EP3810589A1 - Substituted 2-heteroaryloxypyridines and salts thereof and their use as herbicidal agents - Google Patents

Substituted 2-heteroaryloxypyridines and salts thereof and their use as herbicidal agents

Info

Publication number
EP3810589A1
EP3810589A1 EP19731734.0A EP19731734A EP3810589A1 EP 3810589 A1 EP3810589 A1 EP 3810589A1 EP 19731734 A EP19731734 A EP 19731734A EP 3810589 A1 EP3810589 A1 EP 3810589A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
alkoxy
methyl
haloalkoxy
general formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP19731734.0A
Other languages
German (de)
French (fr)
Inventor
Michael Charles MCLEOD
Ralf Braun
Anu Bheemaiah MACHETTIRA
Dirk Schmutzler
Elisabeth ASMUS
Christopher Hugh Rosinger
Elmar Gatzweiler
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Bayer AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Publication of EP3810589A1 publication Critical patent/EP3810589A1/en
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines

Definitions

  • the invention relates to the technical field of crop protection agents, in particular that of herbicides for the selective control of weeds and weeds in crops of useful plants.
  • this invention relates to substituted 2-heteroaryloxypyridines and their salts, processes for their preparation and their use as herbicides.
  • Crop crops or active ingredients to combat undesirable plant growth sometimes have disadvantages when used, either because they (a) have no or an inadequate herbicidal activity against certain harmful plants, (b) the spectrum of the harmful plants is too small to combat with an active ingredient can be (c) insufficient selectivity in crops and / or (d) have a toxicologically unfavorable profile.
  • active ingredients which can be used as plant growth regulators in some crop plants lead to undesirably reduced crop yields in other crop plants or are incompatible or only compatible with the crop plant in a narrow range of application rates.
  • Some of the known active ingredients cannot be economically manufactured on an industrial scale because of precursors and reagents that are difficult to access, or they have insufficient chemical stabilities. For other active substances, the effect depends too much on environmental conditions such as weather and soil conditions.
  • heteroaryloxybenzenes have been described in WO2015 / 89003, WO2015 / 108779, WO2016 / 10731, WO2016 / 196606 and WO2017 / 11288, to which a herbicidal action has been attributed.
  • the present invention thus relates to substituted 2-heteroaryloxypyridines of the general formula (1) or their salts
  • X represents nitrogen, -CF- or -CH-
  • n 0, 1 or 2
  • R 1 represents an optionally substituted aryl, heteroaryl, heterocylyl, (C3-Cio) cycloalkyl or (C3-Cio) cycloalkenyl, each ring or ring system optionally having up to 5
  • R 2 independently of one another for halogen, cyano, nitro, formyl, formamide, (Ci -Cs) - alkyl, (Ci-C 8 ) - haloalkyl, (C 2 -C 8 ) alkenyl, (C 2 -C 8 ) - Alkynyl, (C 2 -C 8 ) -haloalkenyl, (C 2 -C 8 ) -haloalkynyl, (Ci-C 4 ) -alkoxy- (Ci-C 4 ) -alkyl, (Ci-C 4 ) -haloalkoxy- ( Ci-C 4 ) -alkyl, (Ci-C 4 ) -alkylthio- (Ci-C 4 ) -alkyl,
  • (Ci-C 4 ) alkyl carboxy- (Ci-C 4 ) alkyl, hydroxy, amino, (Ci-C 8 ) alkoxy, (Ci-C 8 ) haloalkoxy, (Ci-C 8 ) alkylthio , (Ci-C 8 ) -haloalkylthio, (C3-C 8 ) -cycloalkylthio, (Ci-C 8 ) -alkylsulfinyl, (Ci-C 8 ) -haloalkylsulfyl, (C3-C 8 ) -cycloalkylsulfinyl, (Ci-C 8 ) -alkylsulfonyl, (Ci-C 8 ) - Haloalkylsulfonyl, (C 3 -Cg) -cycloalkylsulfonyl, (Ci-C 8 ) -alkylaminosulfon
  • R 3 for hydrogen, halogen, cyano, nitro, formyl, (Ci-Cg) alkyl, (Ci-Cg) haloalkyl, (C 2 -Cg) alkenyl, (C 2 -Cg) alkynyl, (C 2 -Cg) haloalkenyl, (C 2 -Cg) haloalkynyl, (Ci-C 4 ) alkoxy- (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkoxy- (Ci-C 4 ) alkyl , (Ci-C 4) alkylthio (Ci-C 4) alkyl, (Ci-C4) - Alkylsulfmyl- (Ci-C 4) alkyl, (Ci-C 4) alkylsulfonyl (Ci-C 4 ) -alkyl, (Ci-Cg) -alkylcarbonyl,
  • R 4 and R 5 independently of one another are hydrogen, hydroxyl, halogen, (Ci-Cg) -alkyl, (Ci-Cs) - haloalkyl, (C 2 -Cg) -alkenyl, (C 2 -Cg) -alkynyl, (Ci -C 4 ) -alkoxy- (Ci-C 4 ) -alkyl, (Ci-C 4 ) -haloalkoxy- (Ci-C 4 ) -alkyl, (Ci-C 4 ) -alkylthio- (Ci-C 4 ) - alkyl, (Ci-C 4 ) -alkylsulfmyl- (Ci-C 4 ) -alkyl, (Ci-C 4 ) -alkylsulfonyl- (Ci-C 4 ) -alkyl, (Ci-Cg) -alkylcarbonyl, (C
  • R 4 and R 5 together form a 3- to 6-membered carbocyclic ring or a 3- to 6-membered saturated heterocyclic ring with up to 2 oxygen atoms, or
  • R 4 and R 5 together form a (Ci-C3) alkylidene radical or (Ci-C3) haloalkylidene radical
  • R 6 is hydrogen, (Ci-Cg) -alkyl, (Ci-Cg) -haloalkyl, aryl- (Ci-C 6 ) -alkyl, heteroaryl- (Ci-C 6 ) -alkyl, (C 3 -C 6 ) -Cycloalkyl, (C3-C 6 ) -cycloalkyl- (Ci-C 6 ) -alkyl, (C 3 -C 6 ) -halocycloalkyl, (C 3 -C 6 ) -halocycloalkyl- (Ci-C 4 ) -alkyl, (C 2 -Cg) alkenyl, (C 2 -Cg) alkynyl, (Ci-C 4 ) alkoxy- (Ci-C 4
  • R 7 represents hydrogen, halogen, cyano, nitro, formyl, (Ci-Cg) alkyl, (Ci-Cg) haloalkyl, (C 2 -Cg) alkenyl, (C 2 -Cg) alkynyl, (C 2 -Cg) haloalkenyl, (C 2 -Cg) haloalkynyl, (Ci-C 4 ) alkoxy- (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkoxy- (Ci-C 4 ) alkyl , (Ci-C 4) alkylthio (Ci-C 4) alkyl, (Ci-C 4) - alkylsulfinyl (Ci-C 4) alkyl, (Ci-C 4) alkylsulfonyl (Ci-C 4 ) -alkyl, (Ci-Cg) -alkylcarbonyl
  • the compounds of general formula (1) can be added by adding a suitable one
  • inorganic or organic acid such as mineral acids, such as HCl, HBr, H 2 S0 4 , H 3 P0 4 or HN0 3 , or organic acids, e.g. B. carboxylic acids, such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid or sulfonic acids, such as p-toluenesulfonic acid, to form a basic group such as amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino, salts. These salts then contain the conjugate base of the acid as an anion. Suitable substituents determined in deprotonated form, such as sulfonic acids
  • Sulphonic acid amides or carboxylic acids are present, inner salts with protonatable groups such as amino groups can form. Salt formation can also be caused by exposure to a base
  • Suitable bases are, for example, organic amines, such as trialkylamines, morpholine, piperidine and pyridine, and ammonium, alkali or
  • Potassium hydroxide, sodium and potassium carbonate and sodium and potassium hydrogen carbonate are compounds in which the acidic hydrogen is replaced by a cation suitable for agriculture, for example metal salts, in particular alkali metal salts or
  • Alkaline earth metal salts especially sodium and potassium salts, or also ammonium salts, salts with organic amines or quaternary ammonium salts, for example with cations of the formula
  • R a to R d each independently represent an organic radical, in particular alkyl, aryl, arylalkyl or alkylaryl.
  • R a to R d each independently represent an organic radical, in particular alkyl, aryl, arylalkyl or alkylaryl.
  • Alkylsulfoxonium salts such as (Ci-C 4 ) -trialkylsulfonium and (Ci-C 4 ) -trialkylsulfoxonium salts.
  • substituted 2-heteroaryloxypyridines of the general formula (I) according to the invention may be present in various tautomeric structures, all of which are encompassed by the general formula (I).
  • Preferred subject matter of the invention are compounds of the general formula (I), in which X represents nitrogen, -CF- or -CH-,
  • n 0, 1 or 2
  • R 1 represents an optionally substituted aryl, heteroaryl or heterocylyl, each ring or ring system optionally being substituted with up to 5 substituents selected independently from the group R 7 ,
  • R 2 independently of one another for halogen, cyano, nitro, formyl, formamide, (GG) - alkyl, (GG) - haloalkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 2 -C 6 ) -haloalkenyl, (C 2 -C 6 ) -haloalkynyl, (Ci-C 4 ) -alkoxy- (Ci-C 4 ) -alkyl, (Ci-C 4 ) -haloalkoxy- (Ci-C 4 ) -alkyl, (Ci-C 4 ) -alkylthio- (Ci-C 4 ) -alkyl, (Ci-C 4 ) -alkylsulfmyl- (Ci-C 4 ) -alkyl, (Ci-C 4 ) -alkylsulfonyl- (
  • R 3 is hydrogen, halogen, cyano, nitro, formyl, (Ci-C 6 ) alkyl, (Ci-C 6 ) haloalkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl , (C 2 -C 6 ) haloalkenyl, (C 2 -C 6 ) haloalkynyl, (Ci-C 4 ) alkoxy- (Ci-C 4 ) - alkyl, (Ci-C 4 ) -haloalkoxy- (Ci -C 4 ) -alkyl, (Ci-C 4 ) -alkylthio- (Ci-C 4 ) -alkyl, (Ci-C 4 ) - alkylsulfmyl- (Ci-C 4 ) -alkyl, (Ci-C 4 ) - Alkylsulfonyl- (C
  • R 4 and R 5 independently of one another are hydrogen, hydroxy, halogen, (Ci-C 6 ) -alkyl, (C ' iG,) - haloalkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) - Alkynyl, (Ci-C 4 ) -alkoxy- (Ci-C 4 ) -alkyl, (Ci-C 4 ) - haloalkoxy- (Ci-C 4 ) -alkyl, (Ci-C 4 ) -alkylthio- (Ci C 4 ) alkyl, (Ci-C 4 ) alkylsulfmyl- (Ci-C 4 ) -alkyl, (Ci-C 4 ) -alkylsulfonyl- (Ci-C 4 ) -alkyl, (Ci-C 6 ) -alkylcarbonyl , (
  • R 4 and R 5 together form a 3- to 6-membered carbocyclic ring or a 3- to 6-membered saturated heterocyclic ring with up to 2 oxygen atoms, or
  • R 4 and R 5 together form a (Ci-C 3 ) alkylidene radical or (Ci-C 3 ) haloalkylidene radical, R 6 for hydrogen, (Ci-C 6 ) -alkyl, (Ci-C 6 ) -haloalkyl, aryl- (Ci-C4) -alkyl, heteroaryl- (Ci-C4) -alkyl, (C 3 -C 6 ) -Cycloalkyl, (C3-C 6 ) -cycloalkyl- (Ci-C 4 ) -alkyl, (C 3 -C 6 ) -halocycloalkyl, (C 3 -C 6 ) -halocycloalkyl- (Ci-C 4 ) -alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (Ci-C 4 ) alkoxy- (Ci-
  • R 7 for hydrogen, halogen, cyano, nitro, formyl, (Ci-C 6 ) alkyl, (Ci-C 6 ) haloalkyl, (GG,) - alkenyl, (C 2 -C 6 ) alkynyl, (C 2 -C 6 ) haloalkenyl, (C 2 -C 6 ) haloalkynyl, (Ci-C 4 ) alkoxy- (Ci-C 4 ) alkyl, (Ci-C 4 ) -haloalkoxy- (Ci-C 4 ) alkyl, (GC 4 ) alkylthio- (GC 4 ) alkyl, (Ci-C 4 ) alkylsulfinyl (Ci-C4) alkyl, (Ci-C4) alkylsulfonyl- (Ci-C4) alkyl , (Ci-C 6 ) alkylcarbonyl, (GC 6 )
  • X represents nitrogen, -CF- or -CH-
  • n 0, 1 or 2
  • R 1 represents an optionally substituted aryl, heteroaryl or heterocylyl, each ring or ring system optionally being substituted with up to 5 substituents, selected independently of one another from the group R 7 ,
  • R 2 independently of one another for halogen, cyano, nitro, formyl, formamide, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 2 -C 4 ) -alkenyl, (C 2 -C 4 ) -Alkynyl, (C 2 -C 4 ) -haloalkenyl, (Ci-C 4 ) -alkoxy- (Ci-C 4 ) - alkyl, (Ci-C 4 ) -haloalkoxy- (Ci-C 4 ) -alkyl, (Ci-C 4 ) -alkylcarbonyl, (Ci-C 4 ) -haloalkylcarbonyl, carboxyl, (Ci-C 4 ) -alkoxycarbonyl, ( C 1 -C 4 ) haloalkoxycarbonyl, (C 3 -C 6 ) cycl
  • R 3 is hydrogen, halogen, cyano, nitro, formyl, (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl , (C 2 -C 4 ) haloalkenyl, (C 2 -C 4 ) haloalkynyl, (Ci-C 4 ) alkylcarbonyl, (Ci-C 4 ) haloalkylcarbonyl, carboxyl, (Ci-C 4 ) alkoxycarbonyl, (C 1 -C 4 ) haloalkoxycarbonyl, (C 3 -C 6 ) cycloalkoxycarbonyl, (Ci-C 4 ) alkylaminocarbonyl, (C 2 -C 6 ) dialkylaminocarbonyl, hydroxy, (Ci-C 4 ) alkoxy, (C
  • R 4 and R 5 are independently hydrogen, hydroxy, halogen, (Ci-C 4) -alkyl, (C 1 -C 4) - haloalkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) -Alkynyl, (Ci-C 4 ) -alkoxycarbonyl, (C 1 -C 4 ) - haloalkoxycarbonyl or (C 3 -C 6 ) -cycloalkoxycarbonyl, or
  • R 4 and R 5 together form a (Ci-C 3 ) alkylidene radical or (Ci-C 3 ) haloalkylidene radical,
  • R 6 is hydrogen, (Ci-C 4 ) -alkyl, (Ci-C 4 ) -haloalkyl, aryl- (Ci-C 4 ) -alkyl, heteroaryl- (Ci-C 4 ) -alkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) alkynyl, (Ci-C 4) alkylcarbonyl, formyl or (Ci-C is 4) alkoxycarbonyl,
  • R 7 is hydrogen, halogen, cyano, nitro, formyl, (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl , (C 2 -C 4 ) haloalkenyl, (C 2 -C 4 ) haloalkynyl, (Ci-C 4 ) alkoxy- (Ci-C 4 ) - alkyl, (Ci-C 4 ) -haloalkoxy- (Ci -C 4 ) -alkyl, (Ci-C 4 ) -alkylcarbonyl, (Ci-C 4 ) -haloalkylcarbonyl, carboxyl, (Ci-C 4 ) -alkoxycarbonyl, (C 1 -C 4 ) - haloalkoxycarbonyl, (C 3 - C 6
  • X represents nitrogen, -CF- or -CH-
  • n 0, 1 or 2
  • R 1 represents an optionally substituted phenyl, pyridyl or pyrimidyl, each ring or ring system optionally being substituted with up to 5 substituents, selected independently of one another from the group R 7 ,
  • R 2 independently of one another for halogen, cyano, (Ci-C i) alkyl, (Ci-C 4 ) haloalkyl, carboxyl,
  • R 3 is hydrogen, halogen, cyano, (Ci-C i) alkyl, (Ci-C 4 ) haloalkyl, (C2-C i) alkenyl, (C 2 -C 4 ) alkynyl, (C2-C4 ) -Haloalkenyl, (C2-C 4 ) -haloalkynyl, (Ci-C 4 ) -alkoxy or (Ci-C 4 ) -haloalkoxy,
  • R 4 and R 5 are independently hydrogen, halogen, (Ci-C 4) -alkyl or (C 1 -C 4) - alkoxycarbonyl,
  • R 6 represents hydrogen, (Ci-C 4 ) -alkyl, (Ci-C 4 ) -alkylcarbonyl or (Ci-C 4 ) -alkoxycarbonyl, and R 7 for hydrogen, halogen, cyano, (Ci-C4) alkyl, (Ci-C4) haloalkyl, carboxyl, (C1-C4) alkoxycarbonyl, hydroxy, (Ci-C4) alkoxy or (Ci-C4) -Haloalkoxy stands.
  • X represents nitrogen, -CF- or -CH-
  • A stands for oxygen, sulfur, -CH2 - or -NR 6 -,
  • R 1 represents an optionally substituted phenyl, pyridyl or pyrimidyl, each ring or ring system optionally being substituted with up to 5 substituents, selected independently of one another from the group R 7 ,
  • R 2 independently of one another for halogen, cyano, (Ci-C i) -alkyl, (Ci-C ij-haloalkyl, carboxyl,
  • R 3 is hydrogen, halogen, cyano, (Ci-C i) -alkyl, (Ci-C ij-haloalkyl, (Ci-C i) -alkoxy or
  • R 6 represents hydrogen or methyl
  • R 7 represents hydrogen, halogen, cyano, (Ci-C i) alkyl, (Ci-C4) haloalkyl, (Ci-C4) alkoxy or
  • X represents -CH-, -CF- or nitrogen
  • A stands for oxygen, sulfur, -CH2 - or -NR 6 -
  • R 1 represents an optionally substituted phenyl, pyrid-2-yl or pyrimid-2-yl, each ring optionally being substituted with up to 5 substituents, selected independently of one another from the group R 7 ,
  • R 2 independently of one another for fluorine, chlorine, bromine, cyano, methyl, ethyl, trifluoromethyl,
  • Methoxy, methoxycarbonylmethyl, carboxylmethyl, m is 0, 1, 2 or 3,
  • R 3 represents hydrogen, fluorine, chlorine, cyano, methyl, trifluoromethyl, methoxy, trifluoromethoxy
  • R 6 represents hydrogen or methyl
  • R 7 represents hydrogen, fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl, methoxy, trifluoromethoxy.
  • X represents -CH-, -CF- or nitrogen
  • A stands for oxygen, sulfur, -CH2 - or -NH-
  • R 1 is phenyl, 4-fluorophenyl, 2,4-difluorophenyl, 3,4-difluorophenyl, 3- (trifluoromethyl) phenyl, 3-methoxyphenyl, 3-chlorophenyl, 4-chlorophenyl 4-cyanophenyl, 4-methylphenyl, 3-fluorine -4-methylphenyl, 4-fluoro-3-methylphenyl, 2,4-difluoro-3-methoxyphenyl, 5-chloro-3-fluoropyrid-2-yl, 5-chloropyrid-2-yl, 5-fluoropyrid-2-yl , 3,5-difluoropyrid-2-yl, 5-fluoropyrimid-2-yl, 5-chloropyrimid-2-yl;
  • R 2 represents methyl, m is 0, 1 or 2, and
  • R 3 represents hydrogen, fluorine, chlorine, trifluoromethyl.
  • alkylsulfonyl alone or as part of a chemical group - stands for straight-chain or branched alkylsulfonyl, preferably with 1 to 8, or with 1 to 6
  • Carbon atoms for example (but not limited to) (Ci-C 6 ) alkylsulfonyl such as methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, l, l-dimethylethylsulfonyl, pentyl 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, l, l-dimethylpropylsulfonyl, 1, 2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonylsulfonyl, 1-methyl-
  • alkylthio alone or as part of a chemical group - stands for straight-chain or branched S-alkyl, preferably with 1 to 8, or with 1 to 6
  • Carbon atoms such as (Ci-Cio) -, (C i-Cr,) - or (Ci-C i) -alkylthio, for example (but not limited to) (Ci-C 6 ) -alkylthio such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1, 1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, l, l-dimethylpropylthio, 1, 2-dimethylpropylthio, 2,2 Dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio,
  • (but not limited to) (Ci-C 6 ) alkylsulfinyl such as methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl,
  • Alkoxy means an alkyl radical bonded via an oxygen atom, eg. B. (but not limited to) (Ci-C 6 ) alkoxy such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, l, l-dimethylethoxy, pentoxy, 1-methylbutoxy, 2 -Methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1, 2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1 - methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, l, l -Dimethylbutoxy, l, 2-dimethylbutoxy, l, 3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, l
  • Alkenyloxy means an alkenyl radical bonded via an oxygen atom
  • alkynyloxy means an alkynyl radical bonded via an oxygen atom, such as (C2-C10) -, (C2-C6) - or (C2-C i) -alkenoxy or (C3-C10) -, ( C3-C6) or (C3-C4) alkynoxy.
  • the number of carbon atoms refers to the alkyl radical in the
  • the number of carbon atoms relates to the alkyl radical in the alkoxycarbonyl group.
  • the number of carbon atoms relates to the alkenyl or alkynyl radical in the alkene or alkynyloxycarbonyl group.
  • aryl means an optionally substituted mono-, bi- or polycyclic aromatic system with preferably 6 to 14, in particular 6 to 10 ring carbon atoms, for example phenyl, naphthyl, anthryl, phenanthrenyl, and the like, preferably phenyl.
  • heterocyclic radical contains at least one heterocyclic ring
  • Substituted heterocyclyl also includes multi-cyclic systems, such as, for example, 8-azabicyclo [3.2.l] octanyl, 8-azabicyclo [2.2.2] octanyl or 1-azabicyclo [2.2.l] heptyl.
  • spirocyclic systems are also included, such as, for example, l-oxa-5-aza-spiro [2.3] hexyl.
  • the heterocyclic ring preferably contains 3 to 9 ring atoms, in particular 3 to 6 ring atoms, and one or more, preferably 1 to 4, in particular 1, 2 or 3, heteroatoms in the heterocyclic ring, preferably from the group N, O, and S, but two oxygen atoms should not be directly adjacent, such as with a hetero atom from the group N, O and S 1- or 2- or 3-pyrrolidinyl, 3,4-dihydro-2H-pyrrole-2- or 3 -yl, 2,3-dihydro-lH-pyrrole-l- or 2- or 3- or 4- or 5-yl; 2,5-dihydro-1H-pyrrole-1- or 2- or 3-yl, 1- or 2- or 3- or 4-piperidinyl; 2, 3,4,5-tetrahydropyridin-2- or 3- or 4- or 5-yl or 6-yl; l, 2,3,6-tetrahydropyridin-l- or 2- or 3- or 4- or 5- or 6-yl
  • 2- or 3- or 4-tetrahydropyranyl 3,4-dihydro-2H-pyran-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-pyran-2- or 3- or 4- or 5- or 6-yl; 2H-pyran-2- or 3- or 4- or 5- or 6-yl; 4H-pyran-2- or 3- or 4-yl, 2- or 3- or 4-oxepanyl; 2,3,4,5-tetrahydrooxepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7-tetrahydrooxepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2, 3,6,7-tetrahydrooxepin-2- or 3- or 4-yl; 2,3-dihydrooxepin-2- or 3- or 4- or 5- or 6- or 7-yl;
  • 4,5-dihydrooxepin-2- or 3- or 4-yl 2,5-dihydrooxepin-2- or 3- or 4- or 5- or 6- or 7-yl; Oxepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2- or 3-tetrahydrothiophenyl; 2,3-dihydrothiophene-2- or 3- or 4- or 5-yl; 2,5-dihydrothiophene-2- or 3-yl; Tetrahydro-2H-thiopyran-2- or 3- or 4-yl; 3,4-dihydro-2H-thiopyran-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-thiopyran-2- or 3- or 4- or 5- or 6-yl; 2H-thiopyran-2- or 3- or 4- or 5- or 6-yl; 4H-thiopyran-2- or 3- or 4-yl.
  • Preferred 3-ring and 4-ring heterocycles are, for example, 1- or 2-aziridinyl, oxiranyl, thiiranyl, 1- or 2- or 3-azetidinyl, 2- or 3-oxetanyl, 2- or 3-thietanyl, 1,3 -Dioxetan-2-yl.
  • heterocyclyl are a partially or fully hydrogenated heterocyclic radical with two heteroatoms from the group N, O and S, such as 1- or 2- or 3- or 4-pyrazolidinyl; 4,5-dihydro-3H-pyrazole-3- or 4- or 5-yl; 4,5-dihydro-1H-pyrazole-l- or 3- or 4- or 5-yl; 2,3-dihydro-1H-pyrazole-1- or 2- or 3- or 4- or 5-yl; 1- or 2- or 3- or 4-imidazolidinyl; 2,3-dihydro-1H-imidazole-1- or 2- or 3- or 4-yl; 2,5-dihydro-1H-imidazole-1- or 2- or 4- or 5-yl; 4,5-dihydro-1H-imidazole-1- or 2- or 4- or 5-yl; Hexahydropyridazin-l- or 2- or 3- or 4-yl; l, 2,3,4-tetrahydropyridazin
  • 1,2-dithiolan-3- or 4-yl 1,2-dithiolan-3- or 4-yl; 3H-l, 2-dithiol-3- or 4- or 5-yl; l, 3-dithiolan-2- or 4-yl; l, 3-dithiol-2- or 4-yl; 1,2-dithian-3- or 4-yl; 3,4-dihydro-l, 2-dithiin-3- or 4- or 5- or 6-yl; 3,6-dihydro-
  • 1,2-dithiin-3- or 4-yl 1,2-dithiin-3- or 4-yl; 1,2-dithiin-3- or 4-yl; l, 3-dithian-2- or 4- or 5-yl; 4H-l, 3-dithiin-2- or 4- or 5- or 6-yl; Isoxazolidin-2- or 3- or 4- or 5-yl; 2,3-dihydroisoxazole-2- or 3- or
  • 6- or 7-yl 2,5-dihydro-l, 3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 2,7-dihydro-l, 3-oxazepine 2- or 4- or 5- or 6- or 7-yl; 4,5-dihydro-l, 3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 4,7-dihydro-l, 3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 6,7-dihydro-l, 3-oxazepin-2- or 4- or 5- or 6- or 7-yl; l, 3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 1, 4-oxazepan-2- or 3- or 5- or 6- or 7-yl; 2,3,4,5-tetrahydro-l, 4-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2, 3,4,7-tetrahydro-l, 4-oxazepin-2
  • heterocyclyl are a partially or fully hydrogenated heterocyclic radical with 3 heteroatoms from the group N, O and S, such as l, 4,2-dioxazolidin-2- or 3- or 5-yl; l, 4,2-dioxazol-3- or 5-yl; 1, 4,2-dioxazinan-2- or -3- or 5- or 6-yl; 5,6-dihydro-l, 4,2-dioxazin-3- or 5- or 6-yl; l, 4,2-dioxazin-3- or 5- or 6-yl; l, 4,2-dioxazepan-2- or 3- or 5- or 6- or 7-yl; 6,7-dihydro-5H-l, 4,2-dioxazepin-3- or 5- or 6- or 7-yl; 2,3-dihydro-7H-l, 4,2-dioxazepin-2- or 3- or 5- or 6- or 7-yl; 2,3-dihydro-5H-l, 4,2-dioxa
  • nitrogen heterocycle is partially or fully saturated, this can be linked to the rest of the molecule via carbon as well as nitrogen.
  • Possible substituents for a substituted heterocyclic radical are the substituents mentioned below, and also oxo and thioxo.
  • the oxo group as a substituent on a ring carbon atom then means, for example, a carbonyl group in the heterocyclic ring. This preferably also includes lactones and lactams.
  • the oxo group can also occur on the hetero ring atoms, which can exist in different oxidation states, for example in the case of N and S, and then form, for example, the divalent groups N (O), S (O) (also SO for short) and S (0) 2 (also briefly SO2) in the heterocyclic ring. In the case of -N (O) - and -S (0) groups, both enantiomers are included.
  • heteroaryl stands for heteroaromatic compounds, ie. H.
  • heteroaryls are, for example, 1H-pyrrol-l-yl; lH-pyrrol-2-yl; lH-pyrrole
  • Carbon atoms are part of a further aromatic ring, so they are fused heteroaromatic systems, such as benzo-fused or multiply fused heteroaromatics.
  • quinolines e.g. quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl
  • Isoquinolines e.g. quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl
  • Isoquinolines e.g.
  • heteroaryl are also 5- or 6-membered benzo-fused rings from the group lH-indol-l-yl, lH-indol-2-yl, lH-indol-3-yl, lH-indol-4-yl, lH- Indol-5-yl, 1H-indol-6-yl, lH-indol-7-yl, l-benzofuran-2-yl, l-benzofuran-3-yl, l-benzofuran-4-yl, l-benzofuran 5- yl, l-benzofuran-6-yl, l-benzofuran-7-yl, l-benzothiophene-2-yl, l-benzothiophene-3-yl, 1-benzothiophene-4-yl, l-benzothiophene-5- yl, l-benzothiophene-6-yl, l-benz
  • halogen means, for example, fluorine, chlorine, bromine or iodine.
  • halogen means for example a fluorine, chlorine, bromine or iodine atom.
  • alkyl means a straight-chain or branched open-chain, saturated hydrocarbon radical which is optionally substituted one or more times and is referred to in the latter case as “substituted alkyl”.
  • Preferred substituents are halogen atoms, alkoxy, haloalkoxy, cyano, alkylthio, haloalkylthio, amino or nitro groups; methoxy, methyl, fluoroalkyl, cyano, nitro, fluorine, chlorine, bromine or iodine are particularly preferred.
  • the prefix "bis” also includes the combination of different alkyl residues, e.g. B. methyl (ethyl) or ethyl (methyl).
  • Haloalkyl mean alkyl, alkenyl or alkynyl, for example monohaloalkyl, which is partially or completely substituted by the same or different halogen atoms
  • ( Monohalogenalkyl) such as B. CH 2 CH 2 CI, CH 2 CH 2 Br, CHCICH 3 , CH 2 CI, CH 2 F; Perhaloalkyl such as
  • the term perhaloalkyl also includes the term perfluoroalkyl.
  • Haloalkoxy is, for example, OCF 3 , OCHF 2 , OCH 2 F, OCF 2 CF 3 , OCH 2 CF 3 and OCH 2 CH 2 CI; The same applies to haloalkenyl and other halogen-substituted radicals.
  • (Ci-C4) -alkyl mentioned here by way of example means a shorthand notation for straight-chain or branched alkyl having one to 4 carbon atoms corresponding to the
  • Range specification for carbon atoms includes the radicals methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl.
  • General alkyl radicals with a larger specified range of carbon atoms e.g. B. "(Ci-C 6 ) alkyl”, also include straight-chain or branched alkyl radicals with a larger number of carbon atoms, ie, according to the example, also the alkyl radicals with 5 and 6 carbon atoms.
  • hydrocarbon radicals such as alkyl, alkenyl and alkynyl radicals, even in composite radicals, are the lower carbon skeletons, e.g. with 1 to 6 carbon atoms or in the case of unsaturated groups with 2 to 6 carbon atoms, preferred.
  • Alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals, at least one double bond or triple bond being present. Residues with a double bond or
  • alkenyl also includes straight-chain or branched open-chain ones
  • Hydrocarbon radicals with more than one double bond such as 1,3-butadienyl and 1,4-pentadienyl, but also allenyl or cumulenyl radicals with one or more cumulative double bonds, such as, for example, allenyl (1,2-propadienyl), 1,1 2-butadienyl and l, 2,3-pentatrienyl.
  • Alkenyl means, for example, vinyl, which can optionally be substituted by further alkyl radicals, for example (but not limited to) (C2-C6) alkenyl such as ethenyl, l-propenyl, 2-propenyl, 1-methylethenyl, l-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3- Pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl- 2-butenyl, l-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1, 1-dimethyl-2-propenyl, 1, 2-dimethyl
  • alkynyl also includes straight-chain or branched open-chain ones
  • C2-C6 alkynyl means e.g. Ethynyl, l-propynyl, 2-propynyl, l-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, l-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, l-methyl- 2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1, 1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-2-pentynyl
  • cycloalkyl means a carbocyclic, saturated ring system with preferably 3-8 ring C atoms, e.g. Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, which is optionally further substituted, preferably by hydrogen, alkyl, alkoxy, cyano, nitro, alkylthio, haloalkylthio, halogen, alkenyl, alkynyl, haloalkyl, AMino, alkylamino, bisalkylamino, alkocycarbonyl,
  • Cycloalkylaminocarbonyl In the case of optionally substituted cycloalkyl, cyclic systems with substituents are included, substituents also having a double bond on
  • Cycloalkyl radical e.g. B. an alkylidene group such as methylidene are included.
  • alkylidene group such as methylidene
  • multi-cyclic aliphatic systems are also included, such as, for example, bicyclo [1.0] butan-1-yl, bicyclo [1.0] butan-2-yl, bicyclo [2.1.0] pentan-1 - yl, bicyclo [l.
  • (C3-C7) cycloalkyl means a shorthand notation for cycloalkyl of three to seven
  • spirocyclic aliphatic systems are also included, such as, for example, spiro [2.2] pent-l-yl, spiro [2.3] hex-l-yl, spiro [2.3] hex-4-yl, 3-spiro [2.3] hex-5-yl,
  • Cycloalkenyl means a carbocyclic, non-aromatic, partially unsaturated ring system with preferably 4-8 C atoms, e.g. 1-Cyclobutenyl, 2-Cyclobutenyl, 1-Cyclopentenyl, 2-Cyclopentenyl, 3-Cyclopentenyl, or 1-Cyclohexenyl, 2-Cyclohexenyl, 3-Cyclohexenyl, l, 3-Cyclohexadienyl or 1, 4-Cyclohexadienyl, whereby also substituents with a Double bond on the cycloalkenyl radical, e.g. B.
  • the explanations for substituted cycloalkyl apply accordingly.
  • alkylidene e.g. B. also in the form (Ci-Cio) alkylidene, means the remainder of a straight-chain or branched open-chain hydrocarbon radical which is bonded via a double bond.
  • Cycloalkylidene means a
  • Arylalkyl stands for an aryl radical bonded via an alkyl group
  • heteroarylalkyl means a heteroaryl radical bonded via an alkyl group
  • heterocyclylalkyl means a heterocyclyl radical bonded via an alkyl group.
  • haloalkylthio alone or as part of a chemical group - stands for straight-chain or branched S -haloalkyl, preferably with 1 to 8, or with 1 to 6 carbon atoms, such as (Ci-Cs) -, (C ' iG,) - or (Ci-C4) -haloalkylthio, for example (but not limited to) trifluoromethylthio, pentafluoroethylthio, difluoromethyl, 2,2-difluoroeth-1-ylthio, 2,2,2-difluoroeth-1-ylthio, 3,3,3 -prop-l-ylthio.
  • Halocycloalkyl means the same or different halogen atoms, such as. B. F, CI and Br, or by haloalkyl, such as. B. trifluoromethyl or difluoromethyl partially or completely substituted cycloalkyl, for example l-fluorocycloprop-l-yl, 2-fluorocycloprop-l-yl, 2,2-difluorocycloprop-l-yl, 1-fluorocyclobut-l-yl, l-trifluoromethylcycloprop- l-yl, 2-trifluoromethylcycloprop-l-yl, l-chlorocycloprop-l-yl, 2-chlorocycloprop-l-yl, 2,2-dichlorocycloprop-l-yl, 3,3-difluorocyclobutyl, According to the invention, "trialkylsilyl" - alone or as part of a chemical group - stands for straight-chain or branchedi
  • Carbon atoms such as tri - [(Ci-Cs) -, (C ' iG,) - or (Ci-C i) alkyl] silyl, for example (but not limited to) trimethylsilyl, triethylsilyl, tri- (n-propyl) silyl, tri- (isopropyl) silyl, tri- (n-butyl) silyl, tri- (l-methylprop-l-yl) silyl, tri- (2-methylprop-l-yl) silyl, tri (l, l-dimethyleth-l-yl) silyl, tri (2,2-dimethyleth-1-yl) silyl.
  • the compounds of the general formula (1) can exist as stereoisomers.
  • the possible stereoisomers defined by their specific spatial shape, such as enantiomers, diastereomers, Z and E isomers, are all encompassed by the general formula (1).
  • enantiomers, diastereomers, Z and E isomers are all encompassed by the general formula (1).
  • diastereomers Z and E isomers
  • enantiomers and diastereomers can occur.
  • Stereoisomers can be derived from the at
  • stereoisomers can be produced selectively by using stereoselective reactions using optically active starting materials and / or auxiliary substances.
  • the invention thus also relates to all stereoisomers which are encompassed by the general formula (1) but are not specified with their specific stereoform, and to mixtures thereof.
  • the cleaning can also be carried out by
  • the present invention also claims processes for the preparation of the compounds of the general formula (I) according to the invention.
  • the compounds of the general formula (I) according to the invention can be prepared, inter alia, using known processes.
  • the synthetic routes used and investigated are based on commercially available or easily manufactured building blocks.
  • the groupings X, A, R 1 , R 2 , R 3 and m of the general formula (I) have the meanings defined above in the following schemes, unless exemplary but not restrictive definitions are given.
  • the pyridines of the general formula (Ia) can be coupled via a coupling of the pyridines (E-III), LG being a leaving group, with the disulfide (E-IV) in the presence of either zinc (O) and palladium catalysts (such as, for example Pd ⁇ ppfjCh.CFbCh), or copper (0) and bases.
  • the base can be an acetate salt of an alkali metal (such as sodium or potassium).
  • the reactions are generally carried out in an organic solvent, such as
  • the pyridines of the general formula (E-III) can be prepared via an alkylation of the pyridines (EI) in the presence of bases with the pyri (mi) din (E-II), where LG is a leaving group and copper salts.
  • the base can be a carbonate salt of an alkali metal (such as sodium, potassium or cesium).
  • the copper salts can be copper halides such as copper (I) iodide.
  • the reactions are generally carried out in an organic solvent such as acetonitrile or dimethylformamide at temperatures between 0 ° C and the boiling point of the solvent.
  • the sulfones and sulfoxides of the general formula (Ib) can be prepared by oxidation of the pyridines (Ia). Such reactions are known to the person skilled in the art and are described, for example, in Advanced Synthesis & Catalysis (201 1), 353 (2 + 3), 295-302.
  • the pyridines of the general formula (Ic) can be coupled via a coupling of the pyridines (E-VII) with the alkyl halide (E-VIII), where shark is a halogen, in the presence of palladium catalysts (such as Example Pd (PPh3) 4) and bases are prepared.
  • the base can be a carbonate salt of an alkali metal (such as sodium or potassium).
  • the reactions are generally carried out in an organic solvent, such as, for example, tetrahydrofuran, toluene or ethanol, with or without the addition of water, at temperatures between 0 ° C. and the boiling point of the solvent.
  • the pyridines of the general formula (E-VII) can be coupled with pinacolborane or bis (pinacolato) diborone in the presence of palladium catalysts (such as, for example, Pd (MeCN)) via a coupling of the pyridines (E-VI), where shark is a halogen. 2Cl2), ligands (such as XPhos) and bases.
  • the base can be an amine (such as triethylamine).
  • the reactions are generally carried out in an organic solvent such as tetrahydrofuran or dioxane at temperatures between 0 ° C and the boiling point of the solvent.
  • the pyridines of the general formula (E-VI) can be prepared via an alkylation of the pyridines (E-V) in the presence of bases with the pyri (mi) din (E-II), where LG is a leaving group and copper salts.
  • the base can be a carbonate salt of an alkali metal (such as sodium, potassium or cesium).
  • the copper salts can be copper halides such as copper (I) iodide.
  • the reactions are generally carried out in an organic solvent such as acetonitrile or dimethylformamide at temperatures between 0 ° C and the boiling point of the solvent.
  • the pyridines of the general formula (Id) can be prepared via an alkylation of the pyridines (E-XII) in the presence of bases with the pyri (mi) din (E-II), where LG is a leaving group and copper salts.
  • the base can be a carbonate salt of an alkali metal (such as sodium, potassium or cesium).
  • the copper salts can be copper halides, such as Copper (I) iodide.
  • the reactions are generally carried out in an organic solvent such as acetonitrile or dimethylformamide at temperatures between 0 ° C and the boiling point of the solvent.
  • the pyridines of the general formula (E-XII) can be prepared by demethylating the pyridines (E-XI) in the presence of either hydrobromic acid and acetic acid or boron tribromide.
  • the reactions with boron tribromide are generally carried out in an organic solvent such as dichloromethane at temperatures between 0 ° C and the boiling point of the solvent.
  • the pyridines of the general formula (E-XI) can be prepared by coupling the pyridines (E-IX) with the boronic acid (EX) in the presence of copper (II) catalysts (such as Cu (OAc) 2) and bases become.
  • the base can be an amine (such as triethylamine).
  • the reactions are generally carried out in an organic solvent such as dichloromethane at temperatures between 0 ° C and the boiling point of the solvent.
  • Synthesis stage 2 2 - [(4-methyl-3-phenylsulfanyl-2-pyridyl) oxy] pyrimidine (table example No. 1-216):
  • the 1 H-NMR data of selected examples are noted in the form of 1 H-NMR peak lists. For each signal peak, the d-value is listed in ppm and then the signal intensity in round brackets. The d-value - signal intensity-number pairs of different signal peaks are listed separated by semicolons.
  • the peak list of an example therefore has the form: di (intensity ⁇ ; 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 of the signal intensities. For wide signals, multiple peaks or the center of the signal and their relative intensity can be shown compared to the most intense signal in the spectrum.
  • the peaks of stereoisomers of the target compounds and / or peaks of impurities usually have a lower intensity on average than the peaks of the target compounds (for example with a purity of> 90%).
  • stereoisomers and / or impurities can be typical of each
  • An expert who calculates the peaks of the target compounds using known methods can isolate the peaks of the target compounds as required, using additional intensity filters if necessary. This isolation would be similar to the relevant peak picking in the classic 1H NMR interpretation.
  • the present invention furthermore relates to the use of one or more
  • the present invention furthermore relates to a process for controlling harmful plants and / or for regulating the growth of plants, characterized in that an effective amount of one or more compounds of the general formula (I) and / or their salts, as defined above, preferably in one the configuration characterized as preferred or particularly preferred, in particular one or more compounds of the formulas (1-001) to (1-662) and / or their salts, in each case as defined above, or an agent according to the invention as defined below,
  • the present invention also relates to a process for controlling unwanted plants, preferably in crops, characterized in that an effective amount of one or more compounds of the general formula (1) and / or their salts, as defined above, preferably in one of the as preferably or particularly preferably characterized embodiment, in particular one or more compounds of the formulas (1-001) to (1-662) and / or their salts, in each case as defined above, or an agent according to the invention, as defined below,
  • undesirable plants e.g. harmful plants such as monocotyledonous or dicotyledon weeds or undesired crop plants
  • the seeds of the undesirable plants i.e. plant seeds, e.g. grains, seeds or vegetative propagation organs such as tubers or shoot parts with buds
  • the soil in or on which the unwanted plants grow e.g. the soil of cultivated land or non-cultivated land
  • the area under cultivation ie the area on which the undesired plants will grow
  • the present invention also relates to methods for combating
  • the compounds according to the invention or the agents according to the invention can e.g. in pre-sowing (possibly also by incorporation into the soil), pre-emergence and / or
  • one or more compounds of the general formula (I) and / or their salts are preferably used for controlling harmful plants or for regulating growth in crops of useful plants or ornamental plants, the useful plants or ornamental plants in a preferred embodiment are transgenic plants.
  • the compounds of the general formula (1) according to the invention and / or their salts are suitable for combating the following genera of monocotyledonous and dicotyledonous harmful plants:
  • Monocotyledonous harmful plants of the genera Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostata, Festiochaperimist, Eriochaperimist, Eriochaperim , lschaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.
  • the compounds of the general formula (1) according to the invention are applied to the surface of the earth before the germinating of the harmful plants (grasses and / or weeds) (pre-emergence method), then either the emergence of the weed or weed seedlings is prevented completely or this grow to the cotyledon stage, but then stop growing and eventually die completely after three to four weeks.
  • Post-emergence treatment stops growing after the treatment and the harmful plants remain in the growth stage at the time of application or die completely after a certain time, so that this is harmful to the crop plants
  • the compounds of the general formula (1) according to the invention have excellent herbicidal activity against mono- and dicotyledon weeds
  • crop plants of economically important crops are e.g. dicotyledon cultures of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, fpomoea, Lactuca, Linum,
  • Phytonutrients and to ease the crop, e.g. by triggering desiccation and stunted growth. Furthermore, they are also suitable for general control and inhibition of undesirable vegetative growth without killing the plants. Inhibiting vegetative growth plays a major role in many monocotyledonous and dicotyledonous crops, since, for example, this can reduce or completely prevent stock formation.
  • the active compounds of the general formula (I) can also be used to control harmful plants in crops of plants which have been modified by genetic engineering or by conventional mutagenesis.
  • the transgenic plants are generally distinguished by special advantageous properties, for example resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
  • Other special properties concern e.g. Emtegut in terms of quantity, quality, shelf life, composition and special ingredients.
  • transgenic plants with an increased starch content or altered starch quality or with a different fatty acid composition of the crop are known.
  • transgenic cultures Preferred with respect to transgenic cultures is the use of the compounds of the general formula (I) and / or their salts in economically important transgenic cultures of useful and ornamental plants, e.g. of cereals such as wheat, barley, rye, oats, millet, rice and corn or also crops of sugar beet, cotton, soybeans, rapeseed, potatoes, tomatoes, peas and other vegetables.
  • cereals such as wheat, barley, rye, oats, millet, rice and corn or also crops of sugar beet, cotton, soybeans, rapeseed, potatoes, tomatoes, peas and other vegetables.
  • the compounds of the general formula (I) according to the invention can preferably also be used as herbicides in crops which are resistant to the phytotoxic effects of the herbicides or have been rendered resistant to genetic engineering.
  • the compounds of the general formula (I) according to the invention can also be used to control harmful plants in crops of known or still to be developed genetically modified plants.
  • the transgenic plants are usually distinguished by special advantageous properties, for example by resistance to certain pesticides, especially certain ones
  • Herbicides resistance to plant diseases or pathogens such as certain insects or microorganisms such as fungi, bacteria or viruses.
  • Other special properties concern e.g. the crop in terms of quantity, quality, storability,
  • transgenic plants with an increased starch content or altered starch quality or with a different fatty acid composition of the crop are known.
  • Other special properties can include tolerance or resistance to abiotic stressors e.g. There is heat, cold, dryness, salt and ultraviolet radiation.
  • cereals such as wheat, barley, rye, oats, triticale, millet, rice, manioc and corn or also crops of sugar beet, cotton, soybean, rapeseed, potato, tomato, pea and other vegetables.
  • the compounds of the general formula (I) can preferably be used as herbicides in
  • Crop crops are used which are resistant to the phytotoxic effects of the herbicides or have been made genetically resistant.
  • Conventional ways of producing new plants which have modified properties in comparison to previously occurring plants are, for example, classic ones
  • nucleic acid molecules can be introduced into plasmids which allow mutagenesis or a sequence change by recombining DNA sequences. With the help of standard procedures e.g. Base exchanges made, partial sequences removed or natural or synthetic sequences added. To connect the DNA fragments to one another, adapters or linkers can be attached to the fragments.
  • the production of plant cells with a reduced activity of a gene product can be achieved, for example, by the expression of at least one corresponding antisense RNA, a sense RNA to achieve a cosuppression effect or the expression of at least one appropriately constructed ribozyme which specifically cleaves transcripts of the above-mentioned gene product.
  • DNA molecules can be used that comprise the entire coding sequence of a gene product, including any flanking sequences that may be present, as well as DNA molecules that only comprise parts of the coding sequence, these parts having to be long enough to be in the cells to cause 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 When nucleic acid molecules are expressed in plants, the synthesized protein can be located in any compartment of the plant cell. However, in order to achieve localization in a certain compartment, e.g. the coding region is linked to DNA sequences which ensure localization in a specific compartment. Such sequences are known to the person skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227). The expression of the nucleic acid molecules can also take place in the organelles of the plant cells.
  • the transgenic plant cells can be regenerated into whole plants using known techniques.
  • the transgenic plants can be any plants
  • the compounds of the general formula (I) according to the invention can preferably be used in transgenic cultures which are active against growth substances, e.g. Dicamba or against herbicides, the essential plant enzymes, e.g. Inhibit acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydoxyphenyl pyruvate dioxygenases (HPPD), or are resistant to herbicides from the group of sulfonylureas, glyphosate, glufosinate or benzoylisoxazole and analogous active ingredients.
  • the essential plant enzymes e.g. Inhibit acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydoxyphenyl pyruvate dioxygenases (HPPD)
  • ALS Inhibit acetolactate synthases
  • EPSP synthases glutamine synthases
  • HPPD hydoxy
  • the invention therefore also relates to the use of the compounds of the general formula (I) according to the invention and / or their salts as herbicides for controlling harmful plants in crops of useful or ornamental plants, optionally in transgenic crop plants.
  • the invention also relates to the use of one or more compounds of the general formula (I) or their salts or an agent according to the invention (as defined below) (in a method) for controlling harmful plants or for regulating the growth of plants, characterized in that an effective amount of one or more compounds of the general formula (I) or their salts are applied to the plants (harmful plants, if appropriate together with the useful plants) plant seeds, the soil , in or on which the plants grow, or the cultivated area is applied.
  • the invention also relates to a herbicidal and / or plant growth-regulating agent, characterized in that the agent
  • (a) contains one or more compounds of the general formula (I) and / or their salts as defined above, preferably in one of those identified as preferred or particularly preferred
  • one or more further agrochemically active substances preferably selected from the group consisting of insecticides, acaricides, nematicides, further herbicides (ie those which do not correspond to the general formula (I) defined above), fungicides, safeners, fertilizers and / or other growth regulators,
  • component (i) of an agent according to the invention are preferably selected from the group of substances described in "The Pesticide Manual”, 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012.
  • a herbicidal or plant growth-regulating agent according to the invention preferably comprises one, two, three or more formulation auxiliaries (ii) customary in crop protection selected from the group consisting of surfactants, emulsifiers, dispersants, film formers, thickeners, inorganic salts, dusts, at 25 ° C. and 1013 mbar solid carriers, preferably adsorbable, granulated inert materials, wetting agents, antioxidants, stabilizers, buffer substances, anti-foaming agents, water, organic solvents, preferably at 25 ° C. and 1013 mbar, water-miscible organic solvents in any ratio.
  • formulation auxiliaries customary in crop protection selected from the group consisting of surfactants, emulsifiers, dispersants, film formers, thickeners, inorganic salts, dusts, at 25 ° C. and 1013 mbar solid carriers, preferably adsorbable, granulated inert materials, wetting agents, antioxidants,
  • the compounds of the general formula (I) according to the invention can be used in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules in the customary formulations.
  • the invention therefore also relates to herbicidal and plant growth-regulating compositions which comprise compounds of the general formula (I) and / or their salts.
  • WP Wettable powder
  • SP water-soluble powder
  • EC emulsifiable concentrates
  • EW emulsions
  • SC suspension concentrates
  • CS Capsule suspensions
  • DP dusts
  • pickling agents granules for the litter
  • granules in the form of micro, spray, elevator and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations,
  • Microcapsules and waxes are Microcapsules and waxes.
  • Spray powders are preparations which are uniformly dispersible in water and which, in addition to the active substance, contain not only a diluent or an inert substance, but also ionic and / or nonionic surfactants (wetting agents,
  • Dispersants for example polyoxyethylated alkylphenols, polyoxethylated fatty alcohols, polyoxethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, ligninsulfonic acid sodium, 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium, sodium dibutyla naphthalenethyl or also containing sulfonate.
  • Dispersants for example polyoxyethylated alkylphenols, polyoxethylated fatty alcohols, polyoxethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, ligninsulfonic acid sodium, 2,2'-dinaphthylmethane-6,6'-d
  • the herbicidal active ingredients are, for example, finely ground in customary equipment, such as hammer mills, fan mills and air jet mills, and mixed at the same time or subsequently with the formulation auxiliaries.
  • Emulsifiable concentrates are prepared by dissolving the active ingredient in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or even higher-boiling aromatics or hydrocarbons or mixtures of the organic solvents with the addition of one or more ionic and / or nonionic surfactants (emulsifiers).
  • organic solvent for example butanol, cyclohexanone, dimethylformamide, xylene or even higher-boiling aromatics or hydrocarbons or mixtures of the organic solvents with the addition of one or more ionic and / or nonionic surfactants (emulsifiers).
  • emulsifiers alkylarylsulfonic acid calcium salts such as
  • Ca-dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters
  • Alkylaryl polyglycol ether fatty alcohol polyglycol ether, propylene oxide-ethylene oxide condensation products, alkyl polyether, sorbitan esters such as e.g. Sorbitan fatty acid esters or
  • Polyoxethylene sorbitan esters such as e.g. Polyoxyethylene.
  • Dusts are obtained by grinding the active ingredient with finely divided solid substances, e.g.
  • Talc natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • Suspension concentrates can be water or oil based. You can, for example, by wet grinding using commercially available bead mills and optionally adding surfactants such as those e.g. already listed above for the other types of formulation.
  • Emulsions e.g. Oil-in-water emulsions (EW) can be mixed using stirrers,
  • Solvents and optionally surfactants e.g. already listed above for the other formulation types.
  • Granules can either be produced by spraying the active ingredient onto adsorbable, granulated inert material or by applying active ingredient concentrates by means of adhesives, e.g. Polyvinyl alcohol, sodium polyacrylic acid or mineral oils, on the surface of carriers such as sand, kaolinite or granulated inert material. Also suitable ones
  • Active ingredients are granulated in the manner customary for the production of fertilizer granules - if desired in a mixture with fertilizers.
  • Water-dispersible granules are generally produced using 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 preferably herbicidal or plant growth-regulating agents of the present invention preferably contain a total amount of 0.1 to 99% by weight, preferably 0.5 to 95% by weight, more preferably 1 to 90% by weight, particularly preferably 2 to 80% by weight of active compounds of the general formula (I) and their salts.
  • the active substance concentration in wettable powders is e.g. about 10 to 90 wt .-%, the rest of 100 wt .-% consists of conventional formulation components. In the case of emulsifiable concentrates, the active substance concentration can be about 1 to 90, preferably 5 to 80,% by weight. Powdery
  • 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 in liquid or solid form and which granulating aids, fillers, etc. are used.
  • the active ingredient content of the water-dispersible granules is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
  • the active ingredient formulations mentioned may contain the customary adhesives, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreezes and solvents, fillers, carriers and dyes, defoamers, evaporation inhibitors and the pH and Agents influencing viscosity.
  • formulation auxiliaries are described, inter alia, in "Chemistry and Technology of Agrochemical Formulations", ed. D. A. Knowles, Kluwer Academic Publishers (1998).
  • the compounds of the general formula (1) according to the invention or their salts can be used as such or in the form of their preparations (formulations) with other pesticidally active substances, e.g. Insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and / or growth regulators can be used in combination, e.g. as a finished formulation or as
  • the combination formulations can be prepared on the basis of the formulations mentioned above, taking into account the physical properties and stabilities of the active compounds to be combined.
  • a combination partner for the compounds of the general formula (1) according to the invention in mixture formulations or in a tank mix there are, for example, known active ingredients which are based on an inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate Synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoendesaturase, Photosystem I, Photosystem II, protoporphyrinogen oxidase, can be used, as described, for example, in Weed Research 26 (1986) 441-445 or "The Pesticide Manual", sixth edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 and the literature cited therein.
  • Compounds (I) according to the invention of particular interest which contain the compounds of the general formula (I) or their combinations with other herbicides or pesticides and safeners.
  • the safeners which are used in an antidotically effective content, reduce the phytotoxic side effects of the herbicides / pesticides used, e.g. in economically important crops such as cereals (wheat, barley, rye, corn, rice, millet), sugar beet, sugar cane, rapeseed, cotton and soybeans, preferably cereals.
  • the weight ratio of herbicide (mixture) to safener generally depends on the
  • herbicide and the effectiveness of the respective safener can vary within wide limits, for example in the range from 200: 1 to 1: 200, preferably 100: 1 to 1: 100, in particular 20: 1 to 1:20.
  • the safeners can be formulated analogously to the compounds of the general formula (I) or their mixtures with further herbicides / pesticides and as
  • the herbicide or herbicide safener formulations present in commercially available form are optionally diluted in the customary manner, for example for wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules using water.
  • Preparations in the form of dust, ground granules or granules as well as sprayable solutions are usually no longer diluted with other inert substances before use.
  • the application rate can vary within wide limits.
  • Control of harmful plants is the total amount of compounds of general formula (I) and their salts preferably in the range from 0.001 to 10.0 kg / ha, preferably in the range from 0.005 to 5 kg / ha, more preferably in the range from 0.01 to 1.5 kg / ha, particularly preferably in the range from 0.05 to 1 kg / ha. This applies to both pre-emergence and post-emergence applications.
  • the total application rate is preferably in the range from 0.001 to 2 kg / ha, preferably in the range from 0.005 to 1 kg / ha, in particular in the range from 10 to 500 g / ha, very particularly preferably in the range from 20 to 250 g / ha Ha. This applies both to the application in
  • the application as a straw shortener can take place in different stages of the growth of the plants. For example, use after planting at the beginning of the
  • the treatment of the seed which includes the different seed dressing and coating techniques, can also be used.
  • the application rate depends on the individual techniques and can be determined in preliminary tests.
  • compositions according to the invention for example mixture formulations or in a tank mix
  • active substances which are based on inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate -3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoendesaturase, Photosystem I, Photosystem II or
  • Protoporphyrinogen oxidase are used, such as those e.g. from Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 and the literature cited therein.
  • Known herbicides or plant growth regulators are mentioned below by way of example, which can be combined with the compounds according to the invention, these active compounds either with their "common name" in the English-language variant according to the International Organization for Standardization (ISO) or with the chemical name or with the code number are designated.
  • flucarbazone flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, fluometuron, flurenol, flurenol-butyl, -dimethylammonoglypane, and -methyl-fluorine-cyanogen flupyrsulfuron, flupyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium, foramsulfuron, fosamine, glufosinate, glufosinate ammonium, pufosinate ammonium P-ammonium, glufosinate-P-sodium
  • metdicazthiazuron metam, metamifop, metamitron, metazachlor, metazosulfuron,
  • plant growth regulators as possible mixing partners are:
  • Sl d compounds of the triazole carboxylic acid type (Sl d ), preferably compounds such as
  • Fenchlorazole ethyl ester
  • ethyl ester i.e. 1- (2,4-dichlorophenyl) -5-trichloromethyl- (lH) -l, 2,4-triazole-3-carboxylic acid ethyl ester (S1-7), and related compounds as described in EP-A-174562 and EP- A-346620;
  • Sl e compounds of the type of 5-benzyl- or 5-phenyl-2-isoxazoline-3-carboxylic acid, or of 5,5-diphenyl-2-isoxazoline-3-carboxylic acid (Sl e ), preferably compounds such as
  • R-29148 (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) from Stauffer (S3-2)
  • R-28725" (3-dichloroacetyl-2,2, -dimethyl- 1,3-oxazolidine) from Stauffer (S3-3)
  • PPG-1292 N-allyl-N - [(1,3-dioxolan-2-yl) methyl] dichloroacetamide
  • TI-35 (l-dichloroacetyl-azepan) from TRI-Chemical RT (S3-8),
  • VA is 0, 1, 2 or 3;
  • RB 1 , RB 2 independently of one another hydrogen, (Ci-C 6 ) alkyl, (C3-C6) cycloalkyl, (C3-C 6 ) alkenyl, (C3-C 6 ) alkynyl,
  • RB 1 cyclopropyl
  • RB 2 hydrogen
  • (RB 3 ) 2-OMe
  • RB 1 isopropyl
  • RB 2 hydrogen
  • (RB 3 ) 5-Cl-2-OMe is (S4-4) and
  • Rc 1 , Rc 2 independently of one another hydrogen, (Ci-Cg) alkyl, (C3-Cg) cycloalkyl, (C3-
  • Rc 3 halogen, (Ci-C4) alkyl, (Ci-C4) alkoxy, CF 3 and
  • mc 1 or 2;
  • C 6 means cycloalkenyl
  • Carboxylic acid derivatives (S5) e.g.
  • S6 active substances from the class of 1,2-dihydroquinoxalin-2-one (S6), e.g.
  • S7 compounds from the class of diphenylmethoxyacetic acid derivatives (S7), e.g.
  • RD 1 is halogen, (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkyl, (Ci-C 4 ) alkoxy, (Ci-C 4 ) haloalkoxy,
  • RD 2 is hydrogen or (Ci-C 4 ) alkyl
  • R D 3 is hydrogen, (Ci-Cg) alkyl, (C2-C4) alkenyl, (C2-C4) alkynyl, or aryl, each of the abovementioned C-containing radicals being unsubstituted or by one or more, preferably up to three of the same or various radicals from the group consisting of halogen and alkoxy is substituted; or their salts,
  • n D is an integer from 0 to 2.
  • S9 active substances from the class of 3- (5-tetrazolylcarbonyl) -2-quinolones (S9), e.g.
  • hey an integer from 0 to 4,
  • RE 2 (Ci-Ciejalkyl, (C2-C6) alkenyl, (C3-C6) cycloalkyl, aryl; benzyl, halobenzyl,
  • RE 3 is hydrogen or (Ci-C 6 ) alkyl.
  • Sl 1 Active substances of the oxyimino compound type (Sl 1), which are known as seed dressings, such as. B.
  • Oxabetrinil ((Z) -l, 3-dioxolan-2-ylmethoxyimino (phenyl) acetonitrile) (Sl l-l), which is known as a seed dressing safener for millet against damage to metolachlor,
  • Fluorofenim (1- (4-chlorophenyl) -2,2,2-trifluoro-l-ethanone-0- (1,3-dioxolan-2-ylmethyl) -oxime) (Sl 1-2), which is used as a seed dressing -Safeer for millet against damage from metolachlor is known
  • Cyometrinil or “CGA-43089” ((Z) -cyanomethoxyimino (phenyl) acetonitrile) (Sl l-3), which is used as a seed dressing safener for millet against damage from metolachlor is known.
  • Cyanamide which is known as a safener for corn against damage to imidazolinones
  • MG 191 (CAS Reg. No. 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5) from Nitrokemia, which is known as a safener for corn,
  • Active ingredients which, in addition to a herbicidal action against harmful plants, also have a safener action on crop plants such as rice, such as. B.
  • COD l-bromo-4- (chloromethylsulfonyl) benzene
  • R H 1 is a (Ci-CejHaloalkylrest and
  • R H 2 represents hydrogen or halogen
  • R H 3 , R H 4 independently of one another are hydrogen, (Ci-Ci 6 ) alkyl, (C2-Ci6) alkenyl or
  • each of the latter 4 residues is unsubstituted or by one or more residues from the group halogen, hydroxy, cyano, (Ci-C4) alkyl, (Ci-C4) haloalkyl, (Ci-C 4 ) alkoxy, (Ci-C 4 ) Haloalkoxy, (Ci-C 4 ) alkylthio, (Ci-C 4 ) alkylamino, di [(Ci-C4) alkyl] amino, [(Ci-C4) alkoxy] carbonyl, [(Ci-C4) haloalkoxy] - carbonyl,
  • R is H 3 (Ci-C4) alkoxy, (C2-C4) alkenyloxy, (C2-C6) alkynyloxy or (C2-C4) haloalkoxy and
  • R H 4 is hydrogen or (Ci-C4) alkyl or
  • R H 3 and R H 4 together with the directly bound N atom form a four- to eight-membered group
  • 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 halogen, cyano, nitro, (Ci C 4 ) alkyl, (Ci-C 4 ) haloalkyl, (Ci-C 4 ) alkoxy, (Ci-C 4 ) haloalkoxy and (Ci-C 4 ) alkylthio is substituted.
  • Preferred safeners in combination with the compounds according to the invention of the general formula (I) and / or their salts, in particular with the compounds of the formulas (1-1) to (1-662) and / or their salts are: Cloquintocet-mexyl, cyprosulfamide, Fenchlorazole-ethyl ester, Isoxadifen-ethyl, Mefenpyr-diethyl, Fenclorim, Cumyluron, S4-1 and S4-5, and particularly preferred safeners are: Cloquintocet-mexyl, Cyprosulfamid, Isoxadifen-ethyl and Mefenpyr-diethyl.
  • the amount of water applied is equivalent to 2200 liters per hectare. After 9 to 12 days
  • test results prove that compounds of the general formula (I) according to the invention have good herbicidal activity against selected harmful plants such as Agrostis tenuis (AGSTE) and Poa annua (POAAN) at a respective application rate of 1900 g of active substance per hectare when treated in the early post-emergence.
  • Agrostis tenuis Agrostis tenuis
  • POAAN Poa annua
  • Seeds of monocotyledonous or dicotyledonous weed plants were placed in plastic pots in sandy loam soil (double sowing, each with one species of monocotyledonous or dicotyledonous weed plant per pot), covered with soil and grown in the greenhouse under controlled growth conditions. The test plants were treated at the single-leaf stage 2 to 3 weeks after sowing.
  • the following tablets B1 to B8 show the effects of selected compounds of the general formula (1) according to Table 1 on various harmful plants and an application rate corresponding to 1280 g / ha, which were obtained according to the aforementioned test instructions.
  • Table B5 Post-emergence effects against Stellaria media (STEME)
  • Table B6 Post-emergence effect against Lolium rigidum (LOLRI)
  • EHCG Echinochloa crus-galli
  • POAAN Poa annua
  • ABUTH Abutilon theophrasti
  • AMARE Amaranthus retroflexus
  • STEM Stellaria media
  • LOLR1 Lolium rigidum
  • Setaria viridis Setaria viridis
  • MAT1N Matricaria inodora
  • Table C5 Pre-emergence effect against Abutilon theophrasti (ABUTH)
  • Table C6 Pre-emergence effect against Amaranthus retroflexus (AMARE)

