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WO2025103929A1 - Uraciles d'acide n-benzoïque substitués et leurs sels, et leur utilisation en tant que substances actives herbicides - Google Patents

Uraciles d'acide n-benzoïque substitués et leurs sels, et leur utilisation en tant que substances actives herbicides Download PDF

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Publication number
WO2025103929A1
WO2025103929A1 PCT/EP2024/081827 EP2024081827W WO2025103929A1 WO 2025103929 A1 WO2025103929 A1 WO 2025103929A1 EP 2024081827 W EP2024081827 W EP 2024081827W WO 2025103929 A1 WO2025103929 A1 WO 2025103929A1
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alkyl
aryl
alkoxy
cycloalkyl
hydrogen
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German (de)
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
    • A01P13/02—Herbicides; Algicides selective
    • 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 plant protection products, in particular herbicides for the selective control of weeds and grass weeds in crops.
  • this invention relates to substituted N-benzoic acid uracils with 4-difluoroalkyl substitution on the uracil and to 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. For other active ingredients, the effect depends too strongly on environmental conditions, such as weather and soil conditions.
  • aryluracils can be used as herbicidal active ingredients (cf. WO2021/013799, W02021/013800, PCT/EP2021/073129 (PCT filing of August 20, 2021), EP408382, EP473551, EP648749, US4,943,309, US5,084,084, US5,127,935, W091/00278, WO95/29168, WO95/30661, WO96/35679, WO97/01541, WO98/25909, WO2001/39597, DE4431219).
  • the known aryluracils have several gaps in their effectiveness, particularly against monocotyledonous weeds.
  • N-aryluracils with optionally further substituted lactic acid groups can also be used as herbicidal active ingredients (cf. JP2000/302764, JP2001/172265, US6,403,534, EP408382). Furthermore, it is known that N-aryluracils with specific, optionally further substituted, thiolactic acid groups also exhibit herbicidal effects (cf. W02010/038953, KR2011110420). Selected substituted tetrahydrofuryl esters of N-aryluracils with optionally further substituted thiolactic acid groups are described in JP09188676.
  • substituted N-benzoic acid uracils that carry chlorine substituents in the benzoic acid moiety
  • substituted N-benzoic acid uracils that carry chlorine substituents in the benzoic acid moiety
  • highly substituted 3-amino-l-(3-carboxy-4-cyanophenyl)uracils with various carboxylate side chains have been described (cf. WO98/25909).
  • Highly substituted N-benzoic acid uracils with an aminosulfonylaminocarbonylalkoxy side chain are also known (cf. WO2004/009561).
  • the present invention thus relates to substituted N-benzoic acid uracils of the general formula (I) or their salts wherein
  • R 1 represents hydrogen, halogen, (C 1 -C 4 )-alkoxy
  • R 2 represents halogen, cyano, nitro, C(O)NH 2 , C(S)NH 2 , (C 1 -C 8 )-haloalkyl, (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, 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-member
  • the compounds of general formula (I) can be prepared by addition of a suitable inorganic or organic acid, such as, for example, mineral acids, such as, for example, HCl, HBr, H2SO4, H3PO4 or HNO3, 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, form salts with 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.
  • a suitable inorganic or organic acid such as, for example, mineral acids, such as, for example, HCl, HBr, H2SO4, H3PO4 or HNO3, or organic acids, e.g. carboxylic acids such as formic acid, acetic acid, prop
  • Suitable substituents which 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 the 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 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 R a to R d each independently represent an organic radical, in particular alkyl, aryl, aralkyl, or alkylaryl.
  • metal salts in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or 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 R a to R d each independently represent an organic radical, in particular alkyl, aryl,
  • alkylsulfonium and alkylsulfoxonium salts such as (C 1 -C 4 )-trialkylsulfonium and (C 1 -C 4 )-trialkylsulfoxonium salts.
  • alkylsulfonium and alkylsulfoxonium salts such as (C 1 -C 4 )-trialkylsulfonium and (C 1 -C 4 )-trialkylsulfoxonium salts.
  • W represents the groups W -1 W-2
  • R 1 represents hydrogen, fluorine, chlorine, bromine
  • R 2 represents fluorine, chlorine, bromine, cyano, nitro, C(O)NH2, C(S)NH2, trifluoromethyl, ethynyl, propyn-1-yl
  • R 3 and R 4 independently of one another represent hydrogen, (C1-C6)-alkyl, R 13 O-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C2-C6)-alkenyl, aryl-(C1-C6)-alkyl, heteroaryl-(C1-C6)-alkyl, heterocyclyl-(C1-C6)-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-membered carbocyclic ring
  • R 5 represents hydrogen, fluorine, chlorine
  • R 6 represents (
  • W represents the groups W -1 W-2
  • R 1 represents hydrogen, fluorine, chlorine
  • R 2 represents fluorine, chlorine, bromine, cyano, nitro, C(O)NH 2 , C(S)NH 2 , trifluoromethyl
  • R 3 and R 4 independently of one another represent hydrogen, (C1-C4)-alkyl, (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, fluorine
  • R 6 represents methyl, ethyl, prop-1-yl
  • R 7 represents hydrogen
  • Q represents hydroxy or a radical of the following formulas
  • R 8 is hydrogen, (C1-C5)-alkyl, (C1-C5)-haloalkyl, aryl, aryl-(C1-C5)-alkyl, heteroaryl, (C
  • Very particularly preferred subject matter of the invention are compounds of the general formula (I), wherein W represents the groups - R 1 represents hydrogen, fluorine, R 2 represents fluorine, chlorine, bromine, cyano, nitro, C(O)NH2, C(S)NH2, R 3 and R 4 independently of one another represent hydrogen, methyl, ethyl, prop-l-yl, prop-2-yl, but-l-yl, but-2-yl, 2-methyl-prop-l-yl, 1,1-dimethyleth-l-yl, 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 stands for hydrogen
  • R 6 stands for methyl, ethyl
  • R 7 stands for hydrogen
  • R 1 stands for hydrogen, fluorine
  • R 2 stands for fluorine, chlorine, bromine, cyano, nitro
  • R 3 and R 4 independently represent hydrogen, methyl, ethyl, propyl,
  • R 5 stands for hydrogen
  • R 6 stands for methyl, ethyl
  • R 7 stands for hydrogen
  • Q stands for one of the above specifically mentioned groupings Q-1 to Q-500.
