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
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
  • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
• • 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
  • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
  • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
  • A01P13/00—Herbicides; Algicides
  • A01P13/02—Herbicides; Algicides selective
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
  • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
  • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
  • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
  • C07D239/32—One oxygen, sulfur or nitrogen atom
  • C07D239/42—One nitrogen atom
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
  • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
  • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
  • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
  • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
  • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
  • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
  • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
  • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Definitions

• the invention relates to the technical field of plant protection products, in particular that of herbicides for the selective control of weeds and grasses in crops.
• this invention relates to substituted 2-aminoazines and their salts, processes for their preparation and their use as herbicides.
• Previously known plant protection products for the selective control of harmful plants in crops or active ingredients for combating undesirable plant growth sometimes have disadvantages when used, be it that they (a) have no or insufficient herbicidal effect against certain harmful plants, (b) too little Spectrum of harmful plants that can be controlled with an active ingredient, (c) insufficient selectivity in crops and/or (d) have a toxicologically unfavorable profile.
• active ingredients that can be used as plant growth regulators in some crops lead to undesirably reduced crop yields in other crops or are not compatible with the crop or are only compatible within a narrow application rate range.
• Some of the known active ingredients cannot be produced economically on an industrial scale due to difficult-to-access precursors and reagents or have inadequate chemical stability. With other active ingredients, the effect depends too heavily on environmental conditions such as weather and soil conditions.
• Heteroaryloxybenzenes were described in AU535637, EP8192, EP61913, JP61236766, WO2016/196606, WO2021/204706, GB2594931 and WO2016/010731, which were recognized as having a herbicidal effect.
• Heteroaryloxypyridines were described in WO2020/002089 and WO2022/002838, which were recognized as having herbicidal activity.
• WO2020/193474 described 2-heteroarylaminobenzenes, which were recognized as having a herbicidal effect.
• substituted 2-aminoazines or their salts have not yet been described as herbicidal active ingredients. Surprisingly, it has now been found that certain substituted 2-aminoazines or their salts are particularly suitable as herbicidal active ingredients.
• the present invention relates to substituted 2-aminoazines of the general formula (I) or their salts wherein
• A stands for nitrogen or CR 1 ,
• R 1 represents hydrogen, CN or halogen
• Q stands for ⁇ -(C2-Ce)-haloalkyl, where Y means direct bond, oxygen, S(O) n , CO or OSO2, or
• Q represents Z-aryl or Z-hetaryl, where aryl is optionally substituted with 1 to 5 substituents independently selected from the group R 4 , or hetaryl is substituted with up to 2 substituents independently selected from the group R 4 is, and where Z means direct bond or CH2,
• R 2 independently of each other for halogen, cyano, nitro, amino, (Ci-C4)-alkyl, (Ci-C -haloalkyl, cyclopropyl, ( 1-C4)-alkoxy, (Ci-CO-haloalkoxy, (Ci-C4) -Alkyl-S(O) n - stands, m is equal to 0, 1, 2 or 3, n is equal to 0, 1 or 2, R 3 for hydrogen, halogen, cyano, nitro, (C1-C4)-alkyl, (Ci-C4)-haloalkyl, (C1-C4)-alkoxy, (Ci-C2)-haloalkoxy, (Ci-C4)-alkyl -S(O) n - is, under the condition that if A is CR 1 , R 3 must not be hydrogen and
• the compounds of the general formula (I) can be prepared by adding a suitable inorganic or organic acid, such as mineral acids such as HCl, HBr, H2SO4, H iPO or HNO3, or organic acids, e.g. B. carboxylic acids, such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid or sulfonic acids, such as p-toluenesulfonic acid, to a basic group, such as amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino, to form salts. These salts then contain the conjugate base of the acid as an anion.
• a suitable inorganic or organic acid such as mineral acids such as HCl, HBr, H2SO4, H iPO or HNO3, or organic acids, e.g. B. carboxylic acids, such as formic acid, acetic acid, propionic acid, oxa
• Suitable substituents that are present in deprotonated form can form internal salts with protonatable groups, such as amino groups. Salt formation can also occur through the action of a base on compounds of general formula (I).
• Suitable bases are, for example, organic amines such as trialkylamines, morpholine, piperidine and pyridine as well as ammonium, alkali or alkaline earth metal hydroxides, carbonates and bicarbonates, in particular sodium and potassium hydroxide, sodium and potassium carbonate and sodium and potassium bicarbonate.
• salts are compounds in which the acidic hydrogen is replaced by a cation suitable for agriculture, for example metal salts, in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or also ammonium salts, salts with organic amines or quaternary ammonium salts, for example with cations the formula [NR a R b R c R d ] + , in which R a to R d each independently represent an organic radical, in particular alkyl, aryl, arylalkyl or alkylaryl.
• alkylsulfonium and alkylsulfoxonium salts such as (Ci-C l-trialkylsulfonium and (Ci-CO-trialkylsulfoxonium salts.
• substituted 2-aminoazines of the general formula (I) according to the invention can, depending on external conditions, such as pH, solvent and temperature, possibly be present in various tautomeric structures, all of which are encompassed by the general formula (I).
• A stands for nitrogen or CR 1 ,
• R 1 represents hydrogen, CN or halogen
• Q stands for Y-(C3-C5)-haloalkyl, where Y means direct bond, oxygen, S(O) n , CO or OSO2, or
• Q represents Z-aryl or Z-hetaryl, where aryl is optionally substituted with 1 to 3 substituents independently selected from the group R 4 , or hetaryl is substituted with up to 2 substituents independently selected from the group R 4 is, and where Z means direct bond or CH2,
• R 2 independently for halogen, cyano, nitro, amino, (Ci-C4)-alkyl, (Ci-C -haloalkyl, (Ci-CO-alkoxy, (Ci-CO-haloalkoxy, (Ci-C4)-alkyl- S(O) n - stands, m is equal to 0, 1, 2 or 3, n is equal to 0, 1 or 2,
• R 3 represents hydrogen, halogen, cyano, (Ci-C4)-alkyl, (Ci-C -haloalkyl, (C1-C4)-alkoxy, (C1-C2)-haloalkoxy, under the condition that if A is CR 1 stands, R 3 cannot be hydrogen and
• R 4 represents halogen, cyano, (CiC ⁇ -alkyl, (CiCO-haloalkyl, (C1C4) -alkoxymethyl.
