WO2021209486A1 - Pyrroline-2-ones à substitution spécifique et leur utilisation en tant qu'herbicides - Google Patents

Pyrroline-2-ones à substitution spécifique et leur utilisation en tant qu'herbicides Download PDF

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WO2021209486A1
WO2021209486A1 PCT/EP2021/059628 EP2021059628W WO2021209486A1 WO 2021209486 A1 WO2021209486 A1 WO 2021209486A1 EP 2021059628 W EP2021059628 W EP 2021059628W WO 2021209486 A1 WO2021209486 A1 WO 2021209486A1
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alkyl
plants
compounds
methyl
general formula
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Hartmut Ahrens
Alfred Angermann
Lars ARVE
Guido Bojack
Estella BUSCATÓ ARSEQUELL
Elisabeth ASMUS
Elmar Gatzweiler
Jan Dittgen
Christopher Hugh Rosinger
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Bayer Aktiengesellschaft
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/54—Spiro-condensed
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • A01N43/38—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings condensed with carbocyclic rings
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • A01N47/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/46—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/52—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a ring other than a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/385—Saturated compounds containing a keto group being part of a ring
    • C07C49/517—Saturated compounds containing a keto group being part of a ring containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
    • C07C57/42—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings having unsaturation outside the rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
    • C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
    • C07C57/60—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings having unsaturation outside the rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/12—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Definitions

  • the present invention relates to new herbicidally active pyrrolin-2-ones according to the general formula (I) or agrochemically acceptable salts thereof, and their use for combating weeds and grass weeds in crops of useful plants.
  • bicyclic phenylpyrrolin-2-one derivatives EP 0355599 A1 and EP 0415211 A2
  • substituted monocyclic 3-phenylpyrrolin-2-one derivatives EP 0377893 A2 and EP 0442077 A2 with herbicidal, insecticidal or fungicidal effect described.
  • the effectiveness of these herbicides against harmful plants depends on numerous parameters, for example on the application rate used, the form of preparation (formulation), the harmful plants to be controlled, the spectrum of harmful plants, the climatic and soil conditions and the duration of the action or the rate of degradation of the herbicide.
  • Numerous herbicides from the 3-phenylpyrrolin-2-ones group require high application rates and / or their weed spectrum to be too narrow in order to develop a sufficient herbicidal action, which makes their use economically unattractive. There is therefore a need for alternative herbicides which have improved properties and are economically attractive and at the same time efficient.
  • the object of the present invention is therefore to provide new compounds which do not have the disadvantages mentioned.
  • the present invention therefore relates to new substituted pyrrolin-2-ones of the general formula
  • X is Ci-Cö-alkyl, Ci-Cö-haloalkyl, C3-C6-cycloalkyl, chlorine, bromine or fluorine;
  • Y is Ci-Cö-alkyl, Ci-Cö-haloalkyl or C3-C6-cycloalkyl;
  • R 1 is C2-C6 difluoroalkoxy
  • R 2 hydrogen, Ci-Cö-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-Cö-haloalkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl, C2-C6- Alkenyl, C2-C6-alkynyl, Ci-Cö-alkoxy or Ci-Cö-haloalkoxy means;
  • G denotes hydrogen, a removable group L or a cation E, where
  • R 3 is Ci-C4-alkyl or Ci-C3-alkoxy-Ci-C4-alkyl
  • R 4 is Ci-C4-alkyl
  • R 5 C1-C4- alkyl, an unsubstituted phenyl or a single or multiple with halogen, C1-C4-
  • R 6 , R 6 'independently of one another denote methoxy or ethoxy
  • R 7 'R 8 each independently represent methyl, ethyl, phenyl or, together with the nitrogen atom to which they are attached, form a saturated 5-, 6- or 7-hydrogen ring, a ring carbon atom optionally replaced by an oxygen or sulfur atom can be replaced;
  • E is an alkali metal ion, an ion equivalent of an alkaline earth metal, an ion equivalent
  • Halogen fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine and particularly preferably fluorine or chlorine.
  • Alkyl saturated, straight-chain or branched hydrocarbon radical having from 1 to 6, (but not limited to) preferably 1 to 4 carbon atoms, for example, CI-C ⁇ - alkyl such as methyl, ethyl, propyl (n-propyl), 1-methylethyl (isopropyl ), Butyl (n-butyl), 1-methylpropyl (sec-butyl), 2-methylpropyl (isobutyl), 1,1-dimethylethyl (tert-butyl), pentyl, 1-methylbutyl, 2-methylbutyl, 3 - methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1 , 2-dimethylbutyl
  • This group is in particular a C1-C4 alkyl group, e.g. B. methyl, ethyl, propyl, 1-methylethyl (isopropyl), butyl, 1-methylpropyl (sec-butyl), 2-methylpropyl (isobutyl) or 1,1-dimethylethyl - (tert-butyl) group.
  • C1-C4 alkyl group e.g. B. methyl, ethyl, propyl, 1-methylethyl (isopropyl), butyl, 1-methylpropyl (sec-butyl), 2-methylpropyl (isobutyl) or 1,1-dimethylethyl - (tert-butyl) group.
  • alkylsulfanyl alkylsulfinyl, alkylsulfonyl, haloalkyl or haloalkylsulfanyl
  • this definition also applies to alkyl as part of a compound substituent, for example cycloalkylalkyl or hydroxyalkyl.
  • Alkenyl unsaturated straight-chain or branched hydrocarbon groups with 2 to 6 and preferably 2 to 4 carbon atoms and a double bond in any position, for example (but not limited to) C2-C6 alkenyl, such as vinyl, allyl, (E) -2- Methyl vinyl, (Z) -
  • Alkynyl straight-chain or branched hydrocarbon groups with 2 to 6 and preferably 2 to 4 carbon atoms and a triple bond in any position, for example (but not limited to) C2-C6-alkynyl, such as ethynyl, prop-1-ynyl, prop-2 -ynyl, but-1-ynyl, but-2-ynyl, but-3-ynyl, 1-methylprop-2-ynyl, pent-1-ynyl, pent-2-ynyl, pent-3-ynyl, pent-4 -ynyl, 2-methylbut-3-ynyl, 1-methylbut-3-ynyl, 1-methylbut-2-ynyl, 3-methylbut-1-ynyl, 1-ethylprop-2-ynyl, hex-1-ynyl, hex -2-ynyl, hex-3-ynyl, hex-4-ynyl, hex-5-
  • alkynyl group is in particular ethynyl, prop-1-ynyl or prop-2-ynyl. Unless otherwise defined, this definition also applies to alkynyl as part of a compound substituent, for example haloalkynyl.
  • Alkoxy saturated, straight-chain or branched alkoxy radicals with 1 to 6 and preferably 1 to 4 carbon atoms, for example (but not limited to) Ci-CT alkoxy such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2 -Methylpropoxy, 1,1-dimethylethoxy, pentoxy, 1 -methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, hexoxy, 1-methylpentoxy , 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1 -Ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylprop
  • Cycloalkyl monocyclic, saturated hydrocarbon groups with 3 to 6
  • Carbon ring members for example (but not limited to) cyclopropyl, cyclopentyl and cyclohexyl. Unless otherwise defined, this definition also applies to cycloalkyl as part of a compound substituent, for example cycloalkylalkyl.
  • Haloalkyl / haloalkyl straight-chain or branched alkyl groups with 1 to 6, preferably 1 to 4 carbon atoms (as described above), some or all of the hydrogen atoms in these groups being replaced by halogen atoms as described above, for example (but not limited to) Ci -C3-haloalkyl such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1 -fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2.2 , 2- trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-
  • Haloalkenyl and haloalkynyl are defined analogously to haloalkyl, however, instead of alkyl groups, alkenyl or alkynyl groups are present as part of the substituent.
  • Haloalkoxy straight-chain or branched alkoxy groups having 1 to 6, preferably 1 to 3 carbon atoms (as described above), with some or all of the hydrogen atoms in these groups being replaced by halogen atoms as described above, for example (but not thereon limited)
  • Ci-C3-haloalkoxy such as chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1 -chloroethoxy, 1-bromoethoxy, 1 -fluoroethoxy, 2-fluorine 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2,2-trichloroethoxy
  • the compounds of the formula (I) can exist as geometric isomers (cis / trans isomerism) or isomer mixtures in different compositions.
  • the geometric isomers are defined as follows:
  • the present invention relates to both the pure isomers or tautomers and the tautomer and isomer mixtures, their preparation and use and agents containing them. This also applies analogously to all isomers that result from the use of chiral substituents. For the sake of simplicity, however, compounds of the formula (I) are always referred to below, although both the pure compounds and, if appropriate, mixtures with different proportions of isomeric and tautomeric compounds are meant.
  • X is Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, chlorine, bromine or fluorine;
  • Y is Ci-C4-alkyl, Ci-C4-haloalkyl or C3-C6-cycloalkyl;
  • R 1 is C2-C4 difluoroalkoxy
  • R 2 denotes hydrogen, Ci-C6-alkyl, Ci-C4-alkoxy-C2-C4-alkyl, Ci-C6-haloalkyl, C3-C6-cycloalkyl, C2-C6-alkenyl or C2-C6-alkynyl;
  • G denotes hydrogen, a removable group L or a cation E, where L is one of the following radicals, wherein
  • R 3 is Ci-C4-alkyl or Ci-C3-alkoxy-Ci-C4-alkyl
  • R 4 is Ci-C4-alkyl
  • R 5 is Ci-C4-alkyl, an unsubstituted phenyl or a phenyl which is mono- or polysubstituted by halogen, C1-C4-alkyl, halogen- (Ci-C4) -alkyl or Ci-C4-alkoxy;
  • E is an alkali metal ion, an ion equivalent of an alkaline earth metal, an ion equivalent
  • X is Ci-C4-alkyl, Ci-C4-haloalkyl, cyclopropyl, chlorine, bromine or fluorine;
  • Y is Ci-C4-alkyl, Ci-C4-haloalkyl or cyclopropyl
  • R 1 is C2-C4 difluoroalkoxy
  • R 2 denotes hydrogen, Ci-C4-alkyl, methoxyethyl or ethoxyethyl, Ci-C2-haloalkyl, cyclopropyl, C2-C4-alkenyl or C2-C4-alkynyl;
  • G denotes hydrogen, a group F which can be split off or a cation E, where
  • R 3 is Ci-C4-alkyl or Ci-C2-alkoxy-Ci-C2-alkyl
  • R 4 is Ci-C4-alkyl
  • E is an alkali metal ion, an ion equivalent of an alkaline earth metal, an ion equivalent
  • Aluminum an ion equivalent of a transition metal, a magnesium-halogen cation or an ammonium ion, in which one, two, three or all four hydrogen atoms are optionally replaced by identical or different radicals from the groups Ci-Cio-alkyl or C3-C7- Cycloalkyl.
