EP3810589A1 - 2-hétéroaryloxypyridines substituées, leurs sels et leur utilisation comme agents herbicides - Google Patents

2-hétéroaryloxypyridines substituées, leurs sels et leur utilisation comme agents herbicides

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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)
English (en)
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
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Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Publication of EP3810589A1 publication Critical patent/EP3810589A1/fr
Pending legal-status Critical Current

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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)

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  • Engineering & Computer Science (AREA)
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Abstract

L'invention concerne des 2-hétéroaryloxypyridines substituées représentés par la formule générale (I) et leur utilisation comme herbicides, en particulier, pour lutter contre les mauvaises herbes et/ou graminées indésirables dans les cultures de plantes utiles et/ou comme régulateurs de croissance des plantes pour influencer la croissance de cultures de plantes utiles. La présente invention concerne en outre des agents herbicides et/ou régulateurs de croissance des plantes comprenant un ou plusieurs composés représentés par la formule générale (I).
EP19731734.0A 2018-06-25 2019-06-19 2-hétéroaryloxypyridines substituées, leurs sels et leur utilisation comme agents herbicides Pending EP3810589A1 (fr)

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MX2022016551A (es) 2020-06-30 2023-02-01 Bayer Ag Heteroariloxipiridinas sustituidas, asi como sus sales y su uso como principios activos herbicidas.
EP4052670A1 (fr) 2021-03-02 2022-09-07 AB Medica Instrument pour souffler un gaz dans un organe vivant pour favoriser une dissection médicale de cet organe
CN114190189A (zh) * 2021-11-18 2022-03-18 山东元泰生物工程有限公司 一种能够促进植物生长的方法
AR128874A1 (es) 2022-03-28 2024-06-19 Bayer Ag 2-aminoazinas sustituidas y sus sales y su uso como ingredientes activos herbicidas
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US4371736A (en) * 1981-03-27 1983-02-01 E. I. Du Pont De Nemours And Company Herbicidal pyridinyloxy(pyrimidinyloxy)benzenes
EP0922032A1 (fr) * 1996-06-06 1999-06-16 E.I. Du Pont De Nemours And Company Pyridinylcetones et pyrazolylphenylcetones herbicides
AR023071A1 (es) * 1998-12-23 2002-09-04 Syngenta Participations Ag Compuestos de piridincetona, compuestos intermediarios, composicion herbicida e inhibidora del crecimiento de plantas, metodo para controlar la vegetacion indeseada, metodo para inhibir el crecimiento de las plantas, y uso de la composicion para controlar el crecimiento indeseado de plantas.
WO2004035564A1 (fr) * 2002-10-17 2004-04-29 Syngenta Participations Ag Derives de pyridine utiles comme 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 (zh) 2013-12-10 2016-03-16 杜邦股份有限公司 除草用經取代嘧啶氧基苯化合物
PE20161143A1 (es) 2014-01-16 2016-11-18 Du Pont Derivados de pirimidiniloxi benceno como herbicidas
TW201625554A (zh) 2014-07-14 2016-07-16 杜邦股份有限公司 作為除草劑之雙芳基兒茶酚衍生物
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RU2745802C2 (ru) * 2015-07-13 2021-04-01 Фмк Корпорейшн Арилоксипиримидиниловые эфиры в качестве гербицидов

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