SPECIFICALLY SUBSTITUTED 3-(2-HALOGEN-6-ALKYL-4-PROPINYLPHENYL)-3-PYRROLIN-2-ONES AND TO THE USE THEREOF AS HERBICIDES
20220151230 · 2022-05-19
Inventors
- Alfred Angermann (Kriftel, DE)
- Guido Bojack (Wiesbaden-Naurod, DE)
- Estella Buscato Arsequell (Frankfurt am Main, DE)
- Hartmut AHRENS (Langen, DE)
- Christopher Hugh Rosinger (Hofheim, DE)
- Elmar Gatzweiler (Bad Nauheim, DE)
- Elisabeth ASMUS (Hoesbach, DE)
Cpc classification
International classification
Abstract
The present invention relates to novel herbicidally active 3-phenylpyrrolidine-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 3-phenyl-3-pyrrolin-2-one of formula (I) or an agrochemically acceptable salt thereof, ##STR00053## where X represents bromine, chlorine or fluorine; 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 hydrogen, C.sub.1-C.sub.6-alkyl, 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-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.4-alkoxy-C.sub.2-C.sub.4-alkoxy or C.sub.2-C.sub.6-alkenyloxy; 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, ##STR00054## 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 represent methoxy or ethoxy; R.sup.7, R.sup.8 each independently of one another represent methyl, ethyl, phenyl or together form a saturated 5-, 6- or 7-membered ring, where one 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 aluminum, 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 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 represents a cyclic secondary or tertiary aliphatic or heteroaliphatic ammonium ion, optionally 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); or represents a heteroaromatic ammonium cation, optionally 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) as claimed in claim 1 or an agrochemically acceptable salt thereof, wherein the radicals have the following meanings: X represents bromine, chlorine or fluorine; 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 hydrogen, C.sub.1-C.sub.6-alkyl, 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.4-haloalkyl, C.sub.2-C.sub.4-alkenyl, C.sub.2-C.sub.4-alkynyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.4-alkoxy-C.sub.2-C.sub.4-alkoxy or C.sub.2-C.sub.4-alkenyloxy; R.sup.2 represents hydrogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy-C.sub.2-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.3-C.sub.6-cycloalkyl, 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 ##STR00055## 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 mono or poly by halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl or C.sub.1-C.sub.4-alkoxy; E represents an alkali metal ion, an ion equivalent of an alkaline earth metal, an ion equivalent of aluminum, 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 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 represents a cyclic secondary or tertiary aliphatic or heteroaliphatic ammonium ion, optionally 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); or represents a heteroaromatic ammonium cation, optionally 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.
3. The compound of formula (I) as claimed in claim 1 or an agrochemically acceptable salt thereof, wherein the radicals have the following meanings: X represents bromine, chlorine or fluorine; 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 hydrogen, C.sub.1-C.sub.4-alkyl, methoxymethyl or ethoxymethyl, cyclopropyl, 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.4-alkoxy, methoxyethoxy or ethoxyethoxy, or allyloxy; R.sup.2 represents hydrogen, C.sub.1-C.sub.4-alkyl, methoxyethyl or ethoxyalkyl, 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 ##STR00056## in which R.sup.3 represents C.sub.1-C.sub.4-alkyl or C.sub.1-C.sub.2-alkoxy-C.sub.1-C.sub.2-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 aluminum, 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.
4. The compound of formula (I) as claimed in claim 1 or an agrochemically acceptable salt thereof, wherein the radicals have the following meanings: X represents bromine, chlorine or fluorine; Y represents methyl, ethyl, halomethyl, haloethyl or cyclopropyl; R.sup.1 represents hydrogen, methyl, ethyl, methoxymethyl, ethoxymethyl, methoxy, ethoxy, n-propyloxy, butoxy, i-propyloxy, allyloxy, butoxy, methoxyethoxy or ethoxyethoxy; 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 ##STR00057## in which R.sup.3 represents methyl, ethyl, isopropyl or t-butyl; R.sup.4 represents methyl or ethyl; E represents a sodium ion or a potassium ion.
5. A process for preparing the compound of formula (I) or an agrochemically acceptable salt thereof as claimed in claim 1 comprising cyclizing a compound of formula (II) ##STR00058## in which R.sup.9 represents alkyl, optionally 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 agrochemically active ingredients other than component a), and optionally c) one or more auxiliaries and/or 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 or an area on which plants grow.
9. A product compromising one or more compounds 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 crop are transgenic or nontransgenic crop plants.
Description
A. CHEMICAL EXAMPLES
[0409] In the evaluation of NMR signals, the following abbreviations are used:
[0410] s (singlet), d (doublet), t (triplet), q (quartet), quint (quintet), sext (sextet), sept (septet), m (multiplet), me (multiplet centered), tt (triplet of triplets). The solvent used in each case is also stated in the table.
Example D1: 3-[2-Chloro-6-methyl-4-(prop-1-yn-1-yl)phenyl]-4-hydroxy-7-propoxy-1-azaspiro[4.5]dec-3-en-2-one
[0411] ##STR00026##
[0412] At room temperature, 396 mg (0.94 mmol) of 2-[2-chloro-6-methyl-4-(prop-1-yn-1-yl)phenyl]-N-(1-methyl-3-propoxycyclohexyl)acetamide in 10 ml of DMF were added dropwise over 30 min to a solution of 237 mg (2.07 mmol) of potassium t-butoxide in 40 ml of DMF, and the mixture was stirred at room temperature for another 12 h. Carefully, the reaction mixture was then added to an ice/water mixture and acidified to pH 1 with 2N hydrochloric acid. The precipitate was filtered off with suction, washed with water, dried and chromatographed on silica gel using hexane/ethyl acetate. This gave 173 mg (45%) of the title compound.