  • X is methyl, ethyl, cyclopropyl, chlorine, bromine or fluorine
  • Y is methyl, ethyl, trifluoromethyl or cyclopropyl
  • R 1 is 2,2-difluoroethoxy, 2,2-difluoropropoxy or 3,3-difluoropropoxy
  • R 2 is hydrogen or methyl
  • G denotes hydrogen, a removable group L or a cation E, where
  • L is one of the following residues, OO r in which
  • R 3 is methyl, ethyl, isopropyl or t-butyl
  • R 4 is methyl or ethyl
  • E is a sodium ion or a potassium ion.
  • the present invention also preferably relates to compounds of the general formula (Ix) and their agrochemically acceptable salts, where the radicals R 2 , G, X and Y correspond to the general, preferred, particularly preferred and very particularly preferred definitions given above:
  • the present invention further relates to the compounds of the general formula (I) in Tables 1 to 10.
  • Is hydrogen and G is a sodium ion.
  • a very particularly preferred embodiment of the present invention are the following compounds:
  • Table 3 Compounds of the general formula (I) according to the invention in which R 2 is hydrogen and G is a 2-methylpropionyl radical.
  • Table 4 Compounds according to the invention of the general formula (I) in which R 2 is
  • Is hydrogen and G is a methoxycarbonyl radical.
  • Methyl group and G is hydrogen.
  • Table 7 Compounds of the general formula (I) according to the invention in which R 2 is a methyl group and G is a sodium ion.
  • Methyl group and G is a 2-methylpropionyl radical.
  • Methyl group and G denotes a methoxycarbonyl radical.
  • Table 10 Compounds of the general formula (I) according to the invention in which R 2 is a methyl group and G is an ethoxycarbonyl radical.
  • the preparation of the compounds of the general formula (I) according to the invention is known in principle or can be carried out on the basis of processes known from the literature, for example by a) a compound of the general formula (II), in which R 1 , R 2 , X and Y have the meanings given above, and R 9 is alkyl, preferably methyl or ethyl, optionally in the presence of a suitable solvent or diluent, with a suitable base with formal cleavage of the group R 9 OH cyclizes, or b) a compound of the general formula (Ia), in which R 1 , R 2 , X and Y have the meanings given above, for example with a compound of the general formula (III),
  • halogen preferably chlorine or bromine
  • the precursors of the general formula (II) can be prepared in analogy to known processes, for example by reacting an amino ester of the general formula (IV), in which R 1 , R 2 and R 9 have the meaning described above, with a phenylacetic acid of the general formula ( V), in which X and Y have the meaning described above, optionally with the addition of a dehydrating agent and a suitable solvent or diluent.
  • Amino esters of the general formula (IV) are, for example, synthetically accessible via a difluoroalkylation of the cyclohexanol (VI), followed by the cleavage of the ketal (VII) to give the substituted cyclohexanone (VIII).
  • Phenylacetic acids of the general formula (V) are known, inter alia, from WO 15/040114 or can be prepared in analogy to processes known from the literature.
  • the propynyl group can be installed via a cross-coupling such as the Sonogashira coupling.
  • a suitable precursor (Vb) is used, for example as an ester, in which there is an exchange of a suitable substituent Z by the propynyl radical.
  • the product (Va) is then saponified to form phenylacetic acid (V).
  • substituent Z examples are in particular the halogens bromine and iodine as well as sulfonic acid esters of the corresponding phenols such as the trifluoromethanesulfonic acid ester.
  • the radical R 10 stands for methyl or ethyl. Further explanations can also be found in the chemical examples.
  • the present invention further relates to the compounds of the formula (II) or an agrochemically acceptable salt thereof, the radicals having the definitions described above, including the preferred, particularly preferred and very particularly preferred radical definitions.
  • Table 11 Compounds of the general formula (II) according to the invention in which R 9 stands for a methyl group.
  • the present invention further relates to the compounds of the formula (IV) or an agrochemically acceptable salt thereof, the radicals having the definitions described above, including the preferred, particularly preferred and very particularly preferred radical definitions.
  • the present invention further relates to the compounds of the formula (IX), where the radicals have the definitions described above, including the preferred, particularly preferred and very particularly preferred radical definitions.
  • Table 14 Compounds of the general formula (IX) according to the invention
  • the present invention further relates to the compounds of the formula (X), where the radicals have the definitions described above, including the preferred, particularly preferred and very particularly preferred radical definitions.
  • Table 15 Compounds of the general formula (X) according to the invention
  • the present invention further relates to the compounds of the formula (VIII), where the radicals have the definitions described above, including the preferred, particularly preferred and very particularly preferred radical definitions.
  • Table 16 Compounds of the general formula (VIII) according to the invention Examples 16-1 and 16-2 are not new and are only used to support the description.
  • the present invention further relates to the compounds of the formula (VII), where the radicals have the definitions described above, including the preferred, particularly preferred and very particularly preferred radical definitions.
  • Table 17 Compounds of the general formula (VII) according to the invention
  • Examples 17-1 and 17-2 are not new and are only used to support the description.
  • the present invention further relates to the compounds of the formula (V), where the radicals have the definitions described above, including the preferred, particularly preferred and very particularly preferred radical definitions.
  • Table 18 Compounds of the general formula (V) according to the invention
  • Examples 18-1, 18-2 and 18-7 are not new and are only used to support the description.
  • the present invention further relates to the compounds of the formula (Va), where the radicals have the definitions described above, including the preferred, particularly preferred and very particularly preferred radical definitions.
  • Table 19 Compounds according to the invention of the general formula (Va) Examples 19-1, 19-2, 19-5, 19-7, 19-22, 19-23, 19-26 and 19-28 are not new and are only used to support the description.
  • the compounds of the formula (I) according to the invention (and / or their salts), hereinafter referred to collectively as “compounds according to the invention”, have excellent herbicidal properties Effectiveness against a broad spectrum of economically important monocotyledon and dicotyledon annual harmful plants.
  • the present invention therefore also provides a method for controlling undesired plants or for regulating the growth of plants, preferably in plant crops, in which one or more compound (s) according to the invention are applied to the plants (for example harmful plants such as monocotyledonous or dicotyledonous weeds or undesired crop plants), the seeds (e.g. grains, seeds or vegetative reproductive organs such as tubers or sprouts with buds) or the area on which the plants grow (e.g. the area under cultivation) are applied.
  • the compounds according to the invention can be applied in the pre-sowing (if necessary also by incorporation into the soil), pre-emergence or post-emergence method, for example.
  • the compounds according to the invention are applied to the surface of the earth before germination, either the emergence of the weed seedlings is completely prevented or the weeds grow up to the cotyledon stage, but then stop growing.
  • the compounds according to the invention can have selectivities in useful crops and can also be used as nonselective herbicides.
  • the active compounds can also be used for controlling harmful plants in crops of known or still to be developed genetically modified plants.
  • the transgenic plants are usually characterized by particularly advantageous properties, for example by resistance to certain active ingredients used in the agricultural industry, especially certain herbicides, resistance to plant diseases or pathogens causing plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
  • Other special properties relate, for example, to the crop in terms of quantity, quality, shelf life, composition and special ingredients.
  • transgenic plants with an increased starch content or a changed quality of the starch or those with a different fatty acid composition of the harvested material are known.
  • Other special properties are tolerance or resistance to abiotic stressors e.g. heat, cold, drought, salt and ultraviolet radiation.
  • the compounds of the formula (I) can be used as herbicides in crops of useful plants which are resistant to the phytotoxic effects of the herbicides or which have been made resistant by genetic engineering.
  • new plants with modified properties can be produced with the aid of genetic engineering (see, for example, EP 0221044, EP 0131624).
  • genetic modifications of crop plants for the purpose of modifying the starch synthesized in the plants e.g.
  • transgenic crop plants which are effective against certain herbicides of the glufosinate type ( See, for example, EP 0242236 A, EP 0242246 A) or glyphosate (WO 92/000377 A) or the sulfonylureas (EP 0257993 A, US 5,013,659) or are resistant to combinations or mixtures of these herbicides by “gene stacking”, such as transgenic crops e.g. . B. corn or soy with the trade name or the designation Optimum TM GAT TM (Glyphosate ALS Tolerant).
  • transgenic cultivated plants for example cotton, with the ability to produce Bacillus thuringiensis toxins (Bt toxins), which the plants against certain Making pests resistant (EP 0142924 A, EP 0193259 A).
  • Bacillus thuringiensis toxins Bacillus thuringiensis toxins
  • transgenic crop plants with modified fatty acid composition WO 91/013972 A
  • genetically modified crop plants with new ingredients or secondary substances, for example new phytoal exines, which cause increased disease resistance EP 0309862 A, EP 0464461
  • nucleic acid molecules can be introduced into plasmids which allow mutagenesis or a sequence change by 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, see, for example, Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd edition. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY; or Winnacker "Genes and Clones", VCH Weinheim 2nd edition 1996
  • 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, one sense RNA to achieve a cosuppression effect or by expressing at least one appropriately constructed ribozyme that specifically cleaves transcripts of the above-mentioned gene product.
  • DNA molecules can be used that include the entire coding sequence of a gene product including any flanking sequences that may be present, as well as DNA molecules that only include parts of the coding sequence, these parts having to be long enough to be in the cells to bring about 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 which are not completely identical.
