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

Abstract

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

X=C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl or C.sub.3-C.sub.6-cycloalkyl, Y=C.sub.1-C.sub.4-alkyl or C.sub.3-C.sub.6-cycloalkyl, R.sup.1=hydrogen, C.sub.1-C.sub.6-alkyl, or C.sub.3-C.sub.6-cycloalkyl, R.sup.2=hydrogen or methyl, R.sup.3=C.sub.1-C.sub.6-alkyl or C.sub.1-C.sub.6-alkoxy-C.sub.2-C.sub.6-alkyl, G=hydrogen, a cleavable group L or a cation E, where R.sup.3 is not equal to methyl if R.sup.1=methyl and R.sup.3 is not equal to C.sub.1-C.sub.3-alkyl if R.sup.1=H.

The invention also relates to a herbicidal composition comprising a compound of the general formula (I) and to the use of the compounds according to the invention for controlling weeds and weed grasses in crops of useful plants.

Claims

1. Alkynyl-substituted 3-phenylpyrrolidine-2,4-dion of formula (I) ##STR00032## or an agrochemically acceptable salt thereof, where X=C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl or C.sub.3-C.sub.6-cycloalkyl, Y=C.sub.1-C.sub.4-alkyl or C.sub.3-C.sub.6-cycloalkyl, R.sup.1=hydrogen, C.sub.1-C.sub.6-alkyl or C.sub.3-C.sub.6-cycloalkyl, R.sup.2=hydrogen or methyl, R.sup.3=C.sub.1-C.sub.6-alkyl or C.sub.1-C.sub.6-alkoxy-C.sub.2-C.sub.6-alkyl, G=hydrogen, a cleavable group L or a cation E; where L=one of the following radicals ##STR00033## in which R.sup.4=C.sub.1-C.sub.4-alkyl or C.sub.1-C.sub.3-alkoxy-C.sub.1-C.sub.4-alkyl; R.sup.5=C.sub.1-C.sub.4-alkyl, R.sup.6=C.sub.1-C.sub.4-alkyl, 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=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, 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[1.1.2]octanes (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 is a sulfonium ion. where R.sup.3 is not equal to methyl if R.sup.1=methyl, and R.sup.3 is not equal to C.sub.1-C.sub.3-alkyl if R.sup.1=H.

2. Compound according to claim 1, where X=C.sub.1-C.sub.4-alkyl or C.sub.3-C.sub.6-cycloalkyl, R.sup.1=hydrogen, methyl, ethyl, isopropyl or cyclopropyl, R.sup.2=hydrogen or methyl, R.sup.3=C.sub.1-C.sub.6-alkyl or C.sub.1-C.sub.4-alkoxy-C.sub.2-C.sub.4-alkyl, G=hydrogen, a cleavable group L or a cation E where L=one of the following radicals ##STR00034## in which R.sup.4=C.sub.1-C.sub.4-alkyl, R.sup.5=C.sub.1-C.sub.4-alkyl, R.sup.6=C.sub.1-C.sub.4-alkyl, an unsubstituted phenyl or phenyl substituted by halogen, C.sub.1-C.sub.4-alkyl or C.sub.1-C.sub.4-alkoxy, R.sup.7, R.sup.7=independently of each other methoxy or ethoxy, E=an alkali metal ion, an ion equivalent of an alkaline earth metal, an ion equivalent of aluminum or an ion equivalent of a transition metal, or an ammonium ion, in which optionally one, two, three or all four hydrogen atoms by identical or different radicals from the groups hydrogen or C.sub.1-C.sub.5-alkyl, or a tertiary aliphatic or heteroaliphatic ammonium ion, or a heterocyclic ammonium cation, for example in each case protonated pyridine, quinoline, quinoxaline, 1,2-dimethylimidazole, 1,3-dimethylimidazolium methylsulfate, or is a sulfonium ion where R.sup.3 is not equal to methyl if R.sup.1=methyl, and R.sup.3 is not equal to C.sub.1-C.sub.3-alkyl if R.sup.1=H.

