WO2024104952A1 - Cyclopropyloxyphényluraciles substitués et leurs sels, et leur utilisation comme principes actifs herbicides - Google Patents

Cyclopropyloxyphényluraciles substitués et leurs sels, et leur utilisation comme principes actifs herbicides Download PDF

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WO2024104952A1
WO2024104952A1 PCT/EP2023/081597 EP2023081597W WO2024104952A1 WO 2024104952 A1 WO2024104952 A1 WO 2024104952A1 EP 2023081597 W EP2023081597 W EP 2023081597W WO 2024104952 A1 WO2024104952 A1 WO 2024104952A1
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alkyl
alkoxy
aryl
methyl
amino
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PCT/EP2023/081597
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German (de)
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Hendrik Helmke
Jens Frackenpohl
Harald Jakobi
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
    • C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D239/08—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms directly attached in position 2
    • C07D239/10—Oxygen or sulfur atoms
    • 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

Definitions

  • the invention relates to the technical field of plant protection products, in particular that of herbicides for the selective control of weeds and grass weeds in crops.
  • this invention relates to cyclopropyloxyphenyluracils with further substituted alkylidenecarboxylic acid esters and salts thereof, processes for their preparation and their use as herbicides, in particular for controlling weeds and/or grass weeds in crops of useful plants and/or as plant growth regulators for influencing the growth of crops of useful plants.
  • Plant protection products known to date for the selective control of harmful plants in crops or active substances for controlling undesirable plant growth sometimes have disadvantages when used, either because they (a) have no or insufficient herbicidal effect against certain harmful plants, (b) have too small a spectrum of harmful plants that can be controlled with an active substance, (c) have too little selectivity in crops and/or (d) have a toxicologically unfavourable profile.
  • active substances that can be used as plant growth regulators in some crops lead to undesirably reduced crop yields in other crops or are not compatible with the crop or are only compatible within a narrow application rate range.
  • Some of the known active substances cannot be produced economically on an industrial scale due to difficult-to-access precursors and reagents or have insufficient chemical stability. With other active substances, the effect depends too strongly on environmental conditions, such as weather and soil conditions.
  • N-linked aryluracils can be used as herbicidal active ingredients (cf. EP408382, EP473551, EP648749, US4943309, US5084084, US5127935, W091/00278, WO95/29168, WO95/30661, WO96/35679, WO97/01541, WO98/25909, WO2001/39597).
  • the known aryluracils have a number of gaps in their effectiveness, particularly against monocotyledonous weeds.
  • a number of herbicidal Active ingredient combinations based on N-linked aryluracils have also become known (cf. DE4437197, EP714602, WO96/07323, WO96/08151, JP11189506).
  • the properties of these active ingredient combinations are not satisfactory in all respects.
  • N-aryluracils with optionally further substituted lactic acid groups can also be used as herbicidal active ingredients (cf. JP2000/302764, JP2001/172265, US6403534, EP408382A1). It is also known that N-aryluracils with specific, optionally further substituted, thiolactic acid groups also exhibit herbicidal effects (cf. W02010/038953, KR2011110420, W 02020/013500). Selected substituted tetrahydrofuryl esters of N-aryluracils with optionally further substituted thiolactic acid groups are described in JP09188676.
  • substituted N-benzoic acid uracils which carry chlorine substituents in the benzoic acid unit (cf. W091/000278, DE19741411, WO95/32952, US6207830, WO88/10254, EP831091). Furthermore, highly substituted 3-amino-l-(3-carboxy-4-cyanophenyl)-uracils with various carboxylate side chains have been described (cf. WO98/25909). Highly substituted N-benzoic acid uracils with aminosulfonylaminocarbonylalkoxy side chains are also known (cf.
  • the present invention relates to substituted cyclopropyloxyphenyluracils of the general formula (I) or their salts wherein R 1 is hydrogen, halogen, (C1-C8)-alkoxy, R 2 is halogen, cyano, nitro, C(O)NH 2 , C(S)NH 2 , (C 1 -C 8 )-haloalkyl, (C 2 -C 8 )-alkynyl, R 3 and R 4 independently of one another are hydrogen, halogen, (C1-C8)-alkyl, (C1-C8)-haloalkyl, (C 1 -C 8 )-alkoxy, where R 3 and R 4 do not simultaneously represent (C 1 -C 8 )-alkoxy, R 7 is hydrogen, fluorine, chlorine, bromine, trifluoromethyl, (C 1 -C 8 )-alkoxy, G is unbranched or branched (C 1 -C 8 )-alkylene, X is
  • the compounds of the general formula (I) can be prepared by addition of a suitable inorganic or organic acid, for example mineral acids, such as HCl, HBr, H2SO4, H3PO4 or HNO3, or organic acids, e.g. B.
  • Carboxylic acids such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid or sulfonic acids, such as p-toluenesulfonic acid, form salts on a basic group, such as amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino. These salts then contain the conjugated base of the acid as an anion.
  • Suitable substituents which are present in deprotonated form can form internal salts with protonatable groups, such as amino groups. Salt formation can also occur through the action of a base on compounds of the general formula (I).
  • Suitable bases are, for example, organic Amines, such as trialkylamines, morpholine, piperidine and pyridine, and ammonium, alkali or alkaline earth metal hydroxides, carbonates and hydrogen carbonates, in particular sodium and potassium hydroxide, sodium and potassium carbonate and sodium and potassium hydrogen carbonate.
  • salts are compounds in which the acidic hydrogen is replaced by a cation suitable for agriculture, for example metal salts, in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or also ammonium salts, salts with organic amines or quaternary ammonium salts, for example with cations of the formula [NR a R b R c R d ] + , in which R a to R d each independently represent an organic radical, in particular alkyl, aryl, aralkyl or alkylaryl.
  • Alkylsulfonium and alkylsulfoxonium salts such as (C 1 -C 4 )-trialkylsulfonium and (C 1 -C 4 )-trialkylsulfoxonium salts, are also suitable.
  • the compounds of the formula (I) and their salts used according to the invention are referred to below as "compounds of the general formula (I)".
  • Preferred subject matter of the invention are compounds of the general formula (I), in which R 1 is hydrogen, halogen, (C 1 -C 6 )-alkoxy, R 2 is halogen, cyano, nitro, C(O)NH 2 , C(S)NH 2 , (C 1 -C 6 )-haloalkyl, (C 2 -C 6 )-alkynyl, R 3 and R 4 independently of one another are hydrogen, halogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C1-C6)-alkoxy, where R 3 and R 4 do not simultaneously represent (C1-C6)-alkoxy, R 7 is hydrogen, fluorine, chlorine, bromine, trifluoromethyl, (C 1 -C 6 )-alkoxy, G is unbranched or branched (C1-C6)-alkylene, X is methyl, amino, Y is oxygen (O), nitrogen (as
  • N-morpholinyl and R 15 and R 16 independently represent (C1-C6)-alkyl, (C3-C6)-cycloalkyl, aryl, heteroaryl, heterocyclyl, or R 15 and R 16 form a fully saturated monocyclic 3- to 7-membered carbocycle with the carbon atom to which they are bonded.
  • R 1 is hydrogen, halogen
  • R 2 is halogen, cyano, nitro, C(O)NH 2 , C(S)NH 2 , (C 1 -C 4 )-haloalkyl, (C 2 -C 4 )-alkynyl
  • R 3 and R 4 independently of one another are hydrogen, halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl
  • R 7 is hydrogen, fluorine, chlorine, bromine, trifluoromethyl
  • G is unbranched or branched (C 1 -C 5 )-alkylene
  • X is methyl
  • Y oxygen (O)
  • Q is a radical of the following formulas Q -A QB
  • R 8 is hydrogen, (C1-C5)-alkyl, (C1-C5)-haloalkyl, aryl, aryl-(C1-C5)
  • N-morpholinyl and R 15 and R 16 independently of one another are (C1-C6)-alkyl, (C3-C6)-cycloalkyl, aryl, heteroaryl, heterocyclyl, or R 15 and R 16 form a fully saturated monocyclic 3- to 6-membered carbocycle with the carbon atom to which they are bonded.
  • R 1 is fluorine, chlorine
  • R 2 is fluorine, chlorine, bromine, iodine, cyano, nitro, C(O)NH2, C(S)NH2,
  • R 3 and R 4 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, prop-1-yl, prop-2-yl, but-1-yl, but-2-yl, 2-methyl-prop-1-yl, 1,1-dimethyleth-1-yl, trifluoromethyl
  • R 7 represents hydrogen, fluorine, chlorine, bromine, trifluoromethyl
  • G represents methylene, (methyl)methylene, (ethyl)methylene, (prop-1-yl)methylene, (prop-2-yl)methylene, (but-1-yl)methylene, (but-2-yl)methylene, (pent-1-yl)methylene, (pent-2-yl)methylene, (pent-3-
  • R 1 is fluorine
  • R 2 stands for chlorine, bromine, iodine, cyano, nitro
  • R 3 and R 4 independently represent hydrogen
  • R 7 stands for hydrogen, fluorine, chlorine,
  • G stands for methylene, (methyl)methylene, (ethyl)methylene, (dimethyl)methylene, ethylene, n-propylene, (l-methyl)ethyl-l-ene, (2-methyl)ethyl-l-ene, n-butylene,
  • X is methyl or amino, preferably methyl
  • Q stands for one of the above specifically mentioned groupings Q-1 to Q-480.
  • R 1 is fluorine
  • R 2 is chlorine, bromine or nitro
  • R 3 and R 4 are hydrogen
  • R 7 stands for fluorine
  • G stands for methylene
  • X stands for methyl Y represents oxygen (O)
  • Q represents one of the groups Q-1, Q-89, Q-176, Q-286, Q-371, Q-444 or Q-471 specifically mentioned above.
  • the general or preferred radical definitions listed above apply both to the end products of the formula (I) and to the starting materials or intermediates required for their preparation. These radical definitions can be combined with one another as desired, including between the preferred ranges given. The terms used above and below are explained with regard to the compounds according to the invention.