• A stands for nitrogen or CR 1 , R 1 represents hydrogen, CN, CI or F,
• Q stands for Y-(C3-Cs)-haloalkyl, where Y means direct bond, oxygen, S(O) n , CO or OSO2, or
• Q represents Z-aryl or Z-hetaryl, where aryl is substituted with 1 or 2 substituents independently selected from the group R 4 , or hetaryl is substituted with up to 2 substituents independently selected from the group R 4 , and where Z means direct bond or CH2,
• R 2 independently represents fluorine, chlorine, bromine, cyano, methyl, CF3 or methoxy, m is equal to 0, 1 or 2, n is equal to 0, 1 or 2,
• R 3 is hydrogen, chlorine, fluorine, cyano, methyl, CF3, methoxy or CHF2O, provided that when A is CR 1 , R 3 must not be hydrogen and
• R 4 represents fluorine, chlorine, methyl, CHF2, CF3, methoxymethyl.
• A stands for nitrogen or CR 1 ,
• R 1 represents hydrogen, CN, CI or F
• B stands for CH or N, Q for (CH 2 ) 3 CF 3 , (CH 2 ) 4 CF 3 , S(CH 2 ) 3 CF 3 , SO(CH 2 ) 3 CF 3 , SO 2 (CH 2 ) 3 CF 3 , O(CH 2 ) 3 CF 3 , C(O)(CH 2 ) 3 CF 3 , OSO 2 (CH 2 ) 3 CF 3 , OSO 2 (CH 2 ) 3 C 2 F 5 Or
• R 2 independently represents fluorine, chlorine, bromine, cyano, methyl, CF 3 or methoxy, m is equal to 0, 1 or 2, n is equal to 0, 1 or 2 and
• R 3 is hydrogen, chlorine, fluorine, cyano, methyl, CF 3 , methoxy or CHF 2 O, with the proviso that when A is CR 1 , R 3 must not be hydrogen.
• A stands for nitrogen, CH, CF or CCN
• R 2 independently represents fluorine, chlorine, bromine, cyano, methyl, CF 3 or methoxy, m is equal to 0, 1 or 2, and
• R 3 is hydrogen, chlorine, fluorine, cyano, methyl, methoxy, CF3, with the proviso that when A is CH, R 3 must not be hydrogen.
• the general rule for the designation of chemical groups is that the connection to the framework or the rest of the molecule occurs via the last-mentioned structural element of the chemical group in question, ie, for example in the case of (C1-C4)-alkoxy via the oxygen atom, in the case of (Ci-C4)-AlkyI-S(O) n - via the sulfur atom and in the case of (C1-C4)-alkoxymethyl via the C atom of the methyl group.
• halogen means, for example, fluorine, chlorine, bromine or iodine. If the name is used for a residue, then “halogen” means, for example, a fluorine, chlorine, bromine or iodine atom.
• (C1-C4)-alkyl mentioned here as an example means a shorthand notation for straight-chain or branched alkyl with one to 4 carbon atoms corresponding to the range for C atoms, ie includes the radicals methyl, ethyl, 1-propyl, 2-propyl , 1-butyl, 2-Butyl, 2-Methylpropyl or tert-Butyl.
• General alkyl radicals with a larger specified range of carbon atoms e.g. B.
• (Ci-Cej-Alkyl) also includes straight-chain or branched alkyl radicals with a larger number of carbon atoms, ie according to the example also the alkyl radicals with 5 and 6 carbon atoms.
• Alkoxy means an alkyl radical bonded via an oxygen atom, e.g. B. (but not limited to) (C1-C4)-alkoxy such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy and 1,1-dimethylethoxy.
• Haloalkoxy is, for example, OCF 3 , OCHF 2 , OCH 2 F, OCF2CF3, OCH2CF3 and OCH2CH2CI.
• aryl means an optionally substituted mono-, bi- or polycyclic aromatic system with preferably 6 to 14, in particular 6 to 10 ring C atoms, for example phenyl, naphthyl, anthryl, phenanthrenyl, and the like, preferably phenyl.
• heteroaromatic compounds ie completely unsaturated aromatic heterocyclic compounds, preferably for 5- to 7-membered rings with 1 to 4, preferably 1 or 2 identical or different heteroatoms, preferably O, S or N.
• Heteroaryls according to the invention are, for example, IH-pyrrol-l-yl; lH-Pyrrol-2-yl; lH-Pyrrol-3-yl; furan-2-yl; furan-3-yl; thien-2-yl; Thien-3-yl, IH-imidazol-l-yl; lH-imidazol-2-yl; lH-imidazol-4-yl; lH-imidazol-5-yl; IH-pyrazol-l-yl; lH-pyrazol-3-yl; lH-pyrazol-4-yl; lH-pyrazol-5-yl, 1H-1,2,3-triazol-l-yl, lH-l,2,3-triazol-4-yl, lH-l,2,3-triazol-5-yl, 2H-l,2,3-triazol-2-yl, 2H-l,2,3
• heteroaryl groups according to the invention can also be substituted with one or more, identical or different radicals. If two neighboring carbon atoms are part of another aromatic ring, these are fused heteroaromatic systems, such as benzofused or multiply fused heteroaromatics. For example, quinolines (e.g.
• quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl) are preferred );
• Isoquinolines e.g., isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl, isoquinolin-8-yl); quinoxaline; quinazoline; cinnoline; 1,5-naphthyridine; 1,6-naphthyridine; 1,7-naphthyridine; 1,8-naphthyridine; 2,6-naphthyridine; 2,7-naphthyridine; phthalazine; Pyridopyr azine; pyridopyrimidine
• heteroaryl are also 5- or 6-membered benzofused rings from the group IH-indol-l-yl, lH-indol-2-yl, lH-indol-3-yl, lH-indol-4-yl, lH- Indol-5-yl, 1H-indol-6-yl, lH-indol-7-yl, l-benzofuran-2-yl, l-benzofuran-3-yl, l-benzofuran-4-yl, l-benzofuran- 5-yl, l-benzofuran-6-yl, l-benzofuran-7-yl, l-benzothiophen-2-yl, l-benzothiophen-3-yl, 1-benzothiophen-4-yl, l-benzothiophen-5-yl yl, l-Benzobenzo
• the compounds of the general formula (I) can, depending on the type and connection of the substituents exist as stereoisomers.
