, halomethoxy, nitro or cyano, E is an alkali metal ion, an ion equivalent of an alkaline earth metal, an ion equivalent of aluminium, 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 can be replaced by identical or different radicals selected from the group consisting of (C.sub.1-C.sub.10)-alkyl and (C.sub.3-C.sub.7)-cycloalkyl, wherein the (C.sub.1-C.sub.10)-alkyl and (C.sub.3-C.sub.7)-cycloalkyl independently of one another may in each case be mono- or polysubstituted by fluorine, chlorine, bromine, cyano, hydroxy or be interrupted by one or more oxygen or sulfur atoms.

3: The compound according to claim 1 or an agrochemically acceptable salt thereof, wherein R.sup.1 is methyl or ethyl; R.sup.2 is methyl or ethyl; R.sup.3 is methyl, fluoromethyl, difluoromethyl or trifluoromethyl; G is hydrogen, a leaving group L or a cation E, where L is one of the radicals below ##STR00045## in which R.sup.4 is methyl, ethyl, n-propyl, isopropyl or t-butyl; R.sup.5 is methyl or ethyl; E is a sodium or potassium ion, an ion equivalent of magnesium, calcium or aluminium.

4: A method for preparing the compound of formula (I) or an agrochemically acceptable salt thereof according to claim 1, wherein the method comprises cyclizing a compound of formula (II) ##STR00046## wherein R.sup.1, R.sup.2 and R.sup.3 are as defined in claim 1 and R.sup.10 represents alkyl, optionally in the presence of a suitable solvent or diluent, with a suitable base.

5: An agrochemical composition, comprising a) at least one compound of formula (I) or an agrochemically acceptable salt thereof as defined in claim 1, and b) auxiliaries and additives customary in crop protection.

6: An agrochemical composition comprising a) at least one compound of formula (I) or an agrochemically acceptable salt thereof as defined in claim 1, b) one or more active agrochemical compounds other than component a), and optionally c) auxiliaries and additives customary in crop protection.

7: A method for controlling unwanted plants or for regulating the growth of crop plants, comprising applying an effective amount of at least one compound of formula (I) or an agrochemically acceptable salt thereof, as defined in claim 1, to the plants, the seed or the area on which the plants grow.

8-9. (canceled)

10: The method according to claim 7, wherein the crop plants are transgenic or nontransgenic crop plants.

11: The compound according to claim 1, wherein E is a cyclic secondary or tertiary aliphatic or heteroaliphatic ammonium ion selected from the group consisting of morpholinium, thiomorpholinium, piperidinium, pyrrolidinium, protonated 1,4-diazabicyclo[1.1.2]octane (DABCO), and protonated 1,5-diazabicyclo[4.3.0]undec-7-ene (DBU).

12: The compound according to claim 1, wherein E is a heteroaromatic ammonium cation selected from the group consisting of protonated pyridine, protonated 2-methylpyridine, protonated 3-methylpyridine, protonated 4-methylpyridine, protonated 2,4-dimethylpyridine, protonated 2,5-dimethylpyridine, protonated 2,6-dimethylpyridine, protonated 5-ethyl-2-methylpyridine, protonated collidine, protonated pyrrole, protonated imidazole, protonated quinoline, protonated quinoxaline, protonated 1,2-dimethylimidazole, and 1,3-dimethylimidazolium methylsulfate.

13: The compound according to claim 4, wherein R.sup.10 is methyl or ethyl.

Description

CHEMICAL EXAMPLES

[0386] The examples which follow illustrate the invention in detail.