##STR00027##
TABLE-US-00001 Example No. R.sup.1 X Y .sup.1H NMR [400 MHz, δ in ppm, d.sub.6-DMSO] D1 nC.sub.3H.sub.7O— CH.sub.3 Cl δ = 0.86 (t, 3H), 1.48 (mc, 2H), 1.55-1.69 (m, 4H), 2.05 (s, 3H), 2.12 (s, 3H), 3.36 (mc, 2H), 3.56 (mc, 1H), 7.22 and 7.28 (je s, je 1H) D2 CH.sub.3OCH.sub.2CH.sub.2O— CH.sub.3 Cl δ = 2.05 (s, 3H), 2.10 and 2.12 (je s, Σ 3H), 3.32 (s, 3H), 3.42 (mc, 2H), 3.52-3.64 (m, 3H), 7.21 and 7.27 (je s, je 1H) D3 nC.sub.3H.sub.7O— C.sub.2H.sub.5— Cl D4 CH.sub.3OCH.sub.2CH.sub.2O— C.sub.2H.sub.5— Cl D5 nC.sub.3H.sub.7O— CH.sub.3 Br δ = 0.86 (t, 3H), 1.49 (mc, 2H), 2.06 (s, 3H), 2.10 and 2.12 (je s, Σ 3H), 3.31-3.40 (m, 3H), 3.55 (mc, 3H), 7.25 and 7.49 (je s, je 1H) D6 CH.sub.3OCH.sub.2CH.sub.2O— CH.sub.3 Br δ = 1.00-1.11 and 1.28-1.40 (je m, je 1H), 2.06 (s, 3H), 2.10 and 2.12 (je s, Σ 3H), 3.40 (mc, 2H), 3.42-3.60 (m, 3H), 7.25 and 7.43 (je s, je 3H) D7 nC.sub.3H.sub.7O— C.sub.2H.sub.5— Br D8 CH.sub.3OCH.sub.2CH.sub.2O— C.sub.2H.sub.5— Br δ = 1.00-1.10 (m, 4H), 1.25 (mc, 1H), 1.60-1.70 (m, 3H), 1.75 (mc, 2H), 2.00 (mc, 1H), 2.10 (s, 3H), 3.25 (s, 3H), 3.40 (mc, 2H), 3.50-3.60 (m, 3H), 7.10 (s, 1H), 7.50 (s, 1H), 8.10 (s, 1H), 10.95 (s, 1H) D9 (CH.sub.3).sub.2CHCH.sub.2O— CH.sub.3 Cl δ = 0.98 and 1.01 (je d, je 3H), 2.04 and 2.25 (je s, je 3H), 3.12-3.22 (m, 3H), 3.78 (mc, 1H), 7.21 and 7.29 (je s, je 1H) D10 CH.sub.3OCH.sub.2CH.sub.2O— cyclopropyl Cl δ = 0.50-0.70 (m, 2H), 0.75-0.90 (m, 2H), 1.05 (mc, 1H), 1.25 (s, br, 1H), 1.35 (mc, 1H), 1.60- 1.80 (m, 5H), 1.95-2.05 (m, 4H), 3.25 (mc, 3H), 3.40 (mc, 2H), 3.45-3.65 (m, 3H), 6.90 (s, 1H), 7.25 (mc, 1H), 8.05 (s, 1H), 11.00 (s, 1H) D11 CH.sub.3OCH.sub.2CH.sub.2O— cyclopropyl Br δ = 0.55 (mc, 1H), 0.65 (mc, 1H), 0.75-0.85 (m, 2H), 1.05 (mc, 1H), 1.25-1.40 (m, 2H), 1.60-1.80 (m, 5H), 1.95-2.05 (m, 4H), 3.25 (mc, 3H), 3.40 (mc, 2H), 3.45-3.65 (m, 3H), 6.90 (s, 1H), 7.40 (mc, 1H), 8.00 (s, 1H), 11.00 (s, 1H)
##STR00028##
TABLE-US-00002 Example No. R.sup.1 X Y .sup.1H NMR [400 MHz, δ in ppm, d.sub.6-DMSO] E1 C.sub.2H.sub.5— CH.sub.3 Cl δ = 0.89 (t, 3H), 1.12 (mc, 1H), 1.20-1.45 (m, 6H), 1.63-1.72 and 1.80-1.88 (je m, je 2H), 2.05 and 2.12 (je s, je 3H), 7.20 and 7.27 (je s, je 3H) E2 C.sub.2H.sub.5— CH.sub.3 Br E4 nC.sub.3H.sub.7O— CH.sub.3 Cl δ = 0.88 (t, 3H), 1.50 (mc, 2H), 2.06 and 2.11 (je s, je 3H), 3.21 (mc, 1H), 3.38 (t, 2H), 7.19 and 7.26 (je s, je 1H) E5 nC.sub.3H.sub.7O— CH.sub.3 Br E7 CH.sub.2═CHCH.sub.2O— CH.sub.3 Cl δ = 2.05 and 2.09 (je s, je 3H), 3.30 (mc, 1H), 4.00 (mc, 2H), 5.12 (mc, 1H), 5.72-5.81 (m, 1H), 5.80-5.98 (m, 1H), 7.21 and 7.28 (je s, je 1H) E8 CH.sub.2═CHCH.sub.2O— C.sub.2H.sub.5— Cl E9 CH.sub.2═CHCH.sub.2O— CH.sub.3 Br E10 C.sub.2H.sub.5O— CH.sub.3 Cl δ = 1.12 (t, 3H), 1.38-1.59 (m, 4H), 1.82-1.99 (m, 4H), 2.06 and 2.11 (je s, je 3H), 3.24 (mc, 1H), 3.49 (q, 2H), 7.21 and 7.28 (je s, je 1H) E11 C.sub.2H.sub.5O— CH.sub.3 Br E12 C.sub.2H.sub.5O— C.sub.2H.sub.5— Cl δ = 1.01 and 1.12 (je t, je 3H), 1.36-1.63 (m, 4H), 2.09 (s, 3H), 2.43 (q, 2H), 3.22 (mc, 1H), 3.48 (q, 2H), 7.12 and 7.38 (je s, je 1H) E13 isopropyl-O— CH.sub.3 Cl δ = 1.09 (d, 6H), 1.38-1.61 (m, 4H), 1.82-1.95 (m, 4H), 2.05 and 2.10 (je