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WO2025103927A1 - Oxyiminométhylphényluraciles substitués, sels de ceux-ci et leur utilisation en tant que substances actives herbicides - Google Patents

Oxyiminométhylphényluraciles substitués, sels de ceux-ci et leur utilisation en tant que substances actives herbicides Download PDF

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Publication number
WO2025103927A1
WO2025103927A1 PCT/EP2024/081820 EP2024081820W WO2025103927A1 WO 2025103927 A1 WO2025103927 A1 WO 2025103927A1 EP 2024081820 W EP2024081820 W EP 2024081820W WO 2025103927 A1 WO2025103927 A1 WO 2025103927A1
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alkyl
aryl
alkoxy
cycloalkyl
heteroaryl
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English (en)
Inventor
Jens Frackenpohl
Harald Jakobi
Hendrik Helmke
Elmar Gatzweiler
Birgit BOLLENBACH-WAHL
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Bayer AG
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Bayer AG
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    • 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
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
    • 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
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms 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
    • C07D413/12—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 chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/08—Bridged systems

Definitions

  • the invention relates to the technical field of crop protection agents, in particular to herbicides for the selective control of weeds and grass weeds in crops of useful plants.
  • this invention relates to substituted oxyiminomethylphenyluracils with 4-difluoroalkyl substitution on the uracil and their salts, processes for their preparation and their use as herbicides, in particular for controlling weeds and/or grass weeds in crops of useful plants and/or as plant growth regulators for influencing the growth of crops of useful plants.
  • Previously known plant protection products for the selective control of weeds in crops or active ingredients for controlling undesirable plant growth sometimes have disadvantages in their use, be it (a) they have no or insufficient herbicidal activity against certain weeds, (b) an insufficient spectrum of weeds that can be controlled with an active ingredient, (c) insufficient selectivity in crops and/or (d) a toxicologically unfavorable profile.
  • active ingredients that can be used as plant growth regulators in some crops lead to undesirably reduced crop yields in others 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 insufficient chemical stability.
  • N-linked aryluracils A number of herbicidal active ingredient combinations based on N-linked aryluracils have also been disclosed. (cf. DE4437197, EP714602, WO96/07323, WO96/08151, JP11189506). However, the properties of these active ingredient combinations are not entirely satisfactory. It is also known that certain N-aryluracils with optionally further substituted lactic acid groups can also be used as herbicidal active ingredients (cf. JP2000/302764, JP2001/172265, US6403534, EP408382A1). Furthermore, it is known that N-aryluracils with specific, optionally further substituted, thiolactic acid groups also exhibit herbicidal effects (cf.
  • N-benzoic acid uracils with an aminosulfonylaminocarbonylalkoxy side chain are also known (cf. WO2004/009561). It is also known that certain substituted N-benzoic acid thiobarbiturates can be used as herbicidal active ingredients (cf. WO2021/259224). Certain oxyiminomethylphenyluracils have been described as herbicidal active ingredients (cf. EP 4089078). Difluoroalkyl-substituted uracils have also been described as herbicidal active ingredients (cf. WO1988010254; WO2023285222).
  • R 1 represents hydrogen, halogen, or (C 1 -C 4 )-alkoxy
  • R 2 represents halogen, cyano, nitro, C(O)NH 2 , C(S)NH 2 , (C 1 -C 8 )-haloalkyl, or (C 2 -C 8 )-alkynyl
  • R 3 and R 4 independently of one another represent hydrogen, (C 1 -C 8 )-alkyl
  • R 13 represents O-(C 1 -C 8 )-alkyl, (C 3 -C 8 )-cycloalkyl, (C 2 -C 8 )-alkenyl, aryl-(C 1 -C 8 )-alkyl, heteroaryl-(C 1 -C 8 )-alkyl, or heterocyclyl-(C 1 -C 8 )-alkyl, or R 3 and R 4 together with the carbon atom to which they are attached form a fully saturated or partially saturated, 3 to 10-membere
  • the compounds of the general formula (I) according to the invention firstly achieve a good herbicidal effect, but secondly also have good, environmentally friendly degradation properties and are therefore less harmful to the environment.
  • the compounds of the general formula (I) can form salts by addition of a suitable inorganic or organic acid, for example mineral acids such as HCl, HBr, H 2 SO 4 , H 3 PO 4 or HNO 3 , or organic acids, e.g.
  • 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.
  • These salts then contain the conjugate base of the acid as an anion.
  • Suitable substituents that are present in deprotonated form, such as sulfonic acids, certain sulfonamides, or carboxylic acids, 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 include, 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.
  • organic amines such as trialkylamines, morpholine, piperidine, and pyridine
  • 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 of the formula [NR a R b R c R d ] + , in which Ra to R d each independently of one another represent an organic radical, in particular alkyl, aryl, aralkyl or alkylaryl.
  • 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 of the formula [NR a R b R c R d ] + , in which Ra to R d each independently of one another represent an organic radical
  • alkylsulfonium and alkylsulfoxonium salts such as (C1-C4)-trialkylsulfonium and (C1-C4)-trialkylsulfoxonium salts.
  • alkylsulfonium and alkylsulfoxonium salts such as (C1-C4)-trialkylsulfonium and (C1-C4)-trialkylsulfoxonium salts.
  • W represents the group W -1 W-2
  • R 1 represents hydrogen, fluorine, chlorine, or bromine
  • R 2 represents fluorine, chlorine, bromine, cyano, nitro, C(O)NH2, C(S)NH2, trifluoromethyl, ethynyl, or propyn-1-yl
  • R 3 and R 4 independently of one another represent hydrogen, (C 1 -C 6 )-alkyl
  • R 13 represents O-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 2 -C 6 )-alkenyl, aryl-(C 1 -C 6 )-alkyl, heteroaryl-(C 1 -C 6 )-alkyl, or heterocyclyl-(C 1 -C 6 )-alkyl, or R 3 and R 4 together with the carbon atom to which they are attached form a fully saturated or partially saturated, 3
  • R 1 represents hydrogen, fluorine, or chlorine
  • R 2 represents fluorine, chlorine, bromine, cyano, nitro, C(O)NH 2 , C(S)NH 2 , or trifluoromethyl
  • R 3 and R 4 independently of one another represent hydrogen, (C1-C4)-alkyl, or (C1-C4)-haloalkyl, or R 3 and R 4 together with the carbon atom to which they are attached form a fully saturated or partially saturated, 3 to 7-membered carbocyclic ring
  • R 5 represents hydrogen, (C1-C4)-alkyl, or (C1-C4)-haloalkyl
  • R 6 represents methyl, ethyl, or prop-1-yl
  • R 7 represents hydrogen
  • Q represents hydroxy or a radical of the following formulas O
  • R 8 represents hydrogen, (C 1 -C 5 )-alkyl, (C 1 -C 5 )-haloalkyl, aryl, aryl-(
  • Very particularly preferred subject matter of the invention are compounds of the general formula (I), wherein 35 W represents the group W -1 W-2 R 1 represents hydrogen, or fluorine, R 2 represents fluorine, chlorine, bromine, cyano, nitro, C(O)NH 2 , or C(S)NH 2 , R 3 and R 4 independently of one another represent hydrogen, methyl, ethyl, prop-1-yl, prop-2-yl, but-1-yl, but-2-yl, 2-methyl-prop-1-yl, 1,1-dimethyleth-1-yl, or trifluoromethyl, or R 3 and R 4 together with the carbon atom to which they are attached form a fully saturated or partially saturated, 3 to 7-membered carbocyclic ring, R 5 represents hydrogen, methyl, ethyl, prop-1-yl, prop-2-yl, but-1-yl, but-2-yl, 2-methyl-prop-1-yl, 1,1-dimethyleth-1-yl, or trifluoro
  • W represents the group W -1 W-2
  • R 1 is hydrogen, or fluorine
  • R 2 is fluorine, chlorine, bromine, cyano, or nitro
  • R 3 and R 4 independently of one another are hydrogen, methyl, ethyl, or prop-1-yl, or R 3 and R 4 together with the carbon atom to which they are attached form a fully saturated or partially saturated, 3 to 6-membered carbocyclic ring
  • R 5 is hydrogen, methyl, ethyl, prop-1-yl, prop-2-yl, but-1-yl, but-2-yl, 2-methyl-prop-1-yl, 1,1-dimethyleth-1-yl, or trifluoromethyl
  • R 6 is methyl or ethyl
  • R 7 is hydrogen
  • Q is one of the above-mentioned groups Q-1 to Q-500.
  • the invention is preferably carried out by compounds of the general formula (I) in which W represents the group W -1 W-2 R 1 represents hydrogen or fluorine, R 2 represents fluorine, chlorine, bromine, cyano or nitro, R 3 and R 4 independently represent hydrogen, methyl or ethyl, R 5 represents hydrogen, methyl, ethyl, prop-1-yl or trifluoromethyl, R 6 represents methyl or ethyl, R 7 represents hydrogen, and Q represents one of the groups Q-1 to Q-500 specifically mentioned above.
