Classifications

• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
  • A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
  • C07C69/013—Esters of alcohols having the esterified hydroxy group bound to a carbon atom of a ring other than a six-membered aromatic ring
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
  • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
  • C07D209/54—Spiro-condensed
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
  • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
  • A01N43/38—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings condensed with carbocyclic rings
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48

Definitions

• the present invention relates to novel herbicidally effective alkynyl-substituted 3-phenylpyrrolidine-2,4-diones according to the general formula (I) or agrochemically acceptable salts thereof, and to the use thereof for controlling weeds and weed grasses in crops of useful plants.
• Alkynyl-substituted N-phenylpyrrolidine-2,4-diones with a herbicidal effect are also known from WO 96/82395, WO 98/05638, WO 01/74770, WO 14/032702 or WO15/040114.
• the object of the present invention is to provide novel compounds which do not have the stated disadvantages.
• the present invention therefore relates to novel alkynyl-substituted N-phenylpyrrolidine-2,4-diones of the general formula (I),
• X C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl or C 3 -C 6 -cycloalkyl,
• Y C 1 -C 4 -alkyl or C 3 -C 6 -cycloalkyl
• R 1 hydrogen, C 1 -C 6 -alkyl, or C 3 -C 6 -cycloalkyl
• R 2 hydrogen or methyl
• R 3 C 1 -C 6 -alkyl or C 1 -C 6 -alkoxy-C 2 -C 6 -alkyl
• G hydrogen, a cleavable group L or a cation E;
• alkyl radicals having more than two carbon atoms may be straight-chain or branched.
• Alkyl radicals are e.g. methyl, ethyl, n- or isopropyl, n-, iso, t- or 2-butyl, pentyls such as n-pentyl, 2,2,-dimethylpropyl and 3-methylbutyl.
• Cycloalkyl is a carbocyclic saturated ring system having three to six carbon atoms, for example cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
• Halogen is fluorine, chlorine, bromine or iodine.
• the compounds of the formula (I) can, depending on the type of substituents, be present as geometric and/or optical isomers or isomer mixtures, in differing composition, for example also in cis or trans form, which are defined as follows:
• the isomer mixtures which may arise in the synthesis can be separated by the conventional technical methods.
• X C 1 -C 4 -alkyl or C 3 -C 6 -cycloalkyl
• Y C 1 -C 4 -alkyl or C 3 -C 6 -cycloalkyl
• R 1 hydrogen, methyl, ethyl, isopropyl or cyclopropyl
• R 2 hydrogen or methyl
• R 3 C 1 -C 6 -alkyl or C 1 -C 4 -alkoxy-C 2 -C 4 -alkyl
• X methyl, ethyl or cyclopropyl
• R 1 hydrogen, methyl, ethyl, isopropyl or cyclopropyl
• R 3 C 1 -C 4 -alkyl
• X methyl, ethyl or cyclopropyl
• R 1 hydrogen, methyl, ethyl, isopropyl or cyclopropyl
• R 3 C 1 -C 4 -alkoxy-C 2 -C 4 -alkyl
• R 1 hydrogen, methyl or cyclopropyl
• R 3 C 1 -C 4 -alkyl
• R 1 hydrogen, methyl or cyclopropyl
• R 3 C 1 -C 4 -alkoxy-C 2 -C 4 -alkyl
• R 10 is alkyl, preferably 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 10 OH, or
• Hal is a halogen, preferably chlorine or bromine or can be a sulphonic acid group, optionally in the presence of a suitable solvent or diluent, and also a suitable base,
• R 1 has the meaning given above and W is hydrogen or a suitable leaving group, optionally in the presence of a suitable catalyst and a suitable base.
• Suitable leaving groups W are, for example, halogen atoms such as chlorine, bromine or iodine, alkylsulphonic ester groups such as, for example, triflate, mesylate or nonaflate, magnesium chloride, zinc chloride, a trialkyltin radical, and boric acid radicals such as —B(OH) 2 or —B(Oalkyl) 2 .
• Pd 0 complexes in particular are very readily suitable as catalysts, where in many cases also the addition of Cu(') salts may be very advantageous.
• a compound of the general formula (IV) can also be reacted with an alkynyl reagent of the general formula (VI) in an analogous application of the coupling methodology described above, then cleaved into ethynyl compounds of the general formula (VIII) and these are finally converted with a suitable alkylating reagent to the compound (I) according to the invention, where in each case X, Y, R 1 , R 2 , R 3 , G, U and W have the described meaning and the cleavable group R 11 can be for example a group (C 1 -C 4 -alkyl) 2 C—OH.
• R 12 is a C 1 -C 4 -trialkylsilyl radical, for example.