s, je 3H), 3.40 (mc, 1H), 3.73 (hept, 1H), 7.21 and 7.28 (je s, je 1H) E14 isopropyl-O— C.sub.2H.sub.5— Cl E15 isopropyl-O— CH.sub.3 Br E16 CH.sub.3OCH.sub.2CH.sub.2O— CH.sub.3 Cl δ = 1.40-1.60 (m, 4H), 1.85-2.00 (m, 4H), 2.05 and 2.10 (je s, je 3H), 3.35 (mc, 1H), 3.43 and 3.55 (je mc, je 2H), 7.20 and 7.26 (je s, je 1H) E17 CH.sub.3OCH.sub.2CH.sub.2O— CH.sub.3 Br E18 CH.sub.3OCH.sub.2CH.sub.2O— C.sub.2H.sub.5— Cl δ = 1.03 (t, 3H), 1.38-1.60 (m, 4H), 1.82-2.00 (m, 4H), 2.10 (s, 3H), 2.42 (q, 2H), 3.25 (mc, 1H), 3.32 (s, 3H), 3.42 and 3.56 (je mc, je 2H), 7.12 and 7.37 (je d, je 1H) E19 CH.sub.3O— CH.sub.3 Cl δ = 1.39-1.59 and 1.82-2.00 (je m, je 4H), 2.04 and 2.10 (je s, je 3H), 3.12 (mc, 1H), 3.35 (s, 3H), 7.20 and 7.28 (je s, je 3H) E20 CH.sub.3O— C.sub.2H.sub.5— Cl δ = 1.03 (t, 3H), 1.38-1.59 (m, 4H), 1.81-2.00 (m, 4H), 2.08 (s, 3H), 2.45 (q, 2H), 3.12 (mc, 1H), 3.26 (s, 3H), 7.13 and 7.38 (je d, je 1H) E21 CH.sub.3O— CH.sub.3 Br δ = 1.38-1.58 (m, 4H), 1.81-2.00 (m, 4H), 2.05 and 2.10 (je s, je 3H), 3.12 (mc, 1H), 3.31 (s, 3H), 7.24 and 7.42 (je s, je 1H) E22 nC.sub.4H.sub.9O— CH.sub.3 Cl E23 nC.sub.4H.sub.9O— CH.sub.3 Br E24 CH.sub.3O— cyclopropyl Cl δ = 0.55 (mc, 1H), 0.65 (mc, 1H), 0.80 (mc, 2H), 1.40-1.60 (m, 4H), 1.75 (mc, 1H), 1.80- 2.00 (m, 4H), 2.05 (s, 3H), 3.15 (mc, 1H), 3.25 (s, 3H), 6.85 (s, 1H), 7.25 (s, 1H), 8.15 (s, 1H), 10.95 (s, 1H) E25 CH.sub.3O— C.sub.2H.sub.5— Br δ = 1.00 (t, 3H), 1.40-1.60 (m, 4H), 1.80-2.00 (m, 4H), 2.05 (s, 3H), 2.40 (mc, 2H), 3.15 (mc, 1H), 3.25 (s, 3H), 7.10 (s, 1H), 7.50 (s, 1H), 8.20 (s, 1H), 10.90 (s, 1H) E26 CH.sub.3O— cyclopropyl Br δ = 0.55 (mc, 1H), 0.65 (mc, 1H), 0.75 (mc, 2H), 1.40-1.60 (m, 4H), 1.75 (mc, 1H), 1.80- 2.00 (m, 4H), 2.05 (s, 3H), 3.15 (mc, 1H), 3.25 (s, 3H), 6.90 (s, 1H), 7.45 (s, 1H), 8.10 (s, 1H), 10.90 (s, 1H) E27 CH.sub.3O— CH.sub.3 F δ = 1.40-1.50 (m, 3H), 1.60-1.90 (m, 3H), 2.00 (s, 3H), 2.10 (s, 3H), 3.10 (mc, 1H), 3.40 (s, 3H), 6.98 (s, 1H), 7.09 (s, 1H), 8.18 (s, 1H), 11.04 (s, br, 1H) E28 C.sub.2H.sub.5O— CH.sub.3 F δ = 1.10 (t, 3H), 1.40-1.50 (m, 3H), 1.60-1.90 (m, 3H), 2.00 (s, 3H), 2.10 (s, 3H), 3.20 (mc, 1H), 3.50 (q, 2H), 6.98 (s, 1H), 7.09 (s, 1H), 8.15 (s, 1H), 11.04 (s, br, 1H)
Example P1: 3-[2-Chloro-6-methyl-4-(prop-1-yn-1-yl)phenyl]-8-ethyl-2-oxo-1-azaspiro[4.5]dec-3-en-4-yl 2-methylpropanoate
[0413] ##STR00029##
[0414] 138.0 mg (0.38 mmol) of 3-[2-chloro-6-methyl-4-(prop-1-yn-1-yl)phenyl]-8-ethyl-4-hydroxy-1-azaspiro[4.5]dec-3-en-2-one and 3 ml of triethylamine were initially charged in 10 ml of dichloromethane and the mixture was stirred at room temperature for 10 min. Subsequently, 45 mg (0.42 mmol) of 2-methylpropionyl chloride in 3 ml of dichloromethane were slowly added dropwise and the mixture was then left to stir at room temperature for 12 h. The mixture was then taken up in 20 ml of dichloromethane, washed with 15 ml of sodium bicarbonate solution and 2×15 ml of water and dried (magnesium sulfate), and the solvent was distilled off. The crude product was purified by column chromatography on silica gel (ethyl acetate/n-heptane). This gave 86 mg (52%) of the title compound as a colorless solid.
