SPECIFICALLY SUBSTITUTED 3-(2-ALKOXY-6-ALKYL-4-PROPINYLPHENYL)-3-PYRROLIN-2-ONES AND THEIR USE AS HERBICIDES

Abstract

The present invention relates to novel herbicidally active 3-phenylpyrrolin-2-ones 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. 3-Phenylpyrrolin-2-one of formula (I) or an agrochemically acceptable salt thereof, ##STR00029## wherein X represents C.sub.1-C.sub.6-alkoxy or C.sub.1-C.sub.6-haloalkoxy, Y represents C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl or C.sub.3-C.sub.6-cycloalkyl, R.sup.1 represents C.sub.3-C.sub.6-alkoxy, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.2-C.sub.6-alkenyloxy or C.sub.2-C.sub.6-haloalkenyloxy, R.sup.2 represents hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.4-alkoxy-C.sub.2-C.sub.4-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy or C.sub.1-C.sub.6-haloalkoxy, G represents hydrogen, a leaving group L or a cation E, where L represents one of the radicals below ##STR00030## in which R.sup.3 represents C.sub.1-C.sub.4-alkyl or C.sub.1-C.sub.3-alkoxy-C.sub.1-C.sub.4-alkyl, R.sup.4 represents C.sub.1-C.sub.4-alkyl, R.sup.5 represents 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.6, R.sup.6′ independently of one another represents methoxy or ethoxy, R.sup.7, R.sup.8 each independently of one another represents methyl, ethyl, phenyl or together form a saturated 5-, 6- or 7-membered ring, wherein a ring carbon atom may optionally be replaced by an oxygen or sulfur atom, E represents 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 are replaced by identical or different radicals from the groups C.sub.1-C.sub.10-alkyl or C.sub.3-C.sub.7-cycloalkyl which may each independently of one another be mono- or polysubstituted by fluorine, chlorine, bromine, cyano, hydroxy or interrupted by one or more oxygen or sulfur atoms, represents a cyclic secondary or tertiary aliphatic or heteroaliphatic ammonium ion, for example morpholinium, thiomorpholinium, piperidinium, pyrrolidinium, or in each case protonated 1,4-diazabicyclo[1.1.2]octane (DABCO) or 1,5-diazabicyclo[4.3.0]undec-7-ene (DBU), represents a heteroaromatic ammonium cation, for example in each case protonated pyridine, 2-methylpyridine, 3-methylpyridine, 4-methylpyridine, 2,4-dimethylpyridine, 2,5-dimethylpyridine, 2,6-dimethylpyridine, 5-ethyl-2-methylpyridine, collidine, pyrrole, imidazole, quinoline, quinoxaline, 1,2-dimethylimidazole, 1,3-dimethylimidazolium methylsulfate or furthermore also represents a trimethylsulfonium ion.

2. The compound of formula (I) according to claim 1 or an agrochemically acceptable salt thereof, wherein the radicals have the following meanings: X represents C.sub.1-C.sub.4-alkoxy or C.sub.1-C.sub.4-haloalkoxy, Y represents C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl or C.sub.3-C.sub.6-cycloalkyl, R.sup.1 represents C.sub.3-C.sub.6-alkoxy, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.2-alkyl, cyclopropyl, C.sub.1-C.sub.6-haloalkyl, C.sub.3-C.sub.6-alkenyloxy or C.sub.3-C.sub.6-haloalkenyloxy, R.sup.2 represents hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.2-haloalkyl, cyclopropyl, C.sub.2-C.sub.4-alkenyl, C.sub.2-C.sub.4-alkynyl, C.sub.1-C.sub.4-alkoxy or C.sub.1-C.sub.4-haloalkoxy, G represents hydrogen, a leaving group L or a cation E, where L represents one of the radicals below ##STR00031## in which R.sup.3 represents C.sub.1-C.sub.4-alkyl or C.sub.1-C.sub.3-alkoxy-C.sub.1-C.sub.4-alkyl, R.sup.4 represents C.sub.1-C.sub.4-alkyl, R.sup.5 represents 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 or C.sub.1-C.sub.4-haloalkyl, E represents 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 are replaced by identical or different radicals from the groups C.sub.1-C.sub.10-alkyl or C.sub.3-C.sub.7-cycloalkyl which are each independently of one another mono- or polysubstituted by fluorine, chlorine, bromine, cyano, hydroxy.