  • the general rule for the designation of chemical groups is that the connection to the skeleton or the rest of the molecule is via the last-mentioned structural element of the chemical group in question, ie for example in the case of (C 2 -C 8 )-alkenyloxy via the oxygen atom, and in the case of heterocyclyl-(C1-C8)-alkyl or R 13 O(O)C-(C1-C8)-alkyl via the C atom of the alkyl group.
  • alkyl In a composite chemical group such as heterocyclyl-(C 1 -C 8 )-alkyl or R 13 O(O)C-(C 1 -C 8 )-alkyl, the designation “alkyl” therefore also stands for an alkylene group.
  • alkylsulfonyl alone or as part of a chemical group - stands for straight-chain or branched alkylsulfonyl, preferably with 1 to 8, or with 1 to 6 carbon atoms, e.g.
  • (but not limited to) (C1-C6)-alkylsulfonyl such as methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, 1,1-dimethylethylsulfonyl, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, 2-methyl
  • heteroarylsulfonyl stands for optionally substituted pyridylsulfonyl, pyrimidinylsulfonyl, pyrazinylsulfonyl or optionally substituted polycyclic heteroarylsulfonyl, here in particular optionally substituted quinolinylsulfonyl, for example substituted by fluorine, chlorine, bromine, iodine, cyano, nitro, alkyl, haloalkyl, haloalkoxy, amino, alkylamino, alkylcarbonylamino, dialkylamino or alkoxy groups.
  • alkylthio alone or as part of a chemical group - stands for straight-chain or branched S-alkyl, preferably with 1 to 8, or with 1 to 6 carbon atoms, such as (Ci-Cio)-, (Ci-Ce)- or (Ci-Cp-alkylthio, e.g. (but not limited to) (Ci-Ce)-alkylthio such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio,
  • 1-Ethylpropylthio Hexylthio, 1-Methylpentylthio, 2-Methylpentylthio, 3-Methylpentylthio, 4-Methyl-pentylthio, 1,1-Dimethylbutylthio, 1,2-Dimethylbutylthio, 1,3-Dimethylbutylthio, 2,2-Dimethylbutylthio, 2,3-Dimethylbutylthio, 3,3-Dimethylbutylthio, 1-Ethylbutylthio, 2-Ethylbutylthio, 1,1,2-Tri-methylpropylthio, 1,2,2-Trimethylpropylthio, 1-Ethyl-1-methylpropylthio and l-Ethyl-2-methyl-propylthio.
  • 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) (Ci-Ce)-alkylsulfinyl such as methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1,1-dimethylethylsulfinyl, pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, hexylsulfinyl, 1-methylpentylsulfinyl, 2-
  • Alkoxy means an alkyl radical bonded via 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 a cycloalkyl radical bonded via an oxygen atom
  • cycloalkenyloxy means a cycloalkenyl radical bonded via an oxygen atom.
  • the number of C atoms refers to the alkyl radical in the alkylcarbonyl group.
  • the number of C atoms refers to the alkenyl or alkynyl radical in the alkenyl or alkynylcarbonyl group.
  • the number of C atoms refers to the alkyl radical in the alkoxycarbonyl group.
  • the number of C atoms refers to the alkenyl or alkynyl radical in the alkene or alkynyloxycarbonyl group.
  • the number of C atoms refers to the alkyl radical in the alkylcarbonyloxy group.
  • the number of C atoms refers to the alkenyl or alkynyl radical in the alkenyl or alkynylcarbonyloxy group.
  • C(O)R 13 , C(O)OR 13 , OC(O)NR 11 R 12 , or C(O)NR 11 R 12 the abbreviation O in brackets stands for an oxygen atom bonded to the adjacent carbon atom via a double bond.
  • abbreviations such as OC(S)OR 13 , OC(S)SR 14 , OC(S)NR 11 R 12 the abbreviation S in 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 having preferably 6 to 14, in particular 6 to 10 ring C atoms, for example phenyl, naphthyl, anthryl, phenanthrenyl, and the like, preferably phenyl.
  • optionally substituted aryl also includes multicyclic systems such as tetrahydronaphthyl, indenyl, indanyl, fluorenyl, biphenylyl, where the bonding site is on the aromatic system. In terms of systematics, “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-
  • multicyclic systems are also included, such as 8-aza-bicyclo[3.2.1]octanyl, 8-aza-bicyclo[2.2.2]octanyl or l-aza-bicyclo[2.2.1]heptyl.
  • spirocyclic systems are also included, such as, for example, l-oxa-5-aza-spiro[2.3]hexyl.
  • the heterocyclic ring preferably contains 3 to 9 ring atoms, in particular 3 to 6 ring atoms, and one or more, preferably 1 to 4, in particular 1, 2 or 3 heteroatoms in the heterocyclic ring, preferably from the group N, O, and S, although two oxygen atoms should not be directly adjacent, such as, for example, with a heteroatom from the group N, O and S 1- or 2- or 3-pyrrolidinyl, 3,4-dihydro-2H-pyrrol-2- or 3-yl, 2,3-dihydro-1H-pyrrol-1- or 2- or 3- or 4- or 5-yl; 2,5-dihydro-lH-pyrrol-l- 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-l- or 2- or 3- or 4- or 5- or 6-yl; 1,2,3,3,6-t
  • heterocyclyl are a partially or fully hydrogenated heterocyclic radical with two heteroatoms from the group N, O and S, such as 1- or 2- or 3- or 4-pyrazolidinyl; 4,5-dihydro-3H-pyrazol- 3- or 4- or 5-yl; 4,5-dihydro-lH-pyrazol-l- or 3- or 4- or 5-yl; 2,3-dihydro-lH-pyrazol-l- or 2- or 3- or 4- or 5-yl; 1- or 2- or
  • 6-yl 1,4-dihydropyrazin-l- or 2- or 3-yl; 2,3-dihydropyrazin-2- or 3- or 5- or 6-yl; 2,5-dihydropyrazin-2- or 3-yl; l,3-dioxolan-2- or 4- or 5-yl; l,3-dioxol-2- or 4-yl; l,3-dioxan-2- or 4- or 5-yl; 4H-l,3-dioxin-2- or 4- or 5- or 6-yl; 1 ,4-dioxan-2- or 3- or 5- or 6-yl;
  • 6-yl 5,6-dihydro-4H-l,2-oxazin-3- or 4- or 5- or 6-yl; 2H-l,2-oxazin-2- or 3- or 4- or 5- or 6-yl; 6H-l,2-oxazin-3- or 4- or 5- or 6-yl; 4H-l,2-oxazin-3- or 4- or 5- or 6-yl; 1,3-oxazinan-2- or 3- or 4- or 5- or 6-yl; 3,4-dihydro-2H-l,3-oxazin-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-l,3-oxazin-2- or 3- or 4- or 5- or 6-yl; 5,6-Dihydro-2H-l,3-oxazin- 2- or 4- or 5- or 6-yl; 5,6-Dihydro-4H-l,3-oxazin-2- or 4- or 5- or 6-yl; 2H-l,3-oxazin-2- or 4- or 5-
  • heterocyclyl are a partially or fully hydrogenated heterocyclic radical with 3 heteroatoms from the group N, O and S, such as, for example, 1,4,2-dioxazolidin-2- or 3- or 5-yl; l,4,2-dioxazol-3- or 5-yl; 1,4,2-dioxazinan-2- or -3- or 5- or 6-yl; 5,6-dihydro-l,4,2-dioxa- zin-3- or 5- or 6-yl; l,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-l,4,2-dioxazepin-3- or 5- or 6- or 7-yl; 2,3-Dihydro-7H-l,4,2-dioxazepin-2- or 3- or 5- or 6- or 7-yl; 2,3-Dihydro-5H-l,4,2-dio
  • heterocycles listed above are preferably, for example, hydrogen, halogen, alkyl, haloalkyl, hydroxy, alkoxy, cycloalkoxy, aryloxy, alkoxyalkyl, alkoxyalkoxy, cycloalkyl, halocycloalkyl, aryl, arylalkyl, heteroaryl, heterocyclyl, alkenyl, alkylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, alkoxycarbonyl, hydroxycarbonyl, cycloalkoxycarbonyl, cycloalkylalkoxycarbonyl, alkoxycarbonylalkyl, arylalkoxycarbonyl, arylalkoxycarbonylalkyl, alkynyl, alkynylalkyl, alkylalkynyl, tris-alkylsilylalkynyl, nitro, amino, cyano, halo
  • the substituents listed below can be used as substituents for a substituted heterocyclic radical, as can 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 appear on the hetero ring atoms, which can exist in different oxidation states, e.g. N and S, and then form, for example, the divalent groups N(O), S(O) (also abbreviated to SO) and S(O)2 (also abbreviated to SO2) in the heterocyclic ring. In the case of -N(O)- and -S(O)- groups, both enantiomers are included.
  • heteroaryl stands for heteroaromatic compounds, i.e. completely unsaturated aromatic heterocyclic compounds, preferably for 5- to 7-membered rings with 1 to 4, preferably 1 or 2 identical or different heteroatoms, preferably O, S or N.
  • Heteroaryls according to the invention are, for example, IH-pyrrol-1-yl; lH-pyrrol-2-yl; IH-pyrrol-
  • heteroaryl groups according to the invention can also be substituted by one or more identical or different radicals. If two adjacent carbon atoms are part of another aromatic ring, these are fused heteroaromatic systems, such as 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 benzofused rings from the group IH-indol-l-yl, lH-indol-2-yl, lH-indol-3-yl, lH-indol-4-yl, lH- Indol-5-yl, lH-Indol-6-yl, 1H- Indol-7-yl, l-Benzofuran-2-yl, l-Benzofuran-3-yl, 1 -Benzofuran-4-yl, l-Benzofuran- 5-yl, 1-benzo- furan-6-yl, l-benzofuran-7-yl, l-benzothiophen-2-yl, l-benzothiophen-3-yl, l-benzothiophen-4-yl, 1-benzothiophen- 5-yl, l-benzothiophen-6-yl, l-benzothiophen-7-yl, I
  • halogen means, for example, fluorine, chlorine, bromine or iodine. If the term is used for a radical, then "halogen" means, for example, a fluorine, chlorine, bromine or iodine atom.
  • alkyl means a straight-chain or branched open-chain, saturated hydrocarbon radical which is optionally mono- or polysubstituted and in the latter case is referred to as "substituted alkyl".