Abstract

The invention relates to substituted 2-heteroaryloxypyridines of general formula (I) and to the use thereof as herbicides, in particular for controlling weeds and/or harmful grasses in useful plant crops and/or as plant growth regulators for influencing the growth of useful plant crops, The present invention further relates to herbicidal and/or plant growth regulating agents comprising one or more compounds of general formula (I).

Description

Bayer AG  Bayer AG
Substituierte 2-Heteroaryloxypyridine sowie deren Salze und ihre Verwendung als herbizide Wirkstoffe Beschreibung Substituted 2-heteroaryloxypyridines and their salts and their use as herbicidal active ingredients Description
Die Erfindung betrifft das technische Gebiet der Pflanzenschutzmittel, insbesondere das der Herbizide zur selektiven Bekämpfung von Unkräutern und Ungräsem in Nutzpflanzenkulturen. The invention relates to the technical field of crop protection agents, in particular that of herbicides for the selective control of weeds and weeds in crops of useful plants.
Speziell betrifft diese Erfindung substituierte 2-Heteroaryloxypyridine sowie deren Salze, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide. In particular, this invention relates to substituted 2-heteroaryloxypyridines and their salts, processes for their preparation and their use as herbicides.
Bisher bekannte Pflanzenschutzmittel zur selektiven Bekämpfung von Schadpflanzen in Known crop protection products for the selective control of harmful plants in
Nutzpflanzenkulturen oder Wirkstoffe zur Bekämpfung von unerwünschtem Pflanzenwuchs weisen bei ihrer Anwendung teilweise Nachteile auf, sei es, dass sie (a) keine oder aber eine unzureichende herbizide Wirkung gegen bestimmte Schadpflanzen, (b) ein zu geringes Spektrum der Schadpflanzen, das mit einem Wirkstoff bekämpft werden kann, (c) zu geringe Selektivität in Nutzpflanzenkulturen und/oder (d) ein toxikologisch ungünstiges Profil besitzen. Weiterhin führen manche Wirkstoffe, die als Pflanzenwachstumsregulatoren bei einigen Nutzpflanzen eingesetzt werden können, bei anderen Nutzpflanzen zu unerwünscht verminderten Emteerträgen oder sind mit der Kulturpflanze nicht oder nur in einem engen Aufwandmengenbereich verträglich. Einige der bekannten Wirkstoffe lassen sich wegen schwer zugänglicher Vorprodukte und Reagenzien im industriellen Maßstab nicht wirtschaftlich hersteilen oder besitzen nur unzureichende chemische Stabilitäten. Bei anderen Wirkstoffen hängt die Wirkung zu stark von Umweltbedingungen, wie Wetter- und Bodenverhältnissen ab. Crop crops or active ingredients to combat undesirable plant growth sometimes have disadvantages when used, either because they (a) have no or an inadequate herbicidal activity against certain harmful plants, (b) the spectrum of the harmful plants is too small to combat with an active ingredient can be (c) insufficient selectivity in crops and / or (d) have a toxicologically unfavorable profile. Furthermore, some active ingredients which can be used as plant growth regulators in some crop plants lead to undesirably reduced crop yields in other crop plants or are incompatible or only compatible with the crop plant in a narrow range of application rates. Some of the known active ingredients cannot be economically manufactured on an industrial scale because of precursors and reagents that are difficult to access, or they have insufficient chemical stabilities. For other active substances, the effect depends too much on environmental conditions such as weather and soil conditions.
Die herbizide Wirkung dieser bekannten Verbindungen, insbesondere bei niedrigen Aufwandmengen, bzw. deren Verträglichkeit gegenüber Kulturpflanzen bleiben verbesserungswürdig. ln WO2011/22313 werden 2-Heteroaryloxypyridine benannt und als Glutamatrezeptoren The herbicidal activity of these known compounds, especially at low application rates, or their compatibility with crop plants remains in need of improvement. In WO2011 / 22313 2-heteroaryloxypyridines are named and as glutamate receptors
beeinflussenende Komponenten beschrieben, die pharmazeutischen Nutzen haben. Daneben wurden Heteroaryloxybenzole in W02015/89003, WO2015/108779, W02016/10731, WO2016/196606 und WO2017/11288 beschrieben, denen eine herbizide Wirkung zuerkannt wurde. influencing components described that have pharmaceutical benefits. In addition, heteroaryloxybenzenes have been described in WO2015 / 89003, WO2015 / 108779, WO2016 / 10731, WO2016 / 196606 and WO2017 / 11288, to which a herbicidal action has been attributed.
Substituierte 2-Heteroaryloxypyridine oder deren Salze als herbizide Wirkstoffe sind dagegen bisher noch nicht beschrieben worden. Überraschenderweise wurde nun gefunden, dass substituierte 2-Heteroaryloxypyridine oder deren Salze als herbizide Wirkstoffe besonders gut geeignet sind. Substituted 2-heteroaryloxypyridines or their salts as herbicidal active ingredients, however, have not yet been described. Surprisingly, it has now been found that substituted 2-heteroaryloxypyridines or their salts are particularly suitable as herbicidal active compounds.
Gegenstand der vorliegenden Erfindung sind damit substituierte 2-Heteroaryloxypyridine der allgemeinen Formel (1) oder deren Salze The present invention thus relates to substituted 2-heteroaryloxypyridines of the general formula (1) or their salts
worin wherein
X für Stickstoff, -CF- oder -CH- steht, X represents nitrogen, -CF- or -CH-,
A für Sauerstoff, -S(0)n-, -C(R4)(R5) -, -C(=0) -, oder -NR6- steht A stands for oxygen, -S (0) n- , -C (R 4 ) (R 5 ) -, -C (= 0) -, or -NR 6 -
mit n gleich 0, 1 oder 2,  with n equal to 0, 1 or 2,
R1 für ein gegebenenfalls substituiertes Aryl, Heteroaryl, Heterocylyl, (C3-Cio)-Cycloalkyl oder (C3-Cio)-Cycloalkenyl steht, wobei jeder Ring oder jedes Ringsystem optional mit bis zu 5R 1 represents an optionally substituted aryl, heteroaryl, heterocylyl, (C3-Cio) cycloalkyl or (C3-Cio) cycloalkenyl, each ring or ring system optionally having up to 5
Substituenten, unabhängig voneinander ausgewählt aus der Gruppe R7, substituiert ist; Substituent, independently selected from the group R 7 , is substituted;
R2 unabhängig voneinander für Halogen, Cyano, Nitro, Formyl, Formamid, (Ci -Cs)- Alkyl, (Ci-C8)- Haloalkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (C2-C8)-Haloalkenyl, (C2-C8)-Haloalkinyl, (Ci- C4)-Alkoxy-(Ci-C4)-alkyl, (Ci-C4)-Haloalkoxy-(Ci-C4)-alkyl, (Ci-C4)-Alkylthio-(Ci-C4)-alkyl,R 2 independently of one another for halogen, cyano, nitro, formyl, formamide, (Ci -Cs) - alkyl, (Ci-C 8 ) - haloalkyl, (C 2 -C 8 ) alkenyl, (C 2 -C 8 ) - Alkynyl, (C 2 -C 8 ) -haloalkenyl, (C 2 -C 8 ) -haloalkynyl, (Ci-C 4 ) -alkoxy- (Ci-C 4 ) -alkyl, (Ci-C 4 ) -haloalkoxy- ( Ci-C 4 ) -alkyl, (Ci-C 4 ) -alkylthio- (Ci-C 4 ) -alkyl,
(Ci-C4)-Alkylsulfmyl-(Ci-C4)-alkyl, (Ci-C4)-Alkylsulfonyl-(Ci-C4)-alkyl, (Ci-C8)- Alkylcarbonyl, (Ci-C8)-Haloalkylcarbonyl, (C3-C8)-Cycloalkylcarbonyl, Carboxyl, (Ci-C8)- Alkoxycarbonyl, (Ci-C8)- Haloalkoxycarbonyl, (C3-C8)-Cycloalkoxycarbonyl, Carbamoyl, (C2-C8)-Alkylaminocarbonyl, (C2-Cio)-Dialkylaminocarbonyl, (C3-C10)- Cycloalkylaminocarbonyl, (Ci-C4)-Alkoxycarbonyl-(Ci-C4)-alkyl, (Ci-C4)-Haloalkoxycarbonyl-(Ci-C 4 ) alkylsulfmyl- (Ci-C 4 ) -alkyl, (Ci-C 4 ) -alkylsulfonyl- (Ci-C 4 ) -alkyl, (Ci-C 8 ) - alkylcarbonyl, (Ci-C 8 ) -Haloalkylcarbonyl, (C3-C 8 ) -cycloalkylcarbonyl, carboxyl, (Ci-C 8 ) - alkoxycarbonyl, (Ci-C 8 ) - haloalkoxycarbonyl, (C3-C 8 ) -cycloalkoxycarbonyl, carbamoyl, (C 2 -C 8 ) -Alkylaminocarbonyl, (C 2 -Cio) -dialkylaminocarbonyl, (C3-C10) - cycloalkylaminocarbonyl, (Ci-C 4 ) -alkoxycarbonyl- (Ci-C 4 ) -alkyl, (Ci-C 4 ) -haloalkoxycarbonyl-
(Ci-C4)-alkyl, Carboxy-(Ci-C4)-alkyl, Hydroxy, Amino, (Ci-C8)-Alkoxy, (Ci-C8)-Haloalkoxy, (Ci-C8)-Alkylthio, (Ci-C8)-Haloalkylthio, (C3-C8)-Cycloalkylthio, (Ci-C8)-Alkylsulfinyl, (Ci-C8)-Haloalkylsulfmyl, (C3-C8)-Cycloalkylsulfinyl, (Ci-C8)-Alkylsulfonyl, (Ci-C8)- Haloalkylsulfonyl, (C3-Cg)-Cycloalkylsulfonyl, (Ci-C8)-Alkylaminosulfonyl, (C2-Cx)- Dialkylaminosulfonyl oder (C3-C8)-Trialkylsilyl steht, m ist gleich 0, 1, 2, oder 3, (Ci-C 4 ) alkyl, carboxy- (Ci-C 4 ) alkyl, hydroxy, amino, (Ci-C 8 ) alkoxy, (Ci-C 8 ) haloalkoxy, (Ci-C 8 ) alkylthio , (Ci-C 8 ) -haloalkylthio, (C3-C 8 ) -cycloalkylthio, (Ci-C 8 ) -alkylsulfinyl, (Ci-C 8 ) -haloalkylsulfyl, (C3-C 8 ) -cycloalkylsulfinyl, (Ci-C 8 ) -alkylsulfonyl, (Ci-C 8 ) - Haloalkylsulfonyl, (C 3 -Cg) -cycloalkylsulfonyl, (Ci-C 8 ) -alkylaminosulfonyl, (C 2 -Cx) -dialkylaminosulfonyl or (C 3 -C 8 ) -trialkylsilyl, m is 0, 1, 2, or 3,
R3 für Wasserstoff, Halogen, Cyano, Nitro, Formyl, (Ci-Cg)-Alkyl, (Ci-Cg)-Haloalkyl, (C2-Cg)- Alkenyl, (C2-Cg)-Alkinyl, (C2-Cg)-Haloalkenyl, (C2-Cg)-Haloalkinyl, (Ci-C4)-Alkoxy-(Ci-C4)- alkyl, (Ci-C4)-Haloalkoxy-(Ci-C4)-alkyl, (Ci-C4)-Alkylthio-(Ci-C4)-alkyl, (Ci-C4)- Alkylsulfmyl-(Ci-C4)-alkyl, (Ci-C4)-Alkylsulfonyl-(Ci-C4)-alkyl, (Ci-Cg)-Alkylcarbonyl, (Ci-Cg)-Haloalkylcarbonyl, (C3-Cg)-Cycloalkylcarbonyl, Carboxyl, (Ci-Cg)-Alkoxycarbonyl, (Ci-Cg)- Haloalkoxycarbonyl, (C3-Cg)-Cycloalkoxycarbonyl, (Ci-Cg)-Alkylaminocarbonyl, (C2-Cg)-Dialkylaminocarbonyl, (C3-Cg)-Cycloalkylaminocarbonyl, Hydroxy, (Ci-Cg)-Alkoxy, (Ci-Cg)-Haloalkoxy, (Ci-Cg)-Alkylthio, (Ci-Cg)-Haloalkylthio, (C3-Cg)-Cycloalkylthio, (Ci-Cg)- Alkylsulfmyl, (Ci-Cg)-Haloalkylsulfinyl, (C3-Cg)-Cycloalkylsulfinyl, (Ci-Cg)-Alkylsulfonyl, (Ci-Cg)-Haloalkylsulfonyl, (C3-Cg)-Cycloalkylsulfonyl, (Ci-Cg)-Alkylaminosulfonyl, (C2-Cg)- Dialkylaminosulfonyl oder (C3-Cg)-Trialkylsilyl steht, R 3 for hydrogen, halogen, cyano, nitro, formyl, (Ci-Cg) alkyl, (Ci-Cg) haloalkyl, (C 2 -Cg) alkenyl, (C 2 -Cg) alkynyl, (C 2 -Cg) haloalkenyl, (C 2 -Cg) haloalkynyl, (Ci-C 4 ) alkoxy- (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkoxy- (Ci-C 4 ) alkyl , (Ci-C 4) alkylthio (Ci-C 4) alkyl, (Ci-C4) - Alkylsulfmyl- (Ci-C 4) alkyl, (Ci-C 4) alkylsulfonyl (Ci-C 4 ) -alkyl, (Ci-Cg) -alkylcarbonyl, (Ci-Cg) -haloalkylcarbonyl, (C 3 -Cg) -cycloalkylcarbonyl, carboxyl, (Ci-Cg) -alkoxycarbonyl, (Ci-Cg) - haloalkoxycarbonyl, (C 3 -Cg) cycloalkoxycarbonyl, (Ci-Cg) alkylaminocarbonyl, (C 2 -Cg) dialkylaminocarbonyl, (C 3 -Cg) cycloalkylaminocarbonyl, hydroxy, (Ci-Cg) alkoxy, (Ci-Cg) haloalkoxy , (Ci-Cg) alkylthio, (Ci-Cg) haloalkylthio, (C 3 -Cg) cycloalkylthio, (Ci-Cg) alkylsulfmyl, (Ci-Cg) haloalkylsulfinyl, (C 3 -Cg) cycloalkylsulfinyl , (Ci-Cg) alkylsulfonyl, (Ci-Cg) haloalkylsulfonyl, (C 3 -Cg) cycloalkylsulfonyl, (Ci-Cg) alkylaminosulfonyl, (C 2 -Cg) dialkylaminosulfonyl or (C 3 -Cg) - Trialkylsilyl stands .
R4 und R5 unabhängig voneinander für Wasserstoff, Hydroxy, Halogen, (Ci-Cg)-Alkyl, (Ci-Cs)- Haloalkyl, (C2-Cg)-Alkenyl, (C2-Cg)-Alkinyl, (Ci-C4)-Alkoxy-(Ci-C4)-alkyl, (Ci-C4)- Haloalkoxy-(Ci-C4)-alkyl, (Ci-C4)-Alkylthio-(Ci-C4)-alkyl, (Ci-C4)-Alkylsulfmyl-(Ci-C4)-alkyl, (Ci-C4)-Alkylsulfonyl-(Ci-C4)-alkyl, (Ci-Cg)-Alkylcarbonyl, (Ci-Cg)-Haloalkylcarbonyl, (C3-Cg)-Cycloalkylcarbonyl, (Ci-Cg)-Alkoxycarbonyl, (Ci-Cs)- Haloalkoxycarbonyl, (C3-C8)- Cycloalkoxycarbonyl, (Ci-Cg)-Alkylaminocarbonyl, (C2-Cg)-Dialkylaminocarbonyl, (C3-C8)- Cycloalkylaminocarbonyl, (Ci-Cg)-Alkoxy, (Ci-Cg)-Alkylthio, (Ci-Cg)-Haloalkylthio, (C3-C8)- Cycloalkylthio, stehen, oder R 4 and R 5 independently of one another are hydrogen, hydroxyl, halogen, (Ci-Cg) -alkyl, (Ci-Cs) - haloalkyl, (C 2 -Cg) -alkenyl, (C 2 -Cg) -alkynyl, (Ci -C 4 ) -alkoxy- (Ci-C 4 ) -alkyl, (Ci-C 4 ) -haloalkoxy- (Ci-C 4 ) -alkyl, (Ci-C 4 ) -alkylthio- (Ci-C 4 ) - alkyl, (Ci-C 4 ) -alkylsulfmyl- (Ci-C 4 ) -alkyl, (Ci-C 4 ) -alkylsulfonyl- (Ci-C 4 ) -alkyl, (Ci-Cg) -alkylcarbonyl, (Ci-Cg ) -Haloalkylcarbonyl, (C 3 -Cg) -cycloalkylcarbonyl, (Ci-Cg) -alkoxycarbonyl, (Ci-Cs) -haloalkoxycarbonyl, (C 3 -C 8 ) -cycloalkoxycarbonyl, (Ci-Cg) -alkylaminocarbonyl, (C 2 -Cg) dialkylaminocarbonyl, (C 3 -C 8 ) cycloalkylaminocarbonyl, (Ci-Cg) alkoxy, (Ci-Cg) alkylthio, (Ci-Cg) haloalkylthio, (C 3 -C 8 ) cycloalkylthio, stand, or
R4 und R5 gemeinsam einen 3- bis 6-gliedrigen carbocyclischen Ring oder einen 3- bis 6-gliedrigen gesättigten heterocyclischen Ring mit bis zu 2 Sauerstoffatomen bilden, oder R 4 and R 5 together form a 3- to 6-membered carbocyclic ring or a 3- to 6-membered saturated heterocyclic ring with up to 2 oxygen atoms, or
R4 und R5 gemeinsam einen (Ci-C3)-Alkylidenrest oder (Ci-C3)-Haloalkylidenrest bilden, R6 für Wasserstoff, (Ci-Cg)-Alkyl, (Ci-Cg)-Haloalkyl, Aryl-(Ci-C6)-alkyl, Heteroaryl-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, (C3-C6)-Halocycloalkyl, (C3-C6)- Halocycloalkyl-(Ci-C4)-alkyl, (C2-Cg)-Alkenyl, (C2-Cg)-Alkinyl, (Ci-C4)-Alkoxy-(Ci-C4)-alkyl, (Ci-C4)-Haloalkoxy-(Ci-C4)-alkyl, (Ci-C4)-Alkylthio-(Ci-C4)-alkyl, (Ci-C4)-Alkylsulfinyl- (Ci-C4)-alkyl, (Ci-C4)-Alkylsulfonyl-(Ci-C4)-alkyl, (Ci-Cg)-Alkylcarbonyl, (Ci-Cg)- Haloalkylcarbonyl, (C3-Cg)-Cycloalkylcarbonyl, Formyl, (Ci-Cg)-Alkoxycarbonyl, (Ci-Cg)- Haloalkoxycarbonyl, (C3-Cg)-Cycloalkoxycarbonyl, (Ci-Cg)-Alkylaminocarbonyl, (C2-Cg)- Dialkylaminocarbonyl, (C3-Cg)-Cycloalkylaminocarbonyl steht, R 4 and R 5 together form a (Ci-C3) alkylidene radical or (Ci-C3) haloalkylidene radical, R 6 is hydrogen, (Ci-Cg) -alkyl, (Ci-Cg) -haloalkyl, aryl- (Ci-C 6 ) -alkyl, heteroaryl- (Ci-C 6 ) -alkyl, (C 3 -C 6 ) -Cycloalkyl, (C3-C 6 ) -cycloalkyl- (Ci-C 6 ) -alkyl, (C 3 -C 6 ) -halocycloalkyl, (C 3 -C 6 ) -halocycloalkyl- (Ci-C 4 ) -alkyl, (C 2 -Cg) alkenyl, (C 2 -Cg) alkynyl, (Ci-C 4 ) alkoxy- (Ci-C 4 ) alkyl, (Ci-C 4 ) -haloalkoxy- (Ci-C 4 ) -alkyl, (Ci-C 4 ) -alkylthio- (Ci-C 4 ) -alkyl, (Ci-C 4 ) -alkylsulfinyl- (Ci-C 4 ) -alkyl, (Ci-C 4 ) -alkylsulfonyl- ( Ci-C 4 ) -alkyl, (Ci-Cg) -alkylcarbonyl, (Ci-Cg) - haloalkylcarbonyl, (C 3 -Cg) -cycloalkylcarbonyl, formyl, (Ci-Cg) -alkoxycarbonyl, (Ci-Cg) - haloalkoxycarbonyl , (C 3 -Cg) cycloalkoxycarbonyl, (Ci-Cg) alkylaminocarbonyl, (C 2 -Cg) dialkylaminocarbonyl, (C 3 -Cg) cycloalkylaminocarbonyl,
R7 für Wasserstoff, Halogen, Cyano, Nitro, Formyl, (Ci-Cg)-Alkyl, (Ci-Cg)-Haloalkyl, (C2-Cg)- Alkenyl, (C2-Cg)-Alkinyl, (C2-Cg)-Haloalkenyl, (C2-Cg)-Haloalkinyl, (Ci-C4)-Alkoxy-(Ci-C4)- alkyl, (Ci-C4)-Haloalkoxy-(Ci-C4)-alkyl, (Ci-C4)-Alkylthio-(Ci-C4)-alkyl, (Ci-C4)- Alkylsulfinyl-(Ci-C4)-alkyl, (Ci-C4)-Alkylsulfonyl-(Ci-C4)-alkyl, (Ci-Cg)-Alkylcarbonyl, (Ci-Cg)-Haloalkylcarbonyl, (C3-Cg)-Cycloalkylcarbonyl, Carboxyl, (Ci-Cg)-Alkoxycarbonyl, (Ci-Cg)- Haloalkoxycarbonyl, (C3-Cg)-Cycloalkoxycarbonyl, (Ci-Cg)-Alkylaminocarbonyl, (C2-Cg)-Dialkylaminocarbonyl, (C3-Cg)-Cycloalkylaminocarbonyl, Hydroxy, (Ci-Cg)-Alkoxy, (Ci-Cg)-Haloalkoxy, (Ci-Cg)-Alkylthio, (Ci-Cg)-Haloalkylthio, (C3-Cg)-Cycloalkylthio, (Ci-Cg)- Alkylsulfinyl, (Ci-Cg)-Haloalkylsulfinyl, (C3-Cg)-Cycloalkylsulfinyl, (Ci-Cg)-Alkylsulfonyl, (Ci-Cg)-Haloalkylsulfonyl, (C3-Cg)-Cycloalkylsulfonyl, (Ci-Cg)-Alkylaminosulfonyl, (C2-Cg)- Dialkylaminosulfonyl oder (C3-Cg)-Trialkylsilyl steht. R 7 represents hydrogen, halogen, cyano, nitro, formyl, (Ci-Cg) alkyl, (Ci-Cg) haloalkyl, (C 2 -Cg) alkenyl, (C 2 -Cg) alkynyl, (C 2 -Cg) haloalkenyl, (C 2 -Cg) haloalkynyl, (Ci-C 4 ) alkoxy- (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkoxy- (Ci-C 4 ) alkyl , (Ci-C 4) alkylthio (Ci-C 4) alkyl, (Ci-C 4) - alkylsulfinyl (Ci-C 4) alkyl, (Ci-C 4) alkylsulfonyl (Ci-C 4 ) -alkyl, (Ci-Cg) -alkylcarbonyl, (Ci-Cg) -haloalkylcarbonyl, (C 3 -Cg) -cycloalkylcarbonyl, carboxyl, (Ci-Cg) -alkoxycarbonyl, (Ci-Cg) - haloalkoxycarbonyl, (C 3 -Cg) cycloalkoxycarbonyl, (Ci-Cg) alkylaminocarbonyl, (C 2 -Cg) dialkylaminocarbonyl, (C 3 -Cg) cycloalkylaminocarbonyl, hydroxy, (Ci-Cg) alkoxy, (Ci-Cg) haloalkoxy , (Ci-Cg) alkylthio, (Ci-Cg) haloalkylthio, (C 3 -Cg) cycloalkylthio, (Ci-Cg) alkylsulfinyl, (Ci-Cg) haloalkylsulfinyl, (C 3 -Cg) cycloalkylsulfinyl , (Ci-Cg) alkylsulfonyl, (Ci-Cg) haloalkylsulfonyl, (C 3 -Cg) cycloalkylsulfonyl, (Ci-Cg) alkylaminosulfonyl, (C 2 -Cg) dialkylaminosulfonyl or (C 3 -Cg) - Trialkylsilyl ste ht.
Die Verbindungen der allgemeinen Formel (1) können durch Anlagerung einer geeigneten The compounds of general formula (1) can be added by adding a suitable one
anorganischen oder organischen Säure, wie beispielsweise Mineralsäuren, wie beispielsweise HCl, HBr, H2S04, H3P04 oder HN03, oder organische Säuren, z. B. Carbonsäuren, wie Ameisensäure, Essigsäure, Propionsäure, Oxalsäure, Milchsäure oder Salicylsäure oder Sulfonsäuren, wie zum Beispiel p- Toluolsulfonsäure, an eine basische Gruppe, wie z.B. Amino, Alkylamino, Dialkylamino, Piperidino, Morpholino oder Pyridino, Salze bilden. Diese Salze enthalten dann die konjugierte Base der Säure als Anion. Geeignete Substituenten, die in deprotonierter Form, wie z.B. Sulfonsäuren, bestimmte inorganic or organic acid, such as mineral acids, such as HCl, HBr, H 2 S0 4 , H 3 P0 4 or HN0 3 , or organic acids, e.g. B. carboxylic acids, such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid or sulfonic acids, such as p-toluenesulfonic acid, to form a basic group such as amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino, salts. These salts then contain the conjugate base of the acid as an anion. Suitable substituents determined in deprotonated form, such as sulfonic acids
Sulfonsäureamide oder Carbonsäuren, vorliegen, können innere Salze mit ihrerseits protonierbaren Gruppen, wie Aminogruppen bilden. Salzbildung kann auch durch Einwirkung einer Base auf Sulphonic acid amides or carboxylic acids are present, inner salts with protonatable groups such as amino groups can form. Salt formation can also be caused by exposure to a base
Verbindungen der allgemeinen Formel (1) erfolgen. Geeignete Basen sind beispielsweise organische Amine, wie Trialkylamine, Morpholin, Piperidin und Pyridin sowie Ammonium-, Alkali- oder Compounds of the general formula (1) are made. Suitable bases are, for example, organic amines, such as trialkylamines, morpholine, piperidine and pyridine, and ammonium, alkali or
Erdalkalimetallhydroxide, -carbonate und -hydrogencarbonate, insbesondere Natrium- und Alkaline earth metal hydroxides, carbonates and bicarbonates, especially sodium and
Kaliumhydroxid, Natrium- und Kaliumcarbonat und Natrium- und Kaliumhydrogencarbonat. Diese Salze sind Verbindungen, in denen der azide Wasserstoff durch ein für die Landwirtschaft geeignetes Kation ersetzt wird, beispielsweise Metallsalze, insbesondere Alkalimetallsalze oder Potassium hydroxide, sodium and potassium carbonate and sodium and potassium hydrogen carbonate. This Salts are compounds in which the acidic hydrogen is replaced by a cation suitable for agriculture, for example metal salts, in particular alkali metal salts or
Erdalkalimetallsalze, insbesondere Natrium- und Kaliumsalze, oder auch Ammoniumsalze, Salze mit organischen Aminen oder quartäre Ammoniumsalze, zum Beispiel mit Kationen der Formel Alkaline earth metal salts, especially sodium and potassium salts, or also ammonium salts, salts with organic amines or quaternary ammonium salts, for example with cations of the formula
[NRaRbRcRd]+, worin Ra bis Rd jeweils unabhängig voneinander einen organischen Rest, insbesondere Alkyl, Aryl, Arylalkyl oder Alkylaryl darstellen. Infrage kommen auch Alkylsulfonium- und [NR a R b R c R d ] + , where R a to R d each independently represent an organic radical, in particular alkyl, aryl, arylalkyl or alkylaryl. Alkylsulfonium and
Alkylsulfoxoniumsalze, wie (Ci-C4)-Trialkylsulfonium- und (Ci-C4)-Trialkylsulfoxoniumsalze. Alkylsulfoxonium salts such as (Ci-C 4 ) -trialkylsulfonium and (Ci-C 4 ) -trialkylsulfoxonium salts.
Die erfindungsgemäßen substituierten 2-Heteroaryloxypyridine der allgemeinen Formel (I) können in Abhängigkeit von äußeren Bedingungen, wie pH-Wert, Lösungsmittel und Temperatur eventuell in verschiedenen tautomeren Strukturen vorliegen, die alle von der allgemeinen Formel (I) umfasst sind. Depending on external conditions such as pH, solvent and temperature, the substituted 2-heteroaryloxypyridines of the general formula (I) according to the invention may be present in various tautomeric structures, all of which are encompassed by the general formula (I).
Im Folgenden werden die erfindungsgemäß verwendeten Verbindungen der Formel (I) und ihre Salze "Verbindungen der allgemeinen Formel (I)" bezeichnet. The compounds of the formula (I) used according to the invention and their salts are referred to below as "compounds of the general formula (I)".
Bevorzugter Erfindungsgegenstand sind Verbindungen der allgemeinen Formel (I), worin X für Stickstoff, -CF- oder -CH- steht, Preferred subject matter of the invention are compounds of the general formula (I), in which X represents nitrogen, -CF- or -CH-,
A für Sauerstoff, -S(0)n-, -C(R4)(R5) -, -C(=0) -, oder -NR6- steht A stands for oxygen, -S (0) n- , -C (R 4 ) (R 5 ) -, -C (= 0) -, or -NR 6 -
mit n gleich 0, 1 oder 2,  with n equal to 0, 1 or 2,
R1 für ein gegebenenfalls substituiertes Aryl, Heteroaryl, oder Heterocylyl steht, wobei jeder Ring oder jedes Ringsystem optional mit bis zu 5 Substituenten, unabhängig voneinander ausgewählt aus der Gruppe R7 substituiert ist, R 1 represents an optionally substituted aryl, heteroaryl or heterocylyl, each ring or ring system optionally being substituted with up to 5 substituents selected independently from the group R 7 ,
R2 unabhängig voneinander für Halogen, Cyano, Nitro, Formyl, Formamid, (G-G)- Alkyl, (G-G)- Haloalkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (C2-C6)-Haloalkenyl, (C2-C6)-Haloalkinyl, (Ci- C4)-Alkoxy-(Ci-C4)-alkyl, (Ci-C4)-Haloalkoxy-(Ci-C4)-alkyl, (Ci-C4)-Alkylthio-(Ci-C4)-alkyl, (Ci-C4)-Alkylsulfmyl-(Ci-C4)-alkyl, (Ci-C4)-Alkylsulfonyl-(Ci-C4)-alkyl, (Ci-C6)- Alkylcarbonyl, (Ci-G)-Haloalkylcarbonyl, (C3-C6)-Cycloalkylcarbonyl, Carboxyl, (G-G,)- Alkoxycarbonyl, (G-G,)- Haloalkoxycarbonyl, (C3-C6)-Cycloalkoxycarbonyl, Carbamoyl, (C2-C6)-Alkylaminocarbonyl, (C2-C8)-Dialkylaminocarbonyl, (C3-C6)-R 2 independently of one another for halogen, cyano, nitro, formyl, formamide, (GG) - alkyl, (GG) - haloalkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 2 -C 6 ) -haloalkenyl, (C 2 -C 6 ) -haloalkynyl, (Ci-C 4 ) -alkoxy- (Ci-C 4 ) -alkyl, (Ci-C 4 ) -haloalkoxy- (Ci-C 4 ) -alkyl, (Ci-C 4 ) -alkylthio- (Ci-C 4 ) -alkyl, (Ci-C 4 ) -alkylsulfmyl- (Ci-C 4 ) -alkyl, (Ci-C 4 ) -alkylsulfonyl- (Ci -C 4 ) alkyl, (Ci-C 6 ) alkylcarbonyl, (Ci-G) haloalkylcarbonyl, (C 3 -C 6 ) cycloalkylcarbonyl, carboxyl, (GG,) - alkoxycarbonyl, (GG,) - haloalkoxycarbonyl, (C 3 -C 6 ) cycloalkoxycarbonyl, carbamoyl, (C 2 -C 6 ) alkylaminocarbonyl, (C 2 -C 8 ) dialkylaminocarbonyl, (C 3 -C 6 ) -
Cycloalkylaminocarbonyl, (Ci-C4)-Alkoxycarbonyl-(Ci-C4)-alkyl, (Ci-C4)-Haloalkoxycarbonyl- (Ci-C4)-alkyl, Carboxy-(Ci-C6)-alkyl, Hydroxy, Amino, (G-G)-Alkoxy, (Ci-G,)-Haloalkoxy, (Ci-Cej-Alkylthio, (Ci-G,)-Haloalkylthio, (C3-C6)-Cycloalkylthio, (Ci-G,)-Alkylsulfinyl, (Ci-C6)-Haloalkylsulfinyl, (C3-C6)-Cycloalkylsulfinyl, (Ci-G,)-Alkylsulfonyl, (C'i-G,)- Haloalkylsulfonyl, (C3-C6)-Cycloalkylsulfonyl, (Ci-C6)-Alkylaminosulfonyl, (C2-Cx)- Dialkylaminosulfonyl oder (C3-C8)-Trialkylsilyl steht, m ist gleich 0, 1, 2, oder 3, Cycloalkylaminocarbonyl, (Ci-C 4 ) -alkoxycarbonyl- (Ci-C 4 ) -alkyl, (Ci-C 4 ) -haloalkoxycarbonyl- (Ci-C 4 ) -alkyl, carboxy- (Ci-C 6 ) -alkyl, hydroxy , Amino, (GG) -alkoxy, (Ci-G,) - haloalkoxy, (Ci-Cej-alkylthio, (Ci-G,) - haloalkylthio, (C 3 -C 6 ) -cycloalkylthio, (Ci-G,) -Alkylsulfinyl, (Ci-C 6 ) -Haloalkylsulfinyl, (C 3 -C 6 ) -cycloalkylsulfinyl, (Ci-G,) - alkylsulfonyl, (C ' iG,) - Haloalkylsulfonyl, (C 3 -C 6 ) cycloalkylsulfonyl, (Ci-C 6 ) alkylaminosulfonyl, (C 2 -Cx) dialkylaminosulfonyl or (C 3 -C 8 ) trialkylsilyl, m is 0, 1, 2, Or 3,
R3 für Wasserstoff, Halogen, Cyano, Nitro, Formyl, (Ci-C6)-Alkyl, (Ci-C6)-Haloalkyl, (C2-C6)- Alkenyl, (C2-C6)-Alkinyl, (C2-C6)-Haloalkenyl, (C2-C6)-Haloalkinyl, (Ci-C4)-Alkoxy-(Ci-C4)- alkyl, (Ci-C4)-Haloalkoxy-(Ci-C4)-alkyl, (Ci-C4)-Alkylthio-(Ci-C4)-alkyl, (Ci-C4)- Alkylsulfmyl-(Ci-C4)-alkyl, (Ci-C4)-Alkylsulfonyl-(Ci-C4)-alkyl, (Ci-C6)-Alkylcarbonyl, (Ci-C6)-Haloalkylcarbonyl, (C3-C6)-Cycloalkylcarbonyl, Carboxyl, (Ci-C6)-Alkoxycarbonyl, (CI-CÖ)- Haloalkoxycarbonyl, (C3-C6)-Cycloalkoxycarbonyl, (Ci-C6)-Alkylaminocarbonyl, (C2-C8)-Dialkylaminocarbonyl, (C3-C6)-Cycloalkylaminocarbonyl, Hydroxy, (Ci-Cö)-Alkoxy, (Ci-C6)-Haloalkoxy, (Ci-C6)-Alkylthio, (Ci-C6)-Haloalkylthio, (C3-C6)-Cycloalkylthio, (Ci-C6)- Alkylsulfmyl, (Ci-C6)-Haloalkylsulfinyl, (C3-C6)-Cycloalkylsulfinyl, (Ci-C6)-Alkylsulfonyl, (Ci-C6)-Haloalkylsulfonyl, (C3-C6)-Cycloalkylsulfonyl, (Ci-C6)-Alkylaminosulfonyl, (C2-Cs)- Dialkylaminosulfonyl oder (C3-C8)-Trialkylsilyl steht, R 3 is hydrogen, halogen, cyano, nitro, formyl, (Ci-C 6 ) alkyl, (Ci-C 6 ) haloalkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl , (C 2 -C 6 ) haloalkenyl, (C 2 -C 6 ) haloalkynyl, (Ci-C 4 ) alkoxy- (Ci-C 4 ) - alkyl, (Ci-C 4 ) -haloalkoxy- (Ci -C 4 ) -alkyl, (Ci-C 4 ) -alkylthio- (Ci-C 4 ) -alkyl, (Ci-C 4 ) - alkylsulfmyl- (Ci-C 4 ) -alkyl, (Ci-C 4 ) - Alkylsulfonyl- (Ci-C 4 ) -alkyl, (Ci-C 6 ) -alkylcarbonyl, (Ci-C 6 ) -haloalkylcarbonyl, (C 3 -C 6 ) -cycloalkylcarbonyl, carboxyl, (Ci-C 6 ) -alkoxycarbonyl, (C I -C Ö ) haloalkoxycarbonyl, (C 3 -C 6 ) cycloalkoxycarbonyl, (Ci-C 6 ) alkylaminocarbonyl, (C 2 -C 8 ) dialkylaminocarbonyl, (C 3 -C 6 ) cycloalkylaminocarbonyl, hydroxy , (Ci-C ö ) alkoxy, (Ci-C 6 ) -haloalkoxy, (Ci-C 6 ) -alkylthio, (Ci-C 6 ) -haloalkylthio, (C 3 -C 6 ) -cycloalkylthio, (Ci- C 6 ) alkylsulfmyl, (Ci-C 6 ) haloalkylsulfinyl, (C 3 -C 6 ) cycloalkylsulfinyl, (Ci-C 6 ) alkylsulfonyl, (Ci-C 6 ) haloalkylsulfonyl, (C 3 -C 6 ) -Cycloalkylsulfonyl, (Ci-C 6 ) -alkylaminosulfonyl, (C 2 -Cs ) - dialkylaminosulfonyl or (C 3 -C 8 ) -trialkylsilyl,
R4 und R5 unabhängig voneinander für Wasserstoff, Hydroxy, Halogen, (Ci-C6)-Alkyl, (C'i-G,)- Haloalkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (Ci-C4)-Alkoxy-(Ci-C4)-alkyl, (Ci-C4)- Haloalkoxy-(Ci-C4)-alkyl, (Ci-C4)-Alkylthio-(Ci-C4)-alkyl, (Ci-C4)-Alkylsulfmyl-(Ci-C4)-alkyl, (Ci-C4)-Alkylsulfonyl-(Ci-C4)-alkyl, (Ci-C6)-Alkylcarbonyl, (Ci-C6)-Haloalkylcarbonyl, (C3-C6)-Cycloalkylcarbonyl, (Ci-C6)-Alkoxycarbonyl, (CI-CÖ)- Haloalkoxycarbonyl, (C3-C6)- Cycloalkoxycarbonyl, (Ci-C6)-Alkylaminocarbonyl, (C2-C8)-Dialkylaminocarbonyl, (C3-C6)- Cycloalkylaminocarbonyl, (Ci-Cö)-Alkoxy, (Ci-C6)-Alkylthio, (Ci-C6)-Haloalkylthio, (C3-C6)- Cycloalkylthio, stehen, oder R 4 and R 5 independently of one another are hydrogen, hydroxy, halogen, (Ci-C 6 ) -alkyl, (C ' iG,) - haloalkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) - Alkynyl, (Ci-C 4 ) -alkoxy- (Ci-C 4 ) -alkyl, (Ci-C 4 ) - haloalkoxy- (Ci-C 4 ) -alkyl, (Ci-C 4 ) -alkylthio- (Ci C 4 ) alkyl, (Ci-C 4 ) alkylsulfmyl- (Ci-C 4 ) -alkyl, (Ci-C 4 ) -alkylsulfonyl- (Ci-C 4 ) -alkyl, (Ci-C 6 ) -alkylcarbonyl , (Ci-C 6 ) -haloalkylcarbonyl, (C 3 -C 6 ) -cycloalkylcarbonyl, (Ci-C 6 ) -alkoxycarbonyl, (C I -C Ö ) - haloalkoxycarbonyl, (C 3 -C 6 ) - cycloalkoxycarbonyl, ( Ci-C 6 ) -alkylaminocarbonyl, (C 2 -C 8 ) -dialkylaminocarbonyl, (C 3 -C 6 ) -cycloalkylaminocarbonyl, (Ci-C ö ) -alkoxy, (Ci-C 6 ) -alkylthio, (Ci-C 6 ) -Haloalkylthio, (C 3 -C 6 ) - cycloalkylthio, stand, or
R4 und R5 gemeinsam einen 3- bis 6-gliedrigen carbocyclischen Ring oder einen 3- bis 6-gliedrigen gesättigten heterocyclischen Ring mit bis zu 2 Sauerstoffatomen bilden, oder R 4 and R 5 together form a 3- to 6-membered carbocyclic ring or a 3- to 6-membered saturated heterocyclic ring with up to 2 oxygen atoms, or
R4 und R5 gemeinsam einen (Ci-C3)-Alkylidenrest oder (Ci-C3)-Haloalkylidenrest bilden, R6 für Wasserstoff, (Ci-C6)-Alkyl, (Ci-C6)-Haloalkyl, Aryl-(Ci-C4)-alkyl, Heteroaryl-(Ci-C4)-alkyl, (C3-C6)-Cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C4)-alkyl, (C3-C6)-Halocycloalkyl, (C3-C6)- Halocycloalkyl-(Ci-C4)-alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (Ci-C4)-Alkoxy-(Ci-C4)-alkyl, (Ci-C4)-Haloalkoxy-(Ci-C4)-alkyl, (Ci-C4)-Alkylthio-(Ci-C4)-alkyl, (Ci-C4)-Alkylsulfmyl- (Ci-C4)-alkyl, (Ci-C4)-Alkylsulfonyl-(Ci-C4)-alkyl, (Ci-C6)-Alkylcarbonyl, (Ci-C6)- Haloalkylcarbonyl, (C3-C6)-Cycloalkylcarbonyl, Formyl, (Ci-C6)-Alkoxycarbonyl, (G-G,)- Haloalkoxycarbonyl, (C3-C6)-Cycloalkoxycarbonyl, (Ci-C6)-Alkylaminocarbonyl, (G-G)- Dialkylaminocarbonyl, (C3-C8)-Cycloalkylaminocarbonyl steht, R 4 and R 5 together form a (Ci-C 3 ) alkylidene radical or (Ci-C 3 ) haloalkylidene radical, R 6 for hydrogen, (Ci-C 6 ) -alkyl, (Ci-C 6 ) -haloalkyl, aryl- (Ci-C4) -alkyl, heteroaryl- (Ci-C4) -alkyl, (C 3 -C 6 ) -Cycloalkyl, (C3-C 6 ) -cycloalkyl- (Ci-C 4 ) -alkyl, (C 3 -C 6 ) -halocycloalkyl, (C 3 -C 6 ) -halocycloalkyl- (Ci-C 4 ) -alkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (Ci-C 4 ) alkoxy- (Ci-C 4 ) alkyl, (Ci-C 4 ) -haloalkoxy- (Ci C 4 ) alkyl, (Ci-C 4 ) alkylthio- (Ci-C 4 ) alkyl, (Ci-C 4 ) -alkylsulfmyl- (Ci-C 4 ) -alkyl, (Ci-C 4 ) -alkylsulfonyl - (Ci-C 4 ) -alkyl, (Ci-C 6 ) -alkylcarbonyl, (Ci-C 6 ) - haloalkylcarbonyl, (C 3 -C 6 ) -cycloalkylcarbonyl, formyl, (Ci-C 6 ) -alkoxycarbonyl, ( GG,) - haloalkoxycarbonyl, (C 3 -C 6 ) -cycloalkoxycarbonyl, (Ci-C 6 ) -alkylaminocarbonyl, (GG) - dialkylaminocarbonyl, (C 3 -C 8 ) -cycloalkylaminocarbonyl,
R7 für Wasserstoff, Halogen, Cyano, Nitro, Formyl, (Ci-C6)-Alkyl, (Ci-C6)-Haloalkyl, (G-G,)- Alkenyl, (C2-C6)-Alkinyl, (C2-C6)-Haloalkenyl, (C2-C6)-Haloalkinyl, (Ci-C4)-Alkoxy-(Ci-C4)- alkyl, (Ci-C4)-Haloalkoxy-(Ci-C4)-alkyl, (G-C4)-Alkylthio-(G-C4)-alkyl, (Ci-C4)- Alkylsulfinyl-(Ci-C4)-alkyl, (Ci-C4)-Alkylsulfonyl-(Ci-C4)-alkyl, (Ci-C6)-Alkylcarbonyl, (G-C6)-Haloalkylcarbonyl, (C3-C6)-Cycloalkylcarbonyl, Carboxyl, (Ci-C6)-Alkoxycarbonyl, (CI-CÖ)- Haloalkoxycarbonyl, (C3-C6)-Cycloalkoxycarbonyl, (Ci-C6)-Alkylaminocarbonyl, (C2-C8)-Dialkylaminocarbonyl, (C3-C6)-Cycloalkylaminocarbonyl, Hydroxy, (G-G)-Alkoxy, (Ci-C6)-Haloalkoxy, (Ci-C6)-Alkylthio, (Ci-C6)-Haloalkylthio, (C3-C6)-Cycloalkylthio, (Ci-C6)- Alkylsulfinyl, (Ci-C6)-Haloalkylsulfinyl, (C3-C6)-Cycloalkylsulfinyl, (G-C6)-Alkylsulfonyl, (Ci-C6)-Haloalkylsulfonyl, (C3-C6)-Cycloalkylsulfonyl, (Ci-C6)-Alkylaminosulfonyl, (C2-Cs)- Dialkylaminosulfonyl oder (C3-C8)-Trialkylsilyl steht. R 7 for hydrogen, halogen, cyano, nitro, formyl, (Ci-C 6 ) alkyl, (Ci-C 6 ) haloalkyl, (GG,) - alkenyl, (C 2 -C 6 ) alkynyl, (C 2 -C 6 ) haloalkenyl, (C 2 -C 6 ) haloalkynyl, (Ci-C 4 ) alkoxy- (Ci-C 4 ) alkyl, (Ci-C 4 ) -haloalkoxy- (Ci-C 4 ) alkyl, (GC 4 ) alkylthio- (GC 4 ) alkyl, (Ci-C 4 ) alkylsulfinyl (Ci-C4) alkyl, (Ci-C4) alkylsulfonyl- (Ci-C4) alkyl , (Ci-C 6 ) alkylcarbonyl, (GC 6 ) haloalkylcarbonyl, (C 3 -C 6 ) cycloalkylcarbonyl, carboxyl, (Ci-C 6 ) alkoxycarbonyl, (C I -C Ö ) - haloalkoxycarbonyl, (C 3 -C 6 ) cycloalkoxycarbonyl, (Ci-C 6 ) alkylaminocarbonyl, (C 2 -C 8 ) dialkylaminocarbonyl, (C 3 -C 6 ) cycloalkylaminocarbonyl, hydroxy, (GG) alkoxy, (Ci-C 6 ) haloalkoxy, (Ci-C 6) alkylthio, (Ci-C 6) haloalkylthio, (C 3 -C 6) -cycloalkylthio, (Ci-C 6) - alkylsulfinyl, (Ci-C 6) haloalkylsulfinyl, (C 3 -C 6 ) cycloalkylsulfinyl, (GC 6 ) alkylsulfonyl, (Ci-C 6 ) haloalkylsulfonyl, (C 3 -C 6 ) cycloalkylsulfonyl, (Ci-C 6 ) alkylaminosulfonyl, (C 2 -Cs ) - Dialkylaminosulfonyl or (C 3 -C 8 ) -trialkylsilyl.
Besonders bevorzugter Erfindungsgegenstand sind Verbindungen der allgemeinen Formel (1), worin Particularly preferred subject matter of the invention are compounds of the general formula (1), in which
X für Stickstoff, -CF- oder -CH- steht, X represents nitrogen, -CF- or -CH-,
A für Sauerstoff, -S(0)n-, -C(R4)(R5) -, -C(=0) -, oder -NR6- steht A stands for oxygen, -S (0) n- , -C (R 4 ) (R 5 ) -, -C (= 0) -, or -NR 6 -
mit n gleich 0, 1 oder 2,  with n equal to 0, 1 or 2,
R1 für ein gegebenenfalls substituiertes Aryl, Heteroaryl, oder Heterocylyl steht, wobei jeder Ring oder jedes Ringsystem optional mit bis zu 5 Substituenten, unabhängig voneinander ausgewählt aus der Gruppe R7, substituiert ist, R 1 represents an optionally substituted aryl, heteroaryl or heterocylyl, each ring or ring system optionally being substituted with up to 5 substituents, selected independently of one another from the group R 7 ,
R2 unabhängig voneinander für Halogen, Cyano, Nitro, Formyl, Formamid, (Ci-C4)-Alkyl, (C1-C4)- Haloalkyl, (C2-C4)-Alkenyl, (C2-C4)-Alkinyl, (C2-C4)-Haloalkenyl, (Ci-C4)-Alkoxy-(Ci-C4)- alkyl, (Ci-C4)-Haloalkoxy-(Ci-C4)-alkyl, (Ci-C4)-Alkylcarbonyl, (Ci-C4)-Haloalkylcarbonyl, Carboxyl, (Ci-C4)-Alkoxycarbonyl, (C1-C4)- Haloalkoxycarbonyl, (C3-C6)- Cycloalkoxycarbonyl, Carbamoyl, (C2-C4)-Alkylaminocarbonyl, (C2-C6)-Dialkylaminocarbonyl, (Ci-C4)-Alkoxycarbonyl-(Ci-C4)-alkyl, (Ci-C4)-Haloalkoxycarbonyl-(Ci-C4)-alkyl, Carboxy- (Ci-C4)-alkyl, Hydroxy, Amino, (Ci-C4)-Alkoxy, (Ci-C4)-Haloalkoxy, (Ci-C4)-Alkylthio, (Ci-C4)-Alkylsulfinyl, (Ci-C4)-Alkylsulfonyl, (Ci-C4)-Alkylaminosulfonyl, (C2-C6)- Dialkylaminosulfonyl oder (C3-C6)-Trialkylsilyl steht, m ist gleich 0, 1, 2, oder 3, R 2 independently of one another for halogen, cyano, nitro, formyl, formamide, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl, (C 2 -C 4 ) -alkenyl, (C 2 -C 4 ) -Alkynyl, (C 2 -C 4 ) -haloalkenyl, (Ci-C 4 ) -alkoxy- (Ci-C 4 ) - alkyl, (Ci-C 4 ) -haloalkoxy- (Ci-C 4 ) -alkyl, (Ci-C 4 ) -alkylcarbonyl, (Ci-C 4 ) -haloalkylcarbonyl, carboxyl, (Ci-C 4 ) -alkoxycarbonyl, ( C 1 -C 4 ) haloalkoxycarbonyl, (C 3 -C 6 ) cycloalkoxycarbonyl, carbamoyl, (C 2 -C 4 ) alkylaminocarbonyl, (C 2 -C 6 ) dialkylaminocarbonyl, (Ci-C 4 ) alkoxycarbonyl- (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkoxycarbonyl- (Ci-C 4 ) alkyl, carboxy- (Ci-C 4 ) alkyl, hydroxy, amino, (Ci-C 4 ) alkoxy , (Ci-C 4 ) -haloalkoxy, (Ci-C 4 ) -alkylthio, (Ci-C 4 ) -alkylsulfinyl, (Ci-C 4 ) -alkylsulfonyl, (Ci-C 4 ) -alkylaminosulfonyl, (C 2 - C 6 ) - dialkylaminosulfonyl or (C 3 -C 6 ) -trialkylsilyl, m is 0, 1, 2 or 3,
R3 für Wasserstoff, Halogen, Cyano, Nitro, Formyl, (Ci-C4)-Alkyl, (Ci-C4)-Haloalkyl, (C2-C4)- Alkenyl, (C2-C4)-Alkinyl, (C2-C4)-Haloalkenyl, (C2-C4)-Haloalkinyl, (Ci-C4)-Alkylcarbonyl, (Ci-C4)-Haloalkylcarbonyl, Carboxyl, (Ci-C4)-Alkoxycarbonyl, (C1-C4)- Haloalkoxycarbonyl, (C3-C6)-Cycloalkoxycarbonyl, (Ci-C4)-Alkylaminocarbonyl, (C2-C6)-Dialkylaminocarbonyl, Hydroxy, (Ci-C4)-Alkoxy, (Ci-C4)-Haloalkoxy, (Ci-C4)-Alkylthio, (Ci-C4)-Haloalkylthio, (Ci-C4)-Alkylsulfinyl, (Ci-C4)-Haloalkylsulfinyl, (Ci-C4)-Alkylsulfonyl, (C1-C4)- Haloalkylsulfonyl, (Ci-C4)-Alkylaminosulfonyl, (C2-C6)-Dialkylaminosulfonyl oder (C3-C6)- Trialkylsilyl steht, R 3 is hydrogen, halogen, cyano, nitro, formyl, (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl , (C 2 -C 4 ) haloalkenyl, (C 2 -C 4 ) haloalkynyl, (Ci-C 4 ) alkylcarbonyl, (Ci-C 4 ) haloalkylcarbonyl, carboxyl, (Ci-C 4 ) alkoxycarbonyl, (C 1 -C 4 ) haloalkoxycarbonyl, (C 3 -C 6 ) cycloalkoxycarbonyl, (Ci-C 4 ) alkylaminocarbonyl, (C 2 -C 6 ) dialkylaminocarbonyl, hydroxy, (Ci-C 4 ) alkoxy, (Ci-C 4 ) haloalkoxy, (Ci-C 4 ) alkylthio, (Ci-C 4 ) haloalkylthio, (Ci-C 4 ) alkylsulfinyl, (Ci-C 4 ) haloalkylsulfinyl, (Ci-C 4 ) Alkylsulfonyl, (C 1 -C 4 ) haloalkylsulfonyl, (Ci-C 4 ) alkylaminosulfonyl, (C 2 -C 6 ) dialkylaminosulfonyl or (C 3 -C 6 ) trialkylsilyl,
R4 und R5 unabhängig voneinander für Wasserstoff, Hydroxy, Halogen, (Ci-C4)-Alkyl, (C1-C4)- Haloalkyl, (C2-C4)-Alkenyl, (C2-C4)-Alkinyl, (Ci-C4)-Alkoxycarbonyl, (C1-C4)- Haloalkoxycarbonyl oder (C3-C6)-Cycloalkoxycarbonyl stehen, oder R 4 and R 5 are independently hydrogen, hydroxy, halogen, (Ci-C 4) -alkyl, (C 1 -C 4) - haloalkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) -Alkynyl, (Ci-C 4 ) -alkoxycarbonyl, (C 1 -C 4 ) - haloalkoxycarbonyl or (C 3 -C 6 ) -cycloalkoxycarbonyl, or
R4 und R5 gemeinsam einen (Ci-C3)-Alkylidenrest oder (Ci-C3)-Haloalkylidenrest bilden, R 4 and R 5 together form a (Ci-C 3 ) alkylidene radical or (Ci-C 3 ) haloalkylidene radical,
R6 für Wasserstoff, (Ci-C4)-Alkyl, (Ci-C4)-Haloalkyl, Aryl-(Ci-C4)-alkyl, Heteroaryl-(Ci-C4)-alkyl, (C2-C4)-Alkenyl, (C2-C4)-Alkinyl, (Ci-C4)-Alkylcarbonyl, Formyl oder (Ci-C4)-Alkoxycarbonyl steht, R 6 is hydrogen, (Ci-C 4 ) -alkyl, (Ci-C 4 ) -haloalkyl, aryl- (Ci-C 4 ) -alkyl, heteroaryl- (Ci-C 4 ) -alkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) alkynyl, (Ci-C 4) alkylcarbonyl, formyl or (Ci-C is 4) alkoxycarbonyl,
R7 für Wasserstoff, Halogen, Cyano, Nitro, Formyl, (Ci-C4)-Alkyl, (Ci-C4)-Haloalkyl, (C2-C4)- Alkenyl, (C2-C4)-Alkinyl, (C2-C4)-Haloalkenyl, (C2-C4)-Haloalkinyl, (Ci-C4)-Alkoxy-(Ci-C4)- alkyl, (Ci-C4)-Haloalkoxy-(Ci-C4)-alkyl, (Ci-C4)-Alkylcarbonyl, (Ci-C4)-Haloalkylcarbonyl, Carboxyl, (Ci-C4)-Alkoxycarbonyl, (C1-C4)- Haloalkoxycarbonyl, (C3-C6)- Cycloalkoxycarbonyl, (Ci-C4)-Alkylaminocarbonyl, (C2-C6)-Dialkylaminocarbonyl, (C3-C6)- Cycloalkylaminocarbonyl, Hydroxy, (Ci-C4)-Alkoxy, (Ci-C4)-Haloalkoxy, (Ci-C4)-Alkylthio, (Ci-C4)-Haloalkylthio, (Ci-C4)-Alkylsulfinyl, (Ci-C4)-Haloalkylsulfinyl, (Ci-C4)-Alkylsulfonyl, (Ci-C4)-Haloalkylsulfonyl, (Ci-C4)-Alkylaminosulfonyl, (C2-C6)-Dialkylaminosulfonyl oder (C3-C6)-Trialkylsilyl steht. R 7 is hydrogen, halogen, cyano, nitro, formyl, (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl , (C 2 -C 4 ) haloalkenyl, (C 2 -C 4 ) haloalkynyl, (Ci-C 4 ) alkoxy- (Ci-C 4 ) - alkyl, (Ci-C 4 ) -haloalkoxy- (Ci -C 4 ) -alkyl, (Ci-C 4 ) -alkylcarbonyl, (Ci-C 4 ) -haloalkylcarbonyl, carboxyl, (Ci-C 4 ) -alkoxycarbonyl, (C 1 -C 4 ) - haloalkoxycarbonyl, (C 3 - C 6 ) - Cycloalkoxycarbonyl, (Ci-C 4 ) alkylaminocarbonyl, (C2-C6) dialkylaminocarbonyl, (C3-C6) cycloalkylaminocarbonyl, hydroxy, (Ci-C 4 ) alkoxy, (Ci-C 4 ) haloalkoxy, (Ci C 4 ) -alkylthio, (Ci-C 4 ) -haloalkylthio, (Ci-C 4 ) -alkylsulfinyl, (Ci-C 4 ) -haloalkylsulfinyl, (Ci-C 4 ) -alkylsulfonyl, (Ci-C 4 ) -haloalkylsulfonyl , (Ci-C 4 ) -alkylaminosulfonyl, (C2-C6) -dialkylaminosulfonyl or (C3-C6) -trialkylsilyl.
Ganz besonders bevorzugter Erfindungsgegenstand sind Verbindungen der allgemeinen Formel (I), worin Very particularly preferred subject matter of the invention are compounds of the general formula (I), in which
X für Stickstoff, -CF- oder -CH- steht, X represents nitrogen, -CF- or -CH-,
A für Sauerstoff, -S(0)n-, -C(R4)(R5) -, -C(=0) -, oder -NR6- steht A stands for oxygen, -S (0) n -, -C (R 4 ) (R 5 ) -, -C (= 0) -, or -NR 6 -
mit n gleich 0, 1 oder 2,  with n equal to 0, 1 or 2,
R1 für ein gegebenenfalls substituiertes Phenyl, Pyridyl oder Pyrimidyl steht, wobei jeder Ring oder jedes Ringsystem optional mit bis zu 5 Substituenten, unabhängig voneinander ausgewählt aus der Gruppe R7, substituiert ist, R 1 represents an optionally substituted phenyl, pyridyl or pyrimidyl, each ring or ring system optionally being substituted with up to 5 substituents, selected independently of one another from the group R 7 ,
R2 unabhängig voneinander für Halogen, Cyano, (Ci-C i)-Alkyl, (Ci-C4)-Haloalkyl, Carboxyl,R 2 independently of one another for halogen, cyano, (Ci-C i) alkyl, (Ci-C 4 ) haloalkyl, carboxyl,
(Ci-C i)-Alkoxycarbonyl, (Ci-C i)-Alkoxycarbonyl-(Ci-C3)-alkyl, (Ci-C4)-Haloalkoxycarbonyl- (Ci-C3)-alkyl, Carboxy-(Ci-C3)-alkyl oder (Ci-C4)-Alkoxy steht, m ist gleich 0, 1, 2, oder 3, (Ci-C i) alkoxycarbonyl, (Ci-C i) alkoxycarbonyl- (Ci-C3) -alkyl, (Ci-C 4 ) -haloalkoxycarbonyl- (Ci-C3) -alkyl, carboxy- (Ci-C3) alkyl or (Ci-C 4 ) alkoxy, m is 0, 1, 2 or 3,
R3 für Wasserstoff, Halogen, Cyano, (Ci-C i)-Alkyl, (Ci-C4)-Haloalkyl, (C2-C i)-Alkenyl, (C2-C4)- Alkinyl, (C2-C4)-Haloalkenyl, (C2-C4)-Haloalkinyl, (Ci-C4)-Alkoxy oder (Ci-C4)-Haloalkoxy steht, R 3 is hydrogen, halogen, cyano, (Ci-C i) alkyl, (Ci-C 4 ) haloalkyl, (C2-C i) alkenyl, (C 2 -C 4 ) alkynyl, (C2-C4 ) -Haloalkenyl, (C2-C 4 ) -haloalkynyl, (Ci-C 4 ) -alkoxy or (Ci-C 4 ) -haloalkoxy,
R4 und R5 unabhängig voneinander für Wasserstoff, Halogen, (Ci-C4)-Alkyl oder (C1-C4)- Alkoxycarbonyl stehen, R 4 and R 5 are independently hydrogen, halogen, (Ci-C 4) -alkyl or (C 1 -C 4) - alkoxycarbonyl,
R6 für Wasserstoff, (Ci-C4)-Alkyl, (Ci-C4)-Alkylcarbonyl oder (Ci-C4)-Alkoxycarbonyl steht, und R7 für Wasserstoff, Halogen, Cyano, (Ci-C4)-Alkyl, (Ci-C4)-Haloalkyl, Carboxyl, (C1-C4)- Alkoxycarbonyl, Hydroxy, (Ci-C4)-Alkoxy oder (Ci-C4)-Haloalkoxy steht. R 6 represents hydrogen, (Ci-C 4 ) -alkyl, (Ci-C 4 ) -alkylcarbonyl or (Ci-C 4 ) -alkoxycarbonyl, and R 7 for hydrogen, halogen, cyano, (Ci-C4) alkyl, (Ci-C4) haloalkyl, carboxyl, (C1-C4) alkoxycarbonyl, hydroxy, (Ci-C4) alkoxy or (Ci-C4) -Haloalkoxy stands.
Ebenfalls weiter bevorzugter Erfindungsgegenstand sind Verbindungen der allgemeinen Formel (I), worin Also more preferred subject matter of the invention are compounds of general formula (I), wherein
X für Stickstoff, -CF- oder -CH- steht, X represents nitrogen, -CF- or -CH-,
A für Sauerstoff, Schwefel, -CH2 - oder -NR6- steht, A stands for oxygen, sulfur, -CH2 - or -NR 6 -,
R1 für ein gegebenenfalls substituiertes Phenyl, Pyridyl oder Pyrimidyl steht, wobei jeder Ring oder jedes Ringsystem optional mit bis zu 5 Substituenten, unabhängig voneinander ausgewählt aus der Gruppe R7, substituiert ist, R 1 represents an optionally substituted phenyl, pyridyl or pyrimidyl, each ring or ring system optionally being substituted with up to 5 substituents, selected independently of one another from the group R 7 ,
R2 unabhängig voneinander für Halogen, Cyano, (Ci-C i)-Alkyl, (Ci-C ij-Haloalkyl, Carboxyl,R 2 independently of one another for halogen, cyano, (Ci-C i) -alkyl, (Ci-C ij-haloalkyl, carboxyl,