3. The compound of formula (I) according to claim 1 or an agrochemically acceptable salt thereof, wherein the radicals have the following meanings: X represents C.sub.1-C.sub.4-alkoxy or C.sub.1-C.sub.4-haloalkoxy, Y represents C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl or cyclopropyl, R.sup.1 represents C.sub.3-C.sub.6-alkoxy, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.2-alkyl, cyclopropyl, C.sub.3-C.sub.6-haloalkyl, C.sub.3-C.sub.4-alkenyloxy or C.sub.3-C.sub.4-haloalkenyloxy, R.sup.2 represents hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.2-haloalkyl, C.sub.2-C.sub.4-alkenyl, C.sub.2-C.sub.4-alkynyl, C.sub.1-C.sub.2-alkoxy or C.sub.1-C.sub.4-haloalkoxy, G represents hydrogen, a leaving group L or a cation E, where L represents one of the radicals below ##STR00032## in which R.sup.3 represents C.sub.1-C.sub.4-alkyl or C.sub.1-C.sub.3-alkoxy-C.sub.1-C.sub.4-alkyl, R.sup.4 represents C.sub.1-C.sub.4-alkyl, E represents 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 are replaced by identical or different radicals from the groups C.sub.1-C.sub.10-alkyl or C.sub.3-C.sub.7-cycloalkyl are substituted.

4. The compound of formula (I) according to claim 1 or an agrochemically acceptable salt thereof, wherein the radicals have the following meanings: X represents methoxy, ethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy or 2,2-difluoroethoxy, Y represents methyl, ethyl or cyclopropyl, R.sup.1 represents n-propoxy, n-butoxy, allyloxy, methoxymethyl or ethoxymethyl, R.sup.2 represents hydrogen or methyl, G represents hydrogen, a leaving group L or a cation E, where L represents one of the radicals below ##STR00033## in which R.sup.3 represents methyl, ethyl, i-propyl or t-butyl, R.sup.4 represents methyl or ethyl, E represents a sodium ion or a potassium ion.

5. A process for preparing a compound of formula (I) or an agrochemically acceptable salt thereof according to claim 1 comprising cyclizing a compound of formula (II) ##STR00034## in which R.sup.1, R.sup.2, X and Y have the meanings given above and R.sup.9 represents alkyl, optionally represents methyl or ethyl, optionally in the presence of a suitable solvent or diluent, with a suitable base with formal cleaving off of the group R.sup.9OH.

6. 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) one or more auxiliaries and/or additives customary in crop protection.

7. 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 ingredients other than component a), and optionally c) one or more auxiliaries and additives customary in crop protection.

8. A method for controlling one or more unwanted plants or for regulating the growth of one or more 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, seed and/or an area on which plants grow.

9. A product comprising a compound of formula (I) or an agrochemically acceptable salt thereof, as defined in claim 1, as an herbicide or plant growth regulator.

10. The product as claimed in claim 9, wherein the compound of formula (I) or an agrochemically acceptable salt thereof is used for controlling one or more harmful plants or for regulating growth in one or more plant crops.

11. The product as claimed in claim 10, wherein the plant crops are transgenic or nontransgenic crop plants.

Description

A. CHEMICAL EXAMPLES

[0356] The following abbreviations are used in the evaluation of NMR signals:

[0357] s (singlet), d (doublet), t (triplet), q (quartet), quint (quintet), sext (sextet), sept (septet), m (multiplet), me (multiplet centred)

Example D1: 4-Hydroxy-3-[2-methoxy-6-methyl-4-(prop-1-yn-1-yl)phenyl]-7-propoxy-1-azaspiro[4.5]dec-3-en-2-one

[0358] ##STR00023##

[0359] At room temperature, 5.35 g (12.4 mmol) of 2-[2-methoxy-6-methyl-4-(prop-1-yn-1-yl)phenyl]-N-(1-methyl-3-propoxycyclohexyl)acetamide in 50 ml of DMF were added dropwise over 30 min to a solution of 3.18 g (28.43 mmol) of potassium t-butoxide in 70 ml of DMF, and stirring was continued for 12 h at room temperature. The reaction mixture was then carefully added to an ice/water mixture and acidified to pH 2 with 2N hydrochloric acid. The precipitated solid was filtered off with suction, washed with water, dried and chromatographed on silica gel using hexane/acetic ester. This gave 4.30 g (87%) of the desired title compound.