Example 1.1

3-[2-Bromo-6-methoxy-4-(prop-1-yn-1-yl)phenyl]-4-hydroxy-8-methoxy-1-azaspiro[4.5]dec-3-en-2-one

[0387] ##STR00030##

[0388] 1.300 g (2.87 mmol) of methyl 1-{2-[2-bromo-6-methoxy-4-(prop-1-yn-1-yl)phenyl]acetamido}-4-methoxycyclohexanecarboxylate were initially charged in 5.8 ml of dimethylformamide, and 0.790 g (6.32 mmol) of potassium tert-butoxide was added. The mixture was stirred at room temperature for 1 h, water was added and the mixture was washed with dichloromethane and acidified with 2N aqueous hydrochloric acid. The precipitated solid was filtered off with suction.

[0389] This gave 900 mg of a yellow solid (74% yield).

Example 1.2

Sodium 3-[2-bromo-6-methoxy-4-(prop-1-yn-1-yl)phenyl]-8-methyl-2-oxo-1-azaspiro[4.5]dec-3-en-4-olate

[0390] ##STR00031##

[0391] 0.102 g (0.243 mmol) of 3-[2-bromo-6-methoxy-4-(prop-1-yn-1-yl)phenyl]-4-hydroxy-8-methoxy-1-azaspiro[4.5]dec-3-en-2-one was dissolved in 0.219 ml of methanol, 0.054 ml of 25% strength methanolic sodium methoxide solution was added and the mixture was stirred for 15 min.

[0392] The mixture was concentrated under reduced pressure.

[0393] This gave 110 mg of the desired salt (yield 100%).

Example 1.3

3-[2-Bromo-6-methoxy-4-(prop-1-yn-1-yl)phenyl]-8-methoxy-2-oxo-1-azaspiro[4.5]dec-3-en-4-yl ethyl carbonate

[0394] ##STR00032##

[0395] 0.750 g (1.78 mmol) of 3-[2-bromo-6-methoxy-4-(prop-1-yn-1-yl)phenyl]-4-hydroxy-8-methoxy-1-azaspiro[4.5]dec-3-en-2-one and 0.361 g of triethylamine were initially charged in 1.16 ml of methylene chloride, and 0.232 g (2.14 mmol) of ethyl chloroformate was added dropwise. The mixture was left to stir at room temperature for 1 h. The mixture was washed with water, dried and concentrated and the residue was purified chromatographically.

[0396] This gave 0.67 g of a light-coloured solid (yield 76%).

[0397] Analogously to this example and also according to the general details relating to the preparation, the following compounds are obtained:

##STR00033##

TABLE-US-00002 TABLE 1 Compounds of the general formula (I) Example No. R.sup.1 R.sup.2 R.sup.3 G .sup.1H-NMR (400 MHz, δ in ppm) 1.1 Me Me Me H (DMSO-d6) δ = 1.40-1.55 (m, 4H), 1.85 (mc, 2H), 1.95 (d, br, 2H), 2.05 (s, 3H), 3.10 (mc, 1H), 3.25 (s, 3H), 3.70 (s, 3H), 6.95 (s, 1H), 7.20 (s, 1H), 7.95 (s, 1H) 1.2 Me Me Me Na (DMSO-d6) δ = 1.20-1.40 (m, 4H), 1.60 (mc, 2H), 1.85 (mc, 2H), 2.05 (s, 3H), 3.05 (mc, 1H), 3.25 (s, 3H), 3.60 (s, 3H), 6.75 (s, 1H), 7.05 (s, 1H) 1.3 Me Me Me —C(O)OEt (CDCl.sub.3) δ = 1.15 (t, 3H), 1.40 (mc, 2H), 1.80 (d, br, 2H), 1.95 (mc, 2H), 2.05 (s, 3H), 2.20 (d, br, 2H), 3.25 (mc, 1H), 3.40 (s, 3H), 3.80 (s, 3H), 4.05 (q, 2H), 6.25 (s, 1H), 6.85 (s, 1H), 7.25 (s, 1H) 1.4 Me Me Me —C(O)CHMe.sub.2 (CDCl.sub.3) δ = 1.10 (mc, 6H), 1.40 (mc, 2H), 1.80 (mc, 2H), 1.90 (mc, 2H), 2.05 (s, 3H), 2.20 (mc, 2H), 2.60 (sept, 1H), 3.20 (mc, 1H), 3.40 (s, 3H), 3.80 (s, 3H), 6.20 (s, 1H), 6.85 (s, 1H), 7.25 (s, 1H) 1.5 Et Me Me H (DMSO-d6) δ = 1.20 (t, 3H), 1.35-1.60 (m, 4H), 1.85 (mc, 2H), 1.95 (d, br, 2H), 2.05 (s, 3H), 3.15 (mc, 1H), 3.25 (s, 3H), 3.95 (q, 2H), 6.95 (s, 1H), 7.20 (s, 1H), 8.00 (s, 1H) 1.6 Et Me Me Na (DMSO-d6) δ = 1.15 (t, 3H), 1.20-1.40 (m, 4H), 1.60 (mc, 2H), 1.90 (d, br, 2H), 2.05 (s, 3H), 3.05 (mc, 1H), 3.25 (s, 3H), 3.85 (q, 2H), 6.75 (s, 1H), 7.05 (s, 1H) 1.7 Et Me Me —C(O)OEt (CDCl.sub.3) δ = 1.15 (t, 3H), 1.35 (t, 3H), 1.25-1.40 (m, 4H), 1.70- 1.85 (m, 2H), 1.95 (mc, 2H), 2.05 (s, 3H), 2.20 (d, br, 2H), 3.20 (mc, 1H), 3.40 (s, 3H), 3.95 (mc, 2H), 4.05 (mc, 2H), 6.20 (s, 1H), 6.80 (s, 1H), 7.25 (s, 1H)

[0398] Preparation Examples Starting Materials:

Example A.1

Methyl 1-{2-[2-bromo-6-methoxy-4-(prop-1-yn-1-yl)phenyl]acetamido}-4-methoxycyclohexanecarboxylate

[0399] ##STR00034##

[0400] 1.000 g (3.53 mmol) of [2-bromo-6-methoxy-4-(prop-1-yn-1-yl)phenyl]acetic acid was dissolved in 3.33 ml of dichloromethane and 2 drops of dimethylformamide were added. At room temperature, 0.616 ml (7.06 mmol) of oxalyl chloride was slowly added dropwise and the mixture was then heated at reflux until the evolution of gas had ceased and concentrated. In a separate reaction, 0.790 g (3.53 mmol) of 4-methoxy-1-(methoxycarbonyl)cyclohexanaminium chloride and 1.969 ml of triethylamine were initially charged in 3.3 ml of dichloromethane, and the acid chloride dissolved in dichloromethane was added dropwise. Stirring at room temperature was continued for 1 h.

[0401] The mixture was washed with water, the phases were separated and the organic phase was dried over sodium sulfate. After concentrating, the residue was purified chromatographically.

[0402] This gave 1.3 g of a light-coloured oil (yield 81%).

[0403] Analogously to this example and also according to the general details relating to the preparation, the following compounds are obtained:

TABLE-US-00003 TABLE A Compounds of the general formula (II) in which R.sup.10 = Me Example No. R.sup.1 R.sup.2 R.sup.3 1H-NMR (400 MHz, δ in ppm) A.1 Me Me Me (CDCl.sub.3) δ = 1.20 (mc, 2H), 1.80 (mc, 2H), 1.90 (mc, 2H), 2.05 (s, 3H), 2.10 (d, br, 2H), 3.15 (mc, 1H), 3.30 (s, 3H), 3.65 (s, 3H), 3.75 (s, 2H), 3.85 (s, 3H), 5.60 (s, 1H), 6.90 (s, 1H), 7.30 (s, 1H) A.2 Et Me Me (DMSO-d6) δ = 1.30 (t, 3H), 1.45 (mc, 2H), 1.65 (mc, 2H), 1.80 (d, br, 2H), 2.05 (mc, 4H), 3.15 (mc, 1H), 3.20 (s, 3H), 3.50 (s, 3H), 3.70 (s, 2H), 4.00 (q, 2H), 6.95 (s, 1H), 7.15 (s, 1H) 8.10 (s, 1H)