  • Preferred substituents are halogen atoms, alkoxy, haloalkoxy, cyano, alkylthio, haloalkylthio, amino or nitro groups, particularly preferred are methoxy, methyl, fluoroalkyl, cyano, nitro, fluorine, chlorine, bromine or iodine.
  • the prefix "bis” also includes the combination of different alkyl radicals, e.g. methyl(ethyl) or ethyl(methyl).
  • 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 can be located as substituents on one or more different carbon atoms of the straight-chain or branched hydrocarbon chain, such as CHFCH3, CH2CH2F, CH2CH2CF3, CHF 2 , CH 2 F, CHFCF2CF3.
  • Partially fluorinated haloalkyl means a straight-chain or branched, saturated hydrocarbon which is substituted by various halogen atoms with at least one fluorine atom, where all other halogen atoms which may be present are selected from the group consisting of fluorine, chlorine, bromine and 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 the complete substitution of the straight-chain or branched chain by halogen with the participation of at least one fluorine atom.
  • Haloalkoxy is e.g. OCF3, OCHF2, OCH2F, OCF2CF3, OCH2CF3 and OCH2CH2CI; the same applies to haloalkenyl and other halogen-substituted radicals.
  • (C1-C4)-alkyl used here as an example means a short form for straight-chain or branched alkyl with one to 4 carbon atoms according to the range specified for C atoms, i.e. includes the radicals methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl.
  • General alkyl radicals with a larger specified range of C atoms e.g. "(Ci-C6)-alkyl” also include straight-chain or branched alkyl radicals with a larger number of C atoms, i.e. according to the example also the alkyl radicals with 5 and 6 C atoms.
  • the lower carbon skeletons e.g. with 1 to 6 C atoms, or with 2 to 6 C atoms in the case of unsaturated groups, are preferred for hydrocarbon radicals such as alkyl, alkenyl and alkynyl radicals, including in compound radicals.
  • hydrocarbon radicals such as alkyl, alkenyl and alkynyl radicals, including in compound radicals.
  • Alkyl radicals, including in compound radicals such as alkoxy, haloalkyl, etc., are e.g.
  • alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals, with at least one double bond or triple bond. Preferred are residues with 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 cumulated double bonds, such as allenyl (1,2-propadienyl), 1,2-butadienyl and 1,2,3-pentatrienyl.
  • Alkenyl means, for example, vinyl, which may optionally be substituted by other alkyl radicals, e.g.
  • (C2-Ce)-alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl- 1-propenyl, 2-methyl-l-propenyl, l-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl- 1-butenyl, 2-methyl-l-butenyl, 3-methyl-l-butenyl, l-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, l-Methyl-3-butenyl, 2-Methyl-3-butenyl, 3-Methyl-3-butenyl, l,l-Dimethyl-2-propenyl, 1,2-Dimethyl-l -propenyl, 1 ,
  • Alkyny 1 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, for example, 1,3-butatrienyl or 3-penten-l-yn-l-yl.
  • (C2-Ce)-Alkynyl means, for example, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, l-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, l-methyl-2-butynyl, l-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-l-butynyl, l,l-dimethyl-2-propynyl, 1-ethyl-
  • 3-Methyl-4-pentynyl 4-methyl-l-pentynyl, 4-methyl-2-pentynyl, l,l-di-methyl-2-butynyl, 1,1-dimethyl-3-butynyl, l,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-l-butynyl, l-ethyl-2-butynyl, l-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-l-methyl-2-propynyl.
  • cycloalkyl means a carbocyclic, saturated ring system with preferably 3-8 ring carbon atoms, e.g. cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, which is optionally further substituted, preferably by hydrogen, alkyl, alkoxy, oxo, cyano, nitro, alkylthio, haloalkylthio, halogen, alkenyl, alkynyl, haloalkyl, amino, alkylamino, bisalkylamino, alkoxycarbonyl, hydroxycarbonyl, arylalkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, cycloalkylaminocarbonyl.
  • cyclic systems with substituents are included, which also includes substituents with a double bond on the cycloalkyl radical, e.g. an alkylidene group such as methylidene.
  • polycyclic aliphatic systems are also included, such as bicyclofl .1.0]butan- 1 -yl, bicyclofl .1.0]butan-2-yl, bicyclo[2.1.0]pentan- 1 -yl, bicyclof 1.1.
  • spirocyclic aliphatic systems are also included, such as spiro[2.2]pent-l-yl, spiro[2.3]hex-l-yl, spiro[2.3]hex-4-yl, 3-spiro[2.3]hex-5-yl, spiro[3.3]hept-l-yl, spiro[3.3]hept-2-yl.
  • “Cycloalkenyl” means a carbocyclic, non-aromatic, partially unsaturated ring system with preferably 4-8 C atoms, e.g. 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1,3-cyclohexadienyl or 1,4-cyclohexadienyl, which also includes substituents with a double bond on the cycloalkenyl radical, e.g. an alkylidene group such as methylidene.
  • the explanations for substituted cycloalkyl apply accordingly.
  • alkylidene e.g. also in the form (Ci-Cio)-alkylidene, means the residue of a straight-chain or branched open-chain hydrocarbon residue that is bonded via a double bond.
  • Cycloalkylidene means a carbocyclic residue that is bonded via a double bond.
  • Cycloalkylalkyloxy means a cycloalkylalkyl radical bonded via an oxygen atom and “arylalkyloxy” means an arylalkyl radical bonded via an oxygen atom.
  • Alkoxyalkyl means an alkoxy radical bonded via an alkyl group and “alkoxyalkoxy” means an alkoxyalkyl radical bonded via an oxygen atom, e.g. (but not limited to) methoxymethoxy, methoxyethoxy, ethoxyethoxy, methoxy-n-propyloxy.
  • Alkylthioalkyl means an alkylthio radical bonded via an alkyl group and “alkylthioalkylthio” means an alkylthioalkyl radical bonded via an oxygen atom.
  • Arylalkoxyalkyl means an aryloxy radical bonded via an alkyl group and “heteroaryloxyalkyl” means a heteroaryloxy radical bonded via an alkyl group.
  • Haloalkoxyalkyl means a bound haloalkoxy radical and “haloalkylthioalkyl” means a bound haloalkylthio radical via an alkyl group.
  • Arylalkyl means an aryl radical attached via an alkyl group
  • heteroarylalkyl means a heteroaryl radical attached via an alkyl group
  • heterocyclylalkyl means a heterocyclyl radical attached via an alkyl group
  • Cycloalkylalkyl means a cycloalkyl radical bonded via an alkyl group, for example (but not limited to) cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, 1-cyclopropyleth-l-yl, 2-cyclopropyleth-l-yl, 1-cyclopropylprop-l-yl, 3-cyclopropylprop-l-yl.
  • Arylalkenyl means an aryl radical attached via an alkenyl group
  • heteroarylalkenyl means a heteroaryl radical attached via an alkenyl group
  • heterocyclylalkenyl means a heterocyclyl radical attached via an alkenyl group
  • Arylalkynyl means an aryl radical attached via an alkynyl group
  • heteroarylalkynyl means a heteroaryl radical attached via an alkynyl group
  • heterocyclylalkynyl means a heterocyclyl radical attached via an alkynyl group
  • haloalkylthio alone or as part of a chemical group - stands for straight-chain or branched S-haloalkyl, preferably with 1 to 8, or with 1 to 6 carbon atoms, such as (Ci-Cs)-, (Ci-Ce)- or (Ci-C4)-haloalkylthio, e.g. (but not limited to) trifluoromethylthio, pentafluoroethylthio, difluoromethyl, 2,2-difluoroeth-l-ylthio, 2,2,2-difluoroeth-l-ylthio, 3,3,3-prop-l-ylthio.
  • Halocycloalkyl and halocycloalkenyl mean cycloalkyl or cycloalkenyl which are partially or fully substituted by identical or different halogen atoms, such as F, CI and Br, or by haloalkyl, such as trifluoromethyl or difluoromethyl, e.g.
  • trialkylsilyl alone or as part of a chemical group - stands for straight-chain or branched Si-alkyl, preferably with 1 to 8, or with 1 to 6 carbon atoms, such as tri-[(Ci-Cs)-, (Ci-Ce)- or (Ci-CO-alkyl]silyl, e.g.
  • Trialkylsilylalkynyl stands for a trialkylsilyl radical bonded via an alkynyl group.
  • the compounds of the general formula (I) can exist as stereoisomers depending on the type and linkage of the substituents.
  • the possible stereoisomers defined by their specific spatial shape, such as enantiomers, diastereomers, Z and E isomers, are all included in the formula (I). If, for example, one or more alkenyl groups are present, diastereomers (Z and E isomers) can occur. If, for example, one or more asymmetric carbon atoms are present, enantiomers and diastereomers can occur.
  • Stereoisomers can be obtained from the mixtures obtained during production using conventional separation methods.
  • the chromatographic separation can be carried out both on an analytical scale to determine the enantiomeric excess or the diastereomeric excess, and on a preparative scale to produce test samples for biological testing.
  • Stereoisomers can also be produced selectively by using stereoselective reactions using optically active starting materials and/or auxiliary materials.
  • the invention thus also relates to all stereoisomers which are encompassed by the general formula (I) but are not indicated with their specific stereoform, as well as mixtures thereof. If the compounds are obtained as solids, purification can also be carried out by recrystallization or digestion. If individual compounds (I) cannot be satisfactorily obtained by the routes described below, they can be prepared by derivatization of other compounds (I).
  • the substituted cyclopropyloxyphenyluracils of the general formula (I) according to the invention can be prepared using known processes.
  • the synthesis routes used and investigated are based on commercially available or easily prepared synthesis building blocks.
  • the groups G, Q, X, Y, R 1 , R 2 , R 3 , R 4 , R 7 , R 8 , R 9 , R 10 , R 12 , R 13 , R 14 , R 15 and R 16 of the general formula (I) have the previously defined meanings in the following schemes, unless exemplary but non-limiting definitions are given.
  • the ester hydrolysis of the alkyl ester side chain of cyclopropanoxyphenyluracil (V) is carried out using a suitable acid such as hydrochloric acid or acetic acid and allows the synthesis of cyclopropyloxyphenyluracil carboxylic acid (VI).