  • R 1 stands for hydrogen, fluorine
  • R 2 stands for fluorine, chlorine, bromine, cyano, nitro
  • R 3 and R 4 independently represent hydrogen, methyl
  • R 5 stands for hydrogen
  • R 6 stands for methyl, ethyl
  • R 7 stands for hydrogen
  • Q stands for one of the above specifically mentioned groupings Q-1 to Q-500.
  • R 1 stands for hydrogen, fluorine
  • R 3 and R 4 independently represent hydrogen, methyl
  • R 5 stands for hydrogen
  • R 6 stands for methyl, ethyl
  • R 7 stands for hydrogen, and Q represents one of the above-mentioned specifically named groups Q-1 to Q-500.
  • Particularly preferred subject matter of the invention are compounds of the general formula (I), wherein W represents the group R 1 represents fluorine, R 2 represents chlorine, bromine, R 3 and R 4 independently represent methyl, R 5 represents hydrogen, R 6 represents methyl, R 7 represents hydrogen, and Q represents one of the groups Q-1, Q-71, Q-176, Q-371, Q-441, Q-442, Q-454, Q-457, Q-471, Q-480, Q-481 or Q-491 specifically mentioned above.
  • radical definitions listed above apply both to the end products of the formula (I) and correspondingly to the respective ones used for the preparation required starting materials or intermediates. These radical definitions can be combined with one another as desired, i.e. also between the stated preferred ranges.
  • the designations used above and below are explained. These are familiar to the person skilled in the art and have in particular the meanings explained below: Unless defined otherwise, the general rule for the designation of chemical groups is that the bond to the skeleton or the rest of the molecule is via the last-mentioned structural element of the chemical group in question, e.g.
  • alkyl therefore also refers to an alkylene group.
  • 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 represents 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 - represents straight-chain or branched S-alkyl, preferably with 1 to 8, or with 1 to 6 Carbon atoms such as (C1-C10), (C1-C6) or (C1-C4) alkylthio, for example (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, Hexyl
  • 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., (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,
  • Alkenyloxy means an alkenyl radical bonded via an oxygen atom
  • alkynyloxy means an alkynyl radical bonded via an oxygen atom, such as (C 2 -C 10 ), (C 2 -C 6 ) or (C 2 -C 4 ) alkenoxy or (C 3 -C 10 ), (C 3 -C 6 ) or (C 3 -C 4 ) alkynoxy.
  • Cycloalkyloxy means a cycloalkyl radical bonded via an oxygen atom
  • cycloalkenyloxy means a cycloalkenyl radical bonded via an oxygen atom.
  • the number of C 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 OC(S)OR 13 , OC(S)SR 14 , OC(S)NR”R 12 the abbreviation S in parentheses stands for a sulfur atom bonded to the neighboring 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 carbon atoms, for example phenyl, naphthyl, anthryl, phenanthrenyl, and the like, preferably phenyl.
  • optionally substituted aryl also encompasses polycyclic systems such as tetrahydronaphthyl, indenyl, indanyl, fluorenyl, and biphenylyl, where the bonding site is on the aromatic system.
  • aryl is generally also encompassed by 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-[
  • polycyclic systems are also included, such as, for example, 8-aza-bicyclo[3.2.1]octanyl, 8-aza-bicyclo[2.2.2]octanyl or 1-aza-bicyclo[2.2.1]heptyl.
  • spirocyclic systems are also included, such as, for example, l-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 two oxygen atoms should not be directly adjacent, such as 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-
  • 3-membered and 4-membered ring heterocycles are, for example, 1- or 2-aziridinyl, oxiranyl, thiiranyl, 1- or 2- or 3-azetidinyl,
  • heterocyclyl are a partially or fully hydrogenated heterocyclic radical with two heteroatoms from the group N, O and S, such as 1- or 2- or 3- or 4-pyrazolidinyl; 4,5-dihydro-3H-pyrazol- 3- or 4- or 5-yl; 4,5-dihydro-lH-pyrazol-l- or 3- or 4- or 5-yl; 2,3-dihydro-lH-pyrazol-l- or 2- or
  • 6-yl 1,4,5,6-tetrahydropyridazin-1- or 3- or 4- or 5- or 6-yl; 3,4,5,6-tetrahydropyridazin-3- or 4- or 5-yl; 4,5-dihydropyridazin-3- or 4-yl; 3,4-dihydropyridazin-3- or 4- or 5- or 6-yl; 3,6-dihydropyridazin-3- or 4-yl; 1,6-dihydropyriazin-1- or 3- or 4- or 5- or 6-yl; hexahydropyrimidin-1- or 2- or 3- or 4-yl; 1,4,5,6-tetrahydropyrimidin-1- or 2- or 4- or 5- or 6-yl; 1,2,5,6-Tetrahydropyrimidin-l- or 2- or 4- or 5- or 6-yl; 1,2,3,4-Tetrahydropyrimidin-1- or 2- or 3- or 4- or 5- or 6-yl; 1,6-Dihydropyrimidin-l-
  • 1,2-Dithiolan-3- or 4-yl 1,2-Dithiolan-3- or 4-yl; 3H-1,2-Dithiol-3- or 4- or 5-yl; l,3-Dithiolan-2- or 4-yl; 1,3-Dithiol-2- or 4-yl; l,2-Dithian-3- or 4-yl; 3,4-Dihydro-1,2-dithiin-3- or 4- or 5- or 6-yl; 3,6-dihydro
  • 6- or 7-yl 2,5-dihydro-l,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 2,7-dihydro-l,3-oxazepin- 2- or 4- or 5- or 6- or 7-yl; 4,5-dihydro-l,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 4,7-dihydro-l,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 6,7-dihydro-l,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; l,3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 1,4-Oxazepan-2- or 3- or 5- or 6- or 7-yl; 2,3,4,5-Tetrahydro-l,4-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2, 3,4,7-Tetrahydro-l
  • 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-l,4,2-dioxazepin-2- or 3- or 5- or 6- or 7-yl; 2,3-Dihydro-5H-l,4,2-dioxazepin-2- or 3-
  • 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
  • Substituents for a substituted heterocyclic residue are those listed below Substituents are also possible, in addition to 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 SO) and S(O)z (also abbreviated SO2) in the heterocyclic ring. In the case of -N(O)- and -S(O) groups, both enantiomers are included.