(Ci-C i)-Alkoxycarbonyl, (Ci-C i)-Alkoxycarbonyl-(Ci-C3)-alkyl, (Ci-C ij-Haloalkoxycarbonyl- (Ci-C3)-alkyl, Carboxy-(Ci-C3)-alkyl oder (Ci-C ij-Alkoxy steht, m ist gleich 0, 1, 2, oder 3, (Ci-C i) alkoxycarbonyl, (Ci-C i) alkoxycarbonyl- (Ci-C3) -alkyl, (Ci-C ij-haloalkoxycarbonyl- (Ci-C3) -alkyl, carboxy- (Ci-C3) - is alkyl or (Ci-C ij-alkoxy, m is 0, 1, 2, or 3,
R3 für Wasserstoff, Halogen, Cyano, (Ci-C i)-Alkyl, (Ci-C ij-Haloalkyl, (Ci-C i)-Alkoxy oder R 3 is hydrogen, halogen, cyano, (Ci-C i) -alkyl, (Ci-C ij-haloalkyl, (Ci-C i) -alkoxy or
(Ci-C4)-Haloalkoxy steht,  (Ci-C4) haloalkoxy,
R6 für Wasserstoff oder Methyl steht, R 6 represents hydrogen or methyl,
R7 für Wasserstoff, Halogen, Cyano, (Ci-C i)-Alkyl, (Ci-C4)-Haloalkyl, (Ci-C4)-Alkoxy oder R 7 represents hydrogen, halogen, cyano, (Ci-C i) alkyl, (Ci-C4) haloalkyl, (Ci-C4) alkoxy or
(Ci-C4)-Haloalkoxy steht.  (Ci-C4) haloalkoxy.
Ebenfalls weiter bevorzugter Erfindungsgegenstand sind Verbindungen der allgemeinen Formel (1), worin Also more preferred subject matter of the invention are compounds of general formula (1), wherein
X für -CH-, -CF- oder Stickstoff steht, A für Sauerstoff, Schwefel, -CH2 - oder -NR6- steht, X represents -CH-, -CF- or nitrogen, A stands for oxygen, sulfur, -CH2 - or -NR 6 -,
R1 für ein gegebnenfalls substituiertes Phenyl, Pyrid-2-yl, oder Pyrimid-2-yl steht, wobei jeder Ring optional mit bis zu 5 Substituenten, unabhängig voneinander ausgewählt aus der Gruppe R7, substituiert ist, R 1 represents an optionally substituted phenyl, pyrid-2-yl or pyrimid-2-yl, each ring optionally being substituted with up to 5 substituents, selected independently of one another from the group R 7 ,
R2 unabhängig voneinander für Fluor, Chlor, Brom, Cyano, Methyl, Ethyl, Trifluormethyl, R 2 independently of one another for fluorine, chlorine, bromine, cyano, methyl, ethyl, trifluoromethyl,
Methoxy, Methoxycarbonylmethyl, Carboxylmethyl, steht, m ist gleich 0, 1, 2, oder 3,  Methoxy, methoxycarbonylmethyl, carboxylmethyl, m is 0, 1, 2 or 3,
R3 für Wasserstoff, Fluor, Chlor, Cyano, Methyl, Trifluormethyl, Methoxy, Trifluormethoxy steht, R6 für Wasserstoff oder Methyl steht, R 3 represents hydrogen, fluorine, chlorine, cyano, methyl, trifluoromethyl, methoxy, trifluoromethoxy, R 6 represents hydrogen or methyl,
R7 für Wasserstoff, Fluor, Chlor, Brom, Cyano, Methyl, Trifluormethyl, Methoxy, Trifluormethoxy steht. R 7 represents hydrogen, fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl, methoxy, trifluoromethoxy.
Äußerst bevorzugter Erfindungsgegenstand sind Verbindungen der allgemeinen Formel (I), worin Extremely preferred subject matter of the invention are compounds of the general formula (I), in which
X für -CH-, -CF- oder Stickstoff steht, X represents -CH-, -CF- or nitrogen,
A für Sauerstoff, Schwefel, -CH2 - oder -NH- steht A stands for oxygen, sulfur, -CH2 - or -NH-
R1 für Phenyl, 4-Fluorphenyl, 2,4-Difluorphenyl, 3,4-Difluorphenyl, 3-(Trifluormethyl)phenyl, 3- Methoxyphenyl, 3 -Chlorphenyl, 4-Chlorphenyl 4-Cyanophenyl, 4-Methylphenyl, 3-Fluor-4- methylphenyl, 4-Fluor-3-methylphenyl, 2,4-Difluor-3-methoxyphenyl, 5-Chlor-3-fluorpyrid-2- yl, 5-Chlorpyrid-2-yl, 5-Fluorpyrid-2-yl, 3,5-Difluorpyrid-2-yl, 5-Fluorpyrimid-2-yl, 5- Chlorpyrimid-2-yl steht; R 1 is phenyl, 4-fluorophenyl, 2,4-difluorophenyl, 3,4-difluorophenyl, 3- (trifluoromethyl) phenyl, 3-methoxyphenyl, 3-chlorophenyl, 4-chlorophenyl 4-cyanophenyl, 4-methylphenyl, 3-fluorine -4-methylphenyl, 4-fluoro-3-methylphenyl, 2,4-difluoro-3-methoxyphenyl, 5-chloro-3-fluoropyrid-2-yl, 5-chloropyrid-2-yl, 5-fluoropyrid-2-yl , 3,5-difluoropyrid-2-yl, 5-fluoropyrimid-2-yl, 5-chloropyrimid-2-yl;
R2 für Methyl steht, m ist gleich 0, 1 oder 2, und R 2 represents methyl, m is 0, 1 or 2, and
R3 für Wasserstoff, Fluor, Chlor, Trifluormethyl steht. R 3 represents hydrogen, fluorine, chlorine, trifluoromethyl.
Die oben aufgeführten allgemeinen oder in Vorzugsbereichen aufgeführten Restedefinitionen gelten sowohl für die Endprodukte der allgemeinenFormel (1) als auch entsprechend für die jeweils zur Herstellung benötigten Ausgangs- oder Zwischenprodukte. Diese Restedefinitionen können The general or preferred radical definitions listed above apply both to the end products of the general formula (1) and correspondingly to the starting or intermediate products required in each case for the preparation. These residual definitions can
untereinander, also auch zwischen den angegebenen bevorzugten Bereichen beliebig kombiniert werden. can be combined with one another, i.e. also between the specified preferred ranges.
Vor allem aus den Gründen der höheren herbiziden Wirkung, besseren Selektivität und/oder besseren Herstellbarkeit sind erfindungsgemäße Verbindungen der genannten allgemeinen Formel (1) oder deren Salze bzw. deren erfindungsgemäße Verwendung von besonderem lnteresse, worin einzelne Reste eine der bereits genannten oder im folgenden genannten bevorzugten Bedeutungen haben, oder insbesondere solche, worin eine oder mehrere der bereits genannten oder im Folgenden genannten bevorzugten Bedeutungen kombiniert auftreten. lm Hinblick auf die erfindungsgemäßen Verbindungen werden die vorstehend und weiter unten verwendeten Bezeichnungen erläutert. Diese sind dem Fachmann geläufig und haben insbesondere die im Folgenden erläuterten Bedeutungen: Especially for the reasons of the higher herbicidal activity, better selectivity and / or better manufacturability, compounds of the general formula (1) according to the invention or their salts or their use according to the invention are of particular interest, in which individual radicals are one of those already mentioned or mentioned below have preferred meanings, or in particular those in which one or more of the preferred meanings already mentioned or mentioned below occur in combination. With regard to the compounds according to the invention, the terms used above and below are explained. These are familiar to the person skilled in the art and in particular have the meanings explained below:
Sofern nicht anders definiert, gilt generell für die Bezeichnung von chemischen Gruppen, dass die Anbindung an das Gerüst bzw. den Rest des Moleküls über das zuletzt genannte Strukturelement der betreffenden chemischen Gruppe erfolgt, d.h. beispielsweise im Falle von (C2-Cg)-Alkenyloxy über das Sauerstoffatom, und im Falle von Heterocyclyl-(Ci-C8)-alkyl oder R120(0)C-(Ci-Cg)-Alkyl jeweils über das C-Atom der Alkylgruppe. Unless otherwise defined, it generally applies to the designation of chemical groups that the connection to the framework or the rest of the molecule takes place via the last-mentioned structural element of the chemical group in question, ie for example in the case of (C2-Cg) -alkenyloxy via the oxygen atom, and in the case of heterocyclyl- (Ci-C 8 ) -alkyl or R 12 0 (0) C- (Ci-Cg) -alkyl each via the C atom of the alkyl group.
Erfindungsgemäß steht "Alkylsulfonyl" - in Alleinstellung oder als Bestandteil einer chemischen Gruppe - für geradkettiges oder verzweigtes Alkylsulfonyl, vorzugsweise mit 1 bis 8, oder mit 1 bis 6 According to the invention, "alkylsulfonyl" - alone or as part of a chemical group - stands for straight-chain or branched alkylsulfonyl, preferably with 1 to 8, or with 1 to 6
Kohlenstoffatomen, z.B. (aber nicht beschränkt auf) (Ci-C6)-Alkylsulfonyl wie Methylsulfonyl, Ethyl- sulfonyl, Propylsulfonyl, 1 -Methylethylsulfonyl, Butylsulfonyl, 1 -Methylpropylsulfonyl, 2-Methyl- propylsulfonyl, l,l-Dimethylethylsulfonyl, Pentylsulfonyl, 1 -Methylbutylsulfonyl, 2-Methylbutyl- sulfonyl, 3 -Methylbutylsulfonyl, l,l-Dimethylpropylsulfonyl, 1 ,2-Dimethylpropylsulfonyl, 2,2-Di- methylpropylsulfonyl, 1 -Ethylpropylsulfonyl, Hexylsulfonyl, 1 -Methylpentylsulfonyl, 2-Methyl- pentylsulfonyl, 3 -Methylpentylsulfonyl, 4-Methylpentylsulfonyl, 1 , 1 -Dimethylbutylsulfonyl, l,2-Di- methylbutylsulfonyl, 1 ,3 -Dimethylbutylsulfonyl, 2,2-Dimethylbutylsulfonyl, 2,3-Dimethylbutylsulfonyl, 3 ,3 -Dimethylbutylsulfonyl, 1 -Ethylbutylsulfonyl, 2-Ethylbutylsulfonyl, 1 , 1 ,2-Trimethylpropylsulfonyl,Carbon atoms, for example (but not limited to) (Ci-C 6 ) alkylsulfonyl such as methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, l, l-dimethylethylsulfonyl, pentyl 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, l, l-dimethylpropylsulfonyl, 1, 2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonylsulfonyl, 1-methyl-pentylsulfonyl, 1-methyl 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1, 1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1, 3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3, 3 -dimethylbutylsulfonyl, 1 -ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1, 1, 2-trimethylpropylsulfonyl,
1 ,2,2-Trimethylpropylsulfonyl, 1 -Ethyl- 1 -methylpropylsulfonyl und 1 -Ethyl-2-methylpropylsulfonyl. 1, 2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl and 1-ethyl-2-methylpropylsulfonyl.
Erfindungsgemäß steht "Alkylthio" - in Alleinstellung oder als Bestandteil einer chemischen Gruppe - für geradketiges oder verzweigtes S-Alkyl, vorzugsweise mit 1 bis 8, oder mit 1 bis 6 According to the invention, "alkylthio" - alone or as part of a chemical group - stands for straight-chain or branched S-alkyl, preferably with 1 to 8, or with 1 to 6
Kohlenstoffatomen, wie (Ci-Cio)-, (C i-Cr,)- oder (Ci-C i)-Alkylthio, z.B. (aber nicht beschränkt auf) (Ci- C6)-Alkylthio wie Methylthio, Ethylthio, Propylthio, 1 -Methylethylthio, Butylthio, 1 -Methylpropylthio, 2-Methylpropylthio, 1 , 1 -Dimethylethylthio, Pentylthio, 1 -Methylbutylthio, 2-Methylbutylthio, 3- Methylbutylthio, l,l-Dimethylpropylthio, 1 ,2-Dimethylpropylthio, 2,2-Dimethylpropylthio, 1- Ethylpropylthio, Hexylthio, 1 -Methylpentylthio, 2-Methylpentylthio, 3-Methylpentylthio, 4-Methyl- pentylthio, l,l-Dimethylbutylthio, 1 ,2-Dimethylbutylthio, l,3-Dimethylbutylthio, 2,2-Dimethylbutyl- thio, 2,3-Dimethylbutylthio, 3,3-Dimethylbutylthio, 1 -Ethylbutylthio, 2-Ethylbutylthio, l,l,2-Tri- methylpropylthio, 1 ,2,2-Trimethylpropylthio, 1 -Ethyl- 1 -methylpropylthio und 1 -Ethyl-2-methyl- propylthio. Carbon atoms, such as (Ci-Cio) -, (C i-Cr,) - or (Ci-C i) -alkylthio, for example (but not limited to) (Ci-C 6 ) -alkylthio such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1, 1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, l, l-dimethylpropylthio, 1, 2-dimethylpropylthio, 2,2 Dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, l, l-dimethylbutylthio, 1, 2-dimethylbutylthio, l, 3-dimethylbutylthio, 2,2-dimethylbutylthio thio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, l, l, 2-trimethylpropylthio, 1, 2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio and 1- Ethyl 2-methylpropylthio.
„Alkylsulfinyl (Alkyl-S(=0)-)“, soweit nicht an anderer Stelle anders definiert steht erfindungsgemäß für Alkylreste, die über -S(=0)- an das Gerüst gebunden sind, wie (Ci-Cio)-, (CI-CÖ)- oder (Ci-C4)- Alkylsulfinyl, z. B. (aber nicht beschränkt auf) (Ci-C6)-Alkylsulfinyl wie Methylsulfinyl, Ethylsulfinyl, Propylsulfinyl, 1 -Methylethylsulfinyl, Butylsulfinyl, 1 -Methylpropylsulfinyl, 2-Methylpropylsulfinyl,"Alkylsulfinyl (alkyl-S (= 0) -)", unless otherwise defined elsewhere, according to the invention stands for alkyl radicals which are bonded to the structure via -S (= 0) -, such as (Ci-Cio) -, ( CI-C Ö ) - or (Ci-C 4 ) - alkylsulfinyl, e.g. B. (but not limited to) (Ci-C 6 ) alkylsulfinyl such as methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl,
1 , 1 -Dimethylethylsulfinyl, Pentylsulfinyl, 1 -Methylbutylsulfinyl, 2-Methylbutylsulfinyl, 3- Methylbutylsulfinyl, l,l-Dimethylpropylsulfinyl, 1 ,2-Dimethylpropylsulfinyl, 2,2-Di- methylpropylsulfinyl, 1 -Ethylpropylsulfinyl, Hexylsulfinyl, 1 -Methylpentylsulfinyl, 2-Methylpentyl- sulfinyl, 3 -Methylpentylsulfinyl, 4-Methylpentylsulfinyl, l,l-Dimethylbutylsulfinyl, 1 ,2-Dimethyl- butylsulfinyl, l,3-Dimethylbutylsulfinyl, 2,2-Dimethylbutylsulfinyl, 2,3-Dimethylbutylsulfinyl, 3,3- Dimethylbutylsulfinyl, 1 -Ethylbutylsulfinyl, 2-Ethylbutylsulfinyl, l,l,2-Trimethylpropylsulfinyl, 1,2,2- Trimethylpropylsulfinyl, 1 -Ethyl- 1 -methylpropylsulfinyl und 1 -Ethyl-2-methylpropylsulfinyl. 1, 1-dimethylethylsulfinyl, pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, l, l-dimethylpropylsulfinyl, 1, 2-dimethylpropylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, 1 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, l, l-dimethylbutylsulfinyl, 1, 2-dimethylbutylsulfinyl, l, 3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3- Dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, l, l, 2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl and 1-ethyl-2-methylpropylsulfinyl.
„Alkoxy“ bedeutet ein über ein Sauerstoffatom gebundenen Alkylrest, z. B. (aber nicht beschränkt auf) (Ci-C6)-Alkoxy wie Methoxy, Ethoxy, Propoxy, 1 -Methylethoxy, Butoxy, 1 -Methylpropoxy, 2- Methylpropoxy, l,l-Dimethylethoxy, Pentoxy, 1 -Methylbutoxy, 2-Methylbutoxy, 3-Methylbutoxy, 1,1- Dimethylpropoxy, 1 ,2-Dimethylpropoxy, 2,2-Dimethylpropoxy, 1 -Ethylpropoxy, Hexoxy, 1 - Methylpentoxy, 2-Methylpentoxy, 3-Methylpentoxy, 4-Methylpentoxy, l,l-Dimethylbutoxy, l,2-Di- methylbutoxy, l,3-Dimethylbutoxy, 2,2-Dimethylbutoxy, 2,3-Dimethylbutoxy, 3,3-Dimethylbutoxy, 1- Ethylbutoxy, 2-Ethylbutoxy, l,l,2-Trimethylpropoxy, 1 ,2,2-Trimethylpropoxy, 1 -Ethyl- 1 -methyl propoxy und 1 -Ethyl-2-methylpropoxy. Alkenyloxy bedeutet ein über ein Sauerstoffatom gebundenen Alkenylrest, Alkinyloxy bedeutet ein über ein Sauerstoffatom gebundenen Alkinylrest wie (C2-C10)-, (C2-C6)- oder (C2-C i)-Alkenoxy bzw. (C3-C10)-, (C3-C6)- oder (C3-C4)-Alkinoxy. „Alkylcarbonyl“ (Alkyl-C(=0)-), soweit nicht an anderer Stelle anders definiert, steht erfindungsgemäß für Alkylreste, die über -C(=0)- an das Gerüst gebunden sind, wie (Ci-Cio)-, (Ci-Cr,)- oder (C 1-C4)- Alkylcarbonyl. Die Anzahl der C-Atome bezieht sich dabei auf den Alkylrest in der “Alkoxy” means an alkyl radical bonded via an oxygen atom, eg. B. (but not limited to) (Ci-C 6 ) alkoxy such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, l, l-dimethylethoxy, pentoxy, 1-methylbutoxy, 2 -Methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1, 2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1 - methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, l, l -Dimethylbutoxy, l, 2-dimethylbutoxy, l, 3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, l, l, 2-trimethylpropoxy , 1, 2,2-trimethylpropoxy, 1-ethyl-1-methyl propoxy and 1-ethyl-2-methylpropoxy. Alkenyloxy means an alkenyl radical bonded via an oxygen atom, alkynyloxy means an alkynyl radical bonded via an oxygen atom, such as (C2-C10) -, (C2-C6) - or (C2-C i) -alkenoxy or (C3-C10) -, ( C3-C6) or (C3-C4) alkynoxy. "Alkylcarbonyl" (alkyl-C (= 0) -), unless otherwise defined elsewhere, stands according to the invention for alkyl radicals which are bonded to the structure via -C (= 0) -, such as (Ci-Cio) -, (Ci-Cr,) - or (C 1-C4) alkylcarbonyl. The number of carbon atoms refers to the alkyl radical in the
Alkylcarbonylgruppe. Alkylcarbonyl.
„Alkoxycarbonyl (Alkyl-0-C(=0)-)“, soweit nicht an anderer Stelle anders definiert: Alkylreste, die über -0-C(=0)- an das Gerüst gebunden sind, wie (C1-C10)-, (CI-CÖ)- oder (Ci-C4)-Alkoxycarbonyl. Die Anzahl der C-Atome bezieht sich dabei auf den Alkylrest in der Alkoxycarbonylgruppe. Analog stehen „Alkenyloxycarbonyl“ und„Alkinyloxycarbonyl“, soweit nicht an anderer Stelle anders definiert, erfindungsgemäß für Alkenyl- bzw. Alkinylreste, die über -0-C(=0)- an das Gerüst gebunden sind, wie (C2-C 10)-, (C2-C6)- oder (C2-C4)-Alkenyloxycarbonyl bzw. (C3-C 10)-, (C3-C6)- oder (C3-C4)- Alkinyloxycarbonyl. Die Anzahl der C-Atome bezieht sich dabei auf den Alkenyl- bzw. Alkinylrest in der Alken- bzw. Alkinyloxycarbonylgruppe. "Alkoxycarbonyl (alkyl-0-C (= 0) -)", unless otherwise defined elsewhere: alkyl residues which are bonded to the structure via -0-C (= 0) -, such as (C1-C10) - , (C I -C Ö ) - or (Ci-C4) alkoxycarbonyl. The number of carbon atoms relates to the alkyl radical in the alkoxycarbonyl group. Analogously, "alkenyloxycarbonyl" and "alkynyloxycarbonyl", unless otherwise defined elsewhere, according to the invention stand for alkenyl or alkynyl radicals which are bonded to the structure via -0-C (= 0) -, such as (C2-C 10) -, (C2-C6) - or (C2-C 4 ) alkenyloxycarbonyl or (C3-C 10) -, (C3-C6) - or (C3-C4) - alkynyloxycarbonyl. The number of carbon atoms relates to the alkenyl or alkynyl radical in the alkene or alkynyloxycarbonyl group.
Der Begriff„Aryl“ bedeutet ein gegebenenfalls substituiertes mono-, bi- oder polycyclisches aromatisches System mit vorzugsweise 6 bis 14, insbesondere 6 bis 10 Ring-C- Atomen, beispielsweise Phenyl, Naphthyl, Anthryl, Phenanthrenyl, und ähnliches, vorzugsweise Phenyl.  The term “aryl” means an optionally substituted mono-, bi- or polycyclic aromatic system with preferably 6 to 14, in particular 6 to 10 ring carbon atoms, for example phenyl, naphthyl, anthryl, phenanthrenyl, and the like, preferably phenyl.
Ein heterocyclischer Rest (Heterocyclyl) enthält mindestens einen heterocyclischen Ring A heterocyclic radical (heterocyclyl) contains at least one heterocyclic ring
(=carbocyclischer Ring, in dem mindestens ein C-Atom durch ein Heteroatom ersetzt ist, vorzugsweise durch ein Heteroatom aus der Gruppe N, O, S, P) der gesättigtoder teilgesättigt ist und dabei unsubstituiert oder substituiert sein kann, wobei die Bindungsstelle an einem Ringatom lokalisiert ist. lst der Heterocyclylrest oder der heterocyclische Ring gegebenenfalls substituiert, kann er mit anderen carbocyclischen oder heterocyclischen Ringen annelliert sein lm Falle von gegebenenfalls (= carbocyclic ring in which at least one C atom is replaced by a hetero atom, preferably by a hetero atom from the group N, O, S, P) which is saturated or partially saturated and can be unsubstituted or substituted, the binding site at one Ring atom is localized. If the heterocyclyl radical or the heterocyclic ring is optionally substituted, it can be fused with other carbocyclic or heterocyclic rings in the case of optionally
substituiertem Heterocyclyl werden auch mehrcyclische Systeme umfasst, wie beispielsweise 8-Aza- bicyclo[3.2.l]octanyl, 8-Aza-bicyclo[2.2.2]octanyl oder l-Aza-bicyclo[2.2.l]heptyl. lm Falle von gegebenenfalls substituiertem Heterocyclyl werden auch spirocyclische Systeme umfasst, wie beispielsweise l-Oxa-5-aza-spiro[2.3]hexyl. Wenn nicht anders definiert, enthält der heterocyclische Ring vorzugsweise 3 bis 9 Ringatome, insbesondere 3 bis 6 Ringatome, und ein oder mehrere, vorzugsweise 1 bis 4, insbesondere 1 , 2 oder 3 Heteroatome im heterocyclischen Ring, vorzugsweise aus der Gruppe N, O, und S, wobei jedoch nicht zwei Sauerstoffatome direkt benachbart sein sollen, wie beispielsweise mit einem Heteroatom aus der Gruppe N, O und S 1- oder 2- oder 3-Pyrrolidinyl, 3,4- Dihydro-2H-pyrrol-2- oder 3-yl, 2,3-Dihydro-lH-pyrrol-l- oder 2- oder 3- oder 4- oder 5-yl; 2,5- Dihydro-lH-pyrrol-l- oder 2- oder 3-yl, 1- oder 2- oder 3- oder 4-Piperidinyl; 2, 3,4,5- Tetrahydropyridin-2- oder 3- oder 4- oder 5-yl oder 6-yl; l,2,3,6-Tetrahydropyridin-l- oder 2- oder 3- oder 4- oder 5- oder 6-yl; l,2,3,4-Tetrahydropyridin-l- oder 2- oder 3- oder 4- oder 5- oder 6-yl; 1,4- Dihydropyridin-l- oder 2- oder 3- oder 4-yl; 2,3-Dihydropyridin-2- oder 3- oder 4- oder 5- oder 6-yl; 2.5-Dihydropyridin-2- oder 3- oder 4- oder 5- oder 6-yl, 1- oder 2- oder 3- oder 4-Azepanyl; 2, 3, 4, 5- Tetrahydro-lH-azepin-l- oder 2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,4,7-Tetrahydro-lH- azepin-l- oder 2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,6,7-Tetrahydro-lH-azepin-l- oder 2- oder 3- oder 4-yl; 3,4,5,6-Tetrahydro-2H-azepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 4,5- Dihydro-lH-azepin-l- oder 2- oder 3- oder 4-yl; 2,5-Dihydro-lH-azepin-l- oder -2- oder 3- oder 4- oderSubstituted heterocyclyl also includes multi-cyclic systems, such as, for example, 8-azabicyclo [3.2.l] octanyl, 8-azabicyclo [2.2.2] octanyl or 1-azabicyclo [2.2.l] heptyl. In the case of optionally substituted heterocyclyl, spirocyclic systems are also included, such as, for example, l-oxa-5-aza-spiro [2.3] hexyl. Unless otherwise defined, the heterocyclic ring preferably contains 3 to 9 ring atoms, in particular 3 to 6 ring atoms, and one or more, preferably 1 to 4, in particular 1, 2 or 3, heteroatoms in the heterocyclic ring, preferably from the group N, O, and S, but two oxygen atoms should not be directly adjacent, such as with a hetero atom from the group N, O and S 1- or 2- or 3-pyrrolidinyl, 3,4-dihydro-2H-pyrrole-2- or 3 -yl, 2,3-dihydro-lH-pyrrole-l- or 2- or 3- or 4- or 5-yl; 2,5-dihydro-1H-pyrrole-1- or 2- or 3-yl, 1- or 2- or 3- or 4-piperidinyl; 2, 3,4,5-tetrahydropyridin-2- or 3- or 4- or 5-yl or 6-yl; l, 2,3,6-tetrahydropyridin-l- or 2- or 3- or 4- or 5- or 6-yl; l, 2,3,4-tetrahydropyridin-l- or 2- or 3- or 4- or 5- or 6-yl; 1,4-dihydropyridin-l- or 2- or 3- or 4-yl; 2,3-dihydropyridin-2- or 3- or 4- or 5- or 6-yl; 2,5-dihydropyridin-2- or 3- or 4- or 5- or 6-yl, 1- or 2- or 3- or 4-azepanyl; 2, 3, 4, 5-tetrahydro-lH-azepine-1- or 2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7-tetrahydro-lH-azepin-l- or 2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,6,7-tetrahydro-lH-azepin-l- or 2- or 3- or 4-yl; 3,4,5,6-tetrahydro-2H-azepin-2- or 3- or 4- or 5- or 6- or 7-yl; 4,5-dihydro-lH-azepine-1- or 2- or 3- or 4-yl; 2,5-dihydro-lH-azepine-l- or -2- or 3- or 4- or
5- oder 6- oder 7-yl; 2,7-Dihydro-lH-azepin-l- oder -2- oder 3- oder 4-yl; 2,3-Dihydro-lH-azepin-l- oder -2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 3,4-Dihydro-2H-azepin-2- oder 3- oder 4- oder 5- oder5- or 6- or 7-yl; 2,7-dihydro-lH-azepine-l- or -2- or 3- or 4-yl; 2,3-dihydro-lH-azepine-l- or -2- or 3- or 4- or 5- or 6- or 7-yl; 3,4-dihydro-2H-azepine-2- or 3- or 4- or 5- or
6- oder 7-yl; 3,6-Dihydro-2H-azepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 5,6-Dihydro-2H- azepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 4,5-Dihydro-3H-azepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; lH-Azepin-l- oder -2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2H-Azepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 3H-Azepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 4H-Azepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl, 2- oder 3-Oxolanyl (= 2- oder 3-Tetrahydrofuranyl); 2,3- Dihydrofuran-2- oder 3- oder 4- oder 5-yl; 2,5-Dihydrofuran-2- oder 3-yl, 2- oder 3- oder 4-Oxanyl (=6- or 7-yl; 3,6-dihydro-2H-azepin-2- or 3- or 4- or 5- or 6- or 7-yl; 5,6-dihydro-2H-azepin-2- or 3- or 4- or 5- or 6- or 7-yl; 4,5-dihydro-3H-azepin-2- or 3- or 4- or 5- or 6- or 7-yl; 1H-azepine-1- or -2- or 3- or 4- or 5- or 6- or 7-yl; 2H-azepin-2- or 3- or 4- or 5- or 6- or 7-yl; 3H-azepin-2- or 3- or 4- or 5- or 6- or 7-yl; 4H-azepin-2- or 3- or 4- or 5- or 6- or 7-yl, 2- or 3-oxolanyl (= 2- or 3-tetrahydrofuranyl); 2,3-dihydrofuran-2- or 3- or 4- or 5-yl; 2,5-dihydrofuran-2- or 3-yl, 2- or 3- or 4-oxanyl (=
2- oder 3- oder 4-Tetrahydropyranyl); 3,4-Dihydro-2H-pyran-2- oder 3- oder 4- oder 5- oder 6-yl; 3,6- Dihydro-2H-pyran-2- oder 3-oder 4- oder 5- oder 6-yl; 2H-Pyran-2- oder 3- oder 4- oder 5- oder 6-yl; 4H-Pyran-2- oder 3- oder 4-yl, 2- oder 3- oder 4-Oxepanyl; 2,3,4,5-Tetrahydrooxepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,4,7-Tetrahydrooxepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2, 3,6,7- Tetrahydrooxepin-2- oder 3- oder 4-yl; 2,3-Dihydrooxepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl;2- or 3- or 4-tetrahydropyranyl); 3,4-dihydro-2H-pyran-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-pyran-2- or 3- or 4- or 5- or 6-yl; 2H-pyran-2- or 3- or 4- or 5- or 6-yl; 4H-pyran-2- or 3- or 4-yl, 2- or 3- or 4-oxepanyl; 2,3,4,5-tetrahydrooxepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7-tetrahydrooxepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2, 3,6,7-tetrahydrooxepin-2- or 3- or 4-yl; 2,3-dihydrooxepin-2- or 3- or 4- or 5- or 6- or 7-yl;
4.5-Dihydrooxepin-2- oder 3- oder 4-yl; 2,5-Dihydrooxepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; Oxepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2- oder 3-Tetrahydrothiophenyl; 2,3- Dihydrothiophen-2- oder 3- oder 4- oder 5-yl; 2,5-Dihydrothiophen-2- oder 3-yl; Tetrahydro-2H- thiopyran-2- oder 3- oder 4-yl; 3,4-Dihydro-2H-thiopyran-2- oder 3- oder 4- oder 5- oder 6-yl; 3,6- Dihydro-2H-thiopyran-2- oder 3- oder 4- oder 5- oder 6-yl; 2H-Thiopyran-2- oder 3- oder 4- oder 5- oder 6-yl; 4H-Thiopyran-2- oder 3- oder 4-yl. Bevorzugte 3-Ring und 4-Ring-Heterocyclen sind beispielsweise 1- oder 2-Aziridinyl, Oxiranyl, Thiiranyl, 1- oder 2- oder 3-Azetidinyl, 2- oder 3- Oxetanyl, 2- oder 3-Thietanyl, l,3-Dioxetan-2-yl. Weitere Beispiele für“Heterocyclyl“ sind ein partiell oder vollständig hydrierter heterocyclischer Rest mit zwei Heteroatomen aus der Gruppe N, O und S, wie beispielsweise 1- oder 2- oder 3- oder 4-Pyrazolidinyl; 4,5-Dihydro-3H-pyrazol- 3- oder 4- oder 5- yl; 4,5-Dihydro-lH-pyrazol-l- oder 3- oder 4- oder 5-yl; 2,3-Dihydro-lH-pyrazol-l- oder 2- oder 3- oder 4- oder 5-yl; 1- oder 2- oder 3- oder 4- Imidazolidinyl; 2,3-Dihydro-lH-imidazol-l- oder 2- oder 3- oder 4-yl; 2,5-Dihydro-lH-imidazol-l- oder 2- oder 4- oder 5-yl; 4,5-Dihydro-lH-imidazol-l- oder 2- oder 4- oder 5-yl; Hexahydropyridazin-l- oder 2- oder 3- oder 4-yl; l,2,3,4-Tetrahydropyridazin-l- oder 2- oder 3- oder 4- oder 5- oder 6-yl; l,2,3,6-Tetrahydropyridazin-l- oder 2- oder 3- oder 4- oder 5- oder 6-yl; l,4,5,6-Tetrahydropyridazin-l- oder 3- oder 4- oder 5- oder 6-yl; 3,4,5,6-Tetrahydropyridazin-3- oder 4- oder 5-yl; 4,5-Dihydropyridazin-3- oder 4-yl; 3,4-Dihydropyridazin-3- oder 4- oder 5- oder 6-yl;4,5-dihydrooxepin-2- or 3- or 4-yl; 2,5-dihydrooxepin-2- or 3- or 4- or 5- or 6- or 7-yl; Oxepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2- or 3-tetrahydrothiophenyl; 2,3-dihydrothiophene-2- or 3- or 4- or 5-yl; 2,5-dihydrothiophene-2- or 3-yl; Tetrahydro-2H-thiopyran-2- or 3- or 4-yl; 3,4-dihydro-2H-thiopyran-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-thiopyran-2- or 3- or 4- or 5- or 6-yl; 2H-thiopyran-2- or 3- or 4- or 5- or 6-yl; 4H-thiopyran-2- or 3- or 4-yl. Preferred 3-ring and 4-ring heterocycles are, for example, 1- or 2-aziridinyl, oxiranyl, thiiranyl, 1- or 2- or 3-azetidinyl, 2- or 3-oxetanyl, 2- or 3-thietanyl, 1,3 -Dioxetan-2-yl. Further examples of “heterocyclyl” are a partially or fully hydrogenated heterocyclic radical with two heteroatoms from the group N, O and S, such as 1- or 2- or 3- or 4-pyrazolidinyl; 4,5-dihydro-3H-pyrazole-3- or 4- or 5-yl; 4,5-dihydro-1H-pyrazole-l- or 3- or 4- or 5-yl; 2,3-dihydro-1H-pyrazole-1- or 2- or 3- or 4- or 5-yl; 1- or 2- or 3- or 4-imidazolidinyl; 2,3-dihydro-1H-imidazole-1- or 2- or 3- or 4-yl; 2,5-dihydro-1H-imidazole-1- or 2- or 4- or 5-yl; 4,5-dihydro-1H-imidazole-1- or 2- or 4- or 5-yl; Hexahydropyridazin-l- or 2- or 3- or 4-yl; l, 2,3,4-tetrahydropyridazin-l- or 2- or 3- or 4- or 5- or 6-yl; l, 2,3,6-tetrahydropyridazin-l- or 2- or 3- or 4- or 5- or 6-yl; l, 4,5,6-tetrahydropyridazin-l- or 3- or 4- or 5- or 6-yl; 3,4,5,6-tetrahydropyridazin-3- or 4- or 5-yl; 4,5-dihydropyridazin-3- or 4-yl; 3,4-dihydropyridazin-3- or 4- or 5- or 6-yl;
3.6-Dihydropyridazin-3- oder 4-yl; l,6-Dihydropyriazin-l- oder 3- oder 4- oder 5- oder 6-yl; 3,6-dihydropyridazin-3- or 4-yl; l, 6-dihydropyriazin-l- or 3- or 4- or 5- or 6-yl;
Hexahydropyrimidin-l- oder 2- oder 3- oder 4-yl; l,4,5,6-Tetrahydropyrimidin-l- oder 2- oder 4- oder 5- oder 6-yl; l,2,5,6-Tetrahydropyrimidin-l- oder 2- oder 4- oder 5- oder 6-yl; 1 ,2,3,4- Tetrahydropyrimidin-l- oder 2- oder 3- oder 4- oder 5- oder 6-yl; l,6-Dihydropyrimidin-l- oder 2- oder 4- oder 5- oder 6-yl; l,2-Dihydropyrimidin-l- oder 2- oder 4- oder 5- oder 6-yl; 2,5-Dihydropyrimidin-Hexahydropyrimidin-l- or 2- or 3- or 4-yl; l, 4,5,6-tetrahydropyrimidine-l- or 2- or 4- or 5- or 6-yl; l, 2,5,6-tetrahydropyrimidin-l- or 2- or 4- or 5- or 6-yl; 1, 2,3,4-tetrahydropyrimidin-l- or 2- or 3- or 4- or 5- or 6-yl; l, 6-dihydropyrimidin-l- or 2- or 4- or 5- or 6-yl; l, 2-dihydropyrimidin-l- or 2- or 4- or 5- or 6-yl; 2,5-dihydropyrimidine
2- oder 4- oder 5-yl; 4,5-Dihydropyrimidin- 4- oder 5- oder 6-yl; l,4-Dihydropyrimidin-l- oder 2- oder 4- oder 5- oder 6-yl; 1- oder 2- oder 3-Piperazinyl; l,2,3,6-Tetrahydropyrazin-l- oder 2- oder 3- oder 5- oder 6-yl; l,2,3,4-Tetrahydropyrazin-l- oder 2- oder 3- oder 4- oder 5- oder 6-yl; l,2-Dihydropyrazin-l- oder 2- oder 3- oder 5- oder 6-yl; l,4-Dihydropyrazin-l- oder 2- oder 3-yl; 2,3-Dihydropyrazin-2- oder2- or 4- or 5-yl; 4,5-dihydropyrimidin-4- or 5- or 6-yl; l, 4-dihydropyrimidin-l- or 2- or 4- or 5- or 6-yl; 1- or 2- or 3-piperazinyl; l, 2,3,6-tetrahydropyrazine-1- or 2- or 3- or 5- or 6-yl; l, 2,3,4-tetrahydropyrazine-1- or 2- or 3- or 4- or 5- or 6-yl; l, 2-dihydropyrazine-1- or 2- or 3- or 5- or 6-yl; l, 4-dihydropyrazine-1- or 2- or 3-yl; 2,3-dihydropyrazine-2- or
3- oder 5- oder 6-yl; 2,5-Dihydropyrazin-2- oder 3-yl; l,3-Dioxolan-2- oder 4- oder 5-yl; l,3-Dioxol-2- oder 4-yl; l,3-Dioxan-2- oder 4- oder 5-yl; 4H-l,3-Dioxin-2- oder 4- oder 5- oder 6-yl; l,4-Dioxan-2- oder 3- oder 5- oder 6-yl; 2,3-Dihydro-l,4-dioxin-2- oder 3- oder 5- oder 6-yl; l,4-Dioxin-2- oder 3-yl;3- or 5- or 6-yl; 2,5-dihydropyrazin-2- or 3-yl; l, 3-dioxolan-2- or 4- or 5-yl; l, 3-dioxol-2- or 4-yl; l, 3-dioxan-2- or 4- or 5-yl; 4H-l, 3-dioxin-2- or 4- or 5- or 6-yl; l, 4-dioxan-2- or 3- or 5- or 6-yl; 2,3-dihydro-l, 4-dioxin-2- or 3- or 5- or 6-yl; 1,4-dioxin-2- or 3-yl;
1.2-Dithiolan-3- oder 4-yl; 3H-l,2-Dithiol-3- oder 4- oder 5-yl; l,3-Dithiolan-2- oder 4-yl; l,3-Dithiol- 2- oder 4-yl; l,2-Dithian-3- oder 4-yl; 3,4-Dihydro-l,2-dithiin-3- oder 4- oder 5- oder 6-yl; 3,6-Dihydro-1,2-dithiolan-3- or 4-yl; 3H-l, 2-dithiol-3- or 4- or 5-yl; l, 3-dithiolan-2- or 4-yl; l, 3-dithiol-2- or 4-yl; 1,2-dithian-3- or 4-yl; 3,4-dihydro-l, 2-dithiin-3- or 4- or 5- or 6-yl; 3,6-dihydro-
1.2-dithiin-3- oder 4-yl; l,2-Dithiin-3- oder 4-yl; l,3-Dithian-2- oder 4- oder 5-yl; 4H-l,3-Dithiin-2- oder 4- oder 5- oder 6-yl; Isoxazolidin-2- oder 3- oder 4- oder 5-yl; 2,3-Dihydroisoxazol-2- oder 3- oder1,2-dithiin-3- or 4-yl; 1,2-dithiin-3- or 4-yl; l, 3-dithian-2- or 4- or 5-yl; 4H-l, 3-dithiin-2- or 4- or 5- or 6-yl; Isoxazolidin-2- or 3- or 4- or 5-yl; 2,3-dihydroisoxazole-2- or 3- or
4- oder 5-yl; 2,5-Dihydroisoxazol-2- oder 3- oder 4- oder 5-yl; 4,5-Dihydroisoxazol-3- oder 4- oder 5-yl;4- or 5-yl; 2,5-dihydroisoxazol-2- or 3- or 4- or 5-yl; 4,5-dihydroisoxazol-3- or 4- or 5-yl;
1.3-Oxazolidin-2- oder 3- oder 4- oder 5-yl; 2,3-Dihydro-l,3-oxazol-2- oder 3- oder 4- oder 5-yl; 2,5- Dihydro-l,3-oxazol-2- oder 4- oder 5-yl; 4,5-Dihydro-l,3-oxazol-2- oder 4- oder 5-yl; l,2-Oxazinan-2- oder 3- oder 4- oder 5- oder 6-yl; 3,4-Dihydro-2H-l,2-oxazin-2- oder 3- oder 4- oder 5- oder 6-yl; 3,6- Dihydro-2H-l,2-oxazin-2- oder 3- oder 4- oder 5- oder 6-yl; 5,6-Dihydro-2H-l,2-oxazin-2- oder 3- oder 4- oder 5- oder 6-yl; 5,6-Dihydro-4H-l,2-oxazin-3- oder 4- oder 5- oder 6-yl; 2H-l,2-Oxazin-2- oder 3- oder 4- oder 5- oder 6-yl; 6H-l,2-Oxazin-3- oder 4- oder 5- oder 6-yl; 4H-l,2-Oxazin-3- oder 4- oder 5- oder 6-yl; l,3-Oxazinan-2- oder 3- oder 4- oder 5- oder 6-yl; 3,4-Dihydro-2H-l,3-oxazin-2- oder 3- oder 4- oder 5- oder 6-yl; 3,6-Dihydro-2H-l,3-oxazin-2- oder 3- oder 4- oder 5- oder 6-yl; 5,6-Dihydro-2H-1,3-oxazolidin-2- or 3- or 4- or 5-yl; 2,3-dihydro-l, 3-oxazol-2- or 3- or 4- or 5-yl; 2,5-dihydro-l, 3-oxazol-2- or 4- or 5-yl; 4,5-dihydro-l, 3-oxazol-2- or 4- or 5-yl; l, 2-oxazinan-2- or 3- or 4- or 5- or 6-yl; 3,4-dihydro-2H-l, 2-oxazin-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-l, 2-oxazin-2- or 3- or 4- or 5- or 6-yl; 5,6-dihydro-2H-l, 2-oxazin-2- or 3- or 4- or 5- or 6-yl; 5,6-dihydro-4H-l, 2-oxazin-3- or 4- or 5- or 6-yl; 2H-l, 2-oxazin-2- or 3- or 4- or 5- or 6-yl; 6H-l, 2-oxazin-3- or 4- or 5- or 6-yl; 4H-l, 2-oxazin-3- or 4- or 5- or 6-yl; l, 3-oxazinan-2- or 3- or 4- or 5- or 6-yl; 3,4-dihydro-2H-l, 3-oxazin-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-l, 3-oxazin-2- or 3- or 4- or 5- or 6-yl; 5,6-dihydro-2H
1.3-oxazin-2- oder 4- oder 5- oder 6-yl; 5,6-Dihydro-4H-l,3-oxazin-2- oder 4- oder 5- oder 6-yl; 2H-1,3-oxazin-2- or 4- or 5- or 6-yl; 5,6-dihydro-4H-l, 3-oxazin-2- or 4- or 5- or 6-yl; 2H
1.3-Oxazin-2- oder 4- oder 5- oder 6-yl; 6H-l,3-Oxazin-2- oder 4- oder 5- oder 6-yl; 4H-l,3-Oxazin-2- oder 4- oder 5- oder 6-yl; Morpholin-2- oder 3- oder 4-yl; 3,4-Dihydro-2H-l,4-oxazin-2- oder 3- oder 4- oder 5- oder 6-yl; 3,6-Dihydro-2H-l,4-oxazin-2- oder 3- oder 5- oder 6-yl; 2H-l,4-oxazin-2- oder 3- oder 5- oder 6-yl; 4H-l,4-oxazin-2- oder 3-yl; 1 ,2-Oxazepan-2- oder 3- oder 4- oder 5- oder 6- oder 7- yl; 2,3,4,5-Tetrahydro-l,2-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,4,7-Tetrahydro-l,2- oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,6,7-Tetrahydro-l,2-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,5,6,7-Tetrahydro-l,2-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7- yl; 4,5,6,7-Tetrahydro-l,2-oxazepin-3- oder 4- oder 5- oder 6- oder 7-yl; 2,3-Dihydro-l,2-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,5-Dihydro-l,2-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,7-Dihydro-l,2-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 4,5-Dihydro-l,2- oxazepin-3- oder 4- oder 5- oder 6- oder 7-yl; 4,7-Dihydro-l,2-oxazepin-3- oder 4- oder 5- oder 6- oder 7-yl; 6,7-Dihydro-l,2-oxazepin-3- oder 4- oder 5- oder 6- oder 7-yl; l,2-Oxazepin-3- oder 4- oder 5- oder 6- oder 7-yl; l,3-Oxazepan-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,4,5-Tetrahydro-l,3- oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,4,7-Tetrahydro-l,3-oxazepin-2- oder 3- oder1,3-oxazin-2- or 4- or 5- or 6-yl; 6H-l, 3-oxazin-2- or 4- or 5- or 6-yl; 4H-l, 3-oxazin-2- or 4- or 5- or 6-yl; Morpholin-2- or 3- or 4-yl; 3,4-dihydro-2H-l, 4-oxazin-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-l, 4-oxazin-2- or 3- or 5- or 6-yl; 2H-l, 4-oxazin-2- or 3- or 5- or 6-yl; 4H-l, 4-oxazin-2- or 3-yl; 1, 2-oxazepan-2- or 3- or 4- or 5- or 6- or 7- yl; 2,3,4,5-tetrahydro-l, 2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7-tetrahydro-l, 2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,6,7-tetrahydro-l, 2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,5,6,7-tetrahydro-l, 2-oxazepine-2- or 3- or 4- or 5- or 6- or 7- yl; 4,5,6,7-tetrahydro-l, 2-oxazepin-3- or 4- or 5- or 6- or 7-yl; 2,3-dihydro-l, 2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,5-dihydro-l, 2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,7-dihydro-l, 2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 4,5-dihydro-l, 2-oxazepin-3- or 4- or 5- or 6- or 7-yl; 4,7-dihydro-l, 2-oxazepin-3- or 4- or 5- or 6- or 7-yl; 6,7-dihydro-l, 2-oxazepin-3- or 4- or 5- or 6- or 7-yl; l, 2-oxazepin-3- or 4- or 5- or 6- or 7-yl; l, 3-oxazepan-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,5-tetrahydro-l, 3- oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7-tetrahydro-l, 3-oxazepine-2- or 3- or
4- oder 5- oder 6- oder 7-yl; 2,3,6,7-Tetrahydro-l,3-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7- yl; 2,5,6,7-Tetrahydro-l,3-oxazepin-2- oder 4- oder 5- oder 6- oder 7-yl; 4,5,6,7-Tetrahydro-l,3- oxazepin-2- oder 4- oder 5- oder 6- oder 7-yl; 2,3-Dihydro-l,3-oxazepin-2- oder 3- oder 4- oder 5- oder4- or 5- or 6- or 7-yl; 2,3,6,7-tetrahydro-l, 3-oxazepine-2- or 3- or 4- or 5- or 6- or 7- yl; 2,5,6,7-tetrahydro-l, 3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 4,5,6,7-tetrahydro-l, 3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 2,3-dihydro-l, 3-oxazepine-2- or 3- or 4- or 5- or
6- oder 7-yl; 2,5-Dihydro-l,3-oxazepin-2- oder 4- oder 5- oder 6- oder 7-yl; 2,7-Dihydro-l,3-oxazepin- 2- oder 4- oder 5- oder 6- oder 7-yl; 4,5-Dihydro-l,3-oxazepin-2- oder 4- oder 5- oder 6- oder 7-yl; 4,7- Dihydro-l,3-oxazepin-2- oder 4- oder 5- oder 6- oder 7-yl; 6,7-Dihydro-l,3-oxazepin-2- oder 4- oder 5- oder 6- oder 7-yl; l,3-Oxazepin-2- oder 4- oder 5- oder 6- oder 7-yl; 1 ,4-Oxazepan-2- oder 3- oder 5- oder 6- oder 7-yl; 2,3,4,5-Tetrahydro-l,4-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2, 3,4,7- Tetrahydro-l,4-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,6,7-Tetrahydro-l,4-oxazepin-6- or 7-yl; 2,5-dihydro-l, 3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 2,7-dihydro-l, 3-oxazepine 2- or 4- or 5- or 6- or 7-yl; 4,5-dihydro-l, 3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 4,7-dihydro-l, 3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 6,7-dihydro-l, 3-oxazepin-2- or 4- or 5- or 6- or 7-yl; l, 3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 1, 4-oxazepan-2- or 3- or 5- or 6- or 7-yl; 2,3,4,5-tetrahydro-l, 4-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2, 3,4,7-tetrahydro-l, 4-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,6,7-tetrahydro-l, 4-oxazepin
2- oder 3- oder 5- oder 6- oder 7-yl; 2,5,6,7-Tetrahydro-l,4-oxazepin-2- oder 3- oder 5- oder 6- oder 7- yl; 4,5,6,7-Tetrahydro-l,4-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3-Dihydro-l,4- oxazepin-2- oder 3- oder 5- oder 6- oder 7-yl; 2,5-Dihydro-l,4-oxazepin-2- oder 3- oder 5- oder 6- oder2- or 3- or 5- or 6- or 7-yl; 2,5,6,7-tetrahydro-l, 4-oxazepine-2- or 3- or 5- or 6- or 7- yl; 4,5,6,7-tetrahydro-l, 4-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3-dihydro-l, 4-oxazepin-2- or 3- or 5- or 6- or 7-yl; 2,5-dihydro-l, 4-oxazepine-2- or 3- or 5- or 6- or
7-yl; 2,7-Dihydro-l,4-oxazepin-2- oder 3- oder 5- oder 6- oder 7-yl; 4,5-Dihydro-l,4-oxazepin-2- oder7-yl; 2,7-dihydro-l, 4-oxazepin-2- or 3- or 5- or 6- or 7-yl; 4,5-dihydro-l, 4-oxazepine-2- or
3- oder 4- oder 5- oder 6- oder 7-yl; 4,7-Dihydro-l,4-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7- yl; 6,7-Dihydro-l,4-oxazepin-2- oder 3- oder 5- oder 6- oder 7-yl; 1 ,4-Oxazepin-2- oder 3- oder 5- oder 6- oder 7-yl; Isothiazolidin-2- oder 3- oder 4- oder 5-yl; 2,3-Dihydroisothiazol-2- oder 3- oder 4- oder 5- yl; 2,5-Dihydroisothiazol-2- oder 3- oder 4- oder 5-yl; 4,5-Dihydroisothiazol-3- oder 4- oder 5-yl; 1,3- Thiazolidin-2- oder 3- oder 4- oder 5-yl; 2,3-Dihydro-l,3-thiazol-2- oder 3- oder 4- oder 5-yl; 2,5- Dihydro-l,3-thiazol-2- oder 4- oder 5-yl; 4,5-Dihydro-l,3-thiazol-2- oder 4- oder 5-yl; l,3-Thiazinan-2- oder 3- oder 4- oder 5- oder 6-yl; 3,4-Dihydro-2H-l,3-thiazin-2- oder 3- oder 4- oder 5- oder 6-yl; 3,6- Dihydro-2H-l,3-thiazin-2- oder 3- oder 4- oder 5- oder 6-yl; 5,6-Dihydro-2H-l,3-thiazin-2- oder 4- oder3- or 4- or 5- or 6- or 7-yl; 4,7-dihydro-l, 4-oxazepine-2- or 3- or 4- or 5- or 6- or 7- yl; 6,7-dihydro-l, 4-oxazepin-2- or 3- or 5- or 6- or 7-yl; 1, 4-oxazepin-2- or 3- or 5- or 6- or 7-yl; Isothiazolidin-2- or 3- or 4- or 5-yl; 2,3-dihydroisothiazol-2- or 3- or 4- or 5-yl; 2,5-dihydroisothiazol-2- or 3- or 4- or 5-yl; 4,5-dihydroisothiazol-3- or 4- or 5-yl; 1,3-thiazolidin-2- or 3- or 4- or 5-yl; 2,3-dihydro-l, 3-thiazol-2- or 3- or 4- or 5-yl; 2,5-dihydro-l, 3-thiazol-2- or 4- or 5-yl; 4,5-dihydro-l, 3-thiazol-2- or 4- or 5-yl; l, 3-thiazinan-2- or 3- or 4- or 5- or 6-yl; 3,4-dihydro-2H-l, 3-thiazin-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-l, 3-thiazin-2- or 3- or 4- or 5- or 6-yl; 5,6-dihydro-2H-l, 3-thiazine-2- or 4- or
5- oder 6-yl; 5,6-Dihydro-4H-l,3-thiazin-2- oder 4- oder 5- oder 6-yl; 2H-l,3-Thiazin-2- oder 4- oder 5- oder 6-yl; 6H-l,3-Thiazin-2- oder 4- oder 5- oder 6-yl; 4H-l,3-Thiazin-2- oder 4- oder 5- oder 6-yl. Weitere Beispiele für“Heterocyclyl“ sind ein partiell oder vollständig hydrierter heterocyclischer Rest mit 3 Heteroatomen aus der Gruppe N, O und S, wie beispielsweise l,4,2-Dioxazolidin-2- oder 3- oder 5-yl; l,4,2-Dioxazol-3- oder 5-yl; 1 ,4,2-Dioxazinan-2- oder -3- oder 5- oder 6-yl; 5,6-Dihydro-l,4,2- dioxazin-3- oder 5- oder 6-yl; l,4,2-Dioxazin-3- oder 5- oder 6-yl; l,4,2-Dioxazepan-2- oder 3- oder 5- oder 6- oder 7-yl; 6,7-Dihydro-5H-l,4,2-Dioxazepin-3- oder 5- oder 6- oder 7-yl; 2,3-Dihydro-7H-l,4,2- Dioxazepin-2- oder 3- oder 5- oder 6- oder 7-yl; 2,3-Dihydro-5H-l,4,2-Dioxazepin-2- oder 3- oder 5- oder 6- oder 7-yl; 5H-l,4,2-Dioxazepin-3- oder 5- oder 6- oder 7-yl; 7H-l,4,2-Dioxazepin-3- oder 5- oder 6- oder 7-yl. Strukturbeispiele für gegebenenfalls weiter substituierte Heterocyclen sind auch im Folgenden aufgeführt: 5- or 6-yl; 5,6-dihydro-4H-l, 3-thiazin-2- or 4- or 5- or 6-yl; 2H-l, 3-thiazin-2- or 4- or 5- or 6-yl; 6H-l, 3-thiazin-2- or 4- or 5- or 6-yl; 4H-l, 3-thiazin-2- or 4- or 5- or 6-yl. Further examples of “heterocyclyl” are a partially or fully hydrogenated heterocyclic radical with 3 heteroatoms from the group N, O and S, such as l, 4,2-dioxazolidin-2- or 3- or 5-yl; l, 4,2-dioxazol-3- or 5-yl; 1, 4,2-dioxazinan-2- or -3- or 5- or 6-yl; 5,6-dihydro-l, 4,2-dioxazin-3- or 5- or 6-yl; l, 4,2-dioxazin-3- or 5- or 6-yl; l, 4,2-dioxazepan-2- or 3- or 5- or 6- or 7-yl; 6,7-dihydro-5H-l, 4,2-dioxazepin-3- or 5- or 6- or 7-yl; 2,3-dihydro-7H-l, 4,2-dioxazepin-2- or 3- or 5- or 6- or 7-yl; 2,3-dihydro-5H-l, 4,2-dioxazepin-2- or 3- or 5- or 6- or 7-yl; 5H-l, 4,2-dioxazepin-3- or 5- or 6- or 7-yl; 7H-l, 4,2-dioxazepin-3- or 5- or 6- or 7-yl. Structural examples of optionally further substituted heterocycles are also listed below:
 