  • the synthesized protein can be localized in any desired compartment of the plant cell.
  • the coding region can be linked with DNA sequences which ensure the localization in a certain compartment.
  • sequences are known to Lachmann (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al., Plant J. 1: 95-106 (1991)).
  • 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 compounds (I) according to the invention can preferably be used in transgenic cultures which are effective against growth substances such as 2,4-D, dicamba or against herbicides, the essential plant enzymes, for example acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydoxyphenylpyruvate Dioxygenases (HPPD) inhibit or are resistant to herbicides from the group of sulfonylureas, glyphosates, glufosinates or benzoylisoxazoles and analogous active ingredients, or to any combination of these active ingredients.
  • the essential plant enzymes for example acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydoxyphenylpyruvate Dioxygenases (HPPD) inhibit or are resistant to herbicides from the group of sulfonylureas, glyphosates, glufosinates or benzoylis
  • the compounds according to the invention can particularly preferably be used in transgenic crop plants which are resistant to a combination of glyphosates and glufosinates, glyphosates and sulfonylureas or imidazolinones.
  • the compounds according to the invention can very particularly preferably be used in transgenic crop plants such as, for. B. corn or soy with the trade name or the designation OptimumTM GATTM (Glyphosate ALS Tolerant) can be used.
  • the active ingredients according to the invention are used in transgenic crops, in addition to the effects on harmful plants that can be observed in other crops, 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 controlled, often occur
  • 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 formula (I) according to the invention as herbicides for controlling harmful plants in transgenic crop plants.
  • the compounds 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 agents which contain the compounds according to the invention.
  • the compounds according to the invention can be formulated in various ways, depending on which biological and / or chemico-physical parameters are given. Possible formulation options include, for example: wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions , Suspension concentrates (SC), oil- or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), dusts (DP), dressings, granules for litter and soil application, granules (GR) in the form of micro, spray, lift - and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), UL V formulas, microcapsules and waxes.
  • WP wettable powders
  • SP water-soluble powders
  • EC emuls
  • combination partners for the compounds according to the invention in mixture formulations or in the tank mix are known active ingredients which are based on an inhibition of, for example Acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate 3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II or protoporphyrinogen oxidase, for example, as they are based from Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc.
  • herbicidal mixing partners are:
  • Dicamba-Biproamin Dicamba-N, N-bis (3-aminopropyl) methylamine, dicamba-butotyl, dicamba-choline, dicamba-diglycolamine, dicamba-dimethylammonium, dicamba-diethanolamine monium, dicamba diethylammonium, dicamba isopropylammonium, dicamba methyl, dicamba monoethanolamine dicamba olamine, dicamba kabum, dicamba sodium, dicamba triethanolamine, dichlobenil, 2- (2,5-dichlorobenzyl) -4,4- dimethyl l, 2-oxazobdin-3-one, dichlorprop, dichlorprop-butotyl, dichloroprop-dimethylammonium, dichlorprop-etexyl, dichlorprop-ethylammonium, dichlorprop-isoctyl, dichlorprop-methyl, dichlorprop-kabum, dichlor
  • plant growth regulators as possible mixing partners are:
  • COs, sometimes also referred to as N-acetylchitooligosaccharides also consist of GlcNAc residues, but have side chain decorations that are derived from chitin molecules [(C8Hi3N05) n, CAS no.
  • chitosan molecules [(CsHnNO ⁇ n, CAS No. 9012-76-4]), chitin compounds, chlormequat chloride, cloprop, cyclanilide, 3- (cycloprop-l-enyl) propionic acid, daminozide, dazomet, dazomet -Sodium, n- decanol, dikegulac, dikegulac sodium, endothal, endothal dipotassium, disodium and mono (N, N- dimethylalkylammonium), ethephon, flumetralin, flurenol, flurenol-butyl, flurenol-methyl, flurprimidol, forchlorfenuron, Inabenfid, indole-3-acetic acid e (IAA), 4-indol-3-ylbutyric acid, isoprothiolane, probenazole, jasmonic acid, jasmonic acid or derivatives thereof
  • lipo-chitooligosaccharides LCO, sometimes also referred to as symbiotic nodulation (Nod) signals (or Nod factors) or as Myc factors)
  • Nod symbiotic nodulation
  • Myc myc factors
  • LCOs differ in the number of GlcNAc residues in the backbone, in the length and degree of saturation of the fatty acyl chain and in the substitutions of reducing and non-reducing sugar residues), linoleic acid or derivatives thereof, linolenic acid or derivatives thereof, maleic hydrazide , Mepiquat chloride, mepiquat pentaborate, 1 -methylcyclopropene, 3'- Methylabsiscisic acid, 2- (l-naphthyl) acetamide, 1-naphthylacetic acid, 2-naphthyloxyacetic acid, nitrophenolate mixture, 4-oxo-4 [(2-phenylethyl) amino] butyric acid, paclobutrazole, 4-phenylbutyric acid, N-phenylphthalamic acid, prohexadione, Prohexadione Calcium, Prohydrojasmone, Salicylic
  • Safeners which can be used in combination with the compounds of the formula (I) according to the invention and, if appropriate, in combinations with other active ingredients such as insecticides, acaricides, herbicides, fungicides as listed above, are preferably selected from the group consisting of:
  • nA is a natural number from 0 to 5, preferably 0 to 3;
  • RA 1 is halogen, (Ci-C4) -alkyl, (Ci-C4) -alkoxy, nitro or halogen- (Ci-C4) -alkyl;
  • WA is an unsubstituted or substituted divalent heterocyclic radical from the group of partially unsaturated or aromatic five-membered ring heterocycles with 1 to 3 hetero ring atoms from the group N and O, with at least one N atom and at most one O atom in the ring, preferably one Remainder from group (WA 1 ) to (WA 4 ),
  • IUA is 0 or 1
  • RA 2 is ORA 3 , SRA 3 or NRA 3 RA 4 or a saturated or unsaturated 3 to 7-membered heterocycle with at least one N atom and up to 3 heteroatoms, preferably from the group O and S, which has the N- Atom is connected to the carbonyl group in (S1) and is unsubstituted or by radicals from the group (Ci-C4) -alkyl, (Ci-C4) -alkoxy or optionally substituted phenyl is substituted, preferably a radical of the formula ORA 3 , NHRA 4 or N (CFE) 2, in particular of the formula ORA 3 ;
  • RA 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably with a total of 1 to 18 carbon atoms;
  • RA 4 is hydrogen, (CI-CO) - alkyl, (Ci-G,) - alkoxy or substituted or unsubstituted phenyl;
  • RA 5 is H, (Ci-Cs) -alkyl, halogen- (Ci-C8) -alkyl, (Ci-C4) -alkoxy- (Ci-Cs) -alkyl, cyano or COORA 9 , where RA 9 is hydrogen, ( Ci-Cs) -alkyl, halogen- (Ci-C8) -alkyl, (Ci-C4) -alkoxy- (Ci-C4) -alkyl, (Ci-C6) -hydroxyalkyl, (C3-Ci2) -cycloalkyl or tri - (Ci-C4) -alkyl-silyl;
  • RA 6 , RA 7 , RA 8 are identically or differently hydrogen, (Ci-C8) -alkyl, halogen- (Ci-C8) -alkyl, (C3-Ci2) -cycloalkyl or substituted or unsubstituted phenyl; preferably: a) compounds of the dichlorophenylpyrazoline-3-carboxylic acid type (Sl a ), preferably compounds such as 1- (2,4-dichlorophenyl) -5- (ethoxycarbonyl) -5-methyl-2-pyrazoline-3-carboxylic acid, l - (2,4-Dichlorophenyl) -5- (ethoxycarbonyl) -5-methyl-2-pyrazoline-3-carboxylic acid ethyl ester (S 1 -1) ("Mefenpyr-diethyl”), and related compounds, as described in WO A-91/07874; b) Derivatives of dichlorophen
  • Diphenyl-2-isoxazoline-3-carboxylic acid (Sl e ), preferably compounds such as
  • Ethyl 5- (2,4-dichlorobenzyl) -2-isoxazoline-3-carboxylate (S 1-8) or ethyl 5-phenyl-2-isoxazoline-3-carboxylate (S1-9) and related compounds, as described in WO-A -91/08202 are described, or 5, 5 -diphenyl-2-isoxazobn-3-carboxylic acid (Sl-10) or 5,5-diphenyl-2-isoxazobn-3-carboxylic acid ethyl ester (Sl-11) ("Isoxadifen- ethyl ") or -n-propyl ester (S 1 -12) or the 5- (4-fluorophenyl) -5-phenyl-2-isoxazobn-3-carboxylic acid ethyl ester (S1-13), as described in the patent application WO-A- 95/07897 are described.