  • heteroaryl stands for heteroaromatic compounds, i.e. 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, 1H-pyrrol-1-yl; 1H-pyrrol-2-yl; 1H-pyrrol-
  • heteroaryl groups according to the invention can also 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 are preferred (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; Pyridopyr azine; pyr
  • 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, l-benzothiophen-6-yl, l-benzothiophen-3
  • halogen means, for example, fluorine, chlorine, bromine, or iodine.
  • 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; particularly preferred are methoxy, methyl, fluoroalkyl, cyano, nitro, fluorine, chlorine, bromine, or iodine.
  • the prefix "bis” also includes the combination of different alkyl radicals, e.g., methyl(ethyl) or ethyl(methyl).
  • Haloalkyl mean alkyl, alkenyl or alkynyl which are partially or fully substituted by identical or different halogen atoms, e.g. monohaloalkyl
  • ( monohaloalkyl) such as CH 2 CH 2 C1, CH 2 CH 2 Br, CHC1CH 3 , CH 2 C1, CH 2 F; perhaloalkyl such as CC1 3 > CC1F 2 , CFC1 2 , CF 2 CC1F 2 , CF 2 CC1FCF 3 ; polyhaloalkyl such as CH 2 CHFC1, CF 2 CC1FH, 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 CHFCH 3 , CH 2 CH 2 F, CH 2 CH 2 CF 3 , CHF 2 , CH 2 F, CHFCF 2 CF 3
  • Partially fluorinated haloalkyl means a straight-chain or branched, saturated
  • the corresponding halogen atoms can be present 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 OCH2CH2CI; the same applies to haloalkenyl and other halogen-substituted radicals.
  • (C1-C4)-alkyl used here as an example is a shorthand notation for straight-chain or branched alkyl with one to four carbon atoms, corresponding to the range specified for C atoms, i.e., it includes the radicals methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl, or tert-butyl.
  • lower carbon skeletons e.g., those with 1 to 6 carbon atoms, or unsaturated groups with 2 to 6 carbon atoms, are preferred for hydrocarbon radicals such as alkyl, alkenyl, and alkynyl radicals, even in compound radicals.
  • Alkyl radicals even in 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 represent the possible unsaturated radicals corresponding to the alkyl radicals, containing at least one double bond or triple bond.
  • 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, for example, 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-C8)-alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, l-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, l-methyl-2-butenyl, 2-methyl-2-butenyl, 3-Methyl-2-butenyl, l-methyl-3-butenyl, 2-methyl-3- butenyl, 3-methyl-3-butenyl, l,l-dimethyl-2-propenyl, 1,2-dimethyl-l-propenyl, 1,2-dimethyl-2-propenyl, 1-
  • alkynyl 1 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-l-yn-l-yl.
  • (Ci-Gj-alkynyl means, for example, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, l-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, l-methyl-2-butynyl, l-Methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-l -butynyl, l,l-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, l-methyl-2-pentynyl, l-methyl-3-pentynyl, l-methyl-4-
  • 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[l.1.0]butan-1-yl, bicyclo[l.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,
  • spirocyclic aliphatic systems are also included, such as spiro[2.2]pent-l-yl, spiro[2.3]hex-l-yl, spiro[2.3]hex-4-yl, 3-spiro[2.3]hex-5-yl, spiro[3.3]hept-l-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., 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1,3-cyclohexadienyl, or 1,4-cyclohexadienyl, which also includes substituents with a double bond on the cycloalkenyl radical, e.g., an alkylidene group such as methylidene.
  • an alkylidene group such as methylidene
  • alkylidene also known as (Ci-Cio)-alkylidene, means the residue of a straight-chain or branched open-chain hydrocarbon radical bonded by a double bond.
  • alkylidene also known as (Ci-Cio)-alkylidene
  • alkylidene means the residue of a straight-chain or branched open-chain hydrocarbon radical bonded by a double bond.
  • Cycloalkylidene means a carbocyclic radical bonded by a double bond.
  • Cycloalkylalkyloxy means a cycloalkylalkyl radical bonded via an oxygen atom and “arylalkyloxy” means an arylalkyl radical bonded via an oxygen atom.
  • Alkoxyalkyl means an alkoxy radical bonded via an alkyl group and “alkoxyalkoxy” means an alkoxyalkyl radical bonded via an oxygen atom, e.g. (but not limited to) methoxymethoxy, methoxyethoxy, ethoxyethoxy, methoxy-n-propyloxy.
  • Alkylthioalkyl means an alkylthio radical bonded via an alkyl group and “alkylthioalkylthio” means an alkylthioalkyl radical bonded via an oxygen atom.
  • Arylalkoxyalkyl means an aryloxy radical bonded via an alkyl group and “heteroaryloxyalkyl” means a heteroaryloxy radical bonded via an alkyl group.
  • Haloalkoxyalkyl means a bound haloalkoxy radical and “haloalkylthioalkyl” means a haloalkylthio radical bound 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 bonded via an alkyl group, for example (but not limited to) cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, 1-cyclopropyleth-l-yl, 2-cyclopropyleth-l-yl, 1-cyclopropylprop-l-yl, 3-cyclopropylprop-l-yl.