  • W represents the group W -1 W-2
  • R 1 represents hydrogen or fluorine
  • R 2 represents fluorine, chlorine, bromine, cyano or nitro
  • R 3 and R 4 independently represent hydrogen, methyl or ethyl
  • R 5 represents hydrogen, methyl, ethyl, prop-1-yl or trifluoromethyl
  • R 6 represents methyl or ethyl
  • R 7 represents hydrogen
  • Q represents one of the groups Q-1 to Q-500 specifically
  • Particularly preferred subject matter of the invention are compounds of the general formula (I), wherein W represents the group R 1 is fluorine, R 2 is chlorine, R 3 and R 4 are each independently hydrogen or methyl, R 5 is hydrogen, R 6 is methyl, R 7 is hydrogen, and Q is one of the groups Q-1, Q-286, Q-371, Q-441, Q-442, or Q-481 specifically mentioned above.
  • the radical definitions given above apply both to the end products of the formula (I) and correspondingly to the starting materials or intermediates required in each case for their preparation. These radical definitions can be combined with one another as desired, i.e. also between the given preferred ranges.
  • the designations used above and below are explained with regard to the compounds according to the invention.
  • the general rule for the designation of chemical groups is that the connection to the skeleton or the rest of the molecule is via the last-mentioned structural element of the chemical group in question, ie for example in the case of (C 2 -C 8 )-alkenyloxy via the Oxygen atom, and in the case of heterocyclyl-(C1-C8)-alkyl or R 13 O(O)C-(C1-C8)-alkyl, each via the C atom of the alkyl group.
  • alkyl In a complex chemical group such as heterocyclyl-(C1-C8)-alkyl or R 13 O(O)C-(C1-C8)-alkyl, the term “alkyl” therefore also stands for an alkylene group.
  • the bond to the skeleton or the rest of the molecule is made via the first-mentioned structural element of the chemical group in question.
  • alkylsulfonyl alone or as part of a chemical group - stands for straight-chain or branched alkylsulfonyl, preferably having 1 to 8, or having 1 to 6 carbon atoms, e.g.
  • (but not limited to) (C 1 -C 6 )-alkylsulfonyl such as methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, 1,1-dimethylethylsulfonyl, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl
  • heteroarylsulfonyl stands for optionally substituted pyridylsulfonyl, pyrimidinylsulfonyl, pyrazinylsulfonyl or optionally substituted polycyclic heteroarylsulfonyl, here in particular optionally substituted quinolinylsulfonyl, for example substituted by fluorine, chlorine, bromine, iodine, cyano, nitro, alkyl, haloalkyl, haloalkoxy, amino, alkylamino, alkylcarbonylamino, dialkylamino or alkoxy groups.
  • alkylthio alone or as part of a chemical group - stands for straight-chain or branched S-alkyl, preferably having 1 to 8, or having 1 to 6 carbon atoms, such as (C1-C10)-, (C1-C6)- or (C1-C4)-alkylthio, e.g.
  • (but not limited to) (C1-C6)-alkylthio such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-di
  • alkenylthio means an alkenyl radical bonded via a sulfur atom
  • alkynylthio means an alkynyl radical bonded via a sulfur atom
  • cycloalkylthio means a cycloalkyl radical bonded via a sulfur atom
  • cycloalkenylthio means a cycloalkenyl radical bonded via a sulfur atom
  • (but not limited to) (C 1 -C 6 )-alkylsulfinyl such as methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1,1-dimethylethylsulfinyl, pentylsulfinyl, 1-Methylbutylsulfinyl, 2-Methylbutylsulfinyl, 3-Methylbutylsulfinyl, 1,1-Dimethylpropylsulfinyl, 1,2-Dimethylpropylsulfinyl, 2,2-Di-methylpropylsulfinyl, 1-Ethylpropylsulfinyl, Hexylsulfinyl, 1-Meth
  • Alkoxy means an alkyl radical bonded via an oxygen atom, e.g. B.
  • (but not limited to) (C1-C6) alkoxy such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-Trimethylpropoxy, 1,2,2-Trimethylpropoxy, 1-ethyl-1-methylpropoxy, and 1-ethyl-2-methylpropoxy.
  • Alkenyloxy means an alkenyl radical bonded via an oxygen atom.
  • Alkynyloxy means an alkynyl radical bonded via an oxygen atom, such as (C2-C10)-, (C2-C6)-, or (C2-C4)-alkenoxy or (C3-C10)-, (C3-C6)-, or (C3-C4)-alkynoxy.
  • Cycloalkyloxy means a cycloalkyl radical bonded via an oxygen atom
  • cycloalkenyloxy means a cycloalkenyl radical bonded via an oxygen atom.
  • the number of carbon atoms refers to the alkyl radical in the alkylcarbonyl group.
  • the number of C atoms refers to the alkenyl or alkynyl radical in the alkenyl or alkynylcarbonyl group.
  • the number of C atoms refers to the alkyl radical in the alkoxycarbonyl group.
  • the number of C atoms refers to the alkenyl or alkynyl radical in the alkene or alkynyloxycarbonyl group.
  • the number of C atoms refers to the alkyl radical in the alkylcarbonyloxy group.
  • the number of C atoms refers to the alkenyl or alkynyl radical in the alkenyl or alkynylcarbonyloxy group.
  • abbreviations such as C(O)R 13 , C(O)OR 13 , OC(O)NR 11 R 12 , or C(O)NR 11 R 12 the abbreviation O in parentheses stands for an oxygen atom bonded to the adjacent carbon atom via a double bond.
  • abbreviations such as OC(S)OR 13 , OC(S)SR 14 , OC(S)NR 11 R 12 the abbreviation S in parentheses stands for a sulfur atom bonded to the adjacent carbon atom via a double bond.
  • aryl means an optionally substituted mono-, bi- or polycyclic aromatic system having preferably 6 to 14, in particular 6 to 10 ring C atoms, for example phenyl, naphthyl, anthryl, phenanthrenyl, and the like, preferably phenyl.
  • optionally substituted aryl also includes polycyclic systems such as tetrahydronaphthyl, indenyl, indanyl, fluorenyl, biphenylyl, where the bonding site is on the aromatic system.
  • aryl is generally also included in the term “optionally substituted phenyl”.
  • Preferred aryl substituents here are, for example, hydrogen, halogen, alkyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, halocycloalkyl, alkenyl, alkynyl, aryl, arylalkyl, arylalkenyl, heteroaryl, heteroarylalkyl, heterocyclyl, heterocyclylalkyl, alkoxyalkyl, alkylthio, haloalkylthio, haloalkyl, Alkoxy, haloalkoxy, cycloalkoxy, cycloalkylalkoxy, aryloxy, heteroraryloxy, alkoxyalkoxy, alkynylalkoxy, alkenyloxy, bis-alkylaminoalkoxy, tris-[alkyl]silyl, bis-[alkyl]arylsilyl, bis-[alkyl]alkylsilyl, tris
  • heterocyclyl radical or the heterocyclic ring is optionally substituted, it can be fused with other carbocyclic or heterocyclic rings.
  • polycyclic systems are also encompassed, such as, for example, 8-azabicyclo[3.2.1]octanyl, 8-azabicyclo[2.2.2]octanyl or 1-azabicyclo[2.2.1]heptyl.
  • spirocyclic systems are also encompassed, such as, for example, 1-oxa-5-aza-spiro[2.3]hexyl.
  • the heterocyclic ring preferably contains 3 to 9 ring atoms, in particular 3 to 6 ring atoms, and one or more, preferably 1 to 4, in particular 1, 2 or 3 heteroatoms in the heterocyclic ring, preferably from the group N, O, and S, but where two oxygen atoms should not be directly adjacent, such as, for example, with a heteroatom from the group N, O and S 1- or 2- or 3-pyrrolidinyl, 3,4-dihydro-2H-pyrrol-2- or 3-yl, 2,3-dihydro-1H-pyrrol- 1- or 2- or 3- or 4- or 5-yl; 2,5-dihydro-1H-pyrrol-1- or 2- or 3-yl, 1- or 2- or 3- or 4-piperidinyl; 2,3,4,5-tetrahydropyridin-2- or 3- or 4- or 5-yl or 6-yl; 1,2,3,6-Tetrahydropyridin-1- or 2- or 3- or 4- or 5- or 6-yl; 1,2,3,4-
  • Preferred 3-membered and 4-membered ring heterocycles are, for example, 1- or 2-aziridinyl, oxiranyl, thiiranyl, 1- or 2- or 3-azetidinyl, 2- or 3-oxetanyl, 2- or 3-thietanyl, and 1,3-dioxetan-2-yl.