  • RB 1 is halogen, (Ci-C4) -alkyl, (Ci-C4) -alkoxy, nitro or halogen- (Ci-C4) -alkyl;
  • nB is a natural number from 0 to 5, preferably 0 to 3;
  • RB 2 is ORB 3 , SRB 3 or NRB 3 RB 4 or a saturated or unsaturated 3- to 7-gbedriger heterocycle with at least one N atom and up to 3 heteroatoms, preferably from the group O and S, which has the N- Atom is connected to the carbonyl group in (S2) and is unsubstituted or substituted by radicals from the group (Ci-C4) -alkyl, (C1-C4) -alkoxy or optionally substituted phenyl, preferably a radical of the formula ORB 3 , NHRB 4 or N (CH3) 2, in particular of the formula ORB 3 ;
  • RB 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably with a total of 1 to 18 carbon atoms;
  • RB 4 is hydrogen, (CI-CO) -alkyl, (Ci-G.) -Alkoxy or substituted or unsubstituted phenyl;
  • TB is a (Ci or C2) alkanediyl chain which is unsubstituted or substituted with one or two (Ci- C4) alkyl radicals or with [(Ci-C3) alkoxy] carbonyl; preferably: a) Compounds of the 8-quinolineoxyacetic acid type (S2 a ), preferably
  • Rc 1 is (Ci-C-alkyl, halogen- (Ci-C4) -alkyl, (C 2 -C4) -alkenyl, halogen- (C 2 -C4) -alkenyl, (C3-C7) -cy cloalkyl, preferably Dichloromethyl;
  • Rc 2 , Rc 3 are identically or differently hydrogen, (Ci-C4) -alkyl, (C 2 -C4) -alkenyl, (C 2 -C4) -alkynyl, halogen- (Ci-C4) -alkyl, halogen- ( C 2 -C4) -alkenyl, (Ci-C4) -alkylcarbamoyl- (Ci-C4) -alkyl, (C2-C4) -alkenylcarbamoyl- (Ci-C4) -alkyl, (Ci-C4) -alkoxy- (Ci -C4) -alkyl, dioxolanyl- (Ci-C4) -alkyl, thiazolyl, furyl, furylalkyl, thienyl, piperidyl, substituted or unsubstituted phenyl, or Rc 2 and Rc 3 together form a substituted or unsubstit
  • R-28725" (3-dichloroacetyl-2,2, -dimethyl-1,3-oxazolidine) from Stauffer (S3-3),
  • Benoxacor (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine) (S3-4),
  • PPG-1292 N-Allyl-N - [(1,3-dioxolan-2-yl) methyl] dichloroacetamide
  • DKA-24 N-Allyl- N - [(allylaminocarbonyl) methyl] dichloroacetamide
  • AD-67 or "MON 4660” (3-dichloroacetyl-l-oxa-3-aza-spiro [4,5] decane) from Nitrokemia or Monsanto (S3-7),
  • TI-35 (1-dichloroacetyl-azepan) from TRI-Chemical RT (S3-8), "Diclonon” (Dicyclonon) or "BAS145138” or “LAB145138” (S3-9)
  • AD is S0 2 -NRD 3 -C0 or C0-NRD 3 -S0 2
  • XD is CH or N
  • RD 1 is CO-NRD 5 RD 6 or NHCO-RD 7 ;
  • RD 2 is halogen, halogen (Ci-C4) -alkyl, halogen- (Ci-C4) -alkoxy, nitro, (Ci-C4) -alkyl, (C1-C4) -alkoxy, (Ci-C4) -alkylsulfonyl , (Ci-C4) -alkoxycarbonyl or (Ci-C4) -alkylcarbonyl;
  • RD 3 is hydrogen, (C1-C4) -alkyl, (C 2 -C4) -alkenyl or (C 2 -C4) -alkynyl;
  • RD 4 is halogen, nitro, (Ci-C4) -alkyl, halogen- (Ci-C4) -alkyl, halogen- (Ci-C4) -alkoxy, (C3-C6) -cycloalkyl, phenyl, (Ci-C4) -Alkoxy, cyano, (Ci-C4) -alkylthio, (Ci-C4) -alkylsulfinyl, (C1-C4) -alkylsulfonyl, (Ci-C4) -alkoxycarbonyl or (Ci-C4) -alkylcarbonyl;
  • RD 5 is hydrogen, (CI-C ⁇ ) - alkyl, (C3-Ce) -cycloalkyl, (C2-Ce) -alkenyl, (C2-Ce) -alkynyl, (C5-C6) -cycloalkenyl, phenyl or 3- up to 6-membered heterocyclyl containing VD heteroatoms from the group nitrogen, oxygen and sulfur, the last seven radicals being replaced by VD substituents from the group halogen, (Ci-G) -alkoxy, halogen- (Ci-G,) alkoxy, ( C1-C2) - alkylsulfinyl, (Ci-C2) -alkylsulfonyl, (C3-Ce) -cycloalkyl, (Ci-C4) -alkoxycarbonyl, (C1-C4) -alkylcarbonyl and phenyl and in the case of cyclic radicals also (C
  • RD 6 is hydrogen, (Ci-G,) - alkyl, (GG) -alkenyl or (GG) -alkynyl, the last three radicals mentioned by VD radicals from the group halogen, hydroxy, (Ci-C4) -alkyl, ( C1-C4) - alkoxy and (C1-C4) - alkyl thio are substituted, or
  • RD 7 is hydrogen, (Ci-C4) -alkylamino, di- (Ci-C4) -alkylamino, (Ci-G) -alkyl, (GG) -cycloalkyl, the last two radicals being replaced by VD substituents from the halogen group , (Ci-C4) -alkoxy, halogen- (Ci-Ce) -alkoxy and (Ci-C4) -alkylthio and in the case of cyclic radicals also (Ci-C4) -alkyl and halogen- (Ci-C4) -alkyl substituted are; hs is 0, 1 or 2; mD is 1 or 2;
  • VD is 0, 1, 2 or 3; Preferred of these are compounds of the N-acylsulfonamide type, for example of the following formula (S4 a ), which z. B. are known from WO-A-97/45016 wherein
  • RD 7 (CI -G,) - alkyl, (C3-C6) -cycloalkyl, where the last 2 radicals mentioned by VD substituents from the group halogen, (Ci-C4) -alkoxy, halogen- (Ci-C6) -alkoxy and (Ci-C4) -Alkylthio and, in the case of cyclic radicals, also (Ci-C4) -alkyl and halogen- (Ci-C4) -alkyl are substituted; RD 4 halogen, (Ci-C 4 ) -alkyl, (Ci-C 4 ) -alkoxy, CF 3; mD 1 or 2;
  • VD is 0, 1, 2 or 3; and acylsulfamoylbenzoic acid amides, for example of the following formula (S4 b ), which are known, for example, from WO-A-99/16744, e.g. those in which
  • RD 8 and Hin 9 independently of one another hydrogen, (Ci-Cs) -alkyl, (C3-Cs) -cycloalkyl, (C3-C6) -alkenyl, (C3-Ce) -alkynyl,
  • RD 4 halogen, (Ci-C 4 ) -alkyl, (Ci-C 4 ) -alkoxy, CF 3 mD is 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, as well as
  • RD 5 denotes hydrogen, (Ci-C 6 ) -alkyl, (C 3 -C6) -cycloalkyl, (C2-C 6 ) -alkenyl, (C 2 -C6) -alkynyl, (Cs-Ce) -cycloalkenyl.
  • 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 the 1,2-dihydroquinoxalin-2-ones (S6), e.g.
  • RE 1 , RE 2 are independently halogen, (Ci-C4) -alkyl, (Ci-C4) -alkoxy, halogen- (Ci-C4) -alkyl, (Ci-C4) -alkylamino, di- (Ci-C4) ) -Alkylamino, nitro;
  • AE is COORE 3 or COSRE 4
  • RE 3 , RE 4 are independently hydrogen, (Ci-C4) -alkyl, (C2-G,) -alkenyl, (C2-C4) -alkynyl, cyanoalkyl, halogen- (Ci-C4) -alkyl, phenyl, nitrophenyl , Benzyl, halobenzyl, pyridinylalkyl and alkylammonium, he 1 is 0 or 1 he 2 , he 3 are independently 0, 1 or 2, preferably:
  • RF 1 halogen, (Ci-C4) -alkyl, halogen- (Ci-C4) -alkyl, (Ci-C4) -alkoxy, halogen- (Ci-C4) -alkoxy, Nitro, (Ci-C4) -Alkylthio, (Ci-C4) -Alkylsulfonyl, (Ci-C4) -Alkoxycarbonyl, optionally substituted. Phenyl, optionally substituted phenoxy,
  • RF 3 is hydrogen, (Ci-Cs) -alkyl, (C2-C4) -alkenyl, (C2-C4) -alkynyl, or aryl, where each of the aforementioned C-containing radicals is unsubstituted or by one or more, preferably up to three identical or different radicals from the group consisting of halogen and alkoxy is substituted; mean, or their salts, preferably compounds in which
  • nF is an integer from 0 to 2
  • RF 3 is hydrogen, (Ci-Cs) -alkyl, (C2-C4) -alkenyl, (C2-C4) -alkynyl, or aryl, where each of the aforementioned C-containing radicals is unsubstituted or by one or more, preferably up to three identical or different radicals from the group consisting of halogen and alkoxy is substituted, or their salts.
  • RG 2 (Ci-Ci6) -alkyl, (C2-Ce) -alkenyl, (C3-Ce) -cycloalkyl, aryl; Benzyl, halobenzyl,
  • RG 3 is hydrogen or (Ci-G,) - alkyl.
  • Active ingredients of the type of oxyimino compounds which are known as seed dressings, such as. B.
  • Oxabetrinil ((Z) -l, 3-Dioxolan-2-ylmethoxyimino (phenyl) acetonitril) (Sll-1), which is known as a seed dressing safener for millet against damage from metolachlor,
  • Fluorofenim (l- (4-chlorophenyl) -2,2,2-trifluoro-l-ethanon-0- (l, 3-dioxolan-2-ylmethyl) oxime) (Sil -2), which is used as a seed dressing Safener for millet is known against damage from metolachlor, and
  • Cyometrinil or “CGA-43089” ((Z) -Cyanomethoxyimino (phenyl) acetonitrile) (S 11-3), which is known as a seed dressing safener for millet against damage from metolachlor.
  • Active ingredients from the class of isothiochromanones such as methyl [(3 -oxo- 1H-2-benzothiopyran-4 (3H) -ylidene) methoxy] acetate (CAS reg. No. 205121-04-6 ) (S12-1) and related compounds from WO-A-1998/13361.
  • Naphthalic anhydride (1,8-naphthalenedicarboxylic acid anhydride) (S13-1), which is known as a seed dressing safener for maize against damage from thiocarbamate herbicides,
  • Active ingredients which, in addition to a herbicidal effect against harmful plants, also have a safener effect
  • CSB (1-bromo-4- (chloromethylsulfonyl) benzene) from Kumiai, (CAS Reg. No. 54091-06-4), which is known as a safener against damage from some herbicides in rice.