  • Arylalkenyl means an aryl radical bonded via an alkenyl group
  • heteroarylalkenyl means a heteroaryl radical bonded via an alkenyl group
  • heterocyclylalkenyl means a heterocyclyl radical bonded via an alkenyl group
  • Arylalkynyl means 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 (Ci-Cs)-, (Ci-Ce)- or (Ci-C4)-haloalkylthio, e.g. (but not limited to) trifluoromethylthio, pentafluoroethylthio, difluoromethyl, 2,2-difluoroethylthio, 2,2,2-difluoroethylthio, 3,3,3-prop-l-ylthio.
  • Halocycloalkyl and halocycloalkenyl mean cycloalkyl or cycloalkenyl which are partially or fully substituted by identical or different halogen atoms, such as F, CI and Br, or by haloalkyl, such as trifluoromethyl or difluoromethyl, e.g.
  • trialkylsilyl alone or as part of a chemical group - stands for straight-chain or branched Si-alkyl, preferably having 1 to 8, or having 1 to 6 carbon atoms, such as tri-[(Ci-Cs)-, (Ci-Ce)- or (Ci-CO-alkyl]silyl, e.g.
  • Trialkylsilylalkynyl means a trialkylsilyl radical bonded via an alkynyl group. If the compounds can form tautomers through hydrogen shift that are not structurally covered by formula (I), these tautomers are nevertheless encompassed by the definition of the compounds of formula (I) according to the invention, unless a specific tautomer is considered. For example, many carbonyl compounds can exist in both the keto and enol forms, with both forms being encompassed by the definition of the compound of formula (I).
  • the compounds of general formula (I) can exist as stereoisomers depending on the nature and linkage of the substituents.
  • the possible stereoisomers defined by their specific spatial shape, such as enantiomers, diastereomers, Z- and E-isomers, are all encompassed by formula (I). If, for example, one or more alkenyl groups are present, diastereomers (Z- and E-isomers) can occur. If, for example, one or more asymmetric carbon atoms are present, enantiomers and diastereomers can occur.
  • 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 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.
  • purification can also be carried out by recrystallization or digestion. If individual compounds (I) are not satisfactorily accessible by the routes 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) include methods generally known to the skilled person from analogous cases, e.g., 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. Synthesis of substituted N-benzoic acid uracils with 4-difluoroalkyl substitution on the uracil of the general formula (I):
  • the substituted N-benzoic acid uracils according to the invention with 4-difluoroalkyl substitution on the uracil of the general formula (I) can be prepared starting from known processes.
  • the synthetic routes used and investigated start from 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 12 , R 13 , R 14 , R 15 and R 16 of the general formula (I) have the previously defined meanings in the following schemes, unless exemplary but non-limiting definitions are given.
  • the synthesis of the compounds of the general formula Ia, Ib or Ic proceeds as follows, for example, in Scheme
  • R 1 is, by way of example but not limitation, fluorine
  • R 5 is, by way of example but not limitation, hydrogen
  • R 6 is, by way of example but not limitation, methyl
  • R 7 is, by way of example but not limitation, hydrogen
  • R 3 and R 4 are, by way of example but not limitation, methyl.
  • nitrated benzoic acid (II) is obtained using nitrating acid (cf. Medicinal Chemistry Letters (2016), 7(12), 1077-1081).
  • nitrating acid cf. Medicinal Chemistry Letters (2016), 7(12), 1077-1081.
  • the esterification can be carried out, as shown by way of example but not limitation in Scheme 1, via transformation into the acid chloride using thionyl chloride, 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)
  • EDC l-ethyl-3-
  • the subsequent condensation reaction of the 3-aminobenzoic acid ester (V) with the resulting oxazin-6-one (VII) using acetic acid as solvent at a suitable temperature yields the uracil (VIII), which can be converted into the N-alkyl-N'-benzoic acid uracil (Ia) by subsequent N-alkylation, represented here by way of example but not limitation as N-methylation.
  • the 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).
  • EDC l-ethyl-3-(3-dimethylaminopropyl)carbodiimide
  • HATU O-(7-azabenzotriazol-l-yl)-N,
  • 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)
  • N-amino-bT-benzoic acid uracil (Id) is carried out starting from the previously described uracil (VIII) by N-amination, as shown below in Scheme 2.
  • the N-amination is carried out with the aid of a suitable amination reagent (e.g. O-(mesitylsulfonyl)hydroxylamine, O-(tolylsulfonyl)hydroxylamine, O-(diphenylphosphoryl)hydroxylamine) 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. O-(mesitylsulfonyl)hydroxylamine, O-(tolylsulfonyl)hydroxylamine, O-(dip
  • EDC l-ethyl-3-(3-dimethylaminopropyl)carbodiimide
  • HATU O-(7-azabenzotriazol-l-yl)-N,
  • 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)
  • 2-Chloro-4-fluoro-5-nitrobenzoic acid (5000 mg, 22.7 mmol; for synthesis, see e.g., CN106905161, W02006090210) was initially dissolved in 50 mL of dichloromethane, and oxalyl chloride (5781 mg, 45.5 mmol) and a catalytic amount of N,N-dimethylformamide (0.3 mL) were added. After stirring for 3 hours at room temperature, a clear reaction solution was obtained, which was subsequently concentrated under reduced pressure.
  • the resulting acid chloride was dissolved in 8 mL of dichloromethane and added dropwise to a solution of allyl 2-hydroxy-2-methylpropanoate (3665 mg, 25.42 mmol), triethylamine (3344 mg, 33.05 mmol), and 4-dimethylaminopyridine (310.6 mg, 2.54 mmol) in 50 mL of dichloromethane.
  • the reaction mixture was stirred for 4 hours and then stood overnight. After the addition of further amounts of allyl 2-hydroxy-2-methylpropanoate (approx. 1000 mg), it was stirred for a further 2 hours at room temperature. Subsequently, a mixture of water and 100 mL of 2N hydrochloric acid was added to the reaction mixture.