  • heterocyclyl are a partially or fully hydrogenated heterocyclic radical having two heteroatoms from the group consisting of N, O, and S, such as, for example, 1- or 2- or 3- or 4-pyrazolidinyl; 4,5-dihydro-3H-pyrazol-3- or 4- or 5-yl; 4,5-Dihydro-1H-pyrazol-1- or 3- or 4- or 5-yl; 2,3-Dihydro-1H-pyrazol-1- or 2- or 3- or 4- or 5-yl; 1- or 2- or 3- or 4-Imidazolidinyl; 2,3-Dihydro-1H-imidazol-1- or 2- or 3- or 4-yl; 2,5-dihydro-1H-imidazol-1- or 2- or 4- or 5-yl; 4,5-dihydro-1H-imidazol-1- or 2- or 4- or 5-yl; hexahydropyridazin-1- or 2- or 3- or 4-yl; 1,2,3,4-tetrahydro
  • heterocyclyl are a partially or fully hydrogenated heterocyclic radical with 3 heteroatoms from the group N, O and S, such as, for example, 1,4,2-dioxazolidin-2- or 3- or 5-yl; 1,4,2-dioxazol-3- or 5-yl; 1,4,2-dioxazinan-2- or -3- or 5- or 6-yl; 5,6-Dihydro-1,4,2-dioxazin-3- or 5- or 6-yl; 1,4,2-Dioxazin-3- or 5- or 6-yl; 1,4,2-Dioxazepan-2- or 3- or 5- or 6- or 7-yl; 6,7-Dihydro-5H-1,4,2-Dioxazepin-3- or 5- or 6- or 7-yl; 2,3-Dihydro-7H-1,4,2-Dioxazepin-2- or 3- or 5- or 6- or 7-yl; 2,3-Dihydro-5H-1,4,2-Dioxazepin-2- or 3- or 5-
  • heterocycles listed above are preferably, for example, hydrogen, halogen, alkyl, haloalkyl, hydroxy, alkoxy, cycloalkoxy, aryloxy, alkoxyalkyl, alkoxyalkoxy, cycloalkyl, halocycloalkyl, aryl, arylalkyl, heteroaryl, heterocyclyl, alkenyl, alkylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, Alkoxycarbonyl, hydroxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, alkoxycarbonylalkyl, arylalkoxycarbonyl, arylalkoxycarbonylalkyl, alkynyl, alkynylalkyl, alkylalkynyl, tris-alkylsilylalkynyl, nitro, amino, cyano, halo
  • the nitrogen heterocycle is partially or fully saturated, it can be linked to the rest of the molecule via either the carbon or the nitrogen atom.
  • Possible substituents for a substituted heterocyclic residue are the substituents listed below, as well as oxo and thioxo.
  • the oxo group as a substituent on a ring C atom then means, for example, a carbonyl group in the heterocyclic ring. This preferably also includes lactones and lactams.
  • the oxo group can also occur on the hetero ring atoms, which can exist in different oxidation states, e.g., N and S, and then form, for example, the divalent groups N(O), S(O) (also abbreviated to SO) and S(O)2 (also abbreviated to SO2) in the heterocyclic ring.
  • N(O), S(O) (also abbreviated to SO) and S(O)2 also abbreviated to SO2
  • both enantiomers are included.
  • heteroaryl stands for heteroaromatic compounds, ie fully 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, 1H-pyrrol-1-yl; 1H-pyrrol-2-yl; 1H-pyrrol-3-yl; furan-2-yl; furan-3-yl; thien-2-yl; thien-3-yl, 1H-imidazol-1-yl; 1H-imidazol-2-yl; 1H-imidazol-4-yl; 1H-imidazol-5-yl; 1H-pyrazol-1-yl; 1H-pyrazol-3-yl; 1H-pyrazol-4-yl; 1H-pyrazol-5-yl, 1H-1,2,3-triazol-1-yl, 1H-1,2,3-triazol-4-yl, 1H-1,2,3-triazol-5-yl, 2H-1,2,3-triazol-2-yl, 2H-1,2,3-triazol-4-yl, 1H-1,2,4-triazol-1-
  • heteroaryl groups according to the invention can further be substituted by one or more identical or different radicals. If two adjacent carbon atoms are part of another aromatic ring, these are fused heteroaromatic systems, such as benzofused or multiply fused heteroaromatics.
  • quinolines e.g., quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl
  • 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; pyridopyrazines; pyr
  • heteroaryl are also 5- or 6-membered benzo-fused rings from the group 1H-indol-1-yl, 1H-indol-2-yl, 1H-indol-3-yl, 1H-indol-4-yl, 1H-indol-5-yl, 1H-indol-6-yl, 1H-indol-7-yl, 1-benzofuran-2-yl, 1-benzofuran-3-yl, 1-benzofuran-4-yl, 1-benzofuran-5-yl, 1-benzofuran-6-yl, 1-benzothiophen-7-yl, 1-benzothiophen-2-yl, 1-benzothiophen-3-yl, 1-benzothiophen-4-yl, 1-benzothiophen-5-yl, 1-benzothiophen-6-yl, 1-Benzothiophen-7-yl, 1H-Indazol-1-yl, 1H-Indazol-3-yl
  • halogen means, for example, fluorine, chlorine, bromine, or iodine. If the term is used for a radical, then "halogen" means, for example, a fluorine, chlorine, bromine, or iodine atom.
  • alkyl means a straight-chain or branched, open-chain, saturated hydrocarbon radical which is optionally mono- or polysubstituted and, in the latter case, is referred to as "substituted alkyl.”
  • Preferred substituents are halogen atoms, alkoxy, haloalkoxy, cyano, alkylthio, haloalkylthio, amino, or nitro groups; particular preference is given to methoxy, methyl, fluoroalkyl, cyano, nitro, fluorine, chlorine, bromine, or iodine.
  • the prefix “bis” also includes the combination of different alkyl radicals, e.g.
  • Haloalkyl mean alkyl, alkenyl or alkynyl that is partially or fully substituted by identical or different halogen atoms, e.g.
  • monohaloalkyl such as CH 2 CH 2 Cl, CH 2 CH 2 Br, CHClCH 3 , CH 2 Cl, CH 2 F; perhaloalkyl such as CCl 3, CClF 2, CFCl 2 , CF 2 CClF 2, CF 2 CClFCF 3 ; polyhaloalkyl such as CH 2 CHFCl, CF 2 CClFH, CF 2 CBrFH, CH 2 CF 3 ; the term perhaloalkyl also includes the term perfluoroalkyl.
  • Partially fluorinated alkyl means a straight-chain or branched, saturated hydrocarbon which is mono- or polysubstituted by fluorine, where the corresponding fluorine atoms can be located as substituents on one or more different carbon atoms of the straight-chain or branched hydrocarbon chain, such as, for example, CHFCH3, CH2CH2F, CH2CH2CF3, CHF2, CH2F, CHFCF2CF3.
  • Partially fluorinated haloalkyl means a straight-chain or branched, saturated hydrocarbon which is substituted by various halogen atoms with at least one fluorine atom, where all other optionally present halogen atoms are selected from the group consisting of fluorine, chlorine, bromine, iodine.
  • the corresponding halogen atoms can be located as substituents on one or more different carbon atoms of the straight-chain or branched hydrocarbon chain.
  • Partially fluorinated haloalkyl also includes the complete substitution of the straight-chain or branched chain by halogen with the participation of at least one Fluorine atom.
  • Haloalkoxy is, for example, OCF3, OCHF2, OCH2F, OCF2CF3, OCH2CF3 and OCH2CH2Cl; the same applies to haloalkenyl and other halogen-substituted radicals.
  • the term “( C1 - C4 )-alkyl” used here as an example is a shorthand notation for straight-chain or branched alkyl having one to four carbon atoms corresponding to the range specified for C atoms, ie includes the radicals methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl.
  • (C 1 -C 6 )-Alkyl also includes straight-chain or branched alkyl radicals with a larger number of C atoms, ie, according to the example, also the alkyl radicals with 5 and 6 C atoms.
  • lower carbon skeletons e.g., with 1 to 6 C atoms or, in the case of unsaturated groups, with 2 to 6 C atoms, are preferred for hydrocarbon radicals such as alkyl, alkenyl, and alkynyl radicals, even in compound radicals.
  • Alkyl radicals including compound radicals such as alkoxy, haloalkyl, etc., are, for example, methyl, ethyl, n- or i-propyl, n-, i-, t-, or 2-butyl, pentyls, hexyls, such as n-hexyl, i-hexyl, and 1,3-dimethylbutyl, and heptyls, such as n-heptyl, 1-methylhexyl, and 1,4-dimethylpentyl.
  • Alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals, wherein at least one double bond or triple bond is contained. Preferred radicals are those containing one double bond or triple bond.
  • alkenyl includes in particular straight-chain or branched open-chain hydrocarbon radicals with more than one double bond, such as 1,3-butadienyl and 1,4-pentadienyl, but also allenyl or cumulenyl radicals with one or more cumulated double bonds, such as allenyl (1,2-propadienyl), 1,2-butadienyl and 1,2,3-pentatrienyl.
  • Alkenyl means, for example, vinyl, which may optionally be substituted by further alkyl radicals, e.g. (but not limited to) (C2-C6)-alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-Methyl-2-butenyl, 1-Methyl-3-butenyl, 2-Methyl-3-butenyl, 3-Methyl-3-butenyl, 1,1-Dimethyl-2
  • alkynyl also includes, in particular, straight-chain or branched open-chain hydrocarbon radicals with more than one triple bond or with one or more triple bonds and one or more double bonds, such as 1,3-butatrienyl or 3-penten-1-yn-1-yl.
  • (C 2 -C 6 )-alkynyl means, for example, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-Methyl-3-pentynyl, 1-Methyl-4-pentynyl, 2-Meth
  • cycloalkyl means a carbocyclic, saturated ring system with preferably 3-8 ring carbon atoms, e.g., cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl, which is optionally further substituted, preferably by hydrogen, alkyl, alkoxy, oxo, cyano, nitro, alkylthio, haloalkylthio, halogen, alkenyl, alkynyl, haloalkyl, amino, alkylamino, bisalkylamino, alkoxycarbonyl, hydroxycarbonyl, arylalkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, or cycloalkylaminocarbonyl.
  • Optionally substituted cycloalkyl encompasses cyclic systems with substituents, including substituents with a double bond on the cycloalkyl radical, e.g., an alkylidene group such as methylidene.