[0415] Analogously to Example P1 and in accordance with the general details relating to the preparation, the following compounds according to the invention are obtained:
##STR00030##
TABLE-US-00003 Example No. R.sup.1 X Y L .sup.1H NMR [400 MHz, δ in ppm, in CDCl.sub.3 unless stated otherwise] P1 C.sub.2H.sub.5— CH.sub.3 Cl —COiPr δ = 0.91 (t, 3H), 1.03 (d, 6H), 1.22 (mc, 1H), 1.29 (pent, 2H), 1.65-1.78 and 1.82-1.96 (je m, je 3H), 2.01 and 2.27 (je s, je 3H), 2.60 (hept, 1H), 7.12 and 7.24 je s, je 1H) P2 C.sub.2H.sub.5— CH.sub.3 Cl —CO.sub.2Me δ = 0.91 (t, 3H), 1.00-1.12 (m, 2H), 1.23 (mc, 1H), 1.28 (pent, 2H), 2.02 and 2.24 (je s, je 3H), 3.64 (s, 3H), 7.15 and 7.27 (je s, je 3H) P3 C.sub.2H.sub.5— CH.sub.3 Cl —CO.sub.2Et δ = 0.91 (t, 3H), 1.15 (t, 3H), 1.28 (m, 3H), 2.02 and 2.26 (je s, je 3H), 4.05 (q, 2H), 7.14 and 7.26 (je s, je 1H) P4 nC.sub.3H.sub.7O— CH.sub.3 Cl —CO.sub.2Et δ = 0.93 and 1.15 (je t, je 3H), 1.41 (mc, 2H), 1.61 (quint., 2H), 1.70-2.01 (m, 4H), 2.03 and 2.27 (je s, je 3H), 3.32 (mc, 1H), 3.43 (t, 2H), 4.04 (q, 2H), 7.15 and 7.26 (je s, je 1H) P6 nC.sub.3H.sub.7O— CH.sub.3 Br —CO.sub.2Et P7 CH.sub.2═CHCH.sub.2O— CH.sub.3 Cl —CO.sub.2Et P8 CH.sub.2═CHCH.sub.2O— C.sub.2H.sub.5— Cl —CO.sub.2Et P9 CH.sub.2═CHCH.sub.2O— CH.sub.3 Br —CO.sub.2Et P10 CH.sub.3O— CH.sub.3 Cl —CO.sub.2Me δ = 1.39 (mc, 2H), 2.03 (s, 3H), 2.25 (s, 3H), 3.32 (mc, 1H), 3.38 and 3.65 (je s, je 3H), 7.15 and 7.28 (je s, je 1H) P11 CH.sub.3O— CH.sub.3 Cl —CO.sub.2Et δ = 1.01 (t, 3H), 1.52 (mc, 4H), 2.06 and 2.15 (je s, je 3H), 3.20 (mc, 1H), 3.28 (s, 3H), 4.02 (q, 2H), 7.26 and 7.33 (je s, je 1H) P12 CH.sub.3O— CH.sub.3 Cl —COiPr δ = 1.05 (mc, 6H), 1.38 (mc, 2H), 2.01 and 2.29 (je s, je 3H), 2.60 (sept, 1H), 3.22 (mc, 1H), 3.39 (s, 3H), 6.39 (s, br, 1H), 7.14 and 7.22 (je s, je 1H) P13 CH.sub.3O— CH.sub.3 Br —CO.sub.2Et δ = 1.15 (t, 3H), 1.48-1.60 (m, 2H), 1.68-2.00 (m, 6H), 2.03 and 2.25 (je s, je 3H), 3.22 (mc, 1H), 3.38 (s, 3H), 4.08 (q, 2H), 7.19 and 7.41 (je s, je 1H) P14 isopropyl-O— CH.sub.3 Cl —CO.sub.2Me P15 isopropyl-O— CH.sub.3 Cl —CO.sub.2Et δ = 1.16 and 1.19 (je d, je 3H), 1.42 (mc, 2H), 2.02 and 2.25 (je s, je 3H), 3.39 (mc, 1H), 3.75 (hept, 1H), 4.05 (q, 2H), 7.15 and 7.27 (je s, je 3H) P16 C.sub.2H.sub.5O— CH.sub.3 Cl —CO.sub.2Et δ = 1.02 and 1.12 (je t, je 3H), 1.48-1.62 (m 4H), 1.78-1.90 (m, 4H), 2.05 and 2.14 (je s, je 3H), 3.30 (mc, 1H), 3.31 (s, 3H), 3.49 and 4.02 (je q, je 2H), 7.25 and 7.31 (je s, je 1H) P17 CH.sub.3OCH.sub.2CH.sub.2O— CH.sub.3 Cl —CO.sub.2Et δ = 1.15 (t, 3H), 1.38-1.52 (m, 2H), 1.68-2.00 (4H), 2.02 (s, 3H), 2.27-2.37 (m, 2H), 2.28 (s, 3H), 3.39 (mc, 1H), 3.40 (s, 3H), 3.54 and 3.65 (je mc, je 2H), 4.04 (q, 2H), 7.14 and 7.28 (je s, je 1H) P18 nC.sub.4H.sub.9O— CH.sub.3 Cl —CO.sub.2Et P19 nC.sub.4H.sub.9O— CH.sub.3 Cl —CO.sub.2Me P20 nC.sub.4H.sub.9O— CH.sub.3 Cl —COiPr P21 CH.sub.3O— C.sub.2H.sub.5— Cl —CO.sub.2Et δ = 1.12 and 1.20 (je t, je 3H), 2.09 (s, 3H), 2.60 (mc, 2H), 3.22 (mc, 1H), 3.38 (s, 3H), 4.03 (q, 2H), 7.10 and 7.38 (je s, je 1H) P22 C.sub.2H.sub.5O— C.sub.2H.sub.5— Cl —CO.sub.2Et δ = 1.10-1.23 (3x t, je 3H), 2.21-2.00 (m, 4H), 2.09 (s, 3H), 2.21 (mc, 2H), 2.59 (mc, 2H), 3.32 (mc, 1H), 3.55 (q, 2H), 4.03 (q, 2H), 7.11 and 7.38 (je d, je 1H) P23 CH.sub.3OCH.sub.2CH.sub.2O— C.sub.2H.sub.5— Cl —CO.sub.2Et δ = 1.02-1.14 (m, 6H), 1.88 (mc, 2H), 2.48 (mc, 2H), 3.31 (s, 3H), 3.39 (mc, 1H), 3.49 and 3.61 (je mc, je 2H), 3.99 (mc, 2H), 4.01 (q, 2H), 7.01 and 7.30 (je d, je 1H) P24 CH.sub.3O— C.sub.2H.sub.5— Cl —CO.sub.2Me δ = 1.19 (t, 3H), 1.32-1.42 (m, 2H), 1.72-2.00 (m, 4H), 2.09 (s, 3H), 1.99- 2.28 (m, 2H), 