  • reaction mixture 20 mE was then added, and the resulting reaction mixture was stirred at room temperature for 2 h. After complete conversion, the reaction mixture was diluted with ethyl acetate, followed by water and saturated sodium chloride solution, and then thoroughly extracted with dichloromethane. The combined organic phases were dried over sodium sulfate, filtered, and concentrated under reduced pressure.
  • reaction mixture was stirred at room temperature for approximately 1 h. Complete conversion was detected by thin-layer chromatography, so the reaction was subsequently quenched by adding 5 mL of water and made basic by adding sodium bicarbonate solution. After phase separation, the aqueous phase was acidified by adding 2N hydrochloric acid and subsequently extracted several times with dichloromethane. The organic phase was dried using a separator cartridge, and after collecting the organic phase, the solvent was removed under reduced pressure.
  • reaction mixture was stirred for 3 h at RT and left to stand overnight. The mixture was then quenched by adding 1 mL of water, and the reaction mixture was stirred. After phase separation, the organic phase was dried, and the solvent was subsequently removed in vacuo.
  • Benzyl alcohol (57 mg, 0.53 mmol) was then added, and the resulting reaction mixture was stirred at room temperature for 5 h. After standing overnight, 5 mL of dichloromethane and 5 mL of water were added. The reaction mixture was separated from the aqueous phase using a separator cartridge, and after collecting the organic phase, the solvent was removed under reduced pressure.
  • Table 1.1 Preferred compounds of formula (1.1) are the compounds 1.1-1 to 1.1-500, wherein Q has the meanings given in the respective row of Table 1.
  • the compounds 1.1-1 to 1.1-500 of Table LI are thus defined by the meaning of the respective entries No. 1 to 500 for Q of the
  • Table 1 Table 1.2: Preferred compounds of formula (1.2) are compounds 1.2-1 to 1.2-500, wherein Q has the meanings given in the respective row of Table 1.
  • the compounds 1.2-1 to 1.2-500 of Table 1.2 are thus defined by the meaning of the respective entries No. 1 to 500 for Q of Table 1.
  • Table 1.3 Preferred compounds of formula (1.3) are compounds 1.3-1 to 1.3-500, wherein Q has the meanings given in the respective row of Table 1.
  • the compounds 1.3-1 to 1.3-500 of Table 1.3 are thus defined by the meaning of the respective entries No. 1 to 500 for Q of Table 1.
  • Table 1.4 Preferred compounds of formula (1.4) are compounds 1.4-1 to 1.4-500, wherein Q has the meanings given in the respective row of Table 1.
  • the compounds 1.4-1 to 1.4-500 of Table 1.4 are thus defined by the meaning of the respective entries No. 1 to 500 for Q of Table 1.
  • Table 1.5: Preferred compounds of formula (1.5) are compounds 1.5-1 to 1.5-500, wherein Q has the meanings given in the respective row of Table 1.
  • the compounds 1.5-1 to 1.5-500 of Table 1.5 are thus defined by the meaning of the respective entries No. 1 to 500 for Q of Table 1.
  • Table 1.6 Preferred compounds of formula (1.6) are compounds 1.6-1 to 1.6-500, wherein Q has the meanings given in the respective row of Table 1.
  • the compounds 1.6-1 to 1.6-500 of Table 1.6 are thus defined by the meaning of the respective entries No. 1 to 500 for Q of Table 1.
  • Table 1.7 Preferred compounds of formula (1.7) are compounds 1.7-1 to 1.7-500, wherein Q has the meanings given in the respective row of Table 1.
  • the compounds 1.7-1 to 1.7-500 of Table 1.7 are thus defined by the meaning of the respective entries No. 1 to 500 for Q of Table 1.
  • Table 1.8 Preferred compounds of formula (1.8) are compounds 1.8-1 to 1.8-500, wherein Q has the meanings given in the respective row of Table 1.
  • the compounds 1.8-1 to 1.8-500 of Table 1.8 are thus defined by the meaning of the respective entries No. 1 to 500 for Q of Table 1.
  • Table 1.9 Preferred compounds of formula (1.9) are the compounds 1.9-1 to 1.9-500, wherein Q has the meanings given in the respective row of Table 1.
  • the compounds 1.9-1 to 1.9-500 are the compounds 1.9-1 to 1.9-500, wherein Q has the meanings given in the respective row of Table 1.
  • the compounds 1.9-1 to 1.9-500 are the compounds 1.9-1 to 1.9-500, wherein Q has the meanings given in the respective row of Table 1.
  • Table 1.12 Preferred compounds of formula (1.12) are the compounds 1.12-1 to 1.12-500, where Q has the meanings given in the respective row of Table 1.
  • NMR data of selected examples The 'H-NMR data of selected examples of compounds of general formula (I) are given in two different ways, namely (a) classical NMR analysis and interpretation or (b) in the form of 'H-NMR peak lists according to the method described below. a) classical NMR interpretation b) NMR peak list method
  • the 'H NMR data of selected examples are recorded in the form of 'H NMR peak lists. For each signal peak, the ⁇ value in ppm is listed first, followed by the signal intensity in parentheses. The ⁇ value - signal intensity number pairs for different signal peaks are listed separated 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 measured in DMSO. Therefore, the tetramethylsilane peak may or may not appear in NMR peak lists.
  • 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 provides a method for controlling unwanted 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 (1.1-1) to (1.14-500) and/or salts thereof, in each case as defined above, or of an agent according to the invention, as defined below, is applied to unwanted plants (e.g. harmful plants such as mono- or dicotyledonous weeds or unwanted crop plants), the seed of the unwanted plants (i.e. plant seeds, e.g.
  • unwanted plants e.g. harmful plants such as mono- or dicotyledonous weeds or unwanted crop plants
  • the seed of the unwanted plants i.e. plant seeds, e.g.