  • the cyclopropyloxyphenyluracil carboxylic acid (VI) thus obtained is subsequently converted into the cyclopropyloxyphenyluracil carboxylic acid allyl ester (VII) by reaction with a suitable, optionally further substituted 2-haloacetal allyl ester, represented here by way of example but not by way of limitation as a-bromoacetic acid allyl ester, using a suitable base (e.g. potassium carbonate, cesium carbonate or sodium carbonate) in a suitable polar aprotic solvent.
  • a suitable base e.g. potassium carbonate, cesium carbonate or sodium carbonate
  • the preparation of the cyclopropyloxyphenyluracil carboxylic acid allyl ester (VII) can be carried out by reacting the cyclopropyloxyphenyluracil carboxylic acid (VI) with a suitable optionally further substituted 2-hydroxyacetallyl ester, shown here by way of example but not by way of limitation as a-hydroxyacetic acid allyl ester, using suitable coupling reagents (e.g.
  • HOBt 1-hydroxybenzotriazole
  • EDC l-ethyl-3-(3-dimethylaminopropyl)carbodiimide
  • HATU O- (7-azabenzotriazol-l-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate
  • T3P 2,4,6-tripropyl- l,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
  • the selective ester cleavage of the terminal allyl ester group of cyclopropyloxyphenyluracil (VII) is achieved using phenylsilane in the presence of a suitable Pd catalyst, e.g. tetrakis(triphenylphosphine)palladium(0) in dichloromethane and yields cyclopropyloxyphenyluracil (VIII) in the form of the carboxylic acid.
  • a suitable Pd catalyst e.g. tetrakis(triphenylphosphine)palladium(0) in dichloromethane
  • This cyclopropyloxyphenyluracilcarboxylic acid (VIII) can then be converted into a wide variety of ester variants of cyclopropyloxyphenyluracil (la) by esterification with a suitable alcohol R-OH.
  • the esterification can be carried out, as shown by way of example but not limitation in Scheme 1, using suitable coupling reagents (e.g.
  • HOBt 1-hydroxybenzotriazole
  • EDC l-ethyl-3-(3-dimethylaminopropyl)carbodiimide
  • HATU O-(7-azabenzotriazol-l-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate
  • T3P 2,4,6-tripropyl-l,3,5,2,4,6-trioxatri-phosphorinane-2,4,6-trioxide) and suitable bases (e.g. diisopropylethylamine, triethylamine) in a suitable polar aprotic solvent (e.g. dichloromethane, chloroform).
  • suitable bases e.g. diisopropylethylamine, triethylamine
  • a suitable polar aprotic solvent e.g. dichloromethane, chloroform
  • esterification with a suitable alcohol R-OH to various ester variants of cycloalkyloxyphenyluracil (la) can be carried out via transformation into the acid chloride using thionyl chloride, using a suitable polar aprotic solvent (e.g. dichloromethane (DCM), chloroform, N,N-dimethylacetamide (DMA) or N,N-dimethylformamide (DMF)).
  • a suitable polar aprotic solvent e.g. dichloromethane (DCM), chloroform, N,N-dimethylacetamide (DMA) or N,N-dimethylformamide (DMF)
  • the N-amination is carried out using a suitable base (e.g. sodium hydride, potassium tert-butoxide or potassium carbonate) in a suitable polar aprotic solvent (e.g. dichloromethane, chloroform, N,N-dimethylacetamide or N,N-dimethylformamide).
  • ester hydrolysis of the alkyl ester side chain of the N-aminouracils is carried out using a suitable acid such as hydrochloric acid or acetic acid and thus allows the synthesis of the cycloalkyloxyphenyluracil carboxylic acid (XIII).
  • the cycloalkyloxyphenyluracil carboxylic acid (XIII) thus obtained is subsequently converted into the cycloalkyloxyphenyluracil carboxylic acid allyl ester (XIV) by reaction with a suitable, optionally further substituted 2-haloacetal allyl ester, represented here by way of example but not by way of limitation as a-bromoacetic acid allyl ester, using a suitable base (e.g. potassium carbonate, cesium carbonate or sodium carbonate) in a suitable polar aprotic solvent.
  • a suitable base e.g. potassium carbonate, cesium carbonate or sodium carbonate
  • the preparation of the cycloalkyloxyphenyluracil carboxylic acid allyl ester (XIV) can be carried out by reacting the cycloalkyloxyphenyluracil carboxylic acid (XIII) with a suitable optionally further substituted 2-hydroxyacetal allyl ester, shown here by way of example but not by way of limitation as a-hydroxyacetic acid allyl ester, using suitable coupling reagents (e.g.
  • HOBt 1-hydroxybenzotriazole
  • EDC l-ethyl-3-(3-dimethylaminopropyl)carbodiimide
  • HATU O-(7-azabenzotriazol-l-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate
  • T3P 2,4,6-tripropyl- l,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
  • the selective ester cleavage of the terminal allyl ester group of the cycloalkyloxyphenyluracil (XIV) is achieved using phenylsilane in the presence of a suitable Pd catalyst, e.g. tetrakis(triphenylphosphine)palladium(0) in dichloromethane and yields the cyclopropyloxyphenyl uracil (XV) in the form of the carboxylic acid.
  • This cycloalkyloxyphenyluracilcarboxylic acid (XV) can then be converted into various ester variants of N-amino-cycloalkyloxyphenyluracil (Ib) by esterification with a suitable alcohol R-OH.
  • EDC l-ethyl
  • nitrophenyluracil (cf. W02021013800)
  • access to cyclopropanoxynitrophenyluracil (XVIII) is achieved by reaction with the commercially available 1-hydroxy-l-cyclopropanecarboxylic acid methyl ester (XVII) using a suitable base (e.g. potassium tert-butoxide, potassium carbonate, cesium carbonate or sodium carbonate) in a suitable polar aprotic solvent at elevated temperature,
  • a suitable base e.g. potassium tert-butoxide, potassium carbonate, cesium carbonate or sodium carbonate
  • Ester hydrolysis of the alkyl ester side chain of cyclopropanoxynitrophenyluracil (XVIII) is carried out using a suitable acid such as hydrochloric acid or acetic acid and allows the synthesis of cyclopropanoxynitrophenyluracil carboxylic acid (XIX).
  • the cyclopropanoxynitrophenyluracil carboxylic acid (XIX) thus obtained is subsequently converted into the cyclopropyloxynitrophenyluracil carboxylic acid allyl ester (XX) by reaction with a suitable, optionally further substituted 2-haloacetal allyl ester, represented here by way of example but not by way of limitation as a-bromoacetic acid allyl ester, using a suitable base (e.g. potassium carbonate, cesium carbonate or sodium carbonate) in a suitable polar aprotic solvent.
  • a suitable base e.g. potassium carbonate, cesium carbonate or sodium carbonate
  • the cyclopropyloxynitrophenyluracil carboxylic acid allyl ester (XX) can be prepared by reacting the cyclopropanoxynitrophenyluracil carboxylic acid (XIX) with a suitable optionally further substituted 2-hydroxyacetal allyl ester, shown here by way of example but not by way of limitation as a-hydroxyacetic acid allyl ester, using suitable coupling reagents (e.g.
  • HOBt 1-hydroxybenzotriazole
  • EDC l-ethyl-3-(3-dimethylaminopropyl)carbodiimide
  • HATU O-(7-azabenzotriazol-l-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate
  • T3P 2,4,6-tripropyl-l,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
  • the selective ester cleavage of the terminal allyl ester group of the cyclopropyloxynitrophenyluracil carboxylic acid allyl ester is achieved using phenylsilane in the presence of a suitable Pd catalyst, e.g. tetrakis(triphenylphosphine)palladium(0) in dichloromethane and yields the cyclopropyloxynitrophenyluracil (XXI) in the form of the carboxylic acid.
  • a suitable Pd catalyst e.g. tetrakis(triphenylphosphine)palladium(0) in dichloromethane
  • This cyclopropyloxyphenylnitrouracilcarboxylic acid (XXI) can then be converted into various ester variants of cyclopropanoxynitrophenyluracil (Ic) by esterification with a suitable alcohol R-OH.
  • the esterification can be carried out, as shown by way of example but not limitation in Scheme 1, using suitable coupling reagents (e.g.
  • HOBt 1-hydroxybenzotriazole
  • EDC l-ethyl-3-(3-dimethylaminopropyl)carbodiimide
  • HATU O-(7-azabenzotriazol-l-yl)- N,N,N',N'-tetramethyluronium hexafluorophosphate
  • T3P 2,4,6-tripropyl-l,3,5,2,4,6-trioxatri-phosphorinane-2,4,6-trioxide) and suitable bases (e.g. diisopropylethylamine, triethylamine) in a suitable polar aprotic solvent (e.g. dichloromethane, chloroform).
  • suitable bases e.g. diisopropylethylamine, triethylamine
  • a suitable polar aprotic solvent e.g. dichloromethane, chloroform
  • esterification with a suitable alcohol R-OH to various ester variants of cycloalkyloxyphenyluracil (Ic) can be carried out via transformation into the acid chloride using thionyl chloride, using a suitable polar aprotic solvent (e.g. dichloromethane (DCM), chloroform, N,N-dimethylacetamide (DMA) or N,N-dimethylformamide (DMF)).
  • a suitable polar aprotic solvent e.g. dichloromethane (DCM), chloroform, N,N-dimethylacetamide (DMA) or N,N-dimethylformamide (DMF)
  • Me CLL.
  • the mixture was stirred for a further 3 hours at 50 degrees Celsius and the reaction progress was monitored by TLC monitoring.
  • the organic phase was then concentrated and the reaction residue was taken up in methylene chloride.
  • the organic phase was washed with water and, after phase separation, was dried over sodium sulfate, filtered and concentrated under reduced pressure.
  • the mixture was stirred at RT for 5 h and left to stand overnight. The mixture was then quenched by adding 5 mL of water and the reaction mixture was stirred. 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.
  • reaction solution was then stirred for 5 hours at 80 degrees Celsius. Complete conversion was detected by thin layer chromatography, so that the reaction was subsequently quenched by adding 20 mL water. Ethyl acetate was added and the aqueous phase was extracted several times. The combined organic phases were washed three times with water, dried over magnesium sulfate, filtered and concentrated under reduced pressure.
