WO2023161172A1 - 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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WO2023161172A1
WO2023161172A1 PCT/EP2023/054143 EP2023054143W WO2023161172A1 WO 2023161172 A1 WO2023161172 A1 WO 2023161172A1 EP 2023054143 W EP2023054143 W EP 2023054143W WO 2023161172 A1 WO2023161172 A1 WO 2023161172A1
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alkyl
aryl
alkoxy
heteroaryl
bis
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PCT/EP2023/054143
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German (de)
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Hendrik Helmke
Jens Frackenpohl
Ines Heinemann
Harald Jakobi
Elmar Gatzweiler
Birgit BOLLENBACH-WAHL
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Bayer Aktiengesellschaft
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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
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • 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
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
    • 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
    • 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
    • C07D401/14—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 three or more hetero rings
    • 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
    • C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
    • C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
    • C07D453/06—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing isoquinuclidine ring 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
    • C07D493/04—Ortho-condensed systems

Definitions

  • Substituted N-benzoic acid uracils and their salts and their use as herbicidally active compounds relates to the technical field of crop protection agents, in particular that of herbicides for the selective control of weeds and weed grasses in crops of useful plants. Specifically, this invention relates to substituted N-benzoic acid uracils and their salts, processes for their preparation and their use as herbicides, in particular for controlling weeds and/or weed grasses in crops of useful plants and/or as plant growth regulators for influencing the growth of crops of useful plants.
  • Previously known crop protection agents for the selective control of harmful plants in crops of useful plants or active ingredients for controlling unwanted plant growth sometimes have disadvantages when they are used, be it that they (a) have no or insufficient herbicidal action against certain harmful plants, (b) too little Spectrum of harmful plants that can be controlled with an active ingredient, (c) have insufficient selectivity in crops of useful plants and/or (d) have a toxicologically unfavorable profile.
  • some active compounds which can be used as plant growth regulators in some useful plants lead to undesirably reduced crop yields in other useful plants or are not compatible with the crop plant or only in a narrow application rate range.
  • the known aryluracils have a number of gaps in their effectiveness, in particular against monocotyledonous weeds.
  • a number of herbicidal active ingredient combinations based on N-linked aryluracils are also known (cf.
  • N-aryluracils with optionally further substituted lactic acid groups can also be used as herbicidal active ingredients (cf. JP2000/302764, JP2001/172265, US Pat. No. 6,403,534, EP408382). It is also known that N-aryluracils with special, optionally further substituted, thiolactic acid groups also exhibit herbicidal effects (cf. WO2010/038953, KR2011110420).
  • 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).
  • WO88/10254 A1 describes and includes special N-benzoic acid uracils with bromine substituents in the benzoic acid unit which are para to the uracil group.
  • N-benzoic acid uracils of the general formula (I) substituted with them or their salts wherein R 1 is hydrogen, methyl, R 2 is hydrogen, halogen, trifluoromethyl, R 3 is NR 7 R 15 , (C 1 -C 8 )-alkyl, R 4 is bromo, iodo, G is a radical the following formula is, Q is hydroxy or a radical of the formulas below R 5 and R 6 are independently hydrogen, (C 1 -C 8 )alkyl, (C 1 -C 8 )haloalkyl, (C 1 -C 8 )alkoxy-(C 1 -C 8 )- alkyl, or R 5 and R 6 with the carbon atom to which they are attached form a fully saturated monocyclic 3- to 7-membered carbocycle, R 8 is hydrogen, (C 1 -C 8 )-alkyl, (C 1 -C 8 )haloalkyl, aryl,
  • the compounds of general formula (I) can be synthesized by addition of a suitable inorganic or organic acid, such as mineral acids such as HCl, HBr, H 2 SO 4 , H 3 PO 4 or HNO 3 , or organic acids, eg. B. carboxylic acids such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid or sulfonic acids such as p-toluenesulfonic acid to a basic group such as amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino. These salts then contain the conjugate base of the acid as an anion.
  • a suitable inorganic or organic acid such as mineral acids such as HCl, HBr, H 2 SO 4 , H 3 PO 4 or HNO 3
  • organic acids eg. B.
  • carboxylic acids such as formic acid, acetic acid, propionic acid, oxalic acid
  • Suitable substituents which are in deprotonated form can form inner salts with groups which in turn can be protonated, such as amino groups. Salt formation can also take place by 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 and ammonium, alkali metal 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 an agriculturally suitable cation, for example metal salts, in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or else 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.
  • an agriculturally suitable cation for example metal salts, in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or else 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 al
  • 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.
  • a preferred subject of the invention are compounds of the general formula (I) in which R 1 is hydrogen, R 2 is hydrogen, fluorine, chlorine, bromine or iodine, R 3 is NR 7 R 15 , (C 1 -C 7 )-alkyl , R 4 is bromo, iodo, G is a radical of the formula below stands, Q stands for hydroxy or a radical of the following formulas, R 5 and R 6 are independently hydrogen, (C 1 -C 7 )-alkyl, or R 5 and R 6 with the carbon atom to which they are attached form a fully saturated monocyclic 3- to 6-membered carbocycle, R 8 is hydrogen, (C 1 -C 7 )alkyl, (C 1 -C 7 )haloalkyl, aryl, aryl(C 1 -C 7 )alkyl, heteroaryl, (C 2 -C 7 )alkynyl , (C 2 -C 7 )alkenyl, C(O)
  • C 7 )alkyl (C 1 -C 7 )alkylthio(C 1 -C 7 )alkyl, (C 1 -C 7 )haloalkylthio(C 1 -C 7 )alkyl, (C 1 -C 7 )-Alkoxy(C 1 -C 7 )haloalkyl, aryl, aryl(C 1 -C 7 )alkyl, heteroaryl, heteroaryl(C 1 -C 7 )alkyl, (C 3 -C 7 ) -Cycloalkyl-(C 1 -C 7 )alkyl, (C 4 -C 10 )cycloalkenyl-(C 1 -C 7 )alkyl, C(O)R 13 , SO 2 R 14 , heterocyclyl, (C 1 -C 7 )-Alkoxycarbonyl, bis[(C 1 -C 7 )alkyl]aminocarbonyl-(C 1
  • a particularly preferred subject of the invention are compounds of the general formula (I) in which R 1 is hydrogen, R 2 is hydrogen, fluorine, chlorine or bromine, R 3 is amino, (C 1 -C 6 )-alkyl, R 4 is bromo, iodo, G is a radical of the following formula stands, Q is hydroxy or a radical of the formulas below R 5 and R 6 are independently hydrogen, (C 1 -C 6 )alkyl, R 5 and R 6 with the carbon atom to which they are attached form a fully saturated monocyclic 3- to 6-membered carbocycle , R 8 is hydrogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, aryl, aryl-(C 1 -C 6 )-alkyl, heteroaryl, (C 2 -C 6 )- alkynyl, (C 2 -C 6 )alkenyl, C(O)R 13 , C(O)OR 13
  • a very particularly preferred subject of the invention are compounds of the general formula (I) in which R 1 is hydrogen, R 2 is hydrogen, fluorine or chlorine, R 3 is amino, methyl, ethyl, prop-1-yl, 1-methylethyl, but -1-yl, 1-methylpropyl, 2-methylpropyl, R 4 is bromo, iodo, G is a radical of the following formula, R 5 and R 6 are independently hydrogen, methyl, ethyl, prop-1-yl, 1-methylethyl, but-1-yl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1- Methylbutyl, 2-Methylbutyl, 3-Methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n- hexyl, 1-methylpentyl, 2-methyl
  • a particularly preferred subject of the invention are compounds of the general formula (I) in which R 1 represents hydrogen, R 2 represents hydrogen, fluorine, chlorine, R 3 represents amino, methyl, R 4 represents bromine, iodine, G for a radical of the following formula R 5 and R 6 are independently hydrogen, methyl, ethyl, preferably methyl, or R 5 and R 6 with the carbon atom to which they are attached form a fully saturated monocyclic 3- to 6-membered carbocycle and Q stands for one of the groups Q-1 to Q-500 specifically mentioned above.
  • preferred subject matter of the invention are compounds of the general formula (I) in which R 1 is hydrogen, R 2 is hydrogen, fluorine, chlorine, R 3 is amino, methyl, R 4 is bromine, iodine, G is one remainder of the formula below, R 5 and R 6 are methyl and Q is one of the groups Q-1, Q-2, Q-23, Q-24, Q-26, Q-31, Q-71, Q-72, Q-115, Q-127, Q-152, Q-176, Q-231, Q-237, Q-286, Q-301, Q-302, Q-441, Q- 442, Q-454, Q-472, Q-481, Q-489, Q-490, Q-491, Q-496, Q-499, Q-500.
  • radicals given above in general or in preferred ranges apply both to the end products of the formula (I) and correspondingly to the starting materials or intermediates required in each case for the preparation. These radical definitions can be combined with one another as desired, ie also between the specified preferred ranges. With regard to the compounds according to the invention, the designations used above and below are explained.