  • the soil in or on which the unwanted plants grow e.g. the soil of cultivated land or non-cultivated land
  • the cultivated area i.e. area on which the unwanted 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 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 of an agent according to the invention, as defined below, is applied to the plant, the seed of the plant (i.e. 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 soil of cultivated land or non-cultivated land) or the cultivation area (i.e. area on which the plants will grow).
  • the seed of the plant i.e. plant seeds, e.g. grains, seeds or vegetative propagation organs such as tubers or shoot parts with buds
  • the compounds or 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 that can be controlled by the compounds according to the invention are mentioned as examples, without implying a restriction to specific species.
  • one or more compounds of the formula (I) and/or salts thereof are used for controlling harmful plants or for regulating the growth in crops of useful plants or ornamental plants, wherein the useful plants or ornamental plants are, in a preferred embodiment, transgenic plants.
  • the compounds of formula (I) according to the invention and/or their salts are suitable for controlling the following genera of monocotyledonous and dicotyledonous weeds:
  • 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 according to the invention are applied to the soil surface before the germination of the harmful plants (grass and/or weeds) (pre-emergence method), the emergence of the weed seedlings is either 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 invention have excellent herbicidal activity against mono- and dicotyledonous weeds, crop plants of economically important crops, e.g. dicotyledonous crops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Depending on the structure of the respective compound according to the invention and the application rate, 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, and Zea are only slightly damaged or not damaged at all. For these reasons, the present compounds are highly suitable for the selective control of undesirable plant growth in plant crops such as agricultural crops or ornamental plants.
  • the compounds of the invention exhibit outstanding growth-regulating properties in crop plants. They regulate the plant's own metabolism and can thus be used to specifically influence plant constituents and facilitate harvesting, for example, by inducing desiccation and stunting. Furthermore, 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 reduce or completely prevent lodging, for example.
  • Transgenic plants are generally characterized by particularly advantageous properties, such as 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 affect, for example, the harvested crop in terms of quantity, quality, storability, composition, and specific ingredients.
  • Transgenic plants with increased starch content or altered starch quality, or those with a different fatty acid composition of the harvested crop 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 crops 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 that are resistant to the phytotoxic effects of the herbicides or have been genetically engineered to be resistant. Due to their herbicidal and plant growth regulatory 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 affect, for example, 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.
  • Other special properties can include tolerance or resistance to abiotic stressors such as heat, cold, drought, salt and ultraviolet radiation.
  • the use of the compounds of formula (I) according to the invention or their salts is preferred in economically important transgenic crops of useful and ornamental plants, e.g. cereals such as wheat, barley, rye, oats, triticale, millet, rice, cassava and maize or also crops of sugar beet, cotton, soybeans, rapeseed, potatoes, tomatoes, peas and other vegetables.
  • cereals such as wheat, barley, rye, oats, triticale, millet, rice, cassava and maize or also crops of sugar beet, cotton, soybeans, rapeseed, potatoes, tomatoes, peas and other vegetables.
  • the compounds of formula (I) can be used as herbicides in crops which are resistant to the phytotoxic effects of the herbicides or have been made resistant by genetic engineering.
  • nucleic acid molecules can be introduced into plasmids that allow mutagenesis or sequence modification through recombination of DNA sequences. Using standard procedures, base substitutions can be performed, partial sequences can be removed, or natural or synthetic sequences can be added. Adapters or linkers can be attached to the DNA fragments to connect them to one another.
  • the production of plant cells with a reduced activity of a gene product can be achieved, for example, by the expression of 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 contain the entire coding sequence of a gene product, including any flanking sequences present, or DNA molecules that contain only parts of the coding sequence. These parts must be long enough to produce an antisense effect in the cells. It is also possible to use DNA sequences that exhibit a high degree of homology to the coding sequences of a gene product, but are not completely identical.
  • nucleic acid molecules When nucleic acid molecules are expressed in plants, the synthesized protein can be localized in any compartment of the plant cell. However, to achieve localization in a specific compartment, the coding region can 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 nucleic acid molecules can also occur 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 (I) according to the invention can be used in transgenic crops which are resistant to growth promoters, such as dicamba, or to herbicides which 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 benzoylisoxazoles and analogous active ingredients.
  • ALS acetolactate synthases
  • EPSP synthases glutamine synthases
  • HPPD hydroxyphenylpyruvate dioxygenases
  • the invention therefore also relates to the use of the compounds of the formula (I) according to the invention and/or salts thereof as herbicides for controlling harmful plants in crops of useful or ornamental plants, optionally in transgenic crops.
  • the preferred use is in cereals, preferably maize, wheat, barley, rye, oats, millet or rice, in pre- or post-emergence.
  • the use according to the invention for controlling harmful plants or for regulating the growth of plants 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
  • (a) contains one or more compounds of 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 formulae (I.1-1) to (I.14-500) and/or salts thereof, each as defined above, and
  • component (i) of a composition according to the invention are preferably selected from the group of substances mentioned in "The Pesticide Manual", 19th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2021.
  • a herbicidal or plant growth regulating agent according to the invention preferably comprises one, two, three or more formulation auxiliaries (ii) customary in plant protection selected from the group consisting of surfactants, emulsifiers, dispersants, film formers, thickeners, inorganic salts, dusting agents, carriers which are solid at 25 °C and 1013 mbar, preferably adsorptive, granulated inert materials, wetting agents, antioxidants, stabilizers, buffer substances, antifoams, water, organic solvents, preferably organic solvents which are miscible with water in any ratio at 25 °C and 1013 mbar.
  • formulation auxiliaries customary in plant protection selected from the group consisting of surfactants, emulsifiers, dispersants, film formers, thickeners, inorganic salts, dusting agents, carriers which are solid at 25 °C and 1013 mbar, preferably adsorptive, granulated inert materials, wetting agents, antioxidants, stabilize
  • 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 their salts can be formulated in various ways, depending on the biological and/or chemical-physical parameters specified. Possible formulation options include, for example, wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), 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 microgranules, spray granules, emulsifiable granules, and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules, and waxes.