2.60 (mc, 2H), 3.35 (mc, 1H), 3.40 and 3.64 (je s, je 3H), 7.11 and 7.38 (je d, je 1H) P25 CH.sub.3O— C.sub.2H.sub.5— Cl —COiPr δ = 1.02 and 1.05 (je d, je 3H), 1.20 (t, 3H), 2.55-2.70 (m, 3H), 3.32 (mc, 1H), 3.39 (s, 3H), 7.10 and 7.35 (je d, je 1H)1 P26 C.sub.2H.sub.5O— C.sub.2H.sub.5— Cl —CO.sub.2Me δ = 1.19 and 1.22 (je t, je 3H), 1.40 (mc, 2H), 1.71-2.00 (m, 4H), 2.10 (s, 3H), 2.21 (mc, 2H), 2.50 (mc, 2H), 3.32 (mc, 1H), 3.58 (q, 2H), 3.64 (s, 3H), P27 C.sub.2H.sub.5O— C.sub.2H.sub.5— Cl —CO.sub.2tBu δ = 1.10 (s, 9H), 1.21 (t, 3H), 1.42 (m, 2H), 1.72-1.90 (m, 4H), 2.08 (s, 3H), 2.18 (mc, 2H), 2.61 (mc, 2H), 3.30 (mc, 1H), 3.55 (q, 2H), 7.10 and 7.35 (je d, je 2H) P28 CH.sub.3OCH.sub.2CH.sub.2O— C.sub.2H.sub.5— Cl —CO.sub.2Me δ = 1.18 (t, 3H), 1.48 (mc, 2H), 1.70-2.00 (m, 4H), 2.09 (s, 3H), 2.15-2.25 (m, 2H), 2.57 (mc, 2H), 3.39 (mc, 1H), 3.40 (s, 3H), 3.53 (mc, 2H), 3.62 (s, 3H), 3.55 (mc, 2H), 7.11 and 7.38 (je d, je 3H) P29 CH.sub.3OCH.sub.2CH.sub.2O— C.sub.2H.sub.5— Cl —CO.sub.2tBu δ = 1.09 (s, 9H), 1.20 (t, 3H), 1.48 (mc, 2H), 1.75 and 1.87 (je mc, je 2H), 2.08 (s, 3H), 2.20 (mc, 2H), 2.60 (mc, 2H), 3.33 (mc, 1H), 3.40 (s, 3H), 3.55 and 3.67 (je mc, je 2H), 7.10 and 7.35 (je d, je 1H) P30 CH.sub.3O— C.sub.2H.sub.5— Cl —CO.sub.2tBu δ = 1.09 (s, 9H), 1.20 (t, 3H), 1.36-1.47 (m, 2H), 2.09 (s, 3H), 2.20 (mc, 2H), 2.62 (mc, 2H), 3.22 (mc, 1H), 3.40 (s, 3H), 7.10 and 7.33 (je d, je 1H) P31 C.sub.2H.sub.5O— C.sub.2H.sub.5— Cl —COiPr δ = 0.99 and 1.02 (je d, je 3H), 1.21 and 1.23 (je t, je 3H), 2.09 (s, 3H), 2.20 (mc, 2H), 2.53-2.69 (m, 3H), 3.31 (mc, 1H), 3.55 (q, 2H), 7.10 and 7.24 (je d, je 1H) P32 CH.sub.3OCH.sub.2CH.sub.2O— C.sub.2H.sub.5— Cl —COiPr δ = 1.00 and 1.02 (je d, je 3H), 1.20 (t, 3H), 1.48 (mc, 2H), 1.72-1.95 (m, 4H), 2.08 (s, 3H), 2.21 (mc, 2H), 2.52-2.69 (m, 3H), 3.35 (mc, 1H), 3.40 (s, 3H), 3.55 and 3.68 (je mc, je 2H), 7.10 and 7.25 (je d, je 1H) P33 CH.sub.3O— cyclopropyl Cl —CO.sub.2Et d.sub.6-DMSO: δ = 0.65 (mc, 2H), 0.75-0.90 (m, 2H), 1.00 (t, 3H), 1.50-1.60 (m, 4H), 1.70- 1.90 (m, 3H), 1.95-2.05 (m, 5H), 3.20 (mc, 1H), 3.25 (s, 3H), 4.00 (q, 2H), 6.90 (s, 1H), 7.30 (s, 1H), 9.00 (s, 1H) P34 CH.sub.3O— C.sub.2H.sub.5— Br —CO.sub.2Et δ = 1.15 (t, 6H), 1.25-1.40 (m, 2H), 1.75 (mc, 2H), 1.90 (mc, 2H), 2.10 (s, 3H), 2.20 (mc, 2H), 2.60 (mc, 2H), 3.25 (mc, 1H), 3.40 (s, 3H), 4.10 (q, 2H), 6.25 (s, 1H), 7.20 (s, 1H), 7.45 (s, 1H) P35 CH.sub.3O— cyclopropyl Br —CO.sub.2Et d.sub.6-DMSO: δ = 0.65 (mc, 2H), 0.80 (mc, 2H), 1.00 (t, 3H), 1.50-1.60 (m, 4H), 1.70-1.90 (m, 4H), 1.95-2.05 (m, 4H), 3.20 (mc, 1H), 3.25 (s, 3H), 4.00 (q, 2H), 6.90 (s, 1H), 7.45 (s, 1H), 9.00 (s, 1H) P36 CH.sub.3OCH.sub.2— CH.sub.3 Cl —CO.sub.2Et P37 CH.sub.3O— CH.sub.3 F —CO.sub.2Et δ = 1.20 (t, 3H), 1.40 (mc, 2H), 1.60-1.90 (m, 4H), 2.00 (s, 3H), 2.20 (mc, 2H), 2.30 (s, 3H), 3.24 (mc, 1H), 3.38 (s, 3H), 4.10 (q, 2H), 6.45 (s, br, 1H), 6.92 (s, 1H), 7.06 (s, 1H) P38 C.sub.2H.sub.5O— CH.sub.3 F —CO.sub.2Et δ = 1.10 (t, 3H), 1.20 (t, 3H), 1.40 (mc, 2H), 1.60-1.90 (m, 4H), 2.00 (s, 3H), 2.30 (mc, 2H), 2.40 (s, 3H), 3.30 (mc, 1H), 3.60 (q, 2H), 4.00 (q, 2H), 6.28 (s, br, 1H), 6.92 (s, 1H), 7.06 (s, 1H)
##STR00031##