  • heterocyclyl C 1 -C 8 alkyl or R 13 O (O) C - (C 1 -C 8 ) alkyl
  • alkyl therefore also stands for an alkylene group.
  • alkylsulfonyl on its own or as part of a chemical group—is straight-chain or branched alkylsulfonyl, preferably having 1 to 8 or 1 to 6 carbon atoms, eg (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-di
  • heteroarylsulfonyl represents optionally substituted pyridylsulfonyl, pyrimidinylsulfonyl, pyrazinylsulfonyl or optionally substituted polycyclic heteroarylsulfonyl, here in particular optionally substituted quinolinylsulfonyl, for example substituted by fluoro, chloro, bromo, iodo, cyano, nitro, alkyl, haloalkyl, haloalkoxy, amino, alkylamino, alkylcarbonylamino, dialkylamino, or alkoxy groups.
  • alkylthio on its own or as part of a chemical group—is straight-chain or branched S-alkyl, preferably having 1 to 8 or 1 to 6 carbon atoms, such as (C 1 -C 10 )-, (C 1 - C 6 )- or (C 1 -C 4 )-alkylthio, for example (but not limited to) (C 1 -C 6 )-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-ethylpropy
  • 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 )-alkylsulphinyl such as methylsulphinyl, ethylsulphinyl, propylsulphinyl, 1-methylethylsulphinyl, butylsulphinyl, 1-methylpropylsulphinyl, 2-methylpropylsulphinyl, 1,1-dimethylethylsulphinyl, pentylsulphinyl, 1-methylbutylsulphinyl, 2-Methylbutylsulphinyl, 3-Methylbutylsulphinyl, 1,1-dimethylpropylsulphinyl, 1,2-dimethylpropylsulphinyl, 2,2-dimethylpropylsulphinyl, 1-ethylpropylsulphinyl, hexylsulphinyl, 1-methylpentylsulphinyl, 2-methylpentylsulphinyl,
  • Alkoxy means an alkyl radical bonded through an oxygen atom, e.g. B.
  • 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 an oxygen-bonded cycloalkyl radical and cycloalkenyloxy means an oxygen-bonded cycloalkenyl radical.
  • the number of carbon atoms refers to the alkyl radical in the alkylcarbonyl group.
  • alkenylcarbonyl and “alkynylcarbonyl”, unless otherwise defined elsewhere, stand for alkenyl or alkynyl radicals which are bonded to the skeleton via -C( O)-, such as (C 2 -C 10 )- , (C 2 -C 6 )- or (C 2 -C 4 )-alkenylcarbonyl or (C 2 -C 10 )-, (C 2 -C 6 )- or (C 2 -C 4 )- alkynylcarbonyl.
  • the number of carbon atoms refers to the alkenyl or alkynyl radical in the alkenyl or alkynylcarbonyl group.
  • the number of carbon atoms refers to the alkyl radical in the alkoxycarbonyl group.
  • alkenyloxycarbonyl and “alkynyloxycarbonyl”, unless otherwise defined elsewhere, stand for alkenyl or alkynyl radicals which are bonded to the skeleton via -OC( O)-, such as (C 2 -C 10 )-. , (C 2 -C 6 )- or (C 2 -C 4 )-alkenyloxycarbonyl or (C 3 -C 10 )-, (C 3 -C 6 )- or (C 3 -C 4 )- alkynyloxycarbonyl.
  • the number of carbon atoms refers to the alkenyl or alkynyl radical in the alkene or alkynyloxycarbonyl group.
  • the number of carbon atoms refers to the alkyl radical in the alkylcarbonyloxy group.
  • the number of carbon atoms refers to the alkenyl or alkynyl radical in the alkenyl or alkynylcarbonyloxy group.
  • C(O)R 13 , C(O)OR 13 , OC(O)NR 11 R 12 , or C(O)NR 11 R 12 the short form O in brackets stands for a via a double bond to the adjacent carbon atom bonded oxygen atom.
  • OC(S)OR 13 , OC(S)SR 14 , OC(S)NR 11 R 12 the short form S given in brackets 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 with 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 includes polycyclic systems such as tetrahydronaphthyl, indenyl, indanyl, fluorenyl, biphenylyl, where the binding site is on the aromatic system. Systematically, “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, heteroaryloxy, alkoxyalkoxy, alkynylalkoxy, alkenyloxy, bis-alkylaminoalkoxy, tris-[alkyl]silyl, bis-[alkyl]arylsilyl, bis-[alkyl]alkylsilyl, tris-[
  • heterocyclyl radical or heterocyclic ring is optionally substituted, it may be fused to other carbocyclic or heterocyclic rings.
  • polycyclic systems are also included, 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 included, such as 1-oxa-5-azaspiro[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 not two oxygen atoms should 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-pyrrole-2- or 3 -yl, 2,3-dihydro-1H-pyrrol-1- or 2- or 3- or 4- or 5-yl; 2,5-dihydro-1H-pyrrole-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-t
  • 3-ring and 4-ring heterocycles are 1- or 2-aziridinyl, oxiranyl, thiiranyl, 1- or 2- or 3-azetidinyl, 2- or 3-oxetanyl, 2- or 3-thietanyl, 1,3 -dioxetan-2-yl.
  • heterocyclyl are a partially or fully hydrogenated heterocyclic radical having 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-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-tetrahydropyridazin-1- or
  • heterocyclyl are a partially or fully hydrogenated heterocyclic radical with 3 heteroatoms from the group N, O and S, such as 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-dioxazepine-2- or 3- or 5- or 6- or 7-yl; 2,3-dihydro-5H-1,4,2-dioxazepine-2- or 3- or 5- or 6-
  • heterocycles listed above are preferably substituted, for example, by 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, Arylalkoxycarbonyl, Arylalkoxycarbonylalkyl, Alkynyl, Alkynylalkyl, Alkylalkynyl, Tris-alkylsilylalkynyl, Nitro, Amin
  • Suitable substituents for a substituted heterocyclic radical are the substituents mentioned 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. with N and S, and then form, for example, the divalent groups N(O), S(O) (also short SO) and S(O) 2 (also short SO 2 ) in the heterocyclic ring.
  • N(O), S(O) (also short SO) and S(O) 2 (also short SO 2 ) in the heterocyclic ring.
  • -N(O)- and -S(O)- groups both enantiomers are included.
  • heteroaryl stands for heteroaromatic compounds, i. H. completely unsaturated aromatic heterocyclic compounds, preferably 5- to 7-membered rings having 1 to 4, preferably 1 or 2, identical or different heteroatoms, preferably O, S or N.
  • heteroaryls are 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-yl, 1H-pyrrol-1-
  • heteroaryl groups according to the invention can also be substituted with 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 benzo-fused or multiply fused heteroaromatics.
  • fused heteroaromatic systems such as benzo-fused or multiply fused heteroaromatics.
  • Preferred are, for example, quinolines (e.g. quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl ); isoquinolines (e.g.
  • 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-benzofuran-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, 1
  • halogen means, for example, fluorine, chlorine, bromine or iodine.
  • halo means, for example, fluoro, chloro, bromo or iodo.
  • 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.
  • bis also includes the combination of different alkyl radicals, e.g. methyl(ethyl) or ethyl(methyl).
  • "Haloalkyl”, "-alkenyl” and “alkynyl” mean alkyl, alkenyl or alkynyl, e.g.
  • perhaloalkyl such as e.g. B.CCl 3 , CCIF 2 , CFCl 2 , CF 2 CCIF 2 , CF 2 CCIFCF 3 ; polyhaloalkyl such as e.g. B.CH 2 CHFCl, CF 2 CCFH, CF 2 CBrFH, CH 2 CF 3 ;
  • perhaloalkyl also includes the term “perfluoroalkyl”.
  • Partially fluorinated alkyl means a straight-chain or branched, saturated hydrocarbon which is mono- or poly-substituted by fluorine, where the corresponding fluorine atoms are as Substituents may be on one or more different carbon atoms of the straight or branched hydrocarbon chain, such as. B.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 hydrocarbon substituted by various halogen atoms having at least one fluorine atom, with all other optionally present halogen atoms being selected from the group consisting of fluorine, chlorine or bromine, iodine.
  • 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 full substitution of the straight or branched chain with halogen involving at least one fluorine atom.
  • haloalkoxy is OCF 3 , OCHF 2 , OH 2 F, OCF 2 CF 3 , OH 2 CF 3 and OCH 2 CH 2 Cl;
  • haloalkenyl and other radicals substituted by halogen are OCF 3 , OCHF 2 , OH 2 F, OCF 2 CF 3 , OH 2 CF 3 and OCH 2 CH 2 Cl;
  • (C 1 -C 4 )-Alkyl means an abbreviation for straight-chain or branched alkyl with one to 4 carbon atoms corresponding to the range specified for carbon atoms, i.e. includes the radicals methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2 -methylpropyl or tert-butyl.