  • reaction was further stirred at 0 degrees Celsius and the reaction progress was monitored every half hour by thin layer chromatography. After a total of 2 hours, the mixture was allowed to slowly reach room temperature and stirred for a further 2 hours. The reaction was then quenched by adding 20 mL of water. After phase separation, the aqueous phase was extracted several times with dichloromethane, the The combined organic phases were dried and the solvent was subsequently removed in vacuo.
  • Table 1.2 Preferred compounds of formula (1.2) are the compounds 1.2-1 to 1.2-480, in which Q has the meanings given in the respective row of Table 1.
  • the compounds 1.2-1 to 1.2-480 of Table 1.2 are thus defined by the meaning of the respective entries No.1 to 480 for Q of the
  • Table 1.3 Preferred compounds of the formula (1.3) are the compounds 1.3-1 to 1.3-480, in which Q has the meanings given in the respective row of Table 1.
  • the compounds 1.3-1 to 1.3-480 of Table 1.3 are thus defined by the meaning of the respective entries No.1 to 480 for Q of Table 1.
  • Table 1.4: Preferred compounds of the formula (1.4) are the compounds 1.4-1 to 1.4-480, in which Q has the meanings given in the respective row of Table 1.
  • the compounds 1.4-1 to 1.4-480 of Table 1.4 are thus defined by the meaning of the respective entries No.1 to 480 for Q of Table 1.
  • Table 1.5 Preferred compounds of the formula (1.5) are the compounds 1.5-1 to 1.5-480, in which Q has the meanings given in the respective row of Table 1.
  • the compounds 1.5-1 to 1.5-480 of Table 1.7 are thus defined by the meaning of the respective entries No.1 to 480 for Q of Table 1.
  • Table 1.6 Preferred compounds of the formula (1.6) are the compounds 1.6-1 to 1.6-480, in which Q has the meanings given in the respective row of Table 1.
  • the compounds 1.6-1 to 1.6-480 of Table 1.6 are thus defined by the meaning of the respective entries No.1 to 480 for Q of Table 1.
  • Table 1.7 Preferred compounds of the formula (1.7) are the compounds 1.7-1 to 1.7-480, in which Q has the meanings given in the respective row of Table 1.
  • the compounds 1.7-1 to 1.7-480 of Table 1.7 are thus defined by the meaning of the respective entries No.1 to 480 for Q of Table 1.
  • Table 1.8 Preferred compounds of the formula (1.8) are the compounds 1.8-1 to 1.8-480, in which Q has the meanings given in the respective row of Table 1.
  • the compounds 1.8-1 to 1.8-480 of Table 1.8 are thus defined by the meaning of the respective entries No.1 to 480 for Q of Table 1.
  • Table 1.9 Preferred compounds of formula (1.9) are the compounds 1.9-1 to 1.9-480, in which Q has the meanings given in the respective row of Table 1.
  • the compounds 1.9-1 to 1.9-480 of Table 1.9 are thus defined by the meaning of the respective entries No.1 to 480 for Q of the
  • Table 1.10 Preferred compounds of the formula (1.10) are the compounds 1.10-1 to 1.10-480, in which Q has the meanings given in the respective row of Table 1.
  • the compounds 1.10-1 to 1.10-480 of Table 1.10 are thus defined by the meaning of the respective entries No.1 to 480 for Q of Table 1.
  • Table 1.11 Preferred compounds of the formula (1.11) are the compounds 1.11-1 to 1.11-480, in which Q has the meanings given in the respective row of Table 1.
  • the compounds 1.11-1 to 1.11-480 of Table 1.11 are thus defined by the meaning of the respective entries No.1 to 480 for Q of Table 1.
  • Table 1.12 Preferred compounds of the formula (1.12) are the compounds 1.12-1 to 1.12-480, in which Q has the meanings given in the respective row of Table 1.
  • the compounds 1.12-1 to 1.12-480 of Table 1.12 are thus defined by the meaning of the respective entries No.1 to 480 for Q of Table 1.
  • Table 1.13 Preferred compounds of the formula (1.13) are the compounds 1.13-1 to 1.13-480, in which Q has the meanings given in the respective row of Table 1.
  • the compounds 1.13-1 to 1.13-480 of Table 1.13 are thus defined by the meaning of the respective entries No.1 to 480 for Q of Table 1.
  • Table 1.14 Preferred compounds of the formula (1.14) are the compounds 1.14-1 to 1.14-480, in which Q has the meanings given in the respective row of Table 1.
  • the compounds 1.14-1 to 1.14-480 of Table 1.14 are thus defined by the meaning of the respective entries No.1 to 480 for Q of Table 1.
  • Table 1.15 Preferred compounds of the formula (1.15) are the compounds 1.15-1 to 1.15-480, in which Q has the meanings given in the respective row of Table 1.
  • the compounds 1.15-1 to 1.15-480 of Table 1.15 are thus defined by the meaning of the respective entries No.1 to 480 for Q of Table 1.
  • Table 1.16 Preferred compounds of the formula (1.16) are the compounds 1.16-1 to 1.16-480, in which Q has the meanings given in the respective row of Table 1.
  • the compounds 1.16-1 to 1.16-480 of Table 1.16 are thus defined by the meaning of the respective entries No.l to
  • Table 1.17 Preferred compounds of the formula (1.17) are the compounds 1.17-1 to 1.17-480, in which Q has the meanings given in the respective row of Table 1.
  • the compounds 1.17-1 to 1.17-480 of Table 1.17 are thus defined by the meaning of the respective entries No.1 to 480 for Q of Table 1.
  • Table 1.18: Preferred compounds of the formula (1.18) are the compounds 1.18-1 to 1.18-480, in which Q has the meanings given in the respective row of Table 1.
  • the compounds 1.18-1 to 1.18-480 of Table 1.7 are thus defined by the meaning of the respective entries No.1 to 480 for Q of Table 1.
  • Table 1.19 Preferred compounds of the formula (1.19) are the compounds 1.19-1 to 1.19-480, in which Q has the meanings given in the respective row of Table 1.
  • the compounds 1.19-1 to 1.19-480 of Table 1.19 are thus defined by the meaning of the respective entries No.1 to 480 for Q of Table 1.
  • Table 1.20 Preferred compounds of the formula (1.20) are the compounds 1.20-1 to 1.20-480, in which Q has the meanings given in the respective row of Table 1.
  • the compounds 1.20-1 to 1.20-480 of Table 1.7 are thus defined by the meaning of the respective entries No.1 to 480 for Q of Table 1.
  • Table 1.21 Preferred compounds of the formula (1.21) are the compounds 1.21-1 to 1.21-480, in which Q has the meanings given in the respective row of Table 1.
  • the compounds 1.21-1 to 1.21-480 of Table 1.21 are thus defined by the meaning of the respective entries No.1 to 480 for Q of Table 1.
  • Table 1.22 Preferred compounds of the formula (1.22) are the compounds 1.22-1 to 1.22-480, in which Q has the meanings given in the respective row of Table 1.
  • the compounds 1.22-1 to 1.22-480 of Table 1.22 are thus defined by the meaning of the respective entries No.1 to 480 for Q of Table 1.
  • Table 1.23 Preferred compounds of the formula (1.23) are the compounds 1.23-1 to 1.23-480, in which Q has the meanings given in the respective row of Table 1.
  • the compounds 1.23-1 to 1.23-480 of Table 1.23 are thus defined by the meaning of the respective entries No.1 to 480 for Q of Table 1.
  • Table 1.24 Preferred compounds of the formula (1.24) are the compounds 1.24-1 to 1.24-480, in which Q has the meanings given in the respective row of Table 1.
  • the compounds 1.24-1 to 1.24-480 of Table 1.24 are thus defined by the meaning of the respective entries No.1 to 480 for Q of Table 1.
  • Table 1.25: Preferred compounds of the formula (1.25) are the compounds 1.25-1 to 1.25-480, in which Q has the meanings given in the respective row of Table 1.
  • the compounds 1.25-1 to 1.25-480 of Table 1.25 are thus defined by the meaning of the respective entries No.1 to 480 for Q of Table 1.
  • Table 1.26 Preferred compounds of the formula (1.26) are the compounds 1.26-1 to 1.26-480, in which Q has the meanings given in the respective row of Table 1.
  • the compounds 1.26-1 to 1.26-480 of Table 1.26 are thus defined by the meaning of the respective entries No.1 to 480 for Q of Table 1.
  • NMR data of selected examples The ’H-NMR data of selected examples of compounds of the general formula (I) are given in two different ways, namely (a) classical NMR evaluation and interpretation or (b) in the form of ’H-NMR peak lists according to the methods described below a) classical NMR interpretation b) NMR peak list method
  • the ’H-NMR data of selected examples can also be recorded in the form of ’H-NMR peak lists. For each signal peak, first the 8-value in ppm and then the signal intensity are listed in parentheses. The 8-value - signal intensity number pairs of different signal peaks are listed separated from each other by semicolons.
  • the peak list of an example therefore has the form:
  • the intensity of sharp signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the true ratios of the signal intensities. For broad signals, several peaks or the center of the signal and their relative intensity compared to the most intense signal in the spectrum can be shown.
  • To calibrate the chemical shift of 'H NMR spectra we use tetramethylsilane and/or the chemical shift of the solvent, especially in the case of spectra measured in DMSO. Therefore, the tetramethylsilane peak may or may not be present in NMR peak lists.
  • the lists of 'H NMR peaks are similar to classical 'H NMR printouts and thus usually contain all peaks that are listed in a classical NMR interpretation.
  • 'FI NMR printouts may show solvent signals, signals from stereoisomers of the target compounds that are also the subject of the invention, and/or peaks from impurities.
  • our lists of 'H NMR peaks show the usual solvent peaks, for example peaks of DMSO in DMSO-De and the peak of water, which usually have a high intensity on average. Peaks of stereoisomers of the target compounds and/or peaks of impurities usually have on average a lower intensity than the peaks of the target compounds (for example with a purity of >90%).
  • Such stereoisomers and/or impurities may be typical for the respective manufacturing process. Their peaks can thus help to detect the reproduction of our manufacturing process by means of “by-product fingerprints”.