3. Compound according to claim 1 , where R.sup.1=methyl, ethyl, isopropyl or cyclopropyl.

4. Compound according to claim 1, where R.sup.2=hydrogen.

5. Compound according to claim 1, where R.sup.3=C.sup.1-C.sup.4-alkyl.

6. Compound according to claim 1, where R.sup.3=C.sub.1-C.sub.4-alkoxy-C.sub.2-C.sub.4-alkyl.

7. Compound according to claim 1, where R.sup.1=methyl and R.sup.3=C.sub.1-C.sub.6-alkyl

8. Compound according to claim 1, where X=methyl, ethyl or cyclopropyl, Y=methyl or ethyl, and R.sup.2=hydrogen.

9. Compound according to claim 1, where G=hydrogen, a cleavable group L or a cation E, in which L=one of the following radicals ##STR00035## with R.sup.4=methyl, ethyl or isopropyl, R.sup.5=methyl or ethyl, and E=a sodium, potassium, trimethylammonium, pyridinium, quinolinium or trimethylsulfonium cation or an ion equivalent of calcium or magnesium.

10. 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.

11. Herbicidal composition according to claim 10, comprising at least one further agrochemically active substance from the group of insecticides, acaricides, herbicides, fungicides, safeners and growth regulators.

12. Herbicidal composition according to claim 11, comprising a safener.

13. Herbicidal composition according to claim 10, comprising a further herbicide.

14. Method of controlling undesired plant growth, comprising applying a compound according to claim 1 to a plant to be controlled, plant parts, plant seeds and/or an area on which the undesired plant growth could take place.

15. Method according to claim 14, where the undesired plant growth is selected from grasslike monocotyledonous weeds.

16. Method according to claim 14, where the plant growth of resistant grasses in one or more useful plants is controlled, and where a herbicidal composition comprising said compound is applied to a weed to be controlled.

17. Method according to claim 16, where the useful plant is selected from wheat, barley, rye, oats, rice, sugar cane, soybean, rapeseed, sunflower and corn.

18. A product comprising a compound of formula (I) or an agrochemically acceptable salt thereof according to claim 1 for controlling one or more harmful plants.

19. A product according to claim 18, wherein the compound of the formula (I) or an agrochemically acceptable salt thereof is used for controlling one or more harmful plants in crops of useful plants.

20. A product according to claim 19, wherein the useful plants are transgenic useful plants.

Description

A. CHEMICAL EXAMPLES

Example D11

cis-3-[4-(Cyclopropylethynyl)-2,6-dimethylphenyl]-4-hydroxy-8-methoxy-1-azaspiro[4.5]dec-3-en-2-one

[0174] ##STR00025##

[0175] 1.46 g (3.67 mmol) of cis-methyl 1-(1[4-(cyclopropylethynyl)-2,6-dimethylphenyl]acetyllamino)-4-methoxycyclohexanecarboxylate in 10 ml DMF were added dropwise over 30 min at room temperature to a solution of 1.03 g of potassium t-butoxide (9.18 mmol) in 5 ml of DMF and the mixture was stirred at this temperature for 18 h. The contents of the flask were then added to water, acidified to pH 1 with 2N hydrochloric acid, stirred for 10 minutes and the resulting precipitate filtered under suction. After drying, this gave 1.29 g (96%) of the title compound in the form of colorless crystals.