  • polycyclic aliphatic systems are also included, such as bicyclo[1.1.0]butan-1-yl, bicyclo[1.1.0]butan-2-yl, bicyclo[2.1.0]pentan-1-yl, bicyclo[1.1.1]pentan-1-yl, bicyclo[2.1.0]pentan-2-yl, bicyclo[2.1.0]pentan-5-yl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]hept-2-yl, bicyclo[2.2.2]octan-2-yl, bicyclo[3.2.1]octan-2-yl, bicyclo[3.2.2]nonan-2-yl, adam
  • (C3-C7)-cycloalkyl is a shorthand notation for cycloalkyl with three to seven carbon atoms, corresponding to the range for C atoms.
  • spirocyclic aliphatic systems are also included, such as spiro[2.2]pent-1-yl, spiro[2.3]hex-1-yl, spiro[2.3]hex-4-yl, 3-spiro[2.3]hex-5-yl, spiro[3.3]hept-1-yl, spiro[3.3]hept-2-yl.
  • Cycloalkenyl means a carbocyclic, non-aromatic, partially unsaturated ring system with preferably 4-8 C atoms, e.g.
  • alkylidene e.g. B.
  • C 1 -C 10 )-alkylidene means the residue of a straight-chain or branched open-chain hydrocarbon residue which is bonded via a double bond.
  • Cycloalkylidene means a carbocyclic residue which is bonded via a double bond.
  • Cycloalkylalkyloxy means a cycloalkylalkyl residue bonded via an oxygen atom and “arylalkyloxy” means an arylalkyl residue bonded via an oxygen atom.
  • Alkoxyalkyl means an alkoxy radical attached via an alkyl group, and “alkoxyalkoxy” means an alkoxyalkyl radical attached via an oxygen atom, e.g., (but not limited to) methoxymethoxy, methoxyethoxy, ethoxyethoxy, methoxy-n-propyloxy.
  • Alkylthioalkyl means an alkylthio radical attached via an alkyl group
  • alkylthioalkylthio means an alkylthioalkyl radical attached via an oxygen atom.
  • Arylalkoxyalkyl means an aryloxy radical attached via an alkyl group
  • heteroaryloxyalkyl means a heteroaryloxy radical attached via an alkyl group.
  • Haloalkoxyalkyl means a haloalkoxy radical attached via an alkyl group
  • haloalkylthioalkyl means a haloalkylthio radical attached via an alkyl group.
  • Arylalkyl means an aryl radical bonded via an alkyl group
  • heteroarylalkyl means a heteroaryl radical bonded via an alkyl group
  • heterocyclylalkyl means a heterocyclyl radical bonded via an alkyl group
  • Cycloalkylalkyl means a cycloalkyl radical attached via an alkyl group, e.g., but not limited to, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, 1-cyclopropyleth-1-yl, 2-cyclopropyleth-1-yl, 1-cyclopropylprop-1-yl, and 3-cyclopropylprop-1-yl.
  • Arylalkenyl means an aryl radical attached via an alkenyl group
  • heteroarylalkenyl means a heteroaryl radical attached via an alkenyl group
  • heterocyclylalkenyl means a heterocyclyl radical attached via an alkenyl group.
  • Arylalkynyl stands for an aryl radical bonded via an alkynyl group
  • heteroarylalkynyl means a heteroaryl radical bonded via an alkynyl group
  • heterocyclylalkynyl means a heterocyclyl radical bonded via an alkynyl group.
  • haloalkylthio alone or as part of a chemical group - stands for straight-chain or branched S-haloalkyl, preferably having 1 to 8, or having 1 to 6 carbon atoms, such as (C 1 -C 8 )-, (C 1 -C 6 )-, or (C 1 -C 4 )-haloalkylthio, e.g. (but not limited to) trifluoromethylthio, pentafluoroethylthio, difluoromethyl, 2,2-difluoroeth-1-ylthio, 2,2,2-difluoroeth-1-ylthio, 3,3,3-prop-1-ylthio.
  • Halocycloalkyl and halocycloalkenyl mean halogen atoms substituted by the same or different halogen atoms, such as F, Cl and Br, or by haloalkyl, such as B. Trifluoromethyl or difluoromethyl partially or fully substituted cycloalkyl or cycloalkenyl, e.g.
  • "trialkylsilyl" - alone or as part of a chemical group - represents straight-chain or branched Si-alkyl, preferably having 1 to 8, or having 1 to 6 carbon atoms, such as tri-[(C1-C8)-, (C1-C6)- or (C1-C4)-alkyl]silyl, e.g.
  • Trialkylsilylalkynyl stands for a trialkylsilyl radical bonded via an alkynyl group.
  • stereoisomers can be obtained from the mixtures obtained during production using conventional separation methods. Chromatographic separation can be carried out both on an analytical scale to determine the enantiomeric excess or diastereomeric excess, and on a preparative scale to produce test samples for biological testing. Stereoisomers can also be selectively produced by using stereoselective reactions using optically active starting materials and/or auxiliaries.
  • the invention thus also relates to all stereoisomers encompassed by the general formula (I) but not indicated with their specific stereoform, as well as mixtures thereof. If the compounds are obtained as solids, purification can also be carried out by recrystallization or digestion. If individual compounds (I) cannot be satisfactorily obtained by the methods described below, they can be prepared by derivatization of other compounds (I). Suitable methods for the isolation, purification, and stereoisomer separation of compounds of formula (I) are methods generally known to the skilled person from analogous cases, e.g., by physical processes such as crystallization, chromatography, especially column chromatography and HPLC (high-pressure liquid chromatography), distillation, optionally under reduced pressure, extraction, and other processes.
  • physical processes such as crystallization, chromatography, especially column chromatography and HPLC (high-pressure liquid chromatography), distillation, optionally under reduced pressure, extraction, and other processes.
  • any remaining mixtures can generally be separated by chromatographic separation, e.g., on chiral solid phases.
  • suitable processes include crystallization, e.g., of diastereomeric salts, which can be obtained from the diastereomer mixtures with optically active acids and, if acidic groups are present, with optically active bases. 35 Synthesis of substituted oxyiminomethylphenyluracils with 4-difluoroalkyl substitution on the uracil of the general formula (I):
  • the substituted oxyiminomethylphenyluracils according to the invention with 4-difluoroalkyl substitution on the uracil of general formula (I) can be prepared using known processes.
  • the synthetic routes used and investigated are based on commercially available or easily prepared synthetic building blocks.
  • the groups W, Q, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 and R 16 of general formula (I) have the meanings defined above in the following schemes, unless exemplary but non-limiting definitions are given.
  • Ethyl (2Z)-3-amino-4,4-difluoropent-2-enoate by reaction with dimethylcarbamoyl chloride in N,N-dimethylformamide (DMF) using a suitable base (e.g., sodium hydride or potassium tert-butoxide) and subsequent cyclization to oxazin-6-one (VII) using phosphorus pentachloride and phosphorus oxychloride.
  • a suitable base e.g., sodium hydride or potassium tert-butoxide
  • the required underlying ⁇ -haloacetic acid esters are commercially available or known from the literature.
  • the O-alkylation is carried out using a suitable base (e.g. sodium hydride, potassium tert-butoxide or potassium carbonate) in a suitable polar aprotic solvent (e.g. dichloromethane, chloroform, N,N-dimethylacetamide or N,N-dimethylformamide).
  • a suitable amination reagent e.g.
  • a suitable base e.g. sodium hydride, potassium tert-butoxide or potassium carbonate
  • a suitable polar aprotic solvent e.g. dichloromethane, chloroform, N,N-dimethylacetamide or N,N-dimethylformamide.
  • ester cleavage of the terminal ester group of N-amino-N'-uracil (Ia) according to ester cleavage processes known to those skilled in the art, the carboxylic acid (Ib) corresponding to N-amino-N'-uracil (Ia) is obtained.
  • This acid can then be converted into various ester variants of N-amino-N'-uracil (Ic) by esterification with a suitable alcohol R-OH.
  • the esterification can be carried out, as shown by way of example but not limitation in Scheme 2, using suitable coupling reagents (e.g.
  • HOBt 1-hydroxybenzotriazole
  • EDC 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide
  • HATU O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate
  • T3P 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphorinane-2,4,6-trioxide) and suitable bases (e.g. diisopropylethylamine, triethylamine) in a suitable polar aprotic solvent (e.g. dichloromethane, chloroform).
  • suitable bases e.g. diisopropylethylamine, triethylamine
  • a suitable polar aprotic solvent e.g. dichloromethane, chloroform
  • esterification can be carried out via transformation into the acid chloride using thionyl chloride and subsequent reaction with the alcohol R-OH, using a suitable polar aprotic solvent (e.g. dichloromethane (DCM), chloroform, N,N-dimethylacetamide (DMA) or N,N-dimethylformamide (DMF)).
  • a suitable polar aprotic solvent e.g. dichloromethane (DCM), chloroform, N,N-dimethylacetamide (DMA) or N,N-dimethylformamide (DMF)
  • suitable trialkylsilyl chlorides represented here by way of example but not limitation as tert-butyldimethylsilyl chloride.
  • the silylation is carried out using a suitable base (e.g. triethylamine or Hünig's base) in a suitable polar aprotic solvent (e.g. dichloromethane, chloroform, N,N-dimethylacetamide or N,N-dimethylformamide).
  • a suitable polar aprotic solvent e.g. dichloromethane, chloroform, N,N-dimethylacetamide or N,N-dimethylformamide.