• a further variant for preparing compounds of the general formula (II) consists, inter alia, also in reacting a compound with the general formula (XIII), in which X, Y, R 2 , R 3 , R 10 and U have the meaning given above, with a compound of the general formula (V) or (VI), in which W, R 3 and R 11 have the meaning given above, by the cross-coupling methodology already described:
• the compounds according to the invention of the formula (I) and/or salts thereof, referred to hereinbelow together as “compounds according to the invention”, have an excellent herbicidal effectiveness against a broad spectrum of economically important mono- and dikotyledonous annual weeds.
• the active ingredients also act efficiently on perennial weeds which produce shoots from rhizomes, root stocks and other perennial organs and which are difficult to control.
• the present invention therefore also provides a method for controlling unwanted plants or for regulating the growth of plants, preferably in plant crops, in which one or more compound(s) according to the invention is/are applied to the plants (for example harmful plants such as monocotyledonous or dicotyledonous weeds or unwanted crop plants), the seed (for example grains, seeds or vegetative propagules such as tubers or shoot parts with buds) or the area on which the plants grow (for example the area under cultivation).
• the compounds of the invention can be deployed, for example, prior to sowing (if appropriate also by incorporation into the soil), prior to emergence or after emergence.
• Monocotyledonous harmful plants of the genera Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, lschaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.
• the compounds of the invention are applied to the soil surface before germination, either the emergence of the weed seedlings is prevented completely or the weeds grow until they have reached the cotyledon stage, but then they stop growing and ultimately die completely after three to four weeks have passed.
• the compounds according to the invention have an excellent herbicidal activity towards mono- and dikotyledonous weeds, crop plants of economically important crops e.g. dicotyledonous crops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous crops of the genera Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea, in particular Zea and Triticum, are damaged only insignificantly, or not at all, depending on the structure of the particular compound according to the invention and its application rate.
• the present compounds are very suitable for selective control of unwanted plant growth in plant crops such as agriculturally useful plants or ornamental
• the compounds according to the invention (depending on their particular structure and the application rate deployed) have outstanding growth-regulating properties in crop plants. They intervene in the plants' own metabolism with regulatory effect, and can thus be used for controlled influencing of plant constituents and to facilitate harvesting, for example by triggering desiccation and stunted growth. Furthermore, they are also suitable for the general control and inhibition of unwanted vegetative growth without killing the plants in the process. An inhibition of the vegetative growth plays a large role in many mono- and dikotyledonous crops since, for example, the storage formation can be reduced or completely prevented as a result.
• transgenic plants are characterized by particular advantageous properties, for example by resistances to certain pesticides, in particular certain herbicides, resistances to plant diseases or pathogens of plant diseases, such as certain insects or microorganisms such as fungi, bacteria or viruses.
• Other particular properties relate, for example, to the harvested material with regard to quantity, quality, storability, composition and specific constituents. For instance, there are known transgenic plants with an elevated starch content or altered starch quality, or those with a different fatty acid composition in the harvested material.
• transgenic crops preference is given to the application of the compounds according to the invention in economically important transgenic crops of useful plants and ornamental plants, e.g. of cereals such as wheat, barley, rye, oats, millet, rice, maniok and corn or else crops of sugar cane, cotton, soybean, rapeseed, potatos, tomatoes, peas and other vegetable varieties.
• the compounds of the invention can be used as herbicides in crops of useful plants which are resistant, or have been made resistant by genetic engineering, to the phytotoxic effects of the herbicides.
• novel plants with modified properties can be generated with the aid of recombinant methods (see, for example, EP-A-0221044, EP-A-0131624). For example, there have been descriptions in several cases of:
• nucleic acid molecules which allow mutagenesis or sequence alteration by recombination of DNA sequences can be introduced into plasmids.
• base exchanges remove parts of sequences or add natural or synthetic sequences.
• adapters or linkers can be placed onto the fragments, see e.g. Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 1st edition Cold Spring Harbor Laboratory Press, Cold Spring Harbor, N.Y., or Winnacker “Gene and Klone [Genes and clones]”, VCH Weinheim 1st edition 1996.
• the generation of plant cells with a reduced activity of a gene product can be achieved by expressing at least one corresponding antisense RNA, a sense RNA for achieving a cosuppression effect, or by expressing at least one suitably constructed ribozyme which specifically cleaves transcripts of the abovementioned gene product.
• DNA molecules which encompass the entire coding sequence of a gene product inclusive of any flanking sequences which may be present and also DNA molecules which only encompass portions of the coding sequence, in which case it is necessary for these portions to be long enough to have an antisense effect in the cells.
• the protein synthesized may be localized in any desired compartment of the plant cell.
• sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106).
• the nucleic acid molecules can also be expressed in the organelles of the plant cells.