Wenn ein Grundkörper "durch einen oder mehrere Reste" aus einer Aufzählung von Resten (= Gruppe) oder einer generisch definierten Gruppe von Resten substituiert ist, so schließt dies jeweils die gleichzeitige Substitution durch mehrere gleiche und/oder strukturell unterschiedliche Reste ein. If a basic body is substituted “by one or more residues” from an enumeration of residues (= group) or a generically defined group of residues, this includes the simultaneous substitution by several identical and / or structurally different residues.
Handelt es sich es sich um einen teilweise oder vollständig gesättigten Stickstoff-Heterocyclus, so kann dieser sowohl über Kohlenstoff als auch über den Stickstoff mit dem Rest des Moleküls verknüpft sein. If the nitrogen heterocycle is partially or fully saturated, this can be linked to the rest of the molecule via carbon as well as nitrogen.
Als Substituenten für einen substituierten heterocyclischen Rest kommen die weiter unten genannten Substituenten in Frage, zusätzlich auch Oxo und Thioxo. Die Oxogruppe als Substituent an einem Ring- C-Atom bedeutet dann beispielsweise eine Carbonylgruppe im heterocyclischen Ring. Dadurch sind vorzugsweise auch Lactone und Lactame umfasst. Die Oxogruppe kann auch an den Heteroringatomen, die in verschiedenen Oxidationsstufen existieren können, z.B. bei N und S, auftreten und bilden dann beispielsweise die divalenten Gruppen N(O) , S(O) (auch kurz SO) und S(0)2 (auch kurz SO2) im heterocyclischen Ring. Im Fall von -N(O)- und -S(0)-Gruppen sind jeweils beide Enantiomere umfasst. Possible substituents for a substituted heterocyclic radical are the substituents mentioned below, and also oxo and thioxo. The oxo group as a substituent on a ring carbon atom then means, for example, a carbonyl group in the heterocyclic ring. This preferably also includes lactones and lactams. The oxo group can also occur on the hetero ring atoms, which can exist in different oxidation states, for example in the case of N and S, and then form, for example, the divalent groups N (O), S (O) (also SO for short) and S (0) 2 ( also briefly SO2) in the heterocyclic ring. In the case of -N (O) - and -S (0) groups, both enantiomers are included.
Erfindungsgemäß steht der Ausdruck„Heteroaryl“ für heteroaromatische Verbindungen, d. h. According to the invention, the term “heteroaryl” stands for heteroaromatic compounds, ie. H.
vollständig ungesättigte aromatische heterocyclische Verbindungen, vorzugsweise für 5- bis 7-gliedrige Ringe mit 1 bis 4, vorzugsweise 1 oder 2 gleichen oder verschiedenen Heteroatomen, vorzugsweise O, S oder N. Erfindungsgemäße Heteroaryle sind beispielsweise lH-Pyrrol-l-yl; lH-Pyrrol-2-yl; lH-Pyrrol-completely unsaturated aromatic heterocyclic compounds, preferably for 5- to 7-membered rings with 1 to 4, preferably 1 or 2 identical or different heteroatoms, preferably O, S or N. Heteroaryls according to the invention are, for example, 1H-pyrrol-l-yl; lH-pyrrol-2-yl; lH-pyrrole
3-yl; Furan-2-yl; Furan-3-yl; Thien-2-yl; Thien-3-yl, lH-Imidazol-l-yl; lH-Imidazol-2-yl; lH-Imidazol-3-yl; Furan-2-yl; Furan-3-yl; Thien-2-yl; Thien-3-yl, lH-imidazol-l-yl; lH-imidazol-2-yl; lH-imidazole
4-yl; lH-Imidazol-5-yl; lH-Pyrazol-l-yl; lH-Pyrazol-3-yl; lH-Pyrazol-4-yl; lH-Pyrazol-5-yl, lH-l,2,3- Triazol-l-yl, lH-l,2,3-Triazol-4-yl, lH-l,2,3-Triazol-5-yl, 2H-l,2,3-Triazol-2-yl, 2H-l,2,3-Triazol-4-yl, lH-l,2,4-Triazol-l-yl, lH-l,2,4-Triazol-3-yl, 4H-l,2,4-Triazol-4-yl, l,2,4-Oxadiazol-3-yl, 1,2,4- Oxadiazol-5-yl, l,3,4-Oxadiazol-2-yl, l,2,3-Oxadiazol-4-yl, l,2,3-Oxadiazol-5-yl, l,2,5-Oxadiazol-3-yl, Azepinyl, Pyridin-2-yl, Pyridin-3-yl, Pyridin-4-yl, Pyrazin-2-yl, Pyrazin-3-yl, Pyrimidin-2-yl, 4-yl; lH-imidazol-5-yl; lH-pyrazol-l-yl; lH-pyrazol-3-yl; lH-pyrazol-4-yl; lH-pyrazol-5-yl, lH-l, 2,3-triazol-l-yl, lH-l, 2,3-triazol-4-yl, lH-l, 2,3-triazol-5-yl, 2H-l, 2,3-triazol-2-yl, 2H-l, 2,3-triazol-4-yl, lH-l, 2,4-triazol-l-yl, lH-l, 2,4- Triazol-3-yl, 4H-l, 2,4-triazol-4-yl, l, 2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, l, 3,4- Oxadiazol-2-yl, l, 2,3-oxadiazol-4-yl, l, 2,3-oxadiazol-5-yl, l, 2,5-oxadiazol-3-yl, azepinyl, pyridin-2-yl, Pyridin-3-yl, pyridin-4-yl, pyrazin-2-yl, pyrazin-3-yl, pyrimidin-2-yl,
Pyrimidin-4-yl, Pyrimidin-5-yl, Pyridazin-3-yl, Pyridazin-4-yl, l,3,5-Triazin-2-yl, l,2,4-Triazin-3-yl, l,2,4-Triazin-5-yl, l,2,4-Triazin-6-yl, l,2,3-Triazin-4-yl, l,2,3-Triazin-5-yl, 1,2,4-, 1,3,2-, 1,3,6- und l,2,6-Oxazinyl, Isoxazol-3-yl, Isoxazol-4-yl, Isoxazol-5-yl, l,3-Oxazol-2-yl, l,3-Oxazol-4-yl, 1,3- Oxazol-5-yl, Isothiazol-3-yl, Isothiazol-4-yl, Isothiazol-5-yl, l,3-Thiazol-2-yl, l,3-Thiazol-4-yl, 1,3- Thiazol-5-yl, Oxepinyl, Thiepinyl, l,2,4-Triazolonyl und 1 ,2,4-Diazepinyl, 2H-l,2,3,4-Tetrazol-5-yl, lH-l,2,3,4-Tetrazol-5-yl, l,2,3,4-Oxatriazol-5-yl, l,2,3,4-Thiatriazol-5-yl, l,2,3,5-Oxatriazol-4-yl, l,2,3,5-Thiatriazol-4-yl. Die erfindungsgemäßen Heteroarylgruppen können ferner mit einem oder mehreren, gleichen oder verschiedenen Resten substituiert sein. Sind zwei benachbarte Pyrimidin-4-yl, pyrimidin-5-yl, pyridazin-3-yl, pyridazin-4-yl, l, 3,5-triazin-2-yl, l, 2,4-triazin-3-yl, l, 2,4-triazin-5-yl, l, 2,4-triazin-6-yl, l, 2,3-triazin-4-yl, l, 2,3-triazin-5-yl, 1,2, 4-, 1,3,2-, 1,3,6- and l, 2,6-oxazinyl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, l, 3-oxazol-2 -yl, 1,3-oxazol-4-yl, 1,3-oxazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1,3-thiazol-2-yl , l, 3-thiazol-4-yl, 1,3-thiazol-5-yl, oxepinyl, thiepinyl, l, 2,4-triazolonyl and 1, 2,4-diazepinyl, 2H-l, 2,3,4 -Tetrazol-5-yl, lH-l, 2,3,4-tetrazol-5-yl, l, 2,3,4-oxatriazol-5-yl, l, 2,3,4-thiatriazol-5-yl , l, 2,3,5-oxatriazol-4-yl, l, 2,3,5-thiatriazole-4-yl. The heteroaryl groups according to the invention can furthermore be substituted by one or more, identical or different radicals. Are two neighboring
Kohlenstoffatome Bestandteil eines weiteren aromatischen Rings, so handelt es sich um annellierte heteroaromatische Systeme, wie benzokondensierte oder mehrfach annellierte Heteroaromaten. Carbon atoms are part of a further aromatic ring, so they are fused heteroaromatic systems, such as benzo-fused or multiply fused heteroaromatics.
Bevorzugt sind beispielsweise Chinoline (z. B. Chinolin-2-yl, Chinolin-3-yl, Chinolin-4-yl, Chinolin-5- yl, Chinolin-6-yl, Chinolin-7-yl, Chinolin-8-yl); Isochinoline (z. B. Isochinolin- l-yl, Isochinolin-3-yl, Isochinolin-4-yl, Isochinolin-5-yl, Isochinolin-6-yl, Isochinolin-7-yl, Isochinolin-8-yl); Chinoxalin; Chinazolin; Cinnolin; l,5-Naphthyridin; l,6-Naphthyridin; l,7-Naphthyridin; l,8-Naphthyridin; 2,6- Naphthyridin; 2,7-Naphthyridin; Phthalazin; Pyridopyrazine; Pyridopyrimidine; Pyridopyridazine; Pteridine; Pyrimidopyrimidine. Beispiele für Heteroaryl sind auch 5- oder 6-gliedrige benzokondensierte Ringe aus der Gruppe lH-Indol-l-yl, lH-Indol-2-yl, lH-Indol-3-yl, lH-Indol-4-yl, lH-Indol-5-yl, 1H- Indol-6-yl, lH-Indol-7-yl, l-Benzofüran-2-yl, l-Benzofüran-3-yl, l-Benzofüran-4-yl, l-Benzofüran-5- yl, l-Benzofüran-6-yl, l-Benzofüran-7-yl, l-Benzothiophen-2-yl, l-Benzothiophen-3-yl, 1- Benzothiophen-4-yl, l-Benzothiophen-5-yl, l-Benzothiophen-6-yl, l-Benzothiophen-7-yl, lH-Indazol-For example, quinolines (e.g. quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl ); Isoquinolines (e.g. isoquinolin-l-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl, isoquinolin-8-yl); quinoxaline; quinazoline; cinnoline; l, 5-naphthyridine; l, 6-naphthyridine; l, 7-naphthyridine; l, 8-naphthyridine; 2,6-naphthyridine; 2,7-naphthyridine; phthalazine; Pyridopyrazine; pyridopyrimidines; Pyridopyridazine; pteridines; Pyrimidopyrimidine. Examples of heteroaryl are also 5- or 6-membered benzo-fused rings from the group lH-indol-l-yl, lH-indol-2-yl, lH-indol-3-yl, lH-indol-4-yl, lH- Indol-5-yl, 1H-indol-6-yl, lH-indol-7-yl, l-benzofuran-2-yl, l-benzofuran-3-yl, l-benzofuran-4-yl, l-benzofuran 5- yl, l-benzofuran-6-yl, l-benzofuran-7-yl, l-benzothiophene-2-yl, l-benzothiophene-3-yl, 1-benzothiophene-4-yl, l-benzothiophene-5- yl, l-benzothiophene-6-yl, l-benzothiophene-7-yl, lH-indazole
1-yl, lH-Indazol-3-yl, lH-Indazol-4-yl, lH-Indazol-5-yl, lH-Indazol-6-yl, lH-Indazol-7-yl, 2H-Indazol-1-yl, 1H-indazol-3-yl, 1H-indazol-4-yl, 1H-indazol-5-yl, 1H-indazol-6-yl, 1H-indazol-7-yl, 2H-indazole
2-yl, 2H-Indazol-3-yl, 2H-Indazol-4-yl, 2H-Indazol-5-yl, 2H-Indazol-6-yl, 2H-Indazol-7-yl, 2H- Isoindol-2-yl, 2H-Isoindol-l-yl, 2H-Isoindol-3-yl, 2H-Isoindol-4-yl, 2H-Isoindol-5-yl, 2H-Isoindol-6-yl; 2H-Isoindol-7-yl, lH-Benzimidazol-l-yl, lH-Benzimidazol-2-yl, lH-Benzimidazol-4-yl, 1H- Benzimidazol-5-yl, lH-Benzimidazol-6-yl, lH-Benzimidazol-7-yl, l,3-Benzoxazol-2-yl, 1,3- Benzoxazol-4-yl, l,3-Benzoxazol-5-yl, l,3-Benzoxazol-6-yl, l,3-Benzoxazol-7-yl, l,3-Benzthiazol-2-yl, l,3-Benzthiazol-4-yl, l,3-Benzthiazol-5-yl, l,3-Benzthiazol-6-yl, l,3-Benzthiazol-7-yl, 1,2- Benzisoxazol-3-yl, l,2-Benzisoxazol-4-yl, l,2-Benzisoxazol-5-yl, l,2-Benzisoxazol-6-yl, 1,2- Benzisoxazol-7-yl, l,2-Benzisothiazol-3-yl, l,2-Benzisothiazol-4-yl, l,2-Benzisothiazol-5-yl, 1,2- Benzisothiazol-6-yl, l,2-Benzisothiazol-7-yl. 2-yl, 2H-indazol-3-yl, 2H-indazol-4-yl, 2H-indazol-5-yl, 2H-indazol-6-yl, 2H-indazol-7-yl, 2H-isoindol-2- yl, 2H-isoindol-1-yl, 2H-isoindol-3-yl, 2H-isoindol-4-yl, 2H-isoindol-5-yl, 2H-isoindol-6-yl; 2H-isoindol-7-yl, 1H-benzimidazol-1-yl, 1H-benzimidazol-2-yl, 1H-benzimidazol-4-yl, 1H-benzimidazol-5-yl, 1H-benzimidazol-6-yl, 1H- Benzimidazol-7-yl, l, 3-benzoxazol-2-yl, 1,3-benzoxazol-4-yl, l, 3-benzoxazol-5-yl, l, 3-benzoxazol-6-yl, l, 3- Benzoxazol-7-yl, l, 3-benzothiazol-2-yl, l, 3-benzothiazol-4-yl, l, 3-benzothiazol-5-yl, l, 3-benzothiazol-6-yl, l, 3- Benzothiazol-7-yl, 1,2-benzisoxazol-3-yl, 1,2-benzisoxazol-4-yl, 1,2-benzisoxazol-5-yl, 1,2-benzisoxazol-6-yl, 1,2- Benzisoxazol-7-yl, l, 2-benzisothiazol-3-yl, l, 2-benzisothiazol-4-yl, l, 2-benzisothiazol-5-yl, 1,2-benzisothiazol-6-yl, l, 2- benzisothiazol-7-yl.
Die Bezeichnung "Halogen" bedeutet beispielsweise Fluor, Chlor, Brom oder Iod. Wird die The term "halogen" means, for example, fluorine, chlorine, bromine or iodine. Will the
Bezeichnung für einen Rest verwendet, dann bedeutet "Halogen" beispielsweise ein Fluor-, Chlor-, Brom- oder lodatom. Name used for a radical, then "halogen" means for example a fluorine, chlorine, bromine or iodine atom.
Erfindungsgemäß bedeutet„Alkyl“ einen geradkettigen oder verzweigten offenkettigen, gesättigten Kohlenwasserstoffrest, der gegebenenfalls ein- oder mehrfach substituiert ist und im letzteren Falle als „substituiertes Alkyl“ bezeichnet wird. Bevorzugte Substituenten sind Halogenatome, Alkoxy-, Haloalkoxy-, Cyano-, Alkylthio, Haloalkylthio-, Amino- oder Nitrogruppen, besonders bevorzugt sind Methoxy, Methyl, Fluoralkyl, Cyano, Nitro, Fluor, Chlor, Brom oder lod. Die Vorsilbe„Bis“ schließt auch die Kombination unterschiedlicher Alkylreste ein, z. B. Methyl(Ethyl) oder Ethyl(Methyl). „Haloalkyl“, ,,-alkenyl“ und ,,-alkinyl“ bedeuten durch gleiche oder verschiedene Halogenatome, teilweise oder vollständig substituiertes Alkyl, Alkenyl bzw. Alkinyl, z.B. Monohaloalkyl According to the invention, “alkyl” means a straight-chain or branched open-chain, saturated hydrocarbon radical which is optionally substituted one or more times and is referred to in the latter case as “substituted alkyl”. Preferred substituents are halogen atoms, alkoxy, haloalkoxy, cyano, alkylthio, haloalkylthio, amino or nitro groups; methoxy, methyl, fluoroalkyl, cyano, nitro, fluorine, chlorine, bromine or iodine are particularly preferred. The prefix "bis" also includes the combination of different alkyl residues, e.g. B. methyl (ethyl) or ethyl (methyl). “Haloalkyl”, “- alkenyl” and “- alkynyl” mean alkyl, alkenyl or alkynyl, for example monohaloalkyl, which is partially or completely substituted by the same or different halogen atoms
(= Monohalogenalkyl) wie z. B. CH2CH2CI, CH2CH2Br, CHCICH3, CH2CI, CH2F; Perhaloalkyl wie z.(= Monohalogenalkyl) such as B. CH 2 CH 2 CI, CH 2 CH 2 Br, CHCICH 3 , CH 2 CI, CH 2 F; Perhaloalkyl such as
B. CCI3, CCIF2, CFC12,CF2CC1F2, CF2CCIFCF3; Polyhaloalkyl wie z. B. CH2CHFC1, CF2CC1FH, CF2CBrFH, CH2CF3; Der Begriff Perhaloalkyl umfasst dabei auch den Begriff Perfluoralkyl. B. CCI3, CCIF 2, CFC1 2 , CF 2 CC1F 2, CF 2 CCIFCF3; Polyhaloalkyl such as B. CH 2 CHFC1, CF 2 CC1FH, CF 2 CBrFH, CH 2 CF 3 ; The term perhaloalkyl also includes the term perfluoroalkyl.
„Haloalkoxy“ ist z.B. OCF3, OCHF2, OCH2F, OCF2CF3, OCH2CF3 und OCH2CH2CI; Entsprechendes gilt für Haloalkenyl und andere durch Halogen substituierten Reste. “Haloalkoxy” is, for example, OCF 3 , OCHF 2 , OCH 2 F, OCF 2 CF 3 , OCH 2 CF 3 and OCH 2 CH 2 CI; The same applies to haloalkenyl and other halogen-substituted radicals.
Der hier beispielhaft genannte Ausdruck "(Ci-C4)-Alkyl" bedeutet eine Kurzschreibweise für geradkettiges oder verzweigtes Alkyl mit einem bis 4 Kohlenstoffatomen entsprechend der The expression "(Ci-C4) -alkyl" mentioned here by way of example means a shorthand notation for straight-chain or branched alkyl having one to 4 carbon atoms corresponding to the
Bereichsangabe für C-Atome, d. h. umfasst die Reste Methyl, Ethyl, 1 -Propyl, 2-Propyl, 1 -Butyl, 2-Butyl, 2-Methylpropyl oder tert-Butyl. Allgemeine Alkylreste mit einem größeren angegebenen Bereich von C-Atomen, z. B. "(Ci-C6)-Alkyl", umfassen entsprechend auch geradkettige oder verzweigte Alkylreste mit einer größeren Zahl von C-Atomen, d. h. gemäß Beispiel auch die Alkylreste mit 5 und 6 C-Atomen. Range specification for carbon atoms, ie includes the radicals methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl. General alkyl radicals with a larger specified range of carbon atoms, e.g. B. "(Ci-C 6 ) alkyl", also include straight-chain or branched alkyl radicals with a larger number of carbon atoms, ie, according to the example, also the alkyl radicals with 5 and 6 carbon atoms.
Wenn nicht speziell angegeben, sind bei den Kohlenwasserstoffresten wie Alkyl-, Alkenyl- und Alkinylresten, auch in zusammengesetzten Resten, die niederen Kohlenstoffgerüste, z.B. mit 1 bis 6 C-Atomen bzw. bei ungesättigten Gruppen mit 2 bis 6 C-Atomen, bevorzugt. Alkylreste, auch in den zusammengesetzten Resten wie Alkoxy, Haloalkyl usw., bedeuten z.B. Methyl, Ethyl, n- oder i-Propyl, n-, i-, t- oder 2-Butyl, Pentyle, Hexyle, wie n-Hexyl, i-Hexyl und l,3-Dimethylbutyl, Heptyle, wie n-Heptyl, 1 -Methylhexyl und 1 ,4-Dimethylpentyl; Alkenyl- und Alkinylreste haben die Bedeutung der den Alkylresten entsprechenden möglichen ungesättigten Reste, wobei mindestens eine Doppelbindung bzw. Dreifachbindung enthalten ist. Bevorzugt sind Reste mit einer Doppelbindung bzw. Unless specifically stated, the hydrocarbon radicals such as alkyl, alkenyl and alkynyl radicals, even in composite radicals, are the lower carbon skeletons, e.g. with 1 to 6 carbon atoms or in the case of unsaturated groups with 2 to 6 carbon atoms, preferred. Alkyl radicals, also in the composite radicals such as alkoxy, haloalkyl etc., mean e.g. Methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, i-hexyl and 1,3-dimethylbutyl, heptyls, such as n-heptyl, 1-methylhexyl and 1, 4-dimethylpentyl; Alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals, at least one double bond or triple bond being present. Residues with a double bond or
Dreifachbindung. Triple bond.
Der Begriff„Alkenyl“ schließt insbesondere auch geradkettige oder verzweigte offenkettige The term “alkenyl” also includes straight-chain or branched open-chain ones
Kohlenwasserstoffreste mit mehr als einer Doppelbindung ein, wie l,3-Butadienyl und 1 ,4-Pentadienyl, aber auch Allenyl- oder Kumulenyl-reste mit einer bzw. mehreren kumulierten Doppelbindungen, wie beispielsweise Allenyl (l,2-Propadienyl), 1 ,2-Butadienyl und l,2,3-Pentatrienyl. Alkenyl bedeutet z.B. Vinyl, welches ggf. durch weitere Alkylreste substituiert sein kann, z B. (aber nicht beschränkt auf) (C2-C6)- Alkenyl wie Ethenyl, l-Propenyl, 2-Propenyl, 1 -Methylethenyl, l-Butenyl, 2-Butenyl, 3- Butenyl, 1 -Methyl- l-propenyl, 2-Methyl- l-propenyl, 1 -Methyl-2-propenyl, 2-Methyl-2-propenyl, 1- Pentenyl, 2-Pentenyl, 3-Pentenyl, 4-Pentenyl, 1 -Methyl- l-butenyl, 2-Methyl- l-butenyl, 3 -Methyl- 1- butenyl, 1 -Methyl-2-butenyl, 2-Methyl-2-butenyl, 3-Methyl-2-butenyl, l-Methyl-3-butenyl, 2-Methyl-3- butenyl, 3-Methyl-3-butenyl, 1 , 1 -Dimethyl-2-propenyl, 1 ,2-Dimethyl- l-propenyl, 1 ,2-Dimethyl-2- propenyl, l-Ethyl-l-propenyl, 1 -Ethyl-2-propenyl, l-Hexenyl, 2-Hexenyl, 3-Hexenyl, 4-Hexenyl, 5- Hexenyl, 1 -Methyl- l-pentenyl, 2-Methyl-l-pentenyl, 3-Methyl-l-pentenyl, 4-Methyl-l-pentenyl, 1- Methyl-2-pentenyl, 2-Methyl-2-pentenyl, 3-Methyl-2-pentenyl, 4-Methyl-2-pentenyl, l-Methyl-3- pentenyl, 2-Methyl-3-pentenyl, 3-Methyl-3-pentenyl, 4-Methyl-3-pentenyl, 1 -Methyl-4-pentenyl, 2- Methyl-4-pentenyl, 3-Methyl-4-pentenyl, 4-Methyl-4-pentenyl, 1 , 1 -Dimethyl-2-butenyl, 1 , 1 -Dimethyl- 3-butenyl, l,2-Dimethyl-l-butenyl, 1 ,2-Dimethyl-2-butenyl, l,2-Dimethyl-3-butenyl, l,3-Dimethyl-l- butenyl, l,3-Dimethyl-2-butenyl, l,3-Dimethyl-3-butenyl, 2,2-Dimethyl-3-butenyl, 2,3-Dimethyl-l- butenyl, 2,3-Dimethyl-2-butenyl, 2,3-Dimethyl-3-butenyl, 3,3-Dimethyl-l-butenyl, 3,3-Dimethyl-2- butenyl, l-Ethyl-l-butenyl, l-Ethyl-2-butenyl, l-Ethyl-3-butenyl, 2-Ethyl-l-butenyl, 2-Ethyl-2-butenyl, 2-Ethyl-3 -butenyl, 1 , 1 ,2-Trimethyl-2-propenyl, 1 -Ethyl- 1 -methyl-2-propenyl, 1 -Ethyl-2-methyl- 1 - propenyl und 1 -Ethyl-2-methyl-2-propenyl. Hydrocarbon radicals with more than one double bond, such as 1,3-butadienyl and 1,4-pentadienyl, but also allenyl or cumulenyl radicals with one or more cumulative double bonds, such as, for example, allenyl (1,2-propadienyl), 1,1 2-butadienyl and l, 2,3-pentatrienyl. Alkenyl means, for example, vinyl, which can optionally be substituted by further alkyl radicals, for example (but not limited to) (C2-C6) alkenyl such as ethenyl, l-propenyl, 2-propenyl, 1-methylethenyl, l-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3- Pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl- 2-butenyl, l-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1, 1-dimethyl-2-propenyl, 1, 2-dimethyl-l-propenyl, 1, 2-dimethyl-2- propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl l-pentenyl, 3-methyl-l-pentenyl, 4-methyl-l-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2- pentenyl, l-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2- Dimethyl-2-butenyl, l, 2-dimethyl-3-butenyl, l, 3-dimethyl-l-butenyl, l, 3-dimethyl-2-butenyl, l, 3-dimethyl-3-butenyl, 2,2- Dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3- Dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl 3-butenyl, 1, 1, 2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1 - pro penyl and 1-ethyl-2-methyl-2-propenyl.
Der Begriff„Alkinyl“ schließt insbesondere auch geradkettige oder verzweigte offenketige The term “alkynyl” also includes straight-chain or branched open-chain ones
Kohlenwasserstoffreste mit mehr als einer Dreifachbindung oder auch mit einer oder mehreren Hydrocarbon residues with more than one triple bond or with one or more
Dreifachbindungen und einer oder mehreren Doppelbindungen ein, wie beispielsweise l,3-Butatrienyl bzw. 3-Penten-l-in-l-yl. (C2-C6)-Alkinyl bedeutet z.B. Ethinyl, l-Propinyl, 2-Propinyl, l-Butinyl, 2- Butinyl, 3-Butinyl, 1 -Methyl-2-propinyl, l-Pentinyl, 2-Pentinyl, 3-Pentinyl, 4-Pentinyl, l-Methyl-2- butinyl, l-Methyl-3-butinyl, 2-Methyl-3-butinyl, 3 -Methyl- l-butinyl, 1 , 1 -Dimethyl-2-propinyl, l-Ethyl- 2-propinyl, l-Hexinyl, 2-Hexinyl, 3-Hexinyl, 4-Hexinyl, 5-Hexinyl, 1 -Methyl-2-pentinyl, l-Methyl-3- pentinyl, 1 -Methyl-4-pentinyl, 2-Methyl-3-pentinyl, 2-Methyl-4-pentinyl, 3 -Methyl- l-pentinyl, 3- Methyl-4-pentinyl, 4-Methyl- l-pentinyl, 4-Methyl-2-pentinyl, 1 , 1 -Di-methyl-2-butinyl, l,l-Dimethyl-3- butinyl, l,2-Dimethyl-3-butinyl, 2,2-Dimethyl-3-butinyl, 3, 3 -Dimethyl- l-butinyl, 1 -Ethyl-2-butinyl, 1- Ethyl-3-butinyl, 2-Ethyl-3-butinyl und 1 -Ethyl- 1 -methyl-2-propinyl. Triple bonds and one or more double bonds, such as 1, 3-butatrienyl or 3-penten-l-in-l-yl. (C2-C6) alkynyl means e.g. Ethynyl, l-propynyl, 2-propynyl, l-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, l-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, l-methyl- 2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1, 1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, l-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2- Methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1, 1-di-methyl-2-butynyl, l, l-dimethyl-3-butynyl, l, 2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3, 3-dimethyl-l-butynyl, 1-ethyl-2-butynyl, 1- Ethyl 3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl.
Der Begriff„Cycloalkyl“ bedeutet ein carbocyclisches, gesätigtes Ringsystem mit vorzugsweise 3-8 Ring-C-Atomen, z.B. Cyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl, das gegebenenfalls weiter substituiert ist, bevorzugt durch Wasserstoff, Alkyl, Alkoxy, Cyano, Nitro, Alkylthio, Haloalkylthio, Halogen, Alkenyl, Alkinyl, Haloalkyl, AMino, Alkylamino, Bisalkylamino, Alkocycarbonyl, The term "cycloalkyl" means a carbocyclic, saturated ring system with preferably 3-8 ring C atoms, e.g. Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, which is optionally further substituted, preferably by hydrogen, alkyl, alkoxy, cyano, nitro, alkylthio, haloalkylthio, halogen, alkenyl, alkynyl, haloalkyl, AMino, alkylamino, bisalkylamino, alkocycarbonyl,
Hydroxycarbonyl, Arylalkoxycarbonyl, Aminocarbonyl, Alkylaminocarbonyl, Hydroxycarbonyl, arylalkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl,
Cycloalkylaminocarbonyl. Im Falle von gegebenenfalls substituiertem Cycloalkyl werden cyclische Systeme mit Substituenten umfasst, wobei auch Substituenten mit einer Doppelbindung am  Cycloalkylaminocarbonyl. In the case of optionally substituted cycloalkyl, cyclic systems with substituents are included, substituents also having a double bond on
Cycloalkylrest, z. B. eine Alkylidengruppe wie Methyliden, umfasst sind. Im Falle von gegebenenfalls substituiertem Cycloalkyl werden auch mehrcyclische aliphatische Systeme umfasst, wie beispielsweise Bicyclo[l .1.0]butan-l -yl, Bicyclo[l .1 0]butan-2-yl, Bicyclo[2.1.0]pentan-l -yl, Bicyclo[l .1.1 ]pentan-l - yl, Bicyclo[2.l.0]pentan-2-yl, Bicyclo[2.l.0]pentan-5-yl, Bicyclo[2.l.l]hexyl, Bicyclo[2.2.l]hept-2-yl, Bicyclo[2.2.2]octan-2-yl, Bicyclo[3.2.l]octan-2-yl, Bicyclo[3.2.2]nonan-2-yl, Adamantan-l-yl und Adamantan-2-yl, aber auch Systeme wie z. B. l,l'-Bi(cyclopropyl)-l-yl, l,l'-Bi(cyclopropyl)-2-yl. Der Ausdruck "(C3-C7)-Cycloalkyl" bedeutet eine Kurzschreibweise für Cycloalkyl mit drei bis 7 Cycloalkyl radical, e.g. B. an alkylidene group such as methylidene are included. In the case of optionally substituted cycloalkyl, multi-cyclic aliphatic systems are also included, such as, for example, bicyclo [1.0] butan-1-yl, bicyclo [1.0] butan-2-yl, bicyclo [2.1.0] pentan-1 - yl, bicyclo [l. 1.1] pentan-1-yl, bicyclo [2.l.0] pentan-2-yl, bicyclo [2.l.0] pentan-5-yl, bicyclo [2.ll] hexyl, Bicyclo [2.2.l] hept-2-yl, bicyclo [2.2.2] octan-2-yl, bicyclo [3.2.l] octan-2-yl, bicyclo [3.2.2] nonan-2-yl, adamantane l-yl and adamantan-2-yl, but also systems such as B. l, l'-Bi (cyclopropyl) -l-yl, l, l'-Bi (cyclopropyl) -2-yl. The The term "(C3-C7) cycloalkyl" means a shorthand notation for cycloalkyl of three to seven
Kohlenstoffatomen entsprechend der Bereichsangabe für C-Atome. lm Falle von substituiertem Cycloalkyl werden auch spirocyclische aliphatische Systeme umfasst, wie beispielsweise Spiro[2.2]pent-l-yl, Spiro[2.3]hex-l-yl, Spiro[2.3]hex-4-yl, 3-Spiro[2.3]hex-5-yl,Carbon atoms according to the range for carbon atoms. In the case of substituted cycloalkyl, spirocyclic aliphatic systems are also included, such as, for example, spiro [2.2] pent-l-yl, spiro [2.3] hex-l-yl, spiro [2.3] hex-4-yl, 3-spiro [2.3] hex-5-yl,
Spiro [3.3 ]hept- 1 -yl, Spiro[3.3 ]hept-2-yl. Spiro [3.3] hept-1-yl, Spiro [3.3] hept-2-yl.
„Cycloalkenyl“ bedeutet ein carbocyclisches, nicht aromatisches, partiell ungesättigtes Ringsystem mit vorzugsweise 4-8 C-Atomen, z.B. 1 -Cyclobutenyl, 2-Cyclobutenyl, 1 -Cyclopentenyl, 2-Cyclopentenyl, 3-Cyclopentenyl, oder 1 -Cyclohexenyl, 2-Cyclohexenyl, 3-Cyclohexenyl, l,3-Cyclohexadienyl oder 1 ,4-Cyclohexadienyl, wobei auch Substituenten mit einer Doppelbindung am Cycloalkenylrest, z. B. eine Alkylidengruppe wie Methyliden, umfasst sind lm Falle von gegebenenfalls substituiertem Cycloalkenyl gelten die Erläuterungen für substituiertes Cycloalkyl entsprechend. "Cycloalkenyl" means a carbocyclic, non-aromatic, partially unsaturated ring system with preferably 4-8 C atoms, e.g. 1-Cyclobutenyl, 2-Cyclobutenyl, 1-Cyclopentenyl, 2-Cyclopentenyl, 3-Cyclopentenyl, or 1-Cyclohexenyl, 2-Cyclohexenyl, 3-Cyclohexenyl, l, 3-Cyclohexadienyl or 1, 4-Cyclohexadienyl, whereby also substituents with a Double bond on the cycloalkenyl radical, e.g. B. In the case of optionally substituted cycloalkenyl, the explanations for substituted cycloalkyl apply accordingly.
Der Begriff„Alkyliden“, z. B. auch in der Form (Ci-Cio)-Alkyliden, bedeutet den Rest eines geradkettigen oder verzweigten offenkettigen Kohlenwasserstoffrests, der über eine Zweifachbindung gebunden ist. Als Bindungsstelle für Alkyliden kommen naturgemäß nur Positionen am Grundkörper in Frage, an denen zwei H- Atome durch die Doppelbindung ersetzt werden können; Reste sind z. B. =CFb, =CH-CH3, =C(CFb)-CF[3, =C(CH3)-C2H5 oder =C(C2FF)-C'2FF. Cycloalkyliden bedeutet ein The term "alkylidene", e.g. B. also in the form (Ci-Cio) alkylidene, means the remainder of a straight-chain or branched open-chain hydrocarbon radical which is bonded via a double bond. As a binding site for alkylidene there are naturally only positions on the base in which two H atoms can be replaced by the double bond; Leftovers are e.g. B. = CFb, = CH-CH3, = C (CFb) -CF [3, = C (CH 3 ) -C 2 H5 or = C (C2FF) -C ' 2FF . Cycloalkylidene means a
carbocyclischer Rest, der über eine Zweifachbindung gebunden ist. carbocyclic radical which is bonded via a double bond.
„Arylalkyl“ steht für einen über eine Alkylgruppe gebundenen Arylrest,„Heteroarylalkyl“ bedeutet einen über eine Alkylgruppe gebundenen Heteroarylrest, und„Heterocyclylalkyl“ bedeutet einen über eine Alkylgruppe gebundenen Heterocyclylrest. “Arylalkyl” stands for an aryl radical bonded via an alkyl group, “heteroarylalkyl” means a heteroaryl radical bonded via an alkyl group, and “heterocyclylalkyl” means a heterocyclyl radical bonded via an alkyl group.
Erfindungsgemäß steht "Haloalkylthio" - in Alleinstellung oder als Bestandteil einer chemischen Gruppe - für geradkettiges oder verzweigtes S -Halogenalkyl, vorzugsweise mit 1 bis 8, oder mit 1 bis 6 Kohlenstoffatomen, wie (Ci-Cs)-, (C'i-G,)- oder (Ci-C4)-Haloalkylthio, z.B. (aber nicht beschränkt auf) Trifluormethylthio, Pentafluorethylthio, Difluormethyl, 2,2-Difluoreth-l-ylthio, 2,2,2-Difluoreth-l- ylthio, 3,3,3-prop-l-ylthio. According to the invention, "haloalkylthio" - alone or as part of a chemical group - stands for straight-chain or branched S -haloalkyl, preferably with 1 to 8, or with 1 to 6 carbon atoms, such as (Ci-Cs) -, (C ' iG,) - or (Ci-C4) -haloalkylthio, for example (but not limited to) trifluoromethylthio, pentafluoroethylthio, difluoromethyl, 2,2-difluoroeth-1-ylthio, 2,2,2-difluoroeth-1-ylthio, 3,3,3 -prop-l-ylthio.
„Halocycloalkyl“ bedeutet durch gleiche oder verschiedene Halogenatome, wie z. B. F, CI und Br, oder durch Haloalkyl, wie z. B. Trifluormethyl oder Difluormethyl teilweise oder vollständig substituiertes Cycloalkyl, z.B. l-Fluorcycloprop-l-yl, 2-Fluorcycloprop-l-yl, 2,2-Difluorcycloprop-l-yl, 1- Fluorcyclobut-l-yl, l-Trifluormethylcycloprop-l-yl, 2-Trifluormethylcycloprop-l-yl, l-Chlor- cycloprop-l-yl, 2-Chlorcycloprop-l-yl, 2,2-Dichlorcycloprop-l-yl, 3,3-Difluorcyclobutyl, Erfindungsgemäß steht "Trialkylsilyl" - in Alleinstellung oder als Bestandteil einer chemischen Gruppe - für geradkettiges oder verzweigtes Si- Alkyl, vorzugsweise mit 1 bis 8, oder mit 1 bis 6 "Halocycloalkyl" means the same or different halogen atoms, such as. B. F, CI and Br, or by haloalkyl, such as. B. trifluoromethyl or difluoromethyl partially or completely substituted cycloalkyl, for example l-fluorocycloprop-l-yl, 2-fluorocycloprop-l-yl, 2,2-difluorocycloprop-l-yl, 1-fluorocyclobut-l-yl, l-trifluoromethylcycloprop- l-yl, 2-trifluoromethylcycloprop-l-yl, l-chlorocycloprop-l-yl, 2-chlorocycloprop-l-yl, 2,2-dichlorocycloprop-l-yl, 3,3-difluorocyclobutyl, According to the invention, "trialkylsilyl" - alone or as part of a chemical group - stands for straight-chain or branched Si-alkyl, preferably with 1 to 8, or with 1 to 6
Kohlenstoffatomen, wie Tri-[(Ci-Cs)-, (C'i-G,)- oder (Ci-C i)-alkyl]silyl, z.B. (aber nicht beschränkt auf) Trimethylsilyl, Triethylsilyl, Tri-(n-propyl)silyl, Tri-(iso-propyl)silyl, Tri-(n-butyl)silyl, Tri-(l- methylprop-l-yl)silyl, Tri-(2-methylprop-l-yl)silyl, Tri(l,l-Dimethyleth-l-yl)silyl, Tri(2,2- Dimethyleth- 1 -yl)silyl. Carbon atoms, such as tri - [(Ci-Cs) -, (C ' iG,) - or (Ci-C i) alkyl] silyl, for example (but not limited to) trimethylsilyl, triethylsilyl, tri- (n-propyl) silyl, tri- (isopropyl) silyl, tri- (n-butyl) silyl, tri- (l-methylprop-l-yl) silyl, tri- (2-methylprop-l-yl) silyl, tri (l, l-dimethyleth-l-yl) silyl, tri (2,2-dimethyleth-1-yl) silyl.
Wenn die Verbindungen durch Wasserstoffverschiebung Tautomere bilden können, welche strukturell formal nicht durch die allgemeine Formel (1) erfasst würden, so sind diese Tautomere gleichwohl von der Definition der erfindungsgemäßen Verbindungen der allgemeinen Formel (1) umfasst, sofern nicht ein bestimmtes Tautomer Gegenstand der Betrachtung ist. So können beispielsweise viele If the compounds can form tautomers by hydrogen shift which would not be structurally formally covered by the general formula (1), these tautomers are nevertheless included in the definition of the compounds of the general formula (1) according to the invention, unless a specific tautomer is the subject of consideration is. For example, many
Carbonylverbindungen sowohl in der Ketoform wie auch in der Enolform vorliegen, wobei beide Formen durch die Definition der Verbindung der allgemeinen Formel (1) umfasst werden. Carbonyl compounds exist both in the keto form and in the enol form, both forms being encompassed by the definition of the compound of the general formula (1).
Die Verbindungen der allgemeinen Formel (1) können je nach Art und Verknüpfung der Substituenten als Stereoisomere vorliegen. Die durch ihre spezifische Raumform definierten möglichen Stereoisomere, wie Enantiomere, Diastereomere, Z- und E-lsomere sind alle von der allgmeinen Formel (1) umfasst. Sind beispielsweise eine oder mehrere Alkenylgruppen vorhanden, so können Diastereomere (Z- und E- lsomere) auftreten. Sind beispielsweise ein oder mehrere asymmetrische Kohlenstoffatome vorhanden, so können Enantiomere und Diastereomere auftreten. Stereoisomere lassen sich aus den bei der Depending on the nature and linkage of the substituents, the compounds of the general formula (1) can exist as stereoisomers. The possible stereoisomers defined by their specific spatial shape, such as enantiomers, diastereomers, Z and E isomers, are all encompassed by the general formula (1). For example, if one or more alkenyl groups are present, diastereomers (Z and E isomers) can occur. For example, if one or more asymmetric carbon atoms are present, enantiomers and diastereomers can occur. Stereoisomers can be derived from the at
Herstellung anfallenden Gemischen nach üblichen Trennmethoden erhalten. Die chromatographische Trennung kann sowohl im analytischen Maßstab zur Feststellung des Enantiomerenüberschusses bzw. des Diastereomerenüberschusses, wie auch im präparativen Maßstab zur Herstellung von Prüfmustern für die biologische Ausprüfüng erfolgen. Ebenso können Stereoisomere durch Einsatz stereoselektiver Reaktionen unter Verwendung optisch aktiver Ausgangs- und/oder Hilfsstoffe selektiv hergestellt werden. Die Erfindung betrifft somit auch alle Stereoisomeren, die von der allgemeinen Formel (1) umfasst, jedoch nicht mit ihrer spezifischen Stereoform angegeben sind, sowie deren Gemische. Obtaining mixtures obtained by conventional separation methods. The chromatographic separation can be carried out on an analytical scale to determine the enantiomeric excess or the diastereomeric excess, as well as on a preparative scale for the production of test samples for the biological test. Likewise, stereoisomers can be produced selectively by using stereoselective reactions using optically active starting materials and / or auxiliary substances. The invention thus also relates to all stereoisomers which are encompassed by the general formula (1) but are not specified with their specific stereoform, and to mixtures thereof.
Sofern die Verbindungen als Feststoffe erhalten werden, kann die Reinigung auch durch If the compounds are obtained as solids, the cleaning can also be carried out by
Umkristallisieren oder Digerieren erfolgen. Sofern einzelne Verbindungen (1) nicht auf den nachstehend beschriebenen Wegen zufriedenstellend zugänglich sind, können sie durch Derivatisierung anderer Verbindungen (1) hergestellt werden. Recrystallize or digest. If individual compounds (1) are not satisfactorily accessible in the ways described below, they can be prepared by derivatizing other compounds (1).
Als lsolierungs-, Reinigungs- und Stereoisomerenauftrennungsverfahren von Verbindungen der allgemeinen Formel (1) kommen Methoden in Frage, die dem Fachmann aus analogen Fällen allgemein bekannt sind, z.B. durch physikalische Verfahren wie Kristallisation, Chromatographieverfahren, vor allem Säulenchromatographie und HPLC (Hochdruckflüssigchromatographie), Destillation, gegebenenfalls unter reduziertem Druck, Extraktion und andere Verfahren, können gegebenfalls verbleibende Gemische in der Regel durch chromatographische Trennung, z.B. an chiralen Festphasen, getrennt werden. Für präparative Mengen oder im industriellen Maßstab kommen Verfahren in Frage wie Kristallisation, z.B. diastereomerer Salze, die aus den Diastereomerengemischen mit optisch aktiven Säuren und gegebenenfalls bei vorhandenen sauren Gruppen mit optisch aktiven Basen erhalten werden können. Methods which are generally known to the person skilled in the art from analogous cases, for example by physical processes such as crystallization, chromatography processes, especially column chromatography and HPLC (high pressure liquid chromatography), and distillation are suitable as isolation, purification and stereoisomer separation processes of compounds of the general formula (1) . optionally under reduced pressure, extraction and other processes, any remaining mixtures can be separated as a rule by chromatographic separation, for example on chiral solid phases. For preparative amounts or on an industrial scale, processes such as crystallization, for example diastereomeric salts, can be used, which can be obtained from the diastereomer mixtures with optically active acids and, if appropriate, with acidic groups present with optically active bases.
Die vorliegende Erfindung beansprucht auch Verfahren zur Herstellung der erfindungsgemäßen Verbindungen der allgemeinen Formel (I). The present invention also claims processes for the preparation of the compounds of the general formula (I) according to the invention.
Die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) können unter anderem ausgehend von bekannten Verfahren hergestellt werden. Die eingesetzten und untersuchten Syntheserouten gehen dabei von kommerziell erhältlichen oder leicht herstellbaren Bausteinen aus. Die Gruppierungen X, A, R1, R2, R3 und m der allgemeinen Formel (I) haben in den nachfolgenden Schemata die zuvor definierten Bedeutungen, sofern nicht beispielhafte, aber nicht einschränkende, Definitionen erfolgen. The compounds of the general formula (I) according to the invention can be prepared, inter alia, using known processes. The synthetic routes used and investigated are based on commercially available or easily manufactured building blocks. The groupings X, A, R 1 , R 2 , R 3 and m of the general formula (I) have the meanings defined above in the following schemes, unless exemplary but not restrictive definitions are given.
Erfindungsgemäße Verbindungen mit A für S(0)n können beispielsweise nach der in Schema 1 angegebenen Methode hergestellt werden. Compounds according to the invention with A for S (0) n can be prepared, for example, by the method given in Scheme 1.
(E-l) (E-M) (E-Ill) (E-IV) (Ia) (E-l) (E-M) (E-Ill) (E-IV) (Ia)
Schema 1. Scheme 1.
Die Pyridine der allgemeinen Formel (Ia) können über eine Kupplung der Pyridine (E-III), wobei LG eine Abgangsgruppe ist, mit dem Disulfid (E-IV) in Gegenwart von entweder Zink(O) und Palladium- Katalysatoren (wie zum Beispiel Pd^ppfjCh.CFbCh), oder Kupfer(0) und Basen, hergestellt werden. Die Base kann ein Acetat-Salz eines Alkali-Metalls (wie zum Beispiel Natrium oder Kalium) sein. Die Reaktionen werden im Allgemeinen in einem organischen Lösungsmittel, wie zum Beispiel The pyridines of the general formula (Ia) can be coupled via a coupling of the pyridines (E-III), LG being a leaving group, with the disulfide (E-IV) in the presence of either zinc (O) and palladium catalysts (such as, for example Pd ^ ppfjCh.CFbCh), or copper (0) and bases. The base can be an acetate salt of an alkali metal (such as sodium or potassium). The reactions are generally carried out in an organic solvent, such as
Tetrahydrofuran, Dimethylsulfoxid oder Dimethylformamid, bei Temperaturen zwischen 0°C und dem Siedepunkt des Lösemittels, durchgeführt. Die Pyridine der allgemeinen Formel (E-III) können über eine Alkyierung der Pyridine (E-I) in Gegenwart von Basen mit dem Pyri(mi)din (E-II), wobei LG eine Abgangsgruppe ist, und Kupfers- Salze, hergestellt werden. Die Base kann ein Carbonat-Salz eines Alkali-Metalls (wie zum Beispiel Natrium, Kalium oder Cäsium) sein. Die Kupfersalze können Kupferhalogenide, wie zum Beispiel Kupfer(I)-Iodid, sein. Die Reaktionen werden im Allgemeinen in einem organischen Lösungsmittel, wie zum Beispiel Acetonitril oder Dimethylformamid, bei Temperaturen zwischen 0°C und dem Siedepunkt des Lösemittels, durchgeführt. Tetrahydrofuran, dimethyl sulfoxide or dimethylformamide, at temperatures between 0 ° C and the boiling point of the solvent. The pyridines of the general formula (E-III) can be prepared via an alkylation of the pyridines (EI) in the presence of bases with the pyri (mi) din (E-II), where LG is a leaving group and copper salts. The base can be a carbonate salt of an alkali metal (such as sodium, potassium or cesium). The copper salts can be copper halides such as copper (I) iodide. The reactions are generally carried out in an organic solvent such as acetonitrile or dimethylformamide at temperatures between 0 ° C and the boiling point of the solvent.
Pyridine der allgemeinen Formel (E-I) sind literaturbekannt und können beispielsweise gemäß der in Organic Leiters (2016), 18, 3106-9, W02013/14170 und ähnlich beschriebenen Methoden hergestellt werden.  Pyridines of the general formula (E-I) are known from the literature and can be prepared, for example, according to the methods described in Organic Leiters (2016), 18, 3106-9, W02013 / 14170 and similar.
Erfindungsgemäße Verbindungen mit n für 1 und 2 können beispielsweise nach der in Schema 2 angegebenen Methode hergestellt werden. Compounds according to the invention with n for 1 and 2 can be prepared, for example, by the method given in scheme 2.
Schema 2 Scheme 2
Die Sulfone und Sulfoxide der allgemeinen Formel (Ib) können über eine Oxidation der Pyridine (Ia) hergestellt werden. Solche Reaktionen sind dem Fachmann bekannt und beispielsweise in Advanced Synthesis & Catalysis (201 1), 353(2+3), 295-302 beschrieben. The sulfones and sulfoxides of the general formula (Ib) can be prepared by oxidation of the pyridines (Ia). Such reactions are known to the person skilled in the art and are described, for example, in Advanced Synthesis & Catalysis (201 1), 353 (2 + 3), 295-302.
Schema 3  Scheme 3
Die Pyridine der allgemeinen Formel (Ic) können über eine Kupplung der Pyridine (E-VII) mit dem Alkylhalid (E-VIII), wobei Hai ein Halogen ist, in Gegenwart von Palladium- Katalysatoren (wie zum Beispiel Pd(PPh3)4) und Basen hergestellt werden. Die Base kann ein Carbonat-Salz eines Alkali- Metalls (wie zum Beispiel Natrium oder Kalium) sein. Die Reaktionen werden im Allgemeinen in einem organischen Lösungsmittel, wie zum Beispiel Tetrahydrofuran, Toluol oder Ethanol mit oder ohne Zugabe von Wasser, bei Temperaturen zwischen 0°C und dem Siedepunkt des Lösemittels, durchgeführt. The pyridines of the general formula (Ic) can be coupled via a coupling of the pyridines (E-VII) with the alkyl halide (E-VIII), where shark is a halogen, in the presence of palladium catalysts (such as Example Pd (PPh3) 4) and bases are prepared. The base can be a carbonate salt of an alkali metal (such as sodium or potassium). The reactions are generally carried out in an organic solvent, such as, for example, tetrahydrofuran, toluene or ethanol, with or without the addition of water, at temperatures between 0 ° C. and the boiling point of the solvent.
Die Pyridine der allgemeinen Formel (E-VII) können über eine Kupplung der Pyridine (E-VI), wobei Hai ein Halogen ist, mit Pinacolboran oder Bis(pinacolato)diboron in Gegenwart von Palladium- Katalysatoren (wie zum Beispiel Pd(MeCN)2Cl2), Liganden (wie zum Beispiel XPhos) und Basen, hergestellt werden. Die Base kann ein Amin (wie zum Beispiel Triethylamin) sein. Die Reaktionen werden im Allgemeinen in einem organischen Lösungsmittel, wie zum Beispiel Tetrahydrofuran oder Dioxan, bei Temperaturen zwischen 0°C und dem Siedepunkt des Lösemittels, durchgeführt. The pyridines of the general formula (E-VII) can be coupled with pinacolborane or bis (pinacolato) diborone in the presence of palladium catalysts (such as, for example, Pd (MeCN)) via a coupling of the pyridines (E-VI), where shark is a halogen. 2Cl2), ligands (such as XPhos) and bases. The base can be an amine (such as triethylamine). The reactions are generally carried out in an organic solvent such as tetrahydrofuran or dioxane at temperatures between 0 ° C and the boiling point of the solvent.
Die Pyridine der allgemeinen Formel (E-VI) können über eine Alkyierung der Pyridine (E-V) in Gegenwart von Basen mit dem Pyri(mi)din (E-II), wobei LG eine Abgangsgruppe ist, und Kupfers- Salze, hergestellt werden. Die Base kann ein Carbonat-Salz eines Alkali-Metalls (wie zum Beispiel Natrium, Kalium oder Cäsium) sein. Die Kupfersalze können Kupferhalogenide, wie zum Beispiel Kupfer(I)-Iodid, sein. Die Reaktionen werden im Allgemeinen in einem organischen Lösungsmittel, wie zum Beispiel Acetonitril oder Dimethylformamid, bei Temperaturen zwischen 0°C und dem Siedepunkt des Lösemittels, durchgeführt. The pyridines of the general formula (E-VI) can be prepared via an alkylation of the pyridines (E-V) in the presence of bases with the pyri (mi) din (E-II), where LG is a leaving group and copper salts. The base can be a carbonate salt of an alkali metal (such as sodium, potassium or cesium). The copper salts can be copper halides such as copper (I) iodide. The reactions are generally carried out in an organic solvent such as acetonitrile or dimethylformamide at temperatures between 0 ° C and the boiling point of the solvent.
Pyridine der allgemeinen Formel (E-V) sind literaturbekannt und können beispielsweise gemäß der in J. Am. Chem. Soc. (1952), 74, 1916-9 ähnlich beschriebenen Methoden hergestellt werden. Pyridines of the general formula (E-V) are known from the literature and can, for example, according to the in J. Am. Chem. Soc. (1952), 74, 1916-9 similar methods described.
Schema 4. Scheme 4.
Die Pyridine der allgemeinen Formel (Id) können über eine Alkyierung der Pyridine (E-XII) in Gegenwart von Basen mit dem Pyri(mi)din (E-II), wobei LG eine Abgangsgruppe ist, und Kupfers- Salze, hergestellt werden. Die Base kann ein Carbonat-Salz eines Alkali-Metalls (wie zum Beispiel Natrium, Kalium oder Cäsium) sein. Die Kupfersalze können Kupferhalogenide, wie zum Beispiel Kupfer(I)-Iodid, sein. Die Reaktionen werden im Allgemeinen in einem organischen Lösungsmittel, wie zum Beispiel Acetonitril oder Dimethylformamid, bei Temperaturen zwischen 0°C und dem Siedepunkt des Lösemittels, durchgeführt. The pyridines of the general formula (Id) can be prepared via an alkylation of the pyridines (E-XII) in the presence of bases with the pyri (mi) din (E-II), where LG is a leaving group and copper salts. The base can be a carbonate salt of an alkali metal (such as sodium, potassium or cesium). The copper salts can be copper halides, such as Copper (I) iodide. The reactions are generally carried out in an organic solvent such as acetonitrile or dimethylformamide at temperatures between 0 ° C and the boiling point of the solvent.
Die Pyridine der allgemeinen Formel (E-XII) können über eine Demethylierung der Pyridine (E-XI) in Gegenwart von entweder Bromwasserstoffsäure und Essigsäure oder Bortribromid hergestellt werden. Die Reaktionen mit Bortribromid werden im Allgemeinen in einem organischen Lösungsmittel, wie zum Beispiel Dichlormethan, bei Temperaturen zwischen 0°C und dem Siedepunkt des Lösemittels, durchgeführt. The pyridines of the general formula (E-XII) can be prepared by demethylating the pyridines (E-XI) in the presence of either hydrobromic acid and acetic acid or boron tribromide. The reactions with boron tribromide are generally carried out in an organic solvent such as dichloromethane at temperatures between 0 ° C and the boiling point of the solvent.