• the possible stereoisomers defined by their specific spatial form, such as enantiomers, diastereomers, Z and E isomers, are all encompassed by the general formula (I).
• enantiomers, diastereomers, Z and E isomers are all encompassed by the general formula (I).
• diastereomers Z and E isomers
• enantiomers and diastereomers can occur.
• Stereoisomers can be obtained from the mixtures resulting from production using conventional separation methods.
• the chromatographic separation can be carried out both on an analytical scale to determine the enantiomeric excess or diastereomeric excess, as well as on a preparative scale to produce test samples for biological testing.
• stereoisomers can be produced selectively by using stereoselective reactions using optically active starting materials and/or auxiliary materials.
• the invention therefore also relates to all stereoisomers that are included in the general formula (I) but are not specified with their specific stereoform, as well as mixtures thereof.
• purification can also be carried out by recrystallization or digestion. If individual compounds of the general formula (I) are not satisfactorily accessible in the routes described below, they can be prepared by derivatization of other compounds of the general formula (I).
• Possible isolation, purification and stereoisomer separation processes for compounds of the general formula (I) include methods that are generally known to those skilled in the art from analogous cases, for example by physical processes such as crystallization, chromatography processes, especially column chromatography and HPEC (high-pressure liquid chromatography), distillation , if necessary under reduced pressure, extraction and other processes, any remaining mixtures can usually be separated by chromatographic separation, for example on chiral solid phases.
• physical processes such as crystallization, chromatography processes, especially column chromatography and HPEC (high-pressure liquid chromatography), distillation , if necessary under reduced pressure, extraction and other processes, any remaining mixtures can usually be separated by chromatographic separation, for example on chiral solid phases.
• crystallization for example diastereomeric salts, which can be obtained from the diastereomeric mixtures with optically active acids and, if necessary, with optically active bases if acidic groups are present, come into consideration.
• the present invention also claims processes for preparing the compounds of general formula (I) according to the invention.
• the compounds of the general formula (I) according to the invention can be prepared, among other things, using known processes.
• the synthesis routes used and investigated are based on commercially available or easily produced building blocks.
• the groups Q, A, R 2 , R 3 and m of the general formula (I) have the previously defined meanings in the following schemes, unless exemplary, but not restrictive, definitions are given.
• Compounds according to the invention can be prepared, for example, by the method given in Scheme 1 below.
• the pyri(mi)dines of the general formula (I) can be prepared via a coupling of the corresponding anilines (E-I) with the pyri(mi)dines (Eil), where LG is a leaving group, in the presence of, for example, a palladium catalyst.
• the base required for this can be, for example, a carbonate salt of an alkali metal (such as sodium or potassium).
• the reactions are generally carried out in an organic solvent, such as dioxane, dimethyl sulfoxide or dimethylformamide, at temperatures between 0°C and the boiling point of the solvent.
• the anilines of the general formula (E-I) are known from the literature and can be used, for example, according to Organic Letters, 19(14), 3855-3858; 2017 and similar methods described.
• the IH NMR data of selected examples are recorded in the form of 'H NMR peak lists. For each signal peak, first the 3 value is listed in ppm and then the signal intensity in round brackets. The 3-value signal intensity number pairs of different signal peaks are listed separated from each other by semicolons.
• the peak list of an example therefore has the form:
• the intensity of sharp signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the true ratios of the signal intensities. For broad signals, multiple peaks or the center of the signal and their relative intensity compared to the most intense signal in the spectrum can be shown.
• tetramethylsilane and/or the chemical shift of the solvent, especially in the case of spectra obtained in DMSO can be measured. Therefore, the tetramethylsilane peak may or may not appear in NMR peak lists.
• the peaks of stereoisomers of the target compounds and/or peaks of impurities usually have, on average, a lower intensity than the peaks of the target compounds (for example with a purity of >90%).
• Such stereoisomers and/or impurities can be typical of the respective manufacturing process. Their peaks can therefore help detect the reproduction of our manufacturing process using “by-product fingerprints”.
• An expert who calculates the peaks of the target compounds using known methods can isolate the peaks of the target compounds as required, using additional intensity filters if necessary. This isolation would be similar to the relevant peak picking in the classical 'H NMR interpretation.
• the present invention furthermore relates to the use of one or more compounds of the general formula (I) and/or their salts, as defined above, preferably in one of the embodiments marked as preferred or particularly preferred, in particular one or more compounds of the formulas (1 -1) to (1-86), (2-1) to (2-10) and/or their salts, each as defined above, as a herbicide and/or plant growth regulator, preferably in crops of useful and/or ornamental plants.
• the present invention further relates to a method for combating harmful plants and/or for regulating the growth of plants, characterized in that an effective amount of one or more compounds of the general formula (I) and/or their salts, as defined above, preferably in one those marked as preferred or particularly preferred Embodiment, in particular one or more compounds of the formulas (1-1) to (1-86), or (2-1) to (2-10) and / or their salts, each as defined above, or an agent according to the invention, as defined below, is applied to the (damaging) plants, (damaging) plant seeds, the soil in or on which the (damaging) plants grow, or the cultivated area.
• an effective amount of one or more compounds of the general formula (I) and/or their salts as defined above, preferably in one those marked as preferred or particularly preferred Embodiment, in particular one or more compounds of the formulas (1-1) to (1-86), or (2-1) to (2-10) and / or their salts, each as defined above, or an agent according to the invention, as defined below,
• the present invention also relates to a method for combating undesirable plants, preferably in useful plant crops, characterized in that an effective amount of one or more compounds of the general formula (I) and / or their salts, as defined above, preferably in one of the as preferred or particularly preferably characterized embodiment, in particular one or more compounds of the formulas (1-1) to (1-86), or (2-1) to (2-10) and / or their salts, each as defined above , or an agent according to the invention, as defined below, on undesirable plants (e.g. harmful plants such as mono- or dicotyledonous weeds or undesirable crop plants), the seeds of the undesirable plants (i.e. plant seeds, e.g.