• the transgenic plant cells can be regenerated by known techniques to give rise to entire plants.
• the transgenic plants may be plants of any desired plant species, i.e. not only monocotyledonous but also dicotyledonous plants.
• the compounds of the invention can be used with preference in transgenic crops which are resistant to growth regulators, for example dicamba, or to herbicides which inhibit essential plant enzymes, for example acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydroxyphenylpyruvate dioxygenases (HPPD), or to herbicides from the group of the sulphonylureas, the glyphosates, glufosinates or benzoylisoxazoles and analogous active ingredients.
• growth regulators for example dicamba
• herbicides which inhibit essential plant enzymes for example acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydroxyphenylpyruvate dioxygenases (HPPD)
• ALS acetolactate synthases
• EPSP synthases glutamine synthases
• HPPD hydroxyphenylpyruvate dioxygenases
• the active ingredients of the invention are used in transgenic crops, not only do the effects toward harmful plants which are observed in other crops occur, but often also effects which are specific to application in the particular transgenic crop, for example an altered or specifically widened spectrum of weeds which can be controlled, altered application rates which can be used for the application, preferably good combinability with the herbicides to which the transgenic crop is resistant, and influencing of growth and yield of the transgenic crop plants.
• the invention therefore also provides for the use of the compounds of the invention as herbicides for control of harmful plants in transgenic crop plants.
• the compounds of the general formula (I) can also be used to control those harmful plants e.g. from the group Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Digitaria, Echinochloa, Eleusine, Eriochloa, Leptochloa, Lolium, Ottochloa, Panicum, Pennisetum, Phalaris, Poa, Rottboellia, Setaria and/or Sorghum weeds; in particular Alopecurus, Apera, Avena, Brachiaria, Bromus, Digitaria, Echinochloa, Eriochloa, Lolium, Panicum, Phalaris, Poa, Setaria and/or Sorghum weeds,
• Such harmful grasses resistant to ACCase and/or ALS inhibitors and/or glyphosate are, inter alia, Alopecurus myosuroides, Apera spica - venti, Avena fatua, Avena sterilis, Brachiaria decumbens, Brachiaria plantaginea, Digitatia horizontalis, Digitaria insularis, Digitaria sanguinalis, Echinochloa colona, Echinochloa crus - galli, Eleusine indica, Lolium multiflorum, Lolium rigidum, Lolium perenne, Phalaris minor, Phalaris paradoxa, Setaria viridis, Setaria faberi or Setaria glauca.
• the compounds according to the invention of the general formula (I) can be used against harmful plants
• the compounds according to the invention exhibit superior properties compared to the compounds from the prior art, for example WO 2015/040114, compound 41.03 (see also the comparison data in Tables 9 and 10).
• the compounds of the invention can be applied in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusting products or granules in the customary formulations.
• the invention therefore also provides herbicidal and plant-growth-regulating compositions which comprise the compounds of the invention.
• the compounds according to the invention can be formulated in various ways according to which biological and/or chemical physical parameters are pregiven.
• Possible formulations include, for example: Wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), dispersions based on oil or water, oil-miscible solutions, capsule suspensions (CS), dusting products (DP), dressings, granules for scattering and soil application, granules (GR) in the form of micro granules, spray granules, absorption and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.
• WP Wettable powders
• SP water-soluble powders
• EC
• the formulation auxiliaries required are likewise known and are described, for example, in: Watkins, “Handbook of Insecticide Dust Diluents and Carriers”, 2nd ed., Darland Books, Caldwell N.J.; H. v. Olphen, “Introduction to Clay Colloid Chemistry”, 2nd ed., J. Wiley & Sons, N.Y.; C. Marsden, “Solvents Guide”, 2nd ed., Interscience, N.Y. 1963; McCutcheon's “Detergents and Emulsifiers Annual”, MC Publ.
• Suitable safeners are e.g. mefenpyr-diethyl, cyprosulphamide, isoxadifen-ethyl, cloquintocet-mexyl and dichlormid.
• Wettable powders are preparations uniformly dispersible in water which, alongside the active ingredient apart from a diluent or inert substance, also comprise surfactants of an ionic and/or non-ionic type (wetting agent, dispersant), e.g.
• the herbicidally active ingredients are finely ground, for example in customary apparatus such as hammer mills, blower mills and air-jet mills, and simultaneously or subsequently mixed with the formulation auxiliaries.
• Emulsifiable concentrates are produced by dissolving the active ingredient in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene, or else relatively high-boiling aromatics or hydrocarbons or mixtures of the organic solvents, with addition of one or more ionic and/or nonionic surfactants (emulsifiers).