  • the present invention further relates to the use of one or more compounds of the formula (I) according to the invention and/or salts thereof, as defined above, preferably in one of the embodiments characterized as preferred or particularly preferred, in particular one or more compounds of the formulas (1.1-1) to (1.26-480) and/or salts thereof, each as defined above, as herbicide and/or plant growth regulator, preferably in crops of useful and/or ornamental plants.
  • the present invention further relates to a method for controlling harmful plants and/or for regulating the growth of plants, characterized in that an effective amount of one or more compounds of the formula (I) according to the invention and/or salts thereof, as defined above, preferably in one of the embodiments identified as preferred or particularly preferred, in particular one or more compounds of the formulas (1.1-1) to (1.26-480) and/or salts thereof, each as defined above, or of an agent according to the invention, as defined below, is applied to the (harmful) plants, (harmful) plant seeds, the soil in or on which the (harmful) plants grow, or the cultivation area.
  • the present invention also relates to a method for controlling undesirable plants, preferably in crops, characterized in that an effective amount one or more compounds of the formula (I) and/or salts thereof, as defined above, preferably in one of the embodiments identified as preferred or particularly preferred, in particular one or more compounds of the formulae (1.1-1) to (1.26-480) and/or salts thereof, each as defined above, or an agent according to the invention, as defined below, is applied to undesirable plants (e.g. harmful plants such as mono- or dicotyledonous weeds or undesirable cultivated plants), the seed of the undesirable plants (ie plant seeds, e.g. grains, seeds or vegetative propagation organs such as tubers or shoot parts with buds), the soil in or on which the undesirable plants grow (e.g. the soil of cultivated land or non-cultivated land) or the cultivation area (ie area on which the undesirable plants will grow).
  • undesirable plants e.g. harmful plants such as mono- or dicotyledonous weeds or undesirable cultivated plants
  • the present invention furthermore also relates to methods for controlling the growth of plants, preferably of crop plants, characterized in that an effective amount of one or more compounds of the formula (I) and/or salts thereof, as defined above, preferably in one of the embodiments identified as preferred or particularly preferred, in particular one or more compounds of the formulas (1.1-1) to (1.26-480) and/or salts thereof, each as defined above, or of an agent according to the invention, as defined below, is applied to the plant, the seed of the plant (i.e. plant seeds, e.g. grains, seeds or vegetative propagation organs such as tubers or shoot parts with buds), the soil in or on which the plants grow (e.g. the soil of cultivated land or non-cultivated land) or the cultivation area (i.e. area on which the plants will grow).
  • the seed of the plant i.e. plant seeds, e.g. grains, seeds or vegetative propagation organs such as tubers or shoot parts with buds
  • the soil in or on which the plants grow e.g.
  • the compounds according to the invention or the agents according to the invention can be applied, for example, by pre-sowing (if necessary also by incorporation into the soil), pre-emergence and/or post-emergence methods.
  • Some representatives of the monocotyledonous and dicotyledonous weed flora which can be controlled by the compounds according to the invention may be mentioned as examples, without the mention being intended to be a restriction to certain species.
  • one or more compounds of the formula (I) and/or salts thereof are used for controlling harmful plants or for regulating growth in crops of useful plants or ornamental plants, wherein the useful plants or ornamental plants in a preferred embodiment are transgenic plants.
  • the compounds of formula (I) according to the invention and/or their salts are suitable for controlling the following genera of monocotyledonous and dicotyledonous weeds:
  • the compounds according to the invention are applied to the soil surface before the germination of the harmful plants (grass weeds and/or weeds) (pre-emergence method), either the emergence of the grass or weed seedlings is completely prevented or they grow to the cotyledon stage, but then stop growing and finally die completely after three to four weeks.
  • the compounds of the invention have excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, crop plants of economically important crops, eg dicotyledonous crops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Miscanthus, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous crops of the genera Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea, are only slightly damaged or not damaged at all, depending on the structure of the respective compound according to the invention and the amount applied. For these reasons, the present compounds are very suitable for the selective control of undesirable plant growth in plant crops such as agricultural crops or ornamental plants.
  • the compounds according to the invention (depending on their respective structure and the amount applied) have excellent growth-regulating properties in cultivated plants. They regulate the plant's own metabolism and can therefore be used to specifically influence plant ingredients and to facilitate harvesting, for example by triggering desiccation and stunting. Furthermore, they are also suitable for the general control and inhibition of undesirable vegetative growth without killing the plants. Inhibiting vegetative growth plays a major role in many monocotyledonous and dicotyledonous crops, as this can reduce or completely prevent lodging, for example.
  • the active ingredients can also be used to control harmful plants in crops of plants modified by genetic engineering or conventional mutagenesis.
  • the transgenic plants are generally characterized by particularly advantageous properties, for example resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
  • Other special properties affect the harvested product in terms of quantity, quality, storability, composition and special ingredients.
  • Transgenic plants with increased starch content or altered starch quality or those with a different fatty acid composition of the harvested product are known.
  • transgenic crops preference is given to using the compounds according to the invention and/or their salts in economically important transgenic crops of crops and ornamental plants, e.g. cereals such as wheat, barley, rye, oats, millet, rice and maize or crops of sugar beet, cotton, soybeans, rapeseed, potatoes, tomatoes, peas and other types of vegetables.
  • the compounds according to the invention can preferably also be used as herbicides in crops which are resistant to the phytotoxic effects of the herbicides or have been made resistant by genetic engineering. Due to their herbicidal and plant growth regulatory properties, the active ingredients can also be used to combat weeds in crops of known or yet-to-be-developed genetically modified plants.
  • the transgenic plants are generally characterized by particularly advantageous properties, for example resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
  • Other special properties relate, for example, to the harvested product in terms of quantity, quality, storability, composition and special ingredients.
  • Transgenic plants with an increased starch content or altered quality of the starch or those with a different fatty acid composition of the harvested product are known.
  • Other special properties can include tolerance or resistance to abiotic stressors such as heat, cold, drought, salt and ultraviolet radiation.
  • cereals such as wheat, barley, rye, oats, triticale, millet, rice, cassava and maize or also crops of sugar beet, cotton, soybeans, rapeseed, potatoes, tomatoes, peas and other vegetables.
  • the compounds of formula (I) can be used as herbicides in crops which are resistant to the phytotoxic effects of the herbicides or have been made resistant by genetic engineering.
  • nucleic acid molecules can be introduced into plasmids that allow mutagenesis or a sequence change through recombination of DNA sequences.
  • base exchanges can be carried out, partial sequences can be removed or natural or synthetic sequences can be added.
  • Adapters or linkers can be attached to the fragments to connect the DNA fragments to one another.
  • the production of plant cells with a reduced activity of a gene product can be achieved, for example, by the expression of at least one corresponding antisense RNA, a sense RNA to achieve a co-suppression effect or the expression of at least one appropriately constructed ribozyme that specifically cleaves transcripts of the above-mentioned gene product.
  • DNA molecules can be used that contain the entire coding sequence of a gene product, including any flanking sequences that may be present, as well as DNA molecules that contain only parts of the coding sequence, whereby these parts must be long enough to produce an antisense effect in the cells. It is also possible to use DNA sequences that have a high degree of homology to the coding sequences of a gene product, but are not completely identical.
  • the synthesized protein can be localized in any compartment of the plant cell.
  • the coding region can, for example, be linked to DNA sequences that ensure localization in a specific compartment.
  • sequences are known to the person skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227).
  • the expression of the nucleic acid molecules can also take place in the organelles of the plant cells.
  • the transgenic plant cells can be regenerated into whole plants using known techniques.
  • the transgenic plants can in principle be plants of any plant species, i.e. both monocotyledonous and dicotyledonous plants.
  • the compounds (I) according to the invention can be used in transgenic cultures which are resistant to growth factors, such as dicamba, or to herbicides which inhibit essential plant enzymes, e.g. acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydroxyphenylpyruvate dioxygenases (HPPD), or to herbicides from the group of sulfonylureas, glyphosates, glufosinates or benzoylisoxazoles and analogous active substances.
  • growth factors such as dicamba
  • herbicides which inhibit essential plant enzymes e.g. acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydroxyphenylpyruvate dioxygenases (HPPD)
  • ALS acetolactate synthases
  • EPSP synthases glutamine synthases
  • HPPD hydroxyphenylpyruvate dioxygenases
  • the invention therefore also relates to the use of the compounds of the formula (I) according to the invention and/or salts thereof as herbicides for controlling harmful plants in crops of useful or ornamental plants, optionally in transgenic crops.
  • the preferred use is in cereals, preferably maize, wheat, barley, rye, oats, millet or rice, in pre- or post-emergence.
  • the use according to the invention for controlling harmful plants or for regulating the growth of plants also includes the case in which the active ingredient of formula (I) or its salt is formed from a precursor substance ("prodrug") only after application to the plant, in the plant or in the soil.
  • the invention also relates to the use of one or more compounds of the formula (I) or salts thereof or of an agent according to the invention (as defined below) (in a method) for controlling harmful plants or for regulating the growth of plants, characterized in that an effective amount of one or more compounds of the formula (I) or salts thereof is applied to the plants (harmful plants, optionally together with the useful plants), plant seeds, the soil in or on which the plants grow, or the cultivation area.
  • the invention also relates to a herbicidal and/or plant growth regulating agent, characterized in that the agent
  • (a) contains one or more compounds of the formula (I) and/or salts thereof as defined above, preferably in one of the embodiments identified as preferred or particularly preferred, in particular one or more compounds of the formulae (1.1-1) to (1.26-480) and/or salts thereof, each as defined above, and
  • the other agrochemically active substances of component (i) of an agent according to the invention are preferably selected from the group of substances mentioned in "The Pesticide Manual", 19th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2021.
  • a herbicidal or plant growth regulating agent according to the invention preferably comprises one, two, three or more formulation aids (ii) customary in plant protection selected from the group consisting of surfactants, emulsifiers, dispersants, film formers, thickeners, inorganic salts, dusting agents, carriers which are solid at 25 °C and 1013 mbar, preferably adsorbent, granulated inert materials, wetting agents, antioxidants, stabilizers, buffer substances, antifoaming agents, water, organic solvents, preferably organic solvents which are miscible with water in any ratio at 25 °C and 1013 mbar.