  • RH 1 is a halogen (Ci-G,) - alkyl radical
  • RH 2 is hydrogen or halogen and RH 3 , RH 4 independently of one another are hydrogen, (Ci-Ci6) -alkyl, (C2-Ci6) -alkenyl or (C2-C16) -alkynyl, each of the last-mentioned 3 radicals being unsubstituted or by one or more radicals from the group consisting of halogen , Hydroxy, cyano, (Ci-C4) -alkoxy, halogen- (Ci-C4) -alkoxy, (C1-C4) -alkyl thio, (Ci-C4) -alkylamino, di [(Ci-C4) -alkyl] -amino, [(Ci-C4) -alkoxy] -carbonyl, [halogen- (Ci-C4) - alkoxy] -carbony l, (C3-G,) - cycloalkyl which is unsubstituted or substituted
  • RH 3 means (Ci-C4) -alkoxy, (C2-C4) -alkenyloxy, (C2-Ce) -alkinyloxy or halogen- (C2-C4) -alkoxy and
  • RH 4 is hydrogen or (Ci-C4) -alkyl or
  • RH 3 and RH 4 together with the directly bonded N atom form a four- to eight-membered heterocyclic ring which, in addition to the N atom, can also contain further hetero-ring atoms, preferably up to two further hetero-ring atoms from the group N, O and S and which is unsubstituted or by one or more radicals from the group consisting of halogen, cyano, nitro, (Ci-C4) -alkyl, halogen- (Ci-C4) -alkyl, (Ci-C4) -alkoxy, halogen- (Ci-C4) -alkoxy and (Ci-C4) -alkylthio is substituted, means.
  • Particularly preferred safeners are Mefenpyr-diethyl, Cyprosulfamid, Isoxadifen-ethyl, Cloquintocet-Mexyl, Dichlormid and Metcamifen.
  • Wettable powders are preparations that are uniformly dispersible in water, which in addition to the active ingredient, in addition to a diluent or inert substance, also surfactants of an ionic and / or nonionic type (wetting agents, dispersants), e.g.
  • the herbicidally active ingredients are finely ground, for example, in customary apparatus such as hammer mills, blower mills and air jet mills and simultaneously or subsequently mixed with the formulation auxiliaries.
  • Emulsifiable concentrates are produced by dissolving the active ingredient in an organic solvent, e.g. butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons or mixtures of organic solvents with the addition of one or more ionic and / or nonionic surfactants (emulsifiers).
  • organic solvent e.g. butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons or mixtures of organic solvents.
  • alkylarylsulphonic acid calcium salts such as calcium dodecylbenzenesulphonate or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products
  • alkyl polyethers such as sorbitan oxyethane fatty esters, eg sorbitan oxyethyl fatty esters, sorbitan oxyethyl esters such as sorbitan oxyethyl fatty esters, eg sorbitan oxyethyl fatty esters, sorbitan oxyethylene fatty esters, sorbitan oxyethylene fatty esters, sorbitan oxyethylene fatty esters, sorbitan oxyethyl esters such as sorbitan oxyethyl fatty esters, sorbitan oxyethyl esters, sorbitan oxye
  • Dusting agents are obtained by grinding the active ingredient with finely divided solid substances, for example talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • Suspension concentrates can be water or oil based. They can be prepared, for example, by wet grinding using commercially available bead mills and, if appropriate, addition of 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
  • aqueous organic solvents and optionally surfactants such as those already listed above for the other types of formulation.
  • Granules can be produced either 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 carrier materials such as sand, kaolinite or granulated inert material.
  • adhesives e.g. polyvinyl alcohol, sodium polyacrylic acid or mineral oils
  • Suitable active ingredients can also be granulated in the manner customary for the production of fertilizer granules - if desired as a mixture with fertilizers.
  • Water-dispersible granules are generally produced by the customary processes such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material.
  • the agrochemical preparations generally contain 0.1 to 99% by weight, in particular 0.1 to 95% by weight, of compounds according to the invention.
  • the active ingredient concentration is about 10 to 90% by weight, the remainder to 100% by weight consists of the usual
  • 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 is solid and which granulating aids, fillers, etc. are used.
  • the content of active ingredient is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
  • the active ingredient formulations mentioned contain, if appropriate, the respective 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 influencing agents.
  • the formulations available in commercially available form are diluted in the customary manner if necessary, e.g. in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules using water.
  • Preparations in the form of dust, soil granules or granules as well as sprayable solutions are usually no longer diluted with other inert substances before use.
  • the required application rate of the compounds of the formula (I) and their salts varies with the external conditions such as temperature, humidity and the type of herbicide used. It can fluctuate within wide limits, for example between 0.001 and 10.0 kg / ha or more active substance, but preferably between 0.005 and 5 kg / ha, more preferably in the range from 0.01 to 1.5 kg / ha, in particular preferably in the range from 0.05 to 1 kg / ha g / ha. This applies to both pre-emergence and post-emergence use.
  • Carrier means a natural or synthetic, organic or inorganic substance with which the active ingredients are mixed or combined for better applicability, especially for application to plants or parts of plants or seeds.
  • the carrier which can be solid or liquid, is generally inert and should be agriculturally useful.
  • Possible solid or liquid carriers are: e.g. ammonium salts and natural rock flours such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock flours such as highly disperse silica, aluminum oxide and natural or synthetic silicates, resins, waxes, solid fertilizers, water, alcohols, especially butanol, organic solvents, mineral and vegetable oils and derivatives thereof. Mixtures of such carriers can also be used.
  • As solid carriers for Granules come into consideration: e.g.
  • broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules made from inorganic and organic flours as well as granules made from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks.
  • Liquefied gaseous extenders or carriers are liquids which are gaseous at normal temperature and under normal pressure, e.g. aerosol propellants such as halogenated hydrocarbons, as well as butane, propane, nitrogen and carbon dioxide.
  • Adhesives such as carboxymethylcellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, and also natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations. Further additives can be mineral and vegetable oils.
  • organic solvents for example, can also be used as auxiliary solvents.
  • the main liquid solvents are: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylene or dichloromethane, aliphatic hydrocarbons such as cyclohexane or paraffins, e.g.
  • the agents according to the invention can additionally contain other constituents, such as surface-active substances.
  • Suitable surface-active substances are emulsifiers and / or foam-generating agents, dispersants or wetting agents with ionic or non-ionic properties or mixtures of these surface-active substances.
  • salts of polyacrylic acid salts of lignosulphonic acid, salts of phenolsulphonic acid or naphthalenesulphonic acid, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, substituted phenols (preferably alkylphenols or arylphenols), salts of sulphobemuccinic acid esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols, and derivatives of the compounds containing sulphates, sulphonates and phosphates, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates, protein hydrolysates, lignin sulphite waste liquors and methyl cellulose.
  • a surface-active substance is necessary if one of the active substances and / or one of the inert carriers is not soluble in water and if the application takes place in water.
  • the proportion of surface-active substances is between 5 and 40 percent by weight of the agent according to the invention.
  • Dyes such as inorganic pigments, for example iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the active ingredients can be combined with any solid or liquid additive commonly used for formulation purposes.
  • the agents and formulations according to the invention contain between 0.05 and 99% by weight, 0.01 and 98% by weight, preferably between 0.1 and 95% by weight, particularly preferably between 0.5 and 90% Active ingredient, very particularly preferably between 10 and 70 percent by weight.
  • the active ingredients or agents according to the invention can be used as such or depending on their respective physical and / or chemical properties in the form of their formulations or the use forms prepared therefrom, such as aerosols, capsule suspensions, cold mist concentrates, hot mist concentrates, encapsulated granules, fine granules, flowable concentrates for the Treatment of seeds, ready-to-use solutions, dustable powders, emulsifiable concentrates, oil-in-water emulsions, water-in-oil emulsions, macrogranules, microgranules, oil-dispersible powders, oil-miscible flowable concentrates, oil-miscible liquids, foams, Pastes, pesticide-coated seeds, suspension concentrates, suspension-emulsion concentrates, soluble concentrates, suspensions, wettable powders, soluble powders, dusts and granulates, water-soluble granulates or tablets, water-soluble powders for seed treatment, wettable powders, active
  • the formulations mentioned can be prepared in a manner known per se, for example by mixing the active ingredients with at least one customary extender, solvent or diluent, emulsifier, dispersant and / or binding or fixing agent, wetting agent, water repellant, optionally siccatives and UV stabilizers and optionally dyes and pigments, defoamers, preservatives, secondary thickeners, adhesives, gibberellins and other processing aids.
  • the agents according to the invention not only include formulations which are already ready for use and can be applied to the plant or the seed with a suitable apparatus, but also commercial concentrates which have to be diluted with water before use.
  • the active compounds according to the invention can be used as such or in their (commercially available) formulations and in the use forms prepared from these formulations as a mixture other (known) active ingredients such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides, fertilizers, safeners or semiochemicals.
  • active ingredients such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides, fertilizers, safeners or semiochemicals.
  • the treatment of the plants and plant parts according to the invention with the active ingredients or agents takes place directly or by acting on their surroundings, living space or storage room according to the usual treatment methods, e.g. by dipping, spraying, spraying, sprinkling, evaporation, Atomizing, misting, scattering, foaming, brushing, spreading, watering (drenching), drip irrigation and, in the case of propagation material, especially seeds, also by dry dressing, wet dressing, slurry dressing, encrusting, single or multi-layer coating, etc. It is it is also possible to apply the active ingredients by the ultra-low-volume method or to inject the active ingredient preparation or the active ingredient itself into the soil.
  • transgenic seeds with the active ingredients or agents according to the invention are of particular importance.
  • the heterologous gene in transgenic seeds can originate, for example, from microorganisms of the species Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium.
  • This heterologous gene preferably originates from Bacillus sp., The gene product having an effect against the European corn borer and / or Western Com Rootworm.
  • the heterologous gene is particularly preferably derived from Bacillus thuringiensis.
  • the agent according to the invention is applied to the seed alone or in a suitable formulation.
  • the seed is preferably treated in a state in which it is so stable that no damage occurs during the treatment.
  • the seed can be treated at any point between harvest and sowing.
  • seeds are used that have been separated from the plant and freed from cobs, peels, stems, husks, wool or pulp.