  • the silyl-protected uracil (X) is converted into N-methyl-N'-phenyluracil (XI) by subsequent N-methylation.
  • the methylation is carried out using a suitable base (e.g. B.
  • a suitable polar aprotic solvent e.g. dichloromethane, chloroform, N,N-dimethylacetamide or N,N-dimethylformamide.
  • the O-alkylation is carried out using a suitable base (e.g., sodium hydride, potassium tert-butoxide, or potassium carbonate) in a suitable polar aprotic solvent (e.g., dichloromethane, chloroform, N,N-dimethylacetamide, or N,N-dimethylformamide).
  • a suitable base e.g., sodium hydride, potassium tert-butoxide, or potassium carbonate
  • a suitable polar aprotic solvent e.g., dichloromethane, chloroform, N,N-dimethylacetamide, or N,N-dimethylformamide.
  • the corresponding carboxylic acid (Ie) is obtained by ester cleavage of the terminal ester group of N-methyl-N'-uracil (Id) according to ester cleavage processes known to those skilled in the art. This can then be converted by esterification with a suitable alcohol R-OH to various ester variants of N-
  • reaction solution was then stirred for 3 h at 30 °C.
  • the mixture was left to stand overnight and, after TLC monitoring, water was added the following day.
  • the aqueous phase was then thoroughly extracted several times with ethyl acetate.
  • the combined organic phases were dried over sodium sulfate, filtered, and carefully concentrated under reduced pressure.
  • Table I.1 Preferred compounds of formula (I.1) are compounds I.1-1 to I.1-500, wherein Q has the meanings given in the respective row of Table 1.
  • the compounds I.1-1 to I.1-500 of Table I.1 are thus defined by the meaning of the respective entries Nos. 1 to 500 for Q in Table 1.
  • Table 1 ) Table I.2: Preferred compounds of formula (I.2) are compounds I.2-1 to I.2-500, wherein Q has the meanings given in the respective row of Table 1.
  • the compounds I.2-1 to I.2-500 of Table I.2 are thus defined by the meaning of the respective entries No. 1 to 500 for Q in Table 1.
  • Table I.3: Preferred compounds of formula (I.3) are compounds I.3-1 to I.3-500, wherein Q has the meanings given in the respective row of Table 1.
  • the compounds I.3-1 to I.3-500 of Table I.3 are thus defined by the meaning of the respective entries No. 1 to 500 for Q of Table 1.
  • Table I.4 Preferred compounds of formula (I.4) are the compounds I.4-1 to I.4-500, wherein Q has the meanings given in the respective row of Table 1.
  • the compounds I.4-1 to I.4-500 of Table I.4 are thus defined by the meaning of the respective entries No. 1 to 500 for Q of Table 1.
  • Table I.5 Preferred compounds of formula (I.5) are compounds I.5-1 to I.5-500, wherein Q has the meanings given in the respective row of Table 1.
  • the compounds I.5-1 to I.5-500 of Table I.5 are thus defined by the meaning of the respective entries No. 1 to 500 for Q of Table 1.
  • Table I.6 Preferred compounds of formula (I.6) are compounds I.6-1 to I.6-500, wherein Q has the meanings given in the respective row of Table 1.
  • the compounds I.6-1 to I.6-500 of Table I.6 are thus defined by the meaning of the respective entries No. 1 to 500 for Q of Table 1.
  • Table I.7: Preferred compounds of formula (I.7) are compounds I.7-1 to I.7-500, wherein Q has the meanings given in the respective row of Table 1.
  • the compounds I.7-1 to I.7-500 of Table I.7 are thus defined by the meaning of the respective entries No. 1 to 500 for Q of Table 1.
  • Table I.8 Preferred compounds of formula (I.8) are compounds I.8-1 to I.8-500, wherein Q has the meanings given in the respective row of Table 1.
  • the compounds I.8-1 to I.8-500 of Table I.8 are thus defined by the meaning of the respective entries No. 1 to 500 for Q of Table 1.
  • Table I.9: Preferred compounds of formula (I.9) are compounds I.9-1 to I.9-500, wherein Q has the meanings given in the respective row of Table 1.
  • the compounds I.9-1 to I.9-500 of Table I.9 are thus defined by the meaning of the respective entries No. 1 to 500 for Q of Table 1.
  • Table I.10 Preferred compounds of formula (I.10) are compounds I.10-1 to I.10-500, wherein Q has the meanings given in the respective row of Table 1.
  • the compounds I.10-1 to I.19-500 of Table I.10 are thus defined by the meaning of the respective entries No. 1 to 500 for Q of Table 1.
  • Table I.11 Preferred compounds of formula (I.11) are compounds I.11-1 to I.11-500, wherein Q has the meanings given in the respective row of Table 1.
  • the compounds I.11-1 to I.11-500 of Table I.11 are thus defined by the meaning of the respective entries No. 1 to 500 for Q of Table 1.
  • Table I.12 Preferred compounds of formula (I.12) are compounds I.12-1 to I.12-500, wherein Q has the meanings given in the respective row of Table 1.
  • the compounds I.12-1 to I.12-500 of Table I.12 are thus defined by the meaning of the respective entries No. 1 to 500 for Q of Table 1.
  • Table I.13: Preferred compounds of formula (I.13) are compounds I.13-1 to I.13-500, wherein Q has the meanings given in the respective row of Table 1.
  • the compounds I.13-1 to I.13-500 of Table I.13 are thus defined by the meaning of the respective entries No. 1 to 500 for Q of Table 1.
  • Table I.14 Preferred compounds of the formula (I.14) are the compounds I.14-1 to I.14-500, wherein Q has the meanings given in the respective row of Table 1.
  • the compounds I.14-1 to I.14-500 of Table I.14 are thus defined by the meaning of the respective entries No. 1 to 500 for Q in Table 1.
  • NMR data of selected examples The 1 H NMR data of selected examples of compounds of the general formula (I) are given in two different ways, namely (a) classical NMR evaluation and interpretation or (b) in the form of 1 H NMR peak lists according to the method described below. a) classical NMR interpretation b) NMR peak list method The 1 H NMR data of selected examples are noted in the form of 1 H NMR peak lists.
  • the ⁇ value in ppm is listed first, followed by the signal intensity in parentheses.
  • the ⁇ value - signal intensity number pairs of different signal peaks are listed separated by semicolons.
  • the peak list of an example therefore has the form: ⁇ 1 (intensity1 ) ; ⁇ 2 (intensity2);........; ⁇ i (intensityi ) ; hence; ⁇ n (intensityn)
  • 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 is used, especially in the case of spectra measured in DMSO. Therefore, the tetramethylsilane peak may or may not appear in NMR peak lists.
  • the lists of 1 H NMR peaks are similar to classical 1 H NMR printouts and thus usually contain all peaks listed in a classical NMR interpretation. Furthermore, like classical 1 H NMR printouts, they may show solvent signals, signals from stereoisomers of the target compounds that are also subject of the invention, and/or impurity peaks.
  • the present invention furthermore relates to the use of one or more compounds of the formula (I) according to the invention and/or salts thereof, as defined above, preferably in one of the embodiments characterized as preferred or particularly preferred, in particular one or more compounds of the formulas (I.1-1) to (I.14-500) and/or salts thereof, each as defined above, as herbicide and/or plant growth regulator, preferably in crops of useful and/or ornamental plants.
  • the present invention further provides a method for controlling harmful plants and/or for regulating the growth of plants, characterized in that an effective amount of - one or more compounds of the formula (I) according to the invention and/or salts thereof, as defined above, preferably in one of the embodiments characterized as preferred or particularly preferred, in particular one or more compounds of the formulae (I.1-1) to (I.14-500) and/or salts thereof, in each case as defined above, or - an agent according to the invention, as defined below, is applied to the (harmful) plants, (harmful) plant seeds, the soil in or on which the (harmful) plants grow, or the area under cultivation.
  • the present invention also relates to a method for controlling undesirable plants, preferably in crops of useful plants, characterized in that an effective amount of - one or more compounds of the formula (I) and/or salts thereof, as defined above, preferably in one of the embodiments characterized as preferred or particularly preferred, in particular one or more compounds of the formulae (I.1-1) to (I.14-500) and/or salts thereof, each as defined above, or - a composition according to the invention, as defined below, is applied to undesirable plants (e.g. harmful plants such as monocotyledonous or dicotyledonous weeds or undesirable cultivated plants), the seeds of the undesirable plants (i.e. plant seeds, e.g.
  • undesirable plants e.g. harmful plants such as monocotyledonous or dicotyledonous weeds or undesirable cultivated plants
  • the seeds of the undesirable plants i.e. plant seeds, e.g.
  • the undesirable plants grow e.g. the soil of cultivated land or non-cultivated land
  • the area under cultivation i.e. area on which the undesirable plants will grow.
  • the present invention furthermore also relates to methods for controlling the growth of plants, preferably of useful plants, characterized in that an effective amount of - one or more compounds of the formula (I) and/or salts thereof, as defined above, preferably in one of the embodiments identified as preferred or particularly preferred, in particular one or more compounds of the formulae (I.1-1) to (I.14-500) and/or salts thereof, in each case as defined above, or - an agent according to the invention, as defined below, is applied to the plant, the seed of the plant (ie plant seeds, e.g. grains, seeds or vegetative propagation organs such as tubers or shoot parts with buds), the soil in or on which the plants grow (e.g.