• undesirable plants e.g. harmful plants such as mono- or dicotyledonous weeds or undesirable crop plants
• the seeds of the undesirable plants i.e. plant seeds, e.g.
• the soil in or on which the undesirable plants grow e.g. the soil of cultivated land or non-cultivated land
• the cultivated area i.e. Area where the unwanted plants will grow
• the present invention also relates to a method for controlling the growth of plants, preferably useful plants, characterized in that an effective amount of one or more compounds of the general formula (I) and / or their salts, as defined above, preferably in one the embodiment marked as preferred or particularly preferred, in particular one or more compounds of the formulas (1-1) to (1-86), or (2-1) to (2-10) and / or their salts, in each case as defined above, or an agent according to the invention as defined below, the plant, the seeds of the plant (ie plant seeds, for example grains, seeds or vegetative propagation organs such as tubers or parts of shoots with buds), the soil in which or on which the plants grow, (e.g.
• the soil of cultivated land or non-cultivated land or the cultivation area (ie area on which the plants will grow).
• the compounds according to the invention or the agents according to the invention can be applied, for example, in the pre-sowing (if necessary also by incorporation into the soil), pre-emergence and/or post-emergence processes.
• some representatives of the monocotyledonous and dicotyledonous weed flora may be mentioned by way of example, through which the compounds according to the invention can be controlled, without the naming being intended to restrict them to certain species.
• one or more compounds of the general formula (I) and/or their salts are used for combating harmful plants or for regulating growth in crops of useful plants or ornamental plants, the useful plants or ornamental plants in a preferred embodiment, transgenic plants are.
• the compounds of the general formula (I) according to the invention and/or their salts are suitable for combating the following genera of monocotyledonous and dicotyledonous harmful plants:
• 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 , Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.
• the compounds of the general formula (I) according to the invention are applied to the surface of the earth before the harmful plants (grasses and/or weeds) germinate (pre-emergence process), then either the emergence of the weed or weed seedlings is completely prevented or they grow to the cotyledon stage , but then stop growing and finally die completely after three to four weeks.
• the compounds of the general formula (I) according to the invention have excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, cultivated plants of economically important cultures, for example dicotyledonous cultures of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Miscanthus, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocot cultures of the genera Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea , depending on the structure of the respective compound according to the invention and its application rate, only insignificantly or not at all damaged.
• the present compounds are very suitable for the selective control of undesirable plant growth in plant crops such as agricultural crops or ornamental planting
• the compounds of the general formula (I) according to the invention (depending on their respective structure and the application rate applied) have excellent growth-regulating properties in cultivated plants. They regulate the plant's own metabolism and can therefore be used to specifically influence plant ingredients and to make harvesting easier, for example by triggering desiccation and stunted growth. Furthermore, they are also suitable for general control and inhibition of undesirable vegetative growth without killing the plants. Inhibition of vegetative growth plays a major role in many monocotyledonous and dicotyledonous cultures, as this can reduce or completely prevent lodging, for example.
• the compounds of the general formula (I) can also be used to combat harmful plants in cultures of plants modified genetically or by conventional mutagenesis.
• the transgenic plants are usually characterized by special advantageous properties, for example resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
• Other special properties concern, for example, the harvested crop in terms of quantity, quality, storage life, composition and special ingredients.
• Transgenic plants with increased starch content or altered starch quality or those with a different fatty acid composition of the crop are known.
• transgenic cultures preference is given to using the compounds according to the invention of the general formula (I) and/or their salts in economically important transgenic cultures of useful and ornamental plants, for example cereals such as wheat, barley, rye, oats, millet, rice and corn or else Crops of sugar beet, cotton, soy, rapeseed, potato, tomato, pea and other vegetables.
• cereals such as wheat, barley, rye, oats, millet, rice and corn or else Crops of sugar beet, cotton, soy, rapeseed, potato, tomato, pea and other vegetables.
• the compounds of the general formula (I) according to the invention can preferably also be used as herbicides in crops of useful plants which are resistant to the phytotoxic effects of the herbicides or have been made resistant by genetic engineering.
• the compounds of the general formula (I) according to the invention can also be used to combat harmful plants in cultures of known or yet to be developed genetically modified plants.
• the transgenic plants are usually characterized by special advantageous properties, for example resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
• Other special properties relate, for example, to the harvested crop in terms of quantity, quality, storage life, composition and special ingredients.
• Transgenic plants with increased starch content or altered starch quality or those with a different fatty acid composition of the crop are known.
• Other special properties may include tolerance or resistance to abiotic stressors such as heat, cold, drought, salt and ultraviolet radiation.
• cereals such as wheat, barley, rye, oats, triticale, millet, rice, cassava and maize or else Crops of sugar beet, cotton, soy, rapeseed, potato, tomato, pea and other vegetables.
• the compounds of the general formula (I) can preferably be used as herbicides in crops of useful plants which are resistant to the phytotoxic effects of the herbicides or which have been made resistant by genetic engineering.
• new plants with modified properties can be created using genetic engineering processes. Numerous molecular biology techniques with which new transgenic plants with modified properties can be produced are known to those skilled in the art.
• nucleic acid molecules can be introduced into plasmids that allow mutagenesis or sequence changes through recombination of DNA sequences. With the help of standard procedures, base exchanges can be carried out, partial sequences can be removed or natural or synthetic sequences can be added.
• adapters or anchors can be attached to the fragments.
• the production of plant cells with a reduced activity of a gene product can be achieved, for example, by expressing at least one corresponding antisense RNA, a sense RNA to achieve a co-suppression effect or the expression of at least one appropriately constructed ribozyme that specifically cleaves transcripts of the above-mentioned gene product.
• DNA molecules can be used that include the entire coding sequence of a gene product, including any flanking sequences that may be present, as well as DNA molecules that only include parts of the coding sequence, whereby these parts must be long enough to be in the cells to cause an antisense effect. It is also possible to use DNA sequences that have a high degree of homology to the coded sequences of a gene product, but are not completely identical.
• the synthesized protein can be localized in any compartment of the plant cell.
• the coding region can, for example, be linked to DNA sequences that ensure localization in a specific compartment.
• sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227).
• the expression of the nucleic acid molecules can also take place in the organelles of plant cells.