[0360] .sup.1H-NMR [400 MHz, δ in ppm, d.sub.6-DMSO]: δ=0.85 (me, 3H), 0.98-1.10 (m, 1H), 1.21-1.30 (m, 1H), 1.49 (me, 2H), 1.45-1.79 (m, 4H), 2.02 (s, 3H), 3.38 (me, 2H), 3.55 (me, 1H), 3.64 and 3.67 (in each case s, Σ 3H), 6.79 and 6.85 (in each case s, in each case 1H)

[0361] Analogously to Example D1 and also according to the general details relating to the production, the following compounds according to the invention are obtained.

##STR00024##

TABLE-US-00001 Example No. R.sup.1 X Y .sup.1H-NMR [400 MHz, δ in ppm, d.sub.6-DMSO] D2 nC.sub.3H.sub.7O− OCH.sub.3 CH.sub.3 δ = 0.88 (t, 3H), 1.78-1.95 (m, 2H), 2.01 and 2.02 (in each case s, in each case 3H), 3.18 (mc, 1H), 3.37 (t, 2H), 3.61 (s, 3H), 6.72 and 6.80 (in each case s, in each case 1H) D3 iC.sub.3H.sub.7O− OCH.sub.3 CH.sub.3 δ = 1.08 (d, 6H), 1.33-1.43 (m, 1H), 1.45-1.54 (m, 1H), 2.00 and 2.10 (in each case s, in each case 3H), 3.38 (mc, 1H), 3.63 (s, 3H), 3.71 (hept., 1H), 6.78 and 6.83 (in each case s, in each case 1H) D4 nC.sub.4H.sub.9O− OCH.sub.3 CH.sub.3 D5 CH.sub.2 = CHCH.sub.2O− OCH.sub.3 CH.sub.3 δ = 1.39 (mc, 1H), 1.50-1.61 (m, 1H), 1.79-1.99 (m, 4H), 2.01 and 2.02 (in each case s, in each case 3H), 3.29 (mc, 1H), 3.62 (s, 3H), 4.00 (mc, 2H), 5.11 and 5.26 (in each case mc, in each case 1H), 5.82-5.95 (m, 1H), 6.79 and 6.84 (in each case s, in each case 1H) D6 CH.sub.3OCH.sub.2− OCH.sub.3 CH.sub.3 δ = 1.21-1.40 (m, 2H), 1.48-1.60 (m, 1H), 1.62-1.88 (m, 4H), 2.02 and 2.03 (in each case s, in each case 3H), 3.12 (d, 2H), 3.22 (s, 3H), 3.63 (s, 3H), 6.78 and 6.83 (in each case s, in each case 1H)

Example P1: 3-[2-Methoxy-6-methyl-4-(prop-1-yn-1-yl)phenyl]-2-oxo-7-propoxy-1-azaspiro[4.5]dec-3-en-4-yl pivalate

[0362] ##STR00025##

[0363] 100.0 mg (0.26 mmol) of 4-hydroxy-3-[2-methoxy-6-methyl-4-(prop-1-yn-1-yl)phenyl]-7-propoxy-1-azaspiro[4.5]dec-3-en-2-one and 2 ml of triethylamine were initially charged in 15 ml of dichloromethane and stirred at room temperature for 10 min. Subsequently, 35 mg (0.28 mmol) of 2,2-dimethylpropanoyl chloride in 3 ml of dichloromethane was slowly added dropwise and the mixture was then left to stir at room temperature for 14 h. It was then taken up in 20 ml of dichloromethane, washed with 10 ml of sodium bicarbonate solution and 2×10 ml of water, dried (magnesium sulfate) and the solvent was removed by distillation. This crude product was purified by chromatography on silica gel (ethyl acetate/n-heptane). Yield 86 mg (52%) as a colourless solid.

[0364] Analogously to Example P1 and also according to the general details relating to the production, the following compounds according to the invention are obtained:

##STR00026##

TABLE-US-00002 Example No. R.sup.1 X Y L .sup.1-NMR [400 MHz, δ in ppm, CDCl.sub.3] P1 nC.sub.3H.sub.7O CH.sub.3 CH.sub.3O− −COtBu δ = 0.91 (t, 3H), 1.09 (s, 9H), 1.58 (mc, 2H), 2.02 (s, 3H), 2.20 and 2.22 (in each case s, Σ3H), 3.39 (mc, 1H), 3.41 (mc, 2H), 3.70 (s, 3H), 6.71 and 6.88 (in each case s, in each case 1H) P2 nC.sub.3H.sub.7O CH.sub.3 CH.sub.3O− −CO.sub.2CH.sub.3 δ = t, 3H), 2.04 (s, 3H), 2.19 and 2.21 (in each case s, Σ 3H), 3.36 (mc, 1H), 3.42 (t, 2H), 3.60 (s, 3H), 3.71 and 3.73 (in each case s, Σ 3H), 6.76 and 6.90 (in each case s, in each case 1H) P3 nC.sub.3H.sub.7O CH.sub.3 CH.sub.3O− −CO.sub.2C.sub.2H.sub.5 δ = 0.90 and 1.11 (in each case t, in each case 3H), 1.59 (mc, 2H), 2.05 (s, 3H), 2.18 and 2.21 (in each case s, Σ 3H), 3.32-3.48 (m, 3H), 3.72 and 3.74 (in each case s, Σ 3H), 4.00 (mc, 2H), 6.75 and 6.89 (in each case s, in each case 1H) P4 nC.sub.3H.sub.7O CH.sub.3 CH.sub.3O− −COiC.sub.3H.sub.7 δ = 0.89 (t, 3H), 1.00 (mc, 6H), 2.03 (s, 3H), 1.99 and 2.01 (in each case s, Σ 3H), 2.52 (hept, 1H), 3.33 (mc, 1H), 3.42 (mc, 2H), 3.70 and 3.71 (in each case s, Σ 3H), 6.71 and 6.88 (in each case s, in each case 1H) P5 nC.sub.3H.sub.7O CH.sub.3 CH.sub.3O− −COC.sub.2H.sub.5 δ = 0.91 and 0.99 (in each case t, in each case 3H), 2.02 (s, 3H), 2.19 and 2.21 (in each case s, Σ 3H), 2.31 (q, 2H), 3.32 (mc, 1H), 3.43 (mc, 2H), 3.71 and 3.72 (in each case s, Σ 3H), 6.74 and 6.89 (in each case s, in each case 1H)

[0365] Analogously to Example P and also according to the general details relating to the production, the following compounds according to the invention are obtained:

##STR00027##

TABLE-US-00003 Example No. R.sup.1 X Y L .sup.1-NMR[400 MHz, δ in ppm, CDCl.sub.3] Q1 nC.sub.3H.sub.7O− CH.sub.3 CH.sub.3O− −CO.sub.2CH.sub.3 Q2 nC.sub.3H.sub.7O− CH.sub.3 CH.sub.3O− −CO.sub.2C.sub.2H.sub.5 δ = 0.93 and 1.12 (in each case t, in each case 3H), 1.38 (mc, 2H), 1.60 (mc, 2H), 1.68-1.71 (m, 2H), 1.85-1.98 (m, 2H), 2.02 and 2.20 (in each case s, in each case 2H), 3.29 (mc, 1H), 3.42 (t, 2H), 3.71 (s, 3H), 4.00 (mc, 2H), 6.72 and 6.87 (in each case s, in each case 2H) Q3 CH.sub.2 = CHCH.sub.2O− CH.sub.3 CH.sub.3O− −CO.sub.2CH.sub.3 δ = 1.38-1.57 (m, 2H), 1.69-1.99 (m, 4H), 2.02 and 2.21 (in each case s, in each case 3H), 3.39 (mc, 1H), 3.59 and 3.72 (in each case s, in each case 3H), 4.03 (mc, 2H), 5.19 and 5.30 (in each case d, in each case 1H), 5.88.5.97 (m, 1H), 6.78 and 6.80 (in each case s, in each case 1H) Q4 CH.sub.2 = CHCH.sub.2O− CH.sub.3 CH.sub.3O− −CO.sub.2C.sub.2H.sub.5 δ = 1.11 (t, 3H), 1.42 (mc, 2H), 1.70-1.99 (m, 4H), 2.02 and 2.20 (in each case s, in each case 3H), 3.38 (mc, 1H), 3.72 (s, 3H), 4.00 (mc, 2H), 4.07 (mc, 2H), 5.20 and 5.29 (in each case d, in each case 1H), 5.88-5.99 (m, 1H), 6.75 and 6.89 (in each case s, in each case 1H) Q5 CH.sub.2 = CHCH.sub.2O− CH.sub.3 CH.sub.3O− −COiC.sub.3H.sub.7 δ = 1.00 and 1.02 (in each case d, in each case 3H), 1.40 (mc, 2H), 2.02 and 2.19 (in each case s, in each case 3H), 2.52 (hept, 1H), 3.35 (mc, 1H), 3.70 (s, 3H), 4.03 (mc, 2H), 5.19 and 5.29 (in each case d, in each case 1H), 5.88-5.99 (m, 1H), 6.71 and 6.89 (in each case s, in each case 1H) Q6 iC.sub.3H.sub.7O− CH.sub.3 CH.sub.3O− −COiC.sub.3H.sub.7 Q7 nC.sub.4H.sub.9O− CH.sub.3 CH.sub.3O− −CO2C.sub.2H.sub.5 Q8 CH.sub.3OCH.sub.2− OCH.sub.3 CH.sub.3 −CO.sub.2C.sub.2H.sub.5 δ = 1.10-1.20 (m, 2H), 1.11 (t, 3H), 1.80-1.98 (m, 4H), 2.02 and 2.20 (in each case s, in each case 1H), 3,22 (d, 2H), 3.32 and 3.72 (in each case s, in each case 3H), 4.00 (mc, 2H), 6.72 and 6.88 (in each case s, in each case 1H)