TABLE-US-00004 Example No. R.sup.1 X Y L .sup.1H NMR [400 MHz, δ in ppm, in CDCl.sub.3 unless stated otherwise] Q1 CH.sub.3OCH.sub.2CH.sub.2O— C.sub.2H.sub.5— Br —CO.sub.2Et δ = 1.15-1.30 (m, 7H), 1.45-1.60 (m, 2H), 1.75 (mc, 2H), 1.90-2.05 (m, 2H), 2.10 (s, 3H), 2.20 (mc, 1H), 2.55 (s, br, 2H), 3.35 (s, 3H), 3.40-3.55 (m, 3H), 3.55-3.70 (m, 2H), 4.10 (q, 2H), 7.20 (s, br, 1H), 7.50 (s, 1H), 7.75 (s, 1H) Q2 CH.sub.3OCH.sub.2CH.sub.2O— cyclopropyl Br —CO.sub.2Et d.sub.6-DMSO: δ = 0.65 (mc, 2H), 0.85 (mc, 2H), 1.05-1.15 (m, 4H), 1.25 (mc, 1H), 1.45 (mc, 1H), 1.50-1.85 (m, 5H), 2.00-2.10 (m, 4H), 3.25 (s, 3H), 3.40 (mc, 2H), 3.45- 3.65 (m, 3H), 4.05 (q, 2H), 6.90 (mc, 1H), 7.45 (mc, 1H), 8.95 (s, 1H) Q3 nC.sub.3H.sub.7O— CH.sub.3 Br —CO.sub.2Et δ = 0.86 and 1.05 (je t, je 3H), 1.35-1.85 (m, 6H), 2.05 (s, 3H), 2.06 and 2.09 (je s, Σ 3H), 3.38 (mc, 2H), 3.58 (mc, 1H), 4.05 (mc, 2H), 7.30 and 7.48 (je s, je 3H) Q4 CH.sub.3OCH.sub.2CH.sub.2O— CH.sub.3 Br —CO.sub.2Et δ = 1.16 (t, 3H), 2.01 (s, 3H), 2.25 and 2.28 (je s, Σ 3H), 3.38 (s, 3H), 3.52 (mc, 2H), 3.56-3.72 (m, 3H), 4.04 (q, 2H), 7.19 and 7.42 (je s, je 1H) Q5 nC.sub.3H.sub.7O— CH.sub.3 Cl —CO.sub.2Et δ = 0.86 and 1.05 (je t, je 3H), 1.35-1.85 (m, 6H), 2.05 (s, 3H), 2.06 and 2.09 (je s, Σ 3H), 3.38 (mc, 2H), 3.58 (mc, 1H), 4.05 (mc, 2H), 7.30 and 7.48 (je s, je 3H) Q6 (CH.sub.3).sub.2CHCH.sub.2O— CH.sub.3 Cl —CO.sub.2Me δ = 0.89 (d, 6H), 1.79 (hept, 1H), 2.05 (s, 3H), 3.21 (mc, 2H), 3.38 (mc, 1H), 3.65 (s, 3H), 7.17 and 7.27 (je s, je 1H) Q7 (CH.sub.3).sub.2CHCH.sub.2O— CH.sub.3 Cl —CO.sub.2tBu δ = 0.89 (mc, 6H), 1.11 (s, 9H), 2.02 (s, 3H), 2.28 and 2.31 (je s, Σ 3H), 3.22 (mc, 2H), 3.38 (mc, 1H), 7.12 and 7.23 (je s, je 1H) Q8 (CH.sub.3).sub.2CHCH.sub.2O— CH.sub.3 Cl —CO.sub.2Et δ = 0.89 (d, 6H), 1.15 (t, 3H), 1.78 (hept, 1H), 2.02 (s, 3H), 2.22 and 2.27 (je s, Σ 3H), 3.21 (mc 2H), 3.38 (mc, 1H), 4.02 (q, 2H), 7.15 and 7.28 (je s, je 3H)
[0416] Preparation of Starting Materials
[0417] Methyl 1-{2-[2-bromo-6-methyl-4-(prop-1-yn-1-yl)phenyl]acetamido}-3-propoxycyclohexanecarboxylate
##STR00032##
[0418] 235 mg (1.05 mmol) of [2-chloro-6-methyl(prop-1-yn-1-yl)phenyl]acetic acid were dissolved in 10 ml of dichloromethane and a drop of DMF was added. 274 mg (2.11 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, admixed twice more with in each case 15 ml of dichloromethane and concentrated again in order finally to take up the residue in 2 ml of dichloromethane (solution 1). 292 mg (1.16 mmol) of 1-(methoxycarbonyl)-3-propoxycyclohexaneaminium chloride and 0.7 ml of triethylamine were initially charged in 10 ml of dichloromethane, and solution 1 was added dropwise over 20 min. After 18 h of stirring at room temperature, 30 ml of water were added and the organic phase was separated off, concentrated and purified by column chromatography (silica gel, gradient ethyl acetate/n-heptane). This gave 353 mg (80%) of the desired precursor.
[0419] .sup.1H-NMR (400 MHz, δ in ppm, d6-DMSO): δ=0.82 (t, 3H), 1.00-1.12 (m, 1H), 1.90-1.98 (m, 2H), 1.95 (me, 2H), 2.02 and 2.24 (je s, je 3H), 3.31 (me, 2H), 3.42 (me, 1H), 3.54 (s, 3H), 3.73 (s, 2H), 7.18 and 7.25 (je s, je 1H)
[0420] The following intermediates were prepared analogously:
TABLE-US-00005 Structure .sup.1H NMR (400 MHz, δ in ppm)
[0421] Preparation of 2-(2-chloro-6-ethyl-4-(prop-1-yn-1-yl)phenylacetic acid
##STR00047##
[0422] A mixture of 4.65 g (13.7 mmol) of methyl 2-(2-chloro-6-ethyl-4-iodophenyl)acetate [CAS-Registry Number 880134-40-7], 1.2 g (14.3 mmol) of but-2-ynoic acid, 4.16 g of DBU (27.3 mmol), Pd(PPh.sub.3).sub.2Cl.sub.2 (0.10 g, 0.14 mmol) and 0.12 g of 1,4-bis(diphenylphosphino)butane (0.273 mmol) was degassed, covered with argon and heated at 90° C. for 16 h. After cooling the mixture was taken up in ethyl acetate and repeatedly washed with water and dried (sodium sulfate) and the solvent was distilled off. Chromatography on silica gel (ethyl acetate/hexane) gave 3.20 g (85%) of methyl 2-(2-chloro-6-ethyl-4-(prop-1-yn-1-ylphenyl)acetate in the form of colorless crystals.