• the transgenic plant cells can be regenerated into whole plants using known techniques.
• the transgenic plants can in principle be plants of any plant species, i.e. both monocotyledonous and dicotyledonous plants.
• the compounds of the general formula (I) according to the invention can preferably be used in transgenic cultures which are active against growth substances, such as dicamba or against herbicides, which contain essential plant enzymes, for example acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydoxyphenylpyruvate dioxygenases (HPPD ) or are resistant to herbicides from the group of sulfonylureas, glyphosates, glufosinates or benzoyl lisoxazole and analogous active ingredients.
• ALS acetolactate synthases
• EPSP synthases glutamine synthases
• HPPD hydoxyphenylpyruvate dioxygenases
• the invention therefore also relates to the use of the compounds of the general formula (I) according to the invention and/or their salts as herbicides for combating harmful plants in crops of useful or ornamental plants, optionally in transgenic crop plants.
• the use of compounds of the formula (I) according to the invention for combating harmful plants or for regulating the growth of plants also includes the case in which a compound of the general formula (I) or its salt is only used after application on the plant, in the plant or in the plant Soil is formed from a precursor substance (“prodrug”).
• the invention also relates to the use of one or more compounds of the general formula (I) or their salts or an agent according to the invention (as defined below) (in a process) for combating harmful plants or for regulating the growth of plants, characterized in that: an effective amount of one or more compounds of the general formula (I) or their salts is applied to the plants (harmful plants, optionally together with the useful plants) plant seeds, the soil in which or on which the plants grow, or the cultivated area.
• the invention also relates to a herbicidal and/or plant growth regulating agent, characterized in that the agent
• (a) contains one or more compounds of the general formula (I) and/or their salts as defined above, preferably in one of the embodiments marked as preferred or particularly preferred, in particular one or more compounds of the formulas (1-1) to ( 1-86) or (2-1) to (2-10) and/or their salts, each as defined above, and
• one or more further agrochemically active substances preferably selected from the group consisting of insecticides, acaricides, nematicides, other herbicides (i.e. those which do not correspond to the general formula (I) defined above), fungicides, safeners, fertilizers and / or other growth regulators,
• component (i) of an agent according to the invention are preferably selected from the group of substances described in "The Pesticide Manual”, 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012.
• a herbicidal or plant growth-regulating agent according to the invention preferably comprises one, two, three or more formulation aids (ii) common in plant protection, selected from the group consisting of surfactants, emulsifiers, dispersants, film formers, thickeners, inorganic salts, dusting agents, at 25 ° C and 1013 mbar solid carrier materials, preferably adsorbable, granulated inert materials, wetting agents, antioxidants, stabilizers, buffer substances, anti-foaming agents, water, organic solvents, preferably organic solvents miscible with water in any ratio at 25 ° C and 1013 mbar.
• formulation aids ii) common in plant protection, selected from the group consisting of surfactants, emulsifiers, dispersants, film formers, thickeners, inorganic salts, dusting agents, at 25 ° C and 1013 mbar solid carrier materials, preferably adsorbable, granulated inert materials, wetting agents, antioxidants
• the compounds of the general formula (I) according to the invention can be used in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusting agents or granules in the usual preparations.
• the invention therefore also relates to herbicidal and plant growth-regulating agents which contain compounds of the general formula (I) and/or their salts.
• the compounds of the general formula (I) according to the invention and/or their salts can be formulated in various ways, depending on which biological and/or chemical-physical parameters are specified.
• Possible formulation options include, for example: wettable powder (WP), water-soluble powder (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions , suspension concentrates (SC), oil- or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), dusts (DP), dressing agents, granules for litter and soil application, granules (GR) in the form of micro, spray, elevator - and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.
• WP wettable powder
• SP water-soluble powder
• EC emulsifiable concentrates
• EW emulsions
• SC suspension concentrates
• CS oil- or water-based dispersions
• CS capsule suspension
• Wettable powders are preparations that are uniformly dispersible in water and which, in addition to the active ingredient, contain a diluent or inert substance, ionic and/or nonionic surfactants (wetting agents, dispersants), e.g.
• the herbicidal active ingredients are finely ground, for example, in conventional equipment such as hammer mills, blower mills and air jet mills and simultaneously or subsequently mixed with the formulation aids.
• Emulsifiable concentrates are produced by dissolving the active ingredient in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons or mixtures of the organic solvents with the addition of one or more ionic and/or nonionic surfactants (emulsifiers).
• organic solvent for example butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons or mixtures of the organic solvents with the addition of one or more ionic and/or nonionic surfactants (emulsifiers).
• Alkylarylsulfonic acid calcium salts such as Ca-dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as sorbitan fatty acid esters or polyoxyethylene sorbitan esters such as polyoxyethylene sorbitan fatty acid esters.
• Dusting agents are obtained by grinding the active ingredient with finely divided solid substances, e.g. talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
• finely divided solid substances e.g. talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
• Suspension concentrates can be water or oil based. They can be produced, for example, by wet grinding using commercially available bead mills and, if necessary, adding surfactants, such as those already listed above for the other types of formulations.
• Emulsions for example oil-in-water emulsions (EW)
• EW oil-in-water emulsions
• stirrers, colloid mills and/or static mixers using aqueous organic solvents and optionally surfactants, such as those already listed above for the other types of formulations.
• Granules can be produced either by spraying the active ingredient onto adsorbable, granulated inert material or by applying active ingredient concentrates using adhesives, e.g. polyvinyl alcohol, sodium polyacrylic acid or mineral oils, to the surface of carrier materials such as sand, kaolinite or granulated inert material.
• adhesives e.g. polyvinyl alcohol, sodium polyacrylic acid or mineral oils
• Suitable active ingredients can also be granulated in the usual way for the production of fertilizer granules - if desired in a mixture with fertilizers.
• Water-dispersible granules are usually produced by the usual methods such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material.
• the agrochemical preparations, preferably herbicidal or plant growth regulating agents, of the present invention preferably contain a total amount of 0.1 to 99% by weight, preferably 0.5 to 95% by weight, more preferably 1 to 90% by weight, particularly preferred 2 to 80% by weight of active ingredients of the general formula (I) and their salts.