  • plant seeds e.g. grains, seeds or vegetative propagation organs such as tubers or shoot parts with buds
  • the soil in or on which the plants grow e.g.
  • the compounds according to the invention or the compositions according to the invention can be applied, for example, by pre-sowing (optionally also by incorporation into the soil), pre-emergence and/or post-emergence methods.
  • Some representatives of the monocotyledonous and dicotyledonous weed flora which can be controlled by the compounds according to the invention may be mentioned specifically by way of example, without the mention being intended to imply a restriction to specific species.
  • one or more compounds of the formula (I) and/or salts thereof are used for controlling weeds or for regulating the growth of crops of useful plants or ornamental plants, where the useful plants or ornamental plants, in a preferred embodiment, are transgenic plants.
  • the compounds of formula (I) according to the invention and/or salts thereof are suitable for controlling the following genera of monocotyledonous and dicotyledonous weeds: Monocotyledonous weeds 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 according to the invention are applied to the soil surface before the germination of the weeds (grass and/or broadleaf weeds) (pre-emergence method), the emergence of the weed or broadleaf seedlings is either completely prevented, or they grow to the cotyledon stage, but then cease growth and finally die completely after three to four weeks.
  • the active ingredients are applied to the green parts of the plant using the post-emergence method, growth stops after treatment, and the weeds remain in the growth stage present at the time of application or die completely after a certain period of time, thus eliminating weed competition that is harmful to the crop plants very early and sustainably.
  • the compounds according to the invention have excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, economically important crops, e.g., dicotyledonous crops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Miscanthus, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous crops of the genera Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea, are only slightly damaged or not damaged at all, depending on the structure of the respective compound according to the invention and the application rate.
  • the present compounds are very suitable for the selective control of undesirable plant growth in crops such as agricultural crops or ornamental plants.
  • the compounds according to the invention (depending on their respective structure and the applied rate) exhibit outstanding growth-regulating properties in crop plants. They exert a regulatory influence on the plant's own metabolism and can thus be used to specifically influence plant constituents and to facilitate harvesting, for example by inducing desiccation and stunting.
  • they are also suitable for the 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 crops, as it can, for example, reduce or completely prevent lodging.
  • the active ingredients can also be used to control weeds in crops of plants modified genetically or by conventional mutagenesis.
  • the transgenic plants are generally characterized by particularly 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 product in terms of quantity, quality, storability, composition and special ingredients. For example, transgenic plants with increased starch content or altered starch quality or those with a different fatty acid composition of the harvested product are known.
  • transgenic crops With regard to transgenic crops, the use of the compounds according to the invention and/or their salts is preferred in economically important transgenic crops of useful and ornamental plants, e.g. cereals such as wheat, barley, rye, oats, millet, rice and maize or also crops of sugar beet, cotton, soybeans, rapeseed, potatoes, tomatoes, peas and other vegetables.
  • the compounds 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 which have been genetically engineered to be resistant. Due to their herbicidal and plant growth-regulating properties, the active ingredients can also be used to control weeds in crops of known or yet-to-be-developed genetically modified plants.
  • the transgenic plants are generally characterized by particularly 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 product in terms of quantity, Quality, storability, composition and special ingredients.
  • transgenic plants with increased starch content or altered starch quality or those with a different fatty acid composition of the harvested product are known.
  • Further special properties can lie in tolerance or resistance to abiotic stressors, e.g. heat, cold, drought, salt and ultraviolet radiation.
  • the compounds of the formula (I) can preferably be used as herbicides in useful plant crops which are resistant to the phytotoxic effects of the herbicides or which have been genetically engineered to be resistant. Conventional methods for producing new plants with modified characteristics compared to previously existing plants include, for example, classic breeding methods and the creation of mutants.
  • new plants with modified characteristics can be created using genetic engineering.
  • Numerous molecular biological techniques with which new transgenic plants with modified characteristics can be created are known to those skilled in the art.
  • nucleic acid molecules can be introduced into plasmids that allow mutagenesis or sequence modification through recombination of DNA sequences.
  • base exchanges can be made, partial sequences can be removed, or natural or synthetic sequences can be added.
  • Adapters or linkers can be attached to the fragments to connect the DNA fragments to one another.
  • the production of plant cells with 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 cosuppression 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 comprise the entire coding sequence of a gene product, including any flanking sequences present, as well as DNA molecules that comprise only parts of the coding sequence, whereby these parts must be long enough to produce an antisense effect in the cells. It is also possible to use DNA sequences that display a high degree of homology to the coding 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.
  • Such sequences are known to the person skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227).
  • Expression of the nucleic acid molecules can also take place in the organelles of the plant cells.
  • the transgenic plant cells can be regenerated into whole plants using known techniques. In principle, the transgenic plants can be plants of any plant species, i.e., both monocotyledonous and dicotyledonous plants.
  • the compounds (I) according to the invention can preferably be used in transgenic crops which are resistant to growth promoters, such as dicamba, or to herbicides that inhibit essential plant enzymes, e.g., acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS), or hydroxyphenylpyruvate dioxygenases (HPPD), or to herbicides from the group of sulfonylureas, glyphosates, glufosinates, or benzoyl isoxazoles and analogous active ingredients.
  • ALS acetolactate synthases
  • EPSP synthases glutamine synthases
  • HPPD hydroxyphenylpyruvate dioxygenases
  • the active compounds according to the invention are used in transgenic crops, in addition to the effects on weeds observed in other crops, effects often occur which are specific to the application in the respective transgenic crop, for example a modified or specifically expanded weed spectrum which can be controlled, modified application rates which can be used for the application, preferably good combinability with the herbicides to which the transgenic crop is resistant, and influence on the growth and yield of the transgenic crops.
  • the invention therefore also relates to the use of the compounds of formula (I) according to the invention and/or salts thereof as herbicides for controlling weeds in crops of useful or ornamental plants, optionally in transgenic crops.
  • the use according to the invention for controlling weeds or for regulating plant growth also includes the case in which the active ingredient of formula (I) or its salt is formed from a precursor substance ("prodrug") only after application to the plant, in the plant, or in the soil.
  • the invention also relates to the use of one or more compounds of the formula (I) or salts thereof or of an agent according to the invention (as defined below) (in a method) for controlling harmful plants or for regulating the growth of plants, characterized in that an effective amount of one or more compounds of the formula (I) or salts thereof is applied to the plants (harmful plants, optionally together with the useful plants), plant seeds, the soil in or on which the plants grow, or the area under cultivation.
  • the invention also relates to a herbicidal and/or plant growth regulating agent, characterized in that the agent contains (a) one or more compounds of the formula (I) and/or salts thereof as defined above, preferably in one of the embodiments identified as preferred or particularly preferred, in particular one or more compounds of the formulae (I.1-1) to (I.14-500) and/or salts thereof, in each case as defined above, and (b) one or more further substances selected from groups (i) and/or (ii): (i) one or more further agrochemically active substances, preferably selected from the group consisting of insecticides, acaricides, nematicides, further herbicides (ie those which do not correspond to the formula (I) defined above), fungicides, safeners, fertilizers 35 and/or further growth regulators, (ii) one or more formulation auxiliaries customary in plant protection.
  • the agent contains (a) one or more compounds of the formula (I) and/or salts thereof as defined above,
  • a herbicidal or plant growth-regulating composition according to the invention preferably comprises one, two, three or more formulation auxiliaries (ii) customary in crop protection, selected from the group consisting of surfactants, emulsifiers, dispersants, film formers, thickeners, inorganic salts, dusting agents, carriers that are solid at 25°C and 1013 mbar, preferably adsorptive, granulated inert materials, wetting agents, antioxidants, stabilizers, buffer substances, antifoam agents, water, organic solvents, preferably organic solvents that are miscible with water in any ratio at 25°C and 1013 mbar.
  • formulation auxiliaries customary in crop protection, selected from the group consisting of surfactants, emulsifiers, dispersants, film formers, thickeners, inorganic salts, dusting agents, carriers that are solid at 25°C and 1013 mbar, preferably adsorptive, granulated inert materials, wetting agents, antioxidants, stabilizer
  • the compounds (I) according to the invention can be used in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts, or granules in the usual preparations.
  • the invention therefore also relates to herbicidal and plant growth regulating compositions containing compounds of formula (I) and/or salts thereof.
  • the compounds of formula (I) and/or salts thereof can be formulated in various ways, depending on the biological and/or chemical-physical parameters required.
  • Possible formulation options include: 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), oil- or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), dusts (DP), seed dressings, granules for broadcast and soil application, granules (GR) in the form of micro-, spray-, lift- and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.
  • WP wettable powders
  • SP water-soluble powders
  • EC emulsifiable concentrates
  • EW emulsions
  • SC suspension concentrates
  • CS oil- or water-based dispersions
  • DP
  • Wettable powders are preparations that are evenly dispersible in water and contain, in addition to the active ingredient and a diluent or inert substance, ionic and/or non-ionic surfactants (wetting agents, dispersants), e.g., polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium ligninsulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalenesulfonate, or sodium oleoylmethyltaurine.
  • ionic and/or non-ionic surfactants e.g., polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, polyoxye
  • the herbicidal active ingredients are, for example, mixed in conventional equipment such as hammer mills, blower mills, and Air jet mills finely ground and simultaneously or subsequently mixed with the formulation auxiliaries.