[0423] .sup.1H-NMR (400 MHz, CDCl3): δ=1.19 (t, 3H), 2.10 (s, 3H), 2.64 (q, 2H), 3.75 (s, 3H), 3.92 (s, 2H), 7.05 and 7.33 (je d, je 1H)
[0424] 1.51 g (37.7 mol) of sodium hydroxide was added a little at a time to 3.19 g (128 mmol) of this phenylacetic acid ester in 30 ml of methanol/water (1:1) and the mixture was stirred at 60° C. for 16 h. The solvent was then distilled off and the residue was taken up in 40 ml of dichloromethane and acidified to pH=5 with 2N hydrochloric acid. Extraction with water, drying (sodium sulfate) and distillative removal of the solvent gave 28.0 g (92%) of the desired compound in the form of colorless crystals.
[0425] 1H-NMR (400 MHz, CDCl3): δ=1.20 (t, 3H), 2.10 (s, 3H), 2.63 (q, 2H), 3.92 (s, 2H), 7.05 (d, 1H), 7.32 (d, 1H)
[0426] The following intermediates can be prepared in an analogous manner.
TABLE-US-00006 Structure .sup.1H-NMR (400 MHz)
B. FORMULATION EXAMPLES
[0427] 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.
[0428] 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-disk mill.
[0429] 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.
[0430] 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.
[0431] e) Water-dispersible granules are obtained by mixing
[0432] 75 parts by weight of a compound of the formula (I) and/or salts thereof,
[0433] 10 parts by weight of calcium lignosulfonate,
[0434] 5 parts by weight of sodium laurylsulfate,
[0435] 3 parts by weight of polyvinyl alcohol and
[0436] 7 parts by weight of kaolin,
[0437] grinding the mixture in a pinned-disk mill, and granulating the powder in a fluidized bed by spray application of water as a granulating liquid.
[0438] f) Water-dispersible granules are also obtained by homogenizing and precomminuting, in a colloid mill,
[0439] 25 parts by weight of a compound of the formula (I) and/or salts thereof,
[0440] 5 parts by weight of sodium 2,2′-dinaphthylmethane-6,6′-disulfonate,
[0441] 2 parts by weight of sodium oleoylmethyltaurate,
[0442] 1 part by weight of polyvinyl alcohol,
[0443] 17 parts by weight of calcium carbonate and
[0444] 50 parts by weight of water,
[0445] 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
[0446] 1. Pre-Emergence Herbicidal Effect and Crop Plant Compatibility
[0447] Seeds of monocotyledonous and dicotyledonous weed plants and crop plants are laid out in sandy loam soil in wood-fiber 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.
[0448] 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).
[0449] Undesired Plants/Weeds:
TABLE-US-00007 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
[0450] As shown by the results from Tables 1-7, the compounds according to the invention have a good herbicidal pre-emergence effectiveness against a broad spectrum of weeds. The compounds of the invention are therefore suitable for control of unwanted plant growth by the pre-emergence method.
TABLE-US-00008 TABLE 1 Pre-emergence action [%] against ALOMY Example number Dosage [g/ha] ALOMY D5 320 100 D6 320 100 D8 320 80 D9 320 100 D11 320 100 E12 320 90 E16 320 100 E20 320 100 E21 320 100 E24 320 100 E26 320 100 P13 320 100 P17 320 100 P21 320 100 P22 320 100 P23 320 100 P24 320 100 P25 320 100 P26 320 100 P28 320 100 P29 320 80 P30 320 100 P31 320 100 P32 320 100 P33 320 100 P35 320 100 Q1 320 90 Q2 320 100 Q3 320 100 Q4 320 100 Q6 320 100 Q7 320 80 Q8 320 100
TABLE-US-00009 TABLE 2 Pre-emergence action [%] against AVEFA Example number Dosage [g/ha] AVEFA D5 320 100 D6 320 100 D9 320 100 D11 320 100 E12 320 90 E16 320 100 E20 320 100 E21 320 100 E24 320 100 E26 320 90 P13 320 100 P17 320 100 P21 320 100 P22 320 90 P23 320 80 P24 320 100 P25 320 100 P26 320 90 P28 320 80 P29 320 80 P30 320 80 P31 320 90 P33 320 100 P35 320 100 Q2 320 100 Q3 320 100 Q4 320 100 Q6 320 90 Q8 320 100
TABLE-US-00010 TABLE 3 Pre-emergence action [%] against DIGSA Example number Dosage [g/ha] DIGSA D5 320 100 D6 320 100 D9 320 100 D11 320 100 E12 320 100 E16 320 100 E20 320 100 E21 320 100 E24 320 100 E26 320 100 P13 320 100 P17 320 100 P21 320 100 P22 320 100 P23 320 100 P24 320 100 P25 320 100 P26 320 100 P28 320 100 P29 320 90 P30 320 100 P31 320 100 P32 320 90 P33 320 100 P35 320 100 Q2 320 100 Q3 320 100 Q4 320 100 Q6 320 100 Q8 320 100
TABLE-US-00011 TABLE 4 Pre-emergence action [%] against LOLRI Example number Dosage [g/ha] LOLRI D5 320 100 D6 320 100 D9 320 100 D11 320 100 E12 320 100 E16 320 100 E20 320 90 E21 320 100 E24 320 100 E26 320 100 P13 320 100 P17 320 100 P21 320 100 P22 320 100 P23 320 100 P24 320 100 P25 320 90 P26 320 100 P30 320 100 P31 320 100 P32 320 90 P33 320 100 P35 320 100 Q1 320 90 Q2 320 100 Q3 320 100 Q4 320 100 Q6 320 100 Q8 320 100