Die Pyridine der allgemeinen Formel (E-XI) können über eine Kupplung der Pyridine (E-IX) mit dem Boronsäure (E-X) in Gegenwart von Kupfer(II)-Katalysatoren (wie zum Beispiel Cu(OAc)2) und Basen, hergestellt werden. Die Base kann ein Amin (wie zum Beispiel Triethylamin) sein. Die Reaktionen werden im Allgemeinen in einem organischen Lösungsmittel, wie zum Beispiel Dichlormethan, bei Temperaturen zwischen 0°C und dem Siedepunkt des Lösemittels, durchgeführt. The pyridines of the general formula (E-XI) can be prepared by coupling the pyridines (E-IX) with the boronic acid (EX) in the presence of copper (II) catalysts (such as Cu (OAc) 2) and bases become. The base can be an amine (such as triethylamine). The reactions are generally carried out in an organic solvent such as dichloromethane at temperatures between 0 ° C and the boiling point of the solvent.
Pyridine der allgemeinen Formel (E-IX) sind literaturbekannt und können beispielsweise gemäß der in EP1357111 und ähnlich beschriebenen Methoden hergestellt werden. Pyridines of the general formula (E-IX) are known from the literature and can be prepared, for example, according to the methods described in EP1357111 and similar.
Ausgewählte detaillierte Synthesebeispiele für die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) sind im Folgenden aufgeführt. Die 'H-NMR-, 13C-NMR- und 19F-NMR-spektroskopischen Daten, die für die in den nachfolgenden Abschnitten beschriebenen chemischen Beispiele angegeben sind, (400 MHz bei *H-NMR und 150 MHz bei 13C-NMR und 375 MHz bei 19F-NMR, Lösungsmittel CDCL, CD3OD oder de- DM SO, interner Standard: Tetramethylsilan d = 0.00 ppm), wurden mit einem Gerät der Firma Broker erhalten, und die bezeichneten Signale haben die nachfolgend aufgeführten Bedeutungen: br = breit(es); s = Singulett, d = Dublett, t = Triplett, dd = Doppeldublett, ddd = Dublett eines Doppeldubletts, m = Multiplett, q = Quartett, quint = Quintett, sext = Sextett, sept = Septett, dq = Doppelquartett, dt = Doppeltriplett. Bei Diastereomerengemischen werden entweder die jeweils signifikanten Signale beider Diastereomere oder das charakteristische Signal des Hauptdiastereomers angegeben. Die verwendeten Abkürzungen für chemische Gruppen haben beispielsweise die nachfolgenden Bedeutungen: Me = CH3, Et = CH2CH3, t-Hex = C(CH3)2CH(CH3)2, t-Bu = C(CH3)3, n- Bu = unverzweigtes Butyl, n-Pr = unverzweigtes Propyl, i-Pr = verzweigtes Propyl, c-Pr = Cyclopropyl, c-Hex = Cyclohexyl. Synthesebeispiele: Selected detailed synthesis examples for the compounds of the general formula (I) according to the invention are listed below. The 'H-NMR, 13 C-NMR and 19 F-NMR spectroscopic data given for the chemical examples described in the following sections (400 MHz at * H-NMR and 150 MHz at 13 C-NMR and 375 MHz at 19 F-NMR, solvent CDCL, CD3OD or de-DM SO, internal standard: tetramethylsilane d = 0.00 ppm) were obtained with a Broker device, and the signals indicated have the meanings given below: br = wide (it); s = singlet, d = doublet, t = triplet, dd = double doublet, ddd = doublet of a double doublet, m = multiplet, q = quartet, quint = quintet, sext = sextet, sept = septet, dq = double quartet, dt = double triplet. In the case of mixtures of diastereomers, either the respectively significant signals of both diastereomers or the characteristic signal of the main diastereomer are given. The abbreviations for chemical groups used have, for example, the following meanings: Me = CH3, Et = CH2CH3, t-Hex = C (CH3) 2CH (CH3) 2, t-Bu = C (CH3) 3, n-Bu = unbranched butyl , n-Pr = unbranched propyl, i-Pr = branched propyl, c-Pr = cyclopropyl, c-Hex = cyclohexyl. Synthesis Examples:
Tabellenbeispiel Nummer 1-216:  Table example number 1-216:
Synthesestufe 1 : 2-[(3-Brom-4-methyl-2-pyridyl)oxy]pyrimidin  Synthesis level 1: 2 - [(3-bromo-4-methyl-2-pyridyl) oxy] pyrimidine
Eine Mischung von 3-Brom-4-methylpyridin-2-ol (1.00 g, 5.32 mmol), 2-Chlorpyrimidin (609 mg, 5.32 mmol), Kupfer(I)-Iodid (1.02 g, 5.36 mmol), Cäsiumcarbonat (3.50 g, 10.8 mmol) und DMF (15 ml) wird in einer Mikrowelle unter Stickstoff bei 150 °C für 1 h erhitzt. Das resultierende Reaktionsgemisch wird filtriet und eingeengt. Das resultierende Rohprodukt wird in Essigester gelöst und mit ges.  A mixture of 3-bromo-4-methylpyridin-2-ol (1.00 g, 5.32 mmol), 2-chloropyrimidine (609 mg, 5.32 mmol), copper (I) iodide (1.02 g, 5.36 mmol), cesium carbonate (3.50 g, 10.8 mmol) and DMF (15 ml) is heated in a microwave under nitrogen at 150 ° C. for 1 h. The resulting reaction mixture is filtered and concentrated. The resulting crude product is dissolved in ethyl acetate and saturated with sat.
Natriumchloridlösung gewaschen, über Magnesiumsulfat getrocknet, filtriert und eingeengt. Durch abschließende säulenchromatographische Reinigung (Gradient Essigester/Heptan) des resultierenden Rohproduktes erhält man 2-[(3-Brom-4-methyl-2-pyridyl)oxy]pyrimidin (110 mg, 8% der Theorie). Washed sodium chloride solution, dried over magnesium sulfate, filtered and concentrated. Final column chromatographic purification (gradient ethyl acetate / heptane) of the resulting crude product gives 2 - [(3-bromo-4-methyl-2-pyridyl) oxy] pyrimidine (110 mg, 8% of theory).
Synthesestufe 2: 2-[(4-Methyl-3-phenylsulfanyl-2-pyridyl)oxy]pyrimidin (Tabellenbeispiel No. 1-216): Synthesis stage 2: 2 - [(4-methyl-3-phenylsulfanyl-2-pyridyl) oxy] pyrimidine (table example No. 1-216):
Eine Mischung von 2-[(3-Brom-4-methyl-2-pyridyl)oxy]pyrimidin (280 mg, 1.05 mmol),  A mixture of 2 - [(3-bromo-4-methyl-2-pyridyl) oxy] pyrimidine (280 mg, 1.05 mmol),
Diphenyldisulfid (138 mg, 0.63 mmol), Kupfer (100 mg, 1.58 mmol), Kaliumacetat (206 mg, 2.10 mmol) und Dimethylsulfoxid (6 ml) wird unter Stickstoff bei 100 °C für 40 h erhitzt. Das resultierende Reaktionsgemisch wird filtriet und eingeengt. Durch abschließende säulenchromatographische Reinigung (Gradient Essigester/Heptan) isoliert man 2-[(4-Methyl-3-phenylsulfanyl-2- pyridyl)oxy]pyrimidin (74 mg, 24% der Theorie). Tabellenbeispiel Nummer 1-533: Diphenyl disulfide (138 mg, 0.63 mmol), copper (100 mg, 1.58 mmol), potassium acetate (206 mg, 2.10 mmol) and dimethyl sulfoxide (6 ml) are heated under nitrogen at 100 ° C. for 40 h. The resulting reaction mixture is filtered and concentrated. Final column chromatographic purification (gradient ethyl acetate / heptane) isolated 2 - [(4-methyl-3-phenylsulfanyl-2-pyridyl) oxy] pyrimidine (74 mg, 24% of theory). Table example number 1-533:
Synthesestufe 1 : 2-Methoxy-6-methyl-3-phenoxypyridin:  Synthesis stage 1: 2-methoxy-6-methyl-3-phenoxypyridine:
Eine Mischung von 2-Methoxy-6-methylpyridin-3-ol (960 mg, 6.89 mmol), Benzolboronsäure (1.00 g, 8.27 mmol), Kupfer(ll)-acetat (2.13 g, 11.7 mmol), Triethylamin (1.92 ml, 13.7 mmol), 4Ä Molsiebe und Dichlormethan (38 ml) wird unter Argon bei Raumtemperatur für 72 h gerührt. Das resultierende Reaktionsgemisch wird filtriet und eingeengt. Durch abschließende säulenchromatographische Reinigung (Gradient Essigester/Heptan) isoliert man 2-Methoxy-6-methyl-3-phenoxypyridin (925 mg, 62% der Theorie).  A mixture of 2-methoxy-6-methylpyridin-3-ol (960 mg, 6.89 mmol), benzene boronic acid (1.00 g, 8.27 mmol), copper (II) acetate (2.13 g, 11.7 mmol), triethylamine (1.92 ml, 13.7 mmol), 4 Å molecular sieves and dichloromethane (38 ml) are stirred under argon at room temperature for 72 h. The resulting reaction mixture is filtered and concentrated. Final column chromatographic purification (gradient ethyl acetate / heptane) isolates 2-methoxy-6-methyl-3-phenoxypyridine (925 mg, 62% of theory).
Synthesestufe 2: 6-Methyl-3-Phenoxypyridin-2-ol: Synthesis stage 2: 6-methyl-3-phenoxypyridin-2-ol:
Eine Mischung von 2-Methoxy-6-methyl-3-phenoxypyridin (925 mg, 4.29 mmol),  A mixture of 2-methoxy-6-methyl-3-phenoxypyridine (925 mg, 4.29 mmol),
Bromwasserstoffsäure (45% Lösung in Essigsäure, 5.2 ml, 42.9 mmol) und Essigsäure (20 ml) wird bei 100 °C für 1 h erhitzt. Das resultierende Reaktionsgemisch wird eingeengt. Das Rohprodukt wird inHydrobromic acid (45% solution in acetic acid, 5.2 ml, 42.9 mmol) and acetic acid (20 ml) is heated at 100 ° C. for 1 h. The resulting reaction mixture is concentrated. The raw product is in
Wasser gelöst, mit 2M NaOH auf pH 5 gebracht und mit Essigester extrahiert. Die vereinigten organischen Phasen werden mit ges. Natriumchloridlösung gewaschen, über Magnesiumsulfat getrocknet, filtriert und eingeengt. Auf diese Weise erhält man 6-Methyl-3-Phenoxypyridin-2-ol (680 mg, 78% der Theorie). Synthesestufe 3: 2-[(6-Methyl-3-phenoxy-2-pyridyl)oxy]-5-(trifluormethyl)pyrimidin (Tabellenbeispiel Nr. 1-533): Dissolved water, brought to pH 5 with 2M NaOH and extracted with ethyl acetate. The combined organic phases are saturated with sat. Washed sodium chloride solution, dried over magnesium sulfate, filtered and concentrated. In this way, 6-methyl-3-phenoxypyridin-2-ol (680 mg, 78% of theory) is obtained. Synthesis stage 3: 2 - [(6-methyl-3-phenoxy-2-pyridyl) oxy] -5- (trifluoromethyl) pyrimidine (table example No. 1-533):
Eine Mischung von 6-Methyl-3-phenoxypyridin-2-ol (150 mg, 0.74 mmol), 2-Chlor-5- trifluormethylpyrimidine (280 mg, 1.52 mmol), Kupfer(I)-iodid (28 mg, 0.14 mmol), Cäsiumcarbonat (485 mg, 1.49 mmol) und Acetonitril (4 ml) wird bei 100 °C für 3 h erhitzt. Das resultierende  A mixture of 6-methyl-3-phenoxypyridin-2-ol (150 mg, 0.74 mmol), 2-chloro-5-trifluoromethylpyrimidine (280 mg, 1.52 mmol), copper (I) iodide (28 mg, 0.14 mmol) , Cesium carbonate (485 mg, 1.49 mmol) and acetonitrile (4 ml) is heated at 100 ° C for 3 h. The resulting
Reaktionsgemisch wird filtriet und eingeengt. Durch abschließende säulenchromatographische Reinigung (Gradient Essigester/Heptan) isoliert man 2-[(6-Methyl-3-phenoxy-2-pyridyl)oxy]-5- (trifluormethyl)pyrimidin (153 mg, 59% der Theorie). The reaction mixture is filtered and concentrated. Final column chromatographic purification (gradient ethyl acetate / heptane) isolated 2 - [(6-methyl-3-phenoxy-2-pyridyl) oxy] -5- (trifluoromethyl) pyrimidine (153 mg, 59% of theory).
Tabellenbeispiel Nummer 1-478: Table example number 1-478:
Synthesestufe 1 : 2-[(3-Brom-4,6-dimethyl-2-pyridyl)oxy]-5-fluorpyrimidin  Synthesis step 1: 2 - [(3-bromo-4,6-dimethyl-2-pyridyl) oxy] -5-fluoropyrimidine
Eine Mischung von 3-Brom-4,6-dimethylpyridin-2-ol (3.35 g, 16.5 mmol), 2-Chlor-5-fluorpyrimidin (3.29 g, 24.8 mmol), Kupfer(I)-iodid (630 mg, 3.31 mmol), Cäsiumcarbonat (10.8 g, 33.1 mmol) und Dimethylformamid (15 ml) wird bei 130 °C für 18 h erhitzt. Das resultierende Reaktionsgemisch wird filtriet und eingeengt. Durch abschließende säulenchromatographische Reinigung (Gradient  A mixture of 3-bromo-4,6-dimethylpyridin-2-ol (3.35 g, 16.5 mmol), 2-chloro-5-fluoropyrimidine (3.29 g, 24.8 mmol), copper (I) iodide (630 mg, 3.31 mmol), cesium carbonate (10.8 g, 33.1 mmol) and dimethylformamide (15 ml) is heated at 130 ° C for 18 h. The resulting reaction mixture is filtered and concentrated. Final column chromatographic purification (gradient
Essigester/Heptan) isoliert man 2-[(3-Brom-4,6-dimethyl-2-pyridyl)oxy]-5-fluorpyrimidin (1.58 g, 32% der Theorie). Synthesestufe 2: 2-[[4,6-dimethyl-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-2-pyridyl]oxy]-5- fluorpyrimidin: Ethyl acetate / heptane), 2 - [(3-bromo-4,6-dimethyl-2-pyridyl) oxy] -5-fluoropyrimidine (1.58 g, 32% of theory) is isolated. Synthesis stage 2: 2 - [[4,6-dimethyl-3- (4,4,5,5-tetramethyl-l, 3,2-dioxaborolan-2-yl) -2-pyridyl] oxy] -5-fluoropyrimidine:
Eine Mischung von 2-[(3-Brom-4,6-dimethyl-2-pyridyl)oxy]-5-fluorpyrimidin (1.54 g, 5.15 mmol), Pinacolboran (920 mg, 7.21 mmol), Triethylamin (4.1 ml, 29.3 mmol), Pd(MeCN)2Cl2 (54 mg, 0.20 mmol), X-Phos (197 mg, 0.41 mmol) und Dioxan (25 ml) wird unter Argon bei 110 °C für 8 h erhitzt. Das resultierende Reaktionsgemisch wird filtriet und eingeengt. Durch abschließende  A mixture of 2 - [(3-bromo-4,6-dimethyl-2-pyridyl) oxy] -5-fluoropyrimidine (1.54 g, 5.15 mmol), pinacolborane (920 mg, 7.21 mmol), triethylamine (4.1 ml, 29.3 mmol), Pd (MeCN) 2Cl2 (54 mg, 0.20 mmol), X-Phos (197 mg, 0.41 mmol) and dioxane (25 ml) are heated under argon at 110 ° C for 8 h. The resulting reaction mixture is filtered and concentrated. By closing
säulenchromatographische Reinigung (Gradient Essigester/Heptan) isoliert man 2-[[4,6-dimethyl-3- (4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-2-pyridyl]oxy]-5-fluorpyrimidin (1.58 g, 89% der Theorie). purification by column chromatography (gradient ethyl acetate / heptane), 2 - [[4,6-dimethyl-3- (4,4,5,5-tetramethyl-l, 3,2-dioxaborolan-2-yl) -2-pyridyl] is isolated oxy] -5-fluoropyrimidine (1.58 g, 89% of theory).
Synthesestufe 3: 2-[(3-Benzyl-4,6-dimethyl-2-pyridyl)oxy]-5-fluorpyrimidin (Tabellenbeispiel Nr. I- 478) Synthesis stage 3: 2 - [(3-benzyl-4,6-dimethyl-2-pyridyl) oxy] -5-fluoropyrimidine (table example No. I- 478)
Eine Mischung von 2-[[4,6-dimethyl-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-2-pyridyl]oxy]-5- fluorpyrimidin (140 mg, 0.40 mmol), Benzylbromid (105 mg, 0.60 mmol), Natriumcarbonat (86 mg, 0.81 mmol), Pd(PPln)4 (47 mg, 0.04 mmol), Toluol (1.3 ml), Ethanol (0.3 ml) und Wasser (0.3 ml) wird unter Argon bei 80 °C für 1.5 Stunden erhitzt. Das resultierende Reaktionsgemisch wird filtriet und eingeengt. Durch abschließende säulenchromatographische Reinigung (Gradient Essigester/Heptan) isoliert man 2-[(3-Benzyl-4,6-dimethyl-2-pyridyl)oxy]-5-fluorpyrimidin (98 mg, 78% der Theorie). ln Analogie zu den oben angeführten und an entsprechender Stelle rezitierten Herstellungsbeispielen erhält man die nachfolgend genannten und in Tabelle 1 dargestellten Verbindungen der allgemeinen Formel (1) A mixture of 2 - [[4,6-dimethyl-3- (4,4,5,5-tetramethyl-l, 3,2-dioxaborolan-2-yl) -2-pyridyl] oxy] -5-fluoropyrimidine ( 140 mg, 0.40 mmol), benzyl bromide (105 mg, 0.60 mmol), sodium carbonate (86 mg, 0.81 mmol), Pd (PPln) 4 (47 mg, 0.04 mmol), toluene (1.3 ml), ethanol (0.3 ml) and Water (0.3 ml) is heated under argon at 80 ° C for 1.5 hours. The resulting reaction mixture is filtered and concentrated. Final column chromatographic purification (gradient ethyl acetate / heptane) isolated 2 - [(3-benzyl-4,6-dimethyl-2-pyridyl) oxy] -5-fluoropyrimidine (98 mg, 78% of theory). Analogously to the preparation examples mentioned above and recited at the appropriate place, the compounds of the general formula (1) mentioned below and shown in Table 1 are obtained.
Tabelle 1 Table 1
NMR-Daten ausgewählter Beispiele (Endprodukte und Intermediate) NMR data of selected examples (end products and intermediates)
NMR-Peak-Listenverfahren NMR peak list procedures
Die lH-NMR-Daten ausgewählter Beispiele werden in Form von lH-NMR-Peaklisten notiert. Zu jedem Signalpeak wird erst der d-Wert in ppm und dann die Signalintensität in runden Klammem aufgeführt. Die d-Wert - Signalintensitäts- Zahlenpaare von verschiedenen Signalpeaks werden durch Semikolons voneinander getrennt aufgelistet. The 1 H-NMR data of selected examples are noted in the form of 1 H-NMR peak lists. For each signal peak, the d-value is listed in ppm and then the signal intensity in round brackets. The d-value - signal intensity-number pairs of different signal peaks are listed separated by semicolons.
Die Peakliste eines Beispieles hat daher die Form: di (Intensität^; d2 (Intensität2); . ; d; (Intensität^; . ; dh (Intensität^ The peak list of an example therefore has the form: di (intensity ^; d2 (intensity2);.; D; (intensity ^;.; D h (intensity ^
Die Intensität scharfer Signale korreliert mit der Höhe der Signale in einem gedruckten Beispiel eines NMR-Spektrums in cm und zeigt die wirklichen Verhältnisse der Signalintensitäten. Bei breiten Signalen können mehrere Peaks oder die Mitte des Signals und ihre relative Intensität im Vergleich zum intensivsten Signal im Spektrum gezeigt werden. 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 of the signal intensities. For wide signals, multiple peaks or the center of the signal and their relative intensity can be shown compared to the most intense signal in the spectrum.
Zur Kalibrierung der chemischen Verschiebung von lH-NMR-Spektren benutzen wir Tetramethylsilan und/oder die chemische Verschiebung des Lösungsmittels, besondem im Falle von Spektren, die in DMSO gemessen werden. Daher kann in NMR-Peaklisten der Tetramethylsilan-Peak Vorkommen, muss es aber nicht. Die Listen der lH-NMR-Peaks sind ähnlich den klassischen 1H-NMR- Ausdrucken und enthalten somit gewöhnlich alle Peaks, die bei einer klassischen NMR-Interpretation aufgeführt werden. 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. Therefore, the tetramethylsilane peak can occur in NMR peak lists, but it does not have to. The lists of the 1H-NMR peaks are similar to the classic 1H-NMR printouts and thus usually contain all the peaks which are listed in a classic NMR interpretation.
Darüber hinaus können sie wie klassische 1H-NMR- Ausdrucke Lösungsmittelsignale, Signale von Stereoisomeren der Zielverbindungen, die ebenfalls Gegenstand der Erfindung sind, und/oder Peaks von Verunreinigungen zeigen. In addition, like classic 1H NMR printouts, they can show solvent signals, signals from stereoisomers of the target compounds, which are also a subject of the invention, and / or peaks of impurities.
Bei der Angabe von Verbindungssignalen im Delta-Bereich von Lösungsmitteln und/oder Wasser sind in unseren Listen von lH-NMR-Peaks die gewöhnlichen Lösungsmittelpeaks, zum Beispiel Peaks von DMSO in DMSO-D6 und der Peak von Wasser, gezeigt, die gewöhnlich im Durchschnitt eine hohe Intensität aufweisen. When indicating connection signals in the delta range of solvents and / or water, our lists of 1 H NMR peaks show the usual solvent peaks, for example peaks of DMSO in DMSO-D 6 and the peak of water, which are usually given in the Have a high intensity on average.
Die Peaks von Stereoisomeren der Targetverbindungen und/oder Peaks von Verunreinigungen haben gewöhnlich im Durchschnitt eine geringere Intensität als die Peaks der Zielverbindungen (zum Beispiel mit einer Reinheit von >90%). The peaks of stereoisomers of the target compounds and / or peaks of impurities usually have a lower intensity on average than the peaks of the target compounds (for example with a purity of> 90%).
Solche Stereoisomere und/oder Verunreinigungen können typisch für das jeweilige Such stereoisomers and / or impurities can be typical of each
Herstellungsverfahren sein. Ihre Peaks können somit dabei helfen, die Reproduktion unseres  Manufacturing process. Your peaks can help reproduce ours
Herstellungsverfahrens anhand von“Nebenprodukt-Fingerabdrücken” zu erkennen.  Recognize manufacturing process based on "by-product fingerprints".
Einem Experten, der die Peaks der Zielverbindungen mit bekannten Verfahren (MestreC, ACD- Simulation, aber auch mit empirisch ausgewerteten Erwartungswerten) berechnet, kann je nach Bedarf die Peaks der Zielverbindungen isolieren, wobei gegebenenfalls zusätzliche Intensitätsfilter eingesetzt werden. Diese Isolierung wäre ähnlich dem betreffenden Peak-Picking bei der klassischen 1H-NMR- Interpretation. An expert who calculates the peaks of the target compounds using known methods (MestreC, ACD simulation, but also using empirically evaluated expected values) can isolate the peaks of the target compounds as required, using additional intensity filters if necessary. This isolation would be similar to the relevant peak picking in the classic 1H NMR interpretation.
Weitere Details zu lH-NMR-Peaklisten können der Research Disclosure Database Number 564025 entnommen werden. Further details on 1H NMR peak lists can be found in Research Disclosure Database Number 564025.
_ _ _ _
NMR-Daten der Endprodukte (manuelle Auswertung) NMR data of the end products (manual evaluation)
Gegenstand der vorliegenden Erfindung ist weiterhin die Verwendung einer oder mehrerer The present invention furthermore relates to the use of one or more
Verbindungen der allgemeinen Formel (I) und/oder deren Salzen, wie oben definiert, vorzugsweise in einer der als bevorzugt bzw. besonders bevorzugt gekennzeichneten Ausgestaltung, insbesondere einer oder mehrerer Verbindungen der Formeln (1-001) bis (1-662) und/oder deren Salze, jeweils wie oben definiert, als Herbizid und/oder Pflanzenwachstumsregulator, vorzugsweise in Kulturen von Nutz- und/oder Zierpflanzen. Gegenstand der vorliegenden Erfindung ist ferner ein Verfahren zur Bekämpfung von Schadpflanzen und/oder zur Wachstumsregulierung von Pflanzen, dadurch gekennzeichnet, dass eine wirksame Menge einer oder mehrerer Verbindungen der allgemeinen Formel (I) und/oder deren Salzen, wie oben definiert, vorzugsweise in einer der als bevorzugt bzw. besonders bevorzugt gekennzeichneten Ausgestaltung, insbesondere einer oder mehrerer Verbindungen der Formeln (1-001) bis (1-662) und/oder deren Salze, jeweils wie oben definiert, oder eines erfindungsgemäßen Mittels, wie nachstehend definiert, Compounds of the general formula (I) and / or their salts, as defined above, preferably in one of the configurations characterized as preferred or particularly preferred, in particular one or more compounds of the formulas (1-001) to (1-662) and / or their salts, each as defined above, as a herbicide and / or plant growth regulator, preferably in crops of useful and / or ornamental plants. The present invention furthermore relates to a process for controlling harmful plants and / or for regulating the growth of plants, characterized in that an effective amount of one or more compounds of the general formula (I) and / or their salts, as defined above, preferably in one the configuration characterized as preferred or particularly preferred, in particular one or more compounds of the formulas (1-001) to (1-662) and / or their salts, in each case as defined above, or an agent according to the invention as defined below,
auf die (Schad)Pflanzen, (Schad)Pflanzensamen, den Boden, in dem oder auf dem die  on the (harmful) plants, (harmful) plant seeds, the soil in or on which the
(Schad)Pflanzen wachsen, oder die Anbaufläche appliziert wird.  (Damaging) plants grow, or the cultivated area is applied.
Gegenstand der vorliegenden Erfindung ist auch ein Verfahren zur Bekämpfung von unerwünschten Pflanzen, vorzugsweise in Nutzpflanzenkulturen, dadurch gekennzeichnet, dass eine wirksame Menge einer oder mehrerer Verbindungen der allgemeinen Formel (1) und/oder deren Salzen, wie oben definiert, vorzugsweise in einer der als bevorzugt bzw. besonders bevorzugt gekennzeichneten Ausgestaltung, insbesondere einer oder mehrerer Verbindungen der Formeln (1-001) bis (1-662) und/oder deren Salze, jeweils wie oben definiert, oder eines erfindungsgemäßen Mittels, wie nachstehend definiert, The present invention also relates to a process for controlling unwanted plants, preferably in crops, characterized in that an effective amount of one or more compounds of the general formula (1) and / or their salts, as defined above, preferably in one of the as preferably or particularly preferably characterized embodiment, in particular one or more compounds of the formulas (1-001) to (1-662) and / or their salts, in each case as defined above, or an agent according to the invention, as defined below,
auf unerwünschte Pflanzen (z.B. Schadpflanzen wie mono- oder dikotyle Unkräuter oder unerwünschte Kulturpflanzen), das Saatgut der unerwünschten Pflanzen (d.h. Pflanzensamen, z.B. Körner, Samen oder vegetative Vermehrungsorgane wie Knollen oder Sprossteile mit Knospen), den Boden, in dem oder auf dem die unerwünschte Pflanzen wachsen, (z.B. den Boden von Kulturland oder Nicht-Kulturland) oder die Anbaufläche (d.h. Fläche, auf der die unerwünschte Pflanzen wachsen werden) appliziert wird.  on undesirable plants (e.g. harmful plants such as monocotyledonous or dicotyledon weeds or undesired crop plants), the seeds of the undesirable plants (i.e. plant seeds, e.g. grains, seeds or vegetative propagation organs such as tubers or shoot parts with buds), the soil in or on which the unwanted plants grow (e.g. the soil of cultivated land or non-cultivated land) or the area under cultivation (ie the area on which the undesired plants will grow) is applied.
Gegenstand der vorliegenden Erfindung ist ferner auch Verfahren zur Bekämpfung zur The present invention also relates to methods for combating
Wachstumsregulierung von Pflanzen, vorzugsweise von Nutzpflanzen, dadurch gekennzeichnet, dass eine wirksame Menge einer oder mehrerer Verbindungen der allgemeinen Formel (I) und/oder deren Salzen, wie oben definiert, vorzugsweise in einer der als bevorzugt bzw. besonders bevorzugt gekennzeichneten Ausgestaltung, insbesondere einer oder mehrerer Verbindungen der Formeln (1-001) bis (1-662) und/oder deren Salze, jeweils wie oben definiert, oder eines erfindungsgemäßen Mittels, wie nachstehend definiert, die Pflanze, das Saatgut der Pflanze (d.h. Pflanzensamen, z.B. Körner, Samen oder vegetative Vermehrungsorgane wie Knollen oder Sprossteile mit Knospen), den Boden, in dem oder auf dem die Pflanzen wachsen, (z.B. den Boden von Kulturland oder Nicht-Kulturland) oder die Anbaufläche (d.h. Fläche, auf der die Pflanzen wachsen werden) appliziert wird. Regulation of the growth of plants, preferably of useful plants, characterized in that an effective amount of one or more compounds of the general formula (I) and / or their salts, as defined above, preferably in one of the preferred or particularly preferred embodiments, in particular one or several compounds of the formulas (1-001) to (1-662) and / or their salts, each as defined above, or an agent according to the invention as defined below, the plant, the seeds of the plant (ie plant seeds, e.g. grains, seeds or vegetative propagation organs such as tubers or shoots with buds), the soil in or on which the plants grow (e.g. the soil of cultivated or non-cultivated land) or the area under cultivation (ie the area on which the plants will grow) is applied.
Dabei können die erfindungsgemäßen Verbindungen bzw. die erfindungsgemäßen Mittel z.B. im Vorsaat- (gegebenenfalls auch durch Einarbeitung in den Boden), Vorauflauf- und/oder The compounds according to the invention or the agents according to the invention can e.g. in pre-sowing (possibly also by incorporation into the soil), pre-emergence and / or
Nachauflaufverfahren ausgebracht werden. Im einzelnen seien beispielhaft einige Vertreter der mono- und dikotylen Unkrautflora genannt, die durch die die erfindungsgemäßen Verbindungen kontrolliert werden können, ohne dass durch die Nennung eine Beschränkung auf bestimmte Arten erfolgen soll. Post-emergence procedures are applied. Some representatives of the monocotyledonous and dicotyledonous weed flora, which can be used to control the compounds according to the invention, should be mentioned by way of example, without any intention that the name should limit the species.
Vorzugsweise werden in einem erfindungsgemäßen Verfahren zur Bekämpfung von Schadpflanzen oder zur Wachstumsregulierung von Pflanzen eine oder mehrere Verbindungen der allgemeinen Formel (I) und/oder deren Salze zur Bekämpfung von Schadpflanzen oder zur Wachstumsregulierung in Kulturen von Nutzpflanzen oder Zierpflanzen eingesetzt, wobei die Nutzpflanzen oder Zierpflanzen in einer bevorzugten Ausgestaltung transgene Pflanzen sind. In a method according to the invention for controlling harmful plants or for regulating the growth of plants, one or more compounds of the general formula (I) and / or their salts are preferably used for controlling harmful plants or for regulating growth in crops of useful plants or ornamental plants, the useful plants or ornamental plants in a preferred embodiment are transgenic plants.
Die erfindungsgemäßen Verbindungen der allgemeinen Formel (1) und/oder deren Salze eignen sich zur Bekämpfung der folgenden Gattungen von monokotylen und dikotylen Schadpflanzen: The compounds of the general formula (1) according to the invention and / or their salts are suitable for combating the following genera of monocotyledonous and dicotyledonous harmful plants:
Monokotyle Schadpflanzen der Gattungen: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, lmperata, lschaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.  Monocotyledonous harmful plants of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostata, Festiochaperimist, Eriochaperimist, Eriochaperim , lschaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.
Dikotyle Schadpflanzen der Gattungen: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, lpomoea, Kochia, Lamium, Lepidium, Lindemia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium. Dicotyledonous harmful plants of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphor , Galinsoga, Galium, Hibiscus, lpomoea, Kochia, Lamium, Lepidium, Lindemia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senec , Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.
Werden die erfindungsgemäßen Verbindungen der allgemeinen Formel (1) vor dem Keimen der Schadpflanzen (Ungräser und/oder Unkräuter) auf die Erdoberfläche appliziert (Vorauflaufverfahren), so wird entweder das Auflaufen der Ungras- bzw. Unkrautkeimlinge vollständig verhindert oder diese wachsen bis zum Keimblattstadium heran, stellen jedoch dann ihr Wachstum ein und sterben schließlich nach Ablauf von drei bis vier Wochen vollkommen ab. If the compounds of the general formula (1) according to the invention are applied to the surface of the earth before the germinating of the harmful plants (grasses and / or weeds) (pre-emergence method), then either the emergence of the weed or weed seedlings is prevented completely or this grow to the cotyledon stage, but then stop growing and eventually die completely after three to four weeks.
Bei Applikation der Wirkstoffe der allgemeinen Formel (I) auf die grünen Pflanzenteile im When applying the active ingredients of the general formula (I) to the green parts of the plant in
Nachauflaufverfahren tritt nach der Behandlung Wachstumsstop ein und die Schadpflanzen bleiben in dem zum Applikationszeitpunkt vorhandenen Wachstumsstadium stehen oder sterben nach einer gewissen Zeit ganz ab, so dass auf diese Weise eine für die Kulturpflanzen schädliche Post-emergence treatment stops growing after the treatment and the harmful plants remain in the growth stage at the time of application or die completely after a certain time, so that this is harmful to the crop plants
Unkrautkonkurrenz sehr früh und nachhaltig beseitigt wird. Weed competition is eliminated very early and sustainably.
Obgleich die erfindungsgemäßen Verbindungen der allgemeinnen Formel (1) eine ausgezeichnete herbizide Aktivität gegenüber mono- und dikotylen Unkräutern aufweisen, werden Kulturpflanzen wirtschaftlich bedeutender Kulturen z.B. dikotyler Kulturen der Gattungen Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, fpomoea, Lactuca, Linum, Although the compounds of the general formula (1) according to the invention have excellent herbicidal activity against mono- and dicotyledon weeds, crop plants of economically important crops are e.g. dicotyledon cultures of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, fpomoea, Lactuca, Linum,
Lycopersicon, Miscanthus, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, oder monokotyler Kulturen der Gattungen Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea, abhängig von der Struktur der jeweiligen erfindungsgemäßen Verbindung und deren Aufwandmenge nur unwesentlich oder gar nicht geschädigt. Die vorliegenden Verbindungen eignen sich aus diesen Gründen sehr gut zur selektiven Bekämpfung von unerwünschtem Pflanzenwuchs in Pflanzenkulturen wie landwirtschaftlichen Nutzpflanzungen oder Zierpflanzungen.  Lycopersicon, Miscanthus, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledon cultures of the genera Allium, Pineapple, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea, depending on the structure of the each connection according to the invention and their application rate is only slightly or not at all damaged. For these reasons, the present compounds are very suitable for the selective control of undesired plant growth in plant crops, such as agricultural crops or ornamental crops.
Darüberhinaus weisen die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) (abhängig von ihrer jeweiligen Struktur und der ausgebrachten Aufwandmenge) hervorragende In addition, the compounds of the general formula (I) according to the invention have excellent properties (depending on their structure and the amount applied)
wachstumsregulatorische Eigenschaften bei Kulturpflanzen auf. Sie greifen regulierend in den pflanzeneigenen Stoffwechsel ein und können damit zur gezielten Beeinflussung von growth regulatory properties in crops. They intervene regulating the plant's own metabolism and can thus be used to influence
Pflanzeninhaltsstoffen und zur Emteerleichterung wie z.B. durch Auslösen von Desikkation und Wuchsstauchung eingesetzt werden. Desweiteren eignen sie sich auch zur generellen Steuerung und Hemmung von unerwünschtem vegetativem Wachstum, ohne dabei die Pflanzen abzutöten. Eine Hemmung des vegetativen Wachstums spielt bei vielen mono- und dikotylen Kulturen eine große Rolle, da beispielsweise die Lagerbildung hierdurch verringert oder völlig verhindert werden kann. Phytonutrients and to ease the crop, e.g. by triggering desiccation and stunted growth. Furthermore, they are also suitable for general control and inhibition of undesirable vegetative growth without killing the plants. Inhibiting vegetative growth plays a major role in many monocotyledonous and dicotyledonous crops, since, for example, this can reduce or completely prevent stock formation.
Aufgrund ihrer herbiziden und pflanzenwachstumsregulatorischen Eigenschaften können die Wirkstoffe der allgemeinen Formel (I) auch zur Bekämpfung von Schadpflanzen in Kulturen von gentechnisch oder durch konventionelle Mutagenese veränderten Pflanzen eingesetzt werden. Die transgenen Pflanzen zeichnen sich in der Regel durch besondere vorteilhafte Eigenschaften aus, beispielsweise durch Resistenzen gegenüber bestimmten Pestiziden, vor allem bestimmten Herbiziden, Resistenzen gegenüber Pflanzenkrankheiten oder Erregern von Pflanzenkrankheiten wie bestimmten Insekten oder Mikroorganismen wie Pilzen, Bakterien oder Viren. Andere besondere Eigenschaften betreffen z.B. das Emtegut hinsichtlich Menge, Qualität, Lagerfähigkeit, Zusammensetzung und spezieller Inhaltsstoffe.Because of their herbicidal and plant growth regulatory properties, the active compounds of the general formula (I) can also be used to control harmful plants in crops of plants which have been modified by genetic engineering or by conventional mutagenesis. The transgenic plants are generally distinguished by special advantageous properties, for example resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses. Other special properties concern e.g. Emtegut in terms of quantity, quality, shelf life, composition and special ingredients.
So sind transgene Pflanzen mit erhöhtem Stärkegehalt oder veränderter Qualität der Stärke oder solche mit anderer Fettsäurezusammensetzung des Emteguts bekannt. Thus, transgenic plants with an increased starch content or altered starch quality or with a different fatty acid composition of the crop are known.
Bevorzugt bezüglich transgener Kulturen ist die Anwendung der erfindungsgemäßen Verbindungen der allgemeinen Formel (I) und/oder deren Salze in wirtschaftlich bedeutenden transgenen Kulturen von Nutz und Zierpflanzen, z.B. von Getreide wie Weizen, Gerste, Roggen, Hafer, Hirse, Reis und Mais oder auch Kulturen von Zuckerrübe, Baumwolle, Soja, Raps, Kartoffel, Tomate, Erbse und anderen Gemüsesorten. Preferred with respect to transgenic cultures is the use of the compounds of the general formula (I) and / or their salts in economically important transgenic cultures of useful and ornamental plants, e.g. of cereals such as wheat, barley, rye, oats, millet, rice and corn or also crops of sugar beet, cotton, soybeans, rapeseed, potatoes, tomatoes, peas and other vegetables.
Vorzugsweise können die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) auch als Herbizide in Nutzpflanzenkulturen eingesetzt werden, welche gegenüber den phytotoxischen Wirkungen der Herbizide resistent sind bzw. gentechnisch resistent gemacht worden sind. The compounds of the general formula (I) according to the invention can preferably also be used as herbicides in crops which are resistant to the phytotoxic effects of the herbicides or have been rendered resistant to genetic engineering.
Aufgrund ihrer herbiziden und pflanzenwachstumsregulatorischen Eigenschaften können die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) auch zur Bekämpfung von Schadpflanzen in Kulturen von bekannten oder noch zu entwickelnden gentechnisch veränderten Pflanzen eingesetzt werden. Die transgenen Pflanzen zeichnen sich in der Regel durch besondere vorteilhafte Eigenschaften aus, beispielsweise durch Resistenzen gegenüber bestimmten Pestiziden, vor allem bestimmten Because of their herbicidal and plant growth regulatory properties, the compounds of the general formula (I) according to the invention can also be used to control harmful plants in crops of known or still to be developed genetically modified plants. The transgenic plants are usually distinguished by special advantageous properties, for example by resistance to certain pesticides, especially certain ones
Herbiziden, Resistenzen gegenüber Pflanzenkrankheiten oder Erregern von Pflanzenkrankheiten wie bestimmten Insekten oder Mikroorganismen wie Pilzen, Bakterien oder Viren. Andere besondere Eigenschaften betreffen z.B. das Emtegut hinsichtlich Menge, Qualität, Lagerfähigkeit, Herbicides, resistance to plant diseases or pathogens such as certain insects or microorganisms such as fungi, bacteria or viruses. Other special properties concern e.g. the crop in terms of quantity, quality, storability,
Zusammensetzung und spezieller Inhaltsstoffe. So sind transgene Pflanzen mit erhöhtem Stärkegehalt oder veränderter Qualität der Stärke oder solche mit anderer Fettsäurezusammensetzung des Emteguts bekannt. Weitere besondere Eigenschaften können in einer Toleranz oder Resistenz gegen abiotische Stressoren z.B. Hitze, Kälte, Trockenheit, Salz und ultraviolette Strahlung liegen. Composition and special ingredients. Thus, transgenic plants with an increased starch content or altered starch quality or with a different fatty acid composition of the crop are known. Other special properties can include tolerance or resistance to abiotic stressors e.g. There is heat, cold, dryness, salt and ultraviolet radiation.
Bevorzugt ist die Anwendung der erfindungsgemäßen Verbindungen der allgemeinen Formel (I) oder deren Salze in wirtschaftlich bedeutenden transgenen Kulturen von Nutz-und Zierpflanzen, z.B. von Getreide wie Weizen, Gerste, Roggen, Hafer, Triticale, Hirse, Reis, Maniok und Mais oder auch Kulturen von Zuckerrübe, Baumwolle, Soja, Raps, Kartoffel, Tomate, Erbse und anderen Gemüsesorten. Preference is given to using the compounds of the general formula (I) according to the invention or their salts in economically important transgenic crops of useful and ornamental plants, e.g. of cereals such as wheat, barley, rye, oats, triticale, millet, rice, manioc and corn or also crops of sugar beet, cotton, soybean, rapeseed, potato, tomato, pea and other vegetables.
Vorzugsweise können die Verbindungen der allgemeinen Formel (I) als Herbizide in The compounds of the general formula (I) can preferably be used as herbicides in
Nutzpflanzenkulturen eingesetzt werden, welche gegenüber den phytotoxischen Wirkungen der Herbizide resistent sind bzw. gentechnisch resistent gemacht worden sind. Herkömmliche Wege zur Herstellung neuer Pflanzen, die im Vergleich zu bisher vorkommenden Pflanzen modifizierte Eigenschaften aufweisen, bestehen beispielsweise in klassischen Crop crops are used which are resistant to the phytotoxic effects of the herbicides or have been made genetically resistant. Conventional ways of producing new plants which have modified properties in comparison to previously occurring plants are, for example, classic ones
Züchtungsverfahren und der Erzeugung von Mutanten. Alternativ können neue Pflanzen mit veränderten Eigenschaften mit Hilfe gentechnischer Verfahren erzeugt werden. Breeding methods and the generation of mutants. Alternatively, new plants with modified properties can be created using genetic engineering methods.
Zahlreiche molekularbiologische Techniken, mit denen neue transgene Pflanzen mit veränderten Eigenschaften hergestellt werden können, sind dem Fachmann bekannt. Für derartige gentechnische Manipulationen können Nucleinsäuremoleküle in Plasmide eingebracht werden, die eine Mutagenese oder eine Sequenzveränderung durch Rekombination von DNA-Sequenzen erlauben. Mit Hilfe von Standardverfahren können z.B. Basenaustausche vorgenommen, Teilsequenzen entfernt oder natürliche oder synthetische Sequenzen hinzugefügt werden. Für die Verbindung der DNA-Fragmente untereinander können an die Fragmente Adaptoren oder Linker angesetzt werden. Numerous molecular biological techniques with which new transgenic plants with modified properties can be produced are known to the person skilled in the art. For such genetic engineering manipulations, nucleic acid molecules can be introduced into plasmids which allow mutagenesis or a sequence change by recombining DNA sequences. With the help of standard procedures e.g. Base exchanges made, partial sequences removed or natural or synthetic sequences added. To connect the DNA fragments to one another, adapters or linkers can be attached to the fragments.
Die Herstellung von Pflanzenzellen mit einer verringerten Aktivität eines Genprodukts kann beispielsweise erzielt werden durch die Expression mindestens einer entsprechenden antisense-RNA, einer sense-RNA zur Erzielung eines Cosuppressionseffektes oder die Expression mindestens eines entsprechend konstruierten Ribozyms, das spezifisch Transkripte des obengenannten Genprodukts spaltet. The production of plant cells with a reduced activity of a gene product can be achieved, for example, by the expression of at least one corresponding antisense RNA, a sense RNA to achieve a cosuppression effect or the expression of at least one appropriately constructed ribozyme which specifically cleaves transcripts of the above-mentioned gene product.
Hierzu können zum einen DNA-Moleküle verwendet werden, die die gesamte codierende Sequenz eines Genprodukts einschließlich eventuell vorhandener flankierender Sequenzen umfassen, als auch DNA- Moleküle, die nur Teile der codierenden Sequenz umfassen, wobei diese Teile lang genug sein müssen, um in den Zellen einen antisense-Effekt zu bewirken. Möglich ist auch die Verwendung von DNA- Sequenzen, die einen hohen Grad an Homologie zu den codiereden Sequenzen eines Genprodukts aufweisen, aber nicht vollkommen identisch sind. For this purpose, DNA molecules can be used that comprise the entire coding sequence of a gene product, including any flanking sequences that may be present, as well as DNA molecules that only comprise parts of the coding sequence, these parts having to be long enough to be in the cells to cause 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.
Bei der Expression von Nucleinsäuremolekülen in Pflanzen kann das synthetisierte Protein in jedem beliebigen Kompartiment der pflanzlichen Zelle lokalisiert sein. Um aber die Lokalisation in einem bestimmten Kompartiment zu erreichen, kann z.B. die codierende Region mit DNA-Sequenzen verknüpft werden, die die Lokalisierung in einem bestimmten Kompartiment gewährleisten. Derartige Sequenzen sind dem Fachmann bekannt (siehe beispielsweise Braun et al., EMBO J. 11 (1992), 3219- 3227). Die Expression der Nukleinsäuremoleküle kann auch in den Organellen der Pflanzenzellen stattfinden. When nucleic acid molecules are expressed in plants, the synthesized protein can be located in any compartment of the plant cell. However, in order to achieve localization in a certain compartment, e.g. the coding region is linked to DNA sequences which ensure localization in a specific compartment. Such sequences are known to the person skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227). The expression of the nucleic acid molecules can also take place in the organelles of the plant cells.
Die transgenen Pflanzenzellen können nach bekannten Techniken zu ganzen Pflanzen regeneriert werden. Bei den transgenen Pflanzen kann es sich prinzipiell um Pflanzen jeder beliebigen The transgenic plant cells can be regenerated into whole plants using known techniques. In principle, the transgenic plants can be any plants
Pflanzenspezies handeln, d.h. sowohl monokotyle als auch dikotyle Pflanzen. So sind transgene Pflanzen erhältlich, die veränderte Eigenschaften durch Überexpression, Suppression oder Inhibierung homologer (= natürlicher) Gene oder Gensequenzen oder Expression heterologer (= fremder) Gene oder Gensequenzen aufweisen. Act plant species, ie both monocot and dicot plants. Thus, transgenic plants are available which have changed properties due to overexpression, suppression or inhibition of homologous (= natural) genes or gene sequences or expression of heterologous (= foreign) genes or gene sequences.