  • formulation aids selected from the group consisting of surfactants, emulsifiers, dispersants, film formers, thickeners, inorganic salts, dusting agents, carriers which are solid at 25 °C and 1013 mbar, preferably adsorbent, granulated inert materials, wetting agents, antioxidants, stabilizers, buffer
  • the compounds (I) according to the invention can be used in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules in the customary preparations.
  • the invention therefore also relates to herbicidal and plant growth regulating agents which contain compounds of the formula (I) and/or salts thereof.
  • the compounds of formula (I) and/or their salts can be formulated in various ways, depending on the biological and/or chemical-physical parameters specified. Possible formulation options include, for example: wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), oil- or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), dusting agents (DP), dressing agents, granules for broadcast and soil application, granules (GR) in the form of micro-, spray, coating and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.
  • WP wettable powders
  • SP water-soluble powders
  • EC emulsifi
  • Wettable powders are preparations that can be evenly dispersed in water and which, in addition to the active ingredient and a diluent or inert substance, also contain ionic and/or non-ionic surfactants (wetting agents, dispersants), e.g.
  • the herbicidal active ingredients are finely ground in conventional equipment such as hammer mills, blower mills and air jet mills and mixed simultaneously or subsequently with the formulation aids.
  • Emulsifiable concentrates are produced by dissolving the active ingredient in an organic solvent, e.g. butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons or mixtures of organic solvents with the addition of one or more ionic and/or non-ionic surfactants (emulsifiers).
  • organic solvent e.g. butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons or mixtures of organic solvents.
  • alkylarylsulfonic acid calcium salts such as Ca-dodecylbenzenesulfonate or non-ionic emulsifiers
  • fatty acid polyglycol esters alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as sorbitan fatty acid esters or polyoxyethylene sorbitan esters such as polyoxyethylene sorbitan fatty acid esters.
  • Dusting agents are obtained by grinding the active ingredient with finely divided solid substances, e.g. talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • finely divided solid substances e.g. talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • Suspension concentrates can be water- or oil-based. They can be produced, for example, by wet grinding using commercially available bead mills and, if necessary, adding surfactants, such as those already listed above for the other formulation types.
  • Emulsions e.g. oil-in-water emulsions (EW)
  • EW oil-in-water emulsions
  • Granules can be produced either by spraying the active ingredient onto adsorbable, granulated inert material or by applying active ingredient concentrates using adhesives, e.g. polyvinyl alcohol, polyacrylic acid sodium or mineral oils, to the surface of carrier materials such as sand, kaolinite or granulated inert material.
  • adhesives e.g. polyvinyl alcohol, polyacrylic acid sodium or mineral oils
  • Suitable active ingredients can also be granulated in the usual way for the production of fertilizer granules - if desired in a mixture with fertilizers.
  • Water-dispersible granules are usually produced by conventional processes such as spray drying, fluid bed granulation, disc granulation, mixing with high-speed mixers and extrusion without solid inert material.
  • the agrochemical preparations preferably herbicidal or plant growth regulating agents of the present invention preferably contain a total amount of 0.1 to 99% by weight, preferably 0.5 to 95% by weight, more preferably 1 to 90% by weight, particularly preferably 2 to 80% by weight, of active ingredients of the formula (I) and salts thereof.
  • the active ingredient concentration is about 10 to 90% by weight, the rest 100% by weight consists of usual formulation components.
  • the active ingredient concentration can be about 1 to 90, preferably 5 to 80% by weight.
  • Dust-like formulations contain 1 to 30% by weight of active ingredient, preferably mostly 5 to 20% by weight of active ingredient, sprayable solutions contain about 0.05 to 80, preferably 2 to 50% by weight of active ingredient.
  • the active ingredient content depends in part on whether the active compound is liquid or solid and which granulation aids, fillers, etc. are used. In the case of water-dispersible granules, the active ingredient content is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
  • the active ingredient formulations mentioned may contain the usual adhesives, wetting agents, dispersants, emulsifiers, penetration agents, preservatives, antifreeze agents and solvents, fillers, carriers and colorants, defoamers, evaporation inhibitors and agents which influence the pH value and viscosity.
  • formulation aids are described in "Chemistry and Technology of Agrochemical Formulations", ed. D. A. Knowles, Kluwer Academic Publishers (1998).
  • the compounds of formula (I) or their salts can be used as such or in the form of their preparations (formulations) in combination with other pesticidally active substances, such as insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and/or growth regulators, e.g. as a ready-made 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-made formulation or as tank mixes.
  • the combination formulations can be prepared on the basis of the abovementioned formulations, taking into account the physical properties and stabilities of the active ingredients to be combined.
  • 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, in particular 20:1 to 1:20.
  • the safeners can be formulated analogously to the compounds (I) or mixtures thereof with other herbicides/pesticides and can be provided and applied as a ready-made formulation or tank mix with the herbicides.
  • the herbicide or herbicide-safener formulations in commercial form are diluted in the usual way if necessary, e.g. in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules using water. Dust-like preparations, soil or spreading granules and sprayable solutions are usually not diluted with other inert substances before use.
  • the application rate of the compounds of formula (I) and/or their salts influences to a certain extent the application rate of the compounds of formula (I) and/or their salts.
  • the application rate can vary within wide limits.
  • the total amount of compounds of formula (I) and their salts is preferably in the range from 0.001 to 10.0 kg/ha, 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 both to pre-emergence and post-emergence applications.
  • the total application rate is preferably in the range from 0.001 to 2 kg/ha, preferably in the range from 0.005 to 1 kg/ha, in particular in the range from 10 to 500 g/ha, very particularly preferably in the range from 20 to 250 g/ha. This applies both to pre-emergence and post-emergence applications.
  • the application as a stalk shortener can be carried out at different stages of plant growth. For example, application after tillering at the beginning of longitudinal growth is preferred.
  • seed treatment when used as a plant growth regulator, seed treatment can also be considered, which includes various seed dressing and coating techniques.
  • the application rate depends on the individual techniques and can be determined in preliminary tests.
  • mixture formulations or in tank mix which can be used are, for example, known active ingredients which are based on an inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II or protoporphyrinogen oxidase, as described, for example, in Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 19th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2021 and the literature cited therein.
  • Known herbicides or plant growth regulators which can be combined with compounds of the general formula (I) include, for example, the following active ingredients (the compounds are designated either by the "common name” according to the International Organization for Standardization (ISO) or by the chemical name or by the code number) and always include all application forms such as acids, salts, esters and isomers such as stereoisomers and optical isomers.
  • Acetochlor Acifluorfen, Acifluorfen-methyl, Acifluorfen-sodium, Aclonifen, Alachlor, Allidochlor, Alloxydim, Alloxydim-sodium, Ametryn, Amicarbazon, Amidochlor, Amidosulfuron, 4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methylphenyl)-5-fluoropyridine-2-carboxylic acid, Aminocyclopyrachlor, Aminocyclopyrachlor-potassium, Aminocyclopyrachlor-methyl, Aminopyralid, Aminopyralid-dimethylammonium, Aminopyralid-tripromine, Amitrol, Ammonium sulfamate, Anilofos, Asulam, Asulam-potassium, Asulam-sodium, Atrazine, Azafenidine, Azimsul
  • 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-l,2-oxazolidin-3-one, 2-(2,5-dichlorobenzyl)-4,4-dimethyl-l,2-oxazolidin-3-one, dichlorprop, dichlorprop butotyl, dichlorprop- Dimethylammonium, Dichlorprop-etexyl, Dichlorprop-ethylammonium, Dichlorprop-isoct
  • growth regulators and plant stimulants as mixing partners are:
  • Abscisic acid and related analogues [e.g. (2Z,4E)-5-[6-ethynyl-l-hydroxy-2,6-dimethyl-4- oxocyclohex-2-en-l-yl]-3-methylpenta-2,4-dienoic acid, methyl-(2Z,4E)-5-[6-ethynyl-l-hydroxy-2,6- dimethyl-4-oxocyclohex-2-en-l-yl]-3-methylpenta-2,4-dienoate, (2Z,4E)-3-ethyl-5-(l-hydroxy-2,6,6- trimethyl-4-oxocyclohex-2-en-l-yl)penta-2,4-dienoic acid, (2E,4E)-5-(l-hydroxy-2,6,6-trimethyl-4- oxocyclohex-2-en-l-yl)-3-(trifluoromethyl)penta-2,4-dienoic
  • aminooxyacetic acid and related esters [e.g. (isopropylidene)-aminooxyacetic acid-2-(methoxy)-2-oxoethyl ester, (isopropylidene)-aminooxyacetic acid-2-(hexyloxy)-2-oxoethyl ester, (cyclohexylidene)-aminooxyacetic acid-2-(isopropyloxy)-2-oxoethyl ester], 1-aminocycloprop-1-ylcarboxylic acid, N-methyl-1-aminocyclopropyl-l-carboxylic acid, 1-aminocyclopropyl-1-carboxylic acid amide, substituted 1-aminocyclopropyl-1-carboxylic acid derivatives as described in DE3335514, EP
  • COs differ from LCOs in that they lack the fatty acid side chain characteristic of LCOs.
  • COs sometimes referred to as N-acetylchitooligosaccharides, are also composed of GlcNAc units, but have side chains that distinguish them from chitin molecules [(CSHBNOS) ⁇ CAS NO. 1398-61-4] and chitosan molecules [(C5H11NO4 CAS No.
  • chitin-like compounds chlormequat chloride, cloprop, cyclanilide, 3-(cycloprop-l-enyl)propionic acid, l-[2-(4-cyano-3,5-dicyclopropylphenyl)acet-amido]cyclohexanecarboxylic acid, l-[2-(4-cyano-3-cyclopropylphenyl)acetamido]cyclohexanecarboxylic acid, 1-cyclopropenylmethanol, daminozide, dazomet, dazomet sodium, n-decanol, dikegulac, dikegulac sodium, endothal, endothal-di-potassium, -di-sodium, and mono(N,N-dimethylalkylammonium), ethephon, l-ethylcyclopropene, flumetralin, flurenol, flurenol-butyl
  • LCO lipochitooligosaccharides
  • Nod or Nod factors symbiotic nodulation signals
  • Myc factors consist of an oligosaccharide backbone of ß-l,4-linked V-acetyl-D-glucosamine residues (“GlcNAc”) with an N-linked fatty acid side chain fused to the non-reducing end.