TABLE-US-00012 TABLE 5 Pre-emergence action [%] against SETVI Example number Dosage [g/ha] SETVI D5 320 100 D6 320 100 D8 320 100 D9 320 100 D11 320 100 E12 320 100 E16 320 100 E20 320 100 E21 320 100 E24 320 100 E26 320 100 P13 320 100 P17 320 100 P21 320 100 P22 320 100 P23 320 100 P24 320 100 P25 320 100 P26 320 100 P28 320 100 P29 320 80 P30 320 100 P31 320 100 P32 320 100 P33 320 100 P34 320 100 P35 320 100 Q1 320 100 Q2 320 100 Q3 320 100 Q4 320 100 Q6 320 100 Q7 320 100 Q8 320 100
TABLE-US-00013 TABLE 6 Pre-emergence action [%] against VIOTR Example number Dosage [g/ha] VIOTR D5 320 100 D6 320 100 D9 320 100 D11 320 100 E12 320 100 E16 320 100 E20 320 100 E21 320 100 E24 320 100 E25 320 80 E26 320 90 P13 320 100 P17 320 100 P21 320 90
TABLE-US-00014 TABLE 7 Pre-emergence action [%] against ECHCG Example number Dosage [g/ha] ECHCG D5 320 100 D6 320 100 D9 320 100 D11 320 100 E12 320 100 E16 320 100 E20 320 100 E21 320 100 E24 320 100 E26 320 100 P13 320 100 P17 320 100 P21 320 100 P22 320 100 P23 320 100 P24 320 90 P25 320 100 P26 320 90 P28 320 100 P29 320 90 P30 320 90 P31 320 100 P32 320 100 P33 320 100 P35 320 100 Q2 320 100 Q3 320 100 Q4 320 100 Q6 320 100 Q8 320 100
[0451] 2. Post-Emergence Herbicidal Effect and Crop Plant Compatibility
[0452] Seeds of monocotyledonous and dicotyledonous weed and crop plants are laid out in sandy loam soil in wood-fiber 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-00015 TABLE 8 Post-emergence action [%] against ALOMY Example number Dosage [g/ha] ALOMY D1 80 100 D2 80 100 D5 80 100 D6 80 100 D8 80 100 D9 80 100 D11 80 100 E1 80 100 E7 80 100 E10 80 100 E13 80 100 E16 80 100 E19 80 100 E21 80 100 E24 80 100 E25 80 90 E26 80 100 P3 80 100 P10 80 100 P11 80 100 P12 80 100 P13 80 100 P15 80 100 P16 80 100 P17 80 100 P21 80 90 P23 80 80 P24 80 100 P25 80 90 P26 80 90 P30 80 90 P31 80 100 P33 80 100 P34 80 100 P35 80 100 Q1 80 80 Q2 80 100 Q3 80 100 Q4 80 100 Q5 80 100 Q6 80 100 Q8 80 100
TABLE-US-00016 TABLE 9 Post-emergence action [%] against AVEFA Example number Dosage [g/ha] AVEFA D1 80 100 D2 80 100 D5 80 100 D6 80 100 D8 80 80 D9 80 90 E1 80 100 E7 80 80 E10 80 100 E13 80 100 E16 80 100 E19 80 100 E20 80 90 E21 80 90 E24 80 100 P10 80 100 P11 80 100 P12 80 100 P13 80 100 P15 80 100 P16 80 100 P17 80 100 P21 80 80 P24 80 90 P30 80 80 P33 80 100 Q4 80 90 Q5 80 100 Q6 80 100 Q8 80 100
TABLE-US-00017 TABLE 10 Post-emergence action [%] against DIGSA Example number Dosage [g/ha] DIGSA D1 80 100 D2 80 100 D5 80 100 D6 80 100 D9 80 90 D11 80 100 E1 80 100 E7 80 100 E10 80 100 E13 80 100 E16 80 100 E19 80 100 E20 80 100 E21 80 100 E26 80 100 P3 80 100 P10 80 100 P11 80 100 P12 80 100 P13 80 100 P15 80 100 P16 80 100 P17 80 100 P21 80 100 P22 80 90 P24 80 90 P25 80 100 P26 80 80 P35 80 100 Q2 80 100 Q3 80 100 Q5 80 100 Q6 80 100
TABLE-US-00018 TABLE 11 Post-emergence action [%] against ECHCG Example number Dosage [g/ha] ECHCG D1 80 100 D2 80 100 D5 80 100 D6 80 100 D8 80 90 D9 80 100 D11 80 100 E1 80 100 E7 80 100 E10 80 100 E12 80 100 E13 80 100 E16 80 100 E19 80 100 E20 80 100 E21 80 100 E24 80 100 E26 80 100 P3 80 100 P10 80 100 P11 80 100 P12 80 100 P13 80 100 P15 80 100 P16 80 100 P17 80 100 P21 80 100 P22 80 90 P24 80 100 P25 80 100 P26 80 100 P28 80 80 P29 80 90 P33 80 100 P34 80 90 P35 80 100 Q2 80 100 Q3 80 100 Q4 80 100 Q5 80 100 Q6 80 100 Q8 80 100
TABLE-US-00019 TABLE 12 Post-emergence action [%] against LOLRI Example number Dosage [g/ha] LOLRI D1 80 100 D2 80 100 D5 80 100 D6 80 100 D8 80 80 D9 80 90 D11 80 100 E1 80 100 E7 80 100 E10 80 100 E13 80 100 E16 80 100 E19 80 100 E20 80 80 E21 80 100 E24 80 100 E26 80 100 P3 80 100 P10 80 100 P11 80 100 P12 80 100 P13 80 100 P15 80 100 P16 80 100 P17 80 100 P21 80 80 P33 80 100 P35 80 100 Q2 80 100 Q3 80 100 Q4 80 100 Q5 80 100 Q6 80 100 Q8 80 90
TABLE-US-00020 TABLE 13 Post-emergence action [%] against SETVI Example number Dosage [g/ha] SETVI D1 80 100 D2 80 100 D5 80 100 D6 80 100 D8 80 90 D9 80 100 D11 80 100 E1 80 100 E7 80 100 E10 80 100 E12 80 100 E13 80 100 E16 80 100 E19 80 100 E20 80 100 E21 80 100 E24 80 100 E25 80 90 E26 80 100 P1 80 100 P3 80 100 P10 80 100 P11 80 100 P12 80 100 P13 80 100 P15 80 100 P16 80 100 P17 80 100 P21 80 100 P22 80 100 P23 80 80 P24 80 100 P25 80 100 P26 80 90 P28 80 80 P29 80 90 P30 80 100 P31 80 100 P32 80 90 P33 80 100 P34 80 100 P35 80 100 Q1 80 90 Q2 80 100 Q3 80 100 Q4 80 100 Q5 80 100 Q6 80 100 Q8 80 100
TABLE-US-00021 TABLE 14 Post-emergence action [%] against HORMU Example number Dosage [g/ha] HORMU D1 80 100 E1 80 100 E7 80 90 E10 80 100 E13 80 100 E19 80 100 P3 80 100 P10 80 100 P11 80 90 P12 80 100 P15 80 90 P16 80 100 Q5 80 100
[0453] As shown by the results from Tables 8-14, the compounds according to the invention have a good herbicidal post-emergence effectiveness against a broad spectrum of weed grasses and weeds. The compounds of the invention are therefore suitable for control of unwanted plant growth by the post-emergence method.