  • hydrocarbon radicals such as alkyl, alkenyl and alkynyl radicals, also in compound radicals, which preferably have lower carbon structures, for example with 1 to 6 carbon atoms or, in the case of unsaturated groups, with 2 to 6 carbon atoms e.g., methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls such as n-hexyl, i-hexyl and 1,3-dimethylbutyl, 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, where at least one double bond or triple bond is present.
  • radicals having a double bond or triple bond Preference is given to radicals having a 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 cumulative double bonds, such as for example allenyl (1,2-propadienyl), 1,2-butadienyl and 1,2,3-pentatrienyl.
  • Alkenyl means, for example, vinyl, which can optionally be substituted by further alkyl radicals, for example (but not limited to) (C 2 -C 6 )-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-propenyl, 1,2-dimethyl
  • 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-pentene-1-in-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-methyl-3 -p
  • cycloalkyl means a carbocyclic, saturated ring system preferably having 3-8 ring carbon atoms, e.g. cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, which is optionally further substituted, preferably by hydrogen, alkyl, alkoxy, cyano, nitro, alkylthio , haloalkylthio, halogen, alkenyl, alkynyl, haloalkyl, amino, alkylamino, bisalkylamino, alcocycarbonyl, hydroxycarbonyl, arylalkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, cycloalkylaminocarbonyl.
  • cyclic Systems with substituents, with substituents having a double bond on the cycloalkyl radical, e.g. an alkylidene group such as methylidene 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,
  • 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 "means a carbocyclic, non-aromatic, partially unsaturated ring system preferably having 4-8 carbon atoms, e.g.
  • C 1 -C 10 )-Alkylidene means the radical of a straight-chain or branched open-chain hydrocarbon radical which is bonded via a double bond.
  • Cycloalkylidene means a carbocyclic radical bonded via a double bond.
  • Cycloalkylalkyloxy means an oxygen-bonded cycloalkylalkyl radical and "arylalkyloxy” means an oxygen-bonded arylalkyl radical.
  • Alkoxyalkyl means an alkoxy radical bonded through an alkyl group and "alkoxyalkoxy” means an alkoxyalkyl radical bonded through an oxygen atom, such as (but not limited to) methoxymethoxy, methoxyethoxy, ethoxyethoxy, methoxy-n-propyloxy.
  • Alkylthioalkyl means an alkylthio radical bonded through an alkyl group and “alkylthioalkylthio” means an alkylthioalkyl radical bonded through an oxygen atom.
  • Arylalkoxyalkyl means an aryloxy radical bonded through an alkyl group and “heteroaryloxyalkyl” means a heteroaryloxy radical bonded through an alkyl group.
  • Haloalkoxyalkyl means a linked haloalkoxy radical and "haloalkylthioalkyl” means a haloalkylthio radical linked through an alkyl group.
  • Arylalkyl means an aryl radical bonded through an alkyl group
  • heteroarylalkyl means a heteroaryl radical bonded through an alkyl group
  • heterocyclylalkyl means a heterocyclyl radical bonded through an alkyl group.
  • Cycloalkylalkyl represents a cycloalkyl radical bonded via an alkyl group, e.g. B.
  • Arylalkenyl means an aryl radical bonded through an alkenyl group
  • heteroarylalkenyl means a heteroaryl radical bonded through an alkenyl group
  • heterocyclylalkenyl means a heterocyclyl radical bonded through an alkenyl group
  • Arylalkynyl means an aryl radical bonded through an alkynyl group
  • heteroarylalkynyl means a heteroaryl radical bonded through an alkynyl group
  • heterocyclylalkynyl means a heterocyclyl radical bonded through an alkynyl group
  • haloalkylthio on its own or as part of a chemical group—is straight-chain or branched S-haloalkyl, preferably having 1 to 8 or 1 to 6 carbon atoms, such as (C 1 -C 8th )-, (C 1 -C 6 )- or (C 1 -C 4 )-haloalkylthio such as (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 denote identical or different halogen atoms, such as e.g. B. F, Cl and Br, or by haloalkyl, such as. B. trifluoromethyl or difluoromethyl partially or fully substituted cycloalkyl or cycloalkenyl, e.g.
  • Trialkylsilylalkynyl represents a trialkylsilyl radical bonded through an alkynyl group. If the compounds can form tautomers by hydrogen shift, which would not be formally covered by the formula (I) structurally, these tautomers are nevertheless included in the definition of the compounds of the formula (I) according to the invention, unless a specific tautomer is the subject of consideration. For example, many carbonyl compounds can exist in both the keto form and the enol form, both forms being encompassed by the definition of the compound of formula (I). Depending on the type and linkage of the substituents, the compounds of the general formula (I) can be present as stereoisomers.
  • stereoisomers defined by their specific spatial form such as enantiomers, diastereomers, Z and E isomers are all encompassed by the formula (I). If, for example, one or more alkenyl groups are present, diastereomers (Z and E isomers) can occur. For example, if one or more asymmetric carbon atoms are present, enantiomers and diastereomers can occur.
  • Stereoisomers can be obtained from the mixtures obtained in the preparation by customary separation methods. The 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 specimens for biological testing.
  • stereoisomers can be prepared selectively by using stereoselective reactions using optically active starting materials and/or auxiliaries.
  • the invention thus also relates to all stereoisomers which are covered by the general formula (I) but are not specified with their specific stereo form, and mixtures thereof. If the compounds are obtained as solids, they can also be purified by recrystallization or digestion. If individual compounds (I) are not satisfactorily accessible by the routes described below, they can be prepared by derivatizing other compounds (I). Suitable methods for isolating, purifying and separating stereoisomers of compounds of the general formula (I) are methods which are generally known to the person skilled in the art from analogous cases, e.g.
  • nitrobenzoic acid esters (IV) can be converted by means of 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
  • 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
  • suitable bases e.g. diisopropylethylamine, triethylamine
  • a suitable polar aprotic solvent e.g. dichloromethane, chloroform
  • the 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)) is used.
  • a suitable polar aprotic solvent e.g. dichloromethane (DCM), chloroform, N,N-dimethylacetamide (DMA) or N ,N-dimethylformamide (DMF)
  • DCM dichloromethane
  • DMA N,N-dimethylacetamide
  • DMF N ,N-dimethylformamide
  • the N-amino-N'-benzoic acid uracil (Id) is synthesized by N-amination starting from the uracil (VIII) described above, as shown in Scheme 2 below.
  • the N-amination is carried
  • 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.
  • EDC 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide
  • HATU O-(7 -Azabenzotriazol-1-yl)-N,N,N′,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)) is used.
  • a suitable polar aprotic solvent e.g. dichloromethane (DCM), chloroform, N,N-dimethylacetamide (DMA) or N ,N-dimethylformamide (DMF)
  • I.4-1 1-(2-Methoxyethoxy)-2-methyl-1-oxopropan-2-yl-5-[3-amino-4-(difluoromethyl)-2,6-dioxo-3,6 -dihydropyrimidin-1(2H)-yl]-2-bromo-4-fluorobenzoate 1-(Allyloxy)-2-methyl-1-oxopropan-2-yl-2-bromo-5-[2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl] -4-fluorobenzoate (1280 mg, 2.44 mmol) was dissolved in abs.
  • Methyl 3-amino-4-fluorobenzoate 60 g, 352.94 mmol was dissolved in acetic acid (600 mL), and sodium periodate (75 g, 352.94 mmol) and sodium chloride (40 g, 705.88 mmol) were added. After stirring at room temperature for 5 min, a solution of potassium iodide (58.5 g, 352.94 mmol) in water (180 mL) was slowly added. The resulting reaction mixture was then stirred at room temperature for 24 hours, checking the progress of the reaction by thin layer chromatography (30% EtOAc in petroleum ether (Rf: 0.5).
  • the resulting reaction mixture was stirred at room temperature for 4 h, then added to ice-water (1.5 L) and stirred at room temperature for 30 minutes. After addition of ethyl acetate, it was thoroughly extracted several times with ethyl acetate. The combined organic phases were washed with sat. Washed NaCl solution, dried over sodium sulfate, filtered off and concentrated under reduced pressure.
  • the resulting reaction mixture was then stirred at 10-20 °C for 4 h, then treated with water (100 mL) and then washed with sat.
  • Sodium bicarbonate solution brought to a pH of about 8.
  • dichloromethane was added and, after phase separation, the aqueous phase was adjusted to a pH of 4-5 using 2N HCl and thoroughly extracted several times with dichloromethane.
  • the combined organic phases were washed with sat. Washed NaCl solution, dried over sodium sulfate, filtered off and concentrated under reduced pressure.
  • Tetrahydrofuran 400 mL dissolved, cooled to a temperature of 0 °C and NaH (60% in mineral oil, 1.11 g, 49.2 mmol) was carefully added in portions. After stirring at 0° C. for 30 minutes, O-diphenylphosphinylhydroxylamine (22.9 g, 98.41 mmol) was added in portions. Thereafter, the resulting reaction mixture was stirred at a temperature of 40° C. for 6 h and then treated with ice water (500 mL). After addition of ethyl acetate and a first extraction, the aqueous phase was extracted several times with ethyl acetate.