Vorzugsweise können die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) in transgenen Kulturen eingesetzt werden, welche gegen Wuchsstoffe, wie z.B. Dicamba oder gegen Herbizide, die essentielle Pflanzenenzyme, z.B. Acetolactatsynthasen (ALS), EPSP Synthasen, Glutaminsynthasen (GS) oder Hydoxyphenylpyruvat Dioxygenasen (HPPD) hemmen, respektive gegen Herbizide aus der Gruppe der Sulfonylharnstoffe, der Glyphosate, Glufosinate oder Benzoylisoxazole und analogen Wirkstoffe, resistent sind. The compounds of the general formula (I) according to the invention can preferably be used in transgenic cultures which are active against growth substances, e.g. Dicamba or against herbicides, the essential plant enzymes, e.g. Inhibit acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydoxyphenyl pyruvate dioxygenases (HPPD), or are resistant to herbicides from the group of sulfonylureas, glyphosate, glufosinate or benzoylisoxazole and analogous active ingredients.
Bei der Anwendung der erfindungsgemäßen Verbindungen der allgemeinen Formel (I) in transgenen Kulturen treten neben den in anderen Kulturen zu beobachtenden Wirkungen gegenüber Schadpflanzen oftmals Wirkungen auf, die für die Applikation in der jeweiligen transgenen Kultur spezifisch sind, beispielsweise ein verändertes oder speziell erweitertes Unkrautspektrum, das bekämpft werden kann, veränderte Aufwandmengen, die für die Applikation eingesetzt werden können, vorzugsweise gute Kombinierbarkeit mit den Herbiziden, gegenüber denen die transgene Kultur resistent ist, sowie Beeinflussung von Wuchs und Ertrag der transgenen Kulturpflanzen. When the compounds of the general formula (I) according to the invention are used in transgenic crops, in addition to the effects on harmful plants which can be observed in other crops, effects often occur which are specific for the application in the respective transgenic crop, for example a modified or specially expanded weed spectrum, that can be combated, changed application rates that can be used for the application, preferably good combinability with the herbicides to which the transgenic crop is resistant, and influencing the growth and yield of the transgenic crop plants.
Gegenstand der Erfindung ist deshalb auch die Verwendung der erfindungsgemäßen Verbindungen der allgemeinen Formel (I) und/oder deren Salze als Herbizide zur Bekämpfung von Schadpflanzen in Kulturen von Nutz- oder Zierpflanzen, gegebenenfalls in transgenen Kulturpflanzen. The invention therefore also relates to the use of the compounds of the general formula (I) according to the invention and / or their salts as herbicides for controlling harmful plants in crops of useful or ornamental plants, optionally in transgenic crop plants.
Bevorzugt ist die Verwendung von Verbindungen der allgemeinen Formel (I) in Getreide, dabei vorzugsweise Mais, Weizen, Gerste, Roggen, Hafer, Hirse, oder Reis, im Vor- oder Nachauflauf. Preference is given to using compounds of the general formula (I) in cereals, preferably maize, wheat, barley, rye, oats, millet or rice, in the pre- or post-emergence.
Bevorzugt ist auch die Verwendung von Verbindungen der allgemeinene Formel (I) in Soja im Vor oder Nachauflauf. Preference is also given to using compounds of the general formula (I) in soya before or after emergence.
Die Verwendung erfindungsgemäßer Verbindungen der Formel (I) zur Bekämpfung von Schadpflanzen oder zur Wachstumsregulierung von Pflanzen schließt auch den Fall ein, bei dem einer Verbindung der allgemeinen Formel (I) oder deren Salz erst nach der Ausbringung auf der Pflanze, in der Pflanze oder im Boden aus einer Vorläufersubstanz ("Prodrug") gebildet wird. The use of compounds of the formula (I) according to the invention for controlling harmful plants or for regulating the growth of plants also includes the case in which a compound of the general formula (I) or its salt is only applied after application to the plant, in the plant or in Soil is formed from a precursor ("prodrug").
Gegenstand der Erfindung ist auch die Verwendung einer oder mehrerer Verbindungen der allgemeinen Formel (I) oder deren Salzen bzw. eines erfindungsgemäßen Mittels (wie nachstehend definiert) (in einem Verfahren) zur Bekämpfung von Schadpflanzen oder zur Wachstumsregulierung von Pflanzen, dadurch gekennzeichnet, dass man eine wirksame Menge einer oder mehreren Verbindungen der allgemeinen Formel (I) oder deren Salzen auf die Pflanzen (Schadpflanzen, gegebenenfalls zusammen mit den Nutzpflanzen) Pflanzensamen, den Boden, in dem oder auf dem die Pflanzen wachsen, oder die Anbaufläche appliziert. The invention also relates to the use of one or more compounds of the general formula (I) or their salts or an agent according to the invention (as defined below) (in a method) for controlling harmful plants or for regulating the growth of plants, characterized in that an effective amount of one or more compounds of the general formula (I) or their salts are applied to the plants (harmful plants, if appropriate together with the useful plants) plant seeds, the soil , in or on which the plants grow, or the cultivated area is applied.
Gegenstand der Erfindung ist auch ein herbizides und/oder pflanzenwachstumsregulierendes Mittel, dadurch gekennzeichnet, dass das Mittel The invention also relates to a herbicidal and / or plant growth-regulating agent, characterized in that the agent
(a) eine oder mehrere Verbindungen der allgemeinen Formel (I) und/oder deren Salze enthält wie oben definiert, vorzugsweise in einer der als bevorzugt bzw. besonders bevorzugt gekennzeichneten (a) contains one or more compounds of the general formula (I) and / or their salts as defined above, preferably in one of those identified as preferred or particularly preferred
Ausgestaltung, insbesondere eine oder mehrere Verbindungen der Formeln Design, in particular one or more compounds of the formulas
(1-001) bis (1-662) und/oder deren Salze, jeweils wie oben definiert,  (1-001) to (1-662) and / or their salts, each as defined above,
und and
(b) ein oder mehrere weitere Stoffe ausgewählt aus den Gruppen (i) und/oder (ii): (b) one or more further substances selected from groups (i) and / or (ii):
(i) ein oder mehrere weitere agrochemisch wirksame Stoffe, vorzugsweise ausgewählt aus der Gruppe bestehend aus Insektiziden, Akariziden, Nematiziden, weiteren Herbiziden (d.h. solche, die nicht der oben definierten allgemeinen Formel (I) entsprechen), Fungiziden, Safenern, Düngemitteln und/oder weiteren Wachstumsregulatoren, (i) one or more further agrochemically active substances, preferably selected from the group consisting of insecticides, acaricides, nematicides, further herbicides (ie those which do not correspond to the general formula (I) defined above), fungicides, safeners, fertilizers and / or other growth regulators,
(ii) ein oder mehrere im Pflanzenschutz übliche Formulierungshilfsmittel. (ii) one or more formulation auxiliaries customary in crop protection.
Die weiteren agrochemischen wirksamen Stoffe des Bestandteils (i) eines erfindungsgemäßen Mittels sind dabei vorzugsweise ausgewählt aus der Gruppe der Stoffe, die in "The Pesticide Manual", l6th edition, The British Crop Protection Council und the Royal Soc. of Chemistry, 2012 genannt sind. The further agrochemically active substances of component (i) of an agent according to the invention are preferably selected from the group of substances described in "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012.
Ein erfindungsgemäßes herbizides oder pflanzenwachstumsregulierendes Mittel, umfasst vorzugsweise ein, zwei, drei oder mehr im Pflanzenschutz übliche Formulierungshilfsmittel (ii) ausgewählt aus der Gruppe bestehend aus Tensiden, Emulgatoren, Dispergiermitteln, Filmbildnem, Verdickungsmitteln, anorganischen Salzen, Stäubemitteln, bei 25 °C und 1013 mbar festen Trägerstoffen, vorzugsweise adsorptionsfähigen, granulierten Inertmaterialien, Netzmitteln, Antioxidationsmitteln, Stabilisatoren, Puffersubstanzen, Antischaummitteln, Wasser, organischen Lösungsmitteln, vorzugsweise bei 25 °C und 1013 mbar mit Wasser in jedem beliebigen Verhältnis mischbare organische Lösungsmittel. Die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) können in Form von Spritzpulvem, emulgierbaren Konzentraten, versprühbaren Lösungen, Stäubemitteln oder Granulaten in den üblichen Zubereitungen angewendet werden. Gegenstand der Erfindung sind deshalb auch herbizide und pflanzenwachstumsregulierende Mittel, die Verbindungen der allgemeinen Formel (I) und/oder deren Salze enthalten. A herbicidal or plant growth-regulating agent according to the invention preferably comprises one, two, three or more formulation auxiliaries (ii) customary in crop protection selected from the group consisting of surfactants, emulsifiers, dispersants, film formers, thickeners, inorganic salts, dusts, at 25 ° C. and 1013 mbar solid carriers, preferably adsorbable, granulated inert materials, wetting agents, antioxidants, stabilizers, buffer substances, anti-foaming agents, water, organic solvents, preferably at 25 ° C. and 1013 mbar, water-miscible organic solvents in any ratio. The compounds of the general formula (I) according to the invention can be used in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules in the customary formulations. The invention therefore also relates to herbicidal and plant growth-regulating compositions which comprise compounds of the general formula (I) and / or their salts.
Die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) und/oder deren Salze können auf verschiedene Art formuliert werden, je nachdem welche biologischen und/oder chemisch-physikalischen Parameter vorgegeben sind. Als Formulierungsmöglichkeiten kommen beispielsweise in Frage: The compounds of general formula (I) and / or their salts according to the invention can be formulated in various ways, depending on which biological and / or chemical-physical parameters are specified. Examples of possible wording are:
Spritzpulver (WP), wasserlösliche Pulver (SP), wasserlösliche Konzentrate, emulgierbare Konzentrate (EC), Emulsionen (EW), wie Öl-in-Wasser- und Wasser-in-Öl-Emulsionen, versprühbare Lösungen, Suspensionskonzentrate (SC), Dispersionen auf Öl- oder Wasserbasis, ölmischbare Lösungen, Wettable powder (WP), water-soluble powder (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW) such as oil-in-water and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), dispersions oil or water based, oil miscible solutions,
Kapselsuspensionen (CS), Stäubemittel (DP), Beizmittel, Granulate für die Streu- und Capsule suspensions (CS), dusts (DP), pickling agents, granules for the litter and
Bodenapplikation, Granulate (GR) in Form von Mikro-, Sprüh-, Aufzugs- und Adsorptionsgranulaten, wasserdispergierbare Granulate (WG), wasserlösliche Granulate (SG), ULV-Formulierungen, Soil application, granules (GR) in the form of micro, spray, elevator and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations,
Mikrokapseln und Wachse. Microcapsules and waxes.
Diese einzelnen Formulierungstypen und die Formulierungshilfsmittel wie Inertmaterialien, Tenside, Lösungsmittel und weitere Zusatzstoffe sind dem Fachmann bekannt, und werden beispielsweise beschrieben in: Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell N.J., H.v. Olphen, "Introduction to Clay Colloid Chemistry"; 2nd Ed., J. Wiley & Sons, N.Y.; C. Marsden, "Solvents Guide"; 2nd Ed., Interscience, N.Y. 1963; McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt, "Grenzflächenaktive These individual formulation types and the formulation auxiliaries such as inert materials, surfactants, solvents and other additives are known to the person skilled in the art and are described, for example, in: Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell N.J., H.v. Olphen, "Introduction to Clay Colloid Chemistry"; 2nd Ed., J. Wiley & Sons, N.Y .; C. Marsden, "Solvents Guide"; 2nd Ed., Interscience, N.Y. 1963; McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood N.J .; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt, "Interface Active
Äthylenoxidaddukte", Wiss. Verlagsgesellschaft, Stuttgart 1976; Winnacker-Küchler, "Chemische Technologie", Band 7, C. Hanser Verlag München, 4. Aufl. 1986. Äthylenoxidaddukte ", Wiss. Verlagsgesellschaft, Stuttgart 1976; Winnacker-Küchler," Chemische Technologie ", Volume 7, C. Hanser Verlag Munich, 4th ed. 1986.
Spritzpulver sind in Wasser gleichmäßig dispergierbare Präparate, die neben dem Wirkstoff außer einem Verdünnungs- oder Inertstoff noch Tenside ionischer und/oder nichtionischer Art (Netzmittel, Spray powders are preparations which are uniformly dispersible in water and which, in addition to the active substance, contain not only a diluent or an inert substance, but also ionic and / or nonionic surfactants (wetting agents,
Dispergiermittel), z.B. polyoxyethylierte Alkylphenole, polyoxethylierte Fettalkohole, polyoxethylierte Fettamine, Fettalkoholpolyglykolethersulfate, Alkansulfonate, Alkylbenzolsulfonate, ligninsulfonsaures Natrium, 2,2'-dinaphthylmethan-6,6'-disulfonsaures Natrium, dibutylnaphthalin-sulfonsaures Natrium oder auch oleoylmethyltaurinsaures Natrium enthalten. Zur Herstellung der Spritzpulver werden die herbiziden Wirkstoffe beispielsweise in üblichen Apparaturen wie Hammermühlen, Gebläsemühlen und Luftstrahlmühlen feingemahlen und gleichzeitig oder anschließend mit den Formulierungshilfsmitteln vermischt. Emulgierbare Konzentrate werden durch Auflösen des Wirkstoffes in einem organischen Lösungsmittel z.B. Butanol, Cyclohexanon, Dimethylformamid, Xylol oder auch höhersiedenden Aromaten oder Kohlenwasserstoffen oder Mischungen der organischen Lösungsmittel unter Zusatz von einem oder mehreren Tensiden ionischer und/oder nichtionischer Art (Emulgatoren) hergestellt. Als Emulgatoren können beispielsweise verwendet werden: Alkylarylsulfonsaure Calcium-Salze wie Dispersants), for example polyoxyethylated alkylphenols, polyoxethylated fatty alcohols, polyoxethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, ligninsulfonic acid sodium, 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium, sodium dibutyla naphthalenethyl or also containing sulfonate. To produce the wettable powders, the herbicidal active ingredients are, for example, finely ground in customary equipment, such as hammer mills, fan mills and air jet mills, and mixed at the same time or subsequently with the formulation auxiliaries. Emulsifiable concentrates are prepared by dissolving the active ingredient in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or even higher-boiling aromatics or hydrocarbons or mixtures of the organic solvents with the addition of one or more ionic and / or nonionic surfactants (emulsifiers). Examples of emulsifiers that can be used are: alkylarylsulfonic acid calcium salts such as
Ca-dodecylbenzolsulfonat oder nichtionische Emulgatoren wie Fettsäurepolyglykolester, Ca-dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters,
Alkylarylpolyglykolether, F ettalkoholpolyglykolether, Propylenoxid-Ethylenoxid- Kondensationsprodukte, Alkylpolyether, Sorbitanester wie z.B. Sorbitanfettsäureester oder Alkylaryl polyglycol ether, fatty alcohol polyglycol ether, propylene oxide-ethylene oxide condensation products, alkyl polyether, sorbitan esters such as e.g. Sorbitan fatty acid esters or
Polyoxethylensorbitanester wie z.B. Polyoxyethylensorbitanfettsäureester. Polyoxethylene sorbitan esters such as e.g. Polyoxyethylene.
Stäubemittel erhält man durch Vermahlen des Wirkstoffes mit fein verteilten festen Stoffen, z.B. Dusts are obtained by grinding the active ingredient with finely divided solid substances, e.g.
Talkum, natürlichen Tonen, wie Kaolin, Bentonit und Pyrophyllit, oder Diatomeenerde. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
Suspensionskonzentrate können auf Wasser- oder Ölbasis sein. Sie können beispielsweise durch Naß- Vermahlung mittels handelsüblicher Perlmühlen und gegebenenfalls Zusatz von Tensiden, wie sie z.B. oben bei den anderen Formulierungstypen bereits aufgeführt sind, hergestellt werden. Suspension concentrates can be water or oil based. You can, for example, by wet grinding using commercially available bead mills and optionally adding surfactants such as those e.g. already listed above for the other types of formulation.
Emulsionen, z.B. Öl-in-Wasser-Emulsionen (EW), lassen sich beispielsweise mittels Rührern, Emulsions, e.g. Oil-in-water emulsions (EW) can be mixed using stirrers,
Kolloidmühlen und/oder statischen Mischern unter Verwendung von wäßrigen organischen Colloid mills and / or static mixers using aqueous organic
Lösungsmitteln und gegebenenfalls Tensiden, wie sie z.B. oben bei den anderen Formulierungstypen bereits aufgeführt sind, hersteilen. Solvents and optionally surfactants, e.g. already listed above for the other formulation types.
Granulate können entweder durch Verdüsen des Wirkstoffes auf adsorptionsfähiges, granuliertes Inertmaterial hergestellt werden oder durch Aufbringen von Wirkstoffkonzentraten mittels Klebemitteln, z.B. Polyvinylalkohol, polyacrylsaurem Natrium oder auch Mineralölen, auf die Oberfläche von Trägerstoffen wie Sand, Kaolinite oder von granuliertem Inertmaterial. Auch können geeignete Granules can either be produced by spraying the active ingredient onto adsorbable, granulated inert material or by applying active ingredient concentrates by means of adhesives, e.g. Polyvinyl alcohol, sodium polyacrylic acid or mineral oils, on the surface of carriers such as sand, kaolinite or granulated inert material. Also suitable ones
Wirkstoffe in der für die Herstellung von Düngemittelgranulaten üblichen Weise - gewünschtenfalls in Mischung mit Düngemitteln - granuliert werden. Active ingredients are granulated in the manner customary for the production of fertilizer granules - if desired in a mixture with fertilizers.
Wasserdispergierbare Granulate werden in der Regel nach den üblichen Verfahren wie Sprühtrocknung, Wirbelbett-Granulierung, Teller-Granulierung, Mischung mit Hochgeschwindigkeitsmischem und Extrusion ohne festes Inertmaterial hergestellt. Water-dispersible granules are generally produced using the customary processes, such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material.
Zur Herstellung von Teller-, Fließbett-, Extruder- und Sprühgranulaten siehe z.B. Verfahren in "Spray- Drying Handbook" 3rd ed. 1979, G. Goodwin Ltd., London; J.E. Browning, "Agglomeration", Chemical and Engineering 1967, Seiten 147 ff; "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York 1973, S. 8-57. Für weitere Einzelheiten zur Formulierung von Pflanzenschutzmitteln siehe z.B. G.C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, Seiten 81-96 und J.D. Freyer, S.A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, Seiten 101-103. For the production of plate, fluidized bed, extruder and spray granules, see, for example, the process in "Spray-Drying Handbook" 3rd ed. 1979, G. Goodwin Ltd., London; JE Browning, "Agglomeration", Chemical and Engineering 1967, pages 147 ff; "Perry's Chemical Engineer's Handbook," 5th Ed., McGraw-Hill, New York 1973, pp. 8-57. For further details on the formulation of crop protection agents, see, for example, GC Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pages 81-96 and JD Freyer, SA Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.
Die agrochemischen Zubereitungen, vorzugsweise herbizide oder pflanzenwachstumsregulierende Mittel der vorliegenden Erfindung enthalten vorzugsweise eine Gesamtmenge von 0,1 bis 99 Gew.-%, bevorzugt 0,5 bis 95 Gew.-%, weiter bevorzugt 1 bis 90 Gew.-%, insbesondere bevorzugt 2 bis 80 Gew.-%, an Wirkstoffen der allgemeinen Formel (I) und deren Salzen. The agrochemical preparations, preferably herbicidal or plant growth-regulating agents of the present invention preferably contain a total amount of 0.1 to 99% by weight, preferably 0.5 to 95% by weight, more preferably 1 to 90% by weight, particularly preferably 2 to 80% by weight of active compounds of the general formula (I) and their salts.
In Spritzpulvem beträgt die Wirkstoffkonzentration z.B. etwa 10 bis 90 Gew.-%, der Rest zu 100 Gew.-% besteht aus üblichen Formulierungsbestandteilen. Bei emulgierbaren Konzentraten kann die Wirkstoffkonzentration etwa 1 bis 90, vorzugsweise 5 bis 80 Gew.-% betragen. Staubförmige The active substance concentration in wettable powders is e.g. about 10 to 90 wt .-%, the rest of 100 wt .-% consists of conventional formulation components. In the case of emulsifiable concentrates, the active substance concentration can be about 1 to 90, preferably 5 to 80,% by weight. Powdery
Formulierungen enthalten 1 bis 30 Gew.-% Wirkstoff, vorzugsweise meistens 5 bis 20 Gew.-% an Wirkstoff, versprühbare Lösungen enthalten etwa 0,05 bis 80, vorzugsweise 2 bis 50 Gew.-% Wirkstoff. Bei wasserdispergierbaren Granulaten hängt der Wirkstoffgehalt zum Teil davon ab, ob die wirksame Verbindung flüssig oder fest vorliegt und welche Granulierhilfsmittel, Füllstoffe usw. verwendet werden. Bei den in Wasser dispergierbaren Granulaten liegt der Gehalt an Wirkstoff beispielsweise zwischen 1 und 95 Gew.-%, vorzugsweise zwischen 10 und 80 Gew.-%. 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. In the case of water-dispersible granules, the active ingredient content depends in part on whether the active compound is in liquid or solid form and which granulating aids, fillers, etc. are used. The active ingredient content of the water-dispersible granules is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
Daneben enthalten die genannten Wirkstofformulierungen gegebenenfalls die jeweils üblichen Haft-, Netz-, Dispergier-, Emulgier-, Penetrations-, Konservierungs-, Frostschutz- und Lösungsmittel, Füll-, Träger- und Farbstoffe, Entschäumer, Verdunstungshemmer und den pH-Wert und die Viskosität beeinflussende Mittel. Beispiele für Formulierungshilfsmittel sind unter anderem in "Chemistry and Technology of Agrochemical Formulations", ed. D. A. Knowles, Kluwer Academic Publishers (1998) beschrieben. In addition, the active ingredient formulations mentioned may contain the customary adhesives, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreezes and solvents, fillers, carriers and dyes, defoamers, evaporation inhibitors and the pH and Agents influencing viscosity. Examples of formulation auxiliaries are described, inter alia, in "Chemistry and Technology of Agrochemical Formulations", ed. D. A. Knowles, Kluwer Academic Publishers (1998).
Die erfindungsgemäßen Verbindungen der allgemeinen Formel (1) oder deren Salze können als solche oder in Form ihrer Zubereitungen (Formulierungen) mit anderen pestizid wirksamen Stoffen, wie z.B. lnsektiziden, Akariziden, Nematiziden, Herbiziden, Fungiziden, Safenern, Düngemitteln und/oder Wachstumsregulatoren kombiniert eingesetzt werden, z.B. als Fertigformulierung oder als The compounds of the general formula (1) according to the invention or their salts can be used as such or in the form of their preparations (formulations) with other pesticidally active substances, e.g. Insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and / or growth regulators can be used in combination, e.g. as a finished formulation or as
Tankmischungen. Die Kombinationsformulierungen können dabei auf Basis der obengenannten Formulierungen hergestellt werden, wobei die physikalischen Eigenschaften und Stabilitäten der zu kombinierenden Wirkstoffe zu berücksichtigen sind. Als Kombinationspartner für die erfindungsgemäßen Verbindungen der allgemeinen Formel (1) in Mischungsformulierungen oder im Tank-Mix sind beispielsweise bekannte Wirkstoffe, die auf einer lnhibition von beispielsweise Acetolactat-Synthase, Acetyl-CoA-Carboxylase, Cellulose-Synthase, Enolpyruvylshikimat-3-phosphat-Synthase, Glutamin-Synthetase, p-Hydroxyphenylpyruvat- Dioxygenase, Phytoendesaturase, Photosystem I, Photosystem II, Protoporphyrinogen-Oxidase beruhen, einsetzbar, wie sie z.B. in Weed Research 26 (1986) 441-445 oder "The Pesticide Manual", l6th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 und der dort zitierten Literatur beschrieben sind. Tank mixes. The combination formulations can be prepared on the basis of the formulations mentioned above, taking into account the physical properties and stabilities of the active compounds to be combined. As a combination partner for the compounds of the general formula (1) according to the invention in mixture formulations or in a tank mix, there are, for example, known active ingredients which are based on an inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate Synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoendesaturase, Photosystem I, Photosystem II, protoporphyrinogen oxidase, can be used, as described, for example, in Weed Research 26 (1986) 441-445 or "The Pesticide Manual", sixth edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 and the literature cited therein.
Von besonderem Interesse ist die selektive Bekämpfung von Schadpflanzen in Kulturen von Nutz- und Zierpflanzen. Obgleich die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) bereits in vielen Kulturen sehr gute bis ausreichende Selektivität aufweisen, können prinzipiell in einigen Kulturen und vor allem auch im Falle von Mischungen mit anderen Herbiziden, die weniger selektiv sind, Phytotoxizitäten an den Kulturpflanzen auftreten. Diesbezüglich sind Kombinationen The selective control of harmful plants in crops of useful and ornamental plants is of particular interest. Although the compounds of the general formula (I) according to the invention already have very good to sufficient selectivity in many crops, phytotoxicity can occur on the crop plants in principle in some crops and especially in the case of mixtures with other herbicides which are less selective. In this regard, combinations are
erfindungsgemäßer Verbindungen (I) von besonderem Interesse, welche die Verbindungen der allgemeinen Formel (I) bzw. deren Kombinationen mit anderen Herbiziden oder Pestiziden und Safenern enthalten. Die Safener, welche in einem antidotisch wirksamen Gehalt eingesetzt werden, reduzieren die phytotoxischen Nebenwirkungen der eingesetzten Herbizide/Pestizide, z.B. in wirtschaftlich bedeutenden Kulturen wie Getreide (Weizen, Gerste, Roggen, Mais, Reis, Hirse), Zuckerrübe, Zuckerrohr, Raps, Baumwolle und Soja, vorzugsweise Getreide. Compounds (I) according to the invention of particular interest which contain the compounds of the general formula (I) or their combinations with other herbicides or pesticides and safeners. The safeners, which are used in an antidotically effective content, reduce the phytotoxic side effects of the herbicides / pesticides used, e.g. in economically important crops such as cereals (wheat, barley, rye, corn, rice, millet), sugar beet, sugar cane, rapeseed, cotton and soybeans, preferably cereals.
Die Gewichtsverhältnisse von Herbizid(mischung) zu Safener hängt im Allgemeinen von der The weight ratio of herbicide (mixture) to safener generally depends on the
Aufwandmenge an Herbizid und der Wirksamkeit des jeweiligen Safeners ab und kann innerhalb weiter Grenzen variieren, beispielsweise im Bereich von 200:1 bis 1 :200, vorzugsweise 100:1 bis 1 :100, insbesondere 20:1 bis 1 :20. Die Safener können analog den Verbindungen der allgemeinen Formel (I) oder deren Mischungen mit weiteren Herbiziden/Pestiziden formuliert werden und als Application rate of herbicide and the effectiveness of the respective safener and can vary within wide limits, for example in the range from 200: 1 to 1: 200, preferably 100: 1 to 1: 100, in particular 20: 1 to 1:20. The safeners can be formulated analogously to the compounds of the general formula (I) or their mixtures with further herbicides / pesticides and as
Fertigformulierung oder Tankmischung mit den Herbiziden bereitgestellt und angewendet werden. Ready formulation or tank mix with the herbicides are provided and applied.
Zur Anwendung werden die in handelsüblicher Form vorliegenden Herbizid- oder Herbizid- Safener- Formulierungen gegebenenfalls in üblicher Weise verdünnt z.B. bei Spritzpulvem, emulgierbaren Konzentraten, Dispersionen und wasserdispergierbaren Granulaten mittels Wasser. Staubförmige Zubereitungen, Boden- bzw. Streugranulate sowie versprühbare Lösungen werden vor der Anwendung üblicherweise nicht mehr mit weiteren inerten Stoffen verdünnt. For use, the herbicide or herbicide safener formulations present in commercially available form are optionally diluted in the customary manner, for example for wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules using water. Preparations in the form of dust, ground granules or granules as well as sprayable solutions are usually no longer diluted with other inert substances before use.
Äußere Bedingungen wie Temperatur, Feuchtigkeit etc. beeinflussen zu einem gewissen Teil die Aufwandmenge der Verbindungen der allgemeinen Formel (I) und/oder deren Salze. Die External conditions such as temperature, humidity, etc. influence to a certain extent the application rate of the compounds of the general formula (I) and / or their salts. The
Aufwandmenge kann dabei innerhalb weiter Grenzen variieren. Für die Anwendung als Herbizid zur Bekämpfung von Schadpflanzen liegt die Gesamtmenge an Verbindungen der allgemeinen Formel (I) und deren Salze vorzugsweise im Bereich von 0,001 bis 10,0 kg/ha, bevorzugt im Bereich von 0,005 bis 5 kg/ha, weiter bevorzugt im Bereich von 0,01 bis 1,5 kg/ha, insbesondere bevorzugt im Bereich von 0,05 bis 1 kg/ha. Dies gilt sowohl für die Anwendung im Vorauflauf oder im Nachauflauf. The application rate can vary within wide limits. For use as a herbicide Control of harmful plants is the total amount of compounds of general formula (I) and their salts preferably in the range from 0.001 to 10.0 kg / ha, preferably in the range from 0.005 to 5 kg / ha, more preferably in the range from 0.01 to 1.5 kg / ha, particularly preferably in the range from 0.05 to 1 kg / ha. This applies to both pre-emergence and post-emergence applications.
Bei der Anwendung von erfindungsgemäßen Verbindungen der allgemeinen Formel (I) und/oder deren Salzen als Pflanzenwachstumsregulator, beispielsweise als Halmverkürzer bei Kulturpflanzen, wie sie oben genannt worden sind, vorzugsweise bei Getreidepflanzen wie Weizen, Gerste, Roggen, Triticale, Hirse, Reis oder Mais, liegt die Gesamt- Aufwandmenge vorzugsweise im Bereich von 0,001 bis 2 kg/ha, vorzugsweise im Bereich von 0,005 bis 1 kg/ha, insbesondere im Bereich von 10 bis 500 g/ha, ganz besonders bevorzugt im Bereich von 20 bis 250 g/ha. Dies gilt sowohl für die Anwendung im When using compounds of general formula (I) according to the invention and / or their salts as plant growth regulators, for example as stalk shorteners in crop plants as mentioned above, preferably in cereal plants such as wheat, barley, rye, triticale, millet, rice or corn , the total application rate is preferably in the range from 0.001 to 2 kg / ha, preferably in the range from 0.005 to 1 kg / ha, in particular in the range from 10 to 500 g / ha, very particularly preferably in the range from 20 to 250 g / ha Ha. This applies both to the application in
Vorauflauf oder im Nachauflauf. Pre-emergence or post-emergence.
Die Applikation als Halmverkürzer kann in verschiedenen Stadien des Wachstums der Pflanzen erfolgen. Bevorzugt ist beispielsweise die Anwendung nach der Bestockung am Beginn des The application as a straw shortener can take place in different stages of the growth of the plants. For example, use after planting at the beginning of the
Längenwachstums . Linear growth.
Alternativ kommt bei der Anwendung als Pflanzenwachstumsregulator auch die Behandlung des Saatguts in Frage, welche die unterschiedlichen Saatgutbeiz- und Beschichtungstechniken einschließt. Die Aufwandmenge hängt dabei von den einzelnen Techniken ab und kann in Vorversuchen ermittelt werden. Alternatively, when used as a plant growth regulator, the treatment of the seed, which includes the different seed dressing and coating techniques, can also be used. The application rate depends on the individual techniques and can be determined in preliminary tests.
Als Kombinationspartner für die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) in erfindungsgemäßen Mitteln (z.B. Mischungsformulierungen oder im Tank-Mix) sind beispielsweise bekannte Wirkstoffe, die auf einer Inhibition von beispielsweise Acetolactat-Synthase, Acetyl-CoA- Carboxylase, Cellulose-Synthase, Enolpyruvylshikimat-3-phosphat-Synthase, Glutamin-Synthetase, p- Hydroxyphenylpyruvat-Dioxygenase, Phytoendesaturase, Photosystem I, Photosystem II oder As a combination partner for the compounds of the general formula (I) according to the invention in compositions according to the invention (for example mixture formulations or in a tank mix), there are, for example, known active substances which are based on inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate -3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoendesaturase, Photosystem I, Photosystem II or
Protoporphyrinogen-Oxidase beruhen, einsetzbar, wie sie z.B. aus Weed Research 26 (1986) 441-445 oder "The Pesticide Manual", l6th edition, The British Crop Protection Council und the Royal Soc. of Chemistry, 2012 und dort zitierter Literatur beschrieben sind. Nachfolgend werden beispielhaft bekannte Herbizide oder Pflanzenwachstumsregulatoren genannt, die mit den erfindungsgemäßen Verbindungen kombiniert werden können, wobei diese Wirkstoffe entweder mit ihrem "common name" in der englischsprachigen Variante gemäß International Organization for Standardization (ISO) oder mit dem chemischen Namen bzw. mit der Codenummer bezeichnet sind. Dabei sind stets sämtliche Protoporphyrinogen oxidase are used, such as those e.g. from Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 and the literature cited therein. Known herbicides or plant growth regulators are mentioned below by way of example, which can be combined with the compounds according to the invention, these active compounds either with their "common name" in the English-language variant according to the International Organization for Standardization (ISO) or with the chemical name or with the code number are designated. There are always everyone
Anwendungsformen wie beispielsweise Säuren, Salze, Ester sowie auch alle isomeren Formen wie Stereoisomere und optische Isomere umfaßt, auch wenn diese nicht explizit erwähnt sind. Beispiele für solche herbiziden Mischungspartner sind: Application forms such as acids, salts, esters and also all isomeric forms such as stereoisomers and optical isomers, even if these are not explicitly mentioned. Examples of such herbicidal mixture partners are:
Acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim- sodium, ametryn, amicarbazone, amidochlor, amidosulfüron, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3- methylphenyl)-5-fluoropyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlor- potassium, aminocyclopyrachlor-methyl, aminopyralid, amitrole, ammoniumsulfamate, anilofos, asulam, atrazine, azafenidin, azimsulfüron, beflubutamid, benazolin, benazolin-ethyl, benfluralin, benfüresate, bensulfüron, bensulfüron-methyl, bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyron, bifenox, bilanafos, bilanafos-sodium, bispyribac, bispyribac-sodium, bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil-butyrate, -potassium, -heptanoate und -octanoate, busoxinone, butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl, chloramben, chlorbromuron, chlorfenac, chlorfenac- sodium, chlorfenprop, chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorophthalim, chlorotoluron, chlorthal-dimethyl, chlorsulfuron, cinidon, cinidon-ethyl, cinmethylin, cinosulfuron, clacyfos, clethodim, clodinafop, clodinafop-propargyl, clomazone, clomeprop, clopyralid, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop, cyhalofop-butyl, cyprazine, 2,4-D, 2,4-D-butotyl, -butyl, - dimethylammonium, -diolamin, -ethyl, 2-ethylhexyl, -isobutyl, -isooctyl, -isopropylammonium, - potassium, -triisopropanolammonium und -trolamine, 2,4-DB, 2,4-DB-butyl, -dimethylammonium, isooctyl, -potassium und -sodium, daimuron (dymron), dalapon, dazomet, n-decanol, desmedipham, detosyl-pyrazolate (DTP), dicamba, dichlobenil, 2-(2,4-dichlorobenzyl)-4,4-dimethyl-l,2-oxazolidin-3- one, 2-(2,5-dichlorobenzyl)-4,4-dimethyl-l,2-oxazolidin-3-one, dichlorprop, dichlorprop-P, diclofop, diclofop-methyl, diclofop-P-methyl, diclosulam, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr- sodium, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimetrasulfuron, dinitramine, dinoterb, diphenamid, diquat, diquat-dibromid, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron, ethametsulfuron-methyl, ethiozin, ethofumesate, ethoxyfen, ethoxyfen- ethyl, ethoxysulfuron, etobenzanid, F-9600, F-5231, i.e. N-[2- Chlor-4-fluor-5-[4-(3-fluorpropyl)-4,5-dihydro-5-oxo-lH-tetrazol-l-yl]-phenyl]-ethansulfonamid, F- 7967, i.e. 3-[7-Chlor-5-fluor-2-(trifluormethyl)-lH-benzimidazol-4-yl]-l-methyl-6- (trifluormethyl)pyrimidin-2,4(lH,3H)-dion, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P- ethyl, fenoxasulfone, fenquinotrione, fentrazamide, flamprop, flamprop-M-isopropyl, flamprop-M- methyl, flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl,  Acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryn, amicarbazone, amidochlor, amidosulfüron, 4-amino-3-chloro-6- (4-chloro-2-fluoro-3-methylphenyl ) -5-fluoropyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlor-potassium, aminocyclopyrachlor-methyl, aminopyralid, amitrole, ammonium sulfamate, anilofos, asulam, atrazine, azafenidin, azimsulfüron, beflubutamid, benazolin, benuralone, benazolin, benazolin , bensulfüron-methyl, bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyron, bifenox, bilanafos, bilanafos-sodium, bispyribac, bispyribac-sodium, bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxanoanoate-butoate-borate-neo-nitrate, busoxinone, butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl, chloramben, chlorbromuron, chlorfenac, chlorfenac-sodium, chlorfenpro p, chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorophthalim, chlorotoluron, chlorthal-dimethyl, chlorsulfuron, cinidon, cinidon-ethyl, cinmethylin, cinosulfuron, clacyfos, clethodim, clodinafop, clargylomopom, clargylopom, clodinafom clopyralid, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop, cyhalofop-butyl, cyprazine, 2,4-D, 2,4-D-butotyl, -butyl, - dimethylammonium -diolamine, -ethyl, 2-ethylhexyl, -isobutyl, -isooctyl, -isopropylammonium, - potassium, -triisopropanolammonium and -trolamine, 2,4-DB, 2,4-DB-butyl, -dimethylammonium, isooctyl, -potassium and -sodium, daimuron (dymron), dalapon, dazomet, n-decanol, desmedipham, detosyl-pyrazolate (DTP), dicamba, dichlobenil, 2- (2,4-dichlorobenzyl) -4,4-dimethyl-l, 2-oxazolidine -3- one, 2- (2,5-dichlorobenzyl) -4,4-dimethyl-1,2-oxazolidin-3-one, dichloroprop, dichloroprop-P, diclofop, diclofop-methyl, diclofop-P-met hyl, diclosulam, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr- sodium, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimetrasulfuron, dinitramine, dinoterb, diphenamid, diquat, didoton, diquatdithiophrod EPTC, esprocarb, ethalfluralin, ethametsulfuron, ethametsulfuron-methyl, ethiozin, ethofumesate, ethoxyfen, ethoxyfen-ethyl, ethoxysulfuron, etobenzanid, F-9600, F-5231, ie N- [2-chloro-4-fluoro-5- [4- (3-fluoropropyl) -4,5-dihydro-5-oxo-lH-tetrazol-l-yl] phenyl] ethanesulfonamide, F-7967, ie 3- [7-chloro-5-fluoro-2- (trifluoromethyl) -lH-benzimidazol-4-yl] -l-methyl-6- (trifluoromethyl) pyrimidine-2,4 (1H, 3H) -dione, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenquinotrione, fentrazamide, flamprop, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazifop-butyl, fluazifop P-butyl,
flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, fluometuron, flurenol, flurenol-butyl, - dimethylammonium und -methyl, fluoroglycofen, fluoroglycofen-ethyl, flupropanate, flupyrsulfuron, flupyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium, foramsulfuron, fosamine, glufosinate, glufosinate-ammonium, glufosinate-P-sodium, glufosinate-P-ammonium, glufosinate-P-sodium, glyphosate, glyphosate-ammonium, -isopropylammonium, -diammonium, -dimethylammonium, - potassium, -sodium und -trimesium, H-9201, i.e. 0-(2,4-Dimethyl-6-nitrophenyl)-0-ethyl- isopropylphosphoramidothioat, halauxifen, halauxifen-methyl, halosafen, halosulfuron, halosulfuron- methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, hexazinone, HW-02, i.e. l-(Dimethoxyphosphoryl)-ethyl-(2,4- dichlorphenoxy)acetat, imazamethabenz, Imazamethabenz-methyl, imazamox, imazamox-ammonium, imazapic, imazapic-ammonium, imazapyr, imazapyr-isopropylammonium, imazaquin, imazaquin- ammonium, imazethapyr, imazethapyr-immonium, imazosulfuron, indanofan, indaziflam, iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, ioxynil-octanoate, -potassium und sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, karbutilate, KUH-043, i.e. 3-({[5-(Difluormethyl)-l- methyl-3-(trifluormethyl)- 1 H-pyrazol-4-yl]methyl} sulfonyl)-5,5-dimethyl-4,5-dihydro- 1 ,2-oxazol, ketospiradox, lactofen, lenacil, linuron, MCPA, MCPA-butotyl, -dimethylammonium, -2-ethylhexyl, - isopropylammonium, -potassium und -sodium, MCPB, MCPB-methyl, -ethyl und -sodium, mecoprop, mecoprop-sodium, und -butotyl, mecoprop-P, mecoprop-P-butotyl, -dimethylammonium, -2-ethylhexyl und -potassium, mefenacet, mefluidide, mesosulfuron, mesosulfuron-methyl, mesotrione, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, fluometuron, flurenol, flurenol-butyl, -dimethylammonoglypane, and -methyl-fluorine-cyanogen flupyrsulfuron, flupyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium, foramsulfuron, fosamine, glufosinate, glufosinate ammonium, pufosinate ammonium P-ammonium, glufosinate-P-sodium, glyphosate, glyphosate-ammonium, -isopropylammonium, -diammonium, -dimethylammonium, - potassium, -sodium and -trimesium, H-9201, ie 0- (2,4-dimethyl-6-nitrophenyl) -0-ethyl-isopropylphosphoramidothioat, halauxifen , halauxifen-methyl, halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, hexazinone, HW-02, ie l- (dimethoxyphosphoryl ) -ethyl- (2,4-dichlorophenoxy) acetate, imazamethabenz, imazamethabenz-methyl, imazamox, imazamox-ammonium, imazapic, imazapic-ammonium, imazapyr, imazapyr-isopropylammonium, imazaquin, imazaquin-ammonium, imazethapyros, imazonapyros, imazonap , indanofan, indaziflam, iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, ioxynil-octanoate, -potassium and sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, karbutilate, KUH-043, ie D - ({ethyl ) -l-methyl-3- (trifluoromethyl) -1 H-pyrazol-4-yl] methyl} sulfonyl) -5,5-dimethyl-4,5-dih ydro-1, 2-oxazole, ketospiradox, lactofen, lenacil, linuron, MCPA, MCPA-butotyl, -dimethylammonium, -2-ethylhexyl, -isopropylammonium, -potassium and -sodium, MCPB, MCPB-methyl, -ethyl and -sodium , mecoprop, mecoprop-sodium, and -butotyl, mecoprop-P, mecoprop-P-butotyl, -dimethylammonium, -2-ethylhexyl and -potassium, mefenacet, mefluidide, mesosulfuron, mesosulfuron-methyl, mesotrione,
methabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazosulfuron,
methabenzthiazuron, methiopyrsulfuron, methiozolin, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinat, monolinuron, monosulfuron, monosulfuron-ester, MT-5950, i.e. N-[3-chlor-4-(l-methylethyl)- phenyl]-2-methylpentanamid, NGGC-011, napropamide, NC-310, i.e. 4-(2,4-Dichlorbenzoyl)-l-methyl- 5-benzyloxypyrazol, neburon, nicosulfuron, nonanoic acid (Pelargonsäure), norflurazon, oleic acid (fatty acids), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefon, oxyfluorfen, paraquat, paraquat dichloride, pebulate, pendimethalin, penoxsulam, pentachlorphenol, pentoxazone, pethoxamid, petroleum oils, phenmedipham, picloram, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propoxycarbazone-sodium, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen, pyraflufen- ethyl, pyrasulfotole, pyrazolynate (pyrazolate), pyrazosulfuron, pyrazosulfuron- ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, SL-261, sulcotrion, sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosulfuron, , SYN-523, SYP-249, i.e. l-Ethoxy-3-methyl-l-oxobut-3-en-2-yl- 5-[2-chlor-4-(trifluormethyl)phenoxy]-2-nitrobenzoat, SYP-300, i.e. l-[7-Fluor-3-oxo-4-(prop-2-in-l- yl)-3,4-dihydro-2H-l,4-benzoxazin-6-yl]-3-propyl-2-thioxoimidazolidin-4,5-dion, 2,3,6-TBA, TCA (Trifluoressigsäure), TCA-sodium, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbumeton, terbuthylazin, terbutryn, thenylchlor, thiazopyr, thiencarbazone, thiencarbazone- methyl, thifensulfuron, thifensulfüron-methyl, thiobencarb, tiafenacil, tolpyralate, topramezone, tralkoxydim, triafamone, tri-allate, triasulfüron, triaziflam, tribenuron, tribenuron-methyl, triclopyr, trietazine, trifloxysulfüron, trifloxysulfüron-sodium, trifludimoxazin, trifluralin, triflusulfuron, triflusulfüron-methyl, tritosulfuron, urea sulfate, vemolate, XDE-848, ZJ-0862, i.e. 3,4-Dichlor-N-{2- [(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}anilin, sowie die folgenden Verbindungen: methabenzthiazuron, methiopyrsulfuron, methiozolin, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinat, monolinuron, monosulfuron, MT-59-chloro-3-ester -4- (l-methylethyl) phenyl] -2-methylpentanamide, NGGC-011, napropamide, NC-310, ie 4- (2,4-dichlorobenzoyl) -l-methyl-5-benzyloxypyrazole, neburon, nicosulfuron, nonanoic acid (pelargonic acid), norflurazon, oleic acid (fatty acids), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefon, oxyfluorfen, paraquat, paraquat dichloride, pebulate, pendimethalin, penoxsulone, pentachlorone, pentachlorone, pentachlorone, pentachlorone phenmedipham, picloram, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propoxycarbazone, propoxycarbazone furon, Propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen, pyraflufen- ethyl, pyrasulfotole, pyrazolynate (pyrazolate), pyrazosulfuron, pyrazosulfuron- ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid , pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofonofulfonyl , sethoxydim, siduron, simazine, simetryn, SL-261, sulcotrione, sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosulfuron,, SYN-523, SYP-249, ie l-ethoxy-3-methyl-l-oxobut-3-en -2-yl- 5- [2-chloro-4- (trifluoromethyl) phenoxy] -2-nitrobenzoate, SYP-300, ie l- [7-fluoro-3-oxo-4- (prop-2-in-l yl) -3,4-dihydro-2H-l, 4-benzoxazin-6-yl] -3-propyl-2-thioxoimidazolidin-4,5-dione, 2,3,6-TBA, TCA (trifluoroacetic acid), TCA-sodium, tebuthiuron, tefuryltrione , tembotrione, tepraloxydim, terbacil, terbucarb, terbumeton, terbuthylazine, terbutryn, thenylchlor, thiazopyr, thiencarbazone, thiencarbazone- methyl, thifensulfuron, thifensulfüron-methyl, thiobencarb, tiafenacil, tolpyralate, topramezone, tralkoxydim, triafamone, tri-allate, triasulfüron, triaziflam, tribenuron, tribenuron-methyl, triclopyr, trietazine, trifloxysulfüron, trifloxysulfüron-sodium, trifludimoxazin, trifluralin, triflusulfuron, triflusulfüron-methyl, tritosulfuron, urea sulfate, vemolate, XDE-848, ZJ-0862, {3,4- [dichloro (3,4- [dichloro (3,4-dichloro , 6-dimethoxypyrimidin-2-yl) oxy] benzyl} aniline, and the following compounds:
Beispiele für Pflanzenwachstumsregulatoren als mögliche Mischungspartner sind: Examples of plant growth regulators as possible mixing partners are:
Acibenzolar, acibenzolar-S-methyl, 5-Amino lävulinsäure, ancymidol, 6-benzylaminopurine, Acibenzolar, acibenzolar-S-methyl, 5-amino levulinic acid, ancymidol, 6-benzylaminopurine,
Brassinolid, Catechin, chlormequat chloride, cloprop, cyclanilide, 3-(Cycloprop-l-enyl)propionsäure, daminozide, dazomet, n-decanol, dikegulac, dikegulac-sodium, endothal, endothal- dipotassium, -disodium, und mono(N,N-dimethylalkylammonium), ethephon, flumetralin, flurenol, flurenol-butyl, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indol-3-acetic acid (IAA), 4- indol-3-ylbutyric acid, isoprothiolane, probenazole, Jasmonsäure, Jasmonsäuremethylester, maleic hydrazide, mepiquat chloride, 1 -methylcyclopropene, 2-(l-naphthyl)acetamide, 1 -naphthylacetic acid, 2- naphthyloxyacetic acid, nitrophenolate-mixture, 4-Oxo-4[(2-phenylethyl)amino]buttersäure, paclobutrazol, N-phenylphthalamic acid, prohexadione, prohexadione-calcium, prohydrojasmone, Salicylsäure, Strigolacton, tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tsitodef, uniconazole, uniconazole-P.  Brassinolide, catechin, chlormequat chloride, cloprop, cyclanilide, 3- (cycloprop-l-enyl) propionic acid, daminozide, dazomet, n-decanol, dikegulac, dikegulac-sodium, endothal, endothal-dipotassium, -disodium, and mono (N, N-dimethylalkylammonium), ethephon, flumetralin, flurenol, flurenol-butyl, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indol-3-acetic acid (IAA), 4-indol-3-ylbutyric acid, isoprothiolane, probenazole, jasmonic acid, jasmonic acid , maleic hydrazide, mepiquat chloride, 1 -methylcyclopropene, 2- (l-naphthyl) acetamide, 1 -naphthylacetic acid, 2-naphthyloxyacetic acid, nitrophenolate-mixture, 4-oxo-4 [(2-phenylethyl) amino] butyric acid, paclobutrazole , N-phenylphthalamic acid, prohexadione, prohexadione-calcium, prohydrojasmone, salicylic acid, strigolactone, tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tsitodef, uniconazole, uniconazole-P.
Ebenfalls als Kombinationspartner für die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) kommen beispielsweise die folgenden Safener in Frage: The following safeners, for example, are also suitable as combination partners for the compounds of the general formula (I) according to the invention:
Sl) Verbindungen aus der Gruppe heterocyclischer Carbonsäurederivate:  Sl) compounds from the group of heterocyclic carboxylic acid derivatives:
Sla) Verbindungen vom Typ der Dichlorphenylpyrazolin-3-carbonsäure (Sla), vorzugsweise Sl a ) Compounds of the dichlorophenylpyrazoline-3-carboxylic acid type (Sl a ), preferably
Verbindungen wie l-(2,4-Dichlorphenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazolin-3-carbonsäure,Connections like l- (2,4-dichlorophenyl) -5- (ethoxycarbonyl) -5-methyl-2-pyrazoline-3-carboxylic acid,
1 -(2,4-Dichlorphenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazolin-3-carbonsäureethylester (S 1 - 1 ) ("Mefenpyr-diethyl"), und verwandte Verbindungen, wie sie in der WO-A-91/07874 beschrieben sind; 1 - (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;
S 1 b) Derivate der Dichlorphenylpyrazolcarbonsäure (S 1 b), vorzugsweise V erbindungen wie S 1 b ) derivatives of dichlorophenylpyrazole carboxylic acid (S 1 b ), preferably compounds such as
1 -(2,4-Dichlorphenyl)-5-methylpyrazol-3 -carbonsäureethylester (S 1 -2),  1 - (2,4-dichlorophenyl) -5-methylpyrazole-3-carboxylic acid ethyl ester (S 1 -2),
l-(2,4-Dichlorphenyl)-5-isopropylpyrazol-3-carbonsäureethylester (Sl-3),  ethyl 1- (2,4-dichlorophenyl) -5-isopropylpyrazole-3-carboxylate (S1-3),
1 -(2,4-Dichlorphenyl)-5-(l , 1 -dimethyl-ethyl)pyrazol-3-carbonsäureethylester (Sl -4) und verwandte Verbindungen, wie sie in EP-A-333131 und EP-A-269806 beschrieben sind;  1 - (2,4-dichlorophenyl) -5- (1,1-dimethyl-ethyl) pyrazole-3-carboxylic acid ethyl ester (Sl -4) and related compounds as described in EP-A-333131 and EP-A-269806 are;
Slc) Derivate der l,5-Diphenylpyrazol-3-carbonsäure (Slc), vorzugsweise Verbindungen wie Sl c ) derivatives of l, 5-diphenylpyrazole-3-carboxylic acid (Sl c ), preferably compounds such as
1 -(2,4-Dichlorphenyl)-5-phenylpyrazol-3-carbonsäureethylester (S 1 -5),  1 - (2,4-dichlorophenyl) -5-phenylpyrazole-3-carboxylic acid ethyl ester (S 1 -5),
l-(2-Chlorphenyl)-5-phenylpyrazol-3-carbonsäuremethylester (Sl-6) und verwandte  1- (2-Chlorophenyl) -5-phenylpyrazole-3-carboxylic acid methyl ester (S1-6) and related
Verbindungen wie sie beispielsweise in der EP-A-268554 beschrieben sind;  Compounds as described for example in EP-A-268554;
Sld) Verbindungen vom Typ der Triazolcarbonsäuren (Sld), vorzugsweise Verbindungen wie Sl d ) compounds of the triazole carboxylic acid type (Sl d ), preferably compounds such as
Fenchlorazol(-ethylester), d.h. l-(2,4-Dichlorphenyl)-5-trichlormethyl-(lH)-l,2,4-triazol-3- carbonsäureethylester (Sl-7), und verwandte Verbindungen, wie sie in EP-A-174562 und EP-A-346620 beschrieben sind;  Fenchlorazole (ethyl ester), i.e. 1- (2,4-dichlorophenyl) -5-trichloromethyl- (lH) -l, 2,4-triazole-3-carboxylic acid ethyl ester (S1-7), and related compounds as described in EP-A-174562 and EP- A-346620;
Sle) Verbindungen vom Typ der 5-Benzyl- oder 5-Phenyl-2-isoxazolin-3- carbonsäure, oder der 5,5- Diphenyl-2-isoxazolin-3-carbonsäure(Sle), vorzugsweise Verbindungen wie Sl e ) compounds of the type of 5-benzyl- or 5-phenyl-2-isoxazoline-3-carboxylic acid, or of 5,5-diphenyl-2-isoxazoline-3-carboxylic acid (Sl e ), preferably compounds such as
5-(2,4-Dichlorbenzyl)-2-isoxazolin-3 -carbonsäureethylester (Sl-8) oder  5- (2,4-dichlorobenzyl) -2-isoxazoline-3-carboxylic acid ethyl ester (Sl-8) or
5-Phenyl-2-isoxazolin-3-carbonsäureethylester (Sl-9) und verwandte Verbindungen, wie sie in WO-A-91/08202 beschrieben sind, bzw. 5,5-Diphenyl-2-isoxazolin-carbonsäure (S1-10) oder 5,5-Diphenyl-2-isoxazolin-3-carbonsäureethylester (Sl-l 1) ("Isoxadifen-ethyl")  5-phenyl-2-isoxazoline-3-carboxylic acid ethyl ester (S1-9) and related compounds, as described in WO-A-91/08202, or 5,5-diphenyl-2-isoxazoline-carboxylic acid (S1-10 ) or 5,5-Diphenyl-2-isoxazoline-3-carboxylic acid ethyl ester (S1-L 1) ("Isoxadifen-ethyl")
oder -n-propylester (S1-12) oder 5-(4-Fluorphenyl)-5-phenyl-2-isoxazolin-3-carbon- säureethylester (S 1-13), wie sie in der Patentanmeldung WO-A-95/07897 beschrieben sind. or -n-propyl ester (S1-12) or 5- (4-fluorophenyl) -5-phenyl-2-isoxazoline-3-carboxylic acid ethyl ester (S 1-13), as described in patent application WO-A-95 / 07897 are described.
S2) Verbindungen aus der Gruppe der 8-Chinolinoxyderivate (S2): S2) Compounds from the group of 8-quinoline oxy derivatives (S2):
S2a) Verbindungen vom Typ der 8-Chinolinoxyessigsäure (S2a), vorzugsweise S2 a ) Compounds of the 8-quinolinoxyacetic acid (S2 a ) type, preferably
(5-Chlor-8-chinolinoxy)essigsäure-(l-methylhexyl)-ester ("Cloquintocet-mexyl") (S2-1), (5-Chlor-8-chinolinoxy)essigsäure-(l,3-dimethyl-but-l-yl)-ester (S2-2),  (5-chloro-8-quinolinoxy) acetic acid (1-methylhexyl) ester ("Cloquintocet-mexyl") (S2-1), (5-chloro-8-quinolinoxy) acetic acid (1,3-dimethyl-but -l-yl) -ester (S2-2),
(5-Chlor-8-chinolinoxy)essigsäure-4-allyl-oxy-butylester (S2-3),  (5-chloro-8-quinolinoxy) 4-allyl-oxy-butyl acetate (S2-3),
(5-Chlor-8-chinolinoxy)essigsäure-l-allyloxy-prop-2-ylester (S2-4),  (5-chloro-8-quinolinoxy) acetic acid l-allyloxy prop-2-yl ester (S2-4),
(5-Chlor-8-chinolinoxy)essigsäureethylester (S2-5),  (5-chloro-8-quinolinoxy) ethyl acetate (S2-5),
(5-Chlor-8-chinolinoxy)essigsäuremethylester (S2-6),  (5-chloro-8-quinolinoxy) methyl acetate (S2-6),
(5-Chlor-8-chinolinoxy)essigsäureallylester (S2-7),  (5-chloro-8-quinolinoxy) allyl acetate (S2-7),
(5-Chlor-8-chinolinoxy)essigsäure-2-(2-propyliden-iminoxy)-l-ethylester (S2-8),  (5-chloro-8-quinolinoxy) acetic acid 2- (2-propylidene-iminoxy) -l-ethyl ester (S2-8),
(5-Chlor-8-chinolinoxy)essigsäure-2-oxo-prop-l-ylester (S2-9) und verwandte Verbindungen, wie sie in EP-A-86750, EP-A-94349 und EP-A-191736 oder EP-A-0 492 366 beschrieben sind, sowie (5-Chlor-8-chinolinoxy)essigsäure (S2-10), deren Hydrate und Salze, beispielsweise deren Lithium-, Natrium- Kalium-, Kalzium-, Magnesium-, Aluminium-, Eisen-, Ammonium-, quartäre Ammonium-, Sulfonium-, oder Phosphoniumsalze wie sie in der WO-A-2002/34048 beschrieben sind; (5-Chloro-8-quinolinoxy) 2-oxo-prop-l-yl acetate (S2-9) and related compounds as described in EP-A-86750, EP-A-94349 and EP-A-191736 or EP-A-0 492 366 are described, and (5-chloro-8-quinolinoxy) acetic acid (S2-10), its hydrates and salts, for example its lithium, sodium, potassium, calcium, magnesium, aluminum, iron, ammonium, quaternary ammonium , Sulfonium or phosphonium salts as described in WO-A-2002/34048;
S2b) Verbindungen vom Typ der (5-Chlor-8-chinolinoxy)malonsäure (S2b), vorzugsweise S2 b ) Compounds of the type of (5-chloro-8-quinolinoxy) malonic acid (S2 b ), preferably
Verbindungen wie (5-Chlor-8-chinolinoxy)malonsäurediethylester,  Compounds such as (5-chloro-8-quinolinoxy) diethyl malonate,
(5-Chlor-8-chinolinoxy)malonsäurediallylester,  (5-chloro-8-quinolinoxy) malonate,
(5-Chlor-8-chinolinoxy)malonsäure-methyl-ethylester und verwandte Verbindungen, wie sie in EP-A-0 582 198 beschrieben sind.  Methyl (5-chloro-8-quinolinoxy) malonic acid and related compounds as described in EP-A-0 582 198.
53) Wirkstoffe vom Typ der Dichloracetamide (S3), die häufig als Vorauflaufsafener  53) Active substances of the type of dichloroacetamide (S3), often as pre-emergence safeners
(bodenwirksame Safener) angewendet werden, wie z. B.  (Soil-effective safeners), such as B.
"Dichlormid" (N,N-Diallyl-2,2-dichloracetamid) (S3-1),  "Dichlormid" (N, N-diallyl-2,2-dichloroacetamide) (S3-1),
"R-29148" (3-Dichloracetyl-2,2,5-trimethyl-l,3-oxazolidin) der Firma Stauffer (S3-2), "R-28725" (3-Dichloracetyl-2,2,-dimethyl-l,3-oxazolidin) der Firma Stauffer (S3-3),  "R-29148" (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) from Stauffer (S3-2), "R-28725" (3-dichloroacetyl-2,2, -dimethyl- 1,3-oxazolidine) from Stauffer (S3-3),
"Benoxacor" (4-Dichloracetyl-3,4-dihydro-3-methyl-2H-l,4-benzoxazin) (S3-4),  "Benoxacor" (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-l, 4-benzoxazine) (S3-4),
"PPG-1292" (N-Allyl-N-[(l,3-dioxolan-2-yl)-methyl]-dichloracetamid) der Firma PPG  "PPG-1292" (N-allyl-N - [(1,3-dioxolan-2-yl) methyl] dichloroacetamide) from PPG
Industries (S3-5),  Industries (S3-5),
"DKA-24" (N-Allyl-N-[(allylaminocarbonyl)methyl]-dichloracetamid) der Firma Sagro-Chem (S3-6),  "DKA-24" (N-allyl-N - [(allylaminocarbonyl) methyl] dichloroacetamide) from Sagro-Chem (S3-6),
"AD-67" oder "MON 4660" (3-Dichloracetyl-l-oxa-3-aza-spiro[4,5]decan) der Firma  "AD-67" or "MON 4660" (3-dichloroacetyl-l-oxa-3-aza-spiro [4,5] decane) from the company
Nitrokemia bzw. Monsanto (S3-7),  Nitrokemia or Monsanto (S3-7),
"TI-35" (l-Dichloracetyl-azepan) der Firma TRI-Chemical RT (S3-8),  "TI-35" (l-dichloroacetyl-azepan) from TRI-Chemical RT (S3-8),
"Diclonon" (Dicyclonon) oder "BAS145138" oder "LAB145138" (S3-9)  "Diclonon" (dicyclonone) or "BAS145138" or "LAB145138" (S3-9)
((RS)-l-Dichloracetyl-3,3,8a-trimethylperhydropyrrolo[l,2-a]pyrimidin-6-on) der Firma BASF, "Furilazol" oder "MON 13900" ((RS)-3-Dichloracetyl-5-(2-furyl)-2,2-dimethyloxazolidin) (S3-10), sowie dessen (R)-Isomer (S3-11).  ((RS) -l-dichloroacetyl-3,3,8a-trimethylperhydropyrrolo [1,2-a] pyrimidin-6-one) from BASF, "Furilazole" or "MON 13900" ((RS) -3-dichloroacetyl- 5- (2-furyl) -2,2-dimethyloxazolidine) (S3-10), as well as its (R) -isomer (S3-11).
54) Verbindungen aus der Klasse der Acylsulfonamide (S4):  54) Compounds from the class of acylsulfonamides (S4):
S4a) N- Acylsulfonamide der Formel (S4a) und deren Salze wie sie in der WO-A-97/45016 S4 a ) N-acylsulfonamides of the formula (S4 a ) and their salts as described in WO-A-97/45016
beschrieben sind, are described
wonn  Wonn
RA 1 (Ci-C6)Alkyl, (C3-C6)Cycloalkyl, wobei die 2 letztgenannten Reste durch VA R A 1 (Ci-C 6 ) alkyl, (C3-C6) cycloalkyl, the 2 last-mentioned radicals by VA
Substituenten aus der Gruppe Halogen, (Ci-C4)Alkoxy, (Ci-C6)Haloalkoxy und (Ci- C4)Alkylthio und im Falle cyclischer Reste auch durch (Ci-C4)Alkyl und (Ci-C4)Haloalkyl substituiert sind; RA2 Halogen, (Ci-C4)Alkyl, (Ci-C4)Alkoxy, CF3; Substituents from the group halogen, (Ci-C4) alkoxy, (Ci-C 6) haloalkoxy and (Ci- C4) alkylthio and in case of cyclic radicals are substituted by (Ci-C4) alkyl and (Ci-C4) haloalkyl; RA 2 halogen, (Ci-C 4 ) alkyl, (Ci-C 4 ) alkoxy, CF 3;
n 1 oder 2;  n 1 or 2;
VA ist 0, 1 , 2 oder 3 bedeuten;  VA is 0, 1, 2 or 3;
S4b) Verbindungen vom Typ der 4-(Benzoylsulfamoyl)benzamide der Formel (S4b) und deren Salze, wie sie in der WO-A-99/16744 beschrieben sind, S4 b ) compounds of the 4- (benzoylsulfamoyl) benzamide type of the formula (S4 b ) and their salts, as described in WO-A-99/16744,
wonn  Wonn
RB1, RB2 unabhängig voneinander Wasserstoff, (Ci-C6)Alkyl, (C3-C6)Cycloalkyl, (C3- C6)Alkenyl, (C3-C6)Alkinyl, RB 1 , RB 2 independently of one another hydrogen, (Ci-C 6 ) alkyl, (C3-C6) cycloalkyl, (C3-C 6 ) alkenyl, (C3-C 6 ) alkynyl,
RB3 Halogen, (Ci-C i)Alkyl, (Ci-C4)Haloalkyl oder (Ci-C4)Alkoxy und RB 3 halogen, (Ci-C i) alkyl, (Ci-C4) haloalkyl or (Ci-C4) alkoxy and
ms 1 oder 2 bedeuten,  ms 1 or 2 mean
z.B. solche worin  e.g. those in
RB1 = Cyclopropyl, RB2 = Wasserstoff und (RB3) = 2-OMe ist ("Cyprosulfamide", S4-1),RB 1 = cyclopropyl, RB 2 = hydrogen and (RB 3 ) = 2-OMe ("Cyprosulfamide", S4-1),
RB1 = Cyclopropyl, RB2 = Wasserstoff und (RB3) = 5-Cl-2-OMe ist (S4-2), RB 1 = cyclopropyl, RB 2 = hydrogen and (RB 3 ) = 5-Cl-2-OMe is (S4-2),
RB1 = Ethyl, RB2 = Wasserstoff und (RB3) = 2-OMe ist(S4-3), RB 1 = ethyl, RB 2 = hydrogen and (RB 3 ) = 2-OMe is (S4-3),
RB1 = Isopropyl, RB2 = Wasserstoff und (RB3) = 5-Cl-2-OMe ist (S4-4) und RB 1 = isopropyl, RB 2 = hydrogen and (RB 3 ) = 5-Cl-2-OMe is (S4-4) and
RB1 = Isopropyl, RB2 = Wasserstoff und (RB3) = 2-OMe ist(S4-5); RB 1 = isopropyl, RB 2 = hydrogen and (RB 3 ) = 2-OMe is (S4-5);
S4C) Verbindungen aus der Klasse der Benzoylsulfamoylphenylhamstoffe der Formel (S4C), wie sie in der EP-A-365484 beschrieben sind, S4 C ) compounds from the class of the benzoylsulfamoylphenylureas of the formula (S4 C ) as described in EP-A-365484,
wonn  Wonn
Rc1, Rc2 unabhängig voneinander Wasserstoff, (Ci-Cg)Alkyl, (C3-Cg)Cycloalkyl, (C3-Rc 1 , Rc 2 independently of one another hydrogen, (Ci-Cg) alkyl, (C3-Cg) cycloalkyl, (C3-
C6)Alkenyl, (C3-C6)Alkinyl, C 6 ) alkenyl, (C3-C 6 ) alkynyl,
Rc3 Halogen, (Ci-C4)Alkyl, (Ci-C4)Alkoxy, CF3 und Rc 3 halogen, (Ci-C4) alkyl, (Ci-C4) alkoxy, CF 3 and
mc 1 oder 2 bedeuten;  mc represents 1 or 2;
beispielsweise  for example
l-[4-(N-2-Methoxybenzoylsulfamoyl)phenyl]-3-methylhamstoff,  l- [4- (N-2-Methoxybenzoylsulfamoyl) phenyl] -3-methylhamstoff,
l-[4-(N-2-Methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylhamstoff,  l- [4- (N-2-Methoxybenzoylsulfamoyl) phenyl] -3,3-dimethylurea,
l-[4-(N-4,5-Dimethylbenzoylsulfamoyl)phenyl]-3-methylhamstoff; S4d) Verbindungen vom Typ der N-Phenylsulfonylterephthalamide der Formel (S4d) und deren Salze, die z.B. bekannt sind aus CN 101838227, l- [4- (N-4,5-Dimethylbenzoylsulfamoyl) phenyl] -3-methylhamstoff; S4 d ) compounds of the N-phenylsulfonylterephthalamide type of the formula (S4 d ) and their salts, which are known, for example, from CN 101838227,
wonn  Wonn
RD4 Halogen, (Ci-C4)Alkyl, (Ci-C4)Alkoxy, CF3; RD 4 halogen, (Ci-C 4 ) alkyl, (Ci-C 4 ) alkoxy, CF 3;
mD 1 oder 2; m D 1 or 2;
RD5 Wasserstoff, (Ci-C6)Alkyl, (C3-C6)Cycloalkyl, (C2-C6)Alkenyl, (C2-C6)Alkinyl, (C5-RD 5 hydrogen, (Ci-C 6 ) alkyl, (C 3 -C 6 ) cycloalkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 5 -
C6)Cycloalkenyl bedeutet. C 6 ) means cycloalkenyl.
S5) Wirkstoffe aus der Klasse der Hydroxyaromaten und der aromatisch-aliphatischen  S5) Active ingredients from the class of the hydroxyaromatics and the aromatic-aliphatic
Carbonsäurederivate (S5), z.B.  Carboxylic acid derivatives (S5), e.g.
3,4,5-Triacetoxybenzoesäureethylester, 3,5-Dimethoxy-4-hydroxybenzoesäure, 3,5- Dihydroxybenzoesäure, 4-Hydroxysalicylsäure, 4-Fluorsalicyclsäure, 2-Hydroxyzimtsäure, 2,4- Dichlorzimtsäure, wie sie in der WO-A-2004/084631, WO-A-2005/015994, WO-A- 2005/016001 beschrieben sind.  3,4,5-triacetoxybenzoic acid ethyl ester, 3,5-dimethoxy-4-hydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4-fluorosalicyclic acid, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid, as described in WO-A- 2004/084631, WO-A-2005/015994, WO-A-2005/016001.
S6) Wirkstoffe aus der Klasse der l,2-Dihydrochinoxalin-2-one (S6), z.B. S6) active substances from the class of 1,2-dihydroquinoxalin-2-one (S6), e.g.
1 -Methyl-3 -(2-thienyl)- 1 ,2-dihydrochinoxalin-2-on, 1 -Methyl-3 -(2-thienyl)- 1 ,2-dihydro- chinoxalin-2-thion, l-(2-Aminoethyl)-3-(2-thienyl)-l,2-dihydro-chinoxalin-2-on-hydrochlorid, l-(2-Methylsulfonylaminoethyl)-3-(2-thienyl)-l,2-dihydro-chinoxalin-2-on, wie sie in der WO- A-2005/112630 beschrieben sind.  1-methyl-3 - (2-thienyl) - 1, 2-dihydroquinoxalin-2-one, 1-methyl-3 - (2-thienyl) - 1, 2-dihydroquinoxalin-2-thione, l- (2nd -Aminoethyl) -3- (2-thienyl) -l, 2-dihydro-quinoxalin-2-one hydrochloride, l- (2-methylsulfonylaminoethyl) -3- (2-thienyl) -l, 2-dihydro-quinoxalin- 2-one, as described in WO-A-2005/112630.
S7) Verbindungen aus der Klasse der Diphenylmethoxyessigsäurederivate (S7), z.B. S7) compounds from the class of diphenylmethoxyacetic acid derivatives (S7), e.g.
Diphenylmethoxyessigsäuremethylester (CAS-Reg.Nr. 41858-19-9) (S7-1),  Diphenylmethoxyacetic acid methyl ester (CAS Reg. No. 41858-19-9) (S7-1),
Diphenylmethoxyessigsäureethylester oder Diphenylmethoxyessigsäure wie sie in der WO-A- 98/38856 beschrieben sind.  Diphenylmethoxyacetic acid ethyl ester or Diphenylmethoxyacetic acid as described in WO-A-98/38856.
S8) Verbindungen der Formel (S8), wie sie in der WO-A-98/27049 beschrieben sind,  S8) compounds of the formula (S8) as described in WO-A-98/27049,
worin die Symbole und Indizes folgende Bedeutungen haben: where the symbols and indices have the following meanings:
RD1 ist Halogen, (Ci-C4)Alkyl, (Ci-C4)Haloalkyl, (Ci-C4)Alkoxy, (Ci-C4)Haloalkoxy, RD 1 is halogen, (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkyl, (Ci-C 4 ) alkoxy, (Ci-C 4 ) haloalkoxy,
RD2 ist Wasserstoff oder (Ci-C4)Alkyl, RD 3 ist Wasserstoff, (Ci-Cg)Alkyl, (C2-C4)Alkenyl, (C2-C4)Alkinyl, oder Aryl, wobei jeder der vorgenannten C-haltigen Reste unsubstituiert oder durch einen oder mehrere, vorzugsweise bis zu drei gleiche oder verschiedene Reste aus der Gruppe, bestehend aus Halogen und Alkoxy substituiert ist; oder deren Salze, RD 2 is hydrogen or (Ci-C 4 ) alkyl, R D 3 is hydrogen, (Ci-Cg) alkyl, (C2-C4) alkenyl, (C2-C4) alkynyl, or aryl, each of the abovementioned C-containing radicals being unsubstituted or by one or more, preferably up to three of the same or various radicals from the group consisting of halogen and alkoxy is substituted; or their salts,
nD ist eine ganze Zahl von 0 bis 2. n D is an integer from 0 to 2.
S9) Wirkstoffe aus der Klasse der 3-(5-Tetrazolylcarbonyl)-2-chinolone (S9), z.B.  S9) active substances from the class of 3- (5-tetrazolylcarbonyl) -2-quinolones (S9), e.g.
l,2-Dihydro-4-hydroxy-l-ethyl-3-(5-tetrazolylcarbonyl)-2-chinolon (CAS-Reg.Nr.: 219479-18- 2), l,2-Dihydro-4-hydroxy-l-methyl-3-(5-tetrazolyl-carbonyl)-2-chinolon (CAS-Reg.Nr.  l, 2-Dihydro-4-hydroxy-l-ethyl-3- (5-tetrazolylcarbonyl) -2-quinolone (CAS Reg.No .: 219479-18-2), l, 2-dihydro-4-hydroxy- l-methyl-3- (5-tetrazolyl-carbonyl) -2-quinolone (CAS reg. no.
95855-00-8), wie sie in der WO-A-1999/000020 beschrieben sind.  95855-00-8), as described in WO-A-1999/000020.
S 10) Verbindungen der Formeln (S 10a) oder (S 10b), S 10) compounds of the formulas (S 10 a ) or (S 10 b ),
wie sie in der WO-A-2007/023719 und WO-A-2007/023764 beschrieben sind,  as described in WO-A-2007/023719 and WO-A-2007/023764,
worin wherein
RE1 Halogen, (Ci-C4)Alkyl, Methoxy, Nitro, Cyano, CF3, OCF3 RE 1 halogen, (Ci-C4) alkyl, methoxy, nitro, cyano, CF3, OCF3
YE, ZE unabhängig voneinander O oder S, YE, ZE independently of one another O or S,
he eine ganze Zahl von 0 bis 4, hey an integer from 0 to 4,
RE2 (Ci-CiejAlkyl, (C2-C6)Alkenyl, (C3-C6)Cycloalkyl, Aryl; Benzyl, Halogenbenzyl, RE 2 (Ci-Ciejalkyl, (C2-C6) alkenyl, (C3-C6) cycloalkyl, aryl; benzyl, halobenzyl,
RE3 Wasserstoff oder (Ci-C6)Alkyl bedeuten. RE 3 is hydrogen or (Ci-C 6 ) alkyl.
Sl 1) Wirkstoffe vom Typ der Oxyimino- Verbindungen (Sl 1), die als Saatbeizmittel bekannt sind, wie z. B.  Sl 1) Active substances of the oxyimino compound type (Sl 1), which are known as seed dressings, such as. B.
"Oxabetrinil" ((Z)-l,3-Dioxolan-2-ylmethoxyimino(phenyl)acetonitril) (Sl l-l), das als Saatbeiz-Safener für Hirse gegen Schäden von Metolachlor bekannt ist,  "Oxabetrinil" ((Z) -l, 3-dioxolan-2-ylmethoxyimino (phenyl) acetonitrile) (Sl l-l), which is known as a seed dressing safener for millet against damage to metolachlor,
"Fluxofenim" (l-(4-Chlorphenyl)-2,2,2-trifluor-l-ethanon-0-(l,3-dioxolan-2-ylmethyl)-oxim) (Sl 1-2), das als Saatbeiz-Safener für Hirse gegen Schäden von Metolachlor bekannt ist, und "Cyometrinil" oder "CGA-43089" ((Z)-Cyanomethoxyimino(phenyl)acetonitril) (Sl l-3), das als Saatbeiz-Safener für Hirse gegen Schäden von Metolachlor bekannt ist.  "Fluxofenim" (1- (4-chlorophenyl) -2,2,2-trifluoro-l-ethanone-0- (1,3-dioxolan-2-ylmethyl) -oxime) (Sl 1-2), which is used as a seed dressing -Safeer for millet against damage from metolachlor is known, and "Cyometrinil" or "CGA-43089" ((Z) -cyanomethoxyimino (phenyl) acetonitrile) (Sl l-3), which is used as a seed dressing safener for millet against damage from metolachlor is known.
512) Wirkstoffe aus der Klasse der lsothiochromanone (S12), wie z.B. Methyl- [(3- oxo- 1H-2- benzothiopyran-4(3H)-yliden)methoxy]acetat (CAS-Reg.Nr. 205121-04-6) (S12-1) und verwandte Verbindungen aus WO-A-1998/13361.  512) active substances from the class of the isothiochromanones (S12), such as Methyl- [(3-oxo-1H-2-benzothiopyran-4 (3H) -ylidene) methoxy] acetate (CAS Reg. No. 205121-04-6) (S12-1) and related compounds from WO-A- 1998/13361.
513) Eine oder mehrere Verbindungen aus Gruppe (S13): "Naphthalic anhydrid" (l,8-Naphthalindicarbonsäureanhydrid) (S13-1), das als Saatbeiz-Safener für Mais gegen Schäden von Thiocarbamatherbiziden bekannt ist, 513) One or more compounds from group (S13): "Naphthalic anhydride" (1,8-naphthalenedicarboxylic anhydride) (S13-1), which is known as a seed dressing safener for maize against damage from thiocarbamate herbicides,
"Fenclorim" (4,6-Dichlor-2-phenylpyrimidin) (S13-2), das als Safener für Pretilachlor in gesätem Reis bekannt ist,  "Fenclorim" (4,6-dichloro-2-phenylpyrimidine) (S13-2), which is known as a safener for pretilachlor in sown rice,
"Flurazole" (Benzyl-2-chlor-4-trifluormethyl-l,3-thiazol-5-carboxylat) (S13-3), das als Saatbeiz-Safener für Hirse gegen Schäden von Alachlor und Metolachlor bekannt ist,  "Flurazole" (benzyl-2-chloro-4-trifluoromethyl-l, 3-thiazole-5-carboxylate) (S13-3), which is known as a seed dressing safener for millet against damage to alachlor and metolachlor,
"CL 304415" (CAS-Reg.Nr. 31541-57-8)  "CL 304415" (CAS reg.no.31541-57-8)
(4-Carboxy-3,4-dihydro-2H-l-benzopyran-4-essigsäure) (S13-4) der Firma American  (4-Carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid) (S13-4) from American
Cyanamid, das als Safener für Mais gegen Schäden von Imidazolinonen bekannt ist, Cyanamide, which is known as a safener for corn against damage to imidazolinones,
"MG 191" (CAS-Reg.Nr. 96420-72-3) (2-Dichlormethyl-2-methyl-l,3-dioxolan) (S13-5) der Firma Nitrokemia, das als Safener für Mais bekannt ist,  "MG 191" (CAS Reg. No. 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5) from Nitrokemia, which is known as a safener for corn,
"MG 838" (CAS-Reg.Nr. 133993-74-5)  "MG 838" (CAS Reg. No. 133993-74-5)
(2-propenyl l-oxa-4-azaspiro[4.5]decan-4-carbodithioat) (S13-6) der Firma Nitrokemia "Disulfoton" (O,O-Diethyl S-2-ethylthioethyl phosphordithioat) (S13-7),  (2-propenyl l-oxa-4-azaspiro [4.5] decane-4-carbodithioate) (S13-6) from Nitrokemia "Disulfoton" (O, O-Diethyl S-2-ethylthioethyl phosphorodithioate) (S13-7),
"Dietholate" (O,O-Diethyl-O-phenylphosphorothioat) (St 3-8),  "Dietholate" (O, O-Diethyl-O-phenylphosphorothioat) (St 3-8),
"Mephenate" (4-Chlorphenyl-methylcarbamat) (St 3-9).  "Mephenate" (4-chlorophenyl methyl carbamate) (St 3-9).
Wirkstoffe, die neben einer herbiziden Wirkung gegen Schadpflanzen auch Safenerwirkung an Kulturpflanzen wie Reis aufweisen, wie z. B. Active ingredients which, in addition to a herbicidal action against harmful plants, also have a safener action on crop plants such as rice, such as. B.
"Dimepiperate" oder "MY-93" (5’- 1 -Methyl- 1 -phcnylcthyl-pipcridin- 1 -carbothioat), das als Safener für Reis gegen Schäden des Herbizids Molinate bekannt ist, "Dimepiperate" or "MY-93" (5 '- 1-methyl-1--phcnylcthyl pipcridin- 1 carbothioate), which is known as safener for rice against damage by the herbicide molinate,
"Daimuron" oder "SK 23" (l-(l-Methyl-l-phenylethyl)-3-p-tolyl-hamstoff), das als Safener für Reis gegen Schäden des Herbizids Imazosulfuron bekannt ist,  "Daimuron" or "SK 23" (l- (l-methyl-l-phenylethyl) -3-p-tolylurea), which is known as a safener for rice against damage to the herbicide imazosulfuron,
"Cumyluron" = "JC-940" (3-(2-Chlorphenylmethyl)-l-(l-methyl-l-phenyl-ethyl)hamstoff, siehe JP-A-60087270), das als Safener für Reis gegen Schäden einiger Herbizide bekannt ist, "Methoxyphenon" oder "NK 049" (3,3'-Dimethyl-4-methoxy-benzophenon), das als Safener für Reis gegen Schäden einiger Herbizide bekannt ist,  "Cumyluron" = "JC-940" (3- (2-chlorophenylmethyl) -l- (l-methyl-l-phenyl-ethyl) urea, see JP-A-60087270), which acts as a safener for rice against damage to some herbicides is known as "methoxyphenone" or "NK 049" (3,3'-dimethyl-4-methoxy-benzophenone), which is known as a safener for rice against damage by some herbicides,
"CSB" (l-Brom-4-(chlormethylsulfonyl)benzol) von Kumiai, (CAS-Reg.Nr. 54091-06-4), das als Safener gegen Schäden einiger Herbizide in Reis bekannt ist.  "COD" (l-bromo-4- (chloromethylsulfonyl) benzene) from Kumiai, (CAS Reg. No. 54091-06-4), which is known as a safener against damage to some herbicides in rice.
V erbindungen der F ormel (S 15) oder deren T automere, Connections of the formula (S 15) or their t automere,
wie sie in der WO-A-2008/131861 und WO-A-2008/131860 beschrieben sind, as described in WO-A-2008/131861 and WO-A-2008/131860,
worin RH 1 einen (Ci-CejHaloalkylrest bedeutet und wherein R H 1 is a (Ci-CejHaloalkylrest and
RH 2 Wasserstoff oder Halogen bedeutet und R H 2 represents hydrogen or halogen and
RH 3, RH 4 unabhängig voneinander Wasserstoff, (Ci-Ci6)Alkyl, (C2-Ci6)Alkenyl oder R H 3 , R H 4 independently of one another are hydrogen, (Ci-Ci 6 ) alkyl, (C2-Ci6) alkenyl or
(C2-Ci6)Alkinyl, (C 2 -Ci 6 ) alkynyl,
wobei jeder der letztgenannten 3 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Cyano, (Ci-C i)Alkoxy, (Ci-C i)Haloalkoxy, (Ci-C ijAlkylthio, (Ci-C ijAlkylamino, Di[(Ci-C4)alkyl]-amino, [(Ci-C4)Alkoxy]- carbonyl, [(Ci-C tjHaloalkoxyj-carbonyl, (C3-C6)Cycloalkyl, das unsubstituiert oder substituiert ist, Phenyl, das unsubstituiert oder substituiert ist, und Heterocyclyl, das unsubstituiert oder substituiert ist, substituiert ist, where each of the latter 3 residues unsubstituted or by one or more residues from the group halogen, hydroxy, cyano, (Ci-C i) alkoxy, (Ci-C i) haloalkoxy, (Ci-C ijalkyl thio, (Ci-C ijalkylamino, Di [(Ci-C4) alkyl] amino, [(Ci-C4) alkoxy] carbonyl, [(Ci-C t j haloalkoxyj-carbonyl, (C3-C6) cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or is substituted, and heterocyclyl which is unsubstituted or substituted is substituted,
oder (C3-C6)Cycloalkyl, (C4-C6)Cycloalkenyl, (C3-C6)Cycloalkyl, das an einer Seite des Rings mit einem 4 bis 6-gliedrigen gesättigten oder ungesättigten carbocyclischen Ring kondensiert ist, oder (C4-C6)Cycloalkenyl, das an einer Seite des Rings mit einem 4 bis 6-gliedrigen gesättigten oder ungesättigten carbocyclischen Ring kondensiert ist,  or (C3-C6) cycloalkyl, (C4-C6) cycloalkenyl, (C3-C6) cycloalkyl fused to one side of the ring with a 4-6 membered saturated or unsaturated carbocyclic ring, or (C4-C6) cycloalkenyl which is condensed on one side of the ring with a 4 to 6-membered saturated or unsaturated carbocyclic ring,
wobei jeder der letztgenannten 4 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Cyano, (Ci-C4)Alkyl, (Ci-C4)Haloalkyl, (Ci-C4)Alkoxy, (Ci-C4)Haloalkoxy, (Ci-C4)Alkylthio, (Ci-C4)Alkylamino, Di[(Ci- C4)alkyl]-amino, [(Ci-C4)Alkoxy]-carbonyl, [(Ci-C4)Haloalkoxy]-carbonyl, where each of the latter 4 residues is unsubstituted or by one or more residues from the group halogen, hydroxy, cyano, (Ci-C4) alkyl, (Ci-C4) haloalkyl, (Ci-C 4 ) alkoxy, (Ci-C 4 ) Haloalkoxy, (Ci-C 4 ) alkylthio, (Ci-C 4 ) alkylamino, di [(Ci-C4) alkyl] amino, [(Ci-C4) alkoxy] carbonyl, [(Ci-C4) haloalkoxy] - carbonyl,
(C3-C6)Cycloalkyl, das unsubstituiert oder substituiert ist, Phenyl, das unsubstituiert oder substituiert ist, und Heterocyclyl, das unsubstituiert oder substituiert ist, substituiert ist,  (C3-C6) cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted and heterocyclyl which is unsubstituted or substituted,
bedeutet oder  means or
RH 3 (Ci-C4)-Alkoxy, (C2-C4)Alkenyloxy, (C2-C6)Alkinyloxy oder (C2-C4)Haloalkoxy bedeutet undR is H 3 (Ci-C4) alkoxy, (C2-C4) alkenyloxy, (C2-C6) alkynyloxy or (C2-C4) haloalkoxy and
RH 4 Wasserstoff oder (Ci-C4)-Alkyl bedeutet oder R H 4 is hydrogen or (Ci-C4) alkyl or
RH 3 und RH 4 zusammen mit dem direkt gebundenen N-Atom einen vier- bis achtgliedrigen R H 3 and R H 4 together with the directly bound N atom form a four- to eight-membered group
heterocyclischen Ring, der neben dem N-Atom auch weitere Heteroringatome, vorzugsweise bis zu zwei weitere Heteroringatome aus der Gruppe N, O und S enthalten kann und der unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Cyano, Nitro, (Ci- C4)Alkyl, (Ci-C4)Haloalkyl, (Ci-C4)Alkoxy, (Ci-C4)Haloalkoxy und (Ci-C4)Alkylthio substituiert ist, bedeutet. 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 halogen, cyano, nitro, (Ci C 4 ) alkyl, (Ci-C 4 ) haloalkyl, (Ci-C 4 ) alkoxy, (Ci-C 4 ) haloalkoxy and (Ci-C 4 ) alkylthio is substituted.
S16) Wirkstoffe, die vorrangig als Herbizide eingesetzt werden, jedoch auch Safenerwirkung auf Kulturpflanzen aufweisen, z. B.  S16) Active ingredients which are primarily used as herbicides, but also have safener action on crops, for. B.
(2,4-Dichlorphenoxy)essigsäure (2,4-D),  (2,4-dichlorophenoxy) acetic acid (2,4-D),
(4-Chlorphenoxy)essigsäure,  (4-chlorophenoxy) acetic acid,
(R,S)-2-(4-Chlor-o-tolyloxy)propionsäure (Mecoprop),  (R, S) -2- (4-chloro-o-tolyloxy) propionic acid (mecoprop),
4-(2,4-Dichlorphenoxy)buttersäure (2,4-DB),  4- (2,4-dichlorophenoxy) butyric acid (2,4-DB),
(4-Chlor-o-tolyloxy)essigsäure (MCPA), 4-(4-Chlor-o-tolyloxy)buttersäure, (4-chloro-o-tolyloxy) acetic acid (MCPA), 4- (4-chloro-o-tolyloxy) butyric acid,
4-(4-Chlorphenoxy)buttersäure,  4- (4-chlorophenoxy) butyric acid,
3,6-Dichlor-2-methoxybenzoesäure (Dicamba),  3,6-dichloro-2-methoxybenzoic acid (dicamba),
l-(Ethoxycarbonyl)ethyl-3,6-dichlor-2-methoxybenzoat (Lactidichlor-ethyl).  1- (Ethoxycarbonyl) ethyl 3,6-dichloro-2-methoxybenzoate (lactidichloro-ethyl).
Bevorzugte Safener in Kombination mit den erfindungsgemäßen Verbindungend der allgemeinen Formel (I) und/oder deren Salze, insbesondere mit den Verbindungen der Formeln (1-1) bis (1-662) und/oder deren Salze sind: Cloquintocet-mexyl, Cyprosulfamid, Fenchlorazol-ethylester, Isoxadifen- ethyl, Mefenpyr-diethyl, Fenclorim, Cumyluron, S4-1 und S4-5, und besonders bevorzugte Safener sind: Cloquintocet-mexyl, Cyprosulfamid, Isoxadifen-ethyl und Mefenpyr-diethyl.  Preferred safeners in combination with the compounds according to the invention of the general formula (I) and / or their salts, in particular with the compounds of the formulas (1-1) to (1-662) and / or their salts, are: Cloquintocet-mexyl, cyprosulfamide, Fenchlorazole-ethyl ester, Isoxadifen-ethyl, Mefenpyr-diethyl, Fenclorim, Cumyluron, S4-1 and S4-5, and particularly preferred safeners are: Cloquintocet-mexyl, Cyprosulfamid, Isoxadifen-ethyl and Mefenpyr-diethyl.
Biologische Beispiele Biological examples
A. Herbizide Wirkung im frühen Nachauflauf A. Early post-herbicidal effects
Samen von mono- bzw. dikotylen Unkrautpflanzen wurden in 96-well Mikrotiterplatten in Quarzsand ausgelegt und in der Klimakammer unter kontrollierten Wachstumsbedingungen angezogen. 5 bis 7 Tage nach der Aussaat wurden die Versuchspflanzen im Keimblattstadium behandelt. Die in Form von Emulsionskonzentraten (EC) formulierten erfindungsgemäßen Verbindungen wurden mit einer Seeds of monocotyledonous or dicotyledonous weed plants were placed in 96-well microtiter plates in quartz sand and grown in the climatic chamber under controlled growth conditions. 5 to 7 days after sowing, the test plants were treated at the cotyledon stage. The compounds according to the invention formulated in the form of emulsion concentrates (EC) were treated with a
Wasseraufwandmenge von umgerechnet 2200 Liter pro Hektar appliziert. Nach 9 bis 12 Tagen The amount of water applied is equivalent to 2200 liters per hectare. After 9 to 12 days
Standzeit der Versuchspflanzen in der Klimakammer unter optimalen Wachstumsbedingungen, wurde die Wirkung der Präparate visuell im Vergleich zu unbehandelten Kontrollen bonitiert. Beispielsweise bedeutet 100% Wirkung = Pflanzen sind abgestorben, 0% Wirkung = wie Kontrollpflanzen. If the test plants remained in the climatic chamber under optimal growth conditions, the effect of the preparations was rated visually in comparison to untreated controls. For example, 100% activity = plants have died, 0% activity = like control plants.
In den nachstehenden Tabllen Al bis A2 sind die Wirkungen ausgewählter Verbindungen der allgemeinen Formel (I) gemäß Tabelle 1 auf verschiedene Schadpflanzen und einer Aufwandmenge entsprechend 1900 g/ha, die gemäß zuvor genannter Versuchvorschrift erhalten wurden, dargestellt. The following tables A1 to A2 show the effects of selected compounds of the general formula (I) according to Table 1 on various harmful plants and an application rate corresponding to 1900 g / ha, which were obtained in accordance with the aforementioned test instructions.
Tabelle Al : Wirkung gegen Agrostis tenuis (AGSTE) im frühen Nachauflauf Table A1: Effect against Agrostis tenuis (AGSTE) in the early post-emergence
Tabelle A2: Wirkung gegen Poa annua (POAAN) im frühen Nachauflauf Table A2: Action against Poa annua (POAAN) in the early post-emergence
Die Versuchsergebnisse belegen, dass erfindungsgemäße Verbindungen der allgemeinen Formel (I) bei Behandlung im frühen Nachauflauf eine gute herbizide Wirksamkeit gegen ausgewählte Schadpflanzen wie Agrostis tenuis (AGSTE) und Poa annua (POAAN) bei einer jeweiligen Aufwandmenge von 1900 g Aktivsubstanz pro Hektar aufweisen. The test results prove that compounds of the general formula (I) according to the invention have good herbicidal activity against selected harmful plants such as Agrostis tenuis (AGSTE) and Poa annua (POAAN) at a respective application rate of 1900 g of active substance per hectare when treated in the early post-emergence.
B. Herbizide Wirkung und Kulturverträglichkeit im Nachauflauf B. Post-emergence herbicidal activity and crop tolerance
Samen von mono- bzw. dikotylen Unkrautpflanzen wurden in Kunststofftöpfen in sandigem Lehmboden ausgelegt (Doppelaussaaten mit jeweils einer Spezies mono- bzw. dikotyler Unkrautpflanzen pro Topf), mit Erde abgedeckt und im Gewächshaus unter kontrollierten Wachstumsbedingungen angezogen. 2 bis 3 Wochen nach der Aussaat wurden die Versuchspflanzen im Einblattstadium behandelt. Die in Form von benetzbaren Pulvern (WP) oder als Emulsionskonzentrate (EC) formulierten erfindungsgemäßen Verbindungen wurden als wässrige Suspension bzw. Emulsion, unter Zusatz von 0,5% Additiv, mit einer Wasseraufwandmenge von umgerechnet 600 Liter pro Hektar, auf die grünen Pflanzenteile appliziert. Nach ca. 3 Wochen Standzeit der Versuchspflanzen im Gewächshaus, unter optimalen Wachstumsbedingungen, wurde die Wirkung der Präparate visuell im Vergleich zu unbehandelten Kontrollen bonitiert. Beispielsweise bedeutet 100% Wirkung = Pflanzen sind abgestorben, 0% Wirkung = wie Kontrollpflanzen. ln den nachstehenden Tabllen Bl bis B8 sind die Wirkungen ausgewählter Verbindungen der allgemeinen Formel (1) gemäß Tabelle 1 auf verschiedene Schadpflanzen und einer Aufwandmenge entsprechend 1280 g/ha, die gemäß zuvor genannter Versuchvorschrift erhalten wurden, dargestellt. Tabelle Bl : Nachauflaufwirkung gegen Echinochloa crus-galli (ECHCG) Seeds of monocotyledonous or dicotyledonous weed plants were placed in plastic pots in sandy loam soil (double sowing, each with one species of monocotyledonous or dicotyledonous weed plant per pot), covered with soil and grown in the greenhouse under controlled growth conditions. The test plants were treated at the single-leaf stage 2 to 3 weeks after sowing. The compounds according to the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) were applied to the green parts of the plant as an aqueous suspension or emulsion, with the addition of 0.5% additive, with a water application rate of 600 liters per hectare , After the test plants had stood in the greenhouse for about 3 weeks under optimal growth conditions, the effect of the preparations was assessed visually in comparison with untreated controls. For example, 100% activity = plants have died, 0% activity = like control plants. The following tablets B1 to B8 show the effects of selected compounds of the general formula (1) according to Table 1 on various harmful plants and an application rate corresponding to 1280 g / ha, which were obtained according to the aforementioned test instructions. Table B1: Post-emergence effect against Echinochloa crus-galli (ECHCG)
Tabelle B2: Nachauflaufwirkung gegen Poa annua (POAAN) Table B2: Post-emergence effects against Poa annua (POAAN)
Tabelle B3: Nachauflaufwirkung gegen Abutilon theophrasti (ABUTH) Table B3: Post-emergence effect against Abutilon theophrasti (ABUTH)
Tabelle B4: Nachauflaufwirkung gegen Amaranthus retroflexus (AMARE) Table B4: Post-emergence effect against Amaranthus retroflexus (AMARE)
Tabelle B5: Nachauflaufwirkung gegen Stellaria media (STEME) Tabelle B6: Nachauflaufwirkung gegen Lolium rigidum (LOLRI) Table B5: Post-emergence effects against Stellaria media (STEME) Table B6: Post-emergence effect against Lolium rigidum (LOLRI)
Tabelle B7: Nachauflaufwirkung gegen Setaria viridis (SETV1) Table B7: Post-emergence effect against Setaria viridis (SETV1)
Tabelle B8: Nachauflaufwirkung gegen Matricaria inodora (MAT1N) Table B8: Post-emergence effect against Matricaria inodora (MAT1N)
Die Versuchsergebnisse belegen, dass erfindungsgemäße Verbindungen der allgemeinen Formel (1) bei Behandlung im Nachauflauf eine gute herbizide Wirksamkeit gegen ausgewählte Schadpflanzen wie z.B. Echinochloa crus-galli (ECHCG), Poa annua (POAAN), Abutilon theophrasti (ABUTH),The test results show that compounds of the general formula (1) according to the invention have good herbicidal activity against selected harmful plants, such as e.g. Echinochloa crus-galli (ECHCG), Poa annua (POAAN), Abutilon theophrasti (ABUTH),
Amaranthus retroflexus (AMARE), Stellaria media (STEME), Lolium rigidum (LOLR1), Setaria viridis (SETV1) und Matricaria inodora (MAT1N) bei einer Aufwandmenge von 1280 g Aktivsubstanz pro Hektar aufweisen. Amaranthus retroflexus (AMARE), Stellaria media (STEME), Lolium rigidum (LOLR1), Setaria viridis (SETV1) and Matricaria inodora (MAT1N) at an application rate of 1280 g of active ingredient per hectare.
C. Herbizide Wirkung und Kulturverträglichkeit im Vorauflauf C. Pre-emergence herbicidal activity and crop tolerance
Samen von mono- und dikotylen Unkrautpflanzen wurden in Kunststofftöpfen, in sandigem Seeds of monocotyledonous and dicotyledonous weed plants were grown in plastic pots, in sandy
Lehmboden, ausgelegt (Doppelaussaaten mit jeweils eine Spezies mono- bzw. dikotyler Loam soil, laid out (double sowing with one species each mono- or dicotyledonous
Unkrautpflanzen pro Topf) und mit Erde abgedeckt. Die in Form von benetzbaren Pulvern (WP) oder als Emulsionskonzentrate (EC) formulierten erfindungsgemäßen Verbindungen wurden dann als wässrige Suspension bzw. Emulsion, unter Zusatz von 0,5% Additiv, mit einer Wasseraufwandmenge von umgerechnet 600 Liter pro Hektar auf die Oberfläche der Abdeckerde appliziert. Nach der Behandlung wurden die Töpfe im Gewächshaus aufgestellt und unter guten Wachstumsbedingungen für die Testpflanzen gehalten. Nach ca. 3 Wochen wurde die Wirkung der Präparate visuell im Vergleich zu unbehandelten Kontrollen in Prozentwerten bonitiert. Beispielsweise bedeutet 100% Wirkung = Pflanzen sind abgestorben, 0% Wirkung = wie Kontrollpflanzen. ln nachstehenden Tabellen Cl bis C8 sind die Wirkungen ausgewählter Verbindungen der allgemeinen Formel (1) gemäß Tabelle 1 auf verschiedene Schadpflanzen und einer Aufwandmenge entsprechend 1280 g/ha, die gemäß zuvor genannter Versuchvorschrift erhalten wurden, dargestellt. Weed plants per pot) and covered with soil. The compounds according to the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) were then applied to the surface of the covering earth as an aqueous suspension or emulsion, with the addition of 0.5% additive, with a water application rate of 600 liters per hectare applied. After the treatment, the pots were placed in the greenhouse and kept under good growth conditions for the test plants. After about 3 weeks, the effect of the preparations was rated visually in percentages compared to untreated controls. For example, 100% activity = plants have died, 0% activity = like control plants. Tables C1 to C8 below show the effects of selected compounds of the general formula (1) according to Table 1 on various harmful plants and an application rate corresponding to 1280 g / ha, which were obtained in accordance with the aforementioned test instructions.
Tabelle Cl : Vorauflaufwirkung gegen Echinochloa crus-galli (ECHCG) Table C1: Pre-emergence effect against Echinochloa crus-galli (ECHCG)
Tabelle C2: Vorauflaufwirkung gegen Lolium rigidum (LOLRI) Table C2: Pre-emergence effect against Lolium rigidum (LOLRI)
Tabelle C3: Vorauflaufwirkung gegen Poa annua (POAAN) Table C3: Pre-emergence effect against Poa annua (POAAN)
Tabelle C4: Vorauflaufwirkung gegen Setaria viridis (SETVI) Table C4: Pre-emergence effect against Setaria viridis (SETVI)
Tabelle C5: Vorauflaufwirkung gegen Abutilon theophrasti (ABUTH) Tabelle C6: Vorauflaufwirkung gegen Amaranthus retroflexus (AMARE) Table C5: Pre-emergence effect against Abutilon theophrasti (ABUTH) Table C6: Pre-emergence effect against Amaranthus retroflexus (AMARE)
Tabelle C7: Vorauflaufwirkung gegen Matricaria inodora (MATIN) Table C7: Pre-emergence effect against Matricaria inodora (MATIN)
Tabelle C8: Vorauflaufwirkung gegen Stellaria media (STEME) Table C8: Pre-emergence effect against Stellaria media (STEME)
Die Versuchsergebnisse belegen, dass erfindungsgemäße Verbindungen der allgemeinen Formel (I) bei Behandlung im Vorauflauf eine gute herbizide Wirksamkeit gegen ausgewählte Schadpflanzen wie Echinochloa crus-galli (ECHCG), Lolium rigidum (LOLRI), Setaria viridis (SETVI), Poa annua (POAAN), Abutilon theophrasti (ABUTH), Amaranthus retroflexus (AMARE), Stellaria mediaThe test results prove that compounds of the general formula (I) according to the invention have good herbicidal activity against selected harmful plants such as Echinochloa crus-galli (ECHCG), Lolium rigidum (LOLRI), Setaria viridis (SETVI), Poa annua (POAAN) when treated beforehand. , Abutilon theophrasti (ABUTH), Amaranthus retroflexus (AMARE), Stellaria media
(STEME) und Matricaria inodora (MATIN) bei einer Aufwandmenge von 1280 g Aktivsubstanz pro Hektar aufweisen. (STEME) and Matricaria inodora (MATIN) at an application rate of 1280 g of active ingredient per hectare.