TABLE-US-00007 TABLE 7 Example numbers D4-D11 Analogously to Example A11 and also according to the general details relating to the production, the following compounds according to the invention were obtained. [00026] Ex. .sup.1H-NMR (400 MHz, ? in ppm No R.sup.3 X Y R.sup.1 Isomerism d.sub.6-DMSO) D4 C.sub.2H.sub.5 C.sub.2H.sub.5 CH.sub.3 CH.sub.3 trans 1.00 (t, 3H), 1.10 (t, 3H), 1.70- 1.89 (m, 4H), 2.49 (q, 2H), 3.40 (q, 2H), 3.41 (mc, 1H), 7.05 (s, 1H), 7.07 (s, 1H) D5 C.sub.2H.sub.5 C.sub.2H.sub.5 CH.sub.3 CH.sub.3 cis 1.01 (t, 3H), 1.12 (t, 3H), 1.41 (mc, 2H), 1.45 (mc, 2H), 1.88- 2.00 (m, 4H), 2.03 (s, 3H), 2.49 (q, 2H), 3.22 (mc, 1H), 3.48 (q, 2H), 7.08 (s, 1H), 7.09 (s, 1H) D6 C.sub.2H.sub.5 CH.sub.3 CH.sub.3 CH.sub.3 cis 1.12 (t, 3H), 1.38-1.60 (m, 4H), 1.85-2.00 (m, 4H), 2.02 (s, 3H), 2.04 (s, 6H), 3.22 (mc, 1H), 3.48 (q, 2H), 7.05 (s, 2H) D7 C.sub.2H.sub.5 CH.sub.3 CH.sub.3 CH.sub.3 trans 1.11 (t, 3H), 1.13-1.20 (m, 2H), 2.02 (s, 3H), 2.06 (s, 6H), 3.41 (q, 2H), 3.52 (mc, 1H), 7.05 (s, 2H) D8 C.sub.3H.sub.7 CH.sub.3 C.sub.2H.sub.5 CH.sub.3 cis 0.88 (t, 3H), 1.00 (t, 3H), 1.35- 1.60 (m, 6H), 2.38 (mc, 2H), 3.21 (mc, 1H), 3.40 (1, 2H), 7.05 (s, 1H), 7.06 (s, 1H) D9 C.sub.3H.sub.7 CH.sub.3 C.sub.2H.sub.5 CH.sub.3 trans 1.08 (t, 3H), 1. 12 (t, 3H), 1.16 (mc, 2H), 1.50 (sext., 2H), 1.70-1.88 (m, 4H), 2.05 (s, 3H), 2.06 (s, 3H), 2.39 (q, 2H), 3.51 (mc, 1H), 7.06 (s, 1H), 7.07 (s, 1H) D10 CH.sub.3 C.sub.2H.sub.5 CH.sub.3 cPr cis ? = 0.70 mc, 2H), 0.88 (mc, 2H), 0.99 (t, 3H), 1.35-1.60, m, 5H), 2.00 (s, 3H), 2.48 q, 2H), 3.12 (mc, 1H), 3.26 (s, 3H), 7.00 s, 1H), 7.04 (s, 1H) D11 CH.sub.3 CH.sub.3 CH.sub.3 cPr cis ? = 0.70 (mc, 2H), 0.86 (mc, 2H), 1.40-1.58 (m, 5H), 2.05 (s, 6H), 3.12 (mc, 1H), 3.25 (s, 3H), 7.02 (s, 2H)