  • seeds can be used that have been harvested, cleaned and dried to a moisture content of less than 15% by weight.
  • seeds can also be used which, after drying, have been treated with water, for example, and then dried again.
  • the agent according to the invention when treating the seed, care must be taken to ensure that the amount of the agent according to the invention and / or further additives applied to the seed is selected so that the germination of the seed is not impaired or the plant resulting therefrom is not damaged. This is especially important for active ingredients that can show phytotoxic effects when applied in certain amounts.
  • the agents according to the invention can be applied directly, that is to say without containing further components and without having been diluted. As a rule, it is preferable to apply the agents to the seeds in the form of a suitable formulation.
  • Suitable formulations and methods for seed treatment are known to the person skilled in the art and are described, for example, in the following documents: US 4,272,417 A, US 4,245,432 A, US 4,808,430, US 5,876,739, US 2003/0176428 A1, WO 2002/080675 A1, WO 2002/028186 A2.
  • the active compounds according to the invention can be converted into the customary seed dressing formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other coating materials for seeds, and also ULV formulations.
  • formulations are prepared in a known manner by mixing the active ingredients with customary additives, such as customary extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, gibberellins and also water .
  • customary additives such as customary extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, gibberellins and also water .
  • Suitable dyes which can be contained in the mordant formulations which can be used according to the invention are all dyes customary for such purposes. Both pigments which are sparingly soluble in water and dyes which are soluble in water can be used here. Examples are those under the names Rhodamine B, C.I. Pigment Red 112 and C.I. Solvent Red 1 known dyes.
  • wetting agents which can be contained in the pickling agent formulations which can be used according to the invention, all substances which promote wetting and which are customary for the formulation of agrochemical active ingredients are suitable.
  • Alkylnaphthalene sulfonates such as diisopropyl or diisobutyl naphthalene sulfonates, can preferably be used.
  • Suitable dispersants and / or emulsifiers which can be contained in the dressing formulations which can be used according to the invention are all nonionic, anionic and cationic dispersants customary for the formulation of agrochemical active ingredients.
  • Nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants can preferably be used.
  • Suitable nonionic dispersants are, in particular, ethylene oxide-propylene oxide block polymers, alkylphenol polyglycol ethers and tristryrylphenol polyglycol ethers and their phosphated or sulfated derivatives.
  • Suitable anionic dispersants are, in particular, lignin sulfonates, polyacrylic acid salts and aryl sulfonate-formaldehyde condensates. All foam-inhibiting substances customary for the formulation of agrochemical active ingredients can be contained as defoamers in the seed dressing formulations which can be used according to the invention. Silicone defoamers and magnesium stearate can preferably be used.
  • All substances which can be used in agrochemical agents for such purposes can be present as preservatives in the seed dressing formulations which can be used according to the invention.
  • Examples are dichlorophene and benzyl alcohol hemiformal.
  • Secondary thickening agents which can be contained in the seed dressing formulations which can be used according to the invention are all substances which can be used in agrochemical agents for such purposes. Cellulose derivatives, acrylic acid derivatives, xanthan gum, modified clays and highly disperse silicic acid are preferred.
  • Suitable adhesives that can be contained in the seed dressing formulations which can be used according to the invention are all conventional binders which can be used in seed dressings.
  • Polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose may be mentioned as preferred.
  • the seed dressing formulations which can be used according to the invention can be used either directly or after prior dilution with water for the treatment of seeds of the most varied of types, including seeds of transgenic plants.
  • additional synergistic effects can also occur in cooperation with the substances formed by expression.
  • the process of dressing is to put the seed in a mixer, add the desired amount of dressing formulations either as such or after prior dilution with water and mix until the formulation is evenly distributed on the seed. If necessary, this is followed by a drying process.
  • the active compounds according to the invention are suitable for protecting plants and plant organs, for increasing crop yields and improving the quality of the crop, given good plant tolerance, favorable warm-blooded toxicity and good environmental compatibility. They can preferably be used as crop protection agents. They are effective against normally sensitive and resistant species and against all or individual stages of development.
  • plants which can be treated according to the invention maize, soybean, cotton, Brassica oilseeds such as Brassica napus (e.g. canola), Brassica rapa, B. juncea (e.g. (field) mustard) and Brassica carinata, rice, wheat Sugar beet, sugar cane, oats, rye, barley, millet, triticale, flax, wine and various fruits and vegetables from various botanical taxa such as Rosaceae sp.
  • pome fruits such as apple and pear, but also stone fruits such as apricots, cherries, almonds and peaches and berries such as strawberries
  • Ribesioidae sp. Juglandaceae sp.
  • Betulaceae sp. Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp., Actinidaceae sp., Lauraceae sp., Musaceae sp. (e.g. banana trees and plantations), Rubiaceae sp. (e.g.
  • Theaceae sp. Sterculiceae sp., Rutaceae sp. (e.g. lemons, organs and grapefruit); Solanaceae sp. (for example tomatoes, potatoes, pepper, eggplant), Liliaceae sp., Compositae sp. (e.g. lettuce, artichoke and chicory - including root chicory, endive or common chicory), Umbelliferae sp. (e.g., carrot, parsley, celery and celeriac), Cucurbitaceae sp. (e.g., cucumber - including pickles, squash, watermelon, bottle gourd, and melons), Alliaceae sp.
  • Solanaceae sp. for example tomatoes, potatoes, pepper, eggplant
  • Liliaceae sp. Compositae sp.
  • Umbelliferae sp. e.g., carrot, parsley, celery and celeriac
  • Cruciferae sp. for example white cabbage, red cabbage, broccoli, cauliflower, Brussels sprouts, pak choi, kohlrabi, radishes, horseradish, cress and Chinese cabbage
  • Leguminosae sp. for example peanuts, peas, and beans - such as runner bean and field bean
  • Chenopodiaceae sp. for example Swiss chard, fodder beet, spinach, beetroot), Malvaceae (for example okra), Asparagaceae (for example asparagus); Useful plants and ornamental plants in gardens and forests; as well as genetically modified species of these plants.
  • plants and their parts can be treated according to the invention.
  • plant species and plant cultivars occurring in the wild or obtained by conventional biological breeding methods such as crossing or protoplast fusion, as well as their parts are treated.
  • transgenic plants and plant cultivars which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods (genetically modified organisms), and their parts are treated.
  • the term “parts” or “parts of plants” or “plant parts” has been explained above.
  • plants of the plant varieties which are commercially available or in use are particularly preferably treated.
  • Plant cultivars are understood to be plants with new properties (“traits”) that have been bred by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be varieties, races, bio and genotypes.
  • the treatment method according to the invention can be used for the treatment of genetically modified organisms (GMOs), e.g. B. plants or seeds can be used.
  • GMOs genetically modified organisms
  • Genetically modified plants are plants in which a heterologous gene has been stably integrated into the genome.
  • heterologous gene essentially means a gene which is provided or assembled outside the plant and which when introduced into the cell nucleus genome, the Chloroplast genome or the mitochondrial genome of the transformed plant gives new or improved agronomic or other properties in that it expresses a protein or polypeptide of interest or that it down-regulates or another gene that is present in the plant or other genes that are present in the plant switches off (for example using antisense technology, cosuppression technology or RNAi technology [RNA interference]).
  • a heterologous gene that is present in the genome is also called a transgene.
  • a transgene that is defined by its specific presence in the plant genome is referred to as a transformation or transgenic event.
  • the treatment according to the invention can also lead to superadditive (“synergistic”) effects.
  • the following effects are possible that go beyond the effects that are actually to be expected: reduced application rates and / or expanded spectrum of activity and / or increased effectiveness of the active ingredients and compositions that can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or water or soil salt content, increased flowering performance, easier harvesting, accelerated ripening, higher yields, larger fruits, higher plant height, more intense green color of the leaves, earlier flowering, higher quality and / or higher nutritional value of the harvested products, higher sugar concentration in the fruits, better storability and / or processability of the harvested products.
  • Plants and plant cultivars that are preferably treated according to the invention include all plants that have genetics which give these plants particularly advantageous, useful characteristics (regardless of whether this was achieved through breeding and / or biotechnology).
  • nematode-resistant plants are described, for example, in the following US patent applications: 11 / 765,491, 11 / 765,494, 10 / 926,819, 10 / 782,020, 12 / 032,479, 10 / 783,417, 10 / 782,096, 11 / 657,964, 12 / 192,904, 11 / 396,808, 12 / 166,253, 12 / 166,239, 12 / 166,124, 12 / 166,209, 11 / 762,886, 12 / 364,335, 11 / 763,947, 12 / 252,453, 12 / 209,354, 12 / 491,396 and 12 / 497,221.
  • Plants which can be treated according to the invention are hybrid plants which already express the properties of heterosis or the hybrid effect, which generally leads to higher yields, higher vigor, better health and better resistance to biotic and abiotic stress factors.
  • Such plants are typically created by crossing an inbred male sterile parent line (the female cross partner) with another inbred male fertile parent line (the male cross partner). That Hybrid seeds are typically harvested from the male-sterile plants and sold to propagators.
  • Male-sterile plants can sometimes (e.g. in maize) be produced by detasseling (ie mechanical removal of the male sexual organs or the male flowers); however, it is more common that male sterility is due to genetic determinants in the plant genome.
  • a particularly favorable means for producing male-sterile plants is described in WO 89/10396, for example a ribonuclease such as a Bamase being selectively expressed in the tapetum cells in the stamens. Fertility can then be restored by expressing a ribonuclease inhibitor such as barstar in the tapetum cells.
  • a ribonuclease such as a Bamase
  • Plants or plant cultivars which are obtained using methods of plant biotechnology, such as genetic engineering which can be treated according to the invention are herbicide-tolerant plants; H. Plants that have been made tolerant to one or more specified herbicides. Such plants can be obtained either by genetic transformation or by selection of plants which contain a mutation which confers such herbicide tolerance.