  • the resulting reaction mixture was then stirred at room temperature for 3 h, then treated with water (100 mL) and then washed with sat.
  • Sodium bicarbonate solution brought to a pH of about 8.
  • dichloromethane was added and, after phase separation, the aqueous phase was adjusted to a pH of 4-5 using 2N HCl and thoroughly extracted several times with dichloromethane.
  • the combined organic phases were washed with sat. Washed NaCl solution, dried over sodium sulfate, filtered off and concentrated under reduced pressure.
  • the reaction mixture was separated from the aqueous phase using a separator cartridge and, after collecting the organic phase, the solvent was removed in vacuo.
  • the crude product obtained was purified by column chromatography to give 1-(cyanomethoxy)-2-methyl-1-oxopropan-2-yl-2-bromo-4-fluoro-5-[3-amino-2,6-dioxo-4-(trifluoromethyl )-3,6-dihydropyrimidin-1(2H)-yl]benzoate (51 mg, 57% of theory) as a colorless solid.
  • Table I.1 Preferred compounds of the formula (I.1) are the compounds I.1-1 to I.1-500, in which the radical Q has the meanings of Table 1 given in the respective line.
  • the compounds I.1-1 to I.1-500 in Table I.1 are thus defined by the meaning of the respective entries No.1 to 500 for Q in Table 1.
  • Table 1: Table I.2: Preferred compounds of the formula (I.2) are the compounds I.2-1 to I.2-500, in which the radical Q has the meanings of Table 1 given in the respective line.
  • the compounds I.2-1 to I.2-500 in 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 the formula (I.3) are the compounds I.3-1 to I.3-500, in which the radical Q has the meanings of Table 1 given in the respective line.
  • the compounds I.3-1 to I.3-500 in Table I.3 are thus defined by the meaning of the respective entries No.1 to 500 for Q in Table 1.
  • Table I.4: Preferred compounds of the formula (I.4) are the compounds I.4-1 to I.4-500, in which the radical Q has the meanings of Table 1 given in the respective line.
  • the compounds I.4-1 to I.4-500 in Table I.4 are thus defined by the meaning of the respective entries No.1 to 500 for Q in Table 1.
  • Table I.5 Preferred compounds of the formula (I.5) are the compounds I.5-1 to I.5-500, in which the radical Q has the meanings of Table 1 given in the respective line.
  • the compounds I.5-1 to I.5-500 in Table I.5 are thus defined by the meaning of the respective entries No.1 to 500 for Q in Table 1.
  • Table I.6 Preferred compounds of the formula (I.6) are the compounds I.6-1 to I.6-500, in which the radical Q has the meanings of Table 1 given in the respective line.
  • the compounds I.6-1 to I.6-500 in Table I.6 are thus defined by the meaning of the respective entries No.1 to 500 for Q in Table 1.
  • Table I.7: Preferred compounds of the formula (I.7) are the compounds I.7-1 to I.7-500, in which the radical Q has the meanings of Table 1 given in the respective line.
  • the compounds I.7-1 to I.7-500 in Table I.7 are thus defined by the meaning of the respective entries No.1 to 500 for Q in Table 1.
  • Table I.8: Preferred compounds of the formula (I.8) are the compounds I.8-1 to I.8-500, in which the radical Q has the meanings of Table 1 given in the respective line.
  • the compounds I.8-1 to I.8-500 in Table I.8 are thus defined by the meaning of the respective entries No.1 to 500 for Q in Table 1.
  • Table I.9: Preferred compounds of the formula (I.9) are the compounds I.9-1 to I.9-500, in which the radical Q has the meanings of Table 1 given in the respective line.
  • the compounds I.9-1 to I.9-500 in Table I.9 are thus defined by the meaning of the respective entries No.1 to 500 for Q in Table 1.
  • Table I.10 Preferred compounds of the formula (I.10) are the compounds I.10-1 to I.10-500, in which the radical Q has the meanings of Table 1 given in the respective line.
  • the compounds I.10-1 to I.10-500 in Table I.10 are thus defined by the meaning of the respective entries No.1 to 500 for Q in Table 1.
  • Table I.11 Preferred compounds of the formula (I.11) are the compounds I.11-1 to I.11-500, in which the radical Q has the meanings of Table 1 given in the respective line.
  • the compounds I.11-1 to I.11-500 in Table I.11 are thus defined by the meaning of the respective entries No.1 to 500 for Q in Table 1.
  • Table I.12 Preferred compounds of the formula (I.12) are the compounds I.12-1 to I.12-500, in which the radical Q has the meanings of Table 1 given in the respective line.
  • the compounds I.12-1 to I.12-500 in Table I.12 are thus defined by the meaning of the respective entries No.1 to 500 for Q in Table 1.
  • Table I.13 Preferred compounds of the formula (I.13) are the compounds I.13-1 to I.13-500, in which the radical Q has the meanings of Table 1 given in the respective line.
  • the compounds I.13-1 to I.13-500 in Table I.13 are thus defined by the meaning of the respective entries No.1 to 500 for Q in Table 1.
  • Table I.14 Preferred compounds of the formula (I.14) are the compounds I.14-1 to I.14-500, in which the radical Q has the meanings of Table 1 given in the respective line.
  • the compounds I.14-1 to I.14-500 in Table I.14 are thus defined by the meaning of the respective entries No.1 to 500 for Q in Table 1.
  • Table I.15 Preferred compounds of the formula (I.15) are the compounds I.15-1 to I.15-500, in which the radical Q has the meanings of Table 1 given in the respective line.
  • the compounds I.15.-1 to I.15-500 in Table I.15 are thus defined by the meaning of the respective entries No.1 to 500 for Q in Table 1.
  • Table I.16 Preferred compounds of the formula (I.16) are the compounds I.16-1 to I.16-500, in which the radical Q has the meanings of Table 1 given in the respective line.
  • the compounds I.16-1 to I.16-500 in Table I.16 are thus defined by the meaning of the respective entries No.1 to 500 for Q in Table 1.
  • Table I.17 Preferred compounds of the formula (I.17) are the compounds I.17-1 to I.17-500, in which the radical Q has the meanings of Table 1 given in the respective line.
  • the compounds I.17-1 to I.17-500 in Table I.17 are thus defined by the meaning of the respective entries No.1 to 500 for Q in Table 1.
  • Table I.18 Preferred compounds of the formula (I.18) are the compounds I.18-1 to I.18-500, in which the radical Q has the meanings of Table 1 given in the respective line.
  • the compounds I.18-1 to I.18-500 in Table I.18 are thus defined by the meaning of the respective entries No.1 to 500 for Q in Table 1.
  • Table I.19: Preferred compounds of the formula (I.19) are the compounds I.19-1 to I.19-500, in which the radical Q has the meanings of Table 1 given in the respective line.
  • the compounds I.19-1 to I.19-500 in Table I.19 are thus defined by the meaning of the respective entries No.1 to 500 for Q in Table 1.
  • Table I.20 Preferred compounds of the formula (I.20) are the compounds I.20-1 to I.20-500, in which the radical Q has the meanings of Table 1 given in the respective line.
  • the connections I.20-1 to I.20-500 in Table I.20 are thus defined by the meaning of the respective entries No.1 to 500 for Q in Table 1.
  • Table I.21: Preferred compounds of the formula (I.21) are the compounds I.21-1 to I.21-500, in which the radical Q has the meanings of Table 1 given in the respective line.
  • the compounds I.21-1 to I.21-500 in Table I.21 are thus defined by the meaning of the respective entries No.1 to 500 for Q in Table 1.
  • Table I.22 Preferred compounds of the formula (I.22) are the compounds I.22-1 to I.22-500, in which the radical Q has the meanings of Table 1 given in the respective line.
  • the connections I.22-1 to I.22-500 in Table I.22 are thus defined by the meaning of the respective entries No.1 to 500 for Q in Table 1.
  • Table I.23 Preferred compounds of the formula (I.23) are the compounds I.23-1 to I.23-500, in which the radical Q has the meanings of Table 1 given in the respective line.
  • the connections I.23-1 to I.23-500 in Table I.23 are thus defined by the meaning of the respective entries No.1 to 500 for Q in Table 1.
  • Table I.24 Preferred compounds of the formula (I.24) are the compounds I.24-1 to I.24-500, in which the radical Q has the meanings of Table 1 given in the respective line.
  • the connections I.24-1 to I.24-500 in Table I.24 are thus defined by the meaning of the respective entries No.1 to 500 for Q in Table 1.
  • Table I.25 Preferred compounds of the formula (I.25) are the compounds I.25-1 to I.25-500, in which the radical Q has the meanings of Table 1 given in the respective line.