TABLE-US-00008 TABLE 8 Example numbers P5-P15 Analogously to Example P1 and according to the general details relating to the production, the following compounds according to the invention are obtained: [00027] Ex. .sup.1H-NMR 400 MHz, ? No R.sup.3 X Y R.sup.1 L Isomerism in ppm CDCl3) P5 C.sub.2H.sub.5 CH.sub.3 CH.sub.3 CH.sub.3 CO.sub.2Et cis 0.98 (t, 3H), 1.12 (t, 3H), 1.48-1.61 (m, 4H), 1.82 (mc, 2H), 2.05 (s, 3H), 2.08 (s, 6H), 3.30 (mc, 1H), 3.49 (q, 2H), 3.99 (q, 2H), 7.08 (s, 2H) P6 C.sub.2H.sub.5 CH.sub.3 CH.sub.3 CH.sub.3 CO.sub.2Et trans 1.10 (t, 3H), 1.21 (t, 3H), 1.40-1.48 (m, 2H), 1.60 mc, 2H), 2.03 (s, 3H), 2.18 (s, 6H), 2.23 (mc, 2H), 3.47 (q, 2H), 3.58 (mc, 1H), 3.99 (q, 2H), 7.08 (s, 2H) P7 C.sub.2H.sub.5 CH.sub.3 CH.sub.3 CH.sub.3 CO.sub.2Me cis 1.10 (t, 3H), 1.48-1.65 (m, 2H), 2.02 (s, 3H), 2.06 (s, 6H), 3.30 (mc, 1H), 3.31 (s, 3H), 3.48 (q, 2H), 3.57 (s, 3H), 7.06 (s, 2H) P8 C.sub.2H.sub.5 CH.sub.3 CH.sub.3 CH.sub.3 COiPr cis 0.89 (d, 6H), 1.11 (t, 3H), 2.02 (s, 3H), 2.05 (s, 6H), 2.62 (quint., 1H), 3.36 (mc, 1H), 3.48 (q, 2H), 7.03 (s, 2H) P9 C.sub.2H.sub.5 C.sub.2H.sub.5 CH.sub.3 CH.sub.3 CO.sub.2Et cis 1.00 (t, 3H), 1.05 (t, 3H), 1.12 (t, 3H), 1.45- 1.61 (m, 4H), 2.05 (s, 3H), 2.10 (s, 3H), 2.38 (mc, 2H), 3.29 (mc, 1H), 3.49 (q, 2H), 3.98 (q, 2H), 7.07 (s, 2H) P10 C.sub.2H.sub.5 C.sub.2H.sub.5 CH.sub.3 CH.sub.3 CO.sub.2Et trans 0.99 (t, 3H), 1.04 (t, 3H), 1.11 (t, 3H), 1.25 (mc, 2H), 1.72-1.91 (m, 4H), 2.05 (s, 3H), 2.10 ( s, 3H), 2.40 (mc, 2H), 3.52 (q, 2H), 3.58 (mc, 1H), 3.99 (q, 2H), 7.09 (s, 2H) P11 C.sub.3H.sub.7 C.sub.2H.sub.5 CH.sub.3 CH.sub.3 CO.sub.2Et cis 0.92 (t, 3H), 1.10 (t, 3H), 1.12 ( t, 3H), 1.39 (mc, 2H), 1.59 (quint, 2H), 1.75 (mc, 2H), 1.91 (mc, 2H), 2.03 (s, 3H), 2.20 (s, 3H), 2.49 (mc, 2H) bzw. 1H), 3.30 (mc, 1H), 3.45 (t, 2H), 3.99 (q, 2H), 7.10 (s, 1H), 7.12 (s, 1H) P12 C.sub.3H.sub.7 C.sub.2H.sub.5 CH.sub.3 CH.sub.3 CO.sub.2Me cis 0.93 (t, 3H), 1.13 (t, 3H), 1.40 (mc, 2H), 1.61 (quint., 2H), 2.03 (s, 3H), 2.20 (s, 3H), 2.48 (mc, 2H), 3.30 (mc, 1H), 3.45 (t, 2H), 3.60 (s, 3H), 7.10 (s, 1H), 7.12 (s, 1H) P13 C.sub.3H.sub.7 C.sub.2H.sub.5 CH.sub.3 CH.sub.3 COiPr cis 0,90-1.03 (mc, ?9H), 1.12 (t, 3H), 1.40 (mc, 2H), 1.60 (mc, 3H), 2.01 (s, 3H), 2.18 (s, 3H), 2.40-2.56 (m, 4H), 3.28 (mc, 1H), 3.52 (t, 2H), 7.09 (s, 1H), 7.11 (s, 1H) P14 CH.sub.3 C.sub.2H.sub.5 CH.sub.3 cPr CO.sub.2Et cis 0.76 (mc, 2H), 0.82 (mc, 2H), 1.11 (mc, 6H), 1.70-1.95 (m, 2H), 2.15 (s, 3H), 2.48 (mc, 2H), 3.23 (mc, 1H), 3.38 (s, 3H), 4.00 (q, 2H), 7.09 (s, 1H), 7.11 (s, 1H) P15 CH.sub.3 C.sub.2H.sub.5 CH.sub.3 cPr COiPr cis 0.80 (mc, 2H), 0.85 (mc, 2H), 0.98 (mc, 6H), 1.12 (t, 3H), 1.70- 1.89 (m, 4H), 2.18 (s, 3H), 2.45 (quint, 1H), 2.50 (mc, 2H), 3.20 (mc, 1H), 3.38 (s, 3H),

Example S5

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

[0176] ##STR00028##

[0177] To 100 mg (0.27 mmol) of cis-8-ethoxy-342-ethyl-6-methyl-4-(prop-1-yn-1-yl)phenyl]-4-hydroxy-1-azaspiro[4.5]dec-3-en-2-on in 1 ml of methanol are added 60 mg of sodium methoxide and the mixture is stirred at 40? C. for 1 h. The solvent is subsequently distilled off and the residue dried under reduced pressure. This gives 102 mg of the desired compound in the form of colorless crystals.