  • LCOs differ in the number of GlcNAc units in the backbone structure, in the length and degree of saturation of the fatty acid chain as well as in the substitution of the reducing and non-reducing sugar units), linoleic acid or its derivatives, linolenic acid or its derivatives, maleic hydrazide, mepiquat chloride, mepiquat pentaborate, 1-methylcyclopropene, 3-methylcyclopropene, methoxyvinylglycine (MVG), 3'-methylabscisic acid, l-(4-methylphenyl)-N-(2- oxo-1 -propyl- 1,2, 3, 4-tetrahydroquinolin-6-yl)methanesulfonamide and related substituted (tetrahydroquinolin-6-yl)methanesulfonamides, (3E,3aR,8ßS)-3-( ⁇ [(2R)-4-methyl-5-oxo
  • nA is a natural number from 0 to 5, preferably 0 to 3
  • RA 1 is halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, nitro or (C1-C4)-haloalkyl
  • WA is an unsubstituted or substituted divalent heterocyclic radical from the group of the partially saturated or aromatic five-membered ring heterocycles with 1 to 3 hetero ring atoms from the group N and O, where at least one N atom and at most one O atom is contained in the ring, preferably a radical from the group (WA 1 ) to (WA 5 ), m A is 0 or 1
  • R A 2 is OR A 3 , SR A 3 or NR A 3 R A 4 or a saturated or unsaturated 3- to 7-membered
  • R B 1 is halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, nitro or (C 1 -C 4 )-haloalkyl;
  • n B is a natural number from 0 to 5, preferably 0 to 3;
  • R B 2 is OR B 3 , SR B 3 or NR B 3 R B 4 or a saturated or unsaturated 3- to 7-membered heterocycle having at least one N atom and up to 3 heteroatoms, preferably from the group O and S, which is linked via the N atom to the carbonyl group in (S2) and is unsubstituted or substituted by radicals from the group (C 1 - C 4 )-alkyl, (C 1 -C 4 )-alkoxy or optionally substituted phenyl, preferably a radical of the formula OR B 3 , NHR B 4 or N
  • RC 1 is (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C2-C4)-alkenyl, (C2-C4)-haloalkenyl, (C3-C7)-cycloalkyl, preferably dichloromethyl;
  • R C 2 , R C 3 are identical or different and are hydrogen, (C1-C4)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C1-C4), haloalkyl, (C2-C4)-haloalkenyl, (C1-C4)-alkylcarbamoyl-(C1-C4)-alkyl, (C2-C4)-alkenylcarbamoyl-(C1-C4)-alkyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, dioxo
  • X D is CH or N;
  • R D 1 is CO-NR D 5 R D 6 or NHCO-R D 7 ;
  • RD 2 is halogen, (C1-C4)haloalkyl, (C1-C4)haloalkoxy, nitro, (C1-C4)alkyl, (C1-C4)alkoxy, (C1-C4)alkylsulfonyl, (C1-C4)alkoxycarbonyl or (C1-C4)alkylcarbonyl;
  • RD 3 is hydrogen, (C1-C4)alkyl, (C2-C4)alkenyl or (C2-C4)alkynyl;
  • RD 4 is halogen, nitro, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)haloalkoxy, (
  • RD 8 and RD 9 independently of one another are hydrogen, (C1-C8)-alkyl, (C3-C8)-cycloalkyl, (C3-C6)-alkenyl, (C3-C6)-alkynyl, RD 4 is halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, CF3 m D 1 or 2; for example 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea, 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea, 1-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea.
  • S5 Active ingredients from the class of hydroxyaromatics and aromatic-aliphatic carboxylic acid derivatives (S5), e.g. ethyl 3,4,5-triacetoxybenzoate, 3,5-dimethoxy-4-hydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4-fluorosalicyclic acid, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid, as described in WO-A-2004/084631, WO-A-2005/015994, WO-A-2005/016001.
  • S6 Active ingredients from the class of 1,2-dihydroquinoxalin-2-ones (S6), e.g.
  • Active ingredients from the class of 3-(5-tetrazolylcarbonyl)-2-quinolones e.g. 1,2-dihydro-4-hydroxy-1-ethyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No. 219479-18-2), 1,2-dihydro-4-hydroxy-1-methyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No. 95855-00-8), as described in WO-A-1999/000020.
  • S11 Active ingredients of the oxyimino compound type (S11), which are known as seed dressing agents, such as. E.g., "Oxabetrinil” ((Z)-1,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile) (S11-1), which is known as a seed dressing safener for millet against metolachlor damage, "Fluxofenim” (1-(4-chloro-phenyl)-2,2,2-trifluoro-1-ethanone-O-(1,3-dioxolan-2-ylmethyl)-oxime) (S11-2), which is known as a seed dressing safener for millet against metolachlor damage, and "Cyometrinil” or “CGA-43089” ((Z)-cyanomethoxyimino(phenyl)acetonitrile) (S11-3), which is known as a seed dressing safener for millet against metolachlor damage.
  • S12 Active ingredients from the class of isothiochromanones (S12), such as methyl [(3-oxo-1H-2-benzothiopyran-4(3H)-ylidene)methoxy]acetate (CAS Reg. No. 205121-04-6) (S12-1) and related compounds from WO-A-1998/13361.
  • S12 isothiochromanones
  • S13 One or more compounds from group (S13): “Naphthalic anhydride” (1,8-naphthalenedicarboxylic anhydride) (S13-1), which is known as a seed dressing safener for maize against damage from thiocarbamate herbicides, "Fenclorim” (4,6-dichloro-2-phenylpyrimidine) (S13-2), which is known as a safener for pretilachlor in sown rice, “Flurazole” (benzyl-2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate) (S13-3), which is known as a seed dressing safener for millet against damage from alachlor and metolachlor, "CL 304415” (CAS Reg.
  • 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.26-480) and/or their salts are: cloquintocet-mexyl, cyprosulfamide, fenchlorazole ethyl ester, isoxadifen-ethyl, mefenpyr-diethyl, fenclorim, cumyluron, S1-14, S1-15, S1-16, S1-17, S1-18, S1-19, S4-1 and S4-5, and particularly preferred safeners are: cloquintocet-mexyl, cyprosulfamide, isoxadifen-ethyl and mefenpyr-diethyl.
  • Biological examples are:
  • ABUTH Abutilon theophrasti
  • BRSNS Brassica napus
  • ECHCG Echinochloa crus-galli
  • KCHSC Kochia scoparia
  • MATIN Matricaria inodora
  • ORYZA Oryza sativa
  • PHPBU Pharbitis purpurea
  • POLCO Polygonum sylvatica
  • VERPE Veronica persica
  • VIOTR Viola tricolor
  • TRZAS Triticum aestivum
  • Emulsion with the addition of 0.5% additive was sprayed onto the green parts of the plant at a water application rate of the equivalent of 600 l/ha. After the test plants had been in the greenhouse for around 3 weeks under optimal growth conditions, the effect of the preparations was assessed visually in comparison to untreated controls. For example, 100% effect means plants have died, 0% effect means like control plants.
  • Tables A1 to A14 below show the effects of selected compounds of the general formula (I) according to Table 1 on various weeds and at an application rate corresponding to 20 g/ha and lower, obtained according to the test procedure mentioned above.
  • Table A6b Post-emergence effect at 5g/ha against ECHCG in %
  • Table A6c Post-emergence effect at 20g/ha against ECHCG in %
  • Table A8b Post-emergence effect at 5g/ha against MATIN in %
  • Table A8c Post-emergence effect at 20g/ha against MATIN in %
  • Table A14b Post-emergence effect at 5g/ha against KCHSC in %
  • Table A14c Post-emergence effect at 20g/ha against KCHSC in %
  • Test plants were treated at the single leaf stage.
  • the compounds according to the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC), were then applied as an aqueous suspension or as a liquid solution.
  • WP wettable powders
  • EC emulsion concentrates
  • Emulsion with the addition of 0.5% additive was sprayed onto the green parts of the plant at a water application rate of the equivalent of 600 l/ha. After the test plants had been in the greenhouse for around 3 weeks under optimal growth conditions, the effect of the preparations was assessed visually in comparison to untreated controls. For example, 100% effect means plants have died, 0% effect means like control plants.
  • Tables Bl to B3 below show the effects of selected compounds of general formula (I) according to Table 1 on various crops and at an application rate corresponding to 20 g/ha and lower, obtained according to the test procedure mentioned above.
  • Table Bla Post-emergence effect at 1.25 g/ha against ZEAMX in %
  • compounds of the general formula (I) according to the invention when applied post-emergence, have good herbicidal activity against harmful plants such as, for example, Abutilon theophrasti, Alopecurus myosuroides, Amaranthus retroflexus, Avena fatua, Digitaria sanguinalis, Echinochloa crus-galli, Lolium rigidum, Matricaria inodora, Pharbitis purpurea, Polygonum convolvulus, Setaria viridis, Veronica persica, Viola tricolor and Kochia scoparia at an application rate of 0.02 kg of active substance or less per hectare, and good crop plant tolerance by organisms such as, for example, Zea mays, Triticum aestivum and Glycine max at an application rate of 0.005 kg per hectare or less.
  • harmful plants such as, for example, Abutilon theophrasti, Alopecurus myosuroides, Amaranthus retroflexus, Avena fatua, Digitaria sanguinalis, E

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  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
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  • Chemical Kinetics & Catalysis (AREA)
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Abstract

La présente invention concerne des cyclopropyloxyphényluraciles 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 mauvaises herbes et/ou les mauvaises herbes graminées dans les cultures, et/ou en tant que régulateurs de croissance des plantes pour influencer la croissance des cultures.
PCT/EP2023/081597 2022-11-16 2023-11-13 Cyclopropyloxyphényluraciles substitués et leurs sels, et leur utilisation comme principes actifs herbicides WO2024104952A1 (fr)

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