  • the compounds I.25-1 to I.25-500 in Table I.25 are thus defined by the meaning of the respective entries No.1 to 500 for Q in Table 1.
  • Table I.26 Preferred compounds of the formula (I.26) are the compounds I.26-1 to I.26-500, in which the radical Q has the meanings of Table 1 given in the respective line.
  • the connections I.26-1 to I.26-500 in Table I.26 are thus defined by the meaning of the respective entries No.1 to 500 for Q in Table 1.
  • Table I.27 Preferred compounds of the formula (I.27) are the compounds I.27-1 to I.27-500, in which the radical Q has the meanings of Table 1 given in the respective line.
  • the compounds I.27.-1 to I.27-500 in Table I.27 are thus defined by the meaning of the respective entries No.1 to 500 for Q in Table 1.
  • Table I.28 Preferred compounds of the formula (I.28) are the compounds I.28-1 to I.28-500, in which the radical Q has the meanings of Table 1 given in the respective line.
  • the connections I.28-1 to I.28-500 in Table I.28 are thus defined by the meaning of the respective entries No.1 to 500 for Q in Table 1.
  • Table I.29 Preferred compounds of the formula (I.29) are the compounds I.29-1 to I.29-500, in which the radical Q has the meanings of Table 1 given in the respective line.
  • the compounds I.29-1 to I.29-500 in Table I.29 are thus defined by the meaning of the respective entries No.1 to 500 for Q in Table 1.
  • Table I.30 Preferred compounds of the formula (I.30) are the compounds I.30-1 to I.30-500, in which the radical Q has the meanings of Table 1 given in the respective line.
  • the connections I.30-1 to I.30-500 in Table I.30 are thus defined by the meaning of the respective entries No.1 to 500 for Q in Table 1.
  • Table I.31 Preferred compounds of the formula (I.31) are the compounds I.31-1 to I.31-500, in which the radical Q has the meanings of Table 1 given in the respective line.
  • the compounds I.31-1 to I.31-500 in Table I.31 are thus defined by the meaning of the respective entries No.1 to 500 for Q in Table 1.
  • Table I.32 Preferred compounds of the formula (I.32) are the compounds I.32-1 to I.32-500, in which the radical Q has the meanings of Table 1 given in the respective line.
  • the connections I.32-1 to I.32-500 in Table I.32 are thus defined by the meaning of the respective entries No.1 to 500 for Q in Table 1.
  • Table I.33 Preferred compounds of the formula (I.33) are the compounds I.33-1 to I.33-500, in which the radical Q has the meanings of Table 1 given in the respective line.
  • the connections I.33-1 to I.33-500 in Table I.33 are thus defined by the meaning of the respective entries No.1 to 500 for Q in Table 1.
  • Table I.34 Preferred compounds of the formula (I.34) are the compounds I.34-1 to I.34-500, in which the radical Q has the meanings of Table 1 given in the respective line.
  • the compounds I.34-1 to I.34-500 in Table I.34 are thus defined by the meaning of the respective entries No.1 to 500 for Q in Table 1.
  • Table I.35 Preferred compounds of the formula (I.35) are the compounds I.35-1 to I.35-500, in which the radical Q has the meanings of Table 1 given in the respective line.
  • the compounds I.35-1 to I.35-500 in Table I.35 are thus defined by the meaning of the respective entries No.1 to 500 for Q in Table 1.
  • Table I.36 Preferred compounds of the formula (I.36) are the compounds I.36-1 to I.36-500, in which the radical Q has the meanings of Table 1 given in the respective line.
  • the connections I.36-1 to I.36-500 in Table I.36 are thus defined by the meaning of the respective entries No.1 to 500 for Q in Table 1.
  • Table I.37 Preferred compounds of the formula (I.37) are the compounds I.37-1 to I.37-500, in which the radical Q has the meanings of Table 1 given in the respective line.
  • the compounds I.37-1 to I.37-500 in Table I.37 are thus defined by the meaning of the respective entries No.1 to 500 for Q in Table 1.
  • Table I.38 Preferred compounds of the formula (I.38) are the compounds I.38-1 to I.38-500, in which the radical Q has the meanings of Table 1 given in the respective line.
  • the connections I.38-1 to I.38-500 in Table I.38 are thus defined by the meaning of the respective entries No.1 to 500 for Q in Table 1.
  • Table I.39: Preferred compounds of the formula (I.39) are the compounds I.39-1 to I.39-500, in which the radical Q has the meanings of Table 1 given in the respective line.
  • the compounds I.39-1 to I.39-500 in Table I.39 are thus defined by the meaning of the respective entries No.1 to 500 for Q in Table 1.
  • Table I.40 Preferred compounds of the formula (I.40) are the compounds I.40-1 to I.40-500, in which the radical Q has the meanings of Table 1 given in the respective line.
  • the connections I.40-1 to I.40-500 in Table I.40 are thus defined by the meaning of the respective entries No.1 to 500 for Q in Table 1.
  • Table I.41: Preferred compounds of the formula (I.41) are the compounds I.41-1 to I.41-500, in which the radical Q has the meanings of Table 1 given in the respective line.
  • the compounds I.41-1 to I.41-500 in Table I.41 are thus defined by the meaning of the respective entries No.1 to 500 for Q in Table 1.
  • Table I.42 Preferred compounds of the formula (I.42) are the compounds I.42-1 to I.42-500, in which the radical Q has the meanings of Table 1 given in the respective line.
  • the connections I.42-1 to I.42-500 in Table I.42 are thus defined by the meaning of the respective entries No.1 to 500 for Q in Table 1.
  • Table I.43 Preferred compounds of the formula (I.43) are the compounds I.43-1 to I.43-500, in which the radical Q has the meanings of Table 1 given in the respective line.
  • the compounds I.43-1 to I.43-500 in Table I.43 are thus defined by the meaning of the respective entries No.1 to 500 for Q in Table 1.
  • Table I.44 Preferred compounds of the formula (I.44) are the compounds I.44-1 to I.44-500, in which the radical Q has the meanings of Table 1 given in the respective line.
  • the connections I.44-1 to I.44-500 of Table I.44 are thus defined by the meaning of the respective entries No.1 to 500 for Q of Table 1.
  • Table I.45 Preferred compounds of the formula (I.45) are the compounds I.45-1 to I.45-500, in which the radical Q has the meanings of Table 1 given in the respective line.
  • the compounds I.45.-1 to I.45-500 in Table I.45 are thus defined by the meaning of the respective entries No.1 to 500 for Q in Table 1.
  • Table I.46 Preferred compounds of the formula (I.46) are the compounds I.46-1 to I.46-500, in which the radical Q has the meanings of Table 1 given in the respective line.
  • the connections I.46-1 to I.46-500 in Table I.46 are thus defined by the meaning of the respective entries No.1 to 500 for Q in Table 1.
  • Table I.47: Preferred compounds of the formula (I.47) are the compounds I.47-1 to I.47-500, in which the radical Q has the meanings of Table 1 given in the respective line.
  • the connections I.47-1 to I.47-500 of Table I.47 are thus defined by the meaning of the respective entries No.1 to 500 for Q of Table 1.
  • Table I.48 Preferred compounds of the formula (I.48) are the compounds I.48-1 to I.48-500, in which the radical Q has the meanings of Table 1 given in the respective line.
  • the ⁇ value – signal intensity number pairs from different signal peaks are listed separated by semicolons.
  • the peak list of an example therefore has the form: ⁇ 1 (intensity1 ) ; ⁇ 2 (intensity2);........; ⁇ i (intensityi ) ; whil; ⁇ n (intensitiesn)
  • 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.
  • the present invention is also a method for controlling harmful plants and / or for regulating the growth of plants, characterized in that an effective amount - one or more compounds of the general formula (I) according to the invention and / or their salts, as defined above, preferably in one of the configurations identified as preferred or particularly preferred, in particular one or more compounds of the formulas (I.1-1) to (I.48-500) and/or their salts, each 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 are growing, or the area under cultivation.
  • the present invention also relates to 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 general formula (I) and/or salts thereof, as defined above, preferably in one of as preferred or particularly preferred embodiment, in particular one or more compounds of the formulas (I.1-1) to (I.48-500) and / or their salts, each as defined above, or - an agent according to the invention, as below defined, on undesired plants (e.g. harmful plants such as monocotyledonous or dicotyledon weeds or undesired cultivated plants), the seeds of the undesired plants (i.e. plant seeds, e.g.
  • undesired plants e.g. harmful plants such as monocotyledonous or dicotyledon weeds or undesired cultivated plants
  • the seeds of the undesired plants i.e. plant seeds, e.g.
  • the soil in which or on where the unwanted plants are growing e.g. the soil of cultivated land or non-cultivated land
  • the cultivated area i.e. area where unwanted plants will grow
  • the present invention is also a method for controlling the growth regulation of plants, preferably useful plants, characterized in that an effective amount - of one or more compounds of the general formula (I) and / or their salts, as defined above, preferably in a the preferred or particularly preferred characterized configuration, in particular one or more compounds of the formulas (I.1-1) to (I.48-500) and / or their salts, each as defined above, or - a composition according to the invention, as defined below, on the plant, the seed of the plant (i.e. plant seeds, e.g. grains, seeds or vegetative propagating organs such as tubers or parts of shoots with buds), the soil in or on which the plants grow (e.g.