• organic solvent for example butanol, cyclohexanone, dimethylformamide, xylene, or else relatively high-boiling aromatics or hydrocarbons or mixtures of the organic solvents.
• emulsifiers which may be used are: Calcium alkylarylsulphonic acid salts such as Ca dodecylbenzenesulphonate or non-ionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide ethylene oxide condensation products, alkylpolyethers, sorbitan esters such as e.g. sorbitan fatty acid esters or polyoxyethylene sorbitan esters such as e.g. polyoxyethylene sorbitan fatty acid esters.
• Calcium alkylarylsulphonic acid salts such as Ca dodecylbenzenesulphonate
• non-ionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide ethylene oxide condensation products, alkylpolyethers, sorbitan esters such
• Dustable powders are obtained by grinding the active ingredient with finely distributed solid substances, for example talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
• solid substances for example talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
• Suspension concentrates can be based on water or oil. They can be produced, for example, by wet grinding by means of standard commercial bead mills and optionally the addition of surfactants, as have already been listed e.g. above for the other types of formulation.
• Emulsions e.g. oil-in-water emulsions (EW)
• EW oil-in-water emulsions
• Granules can be prepared either by spraying the active ingredient onto adsorptive granular inert material or by applying active ingredient concentrates to the surface of carriers, such as sand, kaolinites or granular inert material, by means of adhesives, for example polyvinyl alcohol, sodium polyacrylate or else mineral oils. Suitable active ingredients can also be granulated in the manner customary for producing fertilizer granules—if desired in a mixture with fertilizers.
• Water-dispersible granules are usually produced by the customary processes such as spray-drying, fluidized-bed granulation, pan granulation, mixing with high-speed mixers and extrusion without solid inert material.
• the agrochemical preparations generally comprise 0.1 to 99% by weight, in particular 0.1 to 95% by weight, of compounds according to the invention.
• the active ingredient concentration is e.g. about 10 to 90% by weight, the remainder to 100% by weight consists of customary formulation constituents. In the case of emulsifiable concentrations, the active ingredient concentration can be about 1 to 90, preferably 5 to 80% by weight. Dust-type formulations contain
• sprayable solutions comprise about 0.05 to 80, preferably 2 to 50% by weight of active ingredient.
• the active ingredient content depends partially on whether the active compound is present in liquid or solid form and on which granulation auxiliaries, fillers, etc., are used.
• the content of active ingredient is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
• the specified active ingredient formulations optionally comprise the adhesives, wetting agents, dispersants, emulsifiers, penetration agents, preservatives, frost protection agents and solvents, fillers, carriers and dyes, antifoams, evaporation inhibitors and agents influencing the pH and viscosity customary in each case.
• the formulations in commercial form are, if appropriate, diluted in a customary manner, for example in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules with water. Dust-type preparations, granules for soil application or granules for scattering and sprayable solutions are not normally diluted further with other inert substances prior to application.
• the required application rate of the compounds of the formula (I) varies with the external conditions, including temperature, humidity and the type of herbicide used. It can vary within wide limits, for example between 0.001 and 1.0 kg/ha or more of active substance, but it is preferably between 0.005 and 750 g/ha.
• 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: Ex. No. R 3 X Y R 1 M 1 H-NMR (400 MHz, ⁇ in ppm, d 6 -DMSO) S3 C 2 H 5 CH 3 CH 3 CH 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 2 H 5 C 2 H 5 CH 3 CH 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.
• Example numbers G1-G8 Analogously to Example G1 and according to the general details relating to the production, the following compounds are obtained Ex. 1H-NMR (400 MHz, ⁇ in ppm, No. R 3 X Y R 1 CDCl3) or melting point G1 CH 3 CH 3 CH 3 H m.p. 141° C. G2 C 2 H 5 CH 3 CH 3 H m.p. 159° C.
• 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.
• 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.
• 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.
• 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.
• 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.
• the pots are placed in a greenhouse and kept under good growth conditions for the trial plants.
• ALOMY Alopecurus myosuroides SETVI: Setaria viridis
• AMARE Amaranthus retroflexus
• AVEFA Avena fatua
• CYPES Cyperus esculentus
• ECHCG Echinochloa crus-galli
• LOLMU Lolium multiflorum
• Stellaria media VERPE: Veronica persica VIOTR: Viola tricolor
• POLCO Polygonum convolvulus LOLRI Lolium rigidium HORMU Hordeum murinum
• the compounds according to the invention have a good herbicidal pre-emergence effectiveness against a broad spectrum of weed grasses and weeds.
• 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.
• 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.
• 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.
• WP wettable powders
• EC emulsion concentrates
• compounds according to the invention have a good herbicidal post-emergence effectiveness against a broad spectrum of weed grasses and weeds.
• 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.

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