  • WP wett
  • Wettable powders are preparations that are evenly dispersible in water.
  • they contain a diluent or inert substance as well as 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.
  • the herbicidal active ingredients are finely ground in conventional equipment such as hammer mills, fan mills, and air jet mills and mixed simultaneously or subsequently with the
  • 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 these organic solvents, with the addition of one or more ionic and/or non-ionic surfactants (emulsifiers).
  • organic solvent e.g., butanol, cyclohexanone, dimethylformamide, xylene, or higher-boiling aromatics or hydrocarbons, or mixtures of these organic solvents.
  • alkylarylsulfonic acid calcium salts such as calcium 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. 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, with the addition of surfactants, such as those 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 adsorbent, granulated inert material or by applying active ingredient concentrates to the surface of carrier materials such as sand, kaolinite, or granulated inert material using adhesives, e.g., polyvinyl alcohol, sodium polyacrylate, 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 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 about 10 to 90% by weight, the remainder to 100% by weight consists of conventional formulation ingredients.
  • the active ingredient concentration can be about 1 to 90, preferably 5 to 80% by weight.
  • Dust-like formulations contain 1 to 30% by weight of active ingredient, preferably 5 to 20% by weight of active ingredient, sprayable solutions contain about 0.05 to 80, preferably 2 to 50% by weight of 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% by weight, preferably between 10 and 80% by weight.
  • the active ingredient formulations mentioned may contain the usual adhesives, wetting agents, dispersing agents, emulsifying agents, penetrants, preservatives, antifreeze agents, solvents, fillers, carriers, dyes, defoamers, evaporation inhibitors, and pH and viscosity adjusters. Examples of formulation aids are described, 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 ready-to-use formulations or as tank mixes.
  • pesticidally active substances such as insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers, and/or growth regulators, e.g., as ready-to-use formulations or as tank mixes.
  • the combination formulations can be prepared based on the above-mentioned formulations, taking into account the physical properties and stability of the active ingredients to be combined.
  • the safeners which are used in an antidote-effective concentration, reduce the phytotoxic side effects of the herbicides/pesticides used, e.g., in economically important crops such as cereals (wheat, barley, rye, maize, rice, millet), sugar beet, sugar cane, rapeseed, cotton, and soybeans, preferably cereals.
  • the weight ratio of herbicide (mixture) to safener generally depends on the
  • the amount of herbicide applied and the effectiveness of the respective safener and can be Limits vary, 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 their mixtures 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 in commercial form are diluted in the usual way, e.g., with water for wettable powders, emulsifiable concentrates, dispersions, and water-dispersible granules. Dust-like preparations, soil or broadcast granules, and sprayable solutions are not usually diluted with other inert substances prior to application.
  • the application rate of the compounds of formula (I) and/or their salts influences to a certain extent the application rate of the compounds of formula (I) and/or their salts.
  • the application rate can vary within wide limits.
  • the total amount of compounds of 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 application.
  • 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. This applies both to pre-emergence and post-emergence application.
  • stem shortener can be carried out 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 an option, which includes various seed dressing and coating techniques.
  • the application rate depends on the individual techniques and can be determined in preliminary trials.
  • 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, phytoene desaturase, photosystem I, photosystem II or protoporphyrinogen oxidase can be used, 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. of Chemistry, 2021 and literature cited therein.
  • Known herbicides or plant growth regulators that can be combined with compounds of the general formula (I) include, for example, the following active ingredients (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.
  • 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- l,2-oxazolidin-3-one, 2-(2,5-dichlorobenzyl)-4,4-dimethyl-l,2-oxazolidin-3-one, dichlorprop, dichlorprop-butotyl, dichlorprop-dimethylammonium, dichlorprop-etexyl, dichlorpropethylammonium, dich
  • growth regulators and plant stimulants as mixing partners are:
  • Abscisic acid and related analogues [e.g. (2Z,4E)-5-[6-ethynyl-l-hydroxy-2,6-dimethyl-4-oxocyclohex-2-en-l-yl]-3-methylpenta-2,4-dienoic acid, methyl-(2Z,4E)-5-[6-ethynyl-l-hydroxy-2,6-dimethyl-4-oxocyclohex-2-en-l-yl]-3-methylpenta-2,4-dienoate, (2Z,4E)-3-ethyl-5-(l-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-l-yl)penta-2,4-dienoic acid, (2E,4E)-5-(l-hydroxy-2,6,6-trimethyl-4- oxocyclohex-2-en-l-yl)-3-(trifluoromethyl)penta-2,4-dieno
  • COs differ from LCOs in that they lack the fatty acid side chain characteristic of LCOs.
  • COs sometimes referred to as N-acetylchitooligosaccharides, are also composed of GlcNAc units, but have side chains that distinguish them from chitin molecules [(CsHoNOsln, CAS No. 1398-61-4] and chitosan molecules [(QHi iNO-ifi, CAS No.