  • Herbicide-tolerant plants are, for example, glyphosate-tolerant plants, ie plants which have been made tolerant to the herbicide glyphosate or its salts. Plants can be made tolerant to glyphosate using a variety of methods. For example, glyphosate-tolerant plants can be obtained by transforming the plant with a gene that codes for the enzyme 5-enolpyruvylshikimate-3-phosphate synthase (EPSPS). Examples of such EPSPS genes are the AroA gene (mutant CT7) of the bacterium Salmonella typhimurium (Comai et al., 1983, Science 221, 370-371), the CP4 gene of the bacterium Agrobacterium sp.
  • EPSPS 5-enolpyruvylshikimate-3-phosphate synthase
  • Glyphosate-tolerant plants can also be obtained by expressing a gene which codes for a glyphosate acetyltransferase enzyme. Glyphosate-tolerant plants can also be obtained by selecting plants which contain naturally occurring mutations of the genes mentioned above. Plants expressing EPSPS genes that confer glyphosate tolerance are described. Plants which confer other genes that confer glyphosate tolerance, e.g., decarboxylase genes, are described.
  • herbicide-resistant plants are, for example, plants which have been made tolerant to herbicides which inhibit the enzyme glutamine synthase, such as bialaphos, phosphinotricin or glufosinate.
  • Such plants can be obtained by expressing an enzyme that detoxifies the herbicide or a mutant of the enzyme glutamine synthase that is resistant to inhibition.
  • an effective detoxifying enzyme is, for example, an enzyme which codes for a phosphinotricin acetyltransferase (such as, for example, the bar or pat protein from Streptomyces species). Plants expressing an exogenous phosphinotricin acetyltransferase have been described.
  • hydroxyphenylpyruvate dioxygenase HPPD
  • HPPD hydroxyphenylpyruvate dioxygenase
  • the hydroxyphenylpyruvate dioxygenases are enzymes that catalyze the reaction in which para-hydroxyphenylpyruvate (HPP) is converted to homogenate.
  • Plants tolerant to HPPD inhibitors can be transformed with a gene encoding a naturally occurring resistant HPPD enzyme or a gene encoding a mutated or chimeric HPPD enzyme, as in WO 96/38567 , WO 99/24585, WO 99/24586, WO 2009/144079, WO 2002/046387 or US 6,768,044.
  • Tolerance to HPPD inhibitors can also be achieved by transforming plants with genes which code for certain enzymes which enable the formation of homogenate despite the inhibition of the native HPPD enzyme by the HPPD inhibitor. Such plants are described in WO 99/34008 and WO 02/36787.
  • the tolerance of plants to HPPD inhibitors can also be improved by transforming plants, in addition to a gene that codes for an HPPD-tolerant enzyme, with a gene that codes for a prephenate dehydrogenase enzyme, as in WO 2004/024928 is described.
  • plants can be made even more tolerant of HPPD inhibitors by inserting a gene into their genome which codes for an enzyme that metabolizes or degrades HPPD inhibitors, such as CYP450 enzymes (see WO 2007/103567 and WO 2008/150473 ).
  • Further herbicide-resistant plants are plants that have been made tolerant to acetolactate synthase (ALS) inhibitors.
  • ALS inhibitors include, for example, sulfonylurea, imidazolinone, triazolopyrimidines, pyrimidinyloxy (thio) benzoates and / or sulfonylaminocarbonyltriazolinone herbicides.
  • ALS also known as acetohydroxy acid synthase, AHAS
  • AHAS acetohydroxy acid synthase
  • Further plants that are tolerant to imidazolinones and / or sulfonylureas can be obtained by induced mutagenesis, selection in cell cultures in the presence of the herbicide or by mutation breeding (cf. eg for soybeans EIS 5,084,082, for rice WO 97/41218, for sugar beet EIS 5,773,702 and WO 99/057965, for salad EIS 5,198,599 or for sunflower WO 01/065922).
  • Plants or plant varieties which were obtained by methods of plant biotechnology, such as genetic engineering), which can also be treated according to the invention, are tolerant of abiotic stress factors. Such plants can be obtained by genetic transformation or by selection of plants which contain a mutation which confers such stress resistance.
  • Particularly useful plants with stress tolerance include the following: a. Plants which contain a transgene which is able to reduce the expression and / or activity of the gene for the poly (ADP-ribose) polymerase (PARP) in the plant cells or plants.
  • PARP poly (ADP-ribose) polymerase
  • Plants which contain a stress tolerance-promoting transgene which is capable of reducing the expression and / or activity of the genes of the plants or plant cells coding for PARG;
  • Enzyme encoded by the nicotinamide adenine dinucleotide salvage biosynthetic pathway including nicotinamidase, nicotinate phosphoribosyl transferase, nicotinic acid mononucleotide adenyl transferase,
  • Nicotinamide adenine dinucleotide synthetase or nicotinamide phosphoribosyl transferase Nicotinamide adenine dinucleotide synthetase or nicotinamide phosphoribosyl transferase.
  • Plants or plant varieties (which were obtained by methods of plant biotechnology, such as genetic engineering), which can also be treated according to the invention, have a changed amount, quality and / or shelf life of the harvested product and / or changed properties of certain components of the harvested product, such as: 1) Transgenic plants that synthesize a modified starch which, with regard to their chemical-physical properties, in particular the amylose content or the amylose / amylopectin ratio, the degree of branching, the average chain length, the distribution of the side chains, the viscosity behavior, the gel strength, the Starch grain size and / or starch grain morphology is changed in comparison with the synthesized starch in wild-type plant cells or plants, so that this modified starch is more suitable for certain applications.
  • a modified starch which, with regard to their chemical-physical properties, in particular the amylose content or the amylose / amylopectin ratio, the degree of branching, the average chain length, the distribution of the side chains, the viscosity behavior, the
  • Transgenic plants that synthesize non-starch carbohydrate polymers or non-starch carbohydrate polymers whose properties are changed compared to wild-type plants without genetic modification. Examples are plants which produce polyfructose, in particular of the inulin and levan type, plants which produce alpha-1,4-glucans, plants which produce alpha-1,4-glucans, and plants which Alteman produce.
  • Transgenic plants or hybrid plants such as onions with certain properties such as “high soluble solids content” (“high soluble solids content”), low heat (“low pungency”, LP) and / or long storage life (“long storage”, LS ).
  • Plants or plant varieties are plants such as cotton plants with modified fiber properties.
  • Such plants can be obtained by genetic transformation or by selection of plants which contain a mutation which confers such altered fiber properties; these include: a) plants such as cotton plants which contain a modified form of cellulose synthase genes, b) plants such as cotton plants which contain a modified form of rsw2- or rsw3 -homologous nucleic acids, such as cotton plants with an increased expression of sucrose phosphate synthase; c) Plants such as cotton plants with an increased expression of sucrose synthase; d) Plants such as cotton plants in which the timing of the flow control of the plasmodesmata is changed at the base of the fiber cell, e.g.
  • Plants such as cotton plants with fibers with altered reactivity, e.g. B. by expression of the N-acetylglucosamine transferase gene, including nodC, and of chitin synthase genes.
  • Plants or plant cultivars (which were obtained by methods of plant biotechnology, such as genetic engineering), which can likewise be treated according to the invention, are plants such as rapeseed or related Brassica plants with modified properties of the oil composition.
  • Such plants can be obtained by genetic transformation or by selection of plants which contain a mutation which confers such altered oil properties; these include: a) Plants such as rape plants that produce oil with a high oleic acid content; b) Plants such as rape plants that produce oil with a low linolenic acid content. c) Plants such as rapeseed that produce oil with a low content of saturated fat.
  • Plants or plant varieties which can be obtained by methods of plant biotechnology, such as genetic engineering), which can also be treated according to the invention, are plants such as potatoes, which are virus-resistant, e.g. against the potato virus Y (Event SY230 and SY233 from Tecnoplant, Argentina), or which are resistant to diseases such as late blight (potato late blight) (e.g. RB gene), or which show a reduced sweetness induced by cold (which carry the genes Nt-Inh, II-INV) or which the dwarf Show phenotype (gene A-20 oxidase).
  • viruses which are virus-resistant, e.g. against the potato virus Y (Event SY230 and SY233 from Tecnoplant, Argentina), or which are resistant to diseases such as late blight (potato late blight) (e.g. RB gene), or which show a reduced sweetness induced by cold (which carry the genes Nt-Inh, II-INV) or which the dwarf Show pheno
  • Plants or plant varieties which were obtained by methods of plant biotechnology, such as genetic engineering), which can also be treated according to the invention, are plants such as rapeseed or related Brassica plants with changed properties in the case of seed shattering. Such plants can, by genetic transformation or by selection of plants containing a mutation, confer such altered traits, and include plants such as oilseed rape with delayed or reduced seed loss.
  • transgenic plants that can be treated according to the invention are plants with transformation events or combinations of transformation events which are the subject of petitions issued or pending in the EISA at the Animal and Plant Health Inspection Service (APHIS) of the United States Department of Agriculture (USDA) are for the non-regulated status. Information on this is available at any time from APHIS (4700 River Road Riverdale, MD 20737, USA), e.g. via the Internet page http://www.aphis.usda.gov/brs/not_reg.html. On the filing date of this application, the petitions with the following information were either granted or pending at APHIS:
  • Transgenic phenotype the trait given to the plant by the transformation event.
  • - Transformation event or line the name of the event or events (sometimes referred to as line (s)) for which non-regulated status is requested.
  • APHIS documents various documents that are published by APHIS regarding the petition or that can be obtained from APHIS on request.
  • transgenic plants which can be treated according to the invention are plants with one or more genes which code for one or more toxins, are the transgenic plants which are sold under the following trade names: YIELD GARD® (for example maize, cotton, Soybeans), KnockOut® (e.g. corn), BiteGard® (e.g. corn), BT-Xtra® (e.g. corn), StarLink® (e.g. corn), Bollgard® (cotton), Nucotn® (cotton), Nucotn 33B® (cotton), NatureGard® (e.g. maize), Protecta® and NewLeaf® (potato).