  • the compounds of the general formula (I) according to the invention or the compositions according to the invention can be applied, for example, pre-sowing (possibly also by incorporation into the soil), pre-emergence and/or post-emergence.
  • some representatives of the monocotyledonous and dicotyledonous weed flora that can be controlled by the compounds according to the invention may be mentioned by way of example, without the naming of a restriction to specific species.
  • one or more compounds of the general formula (I) and/or salts thereof are preferably used for controlling harmful plants or for regulating growth in crops of useful plants or ornamental plants, the useful plants or ornamental plants in a preferred embodiment are transgenic plants.
  • the compounds of the general formula (I) according to the invention and/or their salts are suitable for controlling the following genera of monocotyledonous and dicotyledonous harmful plants: monocotyledonous harmful plants of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.
  • the compounds of the general formula (I) according to the invention are applied to the surface of the soil before the harmful plants (grasses and/or weeds) germinate (pre-emergence method), then either the emergence of the weed or weed seedlings is completely prevented or they grow up to the cotyledon stage , but then stop growing and finally die off completely after three to four weeks.
  • the active ingredients are applied to the green parts of the plant post-emergence, growth stops after the treatment and the harmful plants remain in the growth stage present at the time of application or die off completely after a certain time, so that weed competition that is harmful to the crop plants occurs very early and is permanently eliminated.
  • the compounds of the general formula (I) according to the invention have excellent herbicidal activity against monocotyledonous and dicotyledon weeds, crop plants of economically important crops, e.g. dicotyledonous crops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Miscanthus, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous cultures of the genera Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea , Depending on the structure of the respective compound according to the invention and the amount applied, only insignificant damage or no damage at all.
  • the present compounds are very suitable for the selective control of undesired plant growth in crops such as agricultural crops or ornamental plants.
  • the compounds of the general formula (I) according to the invention (depending on their particular structure and the application rate applied) have excellent growth-regulating properties in crop plants. They intervene to regulate the plant's own metabolism and can therefore be used to specifically influence plant constituents and to facilitate harvesting, e.g. by triggering desiccation and growth stunted growth.
  • they are also suitable for the general control and inhibition of unwanted vegetative growth without killing the plants. Inhibition of vegetative growth plays a major role in many monocotyledonous and dicotyledonous crops, since this can reduce or completely prevent the formation of beds.
  • the active compounds can also be used for combating harmful plants in crops of plants modified by genetic engineering or by conventional mutagenesis.
  • the transgenic plants are characterized in the Usually 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 crop in terms of quantity, quality, shelf life, composition and special ingredients.
  • transgenic plants with an increased starch content or altered starch quality or those with a different fatty acid composition in the harvested crop are known.
  • transgenic crops preference is given to using the compounds according to the invention and/or their salts in economically important transgenic crops of useful and ornamental plants, e.g. of cereals such as wheat, barley, rye, oats, millet, rice and corn or also crops of sugar beets, cotton, Soy, rapeseed, potato, tomato, pea 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 have been made resistant by genetic engineering. Because of their herbicidal and plant growth-regulating properties, the active compounds can also be used to control harmful plants in crops of known or genetically modified plants that are still to be developed.
  • the transgenic plants are generally distinguished 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 crop in terms of quantity, quality, shelf life, composition and special ingredients.
  • transgenic plants with an increased starch content or altered starch quality or those with a different fatty acid composition in the harvested crop are known.
  • Other special properties can be tolerance or resistance to abiotic stressors such as heat, cold, drought, salt and ultraviolet radiation. Preference is given to using the compounds of the formula (I) according to the invention or their salts in economically important transgenic crops of useful and ornamental plants, e.g.
  • the compounds of the general formula (I) can preferably be used as herbicides in crops of useful plants which are resistant to the phytotoxic effects of the herbicides or have been made resistant by genetic engineering.
  • Conventional ways of producing new plants that have modified properties compared to previously existing plants include, for example, classical breeding methods and the generation of mutants.
  • new plants with modified properties can be created using genetic engineering methods. Numerous molecular biological techniques with which new transgenic plants with modified properties can be produced are known to the person skilled in the art.
  • nucleic acid molecules can be introduced into plasmids, which allow mutagenesis or sequence modification by 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.
  • the production of plant cells with a reduced activity of a gene product can be achieved, for example, by expressing at least one corresponding antisense RNA, a sense RNA to achieve a co-suppression effect or the expression of at least one correspondingly constructed ribozyme that specifically cleaves transcripts of the above gene product .
  • DNA molecules can be used which include the entire coding sequence of a gene product, including any flanking sequences present, as well as DNA molecules which only include parts of the coding sequence, these parts having to be long enough to enter the cells produce an antisense effect. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product but are not completely identical.
  • the synthesized protein can be located in any compartment of the plant cell. However, in order to achieve localization in a specific compartment, for example the coding region can be linked to DNA sequences which ensure localization in a specific compartment.
  • transgenic plant cells can be regenerated into whole plants using known techniques.
  • the compounds of the general formula (I) according to the invention can preferably be used in transgenic crops which are active against growth substances, such as dicamba, or against herbicides which contain essential plant enzymes, e.g. acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydroxyphenylpyruvate dioxygenases (HPPD ) inhibit or are resistant to herbicides from the group of sulfonylureas, glyphosate, glufosinate or benzoylisoxazoles and analogous active ingredients.
  • ALS acetolactate synthases
  • EPSP synthases glutamine synthases
  • HPPD hydroxyphenylpyruvate dioxygenases
  • the active compounds of the general formula (I) according to the invention are used in transgenic crops, in addition to the effects on harmful plants that can be observed in other crops, there are often effects that are specific to the application in the respective transgenic crop, for example a modified or specially expanded spectrum of weeds, that can be combated, changed application rates that can be used for the application, preferably good compatibility with the herbicides to which the transgenic culture is resistant, and influencing the growth and yield of the transgenic crop plants.
  • the invention therefore also relates to the use of the compounds of the general formula (I) according to the invention and/or their salts as herbicides for controlling harmful plants in crops of useful or ornamental plants, optionally in transgenic crop plants.
  • the use according to the invention for controlling harmful plants or for regulating the growth of plants also includes the case in which compounds of the general formula (I) or salts thereof are derived from a precursor substance ("prodrug ") is formed.
  • the invention also relates to the use of one or more compounds of the general formula (I) or salts thereof or 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 general formula (I) or salts thereof to the plants (harmful plants, optionally together with the useful plants), plant seeds, the soil in which or on which the plants grow, or the area under cultivation applied.
  • the invention also relates to a herbicidal and/or plant growth-regulating agent, characterized in that the agent (a) contains one or more compounds of the general formula (I) and/or salts thereof as defined above, preferably in one of the preferred or particularly preferred embodiment, in particular one or more compounds of the formulas (I.1-1) to (I.48-500) and / or their salts, each as defined above, and (b) one or more other substances selected from the Groups (i) and/or (ii): (i) one or more other agrochemically active substances, preferably selected from the group consisting of insecticides, acaricides, nematicides, other herbicides (i.e.
  • component (i) of a composition according to the invention are preferably selected from the group of substances that are listed in "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012.
  • a herbicidal or plant growth-regulating agent according to the invention preferably comprises one, two, three or more formulation auxiliaries (ii) customary in crop protection selected from the group consisting of surfactants, emulsifiers, dispersants, film formers, thickeners, inorganic salts, dusts, at 25 ° C and 1013 mbar solid carriers, preferably adsorptive, granulated inert materials, wetting agents, antioxidants, stabilizers, Buffer substances, antifoam agents, water, organic solvents, preferably organic solvents 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, dusts, at 25 ° C and 1013 mbar solid carriers, preferably adsorptive, granulated inert materials, wetting agents, antioxidants, stabilizers, Buffer substances,
  • the compounds of the general formula (I) according to the invention can be used in the customary preparations in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules.
  • the invention therefore also relates to herbicidal and plant growth-regulating compositions which contain the compounds of the formula (I) according to the invention and/or their salts.
  • the compounds of the general formula (I) according to the invention and/or their salts can be formulated in various ways, depending on the given biological and/or chemico-physical parameters.
  • WP wettable powder
  • SP water-soluble powder
  • EC emulsifiable concentrates
  • EW emulsions
  • SC suspension concentrates
  • SC oil- or water-based dispersions
  • CS capsule suspensions
  • DP dusts
  • dressings granules for spreading and floor application
  • granules GR
  • WG water-dispersible granules
  • SG water-soluble granules
  • Wettable powders are preparations that are evenly dispersible in water and which, in addition to the active ingredient, contain a diluent or inert substance as well as ionic and/or nonionic surfactants (wetting agents, dispersing agents), e.g , 2,2'-dinaphthylmethane-6,6'-sodium disulfonate, sodium dibutylnaphthalenesulfonate or sodium oleoylmethyltaurine.