[0366] Preparation of Starting Materials of the Formula II

Methyl 1-{2-[2-methoxy-6-methyl-4-(prop-1-yn-1-yl)phenyl]acetamido}-3-propoxycyclohexanecarboxylate

[0367] ##STR00028##

[0368] 3.00 mg (13.7 mmol) of [2-methoxy-6-methyl-4-(prop-1-yn-1-yl)phenyl]acetic acid were dissolved in 50 ml of dichloromethane and a drop of dimethylformamide was added. 3.49 g (27.4 mmol) of oxalyl chloride were added and the mixture was heated at the boil under reflux until the evolution of gas had stopped. Then, the reaction solution was concentrated to dryness, admixed twice more with in each case 50 ml of dichloromethane and concentrated again in order finally to take up the residue in 30 ml of dichloromethane (solution 1). 3.46 g (27.4 mmol) of 1-(methoxycarbonyl)-3-propoxycyclohexaneaminium chloride and 8 ml of triethylamine were initially charged in 80 ml of dichloromethane, and solution 1 was added dropwise over 20 min. After 16 h of stirring at room temperature, 100 ml of water were added, the organic phase was separated off, the solvent was removed by distillation and the mixture was purified by column chromatography (silica gel gradient ethyl acetate/n-heptane). This gave 5.35 g (93%) of the desired precursor.

[0369] .sup.1H-NMR (400 MHz, δ in ppm, CDCl.sub.3): δ=0.87 (t, 3H), 1.12 (me, 2H), 2.05 and 2.22 (in each case s, in each case 3H), 2.89 (me, 1H), 3.15-3.28 (m, 2H), 3.64 and 3.88 (in each case s, in each case 3H), 6.82 and 6.92 (in each case s, in each case 1H)

[0370] Analogously, the following intermediates of the formula II were produced:

TABLE-US-00004 Structure .sup.1H-NMR (400 MHz) (d6-DMSO): δ = 1.06 (d, 6H), 1.31-1.75 (m, 6H), 2.01 and 2.17 (in each case s, in each case 3H), 3.50 (s, 3H), 3.67 (hept, 1H), 3.72 (s, 2H), 6.78 and 6.80 (in each case s, in each case 1H) (CDC1.sub.3): δ = 1.10-1.34 (m, 4H), 2.05 and 2.32 (in each case s, in each case 3H), 3.37 (mc, 1H), 3.62 (s, 3H), 3.86 (s, 2H), 3.97 (mc, 2H), 6.91 (mc, 2H), 6.81 and 6.92 (in each case s, in each case 1H) (CDC1.sub.3): δ = 068-0.80 (m, 2H), 2.05 and 2.21 (in each case s, in each case 3H), 3.05 (d, 2H), 3.30 (s, 3H), 3.60 (s, 2H), 3.62 and 3.87 (in each case s, in each case 3H), 6.82 and 6.90 (in each case s, in each case 1H) (CDC1.sub.3): δ = 0.90 (t, 3H), 1.55 (mc, 2H), 2.05 and 2.31 (in each case s, in each case 3H), 3.20 (mc, 1H), 3.33 (t, 2H), 3.57 (s, 2H), 3.63 (s, 3H), 3.84 (s, 3H), 6.81 and 6.91 (in each case s, in each case 1H)

B. FORMULATION EXAMPLES

[0371] 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.

[0372] 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.

[0373] 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.

[0374] 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.

[0375] e) Water-dispersible granules are obtained by mixing

[0376] 75 parts by weight of a compound of the formula (I) and/or salts thereof,

[0377] 10 parts by weight of calcium lignosulfonate,

[0378] 5 parts by weight of sodium laurylsulfate,

[0379] 3 parts by weight of polyvinyl alcohol and

[0380] 7 parts by weight of kaolin,

[0381] 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.