• the active ingredient concentration is, for example, around 10 to 90% by weight, the remainder, 100% by weight, consists of usual formulation components.
• the active ingredient concentration can be approximately 1 to 90, preferably 5 to 80% by weight.
• Dusty formulations contain 1 to 30% by weight of active ingredient, preferably usually 5 to 20% by weight of active ingredient, sprayable solutions contain approximately 0.05 to 80, preferably 2 to 50% by weight of active ingredient.
• the active ingredient content depends in part on whether the active compound is liquid or solid and which granulation aids, fillers, etc. are used.
• the active ingredient content is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
• the active ingredient formulations mentioned may contain the usual adhesive, wetting, dispersing, emulsifying, penetrating, preservatives, antifreeze and solvents, fillers, carriers and dyes, defoamers, evaporation inhibitors and the pH value and Agents influencing viscosity.
• formulation aids are described, among others, in “Chemistry and Technology of Agrochemical Formulations”, ed. D. A. Knowles, Kluwer Academic Publishers (1998).
• the compounds of the general formula (I) according to the invention or their salts can be used as such or in the form of their preparations (formulations) combined with other pesticide-active substances, such as insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and / or growth regulators e.g. as ready-made formulations or as tank mixes.
• pesticide-active substances such as insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and / or growth regulators e.g. as ready-made formulations or as tank mixes.
• the combination formulations can be produced based on the above-mentioned formulations, taking into account the physical properties and stability of the active ingredients to be combined.
• combination partners for the compounds of the general formula (I) according to the invention in mixture formulations or in the tank mix are known active ingredients which are based on an inhibition of, for example, acetolactate synthase, acetyl-Co A carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate -synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoenesaturase, photosystem I, photosystem II, protoporphyrinogen oxidase, can be used, for example in Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 16th edition , The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 and the one cited there
• the weight ratio of herbicide (mixture) to safener generally depends on the amount of herbicide applied and the effectiveness of the respective safener and can vary within wide limits, for example in the range from 200:1 to 1:200, preferably 100:1 to 1: 100, especially 20:1 to 1:20.
• the safeners can be formulated analogously to the compounds of the general formula (I) or mixtures thereof with other herbicides/pesticides and can be provided and used as a ready-made formulation or tank mixture with the herbicides.
• the herbicide or herbicide-safener formulations available in commercial form are, if necessary, diluted in the usual way, for example in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules using water. Dusty preparations, soil or litter granules and sprayable solutions are usually no longer diluted with other inert substances before use.
• the application rate of the compounds of the general formula (I) and/or their salts influences to a certain extent the application rate of the compounds of the general formula (I) and/or their salts.
• the application rate can vary within wide limits.
• the total amount of compounds of the general formula (I) and their salts is preferably in the range from 0.001 to 10.0 kg/ha, preferably in the range from 0.005 to 5 kg/ha, more preferably in Range from 0.01 to 1.5 kg/ha, particularly preferably in the range from 0.05 to 1 kg/ha. This applies to both pre-emergence and post-emergence applications.
• the total application rate is preferably in the range from 0.001 to 2 kg/ha, preferably in the range from 0.005 to 1 kg/ha, in particular in the range from 10 to 500 g/ha, very particularly preferably in the range from 20 to 250 g/ha. Ha. This applies to both pre-emergence and post-emergence applications.
• the application as a stalk shortener can take place at different stages of plant growth. For example, application after tillering at the beginning of longitudinal growth is preferred.
• treatment of the seeds can also be considered, which includes various seed dressing and coating techniques.
• the application rate depends on the individual techniques and can be determined in preliminary tests.
• combination partners for the compounds according to the invention of the general formula (I) in agents according to the invention are known active ingredients which are based on an inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate -3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoenesaturase, photosystem I, photosystem II or protoporphyrinogen oxidase, can be used, as for example from Weed Research 26 (1986) 441-445 or "The Pesticide Manual ", 16th edition, The British Crop Protection Council and the Royal Soc.
• herbicidal mixing partners are:
• plant growth regulators as possible mixing partners are: Acibenzolar, acibenzolar-S-methyl, 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine, brassinolide, catechin, chlormequat chloride, cloprop, cyclanilide, 3-(cycloprop-l-enyl)propionic acid, daminozide, dazomet, n-decanol, dikegulac, dikegulac-sodium, endothal, endothal-dipotassium, -disodium, and mono(N,N-dimethylalkylammonium), ethephon, flumetralin, flurenol, flurenol-butyl, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid (IAA), 4-indol-3-ylbutyric acid, isoprothiolane, probeazole