TABLE-US-00009 TABLE 9 Example numbers S3-S5 In analogy to Example S5 and according to the general preparation details, the following compounds according to the invention are obtained: [00029] Ex. No. R.sup.3 X Y R.sup.1 M .sup.1H-NMR (400 MHz, ? in ppm, d.sub.6-DMSO) S3 C.sub.2H.sub.5 CH.sub.3 CH.sub.3 CH.sub.3 Na 1.10 (t, 3H), 1.22 (mc, 2H), 1.39 (mc, 2H), 1.65 (mc, 2H), 1.86 (mc, 2H), 2.00 (s, 3H), 2.09 (s, 3H), 3.15 (mc, 1H), 3.45 (q, 2H), 6.88 (s, 2H) S4 C.sub.2H.sub.5 C.sub.2H.sub.5 CH.sub.3 CH.sub.3 Na 0.98 (t, 3H), 1.10 (t, 3H), 1.22 (mc, 2H), 1.40 (mc, 2H), 1.66 (mc, 2H), 1.88 (mc, 2H), 2.00 (s, 3H), 2.08 (s, 3H), 3.15 (mc, 1H), 3.48 (q, 2H), 6.86 (s, 1H), 6.88 (s, 1H) S5 C.sub.3H.sub.7 C.sub.2H.sub.5 CH.sub.3 CH.sub.3 Na 0.88 (t, 3H), 0.98 (t, 3H), 1.22 (mc, 2H), 1.31-1.50 (m, 4H), 1.65 (mc, 2H), 1.86 (mc, 2H), 2.00 (s, 3H), 2.06 (s, 3H), 3.15 (mc, 1H), 3.35 (q, 2H), 6.86 (s, 1H), 6.87 (s, 3H)

B. PREPARATION EXAMPLES

Starting Materials

Example G1

Methyl cis-1-({[2,6-dimethyl-4-(prop-1-yn-1-yl)phenyl]acetyl}amino)-4-ethoxycyclohexanecarboxylate

[0178] ##STR00030##

[0179] 1.00 g (4.9 mmol) of 2,6-dimethyl-4-propynylphenyl acetic acid were dissolved in 20 ml of dichloromethane and admixed with one drop of DMF. 1.25 g (9.88 mmol) 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). 1.06 g (5 mmol) of cis-4-ethoxy-1-(methoxycarbonyl)cyclohexanaminium chloride 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 ethyl acetate/n-heptane). This gave 1.84 g (94%) of the desired target compound.

TABLE-US-00010 TABLE 10 Example numbers G1-G8 Analogously to Example G1 and according to the general details relating to the production, the following compounds are obtained [00031] Ex. 1H-NMR (400 MHz, ? in ppm, No. R.sup.3 X Y R.sup.1 CDCl3) or melting point G1 CH.sub.3 CH.sub.3 CH.sub.3 H m.p. 141? C. G2 C.sub.2H.sub.5 CH.sub.3 CH.sub.3 H m.p. 159? C. G3 C.sub.2H.sub.5 CH.sub.3 CH.sub.3 CH.sub.3 1.20 (t, 3H), 2.00 (s, 3H), 2.30 (s, 3H), 2.81 (mc, 2H), 3.20 (mc, 1H); 3.60 (s, 2H), 3.69 (s, 3H), 7.15 (s, 2H) G4 C.sub.2H.sub.5 C.sub.2H.sub.5 CH.sub.3 CH.sub.3 1.15 (t, 3H), 1.20 (t, 3H), 1.65-1.88 (m, 4H), 2.05 (s, 3H), 2.30 (s, 3H), 2.62 (mc, 2H), 3.20 (mc, 2H), 3.61 (s, 2H), 3.60 (s, 3H), 7.15 (s, 1H), 7.18 (s, 2H) G5 C.sub.3H.sub.7 CH.sub.3 CH.sub.3 CH.sub.3 G6 C.sub.3H.sub.7 C.sub.2H.sub.5 CH.sub.3 CH.sub.3 0.88 (t, 3H), 1.10 (mc, 2H), 1.22 (t, 3H), 1.52 (quint., 2H), 2.05 (s, 3H), 2.30 (s, 3H), 3.33 (t, 2H), 3.62 (s, 2H), 3.68 (s, 3H), 7.16 (s, 1H), 7.18 (s, 3H) G7 CH.sub.3 C.sub.2H.sub.5 CH.sub.3 cPr 0.80 (mc, 2H), 0.85 (mc, 2H), 1.05 (mc, 2H), 2.28 (s, 3H), 2.61 (q, 2H), 3.10 (mc, 1H), 3.28 (s, 3H), 3.61 (s, 2H), 3.69 (s, 3H), 7.15 (s, 1H), 7.17 (s, 1H) G8 CH.sub.3 CH.sub.3 CH.sub.3 cPr m.p. 129.5? C.

C. FORMULATION EXAMPLES

[0180] 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.

[0181] 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.

[0182] 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.

[0183] 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.

[0184] e) Water-dispersible granules are obtained by mixing

[0185] 75 parts by weight of a compound of the formula (I) and/or salts thereof,

[0186] 10 parts by weight of calcium ligninosulphonate,

[0187] 5 parts by weight of sodium laurylsulphate,

[0188] 3 parts by weight of polyvinyl alcohol and

[0189] 7 parts by weight of kaolin,

[0190] 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.