  • Emulsifiable concentrates are produced by dissolving the active ingredient in an organic solvent, e.g. butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons or mixtures of organic solvents with the addition of one or more ionic and/or non-ionic surfactants (emulsifiers).
  • alkylarylsulfonic acid calcium salts such as Ca-dodecylbenzenesulfonate or non-ionic emulsifiers
  • 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.
  • Dusts are obtained by grinding the active ingredient with finely divided solid substances, e.g.
  • 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, with the addition of surfactants, as already listed above for the other formulation types.
  • Emulsions e.g. oil-in-water emulsions (EW)
  • EW oil-in-water emulsions
  • Granules can be produced either by spraying the active ingredient onto adsorptive, granulated inert material or by applying active ingredient concentrates to the surface of Carrier materials such as sand, kaolinite, or granulated inert material. Suitable active ingredients can also be granulated in the manner customary for the production of fertilizer granules—if desired, mixed with fertilizers. Water-dispersible granules are generally produced using conventional processes such as spray drying, fluidized-bed granulation, disc 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 preferably 2 to 80% by weight, of active ingredients of the formula (I) and salts thereof.
  • the active ingredient concentration is, for example, about 10 to 90% by weight, the remainder to 100% by weight consisting of conventional formulation components.
  • the active ingredient concentration can be approximately 1 to 90, preferably 5 to 80 wt.%.
  • Dust-like formulations contain 1 to 30 wt.% active ingredient, preferably mostly 5 to 20 wt.% active ingredient; sprayable solutions contain approximately 0.05 to 80, preferably 2 to 50 wt.% active ingredient.
  • the active ingredient content depends partly 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 wt.%, preferably between 10 and 80 wt.%.
  • the active ingredient formulations mentioned may contain the usual adhesives, wetting agents, dispersing agents, emulsifying agents, penetrating agents, preservatives, antifreeze agents, solvents, fillers, carriers, dyes, defoamers, evaporation inhibitors, and agents that influence pH and viscosity. Examples of formulation aids are listed, among others, in “Chemistry and Technology of Agrochemical Formulations", ed. DA Knowles, Kluwer Academic Publishers (1998).
  • the compounds of formula (I) or their salts can be used as such or in the form of their preparations (formulations) in combination with other pesticidally active substances, such as insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and/or growth regulators, e.g. as a ready-to-use formulation or as tank mixes.
  • pesticidally active substances such as insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and/or growth regulators, e.g. as a ready-to-use formulation or as tank mixes.
  • the combination formulations can be prepared on the basis of the abovementioned formulations, taking into account the physical properties and stabilities of the active ingredients to be combined.
  • Suitable combination partners for the compounds of formula (I) according to the invention in mixture formulations or in the tank mix are, for example, known active ingredients which are based on the inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, Enolpyruvylshikimate 3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II, protoporphyrinogen oxidase, as described, for example, in Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 19th edition, The British Crop Protection Council and the Royal Soc.
  • the weight ratios of herbicide (mixture) to safener generally depend on the application rate of herbicide 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, in particular 20:1 to 1:20.
  • the safeners can be formulated analogously to the compounds (I) or mixtures thereof with other herbicides/pesticides and can be supplied and applied as a ready-to-use formulation or tank mix with the herbicides.
  • the herbicide or herbicide safener formulations available in commercial form are diluted, if appropriate, in the usual way, e.g. in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules, with water. Dust-like preparations, soil or broadcast granules and sprayable solutions are not normally diluted with other inert substances before use. External conditions such as temperature, humidity etc. influence to a certain extent the application rate of the compounds of the formula (I) and/or their salts. The application rate can vary within wide limits.
  • the total amount of compounds of the formula (I) and their salts is preferably in the range from 0.001 to 10.0 kg/ha, more preferably in the range from 0.005 to 5 kg/ha, more preferably in the 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.
  • Application as a stem shortener can take place at various stages of plant growth. For example, application after tillering at the beginning of longitudinal growth is preferred.
  • seed treatment when used as a plant growth regulator, seed treatment is also possible, which includes various seed dressing and coating techniques.
  • the application rate depends on the individual techniques and can be determined in preliminary tests.
  • suitable combination partners for the compounds of formula (I) according to the invention in compositions according to the invention include known active ingredients based on the inhibition of, for example, acetolactate synthase, acetyl-CoA-35 carboxylase, cellulose synthase, enolpyruvylshikimate 3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II, or protoporphyrinogen oxidase, as described, for example, in Weed Research 26 (1986) 441-445.
  • herbicidal mixture partners The following active ingredients are known herbicides or plant growth regulators that can be combined with compounds of the general formula (I) (the compounds are designated either by the "common name” according to the International Organization for Standardization (ISO) or by the chemical name or by the code number) and always include all application forms such as acids, salts, esters and isomers such as stereoisomers and optical isomers.
  • ISO International Organization for Standardization
  • Icaeine examples include Acetochlor, Acifluorfen, Acifluorfen-methyl, Acifluorfen-sodium, Aclonifen, Alachlor, Allidochlor, Alloxydim, Alloxydim-sodium, Ametryn, Amicarbazon, Amidochlor, Amidosulfuron, 4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methylphenyl)-5-fluoropyridine-2-carboxylic acid, Aminocyclopyrachlor, Aminocyclopyrachlor-potassium, Aminocyclopyrachlor-methyl, Aminopyralid, Aminopyralid-dimethylammonium, Aminopyralid-tripromine, Amitrol, Ammonium sulfamate, Anilofos, Asulam, Asulam-potassium, Asulam-sodium, Atrazine, Azaf
  • Dicamba-biproamine Dicamba-N,N-Bis(3-aminopropyl)methylamine, Dicamba-butotyl, Dicamba-choline, Dicamba diglycolamine, dicamba dimethyl ammonium, dicamba diethanolaminemmonium, dicamba diethylammonium, dicamba isopropyl ammonium, dicamba methyl, dicamba monoethanolamine, dicamba olamine, dicamba potassium, dicamba sodium, dicamba triethanolamine), dichlobenil, 2-(2,4-Dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, 2-(2,5-Dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, dichlorprop, dichloroprop-butotyl, dichlorprop-dimethylammonium, dichlorprop-etexyl, dichloroprop-ethylammonium, Dich
  • Abscisic acid and related analogues [e.g. (2Z,4E)-5-[6-ethynyl-1-hydroxy-2,6-dimethyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoic acid, methyl-(2Z,4E)-5-[6-ethynyl-1-hydroxy-2,6-dimethyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoate, (2Z,4E)-3-ethyl-5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)penta-2,4-dienoic acid, (2E,4E)-5-(1-hydroxy-2,6,6-trimethyl-4- oxocyclohex-2-en-1-yl)-3-(trifluoromethyl)penta
  • COs differ from LCOs in that they lack the fatty acid side chain characteristic of LCOs.
  • COs sometimes referred to as N-acetylchitooligosaccharides 35, are also composed of GlcNAc units, but have side chains that distinguish them from chitin molecules [(C8H13NO5)n, CAS No. 1398-61-4] and chitosan molecules [(C5H11NO4)n, CAS No.
  • LCO lipochitooligosaccharides
  • Nod or Nod factors lipochitooligosaccharides
  • Myc factors consist of an oligosaccharide backbone of ⁇ -l,4-linked N-acetyl-D-glucosamine residues (“GlcNAc”) with an N-linked fatty acid side chain fused to the non-reducing end.
  • LCOs differ in the number of GlcNAc units in the backbone structure, in the length and degree of saturation of the fatty acid chain, as well as in the substitution of the reducing and non-reducing sugar units), linoleic acid or its derivatives, linolenic acid or its derivatives, Maleic hydrazide, mepiquat chloride, mepiquat pentaborate, 1-methylcyclopropene, 3-methylcyclopropene, methoxyvinylglycine (MVG), 3'-methylabscisic acid, 1-(4-methylphenyl)-N-(2-oxo-1-propyl-1,2,3,4-tetrahydroquinolin-6-yl)methanesulfonamide and related substituted (tetrahydroquinolin-6-yl)methanesulfonamides, (3E,3 ⁇ R,8 ⁇ S)-3-( ⁇ [(2R)-4-methyl-5-oxo-2,
  • n A is a natural number from 0 to 5, preferably 0 to 3;
  • RA 1 is halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, nitro or (C1-C4)-haloalkyl;
  • WA is an unsubstituted or substituted divalent heterocyclic radical from the group of the partially saturated or aromatic five-membered ring heterocycles with 1 to 3 hetero ring atoms from the group N and O, wherein at least one N atom and at most one O atom is contained in the ring, preferably a radical from the group (WA 1 ) to (WA 5 ), mA is 0 or 1;
  • R A 2 is OR A 3 , SR A 3 or NR A 3 R A 4 or a saturated or unsaturated 3- to
  • RB 1 is halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, nitro or (C1-C4)-haloalkyl
  • nB is a natural number from 0 to 5, preferably 0 to 3
  • R B 2 is OR B 3 , SR B 3 or NR B 3 R B 4 or a saturated or unsaturated 3- to 7-membered heterocycle having at least one N atom and up to 3 heteroatoms, preferably from the group O and S, which is linked to the carbonyl group in (S2) via the N atom and is unsubstituted or substituted by radicals from the group (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy or optionally substituted phenyl, preferably a radical of the formula OR B 3 , NHR B 4 or N(CH 3 ) 2
  • RC 1 is (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C2-C4)-alkenyl, (C2-C4)-haloalkenyl, (C3-C7)-cycloalkyl, preferably dichloromethyl;
  • RC 2 , RC 3 are the same or different hydrogen, (C1-C4)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C1-C4), haloalkyl, (C2-C4)-haloalkenyl, (C1-C4)-alkylcarbamoyl-(C1-C4)-alkyl, (C2-C4)- Alkenylcarbamoyl-(C1-C4)-alkyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, diox
  • XD is CH or N;
  • R D 1 is CO-NR D 5 R D 6 or NHCO-R D 7 ;
  • R D 2 is halogen, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-haloalkoxy, nitro, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-alkylsulfonyl, (C 1 -C 4 )-alkoxycarbonyl or (C 1 -C 4 )-alkylcarbonyl;
  • R D 3 is hydrogen, (C 1 -C 4 )-alkyl, (C 2 -C 4 )-alkenyl or (C 2 -C 4 )-alkynyl;
  • S5 Active ingredients from the class of hydroxyaromatics and aromatic-aliphatic carboxylic acid derivatives (S5), e.g. 3,4,5-triacetoxybenzoic acid ethyl ester, 3,5-dimethoxy-4-hydroxybenzoic acid, 3,5-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.