• Sl a Compounds of the dichlorophenylpyrazoline-3-carboxylic acid type (Sl a ), preferably compounds such as l-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazolin-3-carboxylic acid, 1 - (2,4-Dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazolin-3-carboxylic acid ethyl ester (S 1 - 1) ("Mefenpyr-diethyl"), and related compounds as described in WO-A -91/07874 are described; Sl b ) Derivatives of dichlorophenylpyrazolecarboxylic acid (Sl b ), preferably compounds such as l-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylic acid ethyl ester (Sl-2), l-(2,4-dichlor
• Sl c Derivatives of l,5-diphenylpyrazole-3-carboxylic acid (Sl c ), preferably compounds such as 1-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylic acid ethyl ester (S 1 -5), l-(2 -Chlorophenyl)-5-phenylpyrazole-3-carboxylic acid methyl ester (Sl-6) and related compounds as described, for example, in EP-A-268554;
• Sl d Compounds of the triazole carboxylic acid type (Sl d ), preferably compounds such as fenchlorazole (ethyl ester), ie l-(2,4-dichlorophenyl)-5-trichloromethyl-(lH)-1,2,4-triazole-3 - ethyl carbonate (Sl-7), and related compounds as described in EP-A-174562 and EP-A-346620;
• S2 a Compounds of the type of 8-quinolinoxyacetic acid (S2 a ), preferably (5-chloro-8-quinolinoxy)acetic acid (l-methylhexyl) ester ("Cloquintocet-mexyl") (S2-1), (5- Chloro-8-quinolinoxy)acetic acid (1,3-dimethyl-but-l-yl) ester (S2-2), (5-chloro-8-quinolinoxy)acetic acid 4-allyl-oxy-butyl ester (S2- 3), (5-chloro-8-quinolinoxy)acetic acid-l-allyloxy-prop-2-yl ester (S2-4), (5-chloro-8-quinolinoxy)acetic acid ethyl ester (S2-5), (5-chloro- 8-quinolinoxy)acetic acid methyl ester (S2-6), (5-chloro-8-quinolinoxy)acetic acid allyl ester (S2-7), (5-chlor
• R-29148 (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) from Stauffer (S3-2),
• R-28725" (3-dichloroacetyl-2, 2, -dimethyl- 1,3-oxazolidine) from Stauffer (S3-3), "Benoxacor” (4-dichloroacetyl-3,4-dihydro-3-methyl- 2H-l,4-benzoxazine) (S3-4), "PPG-1292” (N-allyl-N-[(l,3-dioxolan-2-yl)-methyl]-dichloroacetamide) from PPG Industries (S3 -5),
• AD-67 or “MON 4660” (3-dichloroacetyl-l-oxa-3-aza-spiro[4,5]decane) from Nitrokemia or Monsanto (S3-7),
• TI-35 (1-dichloroacetyl-azepane) from TRI-Chemical RT (S3-8),
• RA 1 (Ci-C6)-alkyl, (C3-C6)-cycloalkyl, where the last two radicals are replaced by VA substituents from the group halogen, (Ci-C4)-alkoxy, (Ci-C6)-haloalkoxy and (Ci- C4)-alkylthio and, in the case of cyclic radicals, also by (Ci-C4)-alkyl and (Ci-C4)-haloalkyl;
• RA 2 halogen (C1-C4)-alkyl, (Ci-C4)-alkoxy, CF3; mA 1 or 2;
• VA means 0, 1, 2 or 3;
• S4 b Compounds of the 4-(benzoylsulfamoyl)benzamide type of the formula (S4 b ) and their salts, as described in WO-A-99/16744, wherein
• RB 1 , RB 2 independently hydrogen, (Ci-Ce)-alkyl, (C 3 -Ce)-cycloalkyl,
• RB 3 means halogen, (C1-C4)-alkyl, (Ci-C4)-haloalkyl or (C1-C4)-alkoxy and ms 1 or 2, for example those in which
• RB 1 cyclopropyl
• RB 2 hydrogen
• (RB 3 ) 2-OMe
• RB 1 isopropyl
• RB 2 hydrogen
• (RB 3 ) 5-Cl-2-OMe is (S4-4) and
• Rc 1 , Rc 2 independently hydrogen, (Ci -Cs)-alkyl, (C 3 -Cs)-cycloalkyl, (C 3 -C 6 )-alkenyl, (C 3 -C 6 )-alkynyl,
• Rc 3 represents halogen, (Ci-C4)-alkyl, (Ci-C4)-alkoxy, CF 3 and me 1 or 2; for example l-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea,
• RD 5 hydrogen, (Ci-C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl,
• Dihydroxybenzoic acid 4-hydroxysalicylic acid, 4-fluorosalicyclic acid, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid, as described in WO-A-2004/084631, WO-A-2005/015994, WO-A-2005/016001.
• RD 1 is halogen, (Ci-C 4 )-alkyl, (Ci-C 4 )-haloalkyl, (Ci-C 4 )-alkoxy, (Ci-C 4 )-haloalkoxy,
• RD 2 is hydrogen or (Ci-C 4 )-alkyl
• RD 3 is hydrogen, (Ci -Cs)-alkyl, (C 2 -C 4 )-alkenyl, (C 2 -C 4 )-alkynyl, or aryl, where each of the aforementioned C-containing radicals is unsubstituted or by one or more , preferably up to three identical or different radicals from the group consisting of halogen and alkoxy are substituted; or their salts, no is an integer from 0 to 2.
• YE, ZE independently O or S, nE an integer from 0 to 4,
• RE 3 means hydrogen or (Ci-Ce)-alkyl.
• Active ingredients of the oxyimino compound type (Sil), which are known as seed dressings, such as: b.
• Oxabetrinil ((Z)-l,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile) (Sl l-1), which is known as a seed dressing safener for millet against damage from metolachlor,
• Naphthalic anhydride (1,8-naphthalenedicarboxylic anhydride) (S13-1), which is known as a seed dressing safener for corn against damage from thiocarbama herbicides,
• Active ingredients that, in addition to having a herbicidal effect against harmful plants, also have a safener effect on cultivated plants such as rice, such as: b.
• RH 1 represents a (Ci-C6)-haloalkyl radical
• RH 2 means hydrogen or halogen
• RH 3 , RH 4 independently of one another hydrogen, (Ci-Cie)-alkyl, (C2-Cie)-alkenyl or (C2-Ci6)-alkynyl, each of the latter 3 radicals being unsubstituted or by one or more radicals from the group halogen , hydroxy, cyano, (Ci-Ct -alkoxy, (Ci-CO-haloalkoxy, (Ci-CO-alkylthio, (Ci-Crj-alkylamino, di[(Ci-C4)alkyl]-amino, [(C1-C4 )alkoxy]-carbonyl, [(Ci-COHaloalkoxy]- carbonyl, (Cs-Cej-cycloalkyl, which is unsubstituted or substituted, phenyl, which is unsubstituted or substituted, and heterocyclyl, which is unsubstituted or substituted, is
• RH 3 means (Ci-Cr-alkoxy, (C2-C4)-alkenyloxy, (C2-Ce)-alkynyloxy or (C2-C4)-haloalkoxy and
• RH 4 means hydrogen or (C1-C4) alkyl, or
• RH 3 and RH 4 together with the directly bonded N atom form a four- to eight-membered heterocyclic ring which, in addition to the N atom, can also contain further heteroring atoms, preferably up to two further heteroring atoms from the group N, O and S and which is unsubstituted or substituted by one or more radicals from the group halogen, cyano, nitro, (Ci-CO-alkyl, (Ci-Ct -haloalkyl, (Ci-Crj-alkoxy, (Ci-Ct -haloalkoxy and (Ci-CO-alkylthio is, means.