Example B.2

[2-Bromo-6-methoxy-4-(prop-1-yn-1-yl)phenyl]acetic acid

[0404] ##STR00035##

[0405] At room temperature, 0.051 g (1.28 mmol) of sodium hydroxide was added to a solution of 0.2 g (0.64 mmol) of methyl [2-bromo-6-ethoxy-4-(prop-1-yn-1-yl)phenyl]acetate in 20 ml of tetrahydrofuran and 20 ml of water and the reaction mixture was heated at 50° C. for 1 h. After cooling to room temperature, the tetrahydrofuran was removed by distillation under reduced pressure and the product was precipitated by addition of 1M aqueous hydrochloric acid.

[0406] Filtration with suction gave 180 mg of a solid (yield 84%) which was used without further purification.

[0407] Analogously to this example and also according to the general details relating to the preparation, the following compounds are obtained:

##STR00036##

TABLE-US-00004 TABLE B Compounds of the general formula (XII) Example No. R.sup.1 R.sup.2 1H-NMR (400 MHz, δin ppm) B.1 Me Me (CDCl.sub.3) δ = 2.05 (s, 3H), 3.80 (s, 3H), 3.90 (s, 2H), 6.80 (s, 1H), 7.25 (s, 1H) B.2 Et Me (DMSO-d6) δ = 1.30 (t, 3H), 2.05 (s, 3H), 3.65 (s, 2H), 4.05 (q, 2H), 7.00 (s, 1H), 7.20 (s, 1H)

Methyl [2-bromo-6-ethoxy-4-(prop-1-yn-1-yl)phenyl]acetate

[0408] ##STR00037##

[0409] At 0° C. and with stirring, 1.5 ml (0.75 mmol) of a 0.5 M solution of 1-propynylmagnesium bromide in tetrahydrofuran were added dropwise to a solution of 0.102 g (0.75 mmol) of zinc chloride and 0.032 g (0.75 mmol) of lithium chloride in 7 ml of dry tetrahydrofuran under nitrogen. With stirring, the solution was warmed to room temperature over 1.5 h.

[0410] In a second reaction, under nitrogen, 2.8 mg (0.01 mmol) of palladium(II) acetate and 10.6 mg (0.02 mmol) of 1,4-bis(diphenylphosphino)butane in 3 ml of dry tetrahydrofuran were stirred at room temperature for 30 min.

[0411] In a third reaction, 0.2 g (0.5 mmol) of methyl (2-bromo-6-ethoxy-4-iodophenyl)acetate in 2 ml of dry tetrahydrofuran was dissolved under nitrogen and stirred at room temperature for 30 min.

[0412] Under nitrogen and with stirring, the solution of the second reaction was added dropwise to the solution of the first reaction, followed by addition of the solution of the third reaction. After the addition had ended, the mixture was stirred at 60° C. for 3.5 h.

[0413] After cooling to room temperature, water and saturated ammonium chloride solution were added, the mixture was extracted with ethyl acetate and the organic phase was dried and concentrated. The crude product was purified chromatographically.

[0414] This gave 98 mg of the desired intermediate (yield 63%).