  • YIELD GARD® for example maize, cotton, Soybeans
  • KnockOut® e.g. corn
  • BiteGard® e.g. corn
  • BT-Xtra® e.g. corn
  • StarLink® e.g. corn
  • Bollgard® cotton
  • Nucotn® cotton
  • Nucotn 33B® cott
  • Herbicide-tolerant plants to be mentioned are, for example, maize varieties, cotton varieties and soybean varieties, which are sold under the following trade names: Roundup Ready® (glyphosate tolerance, e.g. corn, cotton, soybean), Liberty Link® (phosphinotricintolerance, e.g. rapeseed) , IMI® (imidazolinone tolerance) and SCS® (sylphonyl urea tolerance), for example corn.
  • the herbicide-resistant plants (plants traditionally bred for herbicide tolerance) that should be mentioned include the varieties sold under the name Clearfield® (e.g. maize). Chemical examples
  • Step 1 Synthesis of 8- (2,2-difluoroethoxy) -l, 3-diazaspiro [4.5] decane-2,4-dione (example no. 15-1) 116.1 g (1.21 mol) ammonium carbonate and 11.3 g (0.23 mol) sodium cyanide were in 500 ml
  • Step 2 Synthesis of l-amino-4- (2,2-difluoroethoxy) cyclohexanecarboxylic acid hydrochloride (Example No. 14-1)
  • a mixture of 66.2 g (0.27 mol) 8- (2,2-difluoroethoxy) -1, 3-diazaspiro [4.5] decane-2,4-dione and 194 g (purity 85% by weight; 2.93 mol) potassium hydroxide in 750 ml of water were stirred under reflux until the LC / MS chromatographic reaction control indicated a substantial conversion.
  • the contents were slowly and carefully concentrated with Hydrochloric acid adjusted to a pH of 3. The mixture was concentrated and the residue was washed with methanol. The liquid was finally freed from the solvent, 47.2 g of the desired product being obtained as residue.
  • Step 3 Synthesis of methyl l-amino-4- (2,2-difluoroethoxy) cyclohexanecarboxylate hydrochloride (example no. 13-1)
  • Step 4 Synthesis of [2-chloro-6-methyl-4- (prop-l-in-l-yl) phenyl] acetic acid (example no. 18-5) 3.69 g (15.6 mmol) of methyl [2-chloro-6-methyl-4- (prop-1-yn-1-yl) phenyl] acetate were in 20 ml
  • Step 5 Synthesis of methyl-l- ⁇ 2- [2-chloro-6-methyl-4- (prop-l-yn-l-yl) phenyl] acetamido ⁇ -4- (2,2- difluoroethoxy) cyclohexanecarboxylate (Example No. 11-5)
  • Step 6 Synthesis of 67.v-3- [2-chloro-6-methyl-4- (prop- 1 -in- 1 -yl) phenyl] -8- (2,2-dif1uoroethoxy) -4-hydroxy- l-azaspiro [4.5] dec-3-en-2-one (example no. 1-5) and of trans- 3 - [2-chloro-6-methyl-4- (prop- 1 -in- 1 - yl) phenyl] -8- (2,2-difluoroethoxy) -4-hydroxy- 1 - azaspiro [4.5] dec-3-en-2-one (example no. 1-26)
  • the aqueous phase was adjusted to a pH of 2 with dilute hydrochloric acid. After extraction with ethyl acetate, the organic phase was dried and the filtrate was freed from the solvent. The residue was purified by chromatography, 682 mg of the c .v-configured product and 443 mg of the trans-configured product being obtained.
  • the mixture was washed with water and then with 2M hydrochloric acid. After the phases had separated, the organic phase was dried and the filtrate was freed from the solvent. The residue was purified by chromatography, 98 mg of the desired product having a purity of 95% by weight being isolated.
  • the 1H-NMR data of selected examples are noted in the form of 1H-NMR peak lists. For each signal peak, first the d-value in ppm and then the signal intensity are listed in round brackets. The d-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: di (intensity i 1 ; d2 (intensity2);.; D ⁇ (intensity ⁇ ;.; D h (intensity)
  • 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 real relationships between 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.
  • To calibrate the chemical shift of 1H-NMR spectra we use tetramethylsilane and / or the chemical shift of the solvent, especially in the case of spectra measured in DMSO. The tetramethylsilane peak can therefore appear in NMR peak lists, but does not have to be.
  • connection signals in the delta range of solvents and / or water our lists of 1H-NMR peaks show the usual solvent peaks, for example peaks from DMSO in DMSO-D ⁇ and the peak from water, which are usually on average have a high intensity.
  • the peaks of stereoisomers of the target compounds and / or peaks of impurities usually have, on average, a lower intensity than the peaks of the target compounds (for example with a purity of> 90%).
  • Such stereoisomers and / or impurities can be typical of the particular manufacturing process. Your peaks can thus help to identify the reproduction of our manufacturing process based on “by-product fingerprints”.
  • An expert who calculates the peaks of the target compounds with known methods can isolate the peaks of the target compounds as required, with additional intensity filters being used if necessary. This isolation would be similar to the relevant peak picking in the classical 1 H-NMR interpretation.
  • Example connection 4-5 To measure this compound in D2O, a drop of NaOD was added in order to achieve better solubility with the sodium salt generated in this way and thus to obtain a better spectrum.
  • the compound characterized here is therefore the corresponding sodium salt.
  • Example connection 4-5 To measure this compound in D2O, a drop of NaOD was added in order to achieve better solubility with the sodium salt generated in this way and thus to obtain a better spectrum.
  • the compound characterized here is therefore the corresponding sodium salt.
  • Example connection 5-43 ⁇ -NMR (400.6 MHz, CDC13, ppm): 7.09 (s, 2H), 6.22 (br s, 1H), 4.00 (q, 2H), 3.65 (t, 2H), 3.50- 3.40 (m, 1H), 2.25-2.15 (m + s, 8H), 2.03 (s, 3H), 2.02-1.90 (m, 2H), 1.80-1.74 (m, 2H), 1.65 (t, 3H), 1.50-1.40 (m, 2H), 1.11 (t, 3H)
  • Example connection 5-44 ⁇ -NMR (400.6 MHz, CDC13, ppm): 7.13 (s, 1H), 7.10 (s, 1H), 6.29 (br s, 1H), 4.01 (q, 2H), 3.65 (t, 2H), 3.50- 3.40 (m, 1H), 2.56-2.40 (m, 2H), 2.25-2.17 (m + s, 5H), 2.04 (s, 3H), 2.02-1.88 (m, 2H), 1.83-1.74 (m, 2H ), 1.65 (t, 3H), 1.52-1.40 (m, 2H), 1.20-1.10 (m, 6H)
  • a dusting agent is obtained by mixing 10 parts by weight of a compound of the formula (I) and / or its salts and 90 parts by weight of talc as an inert substance and comminuting it in a hammer mill.
  • a wettable powder which is easily dispersible in water is obtained by adding 25 parts by weight of a compound of the formula (I) and / or salts thereof, 64 parts by weight of kaolin-containing quartz as an inert substance, 10 parts by weight of potassium lignosulfonate and 1 part by weight of sodium oleoylmethyltaurinate mixes as a wetting agent and dispersant and grinds in a pin mill.
  • a dispersion concentrate which is easily dispersible in water is obtained by adding 20 parts by weight of a compound of the formula (I) and / or its salts with 6 parts by weight of alkylphenol polyglycol ether ( ⁇ Triton X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO ) and 71 parts by weight of paraffinic mineral oil (boiling range for example approx. 255 ° C to over 277 ° C) and ground in a friction ball mill to a fineness of less than 5 microns.
  • An emulsifiable concentrate is obtained from 15 parts by weight of a compound of the formula (I) and / or its salts, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of ethoxylated nonylphenol as emulsifier.
  • a water-dispersible granulate is obtained by adding 75 parts by weight of a compound of the formula (I) and / or its salts,
  • a water-dispersible granulate is also obtained by adding 25 parts by weight of a compound of the formula (I) and / or its salts,
  • Seeds of monocotyledonous or dicotyledonous weed or crop plants are placed in wooden fiber pots in sandy loam soil, covered with soil and grown in a greenhouse under good growth conditions. 2 to 3 weeks after sowing, the test plants are treated in the single-leaf stage.
  • the compounds according to the invention formulated in the form of wettable powders (WP) or emulsion concentrates (EC) are then sprayed onto the green parts of the plant as an aqueous suspension or emulsion with a water application rate of 600 to 800 l / ha with the addition of 0.2% wetting agent .
  • WP wettable powders
  • EC emulsion concentrates
  • the Compounds according to the invention have good herbicidal post-emergence activity against a broad spectrum of grass weeds and weeds.
  • the examples given show an 80-100% effect at an application rate of 80/20 g / ha against Alopecurus myo suroide s, Avena fatua, Digitaria sanguinalis, Echinochloa crus-galli, Lolium rigidum and Setaria viridis.
  • the compounds according to the invention are therefore suitable in the post-emergence process for combating undesired vegetation.
  • Seeds of monocotyledonous or dicotyledonous weed or crop plants are laid out in wooden fiber pots in sandy loam and covered with soil.
  • the compounds according to the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC), are then applied to the surface of the covering soil as an aqueous suspension or emulsion with a water application rate of the equivalent of 600 to 800 1 / ha with the addition of 0.2% wetting agent applied.
  • the compounds each show an 80-100% action against, inter alia, Alopecurus myosuroides, Avena fatua, Digitaria sanguinalis, Echinochloa crus-galli, Lolium rigidum, Setaria viridis, Amaranthus retroflexus, Matricaria inodora, Viola tricolor and Veronica persica.
  • the compounds according to the invention are therefore suitable in the pre-emergence method for controlling undesired vegetation.

Abstract

La présente invention concerne de nouvelles pyrroline-2-ones à action herbicide représentées par la formule générale (I) ou des sels agrochimiquement acceptables de celles-ci, ainsi que leur utilisation dans la lutte contre les plantes adventices et les mauvaises herbes dans des cultures de plantes utiles.
PCT/EP2021/059628 2020-04-15 2021-04-14 Pyrroline-2-ones à substitution spécifique et leur utilisation en tant qu'herbicides WO2021209486A1 (fr)

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