  • S6 Active ingredients from the class of 1,2-dihydroquinoxalin-2-ones (S6), e.g.
  • R E 1 , R E 2 are independently of one another halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-alkylamino, di-(C 1 -C 4 )-alkylamino, nitro; 25 A E is COOR E 3 or COSR E 4 RE 3 , RE 4 are independently hydrogen, (C1-C4)-alkyl, (C2-C6)-alkenyl, (C2-C4)-alkynyl, cyanoalkyl, (C1-C4)-haloalkyl, phenyl, nitrophenyl, benzyl, halobenzyl, pyridinylalkyl and alkylammonium, nE 1 is
  • Active ingredients from the class of 3-(5-tetrazolylcarbonyl)-2-quinolones e.g. 1,2-dihydro-4-hydroxy-1-ethyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No. 219479-18-2), 1,2-dihydro-4-hydroxy-1-methyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No. 95855-00-8), as described in WO-A-1999/000020.
  • S11 Active substances of the oxyimino compound type (S11), which are known as seed dressings, such as: B. "Oxabetrinil” ((Z)-1,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile) (S11-1), which is known as a seed dressing safener for millet against metolachlor damage, "Fluxofenim” (1-(4-chlorophenyl)-2,2,2-trifluoro-1-ethanone-O-(1,3-dioxolan-2-ylmethyl)-oxime) (S11-2), which is known as a seed dressing safener for millet against metolachlor damage, and "Cyometrinil” or “CGA-43089” ((Z)-cyanomethoxyimino(phenyl)acetonitrile) (S11-3), which is known as a seed dressing safener for millet against metolachlor damage.
  • S12 Active ingredients from the class of isothiochromanones (S12), such as methyl [(3-oxo-1H-2-benzothiopyran-4(3H)-ylidene)methoxy]acetate (CAS Reg. No. 205121-04-6) (S12-1) and related compounds from WO-A-1998/13361.
  • S12 isothiochromanones
  • S13 One or more compounds from group (S13): "Naphthalic anhydride” (1,8-naphthalenedicarboxylic anhydride) (S13-1), known as a seed dressing safener for maize against damage from thiocarbamate herbicides, "Fenclorim” (4,6-dichloro-2-phenylpyrimidine) (S13-2), known as a safener for pretilachlor in sown rice, "Flurazole” (benzyl 2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate) (S13-3), known as a seed dressing safener for millet against damage from alachlor and metolachlor, "CL 304415” (CAS Reg. No.
  • Preferred safeners in combination with the compounds of the formula (I) according to the invention and/or their salts, in particular with the compounds of the formulas (I.1-1) to (I.14-500) and/or their salts are: cloquintocet-mexyl, cyprosulfamide, fenchlorazole ethyl ester, isoxadifen ethyl, mefenpyr diethyl, fenclorim, cumyluron, S1-14, S1-15, S1-16, S1-17, S1-18, S1-19, S4-1 and S4-5, and particularly preferred safeners are: cloquintocet-mexyl, cyprosulfamide, isoxadifen ethyl and mefenpyr diethyl.
  • ABUTH Abutilon theophrasti
  • ALOMY Alopecurus myosuroides
  • AMARE Amaranthus retroflexus
  • AVEFA Avena fatua
  • BRSNW Brassica napus
  • DIGSA Digitaria sanguinalis
  • ECHCG Echinochloa crus-galli
  • GLXMA Glycine max
  • KCHSC Kochia scoparia
  • LOLRI Lolium rigidum
  • MATIN Matricaria inodora
  • ORYZA Oryza sativa
  • PHPBU Pharbitis purpurea
  • POLCO Polygonum convolvulus SETVI: Setaria viridis VERPE: Veronica persica VIOTR: Viola tricolor
  • TRZAS Triticum aestivum
  • ZEAMX Zea mays A.
  • Tables A1 to A13 below show the effects of selected compounds of general formula (I) according to Table 1 on various weeds and at an application rate corresponding to 20 g/ha and lower, which were obtained according to the aforementioned test procedure.
  • Table A1a Post-emergence effect at 1.25g/ha against ABUTH in %
  • Table A1b Post-emergence effect at 5g/ha against ABUTH in %
  • Table A1c Post-emergence effect at 20g/ha against ABUTH in %
  • Table A2a Post-emergence effect at 1.25g/ha against ALOMY in %
  • Table A2b Post-emergence effect at 5g/ha against ALOMY in %
  • Table A2c Post-emergence effect at 20g/ha against ALOMY in %
  • Table A3 Post-emergence effect at 20g/ha against AVEFA in %
  • Table A4a Post-emergence effect at 5g/ha against DIGSA in %
  • Table A4b Post-emergence effect at 20g/ha against DIGSA in %
  • Table A5a Post-emergence efficacy at 1.25g/ha against ECHCG in % 10
  • Table A5b Post-emergence effect at 5g/ha against ECHCG in %
  • Table A5c Post-emergence effect at 20g/ha against ECHCG in %
  • Table A6a Post-emergence effect at 5g/ha against LRI in %
  • Table A6b Post-emergence effect at 20g/ha against LOLRI in %
  • Table A7a Post-emergence effect at 1.25g/ha against MATIN in %
  • Table A7b Post-emergence effect at 5g/ha against MATIN in %
  • Table A7c Post-emergence effect at 20g/ha against MATIN in %
  • Table A8a Post-emergence effect at 1.25g/ha against PHBPU in %
  • Table A8b Post-emergence effect at 5g/ha against PHBPU in %
  • Table A8c Post-emergence effect at 20g/ha against PHBPU in %
  • Table A9a Post-emergence effect at 1.25g/ha against POLCO in %
  • Table A9b Post-emergence effect at 5g/ha against POLCO in %
  • Table A9c Post-emergence effect at 20g/ha against POLCO in %
  • Table A10a Post-emergence effect at 1.25g/ha against SETVI in %
  • Table A10b Post-emergence effect at 5g/ha against SETVI in %
  • Table A10c Post-emergence effect at 20g
  • Table A12c Post-emergence effect at 20g/ha against VIOTR in %
  • Table A13a Post-emergence effect at 1.25g/ha against KCHSC in %
  • Table A13b Post-emergence effect at 5g/ha against KCHSC in %
  • Table A13c Post-emergence effect at 20g/ha against KCHSC in %
  • Table A14a Post-emergence effect at 1.25g/ha against AMARE in %
  • Table A14b Post-emergence effect at 5g/ha against AMARE in %
  • Table A14c Post-emergence effect at 20g/ha against AMARE in % B. Effect on crop plants in post-emergence Seeds of monocotyledonous and dicotyledonous crop plants were sown in plastic or wood fiber pots in sandy loam soil, covered with soil and grown in the greenhouse under controlled growth conditions.
  • test plants were The compounds of the invention, formulated as wettable powders (WP) or emulsion concentrates (EC), were then sprayed onto the green plant parts as an aqueous suspension or emulsion with the addition of 0.5% additive at a water application rate equivalent to 600 l/ha.
  • WP wettable powders
  • EC emulsion concentrates
  • the effect of the preparations was visually assessed in comparison to untreated controls. For example, 100% effect means plants have died, 0% effect means the same as the control plants.
  • Tables B1 to B4 below show the effects of selected compounds of general formula (I) according to Table 1 on various crops and at an application rate corresponding to 20 g/ha and lower, obtained according to the aforementioned test procedure.

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  • Life Sciences & Earth Sciences (AREA)
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  • Engineering & Computer Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Agronomy & Crop Science (AREA)
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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

La présente invention concerne des oxyiminométhylphényluraciles de formule générale (I) ayant une substitution 4-difluoroalkyle sur l'uracile et des sels de ceux-ci, les radicaux dans la formule générale (I), (I) correspondant aux définitions données dans la description, et leur utilisation en tant qu'herbicides, en particulier pour lutter contre les mauvaises herbes et/ou les mauvaises herbes dans des cultures de plantes utiles, et/ou en tant que régulateurs de croissance de plantes pour réguler la croissance de cultures de plantes utiles.
PCT/EP2024/081820 2023-11-15 2024-11-11 Oxyiminométhylphényluraciles substitués, sels de ceux-ci et leur utilisation en tant que substances actives herbicides Pending WO2025103927A1 (fr)

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