  • wetting agents, dispersing agents e.g , 2,2'-dinaphthylmethane-6,6'-sodium disulfonate, sodium dibutylnaphthalenesulfonate or sodium oleoylmethyltaurine.
  • the herbicidal active ingredients are, for example, in conventional apparatus such as hammer mills, blower mills and Air jet mills finely ground and simultaneously or subsequently mixed with the formulation auxiliaries.
  • Emulsifiable concentrates are prepared 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 nonionic surfactants (emulsifiers).
  • organic solvent e.g. butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons or mixtures of organic solvents.
  • emulsifiers examples include: alkylarylsulfonic acid calcium salts such as cadodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as sorbitan fatty acid esters or polyoxyethylene sorbitan esters such as polyoxyethylene sorbitan fatty acid esters. 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 prepared, for example, by wet grinding using commercially available bead mills and optionally adding surfactants, such as those already listed above for the other types of formulation.
  • Emulsions e.g. oil-in-water emulsions (EW)
  • EW oil-in-water emulsions
  • Granules can either be produced by spraying the active ingredient onto adsorptive, granulated inert material or by applying active ingredient concentrates using adhesives, e.g. polyvinyl alcohol, sodium polyacrylic acid or mineral oils, to the surface of carriers such as sand, kaolinite or granulated inert material.
  • adhesives e.g. polyvinyl alcohol, sodium polyacrylic acid or mineral oils
  • Suitable active ingredients can also be granulated in the manner customary for the production of fertilizer granules—if desired in a mixture with fertilizers.
  • Water-dispersible granules are usually produced without solid inert material by the usual processes such as spray drying, fluidized bed granulation, pan granulation, mixing with high-speed mixers and extrusion.
  • 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 compounds of the formula (I) and their salts.
  • the active substance concentration is about 10 to 90% by weight, the remainder to 100% by weight consists of the usual formulation components.
  • the active substance concentration can be about 1 to 90% by weight, preferably 5 to 80% by weight.
  • Formulations in dust form contain 1 to 30% by weight of active ingredient, preferably mostly 5 to 20% by weight of active ingredient, and sprayable solutions contain about 0.05 to 80% by weight, preferably 2 to 50% by weight of active ingredient.
  • the active ingredient content depends in part on whether the active compound is in liquid or solid form and on the granulation aids, fillers, etc. used.
  • the active substance content is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
  • the active ingredient formulations mentioned optionally contain the customary adhesives, wetting agents, dispersants, emulsifiers, penetration agents, preservatives, antifreeze agents and solvents, fillers, carriers and dyes, defoamers, evaporation inhibitors and the pH and the Viscosity affecting agents.
  • formulation aids are described inter alia in "Chemistry and Technology of Agrochemical Formulations", ed. DA Knowles, Kluwer Academic Publishers (1998).
  • the compounds of the general 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 based on the above Formulations are prepared, taking into account the physical properties and stability of the active ingredients to be combined.
  • Combination partners for the compounds of the general formula (I) according to the invention in mixture formulations or in a tank mix are, for example, known active substances 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, protoporphyrinogen oxidase can be used, as described, for example, in Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc.
  • the weight ratio of herbicide (mixture) to safener generally depends on the amount of herbicide applied and the effectiveness of the respective safener and can vary within wide limits, for example in the range from 200:1 to 1:200, preferably 100:1 to 1: 100, especially 20:1 to 1:20.
  • the safeners can be formulated analogously to the compounds of general formula (I) or mixtures thereof with other herbicides/pesticides and provided and used as a ready-to-use formulation or tank mix with the herbicides.
  • the herbicide or herbicide-safener formulations which are in commercial form, are optionally diluted in a customary manner, for example with water for wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules.
  • Preparations in the form of dust, ground or granulated granules and sprayable solutions are usually not 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 general 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, 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 Ha.
  • the application as a stalk shortener can take place at different stages of the growth of the plants. For example, application after tillering at the start of growth in length is preferred.
  • the treatment of the seed can also be considered, which includes the different seed dressing and coating techniques.
  • the application rate depends on the individual techniques and can be determined in preliminary tests.
  • mixture formulations or in the tank mix are, for example, known active substances 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 they are, for example, from Weed Research 26 (1986) 441-445 or "The Pesticide Manual ", 16th edition, The British Crop Protection Council and the Royal Soc.
  • herbicides or plant growth regulators which can be combined with compounds of the general formula (I) include the following active ingredients (the compounds are either identified by the "common name” according to the International Organization for Standardization (ISO ) or with the chemical name or with the code number) and always include all application forms such as acids, salts, esters and isomers such as stereoisomers and optical isomers.
  • dicamba-biproamine dicamba -N,N-bis(3-aminopropyl)methylamine, dicamba-butotyl, dicamba-choline, dicamba-diglycolamine, dicamba-dimethylammonium, dicamba-diethanolamine-ammonium, dicamba-diethylammonium, dicamba-isopropylammonium, 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, Dichloroprop, Dichloroprop-butotyl, Dichloroprop-dimethylammonium, Dichloroprop-etexyl
  • Ketospiradox Ketospiradox Potassium, Lactofen, Lenacil, Linuron, MCPA, MCPA-Butotyl, -Butyl, -dimethyl-ammonium, -diolamine, -2-ethylhexyl, -ethyl, -isobutyl, isoctyl, -isopropyl, -isopropylammonium, - Methyl, Olamine, -Potassium, -Sodium and -Trolamine, MCPB, MCPB-Methyl, -Ethyl and -Sodium, Mecoprop, Mecoprop-Butoty
  • growth regulators and plant stimulants as mixing partners are: 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)p
  • COs (2S,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3 ,5,7-triol), chitooligosaccharides (CO; 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 , by which they are distinguished from chitin molecules [(C8H13NO5)n, CAS No.1398-61-4] and chitosan molecules [(C 5 H11NO4)n, CAS No.9012-76-4]), Chitin-Like Compounds, Chlormequat chloride, Cloprop, Cyclanilide, 3-(Cycloprop-1-enyl)propionic acid, 1-[2-(4-Cyano-3, 5-dicyclopropylphenyl)acetamido]cyclohexanecarboxylic acid, 1-[2-(4-cyano-3-cyclopropylphenyl)acetamido]cyclohexanecarboxylic acid, 1-cyclopropenylmethanol, daminozide, dazomet, dazomet sodium, n-decanol, d
  • LCO lipochitooligosaccharides
  • Nod or Nod factors symbiotic nodulation signals
  • Myc factors they consist of an oligosaccharide backbone of ⁇ -1,4-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, and in the substitution of the reducing and non-reducing sugar units), linoleic acid or its derivatives, linolenic acid or their 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, 5-d
  • n A is a natural number from 0 to 5, preferably from 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;
  • W A is an unsubstituted or substituted divalent heterocyclic radical from the group of partially saturated or aromatic five-membered heterocycles having 1 to 3 hetero ring atoms from the group N and O, where at least one N atom and at most one O atom is contained in the ring, preferably a radical from the group (W A 1 ) to (W A 5 ), mA is 0 or 1;
  • R A 2 is OR A 3 , SR
  • S1f compounds of the triazolyloxyacetic acid derivative type (S1 f ), preferably compounds such as methyl ⁇ [1,5-bis(4-chloro-2-fluorophenyl)-1H-1,2,4-triazol-3-yl]oxy ⁇ acetate (S1-14) or ⁇ [1 ,5-bis(4-chloro-2-fluorophenyl)-1H-1,2,4-triazol-3-yl]oxy ⁇ acetic acid (S1-15) or methyl- ⁇ [5-(4-chloro-2- fluorophenyl)-1-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy ⁇ acetate (S1-16) or ⁇ [5-(4-chloro-2-fluorophenyl)- 1-(2,4-difluorophenyl)-1H-1,2,4-triazol-3-yl]oxy ⁇ acetic acid (S1-17) or methyl ⁇
  • R C 1 is (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 2 -C 4 )-alkenyl, (C 2 -C 4 )-haloalkenyl, (C 3 -C 7 )-cycloalkyl, preferably dichloromethyl;
  • R C 2 , R C 3 are identical or different hydrogen, (C 1 -C 4 )-alkyl, (C 2 -C 4 )-alkenyl, (C 2 -C 4 )-alkynyl, (C 1 -C 4 )-haloalkyl, (C 2 -C 4 )-haloalkenyl, (C 1 -C 4 )-alkylcarbamoyl-(C 1 -C 4 )-alkyl, (C 2 -C 4 )- alkenylcarbam
  • S4 a N-acylsulfonamides of formula (S4 a ) and their salts as described in WO-A-97/45016, wherein R A 1 (C 1 -C 6 )-alkyl, (C 3 -C 6 )-Cycloalkyl, where the last 2 radicals are replaced by v A Substituents from the group halogen, (C 1 -C 4 )-alkoxy, (C 1 -C 6 )-haloalkoxy and (C 1 - C 4 )-alkylthio and in the case of cyclic radicals also by (C 1 -C 4 )-alkyl and (C 1 -C 4 )-haloalkyl are substituted; R A 2 halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, CF 3
  • S5 Active substances from the class of hydroxyaromatics and aromatic-aliphatic carboxylic acid derivatives (S5), e.g , 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid, as described in WO-A-2004/084631, WO-A-2005/015994, WO-A-2005/016001.