[0415] .sup.1H-NMR (400 MHz, δ in ppm, CDCl.sub.3)

[0416] δ=1.35 (t, 3H), 2.05 (s, 3H), 3.70 (s, 3H), 3.85 (s, 2H), 4.00 (q, 2H), 6.80 (s, 1H), 7.20 (s, 1H)

Methyl (2-bromo-4-iodo-6-methoxyphenyl)acetate

[0417] ##STR00038##

[0418] 1.300 g (4.74 mmol) of methyl (4-amino-2-bromo-6-methoxyphenyl)acetate were dissolved in 19 ml of acetonitrile, and 2.706 g (14.2 mmol) of p-toluenesulfonic acid were added. The suspension was cooled to 10-15° C., and a solution of 0.654 g (9.48 mmol) of sodium nitrite and 1.968 g (11.08 mmol) of potassium iodide in 1.8 ml of water was slowly added. After 10 min, the mixture was warmed to room temperature and stirred at 20° C. for a further 30 min.

[0419] Water was added, the pH was adjusted to pH 8 with saturated sodium bicarbonate solution, and saturated sodium thiosulfate was added. Following extraction with ethyl acetate, the extract was concentrated and the residue was purified chromatographically.

[0420] This gave 1.005 g of a yellow-orange oil (55% yield).

[0421] .sup.1H-NMR (400 MHz, δ in ppm, CDCl.sub.3)

[0422] δ=3.70 (s, 3H), 3.80 (s, 3H), 3.85 (s, 2H), 7.10 (s, 1H), 7.55 (s, 1H)

Methyl (4-amino-2-bromo-6-methoxyphenyl)acetate

[0423] ##STR00039##

[0424] 1.450 g (4.76 mmol) of methyl (2-bromo-6-methoxy-4-nitrophenyl)acetate were dissolved in 11 ml of tetrahydrofuran, and a solution of 2.040 g (38.1 mmol) of ammonium chloride in 5.3 ml of water and 2.494 g (38.1 mmol) of zinc were added. The mixture was stirred at room temperature for 30 min. The mixture was filtered, the filtrate was diluted with water and extracted with ethyl acetate, adjusting the pH to greater than 7. The extract was dried with sodium sulfate and concentrated. This gave 1.3 g of an orange oil (99% yield).

[0425] .sup.1H-NMR (400 MHz, δ in ppm, CDCl.sub.3)

[0426] δ=3.70 (s, 3H), 3.75 (s, 5H), 6.15 (s, 1H), 6.55 (s, 1H)

Methyl (2-bromo-6-methoxy-4-nitrophenyl)acetate

[0427] ##STR00040##

[0428] 3.636 g (10.0 mmol) of 1-bromo-3-methoxy-5-nitro-2-(2,2,2-trichloroethyl)benzene were dissolved in 10 ml of methanol, and 10 ml (54.4 mmol) of a 30% strength methanolic sodium methoxide solution were added slowly, resulting in the evolution of heat. The mixture was then heated under reflux for 12 h.

[0429] 1.1 ml of concentrated sulfuric acid were added carefully, resulting in the evolution of heat. The mixture was heated under reflux for 1 h. The mixture was concentrated and the residue was dissolved in water and extracted with dichloromethane. The extract was dried with sodium sulfate, concentrated and chromatographed. This gave 1.45 g of a yellow oil (48% yield).

[0430] .sup.1H-NMR (400 MHz, δ in ppm, CDCl.sub.3)

[0431] δ=3.70 (s, 3H), 3.94 (s, 3H), 3.96 (s, 2H), 7.70 (s, 1H), 8.10 (s, 1H)

1-Bromo-3-methoxy-5-nitro-2-(2,2,2-trichloroethyl)benzene

[0432] ##STR00041##

[0433] 1.547 g (15.0 mmol) of tert-butyl nitrite and 1.842 g (13.7 mmol) of copper(II) chloride were suspended in 7.8 ml of acetonitrile and cooled to 0° C. 16.48 g (170 mmol) of vinylidene chloride were then slowly added dropwise and the mixture was allowed to warm to room temperature. 2.470 g (10 mmol) of 2-bromo-6-methoxy-4-nitroaniline, dissolved in 10 ml of acetonitrile and 25 ml of acetone, were then slowly added dropwise. Stirring at room temperature was continued until the evolution of gas had ceased.