[0382] f) Water-dispersible granules are also obtained by homogenizing and precomminuting, in a colloid mill,

[0383] 25 parts by weight of a compound of the formula (I) and/or salts thereof,

[0384] 5 parts by weight of sodium 2,2′ dinaphthylmethane-6,6′ disulfonate,

[0385] 2 parts by weight of sodium oleoylmethyltaurate,

[0386] 1 part by weight of polyvinyl alcohol,

[0387] 17 parts by weight of calcium carbonate and

[0388] 50 parts by weight of water,

[0389] then grinding the mixture in a bead mill and atomizing and drying the resulting suspension in a spray tower by means of a one-phase nozzle.

C. BIOLOGICAL DATA

[0390] 1. Pre-Emergence Herbicidal Effect and Crop Plant Compatibility

[0391] 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.

[0392] After the treatment, the pots are placed in a greenhouse and kept under good growth conditions for the trial plants. The damage to the test plants is scored visually after a test period of 3 weeks by comparison with untreated controls (herbicidal activity in percent (%): 100% activity=the plants have died, 0% activity=like control plants).

TABLE-US-00005 Undesired plants/weeds: 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 PHBPU: Pharbitis purpurea MATIN: Matricaria inodora HORMU: Hordeum murinum DIGSA: Digitaria sanguinalis

[0393] As the results from Tables 1 and 2 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, at an application rate of 320 g ai/ha or 80 g/ha the compounds each had 80-100% activity inter alia against Alopecurus myosuroides, Avena fatua, Digitaria sanguinalis, Echinochloa crus-galli, Lolium rigidum, Setaria viridis, Amaranthus retroflexus, Matricaria inodora, Stellaria medi, Viola tricolor, Veronica persica and Hordeum murinum. The compounds of the invention are therefore suitable for control of unwanted plant growth by the pre-emergence method.

TABLE-US-00006 TABLE 1 Pre-emergence activity at 320 g ai/ha Example Dosage number [g/ha] ALOMY AVEFA DIGSA ECHCG LOLRI SETVI ABUTH AMARE MATIN VIOTR VERPE D2 320 100 100 100 100 100 100 100 100 100 100 80 D6 320 100 100 100 100 100 100 100 100 90 100 100 Q2 320 100 100 100 100 100 100 90 100 100 100 90 Q8 320 100 100 100 100 100 100 100 100 100 100 100

TABLE-US-00007 TABLE 2 Pre-emergence activity at 80 g ai/ha Example Dosage number [g/ha] ALOMY AVEFA DIGSA ECHCG LOLRI SETVI VIOTR D2 80 80 100 80 90 100 100 D3 80 100 80 100 100 100 100 100 D6 80 80 80 100 100 100 Q2 80 100 80 100 100 100 100 100 Q4 80 100 90 100 100 100 100 100 Q8 80 100 80 100 100 100 100 100

[0394] 2. Post-Emergence Herbicidal Effect and Crop Plant Compatibility

[0395] 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-00008 TABLE 3 Post-emergence activity at 80 g ai/ha Example Dosage number [g/ha] ALOMY AVEFA DIGSA ECHCG LOLRI SETVI HORMU D1 80 100 100 100 100 100 100 100 D2 80 100 100 100 100 100 100 D3 80 100 100 100 100 100 100 80 D5 80 100 100 100 100 100 100 100 D6 80 100 100 100 100 100 100 P2 80 100 100 100 100 100 100 100 P3 80 100 100 100 100 100 100 100 P4 80 100 100 90 100 100 100 100 P5 80 100 100 100 100 100 100 100 Q2 80 100 90 100 100 100 100 Q3 80 100 80 90 100 100 100 100 Q4 80 100 90 100 100 100 100 100 Q5 80 100 100 100 100 100 90 Q8 80 100 100 100 100 100 100

[0396] As the results from Table 3 show, the compounds according to the invention have a good herbicidal post-emergence effectiveness against a broad spectrum of weed grasses and weeds. For example, the given examples, at an application rate of 80 g/ha show 80-100% activity inter alia against Alopecurus myosuroides, Avena fatua, Digitaria sanguinalis, Echinochloa crus-galli, Lolium rigidum, Setaria viridis and Hordeum murinum. The compounds of the invention are therefore suitable for control of unwanted plant growth by the post-emergence method.