[0191] f) Water-dispersible granules are also obtained by homogenizing and precomminuting

[0192] 25 parts by weight of a compound of the formula (I) and/or salts thereof,

[0193] 5 parts by weight of sodium 2,2 dinaphthylmethane-6,6 disulphonate,

[0194] 2 parts by weight of sodium oleoylmethyltaurate,

[0195] 1 part by weight of polyvinyl alcohol,

[0196] 17 parts by weight of calcium carbonate and

[0197] 50 parts by weight of water on a colloid mill,

[0198] 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

[0199] 1. Pre-Emergence Herbicidal Effect

[0200] 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.

[0201] 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).

[0202] Undesired Plants/Weeds:

TABLE-US-00011 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 LOLRI Lolium rigidium HORMU Hordeum murinum

TABLE-US-00012 TABLE 5 Pre-emergence effect Dosage Herbicidal effect against [%] Ex. No. [g a.i./ha] ALOMY AVEFA CYPES ECHCG LOLRI SETVI HORMU D1 320 100 100 100 100 100 100 100 D2 320 100 100 90 100 100 100 100 D4 320 100 100 70 100 100 100 100 D6 320 100 100 100 100 100 100 100 D7 320 100 70 0 100 100 100 100 P3 320 100 100 100 100 100 100 100 P4 320 100 100 100 100 100 100 100 P5 320 100 100 100 100 100 100 100 P6 320 100 90 90 100 100 100 90 P7 320 100 100 100 100 100 100 100 P8 320 100 90 100 100 100 100 100 P9 320 100 100 60 100 100 100 100 P10 320 100 90 0 100 100 100 90 S1 320 100 100 100 100 100 100 100 S3 320 100 100 80 100 100 100 100 S4 320 100 100 60 100 100 100 100

TABLE-US-00013 TABLE 6 Pre-emergence effect Dosage Herbicidal effect against [%] Ex. No. [g a.i./ha] ALOMY AVEFA ECHCG LOLMU SETVI D10 320 100 100 100 100 100 D11 320 100 100 100 100 100 P14 320 100 100 100 100 100 P15 320 100 90 100 100 100

[0203] As the results from Tables 5 and 6 show, the 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 D1, D2, D4, D6, D7, P3-P10, S1, S3 and S4 at an application rate of 320 g/ha in each case exhibit an 80-100% effect against Alopecurus myosuroides, Avena fatua, Cyperus esculentus, Echinochloa crus-galli, Lolium rigidium, Setaria viridis and Hordeum murinum. Furthermore, the compounds D10, D11, P14 and P15 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. Accordingly, the compounds according to the invention are suitable for controlling unwanted plant growth by the pre-emergence method.

[0204] 2. Post-Emergence Herbicidal Effect

[0205] 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-00014 TABLE 7 Post-emergence effect Dosage Herbicidal effect against [%] Ex. No. [g a.i./ha] ALOMY AVEFA ECHCG LOLRI STEME HORMU D2 80 100 90 100 100 50 90 D4 80 100 100 100 100 10 100 D6 80 100 100 100 100 90 100 D7 80 100 100 100 100 20 60 P3 80 90 90 100 90 20 90 P4 80 100 90 100 100 30 90 P5 80 100 100 100 100 100 100 P6 80 100 90 100 100 20 80 P7 80 100 100 100 100 100 100 P8 80 100 100 100 100 60 100 P9 80 100 100 100 100 40 100 P10 80 100 90 100 100 10 100 S3 80 100 100 100 100 100 100 S4 80 100 100 100 100 10 100

TABLE-US-00015 TABLE 8 Post-emergence effect Herbicidal effect Dosage against [%] Ex. No. [g a. i./ha] ALOMY ECHCG SETVI D1 80 100 100 100 D10 80 100 100 100 D11 80 90 100 100 P14 80 100 100 100 P15 80 90 100 100 S1 80 90 100 100

[0206] 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 D2, D4, D6, D7, P3-P10, S3 and S4 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. The compounds D1, D10, D11, P14, P15 and S1 exhibit a 90-100% effect against Alopecurus myosuroides, Echinochloa crus-galli and Setaria viridis even at an application rate of only 80 g a.i./ha. Accordingly, the compounds according to the invention are suitable for controlling unwanted plant growth by the post-emergence method.