• Preferred safeners in combination with the compounds of the general formula (I) according to the invention and/or their salts, in particular with the compounds of the formulas (1-1) to (1-86) or (2-1) to (2-10) and/or their salts are: cloquintocet-mexyl, cyprosulfamide, fenchlorazole ethyl ester, Isoxadifen-ethyl, Mefenpyr-diethyl, Fenclorim, Cumyluron, S4-1 and S4-5, and particularly preferred safeners are: Cloquintocet-mexyl, Cyprosulfamide, Isoxadifen-ethyl and Mefenpyr-diethyl.
• ABUTH Abutilon theophrasti
• ECHCG Echinochloa crus-galli
• KCHSC Kochia scoparia
• MATIN Matricaria inodora
• VERPE Veronica persica
• VIOTR Viola tricolor
• Tables A1 to A10 below show the effects of selected compounds of the general formula (I) according to Table 1 on various harmful plants and an application rate corresponding to 320 g/ha, which were obtained according to the aforementioned test instructions.
• Table A3 Post-emergence effect at 320g/ha against AM ARE in %
• Table A4 Post-emergence effect at 320g/ha against DIGS A in %
• Table A8 Post-emergence effect at 320g/ha against SETVI in %
• Table A9 Post-emergence effect at 320g/ha against STEME in %
• Tables B1 to B11 below show the effects of selected compounds of the general formula (I) according to Table 1 on various harmful plants and an application rate corresponding to 80 g/ha, which were obtained in accordance with the aforementioned test instructions.
• Table B2 Post-emergence effect at 80g/ha against ALOMY in %
• Table B3 Post-emergence effect at 80g/ha against AMARE in %
• Table Bl l Post-emergence effect at 80g/ha against VIOTR in %
• Table Bl l Post-emergence effect at 80g/ha against VIOTR in %
• the test results demonstrate that compounds of the general formula (I) according to the invention, when treated post-emergence, have good herbicidal activity against selected harmful plants such as Abutilon theophrasti, Alopecurus myosuroides, Amaranthus retroflexus, Digitaria sanguinalis, Echinochloa crus-galli, Kochia scoparia, Polygonum convolvulus, Veronica persica and Viola tricolor at a respective application rate of 80 g of active substance per hectare.
• selected harmful plants such as Abutilon theophrasti, Alopecurus myosuroides, Amaranthus retroflexus, Digitaria sanguinalis, Echinochloa crus-galli, Kochia scoparia, Polygonum convolvulus, Veronica persica and Viola tricolor at a respective application rate of
• Seeds of monocotyledonous and dicotyledonous weed plants were placed in plastic pots in sandy loam soil (double sowing with one species of monocotyledonous or dicotyledonous weed plant per pot) and covered with soil.
• the compounds according to the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC), were then applied as an aqueous suspension or emulsion, with the addition of 0.5% additive, with a water application rate of the equivalent of 600 liters per hectare to the surface of the covering soil applied. After treatment, the pots were placed in the greenhouse and maintained under good growth conditions for the test plants. After about 3 weeks, the effect of the preparations was assessed visually in percentage values compared to untreated controls.
• Tables CI to C12 below show the effects of selected compounds of the general formula (I) according to Table 1 on various harmful plants and an application rate corresponding to 320 g/ha, which were obtained according to the aforementioned test instructions.
• Table CI Pre-emergence effect at 320g/ha against ABUTH in %
• Table C2 Pre-emergence effect at 320g/ha against ALOMY in %
• Table C3 Pre-emergence effect at 320g/ha against AMARE in %
• Table C4 Pre-emergence effect at 320g/ha against DIGSA in %
• Table C5 Pre-emergence effect at 320g/ha against ECHCG in %
• Table C6 Pre-emergence effect at 320g/ha against KCHSC in %
• Table C8 Pre-emergence effect at 320g/ha against MATIN in %
• Table C9 Pre-emergence effect at 320g/ha against POAAN in %
• test results prove that compounds of the general formula (I) according to the invention, when treated in advance of emergence, have good herbicidal activity against selected harmful plants such as Abutilon theophrasti, Alopecurus myosuroides, Amaranthus retroflexus, Digitaria sanguinalis, Echinochloa crus-galli, Kochia scoparia, Lolium rigidum, Matricaria inodora, Poa annua, Setaria viridis, Stellaria media and Veronica persica at a respective application rate of 320 g of active substance per hectare.
• selected harmful plants such as Abutilon theophrasti, Alopecurus myosuroides, Amaranthus retroflexus, Digitaria sanguinalis, Echinochloa crus-galli, Kochia scoparia, Lolium rigidum, Matricaria inodora, Poa annua, Setaria viridis, Stellaria media and Veronica persica at a respective application rate of 320 g of active substance per hectare
• Seeds of monocotyledonous or dicotyledonous weeds and crop plants were placed in plastic or organic plant pots and covered with soil.
• Tables D1 to D12 below show the effects of selected compounds of the general formula (I) according to Table 1 on various harmful plants and an application rate corresponding to 80 g/ha, which were obtained according to the aforementioned test instructions.
• Table Dl Pre-emergence effect at 80g/ha against ABUTH in %
• Table D7 Pre-emergence effect at 80g/ha against KCHSC in %
• Table D8 Pre-emergence effect at 80g/ha against MATIN in %
• Table DIO Pre-emergence effect at 80g/ha against SETVI in %
• Table Dl l Pre-emergence effect at 80g/ha against VERPE in %
• test results prove that compounds of the general formula (I) according to the invention, when treated in advance of emergence, have good herbicidal activity against selected harmful plants such as Abutilon theophrasti, Alopecurus myosuroides, Amaranthus retroflexus, Digitaria sanguinalis, Echinochloa crus-galli, Kochia scoparia, Lolium rigidum, Matricaria inodora, Polygonum convolvulus, Setaria viridis, Veronica persica and Viola tricolor at a respective application rate of 80 g of active substance per hectare.
• harmful plants such as Abutilon theophrasti, Alopecurus myosuroides, Amaranthus retroflexus, Digitaria sanguinalis, Echinochloa crus-galli, Kochia scoparia, Lolium rigidum, Matricaria inodora, Polygonum convolvulus, Setaria viridis, Veronica persica and Viola tricolor at a respective application rate of 80 g of active substance per

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• 2023
  • 2023-03-23 WO PCT/EP2023/057450 patent/WO2023186690A1/de not_active Ceased
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