[0434] With ice-cooling, the mixture was slowly added to 2 ml of 10% strength aqueous hydrochloric acid and extracted with ethyl acetate, and the extract was dried with magnesium sulfate and concentrated.

[0435] This gave 3.636 g of a crude product which still contained copper salts and was used directly for the next reaction.

[0436] A. Formulation Examples

[0437] 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.

[0438] 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-disc mill.

[0439] 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.

[0440] 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 oxyethylated nonylphenol as emulsifier.

[0441] e) Water-dispersible granules are obtained by mixing

[0442] 75 parts by weight of a compound of the formula (I) and/or salts thereof,

[0443] 10 parts by weight of calcium lignosulfonate,

[0444] 5 parts by weight of sodium laurylsulfate,

[0445] 3 parts by weight of polyvinyl alcohol and

[0446] 7 parts by weight of kaolin,

[0447] 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.

[0448] f) Water-dispersible granules are also obtained by homogenizing and precomminuting, in a colloid mill,

[0449] 25 parts by weight of a compound of the formula (I) and/or salts thereof,

[0450] 5 parts by weight of sodium 2,2′-dinaphthylmethane-6,6′-disulfonate,

[0451] 2 parts by weight of sodium oleoylmethyltaurate,

[0452] 1 part by weight of polyvinyl alcohol,

[0453] 17 parts by weight of calcium carbonate and

[0454] 50 parts by weight of water,

[0455] 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.

[0456] B. Biological Data

[0457] 1. Pre-emergence herbicidal effect and crop plant compatibility Seeds of monocotyledonous and dicotyledonous weed plants and crop plants are laid out in sandy loam soil in wood-fibre 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.

[0458] 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).

[0459] 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 LOLRI: Lolium rigidum STEME: Stellaria media VERPE: Veronica persica VIOTR: Viola tricolor POLCO: Polygonum convolvulus ABUTH: Abutylon threophrasti HORMU: Hordeum murinum

[0460] 1. Pre-Emergence Effectiveness

[0461] As the results from Table 2 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 each show, at an application rate of 320 g/ha, an activity of 100% against Alopecurus myosuroides, Avena fatua, Echinochloa crus-galli, Lolium multiflorum and Setaria viridis. The compounds of the invention are therefore suitable for control of unwanted plant growth by the pre-emergence method.

TABLE-US-00006 TABLE 2 Pre-emergence action Example Dosage number [g/ha] ALOMY AVEFA CYPES ECHCG LOLRI SETVI 1.1 320 100 100 100 100 100 100 1.2 320 100 100 100 100 100 100 1.3 320 100 100 100 100 100 100 1.4 320 100 100 100 100 100 100 Example number ABUTH AMARE POLCO STEME VIOTR VERPE HORMU 1.1 100 100 100 100 100 100 100 1.2 100 100 100 100 100 100 100 1.3 100 100 100 100 100 100 100 1.4 100 100 100 100 100 100 100

[0462] 2. Post-Emergence Herbicidal Effect and Crop Plant Compatibility

[0463] Seeds of monocotyledonous and dicotyledonous weed and crop plants are laid out in sandy loam soil 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 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-00007 TABLE 3 Post-emergence action Example Dosage number [g/ha] ALOMY AVEFA ECHCG LOLRI SETVI HORMU 1.1 80 90 100 100 100 90 100 1.2 80 90 90 100 90 90 100 1.3 80 90 90 100 100 90 100 1.4 80 90 90 90 100 90 100

[0464] As the results from Table 3 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 Nos. 1.1, 1.2, 1.3, 1.4 each show, at an application rate of 80 g/ha, an activity of 90-100% against Alopecurus myosuroides, Avena fatua, Echinochloa crus-galli, Lolium multiflorum, Setaria viridis and Hordeum murinum. The compounds of the invention are therefore suitable for control of unwanted plant growth by the post-emergence method.