  • chitin-like compounds chlormequat chloride, cloprop, cyclanilide, 3-(cycloprop-l-enyl)propionic acid, l-[2-(4-Cyano-3,5-dicyclopropylphenyl)acetamido]cyclohexanecarboxylic acid, l-[2-(4-Cyano-3-cyclopropylphenyl)acetamido]cyclohexanecarboxylic acid, 1-Cyclopropenylmethanol, Daminozide, Dazomet, Dazomet sodium, n-Decanol, Dikegulac, Dikegulac sodium, Endothal, Endothal di-potassium, di-sodium, and mono(N,N-dimethylalkylammonium), Ethephon, l-Ethylcyclopropene, Flumetralin, Flurenol, Flurenol butyl, Flurenol methyl
  • LCO lipochitooligosaccharides
  • Nod or Nod factors lipochitooligosaccharides
  • Myc factors consist of an oligosaccharide backbone of ß-l,4-linked A-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 acid hydrazide, mepiquat chloride, mepiquat pentaborate, 1-methylcyclopropene, 3-methylcyclopropene, Methoxyvinylglycine (MVG), 3'-methylabscisic acid, l-(4-methylphenyl)-N-(2-oxo-1-propyl-1,2,3,4-tetrahydroquinolin-6-yl)methanesulfonamide and related substituted (tetrahydroquinolin-6-yl)methanesulfonamides, (3E,3aR,8ßS)-3-( ⁇ [(2R)-4-methyl-5-oxo
  • n A is a natural number from 0 to 5, preferably 0 to 3;
  • R A 1 is halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, nitro or (C 1 -C 4 )-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;
  • RA 2 is ORA 3 , SRA 3 or NRA 3 RA 4 or a saturated or
  • 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;
  • RB 2 is ORB 3 , SRB 3 or NRB 3 RB 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 (C1-C4)-alkyl, (C1-C4)-alkoxy or optionally substituted phenyl, preferably a radical of the formula ORB 3 , NHRB 4 or N(CH3)2, in particular of the formula ORB 3 ;
  • RB 3 is halogen, (C1-C4)-alkyl, (C1-
  • 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 identical or different and are 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, dioxolanyl-(C
  • X D 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 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;
  • 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 0 or 1,
  • 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.
  • Active substances 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 metolachlor damage, "Fluxofenim” (l-(4-chlorophenyl)-2,2,2-trifluoro-l-ethanone-O-(l,3-dioxolan-2-ylmethyl)-oxime) (Sl l-2), which is known as a seed dressing safener for millet against metolachlor damage, and "Cyometrinil” or “CGA-43089” ((Z)-cyanomethoxyimino(phenyl)acetonitrile) (Sl l-3), which is known as a seed dressing safener for millet against metolach
  • Active ingredients from the class of isothiochromanones 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.
  • Active substances which, in addition to a herbicidal effect against harmful plants, also have a safener effect on crops such as rice, such as
  • 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.
  • Biological examples The following abbreviations are used for the cultivated and harmful plants listed in the following tables: ABUTH: Abutilon theophrasti
  • BRSNW Brassica napus
  • ECHCG Echinochloa crus-galli
  • KCHSC Kochia scoparia
  • MATIN Matricaria inodora
  • ORYZA Oryza sativa
  • PHPBU Pharbitis purpurea
  • VERPE Veronica persica
  • VIOTR Viola tricolor
  • TRZAS Triticum aestivum
  • the emulsion was sprayed onto the green parts of the plants with a 0.5% additive at a water application rate equivalent to 600 l/ha. After approximately three weeks of the test plants standing in the greenhouse under optimal growth conditions, the effectiveness of the preparations was visually assessed in comparison to untreated controls. For example, 100% effectiveness means plants died, 0% effectiveness means the same as the control plants.
  • Tables A1 to A1 1 show the effects of selected compounds of the general formula (I) according to Table 1 on various weeds and an application rate corresponding to 20 g/ha and lower, obtained according to the previously mentioned test procedure.
  • Table Ala Postemergence effect at 1.25 g/ha against ABUTH in %
  • Table A2c Post-emergence effect at 20g/ha against ALOMY in %
  • Table A3a Post-emergence effect at 1.25g/ha against DIGSA in %
  • Table A4a Post-emergence effect at 1.25g/ha against LOLRI in %
  • Table A4b Post-emergence effect at 5g/ha against LOLRI in %
  • Table A5a Post-emergence effect at 1.25g/ha against MATIN in %
  • Table A5b Post-emergence effect at 5g/ha against MATIN in %
  • Table A5c Post-emergence effect at 20g/ha against MATIN in %
  • Table A6a Post-emergence effect at 1.25g/ha against PHBPU in %
  • Table A7a Post-emergence effect at 1.25g/ha against POLCO in %
  • Table A7b Post-emergence effect at 5g/ha against POLCO in %
  • Table A7c Post-emergence effect at 20g/ha against POLCO in %
  • Table A8a Post-emergence effect at 1.25g/ha against SETVI in %
  • Table A8b Post-emergence effect at 5g/ha against SETVI in %
  • Table A8c Post-emergence effect at 20g/ha against SETVI in %
  • Table A9a Post-emergence effect at 1.25g/ha against VERPE in %
  • Table A9b Post-emergence effect at 5g/ha against VERPE in %
  • Table A9c Post-emergence effect at 20g/ha against VERPE in %
  • Table A 10c Post-emergence effect at 20g/ha against VIOTR in %
  • Table A1 la Post-emergence effect at 1.25g/ha against KCHSC in %
  • the emulsion was sprayed onto the green parts of the plants with a 0.5% additive at a water application rate equivalent to 600 l/ha. After approximately three weeks of the test plants standing in the greenhouse under optimal growth conditions, the effectiveness of the preparations was visually assessed in comparison to untreated controls. For example, 100% effectiveness means plants died, 0% effectiveness means the same as the control plants.
  • Tables B1 to B2 show the effects of selected compounds of general formula (I) according to Table 1 on various crops and at an application rate corresponding to 5 g/ha and lower, which were obtained according to the test procedure mentioned above.
  • Table Bl Post-emergence effect at 1.25g/ha against ZEAMX in %

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  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Wood Science & Technology (AREA)
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  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
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Abstract

La présente invention concerne des uraciles d'acide N-benzoïque substitués de formule générale (I) et des sels de ceux-ci, les radicaux dans la formule générale (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 graminées dans des cultures de plantes utiles, et/ou en tant que régulateurs de croissance de plantes pour influencer la croissance de cultures de plantes utiles.
PCT/EP2024/081827 2023-11-15 2024-11-11 Uraciles d'acide n-benzoïque substitués et leurs sels, et leur utilisation en tant que substances actives herbicides Pending WO2025103929A1 (fr)

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