Claims

Patentansprüche claims
1. Substituierte 2-Heteroaryloxypyridine der allgemeinen Formel (I) oder deren Salze 1. Substituted 2-heteroaryloxypyridines of the general formula (I) or their salts
worin  wherein
X für Stickstoff, -CF- oder -CH- steht, X represents nitrogen, -CF- or -CH-,
A für Sauerstoff, -S(0)n-, -C(R4)(R5) -, -C(=0) -, oder -NR6- steht A stands for oxygen, -S (0) n- , -C (R 4 ) (R 5 ) -, -C (= 0) -, or -NR 6 -
mit n gleich 0, 1 oder 2,  with n equal to 0, 1 or 2,
R1 für ein gegebenenfalls substituiertes Aryl, Heteroaryl, Heterocylyl, (C3-Cio)-Cycloalkyl oder (C3-Cio)-Cycloalkenyl steht, wobei jeder Ring oder jedes Ringsystem optional mit bis zu 5 Substituenten, unabhängig voneinander ausgewählt aus der Gruppe R7, substituiert ist; R 1 represents an optionally substituted aryl, heteroaryl, heterocylyl, (C3-Cio) cycloalkyl or (C3-Cio) cycloalkenyl, each ring or ring system optionally having up to 5 substituents, independently selected from the group R 7 , is substituted;
R2 unabhängig voneinander für Halogen, Cyano, Nitro, Formyl, Formamid, (Ci -Cs)- Alkyl, (Ci-Csj-Haloalkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (C2-C8)-Haloalkenyl, (C2-C8)- Haloalkinyl, (Ci-C4)-Alkoxy-(Ci-C4)-alkyl, (Ci-C4)-Haloalkoxy-(Ci-C4)-alkyl, (Ci-C4)- Alkylthio-(Ci-C4)-alkyl, (Ci-C4)-Alkylsulfinyl-(Ci-C4)-alkyl, (Ci-C4)-Alkylsulfonyl- (Ci-C4)-alkyl, (Ci-C8)-Alkylcarbonyl, (Ci-C8)-Haloalkylcarbonyl, (C3-C8)- Cycloalkylcarbonyl, Carboxyl, (Ci-C8)-Alkoxycarbonyl, (Ci-C8)- Haloalkoxycarbonyl, (C3-C8)-Cycloalkoxycarbonyl, Carbamoyl, (C2-C8)-Alkylaminocarbonyl, (C2-Cio)- Dialkylaminocarbonyl, (C3-Cio)-Cycloalkylaminocarbonyl, (Ci-C4)-Alkoxycarbonyl- (Ci-C4)-alkyl, (Ci-C4)-Haloalkoxycarbonyl-(Ci-C4)-alkyl, Carboxy-(Ci-C4)-alkyl, Hydroxy, Amino, (Ci-C8)-Alkoxy, (Ci-C8)-Haloalkoxy, (Ci-C8)-Alkylthio, (Ci-C8)- Haloalkylthio, (C3-C8)-Cycloalkylthio, (Ci-C8)-Alkylsulfinyl, (Ci-C8)-Haloalkylsulfinyl, (C3-C8)-Cycloalkylsulfinyl, (Ci-C8)-Alkylsulfonyl, (Ci-C8)-Haloalkylsulfonyl, (C3-C8)- Cycloalkylsulfonyl, (Ci-C8)-Alkylaminosulfonyl, (C2-C8)-Dialkylaminosulfonyl oder (C3-C8)-Trialkylsilyl steht, m ist gleich 0, 1, 2, oder 3, R 2 independently of one another for halogen, cyano, nitro, formyl, formamide, (Ci-Cs) -alkyl, (Ci-Csj-haloalkyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, (C 2 -C 8 ) haloalkenyl, (C 2 -C 8 ) haloalkynyl, (Ci-C 4 ) alkoxy- (Ci-C 4 ) alkyl, (Ci-C 4 ) -haloalkoxy- (Ci C 4 ) alkyl, (Ci-C 4 ) alkylthio- (Ci-C 4 ) -alkyl, (Ci-C 4 ) -alkylsulfinyl- (Ci-C 4 ) -alkyl, (Ci-C 4 ) -alkylsulfonyl - (Ci-C 4 ) -alkyl, (Ci-C 8 ) -alkylcarbonyl, (Ci-C 8 ) -haloalkylcarbonyl, (C3-C 8 ) - cycloalkylcarbonyl, carboxyl, (Ci-C 8 ) -alkoxycarbonyl, (Ci -C 8 ) - Haloalkoxycarbonyl, (C3-C 8 ) -cycloalkoxycarbonyl, carbamoyl, (C 2 -C 8 ) -alkylaminocarbonyl, (C 2 -Cio) - dialkylaminocarbonyl, (C3-Cio) -cycloalkylaminocarbonyl, (Ci-C 4 ) -Alkoxycarbonyl- (Ci-C 4 ) -alkyl, (Ci-C 4 ) -haloalkoxycarbonyl- (Ci-C 4 ) -alkyl, carboxy- (Ci-C 4 ) -alkyl, hydroxy, amino, (Ci-C 8 ) alkoxy, (Ci-C 8 ) -haloalkoxy, (Ci-C 8 ) -alkylthio, (Ci-C 8 ) -haloalkylthio, (C3-C 8 ) -cycloalkylthio, (Ci-C 8 ) -alkylsulfinyl, (Ci-C 8 ) haloalkylsulfinyl, (C3-C 8 ) cyc loalkylsulfinyl, (Ci-C 8 ) -alkylsulfonyl, (Ci-C 8 ) -haloalkylsulfonyl, (C3-C 8 ) - Cycloalkylsulfonyl, (Ci-C 8 ) -alkylaminosulfonyl, (C 2 -C 8 ) -dialkylaminosulfonyl or (C 3 -C 8 ) -trialkylsilyl, m is 0, 1, 2 or 3,
R3 für Wasserstoff, Halogen, Cyano, Nitro, Formyl, (Ci-C8)-Alkyl, (Ci-C8)-Haloalkyl,R 3 represents hydrogen, halogen, cyano, nitro, formyl, (Ci-C 8 ) -alkyl, (Ci-C 8 ) -haloalkyl,
(C2-C8)-Alkenyl, (C2-C8)-Alkmyl, (C2-C8)-Haloalkenyl, (C2-C8)-Haloalkinyl, (Ci-C4)- Alkoxy-(Ci-C4)-alkyl, (Ci-C4)-Haloalkoxy-(Ci-C4)-alkyl, (Ci-C4)-Alkylthio-(Ci-C4)- alkyl, (Ci-C4)-Alkylsulfinyl-(Ci-C4)-alkyl, (Ci-C4)-Alkylsulfonyl-(Ci-C4)-alkyl, (Ci-Cs)- Alkylcarbonyl, (Ci-C8)-Haloalkylcarbonyl, (C3-C8)-Cycloalkylcarbonyl, Carboxyl, (Ci-C8)-Alkoxycarbonyl, (Ci-Cs)- Haloalkoxycarbonyl, (C3-C8)-Cycloalkoxycarbonyl, (Ci-C8)-Alkylaminocarbonyl, (C2-C8)-Dialkylaminocarbonyl, (C3-Cs)- Cycloalkylaminocarbonyl, Hydroxy, (Ci-C8)-Alkoxy, (Ci-C8)-Haloalkoxy, (Ci-Cs)- Alkylthio, (Ci-C8)-Haloalkylthio, (C3-C8)-Cycloalkylthio, (Ci-C8)-Alkylsulfinyl, (Ci-C8)-Haloalkylsulfinyl, (C3-C8)-Cycloalkylsulfinyl, (Ci-C8)-Alkylsulfonyl, (Ci-Cs)- Haloalkylsulfonyl, (C3-C8)-Cycloalkylsulfonyl, (Ci-C8)-Alkylaminosulfonyl, (C2-Cs)- Dialkylaminosulfonyl oder (C3-C8)-Trialkylsilyl steht, (C 2 -C 8 ) alkenyl, (C 2 -C 8 ) alkyl, (C 2 -C 8 ) haloalkenyl, (C 2 -C 8 ) haloalkynyl, (Ci-C 4 ) alkoxy- ( Ci-C 4 ) -alkyl, (Ci-C 4 ) -haloalkoxy- (Ci-C 4 ) -alkyl, (Ci-C 4 ) -alkylthio- (Ci-C 4 ) - alkyl, (Ci-C 4 ) -Alkylsulfinyl- (Ci-C 4 ) -alkyl, (Ci-C 4 ) -alkylsulfonyl- (Ci-C 4 ) -alkyl, (Ci-Cs) -alkylcarbonyl, (Ci-C 8 ) -haloalkylcarbonyl, (C 3 -C 8 ) -cycloalkylcarbonyl, carboxyl, (Ci-C 8 ) -alkoxycarbonyl, (Ci-Cs) - haloalkoxycarbonyl, (C 3 -C 8 ) -cycloalkoxycarbonyl, (Ci-C 8 ) -alkylaminocarbonyl, (C 2 -C 8 ) -Dialkylaminocarbonyl, (C 3 -Cs) -cycloalkylaminocarbonyl, hydroxy, (Ci-C 8 ) -alkoxy, (Ci-C 8 ) -haloalkoxy, (Ci-Cs) -alkylthio, (Ci-C 8 ) -haloalkylthio , (C 3 -C 8 ) cycloalkylthio, (Ci-C 8 ) alkylsulfinyl, (Ci-C 8 ) haloalkylsulfinyl, (C 3 -C 8 ) cycloalkylsulfinyl, (Ci-C 8 ) alkylsulfonyl, (Ci -Cs) - haloalkylsulfonyl, (C 3 -C 8 ) -cycloalkylsulfonyl, (Ci-C 8 ) -alkylaminosulfonyl, (C 2 -Cs) - dialkylaminosulfonyl or (C 3 -C 8 ) -trialkylsilyl,
R4 und R5 unabhängig voneinander für Wasserstoff, Hydroxy, Halogen, (Ci-C8)-Alkyl, (Ci-Cs)- Haloalkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkmyl, (Ci-C4)-Alkoxy-(Ci-C4)-alkyl, (Ci-C4)- Haloalkoxy-(Ci-C4)-alkyl, (Ci-C4)-Alkylthio-(Ci-C4)-alkyl, (Ci-C4)-Alkylsulfmyl- (Ci-C4)-alkyl, (Ci-C4)-Alkylsulfonyl-(Ci-C4)-alkyl, (Ci-C8)-Alkylcarbonyl, (Ci-C8)- Haloalkylcarbonyl, (C3-C8)-Cycloalkylcarbonyl, (Ci-C8)-Alkoxycarbonyl, (Ci-Cs)- Haloalkoxycarbonyl, (C3-C8)-Cycloalkoxycarbonyl, (Ci-C8)-Alkylaminocarbonyl, (C2-C8)-Dialkylaminocarbonyl, (C3-C8)-Cycloalkylaminocarbonyl, (Ci-C8)-Alkoxy, (Ci-C8)-Alkylthio, (Ci-C8)-Haloalkylthio, (C3-C8)-Cycloalkylthio, stehen, oder R 4 and R 5 independently of one another are hydrogen, hydroxy, halogen, (Ci-C 8 ) -alkyl, (Ci-Cs) - haloalkyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkyl , (Ci-C 4 ) -alkoxy- (Ci-C 4 ) -alkyl, (Ci-C 4 ) -haloalkoxy- (Ci-C 4 ) -alkyl, (Ci-C 4 ) -alkylthio- (Ci-C 4 ) -alkyl, (Ci-C 4 ) -alkylsulfmyl- (Ci-C 4 ) -alkyl, (Ci-C 4 ) -alkylsulfonyl- (Ci-C 4 ) -alkyl, (Ci-C 8 ) -alkylcarbonyl, (Ci-C 8 ) haloalkylcarbonyl, (C 3 -C 8 ) cycloalkylcarbonyl, (Ci-C 8 ) alkoxycarbonyl, (Ci-Cs) haloalkoxycarbonyl, (C 3 -C 8 ) cycloalkoxycarbonyl, (Ci-C 8 ) -alkylaminocarbonyl, (C 2 -C 8 ) -dialkylaminocarbonyl, (C 3 -C 8 ) -cycloalkylaminocarbonyl, (Ci-C 8 ) -alkoxy, (Ci-C 8 ) -alkylthio, (Ci-C 8 ) - Haloalkylthio, (C 3 -C 8 ) cycloalkylthio, stand, or
R4 und R5 gemeinsam einen 3- bis 6-gliedrigen carbocyclischen Ring oder einen 3- bis 6- gliedrigen gesättigten heterocyclischen Ring mit bis zu 2 Sauerstoffatomen bilden, oder R 4 and R 5 together form a 3- to 6-membered carbocyclic ring or a 3- to 6-membered saturated heterocyclic ring with up to 2 oxygen atoms, or
R4 und R5 gemeinsam einen (Ci-C3)-Alkylidenrest oder (Ci-C3)-Haloalkylidenrest bilden, R6 für Wasserstoff, (Ci-Cg)-Alkyl, (Ci-Cg)-Haloalkyl, Aryl-(Ci-C6)-alkyl, Heteroaryl-(Ci- C6)-alkyl, (C3-C6)-Cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, (C3-C6)- Halocycloalkyl, (C3-C6)-Halocycloalkyl-(Ci-C4)-alkyl, (C2-Cg)-Alkenyl, (C2-Cg)- Alkinyl, (Ci-C4)-Alkoxy-(Ci-C4)-alkyl, (Ci-C4)-Haloalkoxy-(Ci-C4)-alkyl, (Ci-C4)- Alkylthio-(Ci-C4)-alkyl, (Ci-C4)-Alkylsulfinyl-(Ci-C4)-alkyl, (Ci-C4)-Alkylsulfonyl- (Ci-C4)-alkyl, (Ci-Cg)-Alkylcarbonyl, (Ci-Cg)-Haloalkylcarbonyl, (C3-Cg)- Cycloalkylcarbonyl, Formyl, (Ci-Cg)-Alkoxycarbonyl, (Ci-Cg)-Haloalkoxycarbonyl, (C3-Cg)-Cycloalkoxycarbonyl, (Ci-Cg)-Alkylaminocarbonyl, (C2-Cg)- Dialkylaminocarbonyl, (C3-Cg)-Cycloalkylaminocarbonyl steht, R 4 and R 5 together form a (Ci-C 3 ) alkylidene radical or (Ci-C 3 ) haloalkylidene radical, R 6 is hydrogen, (Ci-Cg) -alkyl, (Ci-Cg) -haloalkyl, aryl- (Ci-C 6 ) -alkyl, heteroaryl- (Ci-C 6 ) -alkyl, (C 3 -C 6 ) -Cycloalkyl, (C3-C 6 ) -cycloalkyl- (Ci-C 6 ) -alkyl, (C 3 -C 6 ) -halocycloalkyl, (C 3 -C6) -halocycloalkyl- (Ci-C4) -alkyl, (C2 -Cg) alkenyl, (C 2 -Cg) alkynyl, (Ci-C 4 ) alkoxy- (Ci-C 4 ) alkyl, (Ci-C 4 ) -haloalkoxy- (Ci-C 4 ) alkyl , (Ci-C 4 ) - alkylthio- (Ci-C 4 ) -alkyl, (Ci-C 4 ) -alkylsulfinyl- (Ci-C 4 ) -alkyl, (Ci-C 4 ) -alkylsulfonyl- (Ci-C 4 ) -alkyl, (Ci-Cg) -alkylcarbonyl, (Ci-Cg) -haloalkylcarbonyl, (C 3 -Cg) -cycloalkylcarbonyl, formyl, (Ci-Cg) -alkoxycarbonyl, (Ci-Cg) -haloalkoxycarbonyl, (C 3 -Cg) -cycloalkoxycarbonyl, (Ci-Cg) -alkylaminocarbonyl, (C 2 -Cg) -dialkylaminocarbonyl, (C 3 -Cg) -cycloalkylaminocarbonyl,
R7 für Wasserstoff, Halogen, Cyano, Nitro, Formyl, (Ci-Cg)-Alkyl, (Ci-Cg)-Haloalkyl,R 7 represents hydrogen, halogen, cyano, nitro, formyl, (Ci-Cg) alkyl, (Ci-Cg) haloalkyl,
(C2-Cg)-Alkenyl, (C2-Cg)-Alkinyl, (C2-Cg)-Haloalkenyl, (C2-Cg)-Haloalkinyl, (Ci-C4)- Alkoxy-(Ci-C4)-alkyl, (Ci-C4)-Haloalkoxy-(Ci-C4)-alkyl, (Ci-C4)-Alkylthio-(Ci-C4)- alkyl, (Ci-C4)-Alkylsulfinyl-(Ci-C4)-alkyl, (Ci-C4)-Alkylsulfonyl-(Ci-C4)-alkyl, (Ci-Cg)- Alkylcarbonyl, (Ci-Cg)-Haloalkylcarbonyl, (C3-Cg)-Cycloalkylcarbonyl, Carboxyl, (Ci-Cg)-Alkoxycarbonyl, (Ci-Cg)- Haloalkoxycarbonyl, (C3-Cg)-Cycloalkoxycarbonyl, (Ci-Cg)-Alkylaminocarbonyl, (C2-Cg)-Dialkylaminocarbonyl, (C3-Cg)- Cycloalkylaminocarbonyl, Hydroxy, (Ci-Cg)-Alkoxy, (Ci-Cg)-Haloalkoxy, (Ci-Cg)- Alkylthio, (Ci-Cg)-Haloalkylthio, (C3-Cg)-Cycloalkylthio, (Ci-Cg)-Alkylsulfmyl, (Ci-Cg)-Haloalkylsulfinyl, (C3-Cg)-Cycloalkylsulfinyl, (Ci-Cg)-Alkylsulfonyl, (Ci-Cg)- Haloalkylsulfonyl, (C3-Cg)-Cycloalkylsulfonyl, (Ci-Cg)-Alkylaminosulfonyl, (C2-Cg)- Dialkylaminosulfonyl oder (C3-Cg)-Trialkylsilyl steht. (C 2 -Cg) alkenyl, (C 2 -Cg) alkynyl, (C 2 -Cg) haloalkenyl, (C 2 -Cg) haloalkynyl, (Ci-C 4 ) alkoxy- (Ci-C 4 ) -alkyl, (Ci-C 4 ) -haloalkoxy- (Ci-C 4 ) -alkyl, (Ci-C 4 ) -alkylthio- (Ci-C 4 ) -alkyl, (Ci-C 4 ) -alkylsulfinyl- ( Ci-C 4 ) -alkyl, (Ci-C 4 ) -alkylsulfonyl- (Ci-C 4 ) -alkyl, (Ci-Cg) -alkylcarbonyl, (Ci-Cg) -haloalkylcarbonyl, (C 3 -Cg) -cycloalkylcarbonyl , Carboxyl, (Ci-Cg) -alkoxycarbonyl, (Ci-Cg) - haloalkoxycarbonyl, (C 3 -Cg) -cycloalkoxycarbonyl, (Ci-Cg) -alkylaminocarbonyl, (C 2 -Cg) -dialkylaminocarbonyl, (C 3 -Cg ) - Cycloalkylaminocarbonyl, hydroxy, (Ci-Cg) alkoxy, (Ci-Cg) -haloalkoxy, (Ci-Cg) - alkylthio, (Ci-Cg) -haloalkylthio, (C 3 -Cg) -cycloalkylthio, (Ci Cg) alkylsulfmyl, (Ci-Cg) haloalkylsulfinyl, (C 3 -Cg) cycloalkylsulfinyl, (Ci-Cg) alkylsulfonyl, (Ci-Cg) haloalkylsulfonyl, (C 3 -Cg) cycloalkylsulfonyl, (Ci Cg) -alkylaminosulfonyl, (C 2 -Cg) - dialkylaminosulfonyl or (C 3 -Cg) -trialkylsilyl.
2. Verbindung der allgemeinen Formel (1) nach Anspruch loder deren Salze, worin 2. A compound of general formula (1) according to claim 1 or its salts, wherein
X für Stickstoff, -CF- oder -CH- steht, X represents nitrogen, -CF- or -CH-,
A für Sauerstoff, -S(0)n-, -C(R4)(R5) -, -C(=0) -, oder -NR6- steht A stands for oxygen, -S (0) n- , -C (R 4 ) (R 5 ) -, -C (= 0) -, or -NR 6 -
mit n gleich 0, 1 oder 2,  with n equal to 0, 1 or 2,
R1 für ein gegebenenfalls substituiertes Aryl, Heteroaryl, oder Heterocylyl steht, wobei jeder Ring oder jedes Ringsystem optional mit bis zu 5 Substituenten, unabhängig voneinander ausgewählt aus der Gruppe R7, substituiert ist, R2 unabhängig voneinander für Halogen, Cyano, Nitro, Formyl, Formamid, (Ci-C4)-Alkyl, (Ci-C4)-Haloalkyl, (C2-C4)-Alkenyl, (C2-C4)-Alkinyl, (C2-C4)-Haloalkenyl, (Ci-C4)- Alkoxy-(Ci-C4)-alkyl, (Ci-C4)-Haloalkoxy-(Ci-C4)-alkyl, (Ci-C4)-Alkylcarbonyl, (Ci-C4)-Haloalkylcarbonyl, Carboxyl, (Ci-C4)-Alkoxycarbonyl, (C1-C4)- Haloalkoxycarbonyl, (C3-C6)-Cycloalkoxycarbonyl, Carbamoyl, (C2-C4)- Alkylaminocarbonyl, (C2-C6)-Dialkylaminocarbonyl, (Ci-C4)-Alkoxycarbonyl-(Ci-C4)- alkyl, (Ci-C4)-Haloalkoxycarbonyl-(Ci-C4)-alkyl, Carboxy-(Ci-C4)-alkyl, Hydroxy, Amino, (Ci-C4)-Alkoxy, (Ci-C4)-Haloalkoxy, (Ci-C4)-Alkylthio, (Ci-C4)-Alkylsulfinyl, (Ci-C4)-Alkylsulfonyl, (Ci-C4)-Alkylaminosulfonyl, (C2-C6)-Dialkylaminosulfonyl oder (C3-C6)-Trialkylsilyl steht, m ist gleich 0, 1, 2, oder 3, R 1 represents an optionally substituted aryl, heteroaryl or heterocylyl, each ring or ring system optionally being substituted with up to 5 substituents, selected independently of one another from the group R 7 , R 2 is independently halogen, cyano, nitro, formyl, formamide, (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) -Alkynyl, (C 2 -C 4 ) -haloalkenyl, (Ci-C 4 ) -alkoxy- (Ci-C 4 ) -alkyl, (Ci-C 4 ) -haloalkoxy- (Ci-C 4 ) -alkyl, ( Ci-C 4 ) -alkylcarbonyl, (Ci-C 4 ) -haloalkylcarbonyl, carboxyl, (Ci-C 4 ) -alkoxycarbonyl, (C 1 -C 4 ) - haloalkoxycarbonyl, (C 3 -C 6 ) -cycloalkoxycarbonyl, carbamoyl, (C 2 -C 4 ) alkylaminocarbonyl, (C 2 -C 6 ) dialkylaminocarbonyl, (Ci-C 4 ) alkoxycarbonyl- (Ci-C 4 ) alkyl, (Ci-C 4 ) -haloalkoxycarbonyl- (Ci C 4 ) -alkyl, carboxy- (Ci-C 4 ) -alkyl, hydroxy, amino, (Ci-C 4 ) -alkoxy, (Ci-C 4 ) -haloalkoxy, (Ci-C 4 ) -alkylthio, (Ci -C 4 ) alkylsulfinyl, (Ci-C 4 ) -alkylsulfonyl, (Ci-C 4 ) -alkylaminosulfonyl, (C 2 -C 6 ) -dialkylaminosulfonyl or (C 3 -C 6 ) -trialkylsilyl, m is 0 , 1, 2, or 3,
R3 für Wasserstoff, Halogen, Cyano, Nitro, Formyl, (Ci-C4)-Alkyl, (Ci-C4)-Haloalkyl,R 3 represents hydrogen, halogen, cyano, nitro, formyl, (Ci-C4) -alkyl, (Ci-C4) -haloalkyl,
(C2-C4)-Alkenyl, (C2-C4)-Alkinyl, (C2-C4)-Haloalkenyl, (C2-C4)-Haloalkinyl, (C1-C4)- Alkylcarbonyl, (Ci-C4)-Haloalkylcarbonyl, Carboxyl, (Ci-C4)-Alkoxycarbonyl, (C1-C4)- Haloalkoxycarbonyl, (C3-C6)-Cycloalkoxycarbonyl, (Ci-C4)-Alkylaminocarbonyl, (C2-C6)-Dialkylaminocarbonyl, Hydroxy, (Ci-C4)-Alkoxy, (Ci-C4)-Haloalkoxy, (C1-C4)- Alkylthio, (Ci-C4)-Haloalkylthio, (Ci-C4)-Alkylsulfinyl, (Ci-C4)-Haloalkylsulfinyl, (Ci-C4)-Alkylsulfonyl, (Ci-C4)-Haloalkylsulfonyl, (Ci-C4)-Alkylaminosulfonyl, (C2-C6)- Dialkylaminosulfonyl oder (C3-C6)-Trialkylsilyl steht, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, (C 2 -C 4 ) haloalkenyl, (C 2 -C 4 ) haloalkynyl, (C 1 -C 4 ) alkylcarbonyl, (Ci-C 4 ) haloalkylcarbonyl, carboxyl, (Ci-C 4 ) alkoxycarbonyl, (C 1 -C 4 ) haloalkoxycarbonyl, (C 3 -C 6 ) cycloalkoxycarbonyl, (Ci-C 4 ) alkylaminocarbonyl, ( C 2 -C 6 ) dialkylaminocarbonyl, hydroxy, (Ci-C 4 ) alkoxy, (Ci-C 4 ) haloalkoxy, (C 1 -C 4 ) alkylthio, (Ci-C 4 ) haloalkylthio, (Ci -C 4 ) alkylsulfinyl, (Ci-C 4 ) -haloalkylsulfinyl, (Ci-C 4 ) -alkylsulfonyl, (Ci-C 4 ) -haloalkylsulfonyl, (Ci-C 4 ) -alkylaminosulfonyl, (C 2 -C 6 ) Dialkylaminosulfonyl or (C 3 -C 6 ) -trialkylsilyl,
R4 und R5 unabhängig voneinander für Wasserstoff, Hydroxy, Halogen, (Ci-C4)-Alkyl, (C1-C4)- Haloalkyl, (C2-C4)-Alkenyl, (C2-C4)-Alkinyl, (Ci-C4)-Alkoxycarbonyl, (C1-C4)- Haloalkoxycarbonyl oder (C3-C6)-Cycloalkoxycarbonyl stehen, oder R 4 and R 5 are independently hydrogen, hydroxy, halogen, (Ci-C 4) -alkyl, (C 1 -C 4) - haloalkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) -Alkynyl, (Ci-C 4 ) -alkoxycarbonyl, (C 1 -C 4 ) - haloalkoxycarbonyl or (C 3 -C 6 ) -cycloalkoxycarbonyl, or
R4 und R5 gemeinsam einen (Ci-C3)-Alkylidenrest oder (Ci-C3)-Haloalkylidenrest bilden, R 4 and R 5 together form a (Ci-C 3 ) alkylidene radical or (Ci-C 3 ) haloalkylidene radical,
R6 für Wasserstoff, (Ci-C i)-Alkyl, (Ci-C4)-Haloalkyl, Aryl-(Ci-C4)-alkyl, Heteroaryl-(Ci- C4)-alkyl, (C2-C4)-Alkenyl, (C2-C4)-Alkinyl, (Ci-C4)-Alkylcarbonyl, Formyl oder (Ci-C4)-Alkoxycarbonyl steht, und R7 für Wasserstoff, Halogen, Cyano, Nitro, Formyl, (Ci-C i)-Alkyl, (Ci-C4)-Haloalkyl,R 6 is hydrogen, (Ci-C i) -alkyl, (Ci-C 4 ) -haloalkyl, aryl- (Ci-C 4 ) -alkyl, heteroaryl- (Ci-C 4 ) -alkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) alkynyl, (Ci-C 4) alkylcarbonyl, formyl or (Ci-C 4) -alkoxycarbonyl, and R 7 represents hydrogen, halogen, cyano, nitro, formyl, (Ci-C i) alkyl, (Ci-C4) haloalkyl,
(C2-C4)-Alkenyl, (C2-C4)-Alkinyl, (C2-C4)-Haloalkenyl, (C2-C4)-Haloalkinyl, (Ci-C4)- Alkoxy-(Ci-C4)-alkyl, (Ci-C4)-Haloalkoxy-(Ci-C4)-alkyl, (Ci-C4)-Alkylcarbonyl, (Ci-C4)-Haloalkylcarbonyl, Carboxyl, (Ci-C4)-Alkoxycarbonyl, (Ci-C4)- Haloalkoxycarbonyl, (C3-C6)-Cycloalkoxycarbonyl, (Ci-C4)-Alkylaminocarbonyl, (C2-C6)-Dialkylaminocarbonyl, (C3-C6)-Cycloalkylaminocarbonyl, Hydroxy, (Ci-C4)- Alkoxy, (Ci-C4)-Haloalkoxy, (Ci-C4)-Alkylthio, (Ci-C4)-Haloalkylthio, (Ci-C4)- Alkylsulfmyl, (Ci-C4)-Haloalkylsulfinyl, (Ci-C4)-Alkylsulfonyl, (Ci-C4)- Haloalkylsulfonyl, (Ci-C4)-Alkylaminosulfonyl, (C2-C6)-Dialkylaminosulfonyl oder (C3-C6)-Trialkylsilyl steht. (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, (C 2 -C 4 ) haloalkenyl, (C 2 -C 4 ) haloalkynyl, (Ci-C 4 ) alkoxy- ( Ci-C 4 ) -alkyl, (Ci-C 4 ) -haloalkoxy- (Ci-C 4 ) -alkyl, (Ci-C 4 ) -alkylcarbonyl, (Ci-C 4 ) -haloalkylcarbonyl, carboxyl, (Ci-C 4 ) -alkoxycarbonyl, (Ci-C 4 ) - haloalkoxycarbonyl, (C3-C6) -cycloalkoxycarbonyl, (Ci-C 4 ) -alkylaminocarbonyl, (C 2 -C 6 ) -dialkylaminocarbonyl, (C3-C6) -cycloalkylaminocarbonyl, hydroxy , (Ci-C 4 ) - alkoxy, (Ci-C 4 ) -haloalkoxy, (Ci-C 4 ) -alkylthio, (Ci-C 4 ) -haloalkylthio, (Ci-C 4 ) - alkylsulfmyl, (Ci-C 4 ) -Haloalkylsulfinyl, (Ci-C 4 ) -alkylsulfonyl, (Ci-C 4 ) -haloalkylsulfonyl, (Ci-C 4 ) -alkylaminosulfonyl, (C 2 -C 6 ) -dialkylaminosulfonyl or (C3-C6) -trialkylsilyl ,
3. Verbindung der allgemeinen Formel (I) nach Anspruch 1 oder deren Salze, worin 3. A compound of general formula (I) according to claim 1 or its salts, wherein
X für -CH-, -CF- oder Stickstoff steht, X represents -CH-, -CF- or nitrogen,
A für Sauerstoff, Schwefel, -CH2 - oder -NR6- steht, A stands for oxygen, sulfur, -CH 2 - or -NR 6 -,
R1 für ein gegebnenfalls substituiertes Phenyl, Pyrid-2-yl, oder Pyrimid-2-yl steht, wobei jeder Ring optional mit bis zu 5 Substituenten, unabhängig voneinander ausgewählt aus der Gruppe R7, substituiert ist, R 1 represents an optionally substituted phenyl, pyrid-2-yl or pyrimid-2-yl, each ring optionally being substituted with up to 5 substituents, selected independently of one another from the group R 7 ,
R2 unabhängig voneinander für Fluor, Chlor, Brom, Cyano, Methyl, Ethyl, Trifluormethyl, Methoxy, Methoxycarbonylmethyl, Carboxylmethyl, steht, m ist gleich 0, 1, 2, oder 3, R 2 independently of one another represents fluorine, chlorine, bromine, cyano, methyl, ethyl, trifluoromethyl, methoxy, methoxycarbonylmethyl, carboxylmethyl, m is 0, 1, 2 or 3,
R3 für Wasserstoff, Fluor, Chlor, Cyano, Methyl, Trifluormethyl, Methoxy, R 3 for hydrogen, fluorine, chlorine, cyano, methyl, trifluoromethyl, methoxy,
Trifluormethoxy steht,  Trifluoromethoxy stands,
R6 für Wasserstoff oder Methyl steht, und R 6 represents hydrogen or methyl, and
R7 für Wasserstoff, Fluor, Chlor, Brom, Cyano, Methyl, Trifluormethyl, Methoxy, R 7 for hydrogen, fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl, methoxy,
Trifluormethoxy steht. Trifluoromethoxy stands.
4. Herbizide Mitel, gekennzeichnet durch einen herbizid wirksamen Gehalt an mindestens einer Verbindung der allgemeinen Formel (I) gemäß einem der Ansprüche 1 bis 3. 4. Herbicidal agents, characterized by a herbicidally active content of at least one compound of the general formula (I) according to one of claims 1 to 3.
5. Herbizide Mittel nach Anspruch 4 in Mischung mit Formulierungshilfsmitteln. 5. Herbicidal compositions according to claim 4 in a mixture with formulation auxiliaries.
6. Herbizide Mittel nach Anspruch 4 oder 5 enthaltend mindestens einen weiteren pestizid 6. Herbicidal compositions according to claim 4 or 5 containing at least one further pesticide
wirksamen Stoff aus der Gruppe Insektizide, Akarizide, Herbizide, Fungizide, Safener und W achstumsregulatoren.  active substance from the group insecticides, acaricides, herbicides, fungicides, safeners and growth regulators.
7. Herbizide Mitel nach Anspruch 6 enthaltend einen Safener. 7. Herbicidal agent according to claim 6 containing a safener.
8. Herbizide Mitel nach Anspruch 7 enthaltend Cyprosulfamid, Cloquintocet-mexyl, Mefenpyr- diethyl oder Isoxadifen-ethyl. 8. Herbicidal agent according to claim 7 containing cyprosulfamide, cloquintocet mexyl, mefenpyr diethyl or isoxadifen-ethyl.
9. Herbizide Mitel nach einem der Ansprüche 4 bis 8 enthaltend ein weiteres Herbizid. 9. Herbicidal agent according to one of claims 4 to 8 containing a further herbicide.
10. Verfahren zur Bekämpfung unerwünschter Pflanzen, dadurch gekennzeichnet, daß man eine wirksame Menge mindestens einer Verbindung der allgemeinen Formel (I) gemäß einem der Ansprüche 1 bis 3 oder eines herbiziden Mittels nach einem der Ansprüche 4 bis 9 auf die Pflanzen oder auf den Ort des unerwünschten Pflanzenwachstums appliziert. 10. A method for controlling unwanted plants, characterized in that an effective amount of at least one compound of the general formula (I) according to one of claims 1 to 3 or a herbicidal composition according to one of claims 4 to 9 on the plants or on the site of unwanted plant growth applied.
11. Verwendung von Verbindungen der allgemeinen Formel (I) gemäß einem der Ansprüche 1 bis 3 oder von herbiziden Mitteln nach einem der Ansprüche 4 bis 9 zur Bekämpfung unerwünschter Pflanzen. 11. Use of compounds of general formula (I) according to one of claims 1 to 3 or of herbicidal compositions according to one of claims 4 to 9 for controlling unwanted plants.
12. Verwendung nach Anspruch 11, dadurch gekennzeichnet, daß die Verbindungen der 12. Use according to claim 11, characterized in that the compounds of
allgemeinen Formel (1) zur Bekämpfung unerwünschter Pflanzen in Kulturen von Nutzpflanzen eingesetzt werden.  general formula (1) can be used to control unwanted plants in crops of useful plants.
13. Verwendung nach Anspruch 12, dadurch gekennzeichnet, daß die Nutzpflanzen transgene Nutzpflanzen sind. 13. Use according to claim 12, characterized in that the crop plants are transgenic crop plants.
EP19731734.0A 2018-06-25 2019-06-19 Substituted 2-heteroaryloxypyridines and salts thereof and their use as herbicidal agents Pending EP3810589A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP18179566 2018-06-25
PCT/EP2019/066197 WO2020002089A1 (en) 2018-06-25 2019-06-19 Substituted 2-heteroaryloxypyridines and salts thereof and their use as herbicidal agents

Publications (1)

Publication Number Publication Date
EP3810589A1 true EP3810589A1 (en) 2021-04-28

Family

ID=62778794

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19731734.0A Pending EP3810589A1 (en) 2018-06-25 2019-06-19 Substituted 2-heteroaryloxypyridines and salts thereof and their use as herbicidal agents

Country Status (10)

Country Link
US (1) US11834434B2 (en)
EP (1) EP3810589A1 (en)
JP (1) JP7394079B2 (en)
CN (1) CN112469712A (en)
AR (1) AR115629A1 (en)
AU (1) AU2019294743A1 (en)
BR (1) BR112020025919A2 (en)
CA (1) CA3105217A1 (en)
EA (1) EA202190111A1 (en)
WO (1) WO2020002089A1 (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112384507A (en) * 2018-06-25 2021-02-19 拜耳公司 Substituted 4-heteroaryloxypyridines and their salts and their use as herbicides
JP2023531060A (en) 2020-06-30 2023-07-20 バイエル・アクチエンゲゼルシヤフト Substituted heteroaryloxypyridines, their salts and their use as herbicides
EP4052670A1 (en) 2021-03-02 2022-09-07 AB Medica Instrument for blowing a gas into a live organ for aiding a medical dissection of said organ
CN114190189A (en) * 2021-11-18 2022-03-18 山东元泰生物工程有限公司 Method for promoting plant growth
WO2023186690A1 (en) 2022-03-28 2023-10-05 Bayer Aktiengesellschaft Substituted 2-aminoazines and salts thereof, and use thereof as herbicidal active substances
WO2023186691A1 (en) 2022-03-28 2023-10-05 Bayer Aktiengesellschaft Substituted 2-c-azines and salts thereof, and use thereof as herbicidal active substances

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4371736A (en) * 1981-03-27 1983-02-01 E. I. Du Pont De Nemours And Company Herbicidal pyridinyloxy(pyrimidinyloxy)benzenes
WO1997046530A1 (en) * 1996-06-06 1997-12-11 E.I. Du Pont De Nemours And Company Herbicidal pyridinyl and pyrazolylphenyl ketones
AR023071A1 (en) * 1998-12-23 2002-09-04 Syngenta Participations Ag PIRIDINCETONE COMPOUNDS, INTERMEDIATE COMPOUNDS, HERBICITY AND INHIBITOR COMPOSITION OF PLANTAGE GROWTH, METHOD FOR CONTROLLING INDESATED VEGETATION, METHOD FOR INHIBITING GROWTH OF PLANTS, AND USE OF COMPOSITION TO GROW GROWTH.
AU2003274025A1 (en) * 2002-10-17 2004-05-04 Syngenta Participations Ag Pyridine derivatives useful as herbicides
US8241618B2 (en) 2005-01-27 2012-08-14 Lubrizol Advanced Materials, Inc. Process for producing a hydrophobically modified polymer for use with personal care compositions
TW201609710A (en) 2013-12-10 2016-03-16 杜邦股份有限公司 Herbicidal substituted pyrimidinyloxy benzene compounds
MD4807C1 (en) 2014-01-16 2022-12-31 Fmc Corporation Pyrimidinyloxy benzene derivatives as herbicides
TW201625554A (en) 2014-07-14 2016-07-16 杜邦股份有限公司 Bis(aryl)catechol derivatives as herbicides
WO2016149315A1 (en) 2015-03-18 2016-09-22 E. I. Du Pont De Nemours And Company Substituted pyrimidinyloxy pyridine derivatives as herbicides
TWI828952B (en) 2015-06-05 2024-01-11 美商艾佛艾姆希公司 Pyrimidinyloxy benzene derivatives as herbicides
RU2745802C2 (en) * 2015-07-13 2021-04-01 Фмк Корпорейшн Aryloxy-pyrimidinyl esters as herbicides

Also Published As

Publication number Publication date
AR115629A1 (en) 2021-02-10
JP2021528448A (en) 2021-10-21
CN112469712A (en) 2021-03-09
CA3105217A1 (en) 2020-01-02
US11834434B2 (en) 2023-12-05
US20210276974A1 (en) 2021-09-09
JP7394079B2 (en) 2023-12-07
AU2019294743A1 (en) 2021-01-14
EA202190111A1 (en) 2021-04-23
WO2020002089A1 (en) 2020-01-02
BR112020025919A2 (en) 2021-03-16

Similar Documents

Publication Publication Date Title
EP3810589A1 (en) Substituted 2-heteroaryloxypyridines and salts thereof and their use as herbicidal agents
EP4003981A1 (en) Substituted n-phenyl uracils, salts thereof and their use as herbicidal agents
WO2019121543A1 (en) Substituted thiophenyl uracils, salts thereof and the use thereof as herbicidal agents
EP3947350A1 (en) Substituted 2-heteroarylaminobenzenes and the salts thereof and their use as herbicidal agents
WO2018114663A1 (en) Substituted azolylpyrrolones and azolylhydantoines and salts thereof and use thereof as herbicidal active substances
EP4003975A1 (en) Substituted n-phenyl-n-aminouarcils and salts thereof and use thereof as herbicidal agents
WO2019025156A1 (en) Substituted pyrrolidinones, salts thereof and use thereof as herbicidal agents
WO2019081477A1 (en) Substituted pyrazoles, salts thereof and use thereof as herbicidal agents
EP3728237A1 (en) Substituted thiophenyl uracils, salts thereof and the use thereof as herbicidal agents
EP3655393A1 (en) Substituted 5-(het-)arylpyrazolamides and salts thereof and their use as herbicidal active substances
WO2018177837A1 (en) 4-cyclopentyl- and 4-cyclopropyl-2-oxopyrrolidine-3-carboxamide derivatives and related compounds as herbicidal plant protection agents
WO2018178008A1 (en) Substituted isoxazoline-5-ones and salts thereof and use thereof as herbicidal agents
WO2018177836A1 (en) N-cyclopropyl-2-oxopyrrolidine-3-carboxamide derivatives and related compounds as herbicidal plant protection agents
EP4200282A1 (en) Substituted n-phenyluracils and salts thereof, and use thereof as herbicidal active substances
WO2021151976A1 (en) [(1,4,5-trisubstituted-1h-pyrazol-3-yl)sulfanyl]acetic acid derivatives, salts thereof, and use thereof as herbicidal ingredients
WO2020002087A1 (en) Substituted 3-heteroaryloxypyridines and salts thereof and their use as herbicidal agents
WO2020002085A1 (en) Substituted 4-heteroaryloxypyridines and salts thereof and their use as herbicidal agents
WO2019179928A1 (en) Substituted succinimide-3-carboxamides, salts thereof and the use thereof as herbicidal agents
WO2018184890A1 (en) 4-substituted n-amino and n-hydroxy 2-oxo-pyrrolidie-3-carboxamide derivatives, salts thereof and use thereof as herbicidal agents
WO2019081485A1 (en) Substituted pyrazoles, salts thereof and use thereof as herbicidal agents
WO2019121547A1 (en) Substituted thiophenyl uracils, salts thereof and the use thereof as herbicidal agents
WO2018114596A1 (en) Substituted heteroaryl pyrrolones and salts thereof and use thereof as herbicidal active substances
EP3497092A1 (en) Substituted pyrazolinyl derivates, method for the production thereof and use thereof as herbicides and/or plant growth regulators
WO2023161172A1 (en) Substituted n-benzoic acid uracils and salts thereof, and use thereof as herbicidal active substances
WO2020064260A1 (en) Substituted 5-(sulfanyl)-3,4-dihydro-2h-pyrrol-4-carboxamides and salts thereof and their use as herbicidal active substances

Legal Events

Date Code Title Description
STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: UNKNOWN

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE INTERNATIONAL PUBLICATION HAS BEEN MADE

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE INTERNATIONAL PUBLICATION HAS BEEN MADE

PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: REQUEST FOR EXAMINATION WAS MADE

17P Request for examination filed

Effective date: 20210125

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR

AX Request for extension of the european patent

Extension state: BA ME

DAV Request for validation of the european patent (deleted)
DAX Request for extension of the european patent (deleted)
STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: EXAMINATION IS IN PROGRESS

17Q First examination report despatched

Effective date: 20230622