  • S6 Active substances from the class of 1,2-dihydroquinoxalin-2-ones (S6), e.g.
  • R D 1 is halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkoxy
  • R D 2 is hydrogen or (C 1 -C 4 )-alkyl
  • R D 3 is hydrogen, (C 1 -C 8th )-alkyl, (C 2 -C 4 )-alkenyl, (C 2 -C 4 )-alkynyl, or aryl, where each of the aforementioned C-containing radicals is unsubstituted or substituted by one or more, preferably up to three, identical or different radicals from the group consisting of halogen and alkoxy; or their salts, n D is an integer from 0 to 2.
  • S9 Active substances from the class of 3-(5-tetrazolylcarbonyl)-2-quinolones (S9), 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-tetrazolyl-carbonyl)-2-quinolone ( CAS Reg No. 95855-00-8) as described in WO-A-1999/000020.
  • S9 3-(5-tetrazolylcarbonyl)-2-quinolones
  • S11 Active substances of the type of oxyimino compounds (S11), which are known as seed dressings, such as. B. "Oxabetrinil” ((Z)-1,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile) (S11-1) known as a seed dressing safener for millet against damage from metolachlor, "Fluxofenim” (1- (4-Chlorophenyl)-2,2,2-trifluoro-1-ethanone-O-(1,3-dioxolan-2-ylmethyl)-oxime) (S11-2) used as a seed dressing safener for sorghum against damage from metolachlor, and "Cyometrinil” or “CGA-43089” ((Z)-cyanomethoxyimino(phenyl)acetonitrile) (S11-3), which is known as a seed dressing safener for sorghum against damage from metolachlor.
  • S12 Active substances from the class of isothiochromanone (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 isothiochromanone
  • S13 One or more compounds from group (S13): "Naphthalic anhydride” (1,8-naphthalenedicarboxylic acid anhydride) (S13-1), known as a seed dressing safener for corn against damage from thiocarbamate herbicides, "Fenclorim” (4.6 -Dichloro-2-phenylpyrimidine) (S13-2), known as a safener for pretilachlor in seeded 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.31541-57-8) (4-carboxy-3,4-dihydro-2H- 1-benzopyran-4-acetic acid) (S13-4) from American Cyanamid, which is known as a safener for corn against damage from imidazolin
  • S16 active substances which are primarily used as herbicides but also have a safener effect on crop plants, e.g. B. (2,4-dichlorophenoxy)acetic acid (2,4-D), (4-chlorophenoxy)acetic acid, (R,S)-2-(4-chloro-o-tolyloxy)propionic acid (Mecoprop), 4-(2,4-dichlorophenoxy)butyric acid (2,4-DB), (4-chloro-o-tolyloxy)acetic acid (MCPA), 4-(4-chloro-o-tolyloxy)butyric acid, 4-(4- chlorophenoxy)butyric acid, 3,6-dichloro-2-methoxybenzoic acid (dicamba), 1-(ethoxycarbonyl)ethyl 3,6-dichloro-2-methoxybenzoate (lactidichloro-ethyl).
  • B (2,4-dichlorophenoxy)acetic acid (2,4-
  • 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.48-500) and/or their salts are: cloquintocet-mexyl , Cyprosulfamide, fenchlorazole ethyl ester, isoxadifen-ethyl, mefenpyr-diethyl, fenclorim, cumyluron, S4-1 and S4-5, and particularly preferred safeners are: cloquintocet-mexyl, cyprosulfamide, isoxadifen-ethyl and mefenpyr-diethyl.
  • ABUTH Abutilon theophrasti
  • ALOMY Alopecurus myosuroides
  • AMARE Amaranthus retroflexus
  • AVEFA Avena Fatua
  • BRSNS Brassica napus
  • DIGSA Digitaria sanguinalis
  • ECCHG 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 the general formula (I) according to Table 1 on various harmful plants and at an application rate corresponding to 20 g/ha and lower, which were obtained according to the test procedure mentioned above.
  • Table A1a Post-emergence effect at 1.25 g/ha against ABUTH in %
  • Table A1c Post-emergence effect at 20 g/ha against ABUTH in %
  • Table A2a Post-emergence effect at 5 g/ha against ALOMYin %
  • Table A3b Post-emergence effect at 5 g/ha against AMARE in %
  • Table A3c Post-emergence effect at 20 g/ha against AMARE in %
  • Table A4c Post-emergence effect at 20 g/ha against DIGSA in %
  • Table A5a Post-emergence effect at 1.25 g/ha against ECHCG in %
  • Table A5b Post-emergence effect at 5 g/ha against ECCHG in %
  • Table A6a Post-emergence effect at 20 g/ha against LOLRI in %
  • Table A7a Post-emergence effect at 1.25 g/ha against MATIN in %
  • Table A7b Post-emergence effect at 5 g/ha against MATIN in %
  • Table A8a Post-emergence effect at 1.25 g/ha against PHBPU in %
  • Table A8b Post-emergence effect at 5 g/ha against PHBPU in %
  • Table A8c Post-emergence effect at 20 g/ha against PHBPU in %
  • Table A9a Post-emergence effect at 1.25 g/ha against POLCO in %
  • Table A9b Post-emergence effect at 5 g/ha against POLCO in %
  • Table A10a Post-emergence effect at 1.25 g/ha against SETVI in %
  • Table A10b Post-emergence effect at 5 g/ha against SETVI in %
  • Table A10c Post-emergence effect at 20 g/ha against SETVI in %
  • Table A11a Post-emergence effect at 1.25 g/ha against VERPE in %
  • Table A11b Post-emergence effect at 5 g/ha against VERPE in %
  • Table A11c Post-emergence effect at 20 g/ha against VERPE in %
  • Table A12a Post-emergence effect at 1.25 g/ha against VIOTR in %
  • Table A13b Post-emergence effect at 5 g/ha against KCHSC in %
  • Table A13c Post-emergence effect at 20 g/ha against KCHSC in %
  • compounds of the general formula (I) according to the invention have good herbicidal activity against harmful plants such as e.g. B. Abutilon theophrasti, Alopecurus myosuroides, Amaranthus retroflexus, Digitaria sanguinalis, Echinochloa crus-galli, Kochia scoparia, Lolium rigidum, Matricaria inodora, Pharbitis purpurea, Polygonum convolvulus, Setaria viridis, Veronica persica and Viola tricolor at an application rate of 20 g of active ingredient or less per hectare, up. B.
  • Tables B1 to B5 below show the effects of selected compounds of the general formula (I) according to Table 1 on various crop plants and an application rate corresponding to 20 g/ha and lower, which were obtained according to the test procedure mentioned above.
  • Table B1a Post-emergence effect at 1.25 g/ha on ZEAMX in %
  • Table B1b Post-emergence effect at 5 g/ha on ZEAMX in %
  • Table B1c Post-emergence effect at 20 g/ha on ZEAMX in %
  • Table B2a Post-emergence effect at 1.25 g/ha on TRZAS in %
  • Table B2b Post-emergence effect at 5 g/ha on TRZAS in %
  • Table B2c Post-emergence effect at 20 g/ha on TRZAS in %
  • Table B3a Post-emergence effect at 1.25 g/ha on ORYZA in %
  • Table B3b Post-emergence effect at 5 g/ha on ORYZA in %
  • Table B4a Post-emergence effect at 1.25 g/ha on GLXMA in %
  • Table B4b Post-emergence effect at 5 g/ha on GLXMA in %
  • Table B5a Post-emergence effect at 1.25 g/ha on BRSNS in %
  • Table B5b Post-emergence effect at 5 g/ha on BRSNS in %
  • post-emergence treatment of compounds of general formula (I) according to the invention has good crop plant tolerance in organisms such as Oryza sativa, Zea mays, Brassica napus, Glycine max and Triticum aestivum at an application rate of 20 g or less per hectare.

Abstract

La présente invention concerne des uraciles d'acide N-benzoïque substitués de formule générale (I) ou 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 adventices et/ou les mauvaises herbes dans les cultures, et/ou en tant que régulateurs de croissance des plantes pour influencer la croissance des cultures.
PCT/EP2023/054143 2022-02-22 2023-02-20 Uraciles d'acide n-benzoïque substitués et leurs sels, et leur utilisation en tant que substances actives herbicides WO2023161172A1 (fr)

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